A wide-bandgap copolymer donor with a 5-methyl-4H-dithieno[3,2-e:2',3'-g]isoindole-4,6(5H)-dione unit

Anxin Sun; Jingui Xu; Guanhua Zong; Zuo Xiao; Yong Hua; Bin Zhang; Liming Ding

doi:10.1088/1674-4926/42/10/100502

J. Semicond. > 2021, Volume 42?>?Issue 10?> 100502

SHORT COMMUNICATION

A wide-bandgap copolymer donor with a 5-methyl-4H-dithieno[3,2-e:2',3'-g]isoindole-4,6(5H)-dione unit

Anxin Sun^{1, 2}, Jingui Xu^{2, 3}, Guanhua Zong², Zuo Xiao^2,, Yong Hua^1,, Bin Zhang^3, and Liming Ding^2,

+ Author Affiliations

1. Yunnan Key Laboratory for Micro/Nano Materials & Technology, School of Materials and Energy, Yunnan University, Kunming 650091, China
2. Center for Excellence in Nanoscience (CAS), Key Laboratory of Nanosystem and Hierarchical Fabrication (CAS), National Center for Nanoscience and Technology, Beijing 100190, China
3. School of Materials Science and Engineering, Changzhou University, Changzhou 213164, China

Author Bio:

Anxin Sun got his BS from Yunnan University. Now he is a master student at Yunnan University under the supervision of Prof. Yong Hua. Since August 2019, he has been working in Liming Ding Lab at National Center for Nanoscience and Technology as a visiting student. His work focuses on organic solar cells.

Jingui Xu got his BS from Yancheng Institute of Technology. Now he is a master student at Changzhou University under the supervision of Prof. Bin Zhang. Since September 2019, he has been working in Liming Ding Lab at National Center for Nanoscience and Technology as a visiting student. His work focuses on organic solar cells.

Zuo Xiao got his BS and PhD degrees from Peking University under the supervision of Prof. Liangbing Gan. He did postdoctoral research in Eiichi Nakamura Lab at the University of Tokyo. In March 2011, he joined Liming Ding Group at National Center for Nanoscience and Technology as an associate professor. In April 2020, he was promoted to be a full professor. His current research focuses on organic solar cells.

Yong Hua received his PhD in Hong Kong Baptist University in 2014. He then moved to KTH-Royal Institute of Technology as a postdoc. Since 2017, he is an associate professor in Materials Chemistry at Yunnan University. His current research focuses on perovskite solar cells.

Bin Zhang got his BS from East China University of Technology in 2005. Then, he got his MS and PhD from South China University of Technology (SCUT) in 2008 and 2012, respectively. From 2013 to 2017, he did postdoctoral research in SCUT and Shenzhen University. In 2018, he joined Changzhou University and was appointed as an associate professor. His research focuses on organic semiconductors and perovskite solar cells.

Liming Ding got his PhD from University of Science and Technology of China (was a joint student at Changchun Institute of Applied Chemistry, CAS). He started his research on OSCs and PLEDs in Olle Ingan?s Lab in 1998. Later on, he worked at National Center for Polymer Research, Wright-Patterson Air Force Base and Argonne National Lab (USA). He joined Konarka as a Senior Scientist in 2008. In 2010, he joined National Center for Nanoscience and Technology as a full professor. His research focuses on innovative materials and devices. He is RSC Fellow, the nominator for Xplorer Prize, and the Associate Editors for Science Bulletin and Journal of Semiconductors.

Corresponding author: Zuo Xiao, xiaoz@nanoctr.cn; Yong Hua, huayong@ynu.edu.cn; Bin Zhang, msbinzhang@outlook.com; Liming Ding, ding@nanoctr.cn

