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Propeller-shaped NI isomers of cathode interfacial material for efficient organic solar cells

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Abstract

Cathode interfacial materials (CIMs) stand as critical elemental in organic solar cells (OSCs), which can align energy levels, and foster ohmic contacts between the cathode and active layer of the OSCs. Nevertheless, the lagging advancement in CIMs has concurrently engendered the oversight of theoretical inquiries pertaining to the impact of molecular structure on their performance. Delving into this realm, we present two propeller-shaped isomers, 4,4′,4″-(benzo[1,2-b:3,4-b′:5,6-b″]trithiophene-2,5,8-triyl)tris(2-(3-(dimethylamino)propyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione) (3ONIN) and 6,6′,6″-(benzo[1,2-b:3,4-b′:5,6-b″]trithiophene-2,5,8-triyl)tris(2-(3-(dimethylamino)propyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione) (3PNIN), distinguished by their molecular planarity, as a promising foundation for crafting highly efficient OSCs. This study illuminates the superiority of 3PNIN with more plane structure, exemplified by its enhanced molar extinction coefficient, deeper lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) energy levels, intensified self-doping effect, heightened electron mobility, and elevated conductivity, in comparison to its counterpart, 3ONIN. As a result, 3PNIN and 3ONIN-treated OSC devices yield efficiencies of 17.73% and 16.82%, respectively. This finding serves as a compelling validation of the critical role played by molecular planarity in influencing CIM performance.

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References

  1. Yao, H. F.; Hou, J. H. Recent advances in single-junction organic solar cells. Angew. Chem. 2022, 134, e202209021.

    Article  ADS  Google Scholar 

  2. Yang, Y.; Wang, J. W.; Zu, Y. E.; Liao, Q.; Zhang, S. Q.; Zheng, Z.; Xu, B. W.; Hou, J. H. Robust and hydrophobic interlayer material for efficient and highly stable organic solar cells. Joule 2023, 7, 545–557.

    Article  CAS  Google Scholar 

  3. Zhang, G. C.; Chen, Q. M.; Zhang, Z.; Fang, J.; Zhao, C. W.; Wei, Y.; Li, W. W. Co-La-based hole-transporting layers for binary organic solar cells with 18.82% efficiency. Angew. Chem. 2023, 135, e202216304.

    Article  ADS  Google Scholar 

  4. Liu, Y. H.; Liu, B. W.; Ma, C. Q.; Huang, F.; Feng, G. T.; Chen, H. Z.; Hou, J. H.; Yan, L. P.; Wei, Q. Y.; Luo, Q. et al. Recent progress in organic solar cells (Part I material science). Sci. China Chem. 2022, 65, 224–268.

    Article  CAS  Google Scholar 

  5. Dai, S. X.; Li, T. F.; Wang, W.; Xiao, Y. Q.; Lau, T. K.; Li, Z. Y.; Liu, K.; Lu, X. H.; Zhan, X. W. Enhancing the performance of polymer solar cells via core engineering of NIR-absorbing electron acceptors. Adv. Mater. 2018, 30, 1706571.

    Article  Google Scholar 

  6. Fan, Q. P.; Xiao, Z.; Wang, E. G.; Ding, L. M. Polymer acceptors based on Y6 derivatives for all-polymer solar cells. Sci. Bull. 2021, 66, 1950–1953.

    Article  CAS  Google Scholar 

  7. Zhao, C. B.; Ma, J. Q.; Ge, H. G.; Tang, Z. H.; Jin, L. X.; Wang, W. L. Theoretical prediction of the photovoltaic properties of BFBPD-PC61BM system as a promising organic solar cell. Chin. J. Struct. Chem. 2018, 37, 15–26.

    CAS  ADS  Google Scholar 

  8. Lin, Y. Z.; Li, Y. F.; Zhan, X. W. Small molecule semiconductors for high-efficiency organic photovoltaics. Chem. Soc. Rev. 2012, 41, 4245–4272.

