Synthesis, Structural Characterization, and Unusual Field-Effect Behavior of Organic Transistor Semiconductor Oligomers: Inferiority of Oxadiazole Compared with Other Electron-Withdrawing Subunits
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- 作者：Taegweon Lee ; Chad A. Landis ; Bal Mukund Dhar ; Byung Jun Jung ; Jia Sun ; Amy Sarjeant ; Ho-Jin Lee ; Howard E. Katz
- 刊名：Journal of the American Chemical Society
- 出版年：2009
- 出版时间：February 11, 2009
- 年：2009
- 卷：131
- 期：5
- 页码：1692-1705
- 全文大小：571K
- 年卷期：v.131,no.5(February 11, 2009)
- ISSN：1520-5126
文摘
A new series of heterocyclic oligomers based on the 1,3,4-oxadiazole ring were synthesized. Other electron-deficient cores (fluorenone and fumaronitrile) were introduced to investigate the oligomers as n-channel materials. The physical properties, thin film morphologies, and field-effect transistor characteristics of the oligomers were evaluated. Thin films were deposited at different substrate temperatures and on variously coated Si/SiO2 for device optimization. Contrary to our expectations, the thin film devices of 4 revealed p-channel behavior, and the average hole mobility was 0.14 cm2 V−1 s−1 (maximum value 0.18 cm2 V−1 s−1). Compound 11 is the first example of an oxadiazole-containing organic semiconductor (OSC) oligomer in an n-channel organic field-effect transistor (OFET) and shows moderate mobilities. Non-oxadiazole-containing oligomers 9 and 12 showed n-channel OFET behavior on hexamethyldisilazane-treated and Cytop spin-coated SiO2 in vacuum. These are the first fluorenone- and fumaronitrile-based n-OSCs demonstrated in transistors. However, oxadiazole-core materials 14 and 16 were inactive in transistor devices.