Unaxisymmetric Non-Fused Electron Acceptors for Efficient Polymer Solar Cells

Si-Ya Liu; Di Wang; Tian-Jiao Wen; Guan-Qing Zhou; Hai-Ming Zhu; Hong-Zheng Chen; Chang-Zhi Li

doi:10.1007/s10118-022-2750-0

Your Location：

Home >

Browse articles >

Unaxisymmetric Non-Fused Electron Acceptors for Efficient Polymer Solar Cells

RESEARCH ARTICLE | Updated：2022-07-21

- Unaxisymmetric Non-Fused Electron Acceptors for Efficient Polymer Solar Cells
- Unaxisymmetric Non-Fused Electron Acceptors for Efficient Polymer Solar Cells
- Chinese Journal of Polymer Science 2022年40卷第8期页码：944-950
- Affiliations：
  
  a.State Key Laboratory of Silicon Materials, MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
  b.Department of Chemistry, Zhejiang University, Hangzhou 310027, China
- Author bio：
  
  czli@zju.edu.cn
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (No. 22125901), and National Key Research and Development Program of China (No. 2019YFA0705900).
- DOI：10.1007/s10118-022-2750-0
  中图分类号：
- 收稿：2022-03-07，
  
  录用：2022-4-2，
  
  网络首发：2022-06-21，
  
  纸质出版：2022-08-01
- Accepted：
Scan QR Code
Liu, S. Y.; Wang, D.; Wen, T. J.; Zhou, G. Q.; Zhu, H. M.; Chen, H. Z.; Li, C. Z. Unaxisymmetric non-fused electron acceptors for efficient polymer solar cells. Chinese J. Polym. Sci. 2022, 40, 944–950

Si-Ya Liu, Di Wang, Tian-Jiao Wen, et al. Unaxisymmetric Non-Fused Electron Acceptors for Efficient Polymer Solar Cells[J]. Chinese Journal of Polymer Science, 2022, 40(8): 944-950.
Liu, S. Y.; Wang, D.; Wen, T. J.; Zhou, G. Q.; Zhu, H. M.; Chen, H. Z.; Li, C. Z. Unaxisymmetric non-fused electron acceptors for efficient polymer solar cells. Chinese J. Polym. Sci. 2022, 40, 944–950 DOI： 10.1007/s10118-022-2750-0.

Si-Ya Liu, Di Wang, Tian-Jiao Wen, et al. Unaxisymmetric Non-Fused Electron Acceptors for Efficient Polymer Solar Cells[J]. Chinese Journal of Polymer Science, 2022, 40(8): 944-950. DOI： 10.1007/s10118-022-2750-0.

摘要

Fully non-fused ring acceptors (NFRAs)

p-PTIC4Cl and t-PTIC4Cl

are developed via a concise synthetic route. It is revealed that the tuning of unaxisymmetric aromatic chains could modulate the self-assemble properties of NFRAs

hence optimizing their optoelectronic properties to construct the cost-effective polymer solar cells.

Abstract

To develop photovoltaics embracing the both features of high performance and low cost has drawn attentions of researchers

yet representing the significant challenges. In this work

two non-fused ring acceptors (NFRAs)

namely p-PTIC4Cl and t-PTIC4Cl

were developed

via

a short synthetic route. By tethering unaxisymmetric aromatic chains to thienyl bridge of NFRAs

we revealed that the tuning of aromatic chains allows modulating the self-assembly and stacking of NFRAs in solid

hence influencing their optoelectronic and photovoltaic properties. As results

p-PTIC4Cl

consisting of 3-hexylbenzene with large axial angle to backbone

can achieve superior PCE of 11.30% than that of t-PTIC4Cl with 2-hexylthiophene chains (PCE of 6.49%)

when pairing with polymer donor PBDB-TF. Despite of the only subtle structural difference

the p-PTIC4Cl based blend films possess better exciton dissociation and charge transfer rates

as well as photostability

to those of t-PTIC4Cl based blends.

关键词

Keywords

references

Chong, K.; Xu, X.; Meng, H.; Xue, J.; Yu, L.; Ma, W.; Peng, Q. . Realizing 19.05% efficiency polymer solar cells by progressively improving charge extraction and suppressing charge recombination . Adv. Mater. , 2022 . 34 2109516 DOI: 10.1002/adma.202109516 http://doi.org/10.1002/adma.202109516 .

