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Title: Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells

Patent ·
OSTI ID:1162114

The inventions disclosed, described, and/or claimed herein relate to copolymers comprising copolymers comprising electron accepting A subunits that comprise thiazolothiazole, benzobisthiazole, or benzobisoxazoles rings, and electron donating subunits that comprise certain heterocyclic groups. The copolymers are useful for manufacturing organic electronic devices, including transistors and solar cells. The invention also relates to certain synthetic precursors of the copolymers. Methods for making the copolymers and the derivative electronic devices are also described.

Research Organization:
Univ. of Washington, Seattle, WA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
FG02-07ER46467
Assignee:
University of Washington (Seattle, WA)
Patent Number(s):
8,871,884
Application Number:
13/504,058
OSTI ID:
1162114
Resource Relation:
Patent File Date: 2010 Oct 26
Country of Publication:
United States
Language:
English

References (49)

Two-photon responsive chromophores containing electron accepting core units patent May 2004
Photovoltaic cell with silole-containing polymer patent August 2011
Poly(benzodithiophenes) patent-application April 2005
Window with photovoltaic cell patent-application June 2007
Tandem Photovoltaic Cells patent-application October 2007
Silole-based polymers and semiconductor materials prepared from the same patent-application December 2007
Photovoltaic Cell With Thiazole-Containing Polymer patent-application May 2008
Benzobisthiazole Compund, Benzobisthiazole Polymer, Organic Film Including the Compound or Polymer and Transistor Including the Organic Film patent-application September 2009
Thiazolothiazole derivatives and organic electronic device using the same patent-application September 2010
Photovoltaic Cell Containing Novel Photoactive Polymer patent-application July 2013
Multilayer formation in spin-coated thin films of low-bandgap polyfluorene:PCBM blends journal December 2005
Synthesis and electroluminescent properties of fluorene-based copolymers containing electron-withdrawing thiazole derivatives journal November 2008
Effect of Molecular Weight and Annealing of Poly(3-hexylthiophene)s on the Performance of Organic Field-Effect Transistors journal August 2004
Fluorene-based alternating polymers containing electron-withdrawing bithiazole units: Preparation and device applications journal January 2005
Non-equilibrium effects on electronic transport in organic field effect transistors journal August 2007
Benzobisthiazole−Thiophene Copolymer Semiconductors: Synthesis, Enhanced Stability, Field-Effect Transistors, and Efficient Solar Cells journal November 2009
Characterization and Field-Effect Transistor Performance of Heterocyclic Oligomers Containing a Thiazolothiazole Unit journal September 2004
High Performance n-Type Organic Field-Effect Transistors Based on π-Electronic Systems with Trifluoromethylphenyl Groups journal March 2005
Physical properties and field-effect transistors based on novel thiazolothiazole/heterocyclic and thiazolothiazole/phenylene co-oligomers journal February 2006
Synthesis, physical properties, and field-effect transistors of novel thiophene/thiazolothiazole co-oligomers journal January 2004
Alkyl chain length dependence of the field-effect carrier mobility in regioregular poly(3-alkylthiophene)s journal January 2005
Tailoring Structure−Property Relationships in Dithienosilole−Benzothiadiazole Donor−Acceptor Copolymers journal June 2009
Synthesis and characterization of novel rigid two-photon absorbing polymers journal January 2005
A Low-Bandgap Poly(2,7-Carbazole) Derivative for Use in High-Performance Solar Cells journal September 2007
A New Poly(2,7-Dibenzosilole) Derivative in Polymer Solar Cells journal November 2007
Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rieke Zinc: Their Characterization and Solid-State Properties journal January 1995
Bandgap and Molecular Level Control of the Low-Bandgap Polymers Based on 3,6-Dithiophen-2-yl-2,5-dihydropyrrolo[3,4- c ]pyrrole-1,4-dione toward Highly Efficient Polymer Solar Cells journal September 2009
Synthesis, Characterization, and Photovoltaic Properties of a Low Band Gap Polymer Based on Silole-Containing Polythiophenes and 2,1,3-Benzothiadiazole journal December 2008
Synthesis and Photovoltaic Properties of Cyclopentadithiophene-Based Low-Bandgap Copolymers That Contain Electron-Withdrawing Thiazole Derivatives journal March 2010
Air-Stable Ambipolar Field-Effect Transistors and Complementary Logic Circuits from Solution-Processed n/p Polymer Heterojunctions journal October 2010
Low band-gap polymers based on quinoxaline derivatives and fused thiophene as donor materials for high efficiency bulk-heterojunction photovoltaic cells journal January 2009
Highly Efficient Solar Cell Polymers Developed via Fine-Tuning of Structural and Electronic Properties journal June 2009
Photovoltaic-Active Dithienosilole-Containing Polymers journal December 2007
Highly Disordered Polymer Field Effect Transistors: N -Alkyl Dithieno[3,2- b :2′,3′- d ]pyrrole-Based Copolymers with Surprisingly High Charge Carrier Mobilities journal October 2008
Synthesis, Characterization, and Transistor Response of Semiconducting Silole Polymers with Substantial Hole Mobility and Air Stability. Experiment and Theory journal June 2008
Preparation, Characterization, and Field-effect Transistor Performance of Benzo[1,2- d :4,5- d ′]bisthiazole Derivatives journal July 2008
Synthesis and Photovoltaic Properties of Copolymers from Benzodithiophene and Thiazole journal September 2010
Highly Air-Stable Thieno[3,2-b]thiophene-Thiophene-Thiazolo[5,4-d]thiazole-Based Polymers for Light-Emitting Diodes journal July 2010
Two Poly(2,5-thienythiazolothiazole)s: Observation of Spontaneous Ordering in Thin Films journal May 2008
High-Lamellar Ordering and Amorphous-Like π-Network in Short-Chain Thiazolothiazole−Thiophene Copolymers Lead to High Mobilities journal February 2009
Highly Stable Semiconducting Polymers Based on Thiazolothiazole journal July 2010
Novel Thiophene-Thiazolothiazole Copolymers for Organic Field-Effect Transistors journal December 2007
Energetics of electrode reactions. II. The relationship between redox potentials, ionization potentials, electron affinities, and solvation energies of aromatic hydrocarbons journal January 1976
Synthesis and Electroluminescent Properties of Copolymers Based on Fluorene and 2,5-Di(2-hexyloxyphenyl)thiazolothiazole journal August 2005
Synthesis of Copolymers Based on Thiazolothiazole and Their Applications in Polymer Solar Cells journal September 2010
Charge Carrier Transporting Molecular Materials and Their Applications in Devices journal April 2007
New n-Type Organic Semiconductors:  Synthesis, Single Crystal Structures, Cyclic Voltammetry, Photophysics, Electron Transport, and Electroluminescence of a Series of Diphenylanthrazolines
  • Tonzola, Christopher J.; Alam, Maksudul M.; Kaminsky, Werner
  • Journal of the American Chemical Society, Vol. 125, Issue 44, p. 13548-13558 https://doi.org/10.1021/ja036314e
journal November 2003
Dithienosilole− and Dibenzosilole−Thiophene Copolymers as Semiconductors for Organic Thin-Film Transistors journal July 2006
Comparative Study of the Field-Effect Mobility of a Copolymer and a Binary Blend Based on Poly(3-alkylthiophene)s journal February 2005