KR101511072B1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. More particularly, the organic electroluminescent compound according to the present invention is selected from the following formulas (1) to (5).

[In the above Chemical Formulas 1 to 5, X and Y are each independently selected from N (Ar _1), O and S, Ar ₁ may be different from each other, in the case where Ar ₁ is plural Ar ₁ or is represented by Ar ₂ ; Z ₁ to Z ₈ are each independently selected from C (Ar ₃ ) and N, Ar ₃ may be different from each other, and adjacent Ar ₃ may combine with each other to form a ring.

The organic electroluminescent compound according to the present invention is advantageous in that it can be used as a host material of an organic electroluminescent material in an OLED device to produce an OLED having a better luminous efficiency and better lifetime characteristics of a device than a conventional host material, have.

Phosphorescent host, organic light emitting compound, organic light emitting element

Description

TECHNICAL FIELD The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the same,

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. More particularly, the present invention relates to a novel organic electroluminescent compound used as a light emitting material and an organic electroluminescent device employing the same as a host.

The most important factor determining the luminous efficiency in an OLED is a light emitting material. Fluorescent materials are widely used as luminescent materials to date, but the development of a phosphorescent material on the mechanism of electroluminescence is one of the best ways to improve the luminous efficiency up to 4 times theoretically. Until now, iridium (III) complexes have been widely known as phosphorescent materials. Materials such as (acac) Ir (btp) ₂ , Ir (ppy) ₃ and Firpic are known for each RGB. Recently, many phosphorescent materials have been studied in Japan and Europe.

CBP is the most widely known host material for a phosphorescent light emitting material, and a high efficiency OLED using a hole blocking layer such as BCP and BAlq is known. In Pioneer, Japan, a high performance OLED using a BAlq derivative as a host is known .

However, existing materials have advantages in terms of luminescence properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, such as material changes when subjected to a high temperature deposition process under vacuum. Since the power efficiency in OLED = (π / voltage) × current efficiency, the power efficiency is inversely proportional to the voltage, and the power efficiency of the OLED should be high if the power consumption is low. OLEDs using real phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials. However, when conventional materials such as BAlq and CBP are used as hosts for phosphorescent materials, OLEDs using fluorescent materials (Lm / w) because the driving voltage is higher than that of the conventional device. In addition, since the lifetime of the OLED device is never satisfactory, development of a more stable and more excellent host material is required.

Accordingly, the present inventors have made efforts to solve the above-mentioned conventional problems, and as a result, they have invented a novel luminescent compound for realizing an organic electroluminescent device having excellent luminous efficiency and remarkably improved lifetime.

It is another object of the present invention to provide an organic luminescent compound having an excellent skeleton with a suitable color coordinate and a luminescent efficiency and a device life better than a conventional host material in order to solve the above problems. And to provide an organic electroluminescent device with high efficiency and long life which is employed as a material.

The present invention relates to an organic light emitting compound represented by the following general formulas (1) to (5) and an organic electroluminescent device including the organic electroluminescent compound. The organic electroluminescent compound according to the present invention is superior in luminous efficiency and life- There is an advantage that an OLED having a very good driving life can be manufactured.

[In the above Chemical Formulas 1 to 5, X and Y are each independently selected from N (Ar _1), O and S, Ar ₁ may be different from each other, in the case where Ar ₁ is plural Ar ₁ or is represented by Ar ₂ ;

Z ₁ To Z ₈ are each independently selected from C (Ar ₃ ) and N, Ar ₃ may be different from each other, and adjacent Ar ₃ may combine with each other to form a ring;

Ar ₁ And Ar ₂ are independently a (C1-C60) alkyl, (C3-C60) cycloalkyl, N, O, S, Si, and 5-6 membered heterocycloalkyl of, containing one or more selected from P (C7 one another C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl;

Ar ₃ is independently selected from the group consisting of hydrogen, (C 1 -C 60) alkyl, halogen, cyano, (C 3 -C 60) cycloalkyl, N, O, S, (C2-C60) alkynyl, (C6-C60) aryl, (C1-C60) alkoxy, (C6-C60) alkynyl, (C6-C60) arylthio, (C1-C60) alkylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) aryl (C6-C30) arylsilyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C30) alkylsilyl, di (C1-C60) alkylboranyl, nitro, and hydroxy;

