WO2011002927A3 - Polymers comprising at least one bithiophene repeat unit, methods synthetising said polymers and compositions comprising the same - Google Patents

Polymers comprising at least one bithiophene repeat unit, methods synthetising said polymers and compositions comprising the same Download PDF

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Publication number
WO2011002927A3
WO2011002927A3 PCT/US2010/040664 US2010040664W WO2011002927A3 WO 2011002927 A3 WO2011002927 A3 WO 2011002927A3 US 2010040664 W US2010040664 W US 2010040664W WO 2011002927 A3 WO2011002927 A3 WO 2011002927A3
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WIPO (PCT)
Prior art keywords
moiety
bithiophene
monomer
polymers
materials
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PCT/US2010/040664
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French (fr)
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WO2011002927A2 (en
Inventor
Christopher Tyler Brown
Chad Landis
Elena Sheina
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Plextronics, Inc.
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Priority to EP10730017A priority Critical patent/EP2449561A2/en
Priority to KR1020127002267A priority patent/KR20120061806A/en
Priority to JP2012518600A priority patent/JP5763632B2/en
Publication of WO2011002927A2 publication Critical patent/WO2011002927A2/en
Publication of WO2011002927A3 publication Critical patent/WO2011002927A3/en

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    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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    • H01B1/124—Intrinsically conductive polymers
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    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
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    • C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
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Abstract

A composition comprising a homopolymer or a copolymer comprising bithiophene units for use in, for example, low band gap materials including uses in organic photovoltaic active layers. The band gap and other properties can be engineered by polymerization methods including selection of monomer structure and ratio of monomer components. In addition, a dimer adapted for making alternating copolymers further comprising one first monomer moiety comprising at least one bithiophene moiety compound covalently linked to one second monomer moiety comprising a different bithiophene moiety or at least one moiety that is not a bithiophene. The composition can be copolymerized to form an alternating copolymer that can be further processed to form a polymeric film used in a printed organic electronic device. A series of novel copolymers are designed that would allow fabrication of materials with tailor made electronic and/or mechanical properties that can be easily manipulated through molecules chemical structure and potentially result in long term stability under ambient conditions that can be advantageous for use in organic electronics (e.g., OPVs, OLEDs, OFETs). Improved methods are disclosed for making monomers comprising a benzo[2,1-b:3,4-b']dithiophene moiety that are useful as electronics materials.
PCT/US2010/040664 2009-06-30 2010-06-30 Novel compositions, methods and polymers WO2011002927A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP10730017A EP2449561A2 (en) 2009-06-30 2010-06-30 Polymers comprising at least one bithiophene repeat unit, methods synthetising said polymers and compositions comprising the same
KR1020127002267A KR20120061806A (en) 2009-06-30 2010-06-30 Polymers comprising at least one bithiophene repeat unit, methods synthetising said polymers and compositions comprising the same
JP2012518600A JP5763632B2 (en) 2009-06-30 2010-06-30 Polymer comprising at least one bithiophene repeat unit, method of synthesizing the polymer, and composition comprising the same

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
US22205309P 2009-06-30 2009-06-30
US61/222,053 2009-06-30
US24013709P 2009-09-04 2009-09-04
US61/240,137 2009-09-04
US24181309P 2009-09-11 2009-09-11
US61/241,813 2009-09-11
US24833509P 2009-10-02 2009-10-02
US61/248,335 2009-10-02
US28931409P 2009-12-22 2009-12-22
US61/289,314 2009-12-22
US29084409P 2009-12-29 2009-12-29
US61/290,844 2009-12-29
US30738710P 2010-02-23 2010-02-23
US61/307,387 2010-02-23

Publications (2)

Publication Number Publication Date
WO2011002927A2 WO2011002927A2 (en) 2011-01-06
WO2011002927A3 true WO2011002927A3 (en) 2011-05-26

