JP5562657B2 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- JP5562657B2 JP5562657B2 JP2010010199A JP2010010199A JP5562657B2 JP 5562657 B2 JP5562657 B2 JP 5562657B2 JP 2010010199 A JP2010010199 A JP 2010010199A JP 2010010199 A JP2010010199 A JP 2010010199A JP 5562657 B2 JP5562657 B2 JP 5562657B2
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- 238000005401 electroluminescence Methods 0.000 title claims description 29
- -1 acylamide group Chemical group 0.000 claims description 196
- 125000001424 substituent group Chemical group 0.000 claims description 159
- 150000001875 compounds Chemical class 0.000 claims description 88
- 239000004215 Carbon black (E152) Substances 0.000 claims description 86
- 229930195733 hydrocarbon Natural products 0.000 claims description 86
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
- 229910052751 metal Inorganic materials 0.000 claims description 76
- 239000002184 metal Substances 0.000 claims description 76
- 150000002430 hydrocarbons Chemical group 0.000 claims description 69
- 125000002252 acyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000004423 acyloxy group Chemical group 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 239000003446 ligand Substances 0.000 claims description 26
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 23
- 150000007942 carboxylates Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 7
- 150000001450 anions Chemical group 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 5
- 229910001431 copper ion Inorganic materials 0.000 claims description 5
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
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- 125000003118 aryl group Chemical group 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
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- 230000015572 biosynthetic process Effects 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- AHTKGFIYHBHGAM-UHFFFAOYSA-N 4-ethenyl-2,6-dimethylpyridine Chemical compound CC1=CC(C=C)=CC(C)=N1 AHTKGFIYHBHGAM-UHFFFAOYSA-N 0.000 description 12
- 239000010949 copper Substances 0.000 description 12
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- 150000001721 carbon Chemical group 0.000 description 10
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- 238000004519 manufacturing process Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229920000642 polymer Chemical class 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
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- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 6
