KR20110104765A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
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- KR20110104765A KR20110104765A KR1020100023851A KR20100023851A KR20110104765A KR 20110104765 A KR20110104765 A KR 20110104765A KR 1020100023851 A KR1020100023851 A KR 1020100023851A KR 20100023851 A KR20100023851 A KR 20100023851A KR 20110104765 A KR20110104765 A KR 20110104765A
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- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- aryl
- fused
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 77
- 239000000126 substance Substances 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims description 92
- -1 nitro, hydroxy Chemical group 0.000 claims description 72
- 239000010410 layer Substances 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 239000002019 doping agent Substances 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 125000002723 alicyclic group Chemical group 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 229910052717 sulfur Chemical group 0.000 claims description 15
- 125000004450 alkenylene group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000005549 heteroarylene group Chemical group 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000011368 organic material Substances 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 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
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 239000001301 oxygen Chemical group 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
- 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
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003831 tetrazolyl 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 38
- 230000001939 inductive effect Effects 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 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
- 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 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 229940125900 compound 59 Drugs 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 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 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 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
- 238000012827 research and development Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- XHZUPQUVMGRPDC-UHFFFAOYSA-N 1,2,3,4-tetratert-butylperylene Chemical group C1=CC(C2=C(C(C(C)(C)C)=C(C=3C2=C2C=CC=3C(C)(C)C)C(C)(C)C)C(C)(C)C)=C3C2=CC=CC3=C1 XHZUPQUVMGRPDC-UHFFFAOYSA-N 0.000 description 1
- YQRNVIBATHFHCC-UHFFFAOYSA-N 1,2-dimethylbenzo[a]anthracene Chemical compound C1=CC=C2C=C(C=3C(=CC=C(C=3C)C)C=C3)C3=CC2=C1 YQRNVIBATHFHCC-UHFFFAOYSA-N 0.000 description 1
- LCAKAXJAQMMVTQ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-2-phenylbenzene Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LCAKAXJAQMMVTQ-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-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
- 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 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- ADSDVEDOVSDRSP-UHFFFAOYSA-N C(C1C=C2)C1c(cc1)c2cc1-c1c(cc(cc2)N3c4ccccc4CCC3)c2c(-c2cc3ccccc3cc2)c2c1ccc(N(CCC1)c3c1cccc3)c2 Chemical compound C(C1C=C2)C1c(cc1)c2cc1-c1c(cc(cc2)N3c4ccccc4CCC3)c2c(-c2cc3ccccc3cc2)c2c1ccc(N(CCC1)c3c1cccc3)c2 ADSDVEDOVSDRSP-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
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- VRNJEBVCIIHSIU-UHFFFAOYSA-N FC1C=CC(c2cc(N(c3c(cccc4)c4ccc3)c3c(ccc(c4c5CC6)ccc5N(C(C5)=CC(c(cc7)ccc7F)=CC5c5ccccc5)c5cccc7c5cccc7)c4c6cc3)cc(-c3ccccc3)c2)=CC1 Chemical compound FC1C=CC(c2cc(N(c3c(cccc4)c4ccc3)c3c(ccc(c4c5CC6)ccc5N(C(C5)=CC(c(cc7)ccc7F)=CC5c5ccccc5)c5cccc7c5cccc7)c4c6cc3)cc(-c3ccccc3)c2)=CC1 VRNJEBVCIIHSIU-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 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
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
- YNDGEMZBYUVHTH-UHFFFAOYSA-N [4-(10-phenylanthracen-9-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YNDGEMZBYUVHTH-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
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 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
- 125000005577 anthracene group Chemical group 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
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 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
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=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
- 150000002739 metals Chemical class 0.000 description 1
- ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction 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
- 238000010992 reflux Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
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- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/30—Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
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- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것으로, 상세하게는 본 발명에 따른 유기 발광 화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다.
[화학식 1]
상기 화학식 1에서, A, B, R1 내지 R2, R3 내지 R11, R12 내지 R19, Ar, a 및 b은 각각 발명의 상세한 설명에서 정의한 바와 같다.
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 a novel organic light emitting compound and an organic electroluminescent device comprising the same, in detail, the organic light emitting compound according to the invention is characterized in that represented by the formula (1).
[Formula 1]
In Chemical Formula 1, A, B, R 1 to R 2 , R 3 to R 11 , R 12 to R 19 , Ar, a and b are as defined in the detailed description of the invention, respectively.
The organic light emitting compound according to the present invention has better luminous efficiency and excellent lifespan characteristics than the conventional materials, and thus, an OLED device having improved power consumption can be manufactured by inducing an increase in power efficiency as well as an excellent driving life of the device. There is an advantage.
Description
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것으로, 보다 구체적으로는 발광 재료로서 사용되는 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic light emitting compound used as a light emitting material and an organic electroluminescent device employing 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 있으며, 1987년 이스트만 코닥(Eastman Kodak)사에서는 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 that has a wide viewing angle, excellent contrast, and high response speed.Eastman Kodak Co., Ltd. in 1987 An organic EL device using a low molecular aromatic diamine and an aluminum complex as a light emitting layer formation material was first developed [Appl. Phys. Lett. 51, 913, 1987].
유기 EL 소자는 전자 주입 전극(음극) 과 정공 주입 전극(양극) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다. 플라스틱 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 EL 디스플레이에 비해 낮은 전압에서 (10V이하) 구동이 가능하고, 또한 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다. 또한 유기 EL 소자는 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 차세대 풍부한 색 디스플레이 소자로 많은 사람들의 많은 관심의 대상이 되고 있다. An organic EL device is a device that emits light when an electron is injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and then disappears after pairing electrons and holes. The device can be formed on a flexible transparent substrate such as plastic, and can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and also consumes power. It is relatively small and has the advantage of excellent color. In addition, the organic EL device can display three colors of green, blue, and red, and thus, has become a subject of much interest as a next-generation rich color display device.
유기 EL 소자에서 발광 효율, 수명 등의 성능을 결정하는 가장 중요한 요인은 발광 재료로서, 이러한 발광 재료에 요구되는 몇 가지 특성으로는 고체상태에서 발광 양자 수율이 커야하고, 전자와 정공의 이동도가 높아야 하며, 진공 증착시 쉽게 분해되지 않아야 하고, 균일한 박막을 형성, 안정해야한다. The most important factor that determines the performance of light emission efficiency, lifespan, etc. in the organic EL device is the light emitting material. Some characteristics required for such a light emitting material include high light emission quantum yield in the solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and should form and stabilize a uniform thin film.
유기EL소자는 보통 anode/HIL/HTL/EML/ETL/EIL/cathode로 구성되는데 발광층(EML)을 어떻게 형성하느냐에 따라 청색, 녹색, 적색의 유기 전기 발광 소자를 각각 구현할 수가 있다. The organic EL device is usually composed of anode / HIL / HTL / EML / ETL / EIL / cathode. The organic electroluminescent device of blue, green, and red can be realized depending on how the emission layer (EML) is formed.
발광재료는 기능적인 측면에서 호스트 재료와 도판트 재료로 구분될 수 있는데 일반적으로 EL 특성이 가장 우수한 소자 구조로는 호스트에 도판트를 도핑하여 발광층을 만드는 것으로 알려져 있다. 최근에 고효율, 장수명 유기 EL 소자의 개발이 시급한 과제로 대두되고 있으며, 특히 중대형 OLED 패널에서 요구하고 있는 EL 특성 수준을 고려해 볼 때 기존의 발광재료에 비해 매우 우수한 재료의 개발이 시급한 실정이다. The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic EL devices has emerged as an urgent task, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials.
