JP2000103786A - Raw material of electroluminescence element and electroluminescence element by using the same - Google Patents
Raw material of electroluminescence element and electroluminescence element by using the sameInfo
- Publication number
- JP2000103786A JP2000103786A JP10278252A JP27825298A JP2000103786A JP 2000103786 A JP2000103786 A JP 2000103786A JP 10278252 A JP10278252 A JP 10278252A JP 27825298 A JP27825298 A JP 27825298A JP 2000103786 A JP2000103786 A JP 2000103786A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- general formula
- derivatives
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000005401 electroluminescence Methods 0.000 title abstract description 7
- 239000002994 raw material Substances 0.000 title abstract 2
- 239000000463 material Substances 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 150000007980 azole derivatives Chemical class 0.000 claims abstract description 27
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 abstract description 7
- ZFYWCVZNRMSXBT-UHFFFAOYSA-N 2-methyl-4,5-diphenyl-1,3-thiazole Chemical compound S1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZFYWCVZNRMSXBT-UHFFFAOYSA-N 0.000 abstract description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 56
- 239000010410 layer Substances 0.000 description 47
- -1 quinolinol aluminum Chemical compound 0.000 description 33
- 238000000034 method Methods 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
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- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000000975 dye Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
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- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- 125000000623 heterocyclic group Chemical group 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
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- 239000011777 magnesium Substances 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Chemical class 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000008376 fluorenones Chemical class 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007733 ion plating Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 238000001451 molecular beam epitaxy Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
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- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
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- 125000004076 pyridyl group Chemical group 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
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- QNXWZWDKCBKRKK-UHFFFAOYSA-N 2-methyl-n-[4-[4-(n-(2-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C(=CC=CC=1)C)C1=CC=CC=C1 QNXWZWDKCBKRKK-UHFFFAOYSA-N 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- AODWRBPUCXIRKB-UHFFFAOYSA-N naphthalene perylene Chemical group C1=CC=CC2=CC=CC=C21.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 AODWRBPUCXIRKB-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical group 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
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 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
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、エレクトロルミネ
ッセンス素子材料及びそれを用いたエレクトロルミネッ
センス素子に関する。さらに、本発明は、新規アゾール
誘導体にも関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electroluminescent device material and an electroluminescent device using the same. Furthermore, the present invention also relates to novel azole derivatives.
【０００２】[0002]
【従来の技術】今日、種々の表示素子に関する研究開発
が活発であり、中でも、有機エレクトロルミネッセンス
素子（ＥＬ素子）は、低電圧で高輝度の発光を得ること
ができ、有望な表示素子として注目されている。例え
ば、有機化合物の蒸着により有機薄膜を形成するＥＬ素
子が知られている（アプライド フィジックス レター
ズ，５１巻，９１３頁，１９８７年参照）。この文献に
記載の有機ＥＬ素子は電子輸送材料と正孔輸送材料の積
層構造を有し、従来の単層型素子に比べてその発光特性
が大幅に向上している。2. Description of the Related Art At present, research and development on various display elements are active. Among them, an organic electroluminescence element (EL element), which can obtain high-luminance light emission at a low voltage, has attracted attention as a promising display element. Have been. For example, an EL device which forms an organic thin film by vapor deposition of an organic compound is known (see Applied Physics Letters, vol. 51, p. 913, 1987). The organic EL device described in this document has a laminated structure of an electron transporting material and a hole transporting material, and its luminous characteristics are greatly improved as compared with a conventional single-layer type device.
【０００３】上記積層型ＥＬ素子の発光効率を改良する
手段として、蛍光色素をドープする方法が知られてい
る。例えば、ジャーナルオブアプライドフィジックス６
５巻３６１０頁１９８９年に記載のクマリン色素をドー
プした有機ＥＬ素子は、ドープしない素子に比べて発光
効率が大幅に向上している。本報告以来、種々のドーパ
ントが検討され、用いるドーパントの種類によってＥＬ
素子の特性が大きく変化することが明らかにされ、高輝
度化可能なドーパントの開発が望まれていた。[0003] As a means for improving the luminous efficiency of the stacked EL device, a method of doping a fluorescent dye is known. For example, Journal of Applied Physics 6
The organic EL device doped with a coumarin dye described in Vol. 5, p. 3610, 1989 has significantly improved luminous efficiency as compared with a device not doped. Since this report, various dopants have been studied, and the EL
It has been clarified that the characteristics of the device greatly change, and development of a dopant capable of increasing luminance has been desired.
【０００４】上記ドープ色素を利用したＥＬ素子は、発
光効率が大幅に向上する反面、ごく微量の色素を素子に
組み込む必要がある等製造適性が低く、また、微量のド
ープ色素が経時で分解すると、その素子特性が大きく悪
化する等の問題がある。ホスト材料（電荷輸送材料）と
発光材料を兼用する化合物（例えば、アプライド フィ
ジックス レターズ、５１巻、９１３頁、１９８７年、
に記載のキノリノールアルミニウム錯体のように、電子
輸送材料と発光材料の機能を併せ持つ化合物）で高輝度
発光可能な化合物を開発できれば、蛍光色素ドープによ
り性能向上する必要がなくなり、上記問題は解決できる
が、一般的には色素濃度（発光材料の濃度）を濃くする
と、色素の会合、エキサイプレックスの生成等により、
発光効率が大きく低下する問題があった。このことか
ら、単一化合物でホスト機能と発光機能を兼ね備え、高
輝度発光する化合物の開発が望まれていた。The EL device using the above-mentioned doped dyes has a large improvement in luminous efficiency, but has a low suitability for production, such as the necessity of incorporating a very small amount of the dye into the device. In addition, there is a problem that the element characteristics are greatly deteriorated. Compound serving as both a host material (charge transport material) and a light emitting material (for example, Applied Physics Letters, 51, 913, 1987,
If a compound capable of emitting light with high luminance can be developed by using a compound having both functions of an electron transporting material and a light emitting material, such as a quinolinol aluminum complex described in (1), it is not necessary to improve the performance by fluorescent dye doping, and the above problem can be solved. In general, when the dye concentration (the concentration of the luminescent material) is increased, the association of the dye, the formation of an exciplex, etc.
There is a problem that luminous efficiency is greatly reduced. Accordingly, it has been desired to develop a single compound having both a host function and a light emitting function and emitting light with high luminance.
【０００５】[0005]
【発明が解決しようとする課題】本発明の目的は、エレ
クトロルミネッセンス素子に用いることができ、高輝度
のエレクトロルミネッセンス素子材料を提供することに
ある。本発明の他の目的は、高輝度化が可能なドープ色
素を用いた有機エレクトロルミネッセンス素子を提供す
ることにある。本発明の他の目的は、ホスト材料（電荷
輸送材料）と発光材料を同時に兼ね備えるエレクトロル
ミネッセンス素子を提供することにある。An object of the present invention is to provide a high-luminance electroluminescent element material which can be used for an electroluminescent element. Another object of the present invention is to provide an organic electroluminescence device using a doped dye capable of increasing luminance. Another object of the present invention is to provide an electroluminescence device having both a host material (charge transport material) and a light emitting material.
【０００６】[0006]
【課題を解決するための手段】本発明によれば、下記構
成の発明が提供され、本発明の上記目的が達成される。 〔１〕下記一般式（１）で表されるアゾール誘導体から
なるエレクトロルミネッセンス素子材料。According to the present invention, an invention having the following constitution is provided, and the above object of the present invention is achieved. [1] An electroluminescent device material comprising an azole derivative represented by the following general formula (1).
【０００７】[0007]
【化３】 Embedded image
【０００８】上記一般式（１）中、Ｒ1，Ｒ2は、同一又
は異なって、水素原子又は置換基を表し、Ｒ1及びＲ2の
少なくともいずれかは、アリール基又は芳香族ヘテロ環
基である。Ｒ3，Ｒ4 は、同一又は異なって、水素原子
又は置換基を表す。Ｒ5は、アリール基又は芳香族ヘテ
ロ環基を表す。Ｘ1は、酸素原子、硫黄原子、置換ある
いは無置換の窒素原子、又は−ＣＲ6（Ｒ7）−を表す。
Ｒ6，Ｒ7 は、同一又は異なって、水素原子又は置換基
を表す。 〔２〕上記アゾール誘導体が下記一般式（２）で表され
るアゾール誘導体であるエレクトロルミネッセンス素子
材料。In the general formula (1), R 1 and R 2 are the same or different and each represent a hydrogen atom or a substituent, and at least one of R 1 and R 2 is an aryl group or an aromatic heterocyclic group. It is. R 3 and R 4 are the same or different and each represent a hydrogen atom or a substituent. R 5 represents an aryl group or an aromatic heterocyclic group. X 1 represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, or —CR 6 (R 7 ) —.
