Naphthalimide end capped anthraquinone based solution-processable n-channel organic semiconductors: effect of alkyl chain engineering on charge transport

Do, Thu-Trang and Takeda, Yasunori and Manzhos, Sergei and Bell, John and Tokito, Shizuo and Sonar, Prashant (2018) Naphthalimide end capped anthraquinone based solution-processable n-channel organic semiconductors: effect of alkyl chain engineering on charge transport. Journal of Materials Chemistry C, 6 (14). pp. 3774-3786. ISSN 2050-7534


Abstract

Herein, we are reporting the synthesis, characterization and organic field effect transistor characteristics of a new class of 1,8-naphthalimide (NAI) and 9,10-anthraquinone (ANQ) strong electron withdrawing group based n-channel small molecule semiconductors with different branched alkyl chain length, namely NAI-ANQ-NAI (BO), NAI-ANQ-NAI (HD), and NAI-ANQ-NAI (DT). All three small molecules exhibit different solubility behavior based on their alkyl chain length in common organic solvents. NAI-ANQ-NAI (BO), NAI-ANQ-NAI (HD), and NAI-ANQ-NAI (DT) show quite deep LUMO energy levels (around -4.2 eV) which is promising for better air-stable electron transport. Under ambient atmosphere, we found that electron mobilities of solution-processed thin-film transistors based on these small molecules were enhanced when annealing temperature increased from 140 to 200 °C due to better thin film microstructures. At 200 °C, devices exhibited the best performances with the maximum electron mobilities of 2.79 × 10-2, 2.09 × 10-2 and 2.40 × 10-2 cm2 V-1 s-1 for NAI-ANQ-NAI (BO), NAI-ANQ-NAI (HD) and NAI-ANQ-NAI (DT), respectively. The spin-coated films of these materials exhibited quite smooth and uniform morphology although these are small molecules forming crystalline structures. These results clearly demonstrate that the fused anthraquinone and naphthalimide are potential functional moieties for constructing solution processable electron transporting materials for organic and printed electronics.


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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Files associated with this item cannot be displayed due to copyright restrictions.
Faculty/School / Institute/Centre: No Faculty
Faculty/School / Institute/Centre: No Faculty
Date Deposited: 28 Sep 2020 04:46
Last Modified: 30 Sep 2020 02:32
Uncontrolled Keywords: field-effect transistors; high-electron-mobility; thin-film transistors; quinoidal small molecules; high-performance; solar-cells; side-chain; nonfullerene acceptor; branching position; air
Fields of Research (2008): 09 Engineering > 0904 Chemical Engineering > 090499 Chemical Engineering not elsewhere classified
Fields of Research (2020): 40 ENGINEERING > 4004 Chemical engineering > 400499 Chemical engineering not elsewhere classified
Identification Number or DOI: https://doi.org/10.1039/c7tc05172g
URI: http://eprints.usq.edu.au/id/eprint/39363

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