JP5297166B2 - キノキサリン誘導体、並びにその誘導体を用いた発光素子、発光装置及び電子機器 - Google Patents
キノキサリン誘導体、並びにその誘導体を用いた発光素子、発光装置及び電子機器 Download PDFInfo
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- JP5297166B2 JP5297166B2 JP2008303549A JP2008303549A JP5297166B2 JP 5297166 B2 JP5297166 B2 JP 5297166B2 JP 2008303549 A JP2008303549 A JP 2008303549A JP 2008303549 A JP2008303549 A JP 2008303549A JP 5297166 B2 JP5297166 B2 JP 5297166B2
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- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title claims abstract description 22
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 134
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 53
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 41
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract description 7
- 239000010410 layer Substances 0.000 description 211
- 239000000126 substance Substances 0.000 description 112
- 150000003252 quinoxalines Chemical class 0.000 description 101
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- 230000015572 biosynthetic process Effects 0.000 description 76
- 238000003786 synthesis reaction Methods 0.000 description 75
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- 239000000463 material Substances 0.000 description 67
- -1 monosubstituted quinoxaline Chemical class 0.000 description 58
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
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- 239000007787 solid Substances 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 20
- 229910052736 halogen Inorganic materials 0.000 description 20
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 16
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
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- 239000011159 matrix material Substances 0.000 description 14
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 229910052763 palladium Inorganic materials 0.000 description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 150000001340 alkali metals Chemical class 0.000 description 12
- 150000001639 boron compounds Chemical class 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 238000000295 emission spectrum Methods 0.000 description 12
- 229910052740 iodine Inorganic materials 0.000 description 12
- 239000011630 iodine Substances 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 150000001342 alkaline earth metals Chemical class 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 10
- LRFPWISSSYZMQB-UHFFFAOYSA-N 2-[4-[4-[3-[4-[4-(1,3-benzoxazol-2-yl)phenyl]phenyl]quinoxalin-2-yl]phenyl]phenyl]-1,3-benzoxazole Chemical compound C1=CC=C2OC(C3=CC=C(C=C3)C3=CC=C(C=C3)C3=NC4=CC=CC=C4N=C3C3=CC=C(C=C3)C3=CC=C(C=C3)C=3OC4=CC=CC=C4N=3)=NC2=C1 LRFPWISSSYZMQB-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 9