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EP (1) EP2449561A2 (en)
JP (1) JP5763632B2 (en)
KR (1) KR20120061806A (en)
WO (1) WO2011002927A2 (en)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8115200B2 (en) * 2007-12-13 2012-02-14 E.I. Du Pont De Nemours And Company Electroactive materials
US8212239B2 (en) 2007-12-13 2012-07-03 E I Du Pont De Nemours And Company Electroactive materials
US8216753B2 (en) 2007-12-13 2012-07-10 E I Du Pont De Nemours And Company Electroactive materials
US8067764B2 (en) * 2007-12-17 2011-11-29 E. I. Du Pont De Nemours And Company Electroactive materials
US8461291B2 (en) * 2007-12-17 2013-06-11 E I Du Pont De Nemours And Company Organic electroactive materials and an organic electronic device having an electroactive layer utilizing the same material
WO2010136401A2 (en) 2009-05-27 2010-12-02 Basf Se Polycyclic dithiophenes
US20110006287A1 (en) * 2009-07-10 2011-01-13 Wei You Polymers with tunable band gaps for photonic and electronic applications
KR20120059573A (en) * 2009-09-04 2012-06-08 플렉스트로닉스, 인크 Organic electronic devices and polymers, including photovoltaic cells and diketone-based and diketopyrrolopyrrole-based polymers
JP5782703B2 (en) * 2009-10-29 2015-09-24 住友化学株式会社 Polymer compound and electronic device using the same
JP2013533895A (en) 2010-05-19 2013-08-29 ビーエーエスエフ ソシエタス・ヨーロピア Diketopyrrolopyrrole-based polymers for use in organic semiconductor devices
WO2011147067A1 (en) * 2010-05-24 2011-12-01 海洋王照明科技股份有限公司 Quinoxaline conjugated polymer containing fused-ring thiophehe unit, preparation method and uses thereof
CN102906151B (en) * 2010-06-25 2014-05-07 海洋王照明科技股份有限公司 Conjugated polymer based on benzodithiophene and thienopyrazine, preparation method and uses thereof
CN102959008B (en) 2010-07-02 2016-03-16 索尔维美国有限公司 Hole transport composition and related device and method (II)
JP5692228B2 (en) * 2010-07-02 2015-04-01 コニカミノルタ株式会社 Organic photoelectric conversion device and solar cell using the same
JP5964553B2 (en) * 2011-01-28 2016-08-03 三菱化学株式会社 Novel copolymer, organic semiconductor material, organic electronic device, photoelectric conversion element and solar cell module using the same
US8816040B2 (en) * 2011-06-24 2014-08-26 University Of Tsukuba Polymer dye
KR101830784B1 (en) * 2011-09-09 2018-02-22 삼성전자주식회사 Polymer and organic light emitting diode comprising the same
EP2768868B1 (en) * 2011-10-21 2018-06-27 Nissan Chemical Industries, Ltd. Improved synthesis of conjugated polymers via oxidative polymerization and related compositions
JP5884423B2 (en) * 2011-11-15 2016-03-15 住友化学株式会社 Polymer compound and organic photoelectric conversion device using the same
JP5859872B2 (en) * 2012-02-17 2016-02-16 富士フイルム株式会社 ORGANIC PHOTOELECTRIC CONVERSION DEVICE COMPOSITION, THIN FILM CONTAINING THE SAME, PHOTOCELL, ORGANIC SEMICONDUCTOR POLYMER, COMPOUND AND METHOD FOR PRODUCING POLYMER
CN104334610A (en) * 2012-04-04 2015-02-04 巴斯夫欧洲公司 Diketopyrrolopyrrole polymers and small molecules
KR20150017718A (en) 2012-05-31 2015-02-17 미쓰비시 가가꾸 가부시키가이샤 Copolymer, organic semiconductor material, organic electrical device, and solar cell module
EP2875028A1 (en) 2012-07-23 2015-05-27 Basf Se Dithienobenzofuran polymers and small molecules for electronic application
JP2014051556A (en) * 2012-09-05 2014-03-20 Kuraray Co Ltd π-ELECTRON CONJUGATED RANDOM COPOLYMER, AND PHOTOELECTRIC CONVERSION ELEMENT USING THE SAME
WO2014086722A1 (en) 2012-12-04 2014-06-12 Basf Se Functionnalized benzodithiophene polymers for electronic application
