Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors

Liu, Qian and Sun, Huabin and Blaikie, Chula and Caporale, Chiara and Manzhos, Sergei and Feron, Krishna and MacLeod, Jennifer M. and Massi, Massimiliano and Bottle, Steven E. and Bell, John and Noh, Yong-Young and Sonar, Prashant (2018) Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors. New Journal of Chemistry, 42 (15). pp. 12374-12385. ISSN 1144-0546

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Abstract

Here, we design and synthesize three new diketopyrrolopyrrole (DPP) derivatives with naphthalene, possessing large-scaled π-delocalized electronic structure, as the flanking groups and both linear (n-decyl and n-dodecyl) and branched (2-hexyldecyl)alkyl chains as substitutions as active layer for high performance organic field-effect transistors (OFETs). The thermal, photophysical properties, energy levels and solid state molecular stacking have been studied in detail. All the materials show excellent thermal stability with a decomposition temperature of 400 °C, high semi-crystallinity feature, suitable HOMO & LUMO energy levels, and varying crystalline domain sizes in thin films. Bottom-contact/top-gate transistor devices are thus fabricated to investigate the mobility. Encouragingly, all compounds function well in OFET devices and show significant potential as p-type semiconducting materials. The monomer with the n-decyl alkyl chain (D-DPPN) shows the highest mobility of 0.019 cm2 V-1 s-1, with the Ion/Ioff ratio reaching 106. We for the first time synthesize naphthalene flanked DPP monomers and achieve high mobility in OFET devices when using these monomers without any further functionalization as semiconductors directly. The primary result that high mobility is observed for monomers only opens a new way for further DPP application and provides more possibilities for constructing high performance polymeric and small molecular semiconductors based on this new DPP dye.


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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Accepted version deposited in accordance with the copyright policy of the publisher.
Faculty/School / Institute/Centre: No Faculty
Faculty/School / Institute/Centre: No Faculty
Date Deposited: 16 Sep 2020 04:16
Last Modified: 24 Sep 2020 06:13
Uncontrolled Keywords: organic field effect transistors; isoindigotin; semiconducting polymers
Fields of Research (2008): 03 Chemical Sciences > 0303 Macromolecular and Materials Chemistry > 030399 Macromolecular and Materials Chemistry not elsewhere classified
Identification Number or DOI: https://doi.org/10.1039/c8nj01453a
URI: http://eprints.usq.edu.au/id/eprint/39373

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