- 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 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
- 239000010453 quartz Substances 0.000 description 9
- 238000004544 sputter deposition Methods 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- 0 *(c1c(*2)cccc1)C(c1ccccc1)=C2c1ccccc1 Chemical compound *(c1c(*2)cccc1)C(c1ccccc1)=C2c1ccccc1 0.000 description 8
- CDRWNQTZRPFMQN-UHFFFAOYSA-N 2-[4-[4-(3-phenylquinoxalin-2-yl)phenyl]phenyl]-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(C=2C=CC(=CC=2)C=2OC3=CC=CC=C3N=2)C=C1 CDRWNQTZRPFMQN-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000012212 insulator Substances 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 230000005284 excitation Effects 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 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 7
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 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 7
- 229910001930 tungsten oxide Inorganic materials 0.000 description 7
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 6
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 6
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- RBVHJNZMSBQFDK-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3-benzoxazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2O1 RBVHJNZMSBQFDK-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 229910052814 silicon oxide Inorganic materials 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- WATVCMJLZPTSSS-UHFFFAOYSA-N 2,3-bis(4-bromophenyl)quinoxaline Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(Br)C=C1 WATVCMJLZPTSSS-UHFFFAOYSA-N 0.000 description 4
- UQVFZEYHQJJGPD-UHFFFAOYSA-N 9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UQVFZEYHQJJGPD-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 4
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 4
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 229940125797 compound 12 Drugs 0.000 description 4
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- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Description
タイシ ツジ,他5名,SID 04 DIGEST,35,PP900−903(2004)
すなわち、本発明者らは、鋭意検討を重ねた結果、キノキサリンの2位または3位の一方の炭素、又は両方の炭素と、ベンゾオキサゾールの2位の炭素とが、アリーレン基を介して結合したキノキサリン誘導体を合成し、該キノキサリン誘導体が発光素子に好適に用いることができることを見出した。
よって、本発明の一は、一般式(G11)で表されるキノキサリン誘導体であり、それは、キノキサリンの2位または3位の一方の炭素とベンゾオキサゾールの2位の炭素とがアリーレン基を介して結合した態様のキノキサリン誘導体である。
また、本発明のキノキサリン誘導体を発光素子に用いることにより、駆動電圧の低い発光素子を得ることができる。また、消費電力の小さい発光素子を得ることができる。
本実施の形態では、本発明のキノキサリン誘導体について示す。
そして、前者の一置換体は、大別された一で、一般式(G11)で表されるキノキサリン誘導体である。
また、一般式(G11)および一般式(G21)において、αで表される置換基としては、例えば、構造式(12−1)〜構造式(12−10)で表されるアリーレン基が挙げられる。構造式(12−4)や、構造式(12−8)〜構造式(12−10)などで示したように、αで表されるアリーレン基は置換基を有していても良い。
