WO1990008792A1 - Fluoroalkylated heteroaromatic polymer - Google Patents
Fluoroalkylated heteroaromatic polymer Download PDFInfo
- Publication number
- WO1990008792A1 WO1990008792A1 PCT/JP1990/000111 JP9000111W WO9008792A1 WO 1990008792 A1 WO1990008792 A1 WO 1990008792A1 JP 9000111 W JP9000111 W JP 9000111W WO 9008792 A1 WO9008792 A1 WO 9008792A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mouth
- polymer
- group
- heteroaromatic polymer
- fluoroalkyl group
- Prior art date
Links
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
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- 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
Definitions
- the present invention relates to a novel fluoroaromatic group-containing heteroaromatic polymer.
- Heteroaromatic polymers represented by polythiophene, polypropylene, polyfuran, and the like have been attracting attention as conductive polymers.
- the conductive polymer has a drawback that it is insoluble in any solvent and does not melt even when heated, and thus has a remarkably poor additivity. Therefore, as an attempt to compensate for such a defect, it has been proposed to introduce a hydrocarbon-based alkyl group at position 3 or 4 of the polythiophene ring. ( ⁇ Chemistry and Industry, Vol. 41, p. 102 (1988).
- the polymer containing an alkyl group in the thiophene ring is soluble in certain solvents and heated at a relatively low temperature. Melting is reported to be possible.
- An object of the present invention is to provide a fluoroalkyl group
- An object of the present invention is to provide a novel fluoroaromatic group-containing heteroaromatic polymer having chemical properties, water repellency, oil repellency and the like, and which can be used for a conductive polymer material and the like.
- R represents a hydrogen atom or an alkyl group having 1 to 25 carbon atoms
- X represents a sulfur atom, a hydrogen nitride or an oxygen atom
- ⁇ represents an integer of 1 to 9
- the present invention provides a fluoroaromatic group-containing heteroaromatic polymer having a degree of polymerization of 5 to 500.
- the structural unit of the fluoroalkyl group-containing heteroaromatic polymer of the present invention can be represented by the following general formula (I): ' ⁇ ( ⁇ )
- R represents a hydrogen atom or an alkyl group having 1 to 25 carbon atoms
- X represents a sulfur atom, hydrogen nitride or an oxygen atom
- ⁇ represents an integer of 1 to 9. In this case, when the number of carbon atoms of R is 26 or more and when ⁇ or ⁇ is 10 or more, production is difficult.
- the general The structural units of the heteroaromatic polymer represented by the formula (I) include, for example, 3-perfluoropropylthiophene, 3-perfluorophenol propyl-14-ethylthiophene, 3-perfluoropropylpyrropropyl, 3 —Perfluro propirfuran 3 —Pinolefluo to the mouth, Petilinolethiophene, 3 — ⁇ Zolefnorre to the mouth, Petilvirol, 3 —Perfluro to the mouth, Petilfuran, 3 — ⁇ Lopropyl-1 4-dodecinolethiophene, 3—Perfunoreo mouth Pupil-1-4-octylthiophene, 3—Perfluro Lopropyl-1 41-docosinorethiophene, 3—Perfluo mouth heptyl-14, 1-year-old octylthiophene , 3 — ⁇ ⁇ ⁇ ⁇
- the monomer having the structural unit structure can be synthesized by a polymerization reaction or the like using a ferric chloride catalyst as described below.
- the above Grignard reaction it is preferable to heat to 0 to 150 ° C. and react for 1 to 70 hours, and when a ferric chloride catalyst is used, it is preferable.
- the reaction is preferably performed at 110 to 100 ° C. for 1 to 50 hours.
- the polymerization degree of the fluoroalkyl group-containing heteroaromatic polymer of the present invention is in the range of 5 to 500. If the degree of polymerization is less than 5, it becomes a liquid, and the desired physical properties cannot be obtained. If it exceeds 50,000, the solubility in a solvent is reduced, making it difficult to use.
- the fluoroaromatic group-containing heteroaromatic polymer of the present invention can be easily dissolved in a common organic solvent, for example, chloroform, methylene chloride, benzene, tetrahydrofuran, toluene and the like.
- a common organic solvent for example, chloroform, methylene chloride, benzene, tetrahydrofuran, toluene and the like.