R 6 and R 7 are the same or different and represent a hydrogen atom or a substituent. [2] An electroluminescent device material, wherein the azole derivative is an azole derivative represented by the following general formula (2).
【０００９】[0009]
【化４】 Embedded image
【００１０】上記一般式（２）中、Ａｒ1，Ａｒ2，Ａｒ
4，Ａｒ5 は、同一又は異なって、アリール基又は芳香
族ヘテロ環基を表す。Ａｒ3は、２価芳香族連結基を表
す。Ｘ2は、請求項１に記載の一般式（１）のＸ1と同義
である。 〔３〕上記〔１〕又は〔２〕記載のエレクトロルミネッ
センス素子材料を含有するエレトロルミネッセンス素
子。 〔４〕上記〔１〕又は〔２〕記載のエレクトロルミネッ
センス素子材料の単一化合物層を発光層に有するエレク
トロルミネッセンス素子。 〔５〕上記一般式（２）で表される新規アゾール誘導
体。In the above general formula (2), Ar 1 , Ar 2 , Ar
4 and Ar 5 are the same or different and represent an aryl group or an aromatic heterocyclic group. Ar 3 represents a divalent aromatic linking group. X 2 has the same meaning as X 1 in the general formula (1) according to claim 1. [3] An electroluminescent device containing the electroluminescent device material according to [1] or [2]. [4] An electroluminescent device having a single compound layer of the electroluminescent device material according to [1] or [2] in a light emitting layer. [5] A novel azole derivative represented by the general formula (2).
【００１１】[0011]
【発明の実施の形態】上記一般式（１）で表されるアゾ
ール誘導体は、一般式（２）で表されるアゾール誘導体
を包含し、本発明のエレクトロルミネッセンス素子の高
輝度の発光材料として用いられる。そして、一般式
（２）で表されるアゾール誘導体は、新規物質である。BEST MODE FOR CARRYING OUT THE INVENTION The azole derivative represented by the general formula (1) includes the azole derivative represented by the general formula (2), and is used as a high-luminance light-emitting material of the electroluminescent device of the present invention. Can be The azole derivative represented by the general formula (2) is a novel substance.
【００１２】まず、一般式（１）で表される化合物につ
いて説明する。Ｒ1，Ｒ2は、同一又は異なって、水素原
子又は置換基を表す。Ｒ1及びＲ2の少なくともいずれか
は、アリール基又は芳香族ヘテロ環基である。上記置換
基としては、下記の基を挙げることができる。 （１）アルキル基：好ましくは炭素数１〜２０、より好
ましくは炭素数１〜１２、特に好ましくは炭素数１〜８
である。具体的には、メチル、エチル、ｉｓｏ−プロピ
ル、ｔｅｒｔ−ブチル、ｎ−オクチル、ｎ−デシル、ｎ
−ヘキサデシル、シクロプロピル、シクロペンチル、シ
クロヘキシル等が挙げられる。 （２）アルケニル基：好ましくは炭素数２〜２０、より
好ましくは炭素数２〜１２、特に好ましくは炭素数２〜
８である。具体的には、ビニル、アリル、２−ブテニ
ル、３−ペンテニル等が挙げられる。 （３）アルキニル基：好ましくは炭素数２〜２０、より
好ましくは炭素数２〜１２、特に好ましくは炭素数２〜
８である。具体的には、プロパルギル、３−ペンチニル
等が挙げられる。 （４）アリール基：好ましくは炭素数６〜３０、より好
ましくは炭素数６〜２０、特に好ましくは炭素数６〜１
２である。具体的には、フェニル、ｐ−メチルフェニ
ル、ナフチル等が挙げられる。First, the compound represented by formula (1) will be described. R 1 and R 2 are the same or different and represent a hydrogen atom or a substituent. At least one of R 1 and R 2 is an aryl group or an aromatic heterocyclic group. Examples of the substituent include the following groups. (1) alkyl group: preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms
It is. Specifically, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n
-Hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. (2) alkenyl group: preferably 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 2 carbon atoms.
8 Specifically, vinyl, allyl, 2-butenyl, 3-pentenyl and the like can be mentioned. (3) Alkynyl group: preferably 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 2 carbon atoms.
8 Specific examples include propargyl and 3-pentynyl. (4) Aryl group: preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 1 carbon atoms.
2. Specifically, phenyl, p-methylphenyl, naphthyl and the like can be mentioned.
【００１３】（５）置換カルボニル基：好ましくは炭素
数１〜２０、より好ましくは炭素数１〜１６、特に好ま
しくは炭素数１〜１２である。具体的には、アセチル、
ベンゾイル、メトキシカルボニル、フェニルオキシカル
ボニル、ジメチルアミノカルボニル、フェニルアミノカ
ルボニル、等が挙げられる。 （６）アミノ基：好ましくは炭素数０〜２０、より好ま
しくは炭素数１〜１６、特に好ましくは炭素数１〜１２
である。具体的には、ジメチルアミノ、メチルカルバモ
イル、エチルスルフォニルアミノ、ジメチルアミノカル
ボニルアミノ基、フタルイミド基等が挙げられる。 （７）スルホニル基：好ましくは炭素数１〜２０、より
好ましくは炭素数１〜１６、特に好ましくは炭素数１〜
１２である。具体的には、メシル、トシル等が挙げられ
る。 （８）ヘテロ環基：脂肪族ヘテロ環基、芳香族ヘテロ環
基のいずれでもよい。好ましくは、酸素原子、硫黄原
子、窒素原子のいずれかを含む。また、好ましくは炭素
数１〜５０、より好ましくは炭素数１〜３０、特に好ま
しくは炭素数２〜１２である。具体的には、イミダゾリ
ル、ピリジル、フリル、ピペリジル、モルホリノ、ベン
ズオキサゾリル、トリアゾリル基等が挙げられる。(5) Substituted carbonyl group: It preferably has 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Specifically, acetyl,
Examples include benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, and the like. (6) amino group: preferably having 0 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
It is. Specific examples include dimethylamino, methylcarbamoyl, ethylsulfonylamino, dimethylaminocarbonylamino group, phthalimide group and the like. (7) Sulfonyl group: preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 1 carbon atoms.
Twelve. Specific examples include mesyl and tosyl. (8) Heterocyclic group: any of an aliphatic heterocyclic group and an aromatic heterocyclic group. Preferably, it contains any of an oxygen atom, a sulfur atom and a nitrogen atom. Further, it preferably has 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 12 carbon atoms. Specific examples include imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, and triazolyl groups.
【００１４】（９）アルコキシ基：好ましくは炭素数１
〜２０、より好ましくは炭素数１〜１６、特に好ましく
は炭素数１〜１２である。具体的には、メトキシ基、ベ
ンジルオキシ基等が挙げられる。 （１０）アリールオキシ基：好ましくは炭素数６〜２
０、より好ましくは炭素数６〜１６、特に好ましくは炭
素数６〜１２である。具体的には、フェノキシ基、ナフ
チルオキシ基等が挙げられる。 （１１）ハロゲン原子：好ましくはフッ素原子、塩素原
子、臭素原子、ヨウ素原子、 （１２）アルキルチオ基：好ましくは炭素数１〜２０、
より好ましくは炭素数１〜１６、特に好ましくは炭素数
１〜１２である。具体的には、メチルチオ基等が挙げら
れる。 （１３）アリールチオ基：好ましくは炭素数６〜２０、
より好ましくは炭素数６〜１６、特に好ましくは炭素数
６〜１２である。具体的には、フェニルチオ基等が挙げ
られる）、 （１４）その他ヒドロキシ基、カルボキシル基、チオー
ル基、スルホ基、シアノ基等が挙げられる。 以上の置換基はさらに置換されてもよい。(9) alkoxy group: preferably having 1 carbon atom
-20, more preferably 1-16 carbon atoms, particularly preferably 1-12 carbon atoms. Specific examples include a methoxy group and a benzyloxy group. (10) aryloxy group: preferably having 6 to 2 carbon atoms
0, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms. Specific examples include a phenoxy group and a naphthyloxy group. (11) halogen atom: preferably fluorine atom, chlorine atom, bromine atom, iodine atom, (12) alkylthio group: preferably having 1 to 20 carbon atoms,
More preferably, it has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms. Specific examples include a methylthio group. (13) arylthio group: preferably having 6 to 20 carbon atoms
More preferably, it has 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms. Specific examples include a phenylthio group and the like), (14) Other examples include a hydroxy group, a carboxyl group, a thiol group, a sulfo group, and a cyano group. The above substituents may be further substituted.
