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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

159 Scopus citations

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 (US)
Pages (from-to)10966-10973
Number of pages8
JournalJournal of the American Chemical Society
Volume134
Issue number26
DOIs
StatePublished - Jul 4 2012

ASJC Scopus subject areas

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

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