CN102089348A - 对有机溶剂具有分散性的导电性聚合物及其制备方法 - Google Patents
对有机溶剂具有分散性的导电性聚合物及其制备方法 Download PDFInfo
- Publication number
- CN102089348A CN102089348A CN2009801271671A CN200980127167A CN102089348A CN 102089348 A CN102089348 A CN 102089348A CN 2009801271671 A CN2009801271671 A CN 2009801271671A CN 200980127167 A CN200980127167 A CN 200980127167A CN 102089348 A CN102089348 A CN 102089348A
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- Prior art keywords
- conductive polymer
- electric conductive
- organic solvent
- acid
- thiophene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 61
- 239000002019 doping agent Substances 0.000 claims abstract description 28
- -1 phosphate compound Chemical class 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 20
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 7
- 150000002500 ions Chemical class 0.000 claims abstract description 7
- 239000010452 phosphate Substances 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- 241000790917 Dioxys <bee> Species 0.000 claims description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000004160 Ammonium persulphate Substances 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 10
- 235000019395 ammonium persulphate Nutrition 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 8
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 claims description 7
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000011669 selenium Chemical group 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 150000001345 alkine derivatives Chemical class 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 150000001343 alkyl silanes Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 4
- UDCASSBIUUGACU-UHFFFAOYSA-N 2,3-diethoxythiophene Chemical compound CCOC=1C=CSC=1OCC UDCASSBIUUGACU-UHFFFAOYSA-N 0.000 claims description 4
