Core-expanded naphthalene diimides fused with 2-(1,3-dithiol-2-ylidene)malonitrile groups for high-performance, ambient-stable, solution-processed n-channel organic thin film transistors

Xike Gao; Chong-an Di; Yunbin Hu; Xiaodi Yang; Hongyu Fan; Feng Zhang; Yunqi Liu; Hongxiang Li; Daoben Zhu

doi:10.1021/ja910667y

Core-expanded naphthalene diimides fused with 2-(1,3-dithiol-2-ylidene)malonitrile groups for high-performance, ambient-stable, solution-processed n-channel organic thin film transistors

J Am Chem Soc. 2010 Mar 24;132(11):3697-9. doi: 10.1021/ja910667y.

Authors

Xike Gao¹, Chong-an Di, Yunbin Hu, Xiaodi Yang, Hongyu Fan, Feng Zhang, Yunqi Liu, Hongxiang Li, Daoben Zhu

Affiliation

¹ Laboratory of Materials Science, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. gaoxk@mail.sioc.ac.cn

PMID: 20187650
DOI: 10.1021/ja910667y

Abstract

A new class of n-type semiconductors for organic thin film transistors (OTFTs), based on core-expanded naphthalene diimides fused with 2-(1,3-dithiol-2-ylidene)malonitrile groups, is reported. The first two representatives of these species, derived from long branched N-alkyl chains, have been successfully used as active layers for high-performance, ambient-stable, solution-processed n-channel OTFTs. Their bottom-gate top-contact devices fabricated by spin-coating methods exhibit high electron mobilities of up to 0.51 cm(2) V(-1) s(-1) with current on/off ratios of 10(5)-10(7), and small threshold voltages below 10 V under ambient conditions. As this class of n-type organic semiconductors has relatively low-lying LUMO levels and good film-formation ability, they also displayed good environmental stability even with prolonged exposure to ambient air. Both the device performance and the ambient stability are among the best for n-channel OTFTs reported to date.