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Issue 51, 2016, Issue in Progress
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Thiophene-S,S-dioxidized indophenines as high performance n-type organic semiconductors for thin film transistors

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Abstract

The synthesis of three new isomerically pure (E,E,E)-form thiophene-S,S-dioxidized indophenine (IDTO) compounds, (3Z,3′Z)-3,3′-((E)-1,1,1′,1′-tetraoxido-5H,5′H-[2,2′-bithiophenylidene]-5,5′-diylidene)bis(1-dodecyl-indolin-2-one) (4a-S1), (3Z,3′Z)-3,3′-((E)-1,1,1′,1′-tetraoxido-5H,5′H-[2,2′-bithiophenylidene]-5,5′-diylidene)bis(5-bromo-1-dodecyl-indolin-2-one) (4b-S1) and (3Z,3′Z)-3,3′-((E)-1,1,1′,1′-tetraoxido-5H,5′H-[2,2′-bithiophenyldene]-5,5′-diylidene)bis(6-bromo-1-dodecyl-indolin-2-one) (4c-S1), and their use as n-channel semiconductors for organic thin film transistors (OTFTs) are reported. Compared to the non-oxidized parent indophenine compound 3,3′-(5H,5′H-[2,2′-bithiophenylidene]-5,5′-diylidene)bis(1-dodecylindolin-2-one) (3a), 4a-S1 exhibited significantly lower HOMO and LUMO energy levels. Having bromine atoms at the 5,5′- (4b-S1) or 6,6′-positions (4c-S1), the HOMO and LUMO energy levels further decreased. In OTFT devices, these IDTO compounds exhibit unipolar n-type semiconductor behavior due to their significantly deeper LUMO and HOMO energy levels than those of 3a that shows ambipolar charge transport performance. The maximum electron mobilities of 4a-S1, 4b-S1 and 4c-S1 are in the order of 10−2 to 10−1 cm2 V−1 s−1, which are much higher than that of 3a (∼10−3 cm2 V−1 s−1), originating from the lower LUMO energy levels and the high isomeric purities of the former compounds. Among the three IDTO compounds, 4c-S1 shows the highest electron mobility of up to 0.11 cm2 V−1 s−1, which is likely due to its most extended π-electron delocalization on the LUMO wavefunction.

Graphical abstract: Thiophene-S,S-dioxidized indophenines as high performance n-type organic semiconductors for thin film transistors

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Supplementary files

Article information


Submitted
09 Mar 2016
Accepted
27 Apr 2016
First published
28 Apr 2016

RSC Adv., 2016,6, 45410-45418
Article type
Paper
Author version available

Thiophene-S,S-dioxidized indophenines as high performance n-type organic semiconductors for thin film transistors

Y. Deng, B. Sun, J. Quinn, Y. He, J. Ellard, C. Guo and Y. Li, RSC Adv., 2016, 6, 45410
DOI: 10.1039/C6RA06316K

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