Of said Ar ₁ to Ar ₃ alkyl, cycloalkyl, heterocycloalkyl, alkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, aryl Amino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylboranyl or alkylboranyl is optionally substituted with (C1-C60) alkyl, halogen, cyano, (C3- C60) cycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, -C60) aryl, (C1-C60) alkoxy, (C6-C60) _{aryloxy, P (= O) R a} R b [R a and R _b are independently (C1-C60) alkyl or (C6-C60 to each other (C3-C60) heteroaryl, (C3-C60) heteroaryl substituted by (C6-C60) aryl, (C3- (C60) alkylthio, (C6-C60) arylthio, (C1-C60) alkylthio, (C6-C30) alkylsilyl, di (C1-C30) alkylsilyl, di (C1-C30) alkylamino, mono- or di Which may be further substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, cyano, nitro, cyano, arylsilyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C60) alkylboranyl, nitro and hydroxy;

Provided that both X and Y are N (Ar ₁ ), and Z ₁ To Z ₈ are both C (Ar ₃ ).]

The substituents containing the "(C1-C60) alkyl" moiety described in the present invention may have 1 to 60 carbon atoms, may have 1 to 20 carbon atoms, and may have 1 to 10 carbon atoms . The substituents containing the "(C6-C60) aryl" moiety may have 6 to 60 carbon atoms, may have 6 to 20 carbon atoms, and may have 6 to 12 carbon atoms. The substituents containing the "(C3-C60) heteroaryl" moiety may have from 3 to 60 carbon atoms, may have from 4 to 20 carbon atoms, and may have from 4 to 12 carbon atoms. The substituents containing the "(C3-C60) cycloalkyl" moiety may have 3 to 60 carbon atoms, 3 to 20 carbon atoms, and may have 3 to 7 carbon atoms. The substituents containing the "(C2-C60) alkenyl or alkynyl" moiety may have 2 to 60 carbon atoms, may have 2 to 20 carbon atoms, and may have 2 to 10 carbon atoms.

Alkyl " as used in the present invention includes a straight-chain or branched saturated monovalent hydrocarbon radical consisting solely of a carbon atom and a hydrogen atom, or a combination thereof, and also "alkoxy" refers to an -O-alkyl group, As defined.

&Quot; Aryl " in the present invention means an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and is a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms, . Also included are structures in which one or more aryls are attached through a chemical bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, But is not limited thereto.

&Quot; Heteroaryl " in the present invention means an aryl group having 1 to 4 hetero atoms selected from N, O and S as the aromatic ring skeletal atoms and the remaining aromatic skeletal atom carbon, Monocyclic heteroaryl, and condensed polycyclic heteroaryl with one or more benzene rings, and may be partially saturated. Also included are structures in which one or more heteroaryls are attached via a chemical bond. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt. Specific examples thereof include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl , Monocyclic heteroaryl such as furanzanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, benzofuryl, benzothienyl, isobenzofuryl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, Wherein R is selected from the group consisting of oxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinolizinyl, quinoxalinyl, (Such as pyridyl N-oxide, quinolyl N-oxide), quaternary salts thereof, and the like, and the like, but are not limited thereto Do not.

Further, the organic luminescent compound of the present invention can be exemplified by a compound having the following structure.

[Wherein Ar ₁ and Ar ₂ are the same as defined in the above Chemical Formulas 1 to 5]

Further, the organic luminescent compound of the present invention can be exemplified by a compound having the following structure.

[Wherein Ar ₁ and Ar ₂ are the same as defined in the above Chemical Formulas 1 to 5]

Further, the organic luminescent compound of the present invention can be exemplified by a compound having the following structure.

[Wherein Ar ₁ is the same as defined in the above Chemical Formulas 1 to 5]

More specifically, Ar ₁ and Ar ₂ are independently of each other phenyl, 1-naphthyl, 2-naphthyl, or substituents selected from the following structures, but are not limited thereto.

