JP4959100B2 - 置換フルオレンポリマー及びその製造方法 - Google Patents
置換フルオレンポリマー及びその製造方法 Download PDFInfo
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- JP4959100B2 JP4959100B2 JP2002589593A JP2002589593A JP4959100B2 JP 4959100 B2 JP4959100 B2 JP 4959100B2 JP 2002589593 A JP2002589593 A JP 2002589593A JP 2002589593 A JP2002589593 A JP 2002589593A JP 4959100 B2 JP4959100 B2 JP 4959100B2
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- 229920000642 polymer Polymers 0.000 title claims abstract description 78
- 238000004519 manufacturing process Methods 0.000 title description 9
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title description 5
- 230000003287 optical effect Effects 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims description 34
- 230000032258 transport Effects 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229920000547 conjugated polymer Polymers 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005259 triarylamine group Chemical group 0.000 claims description 4
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000000178 monomer Substances 0.000 description 31
- 125000003118 aryl group Chemical group 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002800 charge carrier Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 150000004820 halides Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- -1 poly (para-phenylene vinylene) Polymers 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 6
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 5
- 125000005620 boronic acid group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PHZFJRZBZBRNFK-UHFFFAOYSA-N 1,1'-biphenyl;9h-fluorene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 PHZFJRZBZBRNFK-UHFFFAOYSA-N 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical group C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 3
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical group C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910010199 LiAl Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000003106 haloaryl group Chemical group 0.000 description 2
- 125000005216 haloheteroaryl group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- VYCFLFGSEQTJGJ-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)-9h-fluorene Chemical compound C1=CC(OC)=CC=C1C1=CC=C2C3=CC=CC=C3CC2=C1C1=CC=C(OC)C=C1 VYCFLFGSEQTJGJ-UHFFFAOYSA-N 0.000 description 1
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical group C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 1
- CWYRHXPKUOMYPX-UHFFFAOYSA-N 1-(4-methoxyphenyl)-9h-fluorene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C21 CWYRHXPKUOMYPX-UHFFFAOYSA-N 0.000 description 1