- JBOAELCPSXBGSR-UHFFFAOYSA-N 2,3-dimethoxythiophene Chemical compound COC=1C=CSC=1OC JBOAELCPSXBGSR-UHFFFAOYSA-N 0.000 claims description 4
- RDEMFXWUHQVWDF-UHFFFAOYSA-N 2,3-dipropoxythiophene Chemical compound CCCOC=1C=CSC=1OCCC RDEMFXWUHQVWDF-UHFFFAOYSA-N 0.000 claims description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 claims description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- INPLNPUUMKZLTP-UHFFFAOYSA-N 2,3-dibutoxythiophene Chemical compound CCCCOC=1C=CSC=1OCCCC INPLNPUUMKZLTP-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000003233 pyrroles Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims description 2
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 claims description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004159 Potassium persulphate Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims description 2
- 229950005953 camsilate Drugs 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 claims description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- FYMCOOOLDFPFPN-UHFFFAOYSA-K iron(3+);4-methylbenzenesulfonate Chemical compound [Fe+3].CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 FYMCOOOLDFPFPN-UHFFFAOYSA-K 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 2
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- 150000002825 nitriles Chemical class 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- 235000019394 potassium persulphate Nutrition 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
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- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 claims 2
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 claims 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
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- 230000015572 biosynthetic process Effects 0.000 description 5
