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Synthesis and characterization of fused-thiophene containing naphthalene diimide n-type copolymers for organic thin film transistor and all-polymer solar cell applications

Authors

  • Mingjian Yuan,

    1. Department of Materials Science and Engineering, University of Washington, Seattle, Washington
    2. Molecular Engineering & Sciences Institute, University of Washington, Seattle, Washington
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  • Matthew M. Durban,

    1. Molecular Engineering & Sciences Institute, University of Washington, Seattle, Washington
    2. Department of Chemistry, University of Washington, Seattle, Washington
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  • Peter D. Kazarinoff,

    1. Department of Materials Science and Engineering, University of Washington, Seattle, Washington
    2. Molecular Engineering & Sciences Institute, University of Washington, Seattle, Washington
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  • David F. Zeigler,

    1. Molecular Engineering & Sciences Institute, University of Washington, Seattle, Washington
    2. Department of Chemistry, University of Washington, Seattle, Washington
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  • Andrew H. Rice,

    1. Department of Materials Science and Engineering, University of Washington, Seattle, Washington
    2. Molecular Engineering & Sciences Institute, University of Washington, Seattle, Washington
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  • Yukari Segawa,

    1. Department of Organic and Polymeric Materials, Graduate School of Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo, Japan
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  • Christine K. Luscombe

    Corresponding author
    1. Molecular Engineering & Sciences Institute, University of Washington, Seattle, Washington
    • Department of Materials Science and Engineering, University of Washington, Seattle, Washington
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Correspondence to: C. K. Luscombe (E - mail: luscombe@u.washington.edu)

ABSTRACT

Naphthalene diimide copolymers are attractive n-type materials due to their high electron affinities, high electron mobilities, and exceptional stability. Herein, we report a series of NDI-fused-thiophene based copolymers with each copolymer differing in the number of fused thiophenes in the donor monomer. Increasing the number of fused-thiophene moieties within an NDI-copolymer backbone is shown to not only enable tuning of the electronic structure but also improve charge mobilities within the active layer of organic field-effect transistors. Electron mobilities and on/off ratios as high as 0.012 cm2 V−1 s-1 and Ion/Ioff > 105 were measured from n-channel thin-film transistors fabricated using NDI-xfTh copolymers. Bulk heterojunction solar cell devices were also fabricated from the NDI-xfTh copolymer series in blends with poly(3-hexylthiophene) (P3HT) with PNDI-4fTh-based devices yielding the largest Jsc (0.57 mA cm−2) and fill factor (55%) in addition to the highest measured PCE for this series (0.13%). © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4061–4069

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