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

• New semiconducting porphyrin derivatives were prepared.
• Their thin film and single-crystal based OFET devices show excellent performances.
• Single-crystal based OFET devices show better performance than thin film based ones.
• These high performances were verified by single crystal structure analysis.
• Unusually free based porphyrin single crystal OFET shows the best performance.

The design and synthesis of new solution processable semiconducting π-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 π–π interactions, new porphyrin derivatives showed high crystallinity in film state and displayed excellent electrical characteristics with high carrier mobilities of 0.15 cm2/Vs for ZnTPEP and 0.029 cm2/Vs for H2TPEP together with high on/off current ratios of >105 and >104, respectively. When the devices were fabricated with their single crystals, ZnTPEP displayed excellent characteristic with a high mobility of 0.2 cm2/Vs and H2TPEP showed 0.3 cm2/Vs with high on/off current ratios of >104 and >105, 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.

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