Further, the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device according to the present invention comprises: a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer comprises at least one organic electroluminescent compound selected from the above formulas (1) to (5).

The organic electroluminescent device according to the present invention is characterized in that the organic material layer includes a light emitting layer and the light emitting layer includes at least one phosphorescent dopant using at least one organic electroluminescent compound selected from the general formulas 1 to 5 as a light emitting host, Is not particularly limited.

In the organic electroluminescent device of the present invention, at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound is further included, can do.

In addition, in the organic light emitting device of the present invention, in addition to at least one organic electroluminescent compound selected from the above-mentioned Chemical Formulas 1 to 5, an organic compound having a group 1, 2, 4, 5 period transition metal, lanthanide metal and d- Organic metal, and organic compound, and the organic material layer may include a light emitting layer and a charge generating layer.

In addition, an organic electroluminescent device emitting white light by simultaneously including at least one organic light emitting layer emitting blue, red or green light in addition to the organic light emitting compound may be formed in the organic material layer.

The organic electroluminescent compound according to the present invention is advantageous in that it can be used as a host material of an organic electroluminescent material in an OLED device to produce an OLED having a better luminous efficiency and better lifetime characteristics of a device than a conventional host material, have.

Hereinafter, the organic luminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described in order to facilitate a detailed understanding of the present invention, but the present invention is not limited thereto. And are not intended to limit the scope of the invention.

[ Manufacturing example ]

[Preparation Example 1] Preparation of Compound A

Preparation of Compound A-1

Bromo-2-nitro-benzene 30g (148.5mmol), 1- naphthalene boronic acid 30.6g (178.2mmol), Pd (PPh 3) 4 5.14g (4.45mmol), 2M K 2 CO 3 aqueous solution (297.01mmol), toluene 500 mL of ethanol and 200 mL of ethanol were added and the mixture was stirred under reflux. After 4 hours, it was cooled to room temperature and distilled water was added. Extracted with EA, dried over magnesium sulfate and distilled under reduced pressure. Followed by column separation to obtain 31 g (124.3 mmol, 84.03%) of Compound A-1.

Preparation of Compound A-2

31 g (124.3 mmol) of the compound A-1 and 300 mL of triethyl phosphite were placed and stirred under reflux. After 10 hours, the reaction mixture was cooled to room temperature and the organic solvent was distilled off under reduced pressure. Distilled water was added and extracted with EA. Dried over magnesium sulfate and distilled under reduced pressure. The column was separated to obtain 18 g (82.84 mmol, 66.81%) of Compound A-2.

Preparation of Compound A-3

Compound A-2 18g (82.84mmol), 1,5- diphenyl-3-chloropyridine 26.4g (99.41mmol), Pd (OAc ) 2 1.85g (8.28mmol), P (t-bu) 3 8.17ml ( 16.5 mmol, 50% in xylene), 23.8 g (248.5 mmol) of NaOt-Bu and 500 mL of toluene were placed and stirred under reflux. After 12 hours, it was cooled to room temperature and distilled water was added. Extracted with EA and dried with magnesium sulfate. The mixture was distilled under reduced pressure and subjected to column separation to obtain 19 g (42.54 mmol, 51.36%) of Compound A-3.

Preparation of Compound A-4

19 g (42.54 mmol) of the compound A-3 was dissolved in 200 mL of DMF, and 8.33 g (46.80 mmol) of NBS was added. After 10 hours at room temperature, the organic solvent was distilled off under reduced pressure. Distilled water was added and extracted with EA. Dried over magnesium sulfate and distilled under reduced pressure. The column was separated to obtain 20 g (38.06 mmol, 89.47%) of Compound A-4.

Preparation of Compound A-5

20 g (38.06 mmol) of the compound A-4 was dissolved in 200 mL of THF, and 15.22 mL (38.06 mmol, 2.5 M in hexane) of n-buLi was slowly added at -78 째 C. After stirring for one hour, 5.51 mL (49.48 mmol) of trimethyl borate was added. The mixture was slowly warmed to room temperature and stirred for 12 hours. Distilled water was added and extracted with EA. Dried over magnesium sulfate and distilled under reduced pressure. Followed by column separation to obtain 8 g (16.31 mmol, 42.86%) of Compound A-5.

