JP5491330B2 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP5491330B2 JP5491330B2 JP2010199428A JP2010199428A JP5491330B2 JP 5491330 B2 JP5491330 B2 JP 5491330B2 JP 2010199428 A JP2010199428 A JP 2010199428A JP 2010199428 A JP2010199428 A JP 2010199428A JP 5491330 B2 JP5491330 B2 JP 5491330B2
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- unsubstituted
- substituted
- carbon atoms
- metal complex
- Prior art date
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 34
- -1 metal complex compound Chemical class 0.000 claims abstract description 50
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- 239000010409 thin film Substances 0.000 claims abstract description 11
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000010408 film Substances 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 abstract description 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
- 239000010410 layer Substances 0.000 description 57
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 239000000463 material Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 229910052786 argon Inorganic materials 0.000 description 14
- 0 *1C=*2OC3C=CC=CC3C2=C1 Chemical compound *1C=*2OC3C=CC=CC3C2=C1 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000004696 coordination complex Chemical class 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 6
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 229940093475 2-ethoxyethanol Drugs 0.000 description 5
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000008376 fluorenones Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000006862 quantum yield reaction Methods 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
- 229910052703 rhodium Inorganic materials 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OURODNXVJUWPMZ-UHFFFAOYSA-N 1,2-diphenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 OURODNXVJUWPMZ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-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
- VWUDGSYCJGEGOI-UHFFFAOYSA-N 1-methyl-2-phenyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1C1=CC=CC=C1 VWUDGSYCJGEGOI-UHFFFAOYSA-N 0.000 description 1
- OQJQPIWVCBJVAZ-UHFFFAOYSA-N 1-methyl-2-phenylimidazole Chemical compound CN1C=CN=C1C1=CC=CC=C1 OQJQPIWVCBJVAZ-UHFFFAOYSA-N 0.000 description 1
- KTGYDKACJATEDM-UHFFFAOYSA-N 1-methyl-4-phenylimidazole Chemical compound CN1C=NC(C=2C=CC=CC=2)=C1 KTGYDKACJATEDM-UHFFFAOYSA-N 0.000 description 1