CN103936966B (en) * 2013-01-17 2016-04-13 海洋王照明科技股份有限公司 Containing 3,6-carbazole-benzo two (diazosulfide) multipolymer and its preparation method and application
CN103936964B (en) * 2013-01-17 2016-02-10 海洋王照明科技股份有限公司 Containing 1,8-carbazole-benzo two (diazosulfide) multipolymer and its preparation method and application
CN103965445B (en) * 2013-01-31 2016-08-17 顾玉奎 Polymer containing bithiophene benzthiadiazole's unit
CN105073902B (en) * 2013-03-06 2018-04-24 巴斯夫欧洲公司 New type heterocycle fluorescent dye and preparation method thereof
CN105324441B (en) * 2013-06-24 2018-01-02 巴斯夫欧洲公司 Polymer based on fusion diketopyrrolopyrrolecocrystals
KR20160076528A (en) 2013-10-22 2016-06-30 메르크 파텐트 게엠베하 Conjugated polymers
US9399698B2 (en) 2014-01-31 2016-07-26 Xerox Corporation Processes for purifying diketopyrrolopyrrole copolymers
CN104448253A (en) * 2014-03-04 2015-03-25 上海大学 Aromatic alkyne copolymer based on benzo[1,2-b:4,5-b']dithiophene and preparation method thereof
US10208145B2 (en) * 2014-04-24 2019-02-19 China Petroleum & Chemical Corporation Catalyst component for olefin polymerization, and catalyst containing the same
WO2015177763A1 (en) * 2014-05-23 2015-11-26 Universita' Degli Studi Di Milano Electro-active macrocyclic oligoarenes and oligoheteroarenes with stereogenic axes
TWI532821B (en) * 2014-08-07 2016-05-11 國立清華大學 Solid-state organic optoelectronic material with hydrogen bond and method for producing solid-state organic optoelectronic material with hydrogen bond
US10875957B2 (en) * 2015-11-11 2020-12-29 The Regents Of The University Of California Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications
US20170358766A1 (en) * 2016-06-09 2017-12-14 Solarwindow Technologies, Inc. Organic semiconductor photovoltaic devices and compositions with acceptor-donor-acceptor type polymer electron donors
JP7053010B2 (en) * 2018-03-05 2022-04-12 公立大学法人大阪 Diarylethene compounds, photochromic materials, and dimming members
CN110582861B (en) 2018-03-09 2023-06-23 株式会社Lg化学 Composition for organic material layer of organic solar cell and organic solar cell
CN108727566B (en) * 2018-04-10 2019-06-14 苏州和颂生化科技有限公司 Exploitation and application of the one kind based on carbazole-anthracene structure hole transport polymer material
FR3091530A1 (en) * 2019-01-09 2020-07-10 Université De Pau Et Des Pays De L'adour FORBIDDEN VERY LOW BAND POLYMERS
CN111647332A (en) * 2019-03-04 2020-09-11 中核华兴达丰机械工程有限公司 Water-based paint for tower crane and preparation method thereof
CN111333820A (en) * 2020-03-13 2020-06-26 江西科技师范大学 Method for preparing self-supporting film by electropolymerization of planar rigid monomer
CN112552489A (en) * 2020-11-09 2021-03-26 山东师范大学 Asymmetric non-fullerene compound and preparation method and application thereof
CN115558412B (en) * 2022-10-12 2023-06-09 深圳市华之美科技有限公司 Polyimide composite material and preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008000664A1 (en) * 2006-06-30 2008-01-03 Ciba Holding Inc. Diketopyrrolopyrrole polymers as organic semiconductors
EP2006291A1 (en) * 2006-03-10 2008-12-24 Osaka University Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film
WO2009115413A2 (en) * 2008-03-17 2009-09-24 Basf Se Substituted oligo- or polythiophenes
WO2010000669A1 (en) * 2008-07-02 2010-01-07 Basf Se Poly(5,5'bis(thiophen-2-yl)-benzo[2,1-b;3,4-b']dithiophene) and its use as high performance solution processable semiconducting polymer

