Abstract
Two conjugated polymers containing benzodithiophene (BDT) unit and the unit of thiophene or thieno[3,2-b]thiophene, P(BDT-T) and P(BDT-TT), were synthesized by Pd-catalyzed Stille coupling method. The UV–Vis absorption, thermal, and electrochemical properties of the two polymers were characterized. Photovoltaic properties of the polymers were studied by using the polymers as donor and PC70BM as acceptor with a weight ratio of polymer: PC70BM of 1:1.5. The power conversion efficiencies of the PSC devices based on P(BDT-T) reached 2.05% with an open-circuit voltage of 0.75 V, a short-circuit current of 4.5 mA cm−2, and a fill factor of 0.61, under the illumination of AM1.5, 100 mW cm−2.
Similar content being viewed by others
References
Dennler G, Scharber MC, Brabec CJ (2009) Polymer-fullerene bulk-heterojunction solar cells. Adv Mater 21:1323
Cheng Y-J, Yang S-H, Hsu C-S (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868
Chen JW, Cao Y (2009) Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices. Acc Chem Res 42:1709
Krebs FC (2009) Fabrication and processing of polymer solar cells: a review of printing and coating techniques. Sol Energy Mater Sol Cells 93:394
Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ (1995) Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science 270:1789
Li G, Shrotriya V, Huang JS, Yao Y, Moriarty Y, Emery K, Yang Y (2005) High-efficiency solution processable polymer. Nat Mater 4:864
Ma WL, Yang CY, Gong X, Lee KH, Heeger AJ (2005) Thermally stable, efficient polymer soar cells with nanoscale control of the interpenetrating network morphology. Adv Funct Mater 15:1617
Hou JH, Chen HY, Zhang SQ, Chen RI, Yang Y, Wu Y, Li G (2009) Synthesis of a low band gap polymer and its application in highly efficient polymer solar cells. J Am Chem Soc 131:15586
Chen HY, Hou JH, Zhang SQ, Liang YY, Yang GW, Yang Y, Yang LP, Wu Y, Li G (2009) Polymer solar cells with enhanced open-circuit voltage and efficiency. Nat Photonics 3:649
Liang YY, Wu Y, Feng DQ, Tsai ST, Son HJ, Li G, Yu LP (2009) Development of new semiconducting polymers for high performance solar cells. J Am Chem Soc 131:56
Liang YY, Xu Z, Xia JB, Tsai ST, Wu Y, Li G, Ray C, Yu LP (2010) For the bright future-bulk heterojunction polymer solar cells with power conversion efficiency of 7.4%. Adv Mater 22:E135
Chu T, Lu J, Beaupr S, Zhang Y, Pouliot J, Wakim S, Zhou J, Leclerc M, Li Z, Ding J, Tao Y (2011) Bulk heterojunction solar cells using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole copolymer with a power conversion efficiency of 7.3%. J Am Chem Soc 133:4250
Zhang MJ, Guo X, Li YF (2011) Synthesis and characterization of a copolymer based on thiazolothiazole and dithienosilole for polymer solar cells. Adv Energy Mater 1:557
He YJ, Li YF (2011) Fullerene derivative acceptors for high performance polymer soalr cells. Phys Chem Chem Phys 13:1970
He YJ, Chen HY, Hou JH, Li YF (2010) Indene-C60 bisadduct: a new acceptor for high-performance polymer solar cells. J Am Chem Soc 132:1377
Zhao GJ, He YJ, Li YF (2010) 6.5% efficiency of polymer solar cells based on poly(3-hexylthiophene) and indene-C60 bisadduct by device optimization. Adv Mater 22:4355
Hou JH, Park MH, Zhang SQ, Yao Y, Chen LM, Li JH, Yang Y (2008) Bandgap and molecular energy level control of conjugated polymer photovoltaic materials based on Benzo[1,2-b:4,5-b′]dithiophene. Macromolecules 41:6012
Huang Y, Huo LJ, Zhang SQ, Guo X, Han CC, Li YF, Hou JH (2011) Sulfonyl: a new application of electron-withdrawing substituent in highly efficient photovoltaic polymer. Chem. Commun 47:8904
Huo LJ, Zhang SQ, Guo X, Xu F, Li YF, Hou JH (2011) Replacing alkoxy groups with alkylthienyl groups: a feasible approach to improve the properties of photovoltaic polymers. Angew Chem Int Ed 50:9697
Zou YP, Naiari A, Berrouard P, Beaupre S, Aich BR, Tao Y, Leclerc M (2010) A thieno[3,4-c]pyrrole-4,6-dione-based copolymer for efficient solar cells. J Am Chem Soc 132:5330
Zhang GB, Fu YY, Zhang Q, Xie ZY (2010) Benzo[1,2-b:4,5-b′]dithiophene-dioxopyrrolothiophen copolymers for high performance solar cells. Chem Commun 46:4997
Piliego C, Holcombe TW, Douglas JD, Woo CH, Beaujuge PM, Frechet MJ (2010) Synthetic control of structural order in N-alkylthieno[3,4-c]pyrrole-4,6-dione-based polymers for efficient solar cells. J Am Chem Soc 132:7595