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- 238000006243 chemical reaction Methods 0.000 description 3
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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Abstract
本发明涉及一种容易分散在有机溶剂中的导电性聚合物及其制备方法,更具体地,涉及一种对有机溶剂具有分散性的导电性聚合物的制备方法,该方法使用在有机溶剂中可溶解的磷酸酯类化合物来作为掺杂阴离子而使单体进行聚合。本发明可通过简易的工序而获得能够在多种不同的有机溶剂中分散的导电性聚合物,因此可被利用在现有的水分散性导电性聚合物的使用受限的应用材料领域中。
Description
技术领域
本发明涉及一种能够分散在各种有机溶剂中的导电性聚合物的制备方法,尤其是关于一种在导电性聚合物合成时利用了在有机溶剂中具有高溶解性的掺杂剂,因而容易分散在有机溶剂中并具有高导电性的导电性聚合物的制备方法。
背景技术
与传统的电绝缘聚合物不同,导电性聚合物,如聚苯胺(polyaniline)、聚吡咯(polypyrrole)、聚噻吩(polythiophene)以及其衍生物,通过掺杂而显示可变的导电性。因此,为将此种导电性聚合物应用在包括抗静电材料、电容器、电致变色(electrochromic)装置或显示器薄膜材料等领域上,已做了许多努力。
然而,导电性聚合物由于强烈的分子间引力以及用作掺杂剂的阴离子的影响无法溶解于溶剂中,而导致加工性降低。即使在克服上述问题且目前商业上可购得的聚(3,4-乙烯二氧噻吩)(3,4-ethylenedioxythiophene)/聚苯乙烯酸(Clevios P,其可购自于德国,H.C.Starck Gmbh公司)的情况下,其仅能提供分散在水中的形式,因此只能应用在特定的领域。
为了解上述问题,已设计出各种不同的方法。
例如,美国专利第2003/0088032A1号公开了一种制备导电性聚合物的方法,此方法通过将杂环芳香(heteroaromatic)导电性聚合物嵌段(polymer block)与能够赋予有机溶剂溶解性的环氧乙烷嵌段(ethyleneoxide block)进行共聚(copolymerizing),或者在导电性聚合物低聚体上封端(end-capping)甲基丙烯酸酯或其他丙烯酸酯基,从而能够分散在硝基甲烷(nitromethane)、碳酸丙烯酯(propylenecarbonate)等有机溶剂中。
上述方法通过改变导电性聚合物链的键结构本身以赋予在有机溶剂中的分散性,合成与聚合过程为多阶段,因此制备难,不容易控制物性,且合成的导电性聚合物的导电性变低。
另外,还报导过一种合成导电性聚合化合物的方法,其中使用例如聚乙烯醇、聚乙酸乙烯酯或纤维素衍生物的立体结构稳定剂,使所合成的聚合化合物颗粒具有小尺寸,因而促进聚合化合物分散于溶液中(Polymer,vol.33,pp.4857,1992)。然而,由于聚乙烯醇仅被用作分散稳定剂而不能作为掺杂剂,当最终形成导电性薄膜时,其作为杂质会降低导电性。
发明内容
因此,本发明旨在解决现有技术中的上述问题,而提供一种利用在各种有机溶解中具有溶解性的掺杂化合物,因而易于分散在有机溶剂中且具有高导电性的导电性聚合物及其制备方法。但本发明所要解决的技术问题并不限于此,未提及的其他技术问题,本领域技术人员可从以下说明中清楚地理解。
根据本发明的对有机溶剂具有分散性的导电性聚合物,通过由下列化学式1所示的导电性聚合物单体作为掺杂剂与由下列化学式2所示的对有机溶剂具有分散性的磷酸酯化合物进行聚合而制得。
化学式1
在化学式1中,R1与R2一起构成3至8元(membered)脂环族环或芳香环结构的亚烃基(alkylene)、亚烯基(alkenylene)、烯氧基(alkenyloxy)、烯二氧基(alkenyldioxy)、炔氧基(alkynyloxy)或炔二氧基(alkynyldioxy),或分别为氢、卤素、C1-C15的烷基、烷氧基、羰基或羟基,且杂原子(hetero atom)X选自硫(S)、氧(O)、硒(Se)以及NH。
化学式2
