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Synthesis and properties of a new conjugated polymer containing benzodithiophene for polymer solar cells

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Abstract

We have synthesized a new conjugated polymer PBDTDT containing 4,8-dioctyloxybenzo[1,2-b;3,4-b′]di-thiophene and 2,2′-dithiophene via a Stille coupling reaction. The copolymer was characterized by FTIR, NMR, GPC, TGA, DSC, UV–vis absorption, and electrochemical cyclic voltammetry. TGA showed that the copolymer exhibited good thermal stability. The optical, electrochemical, photovoltaic properties, and hole mobility of the copolymer were investigated and discussed. As a result, the polymer solar cell based on PBDTDT with a conventional device configuration of ITO/PEDOT:PSS/PBDTDT:PC61BM/LiF/Al showed a power conversion efficiency of 1.19 %, with a short-circuit current density (J sc) of 4.72 mA/cm2, an open-circuit voltage (V oc) of 0.6 V and a fill factor of 53.3 % under the AM 1.5G illumination with an intensity of 100 mW/cm2 from a solar simulator.

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References

  1. Günes S, Neugebauer H, Sariciftci NS (2007) Conjugated polymer-based organic solar cells. Chem Rev 107:1324–1338

    Article  CAS  Google Scholar 

  2. Coakley KM, McGehee MD (2004) Conjugated polymer photovoltaic cells. Chem Mater 16:4533–4542

    Article  CAS  Google Scholar 

  3. Spanggaard H, Krebs FC (2004) A brief history of the development of organic and polymeric photovoltaics. Sol Energy Mater Sol Cells 83(2–3):125–146

    Article  CAS  Google Scholar 

  4. Brabec CJ, Durrant JR (2008) Solution-processed organic solar cells. MRS Bull 33:670–675

    Article  CAS  Google Scholar 

  5. Krebs FC, Jørgensen M, Norrman K, Hagemann O, Alstrup J, Nielsen TD, Fyenbo J, Larsen K, Kristensen J (2009) A complete process for production of flexible large area polymer solar cells entirely using screen printing—First public demonstration. Sol Energy Mater Sol Cells 93(4):422–441

    Article  CAS  Google Scholar 

  6. Krebs FC (2009) Polymer solar cell modules prepared using roll-to-roll methods: knife-over-edge coating, slot-die coating and screen printing. Sol Energy Mater Sol Cells 93(4):465–475

    Article  CAS  Google Scholar 

  7. Helgesen M, Søndergaard R, Krebs FC (2010) Advanced materials and processes for polymer solar cell devices. J Mater Chem 20(1):36

    Article  CAS  Google Scholar 

  8. Huo L, Hou J, Zhang S, Chen H-Y, 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 49:1500–1503

    Article  CAS  Google Scholar 

  9. Winder C, Sariciftci NS (2004) Low bandgap polymers for photon harvesting in bulk heterojunction solar cells. J Mater Chem 14:1077–1086

    Article  CAS  Google Scholar 

  10. Yu G, Heeger AJ (1995) Charge separation and photovoltaic conversion in polymer composites with internal donor–acceptor heterojunctions. J Appl Phys 78(7):4510–4515

    Article  CAS  Google Scholar 

  11. Inganäs O, Svensson M, Gadisa A, Zhang F, Persson NK, Wang X, Andersson MR (2004) Low bandgap alternating polyfluorene copolymers in plastic photodiodes and solar cells. Appl Phys A Mater Sci Process 79(1):31–35

    Article  CAS  Google Scholar 

  12. Shaheen SE, Brabec CJ, Sariciftci NS, Padinger F, Fromherz T, Hummelen JC (2001) 2.5% efficient organic plastic solar cells. Appl Phys Lett 78:841–843

    Article  CAS  Google Scholar 

  13. McNeill CR, Halls JJM, Wilson R, Whiting GL, Berkebile S, Ramsey MG, Friend RH, Greenham NC (2008) Efficient polythiophene/polyfluorene copolymer bulk heterojunction photovoltaic devices: device physics and annealing effects. Adv Funct Mater 18(16):2309–2321

    Article  CAS  Google Scholar 

  14. Cheyns D, Vasseur K, Rolin C, Genoe J, Poortmans J, Heremans P (2008) Nanoimprinted semiconducting polymer films with 50 nm features and their application to organic heterojunction solar cells. Nanotechnology 19(42):424016

    Article  CAS  Google Scholar 

  15. Liang Y, Xu Z, Xia J, Tsai S-T, Wu Y, Li G, Ray C, Yu L (2010) For the bright future-bulk heterojunction polymer solar cells with power conversion efficiency of 7.4 %. Adv Mater 22(20):E135–E138

