Ambipolar Organic Field-Effect Transistors Based on Indigo Derivatives

Authors

  • Oratai Pitayatanakul Tokyo Institute of Technology
  • Kodai Iijima Tokyo Institute of Technology
  • Tomofumi Kadoya Tokyo Institute of Technology
  • Minoru Ashizawa Tokyo Institute of Technology
  • Tadashi Kawamoto Tokyo Institute of Technology
  • Hidetoshi Matsumoto Tokyo Institute of Technology
  • Takehiko Mori Tokyo Institute of Technology

DOI:

https://doi.org/10.4186/ej.2015.19.3.61

Keywords:

Organic transistor, ambipolar, organic semiconductor, natural material.

Abstract

In order to improve the ambipolar performance of indigo-based semiconductors, we have investigated halogen-substituted (1 - 4) and phenyl-substituted (5) indigo derivatives at the 5-position. We show that introduction of iodine atoms, namely 5,5'-diiodoindigo (4), leads to the strong halogen-halogen interaction (iodine-iodine interaction) that gives a significant effect on the molecular packing. Thanks to the supramolecular network coming from the extra iodine-iodine interaction, the molecules are arranged approximately perpendicular to the substrate in the thin film. This results in remarkable transistor performance of the maximum hole and electron mobilities (µh/µe) = 0.42/0.85 cm2V–1s–1, which are one of the highest among small-molecule ambipolar organic transistors. Furthermore, introducing phenyl groups, 5 improves the transistor performances up to the maximum mobilities µh/µe = 0.56/0.95 cm2V–1s–1. We have found that the phenyl groups destroy the standard molecular packing of indigo to achieve a unique structure that is a hybrid of the herringbone and brickwork structures.

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Author Biographies

Oratai Pitayatanakul

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan

Kodai Iijima

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan

Tomofumi Kadoya

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan

Minoru Ashizawa

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan

Tadashi Kawamoto

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan

Hidetoshi Matsumoto

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan

Takehiko Mori

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8552, Japan
ACT-C, JST, Honcho, Kawaguchi, Saitama 332-0012, Japan

Published

Vol 19 No 3, May 28, 2015

How to Cite

[1]
O. Pitayatanakul, “Ambipolar Organic Field-Effect Transistors Based on Indigo Derivatives”, Eng. J., vol. 19, no. 3, pp. 61-74, May 2015.

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