- QYNWFBYWVPMMRL-UHFFFAOYSA-N 1-bromo-4-(4-tert-butylphenyl)benzene Chemical group C1=CC(C(C)(C)C)=CC=C1C1=CC=C(Br)C=C1 QYNWFBYWVPMMRL-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- UFJKWSXGFWPAOD-UHFFFAOYSA-N 1-tert-butyl-4-phenylbenzene 9H-fluorene Chemical compound C1=CC=CC=2C3=CC=CC=C3CC12.C(C)(C)(C)C1=CC=C(C=C1)C1=CC=CC=C1 UFJKWSXGFWPAOD-UHFFFAOYSA-N 0.000 description 1
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 1
- CYKLQIOPIMZZBZ-UHFFFAOYSA-N 2,7-dibromo-9,9-dioctylfluorene Chemical compound C1=C(Br)C=C2C(CCCCCCCC)(CCCCCCCC)C3=CC(Br)=CC=C3C2=C1 CYKLQIOPIMZZBZ-UHFFFAOYSA-N 0.000 description 1
- AJYDOCCGNIBJBY-UHFFFAOYSA-N 2,7-dibromo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=C(Br)C=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 AJYDOCCGNIBJBY-UHFFFAOYSA-N 0.000 description 1
- FYEFHYMUEWRCRF-UHFFFAOYSA-N 2,7-dibromofluoren-1-one Chemical compound BrC1=CC=C2C3=CC=C(Br)C(=O)C3=CC2=C1 FYEFHYMUEWRCRF-UHFFFAOYSA-N 0.000 description 1
- AOXLNBAKWXCQBZ-UHFFFAOYSA-N 2-(4-butylphenyl)benzene-1,4-diamine Chemical compound C1=CC(CCCC)=CC=C1C1=CC(N)=CC=C1N AOXLNBAKWXCQBZ-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- LQQKFGSPUYTIRB-UHFFFAOYSA-N 9,9-dihexylfluorene Chemical compound C1=CC=C2C(CCCCCC)(CCCCCC)C3=CC=CC=C3C2=C1 LQQKFGSPUYTIRB-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- HPOXYGHTBIMOHV-UHFFFAOYSA-N n,n-bis(4-bromophenyl)-2-butan-2-ylaniline Chemical compound CCC(C)C1=CC=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 HPOXYGHTBIMOHV-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000523 sample Substances 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K85/115—Polyfluorene; Derivatives thereof
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- H—ELECTRICITY
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Description
DE19846767はセクションc)において9,9−ジアリールフルオレンモノマーの製造を開示している。
したがって、本発明の1つの目的は、上記ポリマーを提供することにある。
本発明の他の目的は、上記ポリマーの製造方法を提供することにある。
好ましくは、製造の容易さから、R1及びR2は同じである。しかし、R1及びR2は異なり得る。
1つの実施例において、R1及びR2は置換され又は置換されていないトリアリールアミンを含まない。
この点において、一般式Iを有する基は、一般式IIIで示される式を有することが好ましい。
本発明のポリマーの重合化の度合いは、好ましくは、少なくとも4であるべきである。
一般的に、本発明のポリマーを製造するために使用されるいくつかの異なった重合方法が知られている。
(a)次のどちらかを含む第1芳香族モノマー
(i)本発明の第1の側面に関係して定義される第1の繰返し単位
(ii)第1の繰返し単位と同じか異なってもよい第2の繰返し単位のいずれか、並びに、ボロン酸基、ボロン酸エステル基及びボラン基から選択される少なくとも2つの反応性ボロン誘導体基
並びに、
(b)第1又は第2繰返し単位の他方、及び少なくとも2つの反応性ハロゲン化物官能基を含む第2芳香族モノマー
(a)次を含む第1芳香族モノマー
(i)本発明の第1の側面で定義される第1繰返し単位
(ii)ボロン酸基、ボロン酸エステル基及びボラン基から選択される反応性ボロン誘導体基
(iii)反応性ハロゲン化物官能基、並びに
(b)次のものを含む第2芳香族モノマー
(i)第1繰返し単位と同じか異なる第2繰返し単位
(ii)ボロン酸基、ボロン酸エステル基及びボラン基から選択される反応性ボロン誘導体基、並びに
(iii)反応性ハロゲン化物官能基
A)モノマーの製造
本発明のモノマーは、次の一般スキームに従って製造された。
2,7−ジブロモ−9,9−ビス(ビフェニル)フルオレン(R1=R2=ビフェニル)
(1)2,7−ジブロモフルオレノン
3Lのフランジフラスコ内に、フルオレノン(100.006g、0.555mol)、五酸化リン(110.148g、0.776mol)及びトリメチルリン酸(1200mL)が混合された。機械的攪拌により、トリメチルリン酸(200mL)中の臭素(63mL、1.23mol)の溶液が速やかに加えられた。この透明溶液は120℃で22時間加熱された。混合物は室温まで冷却され、3Lの水に注がれた。チオ硫酸ナトリウム(50.045g)が加えられ、混合物は黄色になった。攪拌は1時間継続され、黄色の固体がろ過された。この固体は、モノ臭素化化合物を除くためにメタノール中で加熱され、176.183g(HPLCにより純度98%、収率94%)が得られた。