DOI: 10.1088/1674-4926/42/10/100502

References

[1]	Tong Y, Xiao Z, Du X, et al. Progress of the key materials for organic solar cells. Sci China Chem, 2020, 63, 758 doi: 10.1007/s11426-020-9726-0
[2]	Duan C, Ding L. The new era for organic solar cells: polymer donors. Sci Bull, 2020, 65, 1422 doi: 10.1016/j.scib.2020.04.044
[3]	Jin K, Xiao Z, Ding L. D18, an eximious solar polymer!. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[4]	Armin A, Li W, Sandberg O J, et al. A history and perspective of non-fullerene electron acceptors for organic solar cells. Adv Energy Mater, 2021, 11, 20003570 doi: 10.1002/aenm.202003570
[5]	Zhang M, Guo X, Ma W, et al. A large-bandgap conjugated polymer for versatile photovoltaic applications with high performance. Adv Mater, 2015, 27, 4655 doi: 10.1002/adma.201502110
[6]	Zhang S, Qin Y, Zhu J, et al. Over 14% efficiency in polymer solar cells enabled by a chlorinated polymer donor. Adv Mater, 2018, 30, 1800868 doi: 10.1002/adma.201800868
[7]	Xu Y, Cui Y, Yao H, et al. A new conjugated polymer that enables the integration of photovoltaic and light-emitting functions in one device. Adv Mater, 2021, 33, 2101090 doi: 10.1002/adma.202101090
[8]	Sun C, Pan F, Bin H, et al. A low cost and high performance polymer donor material for polymer solar cells. Nat Commun, 2018, 9, 743 doi: 10.1038/s41467-018-03207-x
[9]	Zhu C, Meng L, Zhang J, et al. A quinoxaline-based D-A copolymer donor achieving 17.62% efficiency of organic solar cells. Adv Mater, 2021, 33, 2100474 doi: 10.1002/adma.202100474
[10]	Fan B, Zhang D, Li M, et al. Achieving over 16% efficiency for single-junction organic solar cells. Sci China Chem, 2019, 62, 746 doi: 10.1007/s11426-019-9457-5
[11]	Xiong J, Jin K, Jiang Y, et al. Thiolactone copolymer donor gifts organic solar cells a 16.72% efficiency. Sci Bull, 2019, 64, 1573 doi: 10.1016/j.scib.2019.10.002
[12]	Jiang Y, Jin K, Chen X, et al. Post-sulphuration enhances the performance of a lactone polymer donor. J Semicond, 2021, 42, 070501 doi: 10.1088/1674-4926/42/7/070501
[13]	Liu Q, Jiang Y, Jin K, et al. 18% efficiency organic solar cells. Sci Bull, 2020, 65, 272 doi: 10.1016/j.scib.2020.01.001
[14]	Qin J, Zhang L, Xiao Z, et al. Over 16% efficiency from thick-film organic solar cells. Sci Bull, 2020, 65, 1979 doi: 10.1016/j.scib.2020.08.027
[15]	Qin J, Zhang L, Zuo C, et al. A chlorinated copolymer donor demonstrates a 18.13% power conversion efficiency. J Semicond, 2021, 42, 010501 doi: 10.1088/1674-4926/42/1/010501
[16]	Jin K, Xiao Z, Ding L. 18.69% PCE from organic solar cells. J Semicond, 2021, 42, 060502 doi: 10.1088/1674-4926/42/6/060502
[17]	Grzybowski M, Skonieczny K, Butenschon H, et al. Comparison of oxidative aromatic coupling and the Scholl reaction. Angew Chem Int Ed, 2013, 52, 9900 doi: 10.1002/anie.201210238
[18]	Ziffer M E, Jo S B, Liu Y, et al. Tuning H- and J-aggregate behavior in π-conjugated polymers via noncovalent interactions. J Phys Chem C, 2018, 122, 18860 doi: 10.1021/acs.jpcc.8b05505
[19]	Jiang K, Wei Q, Lai J Y L, et al. Alkyl chain tuning of small molecule acceptors for efficient organic solar cells. Joule, 2019, 3, 3020 doi: 10.1016/j.joule.2019.09.010
[20]	Zhao W, Li S, Yao H, et al. Molecular optimization enables over 13% efficiency in organic solar cells. J Am Chem Soc, 2017, 139, 7148 doi: 10.1021/jacs.7b02677
[21]	Liu J, Liu L, Zuo C, et al. 5H-dithieno[3,2-b:2',3'-d]pyran-5-one unit yields efficient wide-bandgap polymer donors. Sci Bull, 2019, 64, 1655 doi: 10.1016/j.scib.2019.09.001
[22]	Xiao Z, Geng X, He D, et al. Development of isomer-free fullerene bisadducts for efficient polymer solar cells. Energy Environ Sci, 2016, 9, 2114 doi: 10.1039/C6EE01026A
[23]	Xiao Z, Jia X, Ding L, et al. Ternary organic solar cells offer 14% power conversion efficiency. Sci Bull, 2017, 62, 1562 doi: 10.1016/j.scib.2017.11.003
[24]	Wang T, Qin J, Xiao Z, et al. A 2.16 eV bandgap polymer donor gives 16% power conversion efficiency. Sci Bull, 2020, 65, 179 doi: 10.1016/j.scib.2019.11.030
[25]	Luo Y, Chen X, Xiao Z, et al. A large-bandgap copolymer donor for efficient ternary organic solar cells. Mater Chem Front, 2021, 5, 6139 doi: 10.1039/D1QM00835H
[26]	Wang T, Qin J, Xiao Z, et al. Multiple conformation locks gift polymer donor high efficiency. Nano Energy, 2020, 77, 105161 doi: 10.1016/j.nanoen.2020.105161
[27]	Xiao Z, Jia X, Li D, et al. 26 mA cm^–2 J_sc from organic solar cells with a low-bandgap nonfullerene acceptor. Sci Bull, 2017, 62, 1494 doi: 10.1016/j.scib.2017.10.017
[28]	Liu L, Liu Q, Xiao Z, et al. Induced J-aggregation in acceptor alloy enhances photocurrent. Sci Bull, 2019, 64, 1083 doi: 10.1016/j.scib.2019.06.005
[29]	Xiao Z, Liu F, Geng X, et al. A carbon-oxygen-bridged ladder-type building block for efficient donor and acceptor materials used in organic solar cells. Sci Bull, 2017, 62, 1331 doi: 10.1016/j.scib.2017.09.017

