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公开(公告)号:JPH08198871A
公开(公告)日:1996-08-06
申请号:JP1276695
申请日:1995-01-30
Applicant: AGENCY IND SCIENCE TECHN , STANLEY ELECTRIC CO LTD
Inventor: TANAKA SUSUMU , KUMEI MASAMI , TOYOTAMA HIDEKI
IPC: C07D333/04 , C08G61/10 , C08G61/12 , H01B1/12
Abstract: PURPOSE: To obtain a thiophene compound, and to obtain an electroconductive high polymer excellent in film formability and doping characteristics by using this thiophene compound. CONSTITUTION: This thiophene compound is expressed by formula I, pref. formula II ((p), (q), (r) and (s) are each 0 or a natural number satisfying the relationships: 0 or Na and/or anions such as I or SO 4 followed by applying a voltage between both the electrodes to effect doping the cations or anions into the polymer, thus affording other objective electroconductive high molecular material.
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公开(公告)号:JPH0782350A
公开(公告)日:1995-03-28
申请号:JP24859693
申请日:1993-09-10
Applicant: AGENCY IND SCIENCE TECHN , TOHO RAYON KK
Inventor: KAERIYAMA KYOJI , TANAKA SUSUMU , SATO HIROYUKI
Abstract: PURPOSE:To provide a production process of poly-2,5-pyridinediylvinylene in which the sulfonium salt elimination process problematic in its inapplicability to industrial production is not used, a monomer stable at room temperature is used as the monomer used in the polymerization, the polymer is easily formed, and the polymer is easily purified, and which is suited for industrial production. CONSTITUTION:A 2,5-dihalomethylpyridine is polymerized in the presence of a base by a process of polymerization through dehydrohalogenation to obtain a polymer represented by the formula. The obtained polymer is subjected to heat treatment at 230-300 deg.C in a nitrogen or inert gas stream or in a vacuum to eliminate the residual halogen part of this polymer and to thereby improve the convertion into the polymer.
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公开(公告)号:JPH02229186A
公开(公告)日:1990-09-11
申请号:JP4649689
申请日:1989-03-01
Applicant: AGENCY IND SCIENCE TECHN , KANTO KOATSU KAGAKU KK
Inventor: KAERIYAMA KYOJI , TANAKA SUSUMU , YAMAUCHI AIZO , MATSUZAKI YOSHINORI
IPC: C07D333/32
Abstract: NEW MATERIAL:A compound expressed by formula I (R is 3-12C alkyl). EXAMPLE:3-Propoxythiophene. USE:A raw material of polymer for organic electronic material. PREPARATION:3-Halogenated thiophene expressed by formula II (X is halogen) is reacted with an alkyl alcoholate (e.g. sodium propoxide) expressed by the formula R-O-M (M is alkali metal) in the presence of cupric oxide in a pressure resistant vessel. Furthermore, the above-mentioned reaction is preferably carried out in the presence of potassium iodide.
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公开(公告)号:JPH02145566A
公开(公告)日:1990-06-05
申请号:JP29995088
申请日:1988-11-28
Applicant: AGENCY IND SCIENCE TECHN
Inventor: KAERIYAMA KYOJI , TANAKA SUSUMU , YAMAUCHI AIZO , KITASHOJI TAKESHI
IPC: C07D207/323 , C08G61/10 , C08G61/12
Abstract: NEW MATERIAL:The pyrrole compound of formula (R is higher alkyl). EXAMPLE:3-Octylpyrrole. USE:The polymer of the compound is useful as an organic conductive polymer. PREPARATION:The objective compound of formula can be produced by acylating N-sulfonated pyrrole with a carboxylic acid chloride in the presence of a Friedel-Crafts catalyst, desulfonating the reaction product, separating an alkyl-3-pyrrolyl ketone from the obtained mixture of 2-substituted pyrrole and 3-substituted pyrrole and purifying and reducing the separated ketone. The Friedel-Crafts catalyst is e.g., stannic chloride or aluminum chloride and the reducing agent is aluminum lithium hydride, etc.
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公开(公告)号:JPS63205316A
公开(公告)日:1988-08-24
申请号:JP3681687
申请日:1987-02-19
Applicant: AGENCY IND SCIENCE TECHN
Inventor: TANAKA SUSUMU , SATO MASAAKI , KAERIYAMA KYOJI , SUDA MASAO , HIRAIDE TAKAO
Abstract: PURPOSE:To obtain a specified thiophene polymer in a neutral state and an organic semiconductor in the form a film which is excellent in heat resistance and smoothness, stable in air and useful as a display material and can be obtained without molding, by doping said polymer with an anion. CONSTITUTION:A compound of formula I, for example, synthesized by adding a Grignard reagent obtained by, for example, reacting 2-bromothiophene with metallic Mg to 2,5-dibromothiazole and condensing the mixture together with a supporting electrolyte comprising an anion-forming substance such as tetrafluoroborate, perchlorate, hexafluorophosphate, halide, SO4 or trifluoroacetate ion is electrolytically polymerized in a polar solvent such as propylene carbonate by using gold, platinum or the like as an electrode at a controlled electric quantity in an inert atmosphere. In this way, an anion-doped thiophene of repeating units of formula II (wherein R is a group of formula III, IV or V) having an electric conductivity of 10 -10 S/cm and a desired film thickness can be obtained. If desired, this polymer is converted into a thiophene polymer in a neutral state by removing the dopant by reversing the polarity.
