JP4593631B2 - 有機電界発光素子用化合物及び有機電界発光素子 - Google Patents
有機電界発光素子用化合物及び有機電界発光素子 Download PDFInfo
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- JP4593631B2 JP4593631B2 JP2007547906A JP2007547906A JP4593631B2 JP 4593631 B2 JP4593631 B2 JP 4593631B2 JP 2007547906 A JP2007547906 A JP 2007547906A JP 2007547906 A JP2007547906 A JP 2007547906A JP 4593631 B2 JP4593631 B2 JP 4593631B2
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- 150000001875 compounds Chemical class 0.000 title claims description 64
- 238000005401 electroluminescence Methods 0.000 title claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 33
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000005647 linker group Chemical group 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 8
- -1 diaralkylamino group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000004986 diarylamino group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 118
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 30
- 239000010409 thin film Substances 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000000843 powder Substances 0.000 description 22
- 239000013078 crystal Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 229910052757 nitrogen Chemical group 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000011521 glass Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001771 vacuum deposition Methods 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 7
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 7
- 229940125851 compound 27 Drugs 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 4
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 4
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000004984 aromatic diamines Chemical class 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
- 0 c(cc1)ccc1-[n]1c2c(*(c3ccccc3-3)c(cc4)ccc4-c4cc(-[n]5c(c6c(cc7)c(cccc8)c8[n]6-c6ccccc6)c7c6c5cccc6)cc(-c(cc5)ccc5-[n]5c(c6c(cc7)c(cccc8)c8[n]6-c6ccccc6)c7c6c5cccc6)c4)c-3ccc2c2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c2c(*(c3ccccc3-3)c(cc4)ccc4-c4cc(-[n]5c(c6c(cc7)c(cccc8)c8[n]6-c6ccccc6)c7c6c5cccc6)cc(-c(cc5)ccc5-[n]5c(c6c(cc7)c(cccc8)c8[n]6-c6ccccc6)c7c6c5cccc6)c4)c-3ccc2c2c1cccc2 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- WZVWSOXTTOJQQQ-UHFFFAOYSA-N 2-bromo-6-(6-bromopyridin-2-yl)pyridine Chemical group BrC1=CC=CC(C=2N=C(Br)C=CC=2)=N1 WZVWSOXTTOJQQQ-UHFFFAOYSA-N 0.000 description 1
