JP6721653B2 - 燐光oledのためのホスト物質 - Google Patents
燐光oledのためのホスト物質 Download PDFInfo
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- JP6721653B2 JP6721653B2 JP2018188220A JP2018188220A JP6721653B2 JP 6721653 B2 JP6721653 B2 JP 6721653B2 JP 2018188220 A JP2018188220 A JP 2018188220A JP 2018188220 A JP2018188220 A JP 2018188220A JP 6721653 B2 JP6721653 B2 JP 6721653B2
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- 239000000463 material Substances 0.000 title claims description 53
- 239000010410 layer Substances 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 239000012044 organic layer Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- 229910052805 deuterium Inorganic materials 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 25
- 150000004820 halides Chemical class 0.000 claims description 24
- 239000003446 ligand Substances 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 239000002019 doping agent Substances 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 21
- 230000000903 blocking effect Effects 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- 125000002560 nitrile group Chemical group 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 46
- -1 azadibenzofuran Chemical compound 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 22
- 125000004404 heteroalkyl group Chemical group 0.000 description 22
- 150000002431 hydrogen Chemical class 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 150000002527 isonitriles Chemical class 0.000 description 20
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000003480 eluent Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 14
- 125000003396 thiol group Chemical group [H]S* 0.000 description 14
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- 230000032258 transport Effects 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 12
- 0 CCCCc1cc(-c2ccccc2C2(CC)C3(CC)CC2)*3cc1 Chemical compound CCCCc1cc(-c2ccccc2C2(CC)C3(CC)CC2)*3cc1 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 8
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 8
- 150000004696 coordination complex Chemical class 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- XHKGWBQWXWPJSF-UHFFFAOYSA-N (3-bromophenyl)-dibenzofuran-4-yl-diphenylsilane Chemical compound BrC1=CC=CC([Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)=C1 XHKGWBQWXWPJSF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 6
- 125000005110 aryl thio group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- CVLVVSBWIBRTHJ-UHFFFAOYSA-N (3-bromophenyl)-dibenzothiophen-4-yl-diphenylsilane Chemical compound BrC1=CC=CC([Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C3=C(C4=CC=CC=C4S3)C=CC=2)=C1 CVLVVSBWIBRTHJ-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
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- 229920000642 polymer Polymers 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
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- 229910000077 silane Inorganic materials 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 3
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
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- 239000012634 fragment Substances 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
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- 238000005215 recombination Methods 0.000 description 3
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
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- YMUANPDSYJLDDR-UHFFFAOYSA-N 1-[3-[3-(3-carbazol-9-ylphenyl)phenyl]carbazol-9-yl]ethanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)C=2C=C3C4=CC=CC=C4N(C3=CC=2)C(=O)C)=CC=C1 YMUANPDSYJLDDR-UHFFFAOYSA-N 0.000 description 2
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- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 2
