CN105377822B - 有机组合物、有机光电子元件及显示装置 - Google Patents
有机组合物、有机光电子元件及显示装置 Download PDFInfo
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- CN105377822B CN105377822B CN201480039630.8A CN201480039630A CN105377822B CN 105377822 B CN105377822 B CN 105377822B CN 201480039630 A CN201480039630 A CN 201480039630A CN 105377822 B CN105377822 B CN 105377822B
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- 239000002131 composite material Substances 0.000 title description 2
- 239000000126 substance Substances 0.000 claims abstract description 55
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000010410 layer Substances 0.000 claims description 61
- 230000005693 optoelectronics Effects 0.000 claims description 22
- 238000006467 substitution reaction Methods 0.000 claims description 17
- 239000012044 organic layer Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 5
- 230000005540 biological transmission Effects 0.000 claims description 4
- 230000004888 barrier function Effects 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 156
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000000203 mixture Substances 0.000 description 46
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- 239000000243 solution Substances 0.000 description 33
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- 229910052757 nitrogen Inorganic materials 0.000 description 25
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- 238000000034 method Methods 0.000 description 24
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- 238000003818 flash chromatography Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- 238000001914 filtration Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 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 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical class N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
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- 229910052763 palladium Inorganic materials 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 3
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
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- 239000002322 conducting polymer Substances 0.000 description 3
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- 238000000151 deposition Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- 239000011368 organic material Substances 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 2
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 2
- DRRHKCZEEPWZHM-UHFFFAOYSA-N 2-methylbenzoic acid;sodium Chemical compound [Na].CC1=CC=CC=C1C(O)=O DRRHKCZEEPWZHM-UHFFFAOYSA-N 0.000 description 2
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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- -1 Normal-butyl Chemical group 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- AVFUHBJCUUTGCD-UHFFFAOYSA-M [Br-].[Mg+]C Chemical class [Br-].[Mg+]C AVFUHBJCUUTGCD-UHFFFAOYSA-M 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
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- 239000004305 biphenyl Substances 0.000 description 2
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- 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 2
- 150000001721 carbon Chemical group 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
- VEWQKVPMDURAQC-UHFFFAOYSA-N hexacyclo[12.11.0.02,7.08,13.015,23.017,22]pentacosa-1(14),2,4,6,8,10,12,15(23),17,19,21,24-dodecaene Chemical group C1=CC=C2C3=C4CC5=CC=CC=C5C4=CC=C3C3=CC=CC=C3C2=C1 VEWQKVPMDURAQC-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
