JP6538460B2 - 有機エレクトロルミネッセンス材料及びデバイス - Google Patents
有機エレクトロルミネッセンス材料及びデバイス Download PDFInfo
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- JP6538460B2 JP6538460B2 JP2015136658A JP2015136658A JP6538460B2 JP 6538460 B2 JP6538460 B2 JP 6538460B2 JP 2015136658 A JP2015136658 A JP 2015136658A JP 2015136658 A JP2015136658 A JP 2015136658A JP 6538460 B2 JP6538460 B2 JP 6538460B2
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- Prior art keywords
- compound
- biphenyl
- group
- phenyl
- mmol
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- 239000000463 material Substances 0.000 title description 98
- 150000001875 compounds Chemical class 0.000 claims description 294
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 96
- 239000000203 mixture Substances 0.000 claims description 92
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 66
- -1 aza-dibenzofuran Chemical compound 0.000 claims description 60
- 235000010290 biphenyl Nutrition 0.000 claims description 48
- 239000004305 biphenyl Substances 0.000 claims description 45
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 33
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 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 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 239000012044 organic layer Substances 0.000 claims description 24
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 24
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 23
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 150000002825 nitriles Chemical class 0.000 claims description 15
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 8
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- PFWJFKBTIBAASX-UHFFFAOYSA-N 9h-indeno[2,1-b]pyridine Chemical compound C1=CN=C2CC3=CC=CC=C3C2=C1 PFWJFKBTIBAASX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 270
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 146
- 238000003786 synthesis reaction Methods 0.000 description 117
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 116
- 230000015572 biosynthetic process Effects 0.000 description 116
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
- 239000007787 solid Substances 0.000 description 98
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- 239000010410 layer Substances 0.000 description 93
- 239000000243 solution Substances 0.000 description 82
- 229910052757 nitrogen Inorganic materials 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- 238000001816 cooling Methods 0.000 description 68