- LUEYUHCBBXWTQT-UHFFFAOYSA-N 4-phenyl-2h-triazole Chemical group C1=NNN=C1C1=CC=CC=C1 LUEYUHCBBXWTQT-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- NGFUATIZGUOJIC-UHFFFAOYSA-N C(C1)C=Cc2c1c(ccc(c1ccccc11)c3[n]1-c1ccccc1)c3[n]2-c1cc(N(c2cccc(-[n]3c(c4c(cc5)c6ccccc6[n]4-c4ccccc4)c5c4c3cccc4)c2)c2cc(-[n](c3ccccc3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)ccc2)ccc1 Chemical compound C(C1)C=Cc2c1c(ccc(c1ccccc11)c3[n]1-c1ccccc1)c3[n]2-c1cc(N(c2cccc(-[n]3c(c4c(cc5)c6ccccc6[n]4-c4ccccc4)c5c4c3cccc4)c2)c2cc(-[n](c3ccccc3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)ccc2)ccc1 NGFUATIZGUOJIC-UHFFFAOYSA-N 0.000 description 1
- OXCNRZVOFHIOKS-UHFFFAOYSA-N C1(=CC=CC=C1)N1N(N(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)N1N(N(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 OXCNRZVOFHIOKS-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Description
Zは置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基からなる連結基を示し、
nは2又は3の数を示し、
Yは下記式(1a)で表わされる基を示す、
環Aは隣接環と縮合する式(1b)で表わされる芳香族環を示し、
環Bは隣接環と縮合する式(1c)で表わされる複素環を示し、
Xは炭素を示し、
R43は、水素、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、
R44は置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、
R41、R42は、水素、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、置換又は未置換の芳香族炭化水素基又は芳香族複素環基を示す。
ここで、
環A、環A’は隣接環と縮合する式(2a)で表される芳香環を示し、
環B、環B’は隣接環と縮合する式(2b)で表される複素環を示す。
ここで、
環C、環C’は隣接環と縮合する式(3a)で表される芳香環を示し、
環D、環D’は隣接環と縮合する式(3b)表される複素環を示し、
環E、環E’は隣接環と縮合する式(3c)で表される複素環を示す。
Xは炭素又は窒素を示し、
R5、R13、R17、R20、R45は独立に、水素、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、
R6、R14〜R15、R22〜R23、R30〜R32、R44、R46は独立に、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、
Ar1〜Ar4は独立に、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基からなる2価の連結基を示し、
R1〜R4、R7〜R12、R16、R18〜R19、R21、R24〜R29、R41〜R42、R47〜R48は独立に、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、置換又は未置換の芳香族炭化水素基又は芳香族複素環基を示す。
式(1b)中のXを含む6員環に縮合する環である場合、この環は縮合環であってもよい。縮合環である場合の例としては、一般式(3)及び(5)中の縮合環を有する環E、E’及び環F、F’がある。すなわち、R9、R12、R25又はR28を有してもよいインドール環が好ましい。この場合、インドール環中の含窒素環がXを含む6員環に縮合する。
2 陽極
3 正孔注入層
4 正孔輸送層
5 発光層
6 電子輸送層
7 陰極
(化合物9の合成)
脱気窒素置換した200ml三口フラスコに1,2-シクロヘキサンジオン5.0g(44.59mmol)、フェニルヒドラジン塩酸塩12.9g(89.21mmol)を加え、これにエタノール145mlを加えて攪拌させた。その後、同フラスコ内に濃硫酸0.45g(4.59mmol)を5分間かけ滴下した。その後65℃まで加熱し、4時間攪拌した。室温まで冷却した後、生じた紫茶色結晶を濾取した後、濾取した結晶をエタノール50mlで二回、リスラリー洗浄をおこなった。これを、減圧乾燥して紫茶色粉末12.0g(43.59mmol、収率97.7%)を得た。
次に、300ml三口フラスコに上記紫茶色粉末12.0g(43.59mmol)を加え、これに酢酸140g、トリフルオロ酢酸8.0gを加えて攪拌させた。その後100℃まで加熱し、15時間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢酸200mlでリンス洗浄をおこなった後、ヘキサン200mlでリンス洗浄をおこなった。これを、減圧乾燥して白色粉末5.0g(19.51mmol、収率44.4%)を得た。
