TWI373483B - Water dispersible polythiophenes made with polymeric acid colloids - Google Patents
Water dispersible polythiophenes made with polymeric acid colloids Download PDFInfo
- Publication number
- TWI373483B TWI373483B TW093111298A TW93111298A TWI373483B TW I373483 B TWI373483 B TW I373483B TW 093111298 A TW093111298 A TW 093111298A TW 93111298 A TW93111298 A TW 93111298A TW I373483 B TWI373483 B TW I373483B
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- Taiwan
- Prior art keywords
- group
- acid
- colloid
- ether
- polymeric
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 132
- 229920000123 polythiophene Polymers 0.000 title claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 68
- 239000000084 colloidal system Substances 0.000 title claims description 62
- 239000006185 dispersion Substances 0.000 claims description 125
- 239000000203 mixture Substances 0.000 claims description 114
- 229920000642 polymer Polymers 0.000 claims description 76
- 239000000178 monomer Substances 0.000 claims description 74
- 239000007788 liquid Substances 0.000 claims description 72
- -1 ether carboxylic acid Chemical class 0.000 claims description 66
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 61
- 238000006116 polymerization reaction Methods 0.000 claims description 47
- 239000000463 material Substances 0.000 claims description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- 239000002245 particle Substances 0.000 claims description 35
- 239000011541 reaction mixture Substances 0.000 claims description 33
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 239000007800 oxidant agent Substances 0.000 claims description 30
- 229930192474 thiophene Natural products 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 239000003456 ion exchange resin Substances 0.000 claims description 25
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 25
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- 230000005669 field effect Effects 0.000 claims description 12
- 238000012546 transfer Methods 0.000 claims description 12
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 10
- 239000002105 nanoparticle Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 9
- 239000010409 thin film Substances 0.000 claims description 9
- KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical compound CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002041 carbon nanotube Substances 0.000 claims description 7
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 6
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical group C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002070 nanowire Substances 0.000 claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 239000002082 metal nanoparticle Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000003990 capacitor Substances 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000011852 carbon nanoparticle Substances 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 3
- 230000005055 memory storage Effects 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000007784 solid electrolyte Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- WXFWXFIWDGJRSC-UHFFFAOYSA-N 2,5-dimethoxy-2,5-dihydrofuran Chemical compound COC1OC(OC)C=C1 WXFWXFIWDGJRSC-UHFFFAOYSA-N 0.000 claims description 2
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 2
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000831 Steel Inorganic materials 0.000 claims description 2
- 239000004917 carbon fiber Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000004146 energy storage Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 239000010959 steel Substances 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims 2
- 235000021419 vinegar Nutrition 0.000 claims 2
- 239000000052 vinegar Substances 0.000 claims 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
- JOWBFITYYIZBFK-UHFFFAOYSA-N 2,2-bis(sulfanyl)acetamide Chemical compound NC(=O)C(S)S JOWBFITYYIZBFK-UHFFFAOYSA-N 0.000 claims 1
- RCJRILMVFLGCJY-UHFFFAOYSA-N 4-phenyl-1,3-dioxane Chemical compound O1COCCC1C1=CC=CC=C1 RCJRILMVFLGCJY-UHFFFAOYSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- YSEFUOLCXKPXDI-UHFFFAOYSA-N C(NN)(=O)O.NC(=N)N Chemical compound C(NN)(=O)O.NC(=N)N YSEFUOLCXKPXDI-UHFFFAOYSA-N 0.000 claims 1
- 241000270666 Testudines Species 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 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 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 229940116269 uric acid Drugs 0.000 claims 1
- 239000010410 layer Substances 0.000 description 152
