Abstract
With the development of photovoltaic materials, especially the small molecule acceptors (SMAs), organic solar cells (OSCs) have made breakthroughs in power conversion efficiencies (PCEs). However, the stability of high-performance OSCs remains a critical challenge for future technological applications. To tackle the inherent instability of SMA materials under the ambient conditions, much effort has been made to improve OSCs stability, including device modification and new materials design. Here we proposed a new electron acceptor design strategy and developed a “quasi-macromolecule” (QM) with an A-π-A structure, where the functionalized π-bridge is used as a linker between two SMAs (A), to improve the long-term stability without deteriorating device efficiencies. Such type of QMs enables excellent synthetic flexibility to modulate their optical/electrochemical properties, crystallization and aggregation behaviors by changing the A and π units. Moreover, QMs possess a unique long conjugated backbone combining high molecular weight over 3.5 kDa with high purity. Compared with the corresponding SMA BTP-4F-OD (Y6-OD), the devices based on newly synthesized A-π-A type acceptors QM1 and QM2 could exhibit better device stability and more promising PCEs of 17.05% and 16.36%, respectively. This kind of “molecular-framework” (A-π-A) structure provides a new design strategy for developing high-efficiency and -stability photovoltaic materials.
Similar content being viewed by others
Change history
20 September 2022
An Erratum to this paper has been published: https://doi.org/10.1007/s11426-022-1393-1
References
Heeger AJ. Adv Mater, 2014, 26: 10–28
Fan X. Adv Funct Mater, 2020, 31: 2009399
Cui Y, Yang C, Yao H, Zhu J, Wang Y, Jia G, Gao F, Hou J. Adv Mater, 2017, 29: 1703080
Chen X, Xu G, Zeng G, Gu H, Chen H, Xu H, Yao H, Li Y, Hou J, Li Y. Adv Mater, 2020, 32: 1908478
Wang Y, Chang Y, Zhang J, Lu G, Wei Z. Chem Res Chin Univ, 2020, 36: 343–350
Kaltenbrunner M, White MS, Glowacki ED, Sekitani T, Someya T, Sariciftci NS, Bauer S. Nat Commun, 2012, 3: 770
Liu Y, Liu B, Ma CQ, Huang F, Feng G, Chen H, Hou J, Yan L, Wei Q, Luo Q, Bao Q, Ma W, Liu W, Li W, Wan X, Hu X, Han Y, Li Y, Zhou Y, Zou Y, Chen Y, Li Y, Chen Y, Tang Z, Hu Z, Zhang ZG, Bo Z. Sci China Chem, 2021, 65: 224–268
Bi P, Zhang S, Wang J, Ren J, Hou J. Chin J Chem, 2021, 39: 2607–2625
Frost JM, Faist MA, Nelson J. Adv Mater, 2010, 22: 4881–4884
Lenes M, Wetzelaer GJAH, Kooistra FB, Veenstra SC, Hummelen JC, Blom PWM. Adv Mater, 2008, 20: 2116–2119
Choi JH, Son KI, Kim T, Kim K, Ohkubo K, Fukuzumi S. J Mater Chem, 2010, 20: 475–482
Liu W, Xu X, Yuan J, Leclerc M, Zou Y, Li Y. ACS Energy Lett, 2021, 6: 598–608
Hou J, Inganäs O, Friend RH, Gao F. Nat Mater, 2018, 17: 119–128
Zhang G, Zhao J, Chow PCY, Jiang K, Zhang J, Zhu Z, Zhang J, Huang F, Yan H. Chem Rev, 2018, 118: 3447–3507
