Abstract
A near-infrared non-fullerene acceptor (NFA) BDTIC, based on thienopyrrole-expanded benzo[1,2-b:4,5-b′]dithiophene unit (heptacyclic S,N-heteroacene) as core, is designed and synthesized. The aromatic pyrrole ring with strong electron-donating ability in the core enhances the intramolecular charge transfer effect, finely tunes the optical bandgap and absorption profile of BDTIC, and thus results in a narrowed optical bandgap (E optg ) of 1.38 eV and a near-infrared absorption to 900 nm. When BDTIC is paired with donor polymer PBDB-T to fabricate organic solar cells, the optimized device achieves a best power conversion efficiency of 12.1% with a short-circuit current density of 20.0 mA·cm−2 and an open-circuit voltage of 0.88 V. The photovoltaic performance benefits from the broad absorption, weak bimolecular recombination, efficient charge separation and collection, and favorable blend morphology. This work demonstrates that thienopyrrole-expanded benzo[1,2-b:4,5-b′]dithiophene unit (heptacyclic S,N-heteroacene) is a promising building unit to construct high-performance NFAs by enhancing the intramolecular charge transfer effect, broadening absorption as well as maintaining good intermolecular stacking property.
Similar content being viewed by others
References
Brabec, C. J.; Gowrisanker, S.; Halls, J. J. M.; Laird, D.; Jia, S.; Williams, S. P. Polymer-fullerene bulk-heterojunction solar cells. Adv. Mater.2010, 22, 3839–3856.
Li, Y. Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption. Acc. Chem. Res.2012, 45, 723–733.
Qu, J. F.; Liu, J.; Li, S. Da; **e, Z. Y.; Geng, Y. H. Donor-acceptor conjugated cooligomers for single molecule solar cells. Chinese J. Polym. Sci.2013, 31, 815–822.
Krebs, F. C.; Espinosa, N.; Hösel, M.; Søndergaard, R. R.; Jørgensen, M. 25th Anniversary article: rise to power-OPV-based solar parks. Adv. Mater.2014, 26, 29–39.
Li, Z. Y.; Zhong, W. K.; 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.
Zhang, K.; Liu, X.; Xu, B.; Cui, Y.; Sun, M.; Hou, J. High-performance fullerene-free polymer solar cells with solution-processed conjugated polymers as anode interfacial layer. Chinese J. Polym. Sci.2017, 35, 219–229.
Liao, Q.; Kang, Q.; Yang, Y.; An, C.; Xu, B.; Hou, J. Tailoring and modifying an organic electron acceptor toward the cathode interlayer for highly efficient organic solar cells. Adv. Mater.2020, 32, 1906557.
Yuan, J.; Zhang, Y.; Zhou, L.; Zhang, C.; Lau, T. K.; Zhang, G.; Lu, X.; Yip, H. L.; So, S. K.; Beaupré, S.; Mainville, M.; Johnson, P. A.; Leclerc, M.; Chen, H.; Peng, H.; Li, Y.; Zou, Y. Fused benzothiadiazole: a building block for n-type organic acceptor to achieve high-performance organic solar cells. Adv. Mater.2019, 31, 1–8.
Yan, C.; Liu, T.; Chen, Y.; Ma, R.; Tang, H.; Li, G.; Li, T.; **ao, Y.; Yang, T.; Lu, X.; Zhan, X.; Yan, H.; Li, G.; Tang, B. ITC-2Cl: a versatile middle-bandgap nonfullerene acceptor for high-efficiency panchromatic ternary organic solar cells. Sol. RRL2020, 4, 1900377.
Chen, T. W.; Peng, K. L.; Lin, Y. W.; Su, Y. J.; Ma, K. J.; Hong, L.; Chang, C. C.; Hou, J.; Hsu, C. S. A chlorinated nonacyclic carbazole-based acceptor affords over 15% efficiency in organic solar cells. J. Mater. Chem. A2020, 8, 1131–1137.
Dong, S.; Zhang, K.; Jia, T.; Zhong, W.; Wang, X.; Huang, F.; Cao, Y. Suppressing the excessive aggregation of nonfullerene acceptor in blade-coated active layer by using n-type polymer additive to achieve large-area printed organic solar cells with efficiency over 15%. EcoMat2019, 1, 12006.