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- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 238000004062 sedimentation Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 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 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical class SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LNGWQXANOHFHGT-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=C4C(=C3C12)CC=1C=CC=CC14.C1=CC=CC=4C2=CC=CC=C2C2=CC=C3C(=C2C14)CC=1C=CC=CC13 Chemical compound C1=CC=CC=2C3=CC=CC=C3C3=CC=C4C(=C3C12)CC=1C=CC=CC14.C1=CC=CC=4C2=CC=CC=C2C2=CC=C3C(=C2C14)CC=1C=CC=CC13 LNGWQXANOHFHGT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002979 perylenes Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000000717 retained effect Effects 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- 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
Classifications
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
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- 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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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Abstract
本发明涉及一种通过由化学式1表示的部分和由化学式2表示的部分的组合表示的有机化合物,并且涉及包括有机化合物的有机光电子元件和显示装置。
Description
技术领域
公开了有机化合物、有机光电子器件以及显示装置。
背景技术
有机光电子器件(有机光电二极管)是将电能转换成光能的器件,并且反之亦然。
根据其驱动原理,有机光电子器件可以分为以下类别。一种是光电子器件,其中激子由光能产生,分离为电子和空穴,并且电子和空穴传输至不同的电极以产生电能,并且另一种是发光装置,其中将电压或电流供给电极以由电能产生光能。
有机光电子器件的实例可以是有机光电器件、有机发光二极管、有机太阳能电池和有机感光鼓。
对于这些,由于对于平板显示器需求的增加,有机发光二极管(OLED)近来已经吸引了关注。这样的有机发光二极管通过将电流施加到有机发光材料而将电能转化为光。它具有这样的结构,其中有机层介于阳极和阴极之间。本文中,有机层可以包括发射层(emission layer)和可选的辅助层,并且辅助层可以包括,例如选自以下的至少一种:空穴注入层、空穴传输层、电子阻挡层、电子传输层、电子注入层、以及空穴阻挡层,以增加有机发光二极管的效率和稳定性。
有机发光二极管的性能可以受有机层特性的影响,并且在此之中,可以主要受有机层的有机材料特性的影响。
具体地,需要开发能够增加空穴和电子迁移率且同时增加电化学稳定性的有机材料,从而可以将有机发光二极管应用于大尺寸的平板显示器。
发明内容
[技术问题]
一个实施方式提供了能够实现具有高效率和长寿命的有机光电子器件的有机化合物。
另一个实施方式提供了包括有机化合物的有机光电子器件。
又一个实施方式提供了包括有机光电子器件的显示装置。
[技术方案]
根据一个实施方式,提供了通过由化学式1表示的部分和由化学式2表示的部分的组合表示的有机化合物:
在化学式1或化学式2中,
X是CRaRb、SiRcRd、O、S、SO或SO2,
Z各自独立地是N或CRe,
至少一个Z是N,
R1至R8以及Ra至Re各自独立地是氢、氘、取代或未取代的C1至C20烷基、取代或未取代的C6至C30芳基、取代或未取代的C3至C30杂芳基、或它们的组合,
L是取代或未取代的C1至C20亚烷基、取代或未取代的C6至C30亚芳基、取代或未取代的C3至C30杂亚芳基、或它们的组合,
n1至n3各自独立地是0或1,并且
化学式1的相邻的两个*与化学式2的两个*键合以形成稠环。
根据另一实施方式,提供了有机光电子器件,其包括彼此面对的阳极和阴极,以及阳极和阴极之间的至少一个有机层,其中有机层包括有机化合物。
根据又一实施方式,提供了包括有机光电子器件的显示装置。
[有益效果]
可以实现具有高效率和长寿命的有机光电子器件。
附图说明
图1和2是示出根据一个实施方式的有机发光二极管的截面图。
具体实施方式
[最佳方式]
在下文中,详细描述本发明的实施方式。然而,这些实施方式是示例性的,并且本公开并不局限于此。
在本说明书中,当没有另外提供定义时,术语“取代的”是指由选自以下的取代基取代来代替取代基或化合物:氘、卤素、羟基、氨基、取代或未取代的C1至C30胺基、硝基、取代或未取代的C1至C40甲硅烷基、C1至C30烷基、C1至C10烷基甲硅烷基、C3至C30环烷基、C3至C30杂环烷基、C6至C30芳基、C6至C30杂芳基、C1至C20烷氧基、氟基、诸如三氟甲基等的C1至C10三氟烷基、或氰基。
此外,相邻的两个选自以下的取代基可以彼此稠合以形成环:取代的卤素、羟基、氨基、取代或未取代的C1至C20胺基、硝基、取代或未取代的C3至C40甲硅烷基、C1至C30烷基、C1至C10烷基甲硅烷基、C3至C30环烷基、C3至C30杂环烷基、C6至C30芳基、C6至C30杂芳基、C1至C20烷氧基、氟基、诸如三氟甲基等的C1至C10三氟烷基、或氰基。例如,取代的C6至C30芳基可以与另一个相邻的取代的C6至C30芳基稠合,形成取代或未取代的芴环。
在本说明书中,当没有另外提供具体定义时,“杂”指包含选自N、O、S、P和Si的1至3个杂原子,并且在一个官能团中保留碳。
在本说明书中,当没有另外提供定义时,术语“它们的组合”是指通过键(linker)彼此连接的至少两种取代基、或彼此缩合的至少两种取代基。
在本说明书中,当没有另外提供定义时,“烷基”是指脂肪族烃基。烷基可以是没有任何双键或三键的“饱和烷基”。
烷基可以是C1至C30烷基。更具体地,烷基可以是C1至C20烷基或C1至C10烷基。例如,C1至C4烷基在烷基链中可以具有1至4个碳原子,其可以选自甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、以及叔丁基。
烷基的具体实例可以是甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、己基、环丙基、环丁基、环戊基、环己基等。
在本说明书中,术语“芳基”是指包括所有环的元素具有p-轨道的取代基,该p-轨道形成共轭,且可以为单环、多环或稠环的多环(即环共享相邻的碳原子对)官能团。
在本说明书中,术语“杂芳基”是指包含1至3个选自N、O、S,P和Si的杂原子,并保留碳的芳基。当杂芳基是稠环时,每个环可以包括1至3个杂原子。
更具体地,取代或未取代的C6至C30芳基和/或取代或未取代的C2至C30杂芳基可以是取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的并四苯基(naphthacenyl)、取代或未取代的芘基、取代或未取代的联苯基、取代或未取代的对三联苯基、取代或未取代的间三联苯基、取代或未取代的屈基、取代或未取代的三亚苯基(triphenylenyl)、取代或未取代的二萘嵌苯基(perylenyl)、取代或未取代的茚基、取代或未取代的呋喃基、取代或未取代的苯硫基、取代或未取代的吡咯基、取代或未取代的吡唑基、取代或未取代的咪唑基、取代或未取代的三唑基、取代或未取代的噁唑基、取代或未取代的噻唑基、取代或未取代的噁二唑基、取代或未取代的噻二唑基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的吡嗪基、取代或未取代的三嗪基、取代或未取代的苯并呋喃基、取代或未取代的苯并苯硫基、取代或未取代的苯并咪唑基、取代或未取代的吲哚基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的喹唑啉基(quinazolinyl)、取代或未取代的喹喔啉基(quinoxalinyl)、取代或未取代的萘啶基、取代或未取代的苯并噁嗪基、取代或未取代的苯并噻嗪基(benzthiazinyl)、取代或未取代的吖啶基、取代或未取代的吩嗪基、取代或未取代的吩噻嗪基、取代或未取代的吩噁嗪基(phenoxazinyl)、取代或未取代的芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并苯硫基(dibenzothiophenyl)、取代或未取代的咔唑基、或它们的组合,但不限于此。
