WO2009034571A3 - Selenophenes and selenophene-based polymers, their preparation and uses thereof - Google Patents

Selenophenes and selenophene-based polymers, their preparation and uses thereof Download PDF

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Publication number
WO2009034571A3
WO2009034571A3 PCT/IL2008/001212 IL2008001212W WO2009034571A3 WO 2009034571 A3 WO2009034571 A3 WO 2009034571A3 IL 2008001212 W IL2008001212 W IL 2008001212W WO 2009034571 A3 WO2009034571 A3 WO 2009034571A3
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WO
WIPO (PCT)
Prior art keywords
selenophene
preparation
based polymers
selenophenes
polyselenophenes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IL2008/001212
Other languages
French (fr)
Other versions
WO2009034571A4 (en
WO2009034571A8 (en
WO2009034571A2 (en
Inventor
Michael Bendikov
Asit Patra
Yair-Haim Wijsboom
Mao Li
Yana Sheynin
Natalia Zamoshchik
Sanjio S. Zade
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Yeda Research and Development Co Ltd
Original Assignee
Yeda Research and Development Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Yeda Research and Development Co Ltd filed Critical Yeda Research and Development Co Ltd
Priority to EP08808020A priority Critical patent/EP2190832A2/en
Priority to US12/677,364 priority patent/US20100283040A1/en
Priority to JP2010523645A priority patent/JP2011517701A/en
Publication of WO2009034571A2 publication Critical patent/WO2009034571A2/en
Publication of WO2009034571A3 publication Critical patent/WO2009034571A3/en
Publication of WO2009034571A4 publication Critical patent/WO2009034571A4/en
Anticipated expiration legal-status Critical
Publication of WO2009034571A8 publication Critical patent/WO2009034571A8/en
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C07D333/10—Thiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D343/00—Heterocyclic compounds containing rings having sulfur and selenium or sulfur and tellurium atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D517/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains three hetero rings
    • C07D517/14—Ortho-condensed systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

This invention is directed to selenophene compounds, selenophene-based polymers (polyselenophene), processes for the preparation of the same and uses thereof. The polyselenophenes of this invention have high conductivity and can be used as electrodes in various devices such as in electrochromic devices, batteries, solar cells, optical amplifiers, organic light emitting diodes, and the like.
PCT/IL2008/001212 2007-09-10 2008-09-10 Selenophenes and selenophene-based polymers, their preparation and uses thereof Ceased WO2009034571A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP08808020A EP2190832A2 (en) 2007-09-10 2008-09-10 Selenophenes and selenophene-based polymers, their preparation and uses thereof
US12/677,364 US20100283040A1 (en) 2007-09-10 2008-09-10 Selenophenes and selenophene-based polymers, their preparation and uses thereof
JP2010523645A JP2011517701A (en) 2007-09-10 2008-09-10 Selenophene and selenophene polymers, their preparation, and uses thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US93597807P 2007-09-10 2007-09-10
US60/935,978 2007-09-10
US12944408P 2008-06-26 2008-06-26
US61/129,444 2008-06-26

Publications (4)

Publication Number Publication Date
WO2009034571A2 WO2009034571A2 (en) 2009-03-19
WO2009034571A3 true WO2009034571A3 (en) 2010-01-07
WO2009034571A4 WO2009034571A4 (en) 2010-02-25
WO2009034571A8 WO2009034571A8 (en) 2010-04-15

Family

ID=40452659

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2008/001212 Ceased WO2009034571A2 (en) 2007-09-10 2008-09-10 Selenophenes and selenophene-based polymers, their preparation and uses thereof

Country Status (5)

Country Link
US (1) US20100283040A1 (en)
EP (1) EP2190832A2 (en)
JP (1) JP2011517701A (en)
KR (1) KR20100061838A (en)
WO (1) WO2009034571A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090140219A1 (en) * 2007-07-13 2009-06-04 Air Products And Chemicals, Inc. Selenium Containing Electrically Conductive Polymers and Method of Making Electrically Conductive Polymers
US8148548B2 (en) * 2007-07-13 2012-04-03 Konarka Technologies, Inc. Heterocyclic fused selenophene monomers
CN103313599B (en) * 2010-12-09 2016-03-23 卡斯纳莱拉创新药物私人有限公司 Substituted 4-(arylamino)selenophenopyrimidine compounds and methods of use thereof
US8513377B2 (en) 2011-03-02 2013-08-20 The University Of Connecticut Selenium-based monomers and conjugated polymers, methods of making, and use thereof
JP5863479B2 (en) * 2012-01-27 2016-02-16 株式会社ダイセル Organic heteropolymer for organic semiconductor and semiconductor device using the same
EP2875033B8 (en) 2012-07-23 2019-09-11 The University of Connecticut Electrochromic copolymers from precursors, method of making, and use thereof
US10585322B2 (en) 2014-04-15 2020-03-10 The Regents Of The University Of California Methods for producing electrochromic films by low temperature condensation of polyoxometalates
US10323178B2 (en) 2014-05-16 2019-06-18 The University Of Connecticut Color tuning of electrochromic devices using an organic dye
CN104387398B (en) * 2014-10-14 2018-04-24 石家庄诚志永华显示材料有限公司 A kind of liquid-crystal compounds and preparation method and application