    Article  CAS  PubMed  Google Scholar 

  9. Cheng, Y. J.; Huang, B.; Huang, X. X.; Zhang, L. F.; Kim, S.; Xie, Q.; Liu, C.; Heumüller, T.; Liu, Z. J.; Zhang, Y. H. et al. Oligomer-assisted photoactive layers enable >18% efficiency of organic solar cells. Angew. Chem. 2022, 134, e202200329.

    Article  Google Scholar 

  10. Dai, S. X.; Zhao, F. W.; Zhang, Q. Q.; Lau, T. K.; Li, T. F.; Liu, K.; Ling, Q. D.; Wang, C. R.; Lu, X. H.; You, W. et al. Fused nonacyclic electron acceptors for efficient polymer solar cells. J. Am. Chem. Soc. 2017, 139, 1336–1343.

    Article  CAS  PubMed  Google Scholar 

  11. Lin, Y. Z.; Wang, J. Y.; Zhang, Z. G.; Bai, H. T.; Li, Y. F.; Zhu, D. B.; Zhan, X. W. An electron acceptor challenging fullerenes for efficient polymer solar cells. Adv. Mater. 2015, 27, 1170–1174.

    Article  CAS  PubMed  Google Scholar 

  12. Dai, S. X.; Xiao, Y. Q.; Xue, P. Y.; James Rech, J.; Liu, K.; Li, Z. Y.; Lu, X. H.; You, W.; Zhan, X. W. Effect of core size on performance of fused-ring electron acceptors. Chem. Mater. 2018, 30, 5390–5396.

    Article  CAS  Google Scholar 

  13. Dai, S.; Zhan, X. Fused-ring electron acceptors for organic solar cells. Acta Polym. Sin. 2017, 11, 1706–1714

    Google Scholar 

  14. Zhu, L.; Zhang, M.; Xu, J. Q.; Li, C.; Yan, J.; Zhou, G. Q.; Zhong, W. K.; Hao, T. Y.; Song, J. L.; Xue, X. N. et al. Single-junction organic solar cells with over 19% efficiency enabled by a refined double-fibril network morphology. Nat. Mater. 2022, 21, 656–663.

    Article  CAS  PubMed  ADS  Google Scholar 

  15. Yao, J.; Chen, Q.; Zhang, C.; Zhang, Z. G.; Li, Y. F. Perylene-diimide-based cathode interlayer materials for high performance organic solar cells. SusMat 2022, 2, 243–263.

    Article  CAS  ADS  Google Scholar 

  16. Cheuh, C. C.; Li, C. Z.; Jen, A. K. Y. Recent progress and perspective in solution-processed Interfacial materials for efficient and stable polymer and organometal perovskite solar cells. Energy Environ. Sci. 2015, 8, 1160–1189.

    Article  Google Scholar 

  17. Duan, C. H.; Wang, L.; Zhang, K.; Guan, X.; Huang, F. Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes. Adv. Mater. 2011, 23, 1665–1669.

    Article  CAS  PubMed  Google Scholar 

  18. Zhang, Z. G.; Qi, B. Y.; Jin, Z. W.; Chi, D.; Qi, Z.; Li, Y. F.; Wang, J. Z. Perylene diimides: A thickness-insensitive cathode interlayer for high performance polymer solar cells. Energy Environ. Sci. 2014, 7, 1966–1973.

    Article  CAS  Google Scholar 

  19. Yao, J.; Qiu, B. B.; Zhang, Z. G.; Xue, L. W.; Wang, R.; Zhang, C. F.; Chen, S. S.; Zhou, Q. J.; Sun, C. K.; Yang, C. et al. Cathode engineering with perylene-diimide interlayer enabling over 17% efficiency single-junction organic solar cells. Nat. Commun. 2020, 11, 2726.

    Article  CAS  PubMed  PubMed Central  ADS  Google Scholar 

  20. Liu, H.; Liu, S. N.; Zhao, Y.; Jiang, J. L.; Feng, X. R.; Sun, M. L.; Yu, L. M.; Dai, S. X. “A-π-A” type naphthalimide-based cathode interlayers for efficient organic solar cells. Dyes Pigm. 2023, 209, 110911.