例えば、構造式(12−8)及び構造式(12−10)においては、フルオレン−ジイル基の9位に結合しているメチル基やフェニル基は主骨格に含まない。また、構造式(12−9)においては、スピロ環を形成している9位の炭素にフェニル基が2つ結合し、その2つのフェニル基が互いに結合してスピロフルオレン骨格を形成しているとする。つまり、構造式(12−9)も主骨格はフルオレン骨格(炭素数13)とする。
次に、N−(2−ヒドロキシフェニル)アリールアミド誘導体(化合物3)を脱水環化させることで、ベンゾオキサゾール環を形成する。このとき用いる脱水剤は、塩酸、硫酸、リン酸等の無機酸や、パラートルエンスルホン酸、トリフルオロ酢酸等の有機酸が挙げられる。また、このとき用いられる溶媒はクロロホルムやジクロロメタンや四塩化炭素などのハロゲン系溶媒や、ベンゼンやトルエンやキシレン等の炭化水素が挙げられる。このようにして、2−アリールベンゾオキサゾール誘導体(化合物4)を得ることができる。合成スキーム(A−1)において、R21〜R24は、それぞれ同一でも異なっていてもよく、水素、又は炭素数1〜4のアルキル基を表し、βは、炭素数6〜14のアリーレン基を表す。また、X1はハロゲンを表し、塩素、臭素、ヨウ素が好ましい。また、X4は、ハロゲン基を表し、特に塩化物が好ましい。
また、合成スキーム(A−2)において得られるボロン酸を、エチルアルコールやプロピルアルコール等で保護した有機ホウ素化合物や、エチレングリコールやピナコールの様なジオールで保護し、環を形成した有機ホウ素化合物としてもよい。
また、合成スキーム(A−4)において得られるボロン酸を、エチルアルコールやプロピルアルコール等で保護した有機ホウ素化合物や、エチレングリコールやピナコールの様なジオールで保護し、環を形成した有機ホウ素化合物としてもよい。
合成スキーム(A−5)において、化合物8の代わりに、化合物8のボロン酸を、エチルアルコールやプロピルアルコール等で保護した有機ホウ素化合物を用いても良く、また、エチレングリコールやピナコールの様なジオールで保護し、環を形成した有機ホウ素化合物を用いても良い。また、鈴木・宮浦カップリング以外の、有機アルミニウム化合物や、有機ジルコニウム化合物、有機亜鉛化合物、有機スズ化合物等を用いるクロスカップリングを用いても良い。
合成スキーム(A−6)において、化合物9の代わりに化合物9のボロン酸を、エチルアルコールやプロピルアルコール等で保護した有機ホウ素化合物を用いても良く、また、エチレングリコールやピナコールの様なジオールで保護し、環を形成した有機ホウ素化合物を用いても良い。また、鈴木・宮浦カップリング以外の有機アルミニウム化合物や、有機ジルコニウム化合物、有機亜鉛化合物、有機スズ化合物等を用いるクロスカップリング反応を用いても良い。
また、合成スキーム(A−8)において得られるボロン酸を、エチルアルコールやプロピルアルコール等で保護した有機ホウ素化合物や、エチレングリコールやピナコールの様なジオールで保護し、環を形成した有機ホウ素化合物としても良い。
合成スキーム(A−9)において、化合物12の代わりに、化合物12のボロン酸を、エチルアルコールやプロピルアルコール等で保護した有機ホウ素化合物を用いても良く、また、エチレングリコールやピナコールの様なジオールで保護し、環を形成した有機ホウ素化合物を用いても良い。また、鈴木・宮浦カップリング以外の有機アルミニウム化合物や、有機ジルコニウム化合物、有機亜鉛化合物、有機スズ化合物等を用いるクロスカップ反応を用いても良い。
合成スキーム(A−10)において、化合物9の代わりに化合物9のボロン酸をエチルアルコールやプロピルアルコール等で保護した有機ホウ素化合物を用いても良く、また、エチレングリコールやピナコールの様なジオールで保護し、環を形成した有機ホウ素化合物を用いても良い。また、鈴木・宮浦カップリング以外の有機アルミニウム化合物や、有機ジルコニウム化合物、有機亜鉛化合物、有機スズ化合物等を用いるクロスカップリングを用いても良い。
本実施の形態では、実施の形態1で示したキノキサリン誘導体を用いた発光素子の一態様について、図1および図2を用いて示す。
’−トリス[N−(3−メチルフェニル)−N−フェニルアミノ]トリフェニルアミン(略称:MTDATA)、4,4’−ビス[N−(4−ジフェニルアミノフェニル)−N−フェニルアミノ]ビフェニル(略称:DPAB)、4,4’−ビス(N−{4−[N’−(3−メチルフェニル)−N’−フェニルアミノ]フェニル}−N−フェニルアミノ)ビフェニル(略称:DNTPD)、1,3,5−トリス[N−(4−ジフェニルアミノフェニル)−N−フェニルアミノ]ベンゼン(略称:DPA3B)、3−[N−(9−フェニルカルバゾール−3−イル)−N−フェニルアミノ]−9−フェニルカルバゾール(略称:PCzPCA1)、3,6−ビス[N−(9−フェニルカルバゾール−3−イル)−N−フェニルアミノ]−9−フェニルカルバゾール(略称:PCzPCA2)、3−[N−(1−ナフチル)−N−(9−フェニルカルバゾール−3−イル)アミノ]−9−フェニルカルバゾール(略称:PCzPCN1)等の芳香族アミン化合物等が挙げられる。
また、緑色系の発光材料として、トリス(2−フェニルピリジナト−N,C2')イリジウム(III)(略称:Ir(ppy)3)、ビス(2−フェニルピリジナト−N,C2')イリジウム(III)アセチルアセトナート(略称:Ir(ppy)2(acac))、ビス(1,2−ジフェニル−1H−ベンゾイミダゾラト)イリジウム(III)アセチルアセトナート(略称:Ir(pbi)2(acac))、ビス(ベンゾ[h]キノリナト)イリジウム(III)アセチルアセトナート(略称:Ir(bzq)2(acac))などが挙げられる。
また、黄色系の発光材料として、ビス(2,4−ジフェニル−1,3−オキサゾラト−N,C2')イリジウム(III)アセチルアセトナート(略称:Ir(dpo)2(acac))、ビス[2−(4’−パーフルオロフェニルフェニル)ピリジナト]イリジウム(III)アセチルアセトナート(略称:Ir(p−PF−ph)2(acac))、ビス(2−フェニルベンゾチアゾラト−N,C2')イリジウム(III)アセチルアセトナート(略称:Ir(bt)2(acac))などが挙げられる。
