Ambipolar organic field-effect transistors based on N-Unsubstituted thienoisoindigo derivatives

Dongho Yoo, Tsukasa Hasegawa, Akihiro Kohara, Haruki Sugiyama, Minoru Ashizawa, Tadashi Kawamoto, Hiroyasu Masunaga, Takaaki Hikima, Noboru Ohta, Hidehiro Uekusa, Hidetoshi Matsumoto, Takehiko Mori

Research output: Contribution to journalArticle

Abstract

To investigate a hybrid of isoindigo and thienoisoindigo (TIIG), a new series of unsymmetrical TIIG analogs, in which one of the outer thiophene rings of TIIG is replaced by benzene (CS) or pyridine (NS) are prepared. In addition, the π-skeleton extension effects are studied by examining α-substituted TIIG derivatives with thienyl (Dth-TIIG), furyl (Dfu-TIIG), and 1-phenyl-5-pyrazolyl groups (Bis(1-ph-5-py)-TIIG). These materials exhibit ambipolar transistor properties as expected from the energy levels. Dth-TIIG and Dfu-TIIG show hole mobilities exceeding 0.05 cm2 V−1 s−1, and electron mobilities about 0.04 cm2 V−1 s−1, which are close to those of the diphenyl derivative. These molecules are arranged nearly perpendicularly to the substrates in the thin films, and Dth-TIIG has a brickwork-like structure, whereas Dfu-TIIG has uniform columns. CS and Bis(1-ph-5-py)-TIIG have uniform stacking structures, but NS has a dimerized stacking structure due to the slightly bent molecular plane that results from largely unbalanced electron density.

Original languageEnglish
Article number108418
JournalDyes and Pigments
Volume180
DOIs
Publication statusPublished - 2020 Sep

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Keywords

  • Ambipolar transistors
  • Organic field-effect transistors
  • Thieno-benzo-isoindigo
  • Thieno-pyridine-isoindigo
  • Thienoisoindigo
  • α-substituted thienoisoindigo derivatives

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

Yoo, D., Hasegawa, T., Kohara, A., Sugiyama, H., Ashizawa, M., Kawamoto, T., Masunaga, H., Hikima, T., Ohta, N., Uekusa, H., Matsumoto, H., & Mori, T. (2020). Ambipolar organic field-effect transistors based on N-Unsubstituted thienoisoindigo derivatives. Dyes and Pigments, 180, [108418]. https://doi.org/10.1016/j.dyepig.2020.108418