Perylene Diimide Based Isomeric Conjugated Polymers as Efficient Electron Acceptors for All-polymer Solar Cells
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摘要
We present here a series of perylene diimide(PDI)based isomeric conjugated polymers for the application as efficient electron acceptors in all-polymer solar cells(all-PSCs).By copolymerizing PDI monomers with 1,4-diethynylbenzene(para-linkage)and 1,3-diethynylbenzene(meta-linkage),isomeric PDI based conjugated polymers with parallel and non-parallel PDI units inside backbones were obtained.It was found that para-linked conjugated polymer(PA)showed better solubility,strongerπ-πstacking,more favorable blend morphology,and better photovoltaic performance than those of meta-linked conjugated polymers(PM)did.Device based on PTB7-Th:PA(PTB7-Th:poly{4,8-bis[5-(2-ethylhexyl)-thiophen-2-yl]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl-alt-3-fluoro-2-[(2-ethylhexyl)-carbonyl]thieno[3,4-b]thiophene-4,6-diyl})showed significantly enhanced photovoltaic performance than that of PTB7-Th:MA(3.29%versus 0.92%).Moreover,the photovoltaic performance of these polymeric acceptors could be further improved via a terpolymeric strategy.By copolymerizing a small amount of meta-linkages into PA,the optimized terpolymeric acceptors enabled to enhance photovoltaic performance with improved the short-circuit current density(Jsc)and fill factor(FF),resulting in an improved power conversion efficiency(PCE)of 4.03%.
We present here a series of perylene diimide(PDI)based isomeric conjugated polymers for the application as efficient electron acceptors in all-polymer solar cells(all-PSCs).By copolymerizing PDI monomers with 1,4-diethynylbenzene(para-linkage)and 1,3-diethynylbenzene(meta-linkage),isomeric PDI based conjugated polymers with parallel and non-parallel PDI units inside backbones were obtained.It was found that para-linked conjugated polymer(PA)showed better solubility,strongerπ-πstacking,more favorable blend morphology,and better photovoltaic performance than those of meta-linked conjugated polymers(PM)did.Device based on PTB7-Th:PA(PTB7-Th:poly{4,8-bis[5-(2-ethylhexyl)-thiophen-2-yl]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl-alt-3-fluoro-2-[(2-ethylhexyl)-carbonyl]thieno[3,4-b]thiophene-4,6-diyl})showed significantly enhanced photovoltaic performance than that of PTB7-Th:MA(3.29%versus 0.92%).Moreover,the photovoltaic performance of these polymeric acceptors could be further improved via a terpolymeric strategy.By copolymerizing a small amount of meta-linkages into PA,the optimized terpolymeric acceptors enabled to enhance photovoltaic performance with improved the short-circuit current density(Jsc)and fill factor(FF),resulting in an improved power conversion efficiency(PCE)of 4.03%.
We present here a series of perylene diimide(PDI)based isomeric conjugated polymers for the application as efficient electron acceptors in all-polymer solar cells(all-PSCs).By copolymerizing PDI monomers with 1,4-diethynylbenzene(para-linkage)and 1,3-diethynylbenzene(meta-linkage),isomeric PDI based conjugated polymers with parallel and non-parallel PDI units inside backbones were obtained.It was found that para-linked conjugated polymer(PA)showed better solubility,strongerπ-πstacking,more favorable blend morphology,and better photovoltaic performance than those of meta-linked conjugated polymers(PM)did.Device based on PTB7-Th:PA(PTB7-Th:poly{4,8-bis[5-(2-ethylhexyl)-thiophen-2-yl]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl-alt-3-fluoro-2-[(2-ethylhexyl)-carbonyl]thieno[3,4-b]thiophene-4,6-diyl})showed significantly enhanced photovoltaic performance than that of PTB7-Th:MA(3.29%versus 0.92%).Moreover,the photovoltaic performance of these polymeric acceptors could be further improved via a terpolymeric strategy.By copolymerizing a small amount of meta-linkages into PA,the optimized terpolymeric acceptors enabled to enhance photovoltaic performance with improved the short-circuit current density(Jsc)and fill factor(FF),resulting in an improved power conversion efficiency(PCE)of 4.03%.
引文
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2 Diao, Y.; Zhou, Y.; Kurosawa, T.; Shaw, L.; Wang, C.; Park,S.; Guo, Y.; Reinspach, J. A.; Gu, K.; Gu, X.; Tee, B. C. K.;Pang, C.; Yan, H.; Zhao, D.; Toney, M. F.; Mannsfeld, S. C. B.;Bao, Z. Flow-enhanced solution printing of all-polymer solar cells. Nat. Commun. 2015, 6, 7955.
3 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. Chem. Int. Ed. 2016, 55,5313-5317.
4 Zhou, N.; Dudnik, A. S.; Li, T. I. N.; Manley, G. E. F.; Aldrich,T. J.; Guo, P.; Liao, H. C.; Chen, Z.; Chen, L. X.; Chang, R. P.H.; Facchetti, A.; Cruz, M. O.; Marks, T. J. All-polymer solar cell performance optimized via systematic molecular weight tuning of both donor and acceptor polymers. J. Am. Chem. Soc.2016,138, 1240-1251.