- 229920000557 Nafion® Polymers 0.000 description 52
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 43
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 41
- 239000010408 film Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 27
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 229920001940 conductive polymer Polymers 0.000 description 25
- 238000001246 colloidal dispersion Methods 0.000 description 21
- 239000008367 deionised water Substances 0.000 description 21
- 229910021641 deionized water Inorganic materials 0.000 description 21
- 239000011347 resin Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 20
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 17
- 230000001590 oxidative effect Effects 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- 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 description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 14
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000007924 injection Substances 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 101001102158 Homo sapiens Phosphatidylserine synthase 1 Proteins 0.000 description 11
- 102100039298 Phosphatidylserine synthase 1 Human genes 0.000 description 11
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- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 239000000126 substance Substances 0.000 description 8
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- 230000002378 acidificating effect Effects 0.000 description 7
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- 239000012530 fluid Substances 0.000 description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
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- 229910000358 iron sulfate Inorganic materials 0.000 description 5
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 5
- XBDUTCVQJHJTQZ-UHFFFAOYSA-L iron(2+) sulfate monohydrate Chemical compound O.[Fe+2].[O-]S([O-])(=O)=O XBDUTCVQJHJTQZ-UHFFFAOYSA-L 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- 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
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/08—Polysulfonates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Nanotechnology (AREA)
- Health & Medical Sciences (AREA)
- Composite Materials (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (3)
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| US46437003P | 2003-04-22 | 2003-04-22 | |
| US10/669,494 US7431866B2 (en) | 2002-09-24 | 2003-09-24 | Water dispersible polythiophenes made with polymeric acid colloids |
| US10/802,704 US7390438B2 (en) | 2003-04-22 | 2004-03-17 | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
Publications (2)
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| TW200502278A TW200502278A (en) | 2005-01-16 |
| TWI373483B true TWI373483B (en) | 2012-10-01 |
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| TW093111298A TWI373483B (en) | 2003-04-22 | 2004-04-22 | Water dispersible polythiophenes made with polymeric acid colloids |
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| JP (1) | JP4851323B2 (https=) |
| CN (2) | CN1777648B (https=) |
| TW (1) | TWI373483B (https=) |
Cited By (1)
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|---|---|---|---|---|
| TWI644463B (zh) * | 2012-10-26 | 2018-12-11 | 黑拉耶烏斯貴金屬公司 | 在ＯＬＥＤｓ中具有高導電度及高效能之透明層及其製造方法 |
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| JP4464277B2 (ja) | 2002-09-24 | 2010-05-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法 |
| CA2499364A1 (en) | 2002-09-24 | 2004-04-08 | E. I. Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
| US7317047B2 (en) | 2002-09-24 | 2008-01-08 | E.I. Du Pont De Nemours And Company | Electrically conducting organic polymer/nanoparticle composites and methods for use thereof |
| WO2004029128A2 (en) | 2002-09-24 | 2004-04-08 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US20050175861A1 (en) * | 2004-02-10 | 2005-08-11 | H.C. Starck Gmbh | Polythiophene compositions for improving organic light-emitting diodes |
| US7250461B2 (en) * | 2004-03-17 | 2007-07-31 | E. I. Du Pont De Nemours And Company | Organic formulations of conductive polymers made with polymeric acid colloids for electronics applications, and methods for making such formulations |
| US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| JP5241997B2 (ja) * | 2005-03-08 | 2013-07-17 | 信越ポリマー株式会社 | 導電性高分子溶液および導電性塗膜 |
| EP1897096A4 (en) | 2005-06-28 | 2009-08-12 | Du Pont | TRANSPARENT LADDER WITH HIGH WORKING FUNCTION |
| WO2007002738A2 (en) * | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Bilayer anode |
