Donor–acceptor copolymers containing quinacridone and benzothiadiazole for thin film transistors

Two donor–acceptor copolymers, PQB and PQBOC8, containing a donor component quinacridone and an acceptor component benzothiadiazole were synthesized. Introduction of two additional alkoxy chains onto the benzothiadiazole in PQBOC8 not only enhanced solubility and molecular weight but also altered photo-electrochemical properties and polymer chain conformation compared with PQB. As a result, they exhibited different film microstructure and transistor performance. Indeed, PQBOC8 exhibited an ordered lamellar structure with a chain-to-chain distance of 21.5 A and a π–π stacking distance of 4.0 A and showed a hole mobility of up to 0.30 cm2 V−1 s−1 in ambient conditions, while PQB revealed a highly disordered film microstructure and a hole mobility of 5.77 × 10−3 cm2 V−1 s−1.

[1]  J. Lee,et al.  Conjugated Polymer Consisting of Quinacridone and Benzothiadiazole as Donor Materials for Organic Photovoltaics: Coplanar Property of Polymer Backbone , 2012 .

[2]  Jean-Luc Brédas,et al.  Donor-Acceptor Copolymers of Relevance for Organic Photovoltaics: A Theoretical Investigation of the Impact of Chemical-Structure Modifications on the Electronic and Optical Properties , 2012 .

[3]  Soo‐Hyoung Lee,et al.  Novel naphtho[1,2-b:5,6-b′]dithiophene core linear donor–π–acceptor conjugated small molecules with thiophene-bridged bithiazole acceptor: design, synthesis, and their application in bulk heterojunction organic solar cells , 2012 .

[4]  H. Sirringhaus,et al.  A new thiophene substituted isoindigo based copolymer for high performance ambipolar transistors. , 2012, Chemical communications.

[5]  T. Koganezawa,et al.  Quinacridone-Based Semiconducting Polymers: Implication of Electronic Structure and Orientational Order for Charge Transport Property , 2012 .

[6]  Yang Yang,et al.  Tandem polymer solar cells featuring a spectrally matched low-bandgap polymer , 2012, Nature Photonics.

[7]  A. Heeger,et al.  Quinacridone‐Based Electron Transport Layers for Enhanced Performance in Bulk‐Heterojunction Solar Cells , 2011 .

[8]  W. Xu,et al.  New air-stable solution-processed organic n-type semiconductors based on sulfur-rich core-expanded naphthalene diimides , 2011 .

[9]  A. Iraqi,et al.  Carbazole and thienyl benzo[1,2,5]thiadiazole based polymers with improved open circuit voltages and processability for application in solar cells , 2011 .

[10]  O. Inganäs,et al.  An easily accessible isoindigo-based polymer for high-performance polymer solar cells. , 2011, Journal of the American Chemical Society.

[11]  W. Li,et al.  Donor-acceptor conjugated polymer based on naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole for high-performance polymer solar cells. , 2011, Journal of the American Chemical Society.

[12]  Jian Pei,et al.  High-performance air-stable organic field-effect transistors: isoindigo-based conjugated polymers. , 2011, Journal of the American Chemical Society.

[13]  H. Sirringhaus,et al.  Thieno[3,2-b]thiophene-diketopyrrolopyrrole-containing polymers for high-performance organic field-effect transistors and organic photovoltaic devices. , 2011, Journal of the American Chemical Society.

[14]  Robert Graf,et al.  Ultrahigh mobility in polymer field-effect transistors by design. , 2011, Journal of the American Chemical Society.

[15]  P. Sonar,et al.  A Low‐Bandgap Diketopyrrolopyrrole‐Benzothiadiazole‐Based Copolymer for High‐Mobility Ambipolar Organic Thin‐Film Transistors , 2010, Advanced materials.

[16]  Teresa L. Chen,et al.  Quinacridone-based molecular donors for solution processed bulk-heterojunction organic solar cells. , 2010, ACS applied materials & interfaces.

[17]  A. Arias,et al.  Materials and applications for large area electronics: solution-based approaches. , 2010, Chemical reviews.

[18]  K. Hashimoto,et al.  Indolo[3,2-b]carbazole-based alternating donor–acceptor copolymers: synthesis, properties and photovoltaic application , 2009 .

[19]  M. Andersson,et al.  A planar copolymer for high efficiency polymer solar cells. , 2009, Journal of the American Chemical Society.

[20]  V. Roy,et al.  Organic field-effect transistors fabricated with N,N′-substituted dialkyl-1,3,8,10-tetramethylquinacridone compounds , 2009 .

[21]  Xiabin Jing,et al.  Novel White Electroluminescent Single Polymer Derived from Fluorene and Quinacridone , 2008 .

[22]  Rui Zhang,et al.  Novel Thiophene‐Thiazolothiazole Copolymers for Organic Field‐Effect Transistors , 2007 .

[23]  S. Jenekhe,et al.  Conjugated donor-acceptor copolymer semiconductors with large intramolecular charge transfer : Synthesis, optical properties, electrochemistry, and field effect carrier mobility of thienopyrazine-based copolymers , 2006 .

[24]  H. Sirringhaus,et al.  High-Resolution Ink-Jet Printing of All-Polymer Transistor Circuits , 2000, Science.

[25]  E. W. Meijer,et al.  Two-dimensional charge transport in self-organized, high-mobility conjugated polymers , 1999, Nature.

[26]  H. Sirringhaus,et al.  Integrated optoelectronic devices based on conjugated polymers , 1998, Science.

[27]  Y. Yamashita,et al.  New Narrow-Bandgap Polymer Composed of Benzobis(1,2,5-thiadiazole) and Thiophenes , 1995 .