Core Fluorination Enhances Solubility and Ambient Stability of an IDT-Based n-Type Semiconductor in Transistor Devices

Abstract
The synthesis of a novel fluorinated n-type small molecule based on an inda-cenodithiophene core is reported. Fluorination is found to have a significant impact on the physical properties, including a surprisingly dramatic improve-ment in solubility, in addition to effectively stabilizing the lowest-unoccupied molecular orbital energy (−4.24 eV). Single-crystal analysis and density func-tional theory calculations indicate the improved solubility can be attributed to backbone torsion resulting from the positioning of the fluorine group in close proximity to the strongly electron-withdrawing dicyanomethylene group. Organic thin-film transistors made via blade coating display high electron mobility (up to 0.49 cm2 V−1 s−1) along with good retention of performance in ambient conditions.

Citation
Hodsden, T., Thorley, K. J., Panidi, J., Basu, A., Marsh, A. V., Dai, H., … Heeney, M. (2020). Core Fluorination Enhances Solubility and Ambient Stability of an IDT-Based n-Type Semiconductor in Transistor Devices. Advanced Functional Materials, 2000325. doi:10.1002/adfm.202000325

Acknowledgements
The authors thank the Engineering and Physical Sciences Research Council (EPSRC) (Grant EP/L016702/1) and the Royal Society and the Wolfson Foundation (for Royal Society Wolfson Fellowship) for support. A.B. and T.D.A. are grateful to KAUST for the financial support.

Publisher
Wiley

Journal
Advanced Functional Materials

DOI
10.1002/adfm.202000325

Additional Links
https://onlinelibrary.wiley.com/doi/abs/10.1002/adfm.202000325

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