JP2019090023A - 含窒素ヘテロポリ芳香族部分を電子アクセプターとして含むドナーアクセプター化合物 - Google Patents
含窒素ヘテロポリ芳香族部分を電子アクセプターとして含むドナーアクセプター化合物 Download PDFInfo
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- JP2019090023A JP2019090023A JP2018231393A JP2018231393A JP2019090023A JP 2019090023 A JP2019090023 A JP 2019090023A JP 2018231393 A JP2018231393 A JP 2018231393A JP 2018231393 A JP2018231393 A JP 2018231393A JP 2019090023 A JP2019090023 A JP 2019090023A
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- light emitting
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- nitrogen
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 68
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title abstract description 6
- -1 amino, silyl Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 150000002527 isonitriles Chemical class 0.000 claims description 19
- 150000002825 nitriles Chemical class 0.000 claims description 19
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
- 150000004820 halides Chemical class 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 8
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 114
- 239000010410 layer Substances 0.000 description 109
- 239000000463 material Substances 0.000 description 80
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- 229910052757 nitrogen Inorganic materials 0.000 description 63
- 239000000243 solution Substances 0.000 description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 37
- 239000000203 mixture Substances 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000003480 eluent Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 239000000370 acceptor Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000001816 cooling Methods 0.000 description 20
- 239000003446 ligand Substances 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 230000003111 delayed effect Effects 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 230000032258 transport Effects 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- ABRHSRPOYMSBOI-UHFFFAOYSA-N 4-chloro-[1]benzofuro[3,2-d]pyrimidine Chemical compound C12=CC=CC=C2OC2=C1N=CN=C2Cl ABRHSRPOYMSBOI-UHFFFAOYSA-N 0.000 description 7
- 150000004696 coordination complex Chemical class 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material 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
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 238000005424 photoluminescence Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- 125000006615 aromatic heterocyclic group Chemical group 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
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 3
- QFMSRGZWWJLTQE-UHFFFAOYSA-N 1h-[1]benzothiolo[3,2-d]pyrimidin-4-one Chemical compound C12=CC=CC=C2SC2=C1NC=NC2=O QFMSRGZWWJLTQE-UHFFFAOYSA-N 0.000 description 3
- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 0.000 description 3
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 3
- GRJAFENSUSLYET-UHFFFAOYSA-N 4-chloro-[1]benzothiolo[3,2-d]pyrimidine Chemical compound C12=CC=CC=C2SC2=C1N=CN=C2Cl GRJAFENSUSLYET-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VSCXBHMPGLUPIK-UHFFFAOYSA-N BrC1=CC=CC=2C3=CC=CC=C3N(C12)C=1C2=C(N=CN1)C1=C(O2)C=CC=C1 Chemical compound BrC1=CC=CC=2C3=CC=CC=C3N(C12)C=1C2=C(N=CN1)C1=C(O2)C=CC=C1 VSCXBHMPGLUPIK-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- DIBIMHRCSPYXGC-UHFFFAOYSA-N Fc1cccnc1-c1nc(Cl)ccc1I Chemical compound Fc1cccnc1-c1nc(Cl)ccc1I DIBIMHRCSPYXGC-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- HJQGCNQEOHKXCB-UHFFFAOYSA-N N1=C(C=CC2=C1C1=NC=CC=C1S2)Cl Chemical compound N1=C(C=CC2=C1C1=NC=CC=C1S2)Cl HJQGCNQEOHKXCB-UHFFFAOYSA-N 0.000 description 3
