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Title: Furan Substituted Diketopyrrolopyrrole and Thienylenevinylene Based Low Band Gap Copolymer for High Mobility Organic Thin Film Transistors

Abstract

A novel solution processable donor-acceptor (D-A) based low band gap polymer semiconductor poly{l_brace}3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-thienylenevinylene{r_brace} (PDPPF-TVT), was designed and synthesized by a Pd-catalyzed Stille coupling route. An electron deficient furan based diketopyrrolopyrrole (DPP) block and electron rich thienylenevinylene (TVT) donor moiety were attached alternately in the polymer backbone. The polymer exhibited good solubility, film forming ability and thermal stability. The polymer exhibits wide absorption bands from 400 nm to 950 nm (UV-vis-NIR region) with absorption maximum centered at 782 nm in thin film. The optical band gap (E{sub g}{sup opt}) calculated from the polymer film absorption onset is around 1.37 eV. The {pi}-energy band level (ionization potential) calculated by photoelectron spectroscopy in air (PESA) for PDPPF-TVT is around 5.22 eV. AFM and TEM analyses of the polymer reveal nodular terrace morphology with optimized crystallinity after 200 C thermal annealing. This polymer exhibits p-channel charge transport characteristics when used as the active semiconductor in organic thin-film transistor (OTFT) devices. The highest hole mobility of 0.13 cm{sup 2} V{sup -1} s{sup -1} is achieved in bottom gate and top-contact OTFT devices with on/off ratios in the range of 10{sup 6}-10{sup 7}. This work reveals that the replacement of thiophene by furan in DPP copolymersmore » exhibits such a high mobility, which makes DPP furan a promising block for making a wide range of promising polymer semiconductors for broad applications in organic electronics.« less

Authors:
 [1];  [2];  [3];  [2];  [4];  [1];  [3];  [3];  [3]
  1. Institute of Materials Research and Engineering (IMRE), Agency for Science, Technology, and Research
  2. National University of Singapore (NUS)
  3. National University of Singapore
  4. ORNL
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Center for Nanophase Materials Sciences
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1047635
DOE Contract Number:  
DE-AC05-00OR22725
Resource Type:
Journal Article
Journal Name:
Journal of Materials Chemistry
Additional Journal Information:
Journal Volume: 22; Journal Issue: 33; Journal ID: ISSN 0959-9428
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ABSORPTION; AIR; ANNEALING; CHARGE TRANSPORT; COPOLYMERS; ELECTRONS; FURANS; HOLE MOBILITY; IONIZATION; MORPHOLOGY; PHOTOELECTRON SPECTROSCOPY; POLYMERS; SOLUBILITY; STABILITY; THIN FILMS; THIOPHENE; TRANSISTORS

Citation Formats

Sonar, Prashant, Zhuo, Jing-Mei, Zhao, Li-Hong, Lim, Kai-Ming, Chen, Jihua, Rondinone, Adam Justin, Singh, Samarendra, Chua, Lay-Lay, Ho, Peter, and Dodabalapur, Ananth. Furan Substituted Diketopyrrolopyrrole and Thienylenevinylene Based Low Band Gap Copolymer for High Mobility Organic Thin Film Transistors. United States: N. p., 2012. Web. doi:10.1039/c2jm32376a.
Sonar, Prashant, Zhuo, Jing-Mei, Zhao, Li-Hong, Lim, Kai-Ming, Chen, Jihua, Rondinone, Adam Justin, Singh, Samarendra, Chua, Lay-Lay, Ho, Peter, & Dodabalapur, Ananth. Furan Substituted Diketopyrrolopyrrole and Thienylenevinylene Based Low Band Gap Copolymer for High Mobility Organic Thin Film Transistors. United States. https://doi.org/10.1039/c2jm32376a
Sonar, Prashant, Zhuo, Jing-Mei, Zhao, Li-Hong, Lim, Kai-Ming, Chen, Jihua, Rondinone, Adam Justin, Singh, Samarendra, Chua, Lay-Lay, Ho, Peter, and Dodabalapur, Ananth. Sun . "Furan Substituted Diketopyrrolopyrrole and Thienylenevinylene Based Low Band Gap Copolymer for High Mobility Organic Thin Film Transistors". United States. https://doi.org/10.1039/c2jm32376a.
@article{osti_1047635,
title = {Furan Substituted Diketopyrrolopyrrole and Thienylenevinylene Based Low Band Gap Copolymer for High Mobility Organic Thin Film Transistors},
author = {Sonar, Prashant and Zhuo, Jing-Mei and Zhao, Li-Hong and Lim, Kai-Ming and Chen, Jihua and Rondinone, Adam Justin and Singh, Samarendra and Chua, Lay-Lay and Ho, Peter and Dodabalapur, Ananth},
abstractNote = {A novel solution processable donor-acceptor (D-A) based low band gap polymer semiconductor poly{l_brace}3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-thienylenevinylene{r_brace} (PDPPF-TVT), was designed and synthesized by a Pd-catalyzed Stille coupling route. An electron deficient furan based diketopyrrolopyrrole (DPP) block and electron rich thienylenevinylene (TVT) donor moiety were attached alternately in the polymer backbone. The polymer exhibited good solubility, film forming ability and thermal stability. The polymer exhibits wide absorption bands from 400 nm to 950 nm (UV-vis-NIR region) with absorption maximum centered at 782 nm in thin film. The optical band gap (E{sub g}{sup opt}) calculated from the polymer film absorption onset is around 1.37 eV. The {pi}-energy band level (ionization potential) calculated by photoelectron spectroscopy in air (PESA) for PDPPF-TVT is around 5.22 eV. AFM and TEM analyses of the polymer reveal nodular terrace morphology with optimized crystallinity after 200 C thermal annealing. This polymer exhibits p-channel charge transport characteristics when used as the active semiconductor in organic thin-film transistor (OTFT) devices. The highest hole mobility of 0.13 cm{sup 2} V{sup -1} s{sup -1} is achieved in bottom gate and top-contact OTFT devices with on/off ratios in the range of 10{sup 6}-10{sup 7}. This work reveals that the replacement of thiophene by furan in DPP copolymers exhibits such a high mobility, which makes DPP furan a promising block for making a wide range of promising polymer semiconductors for broad applications in organic electronics.},
doi = {10.1039/c2jm32376a},
url = {https://www.osti.gov/biblio/1047635}, journal = {Journal of Materials Chemistry},
issn = {0959-9428},
number = 33,
volume = 22,
place = {United States},
year = {2012},
month = {1}
}