Preparation of new semiconducting tetraphenylethynyl porphyrin derivatives and their high-performing organic field-effect transistors

Abstract

The design and synthesis of new solution processable semiconducting pi-extended porphyrin derivatives H2TPEP and ZnTPEP were introduced and their use in the fabrication of high-performing thin film and single-crystal OFET devices were described. Due to strong pi-pi interactions, new porphyrin derivatives showed high crystallinity in film state and displayed excellent electrical characteristics with high carrier mobilities of 0.15 cm(2)/Vs for ZnTPEP and 0.029 cm(2)/Vs for H2TPEP together with high on/off current ratios of >10(5) and >10(4), respectively. When the devices were fabricated with their single crystals, ZnTPEP displayed excellent characteristic with a high. mobility of 0.2 cm(2)/Vs and H2TPEP showed 0.3 cm(2)/Vs with high on/off current ratios of >10(4) and >10(5), respectively. Remarkably, although Zn(II)-porphyrin based single-crystal device usually shows much higher mobility than the device made of free-based porphyrin single-crystal, the mobility of H2TPEP single-crystal device was significantly higher than that of the ZnTPEP one, because of effective crystalline packing with short layer distances found in the single crystal prepared from H2TPEP. (C) 2016 Elsevier B.V. All rights reserved.