Synthesis of a New Random Terpolymer Donor with an Application to Organic Solar Cells
REN Jingkun1, LIU Weipeng1, LI Zhanfeng1, SUN Qinjun1, WANG Hua2, SHI Fang1, HAO Yuying1
1 Key Lab of Advanced Transducers and Intelligent Control System of Ministry of Education and Shanxi Province, College of Physics and Optoelectronics, Taiyuan University of Technology, Taiyuan 030024; 2 Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024
Abstract: A new random 2D/A terpolymer PDPP-BDT-NT comprising diketopyrrolo[3,4-c]pyrrole-1,4-dione (DPP) as A unit, benzo[1,2-b∶4,5-b′]dithiophene (BDT) and naphthalene (NT) as D units has been designed and synthesized via Stille coupling polymerization specifically for polymer solar cells (PSCs). Its structure was defined by proton nuclear magnetic resonance (1H NMR). And its thermogravimetric analysis, photophysical properties and energy-level structure were studied by thermal property, ultraviolet-visble (UV-Vis) absorption spectra, and cyclic voltammetry(CV). PDPP-BDT-NT exhibited good thermal stability with a decomposition temperature over 401 ℃. The terpolymer presented both broad absorption (300—900 nm) and low highest occupied molecular orbital level for -5.35 eV. Preliminary studies of bulk heterojunction (BHJ) solar cells based on PDPP-BDT-NT as donor material with PC60BM as acceptor material showed a promising power conversion efficiency (PCE) of 2.09% without any processing and post-treatment (under the illumination of AM 1.5, 100 mW·cm-2), after MeOH treatment, the PCE of polymer solar cell was raised to 2.34%.
任静琨, 刘伟鹏, 李战峰, 孙钦军, 王华, 史方, 郝玉英. 新型三元聚合物给体材料的合成及在有机太阳能电池中的应用*[J]. 《材料导报》期刊社, 2017, 31(17): 133-137.
REN Jingkun, LIU Weipeng, LI Zhanfeng, SUN Qinjun, WANG Hua, SHI Fang, HAO Yuying. Synthesis of a New Random Terpolymer Donor with an Application to Organic Solar Cells. Materials Reports, 2017, 31(17): 133-137.
1 Zhang F, Inganäs O, Zhou Y, et al.Development of polymer-fullerene solar cells[J]. National Sci Rev,2016,3(2):222. 2 Zhou H X, Yang L Q, You W. Rational design of high performance conjugated polymers for organic solar cells[J]. Macromolecules,2012,45(2):607. 3 Somasundaram S, Jeon S, Park S.Triphenylamine and benzothiadiazole-based D-A-A’ and A’-A-D-D-A-A’ type small molecules for solution-processed organic solar cells[J]. Macromolecular Res,2016,24(3):226. 4 Zhao W, Li S, Yao H, et al.Molecular optimization enables over 13% efficiency in organic solar cells[J]. J Am Chem Soc,2017,139(21):7148. 5 Chen J W, Cao Y. Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices[J]. Accounts Chem Res,2009,42(11):1709. 6 Goker S, Hizalan G, Aktas E, et al. 2,1,3-Benzooxadiazole, thiophene and benzodithiophene based random copolymers for organic photovoltaics: Thiophene versus thieno[3,2-b]thiophene as π-conjugated linkers[J]. New J Chem,2016,40(12):10455. 7 Keshtov M L, Khokhlov A R, Kuklin S A, et al. Benzothiadiazole-pyrrolo[3,4-b]dithieno[2,3-f:3′,2′-h] quinoxalindione-based random terpolymer incorporating strong and weak electron accepting [1,2,5]thiadiazolo[3,4g]quinoxalinefor polymer solar cells[J]. Organ Electron,2017,41:1. 8 Hendriks K H, Heintges G H L, Wienk M M, et al.Comparing random and regular diketopyrrolopyrrole-bithiophene-thienopyrrolo-dione terpolymers for organic photovoltaics[J]. J Mater Chem A,2014,2(42):17899. 9 Tamilavan V, Song M, Jin S H, et al.Synthesis of new broad absorption low band gap random copolymers for bulk heterojunction solar cell applications[J]. Macromol Res,2013,21:406. 10 Kang T E, Kim K H, Kim B J. Design of terpolymers as electron donors for highly efficient polymer solar cells[J]. J Mater Chem A,2014,2(37):15252. 11 Li Z, Qiao Z, Liu W, et al.Conjugated random copolymer of benzodithiophene-difluorobenzene-diketopyrrolopyrrole-benzothia-diazole with a broad absorption range of 300-900nm for bulk heterojunction solar cells[J]. Mater Lett,2015,139: 307. 12 Ha Y H, Lee J E, Hwang M C, et al.A new BDT-based conjugated polymer with donor-donor composition for bulk heterojunction solar cells[J]. Macromol Res,2016,24:457. 13 Yao H, Ye L, Zhang H, et al.Molecular design of benzodithiophene-based organic photovoltaic materials[J]. Chem Rev,2016,116(12):7397. 14 Wang Z H, Li Z F, Zhang H Q, et al.A conjugated random copolymer of benzodithiophene-difluorobenzene-diketopyrrolopyrrole with full visible-light absorption for bulk-heterojunction solar cells[J]. Macromol Chem Phys,2014,215(21):2119. 15 Kim K H, Park S, Yu H, et al.Determining optimal crystallinity of diketopyrrolopyrrole-based terpolymers for highly efficient polymer solar cells and transistors[J]. Chem Mater,2014, 26(24):6963. 16 Huang Y S, Chen H J, Wu F, et al. Efficient polymer solar cells based on terpolymers with a broad absorption range of 300—900 nm[J]. J Mater Chem A,2014,2:5218. 17 Sambathkumar B P, Deepakrao F, Iyer S, et al.Two donor-one acceptor random terpolymer comprised of diketopyrrolopyrrole quaterthiophene with various donor π-linkers for organic photovoltaic application[J]. J Phys Chem C,2016,120:26609. 18 Hendriks K H, Li W W, Heintges G H L, et al. Homocoupling defects in diketopyrrolopyrrole-based copolymers and their effect on photovoltaic performance[J]. J Am Chem Soc,2014,136(31):11128. 19 Becke A D. Density-functional thermochemistry. III. The role of exact exchange[J]. J Chem Phys,1993,98(7):5648. 20 Stephens P J, Frisch M J, Devlin F J. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields[J]. J Phys Chem,1994,98(45):11623. 21 Dou L T, Gao J, Richard E, et al. Systematic Investigation of benzodithiophene- and diketopyrrolopyrrole-based low-bandgap polymers designed for single junction and tandem polymer solar cells[J]. J Am Chem Soc,2012,134(24):10071. 22 Zheng Y, Li S, Zheng D, et al.Effects of different polar solvents for solvent vapor annealing treatment on the performance of polymer solar cells[J]. Organ Electron,2014,15(11):2647.
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2017, Vol. 31 
