Versatile α,ω‐Disubstituted Tetrathienoacene Semiconductors for High Performance Organic Thin‐Film Transistors

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Abstract
Facile one‐pot [1 + 1 + 2] and [2 + 1 + 1] syntheses of thieno[3,2‐b]thieno[2′,3′:4,5]thieno[2,3‐d]thiophene (tetrathienoacene; TTA) semiconductors are described which enable the efficient realization of a new TTA‐based series for organic thin‐film transistors (OTFTs). For the perfluorophenyl end‐functionalized derivative DFP‐TTA, the molecular structure is determined by single‐crystal X‐ray diffraction. This material exhibits n‐channel transport with a mobility as high as 0.30 cm2V−1s−1 and a high on‐off ratio of 1.8 × 107. Thus, DFP‐TTA has one of the highest electron mobilities of any fused thiophene semiconductor yet discovered. For the phenyl‐substituted analogue, DP‐TTA, p‐channel transport is observed with a mobility as high as 0.21 cm2V−1s−1. For the 2‐benzothiazolyl (BS‐) containing derivative, DBS‐TTA, p‐channel transport is still exhibited with a hole mobility close to 2 × 10−3 cm2V−1s−1. Within this family, carrier mobility magnitudes are strongly dependent on the semiconductor growth conditions and the gate dielectric surface treatment.

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