Geng, S. Z.; Yang, W. T.; Gao, J.; Li, S. X.; Shi, M. M.; Lau, T. K.; Lu, X. H.; Li, C. Z.; Chen, H. Z. Non-fullerene acceptors with a thieno[3,4-c]pyrrole-4,6-dione (TPD) core for efficient organic solar cells. Chinese J. Polym. Sci.2019, 37, 1005–1014.
Meng, L.; Zhang, Y.; Wan, X.; Li, C.; Zhang, X.; Wang, Y.; Ke, X.; **ao, Z.; Ding, L.; **a, R.; Yip, H. L.; Cao, Y.; Chen, Y. Organic and solution-processed tandem solar cells with 17.3% efficiency. Science2018, 361, 1094–1098.
Lin, Y.; Adilbekova, B.; Firdaus, Y.; Yengel, E.; Faber, H.; Sajjad, M.; Zheng, X.; Yarali, E.; Seitkhan, A.; Bakr, O. M.; El-Labban, A.; Schwingenschlögl, U.; Tung, V.; McCulloch, I.; Laquai, F.; Anthopoulos, T. D. 17% Efficient organic solar cells based on liquid exfoliated WS2 as a replacement for PEDOT:PSS. Adv. Mater.2019, 31, 1902965.
Zhan, L.; Li, S.; Lau, T.-K.; Cui, Y.; Lu, X.; Shi, M.; Li, C. Z.; Li, H.; Hou, J.; Chen, H. Over 17% efficiency ternary organic solar cells enabled by two non-fullerene acceptors working in an alloy-like model. Energy Environ. Sci.2020, 13, 635–645.
Lin, Y.; Wang, J.; Zhang, Z. G.; Bai, H.; Li, Y.; Zhu, D.; Zhan, X. An electron acceptor challenging fullerenes for efficient polymer solar cells. Adv. Mater.2015, 27, 1170–1174.
Mihailetchi, B. V. D.; van Duren, J. K. J; Blom, P. W. M.; Hummelen, J. C.; Janssen, R. A. J.; Kroon, J. M.; Rispens, M. T.; Verhees, W. J. H.; Wienk, M. M. Electron transport in a methanofullerene. Int. J. Eng. Sci. Technol.2010, 2, 610–617.
Huang, F.; Bo, Z. S.; Geng, Y. H.; Wang, X. H.; Wang, L. X.; Ma, Y. G.; Hou, J. H.; Hu, W. P.; Pei, J.; Dong, H. L.; Wang, S.; Li, Z.; Shuai, Z. G.; Li, Y. F.; Cao, Y. Study on optoelectronic polymers: an overview and outlook. Acta Polymerica Sinica (in Chinese) 2019, 50, 988–1046.
Wu, Y.; Zheng, Y.; Yang, H.; Sun, C.; Dong, Y.; Cui, C.; Yan, H.; Li, Y. Rationally pairing photoactive materials for high-performance polymer solar cells with efficiency of 16.53%. Sci. China Chem.2019, 63, 265–271.
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.
Lin, Y.; Li, T.; Zhao, F.; Han, L.; Wang, Z.; Wu, Y.; He, Q.; Wang, J.; Huo, L.; Sun, Y.; Wang, C.; Ma, W.; Zhan, X. Structure evolution of oligomer fused-ring electron acceptors toward high efficiency of as-cast polymer solar cells. Adv. Energy Mater.2016, 6, 1600854.
Wang, W.; Lu, H.; Chen, Z.; Jia, B.; Li, K.; Ma, W.; Zhan, X. Highperformance NIR-sensitive fused tetrathienoacene electron acceptors. J. Mater. Chem. A2020, 8, 3011–3017.
Jia, B.; Wang, J.; Wu, Y.; Zhang, M.; Jiang, Y.; Tang, Z.; Russell, T. P.; Zhan, X. Enhancing the performance of a fused-ring electron acceptor by unidirectional extension. J. Am. Chem. Soc.2019, 141, 19023–19031.
Wang, H.; Cao, J.; Yu, J.; Zhang, Z.; Geng, R.; Yang, L.; Tang, W. Molecular engineering of central fused-ring cores of non-fullerene acceptors for high-efficiency organic solar cells. J. Mater. Chem. A2019, 7, 4313–4333.
