Air-stable and high-mobility organic semiconductors based on heteroarenes for field-effect transistors

Abstract

Recent developments on heteroarene-based organic semiconductors applicable to high-performance, air-stable thin-film p-channel transistors are described. For the development of these new materials, including benzo[1,2-b:4,5-b'] dichalcogenophenes (BDXs), [1]benzochalcogenopheno- [3,2-b][1] benzochalcogenophenes (BXBXs), and dinaphtho[2,3-b:2',3'-f]- chalcogenopheno[3,2-b]chalcogenophenes (DNXXs), new efficient synthetic methods are established. These materials are then evaluated as active layers in organic field-effect transistors (OFETs) fabricated by vacuum or solution processes. In the present work, molecular factors (molecular structures, energy levels and shapes of highest occupied molecular orbitals, molecular arrangements in the thin film) and the device performances are correlated and discussed to understand a structure-properties relationship. As a consequence of this approach, several air-stable and high-performance semiconductors for the OTFTs are successfully developed. For example, vapor-processable DNTT and solution-processable alkylated-BTBTs showing field-effect mobility as high as 3.0 cm2 V-1 s-1 and with 2.8 cm2 V-1 s-1, respectively, are among the best for recently developed new materials. © 2011 The Japan Institute of Heterocyclic Chemistry.