CN100594560C - 制备导电涂层的方法 - Google Patents
制备导电涂层的方法 Download PDFInfo
- Publication number
- CN100594560C CN100594560C CN200480023731A CN200480023731A CN100594560C CN 100594560 C CN100594560 C CN 100594560C CN 200480023731 A CN200480023731 A CN 200480023731A CN 200480023731 A CN200480023731 A CN 200480023731A CN 100594560 C CN100594560 C CN 100594560C
- Authority
- CN
- China
- Prior art keywords
- reaction medium
- compound
- pedot
- polymer
- pss
- 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.)
- Expired - Fee Related
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000006185 dispersion Substances 0.000 claims abstract description 92
- 239000012429 reaction media Substances 0.000 claims abstract description 61
- 239000004816 latex Substances 0.000 claims abstract description 59
- 229920000126 latex Polymers 0.000 claims abstract description 59
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000002245 particle Substances 0.000 claims abstract description 39
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 38
- 239000011248 coating agent Substances 0.000 claims abstract description 29
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims abstract description 4
- 239000011164 primary particle Substances 0.000 claims abstract description 4
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 132
- 239000007788 liquid Substances 0.000 claims description 69
- 229910052760 oxygen Inorganic materials 0.000 claims description 59
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 54
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 54
- 239000001301 oxygen Substances 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 44
- 238000002360 preparation method Methods 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- -1 2-cyclohexylidene Chemical group 0.000 claims description 33
- 229930192474 thiophene Natural products 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000010276 construction Methods 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 17
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 241000790917 Dioxys <bee> Species 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000008199 coating composition Substances 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 10
- 239000012457 nonaqueous media Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 4
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical group O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- CJNYCXOZPQVMIV-UHFFFAOYSA-M sodium;4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)butane-1-sulfonate Chemical compound [Na+].O1C(COCCCCS(=O)(=O)[O-])COC2=CSC=C21 CJNYCXOZPQVMIV-UHFFFAOYSA-M 0.000 claims description 2
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 229920000447 polyanionic polymer Polymers 0.000 abstract description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 150000003951 lactams Chemical group 0.000 abstract 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 142
- 239000000203 mixture Substances 0.000 description 35
- 229910052799 carbon Inorganic materials 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 230000000875 corresponding effect Effects 0.000 description 19
- 230000003287 optical effect Effects 0.000 description 14
- 229920000123 polythiophene Polymers 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 101001102158 Homo sapiens Phosphatidylserine synthase 1 Proteins 0.000 description 9
- 102100039298 Phosphatidylserine synthase 1 Human genes 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000006056 electrooxidation reaction Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003233 pyrroles Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 238000004482 13C cross polarization magic angle spinning Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000004984 smart glass Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- JNQCCAPUTUZTTP-UHFFFAOYSA-N 3,3-dichloro-2-methylprop-2-enoic acid Chemical compound ClC(Cl)=C(C)C(O)=O JNQCCAPUTUZTTP-UHFFFAOYSA-N 0.000 description 1