1H NMR (CDCl3) 7.73 (2H, d, J 2.0), 7.61 (2H, dd, J 7.6, 2.0), 7.36 (2H, d, J 8.0) ; 13C NMR (CDCl3) 142.3, 137.5, 135.3, 127.9, 123.3, 121.8, 109.8。
2Lのフランジフラスコ中に、2,7−ジブロモフルオレノン(120.526g、0.356mol)、水酸化カリウム(微細粉末168.327g、3.000mol)及びトルエン(600mL)が加えられた。この混合物は、120℃で4時間加熱され、室温まで冷却された。固体を溶解するため、激しく攪拌しながら水(約2L)が加えられた。緑がかった水性層が除去され、黄色のトルエン層が水で2回洗浄された。合わせた水性層が濃塩酸により酸性化され、次いで沈殿物がろ過され、乾燥され、トルエンから再結晶され、100.547gのオフホワイトの結晶が得られた。(収率79%)
1H NMR ((CD3)2CO) 8.00 (1H, d, J 2.0), 7.77 (1H, dd, J 8.0, 2.4), 7.57 (2H, d, J8.0), 7.34 (1H, d, J 8.4), 7.29 (2H, d, J 8.8) ; 13C NMR ((CD3)2CO) 167.1, 140.4, 139.8, 134.2, 133.5, 132.8, 132.7, 131.2, 130.6, 121.4, 121.1。
4,4−ジブロモ−2−カルボン酸ビフェニル(171.14g、0.481mol)がメタノール(700mL)及び硫酸(15mL)中に懸濁され、80℃で21時間加熱された。溶媒は除去され、油が酢酸エチル中に溶解された。この溶液は、2Nの水酸化ナトリウム、水、飽和塩化ナトリウムで洗浄され、硫酸マグネシウム上で乾燥され、ろ過され、蒸発されてオレンジ色の油を得た。この油は、熱いメタノールで処理され、冷却するとエステルが析出し、ろ過された。母液が蒸発され、固体を再結晶化するとさらに生成物が得られた。エステルはGCMSにより純度100%であり、123.27g(69%)の収量が得られた。
1H NMR (CDCl3) 7.99 (1H, d, J 2.0), 7.64 (1H, dd, J 8.0, 1.6), 7.51 (2H, d, J 8.4), 7.19 (1H, d, J 8.8), 7.13 (2H, d, J 8.8), 3.67 (3H, s); 13C NMR (CDCl3) 167.1, 140.3, 139.1, 134.4, 132.9, 132.1, 132.0, 131.3, 129.8, 121.9, 121.5, 52.3.
GCMS: M+ = 370。
参考文献:J.Am.Chem.Soc.,114,15(1992)
4−ブロモビフェニル(63.766g、0.27mol)が乾燥THF(400ml)中に溶解された。溶液はマイナス65℃まで冷却され、そこで、n−BuLi(109ml、へキサン中2.5M、0.27mol)が攪拌されながら滴下された。添加が完了すると、混合物はマイナス65℃で1時間攪拌された。乾燥THF(200ml)中の4,4’−ジブロモ−2−メチルエステルビフェニル(39.14g、0.106mol)溶液が、混合物の温度がマイナス60℃未満に保たれるようにしながら滴下された。添加が完了すると、混合物は室温まで暖められた。反応物は水(10ml)でクエンチされ、溶媒は蒸発された。残留物はトルエンに溶解され、飽和塩化アンモニウム溶液及び塩水で洗浄された。溶液はMgSO4上で乾燥され、蒸発された。生成物は石油エーテル(100〜120℃)及び少しの酢酸エチルで処理された。得られた結晶は、ろ過され、乾燥され、54.535g(78%)が得られた。
アルコール(14.03g、21.7mmol)がジクロロメタン(70ml)中に溶解された。得られた溶液は氷浴で冷却された。三フッ化ホウ素ジエチルエーテル錯体(14ml)が滴下され、濃青色の混合物を得た。混合物は2lの氷水中に注がれ、混合物がアルカリ(pH8)になるまで炭酸カリウムが添加された。ジクロロメタンが添加され、分離され、さらに追加のジクロロメタンによって水性相が抽出された。有機相が合わされ、セライトを通してろ過され、メタノール中で沈殿された。得られた固体はろ過され、酢酸エチル/ジクロロメタン(50/50)から数回にわたり再結晶化され、3.28g(収率24%、HPLCにより99.44%)が得られた。
2,7−ジブロモ−9,9−ビス(4−t−ブチルビフェニル)フルオレン
4−ブロモビフェニルの代わりに4−ブロモ−4’−t−ブチル−1,1’−ビフェニルが使用された以外はモノマーの実施例M1と同様の合成が行われた。
ポリマーの実施例 P1
本発明の青色発光ポリマーは、WO00/53656のプロセスにしたがって、9,9−ジ−n−オクチルフルオレン−2,7−ジ(エチレニルボロネート)(0.5当量)、2,7−ジブロモ−9,9−ジフェニルフルオレン(0.3当量)、N,N−ジ(4−ブロモフェニル)−sec−ブチルフェニルアミン(0.1当量)及びN,N’−ジ(4−ブロモフェニル)−N,N’−ジ(4−n−ブチルフェニル)−1,4−ジアミノベンゼン(0.1当量)の反応により製造され、次のポリマーP1が得られた。
ポリマーの比較例
WO00/55927に開示されているように、青色の発光ポリマーが、ポリマーの実施例1における全ての9,9−ジフェニルフルオレン繰返し単位が9,9−ジ−n−オクチルフルオレン繰返し単位に交換された場合にしたがって製造された。これは、2,7−ジブロモ−9,9−ジフェニルフルオレンの代わりに0.3当量の2,7−ジブロモ−9,9−ジ−n−オクチルフルオレンを使用した点以外はポリマーの実施例1の調製にしたがって、行われた。
本比較例のポリマーは約80℃のTgを有している。
270ミクロンの厚さのITO基板を保持したガラス基板上に、ポリ(エチレンジオキシチオフェン)/ポリスチレンスルホネート(Baytron PTMとして、BayerTMから利用可能)をスピンコーティングにより、270ミクロンの厚さまで堆積させた。この基板上に、本発明のポリマーを、スピンコーティングにより50nmの厚さまで堆積させた。フッ化リチウム(厚さ4nm)の層がポリマー上に蒸着され、次にカルシウムのカソード(50nmの厚さ)が蒸着された。この装置は、金属缶を用いて封止された。
前述した比較例のポリマーを使用した以外は上記の光学装置例に類似する装置が製造された。この装置の寿命は、約1000時間である。ポリマーP1及び比較例のポリマーは、共に青色発光ポリマーである。
2 LiAl層
3 PPV発光層
