JP2012525487A - 非水性溶媒による水性溶媒の置換法 - Google Patents
非水性溶媒による水性溶媒の置換法 Download PDFInfo
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- JP2012525487A JP2012525487A JP2012508776A JP2012508776A JP2012525487A JP 2012525487 A JP2012525487 A JP 2012525487A JP 2012508776 A JP2012508776 A JP 2012508776A JP 2012508776 A JP2012508776 A JP 2012508776A JP 2012525487 A JP2012525487 A JP 2012525487A
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- mixture
- sulfonated
- polythiophene
- iii
- aqueous dispersion
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- 229920001157 Poly(2-vinylnaphthalene) Polymers 0.000 description 2
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- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical group C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 2
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- FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- 229920001643 poly(ether ketone) Polymers 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
-
- 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
- C08L81/06—Polysulfones; Polyethersulfones
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- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
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- 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
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- Manufacturing & Machinery (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US17482809P | 2009-05-01 | 2009-05-01 | |
| US61/174,828 | 2009-05-01 | ||
| PCT/US2010/033180 WO2010127253A1 (en) | 2009-05-01 | 2010-04-30 | Replacing aqueous with non-aqueous solvent |
Publications (2)
| Publication Number | Publication Date |
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| JP2012525487A true JP2012525487A (ja) | 2012-10-22 |
| JP2012525487A5 JP2012525487A5 (enExample) | 2013-05-30 |
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| EP (1) | EP2424925A1 (enExample) |
| JP (1) | JP2012525487A (enExample) |
| KR (1) | KR20120006562A (enExample) |
| WO (1) | WO2010127253A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014148664A (ja) * | 2013-01-31 | 2014-08-21 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | 光電子工学装置、特に逆型opvセルの形成 |
| JP2018516999A (ja) * | 2015-04-22 | 2018-06-28 | 日産化学工業株式会社 | 有機エレクトロニクスにおける使用に適した非水系組成物 |
| JP2018528285A (ja) * | 2015-07-17 | 2018-09-27 | 日産化学株式会社 | 有機エレクトロニクスにおける使用に適した半金属ナノ粒子を含有する非水系インク組成物 |
| JP2019508515A (ja) * | 2016-01-20 | 2019-03-28 | 日産化学株式会社 | 遷移金属錯体を含有する非水性インク組成物及び有機エレクトロニクスにおけるその使用 |
| KR20200106275A (ko) * | 2019-03-04 | 2020-09-14 | 한국생산기술연구원 | 물성이 향상된 전도성 고분자 분산액의 제조방법 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9411058B2 (en) * | 2012-04-13 | 2016-08-09 | University Of Tennessee Research Foundation | Polymer composite based thermal neutron detectors |
| JP2013247312A (ja) * | 2012-05-29 | 2013-12-09 | Sanyo Chem Ind Ltd | 固体電解コンデンサ用導電性高分子 |
| KR101679711B1 (ko) | 2014-06-13 | 2016-11-25 | 주식회사 엘지화학 | 중성화된 전도성 수분산액 조성물 및 그 제조방법 |
| WO2015190727A1 (ko) * | 2014-06-13 | 2015-12-17 | 주식회사 엘지화학 | 전도성 고분자 잉크 조성물 |
| JP7077944B2 (ja) * | 2017-01-18 | 2022-05-31 | 日産化学株式会社 | インク組成物 |
