Skip to main content
Log in

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

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Dennler G, Scharber MC, Brabec CJ (2009) Polymer-fullerene bulk-heterojunction solar cells. Adv Mater 21:1323

    Article  CAS  Google Scholar 

  2. Cheng Y-J, Yang S-H, Hsu C-S (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868

    Article  CAS  Google Scholar 

  3. Chen JW, Cao Y (2009) Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices. Acc Chem Res 42:1709

    Article  CAS  Google Scholar 

  4. Krebs FC (2009) Fabrication and processing of polymer solar cells: a review of printing and coating techniques. Sol Energy Mater Sol Cells 93:394

    Article  CAS  Google Scholar 

  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 270:1789

    Article  CAS  Google Scholar 

  6. Li G, Shrotriya V, Huang JS, Yao Y, Moriarty Y, Emery K, Yang Y (2005) High-efficiency solution processable polymer. Nat Mater 4:864

    Article  CAS  Google Scholar 

  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 15:1617

    Article  CAS  Google Scholar 

  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 131:15586

    Article  CAS  Google Scholar 

  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 3:649

    Article  CAS  Google Scholar 

  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 131:56

    Article  CAS  Google Scholar 

  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:E135

    Article  CAS  Google Scholar 

  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 133:4250

    Article  CAS  Google Scholar 

  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 1:557

    Article  CAS  Google Scholar 

  14. He YJ, Li YF (2011) Fullerene derivative acceptors for high performance polymer soalr cells. Phys Chem Chem Phys 13:1970

    Article  CAS  Google Scholar 

  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 132:1377

    Article  CAS  Google Scholar 

  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 22:4355

    Article  CAS  Google Scholar 

  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 41:6012

    Article  CAS  Google Scholar 

  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 47:8904

    Article  CAS  Google Scholar 

  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 50:9697

    Google Scholar 

  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 132:5330

    Article  CAS  Google Scholar 

  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 46:4997

    Article  CAS  Google Scholar 

  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 132:7595

    Article  CAS  Google Scholar 

  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 22:2696

    Article  CAS  Google Scholar 

  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 49:1500

    Article  CAS  Google Scholar 

  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 44:4035

    Article  CAS  Google Scholar 

  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 133:9638

    Article  CAS  Google Scholar 

  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 43:8714

    Article  CAS  Google Scholar 

  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 48:1822

    Article  CAS  Google Scholar 

  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 5:328

    Article  Google Scholar 

  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 129:3226

    Article  CAS  Google Scholar 

  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 41:9760

    Article  CAS  Google Scholar 

  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 18:3029

    Article  CAS  Google Scholar 

  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 18:2884

    Article  Google Scholar 

  34. He MQ, Zhang FX (2007) Synthesis and structure of alkyl-substituted fused thiophenes containing up to seven rings. J Org Chem 72:442

    Article  CAS  Google Scholar 

  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 113:14981

    Article  CAS  Google Scholar 

  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 119:3198

    Article  CAS  Google Scholar 

  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 13:121

    Article  CAS  Google Scholar 

  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 127:1078

    Article  CAS  Google Scholar 

  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 99:243

    Article  CAS  Google Scholar 

  40. Sun QJ, Wang HQ, Yang CH, Li YF (2003) Synthesis and electroluminescence of novel copolymers containing crown ether spacers. J Mater Chem 13:800

    Article  CAS  Google Scholar 

  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 128:4911

    Article  CAS  Google Scholar 

  42. Johansson T, Mammo W, Svensson M, Andersson MR, Inganas O (2003) Electrochemical bandgaps of substituted polythiophenes. J Mater Chem 13:1316

    Article  CAS  Google Scholar 

  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 37:5959

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was supported by NSFC (Nos. 20874106, 20821120293) and Chinese Academy of Sciences.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yongfang Li.

Rights and permissions

Reprints 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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-011-0672-z

Keywords

Navigation