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Naphthalene diimide-based polymeric semiconductors. Effect of chlorine incorporation and n-channel transistors operating in water

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Abstract

We demonstrate here the design, synthesis and characterization of two new chlorinated polymers, P(NDI2HD-T2CI2) and P(NDI20D-T2CI2) based on N.N-difunctionalized naphthalene diimide (NDI) and 3, 3’-dichloro-2, 2’-bithiophene (T2CI2) moieties. Our results indicate that organic thin-film transistors (OTFTs) based on these new chlorinated polymers exhibit electron mobilities approaching 0.1 cm2V−1s−1 (Ion:/off ~ 106-107), with far less ambipolarity due to their lower highest occupied molecular orbital energies, and they are more stable under deleterious high-humidity conditions (RH ~ 60%) and upon submersion in water, compared with those fabricated with the parent non-chlorinated polymers. In addition, OTFTs fabricated with the new chlorinated polymers exhibit excellent operational stabilities with <3% degradations upon bias-stress test.

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Acknowledgments

AF thanks KAU (grant no. 4-130-36-HiCi) for support. This work was supported by a National Research Foundation of Korea (NRF) grant, funded by the Korean Government (MSIP) (NRF-2014R1A2A2A01007159). GSR and YYN thanks to Paul S. K. Amegadze for helpful discussion.

Author information

Authors and Affiliations

  1. Advanced Energy and Electronic Materials Research Center, Dongguk University, 30, Pil-dong-ro, 1-gil, Jung-gu, Seoul, 100-715, Korea

    Gi-Seong Ryu & Yong-Young Noh

  2. Polyera Corporation, 8045 Lamon Avenue, Skokie, lllinios, 60077, USA

    Zhihua Chen & Antonio Facchetti

  3. Department of Materials Science and Nanotechnology Engineering, Abdullah Gül University, Kayseri, Turkey

    Hakan Usta

  4. Department of Energy and Materials Engineering, Dongguk University, 30, Pil-dong-ro, 1-gil, Jung-gu, Seoul, 100-715, Korea

    Yong-Young Noh

  5. Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah, Saudi Arabia

    Antonio Facchetti

Authors
  1. Gi-Seong Ryu
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  2. Zhihua Chen
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  3. Hakan Usta
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  4. Yong-Young Noh
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  5. Antonio Facchetti
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Corresponding author

Correspondence to Yong-Young Noh.

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For supplementary material for this article, please visit http://dx.doi.org/10.1557/mrc.2016.4

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Ryu, GS., Chen, Z., Usta, H. et al. Naphthalene diimide-based polymeric semiconductors. Effect of chlorine incorporation and n-channel transistors operating in water. MRS Communications 6, 47–60 (2016). https://doi.org/10.1557/mrc.2016.4

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  • DOI: https://doi.org/10.1557/mrc.2016.4

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