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J. Semicond. > 2022, Volume 43?>?Issue 5?> 050501

SHORT COMMUNICATION

A chlorinated lactone polymer donor featuring high performance and low cost

Ke Jin1, Zongliang Ou2, Lixiu Zhang1, Yongbo Yuan4, Zuo Xiao1, , Qiuling Song2, , Chenyi Yi3, and Liming Ding1,

+ Author Affiliations

 Corresponding author: Zuo Xiao, xiaoz@nanoctr.cn; Qiuling Song, qsong@hqu.edu.cn; Chenyi Yi, yicy@mail.tsinghua.edu.cn; Liming Ding, ding@nanoctr.cn

DOI: 10.1088/1674-4926/43/5/050501

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[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]
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
[3]
Xiao Z, Yang S, Yang Z, et al. Carbon-oxygen-bridged ladder-type building blocks for highly efficient nonfullerene acceptors. Adv Mater, 2018, 31, 1804790 doi: 10.1002/adma.201804790
[4]
Xiao Z, Jia X, Ding L. Ternary organic solar cells offer 14% power conversion efficiency. Sci Bull, 2017, 62, 1562 doi: 10.1016/j.scib.2017.11.003
[5]
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
[6]
Li H, Xiao Z, Ding L, et al. Thermostable single-junction organic solar cells with a power conversion efficiency of 14.62%. Sci Bull, 2018, 63, 340 doi: 10.1016/j.scib.2018.02.015
[7]
Liu B, Xu Y, Xia D, et al. Semitransparent organic solar cells based on non-fullerene electron acceptors. Acta Phys Chim Sin, 2021, 37, 2009056 doi: 10.3866/PKU.WHXB202009056
[8]
Yuan J, Zhang Y, Zhou L, et al. Single-junction organic solar cell with over 15% efficiency using fused-ring acceptor with electron-deficient core. Joule, 2019, 3, 1140 doi: 10.1016/j.joule.2019.01.004
[9]
Cui Y, Yao H, Zhang J, et al. Single-junction organic photovoltaic cells with approaching 18% efficiency. Adv Mater, 2020, 32, 1908205 doi: 10.1002/adma.201908205
[10]
Li C, Zhou J, Song J, et al. Non-fullerene acceptors with branched side chains and improved molecular packing to exceed 18% efficiency in organic solar cells. Nat Energy, 2021, 6, 605 doi: 10.1038/s41560-021-00820-x
[11]
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
[12]
Wang T, Qin J, Xiao Z, et al. Mutiple conformation locks gift polymer donor high efficiency. Nano Energy, 2020, 77, 105161 doi: 10.1016/j.nanoen.2020.105161
[13]
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
[14]
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
[15]
Jin K, Xiao Z, Ding L. D18, an eximious solar polymer!. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[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]
Cui Y, Xu Y, Yao H, et al. Single-junction organic photovoltaic cell with 19% efficiency. Adv Mater, 2021, 33, 2102420 doi: 10.1002/adma.202102420
[18]
Cai Y, Huo L, Sun Y. Recent adcances in wide-bandgap photovoltaic polymers. Adv Mater, 2017, 29, 1605437 doi: 10.1002/adma.201605437
[19]
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
[20]
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
[21]
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
[22]
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
[23]
