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Vol. 15 (2023)

All-Polymer Solar Cells and Photodetectors with Improved Stability Enabled by Terpolymers Containing Antioxidant Side Chains

https://doi.org/10.1007/s40820-023-01114-5
Chunyang Zhang
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Ao Song
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Qiri Huang
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Yunhao Cao
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Zuiyi Zhong
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Youcai Liang
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Kai Zhang
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Chunchen Liu
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Fei Huang
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China
Yong Cao
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, People’s Republic of China

Corresponding Author: Fei Huang

msfhuang@scut.edu.cn

Nano-Micro Letters, Vol. 15 (2023), Article Number: 140

Abstract

It is of vital importance to improve the long-term and photostability of organic photovoltaics, including organic solar cells (OSCs) and organic photodetectors (OPDs), for their ultimate industrialization. Herein, two series of terpolymers featuring with an antioxidant butylated hydroxytoluene (BHT)-terminated side chain, PTzBI-EHp-BTBHTx and N2200-BTBHTx (x = 0.05, 0.1, 0.2), are designed and synthesized. It was found that incorporating appropriate ratio of benzothiadiazole (BT) with BHT side chains on the conjugated backbone would induce negligible effect on the molecular weight, absorption spectra and energy levels of polymers, however, which would obviously enhance the photostability of these polymers. Consequently, all-polymer solar cells (all-PSCs) and photodetectors were fabricated, and the all-PSC based on PTzBI-EHp-BTBHT0.05: N2200 realized an optimal power conversion efficiency (PCE) approaching ~ 10%, outperforming the device based on pristine PTzBI-EHp: N2200. Impressively, the all-PSCs based on BHT-featuring terpolymers displayed alleviated PCEs degradation under continuous irradiation for 300 h due to the improved morphological and photostability of active layers. The OPDs based on BHT-featuring terpolymers achieved a lower dark current at − 0.1 bias, which could be stabilized even after irradiation over 400 h. This study provides a feasible approach to develop terpolymers with antioxidant efficacy for improving the lifetime of OSCs and OPDs.


Highlights:


1 Two series of terpolymers with improved photostability were realized by the introduction of appropriate ratio of antioxidant butylated hydroxytoluene unit containing side chains.
2 All-polymer solar cells and organic photodetectors (OPDs) with these terpolymers as both donors and acceptors have been prepared with simultaneously improved efficiency and stability.
3 A feasible approach to develop terpolymers with antioxidant efficacy for improving the lifetime of organic solar cells and OPDs is proposed.

