WO2011020712A3 - Oligothiophenes derivatives - Google Patents

Oligothiophenes derivatives Download PDF

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Publication number
WO2011020712A3
WO2011020712A3 PCT/EP2010/061475 EP2010061475W WO2011020712A3 WO 2011020712 A3 WO2011020712 A3 WO 2011020712A3 EP 2010061475 W EP2010061475 W EP 2010061475W WO 2011020712 A3 WO2011020712 A3 WO 2011020712A3
Authority
WO
WIPO (PCT)
Prior art keywords
derivatives
oligothiophenes
new
present
dicyanooligothiophenes
Prior art date
Application number
PCT/EP2010/061475
Other languages
French (fr)
Other versions
WO2011020712A2 (en
Inventor
Jean-Yves Balandier
Florence Quist
Claire Amato
Serguei Sergueev
Yves Geerts
Jérôme CORNIL
Saïd BOUZAKRAOUI
Original Assignee
Universite Libre De Bruxelles
Universite De Mons
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 Universite Libre De Bruxelles, Universite De Mons filed Critical Universite Libre De Bruxelles
Publication of WO2011020712A2 publication Critical patent/WO2011020712A2/en
Publication of WO2011020712A3 publication Critical patent/WO2011020712A3/en

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Classifications

    • 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
    • C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C08G61/126—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 with a five-membered ring containing one sulfur atom in the ring
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • 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
    • C08G2261/143—Side-chains containing nitrogen
    • 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
    • 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
    • C08G2261/22—Molecular weight
    • C08G2261/226—Oligomers, i.e. up to 10 repeat units
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/414—Stille reactions
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/92—TFT applications

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Thin Film Transistor (AREA)

Abstract

The present invention is directed to new oligothiophene derivatives and their use as a semiconductor material in electronic devices. More specifically, the present invention relates to new 3,4-dicyanooligothiophenes derivatives, processes for manufacturing thereof, and to their use as organic n-type (electron-transporting) semiconductors, in particular, in field-effect transistors (FET).
PCT/EP2010/061475 2009-08-18 2010-08-06 Oligothiophenes derivatives WO2011020712A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09168111 2009-08-18
EP09168111.4 2009-08-18

Publications (2)

Publication Number Publication Date
WO2011020712A2 WO2011020712A2 (en) 2011-02-24
WO2011020712A3 true WO2011020712A3 (en) 2011-05-12

Family

ID=41571076

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/061475 WO2011020712A2 (en) 2009-08-18 2010-08-06 Oligothiophenes derivatives

Country Status (1)

Country Link
WO (1) WO2011020712A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110156964B (en) * 2019-05-31 2022-01-18 华南理工大学 P-type conjugated polymer containing 3, 4-dicyanothiophene, preparation method and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030045540A1 (en) * 2001-06-12 2003-03-06 Wishka Donn G. Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6414164B1 (en) 2000-07-12 2002-07-02 International Business Machines Corporation Synthesis of soluble derivatives of sexithiophene and their use as the semiconducting channels in thin-film filed-effect transistors
EP1398336B1 (en) 2002-09-14 2005-10-26 MERCK PATENT GmbH Mono-, Oligo- and Poly(3-alkynylthiophenes) and their Use as Charge Transport Materials
US7312469B2 (en) 2004-06-10 2007-12-25 Xerox Corporation Device with small molecular thiophene compound
US7488834B2 (en) 2005-09-30 2009-02-10 Alcatel-Lucent Usa Inc. Organic semiconductors

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030045540A1 (en) * 2001-06-12 2003-03-06 Wishka Donn G. Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
AYRES ET AL.: "Synthesis of derivatives of cyclobuteno[c]thiphen and attempts to synthesise thiophen analogues of biphenylene", TETRAHEDRON, vol. 31, 1975, pages 1755 - 1760, XP002566076 *
DEMANZE ET AL.: "Tuning of the Electronic and Optical Properties of Oligothiophenes via Cyano Substitution: a Joint Experimental and Theoretical Study", J. PHYS. CHEM. B, vol. 101, 1997, pages 4553 - 4558, XP002566074 *
YOKOOJI ET AL.: "Synthesis of 5,5'-bithiophenes via palladium-catalysed arylation reactions", TETRAHEDRON, vol. 60, no. 32, 2004, pages 6757 - 6764, XP002566075 *

Also Published As

Publication number Publication date
WO2011020712A2 (en) 2011-02-24

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