また、橙色系の発光材料として、トリス(2−フェニルキノリナト−N,C2')イリジウム(III)(略称:Ir(pq)3)、ビス(2−フェニルキノリナト−N,C2')イリジウム(III)アセチルアセトナート(略称:Ir(pq)2(acac))などが挙げられる。
また、赤色系の発光材料として、ビス[2−(2’−ベンゾ[4,5−α]チエニル)ピリジナト−N,C3']イリジウム(III)アセチルアセトナート(略称:Ir(btp)2(acac))、ビス(1−フェニルイソキノリナト−N,C2')イリジウム(III)アセチルアセトナート(略称:Ir(piq)2(acac))、(アセチルアセトナト)ビス[2,3−ビス(4−フルオロフェニル)キノキサリナト]イリジウム(III)(略称:Ir(Fdpq)2(acac))、2,3,7,8,12,13,17,18−オクタエチル−21H,23H−ポルフィリン白金(II)(略称:PtOEP)等が挙げられる。 また、トリス(アセチルアセトナト)(モノフェナントロリン)テルビウム(III)(略称:Tb(acac)3(Phen))、トリス(1,3−ジフェニル−1,3−プロパンジオナト)(モノフェナントロリン)ユーロピウム(III)(略称:Eu(DBM)3(Phen))、トリス[1−(2−テノイル)−3,3,3−トリフルオロアセトナト](モノフェナントロリン)ユーロピウム(III)(略称:Eu(TTA)3(Phen))等の希土類金属錯体は、希土類金属イオンからの発光(異なる多重度間の電子遷移)であるため、燐光性化合物として用いることができる。
フェニル−1,4−フェニレンジアミン(略称:2DPAPA)、N−[9,10−ビス(1,1’−ビフェニル−2−イル)−2−アントリル]−N,N’,N’−トリフェニル−1,4−フェニレンジアミン(略称:2DPABPhA)、N−[9,10−ビス(1,1’−ビフェニル−2−イル)]−N−[4−(9H−カルバゾール−9−イル)フェニル]−N−フェニルアントラセン−2−アミン(略称:2YGABPhA)、N,N,9−トリフェニルアントラセン−9−アミン(略称:DPhAPhA)などが挙げられる。また、黄色系の発光材料として、ルブレン、5,12−ビス(1,1’−ビフェニル−4−イル)−6,11−ジフェニルテトラセン(略称:BPT)などが挙げられる。また、赤色系の発光材料として、N,N,N’,N’−テトラキス(4−メチルフェニル)テトラセン−5,11−ジアミン(略称:p−mPhTD)、7,13−ジフェニル−N,N,N’,N’−テトラキス(4−メチルフェニル)アセナフト[1,2−a]フルオランテン−3,10−ジアミン(略称:p−mPhAFD)などが挙げられる。
なお、各電極の成膜においても前記したとおり同様の方法を採用できる。
本実施の形態では、本発明に係る発光素子の一態様として、実施の形態1で示したキノキサリン誘導体を発光層に用いた構成を示す。
本実施の形態では、本発明に係る発光素子の一態様として、実施の形態1で示したキノキサリン誘導体を電子注入層に用いた構成を示す。
本実施の形態は、本発明に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の態様について、図3を用いて示す。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する積層型発光素子である。各発光ユニットの構成としては、実施の形態1〜実施の形態4で示した構成と同様な構成を用いることができる。つまり、実施の形態2で示した発光素子は、1つの発光ユニットを有する発光素子である。本実施の形態では、複数の発光ユニットを有する発光素子について説明する。
テニウム等の半導体や絶縁体を用いることができる。あるいは、正孔輸送性の高い物質に、アクセプター物質が添加された構成であってもよい。正孔輸送性の高い物質とアクセプター性物質を含む層は、実施の形態2で示した複合材料であり、アクセプター物質として、7,7,8,8−テトラシアノ−2,3,5,6−テトラフルオロキノジメタン(略称:F4−TCNQ)や、酸化バナジウムや酸化モリブデンや酸化タングステン等の金属酸化物を含む。正孔輸送性の高い物質としては、芳香族アミン化合物、カルバゾール誘導体、芳香族炭化水素、高分子化合物、オリゴマー、デンドリマー、ポリマーなど、種々の化合物を用いることができる。なお、正孔輸送性の高い物質としては、正孔移動度が10-6cm2/Vs以上であるものを適用することが好ましい。但し、電子よりも正孔の輸送性の高い物質であれば、これら以外のものを用いてもよい。正孔輸送性の高い物質とアクセプター性物質を含む複合材料は、キャリア注入性、キャリア輸送性に優れているため、低電圧駆動、低電流駆動を実現することができる。
本実施の形態では、本発明の発光素子を有する発光装置を示す。
本実施の形態では、実施の形態6に示す発光装置をその一部に含む本発明の電子機器について示す。本発明の電子機器は、実施の形態2〜実施の形態5で示した発光素子を有し、低消費電力の表示部を有する。
が図られているので、環境に適合した製品を提供することができる。
タ保存及び移動に対応できる。
4−ブロモ−N−(2−ヒドロキシフェニル)ベンズアミドの合成スキームを(B−1)に示す。
2−(4−ブロモフェニル)ベンゾオキサゾールの合成スキームを(B−2)に示す。
(4−ブロモフェニル)フェニルアセチレンの合成スキームを(B−3)に示す。
1−(4−ブロモフェニル)−2−フェニルエタンジオンの合成スキームを(B−4)に示す。
2−(4−ブロモフェニル)−3−フェニルキノキサリンの合成スキームを(B−5)に示す。
BOx1PQの合成スキームを(B−7)に示す。
2,3−ビス(4−ブロモフェニル)キノキサリンの合成スキームを(C−1)に示す。
4,4’−(キノキサリン−2,3−ジイル)ジフェニルボロン酸の合成スキームを(C−2)に示す。
BOx2PQの合成スキームを(C−3)に示す。
