KR20120116282A - Novel organic electroluminescence compounds and organic electroluminescence device using the same - Google Patents
Novel organic electroluminescence compounds and organic electroluminescence device using the same Download PDFInfo
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- KR20120116282A KR20120116282A KR1020110033928A KR20110033928A KR20120116282A KR 20120116282 A KR20120116282 A KR 20120116282A KR 1020110033928 A KR1020110033928 A KR 1020110033928A KR 20110033928 A KR20110033928 A KR 20110033928A KR 20120116282 A KR20120116282 A KR 20120116282A
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- South Korea
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- independently
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 93
- 238000005401 electroluminescence Methods 0.000 title abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 44
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 25
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 150000002367 halogens Chemical group 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000000732 arylene group Chemical group 0.000 claims abstract description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 3
- -1 cyano, carbazolyl Chemical group 0.000 claims description 62
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 26
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 239000004305 biphenyl Chemical group 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 13
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 13
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 13
- 125000005561 phenanthryl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001725 pyrenyl group Chemical group 0.000 claims description 13
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 12
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 11
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000011368 organic material Substances 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005730 thiophenylene group Chemical group 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 34
- 238000004519 manufacturing process Methods 0.000 abstract description 23
- 239000010410 layer Substances 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000012153 distilled water Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000012776 electronic material Substances 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125851 compound 27 Drugs 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 2
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- TWOIWLFSUGLFHY-UHFFFAOYSA-N 1,4-diphenylbenzimidazole Chemical compound C1=NC2=C(C=3C=CC=CC=3)C=CC=C2N1C1=CC=CC=C1 TWOIWLFSUGLFHY-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- JXMZUNPWVXQADG-UHFFFAOYSA-N 1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1I JXMZUNPWVXQADG-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- NBHFYZDOQSDARS-UHFFFAOYSA-N Bc1ccc(c(cccc2)c2c2ccccc22)c2c1 Chemical compound Bc1ccc(c(cccc2)c2c2ccccc22)c2c1 NBHFYZDOQSDARS-UHFFFAOYSA-N 0.000 description 1
- VONZPTILZGVNOJ-UHFFFAOYSA-N C(C1)C=Cc2c1c(cccc1)c1[nH]2 Chemical compound C(C1)C=Cc2c1c(cccc1)c1[nH]2 VONZPTILZGVNOJ-UHFFFAOYSA-N 0.000 description 1
- 0 C*c1cccc(-c(cc2)cc3c2c(cccc2)c2c2ccccc32)c1 Chemical compound C*c1cccc(-c(cc2)cc3c2c(cccc2)c2c2ccccc32)c1 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CIFHCCDFUSHIQW-UHFFFAOYSA-N Cc1cc(-c(cc2)cc3c2c2ccccc2c2ccccc32)cc(Br)c1 Chemical compound Cc1cc(-c(cc2)cc3c2c2ccccc2c2ccccc32)cc(Br)c1 CIFHCCDFUSHIQW-UHFFFAOYSA-N 0.000 description 1
- CZGFFIWRMVPTKV-UHFFFAOYSA-N Clc1nc(-[n]2c3ccccc3c3c2cccc3)ncc1 Chemical compound Clc1nc(-[n]2c3ccccc3c3c2cccc3)ncc1 CZGFFIWRMVPTKV-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- YMXDKUJKRMOGEK-UHFFFAOYSA-N c(cc1c2ccccc22)ccc1[n]2-c1nccc(-c2cccc(-c(cc3)cc4c3c3ccccc3c3ccccc43)c2)n1 Chemical compound c(cc1c2ccccc22)ccc1[n]2-c1nccc(-c2cccc(-c(cc3)cc4c3c3ccccc3c3ccccc43)c2)n1 YMXDKUJKRMOGEK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- HSSPXXSSTKINGH-UHFFFAOYSA-L dilithium quinoline-2-carboxylate Chemical compound N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[Li+].[Li+].N1=C(C=CC2=CC=CC=C12)C(=O)[O-] HSSPXXSSTKINGH-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
Description
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same.
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].
OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. 현재까지 이리듐(III)착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp)2, Ir(ppy)3 및 Firpic 등의 재료가 알려져 있다. 특히, 최근 일본, 구미에서 많은 인광 재료들이 연구되고 있다.The most important factor determining the luminous efficiency in OLEDs is the luminous material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, materials such as (acac) Ir (btp) 2 , Ir (ppy) 3, and Firpic are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.
인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있고, BCP 및 BAlq 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq 유도체를 호스트로 이용해 고성능의 OLED를 개발한 바 있다.CBP is the most widely known host material for phosphorescent emitters. To date, high-efficiency OLEDs with hole blocking layers such as BCP and BAlq have been known. In Japan, Pioneer has developed high-performance OLEDs using BAlq derivatives as hosts. I've done it.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 단점을 갖고 있다. OLED에서 전력효율 = [(π/전압) × 전류효율]의 관계에 있으므로 전력 효율은 전압에 반비례하고, 따라서 OLED의 소비 전력을 낮으려면 전력 효율을 높여야 한다. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 사용되던 BAlq 또는 CBP와 같은 종래재료의 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없었다. 또한, OLED 소자에 사용할 경우 수명 측면에서도 만족스럽지 못하였다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, so that the material changes when undergoing a high temperature deposition process under vacuum. In the relationship of power efficiency = [(π / voltage) × current efficiency] in OLED, power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of OLED, power efficiency must be increased. In fact, OLEDs using phosphorescent materials have considerably higher current efficiency (cd / A) than OLEDs using fluorescent materials, but in the case of conventional materials such as BAlq or CBP used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). In addition, when used in OLED devices, it was not satisfactory in terms of lifetime.
