CN112789273B - 化合物及包含其的有机发光器件 - Google Patents
化合物及包含其的有机发光器件 Download PDFInfo
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- CN112789273B CN112789273B CN201980063285.4A CN201980063285A CN112789273B CN 112789273 B CN112789273 B CN 112789273B CN 201980063285 A CN201980063285 A CN 201980063285A CN 112789273 B CN112789273 B CN 112789273B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 89
- 239000000126 substance Substances 0.000 claims description 78
- 239000012044 organic layer Substances 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000004305 biphenyl Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 138
- -1 hole transport Substances 0.000 description 43
- 238000002347 injection Methods 0.000 description 33
- 239000007924 injection Substances 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 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 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
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- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- GPGIIKKUKINTGW-UHFFFAOYSA-N 2-bromo-4,6-diphenylpyrimidine Chemical compound N=1C(Br)=NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 GPGIIKKUKINTGW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 229940125898 compound 5 Drugs 0.000 description 3
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- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- YGUPAQDKOAPZHC-UHFFFAOYSA-N tricyclohexylphosphane Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 YGUPAQDKOAPZHC-UHFFFAOYSA-N 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- QNEGDGPAXKYZHZ-UHFFFAOYSA-N (2,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1Cl QNEGDGPAXKYZHZ-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- UJCQCUHXXOYHGI-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1.ClC1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 UJCQCUHXXOYHGI-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
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- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- 239000002019 doping agent Substances 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- 125000005462 imide group Chemical group 0.000 description 2
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- 150000002894 organic compounds Chemical class 0.000 description 2
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- 125000002971 oxazolyl group Chemical group 0.000 description 2