Liu, Q.; Jiang, Y.; Jin, K.; Qin, J.; Xu, J.; Li, W.; Xiong, J.; Liu, J.; Xiao, Z.; Sun, K.; Yang, S.; Zhang, X.; Ding, L . 18% Efficiency organic solar cells . Sci. Bull. , 2020 . 65 272 - 275 . DOI: 10.1016/j.scib.2020.01.001 http://doi.org/10.1016/j.scib.2020.01.001 .

Song, J.; Zhu, L.; Li, C.; Xu, J.; Wu, H.; Zhang, X.; Zhang, Y.; Tang, Z.; Liu, F.; Sun, Y . High-efficiency organic solar cells with low voltage loss induced by solvent additive strategy . Matter , 2021 . 4 2542 - 2552 . DOI: 10.1016/j.matt.2021.06.010 http://doi.org/10.1016/j.matt.2021.06.010 .

He, C.; Bi, Z.; Chen, Z.; Guo, J.; Xia, X.; Lu, X.; Min, J.; Zhu, H.; Ma, W.; Zuo, L.; Chen, H . Compromising charge generation and recombination with asymmetric molecule for high-performance binary organic photovoltaics with over 18% certified efficiency . Adv. Funct. Mater. , 2022 . 32 2112511 DOI: 10.1002/adfm.202112511 http://doi.org/10.1002/adfm.202112511 .

Wang, D.; Zhou, G.; Li, Y.; Yan, K.; Zhan, L.; Zhu, H.; Lu, X.; Chen, H.; Li, C. Z . High-performance organic solar cells from non-halogenated solvents . Adv. Funct. Mater. , 2021 . 32 2107827 .

Tao, Y.; Liu, H.; Wang, D.; Zhao, F.; Chen, Z.; Zhu, H.; Chen, H.; Li, C. Z. . Healing the degradable organic-inorganic heterointerface for highly efficient and stable organic solar cells . InfoMat , 2022 . 4 e12276 DOI: 10.1002/inf2.12276 http://doi.org/10.1002/inf2.12276 .

Hou, J.; Inganäs, O.; Friend, R. H.; Gao, F . Organic solar cells based on non-fullerene acceptors . Nat. Mater. , 2018 . 17 119 - 128 . DOI: 10.1038/nmat5063 http://doi.org/10.1038/nmat5063 .

Wei, Q.; Liu, W.; Leclerc, M.; Yuan, J.; Chen, H.; Zou, Y . A-DA′D-A non-fullerene acceptors for high-performance organic solar cells . Sci. Chi. Chem. , 2020 . 63 1352 - 1366 . DOI: 10.1007/s11426-020-9799-4 http://doi.org/10.1007/s11426-020-9799-4 .

Ren, J.; Shu, X.; Wang, Y.; Wang, D.; Wu, G.; Zhang, X.; Jin, Q.; Liu, J.; Wu, Z.; Xu, Z.; Li, C. Z.; Li, H. Key progresses of MOE key laboratory of macromolecular synthesis and functionalization in 2020. Chin. Chem. Lett. 2021 , DOI: 10.1016/j.cclet.2021.10.052.

Yue, Q.; Liu, W.; Zhu, X . n-Type molecular photovoltaic materials: design strategies and device applications . J. Am. Chem. Soc. , 2020 . 142 11613 - 11628 . DOI: 10.1021/jacs.0c04084 http://doi.org/10.1021/jacs.0c04084 .

Wang, C.; Liu, F.; Chen, Q. M.; Xiao, C. Y.; Wu, Y. G.; Li, W. W . Benzothiadiazole-based conjugated polymers for organic solar cells . Chinese J. Polym. Sci. , 2021 . 39 525 - 536 . DOI: 10.1007/s10118-021-2537-8 http://doi.org/10.1007/s10118-021-2537-8 .

Chen, Z.; Ma, S. S.; Zhang, K.; Hu, Z. C.; Yin, Q W.; Huang, F.; Cao, Y . A near-infrared non-fullerene acceptor with thienopyrrole-expanded benzo[1,2- b :4,5- b ′]dithiophene core for polymer solar cells . Chinese J. Polym. Sci. , 2020 . 39 35 - 42 . DOI: 10.1007/s10118-020-2440-8 http://doi.org/10.1007/s10118-020-2440-8 .