Keywords

Organic photovoltaics Device operational stability All-polymer solar cell Organic photodetector Antioxidant
Zhang, Chunyang, Ao Song, Qiri Huang, Yunhao Cao, Zuiyi Zhong, Youcai Liang, Kai Zhang, Chunchen Liu, Fei Huang, and Yong Cao. 2023. “All-Polymer Solar Cells and Photodetectors With Improved Stability Enabled by Terpolymers Containing Antioxidant Side Chains”. Nano-Micro Letters 15 (May):140. https://doi.org/10.1007/s40820-023-01114-5.
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References
  1. H. Yan, Z. Chen, Y. Zheng, C. Newman, J.R. Quinn et al., High-mobility electron-transporting polymer for printed transistors. Nature 457, 679 (2009). https://doi.org/10.1038/nature07727
  2. S. Dong, T. Jia, K. Zhang, J. Jing, F. Huang, Single-component non-halogen solvent-processed high-performance organic solar cell module with efficiency over 14%. Joule 4, 2004 (2020). https://doi.org/10.1016/j.joule.2020.07.028
  3. S.D. Collins, N.A. Ran, M.C. Heiber, T.-Q. Nguyen, Small is powerful: recent progress in solution-processed small molecule solar cells. Adv. Energy Mater. 7, 1602242 (2017). https://doi.org/10.1002/aenm.201602242
  4. Y. Song, K. Zhang, S. Dong, R. Xia, F. Huang et al., Semitransparent organic solar cells enabled by a sequentially deposited bilayer structure. ACS Appl. Mater. Interfaces 12, 18473 (2020). https://doi.org/10.1021/acsami.0c00396
  5. N. Cui, Y. Song, C.-H. Tan, K. Zhang, X. Yang et al., Stretchable transparent electrodes for conformable wearable organic photovoltaic devices. Npj Flex. Electron. 5, 31 (2021). https://doi.org/10.1038/s41528-021-00127-7
  6. P. Bi, S. Zhang, Z. Chen, Y. Xu, Y. Cui et al., Reduced non-radiative charge recombination enables organic photovoltaic cell approaching 19% efficiency. Joule 5, 2408 (2021). https://doi.org/10.1016/j.joule.2021.06.020
  7. L. Duan, A. Uddin, Progress in stability of organic solar cells. Adv. Sci. 7, 1903259 (2020). https://doi.org/10.1002/advs.201903259
  8. X. Huang, Z. Zhao, S. Chung, K. Cho, J. Lv et al., Balancing the performance and stability of organic photodiodes with all-polymer active layers. J. Mater. Chem. C 10, 17502 (2022). https://doi.org/10.1039/D2TC04132D
  9. M. Jørgensen, K. Norrman, F.C. Krebs, Stability/degradation of polymer solar cells. Solar Energy Mater. Solar Cells 92, 686 (2008). https://doi.org/10.1016/j.solmat.2008.01.005
  10. Y. Wang, J. Lee, X. Hou, C. Labanti, J. Yan et al., Recent progress and challenges toward highly stable nonfullerene acceptor-based organic solar cells. Adv. Energy Mater. 11, 2003002 (2021). https://doi.org/10.1002/aenm.202003002
  11. I. Fraga Domínguez, A. Distler, L. Lüer, Stability of organic solar cells: the influence of nanostructured carbon materials. Adv. Energy Mater. 7, 1601320 (2017). https://doi.org/10.1002/aenm.201601320
  12. M. Riede, D. Spoltore, K. Leo, Organic solar cells—the path to commercial success. Adv. Energy Mater. 11, 2002653 (2021). https://doi.org/10.1002/aenm.202002653
  13. J. Oh, S.M. Lee, S. Jung, J. Lee, G. Park et al., Antioxidant additive with a high dielectric constant for high photo-oxidative stabilization of organic solar cells without almost sacrificing initial high efficiencies. Solar RRL 5, 2000812 (2021). https://doi.org/10.1002/solr.202000812
  14. I. Björkhem, A. Henriksson-Freyschuss, O. Breuer, U. Diczfalusy, L. Berglund et al., The antioxidant butylated hydroxytoluene protects against atherosclerosis. Arterioscler. Thromb. J. Vasc. Biol. 11, 15 (1991). https://doi.org/10.1161/01.ATV.11.1.15
  15. X. Wen, Y. Zhang, G. Xie, R. Rausch, N. Tang et al., Phenol-functionalized perylene bisimides as amine-free electron transporting interlayers for stable nonfullerene organic solar cells. Adv. Funct. Mater. 32, 2111706 (2022). https://doi.org/10.1002/adfm.202111706
  16. A. Guerrero, G. Garcia-Belmonte, Recent advances to understand morphology stability of organic photovoltaics. Nano-Micro Lett. 9, 10 (2017). https://doi.org/10.1007/s40820-016-0107-3
  17. S. Chen, L. Hong, M. Dong, W. Deng, L. Shao et al., A polyfluoroalkyl-containing non-fullerene acceptor enables self-stratification in organic solar cells. Angew. Chem. Int. Ed. 62, e202213869 (2023). https://doi.org/10.1002/anie.202213869
  18. L. Zhan, S. Li, X. Xia, Y. Li, X. Lu et al., Layer-by-layer processed ternary organic photovoltaics with efficiency over 18%. Adv. Mater. 33, 2007231 (2021). https://doi.org/10.1002/adma.202007231
