JP6332904B2 - 新規有機発光材料 - Google Patents
新規有機発光材料 Download PDFInfo
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- JP6332904B2 JP6332904B2 JP2012268175A JP2012268175A JP6332904B2 JP 6332904 B2 JP6332904 B2 JP 6332904B2 JP 2012268175 A JP2012268175 A JP 2012268175A JP 2012268175 A JP2012268175 A JP 2012268175A JP 6332904 B2 JP6332904 B2 JP 6332904B2
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- 239000000463 material Substances 0.000 title description 57
- 150000001875 compounds Chemical class 0.000 claims description 62
- 239000003446 ligand Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- 150000002527 isonitriles Chemical class 0.000 claims description 15
- 150000002825 nitriles Chemical class 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 208000002925 dental caries Diseases 0.000 claims 1
- 239000010410 layer Substances 0.000 description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- -1 amino, silyl Chemical group 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 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
- 150000004820 halides Chemical class 0.000 description 14
- 125000004404 heteroalkyl group Chemical group 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 230000032258 transport Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- 125000003800 germyl group Chemical group [H][Ge]([H])([H])[*] 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 150000004696 coordination complex Chemical class 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 0 *(C(C12)[C@@]1C(C1)(C3)C2Oc2cccc4c2c3c1cc4)Oc(cc1)ccc1-c1ccccc1 Chemical compound *(C(C12)[C@@]1C(C1)(C3)C2Oc2cccc4c2c3c1cc4)Oc(cc1)ccc1-c1ccccc1 0.000 description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 7
- 229940093475 2-ethoxyethanol Drugs 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000000859 sublimation Methods 0.000 description 7
- 230000008022 sublimation Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229940126208 compound 22 Drugs 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- CESZJQXARBXWET-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)isoquinoline iridium Chemical class [Ir].CC1=CC(C)=CC(C=2C3=CC=CC=C3C=CN=2)=C1 CESZJQXARBXWET-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- PPEPCRUWMIVQRK-UHFFFAOYSA-N 4,6-dichloro-2h-isoquinolin-1-one Chemical compound ClC1=CC=C2C(O)=NC=C(Cl)C2=C1 PPEPCRUWMIVQRK-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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-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
- 125000004122 cyclic group Chemical group 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- QLPUTPLSFBYUJO-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-n-(2,2-diethoxyethyl)methanimine Chemical compound CCOC(OCC)CN=CC1=CC(Cl)=CC(Cl)=C1 QLPUTPLSFBYUJO-UHFFFAOYSA-N 0.000 description 3
- PUFUMWBNIQYDCW-UHFFFAOYSA-N 4,6-dichloro-1-(3,5-dimethylphenyl)isoquinoline Chemical compound CC1=CC(C)=CC(C=2C3=CC=C(Cl)C=C3C(Cl)=CN=2)=C1 PUFUMWBNIQYDCW-UHFFFAOYSA-N 0.000 description 3