在化学式2中,R3与R4分别为选自C1-C20的烷基、异烷基、烷氧基、烷氧烷基(alkoxyalkyl)、烷基磺酰基(alkylsulfonyl)、烷氧磺酰基(alkoxysulfonyl)、烷基硅烷(alkylsilane)以及烷氧硅烷(alkoxysilane)中的一种。
另外,本发明还提供一种为赋予通过上述方法制备的导电性聚合物多种功能,而与各种粘合剂混合的导电性聚合物复合体的制备方法。
有益效果
根据本发明的对有机溶剂具有分散性的导电性聚合物,使用在有机溶剂中具有高溶解性的磷酸酯类化合物来作为掺杂剂,不仅可在各种有机溶剂中表现出高分散性,还显示优异的导电性。此外,本发明的导电性聚合物的制备方法除具有高导电性和对有机溶剂具有分散性之外,还具有制备方法简单的优点。
具体实施方式
以下,将对本发明进行详细说明。
本发明可提供一种由下列化学式3所示的对有机溶剂具有分散性的导电性聚合物及其制备方法,该聚合物使用由下列化学式2所示的磷酸酯类化合物作为掺杂剂阴离子,对由下列化学式1所示的单体进行化学聚合。
化学式1
在化学式1中,R1与R2一起构成3至8元脂环族环或芳香环结构的亚烷基、亚烯基、烯氧基、烯二氧基、炔氧基或炔二氧基,或分别为氢、卤素、C1-C15的烷基、烷氧基、羰基或羟基。另外,杂原子X选自硫(S)、氧(O)、硒(Se)以及NH。
化学式2
在化学式2中,R3与R4分别为选自C1-C20的烷基、异烷基、烷氧基、烷氧烷基、烷基磺酰基、烷氧磺酰基、烷基硅烷以及烷氧硅烷中的一种。
另外,本发明还提供一种为赋予通过上述方法制备的导电性聚合物多种功能,而与各种粘合剂混合的导电性聚合物复合体的制备方法。
化学式3
在化学式3中,Y是表示包括由化学式2所示的磷酸酯类化合物的掺杂剂阴离子。
根据本发明的对有机溶剂具有分散性的导电性聚合物的制备方法可包括:将化学式1的单体以及化学式2的磷酸酯类化合物添加到含水或不含水的合成溶剂中而获得混合溶液;另将氧化剂溶于水并将此添加到上述混合溶液中进行聚合反应即可。另外,将聚合反应完成后的有机层进行分离,除去未反应的物质和杂质,代替导电性聚合物质沉淀为颗粒相然后将其再次溶于溶剂,就可以在聚合反应后直接获得导电性聚合物被分散在溶剂内的导电性聚合物分散溶液。
由化学式1所示的单体优选苯胺、吡咯与其盐类或衍生物、3-甲基噻吩(3-methylthiophene)、3-己基噻吩(3-hexylthiophene)、3-辛基噻吩(3-octylthiophene)、3-甲氧基噻吩(3-methoxythiophene)、二甲氧基噻吩(dimethoxythiophene)、二乙氧基噻吩(diethoxythiophene)、二丙氧基噻吩(dipropoxythiophene)、二丁氧基噻吩(dibutoxythiophene)、亚甲二氧基噻吩(methylenedioxythiophene)、亚乙二氧基噻吩(ethylenedioxythiophene)、亚丙二氧基噻吩(propylenedioxythiophene)、以及亚丁二氧基噻吩(butylenedioxythiophene)。
由化学式2所示的化合物优选包括双(2-乙己基)磷酸酯酸或其盐类,其具有极性官能团磷酸酯基以及非极性官能团2-乙己基。其中,磷酸酯基用作导电性聚合物的掺杂阴离子,2-乙己基可有效进行在各种有机溶剂中的分散。另外,双(2-乙己基)磷酸酯酸中的2-乙己基为疏水性,相反其磷酸酯酸亲水性,双(2-乙己基)磷酸酯酸溶于亲水性溶剂与疏水性溶剂的混合溶剂中时,可形成微胞(micelle)结构,因此可通过乳液聚合来制备导电性聚合物。如此制备的对有机溶剂具有分散性的导电性聚合物,通过上述化合物在各种有机溶剂中具有高分散性。
另外,化学式2的化合物与其他掺杂剂一起使用时,化学式2的化合物可用以增加在有机溶剂中的分散性,而其他掺杂剂可增加最终形成的导电性聚合物的导电性,由此可提供更理想形态的导电性聚合物。可与化学式2的化合物一起使用的其他掺杂剂为芳香磺酸(aromatic sulfonic acid),包括苯磺酸(benzene sulfonic acid)、甲苯磺酸(toluene sulfonic acid)、2-萘磺酸(2-naphthalene sulfonic acid)、2,6-萘二磺酸(2,6-naphthalene disulfonic acid)、蒽醌磺酸(anthraquinone sulfonic acid)以及蒽醌二磺酸(anthraquinone disulfonic acid);或(二)烷基硫酸酯((di)alkylsulfate),包括甲基硫酸酯(methylsulfate)、二甲基硫酸酯(dimethylsulfate)、乙基硫酸酯(ethylsulfate)以及二乙基硫酸酯(diethylsulfate),但并不限于此。