한편, 종래 청색 재료의 경우, 이데미쓰-고산의 디페닐비닐-비페닐(DPVBi, 화합물 a) 이후로 많은 재료들이 개발되어 상업화되어 있으며, 이데미쓰-고산의 청색 재료 시스템과 코닥의 디나프틸안트라센(dinaphthylanthracen; DNA, 화합물 b), 테트라(t-부틸)페릴렌(tetra(t-butyl)perlyene, 화합물 c) 시스템 등이 알려져 있으나, 아직도 많은 연구 개발이 이루어져야 할 것으로 판단된다. On the other hand, in the case of the conventional blue material, many materials have been developed and commercialized since Idemitsu-high acid diphenylvinyl-biphenyl (DPVBi, compound a), and the Idemitsu-high acid blue material system and Kodak's dinaphthyl Although anthracene (dinaphthylanthracen; DNA, compound b), tetra (t-butyl) perylene (compound c) system, etc. are known, many research and developments are still required.
현재까지 가장 효율이 좋다고 알려진 이데미쓰-고산의 디스트릴(distryl)화합물의 시스템은 파워 효율의 경우, 6 lm/W이고, 소자 수명이 30,000 시간 이상으로 좋기는 하나, 구동 시간에 따른 색순도의 저하로 인하여 풀컬러 디스플레이에 적용했을 때, 수명이 불과 수천시간에 불과하다. 청색 발광은 발광 파장이 장파장 쪽으로 조금만 이동해도 발광 효율 측면에서는 유리해지나, 순청색을 만족시키지 못해 고품위의 디스플레이에는 적용이 쉽지 않은 문제점을 갖고 있으며, 색순도, 효율 및 열안정성에 문제가 있어 연구 개발이 시급한 부분이라고 하겠다.The system of Idemitsu-high acid disryl compound, which is known to be the most efficient so far, has a power efficiency of 6 lm / W and a device life of more than 30,000 hours, but the color purity decreases with driving time. When applied to a full-color display, its lifetime is only thousands of hours. Blue light emission is advantageous in terms of luminous efficiency even if the light emission wavelength is shifted toward the longer wavelength, but it is not easy to apply to high-quality display because it does not satisfy pure blue color, and there is a problem in color purity, efficiency and thermal stability, so that research and development It is an urgent part.
이처럼 종래의 재료들은 호스트-도판트 박막층을 구성하지 않고 단일층으로 구성되어져 있으며, 색순도 및 효율 측면에서 상용화가 어려운 것으로 판단되며, 장수명에 대한 신뢰성 있는 데이터도 미비한 상황이다. As described above, the conventional materials are composed of a single layer without forming a host-dopant thin film layer, and it is determined that commercialization is difficult in terms of color purity and efficiency, and reliable data on long life is insufficient.
또한, 녹색 형광 재료로는 Alq를 호스트로 하여, 도판트로는 쿠마린 유도체(화합물 d, C545T), 퀴나크리돈 유도체(화합물 e), DPT(화합물 f) 등을 수 내지 십수 % 정도로 도핑을 하는 시스템이 개발되어 널리 쓰이고 있다. 그러나, 이들 종래의 발광재료는 초기 발광효율의 경우, 상용화 가능한 수준의 성능을 보이나, 초기 효율 저하가 두드러지며 수명 측면에서 상당한 문제점을 보이고 있어, 대화면의 고성능 패널에서는 채택하기가 힘든 한계를 보이고 있다.In addition, as a green fluorescent material, Alq is used as a host, and as a dopant, doping of coumarin derivatives (compounds d and C545T), quinacridone derivatives (compound e), DPT (compound f) and the like is performed in the order of several to several ten percent. It is developed and widely used. However, these conventional light emitting materials show a commercially available level of performance in the case of the initial luminous efficiency, but the initial efficiency decreases remarkably and shows considerable problems in terms of lifespan. .
또한, OLED 소자에서의 수명 측면에서도 결코 만족할만한 수준이 되질 못하여 더욱 안정되고, 더욱 성능이 뛰어난 호스트 재료의 개발이 요구되고 있다.In addition, in terms of lifespan in OLED devices, they are never satisfactory, and development of a more stable and more excellent host material is required.
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,
R1 내지 R2은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴 또는 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬이고;R 1 to R 2 are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl or substituted or unsubstituted 5 to 7 membered heterocycloalkyl;
R3 내지 R11은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 시아노, 나이트로, 하이드록시, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31 또는 -YR32이며;R 3 to R 11 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, cyano, nitro, hydroxy, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R 26 , -P (= O) R 27 R 28 , -SiR 29 R 30 R 31, or -YR 32 ;
R12 내지 R19은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, 하이드록시, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐이거나, 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 있고;R 12 to R 19 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cyclo Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted, with one or more alkyl fused To 7-membered heterocycloalkyl fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic rings with one or more fused (C3-C30) cycloalkyl , Cyano, nitro, hydroxy, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R 26 , -P (= O) R 27 R 28 , -SiR 29 R 30 R 31 , -YR 32 Or substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, or fused with an adjacent substituent Including collars It may be connected to a substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene which do not include to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, The carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
Ar은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, 하이드록시, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 또는 치환 또는 비치환된(C2-C30)알키닐이며;Ar is independently of one another hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Fused substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring At least one fused 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring at least one fused (C3-C30) cycloalkyl, cyano, Nitro, hydroxy, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R 26 , -P (= O) R 27 R 28 , -SiR 29 R 30 R 31 , -YR 32 , substituted or unsubstituted Substituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, or substituted or unsubstituted (C2-C30) alkynyl;
A는 화학결합이거나, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C2-C30)헤테로아릴렌 또는 치환 또는 비치환된(C6-C30)아릴렌티오이고; A is a chemical bond or is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene or substituted or unsubstituted (C6-C30) arylenethio;
B는 화학결합이거나, 치환 또는 비치환된(C2-C30)알킬렌, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C3-C30)헤테로아릴렌, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된(C3-C30)시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬렌, 치환 또는 비치환된 지환족고리가 하나 이상 융합된 (C6-C30)아릴렌, 치환 또는 비치환된(C2-C30)알케닐렌, 치환 또는 비치환된(C2-C30)알키닐렌, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬렌, 치환 또는 비치환된(C1-C30)알킬렌티오, 치환 또는 비치환된(C1-C30)알킬렌옥시, 치환 또는 비치환된(C6-C30)아릴렌옥시이거나, 치환 또는 비치환된(C6-C30)아릴렌티오이고; B is a chemical bond, substituted or unsubstituted (C2-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) heteroarylene, substituted or unsubstituted 5- to 7-membered heterocycloalkylene, substituted or unsubstituted aromatic ring, 5- to 7-membered heterocycloalkylene, substituted or unsubstituted (C3-C30) cycloalkylene, substituted Or (C3-C30) cycloalkylene in which one or more unsubstituted aromatic rings are fused, (C6-C30) arylene in which one or more substituted or unsubstituted alicyclic rings are fused, substituted or unsubstituted (C2-C30). ) Alkenylene, substituted or unsubstituted (C2-C30) alkynylene, substituted or unsubstituted (C6-C30) ar (C1-C30) alkylene, substituted or unsubstituted (C1-C30) alkylenethio, Substituted or unsubstituted (C1-C30) alkyleneoxy, substituted or unsubstituted (C6-C30) aryleneoxy, or substituted or unsubstituted (C6-C30) arylenethio;
R21 내지 R32는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C3-C30)헤테로시클로알킬이거나, 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;R 21 to R 32 are independently of each other hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or Unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) heterocycloalkyl, substituted or unsubstituted (C3-C30) alkylene with or without fused ring with adjacent substituents or Linked with substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
Y는 S 또는 O이며;Y is S or O;
a 및 b는 서로 독립적으로 1 내지 3의 정수이고; a가 2 이상의 정수인 경우 A는 동일하거나 상이할 수 있고, b가 2 이상의 정수인 경우 B는 동일하거나 상이할 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있고;a and b are each independently an integer of 1 to 3; when a is an integer of 2 or more, A may be the same or different, and when b is an integer of 2 or more, B may be the same or different, and adjacent substituents may combine with each other to form a ring;
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 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 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 연걸된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 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 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다.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, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthasenyl, fluoranthenyl, and the like. It is not limited to 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. The "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. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked 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, tetra Monocyclic heteroaryl such as zolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothia Zolyl, Benzoisoxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl , Polycyclic heteroaryls such as benzodioxolyl and the like, and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. .
