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CC BY-NC-ND 4.0 · Organic Materials 2019; 01(01): 078-087
DOI: 10.1055/s-0039-3402057
Original Article
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2019) The Author(s).

Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Dizao Li 
a   Beijing National Laboratory for Molecular Sciences, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. China
,
Qiang Wang
b   School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing, P. R. China
,
Liping Wang
b   School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing, P. R. China
,
Weifeng Zhang
a   Beijing National Laboratory for Molecular Sciences, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. China
,
Gui Yu 
a   Beijing National Laboratory for Molecular Sciences, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. China
c   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing, P. R. China
› Author Affiliations
Funding Information This study was funded by the National Key Research and Development Program of China (2016YFB0401100, 2017YFA0204703) and the National Natural Science Foundation of China (21673258, 21774134, and 51773016)
Further Information

Publication History

Received: 20 August 2019

Accepted after revision: 08 November 2019

Publication Date:
26 December 2019 (online)

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Abstract

Based on diketopyrrolopyrrole (DPP) and (E)-3-phenyl-2-(thiophen-2-yl)acrylonitrile (BVCNT)-linked conjugated backbones, three donor–acceptor type conjugated organic small-molecule compounds DPP-BVCNT, DPP-2FBVCNT, and DPP-3FBVCNT were designed and synthesized. Among them, the 2-decyltetradecyl side chain on the DPP acceptor unit was used to ensure the solubility of the material. The fluorine (F) atoms combined with the nitrile on the BVCNT donor unit were used to adjust electronic structures and charge carrier transport properties of the conjugated system. All the three small molecules exhibited good solution dispersibility and thermal stability, providing an important guarantee for the solution processing and annealing optimization of organic field-effect transistors (OFETs). The top-gate-bottom-contact OFET devices based on these compounds showed good ambipolar or p-type performances. The relationship between molecular structures and OFET performances indicated that the F-substitution and its position significantly affected their charge carrier transport properties. The F-substitution could remarkably change the performance from p-type to ambipolar especially for the outer-side-F-substituted compound DPP-2FBVCNT, which showed the best OFET performances with the maximum hole/electron mobilities of 0.023/0.220 cm2 V−1 s−1. These results provided a promising idea for developing small-molecule OFET materials with good solution processability, good thermal stability, and high ambipolar performances.

Key words

small-molecule semiconductors - organic field-effect transistors - mobility

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0039-3402057.


Supporting Information