- SULWTXOWAFVWOY-PHEQNACWSA-N 2,3-bis[(E)-2-phenylethenyl]pyrazine Chemical class C=1C=CC=CC=1/C=C/C1=NC=CN=C1\C=C\C1=CC=CC=C1 SULWTXOWAFVWOY-PHEQNACWSA-N 0.000 description 1
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 description 1
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical class O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
- IMGQSZWEDCRZTQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-phenylethanone Chemical compound FC1=CC(F)=CC=C1CC(=O)C1=CC=CC=C1 IMGQSZWEDCRZTQ-UHFFFAOYSA-N 0.000 description 1
- ZNRHVRLVJFJFAF-UHFFFAOYSA-N 2-(2,4-difluorophenyl)imidazo[1,2-a]pyridine Chemical compound FC1=CC(F)=CC=C1C1=CN(C=CC=C2)C2=N1 ZNRHVRLVJFJFAF-UHFFFAOYSA-N 0.000 description 1
- AKFOKSAJGCSUBT-UHFFFAOYSA-N 2-bromo-2-(2,4-difluorophenyl)-1-phenylethanone Chemical compound FC1=CC(F)=CC=C1C(Br)C(=O)C1=CC=CC=C1 AKFOKSAJGCSUBT-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 1
- KDHWCFCNNGUJCP-UHFFFAOYSA-N 2-phenylimidazo[1,2-a]pyridine Chemical compound N1=C2C=CC=CN2C=C1C1=CC=CC=C1 KDHWCFCNNGUJCP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical class C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- 101100512896 Arabidopsis thaliana MES2 gene Proteins 0.000 description 1
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Classifications
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Description
devices based on electrophosphorescence" Applied Physics letters Vol. 75 No.1, pp4-6, July 5, 1999) 。
げられる。
Ph及びOLにおけるT1〜T4は、それぞれ独立に、シアノ基、ニトロ基、ハロゲン原子、置換もしくは無置換の炭素数1〜20のアルキル基、置換もしくは無置換のアミノ基、置換もしくは無置換の炭素数1〜20のアルコキシル基、置換もしくは無置換の炭素数1〜20のアルキルシリル基、置換もしくは無置換の炭素数1〜20のアシル基、又は置換もしくは無置換の炭素数1〜30の芳香族基を表していてもよく、これら各基及びこれらの置換基の例としては、前記一般式(I)のR1〜R5で説明したものと同じであり、好ましい例としても同様のものが挙げられる。
い。また、通常、前記発光層は真空蒸着又は塗布により薄膜化するが、塗布の方が製造プロセスが簡略化できることから、本発明の金属錯体化合物を含有する層が、塗布により成膜されてなると好ましい。
のであればよい。その具体例としては、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、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、ペリレン等の芳香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、有機シラン誘導体、本発明の金属錯体化合物等が挙げられる。また、前記電子注入層及び前記電子輸送層は、前記材料の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。
実施例1(金属錯体化合物1−1の合成)
金属錯体化合物1−1の合成経路を以下に示す。
(1)中間体1−1bの合成
