Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors

5 years ago

Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors

Long-Huan Li, Pragya Priyanka, Chien-Lung Wang, Bo-Chun Yu, Yi-Yo Lai, Antonio Facchetti, Shao-Huan Hong, Deng-Yi Huang, Bo-Chin Chang, Cheng-Liang Liu, Kuan-Yi Wu, Sureshraju Vegiraju, Ming-Chou Chen, Wei-Chieh Chang, Wen-Jung Chang

New 3,3′-dithioalkyl-2,2′-bithiophene (SBT)-based small molecular and polymeric semiconductors are synthesized by end-capping or copolymerization with dithienothiophen-2-yl units. Single-crystal, molecular orbital computations, and optical/electrochemical data indicate that the SBT core is completely planar, likely via S(alkyl)⋯S(thiophene) intramolecular locks. Therefore, compared to semiconductors based on the conventional 3,3′-dialkyl-2,2′-bithiophene, the resulting SBT systems are planar (torsional angle <1°) and highly π-conjugated. Charge transport is investigated for solution-sheared films in field-effect transistors demonstrating that SBT can enable good semiconducting materials with hole mobilities ranging from ≈0.03 to 1.7 cm2 V−1 s−1. Transport difference within this family is rationalized by film morphology, as accessed by grazing incidence X-ray diffraction experiments. New 3,3′-dithioalkyl-2,2′-bithiophene (SBT) based small molecular and polymeric semiconductors are synthesized by end-capping or copolymerization with dithienothiophen-2-yl units. Charge transport is investigated for solution-sheared films in field-effect transistors demonstrating that SBT can enable good charge transport with hole mobilities ranging from ≈0.03 to 1.7 cm2 V−1 s−1.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adma.201702414