한편, 국제특허공보 제WO03/078541호에는 카바졸기를 골격에 헤테로아릴이 치환된 유기 전기 발광 소재용 화합물을 언급하고 있다. 그러나, 상기 문헌에는 카바졸 골격에 트리페닐렌이 치환된 헤테로아릴을 모두 겸비한 화합물을 개시하고 있지 않다. Meanwhile, International Patent Publication No. WO03 / 078541 mentions a compound for an organic electroluminescent material in which a carbazole group is substituted with a heteroaryl in a skeleton. However, this document does not disclose a compound having both a heteroaryl substituted with triphenylene in a carbazole skeleton.
따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며 둘째로, 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. It is to provide a high efficiency and long life organic electroluminescent element employed as a light emitting material.
본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 기존 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수할 뿐만 아니라 전력효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better light emission efficiency and excellent life characteristics of the material than the existing material, the driving life of the device This is not only very good, but also has an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.
[화학식 1][Formula 1]
[상기 화학식 1에서, [In Formula 1,
X1 내지 X3는 각각 독립적으로 CH 또는 N이고, 단 X1 내지 X3가 동시에 CH인 경우는 제외하며;X 1 to X 3 are each independently CH or N, provided that X 1 to X 3 are Except when CH at the same time;
L1 및 L2는 서로 독립적으로 화학결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C3-C30)헤테로아릴렌이고; L 1 and L 2 are independently of each other a chemical bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (C3-C30) heteroarylene;
R은 수소, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이며;R is hydrogen, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) heteroaryl;
R1 내지 R10는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, -NR11R12, -SiR13R14R15, -SR16, -OR17 , 시아노, 나이트로 또는 하이드록시이고;R 1 To R 10 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitro or hydroxy;
R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있으며;R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero A cycloaliphatic ring and a monocyclic ring or a polycyclic ring which is connected to a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene, which is aryl or does not include or include a fused ring with adjacent substituents. An aromatic ring of the ring may be formed, and the carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen, and sulfur;
a 및 b는 각각 독립적으로 1 내지 4의 정수이고, a 및 b가 2 이상의 정수인 경우 동일하거나 상이할 수 있으며;a and b are each independently an integer of 1 to 4, and may be the same or different when a and b are integers of 2 or more;
m 및 n은 각각 독립적으로 1 내지 3의 정수이고, m 및 n이 2 이상의 정수인 경우 동일하거나 상이할 수 있으며;m and n are each independently an integer of 1 to 3, and may be the same or different when m and n are an integer of 2 or more;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]Wherein said heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
본 발명에 기재된 「알킬」, 「알콕시」 및 그 외 「알킬」부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, 「시클로알킬」은 단일 고리계 뿐만 아니라 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된 (C7-C30)바이시클로알킬과 같은 여러 고리계 탄화수소도 포함한다. 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로서 페닐, 나프틸, 비페닐, 터페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등이 있다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로서 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴, 다이벤조퓨란닐, 다이벤조싸이오페닐 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 들수 있다.Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. There is this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. "Heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Means an aryl group, 5-6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, Monocyclic heteroaryl such as tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoiso Thiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnaolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenantri Polycyclic heteroaryls such as dinyl, benzodioxyl, dibenzofuranyl, dibenzothiophenyl and their corresponding N-oxides (e.g. pyridyl N-oxides, quinolyl N-oxides), Quaternary salts;
또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 바람직하게는 (C1-C20)알킬이고, 더 바람직하게는 (C1-C10)알킬이며, ‘(C6-C30)아릴’기는 바람직하게는 (C6-C20)아릴이고, 더 바람직하게는 (C6-C12)아릴이다. ‘(C3-C30)헤테로아릴’기는 바람직하게는 (C3-C20)헤테로아릴이고, 더 바람직하게는 (C3-C12)헤테로아릴이다. ‘(C3-C30)시클로알킬’기는 바람직하게는 (C3-C20)시클로알킬이고, 더 바람직하게는 (C3-C7)시클로알킬이다. ‘(C2-C30)알케닐 또는 알키닐’기는 바람직하게는 (C2-C20)알케닐 또는 알키닐이고, 더 바람직하게는 (C2-C10)알케닐 또는 알키닐이다.Further, the '(C1-C30) alkyl' group described in the present invention is preferably (C1-C20) alkyl, more preferably (C1-C10) alkyl, and the '(C6-C30) aryl' group is preferred. Preferably (C6-C20) aryl, more preferably (C6-C12) aryl. The '(C3-C30) heteroaryl' group is preferably (C3-C20) heteroaryl, more preferably (C3-C12) heteroaryl. The '(C3-C30) cycloalkyl' group is preferably (C3-C20) cycloalkyl, more preferably (C3-C7) cycloalkyl. The '(C2-C30) alkenyl or alkynyl' group is preferably (C2-C20) alkenyl or alkynyl, more preferably (C2-C10) alkenyl or alkynyl.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 L1, L2, R, R1 내지 R10 및 R11 내지 R17에 더 치환되는 치환기는 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C5-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C5-C30)헤테로아릴, (C3-C30)시클로알킬, 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C6-C30)알키닐, 시아노, 카바졸릴, 디C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 또는 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미한다.In addition, in the description of "substituted or unsubstituted" described in the present invention, "substituted" means a case where is further substituted with an unsubstituted substituent, the L 1 , L 2 , R, R 1 To R 10 and R 11 to R 17 are further substituted with deuterium, halogen, (C1-C30) alkyl, halogen-substituted (C1-C30) alkyl, (C6-C30) aryl, (C5-C30) hetero Aryl, (C6-C30) aryl substituted (C5-C30) heteroaryl, (C3-C30) cycloalkyl, heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C6-C30) alkynyl, cyano, carbazolyl , DiC1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkyl Boronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro Or one or more selected from the group consisting of hydroxy.