フラスコに2 −アミノピリジン 3.5g(36mmol) 、α−ブロモアセトフェノン 7.2g(36mmol) 及び炭酸水素ナトリウム 3.6g(43mmol) を入れ、エタノール120ml 中、室温にて4時間、次いで還流下で2時間反応させた。不溶物をろ別し、ろ液を濃縮した。塩化メチレン150ml にて抽出し、水 200mlにて3回洗浄した。有機層を硫酸マグネシウムで乾燥した後、溶媒を除き、茶色の結晶を得た。シリカゲルカラム(ヘキサン/ 塩化メチレン)で精製を行い、2−フェニルイミダゾ[1,2-a] ピリジン中間体1−1bを白色結晶として、6.3g得た(収率90%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CDCl3) :δ 7.8-8.3 (m,4H),δ7.0-8.3 (m,5H), δ .6-6.9 (m,1H)
(2)中間体1−1aの合成
フラスコに1−1b 5.0g(25.7mmol) 、IrCl3 水和物(strem製) 1.9g(6.4mmol)を入れ、アルゴン置換し、2 −エトキシエタノール 40ml を入れ、還流下15時間反応させた。得られた黄色沈殿をろ別し、エタノール 5mlで2回洗浄した。さらに塩化メチレン 150mlに溶解させ、HCl水溶液で3回、水で2回洗浄を行った。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、黄色結晶として、中間体1−1aを1.39g 得た(収率35%)。
(3)金属錯体化合物1−1の合成
フラスコに中間体1−1a 1.39g(1.13mmol)、2−ピコリン酸 0.55g(4.52mmol)を入れ、アルゴン置換し、1 ,2 −ジクロロエタン20mlを入れて、還流下で17時間反応させた。得られた黄色沈殿をろ別し、塩化メチレン 400mlに溶解させ、水150ml にて3回洗浄した。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、少量の塩化メチレンで洗って、黄色結晶として金属錯体化合物1−1を0.85g 得た(収率54%)。FD−MS(フィールドディソープションマス分析)により目的物であることを確認した。また、測定結果を以下に示す。
FD-MS : m/z=701
また、得られた金属錯体化合物1−1のりん光を測定(塩化メチレン溶液)したところ、りん光のλmax(最大発光強度の波長)は580nm であった。
実施例2(金属錯体化合物1−2の合成)
金属錯体化合物1−2の合成経路を以下に示す。
(1)中間体1−2cの合成
2 ,4 −ジフルオロフェニルアセトフェノン 25g(160.1mmol) の酢酸 50ml 溶液を10℃以下に冷却しながら、臭素 25.5g(160.1mmol) を適下し、7時間反応を行った。生成溶液を水300ml に投入し、塩化メチレンで抽出した。有機層を塩化マグネシウムで乾燥した後、溶媒を除いた。得られた残渣をシリカカラム精製 (ヘキサン) し、褐色オイルとして、α−ブロモ−2 ,4 −ジフルオロフェニルアセトフェノン中間体1−2cを23.4g 得た(収率62%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CDCl3) :δ 7.87-8.14 (m,1H),δ 6.8-7.13 (m,2H), δ 4.49 (d,2H)
(2)中間体1−2bの合成
フラスコに2−アミノピリジン 3.3g(35.5mmol) 、中間体1−2c 8.4g(35.5mmol) 及び炭酸水素ナトリウム 3.6g (43mmol)を入れ、エタノール120ml 中、室温にて4時間、次いで還流下で2時間反応させた。不溶物をろ別し、ろ液を濃縮した。塩化メチレン150ml にて抽出し、水 200mlにて3回洗浄した。有機層を硫酸マグネシウムで乾燥した後、溶媒を除き、茶色の結晶を得た。シリカゲルカラム(ヘキサン/塩化メチレン)で精製を行い、2 ‐(2’,4’‐ジフルオロフェニル) イミダゾ[1,2-a] ピリジン中間体1−2bを7.3g得た(収率89%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CDCl3) :δ 7.9-8.45 (m,3H), δ 7.5-7.7 (m,1H), δ 6.7-7.28 (m, 4H)
(3)中間体1−2aの合成
フラスコに中間体1−2b 4.7g(20.6mmol) 、IrCl3 水和物(strem製) 1.53g(5.1mmol)を入れ、アルゴン置換し、2−エトキシエタノール 25ml を入れ、還流下15時間反応させた。得られた淡黄色沈殿をろ別し、エタノール 5mlで2回洗浄した。さらに塩化メチレン 150mlに溶解させ、HCl水溶液で3回、水で2回洗浄を行った。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、黄色結晶として、中間体1−2aを1.39g 得た(収率35%)。
(4)金属錯体化合物1−2の合成
フラスコに中間体1−2a 1.39g(1.13mmol)、2 −ピコリン酸 0.55g(4.52mmol)を入れ、アルゴン置換した。1 ,2 −ジクロロエタン20mlを入れて、還流下で17時間反応させた。得られた黄色沈殿をろ別し、塩化メチレン 400mlに溶解させ、水150ml にて3回洗浄した。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、少量の塩化メチレンで洗って、黄色結晶として金属錯体化合物1−2を0.85g 得た(収率54%)。 1H−NMR及びFD−MSにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CDCl3) :δ 7.84-8.30 (m,7H),δ 7.2-7.47 (m,2H), δ 6.7-7.0 (m, 3H), δ 6.2-6.6 (m,2H),δ 5.44-5.88 (m,4H)
