Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer

Itaru Osaka, Masafumi Shimawaki, Hiroki Mori, Iori Doi, Eigo Miyazaki, Tomoyuki Koganezawa, Kazuo Takimiya

Research output: Contribution to journalArticle

245 Citations (Scopus)

Abstract

We report the synthesis and characterization of a novel donor-acceptor semiconducting polymer bearing naphthobisthiadiazole (NTz), a doubly benzothiadiazole (BTz)-fused ring, and its applications to organic field-effect transistors and bulk heterojunction solar cells. With NTz's highly π-extended structure and strong electron affinity, the NTz-based polymer (PNTz4T) affords a smaller bandgap and a deeper HOMO level than the BTz-based polymer (PBTz4T). PNTz4T exhibits not only high field-effect mobilities of ∼0.56 cm 2/(V s) but also high photovoltaic properties with power conversion efficiencies of ∼6.3%, both of which are significantly high compared to those for PBTz4T. This is most likely due to the more suitable electronic properties and, importantly, the more highly ordered structure of PNTz4T in the thin film than that of PBTz4T, which might originate in the different symmetry between the cores. NTz, with centrosymmetry, can lead to a more linear backbone in the present polymer system than BTz with axisymmetry, which might be favorable for better molecular ordering. These results demonstrate great promise for using NTz as a bulding unit for high-performance semiconducting polymers for both transistors and solar cells.

Original languageEnglish
Pages (from-to)3498-3507
Number of pages10
JournalJournal of the American Chemical Society
Volume134
Issue number7
DOIs
Publication statusPublished - Feb 22 2012
Externally publishedYes

ASJC Scopus subject areas

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

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