더욱 구체적으로, 상기 R은 수소, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐 또는 페릴렌일이고;More specifically, R is hydrogen, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthenyl or peryleneyl;
L1 및 L2는 서로 독립적으로 화학결합, 페닐렌, 나프틸렌, 비페닐렌, 플루오레닐렌, 안트라세닐렌, 피리디닐렌, 퓨란닐렌, 티오페닐렌, 다이벤조티오페닐렌,, 다이벤조퓨란닐렌 또는 -페닐렌-다이벤조티오페닐렌이고; L 1 and L 2 are each independently a chemical bond, phenylene, naphthylene, biphenylene, fluorenylene, anthracenylene, pyridinylene, furanylene, thiophenylene, dibenzothiophenylene, dibenzo Furanylene or -phenylene-dibenzothiophenylene;
R1 내지 R8은 서로 독립적으로 수소, 중수소, 클로로, 플루오르, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일 또는 N-카바졸릴이고;R 1 To R 8 are independently of each other hydrogen, deuterium, chloro, fluorine, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, Peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl , Benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl or N-carbazolyl;
R9 및 R10은 서로 독립적으로 수소, 중수소, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 다이벤조티오페닐, 벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일 또는 N-카바졸릴이고;R 9 and R 10 are independently of each other hydrogen, deuterium, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl , Pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl or N-carbazolyl;
상기 R의 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐 또는 페릴렌일, 및 R1 내지 R10의 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 다이벤조티오페닐, 벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴 또는 페난트롤린일은 각각 중수소, 클로로, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴 및 트리페닐실릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.Phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl or peryleneyl of said R, and R 1 To R 10 phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl , Thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazineyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothiophenyl, Pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl or phenanthrolinyl are deuterium, chloro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i- Butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl , Trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, tri Consisting of riphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl and triphenylsilyl It may be further substituted with one or more substituents selected from the group.
본 발명에 따른 유기 발광 화합물로는 대표적으로 하기의 화합물을 들 수 있다.Examples of the organic light emitting compound according to the present invention include the following compounds.
본 발명에 따른 유기 발광 화합물은 하기 반응식에 나타난 바와 같이 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in the following scheme.
[반응식 1][Reaction Scheme 1]
[상기 반응식 1에서, X1 내지 X3, L1, L2, R, R1 내지 R10, n, m, a 및 b는 화학식 1에서의 정의와 동일하고, X는 할로겐이다.][In Reaction Scheme 1, X 1 to X 3 , L 1 , L 2 , R, R 1 to R 10 , n, m, a and b are the same as defined in Formula 1, and X is halogen.]
또한, 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖는 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 화합물을 하나 이상 포함한다. 또한 상기 유기물층은 발광층을 포함하고, 이 발광층에서 상기 화학식 1의 화합물을 호스트 물질로 사용할 수 있다. In addition, the present invention provides an organic electroluminescent device, 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 includes at least one compound represented by Chemical Formula 1. The organic material layer may include a light emitting layer, and the compound of Formula 1 may be used as a host material in the light emitting layer.
또한 본 발명에 따른 호스트와 함께 사용되는 유기 전계 발광 소자용 인광 도판트에는 대표적으로 하기 화학식 2의 화합물이 있다. In addition, a phosphorescent dopant for an organic electroluminescent device used with a host according to the present invention typically includes a compound represented by the following Chemical Formula 2.
[화학식 2][Formula 2]
MM 1One LL 101101 LL 102102 LL 103103
[상기 화학식 2에서,[In the formula (2)
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고,Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os,
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고;R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q는 
구체적으로 상기 화학식 2의 도판트 화합물로서 다음과 같은 화합물을 사용하는 것이 바람직하다. Specifically, it is preferable to use the following compounds as the dopant compound of Chemical Formula 2.
본 발명의 유기 전계 발광 소자는 화학식 1의 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. The organic electroluminescent device of the present invention includes a compound of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고,나아가 상기 유기물층은 발광층 및 전하생성층을 더 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, the organic material layer is selected from the group consisting of Group 1, Group 2, Group 4, Period 5 transition metals, Lanthanide series metals and organic metals of d-transition elements in addition to the compound of Formula 1 One or more metal or complex compounds may be further included. Furthermore, the organic material layer may further include a light emitting layer and a charge generating layer.
또한, 상기 유기물층은 상기 유기 전자재료용 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. In addition, the organic material layer may include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the compound for organic electronic materials to form an organic light emitting device that emits white light.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO 등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferred examples of the chalcogenide include SiO X (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like, and preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.
본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same, and light emitting characteristics of the device will be described with reference to a representative compound of the present invention for a detailed understanding of the present invention.
[제조예 1]화합물 9의 제조Preparation Example 1 Preparation of Compound 9
화합물 compound 1-11-1 의 제조Manufacturing
NaH(60% in mineral oil) 3.3g(83.90mmol)을 DMF 10mL에 희석시켰다. 카바졸 11.2g(67.12mmol)을 DMF 60mL에 녹인 후 상기 반응액에 첨가하였다. 1시간동안 상온에서 교반시켰다. 2,4-디클로로피리미딘 10g(67.12mmol)을 DMF 60mL에 녹인 후 상기 반응액에 첨가하였다. 4시간동안 상온에서 교반시킨 후 증류수 40mL를 가하였다. MC로 추출하고 증류수와 NaCl 수용액으로 씻어준 후 무수 MgSO4로 건조하고 감압 증류시킨 다음, 컬럼(헥산/EA)분리하여 화합물 1-1 4.0g(21%)을 얻었다.3.3 g (83.90 mmol) of NaH (60% in mineral oil) was diluted in 10 mL of DMF. 11.2 g (67.12 mmol) of carbazole was dissolved in 60 mL of DMF and added to the reaction solution. Stirred at room temperature for 1 hour. 10 g (67.12 mmol) of 2,4-dichloropyrimidine was dissolved in 60 mL of DMF, and then added to the reaction solution. After stirring at room temperature for 4 hours, 40 mL of distilled water was added thereto. Extraction with MC, washing with distilled water and aqueous NaCl solution, drying with anhydrous MgSO 4 , distillation under reduced pressure, and column (hexane / EA) separation gave Compound 1-1 4.0g (21%).