Preparation of Compound A-6

Compound A-5 8g (16.31mmol), bromo-2-nitro-benzene 3.95g (19.57mmol), Pd (PPh 3) 4 0.56g (0.48mmol), 2M K 2 CO 3 aqueous solution of 16mL (32.62mmol), toluene And 20 mL of ethanol were placed, and the mixture was stirred under reflux. 7 g (12.33 mmol, 75.62%) of Compound A-6 was obtained in the same manner as in the synthesis of Compound A-1.

Preparation of Compound A-7

7 g (12.33 mmol) of the compound A-6 was mixed with 100 mL of triethyl phosphite, and 4 g (7.46 mmol, 58.33%) of the compound A-7 was obtained in the same manner as in the synthesis of the compound A-2.

Preparation of Compound A

(11.20 mmol) of copper powder, 3.09 g of K ₂ CO ₃ , 0.15 g (0.59 mmol) of 18-crown-6, 1, And 100 mL of 2-dichlorobenzene were mixed and stirred under reflux. After 15 hours, it was cooled to room temperature. The organic solvent was distilled off under reduced pressure and distilled water was added. The mixture was extracted with EA and subjected to column separation to obtain 3.6 g (5.88 mmol, 78.88%) of Compound A.

[ Manufacturing example  2] Preparation of compound B

Preparation of Compound B-1

1,4-dibromo-2,3-dinitrobenzene 20g (61.36mmol), naphthalene-1- boronic acid 26g (153.42mmol), Pd ₍₃ PPh) 3.54g ₄ (3.06mmol), 2M K ₂ CO ₃ 90 mL of the aqueous solution, 200 mL of toluene and 100 mL of ethanol were mixed and stirred under reflux. After 10 hours, the solution was cooled to room temperature, distilled water was added, and the solution was extracted with EA. Dried over magnesium sulfate and distilled under reduced pressure. The column was separated to obtain 22 g (52.32 mmol, 85.28%) of the compound B-1.

Preparation of compound B-2

22 g (52.32 mmol) of the compound B-1 and 200 mL of triethyl phosphite were mixed and stirred at 180 占 폚. 10 g (28.05 mmol, 53.95%) of the compound B-2 was obtained in the same manner as in the synthesis of the compound A-2.

Preparation of Compound B-3

(28.05 mmol) of compound B-2, 7.1 g (28.05 mmol) of 2-iodonaphthalene, 2.67 g (42.08 mmol) of copper powder, 11.63 g (84.17 mmol) of K ₂ CO ₃ , 2.24 mmol) and 100 mL of 1,2-dichlorobenzene were mixed, and the mixture was stirred at 190 占 폚 for 20 hours. The mixture was cooled to room temperature and the organic solvent was distilled off under reduced pressure. Distilled water was added and extracted with EA. Dried over magnesium sulfate and distilled under reduced pressure. The obtained residue was subjected to column separation to obtain 4 g (8.28 mmol, 29.60%) of Compound B-3.

Preparation of Compound B

4 g (8.28 mmol) of the compound B-3 was dissolved in 20 mL of DMF, and 0.49 g (12.43 mmol, 60% dispersion in mineral oil) of NaH was added to the reaction vessel dissolved in 20 mL of DMF. After one hour, 2.66 g (9.94 mmol) of 2-chloro-4,6-diphenyltriazine was dissolved in 20 mL of DMF. After stirring for 12 hours, distilled water was added and the resulting solid was filtered under reduced pressure. EA and DMF to obtain 3.5 g (4.90 mmol, 59.21%) of Compound B.