또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 (C1-C20)알킬 또는 (C1-C10)알킬을 포함하고, ‘(C6-C30)아릴’기는 (C6-C20)아릴 또는 (C6-C12)아릴을 포함한다. ‘(C3-C30)헤테로아릴’기는 (C3-C20)헤테로아릴 또는 (C3-C12)헤테로아릴을 포함하고, ‘(C3-C30)시클로알킬’기는 (C3-C20)시클로알킬 또는 (C3-C7)시클로알킬을 포함한다. ‘(C2-C30)알케닐 또는 알키닐’기는 (C2-C20)알케닐 또는 알키닐, (C2-C10)알케닐 또는 알키닐을 포함한다.In addition, the '(C1-C30) alkyl' groups described herein include (C1-C20) alkyl or (C1-C10) alkyl, and the '(C6-C30) aryl' group is a (C6-C20) aryl or (C6-C12) aryl. '(C3-C30) heteroaryl' group includes (C3-C20) heteroaryl or (C3-C12) heteroaryl, and the '(C3-C30) cycloalkyl' group is (C3-C20) cycloalkyl or (C3- C7) cycloalkyl. '(C2-C30) alkenyl or alkynyl' groups include (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 R1 내지 R2, R3 내지 R11, R12 내지 R19, Ar, A, B 및 R21 내지 R32에 더 치환되는 치환기는 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C6-C30)시클로알킬, RaRbRcSi-, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NRdRe, BRfRg, PRhRi, P(=O)RjRk, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, RlX-, RmC(=O)-, RmC(=O)O-, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상이고, Ra 내지 Rl는 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이고; X는 S 또는 O이고; Rm는 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴 또는 (C6-C30)아릴옥시인 것을 의미한다.In addition, in the description of "substituted or unsubstituted" described in the present invention, 'substituted' refers to a case where it is further substituted with an unsubstituted substituent, the R 1 to R 2 , Substituents further substituted with R 3 to R 11 , R 12 to R 19 , Ar, A, B and R 21 to R 32 independently of each other, deuterium, halogen, (C 1 -C 30) alkyl unsubstituted or substituted with halogen, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered fused at least one aromatic ring Heterocycloalkyl, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, R a R b R c Si-, (C2-C30) alkenyl, (C2-C30) alky Nyl, cyano, carbazolyl, NR d R e , BR f R g , PR h R i , P (= O) R j R k , (C6-C30) ar (C1-C30) alkyl, (C1-C30 One or more selected from the group consisting of alkyl (C6-C30) aryl, R 1 X-, R m C (= 0)-, R m C (= 0) O-, carboxyl, nitro or hydroxy , R a to R l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; X is S or O; R m means (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy.
상기 A는 화학결합이거나, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C2-C30)헤테로아릴렌 또는 치환 또는 비치환된(C6-C30)아릴렌티오(화합물 68번 참고)이고; B는 화학결합이거나, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C3-C30)헤테로아릴렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬렌, 치환 또는 비치환된 지환족고리가 하나 이상 융합된 (C6-C30)아릴렌, 치환 또는 비치환된(C2-C30)알케닐렌 또는 치환 또는 비치환된(C2-C30)알키닐렌이고; R1 내지 R19는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴 또는 -NR21R22 이거나, 인접한 치환체와 C5알킬렌 또는 
또한, 상기 Ar은 수소, 중수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 플루오르, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴, 트리페닐실릴, 메톡시, 에톡시, n-프로폭시, i-프로폭시, n-부톡시, i-부톡시, t-부톡시, n-펜톡시, i-펜톡시, n-헥실옥시, n-헵톡시, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 테트라졸릴, 피라지닐, 피리미딜, 벤조퓨란일, 벤조티오펜일, 피라졸릴, 인돌릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 디메틸아미노, 디페닐아미노, 모노메틸아미노, (4-t-부틸페닐)(페닐)아미노, 모노페닐아미노, 페닐옥시, 페닐티오, 트리페닐메틸, 페닐, 나프틸, 바이페닐, 페난트릴, 피레닐, 플루오란테닐, 피리딜, 인데닐, 트리페닐레닐, 테트라하이드로나프틸, 7H-벤조[c]플루오레닐, 7H-벤조[de]안트라세닐, 테트라하이드로퀴놀릴, 안트라세닐, 7H-벤조[c]카바졸릴, 에티닐, 에테닐, 퀴놀릴, 
더욱 구체적으로 상기 A는 화학결합 또는 하기 구조로부터 선택되고;More specifically, A is selected from chemical bonds or the following structures;
본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 하기 화합물이 본 발명을 한정하는 것은 아니다.The organic light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.
본 발명에 따른 유기 발광 화합물은 하기 반응식 1에 나타난 바와 같이, 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in Scheme 1 below.
[반응식 1]Scheme 1
[상기 반응식 1에서 R1 내지 R2, R3 내지 R11, R12 내지 R19, A, B, Ar, a 및 b는 상기 화학식 1에서의 정의와 동일하다.][R 1 to R 2 in Scheme 1, R 3 to R 11 , R 12 to R 19 , A, B, Ar, a and b are the same as defined in Formula 1 above.]
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 유기물층으로 이루어진 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. 상기 유기물층은 발광층을 포함하고, 상기 발광층에서 상기 화학식 1의 유기 발광 화합물은 호스트 또는 도판트 물질로 사용되어진다. 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 organic light emitting compound of Formula 1. The organic material layer includes a light emitting layer, and the organic light emitting compound of Formula 1 is used as a host or dopant material in the light emitting layer.
상기 발광층에서 상기 화학식 1의 유기발광화합물이 호스트로 사용되어질 때 하나 이상의 도판트를 포함하는 것을 특징으로 한다. 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 특별히 제한되지는 않으나, 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 하기 화학식 2로 표시되는 화합물로부터 선택되는 것이 바람직하다.When the organic light emitting compound of Formula 1 is used as a host in the light emitting layer is characterized in that it comprises one or more dopants. The dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but the dopant applied to the organic electroluminescent device of the present invention is preferably selected from a compound represented by the following formula (2).