화합물 compound 1-21-2 의 제조Manufacturing
1,3-다이브로모벤젠 17.8g(75.36mmol), 트리페닐렌-2-일보론산 22.6g(82.89mmol), Pd(PPh3)4 2.4g(3.76mmol), 2M Na2CO3 110mL 및 에탄올 50mL을 톨루엔 300mL에 녹인 후 100℃에서 3시간 동안 환류 교반시켰다. 반응이 끝나면 상온으로 냉각하여 EA로 추출한 뒤 증류수로 세척하고 무수MgSO4로 잔여 수분을 제거하고 건조시킨 후 컬럼(헥산/EA) 분리하여 화합물 1-2 14.4g(50%)을 얻었다. 17.8 g (75.36 mmol) of 1,3-dibromobenzene, 22.6 g (82.89 mmol) of triphenylene-2-ylboronic acid, 2.4 g (3.76 mmol) of Pd (PPh 3 ) 4 , 110 mL of 2M Na 2 CO 3 and ethanol 50 mL was dissolved in 300 mL of toluene and stirred at reflux at 100 ° C. for 3 hours. After the reaction, the mixture was cooled to room temperature, extracted with EA, washed with distilled water, residual water was removed with anhydrous MgSO 4 , dried, and column (hexane / EA) was separated to obtain compound 1-2 14.4 g (50%).
화합물 compound 1-31-3 의 제조Manufacturing
화합물 1-2 3.8g(0.010mol)을 THF 100mL에 녹인 다음 -78℃로 냉각시켰다. n-부틸리튬(2.5M) 6.2mL(0.015mol)을 천천히 첨가하고 1시간 동안 저온을 유지하며 교반한 후 -78℃에서 B(OMe)3 1.7mL(0.015mmol)을 첨가하고 12시간 동안 환류 교반시켰다. 반응이 종결되면 1M HCl을 첨가한 후 10분 뒤 증류수로 씻어주고 EA로 추출하였다. 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 화합물 1-3 1.8g(53%)를 얻었다. 3.8 g (0.010 mol) of Compound 1-2 was dissolved in 100 mL of THF, and then cooled to -78 ° C. 6.2 mL (0.015 mol) of n-butyllithium (2.5M) was added slowly and stirred at low temperature for 1 hour, followed by addition of 1.7 mL (0.015 mmol) of B (OMe) 3 at -78 ° C and refluxed for 12 hours. Stirred. After the reaction was completed, 10 minutes after adding 1M HCl, washed with distilled water and extracted with EA. The organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator, followed by column (hexane / EA) separation to obtain compound 1-3 1.8 g (53%).
화합물 compound 99 의 제조Manufacturing
화합물 1-3 8.2g(23.44mmol), 화합물 1-1 9.8g(35.16mmol), Pd(OAc)2 790mg(3.51mmol), P(t-Bu)3 4.7mL(7.03mmol) 및 2M K3PO4 46mL(93.76mmol)을 혼합하고, 에탄올 46mL 및 톨루엔 200mL를 첨가한 후 120℃로 가열시킨 후 2시간동안 교반시켰다. 반응이 끝나면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 목적 화합물 9 5.4g(42%)를 얻었다.Compound 1-3 8.2 g (23.44 mmol), Compound 1-1 9.8 g (35.16 mmol), Pd (OAc) 2 790 mg (3.51 mmol), P (t-Bu) 3 4.7 mL (7.03 mmol) and 2M K 3 46 mL (93.76 mmol) of PO 4 were mixed, 46 mL of ethanol and 200 mL of toluene were added, then heated to 120 ° C. and stirred for 2 hours. After the reaction was washed with distilled water, extracted with EA, the organic layer was dried over anhydrous MgSO 4 and the solvent was removed by a rotary evaporator to separate the column (hexane / EA) to obtain the target compound 9 5.4g (42%).
MS/FAB found 548, calculated 547.65MS / FAB found 548, calculated 547.65
[제조예 2] 화합물 4의 제조Preparation Example 2 Preparation of Compound 4
화합물 compound 2-12-1 의 제조Manufacturing
1-아이오도-2-니트로벤젠 30g(120.4mmol), 4-브로모페닐보론산 26g(132.5mmol), Pd(PPh3)4 6.9g(6.02mmol), 2M Na2CO3 150mL 및 톨루엔 500mL를 혼합하고 100℃에서 4시간동안 교반시킨 다음, 상온으로 냉각시키고 EA로 추출하였다. 증류수로 씻어 주고 무수MgSO4로 건조시킨 후 감압 증류하고 컬럼(헥산/EA)분리하여 화합물 2-1 28g(100.68mmol, 83,33%)을 얻었다. 30 g (120.4 mmol) of 1-iodo-2-nitrobenzene, 26 g (132.5 mmol) of 4-bromophenylboronic acid, 6.9 g (6.02 mmol) of Pd (PPh 3 ) 4 , 150 mL of 2M Na 2 CO 3 and 500 mL of toluene Were mixed and stirred at 100 ° C. for 4 hours, then cooled to room temperature and extracted with EA. Washed with distilled water, dried over anhydrous MgSO 4 and distilled under reduced pressure and separated by column (hexane / EA) to give a compound 2-1 28g (100.68mmol, 83,33%).
화합물 compound 2-22-2 의 제조Manufacturing
화합물 2-1 28g(100.68mmol)을 트리페닐포스파이트(triethylphosphite) 300mL에 섞고 150℃에서 교반시켰다. 6시간 후 상온으로 냉각하고 감압 증류하였다. EA로 추출하고 증류수로 씻어 주었다. 무수MgSO4로 건조하고 감압 증류하였다. 컬럼(헥산/EA)분리하여 화합물 2-2 11g(44.69mmol, 44.38%)을 얻었다.28 g (100.68 mmol) of Compound 2-1 were mixed with 300 mL of triphenylphosphite and stirred at 150 ° C. After 6 hours, the mixture was cooled to room temperature and distilled under reduced pressure. Extracted with EA and washed with distilled water. It was dried over anhydrous MgSO 4 and distilled under reduced pressure. Column (hexane / EA) was separated to give 11 g (44.69 mmol, 44.38%) of compound 2-2 .