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 125000006410 propenylene group Chemical group 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910052761 rare earth metal Chemical group 0.000 description 5
- 150000002910 rare earth metals Chemical group 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- WLUJHMKCLOIRSK-UHFFFAOYSA-N 1,2,4,5-tetramethylimidazole Chemical compound CC=1N=C(C)N(C)C=1C WLUJHMKCLOIRSK-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
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- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N c1cnccn1 Chemical compound c1cnccn1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
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- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
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- 229920001577 copolymer Polymers 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
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- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
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- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 238000007650 screen-printing Methods 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/18—Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- H—ELECTRICITY
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Description
そこで、コスト面で有利であるより安価な金属を用いる種々の金属配位化合物が発光材料として検討されている。
〔1〕 陽極及び陰極からなる1対の電極間に、下記式(1)で示される金属配位化合物を含有する有機層が挟持された有機電界発光素子。
MLaXb (1)
(式中、Mは周期律表第11族の金属イオンであり、Lは下記式(2)で表される配位子であり、Xはアニオンであり、aは0<a≦6を満たす数であり、bは0以上の数である。)
〔2〕 前記式(3)及び(4)において、前記R1からR9が水素原子以外の基である場合には、前記R1からR9が、置換基を有していてもよい炭化水素基である、〔1〕に記載の有機電界発光素子。
〔3〕 前記式(2)において、前記Aが、下記式(5)又は(6)から水素原子を2個除いた2価の基である、〔1〕又は〔2〕に記載の有機電界発光素子。
〔4〕 前記式(2)において、Aが複数個存在するとき、配位窒素原子同士間を結ぶ最短の共有結合の数がいずれにおいても5以上である、〔1〕から〔3〕のいずれか一項に記載の有機電界発光素子。
〔5〕 前記式(2)において、m1が2〜10000の数である〔1〕から〔4〕のいずれか一項に記載の有機電界発光素子。
〔6〕 前記式(1)で示される金属配位化合物において、Lが下記式(7)、(8)又は(9)で表される配位子である、〔1〕から〔5〕のいずれか一項に記載の有機電界発光素子。
〔7〕 前記式(1)の金属配位化合物において、Lが下記式(10)で表される配位子である、〔1〕から〔6〕のいずれか一項に記載の有機電界発光素子。
〔8〕 前記式(1)で示される金属配位化合物において、Mが一価の銅イオン又は銀イオンである、〔1〕から〔7〕のいずれか一項に記載の有機電界発光素子。
〔9〕 下記式(11)で示される配位子。
〔10〕 下記式(12)で示される金属配位化合物。
MLaXb (12)
(式中、Mは金属イオンであり、Lは下記式(11)で示される配位子であり、Xはアニオンであり、aは0<a≦6を満たす数であり、bは0以上の数である。)
本発明の有機電界発光素子に好適に適用できる発光材料は、下記式(1)で表される金属配位化合物である。
MLaXb (1)
bは0以上の数であり、好ましくは0≦b≦2を満たす数であり、より好ましくは0<a≦1を満たす数である。
ただし、R1及びR5のうちの少なくとも1個は水素原子以外の基であり、R6及びR9のうちの少なくとも1個は水素原子以外の基である。R1とR2との組み合わせ、R2とR3との組み合わせ、R3とR4との組み合わせ、R4とR5との組み合わせ、R6とR7との組み合わせ、R7とR8との組み合わせ、及びR8とR9との組み合わせは、それぞれ一緒になって環を形成していてもよい。