化合物9のEI−MS(M+1)は814、融点は398℃であった。
(化合物40の合成)
脱気窒素置換した2000ml三口フラスコに1,2-シクロヘキサンジオン33.3g(297.0mmol)、フェニルヒドラジン塩酸塩86.0g(594.7mmol)を加え、これにエタノール1000mlを加えて攪拌させた。その後、同フラスコ内に濃硫酸3.0g(30.6mmol)を5分間かけ滴下した。その後65℃まで加熱し、4時間攪拌した。室温まで冷却した後、生じた紫茶色結晶を濾取した後、濾取した結晶をエタノール500mlで二回、リスラリー洗浄をおこなった。これを、減圧乾燥して紫茶色粉末80.0g(280.5mmol、収率96.3%)を得た。
次に、1000ml三口フラスコに上記紫茶色粉末72.0g(261.5mmol)を加え、これに酢酸720g、トリフルオロ酢酸72.0gを加えて攪拌させた。その後100℃まで加熱し、15時間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢酸200mlでリンス洗浄をおこなった後、ヘキサン200mlでリンス洗浄をおこなった。これを、減圧乾燥して白色粉末30.0g(117.1mmol、収率44.8%)を得た。
次に、脱気窒素置換した500ml三口フラスコに55%水素化ナトリウム2.16g(49.5mmol)、脱水N,N’-ジメチルホルムアミド70mlを加え、窒素気流中下で攪拌を行う。上記で得た白色粉末13.7g(41.2mmol)に脱水N,N’-ジメチルホルムアミド70mlを加え、溶解させ、その後、同フラスコ内に15分間かけ滴下した。滴下終了後、1時間攪拌を継続した。その後、塩化シアヌル3.76g(20.4mmol)に脱水N,N’-ジメチルホルムアミド70mlを加え、溶解させ、その後、同フラスコ内に15分間かけ滴下した。滴下終了後、2時間攪拌を継続した後、水350gを加え、析出した結晶を濾取した。濾取した結晶を水300gで二回リスラリーを行い、その後、メタノール300gにてリスラリーを行った。これを減圧乾燥した後、カラムクロマトグラフィーで精製して白色粉末10.9g(14.0mmol、収率70.0%)を得た。
化合物40のEI−MS(M+1)は818、融点は未検出であった。
(化合物27の合成)
脱気窒素置換した2000ml三口フラスコに1,2-シクロヘキサンジオン33.3g(297.0mmol)、フェニルヒドラジン塩酸塩86.0g(594.7mmol)を加え、これにエタノール1000mlを加えて攪拌させた。その後、同フラスコ内に濃硫酸3.0g(30.6mmol)を5分間かけ滴下した。その後65℃まで加熱し、4時間攪拌した。室温まで冷却した後、生じた紫茶色結晶を濾取した後、濾取した結晶をエタノール500mlで二回、リスラリー洗浄をおこなった。これを、減圧乾燥して紫茶色粉末80.0g(280.5mmol、収率96.3%)を得た。
次に、1000ml三口フラスコに上記紫茶色粉末72.0g(261.5mmol)を加え、これに酢酸720g、トリフルオロ酢酸72.0gを加えて攪拌させた。その後100℃まで加熱し、15時間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢酸200mlでリンス洗浄をおこなった後、ヘキサン200mlでリンス洗浄をおこなった。これを、減圧乾燥して白色粉末30.0g(117.1mmol、収率44.8%)を得た。
次に、脱気窒素置換した2000ml三口フラスコに上記で得た白色粉末13.7g(41.2mmol)、6,6’-ジブロモ-2,2’-ビピリジル6.4g(20.4mmol)、よう化銅1.14g(5.98mmol)、リン酸三カリウム25.22g(118.8mmol)これに1,4-ジオキサン200mlを加えて攪拌させた。攪拌を継続しながらtranc-1,2-シクロヘキサンジアミン10mlを加えた。その後115℃まで加熱し、15時間攪拌した。一旦、室温まで冷却した後、不溶物を濾取した。濾液を減圧留去した後、メタノールを加え、析出した白色固体を濾取した。その後、カラムクロマトグラフィーで精製して白色固体5.0g(6.14mmol、収率30.0%)を得た。
化合物27のEI−MS(M+1)は816、融点は362℃であった。
ガラス基板上に真空蒸着法にて、真空度4.0×10-4Paの条件にて化合物9を蒸着源から蒸着し、薄膜を1.0Å/秒にて50nmの厚さで形成した。作成した薄膜を、蛍光測定装置にて評価した。
次にガラス基板上に真空蒸着法にて、真空度4.0×10-4 Pa の条件にて化合物9とIr(ppy)3とを異なる蒸着源から蒸着し、Ir(ppy)3の濃度が7.0 %であるような薄膜を1.0Å/秒にて50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物9の極大吸収波長を使用し、そのときに出てくる光を観察し、化合物9単独の薄膜の場合に出てくる光と比較した。結果を表1に示す。
ガラス基板上に真空蒸着法にて、真空度4.0×10-4Paの条件にて化合物40を蒸着源から蒸着し、薄膜を1.0Å/秒にて50nmの厚さで形成した。作成した薄膜を、蛍光測定装置にて評価した。
