JP2023511161A - 多環芳香族誘導体化合物及びこれを用いた有機発光素子 - Google Patents
多環芳香族誘導体化合物及びこれを用いた有機発光素子 Download PDFInfo
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- -1 Polycyclic aromatic derivative compound Chemical class 0.000 title abstract description 68
- 239000012044 organic layer Substances 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 100
- 239000010410 layer Substances 0.000 claims description 65
- 239000000126 substance Substances 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000003367 polycyclic group Chemical group 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 125000005264 aryl amine group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000002723 alicyclic group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 125000005104 aryl silyl group Chemical group 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 6
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
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- 150000001454 anthracenes Chemical class 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000032258 transport Effects 0.000 description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[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.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
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- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
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- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 3
- KXSCVTKVAASZEO-UHFFFAOYSA-N 1,2-dichloro-3-iodo-5-methylbenzene Chemical compound ClC=1C=C(C=C(C1Cl)I)C KXSCVTKVAASZEO-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- LQJJCCZSSLQQHY-UHFFFAOYSA-N 4a,9a-dimethyl-2,3,4,9-tetrahydro-1h-carbazole Chemical compound C12=CC=CC=C2NC2(C)C1(C)CCCC2 LQJJCCZSSLQQHY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940127271 compound 49 Drugs 0.000 description 3
- 229940125900 compound 59 Drugs 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 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
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
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- 238000002207 thermal evaporation Methods 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
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- 238000001771 vacuum deposition Methods 0.000 description 2
- PRRIGGBFRPGBRY-UHFFFAOYSA-N (3-diphenylphosphanyl-1-naphthalen-1-ylnaphthalen-2-yl)-diphenylphosphane Chemical group C1=CC=CC=C1P(C=1C(=C(C=2C3=CC=CC=C3C=CC=2)C2=CC=CC=C2C=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 PRRIGGBFRPGBRY-UHFFFAOYSA-N 0.000 description 1
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- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
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- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
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- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYKFPJAARRNNRX-UHFFFAOYSA-N 2,3,4,4a,9,9a-hexahydro-1h-carbazole Chemical compound C1=CC=C2C3CCCCC3NC2=C1 HYKFPJAARRNNRX-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 1
