WO2015137630A1 - Condensed-ring compound and organic light-emitting element comprising same - Google Patents

Condensed-ring compound and organic light-emitting element comprising same Download PDF

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WO2015137630A1
WO2015137630A1 PCT/KR2015/001286 KR2015001286W WO2015137630A1 WO 2015137630 A1 WO2015137630 A1 WO 2015137630A1 KR 2015001286 W KR2015001286 W KR 2015001286W WO 2015137630 A1 WO2015137630 A1 WO 2015137630A1
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group
substituted
formula
unsubstituted
salt
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PCT/KR2015/001286
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French (fr)
Korean (ko)
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김창우
김병구
김영권
김형선
서주희
신창주
이승재
황규영
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삼성에스디아이 주식회사
삼성전자 주식회사
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Priority to CN201580005190.9A priority Critical patent/CN106414452B/en
Priority to US15/104,017 priority patent/US20160322585A1/en
Priority claimed from KR1020150019192A external-priority patent/KR101929859B1/en
Publication of WO2015137630A1 publication Critical patent/WO2015137630A1/en

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Definitions

  • Organic light emitting diodes are self-luminous devices that have a wide viewing angle, excellent contrast, quick response time, excellent luminance, driving voltage, and quick response speed, and are capable of multicoloring.
  • the organic light emitting diode may include an anode, a cathode, and a light emitting layer interposed between the anode and the cathode.
  • a hole transport region may be provided between the anode and the light emitting layer, and an electron transport region may be provided between the light emitting layer and the cathode.
  • Holes injected from the anode move to the light emitting layer via the hole transport region, and electrons injected from the cathode move to the light emitting layer via the electron transport region.
  • Carriers such as holes and electrons recombine in the emission layer to generate excitons. The excitons change from excited state to ground state and light is generated.
  • a novel condensed cyclic compound and an organic light emitting device employing the same are provided.
  • a condensed cyclic compound represented by Formula 1 is provided:
  • Ring Au and ring A 12 are each independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine and triazine;
  • L, to L 4 , L U and L 12 are each independently a substituted or unsubstituted
  • c 2 -c 10 heterocycloalkenylene group substituted or unsubstituted C 6 -C 60 arylene group, substituted or An unsubstituted C 2 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group;
  • al to a4, al l and al2 are each independently selected from an integer of 0 to 3;
  • Ri to 3 ⁇ 4 and Ru to R 20 are each independently hydrogen, deuterium, -F (fluoro group), -C1 (chloro group), -Br (bromo group), -1 (iodo group), hydroxyl group, Cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted -C 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted Cl _C 60 alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted
  • bl to b4, bl 1, M2 and bl6 to b20 are each independently selected from an integer of 1 to 3;
  • At least one of the substituents of the condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group is
  • C 2 -C 10 hetero come cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea,
  • C 2 -C 10 year Tero cycloalkenyl group C 6 -C 60 aryl group import, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea, c 2 -c 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q 21 ) (Q 22 ), -Si (Q 23 XQ 24 ) (Q 25 C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, substituted with at least one of -B (Q 26 ) (Q 27 ),
  • c 2 -c 10 by interrogating cycloalkenyl group, c 6 -c 60 aryl group, c 6 -c 60 aryloxy group, c 6 -c 60 aryl come tea, C 2 -C 60 heteroaryl group, a monovalent non- Aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group; And
  • Qu to Q 17 , Q 21 to Q 27, and Q 3 i to Q 37 are each independently hydrogen, d-oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, ⁇ -0 alkoxy group, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
  • the first electrode Second electrode; And an organic layer interposed between the first electrode and the second electrode and including an emission layer, the organic layer including at least one or more condensed cyclic compounds represented by Formula 1.
  • the condensed cyclic compound may be included in the emission layer, the emission layer may further include a dopant, and the condensed cyclic compound included in the emission layer may serve as a host.
  • the condensed cyclic compound has excellent electrical properties and thermal stability, the organic light emitting device employing the condensed cyclic compound may have a low driving voltage, high efficiency, high brightness and long life.
  • FIG. 1 schematically shows an organic light emitting device according to one embodiment
  • the condensed cyclic compound is represented by the following Chemical Formula 1:
  • ring A u and ring A 12 may be independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, and triazine.
  • the ring A u and ring A 12 may be benzene, but are not limited thereto.
  • R I2 (R I2) bl2] if it is not, the above formula (1) of bl7 of R 17, bll - i) and Xn is the formula N-Rn KLu ⁇ u] of 1, 2, N - [(L 12) al2
  • At least one of R n , bl 8 R 1S , M 9 R 19 and b20 R 20 is selected from the group represented by Formula 2A to the group represented by Formula 2F;
  • N - [(L 12) al2 - (R 12) bl2] be the case, of the formula 1 bl7 of R I7, M8 of R 18, M9 of R 19, at least one of the bl2 of R 12 and b20 of R 20 is Selected from the group represented by Formula 2A to the group represented by Formula 2F;
  • X u in Formula 1 is May be selected from S and 0.
  • two of the formula 1B is N - and can be selected from, S and 0 - [(R 12) bl2 (L 12) al2].
  • 2 N - [(L l2) al2 - may be a (R 12) bl2], but not limited to eu
  • 3 ⁇ 4 of Formulas 2A to 2F may be selected from N-[(LO al- (RO bl ), S and 0.
  • L 4 , L U and L 12 in the above formulas may be each independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted group.
  • L 4 , Lu, and L 12 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, or an azule group.
  • Fluorenylene group spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, phenanthrenylene group, anthracenylene group,
  • Fluoranthrenylene group triphenylenylene group
  • Naphthacenylene group picenylene group, picenylene group, perylenylene group, pentaphenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group (imidazolylene) , Pyrazolylene group, pyridinylene group, pyrazinylene group, pyrazinylene group, pyrimidinylene group,
  • Phenanthridinylene group (phenanthridinylene), acridinylene group (acridinylene),
  • Phenanthrolinylene phenazinylene
  • Benzooxazolylene group benzoimidazolylene group, benzoimidazolylene, furanylene group, foranylene, benzofuranylene group, thiophenylene group, benzothiophenylene group, benzothiophenylene group, thiazolylene group (thiazolylene),
  • Azulenylene group heptalenylene group, indasenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, penalenylene group, phenanthrenylene group, anthracenylene group,
  • Fluoranthrenylene group triphenylenylene group, pyrenylene group, crysenylene group,
  • Quinolinyl group isoquinolinyl group, benzoquinolinyl group, phthalazinylene group,
  • Naphthyridinylene group quinoxalinylene group, quinazolinyl group, cynolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrylinylene group, phenazinylene group,
  • Benzoxazolylene group benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazoleylene group,
  • Oxadiazolylene group triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazole ylene group, dibenzo carbazole ylene group imidazopyrimidinylene group and
  • Q 33 to Q 35 are each independently hydrogen, ⁇ -0 alkyl group, dC 2 .alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarba Solyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group,
  • It may be selected from a quinoxalinyl group, a cynolinyl group, and a quinazolinyl group.
  • L U and L 12 are mutually
  • Z, to Z 4 are independently of each other hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acids or salts thereof, sulfonic acids or salts thereof, phosphoric acid or salts thereof, CC 20 alkyl groups, CrC 20 alkoxy groups, phenyl groups, naphthyl groups, anthracenyl groups, triphenylenyl groups, pyrenyl groups, phenanthrenyl groups, fluorenyl groups, Chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl
  • Q 33 to Q 35 are each independently hydrogen, C! -Oalkyl, C ⁇ ) alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, chrysenyl, Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group,
  • dl is selected from integers of 1 to 4
  • d2 is selected from integers of 1 to 3
  • d3 is selected from integers of 1 to 6
  • d4 is selected from integers of 1 to 8
  • d6 is selected from 1 to 5
  • And * and * may be binding sites with neighboring atoms.
  • L 4 , L U, and L 12 of the above formulas may be independently selected from the following Formulas 3-1 to 3-12, but are not limited thereto.
  • al represents the number of and is selected from an integer of 0 to 3. For example, al can be 0 or 1. If al is 0, 3 ⁇ 4 is directly connected to N. When al is 2 or more, two or more Lr may be the same as or different from each other. Description of a2 to a4, al l and al2 is described for al and formula 1 and formula See the description of 2A through 2F.
  • al to a4, al l and al2 may be 0 or 1, independently of each other.
  • R 6 and R n to R 20 in the above formulas independently of each other, hydrogen, hydrogen, -F (pluoro group), -Cl (chloro group), -Br (bromo group), -1 (Io) Earthenware), hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted
  • C 3 -C 10 cycloalkyl group substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -CK> cycloalkenyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group , Substituted or unsubstituted C 6 -C 6 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 arylthio group, substituted or unsubstituted C 2 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic
  • the R, to R6 and Ru to R 20 are mutually, hydrogen, deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, Amidino groups, hydrazine groups, hydrazone groups, carboxylic acids or salts thereof, sulfonic acids or salts thereof, phosphoric acid or salts thereof, -0 alkyl groups and CrC 20 alkoxy groups;
  • Phenanthrenyl phenanthrenyl
  • anthracenyl anthracenyl
  • fluoroanthhenyl fluoranthenyl
  • Triphenylenyl pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl,
  • Pentaphenyl group (pentaphenyl), nucleasenyl group (hexacenyl), pentaxenyl group (pentacenyl),
  • Rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group (thiophenyl), furanyl group (fur any 1), imidazolyl group (imidazolyl),
  • Phenanthridinyl group (phenanthridinyl), acridinyl group (acridinyl),
  • Phenanthrolinyl phenazinyl
  • Triazolyl group tetrazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzofuranyl group,
  • Dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group, dibenzocarbazolyl group,
  • Fluorenyl Fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzopolorenyl, penalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl,
  • Q 3 to Q 5 and Q 33 to Q 35 are each independently hydrogen, ⁇ -0 alkyl, C! -Oalkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl or fluore.
  • R, to 3 ⁇ 4 are represented by the group represented by the formula (2A) to (2F), but are not limited thereto:
  • Y 31 is 0, S, C (Z 33 ) (Z 34 ), N (Z 35 ) or Si (Z 36 ) (3 ⁇ 4 7 ), provided that Y 31 in Formula 4-23 is not ⁇ ;
  • ⁇ ⁇ 31 to 37 are, independently of each other, hydrogen, heavy hydrogen, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic Acids or salts thereof, sulfonic acids or salts thereof, phosphoric acid or salts thereof, Ci-oalkyl groups, C!
  • -Oalkoxy groups phenyl groups, naphthyl groups, anthracenyl groups, triphenylenyl groups, pyrenyl groups, phenanthrenyl groups, Fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso Quinolinyl group, quinazolinyl group, quinoxalinyl group, biphenyl group, and
  • Q 3 to Q 5 and Q 33 to Q 35 are each independently hydrogen, d-oalkyl group, alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, flu Orenyl group, chrysenyl group, carbazole group, benzocarbazole group,
  • Dibenzocarbazolyl dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl and quinoxalinyl;
  • el is selected from integers of 1 to 5
  • e2 is selected from integers of 1 to 7
  • e3 is selected from integers of 1 to 3
  • e4 is selected from integers of 1 to 4
  • e5 is 1 or 2
  • e6 is selected from an integer of 1 to 6 and * is a binding site with a neighboring atom.
  • R 2 of Formulas 2A and 2B, R 3 of Formulas 2C and 2D, and R 2 and R 3 of Formulas 2E and 2F are each independently,
  • Phenyl group pentalenyl group, indenyl group, naphthyl group, azelenyl group, heptalenyl group, indasenyl group acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group,
  • Dibenzofluorenyl group phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, fisenyl group, perenyl group, pentaphenyl group Nucleasenyl, pentacenyl, rubisenyl, coronyl, ovarenyl, pyridyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl
  • -oalkyl group dC 2 oalkoxy group, -Si (Q 33 ) (Q 34 ) (Q 35 ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, ace Naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzopolorenyl, penalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl ,
  • Phenantridinyl group acridinyl group, phenanthlinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group,
  • Isobenzooxazolyl group triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group,
  • Phenyl group pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorene substituted with at least one of imidazopyridinyl group, imidazopyrimidinyl group and biphenyl Nyl group, spiro-fluorenyl group, benzofluorenyl group,
  • Dibenzofluorenyl group phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group , Nucleoxenyl group, pentaxenyl group, rubisenyl group, coronyl group, ovalenyl group, piryl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furiny
  • Q 33 to Q 35 may be each independently selected from hydrogen, ⁇ -oalkyl group, d-oalkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group,
  • Chrysenyl group carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group,
  • It may be selected from an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group.
  • R 2 of Formulas 2A and 2B, of Formulas 2C and 2D are independently selected from
  • R 3 and at least one of the general formula 2E and 2F of the R 2 and R 3 are,
  • Phenyl group pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, pulluorenyl group, spiro-fluorenyl group, cofluorenyl group,
  • Dibenzofluorenyl group penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group Nucleasenyl, pentacenyl, rubisenyl, coronyl, ovalenyl, pyryl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, is
  • Benzoxazolyl group isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
  • Isobenzooxazolyl group triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group,
  • Phenyl group pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorene substituted with at least one of imidazopyridinyl group, imidazopyrimidinyl group and biphenyl Nyl group, spiro-fluorenyl group, benzofluorenyl group,
  • Dibenzofluorenyl group phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, fisenyl group, perenyl group, pentaphenyl group , Nuxasenyl group, pentaxenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazole group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furin
  • Benzoxazolyl group isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
  • Q 33 to Q 35 may be each independently selected from a hydrogen, a C o alkyl group, an o-alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, and a chrysenyl group.
  • Carbazolyl benzocarbazolyl, dibenzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, It may be selected from an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group.
  • R 2 of Formulas 2A and 2B, R 3 of Formulas 2C and 2D, and R 2 and R 3 of Formulas 2E and 2F are examples of at least one of R 2 of Formulas 2A and 2B, R 3 of Formulas 2C and 2D, and R 2 and R 3 of Formulas 2E and 2F,
  • Q 33 to Q 35 are independently of each other, may be selected from hydrogen, -3 ⁇ 4 ⁇ 0 alkyl, C ⁇ o alkoxy group, a phenyl group and a naphthyl group.
  • At least one of R 3 and 2D of the general formula 2E and 2F R 2 and R 3, may be selected from Formula 5-1 to 5-63, and the like.
  • the formula 2A to 2F of R l 5 of the formula (I) and of formula (1) B X 12 ⁇ of R 12 are each independently of the substituted or unsubstituted
  • R u of X u of Formula 1 and R 12 of X 12 of Formula 1B of Formulas 2A to 2F may be each independently,
  • R 4 in Formulas 2A to 2F are each independently hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, or amidino group.
  • Hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, d-oalkyl group and CrC 20 alkoxy group can be selected, but is not limited thereto.
  • Bl represents the number of and may be selected from integers of 1 to 3. When bl is 2 or more, two or more R1 may be the same or different from each other.
  • bl1, bl2 and M7 to b20 refer to the description of bl and the structures of Formula 1 and Formulas 2A to 2F.
  • the condensed cyclic compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas 1-1 to 1-9:
  • X n and 12 in Formulas 1-1 to 1-9 are the same as described in claim 1, and for the description of R 21 to R 24 , refer to the description for R 17 , and R 25 to R 27.
  • R 21 to R 24 refers to the description for R 17 , and R 25 to R 27.
  • R 31 to R 34 refers to the description of R 20
  • R 35 to R 37 refer to the description of R 19 .
  • Is selected from N-[(L,) al- (R,) bl ], S and 0;
  • N is N-KLu ⁇ Ru u]
  • 2 is
  • N - [(L 12) al2 - (R 12) bl2] be the case, of the formula 1 Ml of R u, bl2 of R 12, R 21 to R 27 and R 31 to 7 at least one of the formula (2A) It is selected from the group represented by the group represented by the formula (2F);
  • L U and L 12 are each independently selected from Formulas 2-1 to 2-13 (eg, Formulas 3-1 to 3-12);
  • At least one of the R 2 and R 3 At least one of the R 2 and R 3 ,
  • 3 ⁇ 4 is hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or Salts thereof, phosphoric acid or salts thereof, CrC 20 alkyl groups and dC 2 oalkoxy groups;
  • R 2 To R 27 and R 31 to 7 are independently of each other,
  • a group represented by Formula 2A to a group represented by Formula 2F provided that the group is not a group represented by Formula 2A to a group represented by Formula 2A; It may be selected from, but is not limited thereto.
  • the condensed cyclic compound represented by Formula 1 is represented by Formula 1-1, 1-3, or 1-5,
  • R u and R 12 are independently of each other
  • At least one of Ru and R 12 may be selected from a group represented by Formula 2A to a group represented by Formula 2F, but is not limited thereto.
  • the condensed cyclic compound represented by Formula 1 may be one of Compounds 1 to 30, but is not limited thereto.
  • the condensed cyclic compound represented by Formula 1 necessarily includes at least one of the group represented by Formula 2A to the group represented by Formula 2F.
  • the condensed cyclic compound represented by Formula 1 may have a bipolar characteristic, and may have a HOMO, LUMQ energy gap, and T1 energy level suitable for use as an organic light emitting device material (for example, a host in the light emitting layer). have.
  • the condensed cyclic compound represented by Chemical Formula 1 may be suitable for use as an organic layer of an organic light emitting device, for example, as a host of a light emitting layer in the organic layer.
  • An organic light-emitting device including an organic layer, which includes a light emitting layer and includes at least one or more types of condensed cyclic compounds represented by the formula (1).
  • the organic light emitting device may have a low driving voltage, high efficiency, high brightness, and long life by including an organic layer including a condensed cyclic compound represented by Formula 1 as described above.
  • the condensed cyclic compound represented by Formula 1 may be used between a pair of electrodes of the organic light emitting device.
  • the condensed cyclic compound may include a light emitting layer, a hole transport region (for example, at least one of a hole injection layer, a hole transport layer, and an electron blocking layer) between the light emitting layer, the first electrode, and the light emitting layer, and the light emitting layer and the second electrode. It may be included in at least one of the electron transport region (eg, including at least one of a hole blocking layer, an electron transport layer and an electron injection layer).
  • the condensed cyclic compound represented by Formula 1 may be included in the emission layer.
  • the light emitting layer may further include a dopant, and the condensed cyclic compound included in the light emitting layer may serve as a host.
  • the light emitting layer may be a blue light emitting layer or a green light emitting layer emitting blue light or green light, and the dopant may be a phosphorescent dopant.
  • (organic layer) contains one or more types of condensed cyclic compounds
  • organic layer may include one condensed cyclic compound belonging to the category of Formula 1 or two or more different condensed cyclic compounds belonging to the category of Formula 1.
  • the organic layer may include only Compound 1 as the condensed cyclic compound.
  • the compound 1 may be present in the light emitting layer of the organic light emitting device.
  • the organic layer may include Compound 1 and Compound 2 as the condensed cyclic compound.
  • the compound 1 and compound 2 may be present in the same layer (for example, both compound 1 and compound 2 may be present in the light emitting layer), or may be present in different layers.
  • the first electrode is an anode which is a hole injection electrode and the second electrode is a cathode which is an electron injection electrode, or the first electrode is a cathode which is an electron injection electrode, and the second electrode is a cathode which is a hole injection electrode.
  • the first electrode is an anode
  • the crab second electrode is a cathode
  • the organic layer is, i) interposed between the first electrode and the light emitting layer, a hole injection layer, a hole A hole transport region comprising at least one of a transport layer and an electron blocking layer; And ii) an electron transport region interposed between the light emitting layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
  • organic layer refers to a single and / or a plurality of layers interposed between the first electrode and the second electrode of the organic light emitting device.
  • the "organic layer” may include not only an organic compound but also an organometallic complex including a metal.
  • FIG. 1 schematically illustrates a cross-sectional view of an organic light emitting device 10 according to one embodiment of the invention.
  • a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. 1.
  • the element 10 has a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked.
  • a substrate may be further disposed below the first electrode 11 or above the second electrode 19.
  • a substrate used in a conventional organic light emitting device can be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.
  • the first electrode 11 may be formed by, for example, providing a material for the first electrode on the substrate by using a deposition method or a sputtering method.
  • the first electrode 11 may be an anode.
  • the material for the first electrode may be selected from materials having a high work function to facilitate hole injection.
  • the first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode.
  • Indium zinc oxide (IZO), tin oxide (Sn0 2 ), zinc oxide (ZnO) and the like can be used.
  • metals such as magnesium (Mg), aluminum (A1), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like can be used. have.
  • the first electrode 11 may have a single layer or a multilayer structure including two or more layers.
  • the organic layer 15 is disposed above the cradle 1 electrode 11.
  • the organic layer 15 may include a hole transport region; An emission layer; And an electron transport region.
  • the hole transport region may be disposed between the crab electrode 1 11 and the light emitting layer.
  • the hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.
  • the hole transport region may include only a hole injection layer or only a hole transport layer.
  • the hole transport region may have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer, which are sequentially stacked from the first electrode 11.
  • the hole injection layer HIL may be formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, cast, LB, and the like. Can be.
  • the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the hole injection layer as desired, and the deposition temperature is about 100 to about, for example. 500 ° C., vacuum degree of about HT 8 to about 10 " 3 torr, and deposition rate of about 0.01 to about 100 A / sec, but is not limited thereto.
  • the coating conditions are:
  • the coating speed of about 2000rpm to about 5000rpm, the heat treatment temperature for removing the solvent after coating is about 80 ° C to 200 ° It may be selected in the temperature range of C : but not limited to.
  • the hole transport layer and the electron blocking layer forming conditions refer to the hole injection layer forming conditions.
  • the hole transport region may be, for example, m-MTDATA, TDATA, 2-TNATA, NPB, ⁇ - ⁇ , TPD, Spiro-TPD, Spiro-NPB, ⁇ - ⁇ , TAPC, HMTPD,
  • TCTA 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine (4,4', 4" -tris (N-carbazolyl) triphenylamme)
  • Pani / DBSA Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / Dodecylbenzenesulfonic acid
  • PEDOT / PSS Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenes ⁇ styrenedioxiophene) / poly (4-styrenesulfonate)
  • Pani / CSA Polyaniline / Camphor
  • sulfonicacid polyaniline / camphor sulfonic acid), PANI / PSS
  • Ar 101 and Ar l02 are each independently,
  • Phenylene group pentalenylene group, indenylene group, naphthylene group, azulenylene group,
  • Heptalenylene group acenaphthylene group, fluorenylene group, phenenylene group, phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenylenylene group, pyrenylene group,
  • C 2 -C 10 hetero come cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea,
  • C 2 -C 60 heteroaryl group a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azule substituted with at least one of a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed polycyclic group.
  • xa and xb may be each independently an integer of 0 to 5, or 0, 1 or 2.
  • xa may be 1 and xb may be 0, but is not limited thereto.
  • R 101 to R 108 , Rm to R, and Rui to R 124 are each independently of one another.
  • R 109 is a phenyl group, a naphthyl group, anthracenyl group, and a pyridinyl group; And deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phenyl, naphthyl, anthracenyl and pyridinyl groups substituted with one or more of phosphoric acid groups or salts thereof, d-oalkyl groups and dC 20 alkoxy groups; It may be one of the.
  • the compound represented by Formula 2 is represented by the formula
  • 201A but is not limited to: ⁇ 201 A>
  • R 101 , R m , R 112, and R 109 may be referred to the foregoing for detailed description.
  • the compound represented by Formula 2 and the compound represented by Formula 202 may include the following compounds HT1 to HT20, but are not limited thereto.
  • the hole transport region may have a thickness of about 100A to about 10000A, for example, about 100A to about 1000A. If the hole transport region includes both a hole injection layer and a hole transport layer, the hole injection layer has a thickness of about 100 A to about 10000 A, for example, about 100 A to about 1000 A, and the hole transport layer has a thickness of about 50 A. To about 2000A, for example about 100A to about 1500A. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.
  • the hole transport region may further include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or heterogeneously dispersed in the hole transport region.
  • the charge-generating material may be, for example, a P-dopant.
  • the P-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.
  • the P-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.
  • TCNQ Tetracyanoquinonedimethane
  • the hole transport region may further include a buffer layer.
  • the buffer layer may serve to increase efficiency by compensating an optical resonance distance according to a wavelength of light emitted from the emission layer.
  • An emission layer may be formed on the hole transport region by using a method such as vacuum deposition, spin coating, casting, and LB.
  • a method such as vacuum deposition, spin coating, casting, and LB.
  • the deposition conditions and coating conditions vary depending on the compound to be used, and in general, may be selected from a range of conditions substantially the same as the formation of the hole injection layer.
  • the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer.
  • the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.
  • the light emitting layer may include a host and a dopant.
  • the host may include a condensed cyclic compound represented by Chemical Formula 1.
  • the light emitting layer may be a green light emitting layer for emitting green light.
  • the dopant in the light emitting layer may include a fluorescent dopant emitting light according to a fluorescence emitting mechanism or a phosphorescent dopant emitting light according to a phosphorescent emitting mechanism.
  • the host is different from the first host and
  • At least one may include:
  • Ring A 61 in Formula 61 is represented by Formula 61 A;
  • Ring A 62 in Formula 61 is represented by Formula 61B;
  • Group X is C (R 71 ) or N
  • X 72 is C (R 72 ) or N
  • X 73 is C (R 73 ) or N
  • X 74 is C (R 74 )
  • N X 75 is C (R 75 ) or N
  • X 76 is C (R 76 ) or N
  • X 77 is C (R 77 ) or N
  • X 78 is C (R 78 ) or N ego;
  • nl and n2 are each independently selected from an integer of 0 to 3;
  • a41, a42, a61 and a62 are each independently selected from an integer of 0 to 3;
  • R41 to R43, R 5 1 to 4, 1 to R64 and R71 to R? 9 are each independently hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted Cr oalkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group , Substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted C!
  • b41, b42, b51 to b54, b61, b62 and b79 may be each independently selected from integers of 1 to 3.
  • the! Ni to 3 ⁇ 4 3 , 11 51 to RM,! ⁇ To R64 and R 7 i to R 79 are each independently,
  • Phenyl group pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group,
  • Dibenzofluorenyl group phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, fisenyl group, perylenyl group, pentaphenyl group , Nuxasenyl group, pentaxenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group,
  • Benzoxazolyl group isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
  • Benzoxazolyl group isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
  • Dibenzocarbazolyl group imidazopyridinyl group, and imidazopyrimidinyl;
  • Benzothiophenyl group isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Phenyl group, pentalenyl group, indenyl group, naphthyl group, azelenyl group, heptalenyl group, indyl substituted with at least one of a zolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl and biphenyl group Senyl, Acenaphthyl,
  • Fluorenyl group spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group,
  • Q 3 to Q 5 and Q 33 to Q 35 are each independently hydrogen, d-oalkyl group, Cr oalkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, Chrysenyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, It may be selected from a quinazolinyl group and a quinoxalinyl group, but is not limited thereto.
  • the first compound may be represented by one of Formula 41 -1 to 41 -12.
  • the second compound may be represented by one of Chemical Formulas 61-1 to 61-6:
  • R 61 to R 64 , b61, b62, R 71 to R 79 and b79 refer to what is described herein.
  • the first compound represented by Formula 41 is the following compound
  • One of A1 to A16, and the second compound represented by Chemical Formula 61 may include one of the following compounds B1 to B4:
  • M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), flow path product (Eu), terbium (Tb) and lium (Tm) ;
  • Y, to Y 4 are, independently of each other, carbon (C) or nitrogen ( ⁇ );
  • ⁇ And ⁇ 2 are linked via a single bond or a double bond, and ⁇ 3 and ⁇ 4 are linked through a single bond or a double bond;
  • CY, and CY 2 are independently of each other, benzene, naphthalene, fluorene,
  • R 81 and 2 independently of each other, hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid Or salts thereof, sulfonic acid or salts thereof, phosphoric acid or salts thereof, -SF 5 , substituted or unsubstituted CrC 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted
  • a81 and a82 are each independently selected from an integer of 1 to 5;
  • n81 is selected from an integer of 0 to 4.
  • n82 is 1, 2 or 3;
  • L 81 is selected from monovalent organic ligand, divalent organic ligand and trivalent organic ligand;
  • a bond between Y 2 and a bond between Y 3 and X 4 are a single bond or a double bond.
  • the phosphorescent dopant may comprise the following PtOEP or compound PhGD:
  • the dopant content is
  • it may be selected from about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
  • the light emitting layer may have a thickness of about 100A to about 1000A, for example, about 200A to about 600A. When the thickness of the light emitting layer satisfies the aforementioned range, the light emitting layer may exhibit excellent light emission characteristics without a substantial increase in driving voltage.
  • an electron transport region is disposed on the emission layer.
  • the electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the electron transport region may be a hole blocking layer / electron transport layer / electron injection layer or It may have a structure of an electron transport layer / electron injection layer, but is not limited thereto.
  • the electron transport layer may have a single layer or a multilayer structure including two or more different materials.
  • the formation conditions of the hole blocking layer, the electron transport layer, and the electron injection layer of the electron transport region may be referred to the formation conditions of the hole injection layer.
  • the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq, but is not limited thereto.
  • the hole blocking layer may have a thickness of about 20 A to about 1000 A, for example, about 30 A to about 300 A. When the thickness of the hole blocking layer satisfies the aforementioned range, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
  • the electron transport layer may further include at least one of BCP, Bphen and Alq 3 , Balq, TAZ, and NTAZ.
  • the electron transport layer may include at least one of the following compounds ET1 and ET2, but is not limited thereto.
  • the electron transport layer may have a thickness of about 100A to about 1000A, for example, about 150A to about 500A .
  • a satisfactory electron transporting characteristic can be obtained without a substantial increase in driving voltage.
  • the electron transport layer may further include a metal-containing material, in addition to the materials described above.
  • the metal-containing material may comprise a Li complex.
  • the Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or ET-D2.
  • the electron transport region may also include an electron injection layer (EIL) that facilitates injection of electrons from the second electrode 19.
  • EIL electron injection layer
  • the electron injection layer may include at least one selected from among LiF, NaCl, CsF, Li 2 O, and BaO.
  • the electron injection layer may have a thickness of about 1 A to about 100 A, about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the aforementioned range, a satisfactory electron injection characteristic may be obtained without a substantial increase in driving voltage.
  • Crab electrodes 19 are provided on the organic layer 15.
  • the crab second electrode 19 may be a cathode.
  • a metal, an alloy, an electrically conductive compound having a relatively low work function, or a combination thereof may be used. Concrete Examples include lithium (Li), magnesium (Mg), aluminum (A1), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. It can be used as a material for forming the two-electrode 19. Alternatively, various modifications are possible, such as the transmissive crab 2 electrode 19 can be formed using ⁇ , ⁇ to obtain a front light emitting element.
  • the organic light emitting device has been described above with reference to FIG. 1, but is not limited thereto.
  • the CrC 60 alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include methyl group, ethyl group, propyl group, isobutyl group, sec -butyl group, ter ⁇ Butyl group, pentyl group, iso-amyl group, nuclear chamber group and the like.
  • C ! oalkylene group means a divalent group having the same structure as said d-oalkyl group.
  • a CrC 60 alkoxy group refers to a monovalent group having a chemical formula of —OA 101 (wherein A 101 is the d-oalkyl group), and specific examples thereof include a methoxy group, an hydroxy group, an isopropyloxy group, and the like. This includes.
  • the C 2 -C 60 alkenyl group has a structure including at least one carbon double bond in the middle or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include an ethenyl group, propenyl group, butenyl group, and the like. do.
  • the c 2 -c 60 alkenylene group is
  • a divalent group having the same structure as a C 2 -C 60 alkenyl group is a divalent group having the same structure as a C 2 -C 60 alkenyl group.
  • the C 2 -C 60 alkynyl group has a structure including one or more carbon triple bonds at the intermediate or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include:
  • C 2 -C 60 alkynylene group refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.
  • a C 3 -C 10 cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclonuxyl group and a cyclohep And a tilt group.
  • C 3 -C 10 cycloalkylene group means a divalent group having the same structure as the C 3 -C 10 cycloalkyl group.
  • C 2 -C 10 heterocycloalkyl group in the present specification includes a monovalent having 2 to 10 carbon atoms containing at least one hetero atom selected from ⁇ , ⁇ , ⁇ , and S as a ring-forming atom.
  • Monocyclic group specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group and the like.
  • C 2 -C 10 heterocycloalkylene group means a divalent group having the same structure as the C 2 -C 10 heterocycloalkyl group.
  • a C 3 -C 10 cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one double bond in a ring, but having no aromacity, and specific examples thereof Examples include a cyclopentenyl group, a cyclonuxenyl group, a cycloheptenyl group, and the like.
  • the C 3 -C 10 cycloalkenylene group is
  • a divalent group having the same structure as a C 3 -C 10 cycloalkenyl group is a divalent group having the same structure as a C 3 -C 10 cycloalkenyl group.
  • the C 2 -C 10 heterocycloalkenyl group of the present specification includes a C 2 -C 10 monovalent monocyclic group containing at least one hetero atom selected from ⁇ , ⁇ , ⁇ , and S as a ring-forming atom, It has one double bond. remind
  • C 2 -C 10 heterocycloalkenyl group examples include a 2,3-hydrofuranyl group, a 2,3-hydrothiophenyl group, and the like.
  • the C 2 -C 10 heterocycloalkenylene group is
  • a divalent group having the same structure as a C 2 -C 10 heterocycloalkenyl group is meant.
  • a C 6 -C 60 aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms
  • a C 6 -C 60 arylene group refers to a carbo having 6 to 60 carbon atoms
  • divalent group having a cyclic aromatic system is meant.
  • Specific examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group,
  • Phenanthrenyl groups pyrenyl groups, chrysenyl groups and the like.
  • the two or more rings may be fused to each other.
  • the C 2 -C 60 heteroaryl group includes at least one hetero atom selected from ⁇ , ⁇ , ⁇ , and S as a ring-forming atom and has 2 to 60 carbon atoms.
  • a monovalent group having a carbocyclic aromatic system wherein the C 2 -C 60 heteroarylene group represents at least one hetero atom selected from N, O, ⁇ and S as a ring-forming atom
  • Divalent group containing a carbocyclic aromatic system having 2 to 60 carbon atoms Divalent group containing a carbocyclic aromatic system having 2 to 60 carbon atoms.
  • the C 2 -C 60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like.
  • the C 2 -C 60 heteroaryl group and C 2 -C 60 heteroarylene group may be a ring of two or more If included, two or more rings may be fused to each other.
  • the C 6 -C 60 aryloxy group is —OA 102 (wherein 102 is
  • the C 6 -C 60 arylthio group refers to -SA 103 (wherein, A 103 is being the C 6 -C 60 aryl device).
  • a monovalent non-aromatic condensed poly cyclic group includes two or more rings condensed with each other and includes only carbon as a ring forming atom (for example, carbon number may be 8 to 60). ), And the whole molecule
  • Non-it means a monovalent group having a - (aromac non ity) aromaticity.
  • Specific examples of the non-aromatic condensed polycyclic group include fluorenyl groups and the like.
  • the divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
  • a monovalent non-aromatic condensed heteropolycyclic group includes two or more rings condensed with each other and carbon as a ring forming atom (for example, carbon number may be 2 to 60). In addition, it means a monovalent group containing a hetero atom selected from ⁇ , ⁇ , ⁇ and S, and the whole molecule has a non-aromacity.
  • the monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group and the like.
  • the divalent non-aromatic heterocondensed polycyclic group is a monovalent non-aromatic polyaromatic group.
  • Qi to Q 7 , Qu to Q 17, and Q 3 1 to Q 37 are each other.
  • It may be selected from a condensed polycyclic group and a monovalent non-aromatic heterocondensed polycyclic group.
  • substituted C r C 60 alkylene group substituted C 2 -C 60 alkenylene group, substituted C 2 -C 60 alkynylene group, substituted c 3 -c 10 cycloalkylene group, substituted c 2 -c 10 heterocycloalkylene group, substituted c 3 -c 10 cycloalkenylene group, substituted c 2 -c 10 heterocycloalkenylene groups, substituted
  • Benzothiazolyl group isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group,
  • Oxadiazolyl group triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group;
  • C 2 -C 10 hetero come cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea,
  • Benzothiazolyl group isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, Oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group; And
  • Qu to Q 17 and Q 31 to Q 37 are each independently hydrogen, a Ci-oalkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a dC 60 alkoxy group, a cyclophene Tyl group, cyclonuclear group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, cyclohepsenyl group, cycloheptenyl group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl, dibenzocarbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl phthala
  • Imidazolyl pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoqui Nolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group benzoxazolyl group, benzo Imidazolyl group, furanyl group, benzofuranyl group, thiophenyl group,
  • It may be selected from an imidazopyrimidinyl group and an imidazopyridinyl group, but is not limited thereto.
