Rational Design of Conjugated Polymers for <italic style="font-style: italic">d</italic>-Limonene Processed All-polymer Solar Cells with Small Energy Loss

Mei-Jing Li; Bao-Bing Fan; Wen-Kai Zhong; Zhao-Mi-Yi Zeng; Jing-Kun Xu; Lei Ying

doi:10.1007/s10118-020-2429-3

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Rational Design of Conjugated Polymers for d-Limonene Processed All-polymer Solar Cells with Small Energy Loss

RAPID COMMUNICATION | Updated：2020-05-18

- Rational Design of Conjugated Polymers for d-Limonene Processed All-polymer Solar Cells with Small Energy Loss
- Chinese Journal of Polymer Science Vol. 38, Issue 8, Pages: 791-796(2020)
- Affiliations：
  
  a.Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China
  b.School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang 330013, China
  c.South China Institute of Collaborative Innovation, Dongguan 523808, China
- Author bio：
  
  msleiying@scut.edu.cn
- Funds：
- DOI：10.1007/s10118-020-2429-3
  CLC：
- Received：26 February 2020，
  
  Revised：2020-3-13，
  
  Accepted：17 March 2020，
  
  Online First：18 May 2020，
  
  Published：2020-08
- Accepted：
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Li, M. J.; Fan, B. B.; Zhong, W. K.; Zeng, Z. M. Y.; Xu, J. K.; Ying, L. Rational design of conjugated polymers for , d,-limonene processed all-polymer solar cells with small energy loss. Chinese J. Polym. Sci. 2020, 38, 791–796

Mei-Jing Li, Bao-Bing Fan, Wen-Kai Zhong, et al. Rational Design of Conjugated Polymers for d-Limonene Processed All-polymer Solar Cells with Small Energy Loss[J]. Chinese Journal of Polymer Science, 2020, 38(8): 791-796. DOI: 10.1007/s10118-020-2429-3.
Li, M. J.; Fan, B. B.; Zhong, W. K.; Zeng, Z. M. Y.; Xu, J. K.; Ying, L. Rational design of conjugated polymers for , d,-limonene processed all-polymer solar cells with small energy loss. Chinese J. Polym. Sci. 2020, 38, 791–796 DOI： 10.1007/s10118-020-2429-3.

Mei-Jing Li, Bao-Bing Fan, Wen-Kai Zhong, et al. Rational Design of Conjugated Polymers for d-Limonene Processed All-polymer Solar Cells with Small Energy Loss[J]. Chinese Journal of Polymer Science, 2020, 38(8): 791-796. DOI: 10.1007/s10118-020-2429-3. DOI：

摘要

Abstract

In this work

we designed and synthesized a novel naphthalenediimide-based n-type conjugated polymer

PNDICl

which bears asymmetric backbone containing a 3-chlorothiophene unit. The asymmetric structure associated with steric effects of the chlorine atom imparts remarkable solubility to

PNDICl

in various organic solvents

enabling the fabrication of all-polymer solar cells (all-PSCs) by using an environmentally friendly solvent of

-limonene. Combined with a novel pyrrolo[3

]benzotriazole-5

7(6

)-dione based p-type conjugated polymer

P2F-Si

with deep highest occupied molecular orbital energy level

the resulting

-limonene-processed all-PSCs presents an impressively high open-circuit voltage of approaching 1.0 V

corresponding to a very small energy loss of 0.49 eV. Through further morphology optimization by using

-valerolactone

we demonstrated an impressive device efficiency of 4.2%

which is among the best photovoltaic performance of devices processed using

-limonene and comparable to that processed by conventional solvent

suggesting the great promise of using greener solvent for fabricating high-performance all-PSCs.

关键词

Keywords

references

Lee, C.; Lee, S.; Kim, G. U.; Lee, W.; Kim, B. J. . Recent advances, design guidelines, and prospects of all-polymer solar cells . Chem. Rev. , 2019 . 119 8028 - 8086 . DOI: 10.1021/acs.chemrev.9b00044 http://doi.org/10.1021/acs.chemrev.9b00044 .

Yan, C.; Barlow, S.; Wang, Z.; Yan, H.; Jen, A. K. Y.; Marder, S. R.; Zhan, X. . Non-fullerene acceptors for organic solar cells . Nat. Rev. Mater. , 2018 . 3 18003 DOI: 10.1038/natrevmats.2018.3 http://doi.org/10.1038/natrevmats.2018.3 .

