Conjugated 1,8-Naphthalimide Based Solution Processable n-Type Semiconductors for Organic Electronics

Thu Trang Do^a, Hong Duc Pham^a, Yasunori Takeda^b, Sergei Manzhos^c, John Bell^a, Shinzo Tokito^b, Prashant Sonar^a^,^d

^aSchool of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), Australia, George Street, 2, Brisbane City, Australia

^bResearch Center for Organic Electronics, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata, 992-8510, Japan.

^cDepartment of Mechanical Engineering, Faculty of Engineering, National University of Singapore, Block EA #07-08, 9 Engineering Drive 1, Singapore 117576

^dInstitute of Future Environment, GPO Box 2434, Brisbane QLD 4001

Asia-Pacific International Conference on Perovskite, Organic Photovoltaics and Optoelectronics
Proceedings of International Conference Asia-Pacific Hybrid and Organic Photovoltaics 2018 (AP-HOPV18)

Kitakyūshū-shi, Japan, 2018 January 28th - 30th

Organizers: Shuzi Hayase, Juan Bisquert and Hiroshi Segawa

Oral, Thu Trang Do, presentation 053
DOI: https://doi.org/10.29363/nanoge.ap-hopv.2018.053
Publication date: 27th October 2017

Organic semiconductors have received great attention for application in field-effect transistors (OFETs), light-emitting diodes, and solar cells (OSCs). Particularly, solution processing is one of the most attractive features of organic semiconductors due to the advantages such as low cost and large-area device fabrication. In practice, the n-type semiconducting materials are as important as the p-type for high-performance OSCs and OFETs. However the development of n-type semiconductors has lagged far behind that of p-type materials. The imbalanced improvement of organic semiconductors limits the broad applications of organic electronics; therefore there is a growing trend in developing n-type semiconducting materials in OSCs and OFETs fields.

Herein, a series of novel electron deficient small molecular n-type based on 1,8-naphthalimide (NAI) and 9-fluorenone (FN) or 9,10-anthraquinone (ANQ) with different branched alkyl chains are synthesized and characterized. These molecules are based on an acceptor–donor–acceptor–donor–acceptor (A1–D–A2–D–A1) molecular design configuration with NAI as the end-capping acceptor (A1), FN or ANQ as electron-withdrawing central (A2) group, and thiophene ring as a donor (D) unit. These materials are named as NAI-FN-NAI (BO), NAI-FN-NAI (HD), NAI-ANQ-NAI (BO), NAI-ANQ-NAI (HD) and NAI-ANQ-NAI (HD) where BO, HD and DT represent butyloctyl, hexyldecyl and decyltetradecyl alkyl groups, respectively. To further modify energy levels, we converted the weak electron withdrawing ketonic group attached to the FN moiety of NAI-FN-NAI (BO) to a stronger electron withdrawing cyano group to obtain the compound NAI-FCN-NAI (BO). The materials exhibited higher to medium band gaps, low LUMO energy levels, and highly thermally stable properties. The first group materials including NAI-FN-NAI (BO), NAI-FN-NAI (HD), and NAI-FCN-NAI (BO) were utilised as electron acceptor for OSCs; and OSC devices based on NAI-FN-NAI (BO) as an acceptor exhibited the highest performance with V_OC of 0.88 V, J_SC of 9.1 mAcm^–2, FF of 45%, and PCE of 3.6%. This is the first report of 9-fluorenone based nonfullerene acceptor with poly(3-hexylthiophene) donor in the devices with such a promising performance. The second group materials of NAI-ANQ-NAI (BO), NAI-ANQ-NAI (HD) and NAI-ANQ-NAI (HD) were applied for n-type OFETs to investigate the effect of alkyl chain length on device performances. NAI-ANQ-NAI (BO) based device showed the best results with the highest electron mobility of 0.042 cm²V^-1s^-1.

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