Amorphous Solid Simulation and Trial Fabrication of the Organic Field-Effect Transistor of Tetrathienonaphthalenes Prepared by Using Microflow Photochemical Reactions: A Theoretical Calculation-Inspired Investigation

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• 作者：Atsushi Yamamoto ; Yasunori Matsui ; Toshio Asada ; Motoki Kumeda ; Kenichiro Takagi ; Yu Suenaga ; Kunihiko Nagae ; Eisuke Ohta ; Hiroyasu Sato ; Shiro Koseki ; Hiroyoshi Naito ; Hiroshi Ikeda
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：81
• 期：8
• 页码：3168-3176
• 全文大小：547K
• 年卷期：0
• ISSN：1520-6904

文摘

The p-type organic semiconductor (OSC) material tetrathieno[2,3-a:3′,2′-c:2″,3″-f:3‴,2‴-h]naphthalene (2TTN) and its alkyl-substituted derivatives C_n-2TTNs (n = 6, 8, and 10) have been developed based on the results of theoretical calculation-inspired investigation. A hole mobility for amorphous C_n-2TTNs (10^–2–10^–3 cm² V^–1 s^–1) was accurately predicted by using a novel statistical method in which the geometric mean of the mobilities for many individual small molecular flocks in an amorphous solid was obtained by using molecular mechanical molecular dynamics simulations and quantum chemical calculations. The simulation also suggests that upon increasing the length of alkyl chains in C_n-2TTNs the mobilities become smaller as a consequence of a decrease in transfer integral values. C_n-2TTNs are synthesized in a microflow reactor through photoreactions of the corresponding precursors. C_n-2TTNs are then utilized in the fabrication of organic field-effect transistors (OFETs). Although spin-coated thin films of C_n-2TTNs are crystalline, the hole mobilities (10^–2–10^–3 cm² V^–1 s^–1) of trial OFETs decrease upon elongation of the alkyl chains. This finding parallels the results of theoretical simulation. The simulation method for amorphous solids developed in this effort should become a useful tool in studies aimed at designing new OSC materials.