[화학식 2][Formula 2]
[상기 화학식 2에서, Ar101 및 Ar102는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C4-C30)헤테로아릴, 치환 또는 비치환된 (C6-C30)아릴아미노, (C1-C30)알킬아미노, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬이고, Ar101 및 Ar102는 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하고; [In Formula 2, Ar 101 and Ar 102 are independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C4-C30) hetero One or more fused aryl, substituted or unsubstituted (C6-C30) arylamino, (C1-C30) alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic rings 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring is a (C3-C30) cycloalkyl fused at least one, Ar 101 and Ar 102 is Linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
c가 1인 경우 Ar103은 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C4-C30)헤테로아릴 또는 하기 구조에서 선택되는 치환기이고;when c is 1 Ar 103 is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;
c가 2인 경우 Ar103는 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된(C4-C30)헤테로아릴렌 또는 하기 구조에서 선택되는 치환기이고;when c is 2, Ar 103 is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;
Ar104 및 Ar105은 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌 또는 치환 또는 비치환된(C4-C30)헤테로아릴렌이고;Ar 104 and Ar 105 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene;
R101 내지 R103는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴, -NR111R112, -BR113R114, -PR115R116, -P(=O)R117R118, -SiR119R120R121 또는 -YR122이며;R 101 to R 103 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl, -NR 111 R 112 , -BR 113 R 114 , -PR 115 R 116 , -P (= 0) R 117 R 118 , -SiR 119 R 120 R 121 or -YR 122 ;
R111 내지 R122는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C3-C30)헤테로시클로알킬이고, R111 내지 R122가 각각 독립적으로 인접한 치환체들 끼리 서로 결합하여 고리를 형성할 경우 치환 또는 비치환된 (C3-C30)의 지방족 고리, 치환 또는 비치환된 (C5-C30)의 헤테로지방족 고리, 치환 또는 비치환된 (C6-C30)의 방향족 고리, 치환 또는 비치환된 (C6-C30)의 헤테로방향족 고리를 형성할 수 있고R 111 to R 122 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or Unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) heterocycloalkyl, and R 111 to R 122 are each independently substituted or unsubstituted when adjacent substituents combine with each other to form a ring; A substituted (C3-C30) aliphatic ring, a substituted or unsubstituted (C5-C30) heteroaliphatic ring, a substituted or unsubstituted (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) Can form a heteroaromatic ring of
상기 Y는 S 또는 O이며; Y is S or O;
d는 1 내지 4의 정수이며, e는 0 또는 1의 정수이다.]
d is an integer of 1 to 4, and e is an integer of 0 or 1.]
상기 화학식 2의 도판트 화합물은 하기 구조의 화합물로 예시될 수 있으나 이에 한정하는 것은 아니다.The dopant compound of Formula 2 may be exemplified as a compound having the following structure, but is not limited thereto.
상기 발광층에서 상기화학식 1의 유기발광화합물이 도판트로 사용되어 질때 하나 이상의 호스트를 포함하는 것을 특징으로 한다. 본 발명의 유기 전계 발광 소자에 적용되는 호스트는 특별히 제한되지는 않으나, 본 발명의 유기 전계 발광 소자에 적용되는 호스트는 하기 화학식 3 내지 4로 표시되는 화합물로부터 선택되는 것이 바람직하다.When the organic light emitting compound of Formula 1 is used as a dopant in the light emitting layer, it characterized in that it comprises at least one host. The host applied to the organic electroluminescent device of the present invention is not particularly limited, but the host applied to the organic electroluminescent device of the present invention is preferably selected from compounds represented by the following Chemical Formulas 3 to 4.
[화학식 3](3)
(Ar11)f-L11-(Ar12)g (Ar 11 ) f -L 11- (Ar 12 ) g
[화학식 4][Formula 4]
(Ar13)h-L12-(Ar14)i (Ar 13 ) h -L 12- (Ar 14 ) i
[상기 화학식 3 내지 4에서,[In Formulas 3 to 4,
L11는 치환 또는 비치환된 (C6-C60)아릴렌 또는 치환 또는 비치환된 (C4-C60)헤테로아릴렌이고;L 11 is substituted or unsubstituted (C6-C60) arylene or substituted or unsubstituted (C4-C60) heteroarylene;
L12는 치환 또는 비치환된 안트라세닐렌이며;L 12 is substituted or unsubstituted anthracenylene;
Ar11 내지 Ar14은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 시아노, 나이트로, -NR201R202, -BR203R204, -PR205R206, -P(=O)R207R208, R209R210R211Si-, R212X-, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐이거나, 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 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소로 치환될 수 있고; Ar 11 to Ar 14 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl fused or substituted at least one (C6-C30) aryl, substituted or unsubstituted 5 5-7 membered heterocycloalkyl, cyano, nitro, fused with one or more membered heterocycloalkyl, substituted or unsubstituted aromatic rings, -NR 201 R 202 , -BR 203 R 204 ,- PR 205 R 206 , -P (= O) R 207 R 208 , R 209 R 210 R 211 Si-, R 212 X-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) alkylene or substituted with or without a fused ring with adjacent substituents Or unsubstituted Linked to a (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the carbon atoms of the monocyclic or polycyclic aromatic ring formed may be substituted with nitrogen;
R201 내지 R212는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고;R 201 to R 212 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;
X는 S 또는 O이고;X is S or O;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P;
f, g, h 및 i는 서로 독립적으로 0 내지 4의 정수이다.]f, g, h and i are each independently an integer from 0 to 4.]
상기 화학식 3 내지 4의 호스트 화합물은 하기 구조의 화합물로 예시될 수 있으나 이에 한정하는 것은 아니다.The host compounds of Formulas 3 to 4 may be exemplified as a compound having the following structure, but are not limited thereto.
본 발명의 유기 전계 발광 소자에 있어서, 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. 상기 아릴아민계 화합물 또는 스티릴아릴아민계 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In the organic electroluminescent device of the present invention, it may include one or more compounds selected from the group consisting of an organic light emitting compound of formula (1) and at the same time an arylamine compound or styrylarylamine compound. The arylamine-based compound or styrylarylamine-based compound is exemplified in Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but is not limited thereto.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층 및 전하생성층을 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic light emitting compound of Chemical Formula 1, a group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element It may further comprise one or more metals or complex compounds selected from, the organic material layer may include a light emitting layer and a charge generating layer.
또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In addition, an organic electroluminescent device that emits white light may be formed by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.
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 칼코제나이드로서는 예컨대 SiOx(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON 등을 바람직하게 들 수 있으며, 할로겐화 금속으로서는 예컨대 LiF, MgF2, CaF2, 불화 희토류 금속 등을 바람직하게 들 수 있으며, 금속 산화물로서는 예컨대 Cs2O, Li2O, MgO, SrO, BaO, CaO 등을 바람직하게 들 수 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. Examples of the chalcogenide include SiO x (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like are preferable. 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 방식으로, 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 있다. 바람직한 환원성 도판트로서는 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 도 있다.Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into 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, the reducing dopant layer The white organic electroluminescent device having two or more light emitting layers may be manufactured using the 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 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.
[제조예 1]화합물 1의 제조Preparation Example 1 Preparation of Compound 1
화합물 compound 1-11-1 의 제조Manufacture
벤즈안트론 40.0g(0.17mol)을 다이에틸이써 1000mL에 녹이고, AlCl3 28g(0.21mol)을 천천히 첨가하였다. 이를 15분동안 교반한 후, 0℃로 냉각하고 리튬알루미늄하이드라이드(LAH) 10g(0.26mol)를 천천히 첨가하였다. 이를 1시간동안 환류 교반한 후 반응이 완결되면 상온으로 천천히 냉각하고, 여기에 EA를 거품이 일어나지 않을 때까지 천천히 넣어주었다. 그런 다음 6M HCl 100mL을 넣어주고, 증류수와 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 다음 회전 증발기로 용매를 제거한 후 디클로로메탄과 헥산을 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 화합물 1-1 36.0g (95%)을 얻었다.40.0 g (0.17 mol) of benzanthrone was dissolved in 1000 mL by diethyl ether, and 28 g (0.21 mol) of AlCl 3 was slowly added. After stirring for 15 minutes, it was cooled to 0 ° C and slowly added 10 g (0.26 mol) of lithium aluminum hydride (LAH). After stirring for 1 hour under reflux, the reaction was slowly cooled to room temperature when the reaction was completed, and EA was slowly added thereto until no foaming occurred. Then, 100 mL of 6M HCl was added thereto, and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 , and then the solvent was removed using a rotary evaporator, and then purified by column chromatography using dichloromethane and hexane as a developing solvent, to obtain 36.0 g (95%) of Compound 1-1 .