Fig. 1. (a) The structures of D18 and P1, and DFT-predicted molecular geometries, HOMO and LUMO of DTBT and MDTID units. (b) The synthetic route for P1. (c) Absorption spectra for P1 in CHCl₃, and P1, N3 and IT-4F films. (d) J–V curves for P1:N3 and P1:IT-4F solar cells. (e) EQE spectra for P1:N3 and P1:IT-4F solar cells.

DownLoad: Full-Size Img PowerPoint

Table 1. Performance data for P1:N3 and P1:IT-4F solar cells.

D/A	V_oc (V)	J_sc (mA/cm²)	FF (%)	PCE (%)
P1:N3	0.90	24.52 (23.34)^a	65.8	14.52 (14.25)^b
P1:IT-4F	0.95	20.31 (19.83)^a	64.6	12.46 (12.29)^b
^a The data in the parentheses are integrated photocurrent densities from EQE spectra; ^bthe data in the parentheses are averages for 10 cells.

DownLoad: CSV

[1]	Tong Y, Xiao Z, Du X, et al. Progress of the key materials for organic solar cells. Sci China Chem, 2020, 63, 758 doi: 10.1007/s11426-020-9726-0
[2]	Duan C, Ding L. The new era for organic solar cells: polymer donors. Sci Bull, 2020, 65, 1422 doi: 10.1016/j.scib.2020.04.044
[3]	Jin K, Xiao Z, Ding L. D18, an eximious solar polymer!. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[4]	Armin A, Li W, Sandberg O J, et al. A history and perspective of non-fullerene electron acceptors for organic solar cells. Adv Energy Mater, 2021, 11, 20003570 doi: 10.1002/aenm.202003570
[5]	Zhang M, Guo X, Ma W, et al. A large-bandgap conjugated polymer for versatile photovoltaic applications with high performance. Adv Mater, 2015, 27, 4655 doi: 10.1002/adma.201502110
[6]	Zhang S, Qin Y, Zhu J, et al. Over 14% efficiency in polymer solar cells enabled by a chlorinated polymer donor. Adv Mater, 2018, 30, 1800868 doi: 10.1002/adma.201800868
[7]	Xu Y, Cui Y, Yao H, et al. A new conjugated polymer that enables the integration of photovoltaic and light-emitting functions in one device. Adv Mater, 2021, 33, 2101090 doi: 10.1002/adma.202101090
[8]	Sun C, Pan F, Bin H, et al. A low cost and high performance polymer donor material for polymer solar cells. Nat Commun, 2018, 9, 743 doi: 10.1038/s41467-018-03207-x
[9]	Zhu C, Meng L, Zhang J, et al. A quinoxaline-based D-A copolymer donor achieving 17.62% efficiency of organic solar cells. Adv Mater, 2021, 33, 2100474 doi: 10.1002/adma.202100474
[10]	Fan B, Zhang D, Li M, et al. Achieving over 16% efficiency for single-junction organic solar cells. Sci China Chem, 2019, 62, 746 doi: 10.1007/s11426-019-9457-5
[11]	Xiong J, Jin K, Jiang Y, et al. Thiolactone copolymer donor gifts organic solar cells a 16.72% efficiency. Sci Bull, 2019, 64, 1573 doi: 10.1016/j.scib.2019.10.002
[12]	Jiang Y, Jin K, Chen X, et al. Post-sulphuration enhances the performance of a lactone polymer donor. J Semicond, 2021, 42, 070501 doi: 10.1088/1674-4926/42/7/070501
