Skip to main content
Log in

Realizing compact three-dimensional charge transport networks of asymmetric electron acceptors for efficient organic solar cells

  • Articles
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Asymmetry has been demonstrated an effective approach in recent years to tune the structural and energetic orders of non-fullerene electron acceptors (NFAs) to prepare efficient organic solar cells (OSCs). In this article, five asymmetric NFAs, namely C9BTP-BO-ThCl-2F, C9BTP-BO-Cl-2F, C9BTP-BO-2Cl-2F, C7BTP-BO-2Cl-2F and C5BTP-BO-2Cl-2F possessing varied asymmetric end-groups and alkyl chains are synthesized to tune the charge transport networks formed within these NFAs. We found that the enhanced planarity in the asymmetric NFA can facilitate closer π-π stacking distance in either the A-to-A or A-to-D type NFA dimers, whilst the larger dipole moment can promote the formation of three-dimensional (3D) charge transport networks among NFAs. Taking those advantages, C7BTP-BO-2Cl-2F exhibit a compact 3D honeycomb network with a high packing coefficient of 72.1% and molecular packing density of 0.48 g/cm3, contributing to a superior power conversion efficiency of 18.0% when employing PM6 as the donor, with an open-circuit voltage of 0.85 V, short-circuit current of 26.7 mA cm−2 and fill factor of 79.3%. Our work provides guidelines in engineering the end group and side chains of asymmetric NFAs to achieve compact charge transport networks for high efficiency OSCs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Zheng Z, Wang J, Bi P, Ren J, Wang Y, Yang Y, Liu X, Zhang S, Hou J. Joule, 2022, 6: 171–184

    Article  CAS  Google Scholar 

  2. Zhu L, Zhang M, Xu J, Li C, Yan J, Zhou G, Zhong W, Hao T, Song J, Xue X, Zhou Z, Zeng R, Zhu H, Chen CC, MacKenzie RCI, Zou Y, Nelson J, Zhang Y, Sun Y, Liu F. Nat Mater, 2022, 21: 656–663

    Article  CAS  Google Scholar 

  3. Cui Y, Yao H, Zhang J, Zhang T, Wang Y, Hong L, Xian K, Xu B, Zhang S, Peng J, Wei Z, Gao F, Hou J. Nat Commun, 2019, 10: 2515

    Article  Google Scholar 

  4. Wei Q, Liu W, Leclerc M, Yuan J, Chen H, Zou Y. Sci China Chem, 2020, 63: 1352–1366

    Article  CAS  Google Scholar 

  5. Cui Y, Yao H, Zhang J, Xian K, Zhang T, Hong L, Wang Y, Xu Y, Ma K, An C, He C, Wei Z, Gao F, Hou J. Adv Mater, 2020, 32: 1908205

    Article  CAS  Google Scholar 

  6. Yu H, Qi Z, Zhang J, Wang Z, Sun R, Chang Y, Sun H, Zhou W, Min J, Ade H, Yan H. J Mater Chem A, 2020, 8: 23756–23765

    Article  CAS  Google Scholar 

  7. Li W, Chen M, Cai J, Spooner ELK, Zhang H, Gurney RS, Liu D, Xiao Z, Lidzey DG, Ding L, Wang T. Joule, 2019, 3: 819–833

    Article  CAS  Google Scholar 

  8. Huang J, Wang H, Yan K, Zhang X, Chen H, Li CZ, Yu J. Adv Mater, 2017, 29: 1606729

    Article  Google Scholar 

  9. Ma W, Yang C, Gong X, Lee K, Heeger AJ. Adv Funct Mater, 2005, 15: 1617–1622

    Article  CAS  Google Scholar 

  10. Li D, Zhang X, Liu D, Wang T. J Mater Chem A, 2020, 8: 15607–15619

    Article  CAS  Google Scholar 

  11. Zhan L, Li S, Li Y, Sun R, Min J, Bi Z, Ma W, Chen Z, Zhou G, Zhu H, Shi M, Zuo L, Chen H. Joule, 2022, 6: 662–675

    Article  CAS  Google Scholar 

  12. Cai Y, Li Y, Wang R, Wu H, Chen Z, Zhang J, Ma Z, Hao X, Zhao Y, Zhang C, Huang F, Sun Y. Adv Mater, 2021, 33: 2101733

    Article  CAS  Google Scholar 

  13. Wang L, Guo C, Zhang X, Cheng S, Li D, Cai J, Chen C, Fu Y, Zhou J, Qin H, Liu D, Wang T. Chem Mater, 2021, 33: 8854–8862

    Article  CAS  Google Scholar 

  14. He C, Bi Z, Chen Z, Guo J, Xia X, Lu X, Min J, Zhu H, Ma W, Zuo L, Chen H. Adv Funct Mater, 2022, 32: 2112511

    Article  CAS  Google Scholar 

  15. Zhang X, Li C, Xu J, Wang R, Song J, Zhang H, Li Y, Jing YN, Li S, Wu G, Zhou J, Li X, Zhang Y, Li X, Zhang J, Zhang C, Zhou H, Sun Y, Zhang Y. Joule, 2022, 6: 444–457