Li, Z.; Zhong, W.; Ying, L.; Liu, F. Li, N.; Huang, F.; Cao, Y. . Morphology optimization via molecular weight tuning of donor polymer enables all-polymer solar cells with simultaneously improved performance and stability . Nano Energy , 2019 . 64 103931 DOI: 10.1016/j.nanoen.2019.103931 http://doi.org/10.1016/j.nanoen.2019.103931 .

Li, Z.; Zhong, W.; Ying, L.; Li, N.; Liu, F.; Huang, F.; Cao, Y. . Achieving efficient thick film all-polymer solar cells using a green solvent additive . Chinese J. Polym. Sci. , 2020 . 38 323 - 331 . DOI: 10.1007/s10118-020-2356-3 http://doi.org/10.1007/s10118-020-2356-3 .

Zhao, R.; Dou, C.; Liu, J.; Wang, L. . An alternating polymer of two building blocks based on B←N unit: non-fullerene acceptor for organic photovoltaics . Chinese J. Polym. Sci. , 2017 . 35 198 - 206 . DOI: 10.1007/s10118-017-1878-9 http://doi.org/10.1007/s10118-017-1878-9 .

Huo, Y.; Zhang, H. L.; Zhan, X. . Nonfullerene all-small-molecule organic solar cells . ACS Energy Lett. , 2019 . 4 1241 - 1250 . DOI: 10.1021/acsenergylett.9b00528 http://doi.org/10.1021/acsenergylett.9b00528 .

Huang. F.; Bo, Z.; Geng Y.; Wang, X.; Wang, L.; Ma, Y.; Hou, J.; Hu, W.; Pei, J.; Dong, H.; Wang, S.; Li, Z.; Shuai, Z.; Li, Y.; Cao, Y. . Study on optoelectronic polymers: an overview and outlook . Acta Polymerica Sinica (in Chinese) , 2019 . 50 988 - 1046 . .

Zhong, W.; Xie, R.; Ying, L.; Huang, F.; Cao, Y. . High performance polymer photodetectors enabled by a naphtho[1,2- c :5,6- c ′]bis([1,2,5] thiadiazole) based π -conjugated polymer . Acta Polymerica Sinica (in Chinese) , 2018 . 217 - 222 . .

Dang, D.; Chen, W.; Himmelberger, S.; Tao, Q.; Lundin, A.; Yang, R.; Zhu, W.; Salleo, A.; Müller, C.; Wang, E. . Enhanced photovoltaic performance of indacenodithiophene-quinoxaline copolymers by side-chain modulation . Adv. Energy Mater. , 2014 . 4 1400680 DOI: 10.1002/aenm.201400680 http://doi.org/10.1002/aenm.201400680 .

Fan, B.; Zhang, D.; Li, M.; Zhong, W.; Zeng, Z.; Ying, L.; Huang, F.; Cao, Y. . Achieving over 16% efficiency for single-junction organic solar cells . Sci. China Chem. , 2019 . 62 746 - 752 . DOI: 10.1007/s11426-019-9457-5 http://doi.org/10.1007/s11426-019-9457-5 .

An, Q.; Ma, X.; Gao, J.; Zhang, F. . Solvent additive-free ternary polymer solar cells with 16.27% efficiency . Sci. Bull. , 2019 . 64 504 DOI: 10.1016/j.scib.2019.03.024 http://doi.org/10.1016/j.scib.2019.03.024 .

Yan, T.; Song, W.; Huang, J.; Peng, R.; Huang, L.; Ge, Z. . 16.67% rigid and 14.06% flexible organic solar cells enabled by ternary heterojunction strategy . Adv. Mater. , 2019 . 31 1902210 DOI: 10.1002/adma.201902210 http://doi.org/10.1002/adma.201902210 .

Li, K.; Wu, Y.; Tang, Y.; Pan, M. A.; Ma, W.; Fu, H.; Zhan, C.; Yao, J. . Ternary blended fullerene-free polymer solar cells with 16.5% efficiency enabled with a higher-LUMO-level acceptor to improve film morphology . Adv. Energy Mater. , 2019 . 9 1901728 DOI: 10.1002/aenm.201901728 http://doi.org/10.1002/aenm.201901728 .

Cui, Y.; Yao, H.; Zhang, J.; Zhang, T.; Wang, Y.; Hong, L.; Xian, K.; Xu, B.; Zhang, S.; Peng, J.; Wei, Z.; Gao, F.; Hou, J. . Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages . Nat. Commun. , 2019 . 10 2515 DOI: 10.1038/s41467-019-10351-5 http://doi.org/10.1038/s41467-019-10351-5 .

Xue, R.; Zhang, J.; Li, Y.; Li, Y. . Organic solar cell materials toward commercialization . Small , 2018 . 14 1801793 DOI: 10.1002/smll.201801793 http://doi.org/10.1002/smll.201801793 .