Zhang, Y.; Wang, Y.; Ma, R.; Luo, Z.; Liu, T.; Kang, S . H.; Yan, H.; Yuan, Z.; Yang, C.; Chen, Y. Wide band-gap two-dimension conjugated polymer donors with different amounts of chlorine substitution on alkoxyphenyl conjugated side chains for non-fullerene polymer solar cells . Chinese J. Polym. Sci. , 2020 . 38 797 - 805 . DOI: 10.1007/s10118-020-2435-5 http://doi.org/10.1007/s10118-020-2435-5 .

Liu, F.; Wang, D.; Li, J. Y.; Xiao, C. Y.; Wu, Y. G.; Li, W. W.; Fu, G. S . Side-chains engineering of conjugated polymers toward additive-free non-fullerene organic solar cells . Chinese J. Polym. Sci. , 2020 . 39 43 - 50 . DOI: 10.1007/s10118-020-2490-y http://doi.org/10.1007/s10118-020-2490-y .

Li, S.; Zhan, L.; Liu, F.; Ren, J.; Shi, M.; Li, C. Z.; Russell, T. P.; Chen, H . An unfused-core-based nonfullerene acceptor enables high-efficiency organic solar cells with excellent morphological stability at high temperatures . Adv. Mater. , 2018 . 30 1705208 DOI: 10.1002/adma.201705208 http://doi.org/10.1002/adma.201705208 .

Zhang, Z. Q.; Zhang, S. H.; Liu, Z. X.; Zhang, Z. G.; Li Y. F.; Li C. Z.; Chen, H. Z . A simple electron acceptor with unfused backbone for polymer solar cells . Acta Phys. -Chim. Sin. , 2019 . 35 394 - 400 . DOI: 10.3866/PKU.WHXB201805091 http://doi.org/10.3866/PKU.WHXB201805091 .

Liu, Z. X.; Yu, Z. P.; Shen, Z.; He, C.; Lau, T. K.; Chen, Z.; Zhu, H.; Lu, X.; Xie, Z.; Chen, H.; Li, C. Z . Molecular insights of exceptionally photostable electron acceptors for organic photovoltaics . Nat. Commun. , 2021 . 12 3049 DOI: 10.1038/s41467-021-23389-1 http://doi.org/10.1038/s41467-021-23389-1 .

Yang, M.; Wei, W.; Zhou, X.; Wang, Z.; Duan, C . Non-fused ring acceptors for organic solar cells . Energy Mater. , 2021 . 1 100008 .

Huang, H.; Guo, Q.; Feng, S.; Zhang, C.; Bi, Z.; Xue, W.; Yang, J.; Song, J.; Li, C.; Xu, X.; Tang, Z.; Ma, W.; Bo, Z . Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells . Nat. Commun. , 2019 . 10 3038 DOI: 10.1038/s41467-019-11001-6 http://doi.org/10.1038/s41467-019-11001-6 .

Wu, Z.; Chen, Y.; Zhang, L.; Yuan, D.; Qiu, R.; Deng, S.; Liu, H.; Zhang, Z.; Chen, J . A ligand-free direct heteroarylation approach for benzodithiophenedione-based simple small molecular acceptors toward high efficiency polymer solar cells . J. Mater. Chem. A , 2021 . 9 3314 - 3321 . DOI: 10.1039/D0TA12288B http://doi.org/10.1039/D0TA12288B .

Geng, S. Z.; Yang, W. T.; Gao, J.; Li, S. X.; Shi, M. M.; Lau, T. K.; Lu, X. H.; Li, C. Z.; Chen, H. Z . Non-fullerene Acceptors with a thieno[3,4- c ]pyrrole-4,6-dione (TPD) core for efficient organic solar cells . Chinese J. Polym. Sci. , 2019 . 37 1005 - 1014 . DOI: 10.1007/s10118-019-2309-x http://doi.org/10.1007/s10118-019-2309-x .

Wen, T. J.; Wang, D.; Tao, L.; Xiao, Y.; Tao, Y. D.; Li, Y.; Lu, X.; Fang, Y.; Li, C . Z.; Chen, H.; Yang, D. Simple near-infrared electron acceptors for efficient photovoltaics and sensitive photodetectors . ACS Appl. Mater. Interfaces , 2020 . 12 39515 - 39523 . DOI: 10.1021/acsami.0c12100 http://doi.org/10.1021/acsami.0c12100 .