これら炭素原子に結合する「置換基」のうち、アシルオキシ基、炭化水素オキシカルボニル基、炭化水素基、炭化水素オキシ基、炭化水素チオ基は、これらの基に含まれる水素原子がハロゲン原子、シアノ基、ニトロ基、アシルオキシ基、炭化水素オキシカルボニル基、カルボキシレート基、アシルアミド基、イミノ基、水酸基、アシル基、炭化水素基、炭化水素オキシ基、炭化水素チオ基、複素環基により、さらに置換されていてもよい。
炭素原子に結合する「置換基」の好ましい例は、ハロゲン原子、シアノ基、アシルオキシ基、炭化水素オキシカルボニル基、アシルアミド基、アシル基、炭化水素基、炭化水素オキシ基、炭化水素チオ基であり、より好ましくは、ハロゲン原子、炭化水素オキシカルボニル基、アシルアミド基、アシル基、炭化水素基、炭化水素オキシ基であり、さらに好ましくは、ハロゲン原子、炭化水素基、炭化水素オキシ基であり、特に好ましくは炭化水素基である。
これら窒素原子に結合する「置換基」のうち、炭化水素オキシカルボニル基、炭化水素基は、ハロゲン原子、シアノ基、ニトロ基、アシルオキシ基、炭化水素オキシカルボニル基、カルボキシレート基、アシルアミド基、イミノ基、水酸基、アシル基、炭化水素基、炭化水素オキシ基、炭化水素チオ基、複素環基により、さらに置換されていてもよい。窒素原子に結合する「置換基」の好ましい例は、炭化水素基である。
Q1及びQ2が炭素原子を含む基である場合には、炭素数が好ましくは1〜20であり、より好ましくは1〜10であり、さらに好ましくは1〜6である。特にQ1及びQ2が芳香環を含む基である場合には、炭素数が好ましくは5〜20であり、より好ましくは6〜10である。
前記式(2)の配位子において、3個以上の配位窒素原子が存在する場合には、配位窒素原子同士間を結ぶ最短の共有結合の数がいずれにおいても5以上である。
R33、R34、R35及びR36が炭素原子を含む基である場合には、炭素数が好ましくは1〜30であり、より好ましくは1〜20であり、さらに好ましくは1〜10であり、特に好ましくは1〜6である。特にR33、R34、R35及びR36が芳香環を含む基である場合には、炭素数が好ましくは5〜30であり、より好ましくは6〜20であり、さらに好ましくは6〜10である。
MLaXb (12)
(a)陽極/正孔注入層/(正孔輸送層)/発光層/陰極
(b)陽極/発光層/電子注入層/(電子輸送層)/陰極
(c)陽極/正孔注入層(正孔輸送層)/発光層/電子注入層/(電子輸送層)/陰極
などが挙げられる。
塗布法の場合には、上記金属配位化合物を溶媒と混合して塗布液を調製し、塗布液を所望の層(又は電極)上に、塗布及び乾燥することによって層形成することができる。塗布液中にはホスト材料及び/又はバインダーとして樹脂を含有させてもよく、樹脂は溶媒に溶解状態とすることも、分散状態とすることもできる。樹脂としては、ポリビニルカルバゾールなどの非共役系高分子、ポリオレフィン系高分子などの共役系高分子を使用することができる。
重合体の重量平均分子量(Mw)、数平均分子量(Mn)は、ゲルパーミエーションクロマトグラフィ−(GPC)(東ソー株式会社製:HLC−8220GPC)を用いて測定し、ポリスチレン換算の数平均分子量及び重量平均分子量として求めた。また、測定する試料は、約0.5wt%の濃度になるようにテトラヒドロフランに溶解させ、GPCに50μLを注入した。更に、GPCの移動相としてはテトラヒドロフランを用い、0.5mL/minの流速で流した。発光スペクトル及び発光寿命は、励起波長に350nmを用い、蛍光分光光度計(JOBINYVON−SPEX社製、商品名:Fluorolog−Tau3)を用いて測定した。励起寿命は発光ピークの波長にて測定した。
<金属配位化合物の合成例>
アルゴン雰囲気下、塩化銅(I)(500mg、5.1mmol)を、2,6−ジメチルピリジン(5mL)に加え、100℃で加熱し撹拌しながら均一溶液にした。この溶液を室温まで放冷したところ無色結晶が析出した。この結晶を濾取し、アセトンにて洗浄後、50℃で5時間真空乾燥することで、金属配位化合物((Cu+)1(2,6−ジメチルピリジン)1(Cl−)1)を得た(702mg、収率68%)。
元素分析 Found(%)C:40.69、H:4.30、N:6.89、Cl:16.50、Calcd for C7H9NCuCl(%) C:40.78、H:4.40、N:6.79、Cl:17.20
粉末サンプルでの発光ピーク波長(励起寿命)は、446nm(4.7μs)であった。
スパッタ法により150nmの厚みでITO膜を形成したガラス基板に、ポリ(エチレンジオキシチオフェン)/ポリスチレンスルホン酸の溶液(バイエル社、商品名:Baytron P)を用いてスピンコート法により65nmの厚みで成膜し、ホットプレート上、200℃で10分間乾燥した。
次に、下記繰り返し単位F5及びF8をモル比でF8:F5=8:2の割合で有するポリマーに、前述の合成例により合成した金属配位化合物を、ポリマー8に対し、2の重量比相当分として混合し、スピンコート法により成膜した。膜厚は約60nmであった。成膜された膜を窒素ガス雰囲気下、130℃で10分間乾燥した後、バリウムを約4nm、次いでアルミニウムを約100nm蒸着して陰極とし、有機電界発光素子を作製した。
得られた有機電界発光素子を大気曝露した後に電圧を印加したところ、500nm付近にピークを有する電界発光が得られた。
<ポリ(4−ビニル−2,6−ジメチルピリジン)の合成例>
ポリ(4−ビニル−2,6−ジメチルピリジン)の合成は以下のスキームに従って行った。
得られた液体に石油エーテル(100mL)を加え、セライトろ過を行った後、溶媒をエバポレートした。残渣をシリカゲルカラムクロマトグラフィ(展開溶媒;ヘキサン:酢酸エチル=3:1)にて精製し、4−ビニル−2,6−ジメチルピリジン3.0g(43%)を得た。
1H NMR(400MHz、CDCl3):δ6.95(s、2H)、6.60(m、1H)、5.92(d、J=17.6Hz、1H)、5.42(d、J=10.8Hz、1H)、2.52(s、6H).