此时,以1mol的导电性聚合物单体为准,使用0.1-100mol的掺杂剂,优选1-10mol。另,双(磷酸酯)基掺杂剂与其他掺杂剂的混合比例优选按重量计为100∶0-10∶90。
在单体聚合中所使用的溶剂可以为水或水与有机溶剂的混合溶剂。在使用水与有机溶剂的混合溶剂的情况下,有机溶剂可为选自由下列所组成的组中的一种或多种:醇类溶剂,包括甲醇、乙醇、丙醇、异丙醇、丁醇以及异丁醇;醚类溶剂,包括二乙醚、二丙醚、二丁醚、丁基乙醚以及四氢呋喃;醇醚类溶剂,包括乙二醇、丙二醇、乙二醇单甲醚、乙二醇单乙醚以及乙二醇单丁醚;酮类溶剂,包括丙酮、甲基乙基酮、甲基异丁基酮以及环己酮;酰胺类溶剂,包括N-甲基-2-吡咯烷酮、2-吡咯烷酮、N-甲基甲酰胺以及N,N-二甲基甲酰胺;亚砜类溶剂,包括二甲基亚砜以及二乙基亚砜;砜类溶剂,包括二乙基砜以及四亚甲基砜;腈类溶剂,包括乙腈以及苯甲腈;胺类溶剂,包括烷基胺、环胺以及芳香胺;酯类溶剂,包括丁酸甲酯、丁酸乙酯以及丙酸丙酯;羧酸酯类溶剂,包括乙酸乙酯以及乙酸丁酯;芳香烃类溶剂,包括苯、乙基苯、氯苯、甲苯以及二甲苯;脂肪烃类溶剂,包括己烷、庚烷以及环己烷;卤代烃类溶剂,包括氯仿、四氯乙烯、四氯化碳、二氯甲烷以及二氯乙烷;碳酸丙烯酯;碳酸乙烯酯;碳酸二甲酯;碳酸二丁酯;碳酸甲乙酯;碳酸二丁酯;硝基甲烷;硝基苯。
其中,水和有机溶剂的混合溶剂的混合比例可设定成按重量计为100∶0-10∶90。
将化学式1的单体以及化学式2的磷酸酯类化合物添加到含水或不含水的合成溶剂中获得混合溶液,然后将氧化剂单独溶于水并将此添加到上述混合溶液中,由此引发聚合反应。聚合反应时,在高速搅拌器(200-3000rpm)中进行会降低合成的导电性聚合物的颗粒尺寸,因此可更有效地增加导电性。
本发明的氧化剂,只要能够诱发导电性聚合物的聚合反应即可,而不受特别的限定。具体地包括:铁(Ⅲ)盐,包括FeCl3、Fe(ClO4)3、Fe2(SO4)3以及Fe2(S2O8)3;铁(Ⅲ)-无机酸盐;铁(Ⅲ)-有机酸盐,包括铁(Ⅲ)-甲苯磺酸盐以及铁(Ⅲ)-樟脑磺酸盐(camphorsulfonate);过硫酸盐,包括过硫酸铵((NH4)2S2O8)、过硫酸钠(Na2S2O8)以及过硫酸钾(K2S2O8);碱性过硼酸盐;过锰酸钾;二铬酸钾;铜盐;以及过氧化氢。
在聚合反应完成后,反应液放置一定时间,含有导电性聚合物的有机层与水层分离。然后,分离并收集含有导电性聚合物的有机层。因为含有导电性聚合物的有机层包括杂质以及未反应的物质,所以用清洗溶剂对其进行数次的清洗以纯化。
清洗溶剂是选自水、甲醇、2-丁醇、乙二醇、二乙二醇、乙基溶纤剂(ethylcellosolve)、丁基溶纤剂、乙基卡必醇(ethylcarbitol)、丁基卡必醇、丙酮以及它们的混合物。
通过本发明获得的导电性聚合物可根据聚合过程中所使用的氧化剂与混合掺杂剂的种类,而表现出从10-5S/cm至100S/cm的导电性,并且根据双(2-乙己基)磷酸酯酸以及混合掺杂剂,而有效分散在正丁醇、二甲基亚砜、N-甲基吡咯烷酮、二甲基甲酰胺、碳酸丙烯酯以及硝基甲烷的有机溶剂中。
依照本发明的导电性聚合物在如乙酸乙酯、甲苯或二甲苯非极性溶剂中具有弱分散性。然而,当导电性聚合物被分散在正丁醇中,然后与非极性溶剂混合时,其与非极性溶剂的混合不会发生凝集(aggregation)。
如上述分散在有机溶剂中的导电性聚合物与在有机溶剂中具有溶解性的各种有机或无机粘合剂的相容性好,因此在有机溶剂中混合导电性聚合物和粘合剂而制造的有机溶剂中,其可被用作抗静电涂布溶液。此时,粘合剂是为了调节最终涂膜的粘合力(adhesivity)、成型性(moldability)、抗刮性(scratch resistance)以及耐用性(durability)而使用,涂膜的表面电阻可根据导电性聚合物与粘合剂的含量比例而进行不同的调整。与导电性聚合物相混合的粘合剂可选自有机粘合剂,包括氨基甲酸酯基、环氧基、羧基、羰基、丙烯酸酯基、羟基、酯基、醚基、酰胺基、亚酰胺基、顺丁烯二酸基以及乙酸乙烯酯基;以及无机粘合剂,包括无机成分,此成分包括硅酸盐以及钛酸盐,但并不限于此。可使用本领域通常使用的有机或无机粘合剂的一种或多种混合使用。此时,上述粘合剂的含量为导电性聚合物重量的0.1-100倍。