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 51
- 238000000151 deposition Methods 0.000 description 47
- 239000002904 solvent Substances 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
- 238000001914 filtration Methods 0.000 description 38
- 230000008021 deposition Effects 0.000 description 37
- 239000000741 silica gel Substances 0.000 description 37
- 229910002027 silica gel Inorganic materials 0.000 description 37
- 238000001704 evaporation Methods 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 230000008020 evaporation Effects 0.000 description 33
- 239000003480 eluent Substances 0.000 description 31
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 29
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000010898 silica gel chromatography Methods 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- 239000003446 ligand Substances 0.000 description 23
- 238000004128 high performance liquid chromatography Methods 0.000 description 21
- 238000009835 boiling Methods 0.000 description 20
- 239000012043 crude product Substances 0.000 description 20
- 239000000758 substrate Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 230000032258 transport Effects 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 230000004888 barrier function Effects 0.000 description 11
- 238000010549 co-Evaporation Methods 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 150000002527 isonitriles Chemical class 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 150000004696 coordination complex Chemical class 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 125000004404 heteroalkyl group Chemical group 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 5
- NTEIZPBYXABJKN-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 NTEIZPBYXABJKN-UHFFFAOYSA-N 0.000 description 5
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 235000011056 potassium acetate Nutrition 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- FNKCOUREFBNNHG-UHFFFAOYSA-N 1,3-dibromo-5-chlorobenzene Chemical compound ClC1=CC(Br)=CC(Br)=C1 FNKCOUREFBNNHG-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
- YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 description 4
- LWKKRKCKDWPJPG-UHFFFAOYSA-N 2-chloro-4,6-bis(3-chlorophenyl)-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC(=CC=C1)Cl)C1=CC(=CC=C1)Cl LWKKRKCKDWPJPG-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002253 acid Substances 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