- VRVMBIZATLJJFO-UHFFFAOYSA-N 4-chloro-2-methylbenzamide Chemical compound CC1=CC(Cl)=CC=C1C(N)=O VRVMBIZATLJJFO-UHFFFAOYSA-N 0.000 description 3
- ZKGMMYWJFPYTGQ-UHFFFAOYSA-N 4-chloro-2-methylbenzoyl chloride Chemical compound CC1=CC(Cl)=CC=C1C(Cl)=O ZKGMMYWJFPYTGQ-UHFFFAOYSA-N 0.000 description 3
- AASHMYKHSULUKP-UHFFFAOYSA-N 4-chloro-n-(dimethylaminomethylidene)-2-methylbenzamide Chemical compound CN(C)C=NC(=O)C1=CC=C(Cl)C=C1C AASHMYKHSULUKP-UHFFFAOYSA-N 0.000 description 3
- LRTAHCUSBZEOBO-UHFFFAOYSA-N 5,7-dichloroisoquinoline Chemical compound C1=CN=CC2=CC(Cl)=CC(Cl)=C21 LRTAHCUSBZEOBO-UHFFFAOYSA-N 0.000 description 3
- AVLGVJHAZWURPZ-UHFFFAOYSA-N 6-chloro-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C=2C1=CC(Cl)=CC=2 AVLGVJHAZWURPZ-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000004128 high performance liquid chromatography 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
- 229910052741 iridium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000002207 thermal evaporation Methods 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
- QJDBRKZQCMWDKJ-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-5,7-bis(2-methylpropyl)isoquinoline Chemical compound C12=CC(CC(C)C)=CC(CC(C)C)=C2C=CN=C1C1=CC(C)=CC(C)=C1 QJDBRKZQCMWDKJ-UHFFFAOYSA-N 0.000 description 2
- RJIXGOTXIQIMLC-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-5,7-di(propan-2-yl)isoquinoline Chemical compound C12=CC(C(C)C)=CC(C(C)C)=C2C=CN=C1C1=CC(C)=CC(C)=C1 RJIXGOTXIQIMLC-UHFFFAOYSA-N 0.000 description 2
- VXDCTHXEYMTMID-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)isoquinoline Chemical compound CC1=CC(C)=CC(C=2C3=CC=CC=C3C=CN=2)=C1 VXDCTHXEYMTMID-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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-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
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- ZEAYJYJKQFXPNY-UHFFFAOYSA-N 5,7-bis(2-methylpropyl)isoquinoline Chemical compound C1=CN=CC2=CC(CC(C)C)=CC(CC(C)C)=C21 ZEAYJYJKQFXPNY-UHFFFAOYSA-N 0.000 description 2
- LHXUFSZCKKLWHT-UHFFFAOYSA-N 5,7-bis(prop-1-en-2-yl)isoquinoline Chemical compound C1=CN=CC2=CC(C(=C)C)=CC(C(C)=C)=C21 LHXUFSZCKKLWHT-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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- 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
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Description
有機発光デバイスにおける特定の層に有用である、本明細書に記載の材料は、デバイスに存在する種々の他の材料と組み合わせて用いられてよい。例えば、本明細書に開示されている発光ドーパントは、存在していてよい種々のホスト、輸送層、ブロック層、注入層、電極および他の層と併せて用いられてよい。以下に記載または称される材料は、本明細書に開示されている化合物と組み合わせて有用であり得る材料の非限定的な例であり、当業者は、組み合わせて有用であり得る他の材料を特定するための文献を容易に閲覧することができる。
本発明において用いられる正孔注入/輸送材料は特に限定されず、正孔注入/輸送材料として典型的に用いられる限りにおいていずれの化合物が用いられてもよい。材料の例として、限定されないが:フタロシアニンまた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;フッ化炭化水素を含有するポリマー;導電ドーパントを有するポリマー;導電性ポリマー、例えばPEDOT/PSS;ホスホン酸およびシラン誘導体などの化合物から誘導される自己集合モノマー;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、ならびに架橋性化合物が挙げられる。