粘合剂的含量大于导电性聚合物重量的100倍时,会增加最终形成的涂膜的表面电阻,因而使其难以符合所需的标准值;粘合剂的用量小于导电性聚合物重量的0.1倍时,将难以达到添加粘合剂而理应得到的涂布特性改善。
上述是关于使用磷酸酯酸化合物用作导电性聚合物的掺杂阴离子而将导电性聚合物分散于有机溶剂的方法,通过适当选择导电性聚合物、掺杂剂以及合成溶剂的种类,可在有机溶剂中具有高分散性以及高导电性,因此可被应用于各种应用领域中。
下面通过实施例详细说明本发明的对有机溶剂具有分散性的导电性聚合物。但下述的实施例只是为了更详细地说明本发明,本发明的权利要求范围并不限于此。
<实施例1>
在含有90ml蒸馏水的圆底烧瓶中,加入1.4g的3,4-乙烯二氧噻吩(EDOT,ethylenedioxythiophene)单体以及3.2g的双(2-乙己基)磷酸酯后搅拌混合。将2.3g的过硫酸铵(APS,ammonium persulfate)单独溶于10ml的蒸馏水中,因而获得APS水溶液。然后将APS水溶液缓慢地添加到EDOT单体与双(2-乙己基)磷酸酯的混合物中,引发聚合反应。在0℃下搅拌此反应物72小时完成聚合反应,分离并回收沉淀物。以水及醇类清洗上述沉淀物3次而除去杂质,然后在60℃下真空干燥24小时。将所获得的产物溶于极性有机溶剂二甲基亚砜中而形成5wt%的溶液,然后进行浇注形成薄膜。根据使用溶剂的种类,导电率为4.0×10-1S/cm。
<实施例2>
在含有110ml蒸馏水的圆底烧瓶中,加入2.1g的吡咯单体以及3.5g的双(2-乙己基)磷酸酯后搅拌混合。将1.3g的四氯化铁(FeCl4)单独地溶于10ml的蒸馏水中,因而获得FeCl4水溶液。然后将FeCl4水溶液缓慢地添加到吡咯单体与双(2-乙己基)磷酸酯的混合物中,引发聚合反应。在0℃下高速搅拌上述反应物3小时完成聚合反应,分离并回收沉淀物。以水及醇类清洗此沉淀物3次而去除杂质,并且在60℃下真空干燥24小时。将所获得的产物溶于极性有机溶剂N-甲基吡咯烷酮而形成3wt%的溶液,然后进行浇铸形成薄膜。根据使用溶剂的种类,导电率(四探针法,Keithley 2400)为1.4S/cm。
<实施例3>
除了使用60ml蒸馏水与40ml正丁醇的混合溶剂替代100ml蒸馏水来引发聚合反应以外,与实施例1的方法来进行聚合反应。在聚合反应完成后,将反应溶液在分液漏斗中放置3小时,分离含有聚(3,4-亚乙二氧基噻吩)(PEDOT,poly(3,4-ethylenedioxythiophene))的有机层与水层。以水及醇类交替清洗经过分离的有机层3次,去除未反应的物质与杂质。使用MgSO4对经过清洗的有机层进行完全除水,所获得的PEDOT可用乙酸乙酯稀释,使用No.16的刮棒涂布机涂布在PET膜上,然后在80℃下进行干燥2分钟形成薄膜。薄膜的表面电阻被测量为106欧姆/sq。
<实施例4>
将1.4g的3,4-乙烯二氧噻吩(EDOT)单体与混合掺杂剂的混合物添加到70ml蒸馏水与30ml正丁醇的混合溶剂中,上述混合掺杂剂是由2.7g的双(2-乙己基)磷酸酯与0.8g的二乙基硫酸酯混合而成。将2.3g的过硫酸铵(APS)单独地溶于10ml的蒸馏水中,因而获得APS水溶液。接著,将APS水溶液缓慢地添加到EDOT单体、双(2-乙己基)磷酸酯与二乙基硫酸酯的混合物中,引发聚合反应。在0℃下搅拌反应物72小时完成聚合反应。将反应物在分液漏斗中放置3小时,分离含有聚(3,4-亚乙二氧基噻吩)(PEDOT)的有机层与水层。以水及醇类交替清洗经过分离的有机层3次,去除未反应的物质与杂质。使用MgSO4对经过清洗的有机层进行完全除水,所获得的PEDOT利用乙酸乙酯加以稀释,使用No.16的刮棒涂布机涂布在PET膜上,然后在80℃下干燥2分钟形成薄膜。薄膜的表面电阻被测量为105欧姆/sq。
<实施例5>