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- 239000001301 oxygen Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
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- 230000008022 sublimation Effects 0.000 description 2
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 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
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- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
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- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
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- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
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- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 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 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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Abstract
本发明提供新型化合物及利用其的有机发光器件。
Description
技术领域
与相关申请的相互引用
本申请主张基于2018年11月27日的韩国专利申请第10-2018-0148563号和2019年11月8日的韩国专利申请第10-2019-0142729号的优先权,包含该韩国专利申请的文献中公开的全部内容作为本说明书的一部分。
本发明涉及新型化合物及包含其的有机发光器件。
背景技术
通常情况下,有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机发光器件具有宽视角、优异的对比度、快速响应时间,亮度、驱动电压和响应速度特性优异,因此正在进行大量的研究。
有机发光器件通常具有包括阳极和阴极以及位于上述阳极与阴极之间的有机物层的结构。为了提高有机发光器件的效率和稳定性,上述有机物层大多情况下由分别利用不同的物质构成的多层结构形成,例如,可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。对于这样的有机发光器件的结构而言,如果在两电极之间施加电压,则空穴从阳极注入有机物层,电子从阴极注入有机物层,当所注入的空穴和电子相遇时会形成激子(exciton),该激子重新跃迁至基态时就会发出光。
对用于如上所述的有机发光器件的有机物,持续要求开发新的材料。
现有技术
专利文献
(专利文献0001)韩国专利公开号第10-2000-0051826号
发明内容
所要解决的课题
本发明涉及新型化合物及包含其的有机发光器件。
课题的解决方法
本发明提供由下述化学式1表示的化合物:
[化学式1]
X各自独立地为N或CH,但X中的1个以上为N,
Ar1和Ar2各自独立地为取代或未取代的C6-60芳基;或者取代或未取代的包含选自N、O和S中的任一个或更多个杂原子的C5-60杂芳基,
Ar3为取代或未取代的包含1个以上N的C5-60杂芳基,
Y1为O、S或NR2,
n各自独立地为0至7的整数,
R1各自独立地为氢;氘;取代或未取代的C1-60烷基;取代或未取代的C3-60环烷基;取代或未取代的C6-60芳基;或者取代或未取代的包含1个以上选自N、O和S中的杂原子的C5-60杂芳基,
R2为取代或未取代的C1-60烷基、或者取代或未取代的C6-60芳基。
另外,本发明提供一种有机发光器件,其中,包括:第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与上述第二电极之间的1层以上的有机物层,上述有机物层中的1层以上包含由上述化学式1表示的化合物。
发明效果
由上述化学式1表示的化合物可以用作有机发光器件的有机物层的材料,在有机发光器件中能够实现效率的提高、较低的驱动电压和/或寿命特性的提高。特别是,由上述化学式1表示的化合物可以用作空穴注入、空穴传输、空穴注入和传输、发光、电子传输、或电子注入的材料。
附图说明
图1图示了由基板1、阳极2、发光层3、阴极4构成的有机发光器件的例子。
图2图示了由基板1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4构成的有机发光器件的例子。
图3图示了由基板1、阳极2、空穴注入层5、空穴传输层6、电子阻挡层9、发光层7、空穴阻挡层10、电子传输层8、电子注入层11和阴极4构成的有机发光器件的例子。
具体实施方式
下面,为了帮助理解本发明而更详细地进行说明。