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
[24]
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
[25]
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
[26]
Meng X, Jin K, Xiao Z, et al. Side chain engineering on D18 polymers yields 18.74% power conversion efficiency. J Semicond, 2021, 42, 100501 doi: 10.1088/1674-4926/42/10/100501
[27]
Bi P, Zhang S, Chen Z, et al. Reduced non-radiative charge recombination enables organic photovoltaic cell approaching 19% efficiency. Joule, 2021, 5, 2408 doi: 10.1016/j.joule.2021.06.020
[28]
Xue R, Zhang J, Li Y, et al. Organic solar cell materials toward commercialization. Small, 2018, 14, 1801793 doi: 10.1002/smll.201801793
[29]
Xu J, Sun A, Xiao Z, et al. Efficient wide-bandgap copolymer donors with reduced synthesis cost. J Mater Chem C, 2021, 9, 16187 doi: 10.1039/D1TC01746B
[30]
Qin X, Li X, Huang Q, et al. Rhodium(III)-catalyzed ortho C-H heteroarylation of (hetero)aromatic carboxylic acids: a rapid and concise access to π-conjugated poly-heterocycles. Angew Chem Int Ed, 2015, 54, 7167 doi: 10.1002/anie.201501982
[31]
Ou Z, Qin J, Jin K, et al. Engineering of the alkyl chain branching point on a lactone polymer donor yields 17.81% efficiency. J Mater Chem A, 2022, 10, 3314 doi: 10.1039/D1TA10233H
[32]
Yao H, Wang J, Xu Y, et al. Recent progress in chlorinated organic photovoltaic materials. Acc Chem Res, 2020, 53, 822 doi: 10.1021/acs.accounts.0c00009
[33]
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
[34]
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
[35]
Xiao Z, Jia X, Li D, et al. 26 mA cm–2 Jsc from organic solar cells with a low-bandgap nonfullerene acceptor. Sci Bull, 2017, 62, 494 doi: 10.1016/j.scib.2017.10.017
[36]
Xiao Z, Geng X, He D, et al. Development of isomer-free fullerene bisadducts for efficient polymer solar cells. Sci Bull, 2016, 9, 2114 doi: 10.1039/C6EE01026A
[37]
Li D, Xiao Z, Wang S, et al. A thieno[3,2-c]isoquinolin-5(4H)-one building block for efficient thick-film solar cells. Adv Energy Mater, 2018, 8, 1800397 doi: 10.1002/aenm.201800397
[38]
Gao Y, Li D, Xiao Z, et al. High-performance wide-bandgap copolymers with dithieno[3,2-b:2',3'-d]pyridin-5(4H)-one units. Mater Chem Front, 2019, 3, 399 doi: 10.1039/C8QM00604K
[39]
Li T, Zhang H, Xiao Z, et al. A carbon-oxygen-bridged hexacyclic ladder-type building block for low-bandgap nonfullerene acceptors. Mater Chem Front, 2018, 2, 700 doi: 10.1039/C8QM00004B
[40]
Jin K, Deng C, Zhang L, et al. A heptacyclic carbon-oxygem-bridged ladder-type building for A-D-A acceptors. Mater Chem Front, 2018, 2, 1716 doi: 10.1039/C8QM00285A
[41]
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
[42]
An M, Xie F, Geng X, et al. A high-performance D-A copolymer based on dithieno[3,2-b:2',3'-d]pyridin-5(4H)-one unit compatible with fullerene and nonfullerene acceptors in solar cells. Adv Energy Mater, 2017, 7, 1602509 doi: 10.1002/aenm.201602509
Fig. 1.  (Color online) (a) Polymer donors offering PCEs over 18%. (b) J–V curves for L4:N3 and L4:N3:PC61BM solar cells. (c) EQE spectra for L4:N3 and L4:N3:PC61BM solar cells.