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 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
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000002207 thermal evaporation Methods 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-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
- RLMXQZYWLSTOBA-UHFFFAOYSA-N 2-(3-bromo-5-chlorophenyl)-9,9-dimethylfluorene Chemical compound BrC=1C=C(C=C(C=1)Cl)C1=CC=2C(C3=CC=CC=C3C=2C=C1)(C)C RLMXQZYWLSTOBA-UHFFFAOYSA-N 0.000 description 3
- OVNPUJOZNPAVJQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 OVNPUJOZNPAVJQ-UHFFFAOYSA-N 0.000 description 3
- OUPMUGIXWNVDSN-UHFFFAOYSA-N 2-[hydroxy-(1-oxido-4-oxoquinoxalin-4-ium-2-yl)methyl]-4-methoxyphenol Chemical compound COC1=CC=C(O)C(C(O)C=2N(C3=CC=CC=C3[N+](=O)C=2)[O-])=C1 OUPMUGIXWNVDSN-UHFFFAOYSA-N 0.000 description 3
- WYUYQFQDVPVKBD-UHFFFAOYSA-N 2-chloro-4-(9,9-dimethylfluoren-2-yl)-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=2C(C3=CC=CC=C3C=2C=C1)(C)C)C1=CC=CC=C1 WYUYQFQDVPVKBD-UHFFFAOYSA-N 0.000 description 3
- SKNADSBKOSKSNG-UHFFFAOYSA-N 2-chloro-4-dibenzothiophen-4-yl-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC2=C1SC1=C2C=CC=C1)C1=CC=CC=C1 SKNADSBKOSKSNG-UHFFFAOYSA-N 0.000 description 3
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 3
- AQHYITKXJMPSHI-UHFFFAOYSA-N 4-(3-bromo-5-chlorophenyl)dibenzothiophene Chemical compound BrC=1C=C(C=C(C=1)Cl)C1=CC=CC2=C1SC1=C2C=CC=C1 AQHYITKXJMPSHI-UHFFFAOYSA-N 0.000 description 3
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- NVGRDODNVUQSKP-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[3-(4-phenylphenyl)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 NVGRDODNVUQSKP-UHFFFAOYSA-N 0.000 description 1
- IVLWVZMFDFZOPL-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[3-phenyl-5-(6-phenyldibenzothiophen-4-yl)phenyl]-1,3,2-dioxaborolane Chemical compound CC1(OB(OC1(C)C)C=1C=C(C=C(C=1)C1=CC=CC2=C1SC1=C2C=CC=C1C1=CC=CC=C1)C1=CC=CC=C1)C IVLWVZMFDFZOPL-UHFFFAOYSA-N 0.000 description 1
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- IYURETRCCXGHQA-UHFFFAOYSA-N 4-(4-chlorophenyl)dibenzothiophene Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC2=C1SC1=CC=CC=C21 IYURETRCCXGHQA-UHFFFAOYSA-N 0.000 description 1
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- FBTSSHSQSPYTJQ-UHFFFAOYSA-N 4-iododibenzoselenophene Chemical compound [se]1C2=CC=CC=C2C2=C1C(I)=CC=C2 FBTSSHSQSPYTJQ-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- IBUHPAMYSPQKBF-UHFFFAOYSA-N CC1(C2=CC=CC=C2C3=C1C=C(C=C3)C4=NC(=NC=N4)C5=CC6=C(C=C5)C7=CC=CC=C7C6(C)C)C Chemical compound CC1(C2=CC=CC=C2C3=C1C=C(C=C3)C4=NC(=NC=N4)C5=CC6=C(C=C5)C7=CC=CC=C7C6(C)C)C IBUHPAMYSPQKBF-UHFFFAOYSA-N 0.000 description 1