FD-MS : m/z=773
また、得られた金属錯体化合物1−2のりん光を測定(塩化メチレン溶液)したところ、りん光のλmaxは529nm であった。
実施例3(金属錯体化合物6−1の合成)
金属錯体化合物6−1の合成経路を以下に示す。
(1)中間体6−1bの合成
滴下漏斗を備えたフラスコに2−フェニルイミダゾール 8.6g(60mmol) を入れ、アルゴン置換した後にテトラヒドロフラン 180mlを入れた。氷冷下で1.56mol/l のn−ブチルリチウム 39.1ml(61mmol) を約30分かけて滴下し、ついでテトラヒドロフラン 10ml に溶解したヨウ化メチル 8.6g(61mmol) を滴下した。滴下終了後、室温にて3時間反応させた。反応溶液を濃縮した後、得られた固体を塩化メチレン150ml にて抽出し、水 150mlにて3回洗浄した。有機層を硫酸マグネシウムで乾燥した後、溶媒を除いた。シリカゲルカラム(ヘキサン/塩化メチレン)で精製を行い、1−メチル−2−フェニルイミダゾール中間体6−1bを白色結晶として、6.1g得た(収率69%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CDCl3) :δ 7.29-7.67 (m,5H),δ 6.93-7.10 (m,2H),δ 3.69 (s,3H)
(2)中間体6−1aの合成
フラスコに中間体6−1b 4.1g(26.2mmol) 、IrCl3 水和物(strem製) 1.95g(6.5mmol)を入れ、アルゴン置換し、2 −エトキシエタノール 30ml を入れ、還流下11時間反応させた。得られた黄色沈殿をろ別し、エタノール 5mlで2回洗浄した。さらに塩化メチレン600ml に溶解させ、水200ml で3回洗浄を行った。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、淡黄色結晶として、中間体6−1aを1.35g 得た(収率38%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CD2Cl2) :δ 7.26-7.42(m,2H),δ 6.47-6.94 (m,3H), δ 6.0-6.09 (m,1H),δ 4.13 (s,3H)
(3)金属錯体化合物6−1の合成
フラスコに中間体6−1a 1.32g(1.21mmol)、2 −ピコリン酸 0.59g(4.87mmol)を入れ、アルゴン置換した。1 ,2 ‐ジクロロエタン15mlを入れて、還流下で8時間反応させた。得られた黄色沈殿をろ別し、塩化メチレン 200mlに溶解させ、水150ml にて4回洗浄した。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、塩化メチレン/ヘキサンから再結晶した。黄色結晶として金属錯体化合物6−1を1.17g 得た(収率78%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CDCl3) :δ 8.1-8.2(m,1H),δ 7.75-7.90 (m,2H), δ 7.2-7.51 (m,3H) , δ 6.3-7.0 (m,9H), δ 6.13 (d,1H),δ 4.06 (s,3H)
また、得られた金属錯体化合物6−1のりん光を測定(塩化メチレン溶液)したところ、りん光のλmaxは562nm であった。
比較例1
フラスコに4−フェニルイミダゾール3.8g(26.3mmol)、IrCl3 水和物(strem製) 1.96g(6.6mmol)を入れ、アルゴン置換した。2−エトキシエタノール 30ml を入れ、還流下18時間反応させたところ、沈殿物はなく、均一の黒褐色の溶液となった。溶媒を留去さ
せ、溶液を処理したところ、黒色固形物が得られたが、目的のIr金属錯体化合物(下記Q)とは確認できなかった。実施例3と比較すると、以下に示すように、イミダゾールのN位にHが存在すると、Ir錯体の合成が困難であり、メチル基等の何らかの置換基が必要である。
金属錯体化合物7−1の合成経路を以下に示す。
(1)中間体7−1bの合成
滴下漏斗を備えたフラスコに2−フェニルイミダゾリン 8.9g(60.8mmol) を入れ、アルゴン置換した後にテトラヒドロフラン 210mlを入れた。氷冷下で1.56mol/l のn−ブチルリチウム 39.3ml(61.2mmol) を約30分かけて滴下し、ついでテトラヒドロフラン 10ml に溶解したヨウ化メチル 8.7g(61.3mmol) を滴下した。滴下終了後、室温にて3時間反応させた。反応溶液を濃縮した後、得られた固体を塩化メチレン150ml にて抽出し、水 150mlにて3回洗浄した。有機層を硫酸マグネシウムで乾燥した後、溶媒を除いた。シリカゲルカラム(ヘキサン/塩化メチレン)で精製を行い、1−メチル−2−フェニルイミダゾリン中間体7−1bを白色結晶として8.0g得た(収率83%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (CDCl3) :δ 7.33-7.60 (m,5H),δ 3.27-3.98 (m,4H),δ 2.76 (s,3H)
(2)中間体7−1aの合成