[Preparation Example 3] Preparation of Compound C

Preparation of Compound C-1

42.52 g (379.26 mmol) of 1,2-cyclohexylidone was dissolved in 1000 mL of ethanol, and 20 g (126.42 mmol) of 2-naphthylhydrazine was slowly added thereto. 0.28 mL (5.05 mmol) of acetic acid was added and the mixture was heated to 40 占 폚. After cooling for 2 hours, distilled water was added and the resulting solid was filtered under reduced pressure. 17 g (67.37 mmol, 53.47%) of the compound C-1 was obtained.

Preparation of Compound C-2

17 g (67.37 mmol) of the compound C-1 was dissolved in 100 mL of acetic acid, and 10 mL of trifluoroacetic acid was added. After stirring at room temperature for 2 hours, distilled water was added. NaOH aqueous solution and then extracted with EA. And dried with magnesium sulfate. The mixture was distilled under reduced pressure and subjected to column separation to obtain 11 g (46.75 mmol, 69.39%) of the compound C-2.

Preparation of Compound C-3

10 g (32.11 mmol, 68.69%) of the compound C-3 was obtained in the same manner as in the synthesis of the compound B-3.

Preparation of Compound C-4

12 g (29.88 mmol, 93.07%) of the compound C-4 was obtained in the same manner as in the synthesis of the compound C-1.

Preparation of Compound C-5

6 g (15.68 mmol, 52.50%) of the compound C-5 was obtained in the same manner as in the synthesis of the compound C-2.

Preparation of Compound C

5 g (8.14 mmol, 51.95%) of Compound C was obtained in the same manner as in the synthesis of Compound B.

[Preparation Example 4] Preparation of Compound D

Preparation of Compound D-2

Using Compound D-1, 11 g (38.02 mmol, 89.22%) of Compound D-2 was prepared in the same manner as Compound A-1.

Preparation of compound D-3

8 g (31.09 mmol, 81.78%) of the compound D-3 was prepared in the same manner as the compound A-2.

Preparation of compound D

6 g (12.30 mmol, 38.70%) of Compound D was prepared in the same manner as Compound B.

[Preparation Example 5] Preparation of compounds E and F

Preparation of Compound E-2

Using Compound E-1, 15 g (51.85 mmol, 86.51%) of Compound E-2 was prepared in the same manner as Compound A-1.

Preparation of Compound E-3

6 g (23.31 mmol, 44.97%) of Compound E-3 was prepared in the same manner as Compound A-2.

Preparation of Compound E

5 g (10.25 mmol, 43.99%) of Compound E was prepared in the same manner as Compound B. [

Preparation of Compound F-1

3 g (11.65 mmol, 22.48%) of Compound F-1 was prepared in the same manner as Compound A-2.

Preparation of Compound F

3g (6.15 mmol, 52.81%) of Compound F was prepared in the same manner as Compound B.

[Preparation Example 6] Preparation of compounds G and H

Preparation of Compound G-1

20 g (179.41 mmol) of iodobenzene, 11.4 g (179.41 mmol) of copper, 49 g (358.8 mmol) of K ₂ CO ₃ , 2.5 g (9.56 mmol) of 18- -Dichlorobenzene (600 mL) was added, and the mixture was stirred at 190 占 폚 for 12 hours. The mixture was cooled to room temperature and distilled under reduced pressure. Distilled water was added and extracted with EA. Dried over magnesium sulfate and distilled under reduced pressure. The column was separated to obtain 22 g (90.42 mmol, 75.60%) of the compound G-1.

Preparation of compound G-2

25 g (77.59 mmol, 85.81%) of Compound G-2 was prepared in the same manner as Compound A-4.

Preparation of compound G-3

11 g (38.31 mmol, 49.37%) of Compound G-3 was prepared in the same manner as Compound A-5.

Preparation of compound G-4

12 g (32.84 mmol, 85.72%) of Compound G-4 was prepared in the same manner as Compound A-1.

Preparation of compound G-5

The reaction was conducted in the same manner as in the case of the compound A-2 for 4 hours to prepare 6 g (17.99 mmol, 54.80%) of the compound G-5.

Preparation of Compound G

7 g (12.39 mmol, 68.91%) of Compound G was prepared in the same manner as Compound B.