本发明提供由上述化学式1表示的化合物。
在本说明书中,或/>表示与其它取代基连接的键。
在本说明书中,“取代或未取代的”这一用语是指被选自氘;卤素基团;腈基;硝基;羟基;羰基;酯基;酰亚胺基;氨基;氧化膦基;烷氧基;芳氧基;烷基硫基(alkyl thioxy);芳基硫基(/> aryl thioxy);烷基磺酰基(/>alkyl sulfoxy);芳基磺酰基(/>aryl sulfoxy);甲硅烷基;硼基;烷基;环烷基;烯基;芳基;芳烷基;芳烯基;烷基芳基;烷基胺基;芳烷基胺基;杂芳基胺基;芳基胺基;芳基膦基;或者包含N、O和S原子中的1个以上的杂环基中的1个以上的取代基取代或未取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。例如,“2个以上的取代基连接而成的取代基”可以为联苯基。即,联苯基可以为芳基,也可以被解释为2个苯基连接而成的取代基。
在本说明书中,羰基的碳原子数没有特别限定,但优选碳原子数为1至40。具体而言,可以为如下结构的基团,但并不限定于此。
在本说明书中,酯基中,酯基的氧可以被碳原子数1至25的直链、支链或环状的烷基、或者碳原子数6至25的芳基取代。具体而言,可以为下述结构式的基团,但并不限定于此。
在本说明书中,酰亚胺基的碳原子数没有特别限定,但优选碳原子数为1至25。具体而言,可以为如下结构的基团,但并不限定于此。
在本说明书中,甲硅烷基具体有三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但并不限定于此。
在本说明书中,硼基具体有三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等,但并不限定于此。
在本说明书中,作为卤素基团的例子,有氟、氯、溴或碘。
在本说明书中,上述烷基可以为直链或支链,碳原子数没有特别限定,但优选为1至40。根据一实施方式,上述烷基的碳原子数为1至20。根据另一实施方式,上述烷基的碳原子数为1至10。根据另一实施方式,上述烷基的碳原子数为1至6。作为烷基的具体例,有甲基、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、5-甲基己基等,但并不限定于此。
在本说明书中,上述烯基可以为直链或支链,碳原子数没有特别限定,但优选为2至40。根据一实施方式,上述烯基的碳原子数为2至20。根据另一实施方式,上述烯基的碳原子数为2至10。根据另一实施方式,上述烯基的碳原子数为2至6。作为具体例,有乙烯基、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-1-基、2-苯基乙烯-1-基、2,2-二苯基乙烯-1-基、2-苯基-2-(萘-1-基)乙烯-1-基、2,2-双(二苯-1-基)乙烯-1-基、茋基、苯乙烯基等,但并不限定于此。
在本说明书中,环烷基没有特别限定,但优选为碳原子数3至60的环烷基,根据一实施方式,上述环烷基的碳原子数为3至30。根据另一实施方式,上述环烷基的碳原子数为3至20。根据另一实施方式,上述环烷基的碳原子数为3至6。具体而言,有环丙基、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、环辛基等,但并不限定于此。
在本说明书中,芳基没有特别限定,但优选为碳原子数6至60的芳基,可以为单环芳基或多环芳基。根据一实施方式,上述芳基的碳原子数为6至30。根据一实施方式,上述芳基的碳原子数为6至20。关于上述芳基,作为单环芳基,可以为苯基、联苯基、三联苯基等,但并不限定于此。作为上述多环芳基,可以为萘基、蒽基、菲基、芘基、苝基、基、芴基等,但并不限定于此。
在本说明书中,芴基可以被取代,2个取代基可以彼此结合而形成螺结构。在上述芴基被取代的情况下,可以为等。但并不限定于此。
在本说明书中,杂环基是包含O、N、Si和S中的1个以上作为杂原子的杂环基,碳原子数没有特别限定,但优选碳原子数为2至60。作为杂环基的例子,有噻吩基、呋喃基、吡咯基、咪唑基、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、菲咯啉基(phenanthroline)、噻唑基、异/>唑基、/>二唑基、噻二唑基、苯并噻唑基、吩噻嗪基和二苯并呋喃基等,但不仅限于此。
在本说明书中,芳烷基、芳烯基、烷基芳基、芳基胺基中的芳基与上述芳基的例示相同。在本说明书中,芳烷基、烷基芳基、烷基胺基中的烷基与上述烷基的例示相同。在本说明书中,杂芳基胺中的杂芳基可以适用上述关于杂环基的说明。在本说明书中,芳烯基中的烯基与上述烯基的例示相同。在本说明书中,亚芳基为2价基团,除此以外,可以适用上述关于芳基的说明。在本说明书中,亚杂芳基为2价基团,除此以外,可以适用上述关于杂环基的说明。在本说明书中,烃环不是1价基团,而是2个取代基结合而成,除此以外,可以适用上述关于芳基或环烷基的说明。在本说明书中,杂环不是1价基团,而是2个取代基结合而成,除此以外,可以适用上述关于杂环基的说明。
优选地,上述化学式1可以由下述化学式2-1至2-3中的任一个表示:
[化学式2-1]
[化学式2-2]
[化学式2-3]
在上述化学式2-1至2-3中,
对于X、Ar1至Ar3、R1、R2和n的说明与上述的定义相同。
优选地,n可以各自独立地为0、1或2。
优选地,R1可以各自独立地为氢、氘、或者取代或未取代的C6-20芳基,更优选地,R1可以各自独立地为氢、氘或苯基。
优选地,R2可以为取代或未取代的C6-20芳基,更优选地,R2可以为苯基。