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公开(公告)号:JPS61209223A
公开(公告)日:1986-09-17
申请号:JP4681685
申请日:1985-03-09
Applicant: AGENCY IND SCIENCE TECHN
Inventor: SATO MASAAKI , TANAKA SUSUMU , KAERIYAMA KYOJI , SUDA MASAO
Abstract: PURPOSE:To obtain an electrically conductive polymer composition having high electrical conductivity and composed of poly-[2,5-(3-ethylthienylene)] doped with an anion and obtained by the electrolytic polymerization of 3-ethylthiophene in a medium containing an anion-containing supporting electrolyte. CONSTITUTION:An electrically conductive polymer composition composed of poly[2,5-(3-ethylthienylene)] doped with an anion (preferably hexafluorophosphoric acid ion, etc.) and having an electrical conductivity of 150-270S/cm can be produced by the electrolytic polymerization of 3- ethylthiophene in a medium (preferably propylene carbonate) containing an anion-containing supporting electrolyte, preferably in an inert atmosphere. USE:Electronic device, polymeric material, etc.
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公开(公告)号:JPH0967429A
公开(公告)日:1997-03-11
申请号:JP24511995
申请日:1995-08-31
Applicant: AGENCY IND SCIENCE TECHN , IBARAKI PREF GOV
Inventor: TANAKA SUSUMU , ISO TOMOAKI
Abstract: PROBLEM TO BE SOLVED: To obtain the subject polymer consisting of a specific recurring unit, soluble in a solvent such as N,N-dimethylformamide, easily formed into a film, etc., capable of being reduced at a mild condition and useful as a substrate for an organic conductive material. SOLUTION: This polymer is a poly(benzonitrile) consisting of a recurring unit of formula I, and obtained e.g. by the polycondensation of a compound of formula II (X is Cl, Br or I) in the presence of a nickel halide, a substituted phosphine (e.g. triarylphosphine or trialkylphosphine) and zinc in a reaction solvent such as N,N-dimethylformamide or N,N-dimethylacetamide at 40-120 deg.C, especially at 50-80 deg.C under the atmosphere of an inert gas such as nitrogen or argon.
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公开(公告)号:JPH02218716A
公开(公告)日:1990-08-31
申请号:JP4011189
申请日:1989-02-20
Applicant: AGENCY IND SCIENCE TECHN
Inventor: TANAKA SUSUMU , KAERIYAMA KYOJI , YAMAUCHI AIZO
Abstract: PURPOSE:To obtain an organic semiconductor, having specific recurring units and useful as electrode and display materials by carrying out electrolytic polymerization of a naphthalene compound having 2 thiophene rings and doping the resultant polymer with anions. CONSTITUTION:The objective semiconductor obtained by carrying out electrolytic polymerization of a naphthalene compound, expressed by formula I (thienyl groups are present on the same benzene ring or different benzene rings) and having 2 thiophene rings and doping the resultant polymer consisting of recurring units expressed by formula II with anions (preferably tetrafluoroborate ions, perchlorade ions, hexafluorophosphate ions, hexafluoroarsenate ions, iodide ions, bromide ions, chloride ions, fluoride ions, sulfate ions, hydrogensulfate ions, trifluoroacetate ions or p-toluenesulfonate ions).
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公开(公告)号:JPS61209224A
公开(公告)日:1986-09-17
申请号:JP4681885
申请日:1985-03-09
Applicant: AGENCY IND SCIENCE TECHN
Inventor: SATO MASAAKI , TANAKA SUSUMU , KAERIYAMA KYOJI , SUDA MASAO
Abstract: PURPOSE:To produce novel poly-[2,5-(3-ethylthienylene)] useful as electronic devices, polymeric materials, optical materials, etc., by carrying out the electrolytic polymerization of 3-ethylthiophene, and subjecting the product to electrolytic reduction. CONSTITUTION:3-Ethylthiophene is subjected to the electrolytic polymerization in a solvent (e.g. propylene carbonate, etc.) containing supporting electrolyte (e.g. hexafluorophosphoric acid ion) and the product is subjected to the electrolytic reduction to obtain the objective polymer.
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10.
公开(公告)号:JPH0687950A
公开(公告)日:1994-03-29
申请号:JP26429592
申请日:1992-09-07
Applicant: AGENCY IND SCIENCE TECHN
Inventor: KAERIYAMA KYOJI , TANAKA SUSUMU
Abstract: PURPOSE:To provide a new poly(benzoic acid) made up of recurring unit having specific structure, having specific average degree of polymerization, formable into films or sheets. CONSTITUTION:The poly(benzoic acid) 30-2000 in average degree of polymerization, made up of recurring unit of formula I, which can be obtained by hydrolyzing a poly(benzoate) of formula II (R is lower alkyl; n is 30-2000) [e.g. poly(methyl benzoate)] using an alkali or acid.
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