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273643A2 (en) * 1986-12-18 1988-07-06 The Regents Of The University Of California Conducting substituted polyisothianophthenes
JPH0275625A (en) * 1988-09-13 1990-03-15 Toyobo Co Ltd Electrically conductive polymer
JPH02170823A (en) * 1988-12-23 1990-07-02 Toyobo Co Ltd Electrically conductive polymer
JPH02180922A (en) * 1988-12-29 1990-07-13 Toyobo Co Ltd Conductive polymer
US20060249712A1 (en) * 2005-03-11 2006-11-09 Martin Heeney Monomers, oligomers and polymers comprising thiophene and selenophene
WO2007059849A1 (en) * 2005-11-24 2007-05-31 Merck Patent Gmbh Regioregular polyselenophenes
WO2007120854A2 (en) * 2006-04-13 2007-10-25 E. I. Du Pont De Nemours And Company Electrically conductive polymer compositions
EP2014665A2 (en) * 2007-07-13 2009-01-14 Air Products and Chemicals, Inc. Selenium containing electrically conductive polymers and method of making them

Family Cites Families (6)

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Publication number Priority date Publication date Assignee Title
JPS6050194A (en) * 1983-08-30 1985-03-19 Shinko Kagaku Kogyo Kk Manufacture of polyselenophene
JPH07116277B2 (en) * 1985-02-22 1995-12-13 三井東圧化学株式会社 Method for producing selenophene polymer
SG142163A1 (en) * 2001-12-05 2008-05-28 Semiconductor Energy Lab Organic semiconductor element
ATE502970T1 (en) * 2005-11-24 2011-04-15 Merck Patent Gmbh METHOD FOR PRODUCING REGIOREGULAR POLYMERS
US20070238854A1 (en) * 2006-04-11 2007-10-11 Air Products And Chemicals, Inc. Heterocyclic Fused Isothiazole and Isoselenazole Monomers and Conducting Polymers
US20080191172A1 (en) * 2006-12-29 2008-08-14 Che-Hsiung Hsu High work-function and high conductivity compositions of electrically conducting polymers

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273643A2 (en) * 1986-12-18 1988-07-06 The Regents Of The University Of California Conducting substituted polyisothianophthenes
JPH0275625A (en) * 1988-09-13 1990-03-15 Toyobo Co Ltd Electrically conductive polymer
JPH02170823A (en) * 1988-12-23 1990-07-02 Toyobo Co Ltd Electrically conductive polymer
JPH02180922A (en) * 1988-12-29 1990-07-13 Toyobo Co Ltd Conductive polymer
US20060249712A1 (en) * 2005-03-11 2006-11-09 Martin Heeney Monomers, oligomers and polymers comprising thiophene and selenophene
WO2007059849A1 (en) * 2005-11-24 2007-05-31 Merck Patent Gmbh Regioregular polyselenophenes
WO2007120854A2 (en) * 2006-04-13 2007-10-25 E. I. Du Pont De Nemours And Company Electrically conductive polymer compositions
EP2014665A2 (en) * 2007-07-13 2009-01-14 Air Products and Chemicals, Inc. Selenium containing electrically conductive polymers and method of making them

Non-Patent Citations (12)

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Title
AQAD, EMAD ET AL: "Synthesis of Benzo[c]selenophene and Derivatives via New Routes", ORGANIC LETTERS , 5(14), 2519-2521 CODEN: ORLEF7; ISSN: 1523-7060, 2003, XP002522897 *
BRAVERMAN, SAMUEL ET AL: "Base catalyzed rearrangement of .pi.-conjugated sulfur and selenium bridged propargylic systems", TETRAHEDRON , 57(44), 9177-9185 CODEN: TETRAB; ISSN: 0040-4020, 2001, XP002522898 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 12 January 1991 (1991-01-12), KUBOTA, FUYUHIKO: "Doped conductive polymers", XP002550049, retrieved from STN Database accession no. 1991:15982 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 27 October 1990 (1990-10-27), KUBOTA, FUYUHIKO: "Electrically conductive polymers from naphthofuran derivatives and their analogs", XP002550048, retrieved from STN Database accession no. 1990:563799 *
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EMAD AQAD ET AL.: "synthesis of 3,4-ethylenedioxyselenophene (EDOS): anovel building block for eletron-rich pi-conjugated ploymers", ORGANIC LETTERS, vol. 3, no. 26, 2001, pages 4283 - 4285, XP002522904 *
JINGKUN XU ET AL.: "electrosyntheses of high quality freestanding polyselenophene films in boron trifluoride diethyl etherate", JOURNAL OF ELECTROANALYTICAL CHEMISTRY, vol. 578, 2005, pages 345 - 355, XP002522903 *
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MUELLER, EUGEN ET AL: "Diyne reaction. XVI. Mono- and bisheterocondensed benzoquinones: benso-, furano-, thiopheno-, selenopheno-isofuranobenzoquinones", JUSTUS LIEBIGS ANNALEN DER CHEMIE , 761, 14-19 CODEN: JLACBF; ISSN: 0075-4617, 1972, XP002522902 *
MUELLER, EUGEN ET AL: "Diyne reaction. XVIII. 4,4-Dimethyl-1,7-diphenyl-1,6-heptadiyne-3,5- dione, a new diyne component", CHEMISCHE BERICHTE , 106(1), 35-40 CODEN: CHBEAM; ISSN: 0009-2940, 1973, XP002522900 *
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PAULMIER, C. ET AL: "Synthesis and chemical properties of carbonylated and hydroxylated thiophenes and selenophenes", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE , (7-8)(PT. 2), 2434-41 CODEN: BSCFAS; ISSN: 0037-8968, 1973, XP002522896 *

Also Published As

Publication number Publication date
WO2009034571A4 (en) 2010-02-25
US20100283040A1 (en) 2010-11-11
WO2009034571A8 (en) 2010-04-15
EP2190832A2 (en) 2010-06-02
WO2009034571A2 (en) 2009-03-19
KR20100061838A (en) 2010-06-09
JP2011517701A (en) 2011-06-16

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