优选地,Ar1和Ar2可以各自独立地为取代或未取代的C6-20芳基,更优选地,Ar1和Ar2可以各自独立地为苯基、联苯基、或者被1个至5个氘取代的苯基。
优选地,Ar3可以为取代或未取代的包含1个以上N的C5-30杂芳基,更优选地,Ar3可以为由下述化学式3-1至3-5中的任一个表示的取代基:
[化学式3-1]
[化学式3-2]
[化学式3-3]
[化学式3-4]
[化学式3-5]
在上述化学式3-1至3-5中,
Z各自独立地为N或CH,但Z中的1个以上为N,
Ar4和Ar5各自独立地为取代或未取代的C6-60芳基;或者取代或未取代的包含选自N、O和S中的任一个或更多个杂原子的C5-60杂芳基,
Ar6为取代或未取代的C6-60芳基,
Y2为N或CH,
Y3为O或S,
m各自独立地为0至4的整数,
R3各自独立地为氢;氘;取代或未取代的C1-60烷基;取代或未取代的C3-60环烷基;取代或未取代的C6-60芳基;或者取代或未取代的包含1个以上选自N、O和S中的杂原子的C5-60杂芳基。
优选地,上述化学式3-1可以为选自下述基团中的任一个:
优选地,Ar4和Ar5可以各自独立地为取代或未取代的C6-20芳基;或者取代或未取代的包含选自N、O和S中的任一个或更多个杂原子的C5-30杂芳基,更优选地,Ar4和Ar5可以各自独立地为选自下述基团中的任一个:
优选地,Ar6可以为取代或未取代的C6-20芳基,更优选地,Ar6可以为苯基。
优选地,m可以各自独立地为0、1或2。
例如,上述化合物可以选自下述化合物:
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另一方面,由上述化学式1表示的化合物可以通过如下述反应式1所示的制造方法进行制造。
[反应式1]
在上述反应式1中,T为卤素,优选为溴或氯,对于其它取代基的定义与上述说明相同。
具体而言,由上述化学式1表示的化合物是通过铃木偶联反应结合起始物质来制造的。这样的铃木偶联反应优选在钯催化剂和碱存在下进行,用于铃木偶联反应的反应基团可以根据该领域中已知的技术进行变更。上述制造方法可以在后述的制造例中更具体化。
另外,本发明提供包含由上述化学式1表示的化合物的有机发光器件。作为一个例子,本发明提供一种有机发光器件,其中,包括:第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与上述第二电极之间的1层以上的有机物层,上述有机物层中的1层以上包含由上述化学式1表示的化合物。
本发明的有机发光器件的有机物层可以由单层结构形成,还可以由层叠有2层以上的有机物层的多层结构形成。例如,本发明的有机发光器件可以具有包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等作为有机物层的结构。但是,有机发光器件的结构并不限定于此,可以包括更少数量的有机物层。
另外,上述有机物层可以包括空穴注入层、空穴传输层、同时进行空穴注入和传输的层、或者电子阻挡层,上述空穴注入层、空穴传输层、同时进行空穴注入和传输的层、或者电子阻挡层可以包含由上述化学式1表示的化合物。
另外,上述有机物层可以包括发光层,上述发光层可以包含由上述化学式1表示的化合物。这时,由上述化学式1表示的化合物在发光层中可以用作主体物质,更具体而言,由上述化学式1表示的化合物可以用作用于绿色有机发光器件的发光层的主体。
另外,上述有机物层可以包括空穴阻挡层、电子传输层、电子注入层、或同时进行电子传输和电子注入的层,上述空穴阻挡层、电子传输层、电子注入层、或同时进行电子传输和电子注入的层可以包含由上述化学式1表示的化合物。
另外,根据本发明的有机发光器件可以是在基板上依次层叠有阳极、1层以上的有机物层和阴极的结构(正常型(normal type))的有机发光器件。另外,根据本发明的有机发光器件可以是在基板上依次层叠有阴极、1层以上的有机物层和阳极的逆向结构(倒置型(inverted type))的有机发光器件。例如,根据本发明的一实施例的有机发光器件的结构例示于图1至3。
图1图示了由基板1、阳极2、发光层3、阴极4构成的有机发光器件的例子。在如上所述的结构中,由上述化学式1表示的化合物可以包含在上述发光层中。
图2图示了由基板1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4构成的有机发光器件的例子。在如上所述的结构中,由上述化学式1表示的化合物可以包含在上述空穴注入层、空穴传输层、发光层和电子传输层中的1层以上中。
图3图示了由基板1、阳极2、空穴注入层5、空穴传输层6、电子阻挡层9、发光层7、空穴阻挡层10、电子传输层8、电子注入层11和阴极4构成的有机发光器件的例子。在如上所述的结构中,由上述化学式1表示的化合物可以包含在上述空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的1层以上中。
根据本发明的有机发光器件除了上述有机物层中的1层以上包含由上述化学式1表示的化合物以外,可以利用该技术领域中已知的材料和方法进行制造。此外,上述有机发光器件包括复数个有机物层时,上述有机物层可以由相同的物质或不同的物质形成。
例如,根据本发明的有机发光器件可以通过在基板上依次层叠第一电极、有机物层和第二电极而制造。这时,可以如下制造:利用溅射法(sputtering)或电子束蒸发法(e-beam evaporation)之类的PVD(physical Vapor Deposition:物理气相沉积)方法,在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极,然后在该阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机物层,之后在该有机物层上蒸镀可用作阴极的物质而制造。除了这种方法以外,也可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件。
