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Fused Heptacyclic-Based Acceptor–Donor–Acceptor Small Molecules: N-Substitution toward High-Performance Solution-Processable Field-Effect Transistors

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    Fused Heptacyclic-Based Acceptor–Donor–Acceptor Small Molecules: N-Substitution toward High-Performance Solution-Processable Field-Effect Transistors
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    • Guobing Zhang*
      Guobing Zhang
      National Engineering Laboratory of Special Display Technology, State Key Laboratory of Advanced Display Technology, Academy of Photo-Electronic Technology, Hefei University of Technology, Hefei 230009, P. R. China
      *E-mail: [email protected] (G.Z.).
      More by Guobing Zhang
      Orcidhttp://orcid.org/0000-0001-6053-2015
    • Yao Zhao
      Yao Zhao
      National Engineering Laboratory of Special Display Technology, State Key Laboratory of Advanced Display Technology, Academy of Photo-Electronic Technology, Hefei University of Technology, Hefei 230009, P. R. China
      More by Yao Zhao
    • Boseok Kang
      Boseok Kang
      Department of Nano Engineering and SKKU Advanced Institute of Nanotechnology (SAINT), Sungkyunkwan University (SKKU), Suwon 16419, Korea
      More by Boseok Kang
    • Sangsik Park
      Sangsik Park
      Department of Chemical Engineering, Pohang University of Science and Technology, Pohang 37673, Korea
      More by Sangsik Park
    • Jiufu Ruan
      Jiufu Ruan
      National Engineering Laboratory of Special Display Technology, State Key Laboratory of Advanced Display Technology, Academy of Photo-Electronic Technology, Hefei University of Technology, Hefei 230009, P. R. China
      More by Jiufu Ruan
    • Hongbo Lu
      Hongbo Lu
      National Engineering Laboratory of Special Display Technology, State Key Laboratory of Advanced Display Technology, Academy of Photo-Electronic Technology, Hefei University of Technology, Hefei 230009, P. R. China
      School of Chemistry and Chemical Engineering, Key Laboratory of Advance Functional Materials and Devices of Anhui Province, Hefei University of Technology, Hefei 23009, P. R. China
      More by Hongbo Lu
    • Longzhen Qiu*
      Longzhen Qiu
      National Engineering Laboratory of Special Display Technology, State Key Laboratory of Advanced Display Technology, Academy of Photo-Electronic Technology, Hefei University of Technology, Hefei 230009, P. R. China
      *E-mail: [email protected] (L.Q.).
      More by Longzhen Qiu
      Orcidhttp://orcid.org/0000-0002-8356-6303
    • Yunsheng Ding
      Yunsheng Ding
      School of Chemistry and Chemical Engineering, Key Laboratory of Advance Functional Materials and Devices of Anhui Province, Hefei University of Technology, Hefei 23009, P. R. China
      More by Yunsheng Ding
    • Kilwon Cho*
      Kilwon Cho
      Department of Chemical Engineering, Pohang University of Science and Technology, Pohang 37673, Korea
      *E-mail: [email protected] (K.C.).
      More by Kilwon Cho
      Orcidhttp://orcid.org/0000-0003-0321-3629
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    Chemistry of Materials

    Cite this: Chem. Mater. 2019, 31, 6, 2027–2035
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    https://doi.org/10.1021/acs.chemmater.8b05054
    Published February 28, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Although various donor–acceptor (D–A) small molecules with high power conversion efficiency have been reported, D–A small molecules with high field-effect mobility are still rare. In this work, two new A–D–A small molecules with a rigid indacenodithieno[3,2-b]thiophene (IDTT) moiety as the central core and both ends capped with strong electron-withdrawing indole-2,3-dione (IDD) and N-substituted pyrrolo[2,3-b]pyridine-2,3-dione (IDD-N) were synthesized and characterized for applications in solution-processable organic field-effect transistors (OFETs). A N atom was introduced to the IDD units to enhance the planarity and structural ordering by noncovalent interactions, leading to a dramatic effect on the small molecule. The unsubstituted small molecule (IDTT–IDD) did not show any field-effect performance, whereas an encouraging hole mobility of 7.7 cm2 V–1 s–1 with an average mobility of 6.1 cm2 V–1 s–1 was obtained for solution-processable OFETs based on the N-substituted one (IDTT–IDD-N). This work provided a simple and effective molecular strategy for the design of D–A small molecules for high-performance solution-processable OFETs.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.chemmater.8b05054.

    • Experimental Section (synthesis and devices) and characterization (TGA, DSC, device performances, NMR, and MALDI-TOF-MS) (PDF)

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    Chemistry of Materials

    Cite this: Chem. Mater. 2019, 31, 6, 2027–2035
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.chemmater.8b05054
    Published February 28, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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