    Article  CAS  Google Scholar 

  16. Li C, Zhou J, Song J, Xu J, Zhang H, Zhang X, Guo J, Zhu L, Wei D, Han G, Min J, Zhang Y, Xie Z, Yi Y, Yan H, Gao F, Liu F, Sun Y. Nat Energy, 2021, 6: 605–613

    Article  CAS  Google Scholar 

  17. Li S, Zhan L, Yao N, Xia X, Chen Z, Yang W, He C, Zuo L, Shi M, Zhu H, Lu X, Zhang F, Chen H. Nat Commun, 2021, 12: 4627

    Article  CAS  Google Scholar 

  18. Zhang J, Bai F, Angunawela I, Xu X, Luo S, Li C, Chai G, Yu H, Chen Y, Hu H, Ma Z, Ade H, Yan H. Adv Energy Mater, 2021, 11: 2102596

    Article  CAS  Google Scholar 

  19. Yuan J, Zhang Y, Zhou L, Zhang G, Yip HL, Lau TK, Lu X, Zhu C, Peng H, Johnson PA, Leclerc M, Cao Y, Ulanski J, Li Y, Zou Y. Joule, 2019, 3: 1140–1151

    Article  CAS  Google Scholar 

  20. Yuan J, Zhang H, Zhang R, Wang Y, Hou J, Leclerc M, Zhan X, Huang F, Gao F, Zou Y, Li Y. Chem, 2020, 6: 2147–2161

    Article  CAS  Google Scholar 

  21. Li S, Li CZ, Shi M, Chen H. ACS Energy Lett, 2020, 5: 1554–1567

    Article  CAS  Google Scholar 

  22. Zhao J, Yao C, Ali MU, Miao J, Meng H. Mater Chem Front, 2020, 4: 3487–3504

    Article  CAS  Google Scholar 

  23. Cai J, Zhang X, Guo C, Zhuang Y, Wang L, Li D, Liu D, Wang T. Adv Funct Mater, 2021, 31: 2102189

    Article  CAS  Google Scholar 

  24. Chen Y, Bai F, Peng Z, Zhu L, Zhang J, Zou X, Qin Y, Kim HK, Yuan J, Ma L-, Zhang J, Yu H, Chow PCY, Huang F, Zou Y, Ade H, Liu F, Yan H. Adv Energy Mater, 2021, 11: 2003141

    Article  CAS  Google Scholar 

  25. Ge J, Hong L, Ma H, Ye Q, Chen Y, Xie L, Song W, Li D, Chen Z, Yu K, Zhang J, Wei Z, Huang F, Ge Z. Adv Mater, 2022, 34: 2202752

    Article  CAS  Google Scholar 

  26. Li S, Zhan L, Jin Y, Zhou G, Lau TK, Qin R, Shi M, Li CZ, Zhu H, Lu X, Zhang F, Chen H. Adv Mater, 2020, 32: 2001160

    Article  CAS  Google Scholar 

  27. Liu T, Zhang Y, Shao Y, Ma R, Luo Z, Xiao Y, Yang T, Lu X, Yuan Z, Yan H, Chen Y, Li Y. Adv Funct Mater, 2020, 30: 2000456

    Article  CAS  Google Scholar 

  28. Lu H, Jin H, Huang H, Liu W, Tang Z, Zhang J, Bo Z. Adv Funct Mater, 2021, 31: 2103445

    Article  CAS  Google Scholar 

  29. Luo Z, Liu T, Yan H, Zou Y, Yang C. Adv Funct Mater, 2020, 30: 2004477

    Article  CAS  Google Scholar 

  30. Luo Z, Ma R, Liu T, Yu J, Xiao Y, Sun R, Xie G, Yuan J, Chen Y, Chen K, Chai G, Sun H, Min J, Zhang J, Zou Y, Yang C, Lu X, Gao F, Yan H. Joule, 2020, 4: 1236–1247

    Article  CAS  Google Scholar 

  31. Sun R, Wu Y, Yang X, Gao Y, Chen Z, Li K, Qiao J, Wang T, Guo J, Liu C, Hao X, Zhu H, Min J. Adv Mater, 2022, 34: 2110147

    Article  CAS  Google Scholar 

  32. Wang J, Zhang M, Lin J, Zheng Z, Zhu L, Bi P, Liang H, Guo X, Wu J, Wang Y, Yu L, Li J, Lv J, Liu X, Liu F, Hou J, Li Y. Energy Environ, Sci, 2022, 15: 1585–1593

    Article  CAS  Google Scholar 

  33. Cai J, Guo C, Wang L, Fu Y, Chen C, Li D, Liu D, Wang T. Org Electron, 2022, 100: 106357

    Article  CAS  Google Scholar 

  34. Zhan L, Li S, Li Y, Sun R, Min J, Chen Y, Fang J, Ma C-, Zhou G, Zhu H, Zuo L, Qiu H, Yin S, Chen H. Adv Energy Mater, 2022, 12: 2201076