另外,由上述化学式1表示的化合物在制造有机发光器件时不仅可以利用真空蒸镀法,还可以利用溶液涂布法来形成有机物层。在这里,所谓溶液涂布法是指旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但不仅限于此。
除了这些方法以外,也可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件(WO2003/012890号)。但是,制造方法并不限定于此。
作为一个例子,上述第一电极为阳极,上述第二电极为阴极,或者上述第一电极为阴极,上述第二电极为阳极。
作为上述阳极物质,通常为了使空穴能够顺利地向有机物层注入,优选为功函数大的物质。作为上述阳极物质的具体例,有钒、铬、铜、锌、金等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:Al或SnO2:Sb等金属与氧化物的组合;聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等,但不仅限于此。
作为上述阴极物质,通常为了使电子容易地向有机物层注入,优选为功函数小的物质。作为上述阴极物质的具体例,有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅等金属或它们的合金;LiF/Al或LiO2/Al等多层结构物质等,但不仅限于此。
上述空穴注入层是注入来自电极的空穴的层,作为空穴注入物质,优选为如下化合物:具有传输空穴的能力,具有注入来自阳极的空穴的效果,具有对于发光层或发光材料的优异的空穴注入效果,防止发光层中生成的激子向电子注入层或电子注入材料迁移,而且薄膜形成能力优异的化合物。优选空穴注入物质的HOMO(最高占有分子轨道,highestoccupied molecular orbital)介于阳极物质的功函数与周围有机物层的HOMO之间。作为空穴注入物质的具体例,有金属卟啉(porphyrin)、低聚噻吩、芳基胺系有机物、六腈六氮杂苯并菲系有机物、喹吖啶酮(quinacridone)系有机物、苝(perylene)系有机物、蒽醌及聚苯胺和聚噻吩系的导电性高分子等,但不仅限于此。
上述空穴传输层是接收来自空穴注入层的空穴并将空穴传输至发光层的层,空穴传输物质是能够接收来自阳极或空穴注入层的空穴并将其转移至发光层的物质,对空穴的迁移率大的物质是合适的。作为具体例,有芳基胺系有机物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等,但不仅限于此。
上述电子阻挡层形成在上述空穴传输层上,优选与发光层相接而具备,通过调节空穴迁移率,防止电子的过度迁移而提高空穴-电子之间的结合几率,从而起到改善有机发光器件的效率的作用。上述电子阻挡层包含电子阻挡物质,作为这样的电子阻挡物质,使电子不能从发光层流出的具有稳定结构的物质是合适的。作为具体例,可以使用芳基胺系的有机物等,但并不限定于此。
上述发光物质是能够从空穴传输层和电子传输层分别接收空穴和电子并使它们结合而发出可见光区域的光的物质,优选为对于荧光或磷光的量子效率高的物质。作为具体示例,有8-羟基喹啉铝配合物(Alq3);咔唑系化合物;二聚苯乙烯基(dimerized styryl)化合物;BAlq;10-羟基苯并喹啉-金属化合物;苯并唑、苯并噻唑及苯并咪唑系化合物;聚(对亚苯基亚乙烯基)(PPV)系高分子;螺环(spiro)化合物;聚芴、红荧烯等,但不仅限于此。
上述发光层可以包含主体材料和掺杂剂材料。主体材料有芳香族稠环衍生物或含杂环化合物等。具体而言,作为芳香族稠环衍生物,有蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,作为含杂环化合物,有咔唑衍生物、二苯并呋喃衍生物、梯型呋喃化合物()、嘧啶衍生物等,但并不限定于此。
作为掺杂剂材料,有芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体而言,芳香族胺衍生物是具有取代或未取代的芳基氨基的芳香族稠环衍生物,有具有芳基氨基的芘、蒽、、二茚并芘等,苯乙烯基胺化合物是在取代或未取代的芳基胺中取代有至少1个芳基乙烯基的化合物,被选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的1个或2个以上的取代基取代或未取代。具体而言,有苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺等,但并不限定于此。此外,作为金属配合物,有铱配合物、铂配合物等,但并不限定于此。
上述空穴阻挡层形成在上述发光层上,具体而言,上述空穴阻挡层与发光层相接而具备,防止空穴的过度迁移而提高空穴-电子之间的结合几率,从而起到改善有机发光器件的效率的作用。上述空穴阻挡层包含空穴阻挡物质,作为这样的空穴阻挡物质,使空穴不能从发光层流出的具有稳定结构的物质是合适的。作为上述空穴阻挡物质,可以使用包含三嗪的嗪类衍生物、三唑衍生物、二唑衍生物、菲咯啉衍生物、氧化膦衍生物等导入有吸电子基团的化合物,但并不限定于此。
