skip to main content
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):
8,871,884
Application Number:
13/504,058
Assignee:
University of Washington (Seattle, WA)
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}
}

Patent:

Save / Share:

Works referenced in this record:

Window with photovoltaic cell
patent-application, June 2007


Tandem Photovoltaic Cells
patent-application, October 2007


Multilayer formation in spin-coated thin films of low-bandgap polyfluorene:PCBM blends
journal, December 2005

  • Björström, Cecilia M.; Bernasik, Andrzej; Rysz, Jakub
  • Journal of Physics: Condensed Matter, Vol. 17, Issue 50
  • DOI: 10.1088/0953-8984/17/50/L01

Synthesis and electroluminescent properties of fluorene-based copolymers containing electron-withdrawing thiazole derivatives
journal, November 2008

  • Jung, In Hwan; Jung, Young Kwan; Lee, Jonghee
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 46, Issue 21
  • DOI: 10.1002/pola.23019

Effect of Molecular Weight and Annealing of Poly(3-hexylthiophene)s on the Performance of Organic Field-Effect Transistors
journal, August 2004

  • Zen, A.; Pflaum, J.; Hirschmann, S.
  • Advanced Functional Materials, Vol. 14, Issue 8, p. 757-764
  • DOI: 10.1002/adfm.200400017

Fluorene-based alternating polymers containing electron-withdrawing bithiazole units: Preparation and device applications
journal, January 2005

  • Lee, Jaemin; Jung, Byung-Jun; Lee, Sang Kyu
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 43, Issue 9
  • DOI: 10.1002/pola.20659

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

  • Ahmed, Eilaf; Kim, Felix S.; Xin, Hao
  • Macromolecules, Vol. 42, Issue 22
  • DOI: 10.1021/ma9015278

Characterization and Field-Effect Transistor Performance of Heterocyclic Oligomers Containing a Thiazolothiazole Unit
journal, September 2004

  • Ando, Shinji; Nishida, Jun-ichi; Fujiwara, Eiichi
  • Chemistry Letters, Vol. 33, Issue 9
  • DOI: 10.1246/cl.2004.1170

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

  • Ando, Shinji; Nishida, Jun-ichi; Inoue, Youji
  • Journal of Materials Chemistry, Vol. 14, Issue 12
  • DOI: 10.1039/b403699a

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

  • Beaujuge, Pierre M.; Pisula, Wojciech; Tsao, Hoi Nok
  • Journal of the American Chemical Society, Vol. 131, Issue 22
  • DOI: 10.1021/ja900519k

Synthesis and characterization of novel rigid two-photon absorbing polymers
journal, January 2005

  • Belfield, Kevin D.; Yao, Sheng; Morales, Alma R.
  • Polymers for Advanced Technologies, Vol. 16, Issue 2-3
  • DOI: 10.1002/pat.550

A Low-Bandgap Poly(2,7-Carbazole) Derivative for Use in High-Performance Solar Cells
journal, September 2007

  • Blouin, N.; Michaud, A.; Leclerc, M.
  • Advanced Materials, Vol. 19, Issue 17, p. 2295-2300
  • DOI: 10.1002/adma.200602496

A New Poly(2,7-Dibenzosilole) Derivative in Polymer Solar Cells
journal, November 2007

  • Boudreault, Pierre-Luc T.; Michaud, Alexandre; Leclerc, Mario
  • Macromolecular Rapid Communications, Vol. 28, Issue 22
  • DOI: 10.1002/marc.200700470

Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rieke Zinc: Their Characterization and Solid-State Properties
journal, January 1995

  • Chen, Tian-An; Wu, Xiaoming; Rieke, Reuben D.
  • Journal of the American Chemical Society, Vol. 117, Issue 1, p. 233-244
  • DOI: 10.1021/ja00106a027

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

  • Hou, Jianhui; Chen, Hsiang-Yu; Zhang, Shaoqing
  • Journal of the American Chemical Society, Vol. 130, Issue 48, p. 16144-16145
  • DOI: 10.1021/ja806687u

Synthesis and Photovoltaic Properties of Cyclopentadithiophene-Based Low-Bandgap Copolymers That Contain Electron-Withdrawing Thiazole Derivatives
journal, March 2010

  • Jung, In Hwan; Yu, Jinyoung; Jeong, Eunjae
  • Chemistry - A European Journal, Vol. 16, Issue 12
  • DOI: 10.1002/chem.200903064

Air-Stable Ambipolar Field-Effect Transistors and Complementary Logic Circuits from Solution-Processed n/p Polymer Heterojunctions
journal, October 2010

  • Kim, Felix Sunjoo; Ahmed, Eilaf; Subramaniyan, Selvam
  • ACS Applied Materials & Interfaces, Vol. 2, Issue 11
  • DOI: 10.1021/am1006996