- KBPKGQGRSOXSAL-UHFFFAOYSA-N Nc1ccc(Cl)nc1-c1ncccc1F Chemical compound Nc1ccc(Cl)nc1-c1ncccc1F KBPKGQGRSOXSAL-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-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
- 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 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- CWPAZQRTFHRMQI-UHFFFAOYSA-N 6-chloro-2-iodopyridin-3-amine Chemical compound NC1=CC=C(Cl)N=C1I CWPAZQRTFHRMQI-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 101100232347 Mus musculus Il11ra1 gene Proteins 0.000 description 2
- OZJFYSUROVZUAH-UHFFFAOYSA-N N-phenyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzofuran-2-amine Chemical compound CC1(C)OB(OC1(C)C)c1cccc(c1)N(c1ccccc1)c1ccc2oc3ccccc3c2c1 OZJFYSUROVZUAH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
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- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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Abstract
Description
R1〜R8の少なくとも1つは、
式中、Lは、連結基であり、
mは、1又は0であり、
nは、1以上であり;
「Donor」は、少なくとも1つの電子供与性窒素を含む電子供与性基であり、nが1より大きいときは、複数の「Donor」は、異なっていてもよい。
他の材料との組合せ
HIL/HTL:
ホスト:
HBL:
ETL:
三つ口の1000mLのRBFを真空下で乾燥し、その後、イソプロピルマグネシウムクロライド(78mL、156mmol)を投入し、ウォーターバスで冷却した。温度が30℃を超えないように、2−ブロモ−3−フルオロピリジン(14.37mL、142mmol)を滴下した。反応生成物を室温で一晩撹拌し、その後、塩化亜鉛(II)(341mL、170mmol)で3時間以上滴下し、室温で一晩撹拌した。この懸濁液をその後、カニューレを介して、脱気された65℃の、テトラヒドロフラン(THF)(体積:474mL)中、Pd(PPh3)4(8.21g、7.10mmol)及び6−クロロ−2−ヨードピリジン−3−アミン(39.8g、156mmol)の溶液に添加し、一晩加熱還流した。室温まで溶液を冷却した後、反応物を飽和NaHCO3水溶液及び水でクエンチした。沈殿物を濾過し、EtOAcで洗浄した。濾液をEtOAcで抽出した。粗生成物を20%のTEA/ヘキサンで調節したカラムを用いて、40−50%EtOAc/ヘキサンによるカラムクロマトグラフィーにより精製し、6−クロロ−3’−フルオロ−[2,2’−ビピリジン]−3−アミン(21.8g、収率69%)を得た。
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 電子ブロッキング層
135 発光層
140 正孔ブロッキング層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 第一の導電層
164 第二の導電層
170 バリア層
200 反転させたOLED、デバイス
210 基板
215 カソード
220 発光層
225 正孔輸送層
230 アノード
Claims (5)
- 下記の式Iで表されることを特徴とする発光体。
Y1〜Y8の少なくとも2つは、Nであり;
Y1〜Y8の少なくとも1つは、C−Rであり;
Xは、O、S、又はSeであり;
各Rは、独立して、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルフォニル、ホスフィノ、及びこれらの組合せからなる群から選択され、前記Rの少なくとも1つは、下記から選択される基である。
(ただし、前記化合物が、前記式Iで表される化合物であって、
Y1〜Y4の少なくとも2つは、Nであり;
Y1〜Y4の少なくとも1つ、及びY5〜Y8のすべては、C−Rであり;かつ
Y1〜Y4の少なくとも1つのC−RにおけるRの少なくとも1つは、D144である場合を除く。) - 下記からなる群から選択される化合物である請求項1に記載の発光体。
(ただし、前記発光体が、式2〜4、9、10、又は14で表される化合物であり、かつR1〜R4の少なくとも1つはD144である場合を除く。) - 下記から選択される化合物である請求項1に記載の発光体。
- 有機発光デバイスを含むデバイスであって、前記有機発光デバイスは、
アノードと;
カソードと;
前記アノードと前記カソードとの間に配置された発光層と、を含み、
前記発光層が、請求項1に記載された発光体を含むことを特徴とするデバイス。 - 前記発光体が下記から選択される化合物である請求項4に記載のデバイス。
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Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105103327B (zh) | 2013-03-26 | 2018-09-07 | 株式会社半导体能源研究所 | 发光元件、化合物、有机化合物、显示模块、照明模块、发光装置、显示装置、照明装置以及电子设备 |
US9553274B2 (en) * | 2013-07-16 | 2017-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9293712B2 (en) * | 2013-10-11 | 2016-03-22 | Universal Display Corporation | Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same |
US20150102290A1 (en) * | 2013-10-11 | 2015-04-16 | Universal Display Corporation | Disubstituted pyrene compounds with amino group containing ortho aryl group |
KR20160007380A (ko) * | 2014-07-11 | 2016-01-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 화합물, 디스플레이 모듈, 조명 모듈, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기 |
JP6506534B2 (ja) | 2014-11-07 | 2019-04-24 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機電界発光素子用材料及びこれを用いた有機電界発光素子 |
CN113292572A (zh) * | 2015-09-04 | 2021-08-24 | 株式会社半导体能源研究所 | 化合物、发光元件、显示装置、电子设备及照明装置 |
US10651392B2 (en) | 2015-09-30 | 2020-05-12 | Samsung Electronics Co., Ltd. | Organic light-emitting device |
WO2017065295A1 (ja) * | 2015-10-15 | 2017-04-20 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および電子機器 |
CN108431010B (zh) | 2015-12-25 | 2021-10-15 | 株式会社半导体能源研究所 | 化合物、发光元件、显示装置、电子设备及照明装置 |
JP6687240B2 (ja) * | 2016-06-23 | 2020-04-22 | 国立大学法人北海道大学 | 新規化合物、化学センサー、センシング装置及びセンシング方法 |
KR102616441B1 (ko) | 2016-12-23 | 2023-12-26 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
TWI787279B (zh) | 2017-06-23 | 2022-12-21 | 日商半導體能源研究所股份有限公司 | 有機化合物、發光元件、發光裝置、電子裝置及照明設備 |
KR102630642B1 (ko) | 2018-02-09 | 2024-01-30 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 |
US11515486B2 (en) | 2018-07-03 | 2022-11-29 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
WO2020022579A1 (ko) | 2018-07-23 | 2020-01-30 | 삼성디스플레이주식회사 | 유기 발광 소자 |
US20220029111A1 (en) * | 2018-11-30 | 2022-01-27 | Semiconductor Energy Laboratory Co., Ltd. | Composition for Light-Emitting Device |
US20210395271A1 (en) * | 2018-11-30 | 2021-12-23 | Semiconductor Energy Laboratory Co., Ltd. | Composition for el device |
KR102661468B1 (ko) | 2019-02-15 | 2024-04-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함한 전자 장치 |
KR20210059153A (ko) | 2019-11-14 | 2021-05-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함한 장치 |
KR20210136224A (ko) | 2020-05-06 | 2021-11-17 | 삼성디스플레이 주식회사 | 발광 소자 및 이를 포함하는 전자 장치 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011084531A (ja) * | 2009-10-19 | 2011-04-28 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
WO2011137072A1 (en) * | 2010-04-26 | 2011-11-03 | Universal Display Corporation | Bicarbazole containing compounds for oleds |
JP2012515216A (ja) * | 2009-01-16 | 2012-07-05 | ユニバーサル ディスプレイ コーポレイション | Pholedのためのアザ−ジベンゾチオフェン又はアザ−ジベンゾフラン核をもつ新物質 |
Family Cites Families (128)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
EP0650955B1 (en) | 1993-11-01 | 1998-08-19 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
JPH07247288A (ja) | 1994-03-10 | 1995-09-26 | Takasago Internatl Corp | 2,3−ジシアノベンゾフロ[2,3−b]ピラジン誘導体及びその製造方法 |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
EP1325671B1 (en) | 2000-08-11 | 2012-10-24 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
WO2003001616A2 (en) | 2001-06-20 | 2003-01-03 | Showa Denko K.K. | Light emitting material and organic light-emitting device |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
US7431968B1 (en) | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
EP2261301A1 (en) | 2002-08-27 | 2010-12-15 | Fujifilm Corporation | Organometallic complexes, organic electroluminescent devices and organic electroluminescent displays |
US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
US7338722B2 (en) | 2003-03-24 | 2008-03-04 | The University Of Southern California | Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir |
US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
US7345301B2 (en) | 2003-04-15 | 2008-03-18 | Merck Patent Gmbh | Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures |
US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
US20060186791A1 (en) | 2003-05-29 | 2006-08-24 | Osamu Yoshitake | Organic electroluminescent element |
JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
EP2325191A1 (en) | 2004-03-11 | 2011-05-25 | Mitsubishi Chemical Corporation | Composition for charge-transporting film and ion compound, charge-transporting film and organic electroluminescent device using same |
TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
WO2005123873A1 (ja) | 2004-06-17 | 2005-12-29 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2006000544A2 (en) | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
EP2271183B1 (en) | 2004-07-23 | 2015-03-18 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminator |
DE102004057072A1 (de) | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
KR101272435B1 (ko) | 2004-12-30 | 2013-06-07 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 유기금속 착체 |
US8377571B2 (en) | 2005-02-04 | 2013-02-19 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device |
KR100803125B1 (ko) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
JP5125502B2 (ja) | 2005-03-16 | 2013-01-23 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子 |
DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5157442B2 (ja) | 2005-04-18 | 2013-03-06 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
EP2277978B1 (en) | 2005-05-31 | 2016-03-30 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
JP4976288B2 (ja) | 2005-06-07 | 2012-07-18 | 新日鐵化学株式会社 | 有機金属錯体及びこれを用いた有機電界発光素子 |
US7638072B2 (en) | 2005-06-27 | 2009-12-29 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
WO2007004380A1 (ja) | 2005-07-01 | 2007-01-11 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US20090295276A1 (en) | 2005-12-01 | 2009-12-03 | Tohru Asari | Organic Electroluminescent Device |
CN102633820B (zh) | 2005-12-01 | 2015-01-21 | 新日铁住金化学株式会社 | 有机电致发光元件用化合物及有机电致发光元件 |
ATE553111T1 (de) | 2006-02-10 | 2012-04-15 | Universal Display Corp | Metallkomplexe aus imidazoä1,2-füphenanthridin- liganden und deren verwendung in oled vorrichtungen |
JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
EP2639231B1 (en) | 2006-04-26 | 2019-02-06 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescence element using the same |
WO2007132678A1 (ja) | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子 |
EP2034538B1 (en) | 2006-06-02 | 2013-10-09 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence element, and organic electroluminescence element using the material |
JP5139297B2 (ja) | 2006-08-23 | 2013-02-06 | 出光興産株式会社 | 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
JP5589251B2 (ja) | 2006-09-21 | 2014-09-17 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料 |
WO2008056746A1 (fr) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
EP2518045A1 (en) | 2006-11-24 | 2012-10-31 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element using the same |
US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
DE602008004738D1 (de) | 2007-02-23 | 2011-03-10 | Basf Se | Elektrolumineszente metallkomplexe mit benzotriazolen |
CN101687893B (zh) | 2007-04-26 | 2014-01-22 | 巴斯夫欧洲公司 | 含有吩噻嗪s-氧化物或吩噻嗪s,s-二氧化物基团的硅烷及其在oled中的用途 |
WO2008156879A1 (en) | 2007-06-20 | 2008-12-24 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
EP2170911B1 (en) | 2007-06-22 | 2018-11-28 | UDC Ireland Limited | Light emitting cu(i) complexes |