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- BLRSLZDXLBTLED-UHFFFAOYSA-N 3-[3-(3-carbazol-9-ylphenyl)phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)C=2C=C3C4=CC=CC=C4NC3=CC=2)=CC=C1 BLRSLZDXLBTLED-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FHJJVSJWFYYPAC-UHFFFAOYSA-N 3-carbazol-9-yl-9h-carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C2NC3=CC=CC=C3C2=C1 FHJJVSJWFYYPAC-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- ZKGHGKNHPPZALY-UHFFFAOYSA-N 9-(3-bromophenyl)carbazole Chemical compound BrC1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 ZKGHGKNHPPZALY-UHFFFAOYSA-N 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
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- 238000004544 sputter deposition Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Description
Ar及びAr′は独立に、フェニル、ビフェニル、ナフチル、ジベンゾチオフェン、及びジベンゾフランからなる群から選択され、これは任意選択によりさらに置換されていてもよい。ZはSi及びGeから選択される。Lは単結合であるか、又はアリール、アミノ、もしくはそれらの組み合わせを含み、且つ、Lは任意選択によりさらに置換されていてもよい。
一般に、OLEDは、アノードとカソードとの間に配置され且つそれらと電気的に接続された少なくとも1つの有機層を含む。電流が流された場合、有機層(1又は複数)にアノードは正孔を注入し、カソードは電子を注入する。注入された正孔と電子はそれぞれ反対に帯電した電極に向かって移動する。電子と正孔が同じ分子上に局在する場合、励起エネルギー状態を有する局在化された電子−正孔対である「励起子」が形成される。励起子が発光機構によって緩和するときに光が発せられる。いくつかの場合には、励起子はエキシマー又はエキシプレックス上に局在化されうる。非放射機構、例えば、熱緩和も起こりうるが、通常は好ましくないと考えられる。
及び、Baldoら,“Very high-efficiency green organic light-emitting devices based on electrophosphorescence”, Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”)、これらを参照により全体を援用する。燐光は、米国特許第7,279,704号明細書の第5〜6欄に、より詳細に記載されており、これを参照により援用する。
Ar及びAr′は独立に、フェニル、ビフェニル、ナフチル、ジベンゾチオフェン、及びジベンゾフランからなる群から選択され、これは任意選択によりさらに置換されていてもよい。ZはSi及びGeから選択される。Lは単結合であるか、又はアリール、アミノ、もしくはそれらの組み合わせを含み、且つ、Lは任意選択によりさらに置換されていてもよい。
有機発光デバイス中の具体的な層に有用として本明細書に記載した物質は、そのデバイス中に存在するその他の広範囲にわたる物質と組み合わせて用いることができる。例えば、本明細書に開示した発光ドーパントは、存在してもよい広い範囲のホスト、輸送層、阻止層、注入層、電極、及びその他の層と組み合わせて用いることができる。以下に記載乃至言及した物質は、本明細書に記載した化合物と組み合わせて有用でありうる物質の非制限的な例であり、当業者は組み合わせて有用でありうるその他の物質を特定するために文献を容易に参考にすることができる。
フタロシアニン又はポルフィリン誘導体;芳香族アミン誘導体;インドロカルバゾール誘導体;フルオロ炭化水素を含むポリマー;導電性ドーパントを伴うポリマー;導電性ポリマー、例えば、PEDOT/PSS;ホスホン酸及びシラン誘導体などの化合物から誘導される自己組織化モノマー;金属酸化物誘導体、例えば、MoOx;p型半導体有機化合物、例えば、1,4,5,8,9,12−ヘキサアザトリフェニレンヘキサカルボニトリル;金属錯体、及び架橋性化合物。
Claims (14)
- 下記式Iの化合物:
ZはSiであり;
Lは
Aは、ジベンゾフラン及びジベンゾチオフェンからなる群から選択される基であり、これらは任意選択により、重水素、アルキル、シクロアルキル、アリールアルキル、アリール、及びそれらの組み合わせから選択された少なくとも1つの基でさらに置換されていてもよく;且つ、
Bは、カルバゾール基を表し、前記カルバゾール基は任意選択で、重水素、アルキル、シクロアルキル、アリールアルキル、アリール、ヘテロアリール、及びそれらの組み合わせからなる群から選択される少なくとも1つの基でさらに置換されていてもよい。 - 式I中、Lがフェニレンを表す、請求項1に記載の化合物。
- 式I中、Ar及びAr′がフェニルである、請求項1に記載の化合物。
- アノード、カソード、及び前記アノードと前記カソードの間に配置され、請求項1〜5のいずれか一項に記載の化合物を含む有機層を含む、有機発光デバイス。
- 前記有機層が発光層であり、且つ、式Iの化合物がホストである、請求項6に記載の有機発光デバイス。
- 前記有機層がさらに発光ドーパントを含む、請求項7に記載の有機発光デバイス。
- 前記発光ドーパントが以下のものからなる群から選択される少なくとも1つの配位子を有する遷移金属錯体である、請求項8に記載の有機発光デバイス。
Ra、Rb、及びRcが置換基を表す場合は独立に、重水素、ハライド、アルキル、シクロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、アルケニル、シクロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボキシル基、ニトリル基、イソニトリル基、及びホスフィノからなる群から選択され;且つ
Ra、Rb、及びRcのうちの2つの隣接置換基は任意選択により結合して縮合環を形成していてもよい。 - 前記発光ドーパントが下記式を有する、請求項8に記載の有機発光デバイス。
R1、R2、及びR3は独立に、非置換であるか、モノ、ジ、トリ、又はテトラ置換を表し;
R1、R2、及びR3が置換基を表す場合、そのそれぞれは独立に、重水素、ハライド、アルキル、シクロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、アルケニル、シクロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボキシル基、ニトリル基、イソニトリル基、及びホスフィノからなる群から選択され;
R1は任意選択により環Dに連結していてもよく;
nは1、2、又は3であり;且つ、X−Yは別の配位子である。 - 非発光層である第二の有機層をさらに含み、且つ、式Iを有する前記化合物が第二の有機層中の物質である、請求項6に記載の有機発光デバイス。
- 前記第二の有機層が阻止層であり、且つ、式Iを有する前記化合物が前記第二の有機層中の阻止性物質である、請求項11に記載の有機発光デバイス。
- 前記第二の有機層が電子輸送層であり、且つ、式Iを有する前記化合物が前記第二の有機層中の電子輸送物質である、請求項11に記載の有機発光デバイス。
- 請求項6に記載の有機発光デバイスを含む消費者製品であって、フラットパネルディスプレイ、コンピュータのモニタ、テレビ、広告板、室内もしくは屋外の照明灯および/または信号灯、ヘッドアップディスプレイ、完全に透明なディスプレイ、フレキシブルディスプレイ、レーザープリンタ、電話機、携帯電話、携帯情報端末、ラップトップコンピュータ、デジタルカメラ、カムコーダ、ビューファインダー、マイクロディスプレイ、乗り物、大面積壁面、映画館またはスタジアムのスクリーン、あるいは標識からなる群から選択される消費者製品。
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EP3401974B1 (en) | 2023-06-28 |
EP2551932B1 (en) | 2018-05-23 |
EP3401974A1 (en) | 2018-11-14 |
US20130026909A1 (en) | 2013-01-31 |
CN103122007B (zh) | 2017-04-12 |
JP6416169B2 (ja) | 2018-10-31 |
JP2019014737A (ja) | 2019-01-31 |
TW201307526A (zh) | 2013-02-16 |
US8409729B2 (en) | 2013-04-02 |
CN103122007A (zh) | 2013-05-29 |
TWI555822B (zh) | 2016-11-01 |
EP2551932A3 (en) | 2015-12-30 |
KR20130018551A (ko) | 2013-02-25 |
JP2013028605A (ja) | 2013-02-07 |
JP2017008107A (ja) | 2017-01-12 |
EP2551932A2 (en) | 2013-01-30 |
KR101919621B1 (ko) | 2018-11-16 |
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