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J. Semicond. > 2021, Volume 42?>?Issue 6?> 060501

SHORT COMMUNICATION

Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels

Xiongfeng Li1, 2, Jingui Xu2, 3, Zuo Xiao2, , Xingzhu Wang1, , Bin Zhang3, and Liming Ding2,

+ Author Affiliations

 Corresponding author: Zuo Xiao, xiaoz@nanoctr.cn; Xingzhu Wang, xzwang@xtu.edu.cn; Bin Zhang, msbinzhang@outlook.com; Liming Ding, ding@nanoctr.cn

DOI: 10.1088/1674-4926/42/6/060501

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[1]
Lin Y, Wang J, Zhang Z, et al. An electron acceptor challenging fullerenes for efficient polymer solar cells. Adv Mater, 2015, 27, 1170 doi: 10.1002/adma.201404317
[2]
Lin Y, He Q, Zhao F, et al. A facile planar fused-ring electron acceptor for as-cast polymer solar cells with 8.71% efficiency. J Am Chem Soc, 2016, 138, 2973 doi: 10.1021/jacs.6b00853
[3]
Holliday S, Ashraf R S, Wadsworth A, et al. High-efficiency and air-stable P3HT-based polymer solar cells with a new non-fullerene acceptor. Nat Commun, 2016, 7, 11585 doi: 10.1038/ncomms11585
[4]
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
[5]
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
[6]
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
[7]
Jin K, Xiao Z, Ding L. D18, an eximious solar polymer!. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[8]
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
[9]
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
[10]
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
[11]
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
[12]
Wu Y, Zheng Y, Yang H, et al. Rationally pairing photoactive materials for high-performance polymer solar cells with efficiency of 16.53%. Sci China Chem, 2020, 63, 265 doi: 10.1007/s11426-019-9599-1
[13]
Lan L, Chen Z, Hu Q, et al. High-performance polymer solar cells based on a wide-bandgap polymer containing pyrrolo[3,4-f] benzotriazole-5,7-dione with a power conversion efficiency of 8.63%. Adv Sci, 2016, 3, 1600032 doi: 10.1002/advs.201600032
[14]
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
[15]
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
[16]
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
[17]
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
[18]
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
[19]
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
[20]
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
[21]
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
[22]
Lee J, Sin D H, Clement J A, et al. Medium-bandgap conjugated polymers containing fused dithienobenzochalcogenadiazoles: Chalcogen atom effects on organic photovoltaics. Macromolecules, 2016, 49, 9358 doi: 10.1021/acs.macromol.6b01569
[23]
Rand B P, Burk D P, Forrest S R. Offset energies at organic semiconductor heterojunctions and their influence on the open-circuit voltage of thin-film solar cells. Phys Rev B, 2007, 75, 115327 doi: 10.1103/PhysRevB.75.115327
[24]
Xiong J, Xu J, Jiang Y, et al. Fused-ring bislactone building blocks for polymer donors. Sci Bull, 2020, 65, 1792 doi: 10.1016/j.scib.2020.07.018
[25]
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
[26]
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
[27]
Deng L, Li X, Wang S, et al. Stereomeric effects of bisPC71BM on polymer solar cell performance. Sci Bull, 2016, 61, 132 doi: 10.1007/s11434-015-0979-5
[28]
Wang J, Gao Y, Xiao Z, et al. A wide-bandgap copolymer donor based on a phenanthridin-6(5H)-one unit. Mater Chem Front, 2019, 3, 2686 doi: 10.1039/C9QM00622B
[29]
Zhang L, Jin K, Xiao Z, et al. Alkoxythiophene and alkylthiothiophene π-bridges enhance the performance of A-D-A electron acceptors. Mater Chem Front, 2019, 3, 492 doi: 10.1039/C8QM00647D
[30]
Jin K, Deng C, Zhang L, et al. A heptacyclic carbon-oxygen-bridged ladder-type building block for A-D-A acceptors. Mater Chem Front, 2018, 2, 1716 doi: 10.1039/C8QM00285A
[31]
Li W, Liu Q, Jin K, et al. Fused-ring phenazine building blocks for efficient copolymer donors. Mater Chem Front, 2020, 4, 1454 doi: 10.1039/D0QM00080A
Fig. 1.  (Color online) (a) DTBT and DTBO building blocks, and DTBO-based copolymers P1 and P2. (b) Molecular models and corresponding frontier molecular orbitals and energy levels for D18, P1 and P2. (c) J–V curves for P1:Y6 and P2:Y6 solar cells. (d) EQE spectra for P1:Y6 and P2:Y6 solar cells.