Preparation of Compound H-1

The reaction was conducted for 4 hours in the same manner as the compound A-2 to prepare 2 g (5.99 mmol, 18.26%) of the compound H-1.

Preparation of Compound H

1.7 g (3.01 mmol, 50.26%) of Compound H was prepared in the same manner as Compound B. [

The organic luminescent compounds (TA, TB and TC) were prepared using the methods of Preparation Examples 1 to 6 and the substituents Ar ₁ and Ar ₂ of the organic light emitting compounds prepared in Table 1 and Table ₂ , ¹ H NMR and MS / FAB.

[Table 1]

[Table 2]

[Examples 1 to 10] Fabrication of an OLED device using an organic light emitting compound according to the present invention

An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (15 Ω / □) obtained from glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol Respectively. Next, an ITO substrate was placed in a substrate folder of a vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine -TNATA) was added and the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr. Then, a current was applied to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate.

The NPB -diphenyl-4,4'-diamine into the (NPB), by applying a current to the cell - Then, to another cell of the vacuum vapor-deposit device structure, N, N 'N, N -bis (α-naphthyl)' And evaporated to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer.

A compound according to the present invention (for example, a compound TA8-H4-H2) which has been vacuum-sublimed and purified with a host material at 10 ^-6 torr is placed in one cell in a vacuum deposition apparatus and a light emitting dopant ) ₂ Ir (acac)). Then, the two materials were evaporated at different rates and doped to 4 to 10 mol% to deposit a 30 nm thick emission layer on the hole transport layer.

Subsequently, tris (8-hydroxyquinoline) -aluminum (III) (Alq) having the following structure was deposited as an electron transporting layer to a thickness of 20 nm and a compound lithium quinolate (Liq) , And then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition apparatus to fabricate an OLED.

[Examples 11 to 20] Preparation of OLED device using electroluminescent compound according to the present invention

As the host material, the compounds according to the invention (e.g., compound TA4-H4-H4), except for using the use of, and to a light emitting dopant, the organic iridium complex of the formula (Ir (ppy) _3), of Example 1-10 OLED devices were fabricated in the same manner as OLED devices.

[Comparative Examples 1 and 2] OLED element fabrication using conventional light emitting material

Except that Bis (2-methyl-8-quinolinato) aluminum (III) (BAlq) was added to another cell in the vacuum vapor deposition apparatus instead of the electroluminescent compound according to the present invention as a luminescent host material. An OLED device was fabricated in the same manner as in Example 11.

The driving voltage of the OLED devices of Examples 1 to 10 and 11 to 20 containing the organic light emitting compound according to the present invention and the OLED device containing the conventional light emitting compound prepared in Comparative Examples 1 and 2, The power efficiency was measured at 1,000 cd / m < 2 > and shown in the following Tables 3 and 4, respectively.

From the following Tables 3 and 4, it can be seen that the organic luminescent compounds developed in the present invention exhibit superior characteristics in terms of performance compared to conventional materials.

[Table 3]

[Table 4]

From Table 3, it can be seen that the luminescent properties of the compounds developed in the present invention are superior to those of conventional materials. It exhibited a driving voltage lower than 1 V due to excellent current characteristics as compared with that of Comparative Example 1 which is a conventional material and showed a power efficiency characteristic of 1.4 times or more higher than that of Comparative Example 1 due to excellent luminescence characteristics.

In addition, when using the compounds developed in the present invention as the host material for green light emission from Table 4, the power efficiency characteristic was remarkably higher than that of the device of Comparative Example 2 by 1.6 times or more because of excellent luminescence characteristics. It was confirmed that the luminescent characteristics were superior to those of the conventional materials. Particularly, in the case of Example 14, the device was driven at a voltage lower than that of the device of Comparative Example 1 by 2.7 V, and the device of Example 17 showed a driving voltage of 5.5 V and a power efficiency of 15.9 lm / W at 1000 cd / .

Therefore, the device using the electroluminescent compound according to the present invention as a host material for red and green luminescence has excellent luminescent characteristics and further lowers the driving voltage. In particular, in the case of a green luminescent device, a power efficiency of 5.1 to 7.7 lm / So that the power consumption can be improved.