WO2009003898A1 (de) | 2007-07-05 | 2009-01-08 | Basf Se | Organische leuchtdioden enthaltend carben-übergangsmetall-komplex-emitter und mindestens eine verbindung ausgewählt aus disilylcarbazolen; disilyldibenzofuranen, disilyldibenzothiophenen, disilyldibenzophospholen, disilyldibenzothiophen-s-oxiden und disilyldibenzothiophen-s,s-dioxiden |
US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
TW200911730A (en) | 2007-07-07 | 2009-03-16 | Idemitsu Kosan Co | Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
WO2009008205A1 (ja) | 2007-07-07 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料 |
JP5473600B2 (ja) | 2007-07-07 | 2014-04-16 | 出光興産株式会社 | クリセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
JPWO2009008099A1 (ja) | 2007-07-10 | 2010-09-02 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2009018009A1 (en) | 2007-07-27 | 2009-02-05 | E. I. Du Pont De Nemours And Company | Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles |
EP3159333B1 (en) | 2007-08-08 | 2020-04-22 | Universal Display Corporation | Benzo-fused thiophene or furan compounds comprising a triphenylene group |
JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
EP2203461B1 (de) | 2007-10-17 | 2011-08-10 | Basf Se | Übergangsmetallkomplexe mit verbrückten carbenliganden und deren verwendung in oleds |
US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
KR101353635B1 (ko) | 2007-11-15 | 2014-01-20 | 이데미쓰 고산 가부시키가이샤 | 벤조크리센 유도체 및 이것을 사용한 유기 전계 발광 소자 |
KR101583097B1 (ko) | 2007-11-22 | 2016-01-07 | 이데미쓰 고산 가부시키가이샤 | 유기 el 소자 및 유기 el 재료 함유 용액 |
KR20100106414A (ko) | 2007-11-22 | 2010-10-01 | 이데미쓰 고산 가부시키가이샤 | 유기 el 소자 |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
CN105859792A (zh) | 2008-02-12 | 2016-08-17 | 巴斯夫欧洲公司 | 具有二苯并[f,h]喹噁啉的电致发光金属络合物 |
KR101070223B1 (ko) * | 2009-05-14 | 2011-10-06 | 덕산하이메탈(주) | 아릴아미노 구조를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
JP5573066B2 (ja) | 2009-09-24 | 2014-08-20 | コニカミノルタ株式会社 | 有機光電変換素子と、それを用いた太陽電池及び光センサアレイ |
KR101788793B1 (ko) | 2010-12-24 | 2017-10-20 | 에스에프씨 주식회사 | 피리딘 유도체 화합물 및 이를 포함하는 유기전계발광소자 |
KR101840313B1 (ko) | 2011-02-14 | 2018-03-21 | 에스에프씨 주식회사 | 피리딘 유도체 화합물 및 이를 포함하는 유기전계발광소자 |
WO2013027633A1 (ja) | 2011-08-19 | 2013-02-28 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
US9685614B2 (en) * | 2012-01-10 | 2017-06-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element, and element using same |
US9553274B2 (en) * | 2013-07-16 | 2017-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2013
- 2013-07-16 US US13/942,879 patent/US9324949B2/en active Active
-
2014
- 2014-07-15 KR KR1020140088961A patent/KR102227407B1/ko active IP Right Grant
- 2014-07-16 JP JP2014146168A patent/JP6483366B2/ja active Active
-
2018
- 2018-12-11 JP JP2018231393A patent/JP6886451B2/ja active Active
-
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- 2021-03-02 KR KR1020210027764A patent/KR102379111B1/ko active IP Right Grant
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012515216A (ja) * | 2009-01-16 | 2012-07-05 | ユニバーサル ディスプレイ コーポレイション | Pholedのためのアザ−ジベンゾチオフェン又はアザ−ジベンゾフラン核をもつ新物質 |
JP2011084531A (ja) * | 2009-10-19 | 2011-04-28 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
WO2011137072A1 (en) * | 2010-04-26 | 2011-11-03 | Universal Display Corporation | Bicarbazole containing compounds for oleds |
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