4 正孔輸送層
Claims (7)
- 置換され又は置換されない一般式IIIを有する基からなる第1繰返し単位を有する共役ポリマーであって、
さらなる繰返し単位として、9,9−ジ−n−オクチルフルオレン、トリアリールアミン、及びビストリアリールアミンを含むポリマー。 - 前記Xがメチル、エチル、n−ブチル、s−ブチル、第3ブチルから選択される請求項1に記載のポリマー。
- Tgが少なくとも100℃である請求項1または2に記載のポリマー。
- 請求項1ないし3のいずれかに記載のポリマーを使用した電子輸送材料。
- 基板及び基板上に支持された請求項1ないし3のいずれかで定義されたポリマーを含む光学装置又はそのための構成要素。
- 光学装置が電子発光(electroluminescent)装置である請求項5に記載の光学装置又はそのための構成要素。
- 電子発光装置が次の構成を有する請求項6に記載の光学装置。
正電荷を注入するための第1電荷輸送体、
負電荷を注入するための第2電荷輸送体、
正電荷と負電荷を受取って結合し、光を発生するための、電荷注入層と負電荷注入層の間に位置する発光層、
負電荷を輸送し、第2電荷注入層と発光層の間、又は発光層中に位置する請求項1ないし3のいずれかに記載のポリマー。
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GB0111549.2 | 2001-05-11 | ||
US31562301P | 2001-08-29 | 2001-08-29 | |
US60/315623 | 2001-08-29 | ||
PCT/GB2002/002179 WO2002092724A1 (en) | 2001-05-11 | 2002-05-10 | Substituted fluorene polymers, their preparation and uses |
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GB0111549D0 (en) * | 2001-05-11 | 2001-07-04 | Cambridge Display Tech Ltd | Polymers, their preparation and uses |
US7632908B2 (en) * | 2001-05-11 | 2009-12-15 | Cambridge Display Technology Limited | Substituted fluorene polymers, their preparation and use in optical devices |
JP5069401B2 (ja) | 2002-05-10 | 2012-11-07 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ポリマー及びその製造方法 |
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US7402343B2 (en) | 2003-01-29 | 2008-07-22 | Samsung Sdi Co., Ltd. | Molecular chemical compounds with structures allowing electron displacement and capable of emitting photoluminescent radiation, and photoluminescence quenching device employing the same |
EP1443093A1 (de) * | 2003-01-29 | 2004-08-04 | Samsung SDI Co., Ltd. | Molekulare zur Emission von Photolumineszenzstrahlen befähigte, chemische Verbindungen mit elektronenverschiebbaren Strukturen und ihre Verwendung in Photolumineszenz-Löschungsanzeigeelementen |
US7138483B2 (en) | 2003-02-12 | 2006-11-21 | E.I. Du Pont De Nemours And Company | Monomers, conjugated polymers and electronic devices using such polymers |
GB0306414D0 (en) * | 2003-03-20 | 2003-04-23 | Cambridge Display Tech Ltd | Polymers,their preparations and uses |
JP4846191B2 (ja) * | 2003-06-04 | 2011-12-28 | 住友化学株式会社 | 色変換膜および発光装置 |
WO2005036666A2 (en) * | 2003-09-16 | 2005-04-21 | Dow Global Technologies Inc. | Method of preparing an insoluble polymer film on a substrate from a soluble polymer containing labile solubilizing groups |
US7652126B2 (en) * | 2003-10-07 | 2010-01-26 | General Electric Company | Monomers and polymers comprising conjugated groups and methods for making thereof |
US7115899B2 (en) * | 2003-10-29 | 2006-10-03 | E. I. Du Pont De Nemours And Company | Light-emitting copolymers and electronic devices using such copolymers |
US7119360B2 (en) | 2003-10-29 | 2006-10-10 | Max-Plank-Society | Light-emitting polymers and electronic devices using such polymers |