次にガラス基板上に真空蒸着法にて、真空度4.0×10-4 Pa の条件にて化合物40とIr(ppy)3とを異なる蒸着源から蒸着し、Ir(ppy)3の濃度が7.0 %であるような薄膜を1.0Å/秒にて50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物40の極大吸収波長を使用し、そのときに出てくる光を観察し、化合物40単独の薄膜の場合に出てくる光と比較した。結果を表1に示す。
ガラス基板上に真空蒸着法にて、真空度4.0×10-4Paの条件にて化合物27を蒸着源から蒸着し、薄膜を1.0Å/秒にて50nmの厚さで形成した。作成した薄膜を、蛍光測定装置にて評価した。
次にガラス基板上に真空蒸着法にて、真空度4.0×10-4 Pa の条件にて化合物27とIr(ppy)3とを異なる蒸着源から蒸着し、Ir(ppy)3の濃度が7.0 %であるような薄膜を1.0Å/秒にて50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物27の極大吸収波長を使用し、そのときに出てくる光を観察し、化合物27単独の薄膜の場合に出てくる光と比較した。結果を表1に示す。
薄膜主成分をAlq3に変えて薄膜を作成した以外は、実施例4と同様に行った。結果を表1に示す。表1から発光層の主たる材料に化合物9、40及び27を用いた場合、Ir(ppy)3にエネルギーが遷移し、Ir(ppy)3からの発光が観察されるが、Alq3を用いた場合は、Ir(ppy)3にエネルギーが遷移せず、Alq3自身が蛍光を発することがわかる。
図1において、正孔注入層を省略し、電子注入層を追加した構成の有機EL素子を作成した。膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔輸送層としてNPBを60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物9とIr(ppy)3とを異なる蒸着源から、共蒸着し、25nmの厚さに形成した。この時、Ir(ppy)3の濃度は7.0 %であった。次に、電子輸送層としてAlq3を50nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
図1において、正孔注入層を省略し、電子注入層を追加した構成の有機EL素子を作成した。膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔輸送層としてNPBを60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物40とIr(ppy)3とを異なる蒸着源から、共蒸着し、25nmの厚さに形成した。この時、Ir(ppy)3の濃度は7.0 %であった。次に、電子輸送層としてAlq3を50nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
図1において、正孔注入層を省略し、電子注入層を追加した構成の有機EL素子を作成した。膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔輸送層としてNPBを60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物27とIr(ppy)3とを異なる蒸着源から、共蒸着し、25nmの厚さに形成した。この時、Ir(ppy)3の濃度は7.0 %であった。次に、電子輸送層としてAlq3を50nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
正孔輸送層としてHMTPDを、発光層の主成分としてTAZを用いた以外は実施例7と同様にして有機EL素子を作成した。
発光層の主成分として、TAZを用いた以外は実施例7と同様にして有機EL素子を作成した。
(化合物103の合成)
脱気窒素置換した200ml三口フラスコに1,2-シクロヘキサンジオン33.3g(0.297mol)、フェニルヒドラジン塩酸塩86.0g(0.595mol)を加え、これにエタノール1000mlを加えて攪拌させた。その後、同フラスコ内に濃硫酸3.0g(0.03mol)を5分間かけ滴下した。その後65℃まで加熱し、4時間攪拌した。室温まで冷却した後、生じた紫茶色結晶を濾取した後、濾取した結晶をエタノール500mlで二回、リスラリー洗浄をおこなった。これを、減圧乾燥して紫茶色粉末80.0g(0.286mol、収率96.3%)を得た。
次に、上記紫茶色粉末72.0g(0.258mol)に、これに酢酸720g、トリフルオロ酢酸72.0gを加えて攪拌させた。その後100℃まで加熱し、15時間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢酸200mlでリンス洗浄をおこなった後、ヘキサン200mlでリンス洗浄をおこなった。これを、減圧乾燥して白色粉末30.0g(0.117mol、収率45.3%)を得た。
次に、脱気窒素置換した500ml三口フラスコに55%水素化ナトリウム2.16g(49.5mmol)、脱水N,N’-ジメチルホルムアミド70mlを加え、窒素気流中下で攪拌を行う。上記で得た白色粉末13.7g(40mmol)に脱水N,N’-ジメチルホルムアミド70mlを加え、溶解させ、その後、同フラスコ内に15分間かけ滴下した。滴下終了後、1時間攪拌を継続した。その後、塩化シアヌル2.46g(13mmol)に脱水N,N’-ジメチルホルムアミド70mlを加え、溶解させ、その後、同フラスコ内に15分間かけ滴下した。滴下終了後、内温80℃で24時間攪拌を継続した後、室温まで冷却した。冷却した後、同フラスコ内に水350gを加え、析出した結晶を濾取した。濾取した結晶を水300gで二回リスラリーを行い、その後、メタノール300gにてリスラリーを行った。これを減圧乾燥した後、カラムクロマトグラフィーで精製して淡黄色粉末2.1g(2.0mmol、収率15.5%)を得た。
