Polymer Bulletin

, Volume 68, Issue 8, pp 2107–2119 | Cite as

Synthesis and photovoltaic properties of alternative copolymers of benzo[1,2-b:4,5-b′]dithiophene and thiophene

  • Jie Min
  • Bo Peng
  • Youjun He
  • Maojie Zhang
  • Zhi-Guo Zhang
  • Jing Zhang
  • Xia Guo
  • Chaohua Cui
  • Dan Deng
  • Yongfang Li
Original Paper

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.

Keywords

Benzodithiophene Conjugated polymers Polymer solar cells 

References

  1. 1.
    Dennler G, Scharber MC, Brabec CJ (2009) Polymer-fullerene bulk-heterojunction solar cells. Adv Mater 21:1323CrossRefGoogle Scholar
  2. 2.
    Cheng Y-J, Yang S-H, Hsu C-S (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868CrossRefGoogle Scholar
  3. 3.
    Chen JW, Cao Y (2009) Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices. Acc Chem Res 42:1709CrossRefGoogle Scholar
  4. 4.
    Krebs FC (2009) Fabrication and processing of polymer solar cells: a review of printing and coating techniques. Sol Energy Mater Sol Cells 93:394CrossRefGoogle Scholar
  5. 5.
    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 270:1789CrossRefGoogle Scholar
  6. 6.
    Li G, Shrotriya V, Huang JS, Yao Y, Moriarty Y, Emery K, Yang Y (2005) High-efficiency solution processable polymer. Nat Mater 4:864CrossRefGoogle Scholar
  7. 7.
    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 15:1617CrossRefGoogle Scholar
  8. 8.
    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 131:15586CrossRefGoogle Scholar
  9. 9.
    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 3:649CrossRefGoogle Scholar
  10. 10.
    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 131:56CrossRefGoogle Scholar
  11. 11.
    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:E135CrossRefGoogle Scholar
  12. 12.
    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 133:4250CrossRefGoogle Scholar
  13. 13.
    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 1:557CrossRefGoogle Scholar
  14. 14.
    He YJ, Li YF (2011) Fullerene derivative acceptors for high performance polymer soalr cells. Phys Chem Chem Phys 13:1970CrossRefGoogle Scholar
  15. 15.
    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 132:1377CrossRefGoogle Scholar
  16. 16.
    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 22:4355CrossRefGoogle Scholar
  17. 17.
    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 41:6012CrossRefGoogle Scholar
  18. 18.
    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 47:8904CrossRefGoogle Scholar
  19. 19.
    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 50:9697Google Scholar
  20. 20.
    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 132:5330CrossRefGoogle Scholar
  21. 21.
    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 46:4997CrossRefGoogle Scholar
  22. 22.
    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 132:7595CrossRefGoogle Scholar
  23. 23.
    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 22:2696CrossRefGoogle Scholar
  24. 24.
    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 49:1500CrossRefGoogle Scholar
  25. 25.
    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 44:4035CrossRefGoogle Scholar
  26. 26.
    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 133:9638CrossRefGoogle Scholar
  27. 27.
    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 43:8714CrossRefGoogle Scholar
  28. 28.
    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 48:1822CrossRefGoogle Scholar
  29. 29.
    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 5:328CrossRefGoogle Scholar
  30. 30.
    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 129:3226CrossRefGoogle Scholar
  31. 31.
    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 41:9760CrossRefGoogle Scholar
  32. 32.
    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 18:3029CrossRefGoogle Scholar
  33. 33.
    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 18:2884CrossRefGoogle Scholar
  34. 34.
    He MQ, Zhang FX (2007) Synthesis and structure of alkyl-substituted fused thiophenes containing up to seven rings. J Org Chem 72:442CrossRefGoogle Scholar
  35. 35.
    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 113:14981CrossRefGoogle Scholar
  36. 36.
    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 119:3198CrossRefGoogle Scholar
  37. 37.
    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 13:121CrossRefGoogle Scholar
  38. 38.
    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 127:1078CrossRefGoogle Scholar
  39. 39.
    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 99:243CrossRefGoogle Scholar
  40. 40.
    Sun QJ, Wang HQ, Yang CH, Li YF (2003) Synthesis and electroluminescence of novel copolymers containing crown ether spacers. J Mater Chem 13:800CrossRefGoogle Scholar
  41. 41.
    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 128:4911CrossRefGoogle Scholar
  42. 42.
    Johansson T, Mammo W, Svensson M, Andersson MR, Inganas O (2003) Electrochemical bandgaps of substituted polythiophenes. J Mater Chem 13:1316CrossRefGoogle Scholar
  43. 43.
    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 37:5959CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Jie Min
    • 1
  • Bo Peng
    • 1
  • Youjun He
    • 1
  • Maojie Zhang
    • 1
  • Zhi-Guo Zhang
    • 1
  • Jing Zhang
    • 1
  • Xia Guo
    • 1
  • Chaohua Cui
    • 1
  • Dan Deng
    • 1
  • Yongfang Li
    • 1
  1. 1.Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic SolidsInstitute of Chemistry, Chinese Academy of SciencesBeijingChina

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