화합물 compound 2-32-3 의 제조Manufacturing
2,4-다이클로로-1,3,5-트리아진 11.3g(75.36mmol), 트리페닐렌-2-일보론산 22.6g(82.89mmol), Pd(PPh3)4 2.4g(3.76mmol), 2M Na2CO3 110mL, 에탄올 50mL 및 톨루엔 300mL를 혼합한 후 100℃에서 3시간동안 환류 교반시켰다. 반응이 끝나면 상온으로 냉각하여 EA로 추출한 뒤 증류수로 세척하고 무수MgSO4로 잔여 수분을 제거하고 건조시킨 후 컬럼(헥산/EA)분리하여 화합물 2-3 12.9g(50%)을 얻었다. 11.3 g (75.36 mmol) of 2,4-dichloro-1,3,5-triazine, 22.6 g (82.89 mmol) of triphenylene-2-ylboronic acid, 2.4 g (3.76 mmol) of Pd (PPh 3 ) 4 , 110 mL of 2M Na 2 CO 3 , 50 mL of ethanol, and 300 mL of toluene were mixed and then stirred under reflux at 100 ° C. for 3 hours. After the reaction, the mixture was cooled to room temperature, extracted with EA, washed with distilled water, residual water was removed with anhydrous MgSO 4 , dried, and column (hexane / EA) was separated to obtain compound 2-3 12.9 g (50%).
화합물 compound 2-42-4 의 제조Manufacturing
화합물 2-3 6.8g(20.0mmol), 화합물 2-2 5.9g(24mmol), Pd(OAc)2 0.14g(0.6mmol), P(t-Bu)3 1.00mL(2.0mmol), NaOt-Bu 5.9g(60mmol) 및 톨루엔 200mL를 혼합하고 120℃에서 12시간동안 환류 교반시켰다. 반응이 완결되면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA)분리하고, 재결정하여 화합물 2-4 6.94g(63%)을 얻었다.Compound 2-3 6.8 g (20.0 mmol), Compound 2-2 5.9 g (24 mmol), Pd (OAc) 2 0.14 g (0.6 mmol), P (t-Bu) 3 1.00 mL (2.0 mmol), NaOt-Bu 5.9 g (60 mmol) and 200 mL of toluene were mixed and stirred at reflux at 120 ° C. for 12 h. After the reaction was completed, washed with distilled water and then dried the organic layer was back extracted with EA over anhydrous MgSO 4 The solvent was removed by rotary evaporation column (hexane / EA) separation, re-crystallization and the compound 2-4 6.94g (63%) Got it.
화합물 compound 44 의 제조Manufacturing
화합물 2-4 11g(20.0mmol), 9H-카바졸 4g(24mmol), Pd(OAc)2 0.14g(0.6mmol), P(t-Bu)3 1.00mL(2.0mmol), NaOt-Bu 5.9g(60mmol) 및 톨루엔 200mL를 넣고 120℃에서 12시간동안 환류 교반시켰다. 반응이 완결되면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA)분리하고 재결정(MeOH/MC)하여 목적 화합물 4 7.7g(63%)을 얻었다.Compound 2-4 11 g (20.0 mmol), 9H-carbazole 4g (24mmol), Pd (OAc) 2 0.14g (0.6mmol), P (t-Bu) 3 1.00mL (2.0mmol), NaOt-Bu 5.9g (60mmol) and 200mL of toluene were added for 12 hours at 120 ℃. It was stirred at reflux. When the reaction was complete then washed with distilled water, drying the organic layer was back extracted with EA over anhydrous MgSO 4 The solvent was removed by rotary evaporation column (hexane / EA) separate and re-crystallization (MeOH / MC) to the desired compound 4 7.7g (63 %) Was obtained.
MS/FAB found 638, calculated 637.73MS / FAB found 638, calculated 637.73
[제조예 3] 화합물 6의 제조Preparation Example 3 Preparation of Compound 6
화합물 compound 3-13-1 의 제조Manufacturing
화합물 2 16g(33.98mmol)를 THF 500mL에 녹이고 0℃에서 10분간 교반시켰다. NBS 7.35g(40.78mmol)을 첨가하고 상온에서 하루 동안 교반시켰다. 반응이 종결되면 증류수와 EA로 추출하고 유기층을 무수MgSO4로 건조시킨 다음 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 화합물 3-1 13.7g(73%)를 얻었다.16 g (33.98 mmol) of Compound 2 were dissolved in 500 mL of THF and stirred at 0 ° C. for 10 min. 7.35 g (40.78 mmol) of NBS were added and stirred for 1 day at room temperature. After completion of the reaction, the mixture was extracted with distilled water and EA, the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator, and then column (hexane / EA) was separated to obtain compound 3-1 13.7 g (73%).
화합물 compound 3-23-2 의 제조Manufacturing
화합물 3-1 5.5g(0.010mol)을 THF 100mL에 녹인 다음 -78℃로 냉각시켰다. n-부틸리튬(2.5M) 6.2mL(0.015mol)을 천천히 첨가하고 1시간동안 저온을 유지하며 교반한 후 -78℃에서 B(OMe)3 1.7mL(0.015mmol)을 첨가하고 12시간동안 환류 교반시켰다. 반응이 종결되면 1M HCl을 첨가한 후 10분 뒤 증류수로 씻어주고 EA로 추출하였다. 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 화합물 3-2 2.6g(51%)를 얻었다. 5.5 g (0.010 mol) of Compound 3-1 was dissolved in 100 mL of THF, and then cooled to -78 ° C. 6.2 mL (0.015 mol) of n-butyllithium (2.5M) was added slowly and stirred at low temperature for 1 hour, followed by addition of 1.7 mL (0.015 mmol) of B (OMe) 3 at -78 ° C and refluxed for 12 hours. Stirred. After the reaction was completed, 10 minutes after adding 1M HCl, washed with distilled water and extracted with EA. The organic layer was dried over anhydrous MgSO 4 , the solvent was removed with a rotary evaporator, and column (hexane / EA) was separated to give 2.6 g (51%) of compound 3-2 .