GB0329364D0 (en) | 2003-12-19 | 2004-01-21 | Cambridge Display Tech Ltd | Optical device |
DE10361385B4 (de) | 2003-12-29 | 2011-07-28 | OSRAM Opto Semiconductors GmbH, 93055 | Polymere, phosphoreszierende, organisch halbleitende Emittermaterialien auf Basis perarylierter Borane, Verfahren zu deren Herstellung und Verwendungen davon |
KR101170168B1 (ko) * | 2004-01-30 | 2012-07-31 | 에스케이이노베이션 주식회사 | 9,9-디(플루오레닐)-2,7-플루오레닐 단위를 함유하는 유기전기발광고분자 및 이를 이용한 전기발광소자 |
DE102004015845B4 (de) * | 2004-03-31 | 2012-12-20 | Osram Opto Semiconductors Gmbh | Organische Leuchtdiode, sowie Verwendungen davon |
GB0422391D0 (en) * | 2004-10-08 | 2004-11-10 | Cambridge Display Tech Ltd | Light emitting device |
JP5588096B2 (ja) | 2004-10-11 | 2014-09-10 | ケンブリッジ ディスプレイ テクノロジー リミテッド | 極性半導体正孔輸送材料 |
DE112005003032T5 (de) * | 2004-12-03 | 2007-12-13 | Sumitomo Chemical Co., Ltd. | Salicylat-substituierte konjugierte Polymere und Vorrichtungen |
US9179518B2 (en) | 2004-12-24 | 2015-11-03 | Cambridge Display Technology Limited | Light emissive device |
GB0428445D0 (en) | 2004-12-29 | 2005-02-02 | Cambridge Display Tech Ltd | Blue-shifted triarylamine polymer |
DE112005003872A5 (de) | 2004-12-29 | 2016-03-03 | Cambridge Display Technology Ltd. | Starre Amine |
GB0507684D0 (en) * | 2005-04-15 | 2005-05-25 | Cambridge Display Tech Ltd | Pulsed driven displays |
JP2007016226A (ja) * | 2005-06-10 | 2007-01-25 | Sumitomo Chemical Co Ltd | 芳香族重合体 |
US7852434B2 (en) | 2005-06-10 | 2010-12-14 | Sumitomo Chemical Company, Limited | Aromatic polymer |
US8927115B2 (en) | 2006-09-14 | 2015-01-06 | Sumitomo Chemical Company, Limited | Organic electroluminescent device |
GB2454890B (en) * | 2007-11-21 | 2010-08-25 | Limited Cambridge Display Technology | Light-emitting device and materials therefor |
JP5353186B2 (ja) | 2007-11-30 | 2013-11-27 | 住友化学株式会社 | アミン系高分子化合物及びそれを用いた発光素子 |
KR101626994B1 (ko) * | 2008-03-07 | 2016-06-03 | 스미또모 가가꾸 가부시끼가이샤 | 적층 구조체 |
GB0814161D0 (en) | 2008-08-01 | 2008-09-10 | Cambridge Display Tech Ltd | Blue-light emitting material |
GB2477426B (en) * | 2010-01-28 | 2016-02-24 | Sumitomo Chemical Co | Fluorene polymers and light emitting device using the same |
TWI504668B (zh) | 2010-01-28 | 2015-10-21 | 住友化學股份有限公司 | 高分子化合物及使用該高分子化合物而構成之發光元件 |
GB2486202A (en) | 2010-12-06 | 2012-06-13 | Cambridge Display Tech Ltd | Adhesion layer for solution-processed transition metal oxides on inert metal contacts of organic thin film transistors. |
GB2486203A (en) | 2010-12-06 | 2012-06-13 | Cambridge Display Tech Ltd | Transition metal oxide doped interface by deposition and drying of precursor |
WO2012086668A1 (ja) | 2010-12-21 | 2012-06-28 | 住友化学株式会社 | 高分子化合物及びそれを用いた発光素子 |
GB2494096B (en) * | 2011-01-31 | 2013-12-18 | Cambridge Display Tech Ltd | Polymer |
CN103339167B (zh) * | 2011-01-31 | 2018-01-12 | 剑桥显示技术有限公司 | 聚合物 |