本発明の有機ELデバイスの発光層は、発光材料として少なくとも金属錯体を好ましくは含有し、ドーパント材料として金属錯体を用いたホスト材料を含有していてもよい。ホスト材料の例は、特に限定されず、ホストの三重項エネルギーがドーパントの三重項エネルギーよりも大きい限りにおいて、いずれの金属錯体または有機化合物が用いられてもよい。以下の表は、種々の色を発するデバイスに好ましいとされるホスト材料を分類するが、三重項の基準が満たされる限りにおいて、いずれのホスト材料がいずれのドーパントと共に用いられてもよい。
正孔ブロック層(HBL)は、発光層を離れる正孔および/または励起子の数を低減するのに用いられ得る。デバイスにおいてかかるブロック層が存在することで、ブロック層を欠く同様のデバイスと比較して実質的により高い効率をもたらし得る。また、ブロック層は、発光をOLEDの所望の領域に制限するのに用いられ得る。
電子輸送層(ETL)は、電子を輸送することが可能である材料を含んでいてよい。電子輸送層は、固有のもの(非ドープ)であっても、ドープされていてもよい。ドーピングは、導電率を向上させるのに用いられ得る。ETL材料の例は特に限定されず、電子を輸送するのに典型的に用いられる限りにおいて、いずれの金属錯体または有機化合物が用いられてもよい。
Claims (12)
- nが2である、請求項1に記載の化合物。
- Lがモノアニオン性二座配位子である、請求項1に記載の化合物。
- Rx、Ry、およびRzが、アルキル、水素、重水素、およびこれらの組み合わせからなる群から独立して選択される、請求項4に記載の化合物。
- Rzが水素または重水素であり、RxおよびRyがメチル、CH(CH3)2、及びCH2CH(CH3)2からなる群から独立して選択される、請求項5に記載の化合物。
- アノードと;
カソードと;
アノードとカソードとの間に配置された有機層を含み、
前記有機層が、請求項1〜7のいずれか一項に記載の化合物を含む、有機発光デバイス。 - フラットパネルディスプレイ、コンピュータモニタ、医療モニタ、テレビ、広告板、室内また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、可撓性ディスプレイ、レーザプリンタ、電話機、携帯電話、携帯情報端末(PDA)、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、マイクロディスプレイ、乗物、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、請求項8に記載の有機発光デバイスが組み込まれた消費者製品。
- 前記有機層が、ホストをさらに含む、請求項8に記載の有機発光デバイス。
- 前記ホストが、金属8−ヒドロキシキノレートである、請求項10に記載の有機発光デバイス。
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US13/316,162 | 2011-12-09 | ||
US13/316,162 US9512355B2 (en) | 2011-12-09 | 2011-12-09 | Organic light emitting materials |
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JP2016198043A Division JP6426676B2 (ja) | 2011-12-09 | 2016-10-06 | 新規有機発光材料 |
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JP2013121957A JP2013121957A (ja) | 2013-06-20 |
JP6332904B2 true JP6332904B2 (ja) | 2018-05-30 |
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JP2012268175A Active JP6332904B2 (ja) | 2011-12-09 | 2012-12-07 | 新規有機発光材料 |
JP2016198043A Active JP6426676B2 (ja) | 2011-12-09 | 2016-10-06 | 新規有機発光材料 |
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US (3) | US9512355B2 (ja) |
EP (1) | EP2602302B1 (ja) |
JP (2) | JP6332904B2 (ja) |
KR (2) | KR102148532B1 (ja) |
CN (2) | CN108358975A (ja) |
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- 2012-12-07 TW TW107121163A patent/TW201920599A/zh unknown
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TW201920599A (zh) | 2019-06-01 |
EP2602302A2 (en) | 2013-06-12 |
TWI642758B (zh) | 2018-12-01 |
US9512355B2 (en) | 2016-12-06 |
EP2602302A3 (en) | 2015-01-28 |
US20170047531A1 (en) | 2017-02-16 |
JP6426676B2 (ja) | 2018-11-21 |
US10454046B2 (en) | 2019-10-22 |
TWI591155B (zh) | 2017-07-11 |
KR20190088453A (ko) | 2019-07-26 |
CN103159798A (zh) | 2013-06-19 |
JP2017014275A (ja) | 2017-01-19 |
KR102148532B1 (ko) | 2020-08-27 |
TW201329203A (zh) | 2013-07-16 |
CN108358975A (zh) | 2018-08-03 |
US11482684B2 (en) | 2022-10-25 |
EP2602302B1 (en) | 2016-06-29 |
JP2013121957A (ja) | 2013-06-20 |
US20200006675A1 (en) | 2020-01-02 |
US20130146848A1 (en) | 2013-06-13 |
KR20130065595A (ko) | 2013-06-19 |
TW201728742A (zh) | 2017-08-16 |
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