【００１５】好ましくは、Ｒ1，Ｒ2 は、水素原子、ア
ルキル基、アリール基、芳香族ヘテロ環基であり、さら
に好ましくは、アルキル基、アリール基、芳香族ヘテロ
環基であり、特に好ましくは、アリール基、芳香族ヘテ
ロ環基である。Preferably, R 1 and R 2 are a hydrogen atom, an alkyl group, an aryl group, or an aromatic heterocyclic group, more preferably, an alkyl group, an aryl group, or an aromatic heterocyclic group, and particularly preferably. Is an aryl group or an aromatic heterocyclic group.
【００１６】Ｒ3，Ｒ4は、同一又は異なって、水素原子
又は置換基を表す。置換基としては、例えば前記Ｒ1、
Ｒ2で説明した置換基が挙げられ、好ましい置換基も同
様である。好ましくは、Ｒ3，Ｒ4は、水素原子、アルキ
ル基、アリール基、芳香族ヘテロ環基であり、さらに好
ましくは、水素原子、アルキル基であり、特に好ましく
は水素原子である。R 3 and R 4 are the same or different and each represents a hydrogen atom or a substituent. As the substituent, for example, the aforementioned R 1 ,
The substituents described for R 2 are exemplified, and preferred substituents are also the same. Preferably, R 3 and R 4 are a hydrogen atom, an alkyl group, an aryl group, or an aromatic heterocyclic group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
【００１７】Ｒ5は、アリール基又は芳香族ヘテロ環基
を表す。アリール基、芳香族ヘテロ環基の具体例、好ま
しい態様は、前記Ｒ1で説明したアリール基、芳香族ヘ
テロ環基と同様である。好ましくは置換又は無置換のア
リール基であり、置換フェニル基がさらに好ましい。Ｒ
5上の置換基は、前記Ｒ1で挙げた置換基が挙げられ、ア
ルケニル基、アルキニル基、アリール基、芳香族ヘテロ
環基、アルコキシ基、アミノ基が好ましく、さらに好ま
しくは、アリール基、アミノ基、アルコキシ基であり、
特に好ましくはアミノ基である。これらのＲ5上の置換
基はさらに置換基を有していてもよい。R 5 represents an aryl group or an aromatic heterocyclic group. Specific examples of the aryl group, aromatic heterocyclic group, preferred embodiment, the aryl group described for R 1, the same as the aromatic heterocyclic group. A substituted or unsubstituted aryl group is preferred, and a substituted phenyl group is more preferred. R
The substituent on 5 includes the substituents described for R 1 above, and is preferably an alkenyl group, an alkynyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group or an amino group, more preferably an aryl group or an amino group. Group, an alkoxy group,
Particularly preferred is an amino group. These substituents on R 5 may further have a substituent.
【００１８】Ｘ1は、酸素原子、硫黄原子、置換あるい
は無置換の窒素原子、又は−ＣＲ6（Ｒ7）−で示される
基を表す。ここで、Ｒ6，Ｒ7 は、水素原子、置換基を
表し、置換基としては前記Ｒ1で説明した置換基が挙げ
られる。X 1 represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, or a group represented by —CR 6 (R 7 ) —. Here, R 6 and R 7 represent a hydrogen atom and a substituent, and examples of the substituent include the substituents described above for R 1 .
【００１９】Ｘ1に係わる窒素原子上の置換基としては
下記の置換基を挙げることができる。 （１）アルキル基：好ましくは炭素数１〜２０、より好
ましくは炭素数１〜１２、特に好ましくは炭素数１〜８
である。具体的には、メチル、エチル、ｉｓｏ−プロピ
ル、ｔｅｒｔ−ブチル、ｎ−オクチル、ｎ−デシル、ｎ
−ヘキサデシル、シクロプロピル、シクロペンチル、シ
クロヘキシル等が挙げられる。 （２）アルケニル基：好ましくは炭素数２〜２０、より
好ましくは炭素数２〜１２、特に好ましくは炭素数２〜
８である。具体的には、ビニル、アリル、２−ブテニ
ル、３−ペンテニル等が挙げられる。 （３）アルキニル基：好ましくは炭素数２〜２０、より
好ましくは炭素数２〜１２、特に好ましくは炭素数２〜
８である。具体的には、プロパルギル、３−ペンチニル
等が挙げられる。 （４）アリール基：好ましくは炭素数６〜３０、より好
ましくは炭素数６〜２０、特に好ましくは炭素数６〜１
２である。具体的には、フェニル、ｐ−メチルフェニ
ル、ナフチル等が挙げられる。 （５）置換カルボニル基：好ましくは炭素数１〜４０、
より好ましくは炭素数１〜２０、特に好ましくは炭素数
１〜１２である。具体的には、アセチル、ベンゾイル、
メトキシカルボニル、ジメチルアミノカルボニル、フェ
ニルアミノカルボニル基等が挙げられる。 （６）置換スルホニル基：好ましくは炭素数１〜２０、
より好ましくは炭素数１〜１６、特に好ましくは炭素数
１〜１２である。具体的には、メシル、トシル等が挙げ
られる。 （７）ヘテロ環基：好ましくは、酸素原子、硫黄原子、
窒素原子のいずれかを含む。そして炭素数１〜２０ヘテ
ロ環基が好ましく、より好ましくは炭素数１〜１６、特
に好ましくは炭素数１〜１２である。具体的には、イミ
ダゾリル、ピリジル、フリル、ピペリジル等が挙げられ
る。）等が挙げられる。これらの置換基はさらに置換さ
れてもよい。Examples of the substituent on the nitrogen atom relating to X 1 include the following substituents. (1) alkyl group: preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms
It is. Specifically, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n
-Hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. (2) alkenyl group: preferably 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 2 carbon atoms.
8 Specifically, vinyl, allyl, 2-butenyl, 3-pentenyl and the like can be mentioned. (3) Alkynyl group: preferably 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 2 carbon atoms.
8 Specific examples include propargyl and 3-pentynyl. (4) Aryl group: preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 1 carbon atoms.
2. Specifically, phenyl, p-methylphenyl, naphthyl and the like can be mentioned. (5) substituted carbonyl group: preferably having 1 to 40 carbon atoms;
More preferably, it has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms. Specifically, acetyl, benzoyl,
Examples include methoxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl and the like. (6) Substituted sulfonyl group: preferably having 1 to 20 carbon atoms;
More preferably, it has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms. Specific examples include mesyl and tosyl. (7) heterocyclic group: preferably an oxygen atom, a sulfur atom,
Contains any of the nitrogen atoms. A heterocyclic group having 1 to 20 carbon atoms is preferable, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Specific examples include imidazolyl, pyridyl, furyl, piperidyl and the like. ) And the like. These substituents may be further substituted.
【００２０】Ｒ6，Ｒ7 は、好ましくは水素原子、アル
キル基、アリール基であり、さらに好ましくは、水素原
子、アルキル基であり、特に好ましくはアルキル基であ
る。R 6 and R 7 are preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably an alkyl group.
【００２１】好ましいＸ1は、酸素原子、硫黄原子、Ｎ
Ｈ基、アルキル基置換窒素原子であり、さらに好ましく
は酸素原子、硫黄原子であり、特に好ましくは硫黄原子
である。Preferred X 1 is an oxygen atom, a sulfur atom, N
It is an H group or an alkyl group-substituted nitrogen atom, more preferably an oxygen atom or a sulfur atom, and particularly preferably a sulfur atom.
【００２２】一般式（１）で表される化合物のなかで
も、一般式（１）に包含される一般式（２）で表される
化合物が好ましい。一般式（２）において、Ａｒ1，Ａ
ｒ2，Ａｒ4，Ａｒ5は、同一又は異なって、アリール
基、芳香族ヘテロ環基を表し、Ａｒ3は２価の芳香族連
結基を表す。アリール基、芳香族ヘテロ環基は、前記Ｒ
1で説明したアリール基、芳香族ヘテロ環基が挙げら
れ、好ましい態様も同様である。芳香族連結基として
は、アリーレン基、芳香族ヘテロ環含有の２価の連結基
が挙げられる。炭素数は１〜５０が好ましく、より好ま
しくは炭素数１〜３０、特に好ましくは炭素数２〜１２
である。具体的には、フェニレン基、ピリジレン基、オ
キサジアゾレン基、ナフチレン基、アントラセニレン
基、チエニレン基、イミダゾレン基、トリアゾレン基、
ビフェニレン基、ターフェニレン基等が挙げられる。こ
れらの芳香族連結基はさらに置換基を有していてもよ
い。Among the compounds represented by the general formula (1), a compound represented by the general formula (2) included in the general formula (1) is preferable. In the general formula (2), Ar 1 , A
r 2 , Ar 4 and Ar 5 are the same or different and each represents an aryl group or an aromatic heterocyclic group, and Ar 3 represents a divalent aromatic linking group. The aryl group and the aromatic heterocyclic group are represented by R
The aryl group and the aromatic heterocyclic group described in 1 are exemplified, and the preferred embodiments are also the same. Examples of the aromatic linking group include an arylene group and a divalent linking group containing an aromatic hetero ring. The carbon number is preferably 1 to 50, more preferably 1 to 30, and particularly preferably 2 to 12.