  • a glass substrate on which an indium tin oxide (ITO) electrode (first electrode, anode) having a thickness of 1500 A was cut to a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, and washed with ultrasonic water with distilled water. After washing the distilled water, ultrasonic washing with isopropyl alcohol, acetone, methane and the like, dried and transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes and then transferred the substrate by vacuum evaporator. .
  • ITO indium tin oxide
  • M-MTDATA was vacuum deposited at a deposition rate of 1 A / sec on a ⁇ electrode of the glass substrate to form a hole injection layer having a thickness of 600 A, and on the hole injection layer
  • ⁇ - ⁇ was vacuum deposited at a deposition rate of 1 A / sec to form a hole transport layer having a thickness of 300 A.
  • Ir (ppy) 3 (dope) and compound 8 (host) were co-deposited on the hole transport layer at a deposition rate of 0.1 A / sec and 1 A / sec, respectively, to form a light emitting layer having a thickness of 400 A.
  • BAlq was vacuum deposited on the light emitting layer at a deposition rate of 1 A / sec to form a hole blocking layer having a thickness of 50 A, and then Alq 3 was vacuum deposited on the hole blocking layer to form an electron transport layer having a thickness of 300A.
  • LiF10A (electron injection layer) and A1 2000 A (cathode) were sequentially vacuum deposited on the electron transport layer, thereby manufacturing an organic light emitting device.
  • Example 3 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 21, instead of Compound 8, was used as a host to form the LED.
  • Example 3
  • Example 4 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 26, instead of Compound 8, was used as a host to form the EML.
  • Example 4
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A, instead of Compound 9, was used as a host to form the EML.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound B, instead of Compound 9, was used as a host to form the EML.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound C, instead of Compound 9, was used as a host to form the EML.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound D, instead of Compound 9, was used as a host to form the EML. ⁇ >
  • the driving voltage, efficiency, and luminance of the organic light emitting diodes of Examples 1 to 4 were evaluated using a current voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000 A).
  • the current efficiency was calculated using the measured brightness, current density and voltage. The results are shown in Table 3 below.

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Abstract

Disclosed are a novel condensed-ring compound and an organic light-emitting element comprising same.

Description

【명세서】  【Specification】
【발명의 명칭】  [Name of invention]
축합환 화합물 및 이를 포함한 유기 발광 소자  Condensed cyclic compound and organic light emitting device including the same
【기술분야】  Technical Field
축합환 화합물 및 이를 포함한 유기 발광 소자가 제시된다.  Condensed cyclic compounds and organic light emitting devices including the same are provided.
【배경기술】  Background Art
유기 발광 소자 (organic light emitting diode)는 자발광형 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라， 웅답시간이 빠르며, 휘도, 구동전압 및 웅답속도 특성이 우수하고 다색화가 가능하다는 장점을 가지고 있다.  Organic light emitting diodes are self-luminous devices that have a wide viewing angle, excellent contrast, quick response time, excellent luminance, driving voltage, and quick response speed, and are capable of multicoloring.
일예에 따르면, 유기 발광 소자는, 애노드, 캐소드 및 상기 애노드와 캐소드 사이에 개재된 발광층을 포함할 수 있다. 상기 애노드와 발광층 사이에는 정공 수송 영역이 구비될 수 있고, 상기 발광층과 캐소드 사이에는 전자 수송 영역이 구비될 수 있다. 상기 애노드로부터 주입된 정공은 정공 수송 영역을 경유하여 발광층으로 이동하고, 캐소드로부터 주입된 전자는 전자 수송 영역을 경유하여 발광층으로 이동한다. 상기 정공 및 전자와 같은 캐리어들은 발광층 영역에서 재결합하여 액시톤 (exciton)을 생성한다. 이 엑시톤이 여기 상태에서 기저상태로 변하면서 광이 생성된다.  According to an example, the organic light emitting diode may include an anode, a cathode, and a light emitting layer interposed between the anode and the cathode. A hole transport region may be provided between the anode and the light emitting layer, and an electron transport region may be provided between the light emitting layer and the cathode. Holes injected from the anode move to the light emitting layer via the hole transport region, and electrons injected from the cathode move to the light emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. The excitons change from excited state to ground state and light is generated.
【발명의 상세한 설명】  [Detailed Description of the Invention]
【기술적 과제】  [Technical problem]
신규 축합환 화합물 및 이를 채용한 유기 발광 소자를 제공하는 것이다. A novel condensed cyclic compound and an organic light emitting device employing the same are provided.
【기술적 해결방법】 Technical Solution
일 측면에 따르면， 하기 화학식 1로 표시되는 축합환 화합물이 제공된다: <화학식 1> According to one aspect, a condensed cyclic compound represented by Formula 1 is provided:
Figure imgf000003_0001
<화학식 2A> <화학식 2B>
Figure imgf000003_0001
<Formula 2A><Formula2B>
Figure imgf000004_0001
Figure imgf000004_0001
<화학식 2E> < 2F>  <Formula 2E> <2F>
Figure imgf000004_0002
Figure imgf000004_0002
상기 화학식들 중,  Of the above formula,
고리 Au 및 고리 A12는 서로 독립적으로, 벤젠, 나프탈렌, 피리딘， 피리미딘, 피라진, 피리다진 및 트리아진 중에서 선택되고; Ring Au and ring A 12 are each independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine and triazine;
제은 N-KLn Ru)^], S, 0, S(=0), S(=0)2, C(=0), C(R13)(RI4), Si(R,3)(R,4),N-KLn Ru) ^], S, 0, S (= 0), S (= 0) 2 , C (= 0), C (R 13 ) (R I4 ), Si (R, 3 ) (R , 4 ),
P(R13), P(=0)(R13) 및 C=N(R13) 중에서 선택되고;P (R 13 ), P (= 0) (R 13 ) and C = N (R 13 );
2는 N-[(L12)al2-(R12)bl2], S, O, S(=0), S(=0)2, C(=0), C(R15)(R16), Si(R15)(R16), P(R15), P(=0)(R15) 및 C=N(R15) 중에서 선택되고;2 shows N - [(L 12) al2 - (R 12) bl2], S, O, S (= 0), S (= 0) 2, C (= 0), C (R 15) (R 16) , Si (R 15 ) (R 16 ), P (R 15 ), P (= 0) (R 15 ) and C═N (R 15 );
은 N-[(L0al-(R0bl], S, O, S(=0), S(=0)2, C(=0), Si(R5)(R6), P(R5), P(=0)(R5) 및 C=N(R5) 중에서 선택되고; Is N-[(L0 al- (R0 bl ], S, O, S (= 0), S (= 0) 2 , C (= 0), Si (R 5 ) (R 6 ), P (R 5 ), P (= 0) (R 5 ) and C = N (R 5 );
L, 내지 L4, LU 및 L12는 서로 독립적으로， 치환 또는 비치환된 L, to L 4 , L U and L 12 are each independently a substituted or unsubstituted
C3-C10시클로알킬렌기， 치환 또는 비치환된 C2-C10헤테로시클로알킬렌기, 치환 또는 비치환된 c3-c10시클로알케닐렌기， 치환 또는 비치환된 C 3 -C 10 cycloalkylene group, substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, substituted or unsubstituted c 3 -c 10 cycloalkenylene group, substituted or unsubstituted
c2-c10헤테로시클로알케닐렌기, 치환 또는 비치환된 C6-C60아릴렌기, 치환 또는 비치환된 C2-C60헤테로아릴렌기， 치환 또는 비치환된 2가 비-방향족 축합다환 그룹 및 치환 또는 비치환된 2가 비-방향족 해테로축합다환 그룹 중에서 선택되고; c 2 -c 10 heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 arylene group, substituted or An unsubstituted C 2 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group;
al 내지 a4, al l 및 al2는 서로 독립적으로, 0 내지 3의 정수 중에서 선택되고; al to a4, al l and al2 are each independently selected from an integer of 0 to 3;
Ri 내지 ¾ 및 Ru 내지 R20은 서로 독립적으로, 수소， 중수소， -F (플루오로기), -C1 (클로로기), -Br (브로모기) , -1(아이오도기), 히드록실기, 시아노기, 니트로기, 아미노기， 아미디노기, 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염， 치환 또는 비치환된 -C60알킬기， 치환 또는 비치환된 C2-C60알케닐기, 치환 또는 비치환된 C2-C60알키닐기, 치환 또는 비치환된 Cl_C60알콕시기, 치환 또는 비치환된 C3-C10시클로알킬기, 치환 또는 비치환된 Ri to ¾ and Ru to R 20 are each independently hydrogen, deuterium, -F (fluoro group), -C1 (chloro group), -Br (bromo group), -1 (iodo group), hydroxyl group, Cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted -C 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted Cl _C 60 alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted
C2-C10헤테로시클로알킬기， 치환 또는 비치환된 C3-C10시클로알케닐기, 치환 또는 비치환된 C2-C10헤테로시클로알케닐기, 치환 또는 비치환된 C6-C60아릴기, 치환 또는 비치환된 c6-c60아릴옥시기, 치환 또는 비치환된 c6-c60아릴티오기, 치환 또는 비치환된 c2-c60헤테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹, -N(Q0(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7) 및 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 증에서 선택되되, 상기 내지 ¾은, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아니고; C 2 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group , Substituted or unsubstituted c 6 -c 60 aryloxy group, substituted or unsubstituted c 6 -c 60 arylthio group, substituted or unsubstituted c 2 -c 60 heteroaryl group, substituted or unsubstituted monovalent Non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N (Q0 (Q 2 ), -Si (Q 3 ) (Q4) (Q 5 ), -B (Q 6 (Q 7 ) and the group represented by the formula (2A) to the group represented by the formula (2F), wherein the ¾ is not the group represented by the formula (2A) to the group represented by the formula (2F);
bl 내지 b4, bl l, M2 및 bl6 내지 b20은 서로 독립적으로, 1 내지 3의 정수 중에서 선택되고;  bl to b4, bl 1, M2 and bl6 to b20 are each independently selected from an integer of 1 to 3;
i) 상기 화학식 1 중 Xu은 N-KLn u Ru u]이고, 2은 N-[(L12)al2-(R12)bl2]이 아닐 경우， 상기 화학식 1 중 bl7개의 R17, bl l개의 RU, M8개의 R18, bl9개의 R19 및 b20개의 R20 중 적어도 하나는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; i) and Xu of Formula 1 is N-KLn u Ru u], 2 is N - [(L 12) al2 - (R 12) bl2] This, of bl7 of R 17, bl l of the above formula (1), if not At least one of R U , M8 R 18 , bl9 R 19, and b20 R 20 is selected from the group represented by Formula 2A to the group represented by Formula 2F;
ii) 상기 화학식 1 중 Xir N- Lu I^Obu]가 아니고 , 2은 ii) is not X ir N-Lu ^ O b u] in Formula 1, and 2 is
N-[(L12)al2-(R12)b |일 경우， 상기 화학식 1 중 bl7개의 R17, bl8개의 R18, bl9개의 R19, M2개의 R12 및 b20개의 R20 중 적어도 하나는， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; N - [(L 12) al2 - (R 12) b | one case, the formula (1) of bl7 of R 17, of R 18 bl8, bl9 of R 19, at least one of the M2 of R 12 and b20 of R 20 is , Selected from the group represented by Formula 2A to the group represented by Formula 2F;
iii) 상기 화학식 1 증 Xu은 N-KLn R^bu]이고， 2은 N-[(L12)al2-(R12)bl2]일 경우, 상기 화학식 1 중 bl7개의 R17, bl l개의 Ru, bl8개의 R18, M9개의 R19, bl2개의 R12 및 b20개의 R20 중 적어도 하나는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; iii) wherein the formula (1) increases Xu is N-KLn R ^ b u] , 2 is N - [(L 12) al2 - (R 12) bl2], of bl7 of R 17, bl l of the above formula (1) if the At least one of R u , bl8 R 18 , M9 R 19 , bl2 R 12, and b20 R 20 is a group represented by Formula 2A to the above It is selected from the group represented by Formula 2F;
상기 치환된 C3-C10시클로알킬렌기, 치환된 C2-C10헤테로시클로알킬렌기, 치환된 C3-C10시클로알케닐렌기， 치환된 C2-C10헤테로시클로알케닐렌기, 치환된 The substituted C 3 -C 10 cycloalkylene group, substituted C 2 -C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 2 -C 10 heterocycloalkenylene group, substitution Done
C6-C60아릴렌기， 치환된 C2-C60해테로아릴렌기, 치환된 2가 비-방향족 축합다환 그룹, 치환된 2가 비-방향족 헤테로축합다환 그룹， 치환된 d- o알킬기, 치환된 C 6 -C 60 arylene group, substituted C 2 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted d-oalkyl group, Substituted
C2-C60알케닐기， 치환된 C2-C60알키닐기， 치환된 d- o알콕시기, 치환된 C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted d-oalkoxy group, substituted
C3-C10시클로알킬기, 치환된 C2-C10헤테로시클로알킬기, 치환된 C3-C10시클로알케닐기, 치환된 C2-C10헤테로시클로알케닐기, 치환된 C6-C60아릴기, 치환된 C6-C60아릴옥시기, 치환된 C6-C60아릴티오기, 치환된 C2-C60헤테로아릴기, 치환된 1가 비-방향족 C 3 -C 10 cycloalkyl group, substituted C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, a substituted C 6 -C 60 aryloxy group, a substituted C 6 -C 60 arylthio group, a substituted C 2 -C 60 heteroaryl group, a substituted a non-aromatic
축합다환 그룹 및 치환된 1가 비-방향족 헤테로축합다환 그룹의 치환기 중 적어도 하나는, At least one of the substituents of the condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group is
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미노기, 아미디노기， 히드라진기, 히드라존기， 카르복실산또는 이의 염， 술폰산 또는 이의 염, 인산또는 이의 염, - o알킬기， C2-C60알케닐기, C2-C60알키닐기 및 d- o알콕시기; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, -oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group and d-oalkoxy group;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염， 술폰산 또는 이의 염, 인산 또는 이의 염, C3-C10시클로알킬기, C2-C10헤테로시클로알킬기, C3-C10시클로알케닐기, c2-c10헤테로시클로알케닐기, C6-C60아릴기, c6-c60아릴옥시기, c6-c60아릴티오기,Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, c 2 -c 10 heterocycloalkenyl group, C 6 -C 60 aryl group, c 6- c 60 aryloxy group, c 6 -c 60 arylthio group,
C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, -N(Qu)(Q12), -Si(Q13)(Q14)(Q15) 및 -B(Q16)(Q17) 중 적어도 하나로 치환된,C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Qu) (Q 12 ), -Si (Q 13 ) (Q 14 ) (Q 15 ) and -B (Q 16 ) (Q 17 ) substituted with at least one of
-C60알킬기, C2-C60알케닐기, C2-C60알키닐기 및 d- o알콕시기; -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group and d-oalkoxy group;
C3-C10시클로알킬기， C2-C10헤테로시클로알킬기, C3-C10시클로알케닐기， C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기,C 2 -C 10 hetero come cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea,
C2-C60해테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹; C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기, 아미노기， 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, d- o알킬기 , C2-C60알케닐기 , C2-C60알키닐기， d- o알콕시기 , Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, d-oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, d-oalkoxy group,
C3-C10시클로알킬기, C2-Cl0헤테로시클로알킬기, C3-C10시클로알케닐기， C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-C10해테로시클로알케닐기 , C6-C60아릴기 , C6-C60아릴옥시기 , C6-C60아릴티오기 , c2-c60헤테로아릴기 , 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, -N(Q21)(Q22), -Si(Q23XQ24)(Q25) 및 -B(Q26)(Q27) 중 적어도 하나로 치환된, C3-C10시클로알킬기， C2-C10헤테로시클로알킬기, C3-C10시클로알케닐기， C 2 -C 10 year Tero cycloalkenyl group, C 6 -C 60 aryl group import, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea, c 2 -c 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q 21 ) (Q 22 ), -Si (Q 23 XQ 24 ) (Q 25 C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, substituted with at least one of -B (Q 26 ) (Q 27 ),
c2-c10해테로시클로알케닐기 , c6-c60아릴기， c6-c60아릴옥시기， c6-c60아릴티오기， C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹; 및 c 2 -c 10 by interrogating cycloalkenyl group, c 6 -c 60 aryl group, c 6 -c 60 aryloxy group, c 6 -c 60 aryl come tea, C 2 -C 60 heteroaryl group, a monovalent non- Aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group; And
-N(Q3i)(Q32), -Si(Q33)(Q34)(Q35) 및 -B(Q36)(Q37); 중에서 선택되고; -N (Q 3 i) (Q 32 ), -Si (Q 33 ) (Q 34 ) (Q3 5 ) and -B (Q 36 ) (Q 37 ); Is selected from;
상기 내지 Q7, Qu 내지 Q17, Q21 내지 Q27 및 Q3i 내지 Q37은 서로 독립적으로, 수소, d- o알킬기, C2-C60알케닐기, C2-C60알키닐기， ^- 0알콕시기, C3-C10시클로알킬기 , C2-C10헤테로시클로알킬기 , C3-C10시클로알케닐기， To Q 7 , Qu to Q 17 , Q 21 to Q 27, and Q 3 i to Q 37 are each independently hydrogen, d-oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, ^ -0 alkoxy group, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기， C6-C60아릴티오기， C2-C60해테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹 중에서 선택된다. C 2 -C 10 hetero cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come tea, C 2 -C 60 year for interrogating an aryl group, a monovalent non- Aromatic condensed polycyclic groups and monovalent non-aromatic heterocondensed polycyclic groups.
다른 측면에 따르면, 제 1전극; 제 2전극; 및 상기 제 1전극과 상기 게 2전극 사이에 개재되고， 발광층을 포함하고， 상기 화학식 1로 표시되는 축합환 화합물을 적어도 1종 이상 포함한 유기층；을 포함한, 유기 발광 소자가 제공된다.  According to another aspect, the first electrode; Second electrode; And an organic layer interposed between the first electrode and the second electrode and including an emission layer, the organic layer including at least one or more condensed cyclic compounds represented by Formula 1.
상기 축합환 화합물은 상기 발광층에 포함되어 있을 수 있고， 상기 발광층은 도펀트를 더 포함하고, 상기 발광층에 포함된 상기 축합환 화합물은 호스트의 역할을 할 수 있다.  The condensed cyclic compound may be included in the emission layer, the emission layer may further include a dopant, and the condensed cyclic compound included in the emission layer may serve as a host.
【유리한 효과】  Advantageous Effects
상기 축합환 화합물은 우수한 전기적 특성 및 열적 안정성을 갖는 바, 상기 축합환 화합물을 채용한 유기 발광 소자는 저구동 전압, 고효율, 고휘도 및 장수명 특성을 가질 수 있다.  The condensed cyclic compound has excellent electrical properties and thermal stability, the organic light emitting device employing the condensed cyclic compound may have a low driving voltage, high efficiency, high brightness and long life.
【도면의 간단한 설명】  [Brief Description of Drawings]
도 1은 일 구현예를 따르는 유기 발광 소자를 개략적으로 나타낸  1 schematically shows an organic light emitting device according to one embodiment
단면도이다. It is a cross section.
<부호의 설명 >  <Description of the sign>
11 : 기판  11: substrate
13: 제 1전극  13: first electrode
15: 유기층 17: 제 2전극 15: organic layer 17: second electrode
【발명의 실시를 위한 최선의 형태】  [Best form for implementation of the invention]
상기 축합환 화합물은 하기 화학식 1로 표시된다:  The condensed cyclic compound is represented by the following Chemical Formula 1:
< 1> <1>
Figure imgf000008_0001
Figure imgf000008_0001
상기 화학식 1 중 고리 Au 및 고리 A12는 서로 독립적으로， 벤젠, 나프탈렌， 피리딘, 피리미딘, 피라진， 피리다진 및 트리아진 중에서 선택될 수 있다. In Formula 1, ring A u and ring A 12 may be independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, and triazine.
예를 들어, 상기 고리 Au 및 고리 A12는 벤젠일 수 있으나， 이에 한정되는 것은 아니다. 상기 화학식 1 중 ¾은 N-KL! an-iRi bii], S, 0, S(=0), S(=0)2, C(=0), For example, the ring A u and ring A 12 may be benzene, but are not limited thereto. ¾ of Formula 1 is N-KL! an-iRi b ii], S, 0, S (= 0), S (= 0) 2 , C (= 0),
C(R13)(R14), Si(R13)(R14), P(R13), P(=0)(R13) 및 C=N(R13) 중에서 선택되고, 상기 화학식 IB 중 2는 N-[(L12)al2-(R12)bl2], S, 0, S(=0), S(=0)2, C(=0), C(R15)(R16), Si(R15)(R16), P(R15), P(0)(R15) 및 C-N(R15) 중에서 선택되고， 상기 화학식 2A 내지 2F 중 X — N-KL a.-CR b!], S, 0， S(=0), S(=0)2, C(=0), )(¾)， P(R5), P(=0)(R5) 및 C=N(R5) 증에서 선택된다. C (R 13 ) (R 14 ), Si (R 13 ) (R 14 ), P (R 13 ), P (= 0) (R 13 ) and C═N (R 13 ) and are selected from Formula IB of 2 N - [(L 12) al2 - (R 12) bl2], S, 0, S (= 0), S (= 0) 2, C (= 0), C (R 15) (R 16 ), Si (R 15 ) (R 16 ), P (R 15 ), P (0) (R 15 ) and CN (R 15 ), wherein X—N—KL a.- in Formulas 2A to 2F. CR b !], S, 0, S (= 0), S (= 0) 2 , C (= 0),) (¾), P (R 5 ), P (= 0) (R 5 ) and C = N (R 5 ) increments.
상기 화학식 1과 화학식 2A 내지 2F와의 관계는 하기와 같다:  The relationship between Formula 1 and Formulas 2A to 2F is as follows:
i) 상기 화학식 1 중 Xn은 N-KLu^^Rn u]이고, 2은 N-[(L12)al2-(RI2)bl2]이 아닐 경우, 상기 화학식 1 중 bl7개의 R17,bll개의 Rn,bl8개의 R1S,M9개의 R19 및 b20개의 R20 중 적어도 하나는， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; of (R I2) bl2] if it is not, the above formula (1) of bl7 of R 17, bll - i) and Xn is the formula N-Rn KLu ^^ u] of 1, 2, N - [(L 12) al2 At least one of R n , bl 8 R 1S , M 9 R 19 and b20 R 20 is selected from the group represented by Formula 2A to the group represented by Formula 2F;
ϋ) 상기 화학식 1 중 Xu은 N-KLu^ R^bu]가 아니고 , 2은 iii) Xu in Formula 1 is not N-KLu ^ R ^ bu], and 2 is
N-[(L12)al2-(R12)bl2]일 경우, 상기 화학식 1 중 bl7개의 RI7,M8개의 R18,M9개의 R19, bl2개의 R12 및 b20개의 R20 중 적어도 하나는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; N - [(L 12) al2 - (R 12) bl2] be the case, of the formula 1 bl7 of R I7, M8 of R 18, M9 of R 19, at least one of the bl2 of R 12 and b20 of R 20 is Selected from the group represented by Formula 2A to the group represented by Formula 2F;
Hi) 상기 화학식 1 중 Χπ은
Figure imgf000009_0001
N-[(L12)al2-(R12)bl2]일 경우, 상기 화학식 1 중 bl7개의 R17,bll개의 Ru,bl8개의 R18,bl9개의 R19,bl2개의 R12 및 b20개의 R20 중 적어도 하나는， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택된다. Hi) Χ π in Formula 1
Figure imgf000009_0001
N - [(L 12) al2 - (R 12) bl2] be the case, of the formula 1 bl7 of R 17, bll of R u, bl8 of R 18, bl9 of R 19, bl2 of R 12 and b20 of R At least one of 20 is selected from the group represented by Formula 2A to the group represented by Formula 2F.
일 구현예에 따르면， 상기 화학식 1 중 Xu은
Figure imgf000009_0002
S및 0 중에서 선택될 수 있다. According to an embodiment, X u in Formula 1 is
Figure imgf000009_0002
May be selected from S and 0.
다른 구현예에 따르면， 상기 화학식 1B 중 2는 N-[(L12)al2-(R12)bl2], S 및 0 중에서 선택될 수 있다. According to another embodiment, two of the formula 1B is N - and can be selected from, S and 0 - [(R 12) bl2 (L 12) al2].
예를 들면, Xu은 N-KLu^ ^Obu]이고， 2는 N-[(Ll2)al2-(R12)bl2]일 수 있으나, 이에 한정되는 것은 아니다ᅳ For instance, Xu is N-KLu ^ ^ O b u ] , and 2 N - [(L l2) al2 - may be a (R 12) bl2], but not limited to eu
또 다른 구현예에 따르면, 상기 화학식 2A 내지 2F 중 ¾은 N-[(LOal-(RObl], S 및 0 중에서 선택될 수 있다. According to another embodiment, ¾ of Formulas 2A to 2F may be selected from N-[(LO al- (RO bl ), S and 0.
상기 화학식들 중 내지 L4,LU 및 L12는 서로 독립적으로， 치환 또는 비치환된 C3-C10시클로알킬렌기， 치환 또는 비치환된 C2-C10헤테로시클로알킬렌기, 치환 또는 비치환된 C3-C10시클로알케닐렌기, 치환 또는 비치환된 c2-c10헤테로시클로알케닐렌기, 치환 또는 비치환된 c6-c60아릴렌기, 치환 또는 비치환된 C2-C60헤테로아릴렌기， 치환 또는 비치환된 2가 비-방향족 축합다환 그룹 및 치환 또는 비치환된 2가 비-방향족 헤테로축합다환 그룹 중에서 선택될 수 있다. 예를 들어, 상기 화학식들 중 내지 L4, Lu 및 L12는 서로 독립적으로， 페닐렌기 (phenylene), 펜탈레닐렌기 (pentalenylene), 인데닐렌기 (indenylene), 나프틸렌기 (naphthylene), 아줄레닐렌기 (azulenylene), 헵탈레닐렌기 (heptalenylene), 인다세닐렌기 (indacenylene), 아세나프틸렌기 (acenaphthylene), L 4 , L U and L 12 in the above formulas may be each independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted group. A substituted C 3 -C 10 cycloalkenylene group, substituted or unsubstituted c 2 -c 10 heterocycloalkenylene group, substituted or unsubstituted c 6 -c 60 arylene group, substituted or unsubstituted C 2 -C 60 heteroarylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic ring Groups and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups. For example, in the above formulas, L 4 , Lu, and L 12 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, or an azule group. Aylene (azulenylene), heptalenylene (heptalenylene), indane ylene (indacenylene), acenaphthylene (acenaphthylene),
플루오레닐렌기 (fluorenylene), 스파이로-플루오레닐렌기, 페날레닐렌기 (phenalenylene), 페난트레닐렌기 (phenanthrenylene), 안트라세닐렌기 (anthracenylene), Fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, phenanthrenylene group, anthracenylene group,
플루오란트레닐렌기 (fluoranthrenylene), 트리페닐레닐렌기 (triphenylenylene), Fluoranthrenylene group, triphenylenylene group,
파이레닐렌기 (pyrenylene), 크라이세닐렌기 (chrysenylene), Pyrenylene, chrysenylene,
나프타세닐렌기 (naphthacenylene), 피세닐렌기 (picenylene), 페릴레닐렌기 (perylenylene), 펜타페닐렌기 (pentaphenylene), 핵사세닐렌기 (hexacenylene), 피롤일렌기 (pyrrolylene), 이미다졸일렌기 (imidazolylene), 피라졸일렌기 (pyrazolylene), 피리디닐렌기 (pyridinylene), 피라지닐렌기 (pyrazinylene), 피리미디닐렌기 (pyrimidinylene), Naphthacenylene group, picenylene group, picenylene group, perylenylene group, pentaphenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group (imidazolylene) , Pyrazolylene group, pyridinylene group, pyrazinylene group, pyrazinylene group, pyrimidinylene group,
피리다지닐렌기 (pyridazinylene), 이소인돌일렌기 (isoindolylene), 인돌일렌기 (indolylene), 인다졸일렌기 (indazolylene), 푸리닐렌기 (purinylene), 퀴놀리닐렌기 (quinolinylene), 이소퀴놀리닐렌기 (isoquinolinylene), 벤조퀴놀리닐렌기 (benzoquinolinylene), Pyridazinylene, isoindoleylene, indolylene, indazole, inzolylene, purinylene, quinolinylene, isoquinolinylene (isoquinolinylene), benzoquinolinylene group (benzoquinolinylene),
프탈라지닐렌기 (phthalazinylene), 나프티리디닐렌기 (naphthyridinylene), Phthalazinylene, naphthyridinylene,
퀴녹살리닐렌기 (quinoxalinylene), 퀴나졸리닐렌기 (quinazolinylene), Quinoxalinylene group (quinoxalinylene), quinazolinylene group (quinazolinylene),
시놀리닐렌기 (cinnolinylene), 카바졸일렌기 (carbazolylene),  Cynolinylene, carbazolylene,
페난트리디닐렌기 (phenanthridinylene), 아크리디닐렌기 (acridinylene),  Phenanthridinylene group (phenanthridinylene), acridinylene group (acridinylene),
페난트롤리닐렌기 (phenanthrolinylene), 페나지닐렌기 (phenazinylene),  Phenanthrolinylene, phenazinylene,
벤조옥사졸일렌기 (benzooxazolylene), 벤조이미다졸일렌기 (benzoimidazolylene), 푸라닐렌기 (foranylene), 벤조푸라닐렌기 (benzofuranylene), 티오페닐렌기 (thiophenylene), 벤조티오페닐렌기 (benzothiophenylene), 티아졸일렌기 (thiazolylene),  Benzooxazolylene group, benzoimidazolylene group, benzoimidazolylene, furanylene group, foranylene, benzofuranylene group, thiophenylene group, benzothiophenylene group, benzothiophenylene group, thiazolylene group (thiazolylene),
이소티아졸일렌기 (isothiazolylene), 벤조티아졸일렌기 (benzothiazolylene),  Isothiazolylene group, benzothiazolylene group,
이소옥사졸일렌기 (isoxazolylene), 옥사졸일렌기 (oxazolylene), 트리아졸일렌기, 테트라졸일렌기， 옥사디아졸일렌기 (oxadiazolyiene), 트리아지닐렌기 (triazinyiene), 디벤조푸라닐렌기 (dibenzofuranylene), 디벤조티오페닐렌기 (dibenzoth phenylene), 벤조카바졸일렌기, 디벤조카바졸일렌기, Isoxazolylene group, oxazolylene group, oxazolylene group, triazolylene group, tetrazoylene group, oxadiazolyiene, triazinyiene group, dibenzofuranylene group, dibenzofuranylene group, dibenzothioan group Phenylene group (dibenzoth phenylene), Benzocarbazole ylene group, dibenzo carbazole ylene group,
이미다조피리미디닐렌기 (imidazopyrimidinylene) 및 Imidazopyrimidinylene and
이미다조피리디닐렌기 (imidazopyridinylene); 및 Imidazopyridinylene group; And
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기， 히드라진기, 히드라존기， 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염， CrC20알킬기, C!- o알콕시기, C6-C20아릴기, C2-C60헤테로아릴기, 1가 비-방향족 축합다환 그룹， 1가 비-방향족 해테로축합환 그룹, -Si(Q33)(Q34XQ35) 중 적어도 하나로 치환된, 페닐렌기, 펜탈레닐렌기, 인데닐렌기, 나프틸렌기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts thereof, C r C 20 alkyl group, C! -Oalkoxy group, C 6 -C 20 aryl group, C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterotero A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, substituted with at least one of a condensed cyclic group, -Si (Q 33 ) (Q 34 XQ 35 ),
아줄레닐렌기, 헵탈레닐렌기， 인다세닐렌기, 아세나프틸렌기, 플루오레닐렌기， 스파이로 -플루오레닐렌기, 페날레닐렌기, 페난트레닐렌기, 안트라세닐렌기, Azulenylene group, heptalenylene group, indasenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, penalenylene group, phenanthrenylene group, anthracenylene group,
플루오란트레닐렌기, 트리페닐레닐렌기, 파이레닐렌기， 크라이세닐렌기， Fluoranthrenylene group, triphenylenylene group, pyrenylene group, crysenylene group,
나프타세닐렌기, 피세닐렌기, 페릴레닐렌기, 펜타페닐렌기, 핵사세닐렌기, 피롤일렌기， 이미다졸일렌기, 피라졸일렌기, 피리디닐렌기, 피라지닐렌기, 피리미디닐렌기, 피리다지닐렌기， 이소인돌일렌기, 인돌일렌기, 인다졸일렌기, 푸리닐렌기, Naphthacenylene group, pisenylene group, peryleneylene group, pentaphenylene group, nuxasenylene group, pyrroleylene group, imidazole ylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinyl Benzene group, isoindoleylene group, indolylene group, indazole ylene group, furinylene group,
퀴놀리닐렌기, 이소퀴놀리닐렌기， 벤조퀴놀리닐렌기, 프탈라지닐렌기, Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinylene group,
나프티리디닐렌기， 퀴녹살리닐렌기， 퀴나졸리닐렌기， 시놀리닐렌기， 카바졸일렌기, 페난트리디닐렌기, 아크리디닐렌기, 페난트를리닐렌기, 페나지닐렌기, Naphthyridinylene group, quinoxalinylene group, quinazolinyl group, cynolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrylinylene group, phenazinylene group,
벤조옥사졸일렌기， 벤조이미다졸일렌기, 푸라닐렌기, 벤조푸라닐렌기, 티오페닐렌기, 벤조티오페닐렌기, 티아졸일렌기， 이소티아졸일렌기, 벤조티아졸일렌기, Benzoxazolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazoleylene group,
이소옥사졸일렌기， 옥사졸일렌기, 트리아졸일렌기, 테트라졸일렌기, Isoxazole ylene group, oxazole ylene group, triazole ylene group, tetrazole ylene group,
옥사디아졸일렌기, 트리아지닐렌기, 디벤조푸라닐렌기, 디벤조티오페닐렌기, 벤조카바졸일렌기， 디벤조카바졸일렌기 이미다조피리미디닐렌기 및 Oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazole ylene group, dibenzo carbazole ylene group imidazopyrimidinylene group and
이미다조피리디닐렌기; 중에서 선택되고, Imidazopyridinylene group; Is selected from,
Q33 내지 Q35는 서로 독립적으로, 수소， ^- 0알킬기, d-C2。알콕시기, 페닐기, 나프틸기， 안트라세닐기, 파이레닐기， 페난쓰레닐기, 플루오레닐기, 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 피리디닐기, 피리미디닐기， 피라지닐기, Q 33 to Q 35 are each independently hydrogen, ^ -0 alkyl group, dC 2 .alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarba Solyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group,
피리다지닐기, 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기 프탈라지닐기, Pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group,
퀴녹살리닐기, 시놀리닐기 및 퀴나졸리닐기 중에서 선택될 수 있다. It may be selected from a quinoxalinyl group, a cynolinyl group, and a quinazolinyl group.
일 구현예에 따르면, 상기 화학식들 중 내지 L4, LU 및 L12는 서로 According to one embodiment, in the formulas to L 4 , L U and L 12 are mutually
독립적으로, 화학식 2-1 내지 2-13 중에서 선택될 수 있으나, 이에 한정되는 것은 : Independently, it may be selected from Chemical Formulas 2-1 to 2-13, but is not limited thereto. :
Figure imgf000012_0001
Figure imgf000012_0001
화학식 2-1 2 화학식 2-13  Chemical Formula 2-1 2 Chemical Formula 2-13
상기 화학식 2-1 내지 2-13 중,  In Formulas 2-1 to 2-13,
Z, 내지 Z4는 서로 독립적으로, 수소, 중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기, 아미노기， 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, C C20알킬기, CrC20알콕사기, 페닐기, 나프틸기， 안트라세닐기, 트리페닐레닐기， 파이레닐기, 페난쓰레닐기, 플루오레닐기, 크라이세닐기， 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 디벤조퓨라닐기, 디벤조티오페닐기, 피리디닐기, 피리미디닐기, 트리아지닐기， 퀴놀리닐기, 이소퀴놀리닐기， 퀴나졸리닐기, 퀴녹살리닐기, 비페닐기 및 Z, to Z 4 are independently of each other hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acids or salts thereof, sulfonic acids or salts thereof, phosphoric acid or salts thereof, CC 20 alkyl groups, CrC 20 alkoxy groups, phenyl groups, naphthyl groups, anthracenyl groups, triphenylenyl groups, pyrenyl groups, phenanthrenyl groups, fluorenyl groups, Chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, Quinazolinyl group, quinoxalinyl group, biphenyl group, and
-Si(Q33)(Q34)(Q35) 중에서 선택되고; 상기 Q33 내지 Q35는 서로 독립적으로, 수소， C!- o알킬기， C ^)알콕시기, 페닐기， 나프틸기, 안트라세닐기， 파이레닐기, 페난쓰레닐기, 플루오레닐기, 크라이세닐기, 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기， 디벤조퓨라닐기, 디벤조티오페닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 퀴놀리닐기, -Si (Q 33 ) (Q 3 4) (Q 35 ); Q 33 to Q 35 are each independently hydrogen, C! -Oalkyl, C ^) alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, chrysenyl, Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group,
이소퀴놀리닐기, 퀴나졸리닐기 및 퀴녹살리닐기 중에서 선택되고; Isoquinolinyl group, quinazolinyl group and quinoxalinyl group;
dl은 1 내지 4의 정수 중에서 선택되고, d2는 1 내지 3의 정수 중에서 선택되고, d3는 1 내지 6의 정수 중에서 선택되고, d4는 1 내지 8의 정수 중에서 선택되고, d6는 1 내지 5의 정수 중에서 선택되고, * 및 *，는 이웃한 원자와의 결합 사이트일 수 있다.  dl is selected from integers of 1 to 4, d2 is selected from integers of 1 to 3, d3 is selected from integers of 1 to 6, d4 is selected from integers of 1 to 8, d6 is selected from 1 to 5 And * and *, may be binding sites with neighboring atoms.