5 Li, Y.; Yang, Y.; Bao, X.; Qiu, M.; Liu,Z.; Wang, N.; Zhang,G.; Yang, R.; Zhang, D. New 7r-conjugated polymers as acceptors designed for all polymer solar cells based on imide/amidederivatives. J. Mater. Chem. C 2016, 4, 185-192.
6 Guo, Y.; Li,Y.; Awartani,O.; Han,H.; Zhang,G.; Ade,H.;Yan, H.; Zhao, D. Side-chain engineering of perylenediimidevinylene polymer acceptors for high-performance all-polymer solar cells. Mater. Chem. Front. 2017, 1, 1362-1398.
7 Zhang, Z. G.; Yang, Y.; Yao, J.; Xue, L.; Chen, S.; Li, X.; Morrison, W.; Yang, C.; Li, Y. Constructing a strongly absorbing low-bandgap polymer acceptor for high-performance all-polymer solar cells. Angew. Chem. Int. Ed. 2017, 56, 13688-13692.
8 Dai,S.; Huang,S.; Yu,H.; Ling,Q.; Zhan, X. Perylene and naphthalene diimide copolymers for all-polymer solar cells:Effect of perylene/naphthalene ratio. J. Polym. Sci., Part A:Polym. Chem. 2017, 55, 682-689.
9 Fan,B.; Zhu,P.; Xin,J.; Li,N.; Ying,L.; Zhong,W.; Li,Z.;Ma, W.; Huang, F.; Cao, Y. High-performance thick-film allpolymer solar cells created via ternary blending of a novel wide-bandgap electron-donating copolymer. Adv. Energy Mater. 2018, 8, 1703085.
10 Yuan, J.; Ford, M. J.; Xu, Y.; Zhang, Y.; Bazan, G. C.; Ma, W.Improved tandem all-polymer solar cells performance by using spectrally matched subcells. Adv. Energy Mater. 2018, 8,1703291.
11 Yin, Y.; Yang, J.; Guo, F.; Zhou, E.; Zhao, L.; Zhang, Y. Highperformance all-polymer solar cells achieved by fused perylenediimide-based conjugated polymer acceptors. ACS App. Mater. Interfaces 2018,10, 15962-15970.
12 Zhou,Y.;Yan,Q.;Zheng,Y.Q.;Wang,J.Y.;Zhao,D.;Pei,J.New polymer acceptors for organic solar cells:The effect of regio-regularity and device configuration. J. Mater. Chem. A2013, 1, 6609-6613.
13 Hu, Z.; Ying, L.; Huang, F.; Cao, Y. Towards a bright future:Polymer solar cells with power conversion efficiencies over10%. Sci. China Chem. 2017, 60, 571-582.
14 Kang, H.; Lee, W.; Oh, J.; Kim, T.; Lee, C.; Kim, B. J. From fullerene-polymer to all-polymer solar cells:The importance of molecular packing, orientation and morphology control Acc.Chem. Res. 2016, 49, 2424-2434.
15 Jung, J.; Lee, W.; Lee, C.; Ahn, H.; Kim, B. J. Controlling molecular orientation of naphthalenediimide-based polymer acceptors for high performance all-polymer solar cells. Adv. Energy Mater. 2016, 6, 1600504.
16 Zhou, N.; Lin, H.; Lou, S. J.; Yu, X.; Guo, P.; Manley, E. F.;Loser, S.; Hartnett, P.; Huang, H.; Wasielewski, M. R.; Chen,L. X.; Chang, R. P. H.; Facchetti, A.; Marks, T. J. Morphologyperformance relationships in high-efficiency all-polymer solar cells.Adv. Energy Mater. 2014, 4, 1300785.
17 Mu, C.; Liu, P.; Ma, W.; Jiang, K.; Zhao, J.; Zhang, K.; Chen,Z.; Wei, Z.; Yi, Y.; Wang, J.; Yang, S.; Huang, F.; Facchetti,A.; Ade, H.; Yan, H. High-efficiency all-polymer solar cells based on a pair of crystalline low-bandgap polymers. Adv. Mater. 2014, 26, 7224-7230.
18 Choi, J.; Kim, K. H.; Yu, H.; Lee, C.; Kang, H.; Song, I.; Kim,Y.; Oh, J. H.; Kim, B. J. Importance of electron transport ability in naphthalene diimide-based polymer acceptors for highperformance, additive-free, all-polymer solar cells. Chem. Ma-.er. 2015, 27, 5230-5237.
19 Ye,L.; Jiao, X.; Zhao, W.; Zhang, S.; Yao, H.; Li,S.; Ade, H.;Hou, J. Manipulation of domain purity and orientational ordering in high performance all-polymer solar cells. Chem. Mater.2016,28, 6178-6185.
20 Hwang, Y. J.; Earmme, T.; Courtright, B. A. E.; Eberle, F. N.;Jenekhe, S. A. N-Type semiconducting naphthalene diimideperylene diimide copolymers:Controlling crystallinity, blend morphology, and compatibility toward high-performance allpolymer solar cells. J. Am. Chem. Soc. 2015, 137, 4424-4434.
21 Suranagi, S. R.; Singh, R.; Kim, J. H.; Kim, M.; Ade, H.; Cho,K. Molecular engineering of perylene-diimide-based polymer acceptors containing heteroacene units for all-polymer solar cells. Org. Electron. 2018, 58, 222-230.
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