Wadsworth A, Moser M, Marks A, Little MS, Gasparini N, Brabec CJ, Baran D, McCulloch I. Chem Soc Rev, 2019, 48: 1596–1625
Wei Q, Liu W, Leclerc M, Yuan J, Chen H, Zou Y. Sci China Chem, 2020, 63: 1352–1366
Zhang Q, Xu X, Chen S, Bodedla GB, Sun M, Hu Q, Peng Q, Huang B, Ke H, Liu F, Russell TP, Zhu X. Sustain Energy Fuels, 2018, 2: 2616–2624
Shi K, Qiu B, Zhu C, Xia X, Xue X, Zhang J, Wan Y, Huang S, Meng L, Lu X, Zhang ZG, Li Y. J Mater Chem C, 2022, 10: 2017–2025
Lin Y, Wang J, Zhang ZG, Bai H, Li Y, Zhu D, Zhan X. Adv Mater, 2015, 27: 1170–1174
Feng L, Yuan J, Zhang Z, Peng H, Zhang ZG, Xu S, Liu Y, Li Y, Zou Y. ACS Appl Mater Interfaces, 2017, 9: 31985–31992
Yuan J, Zou Y. Org Electron, 2022, 102: 106436
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
Fan B, Zhang D, Li M, Zhong W, Zeng Z, Ying L, Huang F, Cao Y. Sci China Chem, 2019, 62: 746–752
Cui Y, Xu Y, Yao H, Bi P, Hong L, Zhang J, Zu Y, Zhang T, Qin J, Ren J, Chen Z, He C, Hao X, Wei Z, Hou J. Adv Mater, 2021, 33: 2102420
Zheng Z, Wang J, Bi P, Ren J, Wang Y, Yang Y, Liu X, Zhang S, Hou J. Joule, 2022, 6: 171–184
Speller EM, Clarke AJ, Aristidou N, Wyatt MF, Francàs L, Fish G, Cha H, Lee HKH, Luke J, Wadsworth A, Evans AD, McCulloch I, Kim JS, Haque SA, Durrant JR, Dimitrov SD, Tsoi WC, Li Z. ACS Energy Lett, 2019, 4: 846–852
Liu X, Li X, Zheng N, Gu C, Wang L, Fang J, Yang C. ACS Appl Mater Interfaces, 2019, 11: 43433–43440
Zhao F, Zhang H, Zhang R, Yuan J, He D, Zou Y, Gao F. Adv Energy Mater, 2020, 10: 2002746
Cheng P, Zhan X. Chem Soc Rev, 2016, 45: 2544–2582
Doumon NY, Houard FV, Dong J, Yao H, Portale G, Hou J, Koster LJA. Org Electron, 2019, 69: 255–262
Azeez A, Narayan KS. J Phys Chem C, 2021, 125: 12531–12540
Park S, Son HJ. J Mater Chem A, 2019, 7: 25830–25837
Ghasemi M, Balar N, Peng Z, Hu H, Qin Y, Kim T, Rech JJ, Bidwell M, Mask W, McCulloch I, You W, Amassian A, Risko C, O’Connor BT, Ade H. Nat Mater, 2021, 20: 525–532
Liu H, Liu Z, Wang S, Huang J, Ju H, Chen Q, Yu J, Chen H, Li C. Adv Energy Mater, 2019, 9: 1900887
Liu B, Han Y, Li Z, Gu H, Yan L, Lin Y, Luo Q, Yang S, Ma CQ. Sol RRL, 2020, 5: 2000638
Zhu X, Hu L, Wang W, Jiang X, Hu L, Zhou Y. ACS Appl Energy Mater, 2019, 2: 7602–7608
Hu L, Zhao N, Jiang X, Jiang Y, Qin F, Sun L, Wang W, Zhou Y. J Mater Chem C, 2020, 8: 12218–12223
Han Y, Dong H, Pan W, Liu B, Chen X, Huang R, Li Z, Li F, Luo Q, Zhang J, Wei Z, Ma CQ. ACS Appl Mater Interfaces, 2021, 13: 17869–17881
Li Y, Huang X, Ding K, Sheriff Jr HKM, Ye L, Liu H, Li CZ, Ade H, Forrest SR. Nat Commun, 2021, 12: 5419
Hu L, Jiang Y, Sun L, Xie C, Qin F, Wang W, Zhou Y. J Phys Chem Lett, 2021, 12: 2607–2614
Zhang QQ, Li Y, Wang D, Chen Z, Li Y, Li S, Zhu H, Lu X, Chen H, Li CZ. Bull Chem Soc Jpn, 2021, 94: 183–190
Zhu X, Liu S, Yue Q, Liu W, Sun S, Xu S. CCS Chem, 2021, 3: 1070–1080
Liu H, Wang W, Zhou Y, Li Z. J Mater Chem A, 2021, 9: 1080–1088
Yu Y, Zhang Y, Miao J, Liu J, Wang L. CCS Chem, 2022: 1–11
Du X, Heumueller T, Gruber W, Classen A, Unruh T, Li N, Brabec CJ. Joule, 2019, 3: 215–226
Liu ZX, Yu ZP, Shen Z, He C, Lau TK, Chen Z, Zhu H, Lu X, Xie Z, Chen H, Li CZ. Nat Commun, 2021, 12: 3049
Guo J, Wu Y, Sun R, Wang W, Guo J, Wu Q, Tang X, Sun C, Luo Z, Chang K, Zhang Z, Yuan J, Li T, Tang W, Zhou E, Xiao Z, Ding L, Zou Y, Zhan X, Yang C, Li Z, Brabec CJ, Li Y, Min J. J Mater Chem A, 2019, 7: 25088–25101
Seo S, Sun C, Lee J-, Lee S, Lee D, Wang C, Phan TN, Kim G, Cho S, Kim Y, Kim BJ. Adv Funct Mater, 2021, 32: 2108508
Zhang ZG, Li Y. Angew Chem Int Ed, 2021, 60: 4422–4433
Zhang ZG, Yang Y, Yao J, Xue L, Chen S, Li X, Morrison W, Yang C, Li Y. Angew Chem Int Ed, 2017, 56: 13503–13507
Luke J, Speller EM, Wadsworth A, Wyatt MF, Dimitrov S, Lee HKH, Li Z, Tsoi WC, McCulloch I, Bagnis D, Durrant JR, Kim J. Adv Energy Mater, 2019, 9: 1803755
Holliday S, Ashraf RS, Wadsworth A, Baran D, Yousaf SA, Nielsen CB, Tan CH, Dimitrov SD, Shang Z, Gasparini N, Alamoudi M, Laquai F, Brabec CJ, Salleo A, Durrant JR, McCulloch I. Nat Commun, 2016, 7: 11585
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
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
Luo Z, Liu T, Ma R, Xiao Y, Zhan L, Zhang G, Sun H, Ni F, Chai G, Wang J, Zhong C, Zou Y, Guo X, Lu X, Chen H, Yan H, Yang C. Adv Mater, 2020, 32: 2005942
Sun Y, Ma Y, Liu Y, Lin Y, Wang Z, Wang Y, Di C, Xiao K, Chen X, Qiu W, Zhang B, Yu G, Hu W, Zhu D. Adv Funct Mater, 2006, 16: 426–432
Chen H, Hu D, Yang Q, Gao J, Fu J, Yang K, He H, Chen S, Kan Z, Duan T, Yang C, Ouyang J, Xiao Z, Sun K, Lu S. Joule, 2019, 3: 3034–3047
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, 2020, 11: 2003141
Zhu C, Yuan J, Cai F, Meng L, Zhang H, Chen H, Li J, Qiu B, Peng H, Chen S, Hu Y, Yang C, Gao F, Zou Y, Li Y. Energy Environ Sci, 2020, 13: 2459–2466
Acknowledgements
This work was supported by the National Natural Science Foundation of China (52125306, 21875286, 22005347), the Natural Science Foundation of Hunan Province (2021JJ20068), and the National Key Research and Development Program of China (2017YFA0206600).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Conflict of interest
The authors declare no conflict of interest.
Supporting information
The supporting information is available online at http://chem.scichina.com and http://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.
The online version of the original article can be found at https://doi.org/10.1007/s11426-022-1393-1
Supporting Information
11426_2022_1281_MOESM1_ESM.docx
A-π-A structured non-fullerene acceptors for stable organic solar cells with efficiency over 17%, approximately 2.83 MB.
Rights and permissions
About this article
Cite this article
Liu, W., Yuan, J., Zhu, C. et al. A-π-A structured non-fullerene acceptors for stable organic solar cells with efficiency over 17%. Sci. China Chem. 65, 1374–1382 (2022). https://doi.org/10.1007/s11426-022-1281-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-022-1281-0