Xu, S.; Zhou, Z.; Liu, W.; Zhang, Z.; Liu, F.; Yan, H.; Zhu, X. A twisted thieno[3,4-b]thiophene-based electron acceptor featuring a 14-TT-electron indenoindene core for high-performance organic photovoltaics. Adv. Mater.2017, 29, 1–6.
Huang, C.; Liao, X.; Gao, K.; Zuo, L.; Lin, F.; Shi, X.; Li, C. Z.; Liu, H.; Li, X.; Liu, F.; Chen, Y.; Chen, H.; Jen, A. K. Y. Highly efficient organic solar cells based on S,N-heteroacene non-fullerene acceptors. Chem. Mater.2018, 30, 5429–5434.
Sun, J.; Ma, X.; Zhang, Z.; Yu, J.; Zhou, J.; Yin, X.; Yang, L.; Geng, R.; Zhu, R.; Zhang, F.; Tang, W. Dithieno[3,2-b:2′,3′-d]pyrrol fused nonfullerene acceptors enabling over 13% efficiency for organic solar cells. Adv. Mater.2018, 30, 1–8.
Lin, Y.; Zhao, F.; He, Q.; Huo, L.; Wu, Y.; Parker, T. C.; Ma, W.; Sun, Y.; Wang, C.; Zhu, D.; Heeger, A. J.; Marder, S. R.; Zhan, X. Highperformance electron acceptor with thienyl side chains for organic photovoltaics. J. Am. Chem. Soc.2016, 138, 4955–4961.
Hu, H.; Jiang, K.; Yang, G.; Liu, J.; Li, Z.; Lin, H.; Liu, Y.; Zhao, J.; Zhang, J.; Huang, F.; Qu, Y.; Ma, W.; Yan, H. Terthiophene-based D-A polymer with an asymmetric arrangement of alkyl chains that enables efficient polymer solar cells. J. Am. Chem. Soc.2015, 137, 14149–14157.
Liu, Q.; **ao, Z.; Li, T.; Yang, S.; You, W.; Wang, M.; Ding, L. Understanding the side-chain effects on A-D-A acceptors: inplane and out-of-plane. Mater. Chem. Front.2018, 2, 1563–1567.
Feng, H.; Song, X.; Zhang, M.; Yu, J.; Zhang, Z.; Geng, R.; Yang, L.; Liu, F.; Baran, D.; Tang, W. Side chain engineering on dithieno[3,2-b:2,3-d]pyrrol fused electron acceptors for efficient organic solar cells. Mater. Chem. Front.2019, 3, 702–708.
Li, Y.; Zhong, L.; Gautam, B.; Bin, H.; Lin, J.; Wu, F.; Zhang, Z.; Jiang, Z.; Zhang, Z.; Gundogdu, K.; Li, Y.; Liao, L. A near-infrared non-fullerene electron acceptor for high performance polymer solar cells. Energy Environ. Sci.2017, 10, 1610–1620.
Warnan, J.; Cabanetos, C.; El Labban, A.; Hansen, M. R.; Tassone, C.; Toney, M. F.; Beaujuge, P. M. Ordering effects in benzo[1,2-b:4,5-b′]difuran-thieno[3,4-c]pyrrole-4,6-dione polymers with < 7% solar cell efficiency. Adv. Mater.2014, 26, 4357–4362.
Li, Y.; Lin, J. D.; Che, X.; Qu, Y.; Liu, F.; Liao, L. S.; Forrest, S. R. High efficiency near-infrared and semitransparent non-fullerene acceptor organic photovoltaic cells. J. Am. Chem. Soc.2017, 139, 17114–17119.
Shi, X.; Chen, J.; Gao, K.; Zuo, L.; Yao, Z.; Liu, F.; Tang, J.; Jen, A. K. Y. Terthieno[3,2-b]thiophene (6T) based low bandgap fused-ring electron acceptor for highly efficient solar cells with a high short-circuit current density and low open-circuit voltage loss. Energy Mater.2018, 8, 2–9.
Brown, P. J.; Thomas, D. S.; Köhler, A.; Wilson, J. S.; Kim, J. S.; Ramsdale, C. M.; Sirringhaus, H.; Friend, R. H. Effect of interchain interactions on the absorption and emission of poly(3-hexylthiophene). Phys. Rev. B Condens. Matter Mater. Phys.2003, 67, 1–16.