또 다른 구현예에 따르면, 상기 화학식들 중 내지 L4, LU 및 L12는 서로 독립적으로 하기 화학식 3-1 내지 3-12 중에서 선택될 수 있으나, 이에 한정되는 According to another embodiment, to L 4 , L U, and L 12 of the above formulas may be independently selected from the following Formulas 3-1 to 3-12, but are not limited thereto.
Figure imgf000013_0001
Figure imgf000013_0001
상기 화학식 2A내지 2F 중 al은 의 개수를 나타낸 것으로서, 0 내지 3의 정수 중에서 선택된다. 예를 들어, al은 0 또는 1일 수 있다. al이 0일 경우， ¾은 N에 직접 연결된다. al이 2 이상일 경우, 2 이상의 Lr 서로 동일하거나 상이할 수 있다. a2 내지 a4, al l 및 al2에 대한 설명은 al에 대한 설명 및 화학식 1 및 화학식 2A내지 2F에 대한 설명을 참조한다. In Formulas 2A to 2F, al represents the number of and is selected from an integer of 0 to 3. For example, al can be 0 or 1. If al is 0, ¾ is directly connected to N. When al is 2 or more, two or more Lr may be the same as or different from each other. Description of a2 to a4, al l and al2 is described for al and formula 1 and formula See the description of 2A through 2F.
일 구현예에 따르면, al 내지 a4, al l 및 al2는 서로 독립적으로, 0 또는 1일 수 있다.  According to one embodiment, al to a4, al l and al2 may be 0 or 1, independently of each other.
상기 화학식들 중 내지 R6 및 Rn 내지 R20은 서로 독립적으로, 수소， 증수소, -F (풀루오로기), -Cl(클로로기), -Br (브로모기) , -1(아이오도기), 히드록실기, 시아노기, 니트로기, 아미노기, 아미디노기, 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, 치환 또는 비치환된 R 6 and R n to R 20 in the above formulas independently of each other, hydrogen, hydrogen, -F (pluoro group), -Cl (chloro group), -Br (bromo group), -1 (Io) Earthenware), hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted
C!- o알킬기, 치환 또는 비치환된 C2-C60알케닐기， 치환 또는 비치환된 C ! oalkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted
C2-C60알키닐기， 치환 또는 비치환된 d- o알콕시기, 치환 또는 비치환된 C 2 -C 60 alkynyl group, substituted or unsubstituted d-oalkoxy group, substituted or unsubstituted
C3-C10시클로알킬기, 치환 또는 비치환된 C2-C10헤테로시클로알킬기， 치환 또는 비치환된 C3-CK>시클로알케닐기, 치환 또는 비치환된 C2-C10헤테로시클로알케닐기, 치환 또는 비치환된 C6-C6。아릴기, 치환 또는 비치환된 C6-C60아릴옥시기， 치환 또는 비치환된 C6-C60아릴티오기， 치환 또는 비치환된 C2-C60헤테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환또는 비치환된 1가 비-방향족 C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -CK> cycloalkenyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group , Substituted or unsubstituted C 6 -C 6 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 arylthio group, substituted or unsubstituted C 2 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic
헤테로축합다환 그룹, -N(Q0(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7) 및 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되되， 상기 내지 R6은， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아니다. Heterocondensed polycyclic group, -N (Q0 (Q 2 ), -Si (Q 3 ) (Q 4 ) (Q 5 ), -B (Q 6 ) (Q 7 ) and the group represented by the above formula 2A to the above formula It is selected from the group represented by 2F, wherein to R 6 is not a group represented by the formula (2A) to the group represented by the formula (2F).
일 구현예에 따르면, 상기 R, 내지 R6 및 Ru 내지 R20는 서로 복립적으로， 수소, 중수소, -F, -CI, -Br, -I, 히드톡실기, 시아노기 , 니트로기 , 아미노기, 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, - 0알킬기 및 CrC20알콕시기; According to one embodiment, the R, to R6 and Ru to R 20 are mutually, hydrogen, deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, Amidino groups, hydrazine groups, hydrazone groups, carboxylic acids or salts thereof, sulfonic acids or salts thereof, phosphoric acid or salts thereof, -0 alkyl groups and CrC 20 alkoxy groups;
중수소， -F, -CI, -Br, -I, 히드록실기， 시아노기, 니트로기, 아미노기, 아미디노기， 히드라진기， 히드라존기， 카르복실산또는 이의 염， 술폰산 또는 이의 염 및 인산 또는 이의 염 중 적어도 하나로 치환된, d- o알킬기 및 d- o알콕시기;  Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or A d-oalkyl group and a d-oalkoxy group substituted with at least one of its salts;
페닐기 (phenyl), 펜탈레닐기 (pentalenyl), 인데닐기 (indenyl), 나프틸기 (naphthyl), 아줄레닐기 (azulenyl), 헵탈레닐기 (heptalenyl), 인다세닐기 (indacenyl),  Phenyl group, pentalenyl group, indenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, heptalenyl group, indaseyl group, and indaneyl group
아세나프틸기 (acenaphthyl), 플루오레닐기 (fluorenyl), 스파이로-플루오레닐기, 벤조플루오레닐기, 디벤조플루오레닐기, 페날레닐기 (phenalenyl), Acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl,
페난트레닐기 (phenanthrenyl), 안트라세닐기 (anthracenyl), 폴루오란테닐기 (fluoranthenyl), 트리페닐레닐기 (triphenylenyl), 파이레닐기 (pyrenyl), 크라이세닐기 (chrysenyl), 나프타세닐기 (naphthacenyl), 피세닐기 (picenyl), 페릴레닐기 (perylenyl), Phenanthrenyl (phenanthrenyl), anthracenyl (anthracenyl), fluoroanthhenyl (fluoranthenyl), Triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl,
펜타페닐기 (pentaphenyl), 핵사세닐기 (hexacenyl), 펜타세닐기 (pentacenyl), Pentaphenyl group (pentaphenyl), nucleasenyl group (hexacenyl), pentaxenyl group (pentacenyl),
루비세닐기 (rubicenyl), 코로네닐기 (coronenyl), 오발레닐기 (ovalenyl), 피롤일기 (pyrrolyl), 티오페닐기 (thiophenyl), 퓨라닐기 (fur any 1), 이미다졸일기 (imidazolyl), Rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group (thiophenyl), furanyl group (fur any 1), imidazolyl group (imidazolyl),
피라졸일기 (pyrazolyl), 티아졸일기 (thiazolyl), 이소티아졸일기 (isothiazolyl), Pyrazolyl, thiazolyl, isothiazolyl,
옥사졸일기 (oxazolyl), 이속사졸일기 (isooxazolyl), 피리디닐기 (pyridinyl), Oxazolyl group, isoxazolyl group, pyridinyl group,
피라지닐기 (pyrazinyl), 피리미디닐기 (pyrimidinyl), 피리다지닐기 (pyridazinyl), Pyrazinyl, pyrimidinyl, pyridazinyl,
이소인돌일기 (isoindolyl), 인돌일기 (indolyl), 인다졸일기 (indazolyl), 푸리닐기 (purinyl), 퀴놀리닐기 (quinolinyl), 이소퀴놀리닐기 (isoquinolinyl), 벤조퀴놀리닐기 (benzoquinolinyl), 프탈라지닐기 (phthalazinyl), 나프티리디닐기 (naphthyridinyl), 퀴녹살리닐기 (quinoxalinyl), 퀴나졸리닐기 (quinazolinyl), 시놀리닐기 (cinnolinyl), 카바졸일기 (carbazolyl), Isoindolyl, indolyl, indazolyl, indazolyl, indolinyl, purinyl, quinolinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, and benzoquinolinyl Phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl,
페난트리디닐기 (phenanthridinyl), 아크리디닐기 (acridinyl), Phenanthridinyl group (phenanthridinyl), acridinyl group (acridinyl),
페난트를리닐기 (phenanthrolinyl), 페나지닐기 (phenazinyl), Phenanthrolinyl, phenazinyl,
벤조이미다졸일기 (benzoimidazolyl), 벤조퓨라닐기 (benzofuranyl), Benzoimidazolyl, benzofuranyl,
벤조티오페닐기 (benzothiophenyl), 이소벤조티아졸일기 (isobenzothiazolyl), Benzothiophenyl group, isobenzothiazolyl,
벤조옥사졸일기 (benzooxazolyl), 이소벤조옥사졸일기 (isobenzooxazolyl), Benzooxazolyl group, isobenzooxazolyl group,
트리아졸일기 (triazolyl), 테트라졸일기 (tetrazolyl), 옥사디아졸일기 (oxadiazolyl), 트리아지닐기 (triazinyl), 디벤조퓨라닐기 (dibenzofuranyl), Triazolyl group, tetrazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzofuranyl group,
디벤조티오페닐기 (dibenzothiophenyl), 벤조카바졸일기, 디벤조카바졸일기, Dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group, dibenzocarbazolyl group,
이미다조피리디닐기 및 이미다조피리미디닐기; Imidazopyridinyl group and imidazopyrimidinyl group;
중수소, -F, -CI, -Br, -I, 히드록실기， 시아노기, 니트로기， 아미노기， 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염， 인산또는 이의 염, CrC20알킬기, CrC20알콕시기, -Si(Q33)(Q34)(Q35), 페닐기， 펜탈레닐기， 인데닐기， 나프틸기, 아즐레닐기, 헵탈레닐기, 인다세닐기, 아세나프틸기, 플루오레닐기, 스파이로-플루오레닐기, 벤조플루오레닐기, 디벤조폴루오레닐기, 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기， 트리페닐레닐기, 파이레닐기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or a salt thereof, C r C 20 alkyl, CrC 20 alkoxy group, -Si (Q 33) (Q 34) (Q 35), a phenyl group, a pen Frontale group, an indenyl group, a naphthyl group, ahjeul LES group, a heptyl group Frontale, indazol Cenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzopolorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group , Pyrenyl,
크라이세닐기, 나프타세닐기, 피세닐기, 페릴레닐기, 펜타페닐기， 핵사세닐기, 펜타세닐기, 루비세닐기, 코로네닐기, 오발레닐기, 피롤일기， 티오페닐기, 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기, 이속사졸일기， 피리디닐기, 피라지닐기，괴리미디닐기， 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기， 벤조퀴놀리닐기, 프탈라지닐기, 나프티리디닐기， 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기, 카바졸일기, 페난트리디닐, 아크리디닐, 페난트롤리닐, 페나지닐, 벤조이미다졸일기, 벤조퓨라닐기, Crysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, nucleusenyl group, pentansenyl group, rubisenyl group, coronyl group, ovarenyl group, pyrroyl group, thiophenyl group, furanyl group, imidazole Diary, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, Pyridinyl, pyrazinyl, pyridinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, Naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl,
벤조티오페닐기, 이소벤조티아졸일기, 벤조옥사졸일기, 이소벤조옥사졸일기, 트리아졸일기, 테트라졸일기, 옥사디아졸일기, 트리아지닐기， 디벤조퓨라닐기, 디벤조티오페닐기, 밴조카바졸일기, 디벤조카바졸일기, 이미다조피리디닐기， 이미다조피리미디닐 및 비페닐기 중 적어도 하나로 치환된， 페닐기, 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기, 헵탈레닐기, 인다세닐기， 아세나프틸기, Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, banjo cover A phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indyl substituted with at least one of a zolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl, and a biphenyl group Senyl, Acenaphthyl,
플루오레닐기， 스파이로-플루오레닐기， 벤조플루오레닐기, 디벤조폴루오레닐기, 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, Fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzopolorenyl, penalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl,
파이레닐기, 크라이세닐기, 나프타세닐기, 피세닐기, 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기, 루비세닐기, 코로네닐기, 오발레닐기, 피를일기, 티오페닐기, 퓨라닐기, 이미다졸일기， 피라졸일기, 티아졸일기, 이소티아졸일기， 옥사졸일기, 이속사졸일기, 피리디닐기, 피라지닐기, 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기, 프탈라지닐기, 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기, 카바졸일기, 페난트리디^, 아크리디닐， 페난트를리닐， 페나지닐， 벤조이미다졸일기, 벤조퓨라닐기, 벤조티오페닐기, 이소벤조티아졸일기, 벤조옥사졸일기, 이소벤조옥사졸일기, 트리아졸일기, 테트라졸일기, 옥사디아졸일기， 트리아지닐기， 디밴조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기, 디벤조카바졸일기, 이미다조피리디닐기 및 이미다조피리미디닐; Pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, peryllenyl group, pentaphenyl group, nucleusenyl group, pentansenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, Furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indole Diary, indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenantri Di ^, acridinyl, phenanthlinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetra Solyl group, oxadiazole group, triazinyl group, dibanzopura Group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a piperidinyl group, and flutes already jopi imidazo pyrimidinyl;
-Si(Q3)(Q4)(Q5) (단, 상기 R13 내지 Ri6 및 및 ¾은 -Si(Q3)(Q4)(Q5)가 아님); 상기 화학식 2Α로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 (단, 상기 Rl 내지 ¾는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아님); 중에서 선택되고; —Si (Q 3 ) (Q 4 ) (Q 5 ) provided that R 13 to Ri 6 and ¾ are not —Si (Q 3 ) (Q 4 ) (Q 5 ); A group represented by Formula 2A to a group represented by Formula 2F, provided that Rl to ¾ are not a group represented by Formula 2A to a group represented by Formula 2F; Is selected from;
상기 Q3 내지 Q5 및 Q33 내지 Q35는 서로 독립적으로, 수소, ^- 0알킬기, C!- o알콕시기, 페닐기， 나프틸기, 안트라세닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, 크라이세닐기, 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 디벤조퓨라닐기， 디벤조티오페닐기， 피리디닐기， 피리미디닐기， 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기， 퀴나졸리닐기 및 퀴녹살리닐기 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다. Q 3 to Q 5 and Q 33 to Q 35 are each independently hydrogen, ^ -0 alkyl, C! -Oalkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl or fluore. Neyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, It may be selected from dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group and quinoxalinyl group, but is not limited thereto.
다른 구현예에 따르면, 상기 화학식들 중 내지 ¾ 및 Ru 내지 R20이 서로 독립적으로, According to another embodiment, to ¾ and R u to R 20 in the above formulas are independently of each other,
수소, 중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기, 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염， C o알킬기 및 CrC20알콕시기; Hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or salts thereof, C o alkyl group and CrC 20 alkoxy group;
중수소， -F, -CI, -Br, -I, 히드톡실기, 시아노기 , 니트로기, 아미노기 , 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염 및 인산 또는 이의 염 중 적어도 하나로 치환된, d- o알킬기 및 d- o알콕시기;  Deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or A d-oalkyl group and a d-oalkoxy group substituted with at least one of its salts;
하기 화학식 4-1 내지 4-31 ;  The following formulas 4-1 to 4-31;
-Si(Q3)(Q4)(Q5) (단, 상기 Rl3 내지 Ri6 및 R5 내지 R6은 -Si(Q3)(Q4)(Q5)가 아님); 및 -Si (Q 3 ) (Q 4 ) (Q 5 ) provided that R 13 to Ri 6 and R 5 to R 6 are not —Si (Q 3 ) (Q 4 ) (Q 5 ); And
상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 (단, A group represented by Formula 2A to a group represented by Formula 2F, provided that
R, 내지 ¾는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그 으나， 이에 한정되는 것은 아니다: R, to ¾ are represented by the group represented by the formula (2A) to (2F), but are not limited thereto:
Figure imgf000017_0001
Figure imgf000017_0001
Figure imgf000017_0002
화학식 4-10 ¾학식 4-11 화^식 4-12 화빡식 4-13
Figure imgf000017_0002
Equation 4-10 Equation 4-11 Equation 4-12 Equation 4-13
Figure imgf000018_0001
Figure imgf000018_0001
Figure imgf000018_0002
Figure imgf000018_0002
화학식 4-19 Sf S|식 4-20 ¾ ¾식 4-21 호ᅡ학식 4-22 Formula 4-19 Sf S | Equation 4-20 ¾ ¾ Formula 4-21 Chemical Formula 4-22
Figure imgf000018_0003
Figure imgf000018_0003
화학식 4-29 화학식 4-30 화학식 4-31 화학식 4-1 내지 4-31 중,  Formula 4-29 Formula 4-30 Formula 4-31 of Formulas 4-1 to 4-31,
Y31은 0, S, C(Z33)(Z34), N(Z35) 또는 Si(Z36)(¾7)이고 (단, 화학식 4-23 중 Y31은 ΝΗ가 아님); Y 31 is 0, S, C (Z 33 ) (Z 34 ), N (Z 35 ) or Si (Z 36 ) (¾ 7 ), provided that Y 31 in Formula 4-23 is not ΝΗ;
Ζ31 내지 Ζ37은 서로 독립적으로， 수소, 중수소， -F, -CI, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미노기, 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염， Ci- o알킬기, C!- o알콕시기, 페닐기, 나프틸기， 안트라세닐기, 트리페닐레닐기, 파이레닐기， 페난쓰레닐기， 플루오레닐기, 크라이세닐기, 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 디벤조퓨라닐기, 디벤조티오페닐기, 피리디닐기, 피리미디닐기, 트리아지닐기， 퀴놀리닐기, 이소퀴놀리닐기, 퀴나졸리닐기， 퀴녹살리닐기, 비페닐기 및 Ζ Ζ 31 to 37 are, independently of each other, hydrogen, heavy hydrogen, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic Acids or salts thereof, sulfonic acids or salts thereof, phosphoric acid or salts thereof, Ci-oalkyl groups, C! -Oalkoxy groups, phenyl groups, naphthyl groups, anthracenyl groups, triphenylenyl groups, pyrenyl groups, phenanthrenyl groups, Fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso Quinolinyl group, quinazolinyl group, quinoxalinyl group, biphenyl group, and
-Si(Q33)(Q34)(Q35) 중에서 선택되고; -Si (Q 33 ) (Q 34 ) (Q 35 );
상기 Q3 내지 Q5 및 Q33 내지 Q35는 서로 독립적으로, 수소, d- o알킬기, 알콕시기， 페닐기, 나프틸기, 안트라세닐기, 트리페닐레닐기， 파이레닐기， 페난쓰레닐기, 플루오레닐기， 크라이세닐기, 카바졸일기， 벤조카바졸일기, Q 3 to Q 5 and Q 33 to Q 35 are each independently hydrogen, d-oalkyl group, alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, flu Orenyl group, chrysenyl group, carbazole group, benzocarbazole group,
디벤조카바졸일기， 디벤조퓨라닐기, 디벤조티오페닐기， 피리디닐기, 피리미디닐기, 트리아지닐기, 퀴놀리닐기， 이소퀴놀리닐기， 퀴나졸리닐기 및 퀴녹살리닐기 중에서 선택되고; Dibenzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl and quinoxalinyl;
el은 1 내지 5의 정수 중에서 선택되고, e2는 1 내지 7의 정수중에서 선택되고， e3는 1 내지 3의 정수 중에서 선택되고, e4는 1 내지 4의 정수 중에서 선택되고, e5는 1 또는 2이고, e6은 1 내지 6의 정수 중에서 선택되고, *는 이웃한 원자와의 결합 사이트이다.  el is selected from integers of 1 to 5, e2 is selected from integers of 1 to 7, e3 is selected from integers of 1 to 3, e4 is selected from integers of 1 to 4, and e5 is 1 or 2 , e6 is selected from an integer of 1 to 6, and * is a binding site with a neighboring atom.
또 다른 구현예에 따르면, 상기 화학식들 중 R, 내지 R6 및 Ru 내지 R20은 서로 독립적으로, According to yet another embodiment, in the formulas R, R 6 And R u And R 20 Are independently of each other,
수소, 중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, C o알킬기 및 CrC20알콕시기; Hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or salts thereof, C o alkyl group and CrC 20 alkoxy group;
중수소, -F, -CI, -Br, -I, 히드록실기 , 시아노기， 니트로기 , 아미노기 , 아미디노기， 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염 및 인산 또는 이의 염 중 적어도 하나로 치환된, d- o알킬기 및 Cr o알콕시기;  Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or A d-oalkyl group and a Cr oalkoxy group substituted with at least one of its salts;
하기 화학식 5-1 내지 5-63;  Formulas 5-1 to 5-63;
-Si(Q3)(Q4)(Q5) (단， 상기 R13 내지 R16, R5 및 R6은 -Si(Q3)(Q4)(Q5)가 아님); 및 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 (단, 상기 R, 내지 ¾는 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아님); 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다: -Si (Q 3 ) (Q 4 ) (Q 5 ) provided that R 13 to R 16 , R 5 and R 6 are not -Si (Q 3 ) (Q 4 ) (Q 5 ); And a group represented by Formula 2A to a group represented by Formula 2F, provided that R and ¾ are not a group represented by Formula 2A to a group represented by Formula 2F. It may be selected from, but is not limited to:
Figure imgf000020_0001
Figure imgf000020_0001
호卜학식 5-17 화학식 5-14 회학식 5-15 화학식 5-16 Chemical Formula 5-17 Chemical Formula 5-14 Chemical Formula 5-15 Chemical Formula 5-16
Figure imgf000021_0001
Figure imgf000021_0001
화학식 5-36 화학식 5-37 화학식 5-38
Figure imgf000022_0001
Chemical Formula 5-36 Chemical Formula 5-37 Chemical Formula 5-38
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000023_0001
Figure imgf000023_0002
Figure imgf000023_0002
화학식 5-60 화학식 5-61 화학식 5-62 화학식 5-63  Formula 5-60 Formula 5-61 Formula 5-62 Formula 5-63
한편, 상기 화학식 2A및 2B의 R2, 상기 화학식 2C 및 2D의 R3 및 상기 화학식 2E 및 2F의 R2 및 R3는 서로 독립적으로, Meanwhile, R 2 of Formulas 2A and 2B, R 3 of Formulas 2C and 2D, and R 2 and R 3 of Formulas 2E and 2F are each independently,
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, CrC20알킬기 및 d-C2o알콕시기; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, CrC 20 alkyl groups and dC 2 oalkoxy groups;
페닐기, 펜탈레닐기, 인데닐기， 나프틸기， 아즐레닐기, 헵탈레닐기, 인다세닐기 아세나프틸기, 플루오레닐기, 스파이로-플루오레닐기, 벤조플루오레닐기,  Phenyl group, pentalenyl group, indenyl group, naphthyl group, azelenyl group, heptalenyl group, indasenyl group acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group,
디벤조플루오레닐기, 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기, 나프타세닐기, 피세닐기， 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기, 루비세닐기， 코로네닐기, 오발레닐기, 피를일기， 티오페닐기, 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기, 이속사졸일기, 피리디닐기, 피라지닐기, 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기, 프탈라지닐기, 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기， 카바졸일기, 페난트리디닐기, 아크리디닐기, 페난트롤리닐기， 페나지닐기 벤조이미다졸일기, 벤조퓨라닐기， 벤조티오페닐기, 이소벤조티아졸일기, 벤조옥사졸일기, 이소벤조옥사졸일기， 트리아졸일기, 테트라졸일기, 옥사디아졸일기， 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기, Dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, fisenyl group, perenyl group, pentaphenyl group Nucleasenyl, pentacenyl, rubisenyl, coronyl, ovarenyl, pyridyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group , Phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group benzoimidazolyl group, benzofuranyl group Benzothiophenyl group, isobenzothiazolyl group, Benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
디벤조카바졸일기, 이미다조피리디닐기 및 이미다조피리미디닐기; 및  Dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group; And
증수소， -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기， 아미노기， 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, C!- o알킬기， d-C2o알콕시기, -Si(Q33)(Q34)(Q35), 페닐기, 펜탈레닐기， 인데닐기, 나프틸기, 아줄레닐기， 헵탈레닐기, 인다세닐기, 아세나프틸기， 플루오레닐기， 스파이로-플루오레닐기, 벤조플루오레닐기， 디벤조폴루오레닐기， 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기， 트리페닐레닐기, 파이레닐기， Hydrogen, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid Or salts thereof, C ! -oalkyl group, dC 2 oalkoxy group, -Si (Q 33 ) (Q 34 ) (Q 35 ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, ace Naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzopolorenyl, penalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl ，
크라이세닐기, 나프타세닐기， 피세닐기, 페릴레닐기, 펜타페닐기， 핵사세닐기， 펜타세닐기， 루비세닐기, 코로네닐기， 오발레닐기, 피를일기, 티오페닐기, 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기， 옥사졸일기， 이속사졸일기， 피리디닐기, 피라지닐기， 피리미디닐기, 피리다지닐기, 이소인돌일기， 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기，'프탈라지닐기， 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기, 카바졸일기,  Crysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, nucleusenyl group, pentansenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group, already Dazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazole Diary, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, 'phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl,
페난트리디닐기, 아크리디닐기, 페난트를리닐기， 페나지닐기, 벤조이미다졸일기, 벤조퓨라닐기, 벤조티오페닐기, 이소벤조티아졸일기, 벤조옥사졸일기,  Phenantridinyl group, acridinyl group, phenanthlinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group,
이소벤조옥사졸일기, 트리아졸일기, 테트라졸일기, 옥사디아졸일기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기， 벤조카바졸일기, 디벤조카바졸일기,  Isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group,
이미다조피리디닐기, 이미다조피리미디닐기 및 비페닐 중 적어도 하나로 치환된， 페닐기， 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기， 헵탈레닐기, 인다세닐기, 아세나프틸기, 플루오레닐기， 스파이로-플루오레닐기, 벤조플루오레닐기，  Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorene substituted with at least one of imidazopyridinyl group, imidazopyrimidinyl group and biphenyl Nyl group, spiro-fluorenyl group, benzofluorenyl group,
디벤조플루오레닐기, 페날레닐기, 페난트레닐기， 안트라세닐기， 플루오란테닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기, 나프타세닐기， 피세닐기, 페릴레닐기, 펜타페닐기， 핵사세닐기, 펜타세닐기, 루비세닐기， 코로네닐기， 오발레닐기， 피를일기， 티오페닐기, 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기, 이속사졸일기, 피리디닐기, 피라지닐기, 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기， 인다졸일기, 푸리닐기， 퀴놀리닐기， 이소퀴놀리닐기, 벤조퀴놀리닐기, 프탈라지닐기， 나프티리디닐기， 퀴녹살리닐기, 퀴나졸리닐기,  Dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group ， Nucleoxenyl group, pentaxenyl group, rubisenyl group, coronyl group, ovalenyl group, piryl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group Phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl,
' 시놀리닐기， 카바졸일기, 페난트리디닐기， 아크리디닐기, 페난트롤리닐기, 페나지닐기, 벤조이미다졸일기， 벤조퓨라닐기, 벤조티오페닐기， 이소벤조티아졸일기, 벤조옥사졸일기, 이소벤조옥사졸일기, 트리아졸일기， 테트라졸일기， 옥사디아졸일기, 트리아지닐기, 디벤조퓨라닐기， 디벤조티오페닐기, 벤조카바졸일기， '' Cynolinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, Benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofura Nil group, dibenzothiophenyl group, benzocarbazolyl group ，
디벤조카바졸일기， 이미다조피리디닐기 및 이미다조피리미디닐기; 중에서 선택되고， 상기 Q33 내지 Q35는 서로 독립적으로， 수소, ^- o알킬기， d- o알콕시기, 페닐기， 나프틸기， 안트라세닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, Dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group; Q 33 to Q 35 may be each independently selected from hydrogen, ^ -oalkyl group, d-oalkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group,
크라이세닐기, 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 디벤조퓨라닐기, 디벤조티오페닐기, 피리디닐기, 피리미디닐기， 트리아지닐기， 퀴놀리닐기, Chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group,
이소퀴놀리닐기, 퀴나졸리닐기 및 퀴녹살리닐기 중에서 선택될 수 있다. It may be selected from an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group.
일 구현예에 따르면, 상기 화학식 2A및 2B의 R2, 상기 화학식 2C 및 2D의According to one embodiment, R 2 of Formulas 2A and 2B, of Formulas 2C and 2D
R3 및 상기 화학식 2E 및 2F의 R2 및 R3 중 적어도 하나는, R 3 and at least one of the general formula 2E and 2F of the R 2 and R 3 are,
페닐기, 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기， 헵탈레닐기, 인다세닐기， 아세나프틸기, 풀루오레닐기, 스파이로-플루오레닐기， 조플루오레닐기,  Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, pulluorenyl group, spiro-fluorenyl group, cofluorenyl group,
디벤조플루오레닐기, 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기， 나프타세닐기, 피세닐기, 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기, 루비세닐기, 코로네닐기, 오발레닐기, 피를일기， 티오페닐기, 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기， 이속사졸일기, 피리디닐기， 피라지닐기， 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기， 프탈라지닐기， 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기， 카바졸일기, 페난트리디닐기, 아크리디닐기, 페난트를리닐기, 페나지닐기， 벤조이미다졸일기, 벤조퓨라닐기, 벤조티오페닐기, 이소벤조티아졸일기, Dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group Nucleasenyl, pentacenyl, rubisenyl, coronyl, ovalenyl, pyryl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group ， Phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthryllinyl group, phenazinyl group, benzoimidazole group, Benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group,
벤조옥사졸일기， 이소벤조옥사졸일기, 트리아졸일기, 테트라졸일기， 옥사디아졸일기， 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기, Benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
디밴조카바졸일기， 이미다조피리디닐기 및 이미다조피리미디닐기; 및 Dibanzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group; And
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기, 아미노기, 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염， 술폰산 또는 이의 염, 인산 또는 이의 염, d-C2o알킬기， d-C2o알콕시기, -Si(Q33)(Q34)(Q35), 페닐기, 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기, 헵탈레닐기， 인다세닐기, 아세나프틸기， 플루오레닐기, 스파이로-플루오레닐기, 벤조플루오레닐기, 디벤조플루오레닐기， 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기， 나프타세닐기， 피세닐기, 페릴레닐기， 펜타페닐기, 핵사세닐기， 펜타세닐기, 루비세닐기, 코로네닐기， 오발레닐기， 피를일기, 티오페닐기， 퓨라닐기， 이미다졸일기， 피라졸일기， 티아졸일기, 이소티아졸일기, 옥사졸일기, 이속사졸일기, 피리디닐기, 피라지닐기, 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기， 이소퀴놀리닐기， 벤조퀴놀리닐기， 프탈라지닐기， 나프티리디닐기, 퀴녹살리닐기， 퀴나졸리닐기, 시놀리닐기， 카바졸일기， Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, dC 2 o alkyl groups, dC 2 o alkoxy groups, —Si (Q 33 ) (Q 34 ) (Q 35 ), phenyl groups, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, and Senyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, Phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, peryllenyl group, pentaphenyl group, nucleasenyl group, pentacenyl group, ruby Senyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, Pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indolyl, indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, Quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group,
페난트리디닐기, 아크리디닐기, 페난트를리닐기， 페나지닐기， 벤조이미다졸일기, 벤조퓨라닐기, 벤조티오페닐기， 이소벤조티아졸일기， 벤조옥사졸일기, Phenantridinyl group, acridinyl group, phenanthrylinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group,
이소벤조옥사졸일기, 트리아졸일기, 테트라졸일기, 옥사디아졸일기， 트리아지닐기， 디벤조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기, 디벤조카바졸일기， Isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group,
이미다조피리디닐기, 이미다조피리미디닐기 및 비페닐 중 적어도 하나로 치환된, 페닐기, 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기, 헵탈레닐기, 인다세닐기, 아세나프틸기, 플루오레닐기， 스파이로-플루오레닐기， 벤조플루오레닐기， Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorene substituted with at least one of imidazopyridinyl group, imidazopyrimidinyl group and biphenyl Nyl group, spiro-fluorenyl group, benzofluorenyl group,
디벤조플루오레닐기, 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기, 나프타세닐기, 피세닐기， 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기, 루비세닐기, 코로네닐기, 오발레닐기, 피를일기, 티오페닐기， 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기， 이속사졸일기， 피리디닐기， 피라지닐기, 피리미디닐기， 피리다지닐기， 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기， 퀴놀리닐기, 이소퀴놀리닐기， 벤조퀴놀리닐기, 프탈라지닐기, 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기, 카바졸일기, 페난트리디닐기, 아크리디닐기, 페난트를리닐기, 페나지닐 7 벤조이미다졸일기, 벤조퓨라닐기, 벤조티오페닐기， 이소벤조티아졸일기, Dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, fisenyl group, perenyl group, pentaphenyl group , Nuxasenyl group, pentaxenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazole group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group , Phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthryllinyl group, phenazinyl 7 benzoimidazolyl group, benzo Furanyl group, benzothiophenyl group, isobenzothiazolyl group,
벤조옥사졸일기, 이소벤조옥사졸일기， 트리아졸일기, 테트라졸일기, 옥사디아졸일기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기, Benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
디벤조카바졸일기, 이미다조피리디닐기 및 이미다조피리미디닐기; 중에서 선택되고, 상기 Q33 내지 Q35는 서로 독립적으로, 수소, C o알킬기, - o알콕시기, 페닐기, 나프틸기, 안트라세닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, 크라이세닐기, 카바졸일기， 벤조카바졸일기, 디벤조카바졸일기, 디벤조퓨라닐기, 디벤조티오페닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 퀴놀리닐기， 이소퀴놀리닐기, 퀴나졸리닐기 및 퀴녹살리닐기 중에서 선택될 수 있다. 예를 들어, 상기 화학식 2A및 2B의 R2, 상기 화학식 2C 및 2D의 R3 및 상기 화학식 2E 및 2F의 R2 및 R3 중 적어도 하나는， Dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group; Q 33 to Q 35 may be each independently selected from a hydrogen, a C o alkyl group, an o-alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, and a chrysenyl group. Carbazolyl, benzocarbazolyl, dibenzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, It may be selected from an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group. For example, at least one of R 2 of Formulas 2A and 2B, R 3 of Formulas 2C and 2D, and R 2 and R 3 of Formulas 2E and 2F,
페닐기, 나프틸기， 트리페닐레닐기， 페난쓰레닐기， 피리디닐기， 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐; 및  Phenyl, naphthyl, triphenylenyl, phenanthrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl; And
중수소, -F, -CI, -Br, -1， 히드록실기， 시아노기，니트로기， 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산또는 이의 염, C ^o알킬기, ^- 0알콕시기, -Si(Q33)(Q34)(Q35), 페닐기， 나프틸기, Deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ^ oalkyl group, ^ -0 alkoxy group, -Si (Q 33 ) (Q 34 ) (Q 35 ), phenyl group, naphthyl group,
트리페닐레닐기, 페난쓰레닐기， 피리디닐기， 피리미디닐기， 피라지닐기, 피리다지닐기 및 트리아지닐 중 적어도 하나로 치환된, 페닐기, 나프틸기， 트리페닐레닐기， 페난쓰레닐기， 피리디닐기， 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐; 중에서 선택되고, Phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridi substituted with at least one of triphenylenyl, phenanthrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl Nyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, and triazinyl; Is selected from,
상기 Q33 내지 Q35는 서로 독립적으로， 수소， ^-¾0알킬기, C ^o알콕시기, 페닐기 및 나프틸기 중에서 선택될 수 있다. And Q 33 to Q 35 are independently of each other, may be selected from hydrogen, -¾ ^ 0 alkyl, C ^ o alkoxy group, a phenyl group and a naphthyl group.