Zhang, K.; Gao, K.; Xia, R.; Wu, Z.; Sun, C.; Cao, J.; Qian, L.; Li, W.; Liu, S.; Huang, F.; Peng, X.; Ding, L.; Yip, H. L.; Cao, Y. . High-performance polymer tandem solar cells employing a new n-type conjugated polymer as an interconnecting layer . Adv. Mater. , 2016 . 28 4817 - 4823 . DOI: 10.1002/adma.201506270 http://doi.org/10.1002/adma.201506270 .

Zhang, M.; Ming, R.; Gao, W.; An, Q.; Ma, X.; Hu, Z.; Yang, C.; Zhang, F. . Ternary polymer solar cells with alloyed non-fullerene acceptor exhibiting 12.99% efficiency and 76.03% fill factor . Nano Energy , 2019 . 59 58 - 65 . DOI: 10.1016/j.nanoen.2019.02.038 http://doi.org/10.1016/j.nanoen.2019.02.038 .

Yuan, J.; Qiu, L.; Zhang, Z. G.; Li, Y.; Chen, Y.; Zou, Y. . Tetrafluoroquinoxaline based polymers for non-fullerene polymer solar cells with efficiency over 9% . Nano Energy , 2016 . 30 312 - 320 . DOI: 10.1016/j.nanoen.2016.10.008 http://doi.org/10.1016/j.nanoen.2016.10.008 .

Meng, B.; Miao, J.; Liu, J.; Wang, L. . A new polymer electron acceptor based on thiophene- S , S -dioxide unit for organic photovoltaics . Macromol. Rapid Commun. , 2018 . 39 1700505 DOI: 10.1002/marc.201700505 http://doi.org/10.1002/marc.201700505 .

Chen, D.; Yao, J.; Chen, L.; Yin, J.; Lv, R.; Huang, B.; Liu, S.; Zhang, Z. G.; Yang, C.; Chen, Y.; Li, Y. . Dye-incorporated polynaphthalenediimide acceptor for additive-free high-performance all-polymer solar cells . Angew. Chem. Int. Ed. , 2018 . 57 4580 - 4584 . DOI: 10.1002/anie.201800035 http://doi.org/10.1002/anie.201800035 .

Wang, M.; Xue, Z.; Wang, Z.; Ning, W.; Zhong, Y.; Liu, Y.; Zhang, C.; Huettner, S.; Tao, Y. . Slight structural disorder in bithiophene-based random terpolymers with improved power conversion efficiency for polymer solar cells . Chinese J. Polym. Sci. , 2018 . 36 1129 - 1138 . DOI: 10.1007/s10118-018-2128-5 http://doi.org/10.1007/s10118-018-2128-5 .

Zhang, L.; Xu, H.; Ding, Z.; Hu, J.; Liu, J.; Liu, Y. . Amino N -oxide functionalized graphene quantum dots as a cathode interlayer for inverted polymer solar cells . J. Mater. Chem. C , 2018 . 6 5684 - 5689 . DOI: 10.1039/C8TC01016A http://doi.org/10.1039/C8TC01016A .

Liu, J.; Wang, L. . Polymer electron acceptors containing boron-nitrogen coordination bond (B←N) for all-polymer solar cells . Acta Polymerica Sinica (in Chinese) , 2017 . 1856 - 1869 . .

Zhao, R.; Dou, C.; Xie, Z.; Liu, J.; Wang, L. . Polymer acceptor based on B←N units with enhanced electron mobility for efficient all-polymer solar cells . Angew. Chem. Int. Ed. , 2016 . 55 5313 - 5317 . DOI: 10.1002/anie.201601305 http://doi.org/10.1002/anie.201601305 .

Fan, B.; Zhong, W.; Ying, L.; Zhang, D.; Li, M.; Lin, Y.; Xia, R.; Liu, F.; Yip, H.; Li, Ning; Ma, Y.; Brabec, C.; Huang, F.; Cao, Y. . Surpassing the 10% efficiency milestone for 1-cm 2 all-polymer solar cells . Nat. Commun. , 2019 . 10 1 DOI: 10.1038/s41467-018-07882-8 http://doi.org/10.1038/s41467-018-07882-8 .

Gao, L.; Zhang, Z. G.; Xue, L.; Min, J.; Zhang, J.; Wei, Z.; Li, Y. . All-polymer solar cells based on absorption-complementary polymer donor and acceptor with high power conversion efficiency of 8.27% . Adv. Mater. , 2016 . 28 1884 - 1890 . DOI: 10.1002/adma.201504629 http://doi.org/10.1002/adma.201504629 .