화합물 compound 1-21-2 의 제조Manufacture
화합물 1-1 36.0g(0.16mol)을 DMSO 420mL에 녹인 다음, 상온에서 소듐 tert-부톡사이드 113.0g(1.2mol)를 넣어주고 70℃에서 15분간 교반하였다. 여기에 요오드화 메틸 (Methyl Iodide) 90 mL(1.4mol)을 천천히 첨가하고 1시간 더 교반하였다. 반응이 완결되면 상온에서 냉각하고 증류수를 넣어 20분간 교반하였다. 이때 고체가 생성되는데 이를 필터하고, 얻어진 고체를 메탄올과 아세톤으로 재결정하여 화합물 1-2 26g (63%)을 얻었다. 36.0 g (0.16 mol) of Compound 1-1 was dissolved in 420 mL of DMSO, and then 113.0 g (1.2 mol) of sodium tert-butoxide was added at room temperature, followed by stirring at 70 ° C. for 15 minutes. 90 mL (1.4 mol) of methyl iodide was slowly added thereto, and the mixture was further stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added and stirred for 20 minutes. At this time, a solid was formed, which was filtered, and the obtained solid was recrystallized from methanol and acetone to obtain 26 g (63%) of compound 1-2 .
화합물 compound 1-31-3 의 제조Manufacture
화합물 1-2 20g(90mmol)을 DMF 300mL에 녹이고, N-브로모숙신이미드 16g (90mmol)를 천천히 첨가하였다. 이를 상온에서 하루동안 교반한 후 반응이 완결되면 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 디클로로메탄과 헥산을 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 목적화합물 1-3 26g(91%)을 얻었다.20 g (90 mmol) of Compound 1-2 were dissolved in 300 mL of DMF, and 16 g (90 mmol) of N-bromosuccinimide was slowly added. After stirring for one day at room temperature, the reaction was extracted with distilled water and EA. The organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent, to obtain 26 g (91%) of the title compound 1-3 .
화합물 compound 1One 의 제조Manufacture
10-페닐안트라센-9-일보론산 32g(107mmol), 화합물 1-3 25g(82mmol), Pd(PPh3)4 6.2g(5.4mmol) 및 Na2CO3 17.4g(164mmol)을 톨루엔/에탄올/증류수 400mL/100mL/80mL에 녹인 다음 100℃에서 교반하였다. 반응이 완결되면 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 디클로로메탄과 헥산을 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 목적화합물 1 33g(81%)을 얻었다.
32 g (107 mmol) of 10-phenylanthracene-9-ylboronic acid, 25 g (82 mmol) of compound 1-3 , 6.2 g (5.4 mmol) of Pd (PPh 3 ) 4 and 17.4 g (164 mmol) of Na 2 CO 3 were added to toluene / ethanol / It was dissolved in 400mL / 100mL / 80mL of distilled water and stirred at 100 ° C. When the reaction was completed, extracted with distilled water and EA. The organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain 33 g (81%) of the title compound 1 .
[제조예 2]화합물 58의 제조Preparation Example 2 Preparation of Compound 58
4-(10-페닐안트라센-9-일)페닐보론산 40g(107mmol), 화합물 1-3 25g(82mmol), Pd(PPh3)4 6.2g(5.4mmol) 및 Na2CO3 17.4g(164mmol)을 톨루엔/에탄올/증류수 400mL/100mL/80mL에 녹인 다음 100℃에서 교반하였다. 반응이 완결되면 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 디클로로메탄과 헥산을 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 목적화합물 58 37g(79%)을 얻었다.40 g (107 mmol) of 4- (10-phenylanthracene-9-yl) phenylboronic acid, 25 g (82 mmol) of compound 1-3 , 6.2 g (5.4 mmol) of Pd (PPh 3 ) 4 and Na 2 CO 3 17.4 g (164 mmol) was dissolved in toluene / ethanol / distilled water 400mL / 100mL / 80mL and stirred at 100 ° C. When the reaction was completed, extracted with distilled water and EA. The organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain 37 g (79%) of the title compound 58 .
상기 제조예 1-2의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 74을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 74 were prepared using the method of Preparation Example 1-2, and the 1 H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.
[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound 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(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 4,4',4"-트리스(N,N-(2-나프틸)-페닐아미노)트리페닐아민 (2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-bis(α-나프틸)-N,N'-디페닐-4,4'-디아민(NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 1을 넣고, 또 다른 셀에는 도판트로서 하기 화합물 D를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 2 내지 5중량%으로 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.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? It was used after. Next, an ITO substrate is placed in the substrate folder of the vacuum deposition equipment, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine ( 2-TNATA), evacuated until the vacuum in the chamber reached 10 -6 torr, and applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition apparatus, and the current was applied to the cell to give NPB. A 20 nm-thick hole transport layer was deposited on the hole injection layer by evaporation, and then a light emitting layer was deposited on the hole injection layer as follows: Compound 1 according to the invention was added, and another cell was added with the following compound D as a dopant, respectively, and the two materials were evaporated at different rates. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping at 2 to 5 wt%.
이어서 상기 발광층 위에 전자전달층으로써 트리스(8-하이드록시퀴놀린)알루미늄(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 리튬퀴놀레이트(Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED소자를 제작하였다. Subsequently, tris (8-hydroxyquinoline) aluminum (III) (Alq) was deposited to a thickness of 20 nm as an electron transport layer on the light emitting layer, and then lithium quinolate (Liq) was deposited to a thickness of 1 to 2 nm as an electron injection layer. Afterwards, an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to fabricate an OLED device.
재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each compound was vacuum sublimated and purified under 10 -6 torr to be used as an OLED light emitting material.
그 결과, 7.0 V의 전압에서 7.4 mA/cm2의 전류가 흘렀으며, 1085 cd/m2의 청색발광이 확인되었다.As a result, a current of 7.4 mA / cm 2 flowed at a voltage of 7.0 V, and blue light emission of 1085 cd / m 2 was confirmed.
[실시예 2] [Example 2]
발광층에서 호스트 재료로서 본 발명의 화합물 4을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 4 of the present invention was used as a host material in the emission layer.
그 결과, 7.2 V의 전압에서 8.0 mA/cm2의 전류가 흘렀으며, 1090 cd/m2의 청색발광이 확인되었다.As a result, a current of 8.0 mA / cm 2 flowed at a voltage of 7.2 V, and blue light emission of 1090 cd / m 2 was confirmed.
[실시예 3] Example 3
발광층에서 호스트 재료로서 본 발명의 화합물 5을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 5 of the present invention was used as a host material in the emission layer.
그 결과, 7.4 V의 전압에서 8.1 mA/cm2의 전류가 흘렀으며, 1020 cd/m2의 청색발광이 확인되었다.As a result, a current of 8.1 mA / cm 2 flowed at a voltage of 7.4 V, and blue light emission of 1020 cd / m 2 was confirmed.
[실시예 4] Example 4
발광층에서 호스트 재료로서 본 발명의 화합물 14을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 14 of the present invention was used as a host material in the emission layer.
그 결과, 7.8 V의 전압에서 8.4 mA/cm2의 전류가 흘렀으며, 1060 cd/m2의 청색발광이 확인되었다.As a result, a current of 8.4 mA / cm 2 flowed at a voltage of 7.8 V, and blue light emission of 1060 cd / m 2 was confirmed.
