Asymmetric dithieno[3,2-b:2',3'-d]thiophene derivatives as solution-processable small molecular organic semiconductors for organic thin film transistors

In this paper, solution-processable asymmetric dithieno[3,2-d:2',3'-d]thiophene (DTT) compounds, 2-octyldithieno[3,2-b:2',3'-d]thiophene (1), 2-octyl-6-(thiophen-2-yl)dithieno[3,2-b:2',3'-d]thiophene (2), 2-octyl-6-(5octylthiophen-2-yl)dithieno[3,2-b:2',3 & PRIME;-d]thiophene (3), and 2-(5-(2-ethylhexyl)thiophen-2-yl)-6-octyldithieno [3,2-b:2',3'-d]thiophene (4) were synthesized and employed as small molecular organic semiconductors for topcontact/bottom-gate organic thin-film transistors. Physicochemical properties of four compounds including decomposition temperature, melting temperature, maximum absorption wavelength, highest occupied molecular orbital / lowest occupied molecular orbital energy level, and band gap were investigated. All DTT compounds exhibited p-channel activity, and especially compound 2 with additional thiophene group and linear alkyl chain (octyl group) showed superior electrical performance with hole mobility up to 0.07 cm(2)/Vs and current on/off ratio > 108 in ambient environment. Moreover, film microstructure and morphology showed correlation with the corresponding electrical performance, where high film texture and terrace-like morphology afforded high device performance.

Automated summary

In this study, solution-processable asymmetric DTT compounds were synthesized and used as small molecular organic semiconductors for organic thin-film transistors. All DTT compounds showed p-channel activity, with compound 2 exhibiting superior electrical performance. The performance of the compounds was correlated with film microstructure and morphology.