It is. Specifically, a phenylene group, a pyridylene group, an oxadiazolene group, a naphthylene group, an anthracenylene group, a thienylene group, an imidazolen group, a triazolen group,
Examples include a biphenylene group and a terphenylene group. These aromatic linking groups may further have a substituent.
【００２３】好ましいＡｒ1，Ａｒ2は、置換又は無置換
のアリール基であり、さらに好ましくは、置換又は無置
換のフェニル基であり、特に好ましくは無置換のフェニ
ル基である。好ましいＡｒ4，Ａｒ5は、置換又は無置換
のアリール基であり、さらに好ましくは、置換又は無置
換のフェニル基であり、特に好ましくは無置換のフェニ
ル基である。好ましいＡｒ3は、置換又は無置換のアリ
ーレン基であり、さらに好ましくは置換又は無置換のフ
ェニレン基であり、特に好ましくは無置換のフェニレン
基である。Preferred Ar 1 and Ar 2 are a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl group, and particularly preferably an unsubstituted phenyl group. Desirable Ar 4 and Ar 5 are a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl group, and particularly preferably an unsubstituted phenyl group. Desirable Ar 3 is a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted phenylene group, and particularly preferably an unsubstituted phenylene group.
【００２４】Ｘ2は、一般式（１）のＸ1と同義であり、
好ましい態様も同じである。X 2 has the same meaning as X 1 in formula (1),
The preferred embodiment is also the same.
【００２５】一般式（１）で表される化合物は低分子量
化合物であってもよいし、一般式（１）で表される残基
がポリマー鎖に接続した高分子量化合物（好ましくは重
量平均分子量１０００〜５００００００、特に好ましく
は５０００〜２００００００、さらに好ましくは１００
００〜１００００００）もしくは、一般式（１）の骨格
を主鎖にもつ高分子量化合物（好ましくは重量平均分子
量１０００〜５００００００、特に好ましくは５０００
〜２００００００、さらに好ましくは１００００〜１０
０００００）であってもよい。高分子量化合物の場合
は、ホモポリマーであってもよいし、他のモノマーとの
共重合体であってもよい。The compound represented by the general formula (1) may be a low molecular weight compound or a high molecular weight compound having a residue represented by the general formula (1) connected to a polymer chain (preferably a weight average molecular weight). 1000 to 5,000,000, particularly preferably 5000 to 2,000,000, more preferably 100
00 to 1,000,000) or a high molecular weight compound having a skeleton of the general formula (1) in the main chain (preferably a weight average molecular weight of 1,000 to 5,000,000, particularly preferably 5,000)
~ 2,000,000, more preferably 10,000 ~ 10
00000). In the case of a high molecular weight compound, it may be a homopolymer or a copolymer with another monomer.
【００２６】一般式（１）で表される化合物としては、
好ましくは一般式（１）の骨格を主鎖にもつ高分子量化
合物又は低分子量化合物であり、さらに好ましくは低分
子量化合物である。The compound represented by the general formula (1) includes
It is preferably a high molecular weight compound or a low molecular weight compound having a skeleton of the general formula (1) in the main chain, and more preferably a low molecular weight compound.
【００２７】一般式（２）で表される化合物を含んで一
般式（１）で表される化合物例を次に示すが、本発明は
これに限定されない。Examples of the compound represented by the general formula (1) including the compound represented by the general formula (2) are shown below, but the present invention is not limited thereto.
【００２８】[0028]
【化５】 Embedded image
【００２９】[0029]
【化６】 Embedded image
【００３０】[0030]
【化７】 Embedded image
【００３１】[0031]
【化８】 Embedded image
【００３２】[0032]
【化９】 Embedded image
【００３３】[0033]
【化１０】 Embedded image
【００３４】一般式（１）で表されるアゾール誘導体
は、それ自体公知の単位操作を組み合わせることによ
り、製造することができる。一般式（２）で表されるア
ゾール誘導体は、前述したように、新規物質であるが、
これもそれ自体公知の単位操作を組み合わせることによ
り、製造することができる。例えば一般式（２）に包含
される上記例示化合物（１−１）は、後記する合成例１
にその製造方法が示されている。また、ホスホニウム
塩、ホスホン酸エステル誘導体を用いるＷｉｔｔｉｇ反
応、アルコール誘導体を脱水する方法、チオエステル誘
導体を用いるＣｈｕｇｑｅ反応、ケイ素化合物を用いる
ピーターソンオレフィン化反応など種々の２重結合生成
反応によって製造することができる。以上の記載を参照
すれば、当業者は一般式（２）で表されるアゾール誘導
体を合成することができる。The azole derivative represented by the general formula (1) can be produced by combining known unit operations. The azole derivative represented by the general formula (2) is a novel substance as described above,
This can also be produced by combining known unit operations. For example, the above-mentioned exemplified compound (1-1) included in the general formula (2) is synthesized in Synthesis Example 1 described below.
The production method is shown in FIG. It can also be produced by various double bond formation reactions such as a Wittig reaction using a phosphonium salt or a phosphonate derivative, a method for dehydrating an alcohol derivative, a Chugqe reaction using a thioester derivative, or a Peterson olefination reaction using a silicon compound. it can. With reference to the above description, those skilled in the art can synthesize the azole derivative represented by the general formula (2).
【００３５】次に、本発明の一般式（１）で表される化
合物を用いたエレクトロルミネッセンス素子（ＥＬ素
子）について説明する。本発明のＥＬ素子は、有機層が
積層構造であることが好ましい。一般式（２）で表され
る化合物含んで一般式（１）で表されるアゾール誘導体
（以下、単に「本発明のアゾール誘導体」ともいう）を
含有するＥＬ素子の有機層の形成方法は、特に限定され
るものではないが、抵抗加熱蒸着、電子ビーム、スパッ
タリング、分子積層法、コーティング法等の方法が用い
られ、特性面、製造面で抵抗加熱蒸着、コーティング法
が好ましい。Next, an electroluminescent device (EL device) using the compound represented by the general formula (1) of the present invention will be described. In the EL device of the present invention, the organic layer preferably has a laminated structure. The method for forming an organic layer of an EL device containing a compound represented by the general formula (2) and an azole derivative represented by the general formula (1) (hereinafter, also simply referred to as “the azole derivative of the present invention”) includes: Although not particularly limited, methods such as resistance heating evaporation, electron beam, sputtering, molecular lamination, and coating are used, and resistance heating evaporation and coating are preferred in terms of characteristics and production.
【００３６】本発明のＥＬ素子は、陽極、陰極の一対の
電極間に発光層もしくは発光層を含む複数の有機化合物
薄膜を形成した素子であり、発光層のほか正孔注入層、
正孔輸送層、電子注入層、電子輸送層、保護層等を有し
てもよく、またこれらの各層はそれぞれ他の機能を備え
たものであってもよい。各層の形成にはそれぞれ種々の
材料を用いることができる。The EL device of the present invention is a device in which a light emitting layer or a plurality of organic compound thin films including the light emitting layer are formed between a pair of anode and cathode electrodes.
It may have a hole transport layer, an electron injection layer, an electron transport layer, a protective layer, and the like, and each of these layers may have another function. Various materials can be used for forming each layer.
【００３７】陽極は、正孔注入層、正孔輸送層、発光層
等に正孔を供給するものであり、金属、合金、金属酸化
物、電気伝導性化合物、又はこれらの混合物等を用いる
ことができ、好ましくは仕事関数が４ｅＶ以上の材料で
ある。具体例としては、酸化スズ、酸化亜鉛、酸化イン
ジウム、酸化インジウムスズ（ＩＴＯ）等の導電性金属
酸化物、あるいは金、銀、クロム、ニッケル等の金属、
さらにこれらの金属と導電性金属酸化物との混合物又は
積層物、ヨウ化銅、硫化銅等の無機導電性物質、ポリア
ニリン、ポリチオフェン、ポリピロール等の有機導電性
材料、及びこれらとＩＴＯとの積層物等が挙げられる。
好ましくは、導電性金属酸化物であり、特に、生産性、
高導電性、透明性等の点からＩＴＯが好ましい。陽極の
膜厚は材料により適宜選択可能であるが、通常１０ｎｍ
〜５μｍの範囲のものが好ましく、より好ましくは５０
ｎｍ〜１μｍであり、さらに好ましくは１００ｎｍ〜５
００ｎｍである。The anode supplies holes to the hole injecting layer, the hole transporting layer, the light emitting layer, etc., and may be made of a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof. And is preferably a material having a work function of 4 eV or more. Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO), and metals such as gold, silver, chromium, and nickel;
Further, mixtures or laminates of these metals and conductive metal oxides, inorganic conductive substances such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and laminates of these with ITO And the like.
