JP5739598B2 - チオフェンまたはセレノフェン化合物の重合方法 - Google Patents
チオフェンまたはセレノフェン化合物の重合方法 Download PDFInfo
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- JP5739598B2 JP5739598B2 JP2006221386A JP2006221386A JP5739598B2 JP 5739598 B2 JP5739598 B2 JP 5739598B2 JP 2006221386 A JP2006221386 A JP 2006221386A JP 2006221386 A JP2006221386 A JP 2006221386A JP 5739598 B2 JP5739598 B2 JP 5739598B2
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- 238000000034 method Methods 0.000 title claims abstract description 69
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- -1 phosphine compound Chemical class 0.000 claims description 88
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
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- 238000005481 NMR spectroscopy Methods 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 5
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- 125000004001 thioalkyl group Chemical group 0.000 description 4
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- IGCWAQUSALHDIF-UHFFFAOYSA-N 2-(5-bromo-4-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound S1C(Br)=C(CCCCCC)C=C1B1OC(C)(C)C(C)(C)O1 IGCWAQUSALHDIF-UHFFFAOYSA-N 0.000 description 3
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 3
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
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- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- IAIIMFYGUSOPKK-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[2,3-b]thiophen-2-yl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C(S1)=CC2=C1SC(B1OC(C)(C)C(C)(C)O1)=C2 IAIIMFYGUSOPKK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
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- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
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- ORMYJVVIKXRZQP-UHFFFAOYSA-N 2,5-bis(3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene Chemical compound C1=CSC(C=2SC=3C=C(SC=3C=2)C2=C(C=CS2)CCCCCCCCCCCC)=C1CCCCCCCCCCCC ORMYJVVIKXRZQP-UHFFFAOYSA-N 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- 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
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/14—Polysulfides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
- Photovoltaic Devices (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05017718 | 2005-08-16 | ||
| EP05017718.7 | 2005-08-16 | ||
| EP06002595.4 | 2006-02-09 | ||
| EP06002595 | 2006-02-09 |
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| JP2014000657A Division JP2014129533A (ja) | 2005-08-16 | 2014-01-06 | チオフェンまたはセレノフェン化合物の重合方法 |
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| JP2007051289A JP2007051289A (ja) | 2007-03-01 |
| JP2007051289A5 JP2007051289A5 (enExample) | 2012-07-12 |
| JP5739598B2 true JP5739598B2 (ja) | 2015-06-24 |
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| JP2006221386A Expired - Fee Related JP5739598B2 (ja) | 2005-08-16 | 2006-08-15 | チオフェンまたはセレノフェン化合物の重合方法 |
| JP2014000657A Pending JP2014129533A (ja) | 2005-08-16 | 2014-01-06 | チオフェンまたはセレノフェン化合物の重合方法 |
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| JP2014000657A Pending JP2014129533A (ja) | 2005-08-16 | 2014-01-06 | チオフェンまたはセレノフェン化合物の重合方法 |
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| JP (2) | JP5739598B2 (enExample) |
| KR (1) | KR101314902B1 (enExample) |
| AT (1) | ATE509055T1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE509055T1 (de) * | 2005-08-16 | 2011-05-15 | Merck Patent Gmbh | Verfahren zur polymerisation von thiophen- oder selenophenderivaten |
| JP5545383B2 (ja) * | 2006-07-18 | 2014-07-09 | 日立化成株式会社 | 有機エレクトロニクス素子の製造方法及び有機エレクトロルミネッセンス素子の製造方法 |
| CN101563389B (zh) * | 2006-12-22 | 2013-07-17 | 默克专利股份有限公司 | 包含稠合硒吩的聚合物 |
| US8723163B2 (en) * | 2008-03-12 | 2014-05-13 | Sumitomo Chemical Company, Limited | Organic photoelectric converter |
| DE112010002086B4 (de) * | 2009-05-27 | 2020-07-09 | Basf Se | Verfahren zum Polymerisieren von (hetero)aromatischen Verbindungen |
| WO2012143081A1 (en) * | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Conjugated polymers |
| KR101424978B1 (ko) * | 2012-05-24 | 2014-07-31 | 경상대학교산학협력단 | 길만시약 화합물을 이용한 헤테로 융합고리 화합물의 신규한 제조방법 |
