Development of π-Conjugated Systems Bearing Annelated-Structure with Electronegative Substituents and Their Application to n-Type Organic Field-Effect Transistor

  • Ie Yutaka
    The Institute of Scientific and Industrial Research, Osaka University, JST-PREST

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  • 電子求引性基の架橋構造を持つπ電子系の開発とn型有機電界効果トランジスタへの応用
  • デンシキュウインセイキ ノ カケハシ コウゾウ オ モツ pデンシケイ ノ カイハツ ト nガタ ユウキ デンカイ コウカ トランジスタ エ ノ オウヨウ
  • Development of π-Conjugated Systems Bearing Annelated-Structure with Electronegative Substituents and Their Application to n-Type Organic Field-Effect Transistor

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Abstract

Development of organic semiconducting materials based on π-conjugated systems for use in organic field-effect transistors (OFETs) has become an active area of research. We have designed and synthesized a series of electronegative units: Carbonyl-bridged bithiazole, dialkyl-substituted naphtho[2,3-c]thiophene-4,9-dione, alkyl-substituted dioxocyclopenta[b]thiophene, and dicyanomethylene-substituted cyclopenta[b]thiophene. The electronegative π-conjugated systems containing these units have been synthesized as potential active materials for air-stable and/or solution-processable n-type OFETs. Electrochemical measurements revealed that the annelation of the electron-withdrawing group contributes both to lowering the lowest unoccupied molecular orbital energy level and to stabilizing the formation of anionic species. Some of compounds are sufficiently soluble to realize the fabrication of their thin films through a solution technique. These electronegative compounds exhibited n-type semiconducting behavior not only in vacuum but also under air-exposed conditions.

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