[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]
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
[3]
Xiao Z, Yang S, Yang Z, et al. Carbon-oxygen-bridged ladder-type building blocks for highly efficient nonfullerene acceptors. Adv Mater, 2018, 31, 1804790 doi: 10.1002/adma.201804790
[4]
Xiao Z, Jia X, Ding L. Ternary organic solar cells offer 14% power conversion efficiency. Sci Bull, 2017, 62, 1562 doi: 10.1016/j.scib.2017.11.003
[5]
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
[6]
Li H, Xiao Z, Ding L, et al. Thermostable single-junction organic solar cells with a power conversion efficiency of 14.62%. Sci Bull, 2018, 63, 340 doi: 10.1016/j.scib.2018.02.015
[7]
Liu B, Xu Y, Xia D, et al. Semitransparent organic solar cells based on non-fullerene electron acceptors. Acta Phys Chim Sin, 2021, 37, 2009056 doi: 10.3866/PKU.WHXB202009056
[8]
Yuan J, Zhang Y, Zhou L, et al. Single-junction organic solar cell with over 15% efficiency using fused-ring acceptor with electron-deficient core. Joule, 2019, 3, 1140 doi: 10.1016/j.joule.2019.01.004
[9]
Cui Y, Yao H, Zhang J, et al. Single-junction organic photovoltaic cells with approaching 18% efficiency. Adv Mater, 2020, 32, 1908205 doi: 10.1002/adma.201908205
[10]
Li C, Zhou J, Song J, et al. Non-fullerene acceptors with branched side chains and improved molecular packing to exceed 18% efficiency in organic solar cells. Nat Energy, 2021, 6, 605 doi: 10.1038/s41560-021-00820-x
[11]
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
[12]
Wang T, Qin J, Xiao Z, et al. Mutiple conformation locks gift polymer donor high efficiency. Nano Energy, 2020, 77, 105161 doi: 10.1016/j.nanoen.2020.105161
[13]
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
[14]
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
[15]
Jin K, Xiao Z, Ding L. D18, an eximious solar polymer!. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[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]
Cui Y, Xu Y, Yao H, et al. Single-junction organic photovoltaic cell with 19% efficiency. Adv Mater, 2021, 33, 2102420 doi: 10.1002/adma.202102420
[18]
Cai Y, Huo L, Sun Y. Recent adcances in wide-bandgap photovoltaic polymers. Adv Mater, 2017, 29, 1605437 doi: 10.1002/adma.201605437
[19]
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
[20]
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
[21]
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
[22]
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
[23]
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
[24]
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
[25]
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
[26]
Meng X, Jin K, Xiao Z, et al. Side chain engineering on D18 polymers yields 18.74% power conversion efficiency. J Semicond, 2021, 42, 100501 doi: 10.1088/1674-4926/42/10/100501
[27]
Bi P, Zhang S, Chen Z, et al. Reduced non-radiative charge recombination enables organic photovoltaic cell approaching 19% efficiency. Joule, 2021, 5, 2408 doi: 10.1016/j.joule.2021.06.020
[28]
Xue R, Zhang J, Li Y, et al. Organic solar cell materials toward commercialization. Small, 2018, 14, 1801793 doi: 10.1002/smll.201801793
[29]
Xu J, Sun A, Xiao Z, et al. Efficient wide-bandgap copolymer donors with reduced synthesis cost. J Mater Chem C, 2021, 9, 16187 doi: 10.1039/D1TC01746B
[30]
Qin X, Li X, Huang Q, et al. Rhodium(III)-catalyzed ortho C-H heteroarylation of (hetero)aromatic carboxylic acids: a rapid and concise access to π-conjugated poly-heterocycles. Angew Chem Int Ed, 2015, 54, 7167 doi: 10.1002/anie.201501982
[31]
Ou Z, Qin J, Jin K, et al. Engineering of the alkyl chain branching point on a lactone polymer donor yields 17.81% efficiency. J Mater Chem A, 2022, 10, 3314 doi: 10.1039/D1TA10233H
[32]
Yao H, Wang J, Xu Y, et al. Recent progress in chlorinated organic photovoltaic materials. Acc Chem Res, 2020, 53, 822 doi: 10.1021/acs.accounts.0c00009
[33]
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
[34]
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
[35]
Xiao Z, Jia X, Li D, et al. 26 mA cm–2 Jsc from organic solar cells with a low-bandgap nonfullerene acceptor. Sci Bull, 2017, 62, 494 doi: 10.1016/j.scib.2017.10.017
[36]
Xiao Z, Geng X, He D, et al. Development of isomer-free fullerene bisadducts for efficient polymer solar cells. Sci Bull, 2016, 9, 2114 doi: 10.1039/C6EE01026A
[37]
Li D, Xiao Z, Wang S, et al. A thieno[3,2-c]isoquinolin-5(4H)-one building block for efficient thick-film solar cells. Adv Energy Mater, 2018, 8, 1800397 doi: 10.1002/aenm.201800397
[38]
Gao Y, Li D, Xiao Z, et al. High-performance wide-bandgap copolymers with dithieno[3,2-b:2',3'-d]pyridin-5(4H)-one units. Mater Chem Front, 2019, 3, 399 doi: 10.1039/C8QM00604K
[39]
Li T, Zhang H, Xiao Z, et al. A carbon-oxygen-bridged hexacyclic ladder-type building block for low-bandgap nonfullerene acceptors. Mater Chem Front, 2018, 2, 700 doi: 10.1039/C8QM00004B
[40]
Jin K, Deng C, Zhang L, et al. A heptacyclic carbon-oxygem-bridged ladder-type building for A-D-A acceptors. Mater Chem Front, 2018, 2, 1716 doi: 10.1039/C8QM00285A
[41]
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
[42]
An M, Xie F, Geng X, et al. A high-performance D-A copolymer based on dithieno[3,2-b:2',3'-d]pyridin-5(4H)-one unit compatible with fullerene and nonfullerene acceptors in solar cells. Adv Energy Mater, 2017, 7, 1602509 doi: 10.1002/aenm.201602509