또 다른 구현예에 따르면, 상기 화학식 2A 및 2B의 R2, 상기 화학식 2C 및According to another embodiment, R 2 of Formulas 2A and 2B, Formula 2C and
2D의 R3 및 상기 화학식 2E 및 2F의 R2 및 R3 중 적어도 하나는, 상기 화학식 5-1 내지 5-63 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다. At least one of R 3 and 2D of the general formula 2E and 2F R 2 and R 3, may be selected from Formula 5-1 to 5-63, and the like.
또 다른 구현예에 따르면, 상기 화학식 2A 내지 2F의 중 Rl 5 화학식 1의 Χπ 중 및 화학식 1 B의 X12 중 R12는 서로 독립적으로， 치환 또는 비치환된 According to yet another embodiment, the formula 2A to 2F of R l 5 of the formula (I) and of formula (1) B X 12 Χπ of R 12 are each independently of the substituted or unsubstituted
C3-Cl0시클로알킬기, 치환 또는 비치환된 C2-C10헤테로시클로알킬기， 치환 또는 비치환된 Cr o시클로알케닐기, 치환 또는 비치환된 C2-C1(r해테로시클로알케닐기, 치환 또는 비치환된 C6-C20아릴기 , 치환 또는 비치환된 C2-C20헤테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹 및 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되되, 단, ¾은 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아니다. C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, substituted or unsubstituted Cr ocycloalkenyl group, substituted or unsubstituted C 2 -C 1 (r heterocycloalkenyl group , Substituted or unsubstituted C 6 -C 20 aryl group, substituted or unsubstituted C 2 -C 20 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent ratio An aromatic heterocondensed polycyclic group and a group represented by Formula 2A to a group represented by Formula 2F, provided that ¾ is not a group represented by Formula 2A to the group represented by Formula 2F.
예를 들어, 상기 화학식 2A 내지 2F의 중 화학식 1의 Xu 중 Ru 및 화학식 1B의 X12 중 R12는 서로 독립적으로, For example, R u of X u of Formula 1 and R 12 of X 12 of Formula 1B of Formulas 2A to 2F may be each independently,
페닐기, 나프틸기, 트리페닐레닐기， 페난쓰레닐기, 피리디닐기, 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐; 중수소, -F， - CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염， 술폰산 또는 이의 염, 인산 또는 이의 염, Ct- o알킬기, d-C^알콕시기， -Si(Q33)(Q34)(Q35), 페닐기, 나프틸기， Phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group and triazinyl; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, Ct-oalkyl group, dC ^ alkoxy group, -Si (Q 33 ) (Q 34 ) (Q 35 ), phenyl group, naphthyl group,
트리페닐레닐기, 페난쓰레닐기, 피리디닐기, 피리미디닐기, 피라지닐기， 피리다지닐기 및 트리아지닐 중 적어도 하나로 치환된, 페닐기, 나프틸기, 트리페닐레닐기, 페난쓰레닐기, 피리디닐기， 피리미디닐기， 피라지닐기, 피리다지닐기 및 트리아지닐; 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹; 중에서 선택 (단， 단, 은 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아님)될 수 있으나, 이에 한정되는 것은 아니다. Phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridi substituted with at least one of triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group and triazinyl Nyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, and triazinyl; A group represented by Formula 2A to a group represented by Formula 2F; (However, may be, but is not a group represented by Formula 2A to a group represented by Formula 2F), but is not limited thereto.
또 다른 구현예에 따르면, 상기 화학식 2A내지 2F 중 R4는 서로 독립적으로, 수소, 중수소, -F, -CI, -Br, -1， 히드록실기, 시아노기 , 니트로기 , 아미노기， 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염， 술폰산 또는 이의 염, 인산 또는 이의 염， d- o알킬기 및 CrC20알콕시기 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다. According to another embodiment, R 4 in Formulas 2A to 2F are each independently hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, or amidino group. , Hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, d-oalkyl group and CrC 20 alkoxy group can be selected, but is not limited thereto.
상기 화학식들 중 bl은 의 개수를 나타낸 것으로서, 1 내지 3의 정수 중에서 선택될 수 있다. bl이 2 이상일 경우, 2 이상의 R1은 서로 동일하거나 상이할 수 있다. b2 내지 b4, bl l, bl2 및 M7 내지 b20에 대한 설명은 bl에 대한 설명 및 화학식 1 및 화학식 2A내지 2F의 구조를 참조한다.  Bl represents the number of and may be selected from integers of 1 to 3. When bl is 2 or more, two or more R1 may be the same or different from each other. For the descriptions of b2 to b4, bl1, bl2 and M7 to b20, refer to the description of bl and the structures of Formula 1 and Formulas 2A to 2F.
또 다른 구현예에 따르면, 상기 화학식 1로 표시되는 축합환 화합물은, 하기 화학식 1-1 내지 1-9 증 하나로 표시될 수 있다: According to another embodiment, the condensed cyclic compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas 1-1 to 1-9:
Figure imgf000029_0001
Figure imgf000029_0001
화학식 1 화학식
Figure imgf000030_0001
Chemical Formula 1 Chemical Formula
Figure imgf000030_0001
화학식 1-9  Formula 1-9
상기 화학식 1-1 내지 1-9 중 Xn 및 12에 대한 설명은 제 1항에 기재된 바와 동일하고, R21 내지 R24에 대한 설명은 R17에 대한 설명을 참조하고, R25 내지 R27에 대한 설명은 R18에 대한 설명을 참조하고， R31 내지 R34에 대한 설명은 R20에 대한 설명을 참조하고, R35 내지 R37에 대한 설명은 R19에 대한 설명을 참조한다. X n and 12 in Formulas 1-1 to 1-9 are the same as described in claim 1, and for the description of R 21 to R 24 , refer to the description for R 17 , and R 25 to R 27. For a description thereof, see the description of R 18 , the description of R 31 to R 34 refer to the description of R 20 , and the description of R 35 to R 37 refer to the description of R 19 .
예를 들어， 상기 화학식 1-1 내지 1-9 중,  For example, in Formulas 1-1 to 1-9,
Xu은
Figure imgf000030_0002
및 0 중에서 선택되고;Xu
Figure imgf000030_0002
And 0;
2는 N-[(L12)aI2-(Rl2)bl2], S 및 0 증에서 선택되고;2 is selected from N-[(L 12 ) aI2- (R l2 ) bl2 ], S and 0 increments;
은 N-[(L,)al-(R,)bl], S 및 0 중에서 선택되고; Is selected from N-[(L,) al- (R,) bl ], S and 0;
i) 상기 화학식 1-1 내지 1-9 중 제은 N-KLu^ R^bn]이고, 2은 i) in Formulas 1-1 to 1-9, N-KLu ^ R ^ bn], and 2 is
N-[(L12)al2-(R12)bl2]이 아닐 경우, 상기 화학식 1 중 bll개의 RU,R21 내지 R27 및 R31 내지 R37 중 적어도 하나는， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; N - if not - [(L 12) al2 ( R 12) bl2], the general formula (1) of the bll of R U, R 21 to R 27 and R 31 to R 37, at least one of which, represented by the formula (2A) A group to a group represented by Formula 2F;
ϋ) 삼기 화학식 1-1 내지 1-6 중 Xu은 N-KLn^ RtObn]가 아니고 , 2은 N-[(L12)al2-(R12)bl2]일 경우, 상기 화학식 1 중 M2개의 R12,R21 내지 R27 및 R31 내지 R37중 적어도 하나는， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; ϋ) is not complaining of the formula 1-1 to 1-6 X u is N-KLn ^ RtObn], 2 is N - [(L 12) al2 - M2 one of (R 12) bl2], the general formula (1) if the At least one of R 12 , R 21 to R 27, and R 31 to R 37 is selected from the group represented by Formula 2A to the group represented by Formula 2F;
iii)상기 화학식 1-1 내지 1-6 중 제은 N-KLu^ Ru u]이고, 2은 iii) In Formulas 1-1 to 1-6, N is N-KLu ^ Ru u], and 2 is
N-[(L12)al2-(R12)bl2]일 경우, 상기 화학식 1 중 Ml개의 Ru,bl2개의 R12, R21 내지 R27 및 R31 내지 7 중 적어도 하나는， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; N - [(L 12) al2 - (R 12) bl2] be the case, of the formula 1 Ml of R u, bl2 of R 12, R 21 to R 27 and R 31 to 7 at least one of the formula (2A) It is selected from the group represented by the group represented by the formula (2F);
상기 내지 L4,LU 및 L12는 서로 독립적으로 상기 화학식 2-1 내지 2-13 (예를 들면, 상기 화학식 3-1 내지 3-12) 중에서 선택되고; To L 4 , L U and L 12 are each independently selected from Formulas 2-1 to 2-13 (eg, Formulas 3-1 to 3-12);
상기 al 내지 a4,all 및 al2는 서로 독립적으로 0 또는 1이고; 상기 Rh Rn 및 R12는 서로 독립적으로, Al to a4, all and al2 are each independently 0 or 1; Rh Rn and R 12 are independently of each other,
페닐기, 나프틸기， 트리페닐레닐기, 페난쓰레닐기, 피리디닐기， 피리미디닐기, 피라지닐기 , 피리다지닐기 및 트리아지닐;  Phenyl, naphthyl, triphenylenyl, phenanthrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;
중수소, -F, -CI, -Br, -1， 히드록실기, 시아노기 , 니트로기， 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염， Ct- o알킬기, d-C20알콕시기, -Si(Q33XQ34)(Q35), 페닐기, 나프틸기， Deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, Ct-oalkyl group, dC 20 alkoxy group, -Si (Q33XQ 34 ) (Q 35 ), phenyl group, naphthyl group,
트리페닐레닐기, 페난쓰레닐기, 피리디닐기, 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐 중 적어도 하나로 치환된, 페닐기, 나프틸기， 트리페닐레닐기， 페난쓰레닐기, 피리디닐기， 피리미디닐기, 피라지닐기， 피리다지닐기 및 트리아지닐; 및 Phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridi substituted with at least one of triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group and triazinyl Nyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, and triazinyl; And
상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹; 중에서 선택 (단, R & 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아님)되고;  A group represented by Formula 2A to a group represented by Formula 2F; Selected from R and not a group represented by Formula 2A to a group represented by Formula 2F;
상기 R2 및 R3 중 적어도 하나는, At least one of the R 2 and R 3 ,
페닐기, 나프틸기， 트리페닐레닐기, 페난쓰레닐기, 피리디닐기, 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐; 및  Phenyl, naphthyl, triphenylenyl, phenanthrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl; And
중수소, -F, -CI, -Br, -I, 히드톡실기, 시아노기， 니트로기， 아미노기， 아미디노기 , 히드라진기, 히드라존기, 카르복실산또는 이의 염， 술폰산 또는 이의 염, 인산 또는 이의 염, Ci- o알킬기, C!- o알콕시기, -Si(Q33)(Q34)(Q35), 페닐기, 나프틸기, Deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, Ci-oalkyl groups, C ! oalkoxy group, -Si (Q 33 ) (Q 34 ) (Q 35 ), phenyl group, naphthyl group,
트리페닐레닐기， 페난쓰레닐기， 피리디닐기, 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐 중 적어도 하나로 치환된, 페닐기, 나프틸기， 트리페닐레닐기， 페난쓰레닐기, 피리디닐기, 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐; 중에서 선택되고; Phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridi substituted with at least one of triphenylenyl, phenanthrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl Nyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, and triazinyl; Is selected from;
상기 ¾는 수소, 중수소， -F, -CI, -Br, -1， 히드록실기， 시아노기， 니트로기, 아미노기 , 아미디노기 , 히드라진기, 히드라존기 , 카르복실산 또는 이의 염 , 술폰산 또는 이의 염, 인산 또는 이의 염, CrC20알킬기 및 d-C2o알콕시기 중에서 선택되고; ¾ is hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or Salts thereof, phosphoric acid or salts thereof, CrC 20 alkyl groups and dC 2 oalkoxy groups;
R2. 내지 R27 및 R31 내지 7은 서로 독립적으로, R 2 . To R 27 and R 31 to 7 are independently of each other,
수소, 중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기， 아미노기 , 아미디노기, 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, CrC20알킬기 및 Cr o알콕시기; 중수소， -F, -CI, -Br, -I, 히드톡실기， 시아노기, 니트로기, 아미노기, 아미디노기， 히드라진기, 히드라존기， 카르복실산 또는 이의 염， 술폰산 또는 이의 염 및 인산 또는 이의 염 중 적어도 하나로 치환된, ^- 0알킬기 및 C!- o알콕시기; Hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C r C 20 alkyl group and a Cr o alkoxy group; Deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or A ^ -0 alkyl group and a C! -Alkoxy group substituted with at least one of its salts;
상기 화학식 4-1 내지 4-31 (예를 들면, 상기 화학식 5-1 내지 5-63);  Formulas 4-1 to 4-31 (eg, Formulas 5-1 to 5-63);
-Si(Q3)(Q4)(Q5)； 및 -Si (Q 3 ) (Q 4 ) (Q 5 ); and
상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 (단， 상기 내지 는 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아님); 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다.  A group represented by Formula 2A to a group represented by Formula 2F, provided that the group is not a group represented by Formula 2A to a group represented by Formula 2A; It may be selected from, but is not limited thereto.
일 구현예에 따르면, 상기 화학식 1로 표시되는 축합환 화합물은, 상기 화학식 1-1, 1-3 또는 1-5로 표시되고,  According to one embodiment, the condensed cyclic compound represented by Formula 1 is represented by Formula 1-1, 1-3, or 1-5,
상기 화학식 1-1, 1-3 및 1-5 중 은 ^[(^ ^ 이고， 는  In Formulas 1-1, 1-3, and 1-5, ^ [(^ ^,
N-[(L12)al2-(Rl2)bl2]이고， N - a - [(R l2) bl2 ( L 12) al2],
상기 Ru 및 R12는 서로 독립적으로， R u and R 12 are independently of each other,
페닐기， 나프틸기, 트리페닐레닐기, 페난쓰레닐기， 피리디닐기, 피리미디닐기， 피라지닐기, 피리다지닐기 및 트리아지닐;  Phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, and triazinyl;
중수소, -F, -CI, -Br, -1， 히드록실기, 시아노기， 니트로기, 아미노기, 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, C!- o알킬기， d-C20알콕시기， -Si(Q33)(Q34)(Q35), 페닐기, 나프틸기, Deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or a salt thereof, C -! o alkyl, dC 20 alkoxy group, -Si (Q3 3) (Q 34) (Q 35), a phenyl group, a naphthyl group,
트리페닐레닐기, 페난쓰레닐기, 피리디닐기， 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐 중 적어도 하나로 치환된, 페닐기, 나프틸기, 트리페닐레닐기, 페난쓰레닐기, 피리디닐기， 피리미디닐기, 피라지닐기, 피리다지닐기 및 트리아지닐; 상기 화학식 2Α로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹; 중에서 선택되고; Phenyl, naphthyl, triphenylenyl, phenanthrenyl, pyridi substituted with at least one of triphenylenyl, phenanthrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl Nyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, and triazinyl; A group represented by Formula 2A to a group represented by Formula 2F; Is selected from;
상기 Ru 및 R12 중 적어도 하나는 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다. At least one of Ru and R 12 may be selected from a group represented by Formula 2A to a group represented by Formula 2F, but is not limited thereto.
상기 화학식 1로 표시되는 축합환 화합물은, 하기 화합물 1 내지 30 중 하나일 수 있으나, 이에 한정되는 것은 아니다. The condensed cyclic compound represented by Formula 1 may be one of Compounds 1 to 30, but is not limited thereto.
Figure imgf000033_0001
Figure imgf000033_0001
98ZTOO/SlOZaM/X3d 0C9.Cl/ST0Z OAV 98ZTOO / SlOZaM / X3d 0C9.Cl/ST0Z OAV
χε χε
Figure imgf000034_0001
Figure imgf000034_0002
Figure imgf000034_0001
Figure imgf000034_0002
Figure imgf000034_0003
Figure imgf000034_0003
29 30  29 30
상기 화학식 1로 표시되는 축합환 화합물은 상기 화학식 2A로 표시되는 그룹 내지 화학식 2F로 표시되는 그룹 중 적어도 하나를 반드시 포함한다. 이로써, 상기 화학식 1로 표시되는 축합환 화합물은 바이폴라 특성을 가질 수 있으며, 유기 발광 소자용 재료 (예를 들면, 발광층 중 호스트)로 사용하기에 적합한 HOMO, LUMQ 에너지 갭 및 T1 에너지 레벨을 가질 수 있다.  The condensed cyclic compound represented by Formula 1 necessarily includes at least one of the group represented by Formula 2A to the group represented by Formula 2F. As a result, the condensed cyclic compound represented by Formula 1 may have a bipolar characteristic, and may have a HOMO, LUMQ energy gap, and T1 energy level suitable for use as an organic light emitting device material (for example, a host in the light emitting layer). have.
상기 화학식 1로 표시되는 축합환 화합물의 합성 방법은, 후술하는 합성예를 참조하여, 당업자가 용이하게 인식할 수 있다.  The synthesis method of the condensed cyclic compound represented by the formula (1) can be easily recognized by those skilled in the art with reference to the synthesis examples described later.
따라서, 상기 화학식 1로 표시되는 축합환 화합물은 유기 발광 소자의 유기층, 예를 들면, 상기 유기층 중 발광층의 호스트로 사용하기 적합할 수 있는 바, 다른 측면에 따르면, 제 1전극; 제 2전극; 및 상기 제 1전극과 상기 제 2전극 사이에 개재되고, 발광층을 포함하고, 상기 화학식 1로 표시되는 축합환 화합물을 적어도 1종 이상 포함한 유기층；을 포함한, 유기 발광 소자가 제공된다. Therefore, the condensed cyclic compound represented by Chemical Formula 1 may be suitable for use as an organic layer of an organic light emitting device, for example, as a host of a light emitting layer in the organic layer. According to another aspect, a first electrode; Second electrode; And between the first electrode and the second electrode. An organic light-emitting device is provided, including an organic layer, which includes a light emitting layer and includes at least one or more types of condensed cyclic compounds represented by the formula (1).
상기 유기 발광 소자는 상술한 바와 같은 화학식 1로 표시되는 축합환 화합물을 포함한 유기층을 구비함으로써, 저구동 전압， 고효율, 고휘도 및 장수명을 가질 수 있다.  The organic light emitting device may have a low driving voltage, high efficiency, high brightness, and long life by including an organic layer including a condensed cyclic compound represented by Formula 1 as described above.
상기 화학식 1로 표시되는 축합환 화합물은 유기 발광 소자의 한 쌍의 전극 사이에 사용될 수 있다. 예를 들어, 상기 축합환 화합물은 발광층, 계 1전극과 발광층 사이의 정공 수송 영역 (예를 들면, 정공 주입층, 정공 수송층 및 전자 저지층 중 적어도 하나를 포함함) 및 발광층과 게 2전극 사이의 전자 수송 영역 (예를 들면， 정공 저지층, 전자 수송층 및 전자 주입층 중 적어도 하나를 포함함) 중 적어도 하나에 포함될 수 있다. 예를 들어, 상기 화학식 1로 표시되는 축합환 화합물은 상기 발광층에 포함되어 있을 수 있다. 이 때, 상기 발광층은 도편트를 더 포함하고, 상기 발광층에 포함된 축합환 화합물은 호스트의 역할을 할 수 있다. 상기 발광층은 청색광 또는 녹색광을 방출하는 청색 발광층 또는 녹색 발광층일 수 있고, 상기 도펀트는 인광 도펀트일 수 있다.  The condensed cyclic compound represented by Formula 1 may be used between a pair of electrodes of the organic light emitting device. For example, the condensed cyclic compound may include a light emitting layer, a hole transport region (for example, at least one of a hole injection layer, a hole transport layer, and an electron blocking layer) between the light emitting layer, the first electrode, and the light emitting layer, and the light emitting layer and the second electrode. It may be included in at least one of the electron transport region (eg, including at least one of a hole blocking layer, an electron transport layer and an electron injection layer). For example, the condensed cyclic compound represented by Formula 1 may be included in the emission layer. In this case, the light emitting layer may further include a dopant, and the condensed cyclic compound included in the light emitting layer may serve as a host. The light emitting layer may be a blue light emitting layer or a green light emitting layer emitting blue light or green light, and the dopant may be a phosphorescent dopant.
본 명세서 중 "(유기층이) 축합환 화합물을 1종 이상 포함한다"란，  In this specification, "(organic layer) contains one or more types of condensed cyclic compounds",
"(유기층이) 상기 화학식 1의 범주에 속하는 1종의 축합환 화합물 또는 상기 화학식 1의 범주에 속하는 서로 다른 2종 이상의 축합환 화합물을 포함할 수 있다"로 해석될 수 있다. It may be interpreted as “(organic layer) may include one condensed cyclic compound belonging to the category of Formula 1 or two or more different condensed cyclic compounds belonging to the category of Formula 1.
예를 들어, 상기 유기층은 상기 축합환 화합물로서， 상기 화합물 1만을 포함할 수 있다. 이 때, 상기 화합물 1은 상기 유기 발광 소자의 발광층에 존재할 수 있다. 또는， 상기 유기층은 상기 축합환 화합물로서， 상기 화합물 1과 화합물 2를 포함할 수 있다. 이 때, 상기 화합물 1과 화합물 2는 동일한 층에 존재 (예를 들면, 상기 화합물 1과 화합물 2는 모두 발광층에 존재할 수 있음)하거나, 서로 다른 층에 존재할 수 있다.  For example, the organic layer may include only Compound 1 as the condensed cyclic compound. In this case, the compound 1 may be present in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the condensed cyclic compound. In this case, the compound 1 and compound 2 may be present in the same layer (for example, both compound 1 and compound 2 may be present in the light emitting layer), or may be present in different layers.
상기 제 1전극은 정공 주입 전극인 애노드이고 상기 제 2전극은 전자 주입 전극인 캐소드이거나， 상기 제 1전극은 전자 주입 전극인 캐소드이고 상기 제 2전극은 정공 주입 전극인 캐소드이다.  The first electrode is an anode which is a hole injection electrode and the second electrode is a cathode which is an electron injection electrode, or the first electrode is a cathode which is an electron injection electrode, and the second electrode is a cathode which is a hole injection electrode.
예를 들어, 상기 제 1전극은 애노드이고, 상기 게 2전극은 캐소드이고, 상기 유기층은, i) 상기 제 1전극과 상기 발광층 사이에 개재되고, 정공 주입층, 정공 수송층 및 전자 저지층 중 적어도 하나를 포함한 정공 수송 영역; 및 ii) 상기 발광층과 상기 제 2전극 사이에 개재되고, 정공 저지층, 전자 수송층 및 전자 주입층 중 적어도 하나를 포함한 전자 수송 영역;을 포함할 수 있다. For example, the first electrode is an anode, the crab second electrode is a cathode, and the organic layer is, i) interposed between the first electrode and the light emitting layer, a hole injection layer, a hole A hole transport region comprising at least one of a transport layer and an electron blocking layer; And ii) an electron transport region interposed between the light emitting layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
본 명세서 중 "유기층"은 유기 발광 소자 중 제 1전극과 제 2전극 사이에 개재된 단일 및 /또는 복수의 층을 가리키는 용어이다. 상기 "유기층"은 유기 화합물뿐만 아니라, 금속을 포함한 유기금속 착체 등도 포함할 수 있다.  As used herein, the term "organic layer" refers to a single and / or a plurality of layers interposed between the first electrode and the second electrode of the organic light emitting device. The "organic layer" may include not only an organic compound but also an organometallic complex including a metal.
도 1은 본 발명의 일 구현예를 따르는 유기 발광 소자 (10)의 단면도를 개략적으로 도시한 것이다. 이하, 도 1을 참조하여 본 발명의 일 구현예를 따르는 유기 발광 소자의 구조 및 제조 방법을 설명하면 다음과 같다. 유기 발광  1 schematically illustrates a cross-sectional view of an organic light emitting device 10 according to one embodiment of the invention. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. 1. Organic luminescence
소자 (10)는 제 1전극 (11), 유기층 (15) 및 제 2전극 (19)이 차례로 적층된 구조를 갖는다. 상기 제 1전극 (11) 하부 또는 제 2전극 (19) 상부에는 기판이 추가로 배치될 수 있다. 상기 기판으로는, 통상적인 유기 발광 소자에서 사용되는 기판을 사용할 수 있는데, 기계적 강도, 열안정성， 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유리 기판 또는 투명 플라스틱 기판을 사용할 수 있다. The element 10 has a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked. A substrate may be further disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a conventional organic light emitting device can be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.
상기 제 1전극 (1 1)은 예를 들면, 기판 상부에, 제 1전극용 물질을 증착법 또는 스퍼터링법 등을 이용하여 제공함으로써 형성될 수 있다. 상기 제 1전극 (1 1)은 애노드일 수 있다. 상기 제 1전극용 물질은 정공 주입이 용이하도록 높은 일함수를 갖는 물질 중에서 선택될 수 있다. 상기 제 1전극 (1 1)은 반사형 전극, 반투과형 전극 또는 투과형 전극일 수 있다. 제 1전극용 물질로는 산화인듐주석 (ΠΌ),  The first electrode 11 may be formed by, for example, providing a material for the first electrode on the substrate by using a deposition method or a sputtering method. The first electrode 11 may be an anode. The material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. Indium tin oxide (ΠΌ) as the material for the first electrode,
산화인듐아연 (IZO), 산화주석 (Sn02), 산화아연 (ZnO) 등을 이용할 수 있다. 또는, 마그네슴 (Mg), 알루미늄 (A1), 알루미늄 -리튬 (Al-Li), 칼슘 (Ca), 마그네슘 -인듐 (Mg-In), 마그네슘-은 (Mg-Ag)등과 같은 금속을 이용할 수 있다. Indium zinc oxide (IZO), tin oxide (Sn0 2 ), zinc oxide (ZnO) and the like can be used. Alternatively, metals such as magnesium (Mg), aluminum (A1), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like can be used. have.
상기 제 1전극 (1 1)은 단일층 또는 2 이상의 층을 포함한 다층 구조를 가질 수 있다.  The first electrode 11 may have a single layer or a multilayer structure including two or more layers.
상기 게 1전극 (11) 상부로는 유기층 (15)이 배치되어 있다.  The organic layer 15 is disposed above the cradle 1 electrode 11.
상기 유기층 (15)은 정공 수송 영역 (hole transport region); 발광층 (emission layer); 및 전자 수송 영역 (electron transport region);을 포함할 수 있다.  The organic layer 15 may include a hole transport region; An emission layer; And an electron transport region.
상기 정공 수송 영역은 게 1전극 (1 1)과 발광층 사이에 배치될 수 있다.  The hole transport region may be disposed between the crab electrode 1 11 and the light emitting layer.
상기 정공 수송 영역은 정공 주입층, 정공 수송층， 전자 저지층 및 버퍼층 중 적어도 하나를 포함할 수 있다. 상기 정공 수송 영역은 정공 주입층만을 포함하거나， 정공 수송층만을 포함할 수 있다. 또는， 상기 정공 수송 영역은, 제 1전극 (1 1)로부터 차례로 적층된， 정공 주입층 /정공 수송층 또는 정공 주입층 /정공 수송층 /전자 저지층의 구조를 가질 수 있다. The hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer. The hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer, which are sequentially stacked from the first electrode 11.
정공 수송 영역이 정공 주입층을 포함할 경우, 정공 주입층 (HIL)은 상기 제 1전극 (1 1) 상부에 진공증착법, 스핀코팅법， 캐스트법, LB법 등과 같은 다양한 방법을 이용하여 형성될 수 있다.  When the hole transport region includes the hole injection layer, the hole injection layer HIL may be formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, cast, LB, and the like. Can be.
진공 증착법에 의하여 정공 주입층을 형성하는 경우, 그 증착 조건은 정공 주입층 재료로 사용하는 화합물, 목적으로 하는 정공 주입층의 구조 및 열적 특성 등에 따라 다르지만, 예를 들면， 증착온도 약 100 내지 약 500 °C , 진공도 약 HT8 내지 약 10"3torr, 증착 속도 약 0.01 내지 약 100A/sec의 범위에서 선택될 수 있으며 이에 한정되는 것은 아니다. When the hole injection layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the hole injection layer as desired, and the deposition temperature is about 100 to about, for example. 500 ° C., vacuum degree of about HT 8 to about 10 " 3 torr, and deposition rate of about 0.01 to about 100 A / sec, but is not limited thereto.
스핀 코팅법에 의하여 정공 주입층을 형성하는 경우， 코팅 조건은  When the hole injection layer is formed by spin coating, the coating conditions are
정공주입층 재료로 사용하는 화합물, 목적하는 하는 정공 주입층의 구조 및 열적 특성에 따라 상이하지만, 약 2000rpm 내지 약 5000rpm의 코팅 속도, 코팅 후 용매 제거를 위한 열처리 온도는 약 80 °C 내지 200 °C의 온도 범위에서 선택될 수 있으며: 이에 한정되는 것은 아니다. Depending on the compound used as the hole injection layer material, the structure and the thermal properties of the desired hole injection layer, the coating speed of about 2000rpm to about 5000rpm, the heat treatment temperature for removing the solvent after coating is about 80 ° C to 200 ° It may be selected in the temperature range of C : but not limited to.
상기 정공 수송층 및 전자 저지층 형성 조건은 정공 주입층 형성 조건을 참조한다.  The hole transport layer and the electron blocking layer forming conditions refer to the hole injection layer forming conditions.
상기 정공 수송 영역은, 예를 들면, m-MTDATA, TDATA, 2-TNATA, NPB, β-ΝΡΒ, TPD, Spiro-TPD, Spiro-NPB, α-ΝΡΒ, TAPC, HMTPD,  The hole transport region may be, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-ΝΡΒ, TPD, Spiro-TPD, Spiro-NPB, α-ΝΡΒ, TAPC, HMTPD,
TCTA(4,4',4"-트리스 (N-카바졸일)트리페닐아민 (4,4',4"-tris(N-carbazolyl)triphenylamme)), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid:폴리아닐린 /도데실벤젠술폰산),  TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine (4,4', 4" -tris (N-carbazolyl) triphenylamme)), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / Dodecylbenzenesulfonic acid),
PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenes^ 틸렌디옥 시티오펜 )/폴리 (4-스티렌술포네이트)) , Pani/CSA (Polyaniline/Camphor PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenes ^ styrenedioxiophene) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor
sulfonicacid:폴리아닐린 /캠퍼술폰산), PANI/PSS sulfonicacid: polyaniline / camphor sulfonic acid), PANI / PSS
(Polyaniline)/Poly(4-styrenesulfonate):폴리아닐린) /폴리 (4-스티렌술포네이트)) , 하기 화학식 2이로 표시되는 화합물 및 하기 화학식 202로 표시되는 화합물 중 적어도 하나를 포함할 수 있다: (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)), a compound represented by the following Chemical Formula 2, and a compound represented by the following Chemical Formula 202 may be included:
Figure imgf000038_0001
Figure imgf000038_0001
98∑I00/SI0ia¾/X3d 98∑I00 / SI0ia¾ / X3d
9S 0f9Z.t:i/SI02 OAS. <화 201> 9S 0f9Z.t: i / SI02 OAS. <Tue 201>
Figure imgf000039_0001
Figure imgf000039_0001
상기 화학식 201 중， Ar101 및 Arl02는 서로 독립적으로, In Formula 201, Ar 101 and Ar l02 are each independently,
페닐렌기, 펜타레닐렌기， 인데닐렌기， 나프틸렌기, 아줄레닐렌기,  Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group,
헵탈레닐렌기, 아세나프틸렌기, 플루오레닐렌기, 페나레닐렌기, 페난트레닐렌기, 안트라세닐렌기, 플루오란테닐렌기, 트리페닐레닐렌기, 파이레닐렌기， Heptalenylene group, acenaphthylene group, fluorenylene group, phenenylene group, phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenylenylene group, pyrenylene group,
크라이세닐레닐렌기, 나프타세닐렌기, 피세닐렌기, 페릴레닐렌기 및 펜타세닐렌기; 및 · Chrysenylenylene group, naphthacenylene group, pisenylene group, peryleneyl group and pentaxenylene group; And ·
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기, 니트로기 , 아미노기, 아미디노기, 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염, d- o알킬기, C2-C60알케닐기， C2-C60알키닐기， d- o알콕시기, C3-C10시클로알킬기， C3-C10시클로알케닐기 , C2-C10헤테로시클로알킬기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, d-oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, d-oalkoxy group, C 3 -C 10 cycloalkyl group, C 3 -C 10 cycloalkenyl group, C 2 -C 10 heterocycloalkyl group,
C2-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C 2 -C 10 hetero come cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea,
C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹 중 적어도 하나로 치환된, 페닐렌기, 펜타레닐렌기， 인데닐렌기, 나프틸렌기， 아줄레닐렌기, 헵탈레닐렌기, 아세나프틸렌기, 플루오레닐렌기, 페나레닐렌기, 페난트레닐렌기, 안트라세닐렌기, 플루오란테닐렌기， 트리페닐레닐렌기, 파이레닐렌기, 크라이세닐레닐렌기， 나프타세닐렌기, 피세닐렌기, 페릴레닐렌기 및 펜타세닐렌기; 중에서 선택될 수 있다. C 2 -C 60 heteroaryl group, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azule substituted with at least one of a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed polycyclic group. A neylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenenylene group, Phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenylenylene group, pyrenylene group, chrysenenylene group, naphthacenylene group, pizenylene group, perenylene group and pentaxenylene group; It can be selected from.
상기 화학식 201 중， 상기 xa 및 xb는 서로 독립적으로 0 내지 5의 정수, 또는 0, 1 또는 2일 수 있다. 예를 들어, 상기 xa는 1이고, xb는 0일 수 있으나， 이에 한정되는 것은 아니다.  In Formula 201, xa and xb may be each independently an integer of 0 to 5, or 0, 1 or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.
상기 화학식 201 및 202 중, 상기 R101 내지 R108, Rm 내지 R 및 Rui 내지 R124는 서로 독립적으로, In Formulas 201 and 202, R 101 to R 108 , Rm to R, and Rui to R 124 are each independently of one another.
수소, 증수소， -F, -CI, -Br, -1， 히드록실기, 시아노기, 니트로기, 아미노기 , 아미디노기, 히드라진기， 히드라존기, 카르복실산기 또는 이의 염， 술폰산기 또는 이의 염, 인산기 또는 이의 염, -C10알킬기 (예를 들면， 메틸기， 에틸기， 프로필기, 부틸기， 펜틸기， 핵실기 등) 및 Cr o알콕시기 (예를 들면, 메록시기, 에톡시기, 프로폭시기， 부록시기, 펜특시기 등); Hydrogen, dihydrogen, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or its Salts, phosphoric acid groups or salts thereof, -C 10 alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, heterosil, etc.) and Cr oalkoxy groups (e.g., hydroxy, ethoxy, pro Typhoons, appendices, pens, etc.);
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기, 니트로기， 아미노기, 아미디노기， 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염 및 인산기 또는 이의 염 중 하나 이상으로 치환된， - o알킬기 및 d-do알콕시기; 페닐기, 나프틸기， 안트라세닐기, 플루오레닐기 및 파이레닐기; 및  Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof and phosphoric acid group Or -oalkyl group and d-doalkoxy group substituted with one or more of its salts; Phenyl group, naphthyl group, anthracenyl group, fluorenyl group and pyrenyl group; And
중수소, -F, -CI, -Br, -I, 히드톡실기, 시아노기 , 니트로기， 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산기 또는 이의 염， 술폰산기 또는 이의 염, 인산기 또는 이의 염, d- o알킬기 및 d-do알콕시기 중 하나 이상으로 치환된, 페닐기, 나프틸기, 안트라세닐기, 풀루오레닐기 및 파이레닐기; 중 하나일 수 있으나, 이에 한정되는 것은 아니다.  Deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a phenyl group, naphthyl group, anthracenyl group, pulluorenyl group and pyrenyl group substituted with one or more of salts, d-oalkyl groups and d-doalkoxy groups thereof; It may be one of, but is not limited thereto.
상기 화학식 201 중， R109는, 페닐기, 나프틸기, 안트라세닐기 및 피리디닐기; 및 중수소, -F, -CI, -Br, -I, 히드톡실기, 시아노기， 니트로기 , 아미노기， 아미디노기 , 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염, d- o알킬기 및 d-C20알콕시기 중 하나 이상으로 치환된, 페닐기, 나프틸기， 안트라세닐기 및 피리디닐기; 중 하나일 수 있다. In Formula 201, R 109 is a phenyl group, a naphthyl group, anthracenyl group, and a pyridinyl group; And deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phenyl, naphthyl, anthracenyl and pyridinyl groups substituted with one or more of phosphoric acid groups or salts thereof, d-oalkyl groups and dC 20 alkoxy groups; It may be one of the.