- TUVDJRXZHABERX-UHFFFAOYSA-N 3-bromo-5-tert-butyl-1-benzothiophene Chemical compound CC(C)(C)C1=CC=C2SC=C(Br)C2=C1 TUVDJRXZHABERX-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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- 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
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- 229920003023 plastic Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001725 pyrenyl group Chemical group 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 235000009566 rice Nutrition 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
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- 235000017281 sodium acetate Nutrition 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 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
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 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
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
本発明は、多環芳香族誘導体化合物、及びこれを用いて発光効率が著しく向上した高効率、長寿命の有機発光素子に関する。
有機発光素子は、電子注入電極(カソード電極)から注入された電子(electron)と、正孔注入電極(アノード電極)から注入された正孔(hole)とが発光層で結合してエキシトン(exciton)を形成し、そのエキシトンがエネルギーを放出しながら発光する自発光型素子であり、このような有機発光素子は、低い駆動電圧、高い輝度、広い視野角及び速い応答速度を有し、フルカラー平板発光ディスプレイに適用可能であるという利点から、次世代光源として脚光を浴びている。
〔発明が解決しようとする課題〕
したがって、本発明は、素子の有機層に採用されて高効率及び長寿命の有機発光素子を実現できる有機発光化合物、及びこれを含む有機発光素子を提供しようとする。
本発明は、上記課題を解決するために、下記化学式A-1または化学式A-2で表される有機発光化合物を提供する。
本発明に係る多環芳香族誘導体化合物は、素子内の有機層に採用されて高効率及び長寿命の有機発光素子を実現することができる。
以下、本発明をさらに詳細に説明する。
Q1及びQ2は、互いに同一又は異なっており、それぞれ独立して、置換もしくは非置換の炭素数6~50の芳香族炭化水素環、置換もしくは非置換の炭素数2~50の芳香族ヘテロ環、または置換もしくは非置換の炭素数3~30の脂肪族芳香族混合環である。
Zは、CRまたはNであり、前記Rは、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数5~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数5~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数5~30のアリールシリル基、ニトロ基、シアノ基及びハロゲン基から選択されるいずれか1つであり、複数のZ及びRは、互いに同一又は異なっていてもよい。
R21~R28は、それぞれ、同一又は異なっており、前記化学式A-1または化学式A-2のR1~R12で定義されたものと同一である。
R31~R35は、それぞれ、同一又は異なっており、前記化学式A-1または化学式A-2のR1~R12で定義されたものと同一であり、互いに隣接する置換基と結合して飽和あるいは不飽和環を形成することができる。
以下、好ましい実施例を挙げて本発明をさらに詳細に説明する。しかし、これらの実施例は、本発明をより具体的に説明するためのもので、本発明の範囲がこれによって制限されないということは、当業界における通常の知識を有する者には自明であろう。
合成例1-1.<中間体1-a>の合成
下記[反応式1]によって<中間体1-a>を合成した。
下記[反応式2]によって<中間体1-b>を合成した。
下記[反応式3]によって<中間体1-c>を合成した。
下記[反応式4]によって<化合物2>を合成した。
MS(MALDI-TOF):m/z 634.36[M+]。
合成例2-1.<中間体2-a>の合成
下記[反応式5]によって<中間体2-a>を合成した。
下記[反応式6]によって<中間体2-b>を合成した。
下記[反応式7]によって<中間体2-c>を合成した。
下記[反応式8]によって<化合物6>を合成した。
MS(MALDI-TOF):m/z 662.40[M+]。
合成例3-1.<中間体3-a>の合成
下記[反応式9]によって<中間体3-a>を合成した。
下記[反応式10]によって<中間体3-b>を合成した。
下記[反応式11]によって<中間体3-c>を合成した。
下記[反応式12]によって<化合物15>を合成した。
MS(MALDI-TOF):m/z 732.46[M+]。
合成例4-1.<中間体4-a>の合成
下記[反応式13]によって<中間体4-a>を合成した。
下記[反応式14]によって<中間体4-b>を合成した。
下記[反応式15]によって<中間体4-c>を合成した。
下記[反応式16]によって<化合物16>を合成した。
MS(MALDI-TOF):m/z 819.48[M+]。
下記[反応式17]によって<化合物49>を合成した。
MS(MALDI-TOF):m/z 696.33[M+]。
下記[反応式18]によって<化合物59>を合成した。
MS(MALDI-TOF):m/z 696.37[M+]。