    Article  CAS  Google Scholar 

  16. Zhang M, Guo X, Wang X, Wang H, Li Y (2011) Synthesis and photovoltaic PROPERTIES of D-A copolymers based on alkyl-substituted indacenodithiophene donor unit. Chem Mater 23(18):4264–4270

    Article  CAS  Google Scholar 

  17. Amb CM, Chen S, Graham KR, Subbiah J, Small CE, So F, Reynolds JR (2011) Dithienogermole as a fused electron donor in bulk heterojunction solar cells. J Am Chem Soc 133(26):10062–10065

    Article  CAS  Google Scholar 

  18. Zhao C, Chen X, Zhang Y, M-k Ng (2008) 4,9-Dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene-4,9-dione functionalized copolymers for organic photovoltaic devices. J Polym Sci Part A Polym Chem 46(8):2680–2688

    Article  CAS  Google Scholar 

  19. Bundgaard E, Krebs F (2007) Low band gap polymers for organic photovoltaics. Sol Energy Mater Sol Cells 91(11):954–985

    Article  CAS  Google Scholar 

  20. Li Y, Zou Y (2008) Conjugated polymer photovoltaic materials with broad absorption band and high charge carrier mobility. Adv Mater 20(15):2952–2958

    Article  CAS  Google Scholar 

  21. Pan H, Li Y, Wu Y, Liu P, Ong BS, Zhu S, Xu G (2007) Low-temperature, solution-processed, high-mobility polymer semiconductors for thin-film transistors. J Am Chem Soc 129:4112–4113

    Article  CAS  Google Scholar 

  22. Hou J, Park M-H, Zhang S, Yao Y, Chen L-M, Li J-H, Yang Y (2008) Bandgap and molecular energy level control of conjugated polymer photovoltaic materials based on benzo[1,2-b4,5-b′]dithiophene. Macromolecules 41:6012–6018

    Article  CAS  Google Scholar 

  23. Wang H, Shi Q, Lin Y, Fan H, Cheng P, Zhan X, Li Y, Zhu D (2011) Conjugated polymers based on a new building block: dithienophthalimide. Macromolecules 44(11):4213–4221

    Article  CAS  Google Scholar 

  24. Liu Y, Liu Y, Zhan X (2011) High-mobility conjugated polymers based on fused-thiophene building blocks. Macromol Chem Phys 212(5):428–443

    Article  CAS  Google Scholar 

  25. Chang Y-T, Hsu S-L, Su M-H, Wei K-H (2009) Intramolecular donor–acceptor regioregular poly(hexylphenanthrenyl-imidazole thiophene) exhibits enhanced hole mobility for heterojunction solar cell applications. Adv Mater 21:2093–2097

    Article  CAS  Google Scholar 

  26. Hou J, Chen H-Y, Zhang S, 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 131:15586–15587

    Article  CAS  Google Scholar 

  27. 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-b4,5-b′]dithiophene). Chem Mater 18:3237–3241

    Article  CAS  Google Scholar 

  28. Yamamoto T, Kamijoh T, Wataru I (2000) Preparation and spectroscopic data of 13C-Labeled Polythiophenes and corresponding iodide monomers. J Polym Sci Part A Polym Chem 38:1642–1646

    Article  CAS  Google Scholar 

  29. Shiraishi K, Yamamoto T (2002) New p-conjugated polymers constituted of dialkoxybenzodithiophene units: synthesis and electronic properties. Synth Met 130:139–147

    Article  CAS  Google Scholar 

  30. Thompson BC, Fréchet JMJ (2008) Polymer–fullerene composite solar cells. Angew Chem Int Ed 47(1):58–77

    Article  CAS  Google Scholar 

  31. Wakim S, Aïch BR, Tao Y, Leclerc M (2008) Charge transport, photovoltaic, and thermoelectric properties of poly(2,7-carbazole) and poly(indolo[3,2-b]carbazole) derivatives. Polym Rev 48(3):432–462

    Article  CAS  Google Scholar 

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Acknowledgments

The financial support provided by the National Science Council (Taiwan, ROC) through project NSC 99-2627-E-006-001 is greatly appreciated.

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Correspondence to Steve Lien-Chung Hsu.

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Chuang, HY., Hsu, S.LC., Lee, PI. et al. Synthesis and properties of a new conjugated polymer containing benzodithiophene for polymer solar cells. Polym. Bull. 71, 1117–1130 (2014). https://doi.org/10.1007/s00289-014-1114-5

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  • DOI: https://doi.org/10.1007/s00289-014-1114-5

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