- IEXLMWZQCURUMB-UHFFFAOYSA-N 3-acetyl-1-(dimethylamino)-4,4a,6,7,11,12-hexahydroxy-11-methyl-1,11a,12,12a-tetrahydrotetracene-2,5-dione Chemical compound C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(=O)C(C(C)=O)=C(O)C4(O)C(=O)C3=C(O)C2=C1O IEXLMWZQCURUMB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- KMHJKRGRIJONSV-UHFFFAOYSA-N dioxygen(.1+) Chemical compound [O+]=O KMHJKRGRIJONSV-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000005838 radical anions Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/48—Conductive polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/56—Solid electrolytes, e.g. gels; Additives therein
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Electrochemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03101827 | 2003-06-20 | ||
| EP03101827.8 | 2003-06-20 | ||
| PCT/EP2004/051073 WO2004114326A1 (en) | 2003-06-20 | 2004-06-09 | Process for preparing electroconductive coatings |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1839448A CN1839448A (zh) | 2006-09-27 |
| CN100594560C true CN100594560C (zh) | 2010-03-17 |
Family
ID=33522381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200480023731A Expired - Fee Related CN100594560C (zh) | 2003-06-20 | 2004-06-09 | 制备导电涂层的方法 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1639607A1 (ja) |
| JP (1) | JP2007526925A (ja) |
| KR (1) | KR100995561B1 (ja) |
| CN (1) | CN100594560C (ja) |
| WO (1) | WO2004114326A1 (ja) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005060159A1 (de) | 2005-12-14 | 2007-06-21 | H. C. Starck Gmbh & Co. Kg | Transparente polymere Elektrode für elektro-optische Aufbauten |
| US20080007518A1 (en) * | 2006-06-23 | 2008-01-10 | Debasis Majumdar | Conductive polymer coating with improved aging stability |
| JP5334856B2 (ja) | 2006-11-06 | 2013-11-06 | アグファ−ゲバルト | 太陽光暴露に対して改善された安定性を備えた層構造 |
| DE102007041722A1 (de) * | 2007-09-04 | 2009-03-05 | H.C. Starck Gmbh | Verfahren zur Herstellung von leitfähigen Polymeren |
| DE102008005568A1 (de) * | 2008-01-22 | 2009-07-23 | H.C. Starck Gmbh | Verfahren zur Herstellung von leitfähigen Polymeren |
| KR101035694B1 (ko) * | 2008-09-02 | 2011-05-19 | 한국기계연구원 | 나노 패턴을 갖는 도전성 폴리머층의 형성 방법 |
| JP4898850B2 (ja) * | 2009-01-22 | 2012-03-21 | 住友化学株式会社 | 有機エレクトロルミネッセンス素子用インクジェットインクおよび有機エレクトロルミネッセンス素子の製造方法 |
| DE102010047087A1 (de) * | 2010-10-01 | 2012-04-05 | Heraeus Clevios Gmbh | Verfahren zur Verbesserung der elektrischen Kenngrößen in Kondensatoren enthaltend PEDOT/PSS als Feststoffelektrolyt durch ein Polyalkylenglykol |
| JP6434906B2 (ja) * | 2013-04-18 | 2018-12-05 | 国立大学法人山梨大学 | 導電性ポリチオフェン化合物の溶液もしくは分散液の製造方法 |
| SG10201610499UA (en) * | 2015-12-14 | 2017-07-28 | Agency Science Tech & Res | Method Of Forming A Polythiophene: Polysulfonate Complex |
| US10658121B2 (en) * | 2017-10-18 | 2020-05-19 | Kemet Electronics Corporation | Process for forming a solid electrolytic capacitor |
| CN112521587B (zh) * | 2020-12-07 | 2023-08-11 | 南京浩瀚高分子新型材料有限公司 | 聚四氟乙烯微粉辅助制备水性聚合物的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59010247D1 (de) * | 1990-02-08 | 1996-05-02 | Bayer Ag | Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung |
| EP0602713B1 (en) * | 1992-12-17 | 1998-10-14 | Agfa-Gevaert N.V. | Permanent antistatic primer layer |
| ATE287929T1 (de) * | 1994-05-06 | 2005-02-15 | Bayer Ag | Leitfähige beschichtungen hergestellt aus mischungen enthaltend polythiophen und lösemittel |
| DE19507413A1 (de) * | 1994-05-06 | 1995-11-09 | 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 |