在说明书中,空穴特性是指在施加电场时能够提供电子以形成空穴的特性,以及在阳极中形成的空穴容易注入发射层,且由于根据HOMO能级的导电特性,发射层中的空穴容易传输至阳极且容易在发射层中传输的特性。
此外,电子特性是指在施加电场时能够接受电子的特性,以及在阴极中形成的电子容易注入发射层,且由于根据LUMO能级的导电特性,发射层中形成的电子容易传输至阴极且容易在发射层中传输的特性。
在下文中,描述了根据一个实施方式的有机化合物。
根据一个实施方式的有机化合物通过由化学式1表示的部分和由化学式2表示的部分的组合表示。
在化学式1或化学式2中,
X是CRaRb、SiRcRd、O、S、SO或SO2,
Z各自独立地是N或CRe,
至少一个Z是N,
R1至R8以及Ra至Re各自独立地是氢、氘、取代或未取代的C1至C20烷基、取代或未取代的C6至C30芳基、取代或未取代的C3至C30杂芳基、或它们的组合,
L是取代或未取代的C1至C20亚烷基、取代或未取代的C6至C30亚芳基、取代或未取代的C3至C30杂亚芳基、或它们的组合,
n1至n3各自独立地是0或1,并且
化学式1的相邻的两个*与化学式2的两个*键合以形成稠环。
有机化合物可以是,例如由化学式3或化学式4表示的,这取决于由化学式1表示的部分和由化学式2表示的部分的键合位置。
在化学式3或化学式4中,
X、Z、R1至R8、Ra至Re、L、和n1至n3与上述相同。
有机化合物包括茚并三亚苯(indenotriphenylene)以及至少一种含氮的杂芳基。
由于至少一个含氮的环,有机化合物具有在施加电场时容易接受电子的结构,从而可以降低包括有机化合物的有机光电器件的驱动电压。
有机化合物包括容易接受空穴的茚并三亚苯部分以及容易接受电子的含氮的环,并且从而具有双极结构以及空穴和电子流动之间的平衡,并且因而可以改善包括有机化合物的有机光电子器件的效率。
有机化合物可以适当地将容易接受空穴的茚并三亚苯部分和容易接受电子的部分局部化(localize),并控制共轭体系的流动,从而示出优异的双极特性。因此,有机化合物可以改善有机光电子器件的寿命。
此外,有机化合物具有能够有效防止有机化合物堆叠(stacking)的结构,从而可以改善工艺稳定性并同时降低沉积温度。
由化学式2表示的部分可以,例如由化学式2-I至化学式2-III之一表示:
在化学式2-I至化学式2-III中,
X1、X2、X3、Z、R5至R8、Ra至Re、L、和n1至n3与上述相同。
在一个实施方式中,在化学式2-I至化学式2-III中,X1和X2各自独立地是CRaRb或SiRcRd,X3是O、S、SO或SO2,且Z、R5至R8、Ra至Re、L、n1至n3与上述相同。
化学式2-I至2-III的相邻的两个*与化学式1的两个*键合以形成稠环。
化学式2可以例如由化学式2a和组1之一的组合表示。
[组1]
在化学式2a或组1中,X、Ra至Rd、以及L和n1与上述相同。
化学式2的L可以是,例如取代或未取代的C6至C30亚芳基,例如取代或未取代的亚苯基、取代或未取代的亚联苯基或取代或未取代的亚三联苯基,但不限于此。
例如,化学式1的R1至R4可以各自独立地是氢、氘或取代或未取代的C1至C20烷基。
有机化合物可以是例如组2的化合物,但不限于此。
[组2]
有机化合物可以具有约-2.0至-2.5eV的LUMO能量。电子注入特性可以在LUMO能量范围内提高。
在下文中描述了包括有机化合物的有机光电子器件。
有机光电子器件可以是任何将电能转换为光能,反之亦然的器件,没有特定限制,且可以是,例如有机光电器件、有机发光二极管、有机太阳能电池、和有机感光鼓。
本文中,将有机发光二极管作为一个有机光电子器件的实例来描述。
图1和2是根据一个实施方式的有机发光二极管的截面图。
参照图1,根据一个实施方式的有机光电子器件(100)包括彼此面向的阳极(120)和阴极(110),以及在阳极(120)和阴极(110)之间的有机层(105)。
阳极(120)可由具有帮助空穴注入的高功函数(work function)的导体制成,例如金属、金属氧化物和/或导电聚合物。阳极(120)可以包括例如金属或其合金:诸如镍、铂、钒、铬、铜、锌、和金;金属氧化物,诸如氧化锌、氧化铟、氧化铟锡(ITO)、和氧化铟锌(IZO);金属和氧化物的组合,诸如ZnO和Al或SnO2和Sb;导电聚合物,诸如聚(3-甲基噻吩)、聚(3,4-(乙烯基-1,2-二氧基)噻吩)(PEDT)、聚吡咯、和聚苯胺,但不限于此。
阴极(110)可由具有帮助电子注入的低功函数的导体制成,例如金属、金属氧化物和/或导电聚合物。阴极(110)可以包括例如金属或其合金,诸如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、铅、铯、钡等;多层结构材料,诸如LiF/Al、LiO2/Al、LiF/Ca、LiF/Al、和BaF2/Ca,但不限于此。
有机层(105)包括含有机化合物的发射层(130)。
发射层(130)可以包括,例如单独的有机化合物,或至少两种有机化合物,或作为与其他不同于所述有机化合物的化合物的混合物。当有机化合物与另一种化合物混合时,例如它们可作为主体和掺杂剂包括,其中有机化合物可以例如作为主体包括。主体可以是例如磷光主体或荧光主体,例如磷光主体。
当有机化合物作为主体包括时,掺杂剂可以选自作为掺杂剂的众所周知的无机、有机、有机/无机化合物。
参考图2,有机发光二极管(200)进一步包括空穴辅助层(140)以及发射层(130)。空穴辅助层(140)可以进一步提高阳极(120)和发射层(130)之间的空穴注入和/或空穴迁移率并阻挡电子。空穴辅助层(140)可以是例如空穴传输层、空穴注入层、和/或电子阻挡层,且可以包括至少一层。有机化合物可包括在发射层(130)和/或空穴辅助层(140)中。
在本发明的一个实施方式中,在图1或图2中,有机层(105)可以进一步包括辅助电子传输层、电子传输层、电子注入层、辅助空穴传输层、空穴注入层等。有机化合物可以包括在发射层(130)和/或空穴辅助层(140)中,或可以包括在辅助电子传输层、电子传输层、电子注入层、辅助空穴传输层和/或空穴注入层中。
有机发光二极管(100,200)可以如此制造:在基板上形成阳极或阴极;根据干法涂覆,诸如蒸发、溅射、等离子镀、和离子镀,或湿法涂覆诸如旋涂、狭缝式涂覆、浸镀(dipping)、浇涂(flow coating)和喷墨印刷来形成有机层;以及在其上形成阴极或阳极。
有机发光二极管可以应用于有机发光二极管显示器。
[发明方式]
下面将参照实施例更详细地说明实施方式。然而,这些实施例不应以任何方式视为限制本发明的范围。
中间体的合成
合成实施例1:中间体I-1的合成
将100g(326mmol)的2-溴三亚苯在氮气环境下溶解于1,000mL的二甲基甲酰胺(DMF)中,将99.2g(391mmol)的双(频那醇合)二硼(bis(pinacolato)diboron)和2.66g(3.26mmol)的1,1'-双(二苯基膦)二茂铁)二氯化钯(II)以及80g(815mmol)的乙酸钾加入其中,并将混合物加热并在150℃下回流5小时。当反应完成时,将水加入反应溶液,并过滤混合物以及在真空烘箱中干燥。通过快速柱色谱分离并纯化获得的残余物,获得113g(98%)的化合物I-1。
HRMS(70eV,EI+):C24H23BO2的m/z计算:354.1791,测量:354。
元素分析:C,81%;H,7%
合成实施例2:中间体I-2的合成
将100g(282mmol)的化合物I-1在氮气环境下溶解于800mL的四氢呋喃(THF)中,将58.5g(338mmol)的2-溴苯酚和3.26g(2.82mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的97.4g(705mmol)的碳酸钾加入其中,并将获得的混合物加热并在80℃下回流12小时。当反应完成时,将水加入反应溶液,使用二氯甲烷(DCM)萃取混合物,用无水MgSO4从其除去水分,然后过滤残留物并在减压下浓缩。通过快速柱色谱分离和纯化获得的残留物,获得77.7g(86%)的化合物I-2。