Claims (10)

An organic light-emitting compound represented by the following formula (1). [Chemical Formula 1]

X and Y are each independently selected from N (Ar ₁ ), O and S, at least one of X and Y is N (Ar ₁ ), Ar ₁ may be different from each other, and Ar ₁ Is plural, it is represented by Ar < ₁ > or Ar < _{2 &} gt ;; Z ₁ to Z ₈ are each independently selected from C (Ar ₃ ) and N, Ar ₃ may be different from each other, and adjacent Ar ₃ may bond to each other to form a ring; Ar ₁ is (C6-C60) aryl substituted with substituted or unsubstituted (C6-C60) heteroaryl, or substituted or unsubstituted (C6-C60) heteroaryl; Ar ₂ is a 5 to 6 membered heterocycloalkyl comprising at least one member selected from (C 1 -C 60) alkyl, (C 3 -C 60) cycloalkyl, N, O, S, Si and P, (C 7 -C 60) (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl; Ar ₃ is independently selected from the group consisting of hydrogen, (C 1 -C 60) alkyl, halogen, cyano, (C 3 -C 60) cycloalkyl, N, O, S, (C6-C60) aryl, (C1-C60) alkoxy, (C6-C60) alkynyl, (C6-C60) arylthio, (C1-C60) alkylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino (C6-C30) arylsilyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C30) alkylsilyl, di C1-C60) alkylboranyl, nitro, and hydroxy; Of said Ar ₁ to Ar ₃ alkyl, cycloalkyl, heterocycloalkyl, alkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, aryl Amino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylboranyl or alkylboranyl is optionally substituted with (C1-C60) alkyl, halogen, cyano, (C3- C60) cycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, -C60) aryl, (C1-C60) alkoxy, (C6-C60) _{aryloxy, P (= O) R a} R b [R a and R _b are independently (C1-C60) alkyl or (C6-C60 to each other (C3-C60) heteroaryl, (C3-C60) heteroaryl substituted by (C6-C60) aryl, (C3- (C60) alkylthio, (C6-C60) arylthio, (C1-C60) alkylthio, (C6-C30) alkylsilyl, di (C1-C30) alkylsilyl, di (C1-C30) alkylamino, mono- or di Which may be further substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, cyano, nitro, cyano, arylsilyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C60) alkylboranyl, nitro and hydroxy; Except that when X and Y are both N (Ar ₁ ) and Z ₁ to Z ₈ are all C (Ar ₃ ) An organic light-emitting compound selected from the following compounds.

[Wherein Ar ₁ is substituted or unsubstituted (C6-C60) substituted with a heteroaryl (C6-C60) aryl, or a substituted or unsubstituted (C6-C60) heteroaryl; Ar ₂ is a 5 to 6 membered heterocycloalkyl comprising at least one member selected from (C 1 -C 60) alkyl, (C 3 -C 60) cycloalkyl, N, O, S, Si and P, (C 7 -C 60) (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl. The method according to claim 1, An organic light-emitting compound selected from the following compounds.

[Wherein Ar ₁ and Ar ₂ are the same as defined in claim 1]. The method according to claim 1, An organic light-emitting compound selected from the following compounds.

[Wherein Ar ₁ is the same as defined in claim 1] An organic electroluminescent device comprising the organic electroluminescent compound according to any one of claims 1 to 4. 6. The method of claim 5, The organic electroluminescent device includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound and at least one phosphorescent dopant. The method according to claim 6, Wherein the organic material layer further comprises at least one amine compound selected from the group consisting of an arylamine compound and a styrylarylamine compound. The method according to claim 6, Wherein the organic material layer further comprises at least one metal or complex compound selected from the group consisting of Group 1, Group 2, Group 4, Periodic transition metal, Lanthanide series metal and d-transition metal organic metal. The method according to claim 6, Wherein the organic layer includes a light emitting layer and a charge generating layer. The method according to claim 6, And at least one organic light emitting layer emitting blue, red or green light is simultaneously included in the organic material layer to emit white light.