Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n-Type Thin-Film Transistors

Macromol Rapid Commun. 2019 Dec;40(23):e1900394. doi: 10.1002/marc.201900394. Epub 2019 Nov 8.

Abstract

Diketopyrrolopyrrole (DPP)-based copolymers have received considerable attention as promising semiconducting materials for high-performance organic thin-film transistors (OTFTs). However, these polymers typically exhibit p-type or ambipolar charge-transporting characteristics in OTFTs due to their high-lying highest occupied molecular orbital (HOMO) energy levels. In this work, a new series of DPP-based n-type polymers have been developed by incorporating fused bithiophene imide oligomers (BTIn) into DPP polymers. The resulting copolymers BTIn-DPP show narrow band gaps as low as 1.27 eV and gradually down-shifted frontier molecular orbital energy levels upon the increment of imide group number. Benefiting from the coplanar backbone conformation, well-delocalized π-system, and favorable polymer chain packing, the optimal polymer in the series shows promising n-type charge transport with an electron mobility up to 0.48 cm2 V-1 s-1 in OTFTs, which is among the highest values for the DPP-based n-type polymers reported to date. The results demonstrate that incorporating fused bithiophene imide oligomers into polymers can serve as a promising strategy for constructing high-performance n-type polymeric semiconductors.

Keywords: bithiophene imide; diketopyrrolopyrrole; n-type polymer semiconductors; organic thin-film transistors.

MeSH terms

  • Density Functional Theory
  • Imides / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Pyrroles / chemistry*
  • Semiconductors
  • Thiophenes / chemistry*
  • Transistors, Electronic

Substances

  • Imides
  • Ketones
  • Polymers
  • Pyrroles
  • Thiophenes
  • diketopyrrolopyrrole dye