Kolhe, N. B.; Tran, D. K.; Lee, H.; Kuzuhara, D.; Yoshimoto, N.; Koganezawa, T.; Jenekhe, S. A. . New random copolymer acceptors enable additive-free processing of 10.1% efficient all-polymer solar cells with near-unity internal quantum efficiency . ACS Energy Lett. , 2019 . 4 1162 - 1170 . DOI: 10.1021/acsenergylett.9b00460 http://doi.org/10.1021/acsenergylett.9b00460 .

Sun, H.; Tang, Y.; Koh, C. W.; Ling, S.; Wang, R.; Yang, K.; Yu, J.; Shi, Y.; Wang, Y.; Woo, H. Y.; Guo, X. . High-performance all-polymer solar cells enabled by an n-type polymer based on a fluorinated imide-functionalized arene . Adv. Mater. , 2019 . 31 1807220 DOI: 10.1002/adma.201807220 http://doi.org/10.1002/adma.201807220 .

Xu, X.; Li, Z.; Zhang, W.; Meng, X.; Zou, X.; Di Carlo Rasi, D.; Ma, W.; Yartsev, A.; Andersson, M. R.; Janssen, R. A. J.; Wang, E. . 8.0% Efficient all-polymer solar cells with high photovoltage of 1.1 V and internal quantum efficiency near unity . Adv. Energy Mater. , 2018 . 8 1700908 DOI: 10.1002/aenm.201700908 http://doi.org/10.1002/aenm.201700908 .

Zhang, Z.; Miao, J.; Ding, Z.; Kan, B.; Lin, B.; Wan, X.; Ma, W.; Chen, Y.; Long, X.; Dou, C.; Zhang, J.; Liu, J.; Wang, L. . Efficient and thermally stable organic solar cells based on small molecule donor and polymer acceptor . Nat. Commun. , 2019 . 10 3271 DOI: 10.1038/s41467-019-10984-6 http://doi.org/10.1038/s41467-019-10984-6 .

He, Y.; Heumüller, T.; Lai, W.; Feng, G.; Classen, A.; Du, X.; Liu, C.; Li, W.; Li, N.; Brabec, C. J. . Evidencing excellent thermal- and photostability for single-component organic solar cells with inherently built-In microstructure . Adv. Energy Mater. , 2019 . 9 1900409 DOI: 10.1002/aenm.201900409 http://doi.org/10.1002/aenm.201900409 .

Shi, Y.; Wang, Y.; Guo, X. . Recent progress of imide-functionalized n-type polymer semiconductors . Acta Polymerica Sinica (in Chinese) , 2019 . 50 873 - 889 . DOI: 10.11777/j.issn1000-3304.2019.19100 http://doi.org/10.11777/j.issn1000-3304.2019.19100 .

Ji, Y.; Xiao, C.; Wang, Q.; Zhang, J.; Li, C.; Wu, Y.; Wei, Z.; Zhan, X.; Hu, W.; Wang, Z.; Janssen, R. A. J.; Li, W. . Asymmetric diketopyrrolopyrrole conjugated polymers for field-effect transistors and polymer solar cells processed from a nonchlorinated solvent . Adv. Mater. , 2016 . 28 943 - 950 . DOI: 10.1002/adma.201504272 http://doi.org/10.1002/adma.201504272 .

Fan, B.; Ying, L.; Wang, Z.; He, B.; Jiang, X. F.; Huang, F.; Cao, Y. . Optimisation of processing solvent and molecular weight for the production of green-solvent-processed all-polymer solar cells with a power conversion efficiency over 9% . Energy Environ. Sci. , 2017 . 10 1243 - 1251 . DOI: 10.1039/C7EE00619E http://doi.org/10.1039/C7EE00619E .

Li, Z.; Ying, L.; Zhu, P.; Zhong, W.; Li, N.; Liu, F.; Huang, F.; Cao, Y. . A generic green solvent concept boosting the power conversion efficiency of all-polymer solar cells to 11% . Energy Environ. Sci. , 2019 . 12 157 - 163 . DOI: 10.1039/C8EE02863J http://doi.org/10.1039/C8EE02863J .

Chen, X.; Liu, X.; Burgers, M. A.; Huang, Y.; Bazan, G. C. . Green-solvent-processed molecular solar cells . Angew. Chem. Int. Ed. , 2014 . 53 14378 - 14381 . DOI: 10.1002/anie.201409208 http://doi.org/10.1002/anie.201409208 .