일 구현예에 따르면, 상기 화학식 2이로 표시되는 화합물은 하기 화학식  According to one embodiment, the compound represented by Formula 2 is represented by the formula
201A로 표시될 수 있으나， 이에 한정되는 것은 아니다: < 201A> 201A, but is not limited to: <201 A>
Figure imgf000041_0001
Figure imgf000041_0001
상기 화학식 201A 중， R101, Rm, R112 및 R109에 대한 상세한 설명은 상술한 바를 참조한다. In Formula 201A, R 101 , R m , R 112, and R 109 may be referred to the foregoing for detailed description.
예를 들어, 상기 화학식 2이로 표시되는 화합물 및 상기 화학식 202로 표시되는 화합물은 하기 화합물 HT1 내지 HT20을 포함할 수 있으나, 이에 한정되는  For example, the compound represented by Formula 2 and the compound represented by Formula 202 may include the following compounds HT1 to HT20, but are not limited thereto.
Figure imgf000041_0002
Figure imgf000041_0002
Figure imgf000042_0001
Figure imgf000042_0002
Figure imgf000042_0001
Figure imgf000042_0002
Figure imgf000042_0003
Figure imgf000042_0003
98ZTOO/SlOZaM/X3d 0C9.Cl/ST0Z OAV 98ZTOO / SlOZaM / X3d 0C9.Cl/ST0Z OAV
Figure imgf000043_0001
Figure imgf000043_0001
Figure imgf000043_0002
Figure imgf000043_0002
HT19 HT20  HT19 HT20
상기 정공 수송 영역의 두께는 약 100A 내지 약 10000A, 예를 들면, 약 100A 내지 약 1000A일 수 있다. 상기 정공 수송 영역이 정공 주입층 및 정공 수송층을 모두 포함한다면, 상기 정공 주입층의 두께는 약 100 A 내지 약 10000 A, 예를 들면, 약 100A 내지 약 1000A이고, 상기 정공 수송층의 두께는 약 50A 내지 약 2000A, 예를 들면 약 100A 내지 약 1500A일 수 있다. 상기 정공 수송 영역, 정공 주입층 및 정공 수송층의 두께가 전술한 바와 같은 범위를 만족할 경우， 실질적인 구동 전압 상승없이 만족스러운 정도의 정공 수송 특성을 얻을 수 있다. 상기 정공 수송 영역은 상술한 바와 같은 물질 외에, 도전성 향상을 위하여 전하 -생성 물질을 더 포함할 수 있다. 상기 전하 -생성 물질은 상기 정공 수송 영역 내에 균일하게 또는 불균일하게 분산되어 있을 수 있다.  The hole transport region may have a thickness of about 100A to about 10000A, for example, about 100A to about 1000A. If the hole transport region includes both a hole injection layer and a hole transport layer, the hole injection layer has a thickness of about 100 A to about 10000 A, for example, about 100 A to about 1000 A, and the hole transport layer has a thickness of about 50 A. To about 2000A, for example about 100A to about 1500A. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage. In addition to the materials described above, the hole transport region may further include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or heterogeneously dispersed in the hole transport region.
상기 전하 -생성 물질은 예를 들면， P-도펀트일 수 있다. 상기 P-도펀트는 퀴논 유도체， 금속 산화물 및 시아노기 -함유 화합물 중 하나일 수 있으나， 이에 한정되는 것은 아니다. 예를 들어, 상기 P-도펀트의 비제한적인 예로는,  The charge-generating material may be, for example, a P-dopant. The P-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the P-dopant,
테트라사이아노퀴논다이메테인 (TCNQ) 및 Tetracyanoquinonedimethane (TCNQ) and
2,3,5,6-테트라플루오로 -테트라사이아노 -1 ,4-벤조퀴논다이메테인 (F4-TCNQ) 등과 같은 퀴논 유도체; 텅스텐 산화물 및 몰리브덴 산화물 등과 같은 금속 산화물; 및 하기 화합물 HT-D1 등과 같은 시아노기 -함유 화합물 등을 들 수 있으나, 이에 한정되는 것은 아니다. < HT-D1> <F4-TCNQ> Quinone derivatives such as 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ) and the like; Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the compound HT-D1, and the like, but are not limited thereto. <HT-D1><F4-TCNQ>
Figure imgf000044_0001
Figure imgf000044_0001
상기 정공 수송 영역은, 버퍼층을 더 포함할 수 있다.  The hole transport region may further include a buffer layer.
상기 버퍼층은 발광층에서 방출되는 광의 파장에 따른 광학적 공진 거리를 보상하여 효율을 증가시키는 역할을 수 있다.  The buffer layer may serve to increase efficiency by compensating an optical resonance distance according to a wavelength of light emitted from the emission layer.
상기 정공 수송 영역 상부에 진공 증착법, 스핀 코팅법, 캐스트법, LB법 등과 같은 방법을 이용하여 발광층 (EML)을 형성할 수 있다. 진공 증착법 및 스핀 코팅법에 의해 발광층을 형성하는 경우, 그 증착 조건 및 코팅 조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공 주입층의 형성과 거의 동일한 조건범위 중에서 선택될 수 있다.  An emission layer (EML) may be formed on the hole transport region by using a method such as vacuum deposition, spin coating, casting, and LB. When the light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions and coating conditions vary depending on the compound to be used, and in general, may be selected from a range of conditions substantially the same as the formation of the hole injection layer.
상기 유기 발광 소자가 풀 컬러 유기 발광 소자일 경우, 발광층은 적색 발광층, 녹색 발광층 및 청색 발광층으로 패터닝될 수 있다. 또는, 상기 발광층은 적색 발광층， 녹색 발광층 및 /또는 청색 발광층이 적층된 구조를 가짐으로써, 백색광을 방출할 수 있는 등 다양한 변형예가 가능하다.  When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.
상기 발광층은 호스트 및 도편트를 포함할 수 있다. 상기 호스트는 상기 화학식 1로 표시되는 축합환 화합물을 포함할 수 있다. 일 구현예에 따르면, 상기 발광층을 녹색광을 방출하는 녹색 발광층일 수 있다.  The light emitting layer may include a host and a dopant. The host may include a condensed cyclic compound represented by Chemical Formula 1. According to one embodiment, the light emitting layer may be a green light emitting layer for emitting green light.
상기 발광층 중 도편트는 형광 방출 메커니즘에 따라 광을 방출하는 형광 도펀트로서 또는 인광 방출 메커니즘에 따라 광을 방출하는 인광 도펀트를 포함할 수 있다.  The dopant in the light emitting layer may include a fluorescent dopant emitting light according to a fluorescence emitting mechanism or a phosphorescent dopant emitting light according to a phosphorescent emitting mechanism.
다른 구현예에 따르면， 상기 호스트는 서로 상이한 제 1호스트 및  According to another embodiment, the host is different from the first host and
제 2호스트를 포함하되, 상기 제 1호스트는 상기 화학식 1로 표시되는 축합환 화합물을 포함하고, 상기 게 2호스트는 하기 화학식 41로 표시되는 게 1화합물 및 하기 화학식 61로 표시되는 제 2화합물 중 적어도 하나를 포함할 수 있다: Including a second host, wherein the first host includes a condensed cyclic compound represented by the formula (1), wherein the crab host 2 is a compound of the first compound represented by the formula (41) and the second compound represented by the formula (61) At least one may include:
<화학식 41>
Figure imgf000045_0001
<Formula 41>
Figure imgf000045_0001
<화학식 61>  <Formula 61>
Figure imgf000045_0002
Figure imgf000045_0002
<화학식 61A> <화학식 61B>
Figure imgf000045_0003
<Formula 61A><Formula61B>
Figure imgf000045_0003
상기 화학식 41 , 61, 61A 및 61B 증 Formula 41, 61, 61A and 61B increase
41은 N-[(L42)a42-(R42)b42], S, 0, S(=0), S(=0)2, C(=0), C(R43)(R44), Si(R43)(R44), P(R43), P(=0)(R43) 및 C=N(R43) 중에서 선택되고; 41 is N - [(L4 2) a42 - (R 42) b42], S, 0, S (= 0), S (= 0) 2, C (= 0), C (R 43) (R 44 ), Si (R4 3 ) (R4 4 ), P (R4 3 ), P (= 0) (R4 3 ) and C = N (R4 3 );
상기 화학식 61 중 고리 A61은 상기 화학식 61 A로 표시되고; Ring A 61 in Formula 61 is represented by Formula 61 A;
상기 화학식 61 중 고리 A62는 상기 화학식 61B로 표시되고; Ring A 62 in Formula 61 is represented by Formula 61B;
【은 N-[(L62)a62-(R62)b62], S, 0, S(=0), S(=0)2, C(=0), C(R63)(R64), (¾3)(¾4), P(R63), P(=0)(R63) 및 C=N(R63) 중에서 선택되고; 【Is N-[(L 62 ) a62- (R 62 ) b62 ], S, 0, S (= 0), S (= 0) 2 , C (= 0), C (R 63 ) (R 64 ) , (¾ 3 ) (¾ 4 ), P (R 63 ), P (= 0) (R 63 ) and C = N (R 63 );
X기은 C(R71) 또는 N이고, X72는 C(R72) 또는 N이고, X73은 C(R73) 또는 N이고, X74는 C(R74) .또는 N이고, X75는 C(R75) 또는 N이고， X76은 C(R76)또는 N이고, X77은 C(R77) 또는 N이고, X78은 C(R78) 또는 N이고; Group X is C (R 71 ) or N, X 72 is C (R 72 ) or N, X 73 is C (R 73 ) or N, and X 74 is C (R 74 ) . Or N, X 75 is C (R 75 ) or N, X 76 is C (R 76 ) or N, X 77 is C (R 77 ) or N, X 78 is C (R 78 ) or N ego;
Ar41, L4,, L42, L61 및 L62에 대한 설명은 본 명세서 중 ！ 에 대한 설명을 참조하고; For the description of Ar 41 , L 4 ,, L 42 , L 61 and L 62 , refer to the description of!
nl 및 n2는 서로 독립적으로， 0 내지 3의 정수 중에서 선택되고;  nl and n2 are each independently selected from an integer of 0 to 3;
a41, a42, a61 및 a62는 서로 독립적으로, 0 내지 3의 정수 중에서 선택되고; R41 내지 R43, R51 내지 4, 1 내지 R64 및 R71 내지 R?9는 서로 독립적으로, 수소, 중수소, -F, -CI, -Br, -1， 히드록실기， 시아노기, 니트로기， 아미노기， 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염， 술폰산 또는 이의 염， 인산 또는 이의 염， 치환 또는 비치환된 Cr o알킬기， 치환 또는 비치환된 C2-C60알케닐기, 치환 또는 비치환된 C2-C60알키닐기， 치환 또는 비치환된 C!- o알콕시기， 치환 또는 비치환된 C3-C10시클로알킬기, 치환 또는 비치환된 C2-C10헤테로시클로알킬기, 치환 또는 비치환된 C3-C10시클로알케닐기， 치환 또는 비치환된 a41, a42, a61 and a62 are each independently selected from an integer of 0 to 3; R41 to R43, R 5 1 to 4, 1 to R64 and R71 to R? 9 are each independently hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted Cr oalkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group , Substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted C! -Oalkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 2 -C 10 hetero Cycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted
c2-c10헤테로시클로알케닐기, 치환 또는 비치환된 c6-c60아릴기, 치환 또는 비치환된 c6-c60아릴옥시기, 치환 또는 비치환된 c6-c60아릴티오기， 치환 또는 비치환된 c 2 -c 10 heterocycloalkenyl group, substituted or unsubstituted c 6 -c 60 aryl group, substituted or unsubstituted c 6 -c 60 aryloxy group, substituted or unsubstituted c 6 -c 60 arylthio group ， Substituted or unsubstituted
C2-C60헤테로아릴기， 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비 -방향족 헤테로축합다환 그룹, -N^!X^), -Si(Q3)(Q4)(Q5) 및 C 2 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -N ^! X ^), -Si (Q 3 ) (Q 4 ) (Q 5 ) and
-B(Q6)(Q7) 중에서 선택되고; -B (Q 6 ) (Q 7 );
b41, b42, b51 내지 b54, b61 , b62 및 b79는 서로 독립적으로, 1 내지 3의 정수 중에서 선택될 수 있다.  b41, b42, b51 to b54, b61, b62 and b79 may be each independently selected from integers of 1 to 3.
일 구현예에 따르면, 상기 ！니 내지 ¾3, 1151 내지 RM, !^ 내지 R64 및 R7i 내지 R79는 서로 독립적으로, According to one embodiment, the！ Ni to ¾ 3 , 11 51 to RM,! ^ To R64 and R 7 i to R 79 are each independently,
수소, 중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, CrC20알킬기 및 Cr"C2o알콕시기; Hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a CrC 20 alkyl group and a Cr ″ C 2 oalkoxy group;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기 , 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염 및 인산 또는 이의 염 중 적어도 하나로 치환된, ^- 0알킬기 및 ^- ο알콕시기; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or A ^ -0 alkyl group and a ^ -οalkoxy group substituted with at least one of its salts;
페닐기， 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기, 헵탈레닐기, 인다세닐기， 아세나프틸기, 플루오레닐기， 스파이로-플루오레닐기, 벤조플루오레닐기，  Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group,
디벤조플루오레닐기， 페날레닐기， 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기, 나프타세닐기, 피세닐기, 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기, 루비세닐기, 코로네닐기， 오발레닐기, 피를일기, 티오페닐기， 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기, 이속사졸일기, 피리디닐기, 피라지닐기, 피리미디닐기， 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기， 프탈라지닐기, 나프티리디닐기， 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기， 카바졸일기, 페난트리디닐, 아크리디닐， 페난트를리닐， 페나지닐， 벤조이미다졸일기, 벤조퓨라닐기, 벤조티오페닐기, 이소벤조티아졸일기, Dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, fisenyl group, perylenyl group, pentaphenyl group , Nuxasenyl group, pentaxenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, Benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenantridinyl, acridinyl, phenanthlinyl, phenazinyl, benzoimidazolyl , Benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group,
벤조옥사졸일기, 이소벤조옥사졸일기, 트리아졸일기， 테트라졸일기, 옥사디아졸일기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기, Benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
디벤조카바졸일기, 이미다조피리디닐기, 이미다조피리미디닐 및 비페닐기 중 적어도 하나로 치환된, 페닐기， 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기， 헵탈레닐기， 인다세닐기, 아세나프틸기， 플루오레날기, 스파이로-플루오레닐기, 벤조플루오레닐기, 디벤조플루오레닐기， 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기， 나프타세닐기， 피세닐기， 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기, 루비세닐기, 코로네닐기, 오발레닐기, 피를일기, 티오페닐기， 퓨라닐기, 이미다졸일기, 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기， 이속사졸일기， 피리디닐기, 피라지닐기, 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기， 벤조퀴놀리닐기, 프탈라지닐기, 나프티리디닐기， 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기, 카바졸일기, 페난트리디닐, 아크리디닐, 페난트를리닐， 페나지닐, 벤조이미다졸일기， 벤조퓨라닐기, 벤조티오페닐기, 이소벤조티아졸일기, A phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indansenyl group, substituted with at least one of dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl and biphenyl group Acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyre Neyl group, chrysenyl group, naphthacenyl group, pisenyl group, peryleneyl group, pentaphenyl group, nucleusenyl group, pentansenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group , Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indolyl, Indazolyl, furinyl, quinolinyl, Isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthlinyl, phenazinyl , Benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group,
벤조옥사졸일기, 이소벤조옥사졸일기, 트리아졸일기, 테트라졸일기, 옥사디아졸일기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기, Benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group,
디벤조카바졸일기, 이미다조피리디닐기 및 이미다조피리미디닐; Dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기 , 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, ^- 0알킬기， d-C20알콕시기, -Si(Q33)(Q34)(Q35), 페닐기, 펜탈레닐기, 인데닐기， 나프틸기， 아줄레닐기, 헵탈레닐기, 인다세닐기, 아세나프틸기, 플루오레닐기, 스파이로-플루오레닐기， 벤조플루오레닐기， 디벤조플루오레닐기, 페날레닐기， 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기， 파이레닐기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, ^ -0 alkyl group, dC 20 alkoxy group, -Si (Q 33 ) (Q 34 ) (Q 35 ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl Group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, Pyrenyl,
크라이세닐기, 나프타세닐기， 피세닐기， 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기， 루비세닐기, 코로네닐기， 오발레닐기, 피를일기， 티오페닐기， 퓨라닐기, 이미다졸일기, 피라졸일기， 티아졸일기, 이소티아졸일기, 옥사졸일기, 이속사졸일기, 피리디닐기, 피라지닐기, 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기， 프탈라지닐기, 나프티리디닐기， 퀴녹살리닐기, 퀴나졸리닐기, 시놀리닐기, 카바졸일기, 페난트리디닐， 아크리디닐， 페난트를리닐， 페나지닐， 벤조이미다졸일기， 벤조퓨라닐기， Crysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, nucleusenyl group, pentansenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, furanyl group, already Dazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, Indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenantridinyl, Acridinyl, phenanthlinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group,
벤조티오페닐기 , 이소벤조티아졸일기, 벤조옥사졸일기, 이소벤조옥사졸일기, 트리아졸일기, 테트라졸일기, 옥사디아졸일기， 트리아지닐기， 디벤조퓨라닐기, 디벤조티오페닐기， 벤조카바졸일기, 디벤조카바졸일기, 이미다조피리디닐기, 이미다조피리미디닐 및 비페닐기 중 적어도 하나로 치환된, 페닐기, 펜탈레닐기, 인데닐기， 나프틸기, 아즐레닐기, 헵탈레닐기, 인다세닐기， 아세나프틸기, Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Phenyl group, pentalenyl group, indenyl group, naphthyl group, azelenyl group, heptalenyl group, indyl substituted with at least one of a zolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl and biphenyl group Senyl, Acenaphthyl,
플루오레닐기， 스파이로-플루오레닐기, 벤조플루오레닐기, 디벤조플루오레닐기， 페날레닐기， 페난트레닐기, 안트라세닐기, 플루오란테닐기, 트리페닐레닐기, Fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group,
파이레닐기， 크라이세닐기, 나프타세닐기, 피세닐기， 페릴레닐기, 펜타페닐기, 핵사세닐기, 펜타세닐기, 루비세닐기, 코로네닐기, 오발레닐기, 피를일기， 티오페닐기， 퓨라닐기, 이미다졸일기， 피라졸일기, 티아졸일기, 이소티아졸일기, 옥사졸일기, 이속사졸일기, 피리디닐기, 피라지닐기, 피리미디닐기, 피리다지닐기， 이소인돌일기, 인돌일기, 인다졸일기， 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기, 프탈라지닐기, 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기， 시놀리닐기, 카바졸일기， 페난트리디닐， 아크리디닐, 페난트롤리닐, 페나지닐, 벤조이미다졸일기, 벤조퓨라닐기, 벤조티오페닐기 , 이소벤조티아졸일기, 벤조옥사졸일기, 이소벤조옥사졸일기， 트리아졸일기， 테트라졸일기, 옥사디아졸일기, 트리아지닐기， 디벤조퓨라닐기, 디벤조티오페닐기, 벤조카바졸일기， 디벤조카바졸일기, 이미다조피리디닐기 및 이미다조피리미디닐; 및 Pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, peryllenyl group, pentaphenyl group, nucleusenyl group, pentansenyl group, rubisenyl group, coronyl group, ovalenyl group, pyryl group, thiophenyl group, Furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indole Diary, indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenantri Dinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group , Oxadiazolyl group, triazinyl group, Benzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a piperidinyl group, and flutes already jopi imidazo pyrimidinyl; And
-Si(( )(Q4)(Q5) (단， 상기 R,3 내지 Ri6 및 및 ¾은 -Si(Q3)(Q4)(Q5)가 아님); 중에서 선택되고; -Si (() (Q 4 ) (Q 5 ), wherein R, 3 to Ri6 and ¾ are not -Si (Q 3 ) (Q 4 ) (Q 5 );
상기 Q3 내지 Q5 및 Q33 내지 Q35는 서로 독립적으로, 수소, d- o알킬기, Cr o알콕시기, 페닐기, 나프틸기, 안트라세닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, 크라이세닐기, 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 디벤조퓨라닐기， 디벤조티오페닐기， 피리디닐기, 피리미디닐기, 트리아지닐기， 퀴놀리닐기, 이소퀴놀리닐기， 퀴나졸리닐기 및 퀴녹살리닐기 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다. Q 3 to Q 5 and Q 33 to Q 35 are each independently hydrogen, d-oalkyl group, Cr oalkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, Chrysenyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, It may be selected from a quinazolinyl group and a quinoxalinyl group, but is not limited thereto.
예를 들어, 상기 제 1화합물은 하기 화학식 41 -1 내지 41 -12 중 하나로 표시되고, 상기 제 2화합물은 하기 화학식 61-1 내지 61-6 중 하나로 표시될 수 있다:
Figure imgf000049_0001
For example, the first compound may be represented by one of Formula 41 -1 to 41 -12. The second compound may be represented by one of Chemical Formulas 61-1 to 61-6:
Figure imgf000049_0001
화학식 41-1 화학식 41-2
Figure imgf000049_0002
Chemical Formula 41-1 Chemical Formula 41-2
Figure imgf000049_0002
화학식 41-5 화학식 41-6
Figure imgf000049_0003
Chemical Formula 41-5 Chemical Formula 41-6
Figure imgf000049_0003
Figure imgf000050_0001
Figure imgf000050_0001
Figure imgf000050_0002
Figure imgf000050_0002
화학식 61-3 화학식 61-4 Chemical Formula 61-3 Chemical Formula 61-4
Figure imgf000051_0001
Figure imgf000051_0001
： f학식 61-5 S학식 61-6  ： F (61-5) S (61-6)
상기 화학식 41-1 내지 41-12 및 61-1 내지 61-6 중 X41, X61, L4h L42, a41, a42, L6i,L62,a61,a62,R4i 내지 4， b41, b42, R61 내지 R64, b61,b62, R71 내지 R79 및 b79에 대한 설명은 본 명세서에 기재된 바를 참조한다. In Formulas 41-1 to 41-12 and 61-1 to 61-6, X 41 , X 61 , L 4h L 42 , a41, a42, L 6 i, L 62 , a61, a62, R 4i to 4 , b41, For descriptions of b42, R 61 to R 64 , b61, b62, R 71 to R 79 and b79, refer to what is described herein.
일 구현예에 따르면, 상기 화학식 41로 표시되는 제 1화합물은 하기 화합물 According to one embodiment, the first compound represented by Formula 41 is the following compound
A1 내지 A16 중 하나를 포함하고, 상기 화학식 61로 표시되는 제 2화합물은 하기 화합물 B1 내지 B4 중 하나를 포함할 수 있다: One of A1 to A16, and the second compound represented by Chemical Formula 61 may include one of the following compounds B1 to B4:
Figure imgf000052_0001
Figure imgf000052_0001
수 있다: <화학식 81> Can: <Formula 81>
Figure imgf000053_0001
Figure imgf000053_0001
상기 화학식 81 중,  In Formula 81,
M은 이리듐 (Ir), 백금 (Pt), 오스뮴 (Os), 티탄 (Ti), 지르코늄 (Zr), 하프늄 (Hf), 유로품 (Eu), 테르븀 (Tb) 및 를륨 (Tm) 중에서 선택되고;  M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), flow path product (Eu), terbium (Tb) and lium (Tm) ;
Y, 내지 Y4는 서로 독립적으로, 탄소 (C) 또는 질소 (Ν)이고; Y, to Y 4 are, independently of each other, carbon (C) or nitrogen (Ν);
^과 Υ2는 단일 결합 또는 이중 결합을 통하여 연결되어 있고 , Υ3와 Υ4는 단일 결합 또는 이중 결합을 통하여 연결되어 있고; ^ And Υ 2 are linked via a single bond or a double bond, and Υ 3 and Υ 4 are linked through a single bond or a double bond;
CY, 및 CY2는 서로 독립적으로， 벤젠, 나프탈렌, 플루오렌, CY, and CY 2 are independently of each other, benzene, naphthalene, fluorene,
스파이로 -플루오렌, 인덴, 피롤, 티오펜, 퓨란 (furan), 이미다졸, 피라졸, 티아졸, 이소티아졸, 옥사졸, 이속사졸 (isooxazole), 피리딘, 피라진, 피리미딘, 피리다진， 퀴놀린, 이소퀴놀린, 벤조퀴놀린, 퀴녹살린， 퀴나졸린, 카바졸, 벤조이미다졸, 벤조퓨란 (benzofumn), 벤조티오펜, 이소벤조티오펜, 벤조옥사졸， 이소벤조옥사졸, 트리아졸, 테트라졸, 옥사디아졸, 트리아진， 디벤조퓨란 (dibenzofuran) 및 디벤조티오펜 중에서 선택되고，。^과 CY2는 선택적으로 (optionally), 단일 결합 또는 유기 연결기 (organic linking group)를 통하여 서로 결합되고; Spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, Quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzooxazole, triazole, tetrazole , Oxadiazole, triazine, dibenzofuran and dibenzothiophene;. ^ And CY 2 are optionally bonded to each other through a single bond or an organic linking group. ;
R81 및 2는 서로 독립적으로， 수소， 중수소， -F, -CI, -Br, -I, 히드록실기， 시아노기, 니트로기, 아미노기, 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, -SF5, 치환 또는 비치환된 CrC60알킬기, 치환 또는 비치환된 C2-C60알케닐기, 치환 또는 비치환된 R 81 and 2 independently of each other, hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid Or salts thereof, sulfonic acid or salts thereof, phosphoric acid or salts thereof, -SF 5 , substituted or unsubstituted CrC 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted
C2-C60알키닐기, 치환 또는 비치환된 d- o알콕시기， 치환 또는 비치환된 C 2 -C 60 alkynyl group, substituted or unsubstituted d-oalkoxy group, substituted or unsubstituted
C3-C10시클로알킬기, 치환 또는 비치환된 C2-C10헤테로시클로알킬기， 치환 또는 비치환된 c3-c10시클로알케닐기, 치환 또는 비치환된 c2-c10헤테로시클로알케닐기, 치환 또는 비치환된 C6-C60아릴기, 치환 또는 비치환된 c6-c60아릴옥시기, 치환 또는 비치환된 C6-C60아릴티오기, 치환 또는 비치환된 C2-C60헤테로아릴기， 치환 또는 비치환된 1가 비 -방향족 축합다환 그룹, 치환 또는 비치환된 1가 비 -방향족 헤테로축합다환 그룹, -N(Q0(Q2), -Si(Q3)(Q4)(Q5) 및 -B(Q6)(Q7) 중에서 선택되고; C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, substituted or Unsubstituted c 3 -c 10 cycloalkenyl group, substituted or unsubstituted c 2 -c 10 heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted c 6 -c 60 Aryloxy group, substituted or unsubstituted C 6 -C 60 arylthio group, substituted or unsubstituted C 2 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted Monovalent non-aromatic heterocondensed polycyclic group, -N (Q0 (Q 2 ), -Si (Q 3 ) (Q 4 ) (Q 5 ) and -B (Q 6 ) (Q 7 );
a81 및 a82는 서로 독립적으로， 1 내지 5의 정수 중에서 선택되고;  a81 and a82 are each independently selected from an integer of 1 to 5;
n81은 0 내지 4의 정수 중에서 선택되고;  n81 is selected from an integer of 0 to 4;
n82는 1 , 2 또는 3이고;  n82 is 1, 2 or 3;
L81은 1가 유기 리간드 , 2가 유기 리간드 및 3가 유기 리간드 중에서 선택되고; L 81 is selected from monovalent organic ligand, divalent organic ligand and trivalent organic ligand;
상기 화학식 81 중 과 Y2 사이의 결합 및 Y3와 Υ4 사이의 결합은, 서로 독립적으로, 단일 결합 또는 이중 결합이다. In Formula 81, a bond between Y 2 and a bond between Y 3 and X 4 , independently of each other, are a single bond or a double bond.
상기 R81 및 R82에 대한 설명은 본 명세서 중
Figure imgf000054_0001
대한 설명을 참조한다. ' 상기 인광 도편트는 하기 화합물 PD1 내지 PD74 중 적어도 하나를 포함할 으나, 이에 한정되는 것은 아니다 (하기 화합물 PD1은 Ir(ppy)3임): Description of the R 81 and R 82 in the present specification
Figure imgf000054_0001
See description for it. "The phosphorescent dopyeon teuneun to, but include at least one of the compounds PD1 to PD74, but not limited to (a compound PD1 is Ir (ppy) 3 Im):
Figure imgf000054_0002
Figure imgf000054_0002
PD4 PD5 PD4 PD5
Figure imgf000055_0001
Figure imgf000055_0001
9i.ad ad emd
Figure imgf000055_0002
9i.ad ad emd
Figure imgf000055_0002
98ZTOO/SlOZaM/X3d 0C9.Cl/ST0Z OAV  98ZTOO / SlOZaM / X3d 0C9.Cl/ST0Z OAV
£
Figure imgf000056_0001
£
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000057_0001
PD43 PD44 PD45 PD43 PD44 PD45
Figure imgf000058_0001
Figure imgf000058_0001
98ZTOO/SlOia¾/X3d 0C9.Cl/ST0i OAV 98ZTOO / SlOia¾ / X3d 0C9.Cl/ST0i OAV
9S 9S
Figure imgf000059_0001
Figure imgf000059_0001
98ZTOO/SlOZaM/X3d 0C9.Cl/ST0Z OAV 98ZTOO / SlOZaM / X3d 0C9.Cl/ST0Z OAV
Figure imgf000060_0001
Figure imgf000060_0002
Figure imgf000060_0001
Figure imgf000060_0002
PD73 PD74  PD73 PD74
또는, 상기 인광 도펀트는 하기 PtOEP또는 화합물 PhGD를 포함할 수 있다:  Alternatively, the phosphorescent dopant may comprise the following PtOEP or compound PhGD:
Figure imgf000060_0003
Figure imgf000060_0003
PtOEP PhGD  PtOEP PhGD
상기 발광층이 호스트 및 도펀트를 포함할 경우， 도편트의 함량은  When the light emitting layer includes a host and a dopant, the dopant content is
통상적으로 호스트 약 100 중량부를 기준으로 하여 약 0.01 내지 약 15 중량부의 범위에서 선택될 수 있으며, 이에 한정되는 것은 아니다. Typically, it may be selected from about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
상기 발광층의 두께는 약 100A 내지 약 1000A, 예를 들면 약 200A 내지 약 600 A일 수 있다. 상기 발광층의 두께가 전술한 바와 같은 범위를 만족할 경우, 실질적인 구동 전압 상승없이 우수한 발광 특성을 나타낼 수 있다.  The light emitting layer may have a thickness of about 100A to about 1000A, for example, about 200A to about 600A. When the thickness of the light emitting layer satisfies the aforementioned range, the light emitting layer may exhibit excellent light emission characteristics without a substantial increase in driving voltage.
다음으로 발광층 상부에 전자 수송 영역이 배치된다.  Next, an electron transport region is disposed on the emission layer.
전자 수송 영역은 정공 저지층, 전자 수송층 및 전자 주입층 중 적어도 하나를 포함할 수 있다.  The electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
예를 들어， 전자 수송 영역은 정공 저지층 /전자 수송층 /전자 주입층 또는 전자 수송층 /전자 주입층의 구조를 가질 수 있으나， 이에 한정되는 것은 아니다. 상기 전자 수송층은 단일층 또는 2 이상의 서로 다른 물질을 포함한 다층 구조를 가질 수 있다ᅳ For example, the electron transport region may be a hole blocking layer / electron transport layer / electron injection layer or It may have a structure of an electron transport layer / electron injection layer, but is not limited thereto. The electron transport layer may have a single layer or a multilayer structure including two or more different materials.
상기 전자 수송 영역의 정공 저지층, 전자 수송층 및 전자 주입층의 형성 조건은 정공 주입층의 형성 조건을 참조한다.  The formation conditions of the hole blocking layer, the electron transport layer, and the electron injection layer of the electron transport region may be referred to the formation conditions of the hole injection layer.
상기 전자 수송 영역이 정공 저지층을 포함할 경우, 상기 정공 저지층은 예를 들면， 하기 BCP, Bphen 및 BAlq 중 적어도 하나를 포함할 수 있으나, 이에 한정되는 것은 아니다.  When the electron transport region includes the hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq, but is not limited thereto.
Figure imgf000061_0001
Figure imgf000061_0001
BCP Bphen  BCP Bphen
상기 정공 저지층의 두께는 약 20 A 내지 약 1000 A, 예를 들면 약 30 A 내지 약 300A일 수 있다. 상기 정공저지층의 두께가 전술한 바와 같은 범위를 만족할 경우, 실질적인 구동 전압 상승없이 우수한 정공 저지 특성을 얻올 수 있다. 상기 전자 수송층은 상기 BCP, Bphen 및 하기 Alq3, Balq, TAZ 및 NTAZ 중 적어도 를 더 포함할 수 있다. The hole blocking layer may have a thickness of about 20 A to about 1000 A, for example, about 30 A to about 300 A. When the thickness of the hole blocking layer satisfies the aforementioned range, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage. The electron transport layer may further include at least one of BCP, Bphen and Alq 3 , Balq, TAZ, and NTAZ.
Figure imgf000061_0002
Figure imgf000061_0002
NTAZ  NTAZ
또는, 상기 전자 수송층은 하기 화합물 ET1 및 ET2 중 적어도 하나를 포함할 수 있으나, 이에 한정되는 것은 아니다. Alternatively, the electron transport layer may include at least one of the following compounds ET1 and ET2, but is not limited thereto.
Figure imgf000062_0001
Figure imgf000062_0001
상기 전자 수송층의 두께는 약 100A 내지 약 1000A, 예를 들면 약 150A 내지 약 500A일 수 있다. 상기 전자 수송층의 두께가 전술한 바와 같은 범위를 만족할 경우, 실질적인 구동 전압 상승없이 만족스러운 정도의 전자 수송 특성을 얻을 수 있다. The electron transport layer may have a thickness of about 100A to about 1000A, for example, about 150A to about 500A . When the thickness of the electron transporting layer satisfies the aforementioned range, a satisfactory electron transporting characteristic can be obtained without a substantial increase in driving voltage.
상기 전자 수송층은 상술한 바와 같은 물질 외에, 금속 -함유 물질을 더 포함할 수 있다.  The electron transport layer may further include a metal-containing material, in addition to the materials described above.
상기 금속 -함유 물질은 Li 착체를 포함할 수 있다. 상기 Li 착체는, 예를 들면, 화합물 ET-D1 (리튬 퀴놀레이트， LiQ) 또는 ET-D2을 포함할 수 있다.  The metal-containing material may comprise a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or ET-D2.
Figure imgf000062_0002
Figure imgf000062_0002
또한 전자 수송 영역은, 제 2전극 (19)으로부터 전자의 주입올 용이하게 하는 전자 주입층 (EIL)을 포함할 수 있다.  The electron transport region may also include an electron injection layer (EIL) that facilitates injection of electrons from the second electrode 19.
상기 전자 주입층은， LiF, NaCl, CsF, Li20 및 BaO 중에성 선택된 적어도 하나를 포함할 수 있다. The electron injection layer may include at least one selected from among LiF, NaCl, CsF, Li 2 O, and BaO.
상기 전자 주입층의 두께는 약 1 A 내지 약 100A, 약 3 A 내지 약 90A일 수 있다. 상기 전자 주입층의 두께가 전술한 바와 같은 범위를 만족할 경우, 실질적인 구동 전압 상승없이 만족스러운 정도의 전자 주입 특성을 얻을 수 있다. 상기 유기층 (15) 상부로는 게 2전극 (19)이 구비되어 있다. 상기 게 2전극 (19)은 캐소드일 수 있다. 상기 제 2전극 (19)용 물질로는 상대적으로 낮은 일함수를 가지는 금속, 합금, 전기전도성 화합물 및 이들의 조합을 사용할 수 있다. 구체적인 예로서는 리튬 (Li), 마그네슘 (Mg), 알루미늄 (A1), 알루미늄 -리튬 (Al-Li), 칼슘 (Ca), 마그네슘 -인듐 (Mg-In), 마그네슘-은 (Mg-Ag) 등을 제 2전극 (19) 형성용 물질로 사용할 수 있다. 또는, 전면 발광 소자를 얻기 위하여 ΠΌ, ΙΖΟ를 이용하여 투과형 게 2전극 (19)을 형성할 수 있는 등, 다양한 변형이 가능하다. The electron injection layer may have a thickness of about 1 A to about 100 A, about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the aforementioned range, a satisfactory electron injection characteristic may be obtained without a substantial increase in driving voltage. Crab electrodes 19 are provided on the organic layer 15. The crab second electrode 19 may be a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound having a relatively low work function, or a combination thereof may be used. Concrete Examples include lithium (Li), magnesium (Mg), aluminum (A1), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. It can be used as a material for forming the two-electrode 19. Alternatively, various modifications are possible, such as the transmissive crab 2 electrode 19 can be formed using πΌ, ΙΖΟ to obtain a front light emitting element.