[1]
Lin Y, Wang J, Zhang Z, et al. An electron acceptor challenging fullerenes for efficient polymer solar cells. Adv Mater, 2015, 27, 1170 doi: 10.1002/adma.201404317
[2]
Lin Y, He Q, Zhao F, et al. A facile planar fused-ring electron acceptor for as-cast polymer solar cells with 8.71% efficiency. J Am Chem Soc, 2016, 138, 2973 doi: 10.1021/jacs.6b00853
[3]
Holliday S, Ashraf R S, Wadsworth A, et al. High-efficiency and air-stable P3HT-based polymer solar cells with a new non-fullerene acceptor. Nat Commun, 2016, 7, 11585 doi: 10.1038/ncomms11585
[4]
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
[5]
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
[6]
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
[7]
Jin K, Xiao Z, Ding L. D18, an eximious solar polymer!. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[8]
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
[9]
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
[10]
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
[11]
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
[12]
Wu Y, Zheng Y, Yang H, et al. Rationally pairing photoactive materials for high-performance polymer solar cells with efficiency of 16.53%. Sci China Chem, 2020, 63, 265 doi: 10.1007/s11426-019-9599-1
[13]
Lan L, Chen Z, Hu Q, et al. High-performance polymer solar cells based on a wide-bandgap polymer containing pyrrolo[3,4-f] benzotriazole-5,7-dione with a power conversion efficiency of 8.63%. Adv Sci, 2016, 3, 1600032 doi: 10.1002/advs.201600032
[14]
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
[15]
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
[16]
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
[17]
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
[18]
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
[19]
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
[20]
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
[21]
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
[22]
Lee J, Sin D H, Clement J A, et al. Medium-bandgap conjugated polymers containing fused dithienobenzochalcogenadiazoles: Chalcogen atom effects on organic photovoltaics. Macromolecules, 2016, 49, 9358 doi: 10.1021/acs.macromol.6b01569
[23]
Rand B P, Burk D P, Forrest S R. Offset energies at organic semiconductor heterojunctions and their influence on the open-circuit voltage of thin-film solar cells. Phys Rev B, 2007, 75, 115327 doi: 10.1103/PhysRevB.75.115327
[24]
Xiong J, Xu J, Jiang Y, et al. Fused-ring bislactone building blocks for polymer donors. Sci Bull, 2020, 65, 1792 doi: 10.1016/j.scib.2020.07.018
[25]
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
[26]
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
[27]
Deng L, Li X, Wang S, et al. Stereomeric effects of bisPC71BM on polymer solar cell performance. Sci Bull, 2016, 61, 132 doi: 10.1007/s11434-015-0979-5
[28]
Wang J, Gao Y, Xiao Z, et al. A wide-bandgap copolymer donor based on a phenanthridin-6(5H)-one unit. Mater Chem Front, 2019, 3, 2686 doi: 10.1039/C9QM00622B
[29]
Zhang L, Jin K, Xiao Z, et al. Alkoxythiophene and alkylthiothiophene π-bridges enhance the performance of A-D-A electron acceptors. Mater Chem Front, 2019, 3, 492 doi: 10.1039/C8QM00647D
[30]
Jin K, Deng C, Zhang L, et al. A heptacyclic carbon-oxygen-bridged ladder-type building block for A-D-A acceptors. Mater Chem Front, 2018, 2, 1716 doi: 10.1039/C8QM00285A
[31]
Li W, Liu Q, Jin K, et al. Fused-ring phenazine building blocks for efficient copolymer donors. Mater Chem Front, 2020, 4, 1454 doi: 10.1039/D0QM00080A

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    Received: 18 March 2021 Revised: Online: Accepted Manuscript: 18 March 2021Uncorrected proof: 18 March 2021Published: 01 June 2021

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      Xiongfeng Li, Jingui Xu, Zuo Xiao, Xingzhu Wang, Bin Zhang, Liming Ding. Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. Journal of Semiconductors, 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501 ****X F Li, J G Xu, Z Xiao, X Z Wang, B Zhang, L M Ding, Dithieno[3\',2\':3,4;2\'\',3\'\':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. J. Semicond., 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501.
      Citation:
      Xiongfeng Li, Jingui Xu, Zuo Xiao, Xingzhu Wang, Bin Zhang, Liming Ding. Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. Journal of Semiconductors, 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501 ****
      X F Li, J G Xu, Z Xiao, X Z Wang, B Zhang, L M Ding, Dithieno[3\',2\':3,4;2\'\',3\'\':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. J. Semicond., 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501.

      Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels

      DOI: 10.1088/1674-4926/42/6/060501
      • 1.

        College of Chemistry, Xiangtan University, Xiangtan 411105, 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

      More Information
      • Xiongfeng Li：got his BS degree from Xiangtan University. Now he is a master student at Xiangtan University under the supervision of Professor Xingzhu Wang. 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
      • Jingui Xu：got his BS degree from Yancheng Institute of Technology. Now he is a master student at Changzhou University under the supervision of Professor 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 Professor 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
      • Xingzhu Wang：obtained his PhD degree from Hong Kong Baptist University in 2009. After postdoctoral works at University of Cambridge and Nanyang Technological University, he worked at National University of Singapore from 2013 to 2017 as a senior research fellow and now he works at Xiangtan University and Southern University of Science and Technology as a professor. His research interests include organic synthesis, organic semiconductors and optoelectronic devices
      • Bin Zhang：got his BS degree from East China University of Technology in 2005. Then, he got his MS and PhD degrees 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 functional 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: xiaoz@nanoctr.cn; xzwang@xtu.edu.cn; msbinzhang@outlook.com; ding@nanoctr.cn
      • Received Date: 2021-03-18
      • Published Date: 2021-06-10

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