上述电子传输层是从电子注入层接收电子并将电子传输至发光层的层,电子传输物质是能够从阴极良好地接收电子并将其转移至发光层的物质,对电子的迁移率大的物质是合适的。作为具体例,有8-羟基喹啉的Al配合物、包含Alq3的配合物、有机自由基化合物、羟基黄铜-金属配合物等,但不仅限于此。电子传输层可以如现有技术中所使用的那样与任意期望的阴极物质一同使用。特别是,合适的阴极物质的例子是具有低功函数且伴有铝层或银层的通常的物质。具体为铯、钡、钙、镱和钐,在各情况下,均伴有铝层或银层。
上述电子注入层是注入来自电极的电子的层,优选为如下物质:具有传输电子的能力,具有注入来自阴极的电子的效果,具有对于发光层或发光材料的优异的电子注入效果,防止发光层中所生成的激子向空穴注入层迁移且薄膜形成能力优异的化合物。具体而言,有芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、/>二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等和它们的衍生物、金属配位化合物、以及含氮五元环衍生物等,但并不限定于此。
作为上述金属配位化合物,有8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯化镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但并不限定于此。
根据所使用的材料,根据本发明的有机发光器件可以为顶部发光型、底部发光型或双向发光型。
另外,由上述化学式1表示的化合物除了包含在有机发光器件中以外,还可以包含在有机太阳能电池或有机晶体管中。
由上述化学式1表示的化合物及包含其的有机发光器件的制造在以下实施例中具体地进行说明。但是,下述实施例用于例示本发明,本发明的范围并不限定于此。
[合成例]
合成例1:化合物1的合成
步骤1)化合物1-a的合成
在氮气氛下,将(2,4-二氯苯基)硼酸((2,4-dichlorophenyl)boronic acid)(15g,78.6mmol)和2-溴二苯并[b,d]呋喃(2-bromodibenzo[b,d]furan)(19.4g,78.6mmol)加入到225ml的THF中,搅拌及回流。然后,将碳酸钾(potassium carbonate)(32.6g,235.8mmol)溶解于98ml的水而进行添加,充分搅拌后,加入四(三苯基膦)钯(0)(tetrakis(triphenylphosphine)palladium(0))(2.7g,2.4mmol)。反应10小时后,冷却至常温,将有机层与水层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了17.2g的化合物1-a。(收率70%,MS:[M+H]+=314)
步骤2)化合物1-b的合成
在氮气氛下,将化合物1-a(15g,47.9mmol)和双(频哪醇合)二硼(bis(pinacolato)diboron)(26.8g,105.4mmol)在300ml的1,4-二烷(1,4-dioxane)中回流并搅拌。然后加入醋酸钾(potassium acetate)(14.1g,143.7mmol),充分搅拌后,加入双(二亚苄基丙酮)钯(0)(bis(dibenzylideneacetone)palladium(0))(0.8g,1.4mmol)和三环己基膦(tricyclohexylphosphine)(0.8g,2.9mmol)。反应7小时,冷却至常温后,将有机层与水层分离,然后蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了16.4g的化合物1-b。(收率69%,MS:[M+H]+=714)
步骤3)化合物1的合成
在氮气氛下,将化合物1-b(15g,30.2mmol)和2-氯-4,6-二苯基-1,3,5-三嗪(2-chloro-4,6-diphenyl-1,3,5-triazine)(8.1g,30.2mmol)加入到225ml的THF中,搅拌及回流。然后,将碳酸钾(potassium carbonate)(12.5g,90.7mmol)溶解于38ml的水中而进行添加,充分搅拌后,加入四(三苯基膦)钯(0)(tetrakis(triphenylphosphine)palladium(0))(1g,0.9mmol)。反应8小时后,冷却至常温,将有机层与水层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化后,通过升华纯化,从而制造了6.4g的化合物1。(收率30%,MS:[M+H]+=708)
合成例2:化合物2的合成
在合成例1中,将2-溴二苯并[b,d]呋喃(2-bromodibenzo[b,d]furan)变更为1-溴-4-苯基二苯并[b,d]呋喃(1-bromo-4-phenyldibenzo[b,d]furan)而使用,除此以外,通过与化合物1的制造方法相同的制造方法制造了化合物2。(MS[M+H]+=784)
合成例3:化合物3的合成
在合成例1中,将2-溴二苯并[b,d]呋喃(2-bromodibenzo[b,d]furan)变更为2-溴二苯并[b,d]噻吩(2-bromodibenzo[b,d]thiophene)而使用,除此以外,通过与化合物1的制造方法相同的制造方法制造了化合物3。(MS[M+H]+=724)
合成例4:化合物4的合成
在合成例1中,将2-溴二苯并[b,d]呋喃(2-bromodibenzo[b,d]furan)变更为3-溴-9-苯基-9H-咔唑(3-bromo-9-phenyl-9H-carbazole)而使用,除此以外,通过与化合物1的制造方法相同的制造方法制造了化合物4。(MS[M+H]+=783)
合成例5:化合物5的合成
步骤1)化合物5-a的合成