| DE69919661T2 (de) * | 1998-11-17 | 2005-09-22 | Agfa-Gevaert | Verfahren zur Herstellung einer Schicht aus leitfähigen Polythiophen bei niedriger Temperatur |
| EP1453877B1 (en) * | 2001-12-04 | 2007-03-28 | Agfa-Gevaert | Process for preparing an aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer |
-
2004
- 2004-06-09 WO PCT/EP2004/051073 patent/WO2004114326A1/en active Application Filing
- 2004-06-09 JP JP2006516142A patent/JP2007526925A/ja active Pending
- 2004-06-09 CN CN200480023731A patent/CN100594560C/zh not_active Expired - Fee Related
- 2004-06-09 KR KR1020057024380A patent/KR100995561B1/ko active IP Right Grant
- 2004-06-09 EP EP04741766A patent/EP1639607A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1639607A1 (en) | 2006-03-29 |
| KR20060015654A (ko) | 2006-02-17 |
| WO2004114326A1 (en) | 2004-12-29 |
| JP2007526925A (ja) | 2007-09-20 |
| KR100995561B1 (ko) | 2010-11-22 |
| CN1839448A (zh) | 2006-09-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7932320B2 (en) | Process for preparing electroconductive coatings | |
| EP1458785B1 (en) | 3,4-alkylenedioxy-thiophene copolymers | |
| JP4187656B2 (ja) | 新規な３，４−アルキレンジオキシチオフェン化合物及びそのポリマー | |
| CN100594560C (zh) | 制备导电涂层的方法 | |
| CN103180386B (zh) | 包含具有确定的噻吩类单体含量的聚噻吩的分散体 | |
| US7378039B2 (en) | Aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer | |
| CN1956988B (zh) | 单体、低聚和聚噻吩并[3,2-b]噻吩 | |
| US6927298B2 (en) | 3,4-alkylenedioxythiophenedioxide compounds and polymers comprising monomeric units thereof | |
| Dai et al. | Electrochemistry, electrochromic and color memory properties of polymer/copolymer based on novel dithienylpyrrole structure | |
| Ye et al. | Pyrrolophthalazine dione (PPD)-based donor–acceptor polymers as high performance electrochromic materials | |
| Mo et al. | Electrochemical synthesis and capacitance properties of a novel poly (3, 4-ethylenedioxythiophene bis-substituted bithiophene) electrode material | |
| US6995223B2 (en) | 3,4-alkylenedioxy-thiophene copolymers | |
| Contal et al. | Investigation of polycarbazoles thin films prepared by electrochemical oxidation of synthesized carbazole derivatives | |
| Xu et al. | Electrosyntheses of high quality poly (5-methylindole) films in mixed electrolytes of boron trifluoride diethyl etherate and diethyl ether | |
| Yang et al. | A Free‐standing electrochromic material of poly (5, 7‐bis (2‐(3, 4‐ethylenedioxy) thienyl)‐indole) and its application in electrochromic device | |
| Wang et al. | One-step electropolymerized thieno [3, 2-b] thiophene-based bifunctional electrode with controlled color conversion for electrochromic energy storage application | |
| Wałęsa-Chorab et al. | Dipyrromethane functionalized monomers as precursors of electrochromic polymers | |
| US7105620B2 (en) | 3,4-alkylenedioxy-thiophene copolymers | |
| Hu et al. | Synthesis and fast switching electrochromic properties of conjugated microporous polymers based on carbazole-thiophene derivatives | |
| Lakard et al. | Electrochemical preparation and physicochemical study of polymers obtained from carbazole and N-((methoxycarbonyl) methyl) carbazole | |
| Olinga et al. | Kinetics of polymerization of thiophene by FeCl3 in choloroform and acetonitrile | |
| Chen et al. | Pyrrole-and polypyrrole-based liquid crystals | |
| EP1323764A1 (en) | Process for preparing an aqueous solution or dispersion of a polythiophene or thiophene copolymer | |
| Thomas et al. | Synthesis and characterization of a new acceptor (n‐type) fluorinated and terminal‐functionalized polythiophene | |
| Ribeiro et al. | Electrochemical polymerisation of thiophene derivative induced by Lewis acid: Electrosynthesis of poly [(R)-(−)-2-(3′-thienyl) ethyl-(3′, 5 ″-dinitrobenzoyl)-α-phenylglycinate] |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20100317 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |