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Non-fullerene Acceptors with a Thieno[3,4-c]pyrrole-4,6-dione (TPD) Core for Efficient Organic Solar Cells

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Abstract

To achieve the red-shifted absorptions and appropriate energy levels of A-D-A type non-fullerene acceptors (NFAs), in this work, we design and synthesize two new NFAs, named TPDCIC and TPDCNC, whose electron-donating (D) unit is constructed by a thieno[3,4-c]pyrrole-4,6-dione (TPD) core attached to two cyclopentadithiophene (CPDT) moieties at both sides, and the electron-accepting (A) end-groups are 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (IC) and 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b] naphthalen-1-ylidene)malononitrile (NC), respectively. Benefiting from TPD core, which easily forms quinoid structure and O⋯H or O⋯S intramolecular noncovalent interactions, TPDCIC and TPDCNC show more delocalization of π-electrons and perfect planar molecular geometries, giving the absorption ranges extended to 822 and 852 nm, respectively. Furthermore, the highest occupied molecular orbital (HOMO) levels of TPDCIC and TPDCNC remain relatively low-lying due to the electronegativity of the carbonyl groups on TPD core. Considering that the absorptions and energy levels of the two NFAs match well with those of a widely used polymer donor, PBDB-T, we fabricate two kinds of organic solar cells (OSCs) based on the PBDB-T:TPDCIC and PBDB-T:TPDCNC blended films, respectively. Through a series of optimizations, the TPDCIC-based devices yield an impressing power conversion efficiency (PCE) of 10.12% with a large short-circuit current density (JSC) of 18.16 mA·cm−2, and the TPDCNC-based ones exhibit a comparable PCE of 9.80% with a JSC of 17.40 mA·cm−2. Our work is the first report of the TPD-core-based A-D-A type NFAs, providing a good reference for the molecular design of high-performance NFAs.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Nos. 21875216, 21734008) and Zhejiang Province Science and Technology Plan (No. 2018C01047). X. Lu and T. K. Lau acknowledge the financial support from Research Grant Council of Hong Kong (General Research Fund No. 14314216, CUHK Direct Grant No. 4053227).

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Authors and Affiliations

  1. Key Laboratory of Macromolecular Synthesis and Functionalization (Ministry of Education), State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China

    Shi-Zhe Geng, Wei-Tao Yang, Jian Gao, Shui-Xing Li, Min-Min Shi, Chang-Zhi Li & Hong-Zheng Chen

  2. Department of Physics, The Chinese University of Hong Kong, New Territories, Hong Kong, China

    Tsz-Ki Lau & Xin-Hui Lu

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  1. Shi-Zhe Geng
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  2. Wei-Tao Yang
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  4. Shui-Xing Li
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Correspondence to Min-Min Shi or Hong-Zheng Chen.

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Invited article for special issue of “The 100th Anniversary of the Birth of Prof. Shi-Lin Yang”

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Geng, SZ., Yang, WT., Gao, J. et al. Non-fullerene Acceptors with a Thieno[3,4-c]pyrrole-4,6-dione (TPD) Core for Efficient Organic Solar Cells. Chin J Polym Sci 37, 1005–1014 (2019). https://doi.org/10.1007/s10118-019-2309-x

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