HRMS(70eV,EI+):C24H16O的计算m/z:320.1201,测量:320。
元素分析:C,90%;H,5%
合成实施例3:中间体I-3的合成
将75g(234mmol)的化合物I-2在空气环境下溶解于800mL的甲苯中,将2.63g(11.7mmol)的乙酸钯(II)、9.09g(23.4mmol)的1,3-双(2,6-二异丙基苯基)-1,3-二氢-2H-咪唑-2-叉基)(IPr)、4.26g(23.4mmol)的4,5-二氮杂芴-9-酮、21.8g(117mmol)的2,4,6-三甲基苯甲酸钠、64.7g(468mmol)的碳酸钾、购自Acros的MS 3A(200mg)和1mL的均三甲苯(mesitylene)顺续加入其中,并将混合物加热并在120℃下回流24小时。当反应完成时,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得35.8g(48%)的化合物I-3。
HRMS(70eV,EI+):C24H14O的计算m/z:318.1045,测量:318。
元素分析:C,91%;H,4%
合成实施例4:中间体I-4的合成
将30g(94.2mmol)的化合物I-3在氮气环境下溶解于300mL的四氢呋喃(THF),并将溶液冷却至-78℃。然后,将溶解于己烷的2.5M的n-BuLi(57mL,141mmol)以逐滴方式在10分钟内缓慢加入其中。在室温搅拌混合物18小时。当反应完成时,将1N HCl(141mL,141mmol)加入其中以中和反应溶液。将生成物使用乙酸乙酯(EA)萃取,用无水MgSO4从中去除水分,并将获得的残留物使用己烷和二氯甲烷(DCM)清洗以去除杂质,获得27.0g(79%)的化合物I-4。
HRMS(70eV,EI+):C24H15BO3的计算m/z:362.1114,测量:362。
元素分析:C,80%;H,4%
合成实施例5:中间体I-5的合成
将100g(282mmol)的化合物I-1在氮气环境下溶解于900mL的四氢呋喃(THF)中,将77.4g(310mmol)的2-溴-5-氯苯甲酸甲酯和3.26g(2.82mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的97.4g(705mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流21小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得112g(94%)的化合物I-5。
HRMS(70eV,EI+):C26H17ClO2的计算m/z:396.0917,测量:396。
元素分析:C,79%;H,4%
合成实施例6:中间体I-6的合成
将110g(277mmol)的化合物I-5在氮气环境下溶解于1,100mL的四氢呋喃(THF),并将溶液冷却至0℃。然后将溶解于二甲基醚中的3.0M(231mL,693mmol)甲基溴化镁以逐滴方式在一个小时内缓慢加入其中。然后,在室温下搅拌混合物17小时。当反应完成时,将溶解于450mL的水中的44.5g(831mmol)的氯化铵加入其中以中和反应溶液。接着,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,并将残余物过滤并在减压下浓缩,获得109g(99%)的化合物I-6。
HRMS(70eV,EI+):C27H21ClO的计算m/z:396.1281,测量:396。
元素分析:C,82%;H,5%
合成实施例7:中间体I-7的合成
将105g(265mmol)的化合物I-6在氮气环境下溶解于1,300mL的二氯甲烷(DCM),并将溶液冷却至0℃。然后,将溶解于二乙基醚合物(diethyl etherate)中的56.4g(398mmol)三氟化硼以逐滴方式在1个小时内缓慢加入其中。在室温搅拌获得的混合物5小时。当反应完成时,将溶解于0.1L的水中的33.4g(398mmol)的碳酸氢钠加入其中以中和反应溶液。接着,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,并将获得的残留物通过快速柱色谱分离并纯化,获得73.3g(73%)的化合物I-7。
HRMS(70eV,EI+):C27H19Cl的计算m/z:378.1175,测量:378。
元素分析:C,86%;H,5%
合成实施例8:中间体I-8的合成
将化合物I-7(70g,185mmol)在氮气环境下溶解于600mL的二甲基甲酰胺(DMF)中,将56.3g(222mmol)的双(频那醇合)二硼、1.51g(1.85mmol)的1,1'-双(二苯基膦)二茂铁)二氯化钯(II)以及54.5g(555mmol)的乙酸钾加入其中,并将混合物加热并在150℃下回流80小时。当反应完成时,将水加入反应溶液,并过滤混合物以及在真空烘箱中干燥。通过快速柱色谱分离和纯化获得的残留物,获得74.0g(85%)的化合物I-8。
HRMS(70eV,EI+):C33H31BO2的计算m/z:470.2417,测量:470。
元素分析:C,84%;H,7%
合成实施例9:中间体I-9的合成
将100g(282mmol)的化合物I-1在氮气环境下溶解于900mL的四氢呋喃(THF)中,将77.4g(310mmol)的2-溴-4-氯苯甲酸甲酯和3.26g(2.82mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的97.4g(705mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流24小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得101g(90%)的化合物I-9。
HRMS(70eV,EI+):C26H17ClO2的计算m/z:396.0917,测量:396。
元素分析:C,79%;H,4%
合成实施例10:中间体I-10的合成
将化合物I-9(100g,252mmol)在氮气环境下溶解于1,000mL的四氢呋喃(THF),并将溶液冷却至0℃。然后,将溶解于二乙醚中的3.0M(210mL,630mmol)甲基溴化镁以逐滴方式在1小时内缓慢加入其中。在室温搅拌混合物20小时。当反应完成时,将溶解于400mL的水中的40.4g(756mmol)的氯化铵加入其中以中和反应溶液。然后,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,并将残余物过滤并在减压下浓缩,获得109g(99%)的化合物I-6。
HRMS(70eV,EI+):C27H21ClO的计算m/z:396.1281,测量:396。
元素分析:C,82%;H,5%
合成实施例11:中间体I-11的合成
将105g(265mmol)的化合物I-10在氮气环境下溶解于1,300mL的二氯甲烷(DCM),并将溶液冷却至0℃。然后,将溶解于二乙基醚合物中的56.4g(398mmol)三氟化硼以逐滴方式在1小时内缓慢加入其中。在室温搅拌混合物7小时。当反应完成时,将溶解于0.1L的水中的33.4g(398mmol)的碳酸氢钠加入其中以中和反应溶液。然后,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,并将获得的残留物通过快速柱色谱分离并纯化,获得79.3g(79%)的化合物I-11。
HRMS(70eV,EI+):C27H19Cl的计算m/z:378.1175,计算:378。
元素分析:C,86%;H,5%
合成实施例12:中间体I-12的合成
将70g(185mmol)的化合物I-11在氮气环境下溶解于600mL的二甲基甲酰胺(DMF)中,将56.3g(222mmol)的双(频那醇合)二硼、1.51g(1.85mmol)的1,1'-双(二苯基膦)二茂铁)二氯化钯(II)以及54.5g(555mmol)的乙酸钾加入其中,并将混合物加热并在150℃下回流68小时。当反应完成时,将水加入反应溶液,并过滤混合物以及在真空烘箱中干燥。通过快速柱色谱分离和纯化获得的残留物,获得71.4g(82%)的化合物I-12。
HRMS(70eV,EI+):C33H31BO2的计算m/z:470.2417,测量:470。