[13]	Liu Q, Jiang Y, Jin K, et al. 18% efficiency organic solar cells. Sci Bull, 2020, 65, 272 doi: 10.1016/j.scib.2020.01.001
[14]	Qin J, Zhang L, Xiao Z, et al. Over 16% efficiency from thick-film organic solar cells. Sci Bull, 2020, 65, 1979 doi: 10.1016/j.scib.2020.08.027
[15]	Qin J, Zhang L, Zuo C, et al. A chlorinated copolymer donor demonstrates a 18.13% power conversion efficiency. J Semicond, 2021, 42, 010501 doi: 10.1088/1674-4926/42/1/010501
[16]	Jin K, Xiao Z, Ding L. 18.69% PCE from organic solar cells. J Semicond, 2021, 42, 060502 doi: 10.1088/1674-4926/42/6/060502
[17]	Grzybowski M, Skonieczny K, Butenschon H, et al. Comparison of oxidative aromatic coupling and the Scholl reaction. Angew Chem Int Ed, 2013, 52, 9900 doi: 10.1002/anie.201210238
[18]	Ziffer M E, Jo S B, Liu Y, et al. Tuning H- and J-aggregate behavior in π-conjugated polymers via noncovalent interactions. J Phys Chem C, 2018, 122, 18860 doi: 10.1021/acs.jpcc.8b05505
[19]	Jiang K, Wei Q, Lai J Y L, et al. Alkyl chain tuning of small molecule acceptors for efficient organic solar cells. Joule, 2019, 3, 3020 doi: 10.1016/j.joule.2019.09.010
[20]	Zhao W, Li S, Yao H, et al. Molecular optimization enables over 13% efficiency in organic solar cells. J Am Chem Soc, 2017, 139, 7148 doi: 10.1021/jacs.7b02677
[21]	Liu J, Liu L, Zuo C, et al. 5H-dithieno[3,2-b:2',3'-d]pyran-5-one unit yields efficient wide-bandgap polymer donors. Sci Bull, 2019, 64, 1655 doi: 10.1016/j.scib.2019.09.001
[22]	Xiao Z, Geng X, He D, et al. Development of isomer-free fullerene bisadducts for efficient polymer solar cells. Energy Environ Sci, 2016, 9, 2114 doi: 10.1039/C6EE01026A
[23]	Xiao Z, Jia X, Ding L, et al. Ternary organic solar cells offer 14% power conversion efficiency. Sci Bull, 2017, 62, 1562 doi: 10.1016/j.scib.2017.11.003
[24]	Wang T, Qin J, Xiao Z, et al. A 2.16 eV bandgap polymer donor gives 16% power conversion efficiency. Sci Bull, 2020, 65, 179 doi: 10.1016/j.scib.2019.11.030
[25]	Luo Y, Chen X, Xiao Z, et al. A large-bandgap copolymer donor for efficient ternary organic solar cells. Mater Chem Front, 2021, 5, 6139 doi: 10.1039/D1QM00835H
[26]	Wang T, Qin J, Xiao Z, et al. Multiple conformation locks gift polymer donor high efficiency. Nano Energy, 2020, 77, 105161 doi: 10.1016/j.nanoen.2020.105161
[27]	Xiao Z, Jia X, Li D, et al. 26 mA cm^–2 J_sc from organic solar cells with a low-bandgap nonfullerene acceptor. Sci Bull, 2017, 62, 1494 doi: 10.1016/j.scib.2017.10.017
[28]	Liu L, Liu Q, Xiao Z, et al. Induced J-aggregation in acceptor alloy enhances photocurrent. Sci Bull, 2019, 64, 1083 doi: 10.1016/j.scib.2019.06.005
[29]	Xiao Z, Liu F, Geng X, et al. A carbon-oxygen-bridged ladder-type building block for efficient donor and acceptor materials used in organic solar cells. Sci Bull, 2017, 62, 1331 doi: 10.1016/j.scib.2017.09.017