GB201110770D0 (en) | 2011-06-24 | 2011-08-10 | Cambridge Display Tech Ltd | Process for controlling the acceptor strength of solution-processed transition metal oxides for OLED applications |
GB201200619D0 (en) * | 2012-01-16 | 2012-02-29 | Cambridge Display Tech Ltd | Polymer |
GB2505893A (en) | 2012-09-13 | 2014-03-19 | Cambridge Display Tech Ltd | Compounds for use in organic optoelectronic devices |
GB201320881D0 (en) | 2013-11-26 | 2014-01-08 | Cambridge Display Tech Ltd | Organic light-emitting device and method |
GB2597797A (en) * | 2020-08-07 | 2022-02-09 | Sumitomo Chemical Co | Light-emitting marker |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2603288B1 (fr) * | 1986-09-03 | 1988-12-09 | France Etat | Polyfluorenes 9,9'-disubstitues, leur procede de preparation et leurs applications en electro-optique et electrochimie |
JP3865406B2 (ja) * | 1995-07-28 | 2007-01-10 | 住友化学株式会社 | 2,7−アリール−9−置換フルオレン及び9−置換フルオレンオリゴマー及びポリマー |
JPH10104861A (ja) * | 1996-08-08 | 1998-04-24 | Canon Inc | 電子写真感光体、該電子写真感光体を有するプロセスカートリッジ及び電子写真装置 |
US6309763B1 (en) * | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
US5777070A (en) * | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
KR100697861B1 (ko) * | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
DE19846768A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere enthaltend 2,7-Fluorenyleinheiten mit verbesserten Eigenschaften |
DE19846766A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
DE69924155T2 (de) * | 1999-02-04 | 2006-04-13 | Dow Global Technologies, Inc., Midland | Fluoren-copolymere und daraus hergestellte vorrichtungen |
WO2000053656A1 (en) * | 1999-03-05 | 2000-09-14 | Cambridge Display Technology Limited | Polymer preparation |
JP2001151868A (ja) * | 1999-11-24 | 2001-06-05 | Toyota Central Res & Dev Lab Inc | 機能性共重合高分子及びそれを使用した有機電界発光素子、光メモリ、正孔移動素子 |
GB0111549D0 (en) * | 2001-05-11 | 2001-07-04 | Cambridge Display Tech Ltd | Polymers, their preparation and uses |
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2001
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CN1513044A (zh) | 2004-07-14 |
WO2002092723A1 (en) | 2002-11-21 |
JP4050988B2 (ja) | 2008-02-20 |
TWI304436B (en) | 2008-12-21 |
EP1385919A1 (en) | 2004-02-04 |
JP2004532325A (ja) | 2004-10-21 |
EP1385919B1 (en) | 2004-08-11 |
EP1385918A1 (en) | 2004-02-04 |
TWI279429B (en) | 2007-04-21 |
DE60200951T2 (de) | 2005-01-27 |
EP1385918B1 (en) | 2005-04-06 |
CN101215370B (zh) | 2012-06-20 |
JP2004527628A (ja) | 2004-09-09 |
DE60203610T2 (de) | 2005-09-15 |
DE60203610D1 (de) | 2005-05-12 |
CN101215370A (zh) | 2008-07-09 |
EP1586617A1 (en) | 2005-10-19 |
WO2002092724A1 (en) | 2002-11-21 |
ATE273363T1 (de) | 2004-08-15 |
GB0111549D0 (en) | 2001-07-04 |
ATE292662T1 (de) | 2005-04-15 |
DE60200951D1 (de) | 2004-09-16 |
CN100417703C (zh) | 2008-09-10 |
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