[실시예 5] Example 5
발광층에서 호스트 재료로서 본 발명의 화합물 59을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 59 of the present invention was used as a host material in the emission layer.
그 결과, 7.2 V의 전압에서 7.9 mA/cm2의 전류가 흘렀으며, 1120 cd/m2의 청색발광이 확인되었다.As a result, a current of 7.9 mA / cm 2 flowed at a voltage of 7.2 V, and blue light emission of 1120 cd / m 2 was confirmed.
[실시예 6] Example 6
발광층에서 호스트 재료로서 본 발명의 화합물 60을 넣고, 발광 도판트로서 N 9 ,N 9 ,N 10 ,N 10 ,2,6-헥사페닐안트라센-9,10-다이아민(화합물 E)을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.Compound 60 of the present invention was used as a host material in the light emitting layer, and N 9 , N 9 , N 10 , N 10 , 2,6-hexaphenylanthracene-9,10-diamine (Compound E) was used as a light emitting dopant. Except for the above, an OLED device was manufactured in the same manner as in Example 1.
그 결과, 7.2 V의 전압에서 8.2 mA/cm2의 전류가 흘렀으며, 1480 cd/m2의 녹색발광이 확인되었다.As a result, a current of 8.2 mA / cm 2 flowed at a voltage of 7.2 V, and green light emission of 1480 cd / m 2 was confirmed.
[실시예 7] Example 7
발광층에서 호스트 재료로서 본 발명의 화합물 54을 이용한 것 외에는, 실시예 6과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 6 , except that Compound 54 of the present invention was used as a host material in the emission layer.
그 결과, 7.0 V의 전압에서 8.9 mA/cm2의 전류가 흘렀으며, 1570 cd/m2의 녹색발광이 확인되었다.As a result, a current of 8.9 mA / cm 2 flowed at a voltage of 7.0 V, and green light emission of 1570 cd / m 2 was confirmed.
[실시예 8] Example 8
발광층에서 호스트 재료로서 본 발명의 화합물 45을 이용한 것 외에는, 실시예 6과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 6, except that Compound 45 of the present invention was used as a host material in the emission layer.
그 결과, 6.8 V의 전압에서 8.5 mA/cm2의 전류가 흘렀으며, 1500 cd/m2의 녹색발광이 확인되었다.As a result, a current of 8.5 mA / cm 2 flowed at a voltage of 6.8 V, and green light emission of 1500 cd / m 2 was confirmed.
[실시예 9] Example 9
발광층에서 호스트 재료로서 본 발명의 화합물 63을 이용한 것 외에는, 실시예 6과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 6, except that Compound 63 of the present invention was used as a host material in the emission layer.
그 결과, 7.0 V의 전압에서 8.7 mA/cm2의 전류가 흘렀으며, 1610 cd/m2의 녹색발광이 확인되었다.As a result, a current of 8.7 mA / cm 2 flowed at a voltage of 7.0 V, and green light emission of 1610 cd / m 2 was confirmed.
[실시예 10] Example 10
발광층에서 호스트 재료로서 디나프틸안트라센(DNA), 도판트로서 본 발명의 화합물 70을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Dnaphthylanthracene (DNA) was used as the host material in the light emitting layer and Compound 70 of the present invention was used as the dopant.
그 결과, 7.2 V의 전압에서 8.6 mA/cm2의 전류가 흘렀으며, 1530 cd/m2의 녹색발광이 확인되었다.As a result, a current of 8.6 mA / cm 2 flowed at a voltage of 7.2 V, and green light emission of 1530 cd / m 2 was confirmed.
[실시예 11] Example 11
발광층에서 호스트 재료로서 디나프틸안트라센(DNA), 도판트로서 본 발명의 화합물 69을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Dnaphthylanthracene (DNA) and the compound 69 of the present invention were used as the dopant in the light emitting layer.
그 결과, 7.4 V의 전압에서 8.7 mA/cm2의 전류가 흘렀으며, 1590 cd/m2의 녹색발광이 확인되었다.As a result, a current of 8.7 mA / cm 2 flowed at a voltage of 7.4 V, and green light emission of 1590 cd / m 2 was confirmed.
[실시예 12] Example 12
발광층에서 호스트 재료로서 디나프틸안트라센(DNA), 도판트로서 본 발명의 화합물 74을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Dnaphthylanthracene (DNA) was used as the host material in the light emitting layer and Compound 74 of the present invention was used as the dopant.
그 결과, 7.4 V의 전압에서 8.6 mA/cm2의 전류가 흘렀으며, 1500 cd/m2의 녹색발광이 확인되었다.As a result, a current of 8.6 mA / cm 2 flowed at a voltage of 7.4 V, and green light emission of 1500 cd / m 2 was confirmed.
[비교예 1] Comparative Example 1
진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 디나프틸안트라센(DNA), 도판트로서 화합물 D를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that dinaphthylanthracene (DNA) and compound D were used instead of the compound of the present invention as a host material in one cell in a vacuum deposition apparatus.
그 결과, 6.7 V의 전압에서 11.0 mA/cm2의 전류가 흘렀으며, 1320 cd/m2의 청색발광이 확인되었다.As a result, a current of 11.0 mA / cm 2 flowed at a voltage of 6.7 V, and blue light emission of 1320 cd / m 2 was confirmed.
[비교예 2] Comparative Example 2
진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 디나프틸안트라센(DNA)을 넣고, 도판트로서 N 9 ,N 9 ,N 10 ,N 10 ,2,6-헥사페닐안트라센-9,10-다이아민(화합물 E)을 이용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.Dinaphthylanthracene (DNA) was added to one cell in the vacuum deposition apparatus instead of the compound of the present invention as a host material, and N 9 , N 9 , N 10 , N 10 , 2,6-hexaphenylanthracene-9, An OLED device was manufactured in the same manner as in Example 1, except that 10-diamine (Compound E) was used.
그 결과, 7.2 V의 전압에서 11.0 mA/cm2의 전류가 흘렀으며, 1793 cd/m2의 청색발광이 확인되었다.
As a result, a current of 11.0 mA / cm 2 flowed at a voltage of 7.2 V, and blue light emission of 1793 cd / m 2 was confirmed.
본 발명의 유기발광화합물들은 종래의 발광화합물 보다 높은 효율 및 색순도를 구현할수 있음을 알수 있었다. 이는 다이메틸벤조안트라센의 공명영향으로 색순도의 장점을 가지고 있다. 화합물 5의 경우에는 입체장애영향으로 더 나은 발광효율을 나타내는 특성을 보였다. 화합물 59의 경우에는 중간의 페닐을 도입함으로써 소비전력 및 수명면에서 커다란 장점을 가지고 있었다. 비교예 2 대비하여 화합물 63의 경우에는 안트라센 2번위치에 결합한 페닐을 도임합으로써 공명길이가 늘어져 녹색유기발광화합물로서 장수명 효과를 가중 시킬 수 있었다. It was found that the organic light emitting compounds of the present invention can achieve higher efficiency and color purity than conventional light emitting compounds. This has the advantage of color purity due to the resonance effect of dimethylbenzoanthracene. In the case of compound 5, the luminous efficiency was better due to steric hindrance. In the case of compound 59, the introduction of intermediate phenyl has a great advantage in terms of power consumption and lifespan. In comparison with Comparative Example 2, in the case of Compound 63, the resonance length was increased by incorporating phenyl bonded to the anthracene 2-position, thereby increasing the long-life effect as a green organic light emitting compound.