Xie, C.; Heumüller, T.; Gruber, W.; Tang, X.; Classen, A.; Schuldes, I.; Bidwell, M.; Späth, A.; Fink, R. H.; Unruh, T.; McCulloch, I.; Li, N.; Brabec, C. J. . Overcoming efficiency and stability limits in water-processing nanoparticular organic photovoltaics by minimizing microstructure defects . Nat. Commun. , 2018 . 9 5335 DOI: 10.1038/s41467-018-07807-5 http://doi.org/10.1038/s41467-018-07807-5 .

Farahat, M. E.; Perumal, P.; Budiawan, W.; Chen, Y. F.; Lee, C. H.; Chu, C. W. . Efficient molecular solar cells processed from green solvent mixtures . J. Mater. Chem. A , 2017 . 5 571 DOI: 10.1039/C6TA09626C http://doi.org/10.1039/C6TA09626C .

Meng, B.; Song, H.; Chen, X.; Xie, Z.; Liu J.; Wang. L. . Replacing alkyl with oligo(ethylene glycol) as side chains of conjugated polymers for close π - π stacking . Macromolecules , 2015 . 48 4357 DOI: 10.1021/acs.macromol.5b00702 http://doi.org/10.1021/acs.macromol.5b00702 .

Fan, B.; Ying, L.; Zhu, P.; Pan, F.; Liu, F.; Chen, J.; Huang, F.; Cao, Y. . All-polymer solar cells based on a conjugated polymer containing siloxane-functionalized side chains with efficiency over 10% . Adv. Mater. , 2017 . 29 1703906 DOI: 10.1002/adma.201703906 http://doi.org/10.1002/adma.201703906 .

Kim, N. K.; Jang, S. Y.; Pace, G.; Caironi, M.; Park, W. T.; Khim, D.; Kim, J.; Kim, D. Y.; Noh, Y. Y. . High-performance organic field-effect transistors with directionally aligned conjugated polymer film deposited from pre-aggregated solution . Chem. Mater. , 2015 . 27 8345 - 8353 . DOI: 10.1021/acs.chemmater.5b03775 http://doi.org/10.1021/acs.chemmater.5b03775 .

Zhu, Y.; Chen, Z.; Yang, Y.; Cai, P.; Chen, J.; Li, Y.; Yang, W.; Peng, J.; Cao, Y. . Using d -limonene as the non-aromatic and non-chlorinated solvent for the fabrications of high performance polymer light-emitting diodes and field-effect transistors . Org. Electron. , 2015 . 23 193 - 198 . DOI: 10.1016/j.orgel.2015.05.004 http://doi.org/10.1016/j.orgel.2015.05.004 .

Chen, H.; Hu, Z.; Wang, H.; Liu, L.; Chao, P.; Qu, J.; Chen, W.; Liu, A.; He, F. . A chlorinated π -conjugated polymer donor for efficient organic solar cells . Joule , 2018 . 2 1623 - 1634 . DOI: 10.1016/j.joule.2018.05.010 http://doi.org/10.1016/j.joule.2018.05.010 .

Fan, B.; Zhu, P.; Xin, J.; Li, N.; Ying, L.; Zhong, W.; Li, Z.; Ma, W.; Huang, F.; Cao, Y. . High-performance thick-film all-polymer solar cells created via ternary blending of a novel wide-bandgap electron-donating copolymer . Adv. Energy Mater. , 2018 . 8 1703085 DOI: 10.1002/aenm.201703085 http://doi.org/10.1002/aenm.201703085 .

Zhong, W.; Hu, Q.; Jiang, Y.; Li, Y.; Chen, T. L.; Ying, L.; Liu, F.; Wang, C.; Liu, Y.; Huang, F.; Cao, Y.; Russell, T. P. . In situ structure characterization in slot-die-printed all-polymer solar cells with efficiency over 9% . Solar RRL , 2019 . 3 1900032 DOI: 10.1002/solr.201900032 http://doi.org/10.1002/solr.201900032 .

Gao, K.; Deng, W.; Xiao, L.; Hu, Q.; Kan, Y.; Chen, X.; Wang, C.; Huang, F.; Peng, J.; Wu, H.; Peng, X.; Cao, Y.; Russell, T. P.; Liu, F. . New insight of molecular interaction, crystallization and phase separation in higher performance small molecular solar cells via solvent vapor annealing . Nano Energy , 2016 . 30 639 - 648 . DOI: 10.1016/j.nanoen.2016.10.031 http://doi.org/10.1016/j.nanoen.2016.10.031 .

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⁰

Rational Design of Conjugated Polymers for d-Limonene Processed All-polymer Solar Cells with Small Energy Loss

DOI：10.1007/s10118-020-2429-3

摘要

Abstract

关键词

Keywords

references