JP4900895B2 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- JP4900895B2 JP4900895B2 JP2005214604A JP2005214604A JP4900895B2 JP 4900895 B2 JP4900895 B2 JP 4900895B2 JP 2005214604 A JP2005214604 A JP 2005214604A JP 2005214604 A JP2005214604 A JP 2005214604A JP 4900895 B2 JP4900895 B2 JP 4900895B2
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- 238000005401 electroluminescence Methods 0.000 title description 11
- 239000000463 material Substances 0.000 claims description 52
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 31
- 229910052796 boron Inorganic materials 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
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- 239000010410 layer Substances 0.000 description 94
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- 238000000034 method Methods 0.000 description 59
- 229910052799 carbon Inorganic materials 0.000 description 40
- 150000001721 carbon Chemical group 0.000 description 28
- 125000001424 substituent group Chemical group 0.000 description 23
- 125000003118 aryl group Chemical group 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 19
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- 125000001072 heteroaryl group Chemical group 0.000 description 15
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- 230000000052 comparative effect Effects 0.000 description 8
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
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- 150000004696 coordination complex Chemical group 0.000 description 4
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
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- 125000004434 sulfur atom Chemical group 0.000 description 4
- 0 Nc(c(*(c(c(N)c(c(N)c1N)N)c1N)c(c(N)c(c(N)c1N)N)c1N)c(c(N)c1N)N)c1N Chemical compound Nc(c(*(c(c(N)c(c(N)c1N)N)c1N)c(c(N)c(c(N)c1N)N)c1N)c(c(N)c1N)N)c1N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
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- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
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- 125000002541 furyl group Chemical group 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
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- 239000011241 protective layer Substances 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 125000005554 pyridyloxy group Chemical group 0.000 description 3
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
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- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
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- 229910000799 K alloy Inorganic materials 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
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- NPRDEIDCAUHOJU-UHFFFAOYSA-N [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical class [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NPRDEIDCAUHOJU-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
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- 125000002252 acyl group Chemical group 0.000 description 1
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- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
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- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical group 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000001769 aryl amino group Chemical group 0.000 description 1
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- 238000007611 bar coating method Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 230000008021 deposition Effects 0.000 description 1
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- 125000000973 dialkylether group Chemical group 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