Preferably, a conductive metal oxide, particularly, productivity,
ITO is preferable in terms of high conductivity, transparency, and the like. The thickness of the anode can be appropriately selected depending on the material, but is usually 10 nm.
-5 μm is preferable, and more preferably 50 μm.
nm to 1 μm, more preferably 100 nm to 5 μm.
00 nm.
【００３８】陽極は、通常ソーダライムガラス、無アル
カリガラス、透明樹脂基板等の上に層形成したものが用
いられる。ガラスを用いる場合、その材質については、
ガラスからの溶出イオンを少なくするため、無アルカリ
ガラスを用いることが好ましい。また、ソーダライムガ
ラスを用いる場合、シリカ等のバリアコートを施したも
のを使用することが好ましい。基板の厚みは、機械的強
度を保つのに十分であれば特に制限はないが、ガラスを
用いる場合には、通常０．２ｍｍ以上、好ましくは０．
７ｍｍ以上のものが用いられる。陽極の作製には材料に
よって種々の方法が採用されるが、例えばＩＴＯの場
合、電子ビーム法、スパッタリング法、抵抗加熱蒸着
法、化学反応法（ゾル−ゲル法等）、酸化インジウムス
ズの分散物の塗布等の方法で膜形成される。陽極は、洗
浄その他の処理により、素子の駆動電圧を下げたり、発
光効率を高めることも可能である。例えばＩＴＯの場
合、ＵＶ−オゾン処理、プラズマ処理等が効果的であ
る。As the anode, a layer formed on a soda lime glass, an alkali-free glass, a transparent resin substrate or the like is usually used. When using glass,
In order to reduce ions eluted from the glass, it is preferable to use an alkali-free glass. Further, when soda lime glass is used, it is preferable to use a glass coated with a barrier coat such as silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength, but when glass is used, it is usually 0.2 mm or more, preferably 0.1 mm or more.
Those having a size of 7 mm or more are used. Various methods are used to produce the anode, depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating evaporation method, a chemical reaction method (such as a sol-gel method), and a dispersion of indium tin oxide are used. Is formed by a method such as coating of The anode can reduce the driving voltage of the element or increase the luminous efficiency by washing or other treatment. For example, in the case of ITO, UV-ozone treatment, plasma treatment and the like are effective.
【００３９】陰極は、電子注入層、電子輸送層、発光層
等に電子を供給するものであり、電子注入層、電子輸送
層、発光層等の負極と隣接する層との密着性やイオン化
ポテンシャル、安定性等を考慮して選ばれる。陰極の材
料としては、金属、合金、金属ハロゲン化物、金属酸化
物、電気伝導性化合物、又はこれらの混合物を用いるこ
とができる。具体的には、アルカリ金属（例えばＬｉ、
Ｎａ、Ｋ等）及びそのフッ化物、アルカリ土類金属（例
えばＭｇ、Ｃａ等）及びそのフッ化物、金、銀、鉛、ア
ルミニウム、ナトリウム−カリウム合金又はそれらの混
合金属、リチウム−アルミニウム合金又はそれらの混合
金属、マグネシウム−銀合金又はそれらの混合金属、イ
ンジウム、イッテリビウム等の希土類金属等が挙げられ
る。好ましくは仕事関数が４ｅＶ以下の材料であり、具
体的にはアルミニウム、リチウム−アルミニウム合金又
はそれらの混合金属、マグネシウム−銀合金又はそれら
の混合金属等である。陰極は、上記材料の単層構造だけ
でなく、上記材料を含む積層構造を取ることもできる。
陰極の膜厚は材料により適宜選択可能であるが、通常１
０ｎｍ〜５μｍの範囲のものが好ましく、より好ましく
は５０ｎｍ〜１μｍであり、さらに好ましくは１００ｎ
ｍ〜１μｍである。陰極の作製には、電子ビーム法、ス
パッタリング法、抵抗加熱蒸着法、コーティング法等の
方法が用いられ、金属を単体で蒸着することも、二成分
以上を同時に蒸着することもできる。さらに、複数の金
属を同時に蒸着して合金電極を形成することも可能であ
り、またあらかじめ調整した合金を蒸着させてもよい。
陽極及び陰極のシート抵抗は低い方が好ましく、数百Ω
／□以下が好ましい。The cathode supplies electrons to the electron injecting layer, the electron transporting layer, the light emitting layer, etc., and provides the adhesion between the negative electrode such as the electron injecting layer, the electron transporting layer, the light emitting layer, and the ionization potential. , Stability and the like. As a material of the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specifically, an alkali metal (for example, Li,
Na, K, etc.) and their fluorides, alkaline earth metals (eg, Mg, Ca, etc.) and their fluorides, gold, silver, lead, aluminum, sodium-potassium alloys or mixed metals thereof, lithium-aluminum alloys or them , A magnesium-silver alloy or a mixed metal thereof, a rare earth metal such as indium, ytterbium and the like. Preferably, the material has a work function of 4 eV or less, and specifically, aluminum, a lithium-aluminum alloy or a mixed metal thereof, a magnesium-silver alloy or a mixed metal thereof, or the like. The cathode can have not only a single-layer structure of the above materials but also a stacked structure including the above materials.
The thickness of the cathode can be appropriately selected depending on the material.
It is preferably in the range of 0 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 100 nm.
m to 1 μm. Methods such as an electron beam method, a sputtering method, a resistance heating evaporation method, and a coating method are used for manufacturing the cathode, and a metal can be evaporated alone or two or more components can be evaporated simultaneously. Further, an alloy electrode can be formed by depositing a plurality of metals at the same time, or an alloy prepared in advance may be deposited.
The sheet resistance of the anode and the cathode is preferably low, and several hundred Ω
/ □ or less is preferred.
【００４０】発光層の材料は、電界印加時に陽極又は正
孔注入層、正孔輸送層から正孔を注入することができる
と共に陰極又は電子注入層、電子輸送層から電子を注入
することができる機能や、注入された電荷を移動させる
機能、正孔と電子の再結合の場を提供して発光させる機
能を有する層を形成することができるものであれば特に
制限はない。好ましくは、発光層に本発明のアゾール誘
導体を含有するものであるが、他の発光材料を用いるこ
ともできる。例えばベンゾオキサゾール誘導体、ベンゾ
イミダゾール誘導体、ベンゾチアゾール誘導体、スチリ
ルベンゼン誘導体、ポリフェニル誘導体、ジフェニルブ
タジエン誘導体、テトラフェニルブタジエン誘導体、ナ
フタルイミド誘導体、クマリン誘導体、ペリレン誘導
体、ペリノン誘導体、オキサジアゾール誘導体、アルダ
ジン誘導体、ピラリジン誘導体、シクロペンタジエン誘
導体、ビススチリルアントラセン誘導体、キナクリドン
誘導体、ピロロピリジン誘導体、チアジアゾロピリジン
誘導体、シクロペンタジエン誘導体、スチリルアミン誘
導体、芳香族ジメチリディン化合物、８−キノリノール
誘導体の金属錯体や希土類錯体に代表される各種金属錯
体等、ポリチオフェン、ポリフェニレン、ポリフェニレ
ンビニレン等のポリマー化合物等が挙げられる。発光層
の膜厚は特に限定されるものではないが、通常１ｎｍ〜
５μｍの範囲のものが好ましく、より好ましくは５ｎｍ
〜１μｍであり、さらに好ましくは１０ｎｍ〜５００ｎ
ｍである。The material of the light emitting layer is capable of injecting holes from the anode or the hole injection layer or the hole transport layer when applying an electric field and also injecting electrons from the cathode or the electron injection layer or the electron transport layer. There is no particular limitation as long as it can form a layer having a function, a function of transferring injected charges, and a function of providing a field of recombination of holes and electrons to emit light. Preferably, the light emitting layer contains the azole derivative of the present invention, but other light emitting materials can be used. For example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, perylene derivatives, perinone derivatives, oxadiazole derivatives, aldazine derivatives , Metal complexes and rare earth complexes of pyrrolidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, aromatic dimethylidin compounds, 8-quinolinol derivatives Polymer compounds such as polythiophene, polyphenylene, polyphenylenevinylene, etc. And the like. Although the thickness of the light emitting layer is not particularly limited, it is usually 1 nm to
It is preferably in the range of 5 μm, more preferably 5 nm
１1 μm, more preferably 10 nm to 500 n
m.