発光素子1aと同一基板を用い、BOx2PQの代わりに、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を用いて、発光素子1aと同様に作製した。つまり、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を30nmの膜厚となるように成膜し、電子輸送層2114を形成した。電子輸送層2114以外は発光素子1aと同様に作製した。
0.16、y=0.16)であり、青色の発光を示した。また、輝度1080cd/m2のときの電流効率は2.7cd/Aであった。また、輝度1080cd/m2のときの電圧は6.4V、電流密度は39.6mA/cm2、パワー効率は1.3lm/Wであった。
発光素子2aと同一基板を用い、BOx1PQの代わりに、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を用いて、発光素子2aと同様に作製した。つまり、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を20nmの膜厚となるように成膜し、電子輸送層(A)2214を形成した。電子輸送層(A)2214以外は発光素子2aと同様に作製した。
16、y=0.17)であり、青色の発光を示した。また、輝度830cd/m2のときの電流効率は3.4cd/Aであった。また、輝度830cd/m2のときの電圧は5.0V、電流密度は24.3mA/cm2、パワー効率は2.1lm/Wであった。
102 第1の電極
103 EL層
104 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
623 Nチャネル型TFT
624 Pチャネル型TFT
701 本体
702 表示部
703 操作スイッチ
704 表示部
710 本体
711 表示部
712 メモリ部
713 操作部
714 イヤホン
901 筐体
902 液晶層
903 バックライト
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
1001 筐体
1002 筐体
1101 表示部
1102 スピーカー
1103 マイクロフォン
1104 操作キー
1105 ポインティングデバイス
1106 カメラ用レンズ
1107 外部接続端子
1108 イヤホン端子
1201 キーボード
1202 外部メモリスロット
1203 カメラ用レンズ
1204 ライト
2001 筐体
2002 光源
2101 ガラス基板
2102 第1の電極
2104 第2の電極
2111 複合材料を含む層
2112 正孔輸送層
2113 発光層
2114 電子輸送層
2115 電子注入層
2201 ガラス基板
2202 第1の電極
2204 第2の電極
2211 複合材料を含む層
2212 正孔輸送層
2213 発光層
2214 電子輸送層(A)
2215 電子輸送層(B)
2216 電子注入層
3001 照明装置
3002 テレビ装置
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9301 本体
9302 表示部
9303 筐体
9304 外部接続ポート
9305 リモコン受信部
9306 受像部
9307 バッテリー
9308 音声入力部
9309 操作キー
9310 接眼部
9401 本体
9402 筐体
9403 表示部
9404 音声入力部
9405 音声出力部
9406 操作キー
9407 外部接続ポート
9408 アンテナ
Claims (13)
- 請求項1乃至請求項4のいずれか一項において、
R1は、フェニル基またはビフェニル基であることを特徴とするキノキサリン誘導体。 - 一対の電極間に、請求項1乃至請求項9のいずれか一項に記載のキノキサリン誘導体を有する発光素子。
- 陽極と陰極との間に、発光層と、請求項1乃至請求項9のいずれか一項に記載のキノキサリン誘導体を含む層を有し、
前記キノキサリン誘導体を含む層は、前記発光層と前記陰極との間に設けられていることを特徴とする発光素子。 - 請求項10または請求項11に記載の発光素子と、前記発光素子の発光を制御する制御回路とを有する発光装置。
- 表示部を有し、
前記表示部は、請求項10または請求項11のいずれか一項に記載の発光素子と前記発光素子の発光を制御する制御回路とを備えたことを特徴とする電子機器。
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-
2008
- 2008-11-25 US US12/277,451 patent/US8119259B2/en not_active Expired - Fee Related
- 2008-11-28 CN CN200810179733.0A patent/CN101691366B/zh not_active Expired - Fee Related
- 2008-11-28 TW TW097146463A patent/TWI436997B/zh not_active IP Right Cessation
- 2008-11-28 CN CN201310287456.6A patent/CN103396411B/zh not_active Expired - Fee Related
- 2008-11-28 JP JP2008303549A patent/JP5297166B2/ja not_active Expired - Fee Related
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US20090140642A1 (en) | 2009-06-04 |
TW200946519A (en) | 2009-11-16 |
JP2009149629A (ja) | 2009-07-09 |
US8119259B2 (en) | 2012-02-21 |
CN103396411A (zh) | 2013-11-20 |
CN103396411B (zh) | 2016-01-20 |
TWI436997B (zh) | 2014-05-11 |
CN101691366B (zh) | 2013-08-14 |
CN101691366A (zh) | 2010-04-07 |
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