アルゴン雰囲気下、塩化銅(I)(7.5mg、0.075mmol)とポリ(4−ビニル−2,6−ジメチルピリジン)(100mg、繰り返し単位:0.75mmol)とを脱水アセトニトリル(30mL)に溶解させ、常温にて撹拌した。溶媒を減圧下エバポレートした。金属配位化合物((Cu+)1(ポリ(4−ビニル−2,6−ジメチルピリジン))0.11(Cl−)1)を得た。
粉末サンプルでの発光ピーク波長(励起寿命)は、480nm(1.0μs)であった。
スパッタ法により150nmの厚みでITO膜を形成したガラス基板に、ポリ(エチレンジオキシチオフェン)とポリスチレンスルホン酸との溶液(バイエル社、商品名:Baytron P)を用いてスピンコート法により65nmの厚みで成膜し、ホットプレート上、200℃で10分間乾燥した。次に、正孔輸送層形成用組成物をスピンコート法により20nmの厚みで成膜し、ホットプレート上、190℃で20分間乾燥して正孔輸送層を形成した。
還流冷却器及びオーバーヘッドスターラを装備した容量1リットルの3口丸底フラスコに、2,7−ビス(1,3,2−ジオキシボロール)−9,9−ジ(1−オクチル)フルオレン(3.863g、7.283mmol)、N,N−ジ(p−ブロモフェニル)−N−(4−(ブタン−2−イル)フェニル)アミン(3.177g、6.919mmol)及びジ(4−ブロモフェニル)ベンゾシクロブタンアミン(156.3mg、0.364mmol)を加えた。
<金属配位化合物の合成例>
アルゴン雰囲気下、ヨウ化銅(I)(400mg、2.1mmol)と、1,2,4,5−テトラメチルイミダゾール(1g、8.1mmol)とを脱水アセトン(10mL)中にて、50℃で加熱撹拌しながら均一溶液にした。溶液を常温まで放冷したところ無色結晶が析出した。この結晶を濾取し、アセトンにて洗浄後、50℃で5時間真空乾燥することで金属配位化合物((Cu+)1(1,2,4,5−テトラメチルイミダゾール)2(I−)1)を得た(674mg、収率73%)。
元素分析 Found(%)C:38.54、H:5.44、N:12.84、I:28.17、Cu:13.3、Calcd for C14H12N2CuI(%) C:38.32、H:5.51、N:12.77、I:28.92、Cu:14.5
粉末サンプルでの発光ピーク波長は425nmであった。
実施例1の有機電界発光素子の作製例と同様に有機電界発光素子を作製し、得られた有機電界発光素子を大気曝露した後に電圧を印加することにより、電界発光が得られる。
<金属配位化合物の合成例>
テトラフルオロホウ酸銀(I)(0.4mg、0.002mmol)とポリ(4−ビニル−2,6−ジメチルピリジン)(1.9mg、繰り返し単位:0.014mmol)とを脱水ジクロロメタン(1mL)に溶解させ、常温にて撹拌した。溶媒を減圧下エバポレートした。金属配位化合物((Ag+)1(ポリ(4−ビニル−2,6−ジメチルピリジン))0.08(BF4 −)1)を得た。
粉末サンプルでの発光ピーク波長(励起寿命)は、390nmであった。
実施例1の有機電界発光素子の作製例と同様に有機電界発光素子を作製し、得られた有機電界発光素子を大気曝露した後に電圧を印加することにより、電界発光が得られる。
<金属配位化合物の合成例>
アルゴン雰囲気下、ヨウ化銅(I)(400mg、2.1mmol)に、ピリジン(5mL)と脱水アセトン(10mL)とを加え、常温にて撹拌しながら均一溶液にした。溶液を−18℃まで冷却したところ無色結晶が析出した。この結晶を濾取し、50℃で5時間真空乾燥することで(Cu+)1(ピリジン)1(I−)1を得た(312mg、収率44%)。
元素分析 Found(%)C:20.89、H:1.76、N:4.82、I:44.15、Calcd for C5H5NCuI(%) C:22.28、H:1.87、N:5.20、I:47.08
粉末サンプルでの発光ピーク波長(励起寿命)560nm(6.3μs)
金属配位化合物として、(Cu)1(ピリジン)1(I)1を用いる他は、実施例1の有機電界発光素子の作製例と同様に有機電界発光素子(比較有機電界発光素子)を作製した。得られた比較有機電界発光素子を大気曝露した後に電圧を印加したところ、電界発光は全く観測されなかった。