元素分析:C,84%;H,7%
合成实施例13:中间体I-13的合成
将100g(282mmol)的化合物I-1在氮气环境下溶解于800mL的四氢呋喃(THF)中,将63.9g(338mmol)的2-溴苯硫酚和3.26g(2.82mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的97.4g(705mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流9小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得85.4g(90%)的化合物I-13。
HRMS(70eV,EI+):C24H16S的计算m/z:336.0973,测量:336。
元素分析:C,86%;H,5%
合成实施例14:中间体I-14的合成
将78.7g(234mmol)的化合物I-13在空气环境下溶解于800mL甲苯中,将2.63g(11.7mmol)的乙酸钯(II)、9.09g(23.4mmol)的1,3-双(2,6-二异丙基苯基)-1,3-二氢-2H-咪唑-2-叉基(IPr)、4.26g(23.4mmol)的4,5-二氮杂芴-9-酮、21.8g(117mmol)的2,4,6-三甲基苯甲酸钠、64.7g(468mmol)的碳酸钾、购自Acros的MS 3A(200mg)和1mL的均三甲苯顺续加入其中,并将混合物加热并在120℃下回流24小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得33.7g(43%)的化合物I-14。
HRMS(70eV,EI+):C24H14S的计算m/z:334.0816,测量:334。
元素分析:C,86%;H,4%
合成实施例15:中间体I-15的合成
将中间体I-14(30g,89.7mmol)在氮气环境下溶解于300mL的四氢呋喃(THF),并将溶液冷却至-78℃。然后,将溶解于己烷的2.5M的n-BuLi(54mL,135mmol)以逐滴方式在10分钟内缓慢加入其中。在室温搅拌混合物18小时。当反应完成时,将1N HCl(135mL,135mmol)加入其中以中和反应溶液。将生成物使用乙酸乙酯(EA)萃取,用无水MgSO4从中去除水分,并将残留物使用己烷和二氯甲烷(DCM)清洗以去除杂质,获得29.2g(86%)的化合物I-15。
HRMS(70eV,EI+):C24H15BO2S的计算m/z:378.0886,测量:378。
元素分析:C,76%;H,4%
合成实施例16:中间体I-16的合成
将20g(55.2mmol)的化合物I-4在氮气环境下溶解于180mL的四氢呋喃(THF)中,将13.7g(55.2mmol)的4-碘代苯硼酸和0.64g(0.55mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将19.1g(138mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流8小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得18.1g(75%)的化合物I-16。
HRMS(70eV,EI+):C30H19BO3的计算m/z:438.1427,测量:438。
元素分析:C,82%;H,4%
合成实施例17:中间体I-17的合成
将20g(55.2mmol)的化合物I-4在氮气环境下溶解于180mL的四氢呋喃(THF)中,将13.7g(55.2mmol)的3-碘代苯硼酸和0.64g(0.55mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的19.1g(138mmol)的碳酸钾加入其中,并将获得的混合物加热并在80℃下回流8小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得16.5g(68%)的化合物I-17。
HRMS(70eV,EI+):C30H19BO3的计算m/z:438.1427,测量:438。
元素分析:C,82%;H,4%
合成实施例18:中间体I-18的合成
将20g(55.2mmol)的化合物I-4在氮气环境下溶解于180mL的四氢呋喃(THF)中,将13.7g(55.2mmol)的2-碘代苯硼酸和0.64g(0.55mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的19.1g(138mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流10小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得13.3g(55%)的化合物I-18。
HRMS(70eV,EI+):C30H19BO3的计算m/z:438.1427,测量:438。
元素分析:C,82%;H,4%
有机化合物的合成
实施例1:化合物4的合成
将20g(55.2mmol)的化合物I-4在氮气环境下溶解于200mL的四氢呋喃(THF)中,将14.8g(55.2mmol)的2-氯-4,6-二苯基-1,3,5-三嗪和0.64g(0.55mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的19.1g(138mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流17小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得24.6g(81%)的化合物4。
HRMS(70eV,EI+):C39H23N3O的计算m/z:549.1841,测量:549。
元素分析:C,85%;H,4%
实施例2:化合物6的合成
将20g(42.5mmol)的化合物I-12在氮气环境下溶解于160mL的四氢呋喃(THF)中,将11.4g(42.5mmol)的2-氯-4,6-二苯基-1,3,5-三嗪和0.49g(0.43mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的14.7g(106mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流8小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得17.1g(70%)的化合物6。
HRMS(70eV,EI+):C42H29N3的计算m/z:575.2361,测量:575。
元素分析:C,88%;H,5%
实施例3:化合物7的合成
将20g(42.5mmol)的化合物I-8在氮气环境下溶解于160mL的四氢呋喃(THF)中,将11.4g(42.5mmol)的2-氯-4,6-二苯基-1,3,5-三嗪和0.49g(0.43mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的14.7g(106mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流10小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得15.7g(64%)的化合物7。
HRMS(70eV,EI+):C42H29N3的计算m/z:575.2361,测量:575。
元素分析:C,88%;H,5%
实施例4:化合物8的合成
将20g(52.9mmol)的化合物I-15在氮气环境下溶解于200mL的四氢呋喃(THF)中,将14.2g(52.9mmol)的2-氯-4,6-二苯基-1,3,5-三嗪和0.61g(0.53mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的18.3g(132mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流15小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化分离获得的残留物,获得26.6g(89%)的化合物8。
HRMS(70eV,EI+):C39H23N3S的计算m/z:565.1613,测量:565。
元素分析:C,83%;H,4%
实施例5:化合物12的合成