【００４１】発光層の形成方法は、特に限定されるもの
ではないが、抵抗加熱蒸着、電子ビーム、スパッタリン
グ、分子積層法、コーティング法（スピンコート法、キ
ャスト法、ディップコート法等）、ＬＢ法等の方法が用
いられ、好ましくは抵抗加熱蒸着、コーティング法であ
る。The method for forming the light emitting layer is not particularly limited, but includes resistance heating evaporation, electron beam, sputtering, molecular lamination, coating (spin coating, casting, dip coating, etc.), and LB method. And the like, and preferably a resistance heating evaporation and a coating method.
【００４２】正孔注入層、正孔輸送層の材料は、陽極か
ら正孔を注入する機能、正孔を輸送する機能、陰極から
注入された電子を障壁する機能のいずれか有しているも
のであればよい。その具体例としては、本発明のアゾー
ル誘導体、カルバゾール誘導体、トリアゾール誘導体、
オキサゾール誘導体、オキサジアゾール誘導体、イミダ
ゾール誘導体、ポリアリールアルカン誘導体、ピラゾリ
ン誘導体、ピラゾロン誘導体、フェニレンジアミン誘導
体、アリールアミン誘導体、アミノ置換カルコン誘導
体、スチリルアントラセン誘導体、フルオレノン誘導
体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘
導体、芳香族第三級アミン化合物、スチリルアミン化合
物、芳香族ジメチリディン系化合物、ポルフィリン系化
合物、ポリシラン系化合物、ポリ（Ｎ−ビニルカルバゾ
ール）誘導体、アニリン系共重合体、チオフェンオリゴ
マー、ポリチオフェン等の導電性高分子オリゴマー等が
挙げられる。正孔注入層、正孔輸送層の膜厚は特に限定
されるものではないが、通常１ｎｍ〜５μｍの範囲のも
のが好ましく、より好ましくは５ｎｍ〜１μｍであり、
さらに好ましくは１０ｎｍ〜５００ｎｍである。正孔注
入層、正孔輸送層は上述した材料の１種又は２種以上か
らなる単層構造であってもよいし、同一組成又は異種組
成の複数層からなる多層構造であってもよい。The material of the hole injection layer and the hole transport layer has a function of injecting holes from the anode, a function of transporting holes, or a function of blocking electrons injected from the cathode. Should be fine. Specific examples thereof include the azole derivative, carbazole derivative, and triazole derivative of the present invention.
Oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives , Aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, aniline copolymers, thiophene oligomers, and polythiophene conductivity High molecular oligomers and the like are mentioned. The thickness of the hole injection layer and the hole transport layer is not particularly limited, but is preferably in the range of usually 1 nm to 5 μm, more preferably 5 nm to 1 μm,
More preferably, it is 10 nm to 500 nm. The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
【００４３】正孔注入層、正孔輸送層の形成方法として
は、真空蒸着法やＬＢ法、前記正孔注入輸送剤を溶媒に
溶解又は分散させてコーティングする方法（スピンコー
ト法、キャスト法、ディップコート法等）が用いられ
る。コーティング法の場合、樹脂成分と共に溶解又は分
散することができ、樹脂成分としては例えば、ポリ塩化
ビニル、ポリカーボネート、ポリスチレン、ポリメチル
メタクリレート、ポリブチルメタクリレート、ポリエス
テル、ポリスルホン、ポリフェニレンオキシド、ポリブ
タジエン、ポリ（Ｎ−ビニルカルバゾール）、炭化水素
樹脂、ケトン樹脂、フェノキシ樹脂、ポリアミド、エチ
ルセルロース、酢酸ビニル、ＡＢＳ樹脂、ポリウレタ
ン、メラミン樹脂、不飽和ポリエステル樹脂、アルキド
樹脂、エポキシ樹脂、シリコン樹脂等が挙げられる。The hole injecting layer and the hole transporting layer may be formed by a vacuum deposition method, an LB method, or a method in which the hole injecting and transporting agent is dissolved or dispersed in a solvent and coated (spin coating, casting, Dip coating method) is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate, ABS resins, polyurethanes, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins and the like.
【００４４】電子注入層、電子輸送層の材料は、陰極か
ら電子を注入する機能、電子を輸送する機能、陽極から
注入された正孔を障壁する機能のいずれか有しているも
のであればよい。その具体例としては、本発明のアゾー
ル誘導体、トリアゾール誘導体、オキサゾール誘導体、
オキサジアゾール誘導体、フルオレノン誘導体、アント
ラキノジメタン誘導体、アントロン誘導体、ジフェニル
キノン誘導体、チオピランジオキシド誘導体、カルボジ
イミド誘導体、フルオレニリデンメタン誘導体、ジスチ
リルピラジン誘導体、ナフタレンペリレン等の複素環テ
トラカルボン酸無水物、フタロシアニン誘導体、８−キ
ノリノール誘導体の金属錯体やメタルフタロシアニン、
ベンゾオキサゾールやベンゾチアゾールを配位子とする
金属錯体に代表される各種金属錯体が挙げられる。電子
注入層、電子輸送層の膜厚は特に限定されるものではな
いが、通常１ｎｍ〜５μｍの範囲のものが好ましく、よ
り好ましくは５ｎｍ〜１μｍであり、さらに好ましくは
１０ｎｍ〜５００ｎｍである。電子注入層、電子輸送層
は上述した材料の１種又は２種以上からなる単層構造で
あってもよいし、同一組成又は異種組成の複数層からな
る多層構造であってもよい。The material of the electron injecting layer and the electron transporting layer is not limited as long as it has a function of injecting electrons from the cathode, a function of transporting electrons, or a function of blocking holes injected from the anode. Good. Specific examples thereof include an azole derivative, a triazole derivative, an oxazole derivative of the present invention,
Heterocyclic tetracarboxylic acids such as oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, and naphthalene perylene Metal complexes and metal phthalocyanines of anhydrides, phthalocyanine derivatives, 8-quinolinol derivatives,
Various metal complexes represented by metal complexes having benzoxazole or benzothiazole as a ligand are exemplified. The thickness of the electron injection layer and the electron transport layer is not particularly limited, but is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 500 nm. The electron injection layer and the electron transport layer may have a single-layer structure composed of one or more of the above-mentioned materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
【００４５】電子注入層、電子輸送層の形成方法として
は、真空蒸着法やＬＢ法、前記電子注入輸送剤を溶媒に
溶解又は分散させてコーティングする方法（スピンコー
ト法、キャスト法、ディップコート法等）等が用いられ
る。コーティング法の場合、樹脂成分と共に溶解又は分
散することができ、樹脂成分としては例えば、正孔注入
輸送層の場合に例示したものが適用できる。The electron injecting layer and the electron transporting layer may be formed by a vacuum deposition method, an LB method, or a method of dissolving or dispersing the electron injecting and transporting agent in a solvent and coating (spin coating, casting, dip coating, etc.). Etc.) are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied.
【００４６】保護層の材料としては水分や酸素等の素子
劣化を促進するものが素子内に入ることを抑止する機能
を有しているものであればよい。その具体例としては、
Ｉｎ、Ｓｎ、Ｐｂ、Ａｕ、Ｃｕ、Ａｇ、Ａｌ、Ｔｉ、Ｎ
ｉ等の金属、ＭｇＯ、ＳｉＯ、ＳｉＯ2、Ａｌ2Ｏ3、Ｇ
ｅＯ、ＮｉＯ、ＣａＯ、ＢａＯ、Ｆｅ2Ｏ3、Ｙ2Ｏ3、Ｔ
ｉＯ2等の金属酸化物、ＭｇＦ2、ＬｉＦ、ＡｌＦ3、Ｃ
ａＦ2等の金属フッ化物、ポリエチレン、ポリプロピレ
ン、ポリメチルメタクリレート、ポリイミド、ポリウレ
ア、ポリテトラフルオロエチレン、ポリクロロトリフル
オロエチレン、ポリジクロロジフルオロエチレン、クロ
ロトリフルオロエチレンとジクロロジフルオロエチレン
との共重合体、テトラフルオロエチレンと少なくとも１
種のコモノマーとを含むモノマー混合物を共重合させて
得られる共重合体、共重合主鎖に環状構造を有する含フ
ッ素共重合体、吸水率１％以上の吸水性物質、吸水率
０．１％以下の防湿性物質等が挙げられる。保護層の形
成方法についても特に限定はなく、例えば真空蒸着法、
スパッタリング法、反応性スパッタリング法、ＭＢＥ
（分子線エピタキシ）法、クラスターイオンビーム法、
イオンプレーティング法、プラズマ重合法（高周波励起
イオンプレーティング法）、プラズマＣＶＤ法、レーザ
ーＣＶＤ法、熱ＣＶＤ法、ガスソースＣＶＤ法、コーテ
ィング法を適用できる。As the material of the protective layer, any material can be used as long as it has a function of preventing a substance which promotes element deterioration such as moisture and oxygen from entering the element. As a specific example,
In, Sn, Pb, Au, Cu, Ag, Al, Ti, N
metal such as i, MgO, SiO, SiO 2 , Al 2 O 3 , G
eO, NiO, CaO, BaO, Fe 2 O 3, Y 2 O 3, T
metal oxides such as iO 2 , MgF 2 , LiF, AlF 3 , C
aF 2 metal fluorides such as, polyethylene, polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, poly-dichloro-difluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, At least one with tetrafluoroethylene
A copolymer obtained by copolymerizing a monomer mixture containing a kind of comonomer, a fluorinated copolymer having a cyclic structure in the copolymer main chain, a water-absorbing substance having a water absorption of 1% or more, a water absorption of 0.1% The following moisture-proof substances are listed. There is no particular limitation on the method of forming the protective layer, for example, a vacuum evaporation method,
Sputtering method, reactive sputtering method, MBE
(Molecular beam epitaxy) method, cluster ion beam method,
An ion plating method, a plasma polymerization method (high-frequency excitation ion plating method), a plasma CVD method, a laser CVD method, a thermal CVD method, a gas source CVD method, and a coating method can be applied.