화합물 compound 66 의 제조Manufacturing
화합물 3-2 12.1g(23.44mmol), 브로모벤젠 5.5g(35.16mmol), Pd(oAc)2 790mg(3.51mmol), P(t-Bu)3 4.7mL(7.03mmol) 및 2M K3PO4 46mL(93.76mmol)을 혼합하고, 에탄올 46mL 및 톨루엔 200mL를 첨가한 후 120℃로 가열시킨 후 2시간동안 교반시켰다. 반응이 끝나면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 목적 화합물 6 5.5g(43%)를 얻었다.Compound 3-2 12.1 g (23.44 mmol), bromobenzene 5.5 g (35.16 mmol), Pd (oAc) 2 790 mg (3.51 mmol), P (t-Bu) 3 4.7 mL (7.03 mmol) and 2M K 3 PO 4 46 mL (93.76 mmol) were mixed, 46 mL of ethanol and 200 mL of toluene were added, then heated to 120 ° C. and stirred for 2 hours. After the reaction was washed with distilled water and extracted with EA, the organic layer was dried over anhydrous MgSO 4 and the solvent was removed by a rotary evaporator to separate the column (hexane / EA) to give the target compound 6 5.5g (43%).
MS/FAB found 548, calculated 547.65MS / FAB found 548, calculated 547.65
[제조예 4]화합물 27의 제조Preparation Example 4 Preparation of Compound 27
화합물 compound 4-14-1 의 제조Manufacturing
화합물 9 18.6g(33.98mmol)를 THF 500mL에 녹이고 0℃에서 10분간 교반시켰다. NBS 7.35g(40.78mmol)을 첨가하고 상온에서 하루 동안 교반시켰다. 반응이 종결되면 증류수와 EA로 추출하고 유기층을 무수MgSO4로 건조시킨 다음 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 화합물 4-1 15.5g(73%)를 얻었다.18.6 g (33.98 mmol) of compound 9 was dissolved in 500 mL of THF and stirred at 0 ° C. for 10 min. 7.35 g (40.78 mmol) of NBS were added and stirred for 1 day at room temperature. After completion of the reaction, the mixture was extracted with distilled water and EA, the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator, and column (hexane / EA) was separated to obtain 15.5 g (73%) of Compound 4-1 .
화합물 compound 4-24-2 의 제조Manufacturing
화합물 4-1 6.3g(0.010mol)을 THF 100mL에 녹인 다음 -78℃로 냉각시켰다. n-부틸리튬(2,5M) 6.2mL(0.015mol)을 천천히 첨가하고 1시간 동안 저온을 유지하며 교반한 후 -78℃에서 B(OMe)3 1.7mL(0.015mmol)을 첨가하고 12시간 동안 환류 교반시켰다. 반응이 종결되면 1M HCl을 첨가한 후 10분 뒤 증류수로 씻어주고 EA로 추출하였다. 얻어진 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 화합물 4-2 3.1g(53%)를 얻었다.6.3 g (0.010 mol) of Compound 4-1 was dissolved in 100 mL of THF, and then cooled to -78 ° C. 6.2 mL (0.015 mol) of n-butyllithium (2,5M) was added slowly and stirred at low temperature for 1 hour, followed by addition of 1.7 mL (0.015 mmol) of B (OMe) 3 at -78 ° C and for 12 hours. It was stirred at reflux. After the reaction was completed, 10 minutes after adding 1M HCl, washed with distilled water and extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 , the solvent was removed with a rotary evaporator, and column (hexane / EA) was separated to obtain 3.1 g (53%) of Compound 4-2 .
화합물 compound 2727 의 제조Manufacturing
화합물 4-2 13.9g(23.44mmol), 3-브로모-9-페닐-9H-카바졸 11.3g(35.16mmol), Pd(OAc)2 790mg(3.51mmol), P(t-Bu)3 4.7mL(7.03mmol), 2M K3PO4 46mL(93.76mmol)넣고, 에탄올 46mL 및 톨루엔 200mL를 첨가한 후 120℃로 가열시킨 후 2시간동안 교반시켰다. 반응이 끝나면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 무수MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼(헥산/EA) 분리하여 화합물 27 8.0g(43%)를 얻었다.Compound 4-2 13.9 g (23.44 mmol), 3-bromo-9-phenyl-9H-carbazole 11.3 g (35.16 mmol), Pd (OAc) 2 790 mg (3.51 mmol), P (t-Bu) 3 4.7 46 mL (93.76 mmol) of 2M K 3 PO 4 , 46 mL (93.76 mmol) was added thereto, 46 mL of ethanol and 200 mL of toluene were added thereto, the mixture was heated to 120 ° C., and stirred for 2 hours. After the reaction, the mixture was washed with distilled water, extracted with EA, the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator, and column (hexane / EA) was separated to obtain compound 27 (8.0 g, 43%).