化合物103のEI−MS(M+1)は1072、融点は492℃であった。
ガラス基板上に真空蒸着法にて、真空度4.0×10-4 Pa の条件にて化合物103を蒸着源から蒸着し、薄膜を1.0Å/秒にて50nmの厚さで形成した。作成した薄膜を、蛍光測定装置にて評価した。次にガラス基板上に真空蒸着法にて、真空度4.0×10-4Pa の条件にて化合物3とIr(ppy)3とを異なる蒸着源から蒸着し、Ir(ppy)3の濃度が7.0 %であるような薄膜を1.0Å/秒にて50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物103の極大吸収波長を使用し、そのときに出てくる光を観察し、化合物103単独の薄膜の場合に出てくる光と比較した。結果を表3に示す。
薄膜主成分をAlq3に変えて薄膜を作成した以外は、実施例11と同様に行った。結果を表3に示す。
図1において、正孔注入層を省略し、電子注入層を追加した構成の有機EL素子を作成した。膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔輸送層としてNPBを60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物103とIr(ppy)3とを異なる蒸着源から、共蒸着し、25nmの厚さに形成した。この時、Ir(ppy)3の濃度は7.0 %であった。次に、電子輸送層としてAlq3を50nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
正孔輸送層としてHMTPDを、発光層の主成分としてTAZを用いた以外は実施例12と同様にして有機EL素子を作成した。
発光層の主成分として、TAZを用いた以外は実施例12と同様にして有機EL素子を作成した。
Claims (14)
- 下記一般式(1)で表わされる有機電界発光素子用化合物。
- 下記一般式(2)で表される請求項1に記載の有機電界発光素子用化合物。
- 下記一般式(4)で示される請求項1記載の有機電界発光素子用化合物。
- 一般式(2)、(4)及び式(2b)中、R6、R22〜R23が置換若しくは未置換のフェニル基又はピリジル基であり、且つ、R1〜R4、R16〜R21が水素又はフェニル基である請求項3又は4に記載の有機電界発光素子用化合物。
- 下記一般式(1)で表わされる有機電界発光素子用化合物。
- 基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、請求項1〜5のいずれかに記載の有機電界発光素子用化合物を含むことを特徴とする有機電界発光素子。
- 基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、該発光層が、燐光発光性ドーパントと請求項1〜5のいずれかに記載の有機電界発光素子用化合物をホスト材料として含有することを特徴とする有機電界発光素子。
- 陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有してなる請求項8記載の有機電界発光素子。
- 発光層と電子注入輸送層の間に正孔阻止層を有してなる請求項9記載の有機電界発光素子。
- 基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、請求項6に記載の有機電界発光素子用化合物を含むことを特徴とする有機電界発光素子。
- 基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、該発光層が、燐光発光性ドーパントと請求項6に記載の有機電界発光素子用化合物をホスト材料として含有することを特徴とする有機電界発光素子。
- 陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有してなる請求項12に記載の有機電界発光素子。
- 発光層と電子注入輸送層の間に正孔阻止層を有してなる請求項13に記載の有機電界発光素子。
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CN101321755A (zh) | 2008-12-10 |
CN102633820B (zh) | 2015-01-21 |
US7993760B2 (en) | 2011-08-09 |
TWI378099B (ja) | 2012-12-01 |
WO2007063754A1 (ja) | 2007-06-07 |
EP1956022B1 (en) | 2012-07-25 |
KR101082258B1 (ko) | 2011-11-09 |
CN101321755B (zh) | 2012-04-18 |
CN102633820A (zh) | 2012-08-15 |
EP1956022A1 (en) | 2008-08-13 |
JPWO2007063754A1 (ja) | 2009-05-07 |
TW200734340A (en) | 2007-09-16 |
US20090302742A1 (en) | 2009-12-10 |
EP1956022A4 (en) | 2011-07-13 |
KR20080085001A (ko) | 2008-09-22 |
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