  19. M. Salvador, N. Gasparini, J.D. Perea, S.H. Paleti, A. Distler et al., Suppressing photooxidation of conjugated polymers and their blends with fullerenes through nickel chelates. Energy Environ. Sci. 10, 2005 (2017). https://doi.org/10.1039/C7EE01403A
  20. V. Turkovic, S. Engmann, N. Tsierkezos, H. Hoppe, U. Ritter et al., Long-term stabilization of organic solar cells using hindered phenols as additives. ACS Appl. Mater. Interfaces 6, 18525 (2014). https://doi.org/10.1021/am5024989
  21. J. Zhang, C. Tan, K. Zhang, T. Jia, Y. Cui et al., π-Extended conjugated polymer acceptor containing thienylene-vinylene-thienylene unit for high-performance thick-film all-polymer solar cells with superior long-term stability. Adv. Energy Mater. 11, 2102559 (2021). https://doi.org/10.1002/aenm.202102559
  22. Z. Yin, Q. Wang, H. Zhao, H. Wang, N. Li et al., 17.13% efficiency and superior thermal stability of organic solar cells based on a comb-shape active blend. Energy Environ. Mater. (2022). https://doi.org/10.1002/eem2.12443
  23. B. Fan, W. Zhong, L. Ying, D. Zhang, M. Li et al., Surpassing the 10% efficiency milestone for 1-cm2 all-polymer solar cells. Nat. Commun. 10, 4100 (2019). https://doi.org/10.1038/s41467-019-12132-6
  24. M. Kielar, O. Dhez, G. Pecastaings, A. Curutchet, L. Hirsch, Long-term stable organic photodetectors with ultra low dark currents for high detectivity applications. Sci. Rep. 6, 39201 (2016). https://doi.org/10.1038/srep39201
  25. G. Li, J. Wu, J. Fang, X. Guo, L. Zhu et al., A non-fullerene acceptor with chlorinated thienyl conjugated side chains for high-performance polymer solar cells via toluene processing. Chin. J. Chem. 38, 697 (2020). https://doi.org/10.1002/cjoc.201900495
  26. U. Würfel, L. Perdigón-Toro, J. Kurpiers, C.M. Wolff, P. Caprioglio et al., Recombination between photogenerated and electrode-induced charges dominates the fill factor losses in optimized organic solar cells. J. Phys. Chem. Lett. 10, 3473 (2019). https://doi.org/10.1021/acs.jpclett.9b01175
  27. M.P. Seah, W.A. Dench, Quantitative electron spectroscopy of surfaces: a standard data base for electron inelastic mean free paths in solids. Surf. Interface Anal. 1, 2 (1979). https://doi.org/10.1002/sia.740010103
  28. Z. Wang, Z. Hong, T. Zhuang, G. Chen, H. Sasabe et al., High fill factor and thermal stability of bilayer organic photovoltaic cells with an inverted structure. Appl. Phys. Lett. 106, 053305 (2015). https://doi.org/10.1063/1.4907399
  29. L.J.A. Koster, V.D. Mihailetchi, R. Ramaker, P.W.M. Blom, Light intensity dependence of open-circuit voltage of polymer: fullerene solar cells. Appl. Phys. Lett. 86, 123509 (2005). https://doi.org/10.1063/1.1889240
  30. Y. Song, Z. Zhong, P. He, G. Yu, Q. Xue et al., Doping compensation enables high-detectivity infrared organic photodiodes for image sensing. Adv. Mater. 34, 2201827 (2022). https://doi.org/10.1002/adma.202201827
  31. S. Dongaonkar, J.D. Servaites, G.M. Ford, S. Loser, J. Moore et al., Universality of non-Ohmic shunt leakage in thin-film solar cells. J. Appl. Phys. 108, 124509 (2010). https://doi.org/10.1063/1.3518509
  32. X. Zhou, D. Yang, D. Ma, Extremely low dark current, high responsivity, all-polymer photodetectors with spectral response from 300 nm to 1000 nm. Adv. Opt. Mater. 3, 1570 (2015). https://doi.org/10.1002/adom.201500224
  33. D. Zhang, D. Zhao, Z. Wang, J. Yu, Processes controlling the distribution of vertical organic composition in organic photodetectors by ultrasonic-assisted solvent vapor annealing. ACS Appl. Electron. Mater. 2, 2188 (2020). https://doi.org/10.1021/acsaelm.0c00378
  34. H. Shekhar, O. Solomeshch, D. Liraz, N. Tessler, Low dark leakage current in organic planar heterojunction photodiodes. Appl. Phys. Lett. 111, 223301 (2017). https://doi.org/10.1063/1.4996826
  35. C. Fuentes-Hernandez, W.-F. Chou, T.M. Khan, L. Diniz, J. Lukens et al., Large-area low-noise flexible organic photodiodes for detecting faint visible light. Science 370, 698 (2020). https://doi.org/10.1126/science.aba2624
  36. Y. Song, G. Yu, B. Xie, K. Zhang, F. Huang, Visible-to-near-infrared organic photodiodes with performance comparable to commercial silicon-based detectors. Appl. Phys. Lett. 117, 093302 (2020). https://doi.org/10.1063/5.0018274
  37. C. Zhang, Y. Cao, Y. Song, G. Yu, L. Lan et al., Organic photodiodes with thermally reliable dark current and excellent detectivity enabled by low donor concentration. ACS Appl. Mater. Interfaces 15, 7175 (2023). https://doi.org/10.1021/acsami.2c15657
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