将20g(55.2mmol)的化合物I-4在氮气环境下溶解于200mL的四氢呋喃(THF)中,将14.7g(55.2mmol)的2-氯-4,6-二苯基嘧啶和0.64g(0.55mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的19.1g(138mmol)的碳酸钾加入其中,并将混合物在80℃下加热和回流20小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得27.3g(90%)的化合物12。
HRMS(70eV,EI+):C40H24N2O的计算m/z:548.1889,测量:548。
元素分析:C,88%;H,4%
实施例6:化合物20的合成
将20g(55.2mmol)的化合物I-4在氮气环境下溶解于200mL的四氢呋喃(THF)中,将14.7g(55.2mmol)的4-氯-2,6-二苯基吡啶和0.64g(0.55mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的19.1g(138mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流16小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得25.4g(84%)的化合物20。
HRMS(70eV,EI+):C41H25NO的计算m/z:547.1936,测量:547。
元素分析:C,90%;H,5%
实施例7:化合物44的合成
将15g(34.2mmol)的化合物I-16在氮气环境下溶解于130mL的四氢呋喃(THF)中,将9.16g(34.2mmol)的2-氯-4,6-二苯基-1,3,5-三嗪和0.39g(0.34mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的11.8g(85.5mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流10小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得18.2g(85%)的化合物44。
HRMS(70eV,EI+):C45H27N3O的计算m/z:625.2154,测量:625。
元素分析:C,86%;H,4%
实施例8:化合物52的合成
将15g(34.2mmol)的化合物I-17在氮气环境下溶解于130mL的四氢呋喃(THF)中,将9.16g(34.2mmol)的2-氯-4,6-二苯基-1,3,5-三嗪和0.39g(0.34mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的11.8g(85.5mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流9小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得17.3g(81%)的化合物52。
HRMS(70eV,EI+):C45H27N3O的计算m/z:625.2154,测量:625。
元素分析:C,86%;H,4%
实施例9:化合物60的合成
将13g(29.7mmol)的化合物I-18在氮气环境下溶解于130mL的四氢呋喃(THF)中,将7.94g(29.7mmol)的2-氯-4,6-二苯基-1,3,5-三嗪和0.35g(0.30mmol)的四(三苯基膦)钯加入其中,并搅拌混合物。然后,将在水中饱和的10.3g(74.3mmol)的碳酸钾加入其中,并将混合物加热并在80℃下回流26小时。当反应完成时,将水加入反应溶液,用二氯甲烷(DCM)萃取,用无水MgSO4从中去除水分,然后过滤并在减压下浓缩残留物。通过快速柱色谱分离和纯化获得的残留物,获得9.85g(53%)的化合物60。
HRMS(70eV,EI+):C45H27N3O的计算m/z:625.2154,测量:625。
元素分析:C,86%;H,4%
有机发光二极管的制造
实施例10
根据实施例1的化合物4作为主体以及Ir(PPy)3作为掺杂剂用于制造有机发光二极管。对于阳极,使用厚度的ITO,并且对于阴极,使用厚度的铝(Al)。
具体地,说明制造有机发光二极管的方法,通过将具有15Ω/cm2薄层电阻(sheetresistance)的ITO玻璃基板切割为50mm×50mm×0.7mm的尺寸,将它们分别在丙酮、异丙醇和纯水中超声波清洗15分钟,并将它们UV臭氧清洗30分钟,以制造阳极。
在基板上,通过在650×10-7Pa的真空度下,以0.1至0.3nm/s范围的沉积速率沉积N4,N4'-二(萘-1-基)-N4,N4'-二苯基联苯基-4,4'-二胺(NPB)(80nm),以形成厚度的空穴传输层。
接着,通过在相同的真空沉积条件下使用根据实施例1的化合物4形成厚度的发射层,且在本文中,同时沉积作为磷光掺杂剂的Ir(PPy)3。本文中,通过调节磷光掺杂剂的沉积速率,基于100wt%的发射层,以7wt%的量沉积磷光掺杂剂。
在发射层上,通过在相同的真空沉积条件下沉积双(2-甲基-8-羟基喹啉)-4-(苯基酚基)铝(bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminum)(BAlq)形成厚度的空穴阻挡层。在空穴阻挡层上,通过在相同的真空沉积条件下沉积Alq3形成厚度的电子传输层。在电子传输层上,通过顺序沉积LiF和Al形成阴极,以制造有机光电器件。
有机光电器件具有以下结构:ITO/NPB(80nm)/EML(化合物4(93wt%)+Ir(PPy)3(7wt%),30nm)/Balq(5nm)/Alq3(20nm)/LiF(1nm)/Al(100nm)。
实施例11
除使用根据实施例2的化合物6代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
实施例12
除使用根据实施例3的化合物7代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
实施例13
除使用根据实施例4的化合物8代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
实施例14
除使用根据实施例5的化合物12代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
实施例15
除使用根据实施例6的化合物20代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
实施例16
除使用根据实施例7的化合物44代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
实施例17
除使用根据实施例8的化合物52代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
实施例18
除使用根据实施例9的化合物60代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。
比较例1
除使用CBP代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。CBP的结构在下文提供。
比较例2
除使用HOST1代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。HOST1的结构在下文提供。
比较例3
除使用HOST2代替根据实施例1的化合物4之外,根据与实施例10相同的方法制造有机发光二极管。HOST2的结构在下文提供。
用于制造有机发光二极管的NPB、BAlq、CBP、Ir(PPy)3、HOST1和HOST2的结构也提供如下。
评价
测量根据实施例10至18和比较例1至3的每种有机发光二极管取决于电压的电流密度和亮度变化以及发光效率。在如下方法中具体进行测量,并且在下表1中提供结果。
(1)取决于电压变化的电流密度变化测量
在使用电流-电压表(Keithley 2400)从0V上升到10V增大电压的同时测量有机发光二极管中流动的电流值,并将测量的电流值除以面积以提供结果。
(2)取决于电压变化的亮度变化测量
使用亮度计(Minolta Cs-1000A)从0V上升到10V增大电压的同时测量有机发光二极管的亮度。
(3)发光效率测量
通过使用来自第(1)和(2)项的亮度、电流密度和电压(V)计算在相同电流密度(10mA/cm2)下的电流效率(cd/A)。
[表1]
参照表1,与比较例1至3的化合物相比,在实施例10至18中用于发射层的化合物示出了发光效率显著增加,而驱动电压降低。因此,结果表明,可以制造具有低电压的高效率器件。具体地,分别包括根据实施例11或12的含有芴基的化合物6或7的有机发光二极管示出了最优异的效率以及低驱动电压。
尽管已经连同目前认为是实用的示例性实施方式一起描述了本发明,但是应该理解的是,本发明并不限于所公开的实施方式,而是,相反,旨在涵盖包括在所附权利要求的精神和范围内的各种修改和等价安排。因此,上述实施方式应理解为示例性的,但不以任何方式限制本发明。
Claims (11)
1.一种通过由化学式1表示的部分和由化学式2表示的部分的组合表示的有机化合物:
其中,在化学式1或化学式2中,
X是CRaRb、O或S,
Z各自独立地是N或CRe,
Z中的至少一个是N,
R1至R8、Ra、Rb和Re各自独立地是氢、氘、取代或未取代的C1至C20烷基、取代或未取代的C6至C30芳基或它们的组合,
L是取代或未取代的C6至C30亚芳基,
n1至n3各自独立地是0或1,并且
化学式1的相邻的两个*与化学式2的两个*键合以形成稠环。
2.根据权利要求1所述的有机化合物,其中,所述有机化合物由化学式3或以下化学式4表示:
其中,在化学式3或化学式4中,
X是CRaRb、O或S,
Z各自独立地是N或CRe,
Z中的至少一个是N,
R1至R8、Ra、Rb和Re各自独立地是氢、氘、取代或未取代的C1至C20烷基、取代或未取代的C6至C30芳基或它们的组合,
L是取代或未取代的C6至C30亚芳基,并且
n1至n3各自独立地是0或1。
3.根据权利要求1所述的有机化合物,其中,所述由化学式2表示的部分由化学式2-I至化学式2-III中的一种表示:
[化学式2-III]
其中,在化学式2-I至化学式2-III中,
X1和X2各自独立地是CRaRb,
X3是O或S,
Z各自独立地是N或CRe,
Z中的至少一个是N,
R5至R8、Ra、Rb和Re各自独立地是氢、氘、取代或未取代的C1至C20烷基、取代或未取代的C6至C30芳基或它们的组合,
L是取代或未取代的C6至C30亚芳基,并且
n1至n3各自独立地是0或1,并且
化学式2-I至2-III的相邻的两个*与化学式1的两个*键合以形成稠环。
4.根据权利要求1所述的有机化合物,其中,所述由化学式2表示的部分由化学式2a和组1中的一种的组合表示:
[化学式2a]
[组1]
其中,在化学式2a或组1中,
X是CRaRb、O或S,
Ra和Rb各自独立地是氢、氘、取代或未取代的C1至C20烷基、取代或未取代的C6至C30芳基或它们的组合,
L是取代或未取代的C6至C30亚芳基,并且
n1是0或1。
5.根据权利要求1所述的有机化合物,其中,R1至R4各自独立地是氢、氘、或者取代或未取代的C1至C20烷基。
6.根据权利要求1所述的有机化合物,其中,所述有机化合物是组2中列出的化合物中的一种:
[组2]
7.一种有机光电子器件,包括
彼此面对的阳极和阴极,以及
所述阳极和所述阴极之间的至少一个有机层,其中,所述有机层包含根据权利要求1至权利要求6中任一项所述的有机化合物。
8.根据权利要求7所述的有机光电子器件,其中,
所述有机层包括发射层,
所述发射层包含所述有机化合物。
9.根据权利要求8所述的有机光电子器件,其中,所述有机化合物作为主体包括在发射层中。
10.根据权利要求7所述的有机光电子器件,其中,所述有机层包括选自以下的至少一种辅助层:空穴注入层、空穴传输层、电子阻挡层、电子传输层、电子注入层、以及空穴阻挡层,并且
所述辅助层包含所述有机化合物。
11.一种包括根据权利要求7所述的有机光电子器件的显示装置。
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Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101542714B1 (ko) * | 2014-04-04 | 2015-08-12 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR20150115622A (ko) | 2014-04-04 | 2015-10-14 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR101537499B1 (ko) * | 2014-04-04 | 2015-07-16 | 주식회사 엘지화학 | 유기 발광 소자 |
KR101537500B1 (ko) | 2014-04-04 | 2015-07-20 | 주식회사 엘지화학 | 유기 발광 소자 |
US9929349B2 (en) * | 2014-12-08 | 2018-03-27 | Samsung Display Co., Ltd. | Organic light emitting device and display device including the same |
KR101745799B1 (ko) | 2014-12-24 | 2017-06-09 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
US9793493B2 (en) * | 2014-12-30 | 2017-10-17 | Luminescence Technology Corp. | Organic material and organic electroluminescent device using the same |
US20160211456A1 (en) * | 2015-01-19 | 2016-07-21 | Luminescence Technology Corp. | PHENANTHRO[9,10-b]TETRAPHENYLENE DERIVATIVE AND USE THEREOF |
US10164194B2 (en) * | 2015-01-26 | 2018-12-25 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
TWI723007B (zh) * | 2015-02-18 | 2021-04-01 | 德商諾瓦發光二極體有限公司 | 半導體材料及其萘并呋喃基質化合物 |
US20160380207A1 (en) * | 2015-06-29 | 2016-12-29 | Feng-wen Yen | Triphenylene-based fused biscarbazole derivative and use thereof |
KR102041588B1 (ko) * | 2016-09-29 | 2019-11-06 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
KR101970000B1 (ko) * | 2016-10-12 | 2019-04-17 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치 |
US10103337B1 (en) * | 2017-04-28 | 2018-10-16 | Feng-wen Yen | Organic electroluminescent material and using the same |
CN107163057A (zh) * | 2017-06-30 | 2017-09-15 | 中节能万润股份有限公司 | 一种含有氮杂二苯并呋喃并邻菲罗啉结构的oled材料、其制备方法及应用 |
WO2019013509A1 (ko) * | 2017-07-10 | 2019-01-17 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
KR102020029B1 (ko) * | 2017-07-10 | 2019-09-10 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
CN110997648B (zh) * | 2017-08-10 | 2023-12-19 | 东曹株式会社 | 稠环化合物 |
US10428269B2 (en) * | 2017-12-27 | 2019-10-01 | Feng-wen Yen | Indenotriphenylene derivative and organic electroluminescence device using the same |
KR102217250B1 (ko) * | 2018-06-12 | 2021-02-18 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
EP3582280B1 (en) * | 2018-06-14 | 2024-03-20 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
US11236075B2 (en) * | 2018-12-17 | 2022-02-01 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
US11296282B2 (en) * | 2018-12-17 | 2022-04-05 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
KR102021294B1 (ko) * | 2018-12-20 | 2019-09-11 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
EP3670510A3 (en) * | 2018-12-20 | 2020-07-01 | Duk San Neolux Co., Ltd. | Benzo[b]naphtho[2,3-d]furanyl- or benzo[b]naphtho[2,3-d]thiophenyl-triazine compounds for organic electronic elements |
US11108001B2 (en) * | 2019-01-17 | 2021-08-31 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
KR102442580B1 (ko) * | 2020-04-09 | 2022-09-13 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
WO2021206502A1 (ko) * | 2020-04-09 | 2021-10-14 | 주식회사 엘지화학 | 유기 발광 소자 |
TWI792166B (zh) * | 2021-01-29 | 2023-02-11 | 機光科技股份有限公司 | 有機化合物和以其作為材料的紅光有機發光裝置 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1661888A1 (en) * | 2004-11-29 | 2006-05-31 | Samsung SDI Co., Ltd. | Phenylcarbazole-based compound and organic electroluminescent device employing the same |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3995402B2 (ja) * | 2000-07-31 | 2007-10-24 | 三井化学株式会社 | 炭化水素化合物および有機電界発光素子 |
KR20160104752A (ko) | 2007-08-08 | 2016-09-05 | 유니버셜 디스플레이 코포레이션 | 인광성 발광 다이오드의 단일 트리페닐렌 발색단 |
JP2009114068A (ja) | 2007-11-01 | 2009-05-28 | Canon Inc | トリフェニレン化合物及びこれを用いた有機発光素子 |
TWI448534B (zh) | 2009-09-28 | 2014-08-11 | Ritdisplay Corp | 有機電致發光元件 |
KR101724304B1 (ko) | 2009-10-16 | 2017-04-10 | 에스에프씨 주식회사 | 축합방향족 화합물 및 이를 포함하는 유기전계발광소자 |
KR101134575B1 (ko) | 2009-11-17 | 2012-04-16 | 주식회사 이엘엠 | 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자 |
US8968887B2 (en) | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
KR101196093B1 (ko) | 2010-05-06 | 2012-11-01 | 주식회사 두산 | 페난스로카바졸 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR101218029B1 (ko) | 2010-05-06 | 2013-01-02 | 주식회사 두산 | 방향족 아민을 포함하는 트리페닐렌계 화합물 및 이를 포함하는 유기 전계 발광 소자 |
JP5735241B2 (ja) | 2010-09-08 | 2015-06-17 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び電荷輸送材料 |
JP5729957B2 (ja) * | 2010-09-29 | 2015-06-03 | キヤノン株式会社 | ジベンゾチオフェン化合物およびそれを有する有機発光素子 |
JP5773638B2 (ja) | 2010-12-24 | 2015-09-02 | キヤノン株式会社 | 縮合多環化合物及びこれを用いた有機発光素子 |
KR101866851B1 (ko) | 2010-12-24 | 2018-06-14 | 에스에프씨 주식회사 | 이형고리 화합물 및 이를 포함하는 유기전계발광소자 |
JP5804797B2 (ja) * | 2011-06-28 | 2015-11-04 | キヤノン株式会社 | ベンゾトリフェニレノフラン化合物およびそれを有する有機発光素子 |
KR101366368B1 (ko) | 2011-07-08 | 2014-02-21 | 주식회사 두산 | 신규 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20130007951A (ko) | 2011-07-11 | 2013-01-21 | 주식회사 두산 | 트리페닐렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR101470055B1 (ko) * | 2011-07-11 | 2014-12-08 | 주식회사 두산 | 트리페닐렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR101971198B1 (ko) * | 2011-10-19 | 2019-04-23 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치 |
KR101618683B1 (ko) | 2013-05-16 | 2016-05-09 | 제일모직 주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
KR102078365B1 (ko) * | 2013-07-01 | 2020-04-03 | 삼성디스플레이 주식회사 | 유기 발광 장치 |
-
2013
- 2013-07-10 KR KR1020130081176A patent/KR101627761B1/ko active IP Right Grant
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- 2014-02-20 JP JP2016525262A patent/JP6335288B2/ja active Active
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1661888A1 (en) * | 2004-11-29 | 2006-05-31 | Samsung SDI Co., Ltd. | Phenylcarbazole-based compound and organic electroluminescent device employing the same |
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