DOE Patents title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

Abstract

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.

Inventors:
; ; ; ;
Issue Date:
Research Org.:
Univ. of Washington, Seattle, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1162114
Patent Number(s):
8871884
Application Number:
13/504,058
Assignee:
University of Washington (Seattle, WA)
Patent Classifications (CPCs):
C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08G - MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
Y - NEW / CROSS SECTIONAL TECHNOLOGIES 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
DOE Contract Number:  
FG02-07ER46467
Resource Type:
Patent
Resource Relation:
Patent File Date: 2010 Oct 26
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 14 SOLAR ENERGY

Citation Formats

Jenekhe, Samson A, Subramaniyan, Selvam, Ahmed, Eilaf, Xin, Hao, and Kim, Felix Sunjoo. Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells. United States: N. p., 2014. Web.
Jenekhe, Samson A, Subramaniyan, Selvam, Ahmed, Eilaf, Xin, Hao, & Kim, Felix Sunjoo. Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells. United States.
Jenekhe, Samson A, Subramaniyan, Selvam, Ahmed, Eilaf, Xin, Hao, and Kim, Felix Sunjoo. Tue . "Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells". United States. https://www.osti.gov/servlets/purl/1162114.
@article{osti_1162114,
title = {Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells},
author = {Jenekhe, Samson A and Subramaniyan, Selvam and Ahmed, Eilaf and Xin, Hao and Kim, Felix Sunjoo},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2014},
month = {10}
}

Works referenced in this record:

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


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


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


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


Synthesis, Characterization, and Photovoltaic Properties of a Low Band Gap Polymer Based on Silole-Containing Polythiophenes and 2,1,3-Benzothiadiazole
journal, December 2008


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


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


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


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
journal, November 2003

  • 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

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