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Isothianaphthene diimide: an air-stable n-type semiconductor

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Abstract

Herein, we propose a new strategy to develop air-stable n-type organic semiconductors with non-classical thiophene aromatic diimide derivatives by replacing aromatic naphthalene with a heteroaromatic isothianaphthene core. We designed and successfully synthesized the isothianaphthene core based diimide material, N,N′-bis(n-hexyl)isothianaphthene-2,3,6,7-tetra-carboxylic acid diimide (BTDI-C6) as an n-type semiconductor. Compared to N,N′-bis(n-hexyl)naphthalene-1,4,5,8-tetracarboxylic acid diimide (NDI-C6), BTDI-C6 possesses a deeper LUMO energy level of −4.21 eV, which is 0.32 eV lower than that of NDI-C6. Both molecular modelling and experimental results elucidated that organic thin film transistors (OTFTs) based on both of these materials exhibit comparable mobilities; however, the threshold voltage of BTDI-C6 based device (+7.5 V) is significantly lower than that of NDI-C6 based counterpart (+34 V). Moreover, the low-lying LUMO energy level of BTDI-C6 ensures excellent air-stability which is further validated by the device performance. In addition, BTDI-C6 shows high luminescence while NDI-C6 is not luminescent at all in solution, which reveals the potential application of our newly synthesized material in n-type light-emitting transistors.

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Acknowledgements

This work was supported by Shenzhen Science and Technology (JCYJ20170412151139619), Shenzhen Engineering Laboratory (Shenzhen development and reform commission [2016]1592), Guangdong Key Research Project (2019B010924003), Guangdong International Science Collaboration Base (2019A050505003), and Shenzhen Peacock Plan (KQTD2014062714543296).

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Authors and Affiliations

  1. School of Advanced Materials, Peking University Shenzhen Graduated School, Shenzhen, 518055, China

    **aolong Chen, Yaowu He, Yu He, Yanan Zhu, Aiyuan Li, Changbin Zhao & Hong Meng

  2. Department of Materials Science and Engineering, College of Engineering, Peking University, Bei**g, 100871, China

    Muhammad Umair Ali

  3. Shaanxi Institute of Flexible Electronics, Northwestern Polytechnical University, **’an, 710072, China

    Igor F. Perepichka

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  1. **aolong Chen
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  2. Yaowu He
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  4. Yu He
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  5. Yanan Zhu
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  6. Aiyuan Li
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  9. Hong Meng
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Correspondence to Hong Meng.

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Chen, X., He, Y., Ali, M.U. et al. Isothianaphthene diimide: an air-stable n-type semiconductor. Sci. China Chem. 62, 1360–1364 (2019). https://doi.org/10.1007/s11426-019-9555-4

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