Family Cites Families (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4356429A (en) 1980-07-17 1982-10-26 Eastman Kodak Company Organic electroluminescent cell
DE3366011D1 (en) 1982-05-17 1986-10-16 Ciba Geigy Ag Preparation of pyrrolo-(3,4-c) pyrroles
US4539507A (en) * 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
US4585878A (en) 1983-06-29 1986-04-29 Ciba-Geigy Corporation N-substituted 1,4-diketopyrrolo-[3,4-c]-pyrroles
DE3435947A1 (en) 1984-09-29 1986-04-03 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING ELECTRICALLY CONDUCTIVE SYSTEMS
US4659775A (en) * 1984-11-07 1987-04-21 Ciba-Geigy Corporation Process for the preparation of pyrrolo[3,4-c]pyrroles, and novel pyrrolo[3,4-c]pyrroles
DE3584138D1 (en) 1984-11-07 1991-10-24 Ciba Geigy Ag PIGMENT MIXTURES.
US4931566A (en) 1987-07-31 1990-06-05 Ciba-Geigy Corporation Process for the preparation of pyrrolo[3,4-c]pyrroles
DE3736509A1 (en) * 1987-10-28 1989-05-11 Hoechst Ag DEVICE FOR LAMINATING AND CUTTING PHOTORIST RESISTANT FILMS
GB8909011D0 (en) 1989-04-20 1989-06-07 Friend Richard H Electroluminescent devices
GB9018698D0 (en) * 1990-08-24 1990-10-10 Lynxvale Ltd Semiconductive copolymers for use in electroluminescent devices
JPH07188399A (en) * 1993-12-27 1995-07-25 Unitika Ltd Moldable or film-forming composition changing to be electrically conductive by light irradiation
US5723873A (en) * 1994-03-03 1998-03-03 Yang; Yang Bilayer composite electrodes for diodes
US5492564A (en) 1994-03-16 1996-02-20 Ciba-Geigy Corporation Diketopyrrolopyrrole pigment with high chroma
EP1029369A4 (en) 1997-10-17 2002-04-03 Univ California Process for fabricating organic semiconductor devices using ink-jet printing technology and device and system employing same
US6057449A (en) 1998-06-02 2000-05-02 Ciba Specialty Chemicals Corporation Direct preparation of pyrrolo[3,4-c]pyrroles
US6566153B1 (en) * 1998-10-14 2003-05-20 The Regents Of The University Of California Process for fabricating organic semiconductor devices using ink-jet printing technology and device and system employing same
US6166172A (en) * 1999-02-10 2000-12-26 Carnegie Mellon University Method of forming poly-(3-substituted) thiophenes
US6369089B1 (en) 2000-09-14 2002-04-09 Allergan Sales, Inc. Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists
US6631712B2 (en) 2001-07-18 2003-10-14 Lawrence J Koncelik, Jr. Aquatic barbecue ash extinguisher and remover
DE10153450A1 (en) 2001-10-30 2003-05-22 Covion Organic Semiconductors Process for the production of arylamines
US6602974B1 (en) * 2001-12-04 2003-08-05 Carnegie Mellon University Polythiophenes, block copolymers made therefrom, and methods of forming the same
US20040004433A1 (en) * 2002-06-26 2004-01-08 3M Innovative Properties Company Buffer layers for organic electroluminescent devices and methods of manufacture and use
US6784017B2 (en) * 2002-08-12 2004-08-31 Precision Dynamics Corporation Method of creating a high performance organic semiconductor device
US7321012B2 (en) * 2003-02-28 2008-01-22 The University Of Connecticut Method of crosslinking intrinsically conductive polymers or intrinsically conductive polymer precursors and the articles obtained therefrom
US7368624B2 (en) * 2004-03-30 2008-05-06 Eastman Kodak Company Synthesis for polycyclic aromatic hydrocarbon compounds
US7554111B2 (en) * 2004-05-20 2009-06-30 The Regents Of The University Of California Nanoparticle-polymer bistable devices
US7238883B2 (en) * 2004-08-11 2007-07-03 Cardiac Pacemakers, Inc. Lead assembly with flexible portions and method therefor
WO2006036755A1 (en) 2004-09-24 2006-04-06 Plextronics, Inc. Heteroatomic regioregular poly(3-substitutedthiophenes) in electroluminescent devices
AU2005333609A1 (en) * 2004-10-25 2007-01-04 Hsing-En Elbert Wu Stacked layer electrode for organic electronic devices
JP4975648B2 (en) 2005-02-10 2012-07-11 プレックストロニクス インコーポレーティッド Hole injection / transport layer composition and device
US7781673B2 (en) 2005-07-14 2010-08-24 Konarka Technologies, Inc. Polymers with low band gaps and high charge mobility
JP5164134B2 (en) * 2006-03-10 2013-03-13 住友化学株式会社 Fused ring compound and method for producing the same, polymer, organic thin film containing them, and organic thin film element and organic thin film transistor comprising the same
JP5004071B2 (en) 2006-03-10 2012-08-22 住友化学株式会社 Process for producing fused ring compound
KR101477703B1 (en) 2006-06-13 2015-01-02 솔베이 유에스에이 인크. Organic photovoltaic devices comprising fullerenes and derivatives thereof
US8017241B2 (en) * 2006-07-21 2011-09-13 Plextronics, Inc. Sulfonation of conducting polymers and OLED, photovoltaic, and ESD devices
JP2008069120A (en) 2006-09-15 2008-03-27 Idemitsu Kosan Co Ltd Aromatic amine derivative and organic electroluminescent element by using the same
US8008424B2 (en) 2006-10-11 2011-08-30 Konarka Technologies, Inc. Photovoltaic cell with thiazole-containing polymer
WO2008066933A2 (en) * 2006-12-01 2008-06-05 The Regents Of The University Of California Enhancing performance characteristics of organic semiconducting films by improved solution processing
KR101128943B1 (en) * 2007-04-13 2012-03-27 주식회사 엘지화학 Dioxypyrrolo-heteroaromatic compounds and organic electronic devices using the same
EP2142584A1 (en) * 2007-05-02 2010-01-13 Plextronics, Inc. Solvent system for conujugated polymers
TW200916498A (en) 2007-05-15 2009-04-16 Plextronics Inc Aryl-substituted conjugated polymers
US8227691B2 (en) * 2007-10-31 2012-07-24 The Regents Of The University Of California Processing additives for fabricating organic photovoltaic cells
JP5599723B2 (en) * 2007-12-21 2014-10-01 プレックストロニクス インコーポレーティッド Fullerenes and derivatives thereof, and an improved method of making fullerenes suitable for organic photovoltaic devices
WO2009103030A1 (en) * 2008-02-15 2009-08-20 Plextronics, Inc. Novel compositions and methods including alternating copolymers comprising dithienopyrrole units
US20090229667A1 (en) * 2008-03-14 2009-09-17 Solarmer Energy, Inc. Translucent solar cell
EP2851383A1 (en) * 2008-04-11 2015-03-25 Solvay USA Inc. Doped conjugated polymers, devices, and methods of making devices
US20100018581A1 (en) * 2008-07-24 2010-01-28 Solarmer Energy, Inc. Large area solar cell
JP2012500500A (en) * 2008-08-20 2012-01-05 プレックストロニクス インコーポレーティッド Improved solvent system for the manufacture of organic solar cells
WO2010108873A1 (en) * 2009-03-23 2010-09-30 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
EP2503835A1 (en) 2011-03-23 2012-09-26 Panasonic Corporation Resouce assignment for single and multiple cluster transmission
US10055491B2 (en) 2012-12-04 2018-08-21 Sonos, Inc. Media content search based on metadata
EP3800643A1 (en) 2019-10-02 2021-04-07 Imec VZW Magnetic device with a hybrid free layer stack
US11305807B2 (en) 2020-08-25 2022-04-19 Thyssenkrupp Presta Ag Vehicle steering column