在氮气氛下,将(2,4-二氯苯基)硼酸((2,4-dichlorophenyl)boronic acid)(15g,78.6mmol)和3-溴二苯并[b,d]呋喃(3-bromodibenzo[b,d]furan)(19.4g,78.6mmol)加入到225ml的THF中,搅拌及回流。然后,将碳酸钾(potassium carbonate)(32.6g,235.8mmol)溶解于98ml的水中而进行添加,充分搅拌后,加入四(三苯基膦)钯(0)(tetrakis(triphenylphosphine)palladium(0))(2.7g,2.4mmol)。反应10小时后,冷却至常温,将有机层与水层分离,然后蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了16.2g的化合物5-a。(收率66%,MS:[M+H]+=314)
步骤2)化合物5-b的合成
在氮气氛下,将化合物5-a(15g,47.9mmol)和双(频哪醇合)二硼(bis(pinacolato)diboron)(13.4g,52.7mmol)在300ml的1,4-二烷(1,4-dioxane)中回流并搅拌。然后加入醋酸钾(potassium acetate)(14.1g,143.7mmol),充分搅拌后,加入双(二亚苄基丙酮)钯(0)(bis(dibenzylideneacetone)palladium(0))(0.8g,1.4mmol)和三环己基膦(tricyclohexylphosphine)(0.8g,2.9mmol)。反应7小时,冷却至常温后,将有机层与水层分离,然后蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了15.1g的化合物5-b。(收率78%,MS:[M+H]+=583)
步骤3)化合物5-c的合成
在氮气氛下,将化合物5-b(15g,37.1mmol)和2-溴-4,6-二苯基嘧啶(2-bromo-4,6-diphenylpyrimidine)(11.5g,37.1mmol)加入到225ml的THF中,搅拌及回流。然后,将碳酸钾(potassium carbonate)(15.4g,111.2mmol)溶解于46ml的水中而进行添加,充分搅拌后,加入四(三苯基膦)钯(0)(tetrakis(triphenylphosphine)palladium(0))(1.3g,1.1mmol)。反应12小时后,冷却至常温,将有机层与水层分离后蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了12.8g的化合物5-c。(收率68%,MS:[M+H]+=510)
步骤4)化合物5-d的合成
在氮气氛下,将化合物5-c(15g,29.5mmol)和双(频哪醇合)二硼(bis(pinacolato)diboron)(8.2g,32.4mmol)在300ml的1,4-二烷(1,4-dioxane)中回流并搅拌。然后加入醋酸钾(potassium acetate)(8.7g,88.4mmol),充分搅拌后,加入双(二亚苄基丙酮)钯(0)(bis(dibenzylideneacetone)palladium(0))(0.5g,0.9mmol)和三环己基膦(tricyclohexylphosphine)(0.5g,1.8mmol)。反应5小时,冷却至常温后,将有机层与水层分离,然后蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了12g的化合物5-d。(收率68%,MS:[M+H]+=532)
步骤5)化合物5的合成
在氮气氛下,将化合物5-d(15g,25mmol)和2-氯-4,6-二苯基-1,3,5-三嗪(2-chloro-4,6-diphenyl-1,3,5-triazine)(6.7g,25mmol)加入到225ml的THF中,搅拌及回流。然后,将碳酸钾(potassium carbonate)(10.4g,74.9mmol)溶解于31ml的水而进行添加,充分搅拌后,加入四(三苯基膦)钯(0)(tetrakis(triphenylphosphine)palladium(0))(0.9g,0.7mmol)。反应8小时后,冷却至常温,将有机层与水层分离后蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化后,通过升华纯化,从而制造了6.7g的化合物5。(收率38%,MS:[M+H]+=707)
合成例6:化合物6的合成
在合成例5中,将2-溴二苯并[b,d]呋喃(2-bromodibenzo[b,d]furan)变更为2-溴二苯并[b,d]噻吩(2-bromodibenzo[b,d]thiophene),将2-溴-4,6-二苯基嘧啶(2-bromo-4,6-diphenylpyrimidine)变更为2-氯-4-(9,9-二甲基-9H-芴-2-基)-6-苯基-1,3,5-三嗪(2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine)而使用,除此以外,通过与化合物5的制造方法相同的制造方法制造了化合物6。(MS[M+H]+=840)
合成例7:化合物7的合成
在合成例5中,将2-溴二苯并[b,d]呋喃(2-bromodibenzo[b,d]furan)变更为2-溴二苯并[b,d]噻吩(2-bromodibenzo[b,d]thiophene),将2-溴-4,6-二苯基嘧啶(2-bromo-4,6-diphenylpyrimidine)变更为2-氯-4-苯基苯并[4,5]噻吩并[3,2-d]嘧啶(2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine)而使用,除此以外,通过与化合物5的制造方法相同的制造方法制造了化合物7。(MS[M+H]+=753)