이상, 상기 유기 발광 소자를 도 1을 참조하여 설명하였으나, 이에 한정되는 것은 아니다.  The organic light emitting device has been described above with reference to FIG. 1, but is not limited thereto.
본 명세서 중 CrC60알킬기는 탄소수 1 내지 60의 선형 또는 분지형 지방족 탄화수소 1가 (monovalent) 그룹을 의미하며, 구체적인 예에는, 메틸기 , 에틸기 , 프로필기, 이소부틸기, sec-부틸기, ter-부틸기, 펜틸기, iso-아밀기, 핵실기 등이 포함된다. 본 명세서 중 C!- o알킬렌기는 상기 d- o알킬기와 동일한 구조를 갖는 2가 (divalent) 그룹을 의미한다. In the present specification, the CrC 60 alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include methyl group, ethyl group, propyl group, isobutyl group, sec -butyl group, ter − Butyl group, pentyl group, iso-amyl group, nuclear chamber group and the like. In the present specification C ! oalkylene group means a divalent group having the same structure as said d-oalkyl group.
본 명세서 중 CrC60알콕시기는 -OA101 (여기서 , A101은 상기 d- o알킬기임)의 화학식을 갖는 1가 그룹올 의미하며, 이의 구체적인 예에는, 메톡시기， 에록시기, 이소프로필옥시기 등이 포함된다. As used herein, a CrC 60 alkoxy group refers to a monovalent group having a chemical formula of —OA 101 (wherein A 101 is the d-oalkyl group), and specific examples thereof include a methoxy group, an hydroxy group, an isopropyloxy group, and the like. This includes.
본 명세서 중 C2-C60알케닐기는 상기 C2-C60알킬기의 중간 또는 말단에 하나 이상의 탄소 이중 결합을 포함한 구조를 가지며， 이의 구체적인 예에는， 에테닐기， 프로페닐기, 부테닐기 등이 포함된다. 본 명세서 중 c2-c60알케닐렌기는 상기In the present specification, the C 2 -C 60 alkenyl group has a structure including at least one carbon double bond in the middle or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include an ethenyl group, propenyl group, butenyl group, and the like. do. In the present specification, the c 2 -c 60 alkenylene group is
C2-C60알케닐기와 동일한 구조를 갖는 2가 그룹을 의미한다. A divalent group having the same structure as a C 2 -C 60 alkenyl group.
본 명세서 중 C2-C60알키닐기는 상기 C2-C60알킬기의 증간 또는 말단에 하나 이상의 탄소 삼중 결합올 포함한 구조를 가지며, 이의 구체적인 예에는, In the present specification, the C 2 -C 60 alkynyl group has a structure including one or more carbon triple bonds at the intermediate or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include:
에티닐기 (ethynyl), 프로피닐기 (propynyl), 등이 포함된다. 본 명세서 중 Ethynyl, propynyl, and the like. Of the present specification
C2-C60알키닐렌기는 상기 C2-C60알키닐기와 동일한 구조를 갖는 2가 그룹을 의미한다. C 2 -C 60 alkynylene group refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.
본 명세서 중 C3-C10시클로알킬기는 탄소수 3 내지 10의 1가 포화 탄화수소 모노시클릭 그룹을 의미하며, 이의 구체예는 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로핵실기, 시클로헵틸기 등을 포함한다. 본 명세서 중 As used herein, a C 3 -C 10 cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclonuxyl group and a cyclohep And a tilt group. Of the present specification
C3-C10시클로알킬렌기는 상기 C3-C10시클로알킬기와 동일한 구조를 갖는 2가 그룹을 의미한다. C 3 -C 10 cycloalkylene group means a divalent group having the same structure as the C 3 -C 10 cycloalkyl group.
본 명세서 중 C2-C10헤테로시클로알킬기는 Ν, Ο, Ρ 및 S 중에서 선택된 적어도 하나의 헤테로 원자를 고리 -형성 원자로서 포함한 탄소수 2 내지 10의 1가 모노시클릭 그룹을 의미하며, 이의 구체예는 테트라히드로퓨라닐기 (tetmhydrofuranyl), 테트라히드로티오페닐기 등을 포함한다. 본 명세서 중 C 2 -C 10 heterocycloalkyl group in the present specification includes a monovalent having 2 to 10 carbon atoms containing at least one hetero atom selected from Ν, Ο, Ρ, and S as a ring-forming atom. Monocyclic group, specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group and the like. Of the present specification
C2-C10해테로시클로알킬렌기는 상기 C2-C10해테로시클로알킬기와 동일한 구조를 갖는 2가 그룹을 의미한다. C 2 -C 10 heterocycloalkylene group means a divalent group having the same structure as the C 2 -C 10 heterocycloalkyl group.
본 명세서 중 C3-C10시클로알케닐기는 탄소수 3 내지 10의 1가 모노시클릭 그룹으로서, 고리 내에 적어도 하나의 이중 결합을 가지나, 방향족성 (aromacity)을 갖지 않는 그룹을 의미하며, 이의 구체예는 시클로펜테닐기, 시클로핵세닐기， 시클로헵테닐기 등을 포함한다. 본 명세서 중 C3-C10시클로알케닐렌기는 상기 As used herein, a C 3 -C 10 cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one double bond in a ring, but having no aromacity, and specific examples thereof Examples include a cyclopentenyl group, a cyclonuxenyl group, a cycloheptenyl group, and the like. In the present specification, the C 3 -C 10 cycloalkenylene group is
C3-C10시클로알케닐기와 동일한 구조를 갖는 2가 그룹을 의미한다. A divalent group having the same structure as a C 3 -C 10 cycloalkenyl group.
본 명세서 증 C2-C10헤테로시클로알케닐기는 Ν, Ο, Ρ 및 S 중에서 선택된 적어도 하나의 헤테로 원자를 고리 -형성 원자로서 포함한 탄소수 2 내지 10의 1가 모노시클릭 그룹으로서, 고리 내에 적어도 하나의 이중 결합을 갖는다. 상기 The C 2 -C 10 heterocycloalkenyl group of the present specification includes a C 2 -C 10 monovalent monocyclic group containing at least one hetero atom selected from Ν, Ο, Ρ, and S as a ring-forming atom, It has one double bond. remind
C2-C10헤테로시클로알케닐기의 구체예는, 2,3-히드로퓨라닐기， 2,3-히드로티오페닐기 등을 포함한다. 본 명세서 중 C2-C10헤테로시클로알케닐렌기는 상기 Specific examples of the C 2 -C 10 heterocycloalkenyl group include a 2,3-hydrofuranyl group, a 2,3-hydrothiophenyl group, and the like. In the present specification, the C 2 -C 10 heterocycloalkenylene group is
C2-C10헤테로시클로알케닐기와 동일한 구조를 갖는 2가 그룹을 의미한다. A divalent group having the same structure as a C 2 -C 10 heterocycloalkenyl group is meant.
본 명세서 중 C6-C60아릴기는 탄소 원자수 6 내지 60개의 카보사이클릭 방향족 시스템을 갖는 1가 (monovalent) 그룹을 의미하며 , C6-C60아릴렌기는 탄소 원자수 6 내지 60개의 카보사이클릭 방향족 시스템을 갖는 2가 (divalent) 그룹을 의미한다. 상기 C6-C60아릴기의 구체예는, 페닐기, 나프틸기， 안트라세닐기, As used herein, a C 6 -C 60 aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C 6 -C 60 arylene group refers to a carbo having 6 to 60 carbon atoms By divalent group having a cyclic aromatic system is meant. Specific examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group,
페난트레닐기, 파이레닐기, 크라이세닐기 등을 포함한다. 상기 C6-C60아릴기 및 Phenanthrenyl groups, pyrenyl groups, chrysenyl groups and the like. The C 6 -C 60 aryl group and
C6-C60아릴렌기가 2 이상의 고리를 포함할 경우, 2 이상의 고리들은 서로 융합될 수 있다. If the C 6 -C 60 arylene group comprises two or more rings, the two or more rings may be fused to each other.
본 명세서 중 C2-C60헤테로아릴기는 Ν, Ο, Ρ 및 S 중에서 선택된 적어도 하나의 헤테로 원자를 고리 -형성 원자로서 포함하고 탄소수 2 내지 60개의 In the present specification, the C 2 -C 60 heteroaryl group includes at least one hetero atom selected from Ν, Ο, Ρ, and S as a ring-forming atom and has 2 to 60 carbon atoms.
카보사이클릭 방향족 시스템을 갖는 1가 그룹을 의미하고, C2-C60헤테로아릴렌기는 N, Ο, Ρ 및 S 중에서 선택된 적어도 하나의 헤테로 원자를 고리 -형성 원자로서 A monovalent group having a carbocyclic aromatic system, wherein the C 2 -C 60 heteroarylene group represents at least one hetero atom selected from N, O, Ρ and S as a ring-forming atom
포함하고 탄소수 2 내지 60개의 카보사이클릭 방향족 시스템을 갖는 2가 그룹을 의미한다. 상기 C2-C60헤테로아릴기의 구체예는, 피리디닐기, 피리미디닐기, 피라지닐기， 피리다지닐기, 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기 등을 Divalent group containing a carbocyclic aromatic system having 2 to 60 carbon atoms. Specific examples of the C 2 -C 60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like.
포함한다. 상기 C2-C60헤테로아릴기 및 C2-C60헤테로아릴렌기가 2 이상의 고리를 포함할 경우, 2 이상의 고리들은 서로 융합될 수 있다. Include. The C 2 -C 60 heteroaryl group and C 2 -C 60 heteroarylene group may be a ring of two or more If included, two or more rings may be fused to each other.
본 명세서 중 C6-C60아릴옥시기는 -OA102(여기서，ᅀ102는 상기 In the present specification, the C 6 -C 60 aryloxy group is —OA 102 (wherein 102 is
C6-C60아릴기임)를 가리키고, 상기 C6-C60아릴티오기 (arylthio)는 -SA103(여기서， A103은 상기 C6-C60아릴기기임)를 가리킨다. C 6 -C 60 aryl group, point a), the C 6 -C 60 arylthio group (arylthio) refers to -SA 103 (wherein, A 103 is being the C 6 -C 60 aryl device).
본 명세서 중 1가 비-방향족 축합다환 그룹 (non-aromatic condensed poly cyclic group)은 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함 (예를 들어, 탄소수는 8 내지 60일 수 있음)하고, 분자 전체가  As used herein, a monovalent non-aromatic condensed poly cyclic group includes two or more rings condensed with each other and includes only carbon as a ring forming atom (for example, carbon number may be 8 to 60). ), And the whole molecule
비 -방향족성 (non-aromacity)를 갖는 1가 그룹을 의미한다. 상기 비-방향족 축합다환 그룹의 구체예는 플루오레닐기 등을 포함한다. 본 명세서 중 2가 비-방향족 축합다환 그룹은 상기 1가 비-방향족 축합다환 그룹과 동일한 구조를 갖는 2가 그룹을 의미한다. Non-it means a monovalent group having a - (aromac non ity) aromaticity. Specific examples of the non-aromatic condensed polycyclic group include fluorenyl groups and the like. As used herein, the divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
본 명세서 중 1가 비-방향족 해테로축합다환 그룹 (non-aromatic condensed heteropolycyclic group)은 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소 (예를 들어, 탄소수는 2 내지 60일 수 있음) 외에 Ν, Ο, Ρ 및 S 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성 (non-aromacity)를 갖는 1가 그룹을 의미한다. 상기 1가 비-방향족 헤테로축합다환 그룹은， 카바졸일기 등을 포함한다. 본 명세서 중 2가 비-방향족 해테로축합다환 그룹은 상기 1가 비-방향족  As used herein, a monovalent non-aromatic condensed heteropolycyclic group includes two or more rings condensed with each other and carbon as a ring forming atom (for example, carbon number may be 2 to 60). In addition, it means a monovalent group containing a hetero atom selected from Ν, Ο, Ρ and S, and the whole molecule has a non-aromacity. The monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group and the like. As used herein, the divalent non-aromatic heterocondensed polycyclic group is a monovalent non-aromatic polyaromatic group.
헤테로축합다환 그룹과 동일한 구조를 갖는 2가 그룹을 의미한다. It means a divalent group having the same structure as the heterofused polycyclic group.
본 명세서 중 상기 치환된 -C60알킬렌기， 치환된 C2-C60알케닐렌기, 치환된 C2-C60알키닐렌기, 치환된 C3-C10시클로알킬렌기, 치환된 C2-C10해테로시클로알킬렌기， 치환된 C3-C10시클로알케닐렌기, 치환된 C2-C10헤테로시클로알케닐렌기, 치환된 In the present specification, the substituted -C 60 alkylene group, substituted C 2 -C 60 alkenylene group, substituted C 2 -C 60 alkynylene group, substituted C 3 -C 10 cycloalkylene group, substituted C 2- C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 2 -C 10 heterocycloalkenylene group, substituted
C6-C60아릴렌기, 치환된 C2-C60헤테로아릴렌기, 치환된 2가 비-방향족 축합다환 그룹, 치환된 2가 비-방향족 헤테로축합다환 그룹, 치환된 C!- o알킬기, 치환된 C 6 -C 60 arylene group, substituted C 2 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted C! -Oalkyl group, Substituted
C2-C60알케닐기, 치환된 C2-C60알키닐기, 치환된 C3-C10시클로알킬기, 치환된 C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 3 -C 10 cycloalkyl group, substituted
C2-Cl 0헤테로시클로알킬기, 치환된 C3-C10시클로알케닐기， 치환된 C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted
C2-C10헤테로시클로알케닐기， 치환된 C6-C60아릴기, 치환된 C6-C60아릴옥시기, 치환된 c6-c60아릴티오기, 치환된 c2-c60헤테로아릴기, 치환된 1가 비-방향족 축합다환 그룹 및 치환된 1가 비-방향족 헤테로축합다환 그룹의 적어도 하나의 치환기는, C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted c 6 -c 60 arylthio group, substituted c 2 -c 60 hetero At least one substituent of the aryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed polycyclic group,
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기， 아미노기 , 아미디노기 , 히드라진기， 히드라존기, 카르복실산기 또는 이의 염, .술폰산기 또는 이의 염, 인산기 또는 이의 염, d-C6o알킬기， C2-C60알케닐기， C2-C60알키닐기 및 d- o알콕시기; 중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기， 아미노기， 아미디노기 , 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염, C3-C10시클로알킬기, C2-C10해테로시클로알킬기， Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof . Sulfonic acid groups or salts thereof, Phosphoric acid groups or salts thereof, dC 6 oalkyl groups, C 2 -C 60 alkenyl groups, C 2 -C 60 alkynyl groups and d-oalkoxy groups; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group,
C3-C10시클로알케닐기， C2-C10해테로시클로알케닐기， C6-C60아릴기, C6- 0아릴옥시기， C6-C60아릴티오기, C2-C60헤테로아릴기， 1가 비-방향족 축합다환 그룹， 1가 비-방향족 해테로축합다환 그룹, -N(Q„)(Q12), -Si(Q13)(Q14)(Q15) 및 -B(Q16)(Q17) 중 적어도 하나로 치환된, C ^o알킬기， C2-C60알케닐기, C2-C60알키닐기 및 d- o알콕시기;C 3 -C 10 cycloalkenyl group, C 2 -C 10 year Tero cycloalkenyl group, C 6 -C 60 aryl group, C 60 aryloxy, C 6 -C 60 aryl come tea, C 2 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed polycyclic groups, -N (Q ') (Q 12 ), -Si (Q 13 ) (Q 14 ) (Q 15 ) and A C ^ oalkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group and a d-oalkoxy group, substituted with at least one of —B (Q 16 ) (Q 17 );
- 0시클로알킬기 , C2-C10해테로시클로알킬기 , C3-C10시클로알케닐기 , C2-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, - 0 cycloalkyl, C 2 -C 10 year Tero cycloalkyl, C 3 -C 10 cycloalkenyl group, C 2 -C 10 hetero cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group , C 6 -C 60 arylthio group,
C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹; C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기, 아미노기， 아미디노기, 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염, d-C60알킬기, C2-C60알케닐기, C2-C60알키닐기 및 d-C6o알콕시기, c3-c10시클로알킬기， C2-C,0헤테로시클로알킬기, c3-c10시클로알케닐기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, dC 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group and dC 6 oalkoxy group, c 3 -c 10 cycloalkyl group, C 2 -C, 0 heterocycloalkyl group, c 3 -c 10 cycloalkenyl group,
C2-Cl0헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, c6-c60아릴티오기, C 2 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, c 6 -c 60 arylthio group,
C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, -N(Q21)(Q22), -Si(Q23)(Q24)(Q25) 및 -B(Q26)(Q27) 중 적어도 하나로 치환된， C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q 21 ) (Q 22 ), -Si (Q 23 ) (Q 24 ) ( Q 25 ) and —B (Q 26 ) (Q 27 ) substituted with at least one of
C3-C10시클로알킬기, C2-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-C10해테로시클로알케닐기 , C6-C60아릴기 , C6-C60아릴옥시기 , C6-C60아릴티오기 , C 2 -C 10 year Tero cycloalkenyl group, C 6 -C 60 aryl group import, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea,
C2-C60해테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹; 및 C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group; And
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35) 및 -B(Q36)(Q37); 중에서 선택될 수 있다. -N (Q 31 ) (Q 32 ), -Si (Q 33 ) (Q 34 ) (Q 35 ) and -B (Q 36 ) (Q 37 ); It can be selected from.
또한, 본 명세서 중 Qi 내지 Q7, Qu 내지 Q17 및 Q3 1 내지 Q37은 서로 In addition, in the present specification, Qi to Q 7 , Qu to Q 17, and Q 3 1 to Q 37 are each other.
독립적으로, 수소, d- o알킬기, C2-C60알케닐기, C2-C60알키닐기， d- o알콕시기, Independently, hydrogen, d-oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, d-oalkoxy group,
C3-C10시클로알킬기, C2-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-C10해테로시클로알케닐기， C6-C60아릴기, C2-C6。헤테로아릴기, 1가 비-방향족 C 2 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 2 -C 6 .heteroaryl group, monovalent non-aromatic
축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹 중에서 선택될 수 있다. It may be selected from a condensed polycyclic group and a monovalent non-aromatic heterocondensed polycyclic group.
예를 들어, 상기 치환된 CrC60알킬렌기, 치환된 C2-C60알케닐렌기, 치환된 C2-C60알키닐렌기， 치환된 c3-c10시클로알킬렌기， 치환된 c2-c10헤테로시클로알킬렌기, 치환된 c3-c10시클로알케닐렌기， 치환된 c2-c10해테로시클로알케닐렌기， 치환된 For example, the substituted C r C 60 alkylene group, substituted C 2 -C 60 alkenylene group, substituted C 2 -C 60 alkynylene group, substituted c 3 -c 10 cycloalkylene group, substituted c 2 -c 10 heterocycloalkylene group, substituted c 3 -c 10 cycloalkenylene group, substituted c 2 -c 10 heterocycloalkenylene groups, substituted
C6-C60아릴렌기, 치환된 C2-C60헤테로아릴렌기， 치환된 2가 비-방향족 축합다환 그룹， 치환된 2가 비-방향족 해테로축합다환 그룹, 치환된 CrC60알킬기, 치환된 C 6 -C 60 arylene group, substituted C 2 -C 60 heteroarylene group, substituted bivalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic heterocondensed polycyclic group, substituted CrC 60 alkyl group, substituted Done
C2-C60알케닐기, 치환된 C2-C60알키닐기, 치환된 c3-c10시클로알킬기, 치환된 C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted c 3 -c 10 cycloalkyl group, substituted
C2-C10헤테로시클로알킬기， 치환된 C3-C10시클로알케닐기, 치환된 C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted
C2-C10헤테로시클로알케닐기, 치환된 c6-c60아릴기, 치환된 c6-c60아릴옥시기, 치환된C 2 -C 10 heterocycloalkenyl group, substituted c 6 -c 60 aryl group, substituted c 6 -c 60 aryloxy group, substituted
C6-C60아릴티오기, 치환된 C2-C60해테로아릴기, 치환된 1가 비-방향족 축합다환 그룹 및 치환된 1가 비-방향족 헤테로축합다환 그룹의 적어도 하나의 치환기는, At least one substituent of a C 6 -C 60 arylthio group, a substituted C 2 -C 60 heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic condensed polycyclic group,
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기 , 아미노기， 아미디노기 , 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염, 알킬기, C2-C60알케닐기, C2-C60알키닐기 및 d- o알콕시기; 중수소, -F, -CI, -Br, -1， 히드톡실기， 시아노기， 니트로기 , 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염, C3-C10시클로알킬기, C2-C10헤테로시클로알킬기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or salts, alkyl groups, C 2 -C 60 alkenyl groups, C 2 -C 60 alkynyl groups and d-oalkoxy groups thereof; Deuterium, -F, -CI, -Br, -1, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group,
C3-C10시클로알케닐기， C2-C10헤테로시클로알케닐기， C6-C60아릴기, C6-C60아릴옥시기， C6-C60아릴티오기， C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹, 1가 비-방향족 해테로축합다환 그룹,
Figure imgf000067_0001
및 -B(Q16)(Q17) 중 적어도 하나로 치환된, Ci- o알킬기, C2-C60알케닐기, C2-C60알키닐기 및 d- o알콕시기; C 3 -C 10 cycloalkenyl group, C 2 -C 10 hetero cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 2 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group,
Figure imgf000067_0001
And Ci-oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group and d-oalkoxy group, substituted with at least one of -B (Q 16 ) (Q 17 );
시클로펜틸기, 시클로핵실기, 시클로헵틸기， 시클로옥틸기, 시클로펜테닐기, 시클로헵세닐기, 시클로헵테닐기, 페닐기, 나프틸기, 안트라세닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, 카바졸일기, 벤조카바졸일기， 디벤조카바졸일기, 피리디닐기, 피리미디닐기, 피라지닐기, 피리다지닐기, 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 프탈라지닐기, 퀴녹살리닐기, 시놀리닐기 및 퀴나졸리닐기 중 적어도 하나로 치환된, 페닐기, 펜탈레닐기, 인데닐기， 나프틸기, 아즐레닐기, 헵탈레닐기, 인다세닐기, 아세나프틸기, 플루오레닐기, 스파이로-플루오레닐기, 페날레닐기, 페난트레닐기, 안트라세닐기, 플루오란트레닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기, 나프타세닐기, 피세닐기, 페릴레닐기, 펜타페닐기, 핵사세닐기， 피를일기, 이미다졸일기, 피라졸일기, 피리디닐기, 피라지닐기,  Cyclopentyl group, cyclonuclear group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, cyclohepsenyl group, cycloheptenyl group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, Carbazolyl, benzocarbazolyl, dibenzocarbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indaseyl group, acenaphthyl group, fluorenyl group, spy substituted with at least one of quinoxalinyl group, cynolinyl group and quinazolinyl group Rho-fluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group , Nucleated selenyl, bloodyl, tooth Group imidazole group, a pyrazole group, a pyridinyl group, pyrazinyl,
피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기， 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기, 프탈라지닐기， 나프티리디닐기， 퀴녹살리닐기, 퀴나졸리닐기， 시놀리닐기, 카바졸일기, 페난트리디닐기， 아크리디닐기， 페난트를리닐기, 페나지닐기， 벤조옥사졸일기， 벤조이미다졸일기, 푸라닐기， Pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, furinyl, Quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazoleyl, phenantridinyl, acridinyl, phenant Arylinyl group, phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group,
벤조푸라닐기, 티오페닐기， 벤조티오페닐기 , 티아졸일기， 이소티아졸일기, Benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group,
벤조티아졸일기, 이소옥사졸일기, 옥사졸일기, 트리아졸일기, 테트라졸일기, Benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group,
옥사디아졸일기, 트리아지닐기， 디벤조푸라닐기， 디벤조티오페닐기, 벤조카바졸일기, 디벤조카바졸일기, 이미다조피리미디닐기 및 이미다조피리디닐기; Oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산기 또는 이의 염, 술폰산기 또는 이의 염, 인산기 또는 이의 염, d- o알킬기, C2-C60알케닐기， C2-C60알키닐기 및 d-Cso알콕시기， ¾- 0시클로알킬기 , C2-C10헤테로시클로알킬기， C C10시클로알케닐기 , Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group Or a salt thereof, d-oalkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group and d-Csoalkoxy group, ¾- 0 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, CC 10 cycloalke Neil,
C2-C10헤테로시클로알케닐기 , C6-C60아릴기 , C6-C60아릴옥시기， C6-C60아릴티오기 , C 2 -C 10 hetero come cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl tea,
C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹 , 1가 비-방향족 헤테로축합다환. 그룹, -N(Q21)(Q22), -Si(Q23)(Q24)(Q25) 및 -B(Q26)(Q27) 중 적어도 하나로 치환된， 시클로펜틸기, 시클로핵실기, 시클로헵틸기， 시클로옥틸기, 시클로펜테닐기, C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group. Cyclopentyl group, cyclonuclear, substituted with at least one of the group, -N (Q 21 ) (Q 22 ), -Si (Q 23 ) (Q 24 ) (Q 25 ) and -B (Q 26 ) (Q 27 ) A real group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group,
시클로헵세닐기, 시클로헵테닐기, 페닐기, 나프틸기, 안트라세닐기, 파이레닐기, 페난쓰레닐기， 플루오레닐기， 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 피리디닐기, 피리 ^디닐기, 피라지닐기, 피리다지닐기, 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 프탈라지닐기, 퀴녹살리닐기, 시놀리닐기 및 퀴나졸리닐기 중 적어도 하나로 치환된, 페닐기， 펜탈레닐기, 인데닐기， 나프틸기, 아줄레닐기， 헵탈레닐기， 인다세닐기 , 아세나프틸기, 플루오레닐기 , 스파이로-플루오레닐기， 페날레닐기, 페난트레닐기, 안트라세닐기， 플루오란트레닐기, 트리페닐레닐기, 파이레닐기, 크라이세닐기, 나프타세닐기, 피세닐기， 페릴레닐기, 펜타페닐기, 핵사세닐기, 피를일기, 이미다졸일기, 피라졸일기, 피리디닐기, 피라지닐기, Cyclohepsenyl group, cycloheptenyl group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyri A phenyl group substituted with at least one of a denyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cynolinyl group, and a quinazolinyl group, Pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indasenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, penalenyl, phenanthrenyl, anthracenyl, fluoro Lanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, peryllenyl group, pentaphenyl group, nucleasenyl group, pyryl group, imidazolyl group, pyrazolyl group, pyridyl Nyl group, pyrazinyl group,
피리미디닐기, 피리다지닐기, 이소인돌일기， 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기， 벤조퀴놀리닐기, 프탈라지닐기, 나프티리디닐기, 퀴녹살리닐기， 퀴나졸리닐기, 시놀리닐기, 카바졸일기, 페난트리디닐기， 아크리디닐기， 페난트를리닐기, 페나지닐기, 벤조옥사졸일기, 벤조이미다졸일기, 푸라닐기, Pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, Quinazolinyl group, cynolinyl group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthryllinyl group, phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group,
벤조푸라닐기, 티오페닐기, 벤조티오페닐기, 티아졸일기， 이소티아졸일기, Benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group,
벤조티아졸일기, 이소옥사졸일기, 옥사졸일기, 트리아졸일기, 테트라졸일기， 옥사디아졸일기, 트리아지닐기, 디벤조푸라닐기, 디벤조티오페닐기, 벤조카바졸일기, 디벤조카바졸일기， 이미다조피리미디닐기 및 이미다조피리디닐기; 및 Benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, Oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group; And
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35) 및 -B(Q36)(Q37); 중에서 선택되고; -N (Q 31 ) (Q 32 ), -Si (Q 33 ) (Q 34 ) (Q 35 ) and -B (Q 36 ) (Q 37 ); Is selected from;
상기 내지 Q7, Qu 내지 Q17 및 Q31 내지 Q37은 서로 독립적으로, 수소, Ci- o알킬기, C2-C60알케닐기, C2-C60알키닐기, d-C60알콕시기, 시클로펜틸기， 시클로핵실기， 시클로헵틸기, 시클로옥틸기， 시클로펜테닐기， 시클로헵세닐기， 시클로헵테닐기， 페닐기, 나프틸기, 안트라세닐기， 파이레닐기, 페난쓰레닐기， 플루오레닐기, 카바졸일기， 벤조카바졸일기, 디벤조카바졸일기, 피리디닐기, 피리미디닐기， 피라지닐기, 피리다지닐기, 트리아지닐기, 퀴놀리닐기， 이소퀴놀리닐기 프탈라지닐기， 퀴녹살리닐기， 시놀리닐기 및 퀴나졸리닐기 중 적어도 하나로 치환된， 페닐기, 펜탈레닐기, 인데닐기, 나프틸기, 아줄레닐기, 헵탈레닐기， 인다세닐기, 아세나프틸기, 플루오레닐기， 스파이로-플루오레닐기, 페날레닐기, 페난트레닐기， 안트라세닐기， 플루오란트레닐기, 트리페닐레닐기, 파이레닐기， 크라이세닐기, 나프타세닐기, 피세닐기, 페릴레닐기, 펜타페닐기, 핵사세닐기, 피를일기, To Q 7 , Qu to Q 17 and Q 31 to Q 37 are each independently hydrogen, a Ci-oalkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a dC 60 alkoxy group, a cyclophene Tyl group, cyclonuclear group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, cyclohepsenyl group, cycloheptenyl group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl, dibenzocarbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl phthalazinyl, quinoxalinyl Phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indasenyl, acenaphthyl, fluorenyl, spiro-fluo substituted with at least one of cynolinyl and quinazolinyl Olenyl, Penalenyl, Phenanthrenyl, Anthra Senyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, peryllenyl group, pentaphenyl group, nucleasenyl group, piryl group,
이미다졸일기, 피라졸일기， 피리디닐기, 피라지닐기， 피리미디닐기, 피리다지닐기, 이소인돌일기, 인돌일기, 인다졸일기, 푸리닐기, 퀴놀리닐기, 이소퀴놀리닐기， 벤조퀴놀리닐기, 프탈라지닐기， 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기， 시놀리닐기， 카바졸일기, 페난트리디닐기， 아크리디닐기, 페난트롤리닐기, 페나지닐기 벤조옥사졸일기, 벤조이미다졸일기, 푸라닐기, 벤조푸라닐기, 티오페닐기, Imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoqui Nolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group benzoxazolyl group, benzo Imidazolyl group, furanyl group, benzofuranyl group, thiophenyl group,
벤조티오페닐기, 티아졸일기， 이소티아졸일기, 벤조티아졸일기, 이소옥사졸일기, 옥사졸일기, 트리아졸일기， 테트라졸일기, 옥사디아졸일기, 트리아지닐기， Benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group,
디벤조푸라닐기, 디벤조티오페닐기, 벤조카바졸일기, 디벤조카바졸일기， Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group,
이미다조피리미디닐기 및 이미다조피리디닐기 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다. It may be selected from an imidazopyrimidinyl group and an imidazopyridinyl group, but is not limited thereto.
이하， 합성예 및 실시예를 들어, 본 발명의 일 구현예를 따르는 화합물 및 유기 발광 소자에 대하여 보다 구체적으로 설명하나, 본 발명이 하기의 합성예 및 실시예로 한정되는 것은 아니다. 하기 합성예 중 "'Α' 대신 'B'를 사용하였다"란 표현 중 Έ，의 사용량과 'A，의 사용량은 몰당량 기준으로 동일하다.  Hereinafter, a compound and an organic light emitting device according to one embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following synthesis examples, "B" was used instead of "Α" "and the amount of Έ ， and the amount of 'A ， are the same on a molar equivalent basis.
또한, 실시예 및 합성예에서 사용된 출발물질 및 반웅물질은 특별한 언급이 없는 한, Sigma-Aldrich 社 또는 TCI 社에서 구입하였으며， 본원 우선일 이전에 용이하게 구입가능한 것이다. In addition, starting materials and reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI unless otherwise stated, and prior to the priority date of the present application. It can be easily purchased.