MS/FAB found 789, calculated 788.93MS / FAB found 789, calculated 788.93
[실시예1] 본 발명에 따른 유기 전자 재료용 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using a Compound for Organic Electronic Materials According to the Present Invention
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine을 넣고 챔버 내의 진공도가 10E-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 화합물 9를 넣고, 또 다른 셀에는 도판트로서 화합물 D-5을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4 내지 20%중량으로 도핑 함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 9,10-디(1-나프틸)-2-(4-페닐-1-페닐-1H-벤조[d]이미다졸)안트라센[9,10-di(1-naphthyl)-2-(4-phenyl-1-phenyl-1H-benzo[d]imidazole)anthracene]을 넣고, 또다른 셀에는 리튬 퀴놀레이트(Lithium quinolate)를 각각 넣은 후, 두 물질을 다른속도로 증발시켜 30 내지 70%중량으로 도핑 함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로 Lithium quinolate를 1내지 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N1- (naphthalen-2-yl) -N4, N4-bis (4- (naphthalen-2-yl (phenyl) amino) is placed on the cell in the vacuum deposition apparatus. ) phenyl) -N1-phenylbenzene-1,4-diamine was added and evacuated until the vacuum in the chamber reached 10E-6 torr. Then, a current was applied to the cell and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Deposited. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was added to another cell in the vacuum deposition apparatus, and the cell was applied with an electric current to evaporate. A 20 nm thick hole transport layer was deposited on the hole injection layer. After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 9 as a host in one cell in a vacuum deposition equipment, Compound D-5 as a dopant in each cell, and then the two materials were evaporated at different rates to be doped at 4-20% by weight to thereby transport the hole transport layer. A light emitting layer having a thickness of 30 nm was deposited on it. Then one cell as the electron transport layer on the light emitting layer, followed by 9,10-di (1-naphthyl) -2- (4-phenyl-1-phenyl-1H-benzo [d] in one cell as the electron transport layer on the light emitting layer. ] Imidazol) anthracene [9,10-di (1-naphthyl) -2- (4-phenyl-1-phenyl-1H-benzo [d] imidazole) anthracene] and another cell is lithium quinolate (Lithium) After each quinolate) was added, the electron transport layer of 30nm was deposited by evaporating the two materials at different rates and doping at 30 to 70% by weight. Subsequently, Lithium quinolate was deposited to a thickness of 1 to 2 nm as an electron injection layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device. Each compound was used by vacuum sublimation purification under 10 -6 torr.
그 결과, 3.6 V의 전압에서 2.14 mA/cm2의 전류가 흘렀으며, 1030 cd/m2의 녹색발광이 확인되었다. As a result, a current of 2.14 mA / cm 2 flowed at a voltage of 3.6 V, and green light emission of 1030 cd / m 2 was confirmed.
[실시예2] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 2 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 9, 도판트에는 화합물 D-58을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 9 was used as a light emitting material and Compound D-58 was used as a dopant.
그 결과, 4.3 V의 전압에서 2.84 mA/cm2의 전류가 흘렀으며, 1060 cd/m2의 주황색발광이 확인되었다. As a result, a current of 2.84 mA / cm 2 flowed at a voltage of 4.3 V, and orange emission of 1060 cd / m 2 was confirmed.
[비교예1] 종래에 발광재료를 이용한 OLED 소자 제작[Comparative Example 1] Conventional OLED element fabrication using a light emitting material
발광재료로서 호스트에는 4,4‘-N,N'-dicarbazole-biphenyl, 도판트에는 화합물 D-5을 사용하고 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate을 10nm 두께로 증착한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-N, N'-dicarbazole-biphenyl is used as a light emitting material and compound D-5 is used as a dopant, and a light emitting layer having a thickness of 30 nm is deposited on the hole transport layer, and aluminum (III) bis is used as a hole blocking layer. An OLED device was manufactured in the same manner as in Example 1, except that (2-methyl-8-quinolinato) 4-phenylphenolate was deposited to a thickness of 10 nm.
그 결과, 4.9 V의 전압에서 2.86 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다. As a result, a current of 2.86 mA / cm 2 flowed at a voltage of 4.9 V, and green light emission of 1000 cd / m 2 was confirmed.
[비교예2] 종래에 발광재료를 이용한 OLED 소자 제작[Comparative Example 2] Fabrication of OLED device using light emitting material
발광재료로서 호스트에는 4,4‘-N,N'-dicarbazole-biphenyl, 도판트에는 화합물 D-58을 사용하고 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate을 10nm 두께로 증착한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-N, N'-dicarbazole-biphenyl is used as a light emitting material and compound D-58 is used as a dopant. A light emitting layer having a thickness of 30 nm is deposited on the hole transport layer, and aluminum (III) bis is used as a hole blocking layer. An OLED device was manufactured in the same manner as in Example 1, except that (2-methyl-8-quinolinato) 4-phenylphenolate was deposited to a thickness of 10 nm.
그 결과, 4.6 V의 전압에서 3.05 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 주황색발광이 확인되었다. As a result, a current of 3.05 mA / cm 2 flowed at a voltage of 4.6 V, and orange emission of 1000 cd / m 2 was confirmed.
[비교예3] 발광재료로서 호스트에는 4,4‘-N,N'-dicarbazole-biphenyl, 도판트에는 화합물 D-59을 사용하고 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate을 10nm 두께로 증착한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.Comparative Example 3 As a light emitting material, 4,4'-N, N'-dicarbazole-biphenyl was used as a host, and compound D-59 was used as a dopant. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer, and a hole blocking layer was used. An OLED device was manufactured in the same manner as in Example 1, except that aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate was deposited to a thickness of 10 nm.
그 결과, 5.2 V의 전압에서 8.2 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 진한주황색발광이 확인되었다.As a result, a current of 8.2 mA / cm 2 flowed at a voltage of 5.2 V, and dark orange light emission of 1000 cd / m 2 was confirmed.
본 발명에서 개발한 유기 전자 재료용 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 전자 재료용 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.It was confirmed that the luminescent properties of the compounds for organic electronic materials developed in the present invention showed superior characteristics compared to the conventional materials. In addition, the device using the organic electronic material compound according to the present invention as a light emitting host material was excellent in the light emitting characteristics, it was possible to improve the power consumption by inducing the increase in power efficiency by lowering the driving voltage.