Bi, P.; Zhang, S.; Ren, J.; Chen, Z.; Zheng, Z.; Cui, Y.; Wang, J.; Wang, S.; Zhang, T.; Li, J.; Xu, Y.; Qin, J.; An, C.; Ma, W.; Hao, X.; Hou, J . High-performance non-fused wide bandgap acceptor for versatile photovoltaic applications . Adv. Mater. , 2022 . 34 2108090 DOI: 10.1002/adma.202108090 http://doi.org/10.1002/adma.202108090 .

Zhou, Y.; Li, M.; Lu, H.; Jin, H.; Wang, X.; Zhang, Y.; Shen, S.; Ma, Z.; Song, J.; Bo, Z . High-efficiency organic solar cells based on a low-cost fully non-fused electron acceptor . Adv. Funct. Mater. , 2021 . 31 2101742 DOI: 10.1002/adfm.202101742 http://doi.org/10.1002/adfm.202101742 .

Chen, Y . N.; Li, M.; Wang, Y.; Wang, J.; Zhang, M.; Zhou, Y.; Yang, J.; Liu, Y.; Liu, F.; Tang, Z.; Bao, Q.; Bo, Z. A fully non-fused ring acceptor with planar backbone and near-IR absorption for high performance polymer solar cells . Angew. Chem. Int. Ed. , 2020 . 59 22714 - 22720 . DOI: 10.1002/anie.202010856 http://doi.org/10.1002/anie.202010856 .

Li, J.; Li, H.; Ma, L.; Xu, Y.; Cui, Y.; Wang, J.; Ren, J.; Zhu, J.; Zhang, S.; Hou, J . Influence of large steric hinderance substituent position on conformation and charge transfer process for non-fused ring acceptors . Small Methods , 2022 . 6 2200007 DOI: 10.1002/smtd.202200007 http://doi.org/10.1002/smtd.202200007 .

Xue, Z. X.; Fang, J.; Li, J.; Zhang, D.; Xu, Z. W.; Liu, L. N.; Yao, J.; Ma, C. Q.; Li, W. S . Non-fused molecular photovoltaic acceptor with a planar core structure enabled by bulky and embracing-type side chains . J. Mater. Chem. C , 2022 . 10 2945 - 2949 . DOI: 10.1039/D1TC05550J http://doi.org/10.1039/D1TC05550J .

Lu, H.; Wang, X. D.; Wang, H.; Zhang, A. D.; Zheng, X. M.; Yu, N.; Tang, Z.; Xu, X. J.; Liu, Y. H.; Chen, Y. N.; Bo, Z. S . High-performance nonfused ring electron acceptor with a steric hindrance induced planar molecular backbone . Sci. Chin. Chem. , 2022 . 65 594 - 601 . DOI: 10.1007/s11426-021-1159-y http://doi.org/10.1007/s11426-021-1159-y .

Yu, Z. P.; Liu, Z. X.; Chen, F. X.; Qin, R.; Lau, T. K.; Yin, J. L.; Kong, X.; Lu, X.; Shi, M.; Li, C. Z.; Chen, H . Simple non-fused electron acceptors for efficient and stable organic solar cells . Nat. Commun. , 2019 . 10 2152 DOI: 10.1038/s41467-019-10098-z http://doi.org/10.1038/s41467-019-10098-z .

Wen, T. J.; Liu, Z. X.; Chen, Z.; Zhou, J.; Shen, Z.; Xiao, Y.; Lu, X.; Xie, Z.; Zhu, H.; Li, C. Z.; Chen, H . Simple non-fused electron acceptors leading to efficient organic photovoltaics . Angew. Chem. Int. Ed. , 2021 . 60 12964 - 12970 . DOI: 10.1002/anie.202101867 http://doi.org/10.1002/anie.202101867 .

Wang, X.; Lu, H.; Liu, Y.; Zhang, A.; Yu, N.; Wang, H.; Li, S.; Zhou, Y.; Xu, X.; Tang, Z.; Bo, Z . Simple nonfused ring electron acceptors with 3D network packing structure boosting the efficiency of organic solar cells to 15.44% . Adv. Energy Mater. , 2021 . 11 2102591 DOI: 10.1002/aenm.202102591 http://doi.org/10.1002/aenm.202102591 .

