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A twisted monomeric perylenediimide electron acceptor for efficient organic solar cells

构筑扭曲苝酰亚胺单分子型电荷受体材料用于高性能有机太阳能电池

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Abstract

Perylenediimide (PDI)-based materials exhibit great potential as non-fullerene acceptors in bulk-heterojunction (BHJ) organic solar cells (OSCs). Recent investigations have revealed that PDI molecules with a twisted structure could disrupt aggregation of perylene unit. Here, we present a PDI monomer via bay-substitutions with four fused naphthalene units by three-step reactions, named TN-PDI. The introduction of four fused naphthalene rings into the bay positions of PDI unit leads to a strong steric hindrance with a twist angle of 33° between the two PDI subplanes. Blended with a wide-band gap polymer donor (PDBT-T1), the TN-PDI based non-fullerene solar cells show power conversion efficiency (PCE) of 3.0%. Our results indicate that the bay-substitutions with fused aromatic substitutions could be an efficient approach to develop monomeric PDI acceptors.

摘要

近年来, 本体异质结型有机太阳能电池领域中, 苝酰亚胺类衍生物作为富勒烯类电荷受体材料的最佳替代材料而得到广泛关注. 很 多研究表明扭曲构型的分子结构设计可以明显地抑制苝酰亚胺的聚集行为. 本研究在苝酰亚胺的四个湾位同时共轭引入萘基官能团, 从 而合成一种简单结构的苝酰亚胺单分子型电荷受体材料TN-PDI. 四个共轭萘基的引入使苝酰亚胺平面骨架扭曲至33°. 分别以TN-PDI和一 种宽带隙聚合物PDBT-T1为电荷受体材料和给体材料构筑本体异质结型有机太阳能电池, 其光电转换效率可达3.0%. 研究结果表明, 四个 湾位同时共轭取代苝酰亚胺是一种制备简单高效苝酰亚胺单分子型电荷受体材料的有效方法.

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Author information

Authors and Affiliations

  1. Heeger Beijing Research and Development Center, School of Chemistry and Environment, Beihang University, Beijing, 100191, China

    Yunhao Cai  (蔡芸皓), Xieyou Guo  (郭谢友), Xiaobo Sun  (孙晓波), Lijun Huo  (霍利军) & Yanming Sun  (孙艳明)

  2. The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, 450001, China

    Donghui Wei  (魏东辉) & Mingming Yu  (于明明)

Authors
  1. Yunhao Cai  (蔡芸皓)
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  2. Xieyou Guo  (郭谢友)
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  3. Xiaobo Sun  (孙晓波)
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  4. Donghui Wei  (魏东辉)
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  5. Mingming Yu  (于明明)
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  6. Lijun Huo  (霍利军)
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  7. Yanming Sun  (孙艳明)
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Corresponding authors

Correspondence to Xiaobo Sun  (孙晓波), Lijun Huo  (霍利军) or Yanming Sun  (孙艳明).

Additional information

Acknowledgments This work was supported by the National Natural Science Foundation of China (51473009 and 51273203), and the Fundamental Research Funds for the Central Universities (YWF-14-HHXY-007 and YWF-14-HXXY-014).

Author contributions Cai Y performed the experiments for organic solar cells andwrote the draft. Guo X synthesized the organic compounds. Sun X conceived the experiments, analyzed the results and wrote the paper. Wei D and Yu M provided theoretical simulation. Huo L analyzed the results. All authors contributed to the general discussion and revised manuscript.

Conflict of interest The authors declare that they have no conflict of interest.

Supplementary information Supplementary data: the TGA thermogram, the calculation for the Dihedral angles of the optimized geometry of TN-PDI, the absorption features of donor-acceptor blends, the SCLC measurement for the electronmobility of TN-PDI and themobility of optimized device are available in the online version of this paper.

Xiaobo Sun received his BSc and MSc degrees in materials science from Jilin University, and PhD degree in chemistry fromthe Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences (ICCAS). Then, he joined Prof. Robert C. Haddon’s group in the University of California at Riverside as a postdoctoral researcher (2006–2011). In 2012, he joined the School of Chemistry and Environment at Beihang University (Beijing, China) as an associate professor. His current research interests include organic photovoltaic materials and devices, and graphite based nanocomposites for electronic packaging.

Yanming Sun is currently a professor at Beihang University. He received his BSc degree in chemistry from Shandong University and PhD degree in chemistry from the Key Laboratory of Organic Solids, ICCAS. In 2007, he became a research assistant at the University of Manchester, UK. Then, he joined Prof. Alan J Heeger's group in the University of California at Santa Barbara as a postdoctoral researcher (Jan. 2009–Aug. 2013). In 2013, he was awarded with the “Youth 1000 Talent Plan” and then joined in Beihang University. He has publishedmore than 60 papers, including Nat. Mater., Nat. Commun., J. Am. Chem. Soc., Adv. Mater., Nano Lett., etc. His current research is focused on organic and polymer solar cells.

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Cai, Y., Guo, X., Sun, X. et al. A twisted monomeric perylenediimide electron acceptor for efficient organic solar cells. Sci. China Mater. 59, 427–434 (2016). https://doi.org/10.1007/s40843-016-5063-3

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