| US11339246B2 (en) * | 2020-03-03 | 2022-05-24 | Lg Energy Solution, Ltd. | Preparation method of polymer |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005511808A (ja) * | 2001-12-04 | 2005-04-28 | アグフア−ゲヴエルト,ナームローゼ・フエンノートシヤツプ | ポリチオフェンまたはチオフェン共重合体の水性もしくは非水性溶液または分散液の製造方法 |
| JP2007280946A (ja) * | 2006-03-16 | 2007-10-25 | Fujifilm Corp | 膜/電極接合体および燃料電池 |
| WO2008073149A2 (en) * | 2006-07-21 | 2008-06-19 | Plextronics, Inc. | Sulfonation of conducting polymers and oled, photovoltaic, and esd devices |
| JP2009046687A (ja) * | 2001-03-12 | 2009-03-05 | Hc Starck Gmbh | 新規のポリチオフェン分散液 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004006583A1 (de) * | 2004-02-10 | 2005-09-01 | H.C. Starck Gmbh | Polythiophenformulierungen zur Verbesserung von organischen Leuchtdioden |
| EP1950246A4 (en) * | 2005-11-16 | 2009-11-25 | Nagase Chemtex Corp | CONDUCTIVE RESIN COMPOSITION, CONDUCTIVE FILM THEREFOR AND RESISTIVE FILM SWITCH THEREFOR |
| US20070264551A1 (en) * | 2006-03-16 | 2007-11-15 | Atsushi Matsunaga | Membrane/Electrode Assembly and Fuel Cell |
| ATE540069T1 (de) * | 2008-02-29 | 2012-01-15 | Plextronics Inc | Planierungsmittel und vorrichtungen |
-
2010
- 2010-04-30 WO PCT/US2010/033180 patent/WO2010127253A1/en not_active Ceased
- 2010-04-30 US US13/265,523 patent/US20120097898A1/en not_active Abandoned
- 2010-04-30 JP JP2012508776A patent/JP2012525487A/ja active Pending
- 2010-04-30 KR KR1020117028618A patent/KR20120006562A/ko not_active Withdrawn
- 2010-04-30 EP EP10719831A patent/EP2424925A1/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009046687A (ja) * | 2001-03-12 | 2009-03-05 | Hc Starck Gmbh | 新規のポリチオフェン分散液 |
| JP2005511808A (ja) * | 2001-12-04 | 2005-04-28 | アグフア−ゲヴエルト,ナームローゼ・フエンノートシヤツプ | ポリチオフェンまたはチオフェン共重合体の水性もしくは非水性溶液または分散液の製造方法 |
| JP2007280946A (ja) * | 2006-03-16 | 2007-10-25 | Fujifilm Corp | 膜/電極接合体および燃料電池 |
| WO2008073149A2 (en) * | 2006-07-21 | 2008-06-19 | Plextronics, Inc. | Sulfonation of conducting polymers and oled, photovoltaic, and esd devices |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014148664A (ja) * | 2013-01-31 | 2014-08-21 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | 光電子工学装置、特に逆型opvセルの形成 |
| JP2018516999A (ja) * | 2015-04-22 | 2018-06-28 | 日産化学工業株式会社 | 有機エレクトロニクスにおける使用に適した非水系組成物 |
| US10407581B2 (en) | 2015-04-22 | 2019-09-10 | Nissan Chemical Industries, Ltd. | Non-aqueous compositions having sulfonated polythiophenes suitable for use in organic electronics |
| JP2018528285A (ja) * | 2015-07-17 | 2018-09-27 | 日産化学株式会社 | 有機エレクトロニクスにおける使用に適した半金属ナノ粒子を含有する非水系インク組成物 |
| JP2020037697A (ja) * | 2015-07-17 | 2020-03-12 | 日産化学株式会社 | 有機エレクトロニクスにおける使用に適した半金属ナノ粒子を含有する非水系インク組成物 |
| JP2019508515A (ja) * | 2016-01-20 | 2019-03-28 | 日産化学株式会社 | 遷移金属錯体を含有する非水性インク組成物及び有機エレクトロニクスにおけるその使用 |
| KR20200106275A (ko) * | 2019-03-04 | 2020-09-14 | 한국생산기술연구원 | 물성이 향상된 전도성 고분자 분산액의 제조방법 |
| KR102186871B1 (ko) | 2019-03-04 | 2020-12-04 | 한국생산기술연구원 | 물성이 향상된 전도성 고분자 분산액의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20120097898A1 (en) | 2012-04-26 |
| KR20120006562A (ko) | 2012-01-18 |
| EP2424925A1 (en) | 2012-03-07 |
| WO2010127253A1 (en) | 2010-11-04 |
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