    Article  CAS  Google Scholar 

  21. Zhao, Y.; Liu, Y.; Liu, X. J.; Kang, X.; Yu, L. M.; Dai, S. X.; Sun, M. L. Aminonaphthalimide-based molecular cathode interlayers for As-cast organic solar cells. ChemSusChem. 2021, 14, 4783–4792.

    Article  CAS  PubMed  Google Scholar 

  22. Zhao, Y.; Liu, X. J.; Jing, X.; Liu, S. N.; Liu, H.; Liu, Y.; Yu, L. M.; Dai, S. X.; Sun, M. L. Multi-armed imide-based molecules promote interfacial charge transfer for efficient organic solar cells. Chem. Eng. J. 2022, 441, 135894.

    Article  CAS  Google Scholar 

  23. Zhao, Y.; Liu, X. J.; Jing, X.; Liu, Y.; Liu, H.; Li, S. N.; Yu, L. M.; Dai, S. X.; Sun, M. L. Achieving the low interfacial tension by balancing crystallization and film-forming ability of the cathode interlayer for organic solar cells. J. Colloid Interface Sci. 2022, 627, 880–890.

    Article  CAS  PubMed  ADS  Google Scholar 

  24. Rossi, S.; Bisello, A.; Cardena, R.; Orian, L.; Santi, S. Benzodithiophene and benzotrithiophene as π cores for two- and three-blade propeller-shaped ferrocenyl-based conjugated systems. Eur. J. Org. Chem. 2017, 2017, 5966–5974.

    Article  CAS  Google Scholar 

  25. Yang, Q. G.; Yu, W. Y.; Lv, J.; Huang, P. H.; He, G. T.; Xiao, Z. Y.; Kan, Z. P.; Lu, S. R. Effects of fluorination position on all-polymer organic solar cells. Dyes Pigm. 2022, 200, 110180.

    Article  CAS  Google Scholar 

  26. Chen, T. Y.; Li, S. X.; Li, Y. K.; Chen, Z.; Wu, H. T.; Lin, Y.; Gao, Y.; Wang, M. T.; Ding, G. Y.; Min, J. et al. Compromising charge generation and recombination of organic photovoltaics with mixed diluent strategy for certified 19.4% efficiency. Adv. Mater. 2023, 35, 2300400.

    Article  CAS  Google Scholar 

  27. Malliaras, G. G.; Salem, J. R.; Brock, P. J.; Scott, C. Electrical characteristics and efficiency of single-layer organic light-emitting diodes. Phys. Rev. B 1998, 58, R13411–R13414.

    Article  CAS  ADS  Google Scholar 

  28. Wu, M. M.; Shi, L. T.; Hu, Y.; Chen, L.; Hu, T.; Zhang, Y. D.; Yuan, Z. Y.; Chen, Y. W. Additive-free non-fullerene organic solar cells with random copolymers as donors over 9% power conversion efficiency. Chin. Chem. Lett. 2019, 30, 1161–1167.

    Article  CAS  Google Scholar 

  29. Liu, M.; Li, M. Y.; Jiang, Y. F.; Ma, Z. F.; Liu, D. Z. J.; Ren, Z. J.; Russell, T. P.; Liu, Y. Conductive ionenes promote interfacial self-doping for efficient organic solar cells. ACS Appl. Mater. Interfaces 2021, 13, 41810–41817.

    Article  CAS  PubMed  Google Scholar 

  30. Xu, W. J.; Zi, M.; Zhang, M.; Hao, R. F.; Shen, P.; Zhao, B.; Tan, S. T. Improved photovoltaic properties of copolymer donors by regulating alkyl and alkylsilyl side chains. Dyes Pigm. 2022, 197, 109842.

    Article  CAS  Google Scholar 

  31. Wang, K.; Xu, Z.; Geng, Y.; Li, H.; Lin, C. L.; Mi, L. W.; Guo, X.; Zhang, M. J.; Li, Y. F. Synthesis of organic molecule donor for efficient organic solar cells with low acceptor content. Org. Electron. 2019, 64, 54–61.