Low band-gap polymers based on quinoxaline derivatives and fused thiophene as donor materials for high efficiency bulk-heterojunction photovoltaic cells
journal, January 2009

  • Lee, Jang-Yong; Shin, Won-Suk; Haw, Jung-Rim
  • Journal of Materials Chemistry, Vol. 19, Issue 28, p. 4938-4945
  • DOI: 10.1039/b823536h

Highly Efficient Solar Cell Polymers Developed via Fine-Tuning of Structural and Electronic Properties
journal, June 2009

  • Liang, Yongye; Feng, Danqin; Wu, Yue
  • Journal of the American Chemical Society, Vol. 131, Issue 22, p. 7792-7799
  • DOI: 10.1021/ja901545q

Photovoltaic-Active Dithienosilole-Containing Polymers
journal, December 2007

  • Liao, Liang; Dai, Liming; Smith, Adam
  • Macromolecules, Vol. 40, Issue 26
  • DOI: 10.1021/ma071825x

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

  • Liu, Junying; Zhang, Rui; Sauvé, Geneviève
  • Journal of the American Chemical Society, Vol. 130, Issue 39
  • DOI: 10.1021/ja803077v

Synthesis, Characterization, and Transistor Response of Semiconducting Silole Polymers with Substantial Hole Mobility and Air Stability. Experiment and Theory
journal, June 2008

  • Lu, Gang; Usta, Hakan; Risko, Chad
  • Journal of the American Chemical Society, Vol. 130, Issue 24
  • DOI: 10.1021/ja800424m

Preparation, Characterization, and Field-effect Transistor Performance of Benzo[1,2- d :4,5- d ′]bisthiazole Derivatives
journal, July 2008

  • Mamada, Masashi; Nishida, Jun-ichi; Tokito, Shizuo
  • Chemistry Letters, Vol. 37, Issue 7
  • DOI: 10.1246/cl.2008.766

Synthesis and Photovoltaic Properties of Copolymers from Benzodithiophene and Thiazole
journal, September 2010

  • Yang, Miao; Peng, Bo; Liu, Bo
  • The Journal of Physical Chemistry C, Vol. 114, Issue 41
  • DOI: 10.1021/jp1063885

Highly Air-Stable Thieno[3,2-b]thiophene-Thiophene-Thiazolo[5,4-d]thiazole-Based Polymers for Light-Emitting Diodes
journal, July 2010

  • Mishra, Sarada P.; Palai, Akshaya K.; Kumar, Amit
  • Macromolecular Chemistry and Physics, Vol. 211, Issue 17
  • DOI: 10.1002/macp.201000132

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

  • Osaka, Itaru; Zhang, Rui; Sauvé, Geneviève
  • Journal of the American Chemical Society, Vol. 131, Issue 7
  • DOI: 10.1021/ja801475h

Highly Stable Semiconducting Polymers Based on Thiazolothiazole
journal, July 2010

  • Osaka, Itaru; Zhang, Rui; Liu, Junying
  • Chemistry of Materials, Vol. 22, Issue 14
  • DOI: 10.1021/cm101052b

Novel Thiophene-Thiazolothiazole Copolymers for Organic Field-Effect Transistors
journal, December 2007

  • Osaka, I.; Sauvé, G.; Zhang, R.
  • Advanced Materials, Vol. 19, Issue 23, p. 4160-4165
  • DOI: 10.1002/adma.200701058

Synthesis and Electroluminescent Properties of Copolymers Based on Fluorene and 2,5-Di(2-hexyloxyphenyl)thiazolothiazole
journal, August 2005

  • Peng, Qiang; Peng, Jun-Biao; Kang, E. T.
  • Macromolecules, Vol. 38, Issue 17
  • DOI: 10.1021/ma050378n

Synthesis of Copolymers Based on Thiazolothiazole and Their Applications in Polymer Solar Cells
journal, September 2010

  • Shi, Qinqin; Fan, Haijun; Liu, Yao
  • The Journal of Physical Chemistry C, Vol. 114, Issue 39
  • DOI: 10.1021/jp106319x

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
  • DOI: 10.1021/ja036314e

Dithienosilole− and Dibenzosilole−Thiophene Copolymers as Semiconductors for Organic Thin-Film Transistors
journal, July 2006

  • Usta, Hakan; Lu, Gang; Facchetti, Antonio
  • Journal of the American Chemical Society, Vol. 128, Issue 28, p. 9034-9035
  • DOI: 10.1021/ja062908g

Comparative Study of the Field-Effect Mobility of a Copolymer and a Binary Blend Based on Poly(3-alkylthiophene)s
journal, February 2005

  • Zen, Achmad; Saphiannikova, Marina; Neher, Dieter
  • Chemistry of Materials, Vol. 17, Issue 4
  • DOI: 10.1021/cm040183e