    Article  CAS  Google Scholar 

  35. He C, Chen Z, Wang T, Shen Z, Li Y, Zhou J, Yu J, Fang H, Li Y, Li S, Lu X, Ma W, Gao F, Xie Z, Coropceanu V, Zhu H, Bredas JL, Zuo L, Chen H. Nat Commun, 2022, 13: 2598

    Article  CAS  Google Scholar 

  36. Gao W, Fu H, Li Y, Lin F, Sun R, Wu Z, Wu X, Zhong C, Min J, Luo J, Woo HY, Zhu Z, Jen AK-. Adv Energy Mater, 2021, 11: 2003177

    Article  CAS  Google Scholar 

  37. Chen Y, Ma R, Liu T, Xiao Y, Kim HK, Zhang J, Ma C, Sun H, Bai F, Guo X, Wong KS, Lu X, Yan H. Adv Energy Mater, 2021, 11: 2003777

    Article  CAS  Google Scholar 

  38. Chen H, Lai H, Chen Z, Zhu Y, Wang H, Han L, Zhang Y, He F. Angew Chem Int Ed, 2021, 60: 3238–3246

    Article  CAS  Google Scholar 

  39. Li D, Sun C, Yan T, Yuan J, Zou Y. ACS Cent Sci, 2021, 7: 1787–1797

    Article  CAS  Google Scholar 

  40. Lai H, He F. Adv Energy Mater, 2020, 10: 2002678

    Article  CAS  Google Scholar 

  41. Wang C, Dong H, Jiang L, Hu W. Chem Soc Rev, 2018, 47: 422–500

    Article  CAS  Google Scholar 

  42. Kini GP, Jeon SJ, Moon DK. Adv Mater, 2020, 32: 1906175

    Article  CAS  Google Scholar 

  43. Chen M, Liu D, Li W, Gurney RS, Li D, Cai J, Spooner ELK, Kilbride RC, McGettrick JD, Watson TM, Li Z, Jones RAL, Lidzey DG, Wang T. ACS Appl Mater Interfaces, 2019, 11: 26194–26203

    Article  CAS  Google Scholar 

  44. Zhang X, Wang H, Li D, Chen M, Mao Y, Du B, Zhuang Y, Tan W, Huang W, Zhao Y, Liu D, Wang T. Macromolecules, 2020, 53: 3747–3755

    Article  CAS  Google Scholar 

  45. Bao F, Xiong Y, Peng R, Zhang C. Cryst Growth Des, 2022, 22: 3252–3263

    Article  CAS  Google Scholar 

  46. Zhan L, Li S, Lau TK, Cui Y, Lu X, Shi M, Li CZ, Li H, Hou J, Chen H. Energy Environ Sci, 2020, 13: 635–645

    Article  CAS  Google Scholar 

  47. Li W, Xiao Z, Cai J, Smith JA, Spooner ELK, Kilbride RC, Game OS, Meng X, Li D, Zhang H, Chen M, Gurney RS, Liu D, Jones RAL, Lidzey DG, Ding L, Wang T. Nano Energy, 2019, 61: 318–326

    Article  CAS  Google Scholar 

  48. Li W, Cai J, Yan Y, Cai F, Li S, Gurney RS, Liu D, McGettrick JD, Watson TM, Li Z, Pearson AJ, Lidzey DG, Hou J, Wang T. Sol RRL, 2018, 2: 1800114

    Article  Google Scholar 

  49. Li D, Chen X, Cai J, Li W, Chen M, Mao Y, Du B, Smith JA, Kilbride RC, O’Kane ME, Zhang X, Zhuang Y, Wang P, Wang H, Liu D, Jones RAL, Lidzey DG, Wang T. Sci China Chem, 2020, 63: 1461–1468

    Article  CAS  Google Scholar 

  50. Cowan SR, Roy A, Heeger AJ. Phys Rev B, 2010, 82: 245207

    Article  Google Scholar 

  51. Koster LJA, Mihailetchi VD, Xie H, Blom PWM. Appl Phys Lett, 2005, 87: 203502

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (52073221, 52273196).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Tao Wang.

Ethics declarations

Conflict of interest The authors declare no conflict of interest.

Additional information

Supporting information The supporting information is available online at https://chem.scichina.com and https://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

Supporting information

11426_2022_1429_MOESM1_ESM.pdf

Realizing compact three dimensional charge transport networks of asymmetric electron acceptors for efficient organic solar cells

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cai, J., Fu, Y., Guo, C. et al. Realizing compact three-dimensional charge transport networks of asymmetric electron acceptors for efficient organic solar cells. Sci. China Chem. 66, 508–517 (2023). https://doi.org/10.1007/s11426-022-1429-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-022-1429-x

Keywords

Navigation