Zhang Y, Hau SK, Yip HL, Sun Y, Acton O, Jen AK (2010) Efficient polymer solar cells based on the copolymers of benzodithiophene and thienopyrroledione. Chem Mater 22:2696
Huo LJ, Hou JH, Zhang SQ, Chen HY, Yang Y (2010) A polybenzo[1,2-b:4,5-b′]dithiophene derivative with deep HOMO Level and its application in high-performance polymer solar cells. Angew Chem Int Ed 49:1500
Huo LJ, Guo X, Zhang SQ, Li YF, Hou JH (2011) PBDTTTZ: a broad band gap conjugated polymer with high photovoltaic performance in polymer solar cells. Macromolecules 44:4035
Wang M, Hu X, Liu P, Li W, Gong X, Huang F, Cao Y (2011) Donor–acceptor conjugated polymer based on naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole for high-performance polymer solar cells. J Am Chem Soc 133:9638
Zhang MJ, Fan HJ, Guo X, He YJ, Zhang ZG, Min J, Zhang J, Zhan XW, Li YF (2010) Synthesis and Photovoltaic properties of a copolymer of benzo[1,2-b:4,5-b′]dithiophene and bithiazole. Macromolecules 43:8714
He YJ, Zhou Y, Zhao GJ, Min J, Guo X, Zhang B, Zhang MJ, Zhang J, Li YF, Zhang FL, Inganas O (2010) Poly(4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]dithiophene vinylene): synthesis, optical and photovoltaic properties. J Polym Sci A 48:1822
McCullch I, Heeney M, Bailey C, Genevicius K, Macdonald I, Shkunov M, Sparrowe D, Tierney S, Wagner R, Zhang WM, Chabinyc ML, Kline RJ, McGehee MD, Toney MF (2006) Liquid-crystalline semiconducting polymers with high charge-carrier mobility. Nat Mater 5:328
Chabinyc ML, Toney MF, Kline RJ, McCulloch I, Heeney M (2007) X-ray scattering study of thin films of poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-b]thiophene). J Am Chem Soc 129:3226
He YJ, Wu WP, Zhao GJ, Liu YQ, Li YF (2008) Poly(3,6-dihexyl-thieno[3,2-b]thiophene vinylene): synthesis, field-effect transistors, and photovoltaic properties. Macromolecules 41:9760
Li Y, Wu Y, Liu P, Birau M, Pan H, Ong BS (2006) Poly(2,5-bis(2-thienyl)-3,6-dialkylthieno[3,2-b]thiophene)s-high-mobility semiconductors for thin-film transistors. Adv Mater 18:3029
Muhlbacher D, Scharber M, Morana M, Zhu ZG, Waller D, Gaudiana R, Brabec CJ (2006) High photovoltaic performance of a low-bandgap polymer. Adv Mater 18:2884
He MQ, Zhang FX (2007) Synthesis and structure of alkyl-substituted fused thiophenes containing up to seven rings. J Org Chem 72:442
He YJ, Zhang MJ, Min J, Zhao GJ, Li YF (2009) Influence of sulfur oxidation on the absorption and electronic energy levels of poly(thienothiophene) derivatives. J Phys Chem B 113:14981
Beimling P, Komehl G (1986) Synthesis of benzo[1,2-b′:4,5-b′]dithiophene and its 4,8-Dimethoxy and 4,8-dimethyl derivatives. Chem Ber 119:3198
Seitz DE, Lee SH, Hanson RN, Bottaro JC (1983) Synthesis and reactivity of the 2,5-bis(Trimethylstannyl) derivatives of thiophene and furan. Synth Commun 13:121
Heeney M, Bailey C, Genevicius K, Shkunov M, Sparrowe D, Tierney S, McCulloch I (2005) Stable polythiophene semiconductors incorporating thieno[2,3-b]thiophene. J Am Chem Soc 127:1078
Li YF, Cao Y, Gao J, Wang DL, Yu G, Heeger AJ (1999) Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells. Synth Met 99:243
Sun QJ, Wang HQ, Yang CH, Li YF (2003) Synthesis and electroluminescence of novel copolymers containing crown ether spacers. J Mater Chem 13:800
Hou JH, Tan ZA, Yan Y, He YJ, Yang CH, Li YF (2006) Synthesis and photovoltaic properties of two-dimensional conjugated polythiophenes with bi(thienylenevinylene) side chains. J Am Chem Soc 128:4911
Johansson T, Mammo W, Svensson M, Andersson MR, Inganas O (2003) Electrochemical bandgaps of substituted polythiophenes. J Mater Chem 13:1316
Chen WC, Liu CL, Yen CT, Tsai FC, Tonzola CJ, Olson N, Jenekhe SA (2004) Theoretical and experimental characterization of small band gap poly(3,4-ethylenedioxythiophene methine)s. Macromolecules 37:5959
Acknowledgments
This study was supported by NSFC (Nos. 20874106, 20821120293) and Chinese Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Min, J., Peng, B., He, Y. et al. Synthesis and photovoltaic properties of alternative copolymers of benzo[1,2-b:4,5-b′]dithiophene and thiophene. Polym. Bull. 68, 2107–2119 (2012). https://doi.org/10.1007/s00289-011-0672-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-011-0672-z