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    Received: 23 February 2022 Revised: Online: Accepted Manuscript: 25 February 2022Uncorrected proof: 25 February 2022Published: 01 May 2022

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      Ke Jin, Zongliang Ou, Lixiu Zhang, Yongbo Yuan, Zuo Xiao, Qiuling Song, Chenyi Yi, Liming Ding. A chlorinated lactone polymer donor featuring high performance and low cost[J]. Journal of Semiconductors, 2022, 43(5): 050501. doi: 10.1088/1674-4926/43/5/050501 ****K Jin, Z L Ou, L X Zhang, Y B Yuan, Z Xiao, Q L Song, C Y Yi, L M Ding. A chlorinated lactone polymer donor featuring high performance and low cost[J]. J. Semicond, 2022, 43(5): 050501. doi: 10.1088/1674-4926/43/5/050501
      Citation:
      Ke Jin, Zongliang Ou, Lixiu Zhang, Yongbo Yuan, Zuo Xiao, Qiuling Song, Chenyi Yi, Liming Ding. A chlorinated lactone polymer donor featuring high performance and low cost[J]. Journal of Semiconductors, 2022, 43(5): 050501. doi: 10.1088/1674-4926/43/5/050501 ****
      K Jin, Z L Ou, L X Zhang, Y B Yuan, Z Xiao, Q L Song, C Y Yi, L M Ding. A chlorinated lactone polymer donor featuring high performance and low cost[J]. J. Semicond, 2022, 43(5): 050501. doi: 10.1088/1674-4926/43/5/050501

      A chlorinated lactone polymer donor featuring high performance and low cost

      DOI: 10.1088/1674-4926/43/5/050501
      • 1.

        Center for Excellence in Nanoscience (CAS), Key Laboratory of Nanosystem and Hierarchical Fabrication (CAS), National Center for Nanoscience and Technology, Beijing 100190, China

      • 2.

        College of Materials Science & Engineering, Huaqiao University, Xiamen 361021, China

      • 3.

        State Key Laboratory of Power System, Department of Electrical Engineering, Tsinghua University, Beijing 100084, China

      • 4.

        School of Physics and Electronics, Central South University, Changsha 410083, China

      More Information
      • Ke Jin：got his MS from Wuhan Institute of Technology in 2019. Now he is a research assistant in Liming Ding Group at National Center for Nanoscience and Technology. His research focuses on organic solar cells
      • Zongliang Ou：got his BS from Henan University of Technology in 2019. Now he is a master student at Huaqiao University under the supervision of Professor Qiuling Song. Since September 2020, he has been working in Liming Ding Group 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 from Peking University under the supervision of Prof. Liangbing Gan. He did postdoctoral research in Eiichi Nakamura Group 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 research focuses on organic solar cells
      • Qiuling Song：obtained her MS in organic chemistry from Peking University under the supervision of Prof. Zhenfeng Xi and her PhD from Princeton University with Prof. Robert A. Pascal. She started her independent work in 2013 after 5 years working in pharmaceutical companies in USA. Currently her research interests include fluorine chemistry, boron chemistry and radical chemistry
      • Chenyi Yi：is an associate professor in Department of Electrical Engineering in Tsinghua University since 2017. He got his PhD from University of Bern, Switzerland in 2010. After that, he worked as a postdoc in Michael Gr?tzel Group in EPFL, Switzerland. His research includes perovskite solar cells, energy storage materials and devices. He is an associate editor for iEnergy
      • 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 Ingans 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 functional materials and devices. He is RSC Fellow, the nominator for Xplorer Prize, and the Associate Editor for Journal of Semiconductors
      • Corresponding author: xiaoz@nanoctr.cn; qsong@hqu.edu.cn; yicy@mail.tsinghua.edu.cn; ding@nanoctr.cn
      • Received Date: 2022-02-23
        Available Online: 2022-04-22

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