- the fluoroaromatic group-containing heteroaromatic polymer of the present invention has a fluoroaromatic ring in the heteroaromatic ring in the polymer. Since the kill group is directly substituted by a chemical bond, the water- and oil-repellent effect caused by the fluoroalkyl group and the chemical resistance effect can be maintained very permanently. Furthermore, since it is soluble in general-purpose organic solvents, it has excellent workability, and is therefore useful as a functional material and a conductive material.
- Example 5 A polymer was synthesized in the same manner as in Example 4 except that controlledpyrrole mononuclear was replaced with 3-perfuthreo-mouth butylfuran, and the obtained polymer was analyzed in the same manner as in Example 1. I got it. The results are shown below.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1/19872 | 1989-01-31 | ||
JP1987289A JPH02202514A (ja) | 1989-01-31 | 1989-01-31 | フルオロアルキル基含有ヘテロ芳香族系重合体 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1990008792A1 true WO1990008792A1 (en) | 1990-08-09 |
Family
ID=12011303
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1990/000111 WO1990008792A1 (en) | 1989-01-31 | 1990-01-30 | Fluoroalkylated heteroaromatic polymer |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0414906A4 (ja) |
JP (1) | JPH02202514A (ja) |
WO (1) | WO1990008792A1 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20030010508A (ko) | 2001-07-25 | 2003-02-05 | 메르크 파텐트 게엠베하 | 모노-, 올리고- 및 폴리-4-플루오로티오펜 및 전하 이동물질로서의 이들의 용도 |
EP1279690A1 (en) * | 2001-07-25 | 2003-01-29 | MERCK PATENT GmbH | Mono-oligo- and poly-3-substituted-4-fluorothiophenes and their use as charge transport materials |
ATE409714T1 (de) | 2001-07-25 | 2008-10-15 | Merck Patent Gmbh | Mono-, oligo and poly-3-(1,1- difluoroalkyl)thiophene und ihre verwendung als ladungstransportmaterial |
JP4731942B2 (ja) * | 2005-02-16 | 2011-07-27 | 住友化学株式会社 | ポリチオフェン |
US7932347B2 (en) | 2005-09-08 | 2011-04-26 | Sumitomo Chemical Company, Limited | Polymer comprising unit comprising fluorocyclopentane ring fused with aromatic ring and organic thin film and organic thin film element both comprising the same |
KR101648072B1 (ko) * | 2009-07-03 | 2016-08-12 | 삼성전자 주식회사 | 유기 반도체 고분자 및 이를 포함하는 트랜지스터 |
KR101730617B1 (ko) | 2010-11-22 | 2017-04-27 | 삼성전자주식회사 | 유기 반도체 소자용 조성물 및 이로부터 얻어지는 고분자를 포함하는 트랜지스터와 전자 소자 |
EP3078657A1 (en) * | 2015-04-09 | 2016-10-12 | Solvay SA | Compounds for dielectrically insulating electric active parts |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61197636A (ja) * | 1985-02-27 | 1986-09-01 | Nitto Electric Ind Co Ltd | 導電性複合材料の製造方法 |
JPS62220517A (ja) * | 1986-03-20 | 1987-09-28 | Agency Of Ind Science & Technol | 導電性重合体組成物及びその製造方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0203438A1 (en) * | 1985-05-31 | 1986-12-03 | Corporation Allied | Solution processible forms of neutral and electrically conductive poly(substituted heterocycles) |
FI74715C (fi) * | 1985-07-24 | 1988-03-10 | Neste Oy | Elledande polytiofen och foerfarande foer dess framstaellning och anvaendning. |
-
1989
- 1989-01-31 JP JP1987289A patent/JPH02202514A/ja active Pending
-
1990
- 1990-01-30 EP EP19900902379 patent/EP0414906A4/en not_active Ceased
- 1990-01-30 WO PCT/JP1990/000111 patent/WO1990008792A1/ja not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61197636A (ja) * | 1985-02-27 | 1986-09-01 | Nitto Electric Ind Co Ltd | 導電性複合材料の製造方法 |
JPS62220517A (ja) * | 1986-03-20 | 1987-09-28 | Agency Of Ind Science & Technol | 導電性重合体組成物及びその製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP0414906A4 * |
Also Published As
Publication number | Publication date |
---|---|
EP0414906A4 (en) | 1992-01-08 |
JPH02202514A (ja) | 1990-08-10 |
EP0414906A1 (en) | 1991-03-06 |
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