ITOガラスの発光面積が2mm×2mmのサイズとなるようにパターニングした後、洗浄した。前記ITOガラスを真空チャンバに装着した後、ベース圧力が1×10-7torrとなるようにした後、前記ITO上にHATCN(700Å)、化学式F(250Å)の順に成膜した。発光層は、下記に記載されたホスト(BH2)と本発明の化合物(3wt%)とを混合して成膜(250Å)した後、以降に電子輸送層として化学式E-1と化学式E-2を1:1の比で300Å、電子注入層として化学式E-1を5Å、Al(1000Å)の順に成膜して、有機発光素子を製造した。前記有機発光素子の発光特性は0.4mAで測定した。
前記実施例1で用いられた化合物の代わりに[BD1]及び[BD2]を用いた以外は、同様にして有機発光素子を作製し、前記有機発光素子の発光特性は0.4mAで測定した。前記[BD1]及び[BD2]の構造は、次の通りである。
本発明の多環芳香族誘導体化合物は有機発光素子内の有機層に採用されて、発光効率が著しく向上した高効率及び長寿命の有機発光素子を実現できるところ、様々なディスプレイ素子及び照明素子に産業的に有用に活用することができる。
Claims (10)
- 下記化学式A-1または化学式A-2で表される化合物。
(前記化学式A-1及び化学式A-2において、
Q1及びQ2は、互いに同一又は異なっており、それぞれ独立して、置換もしくは非置換の炭素数6~50の芳香族炭化水素環、置換もしくは非置換の炭素数2~50の芳香族ヘテロ環、または置換もしくは非置換の炭素数3~30の脂肪族芳香族混合環であり、
Xは、B、P、P=O及びP=Sから選択されるいずれか1つであり、
Y1及びY2は、互いに同一又は異なっており、それぞれ独立して、N-R8、CR9R10、O、S、Se及びSiR11R12から選択されるいずれか1つであり、
Vは、N及びPから選択され、
R1~R12は、互いに同一又は異なっており、それぞれ独立して、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数5~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数5~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数5~30のアリールシリル基、ニトロ基、シアノ基及びハロゲン基から選択されるいずれか1つであり、
前記R2とR3は、互いに連結されて単環または多環を形成することができ、
前記R7は、隣接する前記Q1環と結合して脂環族または芳香族の単環もしくは多環をさらに形成することができ、
前記R8~R12は、それぞれ、前記Q1乃至Q2環と結合して脂環族または芳香族の単環もしくは多環をさらに形成することができ、
前記R5とR6、R9とR10及びR11とR12は、それぞれ、互いに連結されて脂環族または芳香族の単環もしくは多環をさらに形成することができる。) - 前記化学式A-1または化学式A-2は、下記化学式A-3または化学式A-4で表されることを特徴とする、請求項1に記載の化合物。
(前記化学式A-3及び化学式A-4において、
Zは、CRまたはNであり、前記Rは、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数5~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数5~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数5~30のアリールシリル基、ニトロ基、シアノ基及びハロゲン基から選択されるいずれか1つであり(複数のZ及びRは、互いに同一又は異なっている)、
前記複数のRは、互いに結合するか、または隣接する置換基と連結されて脂環族または芳香族の単環もしくは多環を形成することができ、前記形成された脂環族または芳香族の単環もしくは多環の炭素原子は、N、S及びOから選択されるいずれか1つ以上のヘテロ原子で置換されてもよく、
X、Y1、Y2、V及びR1~R7は、前記化学式A-1及び化学式A-2での定義と同一である。) - 第1電極、前記第1電極に対向する第2電極、及び前記第1電極と第2電極との間に介在する有機層を含み、
前記有機層が、請求項1に記載の化学式A-1または化学式A-2で表される化合物を1種以上含む、有機発光素子。 - 前記有機層は、電子注入層、電子輸送層、正孔注入層、正孔輸送層、電子阻止層、正孔阻止層及び発光層のうちの1層以上を含み、
前記層のうちの1層以上が、前記化学式A-1または化学式A-2で表される化合物を含むことを特徴とする、請求項4に記載の有機発光素子。 - 前記発光層は、下記化学式Cで表されるアントラセン誘導体をホスト化合物として含むことを特徴とする、請求項5に記載の有機発光素子。
(前記化学式Cにおいて、
R21~R28は、それぞれ、同一又は異なっており、前記請求項1に記載の化学式A-1または化学式A-2のR1~R12で定義されたものと同一であり、
Ar9及びAr10は、それぞれ、互いに同一又は異なっており、互いに独立して、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~20のアルキニル基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数5~30のシクロアルケニル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数2~30のヘテロシクロアルキル基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数6~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数6~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、及び置換もしくは非置換の炭素数6~30のアリールシリル基から選択されるいずれか1つであり、
L13は、単結合であるか、または置換もしくは非置換の炭素数6~20のアリーレン基、及び置換もしくは非置換の炭素数2~20のヘテロアリーレン基から選択されるいずれか1つであり、
kは、1~3の整数であり、前記kが2以上である場合に、それぞれのL13は互いに同一又は異なっている。) - 前記それぞれの層から選択された1つ以上の層は、蒸着工程または溶液工程によって形成されることを特徴とする、請求項5に記載の有機発光素子。
- 前記有機発光素子は、平板ディスプレイ装置、フレキシブルディスプレイ装置、単色又は白色の平板照明用装置、及び単色又は白色のフレキシブル照明用装置から選択されるいずれか1つに使用されることを特徴とする、請求項4に記載の有機発光素子。
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KR20210095072A (ko) | 2021-07-30 |
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