実施例2の金属配位化合物合成例において、ポリ(4−ビニル−2,6−ジメチルピリジン)の代わりにポリ(4−ビニルピリジン)(アルドリッチ社、average Mw 〜60000)を用いる他は、実施例2の金属配位化合物合成例と同様な操作を行い、比較化合物を得た。得られた比較化合物は、大気曝露により速やかに黒色に変化し、分解した。分解に伴い、紫外光励起(励起波長:365nm)による発光も消光した。そのため、実施例2の有機電界発光素子の作製例と同様の操作にて素子を作成し、得られた有機電界発光素子を大気曝露すると、電圧を印加しても電界発光は観測されない。
実施例3の金属配位化合物合成例において、1,2,4,5−テトラメチルイミダゾールの代わりにイミダゾールを用いる他は、金属配位化合物合成例2と同様な操作を行い、比較化合物3を得た。得られた比較化合物3は、大気曝露により速やかに黒色に変化し、分解した。分解に伴い、紫外光励起(励起波長:365nm)による発光も消光した。そのため、実施例1の有機電界発光素子の作製例と同様の操作にて素子を作成し、得られた有機電界発光素子を大気曝露すると、電圧を印加しても電界発光は観測されない。
Claims (3)
- 陽極及び陰極からなる1対の電極間に、下記式(1)で示される金属配位化合物を含有する有機層が挟持された有機電界発光素子。
MLaXb (1)
(式中、Mは周期律表第11族の金属イオンであり、Lは下記式(7)、(8)又は(9)で表される配位子であり、Xはアニオンであり、aは0<a≦6を満たす数であり、bは0以上の数である。)
- 前記式(1)の金属配位化合物において、Lが下記式(10)で表される配位子である、請求項1に記載の有機電界発光素子。
- 前記式(1)で示される金属配位化合物において、Mが一価の銅イオン又は銀イオンである、請求項1又は2に記載の有機電界発光素子。
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CN107108861B (zh) | 2014-11-20 | 2019-11-12 | 株式会社Lg化学 | 空穴传输材料 |
US9954174B2 (en) * | 2015-05-06 | 2018-04-24 | E I Du Pont De Nemours And Company | Hole transport materials |
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JP3268878B2 (ja) * | 1993-03-25 | 2002-03-25 | 三洋電機株式会社 | 電界発光素子 |
JP2003253257A (ja) * | 2002-02-28 | 2003-09-10 | Jsr Corp | 燐光発光剤、その製造方法および発光性組成物 |
JP2003332074A (ja) * | 2002-05-09 | 2003-11-21 | Canon Inc | 金属配位化合物を用いた発光素子 |
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- 2010-01-21 WO PCT/JP2010/050699 patent/WO2010084908A1/ja active Application Filing
- 2010-01-21 EP EP10733515A patent/EP2383814A4/en not_active Withdrawn
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EP2383814A1 (en) | 2011-11-02 |
EP2383814A4 (en) | 2012-10-24 |
KR20110124210A (ko) | 2011-11-16 |
JP2010192887A (ja) | 2010-09-02 |
CN102292842A (zh) | 2011-12-21 |
TW201035286A (en) | 2010-10-01 |
US20120049167A1 (en) | 2012-03-01 |
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