将在实施例4中所制备的对有机溶剂具有分散性的导电性聚合物分散溶液与有机溶剂型丙烯酸粘合剂混合,因而获得抗静电涂布溶液。对有机溶剂具有分散性的导电性聚合物被分散在正丁醇/乙酸乙酯(体积比:10/90)的混合溶剂中,固形物含量为5%,并且使用光聚合性双酚A-二丙烯酸乙二醇酯(bisphenol A-ethyleneglycol diacrylate)来作为丙烯酸粘合剂。上述抗静电涂布溶液是混合40重量份的导电性聚合物、30重量份的双酚A-二丙烯酸乙二醇酯、2重量份的光起始剂1-羟基环己苯基酮(1-hydroxy cyclohexylphenylketone)、0.5重量份的光稳定剂Disperbyk-106(BYK公司)以及27.5重量份的乙酸乙酯而制成。使用No.16的刮棒涂布机,将上述抗静电涂布溶液涂布在PET膜上,在80℃下干燥2分钟,然后使用UV灯以300mJ/cm3的光量进行硬化。测得的表面电阻为109欧姆/sq,并且通过铅笔硬度测试测得的表面硬度为2H,确认表面硬度增加。
工业实用性
依照本发明,对有机溶剂具有分散性的导电性聚合物可用于包括抗静电涂布剂等等的各种抗静电领域中,或者用于电容器、电致变色装置或显示器薄膜材料等各种领域中。
Claims (19)
2.根据权利要求1所述的对有机溶剂具有分散性的导电性聚合物,其中,以1mol的所述单体为基准,所述掺杂剂的含量为0.1-100mol。
3.根据权利要求1或2所述的对有机溶剂具有分散性的导电性聚合物,其中,由化学式2所示的所述磷酸酯类化合物掺杂剂是与芳香磺酸或芳香磺酸酯或具有C1-C10的烷基的烷基硫酸酯混合作为混合掺杂剂使用的。
4.根据权利要求3所述的对有机溶剂具有分散性的导电性聚合物,其中,所述芳香磺酸或芳香磺酸酯是选自苯磺酸、甲苯磺酸、2-萘磺酸、2,6-萘二磺酸、蒽醌磺酸以及蒽醌二磺酸的芳香磺酸中的一种;所述烷基硫酸酯是选自甲基硫酸酯、二甲基硫酸酯、乙基硫酸酯以及二乙基硫酸酯的(二)烷基硫酸酯中的一种。
5.根据权利要求1-4中任意一项所述的对有机溶剂具有分散性的导电性聚合物,其中,所述化学式1所示的单体是选自苯胺、吡咯及其盐类或衍生物、3-甲基噻吩、3-己基噻吩、3-辛基噻吩、3-甲氧基噻吩、二甲氧基噻吩、二乙氧基噻吩、二丙氧基噻吩、二丁氧基噻吩、亚甲二氧基噻吩、亚乙二氧基噻吩、亚丙二氧基噻吩、以及亚丁二氧基噻吩中的一种;
所述化学式2所示的化合物为具有极性官能团磷酸酯基以及非极性官能团2-乙己基的双(2-乙己基)磷酸酯酸或其盐类。
7.根据权利要求6所述的对有机溶剂具有分散性的导电性聚合物,其中,所述Y的磷酸酯类化合物的阴离子是由下列掺杂剂所产生的:包括极性官能团磷酸酯基和非极性官能团2-乙己基的双(2-乙己基)磷酸酯酸或其盐类;或者磷酸酯类化合物与芳香磺酸或芳香磺酸酯或具有C1-C10的烷基的烷基硫酸酯混合的混合掺杂剂。
9.根据权利要求8所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,以1mol的所述单体为基准,所述掺杂剂的用量为0.1-100mol。
10.根据权利要求8或9所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,与化学式2所示的磷酸酯类化合物一起混合使用的掺杂剂为芳香磺酸或芳香磺酸酯或具有C1-C10的烷基的烷基硫酸酯。
11.根据权利要求10所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,所述芳香磺酸或其盐类是选自苯磺酸、甲苯磺酸、2-萘磺酸、2,6-萘二磺酸、蒽醌磺酸以及蒽醌二磺酸的芳香磺酸中的一种;烷基硫酸酯是选自甲基硫酸酯、二甲基硫酸酯、乙基硫酸酯以及二乙基硫酸酯的(二)烷基硫酸酯中的一种。
12.根据权利要求8-11中任意一项所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,所述氧化剂选自铁(Ⅲ)盐,包括FeCl3、Fe(ClO4)3、Fe2(SO4)3以及Fe2(S2O8)3;铁(Ⅲ)-无机酸盐;铁(Ⅲ)-有机酸盐,包括铁(Ⅲ)-甲苯磺酸盐以及铁(Ⅲ)-樟脑磺酸盐;过硫酸盐,包括过硫酸铵、过硫酸钠以及过硫酸钾;碱性过硼酸盐;过锰酸钾;二铬酸钾;铜盐;以及过氧化氢。
13.根据权利要求8-12中任意一项所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,所述溶剂为水、有机溶剂或水与有机溶剂的混合溶剂。