[实验例]
实验例1
将ITO(氧化铟锡,Indium Tin Oxide)以的厚度被涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中,利用超声波进行洗涤。这时,洗涤剂使用菲希尔公司(Fischer Co.)制品,蒸馏水使用了利用密理博公司(Millipore Co.)制造的过滤器(Filter)过滤两次的蒸馏水。将ITO洗涤30分钟后,用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后,用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后,输送至等离子体清洗机。此外,利用氧等离子体,将上述基板清洗5分钟后,将基板输送至真空蒸镀机。
在这样准备的ITO透明电极上,将下述HT-A化合物和下述PD化合物以95:5的重量比并以的厚度进行热真空蒸镀,接着,只将下述HT-A化合物以/>的厚度进行蒸镀而形成空穴传输层。在上述空穴传输层上,将下述HT-B化合物以/>的厚度进行热真空蒸镀而形成电子阻挡层。在上述电子阻挡层上,将上述制造的化合物1和下述GD化合物以85:15的重量比并以/>的厚度进行真空蒸镀而形成发光层。在上述发光层上,将下述ET-A化合物以/>的厚度进行真空蒸镀而形成空穴阻挡层。在上述空穴阻挡层上,将下述ET-B化合物和下述Liq化合物以2:1的重量比并以/>的厚度进行热真空蒸镀,接着,将LiF和镁以1:1的重量比并以/>的厚度进行真空蒸镀而形成电子传输和注入层。在上述电子注入层上,将镁和银以1:4的重量比并以/>的厚度进行蒸镀而形成阴极,从而制造了有机发光器件。
在上述过程中,有机物的蒸镀速度维持阴极的氟化锂维持/>的蒸镀速度,银和镁维持/>的蒸镀速度,在蒸镀时,真空度维持2×10-7~5×10-6托,从而制作了有机发光器件。
实验例2至7
使用下述表1中记载的化合物代替化合物1,除此以外,通过与上述实验例1相同的方法制造了有机发光器件。
比较实验例1至2
使用下述表1中记载的化合物代替化合物1,除此以外,通过与上述实验例1相同的方法制造了有机发光器件。在下述表1中,化合物GH-A和GH-B分别如下所示。
对上述实验例和比较实验例中制造的有机发光器件施加电流而测定了电压、效率、寿命(T95),将其结果示于下述表1。这时,电压和效率是在施加10mA/cm2的电流密度而测定的。此外,下述表1的T95是指在20mA/cm2的电流密度下初始亮度降低至95%时测定的时间。
【表1】
化学式1的化合物由于在分子内起到电子供体作用的二苯并呋喃、二苯并噻吩或咔唑与起到电子受体作用的单环的含氮杂环彼此在邻位结合,从而能够容易地实现内部电荷迁移(intra charge transfer)。由此,分子的稳定性高,对空穴和电子的传输均有利。此外,Ar3中进一步取代有各种含氮杂环,从而可以多样地调节电子传输特性,因此对达到根据共同层的变化的电荷平衡有利。
因此,如上述表1所示的那样,可以确认将化学式1的化合物用作有机发光器件的主体时显示低电压、高效率、长寿命的特性。
符号说明
1:基板 2:阳极
3:发光层 4:阴极
5:空穴注入层 6:空穴传输层
7:发光层 8:电子传输层
9:电子阻挡层 10:空穴阻挡层
11:电子注入层。
Claims (9)
1.一种由下述化学式1表示的化合物:
化学式1
X各自独立地为N或CH,条件是X中的1个以上为N,
Ar1和Ar2各自独立地为经氘取代或未取代的C6-30芳基,
Y1为O、S或NR2,
n各自独立地为0至7的整数,
R1各自独立地为氢;氘;或者C6-30芳基,
R2为C6-30芳基,以及
Ar3由下述化学式3-1和3-5中的任一个表示:
化学式3-1
化学式3-5
在所述化学式3-1和3-5中,
Z各自独立地为N或CH,条件是Z中的1个以上为N,
Ar4和Ar5各自独立地为经氘或C1-6烷基取代或未取代的C6-30芳基,
Ar6为C6-30芳基,
Y3为O或S,
m各自独立地为0至4的整数,以及
R3各自独立地为氢;或氘。
2.根据权利要求1所述的化合物,其中,所述化学式1由下述化学式2-1至2-3中的任一个表示:
化学式2-1
化学式2-2
化学式2-3
在所述化学式2-1至2-3中,
对于X、Ar1至Ar3、R1和R2的说明与权利要求1中的定义相同,
n为0。
3.根据权利要求1所述的化合物,其中,R1各自独立地为氢、氘或苯基。
4.根据权利要求1所述的化合物,其中,R2为苯基。
5.根据权利要求1所述的化合物,其中,Ar1和Ar2各自独立地为苯基、联苯基、或者被1个至5个氘取代的苯基。
6.根据权利要求1所述的化合物,其中,Ar4和Ar5各自独立地为选自下述基团中的任一个:
7.根据权利要求1所述的化合物,其中,Ar6为苯基。
8.根据权利要求1所述的化合物,其中,由所述化学式1表示的化合物为选自下述化合物中的任一个:
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9.一种有机发光器件,其中,包括:第一电极、与所述第一电极对置而具备的第二电极、以及具备在所述第一电极与所述第二电极之间的1层以上的有机物层,所述有机物层中的1层以上包含权利要求1至8中任一项所述的化合物。
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