【발명의 실시를 위한 형태】  [Form for implementation of invention]
[실시예 j Example j
합성예 1 : 화합물 8의 합성  Synthesis Example 1 Synthesis of Compound 8
Figure imgf000070_0001
Figure imgf000070_0001
중간 A 중간제 B
Figure imgf000070_0002
Medium A Intermediate B
Figure imgf000070_0002
화합울 8  Harmony Wool 8
증간체 A (벤조 -1H-티에노 ,2-dl피리미딘 -2,4-디은ᅵ의 합성  Synthesis of Intermediate A (benzo-1H-thieno, 2-dlpyrimidine-2,4-diene
2000 mL 등근 플라스크에 3-아미노벤조-티오펜 -2-카르복실레이트 (47.5 g, 0.23 mol) 및 우레아 (79.4 g, 1.15 mol)의 흔합물을 200 °C에서 2 시간 동안 교반하였다. 고온의 반웅 흔합물을 상온으로 식힌 후, 수산화나트륨 용액에 붓고， 불순물올 여과하여 제거한 다음, 반응물을 산성화하여 (HC1, 2N), 수득한 침전물을 건조시켜 중간체 A을 수득하였다. (35 g, 75 %) A mixture of 3-aminobenzo-thiophene-2-carboxylate (47.5 g, 0.23 mol) and urea (79.4 g, 1.15 mol) was stirred in a 2000 mL equine flask at 200 ° C for 2 hours. The hot reaction mixture was cooled to room temperature, poured into a sodium hydroxide solution, filtered off with impurities, and then the reaction was acidified (HC1, 2N), and the precipitate obtained was dried to give intermediate A. ( 3 5 g, 75 %)
calcd. C,0H6N2O2S： C, 55.04; H, 2.77; N, 12.84; O, 14.66; S, 14.69; found： C, 55.01 ; H, 2.79; N, 12.81 ; O, 14.69; S, 14.70 calcd. C, 0 H 6 N 2 O 2 S: C, 55.04; H, 2.77; N, 12.84; 0, 14.66; S, 14.69; found: C, 55.01; H, 2.79; N, 12.81; 0, 14.69; S, 14.70
중간체 B (벤조 -2,4-디클로로-티에노 ,2-dl피리미딘)의 합성  Synthesis of Intermediate B (benzo-2,4-dichloro-thieno, 2-dlpyrimidine)
1000 mL 등근 플라스크에 중간체 A (벤조 -1H-티에노 [3,2-d]피리미딘 -2,4-디온) (35 g, 0.16 mol) 및 옥시염화인 (600 mL)의 흔합물을 환류하에 6 시간 동안  Reflux a mixture of intermediate A (benzo-1H-thieno [3,2-d] pyrimidine-2,4-dione) (35 g, 0.16 mol) and phosphorus oxychloride (600 mL) into a 1000 mL back flask For 6 hours under
교반하였다. 반응 흔합물을 상온으로 냉각시키고, 세게 교반하면서 얼음 /물에 부어, 침전물을 생성하였다. 이로부터 수득한 반응물을 여과하여, 중간체 Stirred. The reaction mixture was cooled to room temperature and poured into ice / water with vigorous stirring to form a precipitate. The reaction product obtained therefrom was filtered to give an intermediate
B (벤조 -2，4ᅳ디클로로-티에노 [3,2-d]피리미딘) (35 g, 85 %)를 수득하였다. 생성된 중간체 B의 원소 분석 결과 및 NMR 분석 결과는 하기와 같다. calcd. Ci0H4Cl2N2S： C, 47.08; H, 1.58; CI, 27.79; N, 10.98; S, 12.57; found： C, 47.03 ; H 1.61 ; CI, 27.81 ; N, 10.98; S, 12.60 B (benzo-2, 4-dichloro-eu-thieno [3, 2 -d] pyrimidine) to give (35 g, 85%). Elemental analysis results and NMR analysis results of the produced intermediate B are as follows. calcd. Ci 0 H 4 Cl 2 N 2 S: C, 47.08; H, 1.58; CI 27.79; N, 10.98; S, 12.57; found: C, 47.03; H 1.61; CI, 27.81; N, 10.98; S, 12.60
300 MHz (CDC13, ppm)： 7.63 (t, 1 H), 7.76 (t, 4H), 7.95 (d, 1H), 8.53 (d, 1H) 300 MHz (CDC1 3 , ppm): 7.63 (t, 1H), 7.76 (t, 4H), 7.95 (d, 1H), 8.53 (d, 1H)
중간체 C의 합성  Synthesis of Intermediate C
2000 mL 등근 플라스크에 중간체 B 3으0 g (1 Π.6 mmol), 페닐보로닉산 15.77 g 0 g (1 Π.6 mmol) of Intermediate B 3, 15.77 g of phenylboronic acid, in a 2000 mL isometric flask
(129.4 mmol), 탄산칼륨 40.63 g (294.0 mmol), Pd(PPh3)4 (Tetrakis(triphenylphosphine) palladium(O)) 6.79 g (5.88 mmol)을 1 ,4-다이옥산 600 mL, 물 200 mL에 넣어준 후， 질소 기류 하에서 12 시간 동안 가열하여 환류하였다. 이로부터 수득한 흔합물을 메탄올 1500 mL에 자하여 결정화된 고형분을 여과한 후, 모노클로로벤젠에 녹여 실리카겔 / 샐라이트로 여과하고, 유기 용매를 적당량 제거한 후, 메탄올로 재결정하여 중간체 C (20.94 g, 60%)를 수득하였다. 생성된 중간체 C의 원소 분석 결과는 하기와 같다. calcd. C16H9C1N2S： C, 64.75; H, 3.06; C1, 1 1.95; N, 9.44; S, 10.80; found： C, 64.77; H, 3.05; C1, 1 1.97; N, 9.47; S, 10.78 (129.4 mmol), 40.63 g (294.0 mmol) of potassium carbonate, 6.79 g (5.88 mmol) of Pd (PPh 3 ) 4 (Tetrakis (triphenylphosphine) palladium (O)) was added to 600 mL of 1,4-dioxane and 200 mL of water. After heating, the mixture was heated to reflux for 12 hours under a nitrogen stream. The resulting mixture was filtered into 1500 mL of methanol, and the crystallized solid was filtered. Then, the mixture was dissolved in monochlorobenzene and filtered through silica gel / salite. An appropriate amount of the organic solvent was removed, and the mixture was recrystallized from methanol to obtain Intermediate C (20.94 g). , 60%) was obtained. Elemental analysis of the resulting intermediate C is as follows. calcd. C 16 H 9 C1N 2 S: C, 64.75; H, 3.06; C1, 1 1.95; N, 9.44; S, 10.80; found: C, 64.77; H, 3.05; C1, 1 1.97; N, 9.47; S, 10.78
화합물 8의 합성  Synthesis of Compound 8
1000 mL 등근 플라스크에 중간체 C 20.0 g (67.39 mmol),  20.0 g (67.39 mmol) of intermediate C in a 1000 mL backbone flask,
9-페닐 -9Η,9Ή-3,3 '-바이카바졸 30.28 g (74.13 mmol), 소듐 t-부톡사이드 19.43 g (202.18 mmol), Pd(dba)2 6.2 g (6.7 mmol), 트리 t-부틸포스핀 6.54 mL (50% in를루엔)를 자일렌 400 mL 에 넣고 질소 기류 하에서 15 시간 동안 가열하여 환류하였다. 이로부터 수득한 흔합물을 메탄올 1000 mL에 가하여 결정화된 고형분을 여과한 후, 다이클로로벤젠에 녹여 실리카겔 /셀라이트로 여과하고, 유기 용매를 적당량 제거한 후, 메탄을로 재결정하여 화합물 8 (29.3 g, 65%의 수율)을 수득하였다. 생성된 화합물 8의 원소 분석 결과는 하기와 같다. 9-phenyl--9Η, 9Ή-3,3 '- bi-carbazol 30.28 g (74.13 mmol), sodium t- butoxide 19.43 g (202.18 mmol), Pd (dba) 2 6.2 g (6.7 mmol), tree t- 6.54 mL (50% inluene) of butylphosphine was placed in 400 mL of xylene and heated to reflux for 15 hours under a stream of nitrogen. The mixture obtained therefrom was added to 1000 mL of methanol, and the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel / celite, and an appropriate amount of an organic solvent was removed, followed by recrystallization with methane, to give compound 8 (29.3 g , 65% yield). Elemental analysis of the resulting compound 8 is as follows.
calcd. C46H28N4S： C, 82.61 ; H, 4.22; N, 8.38; S,4.79; found： C, 82.63 ; H, 4.21 ; N, 8.36;calcd. C 46 H 28 N 4 S: C, 82.61; H, 4. 22; N, 8.38; S, 4.79; found: C, 82.63; H, 4. 21; N, 8.36;
S, 4.80 합성예 2 : 화합물 21의 합성 S, 4.80. Synthesis Example 2: Synthesis of Compound 21
Figure imgf000071_0001
1000 mL 등근 플라스크에 중간체 10 14.5 g (70.87 mmol, (주) 유엠티， (주) 덕산테코피아 구입) , 9，-페닐 -9Η,9Ή-2,3'-바이카바졸 31.84 g (77.95 mmol), 소듐 t-부톡사이드 20.43 g (212.6 mmol), Pd(dba)2 6.49 g (7.09 mmol), 트리 t-부틸포스핀 6.88 mL (50% in 를루엔)를 자일렌 400 mL 에 넣고 질소 기류 하에서 15 시간 동안 가열하여 환류하였다. 이로부터 수득한 흔합물을 메탄을 1000 mL에 가하여 결정화된 고형분을 여과한 후, 다이클로로벤젠에 녹여 실리카겔 /샐라이트로
Figure imgf000071_0001
14.5 g of Intermediate 10 (70.87 mmol, purchased by Duksan Tecopia Co., Ltd.), 9, -phenyl -9Η, 9Ή-2,3'-bicarbazole 31.84 g (77.95 mmol) ), 20.43 g (212.6 mmol) of sodium t-butoxide, 6.49 g (7.09 mmol) of Pd (dba) 2 , 6.88 mL (50% in toluene) of tri t-butylphosphine were added to 400 mL of xylene, followed by a nitrogen stream. Heated to reflux under 15 hours. The mixture obtained therefrom was added to 1000 mL of methane, and the crystallized solid was filtered, and then dissolved in dichlorobenzene to give silica gel / salite.
여과하고， 유기 용매를 적당량 제거한 후, 메탄올로 재결정하여 화합물 21 (27.8 g, 68%의 수율)을 수득하였다. 생성된 화합물 21의 원소 분석 결과는 하기와 같다. calcd. C40H24N4O： C, 83.31 ; H, 4.20; N, 9.72; 0, 2.77; found： C, 83.30; H, 4.21 ; N, 9.76; 0, 2.79 After filtration, an appropriate amount of organic solvent was removed and then recrystallized with methanol to give compound 21 (27.8 g, 68% yield). Elemental analysis of the resulting compound 21 is as follows. calcd. C 40 H 24 N 4 O: C, 83.31; H, 4. 20; N, 9.72; 0, 2.77; found: C, 83.30; H, 4. 21; N, 9.76; 0, 2.79
300 MHz (CDC13, ppm)： 7.28-7.59 (m, 8H), 7.59-7.80 (m, 7H), 7.87 (dd, 1H), 8.13 (d, 1H), 8.19 (d, 1H), 8.26 (d, 1H), 8.39 (d, 1H), 8.57 (d, 1H), 8.93 (d, 1H), 9.12 (s, 1H), 9.34 (s, 1H) 합성예 3 : 화합물 26의 합성 300 MHz (CDC1 3 , ppm): 7.28-7.59 (m, 8H), 7.59-7.80 (m, 7H), 7.87 (dd, 1H), 8.13 (d, 1H), 8.19 (d, 1H), 8.26 ( d, 1H), 8.39 (d, 1H), 8.57 (d, 1H), 8.93 (d, 1H), 9.12 (s, 1H), 9.34 (s, 1H) Synthesis Example 3: Synthesis of Compound 26
Figure imgf000072_0001
Figure imgf000072_0001
1000 mL 등근 플라스크에 중간체 11 16.0 g (72.60 mmol, (주) 유엠티, (주) 덕산테코피아 구입)， 9'-([1 ,1，-바이페닐] -3-일) -9Η,9Ή-2,3'-바이카바졸 38.70 g (79.86 mmol), 소듐 t-부톡사이드 20.93 g (217.8 mmol), Pd(dba)2 6.65 g (7.26 mmol), 트리 t-부틸포스핀 7.04 mL (50% in 롤루엔)를 자일렌 400 mL 에 넣고 질소 기류 하에서 15 시간 동안 가열하여 환류하였다. 이로부터 수득한 흔합물을 메탄올 lOOO mL에 가하여 결정화된 고형분을 여과한 후, 다이클로로벤젠에 녹여 실리카겔 /셀라이트로 여과하고, 유기 용매를 적당량 제거한 후, 메탄올로 재결정하여 화합물 26 (2그 8 g, 68%의 수율)을 수득하였다. 생성된 화합물 26의 원소 분석 결과는 하기와 같다. calcd. C46H28N4S： C, 82.61 ; H, 4.22; N, 8.38; S, 4.79; found： C, 82.64; H, 4.24; N,16.0 g of Intermediate 11 (72.60 mmol, purchased by UMT Co., Ltd., Duksan Tecopia), 9 '-([1,1, -biphenyl] -3-yl) -9Η, 9 -2,3'-bicarbazole 38.70 g (79.86 mmol), sodium t-butoxide 20.93 g (217.8 mmol), Pd (dba) 2 6.65 g (7.26 mmol), trit-butylphosphine 7.04 mL (50 % in roluene) was added to 400 mL of xylene and heated to reflux for 15 hours under a stream of nitrogen. The obtained mixture was added to 100 mL of methanol, and the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel / celite, and an appropriate amount of an organic solvent was removed. g, yield 68%). Elemental analysis of the resulting compound 26 is as follows. calcd. C 46 H 28 N 4 S: C, 82.61; H, 4. 22; N, 8.38; S, 4.79; found: C, 82.64; H, 4. 24; N,
8.36; S, 4.78 합 4： 화합물 29의 합성 8.36; S, 4.78 Sum 4: Synthesis of Compound 29
Figure imgf000073_0001
Figure imgf000073_0001
중간체 D의 합성  Synthesis of Intermediate D
2000 mL 등근 플라스크에 중간체 1 1 30.0 g (135.94 mmol),  30.0 g (135.94 mmol) of intermediate 1 1 in a 2000 mL equipotent flask,
(3-클로로페닐)보로닉산 19.07 g (156.37 mmol), 탄산칼륨 37.58 g (271.89 mmol), Pd(PPh3)4 (Tetrakis(triphenylphosphine)palladium(O)) 7.85 g (6.80 mmol)을 1,4-다이옥산 800 mL, 물 250 mL에 넣어준 후, 질소 기류 하에서 12 시간 동안 가열하여 19.07 g (156.37 mmol) of (3-chlorophenyl) boronic acid, 37.58 g (271.89 mmol) of potassium carbonate, 7.85 g (6.80 mmol) of Pd (PPh 3 ) 4 (Tetrakis (triphenylphosphine) palladium (O)) Put 800 mL of dioxane and 250 mL of water, and heat under nitrogen stream for 12 hours.
환류하였다. 이로부터 수득한 흔합물을 메탄올 2000 mL에 가하여 결정화된 고형분을 여과한 후, 모노클로로벤젠에 녹여 실리카겔 / 셀라이트로 여과하고, 유기 용매를 적당량 제거한 후, 메탄을로 재결정하여 중간체 D (22.19 g, 55%)를 It was refluxed. The resulting mixture was added to 2000 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, an appropriate amount of organic solvent was removed, and the mixture was recrystallized with methane to give an intermediate D (22.19 g). , 55%)
수득하였다. Obtained.
화합물 29의 합성  Synthesis of Compound 29
1000 mL 등근 플라스크에 중간체 D 18.0 g (60.65 mmol),  18.0 g (60.65 mmol) of Intermediate D in a 1000 mL backbone flask,
9-페닐 -9Η,9Ή-3,3'-바이카바졸 27.25 g (66.72 mmol), 소듬 t-부톡사이드 17.49 g (181.96 mmol), Pd(dba)2 5.55 g (6.07 mmol), 트리 t-부틸포스핀 5.88 mL (50% in를루엔)를 자일렌 350 mL 에 넣고 질소 기류 하에서 15 시간 동안 가열하여 환류하였다. 9-phenyl-9,9, -3,3'-bicarbazole 27.25 g (66.72 mmol), bulge t-butoxide 17.49 g (181.96 mmol), Pd (dba) 2 5.55 g (6.07 mmol), tri-t- 5.88 mL (50% inluene) of butylphosphine was placed in 350 mL of xylene and heated to reflux for 15 hours under a stream of nitrogen.
이로부터 수득한 흔합물을 메탄올 1000 mL에 가하여 결정화된 고형분을 여과한 후, 다이클로로벤젠에 녹여 실라카겔 /샐라이트로 여과하고, 유기 용매를 적당량 제거한 후, 메탄올로 재결정하여 화합물 29 (23.1 g, 57%의 수율)을 수득하였다. 생성된 화합물 29의 원소 분석 결과는 하기와 같다. The mixture obtained therefrom was added to 1000 mL of methanol, and the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel / salite, an appropriate amount of an organic solvent was removed, and then recrystallized from methanol, Compound 29 (23.1 g , 57% yield). Elemental analysis of the resulting compound 29 is as follows.
calcd. C46H28N4S： C, 82.61 ; H, 4.22; N, 8.38; S, 4.79; found： C, 82.62; H, 4.21 ; N, 8.39; S, 4.77 평가예 1 : 합성된 화합물의 HOMO, LUMO 및 삼중항 (T1) 에너지 레벨 평가 표 1의 방법에 따라, 합성된 화합물의 HOMO, LUMO 및 T1 에너지 레벨을 평가하여 그 결과를 표 2에 나타내었다. calcd. C 46 H 28 N 4 S: C, 82.61; H, 4. 22; N, 8.38; S, 4.79; found: C, 82.62; H, 4. 21; N, 8.39; S, 4.77 Evaluation Example 1: Evaluation of HOMO, LUMO and Triplet (T1) Energy Levels of Synthesized Compounds According to the method of Table 1, the HOMO, LUMO and T1 energy levels of the synthesized compounds were evaluated and the results are shown in Table 2. Indicated.
【표 1】  Table 1
Figure imgf000074_0001
Figure imgf000074_0001
【표 2】 Table 2
화합물 No. HOMO(eV) LUMO(eV) T1 에너지 레벨 (eV) 화합물 6 -5.006 -2.016 2.409 화합물 8 -5.022 -1.927 2.489 화합물 17 -5.039 -1.859 2.568 화합물 18 -5.096 -1.864 2.687 화합물 19 -5.101 -1.898 2.671 화합물 20 -5.045 -1.857 2.569 Compound no. HOMO (eV) LUMO (eV) T1 Energy Level (eV) Compound 6 -5.006 -2.016 2.409 Compound 8 -5.022 -1.927 2.489 Compound 17 -5.039 -1.859 2.568 Compound 18 -5.096 -1.864 2.687 Compound 19 -5.101 -1.898 2.671 Compound 20 -5.045 -1.857 2.569
화합물 21 -5.103 -1.860 2.688  Compound 21 -5.103 -1.860 2.688
화합물 22 -4.924 -1.845 2.764  Compound 22 -4.924 -1.845 2.764
화합물 23 -5.058 -1.832 2.885  Compound 23 -5.058 -1.832 2.885
화합물 24 -5.057 -1.828 2.604  Compound 24 -5.057 -1.828 2.604
화합물 25 -5.117 -1.829 2.708  Compound 25 -5.117 -1.829 2.708
화합물 26 -5.131 -1.871 ' 2.690 Compound 26 -5.131 -1.871 ' 2.690
화합물 27 -5.061 -1.825 2.605  Compound 27 -5.061 -1.825 2.605
화합물 28 -5.125 -1.826 2.708  Compound 28 -5.125 -1.826 2.708
화합물 29 -4.938 -1.808 2.814  Compound 29 -4.938 -1.808 2.814
화합물 30 -5.067 -1.800 2.882 상기 표 2로부터, 합성된 화합물들은 삼중항 에너지가 높고 밴드갭이 넓어 유기 발광 소자용 재료로 사용하기에 적합한 전기적 특성을 가짐을 확인할 수 있다. 실시예 1  Compound 30 -5.067 -1.800 2.882 From Table 2, it can be seen that the synthesized compounds have high triplet energy and wide bandgap, and thus have suitable electrical properties for use as a material for an organic light emitting device. Example 1
1500 A 두께의 ITO (Indium tin oxide)전극 (제 1전극, 애노드)이 형성된 유리 기판을 50mm X 50mm X 0.5mm 크기로 잘라서 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄을 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 진공 증착기로 상기 기판을 이송하였다.  A glass substrate on which an indium tin oxide (ITO) electrode (first electrode, anode) having a thickness of 1500 A was cut to a size of 50 mm × 50 mm × 0.5 mm, and washed with ultrasonic water with distilled water. After washing the distilled water, ultrasonic washing with isopropyl alcohol, acetone, methane and the like, dried and transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes and then transferred the substrate by vacuum evaporator. .
상기 유리 기판의 ΠΌ 전극 상에 m-MTDATA를 증착 속도 1 A/sec로 진공 증착하여 600A 두께의 정공 주입층을 형성하고， 상기 정공 주입층 상에 상기  M-MTDATA was vacuum deposited at a deposition rate of 1 A / sec on a πΌ electrode of the glass substrate to form a hole injection layer having a thickness of 600 A, and on the hole injection layer
α-ΝΡΒ를 증착 속도 1 A/sec로 진공 증착하여 300A 두께의 정공 수송층을 α-ΝΡΒ was vacuum deposited at a deposition rate of 1 A / sec to form a hole transport layer having a thickness of 300 A.
형성하였다. 이어서, 상기 정공 수송층 상에 Ir(ppy)3(도편트) 및 화합물 8(호스트)를 각각 증착 속도 0.1 A/sec와 1 A/sec로 공증착하여 400 A 두께의 발광층을 형성하였다. 상기 발광층 상에 BAlq을 증착 속도 1 A/sec로 진공 증착하여 50 A 두께의 정공 저지층을 형성한 후， 상기 정공 저지층 상에 Alq3를 진공 증착하여 300A 두께의 전자 수송층을 형성하였다. 상기 전자 수송층 상에 LiF lOA (전자 주입층)과 A1 2000 A (캐소드)을 순차적으로 진공 증착하여, 유기 발광 소자를 제작하였다.
Figure imgf000076_0001
Formed. Subsequently, Ir (ppy) 3 (dope) and compound 8 (host) were co-deposited on the hole transport layer at a deposition rate of 0.1 A / sec and 1 A / sec, respectively, to form a light emitting layer having a thickness of 400 A. BAlq was vacuum deposited on the light emitting layer at a deposition rate of 1 A / sec to form a hole blocking layer having a thickness of 50 A, and then Alq 3 was vacuum deposited on the hole blocking layer to form an electron transport layer having a thickness of 300A. LiF10A (electron injection layer) and A1 2000 A (cathode) were sequentially vacuum deposited on the electron transport layer, thereby manufacturing an organic light emitting device.
Figure imgf000076_0001
BAIq Alq3 실시예 2 BAIq Alq 3 Example 2
발광충 형성시 호스트로서 화합물 8 대신 화합물 21을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여, 유기 발광 소자를 제작하였다. 실시예 3  An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 21, instead of Compound 8, was used as a host to form the LED. Example 3
발광층 형성시 호스트로서 화합물 8 대신 화합물 26을 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여, 유기 발광 소자를 제작하였다. 실시예 4  An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 26, instead of Compound 8, was used as a host to form the EML. Example 4
발광층 형성시 호스트로서 화합물 8 대신 화합물 29를 사용하였다는 점올 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여, 유기 발광 소자를 제작하였다. 비교예 1  An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 29, instead of Compound 8, was used as a host to form the EML. Comparative Example 1
발광층 형성시 호스트로서 화합물 9 대신 화합물 A를 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여, 유기 발광 소자를 제작하였다ᅳ  An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A, instead of Compound 9, was used as a host to form the EML.
<화합물 A> <Compound A>
Figure imgf000076_0002
비교예 2
Figure imgf000076_0002
Comparative Example 2
발광층 형성시 호스트로서 화합물 9 대신 화합물 B를 사용하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여, 유기 발광 소자를 제작하였다.  An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound B, instead of Compound 9, was used as a host to form the EML.
< B>
Figure imgf000077_0001
비교예 3 <B>
Figure imgf000077_0001
Comparative Example 3
발광층 형성시 호스트로서 화합물 9 대신 화합물 C를 사용하였다는 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여, 유기 발광 소자를 제작하였다.  An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound C, instead of Compound 9, was used as a host to form the EML.
< > <>
Figure imgf000077_0002
비교예 4
Figure imgf000077_0002
Comparative Example 4
발광층 형성시 호스트로서 화합물 9 대신 화합물 D를 사용하였다는 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여, 유기 발광 소자를 제작하였다. < > An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound D, instead of Compound 9, was used as a host to form the EML. <>
Figure imgf000078_0001
평가예 2: 유기 발광소자의 특성 평가
Figure imgf000078_0001
Evaluation Example 2: Evaluation of Characteristics of Organic Light-Emitting Device
상기 실시예 1 내지 4 의 유기 발광 소자에 대하여 구동 전압, 효율 및 휘도를 전류 전압계 (Keithley 2400), 휘도계 (Minolta Cs- 1000 A)를 이용하여 평가하였다. 측정된 휘도와 전류밀도 및 전압을 이용하여 전류 효율을 계산하였다. 그 결과는 하기 표 3과 같다.  The driving voltage, efficiency, and luminance of the organic light emitting diodes of Examples 1 to 4 were evaluated using a current voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000 A). The current efficiency was calculated using the measured brightness, current density and voltage. The results are shown in Table 3 below.
【표 3】  Table 3
Figure imgf000078_0002
상기 표 3에 따르면, 실시예 1 내지 4의 유기 발광 소자가 비교예 1 내^ 기 발광 소자보다 우수한 발광 효율을 가짐을 확인할 수 있다.
Figure imgf000078_0002
According to Table 3, it can be seen that the organic light emitting device of Examples 1 to 4 has better luminous efficiency than the light emitting device in Comparative Example 1.

Claims

【청구의 범위】  [Range of request]
【청구항 1】  [Claim 1]
하기 화학식 1로 표시되는 축합환 화합물:  A condensed cyclic compound represented by Formula 1 below:
< 1〉  <1>
Figure imgf000079_0001
Figure imgf000079_0001
<화학식 2C> < >  <Formula 2C> <>
Figure imgf000079_0002
Figure imgf000079_0002
<화학식 2E> <화학식 2F>  <Formula 2E> <Formula 2F>
Figure imgf000079_0003
Figure imgf000079_0003
상기 화학식들 중，  Of the above formula,
고리 Al l 및 고리 A12는 서로 독립적으로, 벤젠, 나프탈렌, 피리딘, 피리미딘, 피라진, 피리다진 및 트리아진 중에서 선택되고; Ring Al 1 and ring A 12 are independently of each other selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine and triazine;
Xu은 N-KL. aii-CR. bii], S, 0, S(=0), S(=0)2, C(=0), C(R13)(Rl4), Si(R13)(R14), P(R13), P(=0)(R13) 및 C=N(R,3) 중에서 선택되고;Xu is N-KL. a ii-CR. b ii], S, 0, S (= 0), S (= 0) 2 , C (= 0), C (R 13 ) (R l4 ), Si (R 13 ) (R 14 ), P (R 13 ), P (= 0) (R 13 ) and C═N (R, 3 );
2는 N-[(L12)al2-(R12)bl2], S, 0， S(=0), S(=0)2, C(=0), C(R15)(R16), Si(R15)(R16), P(R15), P(=0)(R15) 및 C=N(R15) 중에서 선택되고; 2 shows N - [(L 12) al2 - (R 12) bl2], S, 0, S (= 0), S (= 0) 2, C (= 0), C (R 15) (R 16) , Si (R 15 ) (R 16 ), P (R 15 ), P (= 0) (R 15 ) and C═N (R 15 );
X)은 N-tCL a CR b!], S, O, S(=0), S(=0)2, C(=0), Si(R5)(R6), P(R5), P(=0)(R5) 및 C=N(R5) 중에서 선택되고; X) is N-tCL a CR b! ], S, O, S (= 0), S (= 0) 2 , C (= 0), Si (R 5 ) (R 6 ), P (R 5 ), P (= 0) (R 5 ) And C = N (R 5 );
L, 내지 L4, Ln 및 Ll2는 서로 독립적으로, 치환 또는 비치환된 L, to L 4 , L n and L l2 are each independently a substituted or unsubstituted
C3-C10시클로알킬렌기, 치환 또는 비치환된 c2-c10헤테로시클로알킬렌기, 치환 또는 비치환된 C3-C10시클로알케닐렌기, 치환 또는 비치환된 C 3 -C 10 cycloalkylene group, substituted or unsubstituted c 2 -c 10 heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 cycloalkenylene group, substituted or unsubstituted
c2ᅳ c10헤테로시클로알케닐렌기, 치환 또는 비치환된 c6-c60아릴렌기, 치환 또는 비치환된 C2-C60헤테로아릴렌기， 치환 또는 비치환된 2가 비-방향족 축합다환 그룹 및 치환 또는 비치환된 2가 비-방향족 헤테로축합다환 그룹 중에서 선택되고; c 2 ᅳ c 10 heterocycloalkenylene group, substituted or unsubstituted c 6 -c 60 arylene group, substituted or unsubstituted C 2 -C 60 heteroarylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic ring Group and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group;
al 내지 a4, al l 및 al2는 서로 독립적으로， 0 내지 3의 정수 중에서 선택되고; al to a4, al l and al2 are each independently selected from an integer of 0 to 3;
R, 내지 ¾ 및 Ru 내지 R20은 서로 독립적으로, 수소， 중수소， -F (플루오로기), -C1 (클로로기), -Br (브로모기) , -1(아이오도기), 히드록실기, 시아노기 , 니트로기, 아미노기, 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염， 인산 또는 이의 염, 치환 또는 비치환된 C!- o알킬기, 치환 또는 비치환된 C2-C60알케닐기, 치환 또는 비치환된 C2-C60알키닐기, 치환 또는 비치환된 Cr o알콕시기, 치환 또는 비치환된 C3-C10시클로알킬기, 치환 또는 비치환된 R, to ¾ and R u to R 20 are each independently hydrogen, deuterium, -F (fluoro group), -C1 (chloro group), -Br (bromo group), -1 (iodo group), hydroxide Real group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C! -Oalkyl group, substituted or Unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted Cr o alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted Lit
C2-C10해테로시클로알킬기, 치환 또는 비치환된 C3-C10시클로알케닐기, 치환 또는 비치환된 C2-C10헤테로시클로알케닐기, 치환 또는 비치환된 C6-C60아릴기, 치환 또는 비치환된 C6-C60아릴옥시기， 치환 또는 비치환된 C6-C60아릴티오기, 치환 또는 비치환된 ¾- 해테로아릴기， 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹, -N(Q0(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7) 및 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되되, 상기 내지 ¾은, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아니고; C 2 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl Groups, substituted or unsubstituted C 6 -C 60 aryloxy groups, substituted or unsubstituted C 6 -C 60 arylthio groups, substituted or unsubstituted ¾-heteroaryl groups, substituted or unsubstituted monovalent ratios -Aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N (Q0 (Q 2 ), -Si (Q 3 ) (Q 4 ) (Q 5 ), -B (Q 6 (Q 7 ) and the group represented by the formula (2A) to the group represented by the formula (2F), wherein ¾ is not the group represented by the formula (2A) to the group represented by the formula (2F);
bl 내지 b4, bl l, bl2 및 M6 내지 b20은 서로 독립적으로 , 1 내지 3의 정수 중에서 선택되고;  bl to b4, bl 1, bl2 and M6 to b20 are each independently selected from an integer of 1 to 3;
i) 상기 화학식 1 중 Xu은 N-KLu^ Ru u]이고, 2은 N-[(L12)al2-(R12)bl2]이 아닐 경우, 상기 화학식 1 중 bl7개의 R17, bl l개의 Rl bl8개의 R18, bl9개의 R19 및 b20개의 R20 중 적어도 하나는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; of i) Formula 1 X u is N-KLu ^ Ru u], and 2 N - [(L 12) al2 - (R 12) , if not bl2], In the formula 1 bl7 of R 17, bl l R l bl8 R 18 , bl9 R 19 and at least one of b20 R 20 is selected from the group represented by Formula 2A to the group represented by Formula 2F;
ϋ) 상기 화학식 1 중 Xu은 N-KLu^ Ru u]가 아니고 , X12은 iii) Xu in Formula 1 is not N-KLu ^ Ru u], and X 12 is
N-[(L12)al2-(R12)bl2]일 경우, 상기 화학식 1 중 M7개의 R17, bl8개의 R18, bl9개의 R19, bl2개의 R12 및 b20개의 R20 중 적어도 하나는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; N - case - [(L 12) al2 ( R 12) bl2] days, M7 one R of the formula 1 17, bl8 of R 18, bl9 of R 19, at least one of the bl2 of R 12 and b20 of R 20 is Selected from the group represented by Formula 2A to the group represented by Formula 2F;
iii) 상기 화학식 1 중 Χ'.ι은 N-KLn^ R!Obu]이고， 2은 N-[(L12)al2-(R12)bl2]일 경우, 상기 화학식 1 중 M7개의 R17, bl l개의 Rn, bl8개의 R18, bl9개의 R19, bl2개의 R12 및 b20개의 R20 중 적어도 하나는, 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고; iii) Χ'.ι in Formula 1 is N-KLn ^ R ! O b u], and 2 N - [(L 12) al2 - (R 12) bl2], Formula M7 of R of 1 17, bl l of Rn, bl8 of R 18, bl9 of R 19 when, at least one of bl 2 R 12 and b 20 R 20 is selected from the group represented by Formula 2A to the group represented by Formula 2F;
상기 치환된 C3-C10시클로알킬렌기, 치환된 C2-C10헤테로시클로알킬렌기, 치환된 C3-C10시클로알케닐렌기, 치환된 C2-C10헤테로시클로알케닐렌기, 치환된 The substituted C 3 -C 10 cycloalkylene group, substituted C 2 -C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 2 -C 10 heterocycloalkenylene group, substitution Done
C6-C60아릴렌기, 치환된 C2-C60헤테로아릴렌기, 치환된 2가 비-방향족 축합다환 그룹, 치환된 2가 비-방향족 헤테로축합다환 그룹, 치환된 d-C 알킬기， 치환된 C 6 -C 60 arylene group, substituted C 2 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted dC alkyl group, substituted
C2-C60알케닐기, 치환된 C2-C60알키닐기, 치환된 - o알콕시기, 치환된 C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted -oalkoxy group, substituted
C3-C10시클로알킬기， 치환된 C2-C10헤테로시클로알킬기, 치환된 C C10시클로알케닐기, 치환된 C2-Cl0헤테로시클로알케닐기, 치환된 C6-C60아릴기, 치환된 C6-C60아릴옥시기, 치환된 C6-C60아릴티오기, 치환된 C2-C60헤테로아릴기, 치환된 1가 비-방향족 C 3 -C 10 cycloalkyl group, substituted C 2 -C 10 heterocycloalkyl group, substituted CC 10 cycloalkenyl group, substituted C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 2 -C 60 heteroaryl group, substituted monovalent non-aromatic
축합다환 그룹 및 치환된 1가 비-방향족 해테로축합다환 그룹의 치환기 중 적어도 하나는， At least one of the substituents of the condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group,
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기, 니트로기， 아미노기， 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염， 술폰산 또는 이의 염， 인산 또는 이의 염, d- o알킬기， C2-C60알케닐기, C2-C60알키닐기 및 -C6。알콕시기; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, d-oalkyl groups, C 2 -C 60 alkenyl groups, C 2 -C 60 alkynyl groups and -C 6 .alkoxy groups;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미노기， 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, C3-C10시클로알킬기, C2-C10헤테로시클로알킬기, C3-Cl0시클로알케닐기， C2-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, -NiQuXQu -S QnXQwXQ^ 및 -B(Q16)(Q,7) 중 적어도 하나로 치환된, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 2 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6- C 60 aryloxy group, C 6 -C 60 arylthio group, C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -NiQuXQu -S QnXQwXQ ^ and -B (Q 16 ) (Q, 7 ) substituted with at least one of
C o알킬기, C2-C60알케닐기, C2-C60알키닐기 및 - o알콕시기; C3-C10시클로알킬기, C2-C10헤테로시클로알킬기, C3-C10시클로알케닐기, A C o alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and an -oalkoxy group; C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-C10헤테로시클로알케닐기, C6-C60아릴기 , C6-C60아릴옥시기， C6-C60아릴티오기， C2-C60해테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹; C 2 -C 10 hetero cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come tea, C 2 -C 60 year for interrogating an aryl group, a monovalent non- Aromatic condensed polycyclic groups and monovalent non-aromatic heterocondensed polycyclic groups;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기 , 아미노기 , 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, d- o알킬기, C2-C60알케닐기, C2-C6( 키닐기, d- o알콕시기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, d-oalkyl groups, C 2 -C 60 alkenyl groups, C 2 -C 6 ( kinyl groups, d-oalkoxy groups,
C3-C10시클로알킬기, C2-C10해테로시클로알킬기, C3-C10시클로알케닐기, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
c2-c10헤테로시클로알케닐기 , c6-c60아릴기， c6-c60아릴옥시기 , c6-c60아릴티오기 ,c 2 -c 10 come hetero cycloalkenyl group, c 6 -c 60 aryl group, c 6 -c 60 aryloxy group, c 6 -c 60 aryl tea,
C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, -N(Q21)(Q22), -Si(Q23)(Q24XQ25) 및 -B(Q26)(Q27) 중 적어도 하나로 치환된, c3-c10시클로알킬기, c2-c10헤테로시클로알킬기, c3-c10시클로알케닐기, C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q 21 ) (Q 22 ), -Si (Q 23 ) (Q 24 XQ 25 C 3 -c 10 cycloalkyl group, c 2 -c 10 heterocycloalkyl group, c 3 -c 10 cycloalkenyl group, substituted with at least one of —B (Q 26 ) (Q 27 ),
c2ᅳ C10헤테로시클로알케닐기， C6-C60아릴기， C6-C60아릴옥시기, c6-c60아릴티오기， C2-C60헤테로아릴기， 1가 비-방향족 축합다환 그룹， 1가 비-방향족 헤테로축합다환 그룹; 및 eu c 2 C 10 alkenyl heterocycloalkyl, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, c 6 -c 60 aryl come tea, C 2 -C 60 heteroaryl group, a monovalent non-aromatic Condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups; And
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35) 및 -B(Q36)(Q37); 중에서 선택되고; -N (Q 31 ) (Q 32 ), -Si (Q 33 ) (Q 3 4) (Q 35 ) and -B (Q 36 ) (Q 37 ); Is selected from;
상기 Qi 내지 Q7, Qn 내지 QI 7, Q21 내지 Q27 및 Q31 내지 Q37은 서로 독립적으로, 수소, -C60알킬기, C2-C60알케닐기， C2-C60알키닐기, d- o알콕시기， C3-C10시클로알킬기， C2-C10해테로시클로알킬기 , C3-C10시클로알케닐기 , Qi to Q 7 , Qn to Q I 7 , Q 21 to Q 27 and Q 31 to Q 37 are each independently hydrogen, a -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group , d-oalkoxy group, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-Cl0헤테로시클로알케닐기, C6-C6。아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C2-C60해테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹 중에서 선택된다. C 2 -C l0 alkenyl heterocycloalkyl, C 6 -C 6. Aryl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 2 -C 60 year for interrogating an aryl group, a monovalent non- An aromatic condensed polycyclic group and a monovalent non-aromatic heterocondensed polycyclic group.
