Abstract
A new accepter unit, 5,6-difluoro-2,2-dimethyl-2H-benzo[d]imidazole, was prepared and utilized for the synthesis of the conjugated polymers containing electron donor–acceptor pair for OPVs. Difluoro-dimethyl-2H-benzoimidazole unit was designed to introduce electron-withdrawing F atom in dimethyl-2H-benzimidazole unit to improve deeper HOMO and higher V OC of the polymer. New semiconducting copolymer with dioctyloxybenzodithiophene, as the electron-rich unit, and difluoro-dimethyl-2H-benzoimidazole, as the electron-deficient unit, was synthesized by Stille polymerization.
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Krebs FC, Gevorgyan SA, Alstrup J (2009) A roll-to-roll process to flexible polymer solar cells: model studies, manufacture and operational stability studies. J Mater Chem 19:5442–5451
Song S, Jin Y, Park SH, Cho S, Kim I, Lee K, Heeger AJ, Suh H (2010) A low-bandgap alternating copolymer containing the dimethyl-2H-benzimidazole moiety. J Mater Chem 20:6517–6523
Song S, Park SH, Jin Y, Park J, Shim JY, Kim I, Lee H, Lee K, Suh H (2010) Synthesis and characterization of low-bandgap copolymers based on dihexyl-2H-benzimidazole and cyclopentadithiophene. J Polym Sci Polym Chem 48:4567–4573
Park SH, Roy A, Beaupre S, Cho S, Coates N, Moon JS, Moses D, Leclerc M, Lee K, Heeger AJ (2009) Bulk heterojunction solar cells with internal quantum efficiency approaching 100%. Nat Photonics 3:297–302
Scharber MC, Muhlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CJ (2006) Design rules for donors in bulk-heterojunction solar cells—towards 10% energy-conversion efficiency. Adv Mater 18:789–794
Li Y, Yao K, Yip HL, Ding FZ, Xu YX, Li X, Chen Y, Jen AKY (2014) Eleven-membered fused-ring low band-gap polymer with enhanced charge carrier mobility and photovoltaic performance. Adv Funct Mater 24(23):3631–3638
Huo L, Guo X, Zhang S, Li Y, Hou J (2011) PBDTTTZ: a broad band gap conjugated polymer with high photovoltaic performance in polymer solar cells. Macromolecules 44:4035–4037
Pan H, Li Y, Wu Y, Liu P, Ong BS, Zhu S, Xu G (2006) Synthesis and thin-film transistor performance of poly(4,8-didodecylbenzo[1,2-b:4,5-b′]dithiophene). Chem Mater 18:3237–3241
Pan H, Wu Y, Li Y, Liu P, Ong BS, Zhu S, Xu G (2007) Benzodithiophene copolymer-a low-temperature, solution-processed high-performance semiconductor for thin-film transistors. Adv Funct Mater 17:3574–3579
Iyer A, Bjorgaard J, Anderson T, Köse ME (2012) Quinoxaline-based semiconducting polymers: effect of fluorination on the photophysical, thermal, and charge transport properties. Macromolecules 16:6380–6389
Chen HC, Chen YH, Liu CC, Chien YC, Chou SW, Chou PT (2012) Prominent short-circuit currents of fluorinated quinoxaline-based copolymer solar cells with a power conversion efficiency of 8.0%. Chem Mate 24(24):4766–4772
Song S, Choi HI, Shin IS, Suh H, Hyun MH, Lee GD, Park SS, Park SH, Jin Y (2014) Synthesis and photovoltaic properties of quinoxaline-based semiconducting polymers with fluoro atoms. Bull Korean Chem Soc 35(8):2245–2250
Dang D, Chen W, Yang R, Zhu W, Mammod W, Wang E (2013) Fluorine substitution enhanced photovoltaic performance of a D-A1–D–A2 copolymer. Chem Commun 49:9335–9337
Song S, Ko SJ, Kim JA, Jin Y, Kim I, Kim JY, Suh H (2013) Synthesis of a conjugated copolymer with benzodithiophene and benzimidazole units. Polym J 45(5):555–559
Cho S, Seo JH, Kim SH, Song S, Jin Y, Lee K, Suh H, Heeger AJ (2008) Effect of substituted side chain on donor-acceptor conjugated copolymers. Appl Phys Lett 93:263301–263301-3
Song S, Ko SJ, Kim JA, Jin Y, Kim I, Kim JY, Suh H (2013) Synthesis of a conjugated copolymer with benzodithiophene and benzimidazole units. Polym J 45(5):555–559
Price SC, Stuart AC, Yang L, Zhou H, You W (2011) Fluorine substituted conjugated polymer of medium band gap yields 7% efficiency in polymer–fullerene solar cells. J Am Chem Soc 133(12):4625–4631
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This work was supported by a Research Grant of Pukyong National University (2016 year).
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Song, S., Kim, T., Kang, D. et al. Synthesis and photovoltaic properties of benzimidazole-based copolymer with fluorine atom. Polym. Bull. 73, 2511–2519 (2016). https://doi.org/10.1007/s00289-016-1679-2
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DOI: https://doi.org/10.1007/s00289-016-1679-2