Combining electron-neutral building blocks with intramolecular "conformational locks" affords stable, high-mobility P- and N-channel polymer semiconductors

Hui Huang, Zhihua Chen, Rocio Ponce Ortiz, Christopher Newman, Hakan Usta, Sylvia Lou, Jangdae Youn, Yong Young Noh, Kang Jun Baeg, Lin X. Chen, Antonio Facchetti, Tobin Marks

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144 Citations (Scopus)

Abstract

Understanding the relationship between molecular/macromolecular architecture and organic thin film transistor (TFT) performance is essential for realizing next-generation high-performance organic electronics. In this regard, planar π-conjugated, electron-neutral (i.e., neither highly electron-rich nor highly electron-deficient) building blocks represent a major goal for polymeric semiconductors, however their realization presents synthetic challenges. Here we report that an easily accessible (minimal synthetic steps), electron-neutral thienyl-vinylene (TVT)-based building block having weak intramolecular S•••O "conformational locks" affords a new class of stable, structurally planar, solution-processable, high-mobility, molecular, and macromolecular semiconductors. The attraction of merging the weak TVT electron richness with supramolecular planarization is evident in the DFT-computed electronic structures, favorable MO energetics, X-ray diffraction-derived molecular structures, experimental lattice coehesion metrics, and excellent TFT performance. TVT-based polymer TFTs exhibit stable carrier mobilities in air as high as 0.5 and 0.05 cm2/V•s (n- and p-type, respectively). All-TVT polymer-based complementary inverter circuitry exhibiting high voltage gains (∼50) and ring oscillator circuitry with high fosc(∼1.25 kHz) is readily fabricated from these materials by simple inkjet printing.

Original languageEnglish
Pages (from-to)10966-10973
Number of pages8
JournalJournal of the American Chemical Society
Volume134
Issue number26
DOIs
Publication statusPublished - Jul 4 2012

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Huang, H., Chen, Z., Ortiz, R. P., Newman, C., Usta, H., Lou, S., Youn, J., Noh, Y. Y., Baeg, K. J., Chen, L. X., Facchetti, A., & Marks, T. (2012). Combining electron-neutral building blocks with intramolecular "conformational locks" affords stable, high-mobility P- and N-channel polymer semiconductors. Journal of the American Chemical Society, 134(26), 10966-10973. https://doi.org/10.1021/ja303401s