따라서 본 발명의 유기발광화합물은 높은효율과 장수명의 발광재료로서 사용될수 있을 것으로 보인다.Therefore, the organic light emitting compound of the present invention is expected to be used as a light emitting material with high efficiency and long life.
Claims (11)
[화학식 1]
[상기 화학식 1에서,
R1 내지 R2은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴 또는 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬이고;
R3 내지 R11은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 시아노, 나이트로, 하이드록시, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31 또는 -YR32이며;
R12 내지 R19은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, 하이드록시, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐이거나, 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 있고;
Ar은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, 하이드록시, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 또는 치환 또는 비치환된(C2-C30)알키닐이며;
A는 화학결합이거나, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C2-C30)헤테로아릴렌 또는 치환 또는 비치환된(C6-C30)아릴렌티오이고;
B는 화학결합이거나, 치환 또는 비치환된(C2-C30)알킬렌, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C3-C30)헤테로아릴렌, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된(C3-C30)시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬렌, 치환 또는 비치환된 지환족고리가 하나 이상 융합된 (C6-C30)아릴렌, 치환 또는 비치환된(C2-C30)알케닐렌, 치환 또는 비치환된(C2-C30)알키닐렌, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬렌, 치환 또는 비치환된(C1-C30)알킬렌티오, 치환 또는 비치환된(C1-C30)알킬렌옥시, 치환 또는 비치환된(C6-C30)아릴렌옥시이거나, 치환 또는 비치환된(C6-C30)아릴렌티오이고;
R21 내지 R32는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C3-C30)헤테로시클로알킬이거나, 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;
Y는 S 또는 O이며;
a 및 b는 서로 독립적으로 1 내지 3의 정수이고; a가 2 이상의 정수인 경우 A는 동일하거나 상이할 수 있고, b가 2 이상의 정수인 경우 B는 동일하거나 상이할 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있고;
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)
R 1 to R 2 are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl or substituted or unsubstituted 5 to 7 membered heterocycloalkyl;
R 3 to R 11 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, cyano, nitro, hydroxy, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R 26 , -P (= O) R 27 R 28 , -SiR 29 R 30 R 31, or -YR 32 ;
R 12 to R 19 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cyclo Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted, with one or more alkyl fused To 7-membered heterocycloalkyl fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic rings with one or more fused (C3-C30) cycloalkyl , Cyano, nitro, hydroxy, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R 26 , -P (= O) R 27 R 28 , -SiR 29 R 30 R 31 , -YR 32 Or substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, or fused with an adjacent substituent Including collars It may be connected to a substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene which do not include to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, The carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
Ar is independently of one another hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Fused substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring At least one fused 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring at least one fused (C3-C30) cycloalkyl, cyano, Nitro, hydroxy, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R 26 , -P (= O) R 27 R 28 , -SiR 29 R 30 R 31 , -YR 32 , substituted or unsubstituted Substituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, or substituted or unsubstituted (C2-C30) alkynyl;
A is a chemical bond or is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene or substituted or unsubstituted (C6-C30) arylenethio;
B is a chemical bond, substituted or unsubstituted (C2-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) heteroarylene, substituted or unsubstituted 5- to 7-membered heterocycloalkylene, substituted or unsubstituted aromatic ring, 5- to 7-membered heterocycloalkylene, substituted or unsubstituted (C3-C30) cycloalkylene, substituted Or (C3-C30) cycloalkylene in which one or more unsubstituted aromatic rings are fused, (C6-C30) arylene in which one or more substituted or unsubstituted alicyclic rings are fused, substituted or unsubstituted (C2-C30). ) Alkenylene, substituted or unsubstituted (C2-C30) alkynylene, substituted or unsubstituted (C6-C30) ar (C1-C30) alkylene, substituted or unsubstituted (C1-C30) alkylenethio, Substituted or unsubstituted (C1-C30) alkyleneoxy, substituted or unsubstituted (C6-C30) aryleneoxy, or substituted or unsubstituted (C6-C30) arylenethio;
R 21 to R 32 are independently of each other hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or Unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) heterocycloalkyl, substituted or unsubstituted (C3-C30) alkylene with or without fused ring with adjacent substituents or Linked with substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
Y is S or O;
a and b are each independently an integer of 1 to 3; when a is an integer of 2 or more, A may be the same or different, and when b is an integer of 2 or more, B may be the same or different, and adjacent substituents may combine with each other to form a ring;
Wherein said heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
상기 R1 내지 R2, R3 내지 R11, R12 내지 R19, Ar, A, B 및 R21 내지 R32에 더 치환되는 치환기는 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C6-C30)시클로알킬, RaRbRcSi-, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NRdRe, BRfRg, PRhRi, P(=O)RjRk, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, RlX-, RmC(=O)-, RmC(=O)O-, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상이고, Ra 내지 Rl는 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이고; X는 S 또는 O이고; Rm는 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴 또는 (C6-C30)아릴옥시인 것을 특징으로 하는 유기 발광 화합물.The method of claim 1,
R 1 to R 2 , Substituents further substituted with R 3 to R 11 , R 12 to R 19 , Ar, A, B and R 21 to R 32 independently of each other, deuterium, halogen, (C 1 -C 30) alkyl unsubstituted or substituted with halogen, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered fused at least one aromatic ring Heterocycloalkyl, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, R a R b R c Si-, (C2-C30) alkenyl, (C2-C30) alky Nyl, cyano, carbazolyl, NR d R e , BR f R g , PR h R i , P (= O) R j R k , (C6-C30) ar (C1-C30) alkyl, (C1-C30 One or more selected from the group consisting of alkyl (C6-C30) aryl, R 1 X-, R m C (= 0)-, R m C (= 0) O-, carboxyl, nitro or hydroxy , R a to R l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; X is S or O; R m is (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy.
A는 화학결합이거나, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C2-C30)헤테로아릴렌 또는 치환 또는 비치환된(C6-C30)아릴렌티오(화합물 68번 참고)이고; B는 화학결합이거나, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C3-C30)헤테로아릴렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬렌, 치환 또는 비치환된 지환족고리가 하나 이상 융합된 (C6-C30)아릴렌, 치환 또는 비치환된(C2-C30)알케닐렌 또는 치환 또는 비치환된(C2-C30)알키닐렌이고; R1 내지 R19는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴 또는 -NR21R22 이거나, 인접한 치환체와 C5알킬렌 또는
A is a chemical bond or substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene or substituted or unsubstituted (C6-C30) arylenethio (Compound No. 68 Reference); B is a 5- to 7-membered chemical bond, or a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (C3-C30) heteroarylene, or a substituted or unsubstituted aromatic ring in which at least one is fused Heterocycloalkylene, (C3-C30) cycloalkylene fused with one or more substituted or unsubstituted aromatic rings, (C6-C30) arylene fused with one or more substituted or unsubstituted alicyclic rings, substituted or Unsubstituted (C2-C30) alkenylene or substituted or unsubstituted (C2-C30) alkynylene; R 1 to R 19 are independently of each other hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl or -NR 21 R 22 or adjacent substituents and C5 alkylene or
Ar은 수소, 중수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 플루오르, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴, 트리페닐실릴, 메톡시, 에톡시, n-프로폭시, i-프로폭시, n-부톡시, i-부톡시, t-부톡시, n-펜톡시, i-펜톡시, n-헥실옥시, n-헵톡시, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 테트라졸릴, 피라지닐, 피리미딜, 벤조퓨란일, 벤조티오펜일, 피라졸릴, 인돌릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 디메틸아미노, 디페닐아미노, 모노메틸아미노, (4-t-부틸페닐)(페닐)아미노, 모노페닐아미노, 페닐옥시, 페닐티오, 트리페닐메틸, 페닐, 나프틸, 바이페닐, 페난트릴, 피레닐, 플루오란테닐, 피리딜, 인데닐, 트리페닐레닐, 테트라하이드로나프틸, 7H-벤조[c]플루오레닐, 7H-벤조[de]안트라세닐, 테트라하이드로퀴놀릴, 안트라세닐, 7H-벤조[c]카바졸릴, 에티닐, 에테닐, 퀴놀릴,
Ar is hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, fluorine, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethyl Silyl, dimethylphenylsilyl, triphenylsilyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy , n-hexyloxy, n-heptoxy, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, tetrazolyl, pyrazinyl, pyrimidyl, benzofuranyl, benzothiophenyl, pyra Zolyl, indolyl, oxazolyl, benzothiazolyl, benzooxazolyl, dimethylamino, diphenylamino, monomethylamino, (4-t-butylphenyl) (phenyl) amino, monophenylamino, phenyloxy, phenylthio, tree Neylmethyl, phenyl, naphthyl, biphenyl, phenanthryl, pyrenyl, fluoranthhenyl, pyridyl, indenyl, triphenylenyl, tetrahydronaphthyl, 7H-benzo [c] fluorenyl, 7H-benzo [ de] anthracenyl, tetrahydroquinolyl, anthracenyl, 7H-benzo [c] carbazolyl, ethynyl, ethenyl, quinolyl,
A는 화학결합 또는 하기 구조로부터 선택되고;
A is selected from chemical bonds or the following structures;
상기 유기 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 하기 화학식 2로 표시되는 도판트 하나 이상을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.