【００４７】[0047]
【実施例】以下に本発明の具体的実施例を述べるが、本
発明の範囲はこれらに限定されない。 合成例１（本発明のアゾール誘導体例示化合物（１−
１）の合成） ２−メチル−４，５−ジフェニル−１，３−チアゾール
１０ｇ，４−ホルミルフェニル−ジフェニルアミン１
０．９ｇにｔ−ＢｕＯＨ３０ｍｌを加え、室温で撹拌し
た。溶液にｔ−ブトキシカリウム６．７ｇを添加した
後、２時間加熱還流した。溶液を室温に冷却した後、水
１００ｍｌを加え、析出した固体をろ別した。シリカゲ
ルカラムクロマトグラフィー（ヘキサン／酢酸エチル）
で精製し、緑色蛍光を有する例示化合物（１−１）６．
２ｇを得た。また、ＦＡＢ−ＭＳスペクトル（ｐｏｓ
ｉ）で、例示化合物（１−１）の生成を確認した。本合
成例１の反応式を下記に示す。EXAMPLES Specific examples of the present invention will be described below, but the scope of the present invention is not limited to these examples. Synthesis Example 1 (Example compound of azole derivative (1-
Synthesis of 1) 2-methyl-4,5-diphenyl-1,3-thiazole 10 g, 4-formylphenyl-diphenylamine 1
T-BuOH (30 ml) was added to 0.9 g, and the mixture was stirred at room temperature. After adding 6.7 g of potassium t-butoxide to the solution, the mixture was heated under reflux for 2 hours. After the solution was cooled to room temperature, 100 ml of water was added, and the precipitated solid was separated by filtration. Silica gel column chromatography (hexane / ethyl acetate)
5. Exemplified compound (1-1) having green fluorescence
2 g were obtained. In addition, FAB-MS spectrum (pos
In i), generation of the exemplary compound (1-1) was confirmed. The reaction formula of Synthesis Example 1 is shown below.
【００４８】[0048]
【化１１】 Embedded image
【００４９】合成２（本発明のアゾール誘導体例示化合
物（１−２）の合成） ２−メチル−４，５−ジフェニル−１，３−チアゾール
１０ｇ，テレフタルアルデヒド２．６７ｇにｔ−ＢｕＯ
Ｈ３０ｍｌを加え、室温で撹拌した。溶液にｔ−ブトキ
シカリウム８．９ｇを添加した後、２時間加熱還流し
た。溶液を室温に冷却した後、１規定塩酸水１００ｍｌ
を加え、析出したワックス状固体をろ別した。シリカゲ
ルカラムクロマトグラフィー（ヘキサン／酢酸エチル）
で精製し、青緑色蛍光を有する例示化合物（１−２）
３．１ｇを得た。ＦＡＢ−ＭＳスペクトル（ｐｏｓｉ）
で例示化合物（１−２）の生成を確認した。本合成例２
の反応式を下記に示す。Synthesis 2 (Synthesis of Exemplified Compound (1-2) of the Azole Derivative of the Present Invention) 10 g of 2-methyl-4,5-diphenyl-1,3-thiazole and 2.67 g of terephthalaldehyde were added to t-BuO.
H30ml was added and stirred at room temperature. After adding 8.9 g of potassium t-butoxide to the solution, the mixture was refluxed for 2 hours. After cooling the solution to room temperature, 100 ml of 1N hydrochloric acid solution
Was added, and the precipitated waxy solid was separated by filtration. Silica gel column chromatography (hexane / ethyl acetate)
Compound (1-2) having blue-green fluorescence after purification
3.1 g were obtained. FAB-MS spectrum (posi)
The formation of the exemplary compound (1-2) was confirmed. Synthesis Example 2
Is shown below.
【００５０】[0050]
【化１２】 Embedded image
【００５１】＜ＥＬ素子の作製、評価＞ 比較例１ 洗浄したＩＴＯ基板を蒸着装置内に設置し、ＴＰＤ
（Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジトリル−ベンジ
ジン）を４０ｎｍ蒸着した後、下記化合物（ａ）を４０
ｎｍ蒸着し、Ａｌｑ（トリス（８−ヒドロキシキノリナ
ト）アルミニウム）を２０ｎｍ蒸着した。有機薄膜上に
パターニングしたマスク（発光面積が５ｍｍ×５ｍｍと
なるマスク）を設置し、蒸着装置内でマグネシウム：銀
＝１０：１を５０ｎｍ共蒸着した後、銀５０ｎｍを蒸着
した。東陽テクニカ製ソースメジャーユニット２４００
型を用いて、直流定電圧をＥＬ素子に印加し発光させ、
その輝度をトプコン社の輝度計ＢＭ−８、発光波長を浜
松フォトニクス社製スペクトルアナライザーＰＭＡ−１
１を用いて測定した。作製した素子の有機膜は不透明で
あり、また、電圧を印加したところ、微弱な緑色発光が
得られたものの、発光面は不均一であった。<Manufacture and Evaluation of EL Element> Comparative Example 1 A washed ITO substrate was set in a vapor deposition apparatus, and TPD
After (N, N′-diphenyl-N, N′-ditolyl-benzidine) was deposited to a thickness of 40 nm, the following compound (a) was added to 40
Alq (tris (8-hydroxyquinolinato) aluminum) was deposited to a thickness of 20 nm. A mask (a mask having a light emitting area of 5 mm × 5 mm) patterned on the organic thin film was provided, and magnesium: silver = 10: 1 was co-deposited in a vapor deposition apparatus at 50 nm, and then 50 nm of silver was vapor deposited. Toyo Technica Source Measure Unit 2400
Using a mold, apply a DC constant voltage to the EL element to emit light,
The luminance was measured using a luminance meter BM-8 manufactured by Topcon Corporation, and the emission wavelength was measured using a spectrum analyzer PMA-1 manufactured by Hamamatsu Photonics.
1 was measured. The organic film of the manufactured device was opaque, and when a voltage was applied, weak green light emission was obtained, but the light emitting surface was non-uniform.
【００５２】[0052]
【化１３】 Embedded image
【００５３】比較例２ ポリビニルカルバゾール４０ｍｇ，ＰＢＤ（２−（ｐ−
ｔ−ブチルフェニル）−５−ビフェニル−１，３，４−
オキサジアゾール）１２ｍｇ，下記化合物（ｂ）１ｍｇ
をジクロロエタン２ｍｌに溶解し、洗浄したＩＴＯ基板
上にスピンコートした。有機膜の膜厚は、約１３０ｎｍ
であった。有機薄膜上にパターニングしたマスク（発光
面積が５ｍｍ×５ｍｍとなるマスク）を設置し、蒸着装
置内でマグネシウム：銀＝１０：１を５０ｎｍ共蒸着し
た後、銀５０ｎｍを蒸着した。１２Ｖの電圧を印加した
ところ、ＥＬｍａｘ：５０５（ｎｍ）（ｘ，ｙ）＝
（０．２０，０．３８）の緑色発光を得、その最高輝度
は３４１ｃｄ／ｍ2（１８Ｖ）であった。Comparative Example 2 40 mg of polyvinyl carbazole, PBD (2- (p-
t-butylphenyl) -5-biphenyl-1,3,4-
Oxadiazole) 12 mg, the following compound (b) 1 mg
Was dissolved in 2 ml of dichloroethane and spin-coated on the washed ITO substrate. The thickness of the organic film is about 130 nm
Met. A mask (a mask having a light emitting area of 5 mm × 5 mm) patterned on the organic thin film was provided, and magnesium: silver = 10: 1 was co-deposited in a vapor deposition apparatus at 50 nm, and then 50 nm of silver was vapor deposited. When a voltage of 12 V was applied, ELmax: 505 (nm) (x, y) =
Green light emission of (0.20, 0.38) was obtained, and the highest luminance was 341 cd / m 2 (18 V).