| JP6103585B2 (ja) * | 2013-03-27 | 2017-03-29 | オリヱント化学工業株式会社 | チエノチオフェン−ベンゾジチオフェン共重合体の製造方法 |
| WO2015108360A1 (ko) * | 2014-01-17 | 2015-07-23 | 경상대학교산학협력단 | 비대칭 헤테로고리-비닐렌-헤테로고리계 다이케토피롤로피롤 중합체, 이를 채용하고 있는 유기 전자 소자 및 이를 제조하기 위한 단량체 |
| CN105482082B (zh) * | 2014-09-19 | 2018-11-06 | 中国科学院苏州纳米技术与纳米仿生研究所 | 结构规整聚噻吩及其合成方法 |
| WO2018220785A1 (ja) * | 2017-06-01 | 2018-12-06 | 住友化学株式会社 | 高分子化合物の製造方法 |
| KR102631550B1 (ko) * | 2018-09-20 | 2024-01-30 | 주식회사 엘지화학 | 중합체 제조방법 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5892244A (en) * | 1989-01-10 | 1999-04-06 | Mitsubishi Denki Kabushiki Kaisha | Field effect transistor including πconjugate polymer and liquid crystal display including the field effect transistor |
| US5198153A (en) * | 1989-05-26 | 1993-03-30 | International Business Machines Corporation | Electrically conductive polymeric |
| WO1996021659A1 (en) | 1995-01-10 | 1996-07-18 | University Of Technology, Sydney | Organic semiconductor |
| US5998804A (en) * | 1997-07-03 | 1999-12-07 | Hna Holdings, Inc. | Transistors incorporating substrates comprising liquid crystal polymers |
| EP0889350A1 (en) | 1997-07-03 | 1999-01-07 | ETHZ Institut für Polymere | Photoluminescent display devices (I) |
| DE19739774A1 (de) * | 1997-09-10 | 1999-03-11 | Basf Ag | Polyselenophene als Materialien mit nichtlinear optischen Eigenschaften |
| EP0902043A3 (de) * | 1997-09-10 | 1999-08-11 | Basf Aktiengesellschaft | Polyselenophene, Verfahren zu deren Herstellung, und deren Verwendung |
| US5777070A (en) | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
| US7223879B2 (en) * | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| DE60035970T2 (de) | 1999-03-05 | 2008-05-15 | Cambridge Display Technology Ltd. | Polymerherstellung |
| CN100461486C (zh) | 1999-06-21 | 2009-02-11 | 剑桥企业有限公司 | 用于有机薄膜晶体管的取向聚合物 |
| US6824706B2 (en) * | 2001-07-25 | 2004-11-30 | Merck Patent Gesellschaft Mit Beschrank Haftung | Mono-, Oligo- and poly-difluorovinyl-(hetero)arylenes, their synthesis and their use as charge transport materials |
| GB0125621D0 (en) | 2001-10-25 | 2001-12-19 | Cambridge Display Technology | Polymer preparation |
| GB0125622D0 (en) * | 2001-10-25 | 2001-12-19 | Cambridge Display Tech Ltd | Method of polymerisation |
| DE10159946A1 (de) | 2001-12-06 | 2003-06-18 | Covion Organic Semiconductors | Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
| US6849348B2 (en) * | 2002-12-31 | 2005-02-01 | Eastman Kodak Company | Complex fluorene-containing compounds |
| US8242235B2 (en) * | 2003-06-05 | 2012-08-14 | Hitachi Chemical Co., Ltd. | Purification process of electroluminescent material, electroluminescent material and electroluminescent device |
| FR2858222A1 (fr) | 2003-07-16 | 2005-02-04 | Oreal | Composition comprenant un polymere conducteur et un agent oxydant,procede de deformation permanente la mettant en oeuvre |
| EP1510535B1 (en) * | 2003-08-28 | 2008-11-05 | MERCK PATENT GmbH | Mono-, Oligo- and Polythieno(2,3-b)thiophenes |
| EP1688424B1 (en) * | 2003-11-28 | 2016-01-13 | Hokko Chemical Industry Co., Ltd. | Phosphonium borate compound and method of using the same |
| EP1751166B1 (en) | 2004-05-18 | 2009-10-28 | MERCK PATENT GmbH | Mono-, oligo- and polythieno[3,2-b]thiophenes |
| JP5474299B2 (ja) * | 2004-08-21 | 2014-04-16 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | チエノ［２，３−ｂ］チオフェンのモノマー、オリゴマーおよびポリマー |
| WO2006094645A1 (en) | 2005-03-11 | 2006-09-14 | Merck Patent Gmbh | Monomers, oligomers and polymers comprising thiophene and selenophene |
| ATE509055T1 (de) * | 2005-08-16 | 2011-05-15 | Merck Patent Gmbh | Verfahren zur polymerisation von thiophen- oder selenophenderivaten |
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2006
- 2006-07-18 AT AT06014918T patent/ATE509055T1/de not_active IP Right Cessation
- 2006-08-14 KR KR1020060076595A patent/KR101314902B1/ko not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20070021055A (ko) | 2007-02-22 |
| ATE509055T1 (de) | 2011-05-15 |
| US8501902B2 (en) | 2013-08-06 |
| JP2007051289A (ja) | 2007-03-01 |
| KR101314902B1 (ko) | 2013-10-04 |
| JP2014129533A (ja) | 2014-07-10 |
| US20070045592A1 (en) | 2007-03-01 |
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