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- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 1
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- FFKVQWCVNYVFQJ-UHFFFAOYSA-N [B]C1=CC=CC(C2=CC=C3)=C1SC2=C3C1=CC=CC=C1 Chemical compound [B]C1=CC=CC(C2=CC=C3)=C1SC2=C3C1=CC=CC=C1 FFKVQWCVNYVFQJ-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- QPJFIVIVOOQUKD-UHFFFAOYSA-N dipyrazino[2,3-f:2,3-h]quinoxaline Chemical group C1=CN=C2C3=NC=CN=C3C3=NC=CN=C3C2=N1 QPJFIVIVOOQUKD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- ANCBHJKEYPZCTE-UHFFFAOYSA-N ethyl 5-carbamoyl-4-methyl-2-[(2,3,4,5,6-pentafluorobenzoyl)amino]thiophene-3-carboxylate Chemical compound CC1=C(C(N)=O)SC(NC(=O)C=2C(=C(F)C(F)=C(F)C=2F)F)=C1C(=O)OCC ANCBHJKEYPZCTE-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZMPYQGQHGLLBQI-UHFFFAOYSA-M magnesium;chlorobenzene;bromide Chemical compound [Mg+2].[Br-].ClC1=CC=C[C-]=C1 ZMPYQGQHGLLBQI-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- RIYPENPUNLHEBK-UHFFFAOYSA-N phenanthro[9,10-b]pyridine Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 RIYPENPUNLHEBK-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical group 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
- 238000003466 welding Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Description
本願は、その開示内容の全体を参照によって援用する、2014年7月9日出願の米国特許出願第62/022,300、2014年8月19日出願の米国特許出願第62/038,925、2014年10月6日出願の米国特許出願第62/060,192、及び2014年11月24日出願の米国特許出願第62/083,490の非仮出願である。
L1、L2、及びL3は、それぞれ独立して、直接的な結合、フェニル、ビフェニル、ターフェニル、ピリジン、ピリミジン、及びこれらの組合せからなる群から選択され;
G4は、フェニル、ビフェニル、ターフェニル、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、及びこれらの組合せからなる群から選択され;
G2、G3、及びG5は、それぞれ独立して、フェニル、ビフェニル、ターフェニル、フルオレン、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、アザ−フルオレン、及びこれらの組合せからなる群から選択され;
G2、G3、G4、及びG5は、それぞれ、重水素、アルキル、アルコキシル、シクロアルキル、シクロアルコキシル、ハロゲン、ニトロ、ニトリル、シリル、フェニル、ビフェニル、ターフェニル、ピリジン、及びこれらの組合せからなる群から選択される1つ以上の非縮合置換基で更に置換されていてもよく;
mは、0から7までの整数であり;
nは、0から4までの整数であり;
m又はnが1よりも大きいとき、G4又はG5は、それぞれ同一であっても異なっていてもよく;
nが0のとき、mは1以上であり、G4はそれぞれフェニル及びビフェニルからなる群から選択され;
nが1以上のとき、L1は、直接的な結合ではなく;
m及びnがいずれも0であるとき、L1は、ビフェニルである。
LA及びLBは、直接的な結合、フェニル、ビフェニル、ピリジン、及びこれらの組合せからなる群から選択され;
GA及びGBは、フェニル、ビフェニル、ピリジン、ジベンゾチオフェン、ジベンゾフラン、ジベンゾセレノフェン、及びフルオレンからなる群から選択され;
GA及びGBは、それぞれ、重水素、アルキル、アルコキシル、シクロアルキル、シクロアルコキシル、ハロゲン、ニトロ、ニトリル、シリル、フェニル、ビフェニル、ターフェニル、ピリジン、及びこれらの組合せからなる群から選択される1つ以上の非縮合置換基で更に置換されていてもよい。