【００５４】[0054]
【化１４】 Embedded image
【００５５】実施例１（化合物（１−１）をホスト材料
（電荷輸送材料）、発光材料として利用） 比較例１の化合物（ａ）の代わりに上記合成例１で合成
した化合物（１−１）を用い、比較例１と同様に素子を
作製、評価した。６Ｖの電圧を印加したところ、ＥＬｍ
ａｘ：５０１（ｎｍ）（ｘ，ｙ）＝（０．２２，０．５
０）の緑色発光を得、その最高輝度は３０４０ｃｄ／ｍ
2（９Ｖ）であった。Example 1 (Compound (1-1) used as host material (charge transporting material) and light emitting material) Compound (1-1) synthesized in Synthesis Example 1 above in place of compound (a) in Comparative Example 1 ) Was fabricated and evaluated in the same manner as in Comparative Example 1. When a voltage of 6 V was applied, ELm
ax: 501 (nm) (x, y) = (0.22, 0.5
0) green light emission, and the maximum brightness is 3040 cd / m
2 (9 V).
【００５６】実施例２（化合物（１−１）をドープ色素
として利用） 比較例２の化合物（ｂ）の代わりに合成例２で合成した
例示化合物（１−１）を用い同様に素子作製、評価し
た。１２Ｖの電圧を印加したところ、ＥＬｍａｘ：４９
６（ｎｍ）（ｘ，ｙ）＝（０．２１，０．４８）の緑色
発光を得、その最高輝度は１００３ｃｄ／ｍ2（２２
Ｖ）であった。Example 2 (Compound (1-1) was used as a dope dye) A device was prepared in the same manner as in Comparative Example 2 except that Compound (1-1) synthesized in Synthesis Example 2 was used instead of Compound (b). evaluated. When a voltage of 12 V was applied, ELmax: 49
Green light emission of 6 (nm) (x, y) = (0.21, 0.48) was obtained, and its maximum luminance was 1003 cd / m 2 (22
V).
【００５７】同様に、本発明のアゾール誘導体含有ＥＬ
素子を評価したところ、発光材料、もしくは、ホスト機
能と発光機能を併せ持つ材料として機能することが確認
された。Similarly, the azole derivative-containing EL of the present invention
When the element was evaluated, it was confirmed that the element functioned as a light-emitting material or a material having both a host function and a light-emitting function.
【００５８】[0058]
【発明の効果】本発明のアゾール誘導体は、発光材料、
もしくはホスト機能と発光機能を併せ持つ材料として利
用可能であり、本発明のアゾール誘導体を含有するＥＬ
素子は高輝度発光が可能である。The azole derivative of the present invention comprises a luminescent material,
Alternatively, an EL which can be used as a material having both a host function and a light emitting function and contains the azole derivative of the present invention
The element can emit light with high luminance.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｃ０７Ｄ 417/10 ２７７ Ｃ０７Ｄ 417/10 ２７７ 417/14 ２７７ 417/14 ２７７ Ｃ０９Ｋ 11/06 ６４５ Ｃ０９Ｋ 11/06 ６４５ ６５０ ６５０ ６５５ ６５５ Ｈ０５Ｂ 33/14 Ｈ０５Ｂ 33/14 Ｂ Ｆターム(参考） 3K007 AB02 AB04 BB00 CA01 CA05 CB01 DA00 DB03 EB00 FA01 4C033 AD06 4C056 AA01 AB01 AC02 AD01 AE03 BA11 BB01 BC01 4C063 AA01 BB01 BB03 CC52 CC62 CC94 DD52 DD62 EE05 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) C07D 417/10 277 C07D 417/10 277 417/14 277 417/14 277 C09K 11/06 645 C09K 11/06 645 650 650 655 655 H05B 33/14 H05B 33/14 B F term (reference) 3K007 AB02 AB04 BB00 CA01 CA05 CB01 DA00 DB03 EB00 FA01 4C033 AD06 4C056 AA01 AB01 AC02 AD01 AE03 BA11 BB01 BC01 CC01 CCB DD03 EE05
Claims (5)
導体からなるエレクトロルミネッセンス素子材料。 【化１】 （上記一般式（１）中、Ｒ1，Ｒ2は、同一又は異なっ
て、水素原子又は置換基を表し、Ｒ1及びＲ2の少なくと
もいずれかは、アリール基又は芳香族ヘテロ環基であ
る。Ｒ3，Ｒ4 は、同一又は異なって、水素原子又は置
換基を表す。Ｒ5は、アリール基又は芳香族ヘテロ環基
を表す。Ｘ1は、酸素原子、硫黄原子、置換あるいは無
置換の窒素原子、又は−ＣＲ6（Ｒ7）−を表す。Ｒ6，
Ｒ7 は、同一又は異なって、水素原子又は置換基を表
す。）1. An electroluminescent device material comprising an azole derivative represented by the following general formula (1). Embedded image (In the general formula (1), R 1 and R 2 are the same or different and each represent a hydrogen atom or a substituent, and at least one of R 1 and R 2 is an aryl group or an aromatic heterocyclic group. R 3 and R 4 are the same or different and represent a hydrogen atom or a substituent, R 5 represents an aryl group or an aromatic heterocyclic group, X 1 represents an oxygen atom, a sulfur atom, substituted or unsubstituted nitrogen atoms, or -CR 6 (R 7) - .R 6 representing a
R 7 is the same or different and represents a hydrogen atom or a substituent. )
で表されるアゾール誘導体である請求項１に記載のエレ
クトロルミネッセンス素子材料。 【化２】 （上記一般式（２）中、Ａｒ1，Ａｒ2，Ａｒ4，Ａｒ5
は、同一又は異なって、アリール基又は芳香族ヘテロ環
基を表す。Ａｒ3は、２価芳香族連結基を表す。Ｘ2は、
請求項１に記載の一般式（１）のＸ1と同義である。）2. The azole derivative according to the following general formula (2)
The electroluminescent device material according to claim 1, which is an azole derivative represented by the following formula: Embedded image (In the above general formula (2), Ar 1 , Ar 2 , Ar 4 , Ar 5
Represents the same or different and represents an aryl group or an aromatic heterocyclic group. Ar 3 represents a divalent aromatic linking group. X 2 is,
It has the same meaning as X 1 in the general formula (1). )
ネッセンス素子材料を含有するエレトロルミネッセンス
素子。3. An electroluminescent device comprising the electroluminescent device material according to claim 1 or 2.
ッセンス素子材料の単一化合物層を発光層に有するエレ
クトロルミネッセンス素子。4. An electroluminescent device having a single compound layer of the electroluminescent device material according to claim 1 in a light emitting layer.
ル誘導体。5. A novel azole derivative represented by the general formula (2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10278252A JP2000103786A (en) | 1998-09-30 | 1998-09-30 | Raw material of electroluminescence element and electroluminescence element by using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10278252A JP2000103786A (en) | 1998-09-30 | 1998-09-30 | Raw material of electroluminescence element and electroluminescence element by using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000103786A true JP2000103786A (en) | 2000-04-11 |
Family
ID=17594754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10278252A Pending JP2000103786A (en) | 1998-09-30 | 1998-09-30 | Raw material of electroluminescence element and electroluminescence element by using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2000103786A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007125692A1 (en) | 2006-04-27 | 2007-11-08 | Toyo Ink Mfg. Co., Ltd. | Material for organic electroluminescence element, and organic electroluminescence element |
| CN102924384A (en) * | 2011-08-12 | 2013-02-13 | 财团法人工业技术研究院 | Vinyl group-containing imidazole derivative and use thereof in electroluminescent element |
| WO2019109608A1 (en) * | 2017-12-08 | 2019-06-13 | 昆山国显光电有限公司 | Organic electroluminescent device |
-
1998
- 1998-09-30 JP JP10278252A patent/JP2000103786A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007125692A1 (en) | 2006-04-27 | 2007-11-08 | Toyo Ink Mfg. Co., Ltd. | Material for organic electroluminescence element, and organic electroluminescence element |
| CN102924384A (en) * | 2011-08-12 | 2013-02-13 | 财团法人工业技术研究院 | Vinyl group-containing imidazole derivative and use thereof in electroluminescent element |
| WO2019109608A1 (en) * | 2017-12-08 | 2019-06-13 | 昆山国显光电有限公司 | Organic electroluminescent device |
| US11778902B2 (en) | 2017-12-08 | 2023-10-03 | Kunshan Go-Visionox Opto-Electronics Co., Ltd. | Organic electroluminescent devices |
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