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2006291A1 (en) * 2006-03-10 2008-12-24 Osaka University Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film
WO2008000664A1 (en) * 2006-06-30 2008-01-03 Ciba Holding Inc. Diketopyrrolopyrrole polymers as organic semiconductors
WO2009115413A2 (en) * 2008-03-17 2009-09-24 Basf Se Substituted oligo- or polythiophenes
WO2010000669A1 (en) * 2008-07-02 2010-01-07 Basf Se Poly(5,5'bis(thiophen-2-yl)-benzo[2,1-b;3,4-b']dithiophene) and its use as high performance solution processable semiconducting polymer

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
SHENGQIANG XIAO ET AL: "Conjugated Polymers Based on Benzo[2,1-b:3,4-b?]dithiophene with Low-Lying Highest Occupied Molecular Orbital Energy Levels for Organic Photovoltaics", ACS APPLIED MATERIAL INTERFACES,, vol. 1, no. 7, 1 January 2009 (2009-01-01), pages 1613 - 1621, XP009141884, DOI: DOI:10.1021/AM900327N *
TOVAR J D ET AL: "Functionalizable polycyclic aromatics through oxidative cyclization of pendant thiophenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 124, no. 26, 1 January 2002 (2002-01-01), pages 7762 - 7769, XP002989180, ISSN: 0002-7863, DOI: DOI:10.1021/JA0262636 *
XIAO, S.; ZHOU, H.; YOU, W.: "Conjugated Polymers of Fused Bithiophenes with Enhanced pi-Electron Delocalization for Photovoltaic Applications", MACROMOLECULES, vol. 41, no. 15, 12 July 2008 (2008-07-12), pages 5688 - 5696, XP002612427, DOI: 10.1021/ma800776q *

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