フラスコに中間体7−1b 4.4g(27.5mmol) 、IrCl3 水和物(strem製) 2.1g(6.9mmol) を入れ、アルゴン置換した。2−エトキシエタノール 30ml を入れ、還流下16時間反応させた。得られた黄色沈殿をろ別し、エタノール 5mlで2回洗浄した。さらに塩化メチレン200ml に溶解させ、水200ml で4回洗浄を行った。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、オレンジ色結晶として、中間体7−1aを2.1g得た (収率57%)。 1H−NMRにより目的物であることを確認した。その測定結果を以下に示す。
1H-NMR (DMSO-d6) :δ 7.51-7.61 (m,1H), δ 6.69-6.97 (m,3H), δ 3.60-4.1 (m,4H),δ 3.33 (s,3H)
(3)金属錯体化合物7−1の合成
フラスコに中間体7−1a 1.95g(1.78mmol)、2 −ピコリン酸 0.88g(7.14mmol)を入れ、アルゴン置換した。1 ,2 ‐ジクロロエタン20mlを入れて、還流下で17時間反応させた。反応溶液から溶媒を除き、得られた褐色固体を塩化メチレン 150mlに溶解させ、水200ml にて5回洗浄した。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、シリカカ
ラム(塩化メチレン/メタノール)により精製した。茶色結晶として7−1を1.2g得た (収率53%)。FD−MSにより目的物であることを確認した。その測定結果を以下に示す。FD-MS : m/z=632
また、得られた金属錯体化合物7−1のりん光を測定(塩化メチレン溶液)したところ、りん光のλmaxは562nm であった。
実施例5(金属錯体化合物5−1の合成)
金属錯体化合物5−1の合成経路を以下に示す。
滴下漏斗を備えたフラスコに4−フェニルイミダゾール9.6g(67mmo1)を入れ、アルゴン置換した後にジメチルスルホキシド50m1を入れた。この溶液にNaH 2.8g(60% in oil,70mmo1 相当) を少しずつ入れ、すべて添加後に80℃で2時間加熱した。ついで、メチルスルホキシド15mlに溶解させたよう化メチル9.6g(68mmol ) を滴下し、80℃でさらに15時間加熱した。
(2)中間体5−1aの合成
フラスコに中間体5−1b 3.Og(18.9mmo1) 、IrCl3 水和物(strem製) 1.41g(4.7mmol)を入れ、アルゴン置換した。2−エトキシエタノール15mlを入れ、還流下13時間反応させた。得られた白色沈殿をろ別し、エタノール5m1 で2回洗浄した。さらに塩化メチレン500ml に溶解させ、水150m1 で3回洗浄を行った。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去し、白色結晶として、中間体5−1aを1.77g 得た(収率69%)。
(3)金属錯体化合物5−1の合成
フラスコに中間体5−1a 1.38g(1.27mmo1)、2−ピコリン酸0.62g(5.1mmol)を入れ、アルゴン置換した。1,2−ジクロロエタン20m1を入れて、還流下で12時間反応させた。得られた黄色沈殿をろ別し、塩化メチレン300ml に溶解させ、水200ml にて4回洗浄した。溶液を硫酸マグネシウムで乾燥させた後、溶媒を留去した。得られた黄色結晶をシリカゲルカラム(塩化メチレンノメタノール) で精製した。淡黄色結晶として5−1を0.4g得た(収率26%)。
実施例6(有機EL素子の作製)
25mm×75mm×0.7mm厚のITO透明電極付きガラス基板をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行なった。洗浄後の透明電極付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極が形成されている側の面上に前記透明電極を覆うようにして膜厚40nmの下記4,4’−ビス[N−(4−ビフェニル)−N−(4−ビフェニル)アミノ]ビフェニルを成膜した。
この膜は正孔輸送層として機能する。さらに、この膜上に膜厚30nmで下記ホスト材料(CBP)と、同時にドーパントとしてりん光発光性のIr金属錯体化合物1−2を添加して蒸着し成膜した。この膜は、発光層として機能する。発光層中における化合物1−1の濃度は5重量%とした。この膜上に膜厚10nmの(1,1’−ビスフェニル)−4−オラート)ビス(2−メチル−8−キノリノラート)アルミニウム(BAlq)を成膜した。このBAlq膜は正孔障壁層として機能する。さらにこの膜上に膜厚30nmの8−ヒドロキシキノリンのアルミニウム錯体(Alq)を成膜した。このAlq膜は電子注入層として機能する。この後、ハロゲン化アルカリ金属であるLiFを0.15nmの厚さに蒸着し、次いでアルミニウムを150nmの厚さに蒸着した。このAl/LiFは陰極として機能する。このようにして有機EL素子を作製した。
Claims (5)
- 一対の電極間に少なくとも発光層を有する一層又は複数層からなる有機薄膜層が挟持されている有機エレクトロルミネッセンス素子において、該有機薄膜層の少なくとも1層が、下記1a〜3a及び5a〜7aのいずれかで表される部分構造を有する金属錯体化合物(ただし、下記化合物6を除く)を含有し、両極間に電圧を印加することにより発光する有機エレクトロルミネッセンス素子。