G1は、ジベンゾフラン、ジベンゾチオフェン、ジベンゾセレノフェン、及びフルオレンからなる群から選択され;
L1、L2、及びL3は、それぞれ独立して、直接的な結合、フェニル、ビフェニル、ターフェニル、ピリジン、ピリミジン、及びこれらの組合せからなる群から選択され;
G4は、フェニル、ビフェニル、ターフェニル、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、及びこれらの組合せからなる群から選択され;
G2、G3、及びG5は、それぞれ独立して、フェニル、ビフェニル、ターフェニル、フルオレン、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、アザ−フルオレン、及びこれらの組合せからなる群から選択され;
G2、G3、G4、及びG5は、それぞれ、重水素、アルキル、アルコキシル、シクロアルキル、シクロアルコキシル、ハロゲン、ニトロ、ニトリル、シリル、フェニル、ビフェニル、ターフェニル、ピリジン、及びこれらの組合せからなる群から選択される1つ以上の非縮合置換基で更に置換されていてもよく;
mは、0から7までの整数であり;
nは、0から4までの整数であり;
m又はnが1よりも大きいとき、G4又はG5は、それぞれ同一であっても異なっていてもよく;
nが0のとき、mは1以上であり、G4はそれぞれフェニル及びビフェニルからなる群から選択され;
nが1以上のとき、L1は、直接的な結合ではなく;
m及びnがいずれも0であるとき、L1は、ビフェニルである。
RB1及びRB2は、独立して、水素、重水素、アルキル、シクロアルキル、アルコキシル、アリール、ヘテロアリール、ハロゲン、及びこれらの組合せからなる群から選択され;
RB1及びRB2は、結合して環を形成してもよい。
RB1及びRB2は、結合して環を形成してもよい。
Ar1は、トリフェニレン及びアザ−トリフェニレンからなる群から選択され;
Ar2は、直接的な結合、フェニル、ビフェニル、ターフェニル、ナフタレン、ピリジン、ジベンゾフラン、ジベンゾチオフェン、ジベンゾセレノフェン、アザ−ジベンゾフラン、アザ−ジベンゾチオフェン、アザ−ジベンゾセレノフェン、及びこれらの組合せからなる群から選択され;
Ar3は、ベンゼン、ビフェニル、ターフェニル、ナフタレン、ピリジン、ジベンゾフラン、ジベンゾチオフェン、ジベンゾセレノフェン、アザ−ジベンゾフラン、アザ−ジベンゾチオフェン、アザ−ジベンゾセレノフェン、カルバゾール、アザ−カルバゾール、及びこれらの組合せからなる群から選択され;
Ar1、Ar2、及びAr3は、それぞれ独立して、重水素、ハロゲン、アルキル、アリール、ヘテロアリール,及びこれらの組合せからなる群から選択される1つ以上の置換基で更に置換されていてもよい。
R1及びR4は、それぞれ独立して、モノ、ジ、トリ、置換を表すか、又は無置換であり;
R2、R3、R5、及びR6は、それぞれ独立して、モノ、ジ、トリ、テトラ置換を表すか、又は無置換であり;
R1〜R6は、それぞれ独立して、水素、重水素、ベンゼン、ビフェニル、ターフェニル、ナフタレン、フルオレン、トリフェニレン、フェナントレン、ジベンゾフラン、ジベンゾチオフェン、カルバゾール、及びこれらの組合せからなる群から選択される。
LA及びLBは、直接的な結合、フェニル、ビフェニル、ピリジン、及びこれらの組合せからなる群から選択され;
GA及びGBは、フェニル、ビフェニル、ピリジン、ジベンゾチオフェン、ジベンゾフラン、ジベンゾセレノフェン、及びフルオレンからなる群から選択され;
GA及びGBは、それぞれ、重水素、アルキル、アルコキシル、シクロアルキル、シクロアルコキシル、ハロゲン、ニトロ、ニトリル、シリル、フェニル、ビフェニル、ターフェニル、ピリジン、及びこれらの組合せからなる群から選択される1つ以上の非縮合置換基で更に置換されていてもよい。
Xは、BR’、NR’、PR’、O、S、Se、C=O、S=O、SO2、CR’R’’、SiR’R’’、及びGeR’R’’からなる群から選択され;
R’及びR’’は、縮合又は結合して環を形成してもよく;
Ra、Rb、Rc、及びRdは、それぞれモノ置換から可能な最も多い数の置換、又は無置換を表すことができ;
R’、R’’、Ra、Rb、Rc、及びRdは、それぞれ独立して、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;
Ra、Rb、Rc、及びRdのうち任意の2つの隣接する置換基は、縮合又は結合して、環を形成する、又は多座配位子を形成してもよい。
他の材料との組合せ
HIL/HTL:
式中、kは1から20までの整数であり;X101からX108はC(CHを含む)又はNであり;Z101はNAr1、O、又はSであり;Ar1は、上記で定義したものと同じ基を有する。
ホスト:
HBL:
ETL:
本明細書で使用されている化学略語は、下記の通りである。
SPhosは、ジシクロヘキシル(2’,6’−ジメトキシ−[1,1’−ビフェニル]−2−イル)ホスフィンである。
Pd2(dba)3は、トリ(ジベンジリデンアセトン)ジパラジウム(0)である。
Pd(PPh3)4は、テトラキス(トリフェニルホスフィン)パラジウム(0)である。
DCMは、ジクロロメタンである。
EtOAcは、酢酸エチルである。
DMEは、ジメトキシエタンである。
THFは、テトラヒドロフランである。
化合物A5の合成
化合物A11の合成
化合物A17の合成
化合物A32の合成
化合物A35の合成
化合物A38の合成
化合物A41の合成
化合物A47の合成
化合物A110の合成
化合物A113の合成
化合物A116の合成
化合物B3の合成