【청구항 2】  [Claim 2]
제 1항에 있어서,  The method of claim 1,
상기 L, 내지 L4, LU 및 L12는 서로 독립적으로, L, to L 4 , L U and L 12 are independently of each other,
페닐렌기 (phenylene), 펜탈레닐렌기 (pentalenylene), 인데닐렌기 (indenylene), 나프틸렌기 (naphthylene), 아줄레닐렌기 (azulenylene), 헵탈레닐렌기 (heptalenylene), 인다세닐렌기 (indacenylene), 아세나프틸렌기 (acenaphthylene),  Phenylene group, pentalenylene group, indenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, heptalenylene group, indaseylene group Naphthylene,
플루오레닐렌기 (fluorenylene), 스파이로-플루오레닐렌기, 페날레닐렌기 (phenalenylene), 페난트레닐렌기 (phenanthrenylene), 안트라세닐렌기 (anthracenylene), 플루오란트레닐렌기 (fluoranthrenylene), 트리페닐레닐렌기 (triphenylenylene), 파이레닐렌기 (pyrenylene), 크라이세닐렌기 (chrysenylene), Fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, phenanthrenylene group, anthracenylene group, Fluoranthrenylene group (fluoranthrenylene), triphenylenylene group (triphenylenylene), pyrenylene group (pyrenylene), chrysenylene group (chrysenylene),
나프타세닐렌기 (naphthacenylene), 피세닐렌기 (picenylene), 페릴레닐렌기 (perylenylene), 펜타페닐렌기 (pentaphenylene), 핵사세닐렌기 (hexacenylene), 피롤일렌기 (pyrrolylene), 이미다졸일렌기 (imidazolylene), 피라졸일렌기 (pyrazolylene), 피리디닐렌기 (pyridinylene), 피라지닐렌기 (pyrazinylene), 피리미디닐렌기 (pyrimidinylene), Naphthacenylene group, picenylene group, picenylene group, perylenylene group, pentaphenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group (imidazolylene) , Pyrazolylene group, pyridinylene group, pyrazinylene group, pyrazinylene group, pyrimidinylene group,
피리다지닐렌기 (pyridazinylene), 이소인돌일렌기 (isoindolylene), 인돌일렌기 (indolylene), 인다졸일렌기 (indazolylene), 푸리닐렌기 (purinylene), 퀴놀리닐렌기 (quinolinylene), 이소퀴놀리닐렌기 (isoquinolmylene), 벤조퀴놀리닐렌기 (benzoquinolinylene), Pyridazinylene, isoindoleylene, indolylene, indazole, inzolylene, purinylene, quinolinylene, isoquinolinylene (isoquinolmylene), benzoquinolinyl group (benzoquinolinylene),
프탈라지닐렌기 (phthalazinylene), 나프티리디닐렌기 (naphthyridinylene), Phthalazinylene, naphthyridinylene,
퀴녹살리닐렌기 (quinoxalinylene), 퀴나졸리닐렌기 (quinazolinylene), Quinoxalinylene group (quinoxalinylene), quinazolinylene group (quinazolinylene),
시놀리닐렌기 (cinnolinylene), 카바졸일렌기 (carbazolylene), Cynolinylene, carbazolylene,
페난트리디닐렌기 (phenanthridinylene), 아크리디닐렌기 (acridinylene), Phenanthridinylene group (phenanthridinylene), acridinylene group (acridinylene),
페난트를리닐렌기 (phenanthrolinylene), 페나지닐렌기 (phenazinylene), Phenanthrolinylene, phenazinylene,
벤조옥사졸일렌기 (benzooxazolylene), 벤조이미다졸일렌기 (benzoimidazolylene), 푸라닐렌기 (furanylene), 벤조푸라닐렌기 (benzofumnylene), 티오페닐렌기 (thiophenylene), 벤조티오페닐렌기 (benzothiophenylene), 티아졸일렌기 (thiazolylene), Benzoxazolylene group, benzoimidazolylene group, benzoimidazolylene group, furanylene group, furanylene group, benzofumnylene group, thiophenylene group, benzothiophenylene group, benzothiophenylene group, thiazolylene group (thiazolylene),
이소티아졸일렌기 (isothiazolylene), 벤조티아졸일렌기 (benzothiazolylene),  Isothiazolylene group, benzothiazolylene group,
이소옥사졸일렌기 (isoxazolylene), 옥사졸일렌기 (oxazolylene), 트리아졸일렌기， 테트라졸일렌기， 옥사디아졸일렌기 (oxadiazolylene), 트리아지닐렌기 (triazinylene), 디벤조푸라닐렌기 (dibenzofuranylene), 디벤조티오페닐렌기 (dibenzothiophenylene), 벤조카바졸일렌기， 디벤조카바졸일렌기，  Isoxazolylene, oxazolylene, triazolylene, tetrazoleylene, oxdiazolylene, triazinylene, dibenzofuranylene, dibenzofuranylene Phenylene group (dibenzothiophenylene), benzocarbazole ylene group, dibenzo carbazole ylene group,
이미다조피리미디닐렌기 (imidazopyrimidinylene) 및  Imidazopyrimidinylene and
이미다조피리디닐렌기 (imidazopyridinylene); 및  Imidazopyridinylene group; And
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기, 아미노기 , 아미디노기， 히드라진기, 히드라존기, 카르복실산기 또는 이의 염， 술폰산기 또는 이의 염' 인산기 또는 이의 염, -C2。알킬기， CrC20알콕시기, -C20아릴기, C2-C60헤테로아릴기, 1가 비-방향족 축합다환 그룹, 1가 비-방향족 해테로축합환 그룹，ᅳ Si(Q33)(Q34)(Q35) 중 적어도 하나로 치환된, 페닐렌기, 펜탈레닐렌기, 인데닐렌기, 나프틸렌기, Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof 'phosphate group Or salts thereof, -C 2 .alkyl group, CrC 20 alkoxy group, -C 20 aryl group, C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed cyclic group, Phenylene group, pentalenylene group, indenylene group, naphthylene group, substituted with at least one of Si (Q 33 ) (Q 34 ) (Q 35 ),
아줄레닐렌기， 헵탈레닐렌기， 인다세닐렌기, 아세나프틸렌기， 플루오레닐렌기, 스파이로 -플루오레닐렌기, 페날레닐렌기, 페난트레닐렌기, 안트라세닐렌기, 플루오란트레닐렌기, 트리페닐레닐렌기, 파이레닐렌기, 크라이세닐렌기, Azulenylene group, heptalenylene group, indasenylene group, acenaphthylene group, fluorenylene group, Spiro-fluorenylene group, phenenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, chrysenylene group,
나프타세닐렌기, 피세닐렌기, 페릴레닐렌기, 펜타페닐렌기, 핵사세닐렌기, 피롤일렌기， 이미다졸일렌기, 피라졸일렌기, 피리디닐렌기, 피라지닐렌기, 피리미디닐렌기, 피리다지닐렌기, 이소인돌일렌기， 인돌일렌기, 인다졸일렌기, 푸리닐렌기, Naphthacenylene group, pisenylene group, peryleneylene group, pentaphenylene group, nuxasenylene group, pyrroleylene group, imidazole ylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinyl Benzene group, isoindoleylene group, indolylene group, indazole ylene group, furinylene group,
퀴놀리닐렌기 , 이소퀴놀리닐렌기 , 벤조퀴놀리닐렌기 , 프탈라지닐렌기 , Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinylene group,
나프티리디닐렌기, 퀴녹살리닐렌기, 퀴나졸리닐렌기, 시놀리닐렌기， 카바졸일렌기, 페난트리디닐렌기, 아크리디닐렌기, 페난트롤리닐렌기, 페나지닐렌기, Naphthyridinylene group, quinoxalinylene group, quinazolinyl group, cynolinylene group, carbazolylene group, phenantridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group,
밴조옥사졸일렌기, 벤조이미다졸일렌기, 푸라닐렌기, 벤조푸라닐렌기, 티오페닐렌기， 벤조티오페닐렌기， 티아졸일렌기, 이소티아졸일렌기, 벤조티아졸일렌기， Banjo oxazolylene group, benzoimidazole ylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazole ylene group, benzothiazole ylene group,
이소옥사졸일렌기, 옥사졸일렌기, 트리아졸일렌기, 테트라졸일렌기， Isoxazole ylene group, oxazole ylene group, triazole ylene group, tetrazole ylene group,
옥사디아졸일렌기， 트리아지닐렌기, 디벤조푸라닐렌기, 디벤조티오페닐렌기, 벤조카바졸일렌기, 디벤조카바졸일렌기 이미다조피리미디닐렌기 및 Oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazole ylene group, dibenzo carbazole ylene group imidazopyrimidinylene group and
이미다조피리디닐렌기; 중에서 선택되고， Imidazopyridinylene group; Selected from
Q33 내지 5는 서로 독립적으로, 수소, C!- o알킬기， C!- o알콕시기, 페닐기, 나프틸기, 안트라세닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, 카바졸일기, 벤조카바졸일기, 디벤조카바졸일기, 피리디닐기, 피리미디닐기， 피라지닐기, Q 33 to 5 independently of each other, hydrogen, C! -Oalkyl group, C! -Oalkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzo Carbazolyl, dibenzocarbazolyl, pyridinyl, pyrimidinyl, pyrazinyl,
피리다지닐기, 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기 프탈라지닐기, Pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group,
퀴녹살리닐기, 시놀리닐기 및 퀴나졸리닐기 중에서 선택되고; It is selected from a quinoxalinyl group, a cynolinyl group, and a quinazolinyl group;
al 내지 a4, al l 및 al2는 서로 독립적으로, 0 또는 1인, 축합환 화합물.  al to a4, al l and al2 are each independently 0 or 1, a condensed cyclic compound.
【청구항 3]  [Claim 3]
거 1 1항에 있어서,  The method of claim 1,
상기 R, 내지 R6 및 내지 R20이 서로 독립적으로, R, to R 6 and to R 20 are independently of each other,
수소, 중수소， -F, -CI, -Br, -I, 히드록실기， 시아노기 , 니트로기， 아미노기 , 아미디노기 , 히드라진기， 히드라존기 , 카르복실산 또는 이의 염， 술폰산 또는 이의 염, 인산 또는 이의 염, d- o알킬기 및 d- o알콕시기;  Hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a d-oalkyl group and a d-oalkoxy group;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기 , 니트로기， 아미노기, 아미디노기， 히드라진기, 히드라존기, 카르복실산또는 이의 염， 술폰산 또는 이의 염 및 인산 또는 이의 염 중 적어도 하나로 치환된, ^- 0알킬기 및 C ^o알콕시기; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or A ^ -0 alkyl group and a C ^ oalkoxy group substituted with at least one of its salts;
하기 화학식 4-1 내지 4-31 ; -Si(Q3)(Q4)(Q5) (단, 상기 R13 내지 i6 및 Rs 내지 ¾은 -Si(Q3)(Q4)(Q5)가 아님); 및 The following formulas 4-1 to 4-31; -Si (Q 3 ) (Q 4 ) (Q 5 ) provided that R 13 to i6 and Rs to ¾ are not -Si (Q 3 ) (Q 4 ) (Q 5 ); And
상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 (단, R, 내지 ¾는， 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그 :  Groups represented by Formula 2A to the groups represented by Formula 2F, provided that R and ¾ are represented by Formula 2A to the groups represented by Formula 2F:
Figure imgf000085_0001
Figure imgf000085_0001
화학식 4-5 호ᅡ학식 4-6 호ᅡ학식 4-7 호 I학식 4-8 화학식 4ᅳ 9
Figure imgf000085_0002
Formula 4-5 Formula 4 -6 Formula 4 -7 Formula I-8 Formula 4 -8 9
Figure imgf000085_0002
¾ ¾식 4-23 호 f학식 4-24 호1학식 4-25
Figure imgf000086_0001
¾ ¾ Equation 4-23 F. Equation 4-24 Equation 4-25
Figure imgf000086_0001
화학식 4-29 화학식 4-30 화학식 4-31 Formula 4-29 Formula 4-30 Formula 4-31
화학식 4-1 내지 4-31 중,  In Formulas 4-1 to 4-31,
Y31은 0, S, C(Z33)(Z34), N(Z35) 또는 Si(Z36)(Z37)이고 (단, 화학식 4-23 중 Y31은 ΝΗ가 아님); Y 31 is 0, S, C (Z 33 ) (Z 34 ), N (Z 35 ) or Si (Z 36 ) (Z 37 ), provided that Y 31 in Formula 4-23 is not ΝΗ;
Ζ31 내지 ¾7은 서로 독립적으로, 수소, 중수소, -F, -CI, -Br, -I, 히드톡실기， 시아노기， 니트로기, 아미노기, 아미디노기， 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, C ^o알킬기, CrC20알콕시기 페닐기, 나프틸기, 안트라세닐기, 트리페닐레닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, 크라이세닐기, 카바졸일기, 밴조카바졸일기, 디벤조카바졸일기, 디벤조퓨라닐기, 디벤조티오페닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 비페닐기 및 Ζ 31 to ¾ 7 are each independently hydrogen, deuterium, -F, -CI, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ^ oalkyl group, CrC 20 alkoxy group phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, Chrysenyl group, carbazolyl group, banjo carbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, Quinazolinyl group, quinoxalinyl group, biphenyl group, and
-Si(Q33)(Q34)(Q35) 중에서 선택되고; -Si (Q 33 ) (Q 34 ) (Q 35 );
상기 내지 Q5 및 Q33 내지 Q35는 서로 독립적으로, 수소， d-Cso알킬기, ^-¾0알콕시기, 페닐기, 나프틸기, 안트라세닐기, 트리페닐레닐기, 파이레닐기, 페난쓰레닐기, 플루오레닐기, 크라이세닐기, 카바졸일기, 벤조카바졸일기, To the Q 5 and Q 33 to Q 35 are each independently hydrogen, d-Cso alkyl, -¾ ^ 0 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylmethyl group les, Pie LES group, a phenanthryl group waste , Fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group,
디벤조카바졸일기, 디벤조퓨라닐기， 디벤조티오페닐기， 피리디닐기, 피리미디닐기， 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 퀴나졸리닐기 및 퀴녹살리닐기 중에서 선택되고; Dibenzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl and quinoxalinyl;
el은 1 내지 5의 정수 중에서 선택되고, e2는 1 내지 7의 정수 중에서 선택되고, e3는 1 내지 3의 정수 중에서 선택되고, e4는 1 내지 4의 정수 중에서 선택되고， e5는 1 또는 2이고, e6은 1 내지 6의 정수 중에서 선택되고, *는 이웃한 원자와의 결합 사이트이다. el is selected from integers of 1 to 5, e2 is selected from integers of 1 to 7, e 3 is selected from integers of 1 to 3, e4 is selected from integers of 1 to 4, and e5 is 1 or 2 E6 is selected from an integer of 1 to 6, and * is adjacent to It is a binding site with an atom.
【청구항 4】  [Claim 4]
제 1항에 있어서,  The method of claim 1,
상기 내지 ¾ 및 내지 R20은 서로 독립적으로， To ¾ and to R 20 are independently of each other,
수소, 중수소， -F, -CI, -Br， - 1, 히드록실기, 시아노기, 니트로기, 아미노기, 아미디노기， 히드라진기， 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염， 인산 또는 이의 염, ^- 0알킬기 및 CrC20알콕시기; Hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or salts thereof, ^ -0 alkyl group and CrC 20 alkoxy group;
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기， 아미노기， 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염 및 인산 또는 이의 염 중 적어도 하나로 치환된, CJ-C20알킬기 및 d- o알콕시기;  Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or CJ-C20 alkyl group and d-oalkoxy group, substituted with at least one of its salts;
하기 화학식 5-1 내지 5-63;  Formulas 5-1 to 5-63;
-Si(Q3)(Q4)(Q5) (단, 상기 Ri3 내지 R16, R5 및 R6은 -Si(Q3)(Q4)(Q5)가 아님); 및 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 (단: 상기 내지 R6는 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아님); 중에서 선택되는, 축합환 화합물： -Si (Q 3 ) (Q 4 ) (Q 5 ) provided that Ri 3 to R 16 , R 5 and R 6 are not -Si (Q 3 ) (Q 4 ) (Q 5 ); And groups represented by the group to the general formula 2F of the formula 2A (only: to the R 6 is not a group represented by the group to the general formula 2F represented by Formula 2A); Condensed cyclic compound selected from:
Figure imgf000088_0001
Figure imgf000088_0001
화학식 5-18 호ᅡ학식 5-19 화학식 5-20 호ᅡ학식 5-21
Figure imgf000088_0002
Formula 5-18 Formula 5-19 Formula 5-20 Formula 5-21
Figure imgf000088_0002
-26 화학식 5ᅳ 27 화학식 5-28 화학식 5-29 화학식 5-30 화학식 5ᅳ 31
Figure imgf000088_0003
-26 Formula 5 '27 Formula 5-28 Formula 5-29 Formula 5-30 Formula 5' 31
Figure imgf000088_0003
화학식 5-36 화학식 5-37 호ᅡ학식 5-38 화학식 5-39 화학식 5-40 화학식 5-41 호ᅡ학식 5ᅳ 42 화학식 5-43
Figure imgf000089_0001
Chemical Formula 5-36 Chemical Formula 5-37 Chemical Formula 5-39 Chemical Formula 5-40 Chemical Formula 5-41 Chemical Formula 5 ′ 42 Chemical Formula 5-43
Figure imgf000089_0001
f " 5-49 5-50 5-51 ί 5-52
Figure imgf000089_0002
f "5-49 5-50 5-51 ί 5-52
Figure imgf000089_0002
Figure imgf000089_0003
Figure imgf000089_0003
5-60 5-61 5-62 5-63 화학식 5-1 내지 5-63 중， *는 이웃한 원자와의 결합 사이트이다. 【청구항 5 ] 5-60 5-61 5-62 5-63 In Formulas 5-1 to 5-63, * is a binding site with a neighboring atom. [Claim 5]
제 1항에 있어서,  The method of claim 1,
상기 R Rn 및 R12는 서로 독립적으로, 치환 또는 비치환된 R Rn and R 12 are each independently substituted or unsubstituted.
CrC10시클로알킬기, 치환 또는 비치환된 C2-C10해테로시클로알킬기, 치환 또는 비치환된 C3-C10시클로알케닐기， 치환 또는 비치환된 C2-C10헤테로시클로알케닐기, 치환 또는 비치환된 -C20아릴기 , 치환 또는 비치환된 C2-C20헤테로아릴기, 치환 또는 비치환된 1가 비 -방향족 축합다환 그룹， 치환 또는 비치환된 1가 비 -방향족 헤테로축합다환 그룹 및 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹 중에서 선택되고 (단, ¾은 상기 화학식 2A로 표시되는 그룹 내지 상기 화학식 2F로 표시되는 그룹이 아님); C r C 10 cycloalkyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group , Substituted or unsubstituted -C 20 aryl group, substituted or unsubstituted C 2 -C 20 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic A heterocondensed polycyclic group and a group represented by Formula 2A to a group represented by Formula 2F (wherein ¾ is not a group represented by Formula 2A to a group represented by Formula 2F);
R4는 수소, 중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기， 아미노기， 아미디노기, 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, -Czo알킬기 및 d- o알콕시기 중에서 선택되는， 축합환 화합물.  R4 is hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or its A condensed cyclic compound selected from salts, phosphoric acid or salts thereof, -Czoalkyl group and d-oalkoxy group.
【청구항 6】  [Claim 6]
계 1항에 있어서,  The method according to claim 1,
하기 화학식 1ᅳ 1 내지 1ᅳ 9 중 하나로 표시되는, 축합환 화합물: A condensed cyclic compound represented by one of Formulas 1 ′ 1 to 1 ′ 9:
Figure imgf000091_0001
Figure imgf000091_0001
화학식 1 -9  Formula 1-9
상기 화학식 1-1 내지 1-9 중 Xn 및 2에 대한 설명은 제 1항에 기재된 바와 동일하고, R21 내지 R24에 대한 설명은 R17에 대한 설명을 참조하고 , R25 내지 R27에 대한 설명은 R18에 대한 설명을 참조하고, R31 내지 R34에 대한 설명은 R20에 대한 설명을 참조하고, R35 내지 R37에 대한 설명은 R19에 대한 설명을 참조한다. Xn and 2 in Formulas 1-1 to 1-9 are the same as described in claim 1, and for the description of R 21 to R 24 , refer to the description for R 17 , and to R 25 to R 27 . For a description, refer to the description of R 18 , the description of R 31 to R 34 refer to the description on R 20 , and the description of R 35 to R 37 refer to the description on R 19 .
【청구항 7】  [Claim 7]
제 1항에 있어서,  The method of claim 1,
하기 화합물 1 내지 30 증 하나인, 축합환 화합물:
Figure imgf000092_0001
29 30 A condensed cyclic compound which is one of Compounds 1 to 30:
Figure imgf000092_0001
29 30
【청구항 8]  [Claim 8]
거 1 1전극; 상기 제 1전극에 대향되는 게 2전극; 및 상기 제 1전극과 상기 제 2전 사이에 개재되며 발광층을 포함한 유기층；을 포함하고, 상기 유기층은 제 1항 내지 제 7항 중 어느 한 항의 축합환 화합물을 1종 이상 포함한, 유기 발광 소자.  Nearly 1 electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electric field and including a light emitting layer, wherein the organic layer comprises at least one condensed cyclic compound according to any one of claims 1 to 7.
【청구항 9】  [Claim 9]
제 8항에 있어서,  The method of claim 8,
상기 축합환 화합물은 상기 발광층에 존재하는， 유기 발광 소자.  The condensed cyclic compound is present in the light emitting layer, organic light emitting device.
【청구항 10】  [Claim 10]
제 8항에 있어서,  The method of claim 8,
상기 발광층은 게 1호스트， 게 2호스트 및 도편트를 포함하고,  The light emitting layer includes a crab host 1, a crab host 2 and a dopant,
상기 제 1호스트와 상기 제 2호스트는 서로 상이하고，  The first host and the second host are different from each other,
상기 제 1호스트는 상기 축합환 화합물을 포함하고,  The first host includes the condensed cyclic compound,
상기 제 2호스트는 하기 화학식 41로 표시되는 제 1화합물 및 하기 화학식 61로 표시되는 제 2화합물 중 적어도 하나를 포함한， 유기 발광 소자:  The second host includes at least one of the first compound represented by the following Chemical Formula 41 and the second compound represented by the following Chemical Formula 61;
<화학식 41>  <Formula 41>
(ᄂ 41)a41 (R41 )b41 <화학식 61> (B 41) a41 (R41) b41 <Formula 61>
Figure imgf000094_0001
Figure imgf000094_0001
<화학식 61A> <화학식 61B>
Figure imgf000094_0002
<Formula 61A><Formula61B>
Figure imgf000094_0002
상기 화학식들 중 Of the above formula
41은 N-[(L42)a42-(R42)b42], S, 0, S(=0), S(=0)2, C(=0), C(R43)(R44), Si(R43)(R44), 41 is N - [(L 42) a42 - (R 42) b42], S, 0, S (= 0), S (= 0) 2, C (= 0), C (R 43) (R 44 ), Si (R 43 ) (R 44 ),
P(R43), P(=0)(R43) 및 C=N(R43) 중에서 선택되고; P (R 43 ), P (= 0) (R 43 ) and C = N (R 43 );
상기 화학식 61 중 고리 A61은 상기 화학식 61 A로 표시되고; Ring A 61 in Formula 61 is represented by Formula 61 A;
상기 화학식 61 중 고리 A62는 상기 화학식 61B로 표시되고;Ring A 62 in Formula 61 is represented by Formula 61B;
(61은 N-[(L62)a62-(R62)b62], S, 0, S(=0), S(=0)2, C(=0), C(R63)(R64), (¾3)(¾4)， P(R63), P(=0)(R63) 및 C=N(R63) 중에서 선택되고; ( 61 is N-[(L 62 ) a62- (R 62 ) b62 ], S, 0, S (= 0), S (= 0) 2 , C (= 0), C (R 63 ) (R 64 ), (¾ 3 ) (¾ 4 ), P (R 63 ), P (= 0) (R 63 ) and C = N (R 63 );
X기은 C(R71) 또는 N이고, X72는 C(R72) 또는 N이고, X73은 C(R73) 또는 N이고， X74는 C(R74) 또는 N이고, X75는 C(R75) 또는 N이고, X76은 C(R76) 또는 N이고, X77은 C(R77) 또는 N이고 , 78은 C(R78) 또는 N이고; X is C (R 71 ) or N, X 72 is C (R 72 ) or N, X 73 is C (R 73 ) or N, X 74 is C (R 74 ) or N, X 75 is C (R 75 ) or N, X 76 is C (R 76 ) or N, X 77 is C (R 77 ) or N, 78 is C (R 78 ) or N;
Ar41, L41, L42, L61 및 L62은 서로 독립적으로, 치환 또는 비치환된 Ar 41 , L 41 , L 42 , L 61 and L 62 are each independently a substituted or unsubstituted
C3-C10시클로알킬렌기, 치환 또는 비치환된 C2-C10헤테로시클로알킬렌기, 치환 또는 비치환된 C3-Cl0시클로알케닐렌기， 치환 또는 비치환된 C 3 -C 10 cycloalkylene group, substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 cycloalkenylene group, substituted or unsubstituted
C2-C10헤테로시클로알케닐렌기， 치환 또는 비치환된 C6-C60아릴렌기, 치환 또는 비치환된 C2-C60헤테로아릴렌기, 치환 또는 비치환된 2가 비-방향족 축합다환 그룹 및 치환 또는 비치환된 2가 비-방향족 헤테로축합다환 그룹 증에서 선택되고; C 2 -C 10 heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 arylene group, substituted or unsubstituted C 2 -C 60 heteroarylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic ring Group and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group polyamide;
nl 및 n2는 서로 독립적으로, 0 내지 3의 정수 중에서 선택되고;  nl and n2 are each independently selected from an integer of 0 to 3;
a41, a42, a61 및 a62는 서로 독립적으로， 0 내지 3의 정수 중에서 선택되고; a41, a42, a61 and a62 are each independently selected from an integer of 0 to 3;
R4! 내지 R43, R51 내지 4, ¾ 1 내지 1 4 및 R71 내지 R?9는 서로 독립적으로， 수소, 중수소, -F, -CI, -Br, -1， 히드록실기， 시아노기 , 니트로기 , 아미노기 , 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, 치환 또는 비치환된 CrC60알킬기， 치환또는 비치환된 C2-C60알케닐기, 치환 또는 비치환된 C2-C60알키닐기, 치환또는 비치환된 - o알콕시기， 치환 또는 비치환된 C3-C10시클로알킬기， 치환 또는 비치환된 C2-C10해테로시클로알킬기, 치환 또는 비치환된 C3-C10시클로알케닐기, 치환 또는 비치환된 R4! To R43, R51 to 4, ¾ 1 to 1 4 and R71 to R? 9 are each independently, Hydrogen, deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, substituted or unsubstituted CrC 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted -oalkoxy group, Substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted
C2-C10헤테로시클로알케닐기, 치환 또는 비치환된 C6-C60아릴기， 치환 또는 비치환된 C6-C60아릴옥시기, 치환 또는 비치환된 C6-C60아릴티오기, 치환 또는 비치환된 C 2 -C 10 heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 arylthio group , Substituted or unsubstituted
C2-C60해테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹, -NiQtXQ ), -Si(Q3)(Q4)(Q5) 및 C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -NiQtXQ), -Si (Q 3 ) ( Q 4 ) (Q 5 ) and
-B(Q6)(Q7) 중에서 선택되고; -B (Q 6 ) (Q 7 );
b41, b42, b51 내지 b54, b61, b62 및 b79는 서로독립적으로， 1 내지 3의 정수 중에서 선택되고;  b41, b42, b51 to b54, b61, b62 and b79 are each independently selected from integers of 1 to 3;
상기 치환된 C3-C10시클로알킬렌기, 치환된 C2-C10헤테로시클로알킬렌기, 치환된 c3-c10시클로알케닐렌기, 치환된 c2-c10헤테로시클로알케닐렌기, 치환된 The substituted C 3 -C 10 cycloalkylene group, substituted C 2 -C 10 heterocycloalkylene group, substituted c 3 -c 10 cycloalkenylene group, substituted c 2 -c 10 heterocycloalkenylene group, substitution Done
C6-C60아릴렌기, 치환된 C2-C60헤테로아릴렌기, 치환된 2가 비-방향족 축합다환 그룹， 치환된 2가 비-방향족 해테로축합다환 그룹, 치환된 -C60알킬기, 치환된 C 6 -C 60 arylene group, substituted C 2 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted -C 60 alkyl group, substituted Done
C2-C60알케닐기, 치환된 C2-C60알키닐기, 치환된 d- o알콕시기, 치환된 C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted d-oalkoxy group, substituted
C3-C10시클로알킬기, 치환된 C2-Cl0헤테로시클로알킬기, 치환된 C3-C10시클로알케닐기, 치환된 C2-C10헤테로시클로알케닐기, 치환된 C6-C60아릴기, 치환된 C6-C60아릴옥시기， 치환된 c6-c60아릴티오기, 치환된 C2-C60헤테로아릴기, 치환된 1가 비-방향족 C 3 -C 10 cycloalkyl group, substituted C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl Groups, substituted C 6 -C 60 aryloxy groups, substituted c 6 -c 60 arylthio groups, substituted C 2 -C 60 heteroaryl groups, substituted monovalent non-aromatics
축합다환 그룹 및 치환된 1가 비-방향족 헤테로축합다환 그룹의 치환기 중 적어도 하나는, At least one of the substituents of the condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group is
중수소, -F, -CI, -Br, -I, 히드록실기, 시아노기， 니트로기 , 아미노기， 아미디노기， 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염, - 。알킬기, C2-C60알케닐기, C2-C60알키닐기 및 C^ o알콕시기; Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or . a salt thereof, - alkyl, C 2 -C 60 alkenyl, C 2 -C 60 alkynyl group and a C ^ o alkoxy;
중수소， -F, -CI, -Br, -1， 히드록실기, 시아노기 , 니트로기 , 아미노기， 아미디노기 , 히드라진기, 히드라존기, 카르복실산 또는 이의 염, 술폰산 또는 이의 염, 인산 또는 이의 염 , C3-C 10시클로알킬기 , C2-C 10해테로시클로알킬기 , C3-C10시클로알케닐기, C2-C10헤테로시클로알케닐기 , C6— C60아릴기 , C6-C60아릴옥시기 , C6-C60아릴티오기, c2-c60헤테로아릴기， 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹， -N(Q„)(Q12), -Si(Q13)(Q,4)(Ql 5) 및 -B(Q16)(Q17) 중 적어도 하나로 치환된, ^ ：60알킬기, C2-C60알케닐기, C2-C60알키닐기 및 C ^o알콕시기; Deuterium, -F, -CI, -Br, -1, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or a salt thereof, C 3 -C 10 cycloalkyl, C 2 -C 10 year Tero cycloalkyl, C 3 -C 10 cycloalkenyl group, C 2 -C 10 hetero cycloalkenyl group, C 6 - C 60 aryl group, C 6 -C 60 aryloxy group, C 6 -C 60 arylthio group, c 2 -c 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ') (Q 12 ), -Si (Q 13 ) (Q, 4 ) ^: 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group and C ^ oalkoxy group, substituted with at least one of (Q l 5 ) and -B (Q 16 ) (Q 17 );
C3-C10시클로알킬기, C2-C10헤테로시클로알킬기， C3-C10시클로알케닐기, c2-c10헤테로시클로알케닐기 , c6-c60아릴기， c6-c60아릴옥시기 , c6-c60아릴티오기 ,C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, c 2 -c 10 heterocycloalkenyl group, c 6 -c 60 aryl group, c 6 -c 60 aryl Oxy group, c 6 -c 60 arylthio group,
C2-C60헤테로아¾기， 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹; C 2 -C 60 heteroa¾ group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic group;
중수소， -F, -CI, -Br, -I, 히드록실기， 시아노기 , 니트로기, 아미노기, 아미디노기 , 히드라진기, 히드라존기， 카르복실산 또는 이의 염， 술폰산 또는 이의 염, 인산 또는 이의 염, ^^60알킬기, C2-C60알케닐기, C2-C60알키닐기, - o알콕시기， Deuterium, -F, -CI, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, ^^ 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, -oalkoxy group,
C3-C10시클로알킬기, C2-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
c2-c10헤테로시클로알케닐기 , c6-c60아릴기， c6-c60아릴옥시기 , c6-c60아릴티오기，c 2 -c 10 come hetero cycloalkenyl group, c 6 -c 60 aryl group, c 6 -c 60 aryloxy group, c 6 -c 60 aryl tea,
C2-C60헤테로아릴기， 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹， -N(Q21)(Q22), -Si(Q23)(Q24)(Q25) 및 -B(Q26)(Q27) 중 적어도 하나로 치환된, Cr 0시클로알킬기, C2-C10해테로시클로알킬기， C3-Cl 0시클로알케닐기， C 2 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q 21 ) (Q 22 ), -Si (Q 23 ) (Q 24 ) ( Q 25) and -B (Q 26) (Q 27 ) of the at least one substituted, C r 0 cycloalkyl, C 2 -C 10 year Tero cycloalkyl, C 3 -C l 0 cycloalkenyl group,
C2-C10헤테로시클로알케닐기 , C6-C60아릴기 , C6-C60아릴옥시기 , C6-C60아릴티오기 , C2-C60헤테로아릴기， 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹; 및 C 2 -C 10 hetero cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come tea, C 2 -C 60 heteroaryl group, a monovalent non-aromatic Condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups; And
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35) 및 -B(Q36)(Q37); 중에서 선택되고; -N (Q 31 ) (Q 32 ), -Si (Q 33 ) (Q 34 ) (Q 35 ) and -B (Q 36 ) (Q 37 ); Is selected from;
상기 내지 Q7, Qu 내지 Q17, Q21 내지 Q27 및 Q3 l 내지 Q37은 서로 독립적으로, 수소, -C60알킬기, C2-C60알케닐기, C2-C60알키닐기, d- o알콕시기， C3-C10시클로알킬기， C2-C10헤테로시클로알킬기 , C3-C10시클로알케닐기 , To Q 7 , Qu to Q 17 , Q 21 to Q 27 and Q 3 l to Q 37 are each independently hydrogen, a -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, d-oalkoxy group, C 3 -C 10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group,
C2-C10헤테로시클로알케닐기， C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C2-C60헤테로아릴기 , 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹 중에서 선택된다. C 2 -C 10 hetero cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come tea, C 2 -C 60 heteroaryl group, a monovalent non-aromatic Condensed polycyclic groups and monovalent non-aromatic heterocondensed polycyclic groups.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017037571A1 (en) * 2015-09-04 2017-03-09 Semiconductor Energy Laboratory Co., Ltd. Compound, light-emitting element, display device, electronic device, and lighting device
CN109721625A (en) * 2017-10-31 2019-05-07 三星显示有限公司 Heterocyclic compound and organic luminescent device including the heterocyclic compound

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080026135A1 (en) * 2003-04-15 2008-01-31 3M Innovative Properties Company Electron transport agents for organic electronic devices
WO2011137072A1 (en) * 2010-04-26 2011-11-03 Universal Display Corporation Bicarbazole containing compounds for oleds
KR20130110051A (en) * 2012-03-27 2013-10-08 에스에프씨 주식회사 Carbazole derivatives and organoelectro luminescent device using the same
KR20140000611A (en) * 2012-06-22 2014-01-03 (주)피엔에이치테크 Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080026135A1 (en) * 2003-04-15 2008-01-31 3M Innovative Properties Company Electron transport agents for organic electronic devices
WO2011137072A1 (en) * 2010-04-26 2011-11-03 Universal Display Corporation Bicarbazole containing compounds for oleds
KR20130110051A (en) * 2012-03-27 2013-10-08 에스에프씨 주식회사 Carbazole derivatives and organoelectro luminescent device using the same
KR20140000611A (en) * 2012-06-22 2014-01-03 (주)피엔에이치테크 Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KIM, S-K. ET AL.: "Synthesis and Hole-Transporting Properties of Phenyl-Carbazyl Derivatives.", MOL. CRYST. LIQ. CRYST., vol. 491, no. 1, 2008, pages 133 - 144, XP008169593, ISSN: 0026-8941 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017037571A1 (en) * 2015-09-04 2017-03-09 Semiconductor Energy Laboratory Co., Ltd. Compound, light-emitting element, display device, electronic device, and lighting device
JP2017210481A (en) * 2015-09-04 2017-11-30 株式会社半導体エネルギー研究所 Compound
CN108137611A (en) * 2015-09-04 2018-06-08 株式会社半导体能源研究所 Compound, light-emitting component, display device, electronic equipment and lighting device
US10230055B2 (en) 2015-09-04 2019-03-12 Semiconductor Energy Laboratory Co., Ltd. Compound, light-emitting element, display device, electronic device, and lighting device
CN108137611B (en) * 2015-09-04 2021-05-28 株式会社半导体能源研究所 Compound, light-emitting element, display device, electronic device, and lighting device
JP2021155435A (en) * 2015-09-04 2021-10-07 株式会社半導体エネルギー研究所 Compound, light-emitting element, display device, electronic device, and lighting device
US11276824B2 (en) 2015-09-04 2022-03-15 Semiconductor Energy Laboratory Co., Ltd. Compound, light-emitting element, display device, electronic device, and lighting device
JP7550838B2 (en) 2015-09-04 2024-09-13 株式会社半導体エネルギー研究所 Light emitting element
CN109721625A (en) * 2017-10-31 2019-05-07 三星显示有限公司 Heterocyclic compound and organic luminescent device including the heterocyclic compound
CN109721625B (en) * 2017-10-31 2023-11-07 三星显示有限公司 Heterocyclic compound and organic light-emitting device including the same

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