| WO2007002740A2 (en) | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Buffer compositions |
| KR101193180B1 (ko) * | 2005-11-14 | 2012-10-19 | 삼성디스플레이 주식회사 | 전도성 고분자 조성물 및 이로부터 얻은 막을 구비한 전자소자 |
| US8216680B2 (en) | 2006-02-03 | 2012-07-10 | E I Du Pont De Nemours And Company | Transparent composite conductors having high work function |
| US20070278458A1 (en) * | 2006-04-13 | 2007-12-06 | Martello Mark T | Electrically conductive polymer compositions |
| US20080191172A1 (en) | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
| WO2008134492A1 (en) * | 2007-04-27 | 2008-11-06 | Konarka Technologies, Inc. | Organic photovoltaic cells |
| CN101125950B (zh) * | 2007-08-03 | 2010-05-26 | 上海复旦天臣新技术有限公司 | 空穴传输材料的制备方法 |
| US8183319B2 (en) * | 2007-10-31 | 2012-05-22 | Air Products And Chemicals, Inc. | Film forming additive formulations of conductive polymers |
| JP5243067B2 (ja) * | 2008-03-10 | 2013-07-24 | 日機装株式会社 | 導電性ポリマーの導電性向上方法 |
| US20110037066A1 (en) * | 2008-04-28 | 2011-02-17 | Sumitomo Chemical Company, Limited. | Organic photoelectric conversion element and manufacturing method thereof |
| JP2010192863A (ja) * | 2008-05-23 | 2010-09-02 | Sumitomo Chemical Co Ltd | 有機光電変換素子およびその製造方法 |
| US8785913B2 (en) | 2008-12-27 | 2014-07-22 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
| US8766239B2 (en) | 2008-12-27 | 2014-07-01 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
| EP2421918B1 (en) | 2009-04-21 | 2020-08-26 | LG Chem, Ltd. | Electrically conductive polymer compositions and films made therefrom |
| TW201100482A (en) | 2009-04-24 | 2011-01-01 | Du Pont | Electrically conductive polymer compositions and films made therefrom |
| JP2011093993A (ja) * | 2009-10-28 | 2011-05-12 | Marubishi Oil Chem Co Ltd | 導電性ポリ（３，４−エチレンジオキシチオフェン）コロイド水溶液及びその製造方法 |
| WO2011105148A1 (ja) * | 2010-02-24 | 2011-09-01 | コニカミノルタホールディングス株式会社 | 透明導電膜、および有機エレクトロルミネッセンス素子 |
| CN101812171B (zh) * | 2010-04-13 | 2012-01-25 | 无锡中美亿芯生物科技有限公司 | 一种用于生物传感器的导电聚合物及其制备方法 |
| JP5573539B2 (ja) * | 2010-09-21 | 2014-08-20 | トヨタ自動車株式会社 | 燃料電池用電極の製造方法 |
| JPWO2013047660A1 (ja) | 2011-09-28 | 2015-03-26 | コニカミノルタ株式会社 | 透明電極、有機電子素子および透明電極の製造方法 |
| JP5764092B2 (ja) * | 2012-06-04 | 2015-08-12 | Ｊｆｅケミカル株式会社 | 導電性高分子の分散体およびその製造方法 |
| JP5955786B2 (ja) | 2013-01-07 | 2016-07-20 | 出光興産株式会社 | 導電性高分子組成物 |
| CN103709417B (zh) * | 2013-12-24 | 2016-06-29 | 深圳新宙邦科技股份有限公司 | 一种聚噻吩类衍生物水分散体及其制备方法 |
| CN104448256B (zh) * | 2014-12-02 | 2017-04-12 | 浙江中科立德新材料有限公司 | 高导电pedot：pss水溶液的制备方法 |
| JP6724526B2 (ja) * | 2016-04-27 | 2020-07-15 | 東ソー株式会社 | 水溶性導電性高分子、その製造方法、その導電性高分子水溶液、及びその用途 |
| WO2018135582A1 (ja) * | 2017-01-18 | 2018-07-26 | 日産化学工業株式会社 | インク組成物 |
| CN111192966B (zh) * | 2020-01-09 | 2023-07-25 | 通威太阳能(眉山)有限公司 | 钙钛矿太阳能电池及其制备方法 |
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| CN114316223B (zh) * | 2021-12-31 | 2022-09-27 | 华中科技大学 | 一种导电聚乙烯二氧噻吩的醇分散液及其制备方法和应用 |
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| EP0440957B1 (de) * | 1990-02-08 | 1996-03-27 | Bayer Ag | Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung |
| DE4211461A1 (de) * | 1992-04-06 | 1993-10-07 | Agfa Gevaert Ag | Antistatische Kunststoffteile |
| DE69319200T2 (de) * | 1992-10-14 | 1999-01-28 | Agfa-Gevaert N.V., Mortsel | Antistatische Beschichtungszusammensetzung |
| ATE228545T1 (de) * | 1994-05-06 | 2002-12-15 | Bayer Ag | Leitfähige beschichtungen |
| JP3937113B2 (ja) * | 1998-06-05 | 2007-06-27 | 日産化学工業株式会社 | 有機−無機複合導電性ゾル及びその製造法 |
| DE19841803A1 (de) * | 1998-09-12 | 2000-03-16 | Bayer Ag | Hilfsschichten für elektrolumineszierende Anordnungen |
| EP1054414B1 (en) * | 1999-05-20 | 2003-03-12 | Agfa-Gevaert | Method for patterning a layer of conductive polymer |
| JP4363050B2 (ja) * | 2002-01-31 | 2009-11-11 | 住友化学株式会社 | 有機エレクトロルミネッセンス素子 |
| JP4464277B2 (ja) * | 2002-09-24 | 2010-05-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法 |
| WO2004029128A2 (en) * | 2002-09-24 | 2004-04-08 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
-
2004
- 2004-04-22 CN CN2004800107982A patent/CN1777648B/zh not_active Expired - Lifetime
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI644463B (zh) * | 2012-10-26 | 2018-12-11 | 黑拉耶烏斯貴金屬公司 | 在ＯＬＥＤｓ中具有高導電度及高效能之透明層及其製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006527277A (ja) | 2006-11-30 |
| JP4851323B2 (ja) | 2012-01-11 |
| CN102212251B (zh) | 2013-06-19 |
| CN1777648A (zh) | 2006-05-24 |
| CN102212251A (zh) | 2011-10-12 |
| TW200502278A (en) | 2005-01-16 |
| CN1777648B (zh) | 2011-06-08 |
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