化合物B6の合成
化合物B7の合成
化合物C21の合成
化合物C23の合成
化合物C29の合成
化合物C47の合成
化合物C56の合成
化合物C65の合成
化合物C68の合成
化合物C71の合成
化合物C73の合成
化合物C74の合成
化合物C75の合成
化合物C83の合成
化合物C101の合成
化合物C110の合成
化合物C119の合成
化合物C131の合成
化合物C134の合成
化合物C139の合成
化合物C173の合成
化合物C185の合成
化合物C251の合成
化合物C254の合成
化合物D1の合成
化合物D2の合成
化合物F1の合成
化合物F2の合成
化合物F3の合成
化合物F4の合成
化合物F7の合成
化合物F13の合成
デバイス実施例
デバイスはいずれも、高真空下(約10−7Torr)における熱蒸着で作製した。アノード電極は、80nmの酸化インジウムスズ(ITO)である。カソード電極は、1nmのLiFと、100nmのAlとからなった。デバイスはいずれも、作製後すぐに、窒素グローブボックス(H2O及びO2は、<1ppm)中で、エポキシ樹脂で封止したガラス製の蓋で封入し、水分ゲッターをパッケージに入れた。
デバイス実施例の第1のセットは、ITO表面から順に、正孔注入層(HIL)として10nmのLG101(LG Chemから)、正孔輸送層(HTL)として45nmの4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノビフェニル(NPD)、発光層(EML)として、30nmの化合物E8と20重量%の本願発明化合物(化合物C65)又は比較化合物(CC−1)、及び10重量%の発光体GDとからなる有機積層体を有する。前記EMLの上に、正孔ブロッキング層(HBL)として、50nmの化合物C65又はCC−1、電子輸送層(ETL)として、40nmのトリス(8−ヒドロキシキノリナト)アルミニウム(Alq3)を堆積した。使用された化合物の構造は、下記に示される。
デバイス実施例の第2のセットは、15%のGDでドープした本願発明化合物C101又は比較化合物CC−2を2成分EMLとして用いた以外は、デバイス実施例1と同様の構造を有する。使用される本願発明化合物及び比較化合物の化学構造は、下記に示される。
デバイス実施例の第3のセットは、デバイス実施例1におけるセットと同様の構造を有する。使用される本願発明化合物及び比較化合物の化学構造は、下記に示される。
デバイスの第4のセットは、デバイス実施例2におけるセットと同様の構造を有する。使用される本願発明化合物及び比較化合物の化学構造は、下記に示される。
デバイスの第5のセットは、デバイス実施例1におけるセットと同様の構造を有する。使用される本願発明化合物及び比較化合物の化学構造は、下記に示される。
予混合実施例
予混合物PM−A4について、化合物E8及び化合物C74を7:3の重量比で準備し、その後物理的に混合、粉砕し、蒸着源に装填した。真空チャンバー内で、2Å/sの速度、10−7Torr未満の圧力下で予混合組成物を熱的に共蒸着し、ガラス基板上に堆積した。500Åの膜の堆積後、堆積の停止及び蒸着源を冷却せずに、基板を連続的に取り替えた。膜の組成物を高速液体クロマトグラフィー(HPLC)で分析し、結果は表PM2に示される。
予混合物PM−A12について、化合物E26及び化合物C74を3:2の重量比で準備し、その後物理的に混合、粉砕し、蒸着源に装填した。真空チャンバー内で、2Å/sの速度、10−7Torr未満の圧力下で予混合組成物を熱的に共蒸着し、ガラス基板上に堆積した。500Åの膜の堆積後、堆積の停止及び蒸着源を冷却せずに、基板を連続的に取り替えた。膜の組成物を高速液体クロマトグラフィー(HPLC)で分析し、結果は表PM3に示される。
予混合物PM−A16について、化合物E30及び化合物C74を1:1の重量比で準備し、その後物理的に混合、粉砕し、蒸着源に装填した。真空チャンバー内で、2Å/秒の速度、10−7Torr未満の圧力下で予混合組成物を熱的に共蒸着し、ガラス基板上に堆積した。500Åの膜の堆積後、堆積の停止及び蒸着源を冷却せずに、基板を連続的に取り替えた。膜の組成物を高速液体クロマトグラフィー(HPLC)で分析し、結果は表PM4に示される。
予混合物PM−B3について、化合物G8及び化合物F13を9:1の重量比で準備し、その後物理的に混合、粉砕し、蒸着源に装填した。真空チャンバー内で、2Å/秒の速度、10−7Torr未満の圧力下で予混合組成物を熱的に共蒸着し、ガラス基板上に堆積した。500Åの膜の堆積後、堆積の停止及び蒸着源を冷却せずに、基板を連続的に取り替えた。材料がなくなったら堆積を停止した。膜の組成物を高速液体クロマトグラフィー(HPLC)で分析し、結果は表PM6に示される。
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 (6)
- 第1の化合物、及び第2の化合物を含む、材料の組成物であって、
前記第1の化合物が式Iで表され、第2の化合物が式IIで表されることを特徴とする組成物。
L1、L2、及びL3は、それぞれ独立して、直接的な結合、フェニル、ビフェニル、ターフェニル、ピリジン、ピリミジン、及びこれらの組合せからなる群から選択され;
G4は、フェニル、ビフェニル、ターフェニル、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、及びこれらの組合せからなる群から選択され;
G2、G3、及びG5は、それぞれ独立して、フェニル、ビフェニル、ターフェニル、フルオレン、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、アザ−フルオレン、及びこれらの組合せからなる群から選択され;
