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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
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.
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Cited by
Functional Naphthalene Diimides: Synthesis, Properties, and Applications
Al Kobaisi, M., Bhosale, S. V., Latham, K., Raynor, A. M., & Bhosale, S. V. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00160 · Cited by 928
Recent Progress in High‐Mobility Organic Transistors: A Reality Check
Paterson, A. F., Singh, S., Fallon, K. J., Hodsden, T., Han, Y., Schroeder, B. C., Bronstein, H., Heeney, M., McCulloch, I., & Anthopoulos, T. D. (2018) · Advanced Materials · doi:10.1002/adma.201801079 · Cited by 641
Core-substituted naphthalenediimides
Sakai, N., Mareda, J., Vauthey, E., & Matile, S. (2010) · Chemical Communications · doi:10.1039/c0cc00078g · Cited by 566
High-Performance Air-Stable Organic Field-Effect Transistors: Isoindigo-Based Conjugated Polymers
Lei, T., Cao, Y., Fan, Y., Liu, C.-J., Yuan, S.-C., & Pei, J. (2011) · Journal of the American Chemical Society · doi:10.1021/ja111066r · Cited by 485
Quinn, J. T. E., Zhu, J., Li, X., Wang, J., & Li, Y. (2017) · Journal of Materials Chemistry C · doi:10.1039/c7tc01680h · Cited by 452
Electron transporting semiconducting polymers in organic electronics
Zhao, X., & Zhan, X. (2011) · Chemical Society Reviews · doi:10.1039/c0cs00194e · Cited by 414
Naphthalene diimides: perspectives and promise
Bhosale, S. V., Al Kobaisi, M., Jadhav, R. W., Morajkar, P. P., Jones, L. A., & George, S. (2021) · Chemical Society Reviews · doi:10.1039/d0cs00239a · Cited by 394
Zhang, Y., Wang, Y., Gao, C., Ni, Z., Zhang, X., Hu, W., & Dong, H. (2023) · Chemical Society Reviews · doi:10.1039/d2cs00720g · Cited by 293
Ultrathin Film Organic Transistors: Precise Control of Semiconductor Thickness via Spin‐Coating
Zhang, F., Di, C., Berdunov, N., Hu, Y., Hu, Y., Gao, X., Meng, Q., Sirringhaus, H., & Zhu, D. (2013) · Advanced Materials · doi:10.1002/adma.201204075 · Cited by 268
Self-citationXiong, Y., Tao, J., Wang, R., Qiao, X., Yang, X., Wang, D., Wu, H., & Li, H. (2016) · Advanced Materials · doi:10.1002/adma.201600120 · Cited by 123
Self-citation
Metadata
- Authors
- Gao, X., Di, C.-A., Hu, Y., Yang, X., Fan, H., Zhang, F., Liu, Y., Li, H., & Zhu, D.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-02-26
- Volume
- 132
- Issue
- 11
- Pages
- 3697-3699
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2043708517
- Cited by
- 284
- References
- 0
- FWCI
- 27.91
- Type
- journal article
- Language
- en
- Open access
- closed
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