14.根据权利要求13所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,所述有机溶剂是选自下列的一种或多种:醇类溶剂,包括甲醇、乙醇、丙醇、异丙醇、丁醇以及异丁醇;醚类溶剂,包括二乙醚、二丙醚、二丁醚、丁基乙醚以及四氢呋喃;醇醚类溶剂,包括乙二醇、丙二醇、乙二醇单甲醚、乙二醇单乙醚以及乙二醇单丁醚;酮类溶剂,包括丙酮、甲基乙基酮、甲基异丁基酮以及环己酮;酰胺类溶剂,包括N-甲基-2-吡咯烷酮、2-吡咯烷酮、N-甲基甲酰胺以及N,N-二甲基甲酰胺;亚砜类溶剂,包括二甲基亚砜以及二乙基亚砜;砜溶剂,包括二乙基砜以及四亚甲基砜;腈溶剂,包括乙腈以及苯甲腈;胺溶剂,包括烷基胺、环胺以及芳香胺;酯类溶剂,包括丁酸甲酯、丁酸乙酯以及丙酸丙酯;羧酸酯类溶剂,包括乙酸乙酯以及乙酸丁酯;芳香烃类溶剂,包括苯、乙基苯、氯苯、甲苯以及二甲苯;脂肪烃类溶剂,包括己烷、庚烷以及环己烷;卤代烃溶剂,包括氯仿、四氯乙烯、四氯化碳、二氯甲烷以及二氯乙烷;碳酸丙烯酯;碳酸乙烯酯;碳酸二甲酯;碳酸二丁酯;碳酸甲乙酯;碳酸二丁酯;硝基甲烷;以及硝基苯。
15.根据权利要求13或14所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,所述混合溶剂中水与有机溶剂的混合比例,按重量计为100∶0-10∶90。
16.根据权利要求8-15中任一项所述的制备对有机溶剂具有分散性的导电性聚合物的方法,其中,所述化学式1所示的单体是选自苯胺、吡咯及其盐类或衍生物、3-甲基噻吩、3-己基噻吩、3-辛基噻吩、3-甲氧基噻吩、二甲氧基噻吩、二乙氧基噻吩、二丙氧基噻吩、二丁氧基噻吩、亚甲二氧基噻吩、亚乙二氧基噻吩、亚丙二氧基噻吩、以及亚丁二氧基噻吩中的一种;
所述由化学式2所示的化合物为具有极性官能团磷酸酯基以及非极性官能团2-乙己基的双(2-乙己基)磷酸酯酸或其盐类。
17.一种导电性聚合物复合体,其特征在于,该导电性聚合物复合体包括根据权利要求1-7中任意一项所述的导电性聚合物或者根据权利要求8-16中任意一项所述的方法制备的导电性聚合物;以及有机或无机粘合剂。
18.根据权利要求17所述的导电性聚合物复合体,其中,所述粘合剂是选自下列的一种或多种:有机粘合剂,包括胺基甲酸酯基、环氧基、羧基、羰基、丙烯酸基、羟基、酯基、醚基、酰胺基、亚酰胺基、顺丁烯二酸基以及乙酸乙烯酯基粘合剂;以及无机粘合剂,包括含有硅酸盐以及钛酸盐的无机成分。
19.根据权利要求17或18所述的导电性聚合物复合体,其中,所述粘合剂的含量为所述导电性聚合物的重量的0.1-100倍。
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CN102956373A (zh) * | 2011-08-18 | 2013-03-06 | 海洋王照明科技股份有限公司 | 电解液及其配制方法 |
CN106062033A (zh) * | 2014-02-27 | 2016-10-26 | 帝化株式会社 | 导电性高分子制造用氧化剂兼掺杂剂、其溶液、使用它们的任意一者制造而成的导电性高分子及使用该导电性高分子作为电解质的电解电容器 |
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CN106519250A (zh) * | 2016-09-29 | 2017-03-22 | 辽宁石油化工大学 | 含氮小分子有机配体调节荧光发射性质的一维链状铜配位聚合物的制备方法 |
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WO2015182954A1 (ko) * | 2014-05-27 | 2015-12-03 | 주식회사 엘지화학 | 전도성 고분자 잉크 조성물 |
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CN102956373A (zh) * | 2011-08-18 | 2013-03-06 | 海洋王照明科技股份有限公司 | 电解液及其配制方法 |
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CN106459638B (zh) * | 2014-05-27 | 2019-04-26 | 株式会社Lg化学 | 导电聚合物油墨组合物 |
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