G2、G3、G4、及びG5は、それぞれ、重水素、アルキル、アルコキシル、シクロアルキル、シクロアルコキシル、ハロゲン、ニトロ、ニトリル、シリル、フェニル、ビフェニル、ターフェニル、ピリジン、及びこれらの組合せからなる群から選択される1つ以上の非縮合置換基で更に置換されていてもよく;
mは、0から7までの整数であり;
nは、0から4までの整数であり;
m又はnが1よりも大きいとき、G4又はG5は、それぞれ同一であっても異なっていてもよく;
nが0で、mが1以上であるとき、G4はそれぞれフェニル及びビフェニルからなる群から選択され;
nが1以上のとき、L1は、直接的な結合ではなく;
m及びnがいずれも0であるとき、L1は、ビフェニルである。)
Ar 2 は、直接的な結合、フェニル、ビフェニル、ターフェニル、ナフタレン、ピリジン、ジベンゾフラン、ジベンゾチオフェン、ジベンゾセレノフェン、アザ−ジベンゾフラン、アザ−ジベンゾチオフェン、アザ−ジベンゾセレノフェン、及びこれらの組合せからなる群から選択され;
Ar 3 は、ベンゼン、ビフェニル、ターフェニル、ナフタレン、ピリジン、ジベンゾフラン、ジベンゾチオフェン、ジベンゾセレノフェン、アザ−ジベンゾフラン、アザ−ジベンゾチオフェン、アザ−ジベンゾセレノフェン、カルバゾール、アザ−カルバゾール、及びこれらの組合せからなる群から選択され;
Ar 1 、Ar 2 、及びAr 3 は、それぞれ独立して、重水素、ハロゲン、アルキル、アリール、ヘテロアリール,及びこれらの組合せからなる群から選択される1つ以上の置換基で更に置換されていてもよい。) - 第1の化合物が下記からなる群から選択される請求項1に記載の組成物。
- 式Iで表されることを特徴とする第1の化合物。
L 1 、L 2 、及びL 3 は、直接的な結合、フェニル、ビフェニル、ターフェニル、ピリジン、ピリミジン、及びこれらの組合せからなる群から選択され;
G 4 は、フェニル、ビフェニル、ターフェニル、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、及びこれらの組合せからなる群から選択され;
G 2 、G 3 、及びG 5 は、それぞれ独立して、フェニル、ビフェニル、ターフェニル、フルオレン、ナフタレン、フェナントレン、ピリジン、ピリミジン、ピラジン、キノリン、イソキノリン、フェナントロリン、アザ−フルオレン、及びこれらの組合せからなる群から選択され;
G 2 、G 3 、G 4 、及びG 5 は、それぞれ、重水素、アルキル、アルコキシル、シクロアルキル、シクロアルコキシル、ハロゲン、ニトロ、ニトリル、シリル、フェニル、ビフェニル、ターフェニル、ピリジン、及びこれらの組合せからなる群から選択される1つ以上の非縮合置換基で更に置換されていてもよく;
mは、0から7までの整数であり;
nは、0から4までの整数であり;
m又はnが1よりも大きいとき、G 4 又はG 5 は、それぞれ同一であっても異なっていてもよく;
nが0で、mが1以上であるとき、G 4 はそれぞれフェニル及びビフェニルからなる群から選択され;
nが1以上のとき、L 1 は、直接的な結合ではなく;
m及びnがいずれも0であるとき、L 1 は、ビフェニルである。)
(ただし、前記第一の化合物が、L 1 が直接的な結合かつG 1 がフルオレンである化合物;L 1 がフェニル且つG 1 がジベンゾフラン、ジベンゾチオフェン、又はフルオレンである化合物;又はL 1 がビフェニル且つG 1 がジベンゾフランである化合物である場合を除く。) - G 1 が下記からなる群から選択される構造で表される請求項3に記載の第1の化合物。
R B1 及びR B2 は、独立して、水素、重水素、アルキル、シクロアルキル、アルコキシル、アリール、ヘテロアリール、ハロゲン、及びこれらの組合せからなる群から選択され;
R B1 及びR B2 は、結合して環を形成してもよい。) - 式IIIで表されることを特徴とする第1の化合物。
GA及びGBは、フェニル、ビフェニル、ピリジン、ジベンゾチオフェン、ジベンゾフラン、ジベンゾセレノフェン、及びフルオレンからなる群から選択され;
GA及びGBは、それぞれ、重水素、アルキル、アルコキシル、シクロアルキル、シクロアルコキシル、ハロゲン、ニトロ、ニトリル、シリル、フェニル、ビフェニル、ターフェニル、ピリジン、及びこれらの組合せからなる群から選択される1つ以上の非縮合置換基で更に置換されていてもよい。) - 第1の有機発光デバイスを含む第1のデバイスであって、前記第1の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の間に配置され、請求項1から2のいずれかに記載の組成物、又は請求項3から5のいずれかに記載の第1の化合物を含む有機層と;を含むことを特徴とする第1のデバイス。
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JP2019194198A (ja) * | 2014-07-09 | 2019-11-07 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネッセンス材料及びデバイス |
US11456423B2 (en) | 2014-07-09 | 2022-09-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11957047B2 (en) | 2014-07-09 | 2024-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
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