Ma, L.; Zhang, S.; Zhu, J.; Wang, J.; Ren, J.; Zhang, J.; Hou, J . Completely non-fused electron acceptor with 3D-interpenetrated crystalline structure enables efficient and stable organic solar cell . Nat. Commun. , 2021 . 12 5093 DOI: 10.1038/s41467-021-25394-w http://doi.org/10.1038/s41467-021-25394-w .

Yang, Y.; Zhang, Z . G.; Bin, H.; Chen, S.; Gao, L.; Xue, L.; Yang, C.; Li, Y. Side-chain isomerization on an n -type organic semiconductor ITIC acceptor makes 11.77% high efficiency polymer solar cells . J. Am. Chem. Soc. , 2016 . 138 15011 - 15018 . DOI: 10.1021/jacs.6b09110 http://doi.org/10.1021/jacs.6b09110 .

Lin, Y.; Zhao, F.; He, Q.; Huo, L.; Wu, Y.; Parker, T. C.; Ma, W.; Sun, Y.; Wang, C.; Zhu, D.; Heeger, A. J.; Marder, S. R.; Zhan, X . High-performance electron acceptor with thienyl side chains for organic photovoltaics . J. Am. Chem. Soc. , 2016 . 138 4955 - 61 . DOI: 10.1021/jacs.6b02004 http://doi.org/10.1021/jacs.6b02004 .

Dou, K.; Wang, X.; Du, Z.; Jiang, H.; Li, F.; Sun, M.; Yang, R . Synergistic effect of side-chain and backbone engineering in thieno[2,3-f]benzofuran-based conjugated polymers for high performance non-fullerene organic solar cells . J. Mater. Chem. A , 2019 . 7 958 - 964 . DOI: 10.1039/C8TA07544A http://doi.org/10.1039/C8TA07544A .

Zhang, Z.; Liu, Z.-X.; Yan, K. R.; Li, H.; Liu, W.; Lu, X.; Li, H; Chen, H.; Li, C. Z . Photovoltaic properties of DPP-based two-and three-component polymers . Acta Polymerica Sinica (in Chinese) , 2018 . 295 - 303 . DOI: 10.1086/191677 http://doi.org/10.1086/191677 .

Mai, J.; Xiao, Y.; Zhou, G.; Wang, J.; Zhu, J.; Zhao, N.; Zhan, X.; Lu, X . Hidden structure ordering along backbone of fused-ring electron acceptors enhanced by ternary bulk heterojunction . Adv. Mater. , 2018 . 30 1802888 DOI: 10.1002/adma.201802888 http://doi.org/10.1002/adma.201802888 .

Xu, J.; Fu, W.; Yang, S.; Liu, T.; Li, C. Z.; Chen, H . Interface engineering in organic and organic/inorganic hybrid solar cells . Acta Polymerica Sinica (in Chinese) , 2018 . 164 - 173 . DOI: 10.1063/1.4895524 http://doi.org/10.1063/1.4895524 .

Zhou, G.; Zhang, M.; Chen, Z.; Zhang, J.; Zhan, L.; Li, S.; Zhu, L.; Wang, Z.; Zhu, X.; Chen, H.; Wang, L.; Liu, F.; Zhu, H . Marcus hole transfer governs charge generation and device operation in nonfullerene organic solar cells . ACS Energy Lett. , 2021 . 6 2971 - 2981 . DOI: 10.1021/acsenergylett.1c01154 http://doi.org/10.1021/acsenergylett.1c01154 .

Yu, Z. P.; Li, X.; He, C.; Wang, D.; Qin, R.; Zhou, G.; Liu, Z. X.; Andersen, T. R.; Zhu, H.; Chen, H.; Li, C. Z . High-efficiency organic solar cells with low voltage-loss of 0.46 V . Chin. Chem. Lett. , 2020 . 31 1991 - 1996 . DOI: 10.1016/j.cclet.2019.12.003 http://doi.org/10.1016/j.cclet.2019.12.003 .

浏览量

222

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

End-group and Side-chain Dual-engineering of Selenium-fused Acceptors for 20.08% Efficiency Polymer Solar Cells with Low Energy Loss

Towards Oxygen-stable Vinylene-linked Covalent Organic Frameworks: Mitigating Photobleaching for Enhanced Photostability

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers

Silk Sericin-inspired Poly-β-homoserine for Protein Protection

Upgrading Commercially Available Polyethylene to High-value Materials with Strong Mechanical Performance and Hydrophilicity by Blending with Ethylene/meta-Methoxystyrene Copolymers