Mは、イリジウム(Ir)又は白金(Pt)の金属原子である。
Gは下記の基のうちのいずれかで表される基である。
(Ph及びOLにおけるT 1 〜T 4 は、それぞれ独立に、水素原子、シアノ基、ニトロ基、ハロゲン原子、置換もしくは無置換の炭素数1〜20のアルキル基、置換もしくは無置換のアミノ基、置換もしくは無置換の炭素数1〜20のアルコキシル基、置換もしくは無置換の炭素数1〜20のアルキルシリル基、又は置換もしくは無置換の炭素数1〜20のアシル基を表す。)
T 1 〜T 9 が置換基を有する場合、当該置換基は、シアノ基、ヒドロキシル基、ニトロ基、ハロゲン原子、無置換のアルキル基、無置換のアミノ基、無置換のアルコキシル基、無置換のアルキルシリル基、無置換のアシル基、又は無置換の芳香族基、無置換のアルケニル基、無置換のシクロアルキル基、無置換の複素環基、無置換のアリールアルキル基、無置換のアリールオキシ基、無置換のアルコキシカルボニル基、及びカルボキシル基から選択される。]
- 前記金属錯体化合物が、前記一般式1a〜3a、5a、及び7aのいずれかで表される部分構造を有する請求項1に記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、前記一般式(I)で表される部分構造を有する金属錯体化合物を含有する請求項1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 前記一般式(I)で表される部分構造を有する金属錯体化合物を含有する層が、塗布により成膜されてなる請求項1〜4のいずれか1項に記載の有機エレクトロルミネッセンス素子。
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- 2004-07-21 KR KR1020067001402A patent/KR101046847B1/ko active IP Right Grant
- 2004-07-21 EP EP10182596.6A patent/EP2336142B1/en not_active Not-in-force
- 2004-07-21 CN CN2011103508712A patent/CN102516312A/zh active Pending
- 2004-07-22 TW TW093121962A patent/TW200504183A/zh unknown
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2010
- 2010-02-18 US US12/656,892 patent/US8106390B2/en not_active Expired - Fee Related
- 2010-09-06 JP JP2010199428A patent/JP5491330B2/ja not_active Expired - Fee Related
- 2010-09-30 US US12/923,633 patent/US8178874B2/en not_active Expired - Fee Related
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2012
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EP2336142A2 (en) | 2011-06-22 |
US8178874B2 (en) | 2012-05-15 |
EP2336142A3 (en) | 2011-12-21 |
EP2336142B1 (en) | 2013-09-04 |
EP1647554A4 (en) | 2008-02-20 |
US20110017984A1 (en) | 2011-01-27 |
TW200504183A (en) | 2005-02-01 |
CN1829724B (zh) | 2012-10-10 |
TWI332977B (ja) | 2010-11-11 |
EP1647554B1 (en) | 2011-08-31 |
WO2005007767A2 (ja) | 2005-01-27 |
CN1829724A (zh) | 2006-09-06 |
US7667228B2 (en) | 2010-02-23 |
CN102516312A (zh) | 2012-06-27 |
KR20060059969A (ko) | 2006-06-02 |
EP1647554A2 (en) | 2006-04-19 |
US20100155713A1 (en) | 2010-06-24 |
US20060197077A1 (en) | 2006-09-07 |
US20120169219A1 (en) | 2012-07-05 |
JPWO2005007767A1 (ja) | 2006-08-31 |
ATE522539T1 (de) | 2011-09-15 |
JP4891615B2 (ja) | 2012-03-07 |
KR101046847B1 (ko) | 2011-07-06 |
WO2005007767A3 (ja) | 2005-03-31 |
JP2011029647A (ja) | 2011-02-10 |
US8106390B2 (en) | 2012-01-31 |
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