    Article  CAS  Google Scholar 

  32. Bolag, A.; López-Andarias, J.; Lascano, S.; Soleimanpour, S.; Atienza, C.; Sakai, N.; Martín, N.; Matile, S. A collection of fullerenes for synthetic access toward oriented charge-transfer cascades in triple-channel photosystems. Angew. Chem., Int. Ed. 2014, 53, 4890–4895.

    Article  CAS  Google Scholar 

  33. Yang, R.; Tian, J.; Liu, W. X.; Wang, Y. X.; Chen, Z.; Russell, T. P.; Liu, Y. Nonconjugated self-doped polymer zwitterions as efficient interlayers for high performance organic solar cells. Chem. Mater. 2022, 34, 7293–7301.

    Article  CAS  Google Scholar 

  34. Dai, S. X.; Zhou, J. D.; Chandrabose, S.; Shi, Y. J.; Han, G. C.; Chen, K.; Xin, J. M.; Liu, K.; Chen, Z. Y.; Xie, Z. Q. et al. High-performance fluorinated fused-ring electron acceptor with 3D stacking and exciton/charge transport. Adv. Mater. 2020, 32, 2000645.

    Article  CAS  Google Scholar 

  35. Schilinsky, P.; Waldauf, C.; Brabec, C. J. Recombination and loss analysis in polythiophene based bulk heterojunction photodetectors. Appl. Phys. Lett. 2002, 81, 3885–3887.

    Article  CAS  ADS  Google Scholar 

  36. Cowan, S. R.; Roy, A.; Heeger, A. J. Recombination in polymer-fullerene bulk heterojunction solar cells. Phys. Rev. B 2010, 82, 245207.

    Article  ADS  Google Scholar 

  37. Meng, Y.; Wu, J. N.; Guo, X.; Su, W. Y.; Zhu, L.; Fang, J.; Zhang, Z. G.; Liu, F.; Zhang, M. J.; Russell, T. P. et al. 11.2% efficiency all-polymer solar cells with high open-circuit voltage. Sci. China Chem. 2019, 62, 845–850.

    Article  CAS  Google Scholar 

  38. Liao, Q.; Kang, Q.; Yang, Y.; An, C. B.; Xu, B. W.; Hou, J. H. Tailoring and modifying an organic electron acceptor toward the cathode interlayer for highly efficient organic solar cells. Adv. Mater. 2020, 32, 1906557.

    Article  CAS  Google Scholar 

  39. Yuan, Y. X.; Wu, F.; Chen, G. H.; Bai, Y.; Wu, C. Porous LiF layer fabricated by a facile chemical method toward dendrite-free lithium metal anode. J. Energy Chem. 2019, 37, 197–203.

    Article  Google Scholar 

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 22105189).

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  1. Hao Liu and Jilei Jiang contributed equally to this work.

Authors and Affiliations

  1. School of Materials Science and Engineering, Ocean University of China, Qingdao, 266100, China

    Hao Liu, Jilei Jiang, Shuixing Dai, Xianbiao Hou & Minghua Huang

  2. Open Studio for Marine Corrosion and Protection, Pilot National Laboratory for Marine Science and Technology, Qingdao, 266100, China

    Liangmin Yu

  3. Science Center for Material Creation and Energy Conversion, Institute of Frontier and Interdisciplinary Science, Shandong University, Qingdao, 266237, China

    Xu Zhang & Ke Gao

  4. Qingdao Key Laboratory of Functional Membrane Material and Membrane Technology, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101, China

    Heqing Jiang

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  1. Hao Liu
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Correspondence to Shuixing Dai or Minghua Huang.

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Liu, H., Jiang, J., Dai, S. et al. Propeller-shaped NI isomers of cathode interfacial material for efficient organic solar cells. Nano Res. 17, 1564–1570 (2024). https://doi.org/10.1007/s12274-024-6482-z

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  • DOI: https://doi.org/10.1007/s12274-024-6482-z

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