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Molecular Requirements for Printable Organic Semiconductors in 7-Alkyl-2-phenyl[1]benzothieno[3,2-b][1]benzothiophenes (Ph-BTBT-Cn ’s)

Published online by Cambridge University Press:  13 June 2016

S. Inoue ,
H. Minemawari ,
J. Tsutsumi ,
T. Hamai ,
S. Arai ,
T. Yamada ,
S. Horiuchi ,
M. Tanaka ,
M. Yoneya  and
R. Kumai
...Show all authors
S. Inoue*
Affiliation:
Nippon Kayaku Co., Ltd., 31-12, Shimo 3-Chome, Kita-ku, Tokyo 115-8588, Japan. National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan.
H. Minemawari
Affiliation:
National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan.
J. Tsutsumi
Affiliation:
National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan.
T. Hamai
Affiliation:
Department of Applied Physics, The University of Tokyo, 7-3-1 Hongo, Tokyo 113-8656, Japan.
S. Arai
Affiliation:
Department of Applied Physics, The University of Tokyo, 7-3-1 Hongo, Tokyo 113-8656, Japan.
T. Yamada
Affiliation:
National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan.
S. Horiuchi
Affiliation:
National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan.
M. Tanaka
Affiliation:
National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan.
M. Yoneya
Affiliation:
National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan.
R. Kumai
Affiliation:
Condensed Matter Research Center (CMRC) and Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK), 1-1 Oho, Tsukuba 305-0801, Japan.
T. Hasegawa
Affiliation:
National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8562, Japan. Department of Applied Physics, The University of Tokyo, 7-3-1 Hongo, Tokyo 113-8656, Japan.
*
*(Email: satoru.inoue@nipponkayaku.co.jp)
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Abstract

Here we discuss requirements for high performance and solution processable organic semiconductors, by presenting a systematic investigation of 7-alkyl-2-phenyl[1]benzothieno[3,2-b][1]benzothiophenes (Ph-BTBT-Cn ’s). We found that the solubility and thermal properties of Ph-BTBT-Cn ’s depend systematically on the substituted alkyl-chain length n. The observed features are well understood in terms of the change of molecular packing motif with n: The compounds with n ≤ 4 do not form independent alkyl chain layers, whereas those with n ≥ 5 form isolated alkyl chain layers. The latter compounds afford a series of isomorphous bilayer-type crystal structures that form two-dimensional carrier transport layers within the crystals. We also show that the Ph-BTBT-C10 afford high performance single-crystalline field-effect transistors the mobility of which reaches as high as 15.9 cm2/Vs. These results demonstrate a crucial role of the substituted alkyl chain length for obtaining high performance organic semiconductors and field-effect transistors.

Keywords

organicsemiconductingcrystallographic structure
Type
Articles
Information
MRS Advances , Volume 1 , Issue 38: Materials Design , 2016 , pp. 2653 - 2658
Copyright
Copyright © Materials Research Society 2016 

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References

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