[화학식 2]
[상기 화학식 2에서, Ar101 및 Ar102는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C4-C30)헤테로아릴, 치환 또는 비치환된 (C6-C30)아릴아미노, (C1-C30)알킬아미노, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬이고, Ar101 및 Ar102는 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하고;
c가 1인 경우 Ar103은 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C4-C30)헤테로아릴 또는 하기 구조에서 선택되는 치환기이고;
c가 2인 경우 Ar103는 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된(C4-C30)헤테로아릴렌 또는 하기 구조에서 선택되는 치환기이고;
Ar104 및 Ar105은 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌 또는 치환 또는 비치환된(C4-C30)헤테로아릴렌이고;
R101 내지 R103는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴, -NR111R112, -BR113R114, -PR115R116, -P(=O)R117R118, -SiR119R120R121 또는 -YR122이며;
R111 내지 R122는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C3-C30)헤테로시클로알킬이고, R111 내지 R122가 각각 독립적으로 인접한 치환체들 끼리 서로 결합하여 고리를 형성할 경우 치환 또는 비치환된 (C3-C30)의 지방족 고리, 치환 또는 비치환된 (C5-C30)의 헤테로지방족 고리, 치환 또는 비치환된 (C6-C30)의 방향족 고리, 치환 또는 비치환된 (C6-C30)의 헤테로방향족 고리를 형성할 수 있고
상기 Y는 S 또는 O이며;
d는 1 내지 4의 정수이며, e는 0 또는 1의 정수이다.]The method of claim 6,
The organic light emitting diode includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, wherein the organic material layer includes one or more organic light emitting compounds and one or more dopants represented by the following Chemical Formula 2. Light emitting element.
(2)
[In Formula 2, Ar 101 and Ar 102 are independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C4-C30) hetero One or more fused aryl, substituted or unsubstituted (C6-C30) arylamino, (C1-C30) alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic rings 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring is a (C3-C30) cycloalkyl fused at least one, Ar 101 and Ar 102 is Linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
when c is 1 Ar 103 is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;
when c is 2, Ar 103 is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;
Ar 104 and Ar 105 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene;
R 101 to R 103 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl, -NR 111 R 112 , -BR 113 R 114 , -PR 115 R 116 , -P (= 0) R 117 R 118 , -SiR 119 R 120 R 121 or -YR 122 ;
R 111 to R 122 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, substituted or Unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) heterocycloalkyl, and R 111 to R 122 are each independently substituted or unsubstituted when adjacent substituents combine with each other to form a ring; A substituted (C3-C30) aliphatic ring, a substituted or unsubstituted (C5-C30) heteroaliphatic ring, a substituted or unsubstituted (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) Can form a heteroaromatic ring of
Y is S or O;
d is an integer of 1 to 4, and e is an integer of 0 or 1.]
상기 유기 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 하기 화학식 3 또는 화학식 4로 표시되는 호스트 화합물 하나 이상을 포함하는 것을 특징으로 하는 유기 발광 소자.
[화학식 3]
(Ar11)f-L11-(Ar12)g
[화학식 4]
(Ar13)h-L12-(Ar14)i
[상기 화학식 3 내지 4에서,
L11는 치환 또는 비치환된 (C6-C60)아릴렌 또는 치환 또는 비치환된 (C4-C60)헤테로아릴렌이고;
L12는 치환 또는 비치환된 안트라세닐렌이며;
Ar11 내지 Ar14은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 시아노, 나이트로, -NR201R202, -BR203R204, -PR205R206, -P(=O)R207R208, R209R210R211Si-, R212X-, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐이거나, 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 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소로 치환될 수 있고;
R201 내지 R212는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고;
X는 S 또는 O이고;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며;
f, g, h 및 i는 서로 독립적으로 0 내지 4의 정수이다.]The method of claim 6,
The organic light emitting diode 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 host compound represented by Formula 3 or Formula 4 below. Organic light emitting device.
(3)
(Ar 11 ) f -L 11- (Ar 12 ) g
[Chemical Formula 4]
(Ar 13 ) h -L 12- (Ar 14 ) i
[In Formulas 3 to 4,
L 11 is substituted or unsubstituted (C6-C60) arylene or substituted or unsubstituted (C4-C60) heteroarylene;
L 12 is substituted or unsubstituted anthracenylene;
Ar 11 to Ar 14 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl fused or substituted at least one (C6-C30) aryl, substituted or unsubstituted 5 5-7 membered heterocycloalkyl, cyano, nitro, fused with one or more membered heterocycloalkyl, substituted or unsubstituted aromatic rings, -NR 201 R 202 , -BR 203 R 204 ,- PR 205 R 206 , -P (= O) R 207 R 208 , R 209 R 210 R 211 Si-, R 212 X-, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) alkylene or substituted with or without a fused ring with adjacent substituents Or unsubstituted Linked to a (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the carbon atoms of the monocyclic or polycyclic aromatic ring formed may be substituted with nitrogen;
R 201 to R 212 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;
X is S or O;
The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P;
f, g, h and i are each independently an integer from 0 to 4.]
상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물 또는 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속을 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자. The method of claim 7, wherein
At least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound or an organic metal of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and d-transition element in the organic layer The organic electroluminescent device further comprises at least one metal selected from the group consisting of.
상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 7, wherein
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer.
상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 7, wherein
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer for emitting blue, red or green light to the organic material layer.
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| PCT/KR2011/001435 WO2011115378A1 (en) | 2010-03-17 | 2011-03-02 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN2011800243671A CN102933530A (en) | 2010-03-17 | 2011-03-02 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| JP2012558067A JP5797672B2 (en) | 2010-03-17 | 2011-03-02 | Novel organic electroluminescent compound and organic electroluminescent device using the same |
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| Publication number | Publication date |
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| TW201211058A (en) | 2012-03-16 |
| JP5797672B2 (en) | 2015-10-21 |
| CN102933530A (en) | 2013-02-13 |
| WO2011115378A1 (en) | 2011-09-22 |
| JP2013528927A (en) | 2013-07-11 |
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| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |