CN114621169A - 有机电致发光化合物和包含其的有机电致发光装置 - Google Patents
有机电致发光化合物和包含其的有机电致发光装置 Download PDFInfo
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- CN114621169A CN114621169A CN202111479829.0A CN202111479829A CN114621169A CN 114621169 A CN114621169 A CN 114621169A CN 202111479829 A CN202111479829 A CN 202111479829A CN 114621169 A CN114621169 A CN 114621169A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
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- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
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- 125000003342 alkenyl group Chemical group 0.000 claims description 7
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- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 150000001975 deuterium Chemical group 0.000 claims description 5
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 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 10
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- HXITXNWTGFUOAU-RALIUCGRSA-N (2,3,4,5,6-pentadeuteriophenyl)boronic acid Chemical compound [2H]C1=C([2H])C([2H])=C(B(O)O)C([2H])=C1[2H] HXITXNWTGFUOAU-RALIUCGRSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 5
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- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 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 3
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 3
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 3
- MINMDCMSHDBHKG-UHFFFAOYSA-N 4-[4-[[6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl]oxymethyl]-5-methyl-1,3-thiazol-2-yl]morpholine Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(=C(S1)C)N=C1N1CCOCC1 MINMDCMSHDBHKG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- MWPLVEDNUUSJAV-XFYSQLSBSA-N 1,2,3,4,5,6,7,10-octadeuterioanthracene Chemical compound [2H]c1cc2cc3c([2H])c([2H])c([2H])c([2H])c3c([2H])c2c([2H])c1[2H] MWPLVEDNUUSJAV-XFYSQLSBSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- AYOVPQORFBWFNO-UHFFFAOYSA-N 5-bromo-1-benzofuran Chemical compound BrC1=CC=C2OC=CC2=C1 AYOVPQORFBWFNO-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 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 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-DYVTXVBDSA-N 1,2,3,4,5-pentadeuterio-6-phenylbenzene Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-DYVTXVBDSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane 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-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及有机电致发光化合物和包含其的有机电致发光装置。公开了具有特定结构的蒽衍生物和包含蒽衍生物的有机电致发光装置。有机电致发光装置包括采用蒽衍生物作为主体化合物和具有特定结构的多环芳族衍生物作为掺杂剂化合物的发光层。使用主体化合物和掺杂剂化合物使有机电致发光装置能够具有长寿命和显著改善的低电压特性。
Description
技术领域
本发明涉及有机电致发光化合物和包含其的有机电致发光装置。更具体地,本发明涉及这样的有机电致发光装置:其中在发光层中采用具有特定结构的蒽衍生物作为主体化合物和多环芳族衍生物作为掺杂剂化合物,实现了装置的长寿命和显著改善的低电压特性。
背景技术
有机电致发光装置是自发光装置,其中从电子注入电极(阴极)注入的电子与从空穴注入电极(阳极)注入的空穴在发光层中复合以形成激子,激子在释放能量的同时发光。这样的有机电致发光装置具有驱动电压低、亮度高、视角大和响应时间短的优点,并且可以应用于全色发光平板显示器。由于这些优点,有机电致发光装置作为下一代光源而受到关注。
有机电致发光装置的以上特性通过装置的有机层的结构优化来实现,并且由用于有机层的稳定且有效的材料(例如空穴注入材料、空穴传输材料、发光材料、电子传输材料、电子注入材料和电子阻挡材料)来支持。然而,仍需要进行更多的研究以开发用于有机电致发光装置的有机层的结构上优化的结构和用于有机电致发光装置的有机层的稳定且有效的材料。
特别地,为了发光层中的最大效率,需要主体和掺杂剂的能带隙的适当组合使得空穴和电子通过稳定的电化学路径迁移至掺杂剂以形成激子。
发明内容
因此,本发明旨在提供这样的有机电致发光装置:其中在发光层中采用特定的主体和掺杂剂材料,实现装置的显著改善的低电压驱动和寿命特性。
本发明的一个方面提供了作为用于装置的有机层,优选地发光层的主体化合物的由式A表示的化合物:
以下描述式A的结构特征和可以由式A表示的特定化合物,并且式A中的Ar1、R1至R14、L1和X如以下所限定。
本发明的另一个方面提供了有机电致发光装置,其包括第一电极、与第一电极相对的第二电极、以及介于第一电极与第二电极之间的发光层,其中发光层包含由式A表示的化合物。
有机电致发光装置的发光层还包含由式D-1或D-2表示的掺杂剂化合物:
以下描述式D-1和D-2的结构特征以及可以由式D-1和D-2表示的特定化合物,并且式D-1和D-2中的X1、Y1至Y3和A1至A3如以下所限定。
本发明的有机电致发光装置包括采用具有特定结构的蒽衍生物作为主体和多环芳族衍生物作为掺杂剂的发光层。使用主体和掺杂剂确保了装置的显著改善的寿命和低电压驱动特性。由于这些优点,本发明的有机电致发光装置不仅可以在照明系统中而且在包括平板显示器、柔性显示器和可穿戴显示器的各种显示器中找到有利的应用。
具体实施方式
现在将更详细地描述本发明。
本发明的一个方面涉及由式A表示的化合物:
其中Ar1选自经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C50杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,R1至R14彼此相同或不同并且各自独立地选自氢、氘、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C30烯基、经取代或未经取代的C2-C30炔基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的C2-C50杂芳基、经取代或未经取代的C2-C30杂环烷基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C50芳氧基、经取代或未经取代的C1-C30烷基硫基、经取代或未经取代的C6-C50芳基硫基、经取代或未经取代的C1-C30烷基胺基、经取代或未经取代的C6-C50芳基胺基、经取代或未经取代的C1-C30烷基甲硅烷基、经取代或未经取代的C6-C50芳基甲硅烷基、经取代或未经取代的C3-C50混合的脂族-芳族环状基团、氰基、硝基和卤素,条件是R9和R10中的一者与L1键合,X为氧(O)或硫原子(S),L1为二价连接基团且为单键或者选自经取代或未经取代的C6-C50亚芳基、经取代或未经取代的C2-C50亚杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,以及n为1至3的整数,条件是当n为2或更大时,连接基团L1彼此相同或不同。
式A的化合物在其结构中包含至少一个苯并呋喃或苯并噻吩部分。在有机电致发光装置的发光层中使用式A的化合物作为主体化合物使有机电致发光装置能够具有长寿命和改善的低电压特性。
如本文所用,Ar1、R1至R14和L1的限定中的术语“经取代的”表示经选自以下的一个或更多个取代基取代:氘、氰基、卤素、羟基、硝基、C1-C24烷基、C1-C24卤代烷基、C3-C30环烷基、C2-C24烯基、C2-C24炔基、C1-C24杂烷基、C6-C30芳基、C7-C30芳基烷基、C7-C30烷基芳基、C2-C30杂芳基、C2-C30杂芳基烷基、C1-C24烷氧基、C1-C24烷基氨基、C6-C30芳基氨基、C2-C30杂芳基氨基、C1-C24烷基甲硅烷基、C6-C30芳基甲硅烷基、C6-C30芳氧基和C3-C30混合的脂族-芳族环状基团。同一限定中的术语“未经取代的”表示不具有取代基。
式A的化合物包含至少一个氘原子(D)。即,式A中的Ar1、R1至R14和L1中的至少一者或者Ar1、R1至R14和L1的取代基中的至少一者为氘。
根据本发明的一个实施方案,由式A表示的蒽衍生物的氘化程度为至少10%,表示由式A表示的化合物的主链上引入的取代基中的至少10%为氘原子。
根据本发明的一个实施方案,由式A表示的蒽衍生物的氘化程度为至少30%。
由式A表示的蒽衍生物的氘化程度为至少50%。
根据本发明的一个实施方案,R11至R14中的至少一者可以选自经取代或未经取代的C6-C20芳基、经取代或未经取代的C3-C20环烷基和经取代或未经取代的C3-C20杂芳基。
根据本发明的一个实施方案,式A中的R11至R14中的至少一者可以为经取代或未经取代的氘化C6-C20芳基、经取代或未经取代的氘化C3-C20环烷基或者经取代或未经取代的氘化C3-C20杂芳基。
根据本发明的一个实施方案,由式A表示的蒽衍生物可以为由式A-1或式A-2表示的化合物:
其中Ar11选自经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C50杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,R21至R33彼此相同或不同并且各自独立地选自氢、氘、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C30烯基、经取代或未经取代的C2-C30炔基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的C2-C50杂芳基、经取代或未经取代的C2-C30杂环烷基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C50芳氧基、经取代或未经取代的C1-C30烷基硫基、经取代或未经取代的C6-C50芳基硫基、经取代或未经取代的C1-C30烷基胺基、经取代或未经取代的C6-C50芳基胺基、经取代或未经取代的C1-C30烷基甲硅烷基、经取代或未经取代的C6-C50芳基甲硅烷基、经取代或未经取代的C3-C50混合的脂族-芳族环状基团、氰基、硝基和卤素,X为氧(O)或硫原子(S),L2为二价连接基团且为单键或者选自经取代或未经取代的C6-C50亚芳基、经取代或未经取代的C2-C50亚杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,以及m为1至3的整数,条件是当m为2或更大时,连接基团L1彼此相同或不同,
其中Ar11、R21至R33、X、L2和m如式A-1中所限定。
如本文所用,Ar11、R21至R33和L2的限定中的术语“经取代的”表示经选自以下的一个或更多个取代基取代:氘、氰基、卤素、羟基、硝基、C1-C24烷基、C1-C24卤代烷基、C3-C30环烷基、C2-C24烯基、C2-C24炔基、C1-C24杂烷基、C6-C30芳基、C7-C30芳基烷基、C7-C30烷基芳基、C2-C30杂芳基、C2-C30杂芳基烷基、C1-C24烷氧基、C1-C24烷基氨基、C6-C30芳基氨基、C2-C30杂芳基氨基、C1-C24烷基甲硅烷基、C6-C30芳基甲硅烷基、C6-C30芳氧基和C3-C30混合的脂族-芳族环状基团。同一限定中的术语“未经取代的”表示不具有取代基。
式A-1和A-2的化合物各自包含至少一个氘原子(D)。即,式A-1和A-2中的每一者中的Ar1、R21至R33和L2中的至少一者或者Ar1、R21至R33和L2的取代基中的至少一者为氘。
在“经取代或未经取代的C1-C30烷基”、“经取代或未经取代的C6-C50芳基”等中,烷基或芳基中的碳原子数表示构成未经取代的烷基或芳基部分的碳原子数而不考虑取代基中的碳原子数。例如,在对位上经丁基取代的苯基对应于经C4丁基取代的C6芳基。
如本文所用,表述“与相邻取代基形成环”意指相应的取代基与相邻取代基结合以形成经取代或未经取代的脂环族或芳族环,并且术语“相邻取代基”可以意指与取代有相应取代基的原子直接连接的原子上的取代基、位于空间上最接近相应取代基的取代基、或者取代有相应取代基的原子上的另外的取代基。例如,苯环的邻位上取代的两个取代基或脂族环中的同一碳上的两个取代基可以被认为是彼此“相邻”的。
在本发明中,烷基可以为直链或支化的。烷基中的碳原子数没有特别限制,但优选为1至20。烷基的具体实例包括但不限于甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基丁基、1-乙基丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基丙基、1,1-二甲基丙基、异己基、2-甲基戊基、4-甲基己基、和5-甲基己基。
烯基旨在包括直链烯基和支化烯基,并且可以任选地经一个或更多个另外的取代基取代。烯基具体地可以为乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、基或苯乙烯基,但不限于此。
炔基旨在包括直链炔基和支化炔基,并且可以任选地经一个或更多个另外的取代基取代。炔基可以为例如乙炔基或2-丙炔基,但不限于此。
环烷基旨在包括单环环烷基和多环环烷基,并且可以任选地经一个或更多个另外的取代基取代。如本文所用,术语“多环”意指环烷基可以与一个或更多个另外的环状基团直接连接或稠合。另外的环状基团可以为环烷基并且其另一些实例包括杂环烷基、芳基和杂芳基。环烷基具体地可以为环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基或环辛基,但不限于此。
杂环烷基旨在包括插入有杂原子例如O、S、Se、N或Si的单环杂环烷基和多环杂环烷基,并且可以任选地经一个或更多个另外的取代基取代。如本文所用,术语“多环”意指杂环烷基可以与一个或更多个另外的环状基团直接连接或稠合。另外的环状基团可以为杂环烷基,并且其另一些实例包括环烷基、芳基和杂芳基。
芳基可以为单环芳基或多环芳基。单环芳基的实例包括但不限于苯基、联苯基、三联苯基和基。多环芳基的实例包括萘基、蒽基、菲基、芘基、基、并四苯基、基、芴基、苊基(acenaphathcenyl)、三亚苯基和荧蒽基,但本发明的范围不限于此。
杂芳基是指插入有一个或更多个杂原子的杂环基。杂芳基的实例包括但不限于噻吩基、呋喃基、吡咯基、咪唑基、三唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、二苯并呋喃基、菲咯啉基、噻唑基、异唑基、二唑基、噻二唑基、苯并噻唑基和吩噻嗪基。
混合的脂族-芳族环状环是指其中至少一个脂族环和至少一个芳族环连接并稠合在一起并且整体上是非芳族的结构。混合的脂族-芳族多环的环可以包含一个或更多个除碳原子(C)之外的选自N、O、P和S的杂原子。
烷氧基具体地可以为甲氧基、乙氧基、丙氧基、异丁氧基、仲丁氧基、戊氧基、异戊氧基或己氧基,但不限于此。
甲硅烷基旨在包括烷基取代的甲硅烷基和芳基取代的甲硅烷基。这样的甲硅烷基的具体实例包括三甲基甲硅烷基、三乙基甲硅烷基、三苯基甲硅烷基、三甲氧基甲硅烷基、二甲氧基苯基甲硅烷基、二苯基甲基甲硅烷基、二苯基乙烯基甲硅烷基、甲基环丁基甲硅烷基、和二甲基呋喃基甲硅烷基。
胺基可以为例如-NH2、烷基胺基和芳基胺基。芳基胺基为芳基取代的胺基,以及烷基胺基为烷基取代的胺基。芳基胺基的实例包括经取代或未经取代的单芳基胺基、经取代或未经取代的二芳基胺基、和经取代或未经取代的三芳基胺基。芳基胺基中的芳基可以为单环芳基或多环芳基。芳基胺基可以包含两个或更多个芳基。在这种情况下,芳基可以为单环芳基或多环芳基。或者,芳基可以由单环芳基和多环芳基组成。芳基胺基中的芳基可以选自以上例示的那些。
芳氧基和芳基硫基中的芳基与上述那些相同。芳氧基的具体实例包括但不限于苯氧基、对甲苯氧基、间甲苯氧基、3,5-二甲基苯氧基、2,4,6-三甲基苯氧基、对叔丁基苯氧基、3-联苯氧基、4-联苯氧基、1-萘氧基、2-萘氧基、4-甲基-1-萘氧基、5-甲基-2-萘氧基、1-蒽氧基、2-蒽氧基、9-蒽氧基、1-菲氧基、3-菲氧基和9-菲氧基。芳基硫基可以为例如苯基硫基、2-甲基苯基硫基或4-叔丁基苯基硫基,但不限于此。
卤素基团可以为例如氟、氯、溴或碘。
根据本发明的一个实施方案,由式A表示的化合物可以选自以下化合物1至104,但本发明的范围不限于此:
本发明的另一个方面涉及有机电致发光装置,其包括第一电极、与第一电极相对的第二电极、以及介于第一电极与第二电极之间的一个或更多个有机层,其中有机层,优选地发光层中的一者包含由式A表示的蒽衍生物。
发光层由主体和掺杂剂构成。使用由式A表示的蒽衍生物作为主体。可以在发光层中混合或堆叠除由式A表示的主体化合物之外的一种或更多种主体化合物。
根据本发明的一个实施方案,有机电致发光装置还可以在发光层中包含掺杂剂化合物。
如本文所用,表述“(有机层)包含一种或更多种有机化合物”意指(有机层)包含属于本发明的范围的有机化合物中的一者或者属于有机化合物的范围的两种或更多种不同的化合物。
有机层可以包括空穴注入层、空穴传输层、具有空穴注入和空穴传输两种功能的功能层、发光层、电子传输层和/或电子注入层。
根据本发明的一个更优选的实施方案,介于第一电极与第二电极之间的有机层中的一者可以为发光层。发光层可以由主体和掺杂剂构成。发光层可以包含可以由式A表示的蒽衍生物中的至少一者作为主体。
发光层中使用的掺杂剂化合物由式D-1或D-2表示:
其中X1选自B、P=O和P=S,Y1至Y3各自独立地选自NR41、CR42R43、O、S、Se和SiR44R45,R41至R45彼此相同或不同并且各自独立地选自氢、氘、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C50芳基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30杂环烷基、经取代或未经取代的C2-C50杂芳基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C30芳氧基、经取代或未经取代的C1-C30烷基硫基、经取代或未经取代的C6-C30芳基硫基、经取代或未经取代的C1-C30烷基胺基、经取代或未经取代的C6-C30芳基胺基、经取代或未经取代的C2-C30杂芳基胺基、经取代或未经取代的C1-C30烷基甲硅烷基、经取代或未经取代的C6-C30芳基甲硅烷基、经取代或未经取代的C3-C20混合的脂族-芳族环状基团、硝基、氰基和卤素,条件是R41至R45各自任选地与环A1至A3中的一者或更多者键合以形成脂环族或芳族单环或多环的环,以及R42和R43一起以及R44和R45一起任选地形成脂环族或芳族单环或多环的环,以及A1至A3各自独立地选自经取代或未经取代的C6-C50芳族烃环、经取代或未经取代的C2-C50杂芳族环、经取代或未经取代的C3-C30脂族环和经取代或未经取代的C3-C30混合的脂族-芳族环状基团,条件是环A1至A3中的每一者的取代基一起任选地形成脂环族或芳族单环或多环的环,
其中X1、Y1至Y3、R41至R45和A1至A3如式D-1中所限定。
如本文所用,A1至A3和R41至R45的限定中的术语“经取代的”表示经选自以下的一个或更多个取代基取代:氘、氰基、卤素、羟基、硝基、C1-C24烷基、C1-C24卤代烷基、C3-C30环烷基、C2-C24烯基、C2-C24炔基、C1-C24杂烷基、C6-C30芳基、C7-C30芳基烷基、C7-C30烷基芳基、C2-C30杂芳基、C2-C30杂芳基烷基、C1-C24烷氧基、C1-C24烷基氨基、C6-C30芳基氨基、C2-C30杂芳基氨基、C1-C24烷基甲硅烷基、C6-C30芳基甲硅烷基、C6-C30芳氧基和C3-C30混合的脂族-芳族环状基团。同一限定中的术语“未经取代的”表示不具有取代基。
根据本发明的一个实施方案,由式D-1和D-2表示的掺杂剂化合物可以选自以下化合物101至210,但本发明的范围不限于此:
基于约100重量份的主体,发光层中的掺杂剂的含量通常在约0.01重量份至约20重量份的范围内选择,但不限于此。
可以在根据本发明的有机电致发光装置的发光层中混合或堆叠除由式D-1或D-2表示的掺杂剂化合物之外的一种或更多种掺杂剂化合物。
总之,根据本发明的有机电致发光装置的发光层可以包含由式A表示的主体和一种或更多种另外的主体材料以及由式D-1或D-2表示的掺杂剂和一种或更多种另外的掺杂剂材料的混合物,其可以任选地形成复数个层。
根据本发明的有机电致发光装置的有机层可以形成单层结构。或者,有机层可以具有多层堆叠结构。例如,有机层可以具有包括空穴注入层、空穴传输层、空穴阻挡层、发光层、电子阻挡层、电子传输层和电子注入层的结构,但不限于该结构。有机层的数目没有限制,并且可以增加或减少。根据本发明的有机电致发光装置的有机层的优选结构将在随后的实施例部分中更详细地说明。
将给出关于根据本发明的有机电致发光装置的示例性实施方案的更详细的描述。
本发明的有机电致发光装置包括阳极、空穴传输层、发光层、电子传输层和阴极。本发明的有机电致发光装置还可以任选地包括在阳极与空穴传输层之间的空穴注入层以及在电子传输层与阴极之间的电子注入层。如有必要,本发明的有机电致发光装置还可以包括一个或两个中间层,例如空穴阻挡层或电子阻挡层。本发明的有机电致发光装置还可以根据装置的期望特性包括具有各种功能的一个或更多个有机层例如覆盖层。
根据本发明的一个实施方案的有机电致发光装置的具体结构、用于制造所述装置的方法、以及用于有机层的材料如下。
首先,在基底上涂覆阳极材料以形成阳极。基底可以为用于一般的电致发光装置的任何基底。基底优选为透明性、表面平滑性、易处理性和防水性优异的有机基底或透明塑料基底。使用高度透明且导电的金属氧化物例如氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锡(SnO2)或氧化锌(ZnO)作为阳极材料。
通过真空热蒸镀或旋涂在阳极上涂覆空穴注入材料以形成空穴注入层。然后,通过真空热蒸镀或旋涂在空穴注入层上涂覆空穴传输材料以形成空穴传输层。
空穴注入材料没有特别限制,只要其通常用于本领域即可。这样的材料的具体实例包括4,4’,4”-三(2-萘基苯基-苯基氨基)三苯胺(2-TNATA)、N,N’-二(1-萘基)-N,N’-二苯基联苯胺(NPD)、N,N’-二苯基-N,N’-双(3-甲基苯基)-1,1’-联苯基-4,4’-二胺(TPD)和N,N’-二苯基-N,N’-双(4-(苯基-间甲苯基氨基)苯基)联苯基-4,4’-二胺(DNTPD)。
空穴传输材料没有特别限制,只要其通常用于本领域即可。这样的材料的实例包括N,N’-双(3-甲基苯基)-N,N’-二苯基-(1,1-联苯基)-4,4’-二胺(TPD)和N,N’-二(萘-1-基)-N,N’-二苯基联苯胺(α-NPD)。
随后,在空穴传输层上顺序地层合空穴辅助层和发光层。可以通过真空热蒸镀或旋涂在发光层上任选地形成空穴阻挡层。空穴阻挡层形成为薄膜并且阻挡空穴通过有机发光层进入阴极。空穴阻挡层的这种作用防止装置的寿命和效率劣化。具有非常低的最高占据分子轨道(HOMO)能级的材料用于空穴阻挡层。空穴阻挡材料没有特别限制,只要其可以传输电子并且具有比发光化合物更高的电离电势即可。合适的空穴阻挡材料的代表性实例包括BAlq、BCP和TPBI。
用于空穴阻挡层的材料的实例包括但不限于BAlq、BCP、Bphen、TPBI、NTAZ、BeBq2、OXD-7和Liq。
通过真空热蒸镀或旋涂在空穴阻挡层上沉积电子传输层,并且在电子传输层上形成电子注入层。通过真空热蒸镀在电子注入层上沉积阴极材料以形成阴极,从而完成有机电致发光装置的制造。
例如,可以使用锂(Li)、镁(Mg)、铝(Al)、铝-锂(Al-Li)、钙(Ca)、镁-铟(Mg-In)或镁-银(Mg-Ag)作为用于形成阴极的金属。有机电致发光装置可以为顶部发射型。在这种情况下,可以使用透射材料例如ITO或IZO来形成阴极。
用于电子传输层的材料用于稳定地传输从阴极注入的电子。电子传输材料可以为本领域已知的任何材料,并且其实例包括但不限于喹啉衍生物,特别是三(8-羟基喹啉)铝(Alq3)、TAZ、Balq、双(苯并喹啉-10-羟基)铍(Bebq2);以及二唑衍生物,例如PBD、BMD和BND。
各有机层可以通过单分子沉积或溶液过程来形成。根据单分子沉积过程,将用于各层的材料在加热和真空或减压下蒸镀成薄膜。根据溶液过程,将用于各层的材料与合适的溶剂混合,然后通过合适的方法例如喷墨印刷、辊对辊涂覆、丝网印刷、喷涂、浸涂或旋涂使混合物形成为薄膜。
本发明的有机电致发光装置还可以包括由在380nm至800nm的波长范围内发射蓝色光、绿色光或红色光的材料构成的发光层。即,本发明的有机电致发光装置可以包括复数个发光层。用于另外的发光层的蓝色、绿色或红色发光材料可以为荧光材料或磷光材料。
本发明的有机电致发光装置可以用于选自以下的显示器或照明系统:平板显示器、柔性显示器、单色平板照明系统、白色平板照明系统、柔性单色照明系统、柔性白色照明系统、用于汽车应用的显示器、用于虚拟现实的显示器和用于增强现实的显示器。
将参照以下实施例更具体地说明本发明。然而,对本领域技术人员而言明显的是,这些实施例决不旨在限制本发明的范围。
合成例1.化合物43的合成
合成例1-1.中间体1-a的合成
在2L反应器中将溴苯(d5)(60.4g,0.373mol)和480mL四氢呋喃冷却至-78℃并搅拌。向冷溶液中滴加正丁基锂(223.6mL,0.357mol)。将混合物在相同温度下搅拌1小时。向所得反应溶液中滴加邻苯二甲醛(20g,0.149mol)在100mL四氢呋喃中的溶液,然后在室温下搅拌。将反应用200mL氯化铵水溶液淬灭。将反应溶液用乙酸乙酯萃取,在减压下浓缩,并通过柱色谱法来纯化以得到中间体1-a(40g,89%)。
合成例1-2:中间体1-b的合成
在500mL反应器中将中间体1-a(40g,0.133mol)溶解在200mL乙酸中并搅拌。向溶液中滴加2mL溴化氢。将混合物在80℃下搅拌2小时。在反应完成之后,将反应溶液冷却至室温。将反应溶液缓慢倒入含有500mL蒸馏水的烧杯中,然后搅拌。将所得固体过滤,用蒸馏水洗涤,并通过柱色谱法来纯化以得到中间体1-b(13g,37%)。
合成例1-3:中间体1-c的合成
在500mL反应器中将中间体1-b(13.0g,0.049mol)溶解在130mL N,N-二甲基酰胺中。将溶液在室温下搅拌。向溶液中滴加N-溴代琥珀酰亚胺(10.54g,0.059mol)在40mL N,N-二甲基酰胺中的溶液。通过薄层色谱法确定反应的完成。将反应溶液倒入含有500mL蒸馏水的烧杯中,然后搅拌。将所得固体过滤,用蒸馏水洗涤,并通过柱色谱法来纯化以得到中间体1-c(14g,83%)。
合成例1-4:中间体1-d的合成
在500mL反应器中将中间体1-c(50g,0.146mol)溶解在500mL四氢呋喃中。将溶液冷却至-78℃并向其中滴加正丁基锂(100mL,0.161mol)。将混合物搅拌5小时。向混合物中添加硼酸三甲酯(18mL,0.161mol),然后在室温下搅拌过夜。在反应完成之后,将反应混合物用2N盐酸酸化并重结晶以得到中间体1-d(25g,56%)。
合成例1-5:中间体1-e的合成
在500mL反应器中放入中间体1-d(30g,0.098mol)、(4-溴苯基)硼酸(23.5g,0.117mol)、乙酸钯(0.4g,0.002mol)、碳酸钾(27g,0.195mol)和Sphos(1.6g,0.004mol),并向其中添加200mL甲苯、90mL乙醇和60mL蒸馏水。将反应器的温度升至90℃,然后搅拌过夜。在反应完成之后,将反应器的温度冷却至室温。将反应混合物用甲醇萃取。将有机层分离,在减压下浓缩,通过柱色谱法来纯化,并从甲苯和丙酮中重结晶以得到中间体1-e(12g,32%)。
合成例1-6:化合物43的合成
以与合成例1-5中相同的方式合成化合物43(产率30%),不同之处在于分别使用中间体1-e和2-溴-3-苯基苯并呋喃代替中间体1-d和(4-溴苯基)硼酸。
MS(MALDI-TOF):m/z 531.25[M+]
合成例2.化合物56的合成
合成例2-1:中间体2-a的合成
在500mL反应器中放入5-溴苯并呋喃(30g,0.152mol)、(苯基-d5)硼酸(23.2g,0.183mol)、四(三苯基膦)钯(0)(5.3g,0.005mol)、碳酸钾(42.1g,0.305mol)、300mL THF和120mL蒸馏水。将混合物在回流下搅拌12小时。在反应完成之后,使反应溶液静置以进行层分离。将有机层在减压下浓缩并通过柱色谱法来纯化以得到中间体2-a(21.2g,70%)。
合成例2-2:中间体2-b的合成
在500mL反应器中放入中间体2-a(21.2g,0.106mol)和二氯甲烷。将混合物冷却至-10℃,并向其中添加溴。将所得混合物搅拌1小时。向反应混合物中添加硫代硫酸钠水溶液,然后搅拌。使混合物静置以进行层分离。将有机层在减压下浓缩,添加乙醇,冷却至-10℃,并添加氢氧化钾的乙醇溶液。将混合物加热以回流4小时。在反应完成之后,使反应溶液静置以进行层分离。将有机层在减压下浓缩并通过柱色谱法来纯化以得到中间体2-b(20g,70%)。
合成例2-3:化合物56的合成
将中间体2-b(20g,0.072mol)、10-苯基-蒽-9-硼酸(25.7g,0.086mol)、四(三苯基膦)钯(0)(2.5g,0.002mol)、碳酸钾(29.8g,0.216mol)、140mL甲苯、60mL乙醇和60mL蒸馏水回流12小时。在反应完成之后,使反应溶液静置以进行层分离。将有机层在减压下浓缩,通过柱色谱法来纯化,并重结晶以得到化合物56(10g,32%)。
MS(MALDI-TOF):m/z 451.20[M+]
合成例3.化合物58的合成
合成例3-1:中间体3-a的合成
以与合成例2-1中相同的方式合成中间体3-a(产率77%),不同之处在于使用苯基硼酸代替(苯基-d5)硼酸。
合成例3-2:中间体3-b的合成
以与合成例2-2中相同的方式合成中间体3-b(产率70%),不同之处在于使用中间体3-a代替中间体2-a。
合成例3-3:中间体3-c的合成
以与合成例2-3中相同的方式合成中间体3-c(产率74%),不同之处在于分别使用中间体3-b和4-(10-苯基-9-蒽基)苯基硼酸代替中间体2-b和10-苯基-蒽-9-硼酸。
合成例3-4:中间体3-d的合成
在500mL反应器中将中间体3-c(20g,0.038mol)和250mL THF冷却至-50℃,并向其中添加正丁基锂(1.6M)。在1小时之后,缓慢添加碘。将温度逐渐升至室温。在室温下向混合物中添加硫代硫酸钠水溶液。使所得混合物静置以进行层分离。将有机层在减压下浓缩并通过柱色谱法来纯化以得到中间体3-d(16g,65%)。
合成例3-5:化合物58的合成
以与合成例2-3中相同的方式合成化合物58(产率50%),不同之处在于分别使用中间体3-d和(苯基-d5)硼酸代替中间体2-b和10-苯基-蒽-9-硼酸。
MS(MALDI-TOF):m/z 603.26[M+]
合成例4.化合物61的合成
合成例4-1:中间体4-a的合成
以与合成例2-3中相同的方式合成中间体4-a(产率71%),不同之处在于使用4-溴苯基硼酸代替10-苯基-蒽-9-硼酸。
合成例4-2:化合物61的合成
以与合成例2-3中相同的方式合成化合物61(产率30%),不同之处在于分别使用中间体4-a和10-苯基(d5)-蒽-9-硼酸代替中间体2-b和10-苯基-蒽-9-硼酸。
MS(MALDI-TOF):m/z 532.26[M+]
合成例5.化合物66的合成
合成例5-1:化合物66的合成
以与合成例2-3中相同的方式合成化合物66(产率30%),不同之处在于分别使用3-溴-2-萘-1-基-苯并呋喃和10-苯基(d5)-蒽-9-硼酸代替中间体2-b和10-苯基-蒽-9-硼酸。
MS(MALDI-TOF):m/z 501.21[M+]
合成例6.化合物14的合成
合成例6-1:中间体6-a的合成
在500mL反应器中将7-氯苯并[b]噻吩(30g,0.178mol)和DMF搅拌,并向其中添加NBS。将混合物在搅拌下回流6小时。向反应溶液中添加蒸馏水。使所得混合物静置以进行层分离。将有机层在减压下浓缩并通过柱色谱法来纯化以得到中间体6-a(27g,62%)。
合成例6-2:中间体6-b的合成
以与合成例2-1中相同的方式合成中间体6-b(产率70%),不同之处在于分别使用中间体6-a和苯基硼酸代替5-溴苯并呋喃和(苯基-d5)硼酸。
合成例6-3:中间体6-c的合成
以与合成例3-4中相同的方式合成中间体6-c(产率70%),不同之处在于使用中间体6-b代替中间体3-c。
合成例6-4:中间体6-d的合成
以与合成例2-3中相同的方式合成中间体6-d(产率68%),不同之处在于分别使用中间体6-c和10-苯基(d5)-蒽-9-硼酸代替中间体2-b和10-苯基-蒽-9-硼酸。
合成例6-5:化合物14的合成
以与合成例2-3中相同的方式合成化合物14(产率33%),不同之处在于分别使用中间体6-d和二苯并[b,d]呋喃-1-基硼酸代替中间体2-b和10-苯基-蒽-9-硼酸。
MS(MALDI-TOF):m/z 633.22[M+]
合成例7.化合物89的合成
合成例7-1:中间体7-a的合成
以与合成例3-3中相同的方式合成中间体7-a(产率70%),不同之处在于使用10-(苯基-d5)-蒽-9-硼酸代替4-(10-苯基-9-蒽基)苯基硼酸。
合成例7-2:中间体7-b的合成
以与合成例3-4中相同的方式合成中间体7-b(产率63%),不同之处在于使用中间体7-a代替中间体3-c。
合成例7-3:化合物89的合成
以与合成例3-5中相同的方式合成化合物89(产率51%),不同之处在于分别使用中间体7-b和苯基硼酸代替中间体3-d和(苯基-d5)硼酸。
MS(MALDI-TOF):m/z 527.23[M+]
合成例8.化合物90的合成
合成例8-1:中间体8-a的合成
以与合成例1-4中相同的方式合成中间体8-a(产率55%),不同之处在于使用(蒽-d8)-9-溴-10-(苯基-d5)代替中间体1-c。
合成例8-2:中间体8-b的合成
以与合成例2-3中相同的方式合成中间体8-b(产率55%),不同之处在于使用中间体8-a代替10-苯基-蒽-9-硼酸。
合成例8-3:中间体8-c的合成
以与合成例3-4中相同的方式合成中间体8-c(产率67%),不同之处在于使用中间体8-b代替中间体3-c。
合成例8-4:化合物90的合成
以与合成例7-3中相同的方式合成化合物90(产率47%),不同之处在于使用中间体8-c代替中间体7-b。
MS(MALDI-TOF):m/z 540.31[M+]
合成例9.化合物91的合成
合成例9-1:中间体9-a的合成
在500mL反应器中放入溴苄基溴(20g,0.08mol)、(苯基-d5)硼酸(10g,0.078mol)、碳酸钠(10g,0.1mol)和四(三苯基膦)钯(0)(1.8g,0.002mol)。将混合物加热以在50℃下回流。在1小时之后,向反应溶液中添加蒸馏水,然后搅拌。使所得混合物静置以进行层分离。将有机层过滤,用甲苯洗涤并在减压下浓缩。此后,将浓缩物通过柱色谱法来纯化以得到中间体9-a(16g,82%)。
合成例9-2:中间体9-b的合成
在500mL反应器中将中间体9-a(20g,0.08mol)和200mL THF冷却至-78℃,并向其中添加正丁基锂(1.6M)。向混合物中缓慢添加硼酸三甲酯。将温度逐渐升至室温。向所得混合物中添加2M HCl水溶液,然后搅拌20分钟。使反应混合物静置以进行层分离。将有机层用蒸馏水洗涤,浓缩,并从THF和庚烷中重结晶以得到中间体9-b(11g,63%)。
合成例9-3:中间体9-c的合成
在500mL反应器中将中间体9-b(15g,0.07mol)、碳酸铯(34g,0.1mol)、四(三苯基膦)钯(0)(2.4g,0.002mol)和150mL甲苯搅拌。在滴加1,1'-(联苯-d5)-2-碳酰氯(20g,0.09mol)之后,将混合物加热以在110℃下回流。在2小时之后,向反应溶液中添加甲苯和蒸馏水,然后搅拌。使混合物静置以进行层分离。将有机层在减压下浓缩并通过柱色谱法来纯化以得到中间体9-c(14g,57%)。
合成例9-4:中间体9-d的合成
在500mL反应器中将中间体9-c(20g,0.06mol)、In(OTf)3(3.1g,0.006mol)和120mL二氯苯加热以在110℃下回流。在24小时之后,将反应溶液在50℃下通过硅藻土过滤并用MC洗涤。将有机层在减压下浓缩并通过柱色谱法来纯化。随后的重结晶得到中间体9-d(8g,43%)。
合成例9-5:中间体9-e的合成
在500mL反应器中将中间体9-d(30g,0.09mol)和300mL DMF搅拌。此后,将混合物冷却至0℃并向其中添加NBS(16g,0.09mol)。将温度升至室温。在搅拌3小时之后,向所得混合物中添加蒸馏水。继续搅拌。将反应混合物过滤,洗涤,通过柱色谱法来纯化并从甲醇中重结晶以得到中间体9-e(33g,89%)。
合成例9-6:中间体9-f的合成
以与合成例1-4中相同的方式合成中间体9-f(产率53%),不同之处在于使用中间体9-e代替中间体1-c。
合成例9-7:化合物91的合成
以与合成例1-5中相同的方式合成化合物91(产率52%),不同之处在于分别使用中间体9-f和3-溴-2-苯基苯并呋喃代替中间体1-d和(4-溴苯基)硼酸。
MS(MALDI-TOF):m/z 531.25[M+]
合成例10.化合物92的合成
合成例10-1:中间体10-a的合成
以与合成例2-3中相同的方式合成中间体10-a(产率52%),不同之处在于使用(蒽-d8)-9-溴-10-(1,1-联苯)代替中间体1-c。
合成例10-2:中间体10-b的合成
以与合成例2-3中相同的方式合成中间体10-b(产率54%),不同之处在于使用中间体10-a代替10-苯基-蒽-9-硼酸。
合成例10-3:中间体10-c的合成
以与合成例3-4中相同的方式合成中间体10-c(产率64%),不同之处在于使用中间体10-b代替中间体3-c。
合成例10-4:化合物92的合成
以与合成例7-3中相同的方式合成化合物92(产率45%),不同之处在于使用中间体8-c代替中间体7-b。
MS(MALDI-TOF):m/z 611.31[M+]
实施例1至10:有机电致发光装置的制造
对ITO玻璃进行图案化以具有2mm×2mm的发光区域,接着进行清洗。在将清洗的ITO玻璃安装在真空室中之后,将基础压力调节至1×10-7托。在ITO玻璃上将DNTPD和α-NPD以此顺序沉积。使用表1中示出的本发明的主体化合物和掺杂剂化合物的混合物以形成厚的发光层。此后,在发光层上以1:1的比率使用式E-1的化合物和式E-2的化合物以形成厚的电子传输层。在电子传输层上使用式E-2的化合物以形成厚的电子注入层。在电子注入层上沉积Al以形成厚的Al电极,从而完成有机电致发光装置的制造。在10mA/cm2下测量有机电致发光装置的发光特性。
比较例1至6
以与实施例1至10中相同的方式制造有机电致发光装置,不同之处在于使用BH1、BH2、BH3、BH4、BH5或BH6代替主体化合物。在10mA/cm2下测量有机电致发光装置的发光特性。BH1、BH2、BH3、BH4、BH5和BH6的结构如下:
表1
如从表1中的结果可以看出的,与分别采用结构与实施例1至10的有机电致发光装置中采用的主体化合物的特定结构不同的BH1、BH2、BH3、BH4、BH5和BH6的比较例1至6的装置相比,各自采用本发明的化合物作为用于发光层的主体化合物的实施例1至10的有机电致发光装置显示出显著改善的寿命特性(包括长寿命)和低电压特性。
Claims (14)
1.一种由式A表示的蒽衍生物:
其中Ar1选自经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C50杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,R1至R14彼此相同或不同并且各自独立地选自氢、氘、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C30烯基、经取代或未经取代的C2-C30炔基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的C2-C50杂芳基、经取代或未经取代的C2-C30杂环烷基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C50芳氧基、经取代或未经取代的C1-C30烷基硫基、经取代或未经取代的C6-C50芳基硫基、经取代或未经取代的C1-C30烷基胺基、经取代或未经取代的C6-C50芳基胺基、经取代或未经取代的C1-C30烷基甲硅烷基、经取代或未经取代的C6-C50芳基甲硅烷基、经取代或未经取代的C3-C50混合的脂族-芳族环状基团、氰基、硝基和卤素,条件是R9和R10中的一者与L1键合,X为氧(O)或硫原子(S),L1为二价连接基团且为单键或者选自经取代或未经取代的C6-C50亚芳基、经取代或未经取代的C2-C50亚杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,以及n为1至3的整数,条件是当n为2或更大时,所述连接基团L1彼此相同或不同,Ar1、R1至R14和L1的限定中的“经取代的”表示经选自以下的一个或更多个取代基取代:氘、氰基、卤素、羟基、硝基、烷基、卤代烷基、环烷基、烯基、炔基、杂烷基、芳基、芳基烷基、烷基芳基、杂芳基、杂芳基烷基、烷氧基、烷基氨基、芳基氨基、杂芳基氨基、烷基甲硅烷基、芳基甲硅烷基、芳氧基和混合的脂族-芳族环状基团,以及其中所述由式A表示的蒽衍生物包含至少一个氘原子(D)。
2.根据权利要求1所述的蒽衍生物,其中所述由式A表示的蒽衍生物为由式A-1或式A-2表示的化合物:
其中Ar11选自经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C50杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,R21至R33彼此相同或不同并且各自独立地选自氢、氘、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C50芳基、经取代或未经取代的C2-C30烯基、经取代或未经取代的C2-C30炔基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的C2-C50杂芳基、经取代或未经取代的C2-C30杂环烷基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C50芳氧基、经取代或未经取代的C1-C30烷基硫基、经取代或未经取代的C6-C50芳基硫基、经取代或未经取代的C1-C30烷基胺基、经取代或未经取代的C6-C50芳基胺基、经取代或未经取代的C1-C30烷基甲硅烷基、经取代或未经取代的C6-C50芳基甲硅烷基、经取代或未经取代的C3-C50混合的脂族-芳族环状基团、氰基、硝基和卤素,X为氧(O)或硫原子(S),L2为二价连接基团且为单键或者选自经取代或未经取代的C6-C50亚芳基、经取代或未经取代的C2-C50亚杂芳基和经取代或未经取代的C3-C50混合的脂族-芳族环状基团,以及m为1至3的整数,条件是当m为2或更大时,所述连接基团L1彼此相同或不同,Ar11、R21至R33和L2的限定中的“经取代的”表示经选自以下的一个或更多个取代基取代:氘、氰基、卤素、羟基、硝基、烷基、卤代烷基、环烷基、烯基、炔基、杂烷基、芳基、芳基烷基、烷基芳基、杂芳基、杂芳基烷基、烷氧基、烷基氨基、芳基氨基、杂芳基氨基、烷基甲硅烷基、芳基甲硅烷基、芳氧基和混合的脂族-芳族环状基团,
其中Ar11、R21至R33、X、L2和m如式A-1中所限定,以及其中由式A-1和A-2表示的化合物各自包含至少一个氘原子(D)。
3.根据权利要求1所述的蒽衍生物,其中式A中的R11至R14中的至少一者选自经取代或未经取代的C6-C20芳基、经取代或未经取代的C3-C20环烷基和经取代或未经取代的C3-C20杂芳基。
4.根据权利要求3所述的蒽衍生物,其中式A中的R11至R14中的至少一者为经取代或未经取代的氘化C6-C20芳基、经取代或未经取代的氘化C3-C20环烷基或者经取代或未经取代的氘化C3-C20杂芳基。
5.根据权利要求2所述的蒽衍生物,其中式A-1中的R29和式A-2中的R29各自为包含至少一个氘原子(D)的经取代或未经取代的氘化C6-C20芳基、经取代或未经取代的氘化C3-C20环烷基或者经取代或未经取代的氘化C3-C20杂芳基。
6.根据权利要求1所述的蒽衍生物,其中所述由式A表示的蒽衍生物的氘化程度为至少10%。
7.根据权利要求1所述的蒽衍生物,其中所述由式A表示的蒽衍生物的氘化程度为至少30%。
9.一种有机电致发光装置,包括第一电极、与所述第一电极相对的第二电极、以及介于所述第一电极与所述第二电极之间的一个或更多个有机层,其中所述有机层中的一者包含根据权利要求1所述的由式A表示的蒽衍生物。
10.根据权利要求9所述的有机电致发光装置,其中所述有机层包括选自空穴注入层、空穴传输层、具有空穴注入和空穴传输两种功能的功能层、发光层、电子传输层和电子注入层的一个或更多个层。
11.根据权利要求10所述的有机电致发光装置,其中介于所述第一电极与所述第二电极之间的有机层中的一者为由主体和掺杂剂构成的发光层,以及使用所述由式A表示的蒽衍生物作为所述主体。
12.根据权利要求11所述的有机电致发光装置,其中在所述发光层中混合或堆叠除由式A表示的主体化合物之外的一种或更多种主体化合物。
13.根据权利要求11所述的有机电致发光装置,其中所述掺杂剂由式D-1或D-2表示:
其中X1选自B、P=O和P=S,Y1至Y3各自独立地选自NR41、CR42R43、O、S、Se和SiR44R45,R41至R45彼此相同或不同并且各自独立地选自氢、氘、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C50芳基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30杂环烷基、经取代或未经取代的C2-C50杂芳基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C30芳氧基、经取代或未经取代的C1-C30烷基硫基、经取代或未经取代的C6-C30芳基硫基、经取代或未经取代的C1-C30烷基胺基、经取代或未经取代的C6-C30芳基胺基、经取代或未经取代的C2-C30杂芳基胺基、经取代或未经取代的C1-C30烷基甲硅烷基、经取代或未经取代的C6-C30芳基甲硅烷基、经取代或未经取代的C3-C20混合的脂族-芳族环状基团、硝基、氰基和卤素,条件是R41至R45各自任选地与环A1至A3中的一者或更多者键合以形成脂环族或芳族单环或多环的环,以及R42和R43一起以及R44和R45一起任选地形成脂环族或芳族单环或多环的环,以及A1至A3各自独立地选自经取代或未经取代的C6-C50芳族烃环、经取代或未经取代的C2-C50杂芳族环、经取代或未经取代的C3-C30脂族环和经取代或未经取代的C3-C30混合的脂族-芳族环状基团,条件是环A1至A3中的每一者的取代基一起任选地形成脂环族或芳族单环或多环的环,A1至A3和R41至R45的限定中的“经取代的”表示经选自以下的一个或更多个取代基取代:氘、氰基、卤素、羟基、硝基、烷基、卤代烷基、环烷基、烯基、炔基、杂烷基、芳基、芳基烷基、烷基芳基、杂芳基、杂芳基烷基、烷氧基、烷基氨基、芳基氨基、杂芳基氨基、烷基甲硅烷基、芳基甲硅烷基、芳氧基和混合的脂族-芳族环状基团,
其中X1、Y1至Y3、R41至R45和A1至A3如式D-1中所限定。
14.根据权利要求10所述的有机电致发光装置,其中所述有机电致发光装置用于选自以下的显示器或照明系统:平板显示器、柔性显示器、单色平板照明系统、白色平板照明系统、柔性单色照明系统、柔性白色照明系统、用于汽车应用的显示器、用于虚拟现实的显示器和用于增强现实的显示器。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009203203A (ja) * | 2008-02-29 | 2009-09-10 | Toyo Ink Mfg Co Ltd | アントラセン誘導体及びその用途 |
CN107004776A (zh) * | 2014-12-31 | 2017-08-01 | Sfc株式会社 | 具有高效率和长寿命的有机发光元件 |
WO2020085829A1 (en) * | 2018-10-26 | 2020-04-30 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of light-emitting materials and organic electroluminescent device comprising the same |
Family Cites Families (9)
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KR100901887B1 (ko) | 2008-03-14 | 2009-06-09 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광소자 |
KR101427605B1 (ko) | 2009-03-31 | 2014-08-07 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 |
KR101550351B1 (ko) * | 2012-11-06 | 2015-09-07 | 에스에프씨 주식회사 | 유기 전계발광 화합물 및 이를 포함하는 유기 전계발광 소자 |
KR102142193B1 (ko) * | 2017-11-16 | 2020-08-06 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR20200047400A (ko) | 2018-10-26 | 2020-05-07 | 롬엔드하스전자재료코리아유한회사 | 복수 종의 발광 재료 및 이를 포함하는 유기 전계 발광 소자 |
KR102094830B1 (ko) | 2018-11-30 | 2020-03-30 | 에스에프씨 주식회사 | 다환 방향족 유도체 화합물 및 이를 이용한 유기발광소자 |
KR102148296B1 (ko) | 2019-07-29 | 2020-08-26 | 에스에프씨주식회사 | 보론 화합물을 포함하는 유기발광소자 |
-
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009203203A (ja) * | 2008-02-29 | 2009-09-10 | Toyo Ink Mfg Co Ltd | アントラセン誘導体及びその用途 |
CN107004776A (zh) * | 2014-12-31 | 2017-08-01 | Sfc株式会社 | 具有高效率和长寿命的有机发光元件 |
WO2020085829A1 (en) * | 2018-10-26 | 2020-04-30 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of light-emitting materials and organic electroluminescent device comprising the same |
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