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- 125000005549 heteroarylene group Chemical group 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 238000007733 ion plating Methods 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- KPWSHFPOXWVUPX-UHFFFAOYSA-N iridium;2,3,4-triphenylpyridine Chemical class [Ir].C1=CC=CC=C1C1=CC=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 KPWSHFPOXWVUPX-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000007759 kiss coating Methods 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N nickel(II) oxide Inorganic materials [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound 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 group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 239000013034 phenoxy resin Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoric acid amide group Chemical group P(N)(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) 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
- 229920003050 poly-cycloolefin Polymers 0.000 description 1
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- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 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
- 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
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 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
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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- 125000006617 triphenylamine group Chemical group 0.000 description 1
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
Description
外部量子効率φ=素子から放出されたフォトン数/素子に注入された電子数
で算出され、この値が大きいほど消費電力の点で有利な素子と言える。
外部量子効率φ=内部量子効率×光取り出し効率
で決まる。有機化合物からの蛍光発光を利用する有機EL素子においては、内部量子効率の限界値が25%であり、光取り出し効率が約20%であることから、外部量子効率の限界値は約5%とされている。
<1>一対の電極間に発光層を含む少なくとも一層の有機化合物層を有する有機電界発光素子であって、該発光層が下記一般式(3)で表される化合物を少なくとも一種含有し、さらに、燐光発光材料を含有することを特徴とする有機電界発光素子。
Ar 31 、Ar 32 はそれぞれペンタフルオロフェニル基を表す。
X 31 は単結合を表す。
Q 31 は、テトラフルオロフェニル基をC=C結合と共に形成する原子群を表す。
Q 32 は、イミダゾール環の窒素原子のうち、ホウ素に配位していない方の窒素原子にメチル基又はフェニル基が置換しているベンズイミダゾール基をN=C結合と共に形成する原子群を表す。
この課題は下記手段によって達成された。
(1)一対の電極間に発光層を含む少なくとも一層の有機化合物層を有する有機電界発光素子であって、該少なくとも一層の有機化合物層が下記一般式(1)で表される化合物を少なくとも一種含有することを特徴とする有機電界発光素子。
(3)一般式(1)で表される化合物が、下記一般式(2)で表される化合物であることを特徴とする上記(1)又は(2)に記載の有機電界発光素子。
い。X31は単結合又は連結基を表す。Q31は芳香族基を表し、Q32は含窒素ヘテロアリール基を表す。
(6)発光層に上記一般式(1)で表される化合物を含有することを特徴とする上記(1)〜(5)のいずれか一項に記載の有機電界発光素子。
内部量子効率=外部量子効率/光取り出し効率
で算出される。通常の有機EL素子では光取り出し効率は約20%であるが、基板の形状、電極の形状、有機層の膜厚、無機層の膜厚、有機層の屈折率、無機層の屈折率等を工夫することにより、光取り出し効率を20%以上にすることが可能である。
.3eV以下であることが好ましく、5.95eV以上、6.25eV以下であることがより好ましく、6.0eV以上6.2eV以下であることがさらに好ましい。
KJ/mol以下) が好ましく、62 Kcal/mol 以上(259.78 KJ/mol 以上)、85 Kcal/mol 以下(356.15 KJ/mol 以下)がより好ましく、65 Kcal/mol 以上(272.35 KJ/mol以上)、80 Kcal/mol 以下(335.2 KJ/mol 以下)がさらに好ましい。
ポリエーテルスルホン、ポリアリレート、アリルジグリコールカーボネート、ポリイミド、ポリシクロオレフィン、ノルボルネン樹脂、ポリ(クロロトリフルオロエチレン)、テフロン(登録商標)、ポリテトラフルオロエチレン−ポリエチレン共重合体等の高分子量材料であっても良い。
陽極の作製には材料によって種々の方法が用いられるが、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−ゲル法など)、酸化インジウムスズの分散物の塗布など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、プラズマ処理などが効果的である。
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、転写法などの方法が用いられ、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。
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、インクジェット法、印刷法、LB法、転写法などの方法が用いられ、好ましくは抵抗加熱蒸着、コーティング法である。
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、前記正孔注入輸送材料を溶媒に溶解又は分散させてコーティングする方法、インクジェット法、印刷法、転写法が用いられる。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、シリコン樹脂などが挙げられる。
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、前記電子注入輸送材料を溶媒に溶解又は分散させてコーティングする方法、インクジェット法、印刷法、転写法などが用いられる。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。
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、印刷法、転写法を適用できる。
洗浄したITO基板を蒸着装置に入れ、銅フタロシアニンを5nm蒸着し、この上に、NPD(N,N’−ジ−α−ナフチル−N,N’−ジフェニル)−ベンジジン)を40nm蒸着した。この上に、Ir(ppy)3と化合物Aを10:90の比率(質量比)で30nm蒸着し、この上に、BAlqを6nm蒸着し、この上に、Alq(トリス(8−ヒドロキシキノリン)アルミニウム錯体)を20nm蒸着した。この上に、フッ化リチウムを3nm蒸着した後、アルミニウム60nmを蒸着し、素子を作製した。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素子に印加して発光させた結果、Ir(ppy)3に由来する緑色発光が得られた。
比較例1の化合物Aの代わりに、本発明の化合物(1−1)を用い、比較例1と同様に素子作製評価した結果、Ir(ppy)3に由来する緑色の発光が得られた。1mA(発光面積4mm2)で駆動した素子の輝度半減期は、比較例1の素子の2倍であった。また、1mA(発光面積4mm2)の電流を流す為に必要な素子の駆動電圧は、約1V低下した。
比較例1の化合物Aの代わりに、本発明の化合物(1−1)と化合物Bの1:1(蒸着レート質量比)の混合物を用い、Ir(ppy)3の代わりに化合物Cを用い、比較例1と同様に素子作製評価した結果、化合物Cに由来する青色の発光が得られた。1mA(発光面積4mm2)で駆動した素子の輝度半減期は、比較例1の素子の3倍であった。また、1mA(発光面積4mm2)の電流を流す為に必要な素子の駆動電圧は、約1.5V低
下した。
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