Claims (9)
[화학식 1]
[상기 화학식 1에서,
X1 내지 X3는 각각 독립적으로 CH 또는 N이고, 단 X1 내지 X3가 동시에 CH인 경우는 제외하며;
L1 및 L2는 서로 독립적으로 화학결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C3-C30)헤테로아릴렌이고;
R은 수소, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이며;
R1 내지 R10는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, -NR11R12, -SiR13R14R15, -SR16, -OR17 , 시아노, 나이트로 또는 하이드록시이고;
R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있으며;
a 및 b는 각각 독립적으로 1 내지 4의 정수이고, a 및 b가 2 이상의 정수인 경우 동일하거나 상이할 수 있으며;
m 및 n은 각각 독립적으로 1 내지 3의 정수이고, m 및 n이 2 이상의 정수인 경우 동일하거나 상이할 수 있으며;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]An organic light emitting compound represented by Formula 1 below.
[Formula 1]
[In the above formula (1)
X 1 to X 3 are each independently CH or N, provided that X 1 to X 3 are Except when CH at the same time;
L 1 And L 2 is independently a chemical bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (C3-C30) heteroarylene;
R is hydrogen, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) heteroaryl;
R 1 To R 10 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitro or hydroxy;
R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero A cycloaliphatic ring and a monocyclic ring or a polycyclic ring which is connected to a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene, which is aryl or does not include or include a fused ring with adjacent substituents. An aromatic ring of the ring may be formed, and the carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen, and sulfur;
a and b are each independently an integer of 1 to 4, and may be the same or different when a and b are integers of 2 or more;
m and n are each independently an integer of 1 to 3, and may be the same or different when m and n are an integer of 2 or more;
Wherein said heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P.
상기 L1, L2, R, R1 내지 R10 및 R11 내지 R17에 더 치환되는 치환기는중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C5-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C5-C30)헤테로아릴, (C3-C30)시클로알킬, 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C6-C30)알키닐, 시아노, 카바졸릴, 디C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 것인 유기 발광 화합물.The method of claim 1,
Substituents further substituted with L 1 , L 2 , R, R 1 to R 10 and R 11 to R 17 are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C30) aryl, (C5-C30) heteroaryl, (C6-C30) aryl substituted (C5-C30) heteroaryl, (C3-C30) cycloalkyl, heterocycloalkyl, tri (C1-C30) alkylsilyl , Tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C6 -C30) alkynyl, cyano, carbazolyl, diC1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) aryl Boronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl An organic light emitting compound selected from the group consisting of (C6-C30) aryl, carboxyl, nitro and hydroxy.
상기 R은 수소, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐 또는 페릴렌일이고;
L1 및 L2는 서로 독립적으로 화학결합, 페닐렌, 나프틸렌, 비페닐렌, 플루오레닐렌, 안트라세닐렌, 피리디닐렌, 퓨란닐렌, 티오페닐렌, 다이벤조티오페닐렌,, 다이벤조퓨란닐렌 또는 -페닐렌-다이벤조티오페닐렌이고;
R1 내지 R8은 서로 독립적으로 수소, 중수소, 클로로, 플루오르, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일 또는 N-카바졸릴이고;
R9 및 R10은 서로 독립적으로 수소, 중수소, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 다이벤조티오페닐, 벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일 또는 N-카바졸릴이고;
상기 R의 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐 또는 페릴렌일, 및 R1 내지 R10의 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 다이벤조티오페닐, 벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴 또는 페난트롤린일은 각각 중수소, 클로로, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴 및 트리페닐실릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것인 유기 발광 화합물.The method of claim 1,
R is hydrogen, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl or peryleneyl;
L 1 and L 2 are each independently a chemical bond, phenylene, naphthylene, biphenylene, fluorenylene, anthracenylene, pyridinylene, furanylene, thiophenylene, dibenzothiophenylene, dibenzo Furanylene or -phenylene-dibenzothiophenylene;
R 1 To R 8 are independently of each other hydrogen, deuterium, chloro, fluorine, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, Peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl , Benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl or N-carbazolyl;
R 9 and R 10 are independently of each other hydrogen, deuterium, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl , Pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl or N-carbazolyl;
Phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl or peryleneyl of said R, and R 1 To R 10 phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl , Thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazineyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothiophenyl, Pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl or phenanthrolinyl are deuterium, chloro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i- Butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl , Trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, tri Consisting of riphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl and triphenylsilyl An organic light emitting compound that can be further substituted with one or more substituents selected from the group.
하기 화합물로부터 선택되는 유기 발광 화합물.
An organic light emitting compound selected from the following compounds.
상기 유기 전계 발광 소자가 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가지며, 이 유기물층이 상기 유기 발광 화합물 중 하나 이상과 하기 화학식 2으로 표시되는 인광도판트 중 하나 이상을 포함하는 것인 유기 전계 발광 소자.
[화학식 2]
M 1 L 101 L 102 L 103
[상기 화학식 2에서,
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고,
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;
Q는
The organic electroluminescent device 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 includes at least one of the organic light emitting compounds and at least one of phosphorescent dopants represented by Formula 2 below. Light emitting element.
(2)
M 1 L 101 L 102 L 103
[In Formula 2,
Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os,
The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q is
상기 인광 도판트는 하기 화합물로부터 선택되는 것인 유기 전계 발광 소자.
The phosphorescent dopant is selected from the following compounds.
상기 유기물층이 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물(A); 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 금속을 포함하는 착체화합물(B); 또는 이들의 혼합물을 포함하는 것인 유기 전계 발광 소자.The method according to claim 6,
At least one amine compound (A) wherein the organic material layer is selected from the group consisting of an arylamine compound or a styrylarylamine compound; Complex compounds (B) comprising at least one metal or metal selected from the group consisting of Group 1, Group 2, 4 and 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements; Or an organic electroluminescent device comprising a mixture thereof.
상기 유기물층이 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것인 유기 전계 발광 소자.The method according to claim 6,
The organic light emitting device of claim 1, wherein the organic material layer further comprises at least one organic light emitting layer emitting blue, red, or green light.
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