Li, W.; Cai, J.; Yan, Y.; Cai, F.; Li, S.; Gurney, R. S.; Liu, D.; McGettrick, J. D.; Watson, T. M.; Li, Z.; Pearson, A. J.; Lidzey, D. G.; Hou, J.; Wang, T. Correlating three-dimensional morphology with function in PBDB-T:IT-M non-fullerene organic solar cells. Sol. RRL2018, 2, 1800114.
Long, G.; Wu, B.; Solanki, A.; Yang, X.; Kan, B.; Liu, X.; Wu, D.; Xu, Z.; Wu, W. R.; Jeng, U. S.; Lin, J.; Li, M.; Wang, Y.; Wan, X.; Sum, T. C.; Chen, Y. New insights into the correlation between morphology, excited state dynamics, and device performance of small molecule organic solar cells. Adv. Energy Mater.2016, 6, 1600961.
**ao, M.; Zhang, K.; **, Y.; Yin, Q.; Zhong, W.; Huang, F.; Cao, Y. Low temperature processed high-performance thick film ternary polymer solar cell with enhanced stability. Nano Energy2018, 48, 53–62.
Duan, C.; Zhong, C.; Liu, C.; Huang, F.; Cao, Y. Highly efficient inverted polymer solar cells based on an alcohol soluble fullerene derivative interfacial modification material. Chem. Mater.2012, 24, 1682–1689.
Zhang, K.; Hu, Z.; Sun, C.; Wu, Z.; Huang, F.; Cao, Y. Toward solution-processed high-performance polymer solar cells: from material design to device engineering. Chem. Mater.2017, 29, 141–148.
Goh, C.; Kline, R. J.; McGehee, M. D.; Kadnikova, E. N.; Fŕchet, J. M. J. Molecular-weight-dependent mobilities in regioregular poly(3-hexyl-thiophene) diodes. Appl. Phys. Lett.2005, 86, 122110–3.
Fan, B.; Du, X.; Liu, F.; Zhong, W.; Ying, L.; **e, R.; Tang, X.; An, K.; **n, J.; Li, N.; Ma, W.; Brabec, C. J.; Huang, F.; Cao, Y. Fine-tuning of the chemical structure of photoactive materials for highly efficient organic photovoltaics. Nat. Energy2018, 3, 1051–1058.
Koster, L. J. A.; Mihailetchi, V. D.; Ramaker, R.; Blom, P. W. M. Light intensity dependence of open-circuit voltage of polymerfullerene solar cells. Appl. Phys. Lett.2005, 86, 123509.
Cowan, S. R.; Roy, A.; Heeger, A. J. Recombination in polymerfullerene bulk heterojunction solar cells. Phys. Rev. B Condens. Matter Mater. Phys.2010, 82, 1–36.
Hexemer, A.; Bras, W.; Glossinger, J.; Schaible, E.; Gann, E.; Kirian, R.; MacDowell, A.; Church, M.; Rude, B.; Padmore, H. A SAXS/WAXS/GISAXS beamline with multilayer monochromator. J. Phys. Conf. Ser.2010, 247, 012007.
Acknowledgments
This work was financially supported by the National Key Research and Development Program of China (No. 2019YFA0705900) funded by MOST, the Basic and Applied Basic Research Major Program of Guangdong Province (No. 2019B030302007), and the Pearl River Nova Program of Guangzhou (NO. 201906010074).
Author information
Authors and Affiliations
Corresponding authors
Electronic Supplementary Information
10118_2020_2440_MOESM1_ESM.pdf
A Near-Infrared Non-Fullerene Acceptor with Thienopyrrole-Expanded Benzo[1,2-b:4,5-b′]dithiophene Core for Polymer Solar Cells
Rights and permissions
About this article
Cite this article
Chen, Z., Ma, SS., Zhang, K. et al. A Near-infrared Non-fullerene Acceptor with Thienopyrrole-expanded Benzo[1,2-b:4,5-b′]dithiophene Core for Polymer Solar Cells. Chin J Polym Sci 39, 35–42 (2021). https://doi.org/10.1007/s10118-020-2440-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10118-020-2440-8