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Synthesis, Characterization and Optoelectronic Properties of Benzodithiophene Based Copolymers for Application in Solar Cells

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Abstract

This paper reports on the synthesis and characterization of novel donor–acceptor (D-A) conjugated polymers containing triisopropylsilylethyny(TIPS)benzo[1,2-b:4,5-b′]dithiophene-diketopyrrolopyrrole (P1 and P2) through Stille co-polymerization method. Thermal stability, optical and electrochemical properties of these polymers were determined. Optical band gaps of the polymers as calculated from their film onset absorption edges were found to be 1.46 and 1.44 eV, respectively. Electrochemical studies revealed HOMO and LUMO energy levels to be −5.22, −5.60 eV, and −3.76, −4.16 eV, respectively. The polymers were thermally stable up to 400–440 °C. Optoelectronic studies indicated that these materials to be promising candidates in solar cell applications.

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References

  1. Tang CW (1986) Two-layer organic photovoltaic cell. Appl. Phys. Lett, appl. Phys. Lett 48:183–185

    CAS  Google Scholar 

  2. Yu G, Gao J, Hummelene JC, Wudl F, Heeger AJ (1995) Polymer photovoltaic cells: enhanced efficiencies via a network ofinternal donor-acceptor heterojunctions. Science 270:1789–1791

    Article  CAS  Google Scholar 

  3. You J, Dou L, Yoshimura K, Kato T, Ohya K, Moriarty T, Emery K, Chen C, Gao J, Li G, Yang Y (2013) A polymer tandem solar cell with 10.6 % powerconversion efficiency, Nat. Commun 4:1–10

    Google Scholar 

  4. Park SH, Roy A, Beaupre S, Cho S, Coates N, Moon JS, Moses D, Leclerc M, Lee K, Heeger AJ (2009) Bulk heterojunction solar cells with internal quantum efficiency approaching 100 %. Nat Photonics 3:297–303

    Article  CAS  Google Scholar 

  5. Lee SK, Cho JM, Goo Y, Shin WS, Lee J-C, Lee W-H, Kang I-N, Shim H-K, Moon S-J (2011) Synthesis and characterization of a thiazolo[5,4-d]thiazole-based co-polymer for high performance polymer solar cells. Chem Commun 47:1791–1793

    Article  CAS  Google Scholar 

  6. Lee SK, Lee W-H, Cho JM, Park SJ, Park J-U, Shin WS, Lee J-C, Kang I-N, Moon S-J (2011) Synthesis and photovoltaic properties of quinoxaline-based alternating copolymers for high-efficiency bulk-heterojunction polymer solar cells. Macromolecules 44:5994–6001

    Article  CAS  Google Scholar 

  7. Angmo D, Larsen-Olsen TT, Jorgensen M, Sondergaard RR, Krebs FC (2013) Roll-to-roll inkjet printing and photonic sintering of electrodes for ITO free polymer solar cell modules and facile product integration. Adv Energy Mater 3(2):172–175

    Article  CAS  Google Scholar 

  8. Chen H-Y, Hou JH, Zhang SQ, Liang Y, Yang GW, Yang Y, Yu LP, Wu Y, Li G (2009) Polymer solar cells with enhanced open-circuit voltage and efficiency. Nat Photonics 3:649–653

    Article  CAS  Google Scholar 

  9. Liang Y, Xu Z, Xia J, Tsai ST, Wu T, 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:E135–E138

    CAS  Google Scholar 

  10. Chen J-T, Hsu C-S (2011) Conjugated polymer nanostructures for organic solar cell applications. Polym Chem 2:2707–2722

    Article  CAS  Google Scholar 

  11. Fu Y, Cha H, Lee G-Y, Moon BJ, Park CE, Park T (2012) 3,6-carbazole incorporated into poly[9,9-dioctylfluorene-alt-(bisthienyl)benzothiadiazoles improving the power conversion efficiency. Macromolecules 45:3004–3009

    Article  CAS  Google Scholar 

  12. 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  PubMed  CAS  Google Scholar 

  13. Kong H, Park SH, Cho NS, Cho S, Shim H-K (2012) Anthradithiophene–thiophene copolymers with broad UV–vis absorption for organic solar cells and field-effect transistors. J. Polym. Sci., part B: polym. Phys 50:4119–4126

    CAS  Google Scholar 

  14. Sanjaykumar SR, Badgujar S, Song CE, Shin WS, Moon S-J, Kang I-N, Lee J, Cho S, Lee SK, Lee J-C (2012) Synthesis and characterization of a novel naphthodithiophene-based copolymer for use in polymer solar cells. Macromolecules 45:6938–6945

    Article  Google Scholar 

  15. Bathula C, Song CE, Sachin B, Hong S-J, Park SY, Shin WS, Lee J-C, Cho S, Ahn T, Cho S, Moon S-J, Lee SK (2013) Naphtho[1,2-b:5,6-b′]dithiophene-based copolymers for applications to polymer solar cells. Polym Chem 4:2132–2139

    Article  CAS  Google Scholar 

  16. Bathula C, Song CE, Sachin B, Hong S-J, Kang I-N, Moon S-J, Lee J, Cho S, Shim H-K, Lee SK (2012) New TIPS-substituted benzo[1,2-b:4,5-b′]dithiophene-based copolymers for application in polymer solar cells. J Mater Chem 22:22224–22232

    Article  CAS  Google Scholar 

  17. Kim J-H, Song CE, Kim HU, Grimsdale AC, Moon S-J, Shin WS, Choi SK, Hwang D-H (2013) High open circuit voltage solution-processed tandem organic photovoltaic cells employing a bottom cell using a new medium band gap semiconducting polymer. Chem Mater 25:2722–2732

    Article  CAS  Google Scholar 

  18. Kim J-H, Song CE, Shin N, Kang H, Wood S, Kang I-N, Kim BJ, Kim BS, Kim J-S, Shin WS, Hwang D-H (2013) High-crystalline medium-band-gap polymers consisting of benzodithiophene and benzotriazole derivatives for organic photovoltaic cells. ACS Appl Mater Interfaces 5:12820–12831

    Article  PubMed  CAS  Google Scholar 

  19. Kim J-H, Lee M, Yang H, Hwang D-H (2014) High molecular weight triisopropylsilylethynyl (TIPS)-benzodithiophene and diketopyrrolopyrrole-based copolymer for high performance organic photovoltaic cells. J Mater Chem A 2:6348–6352

    Article  CAS  Google Scholar 

  20. Shi Q, Fan H, Liu Y, Hu W, Li Y, Zhan X (2011) A copolymer of benzodithiophene with TIPS side chains for enhanced photovoltaic performance. Macromolecules 44:9173–9179

    Article  CAS  Google Scholar 

  21. Kim HG, Jo SB, Shim C, Lee J, Shin J, Cho EC, Ihn S-G, Choi YS, Kim Y, Cho K (2012) Synthesis and photovoltaic properties of benzo[1,2-b:4,5-b′]dithiophenederivative-based polymers with deep HOMO levels. J Mater Chem 22:17709–17717

    Article  CAS  Google Scholar 

  22. Woo CH, Beaujuge PM, Holcombe TW, Lee OP, Fréchet JM (2010) J. M. J. Incorporation of furan into low band-gap polymers for efficient solar cells. J. Am. Chem Soc 132:15547–15549

    Article  CAS  Google Scholar 

  23. Liang Y, Feng D, Wu Y, Tsai ST, Li G, Ray C, Yu L (2009) Highly efficient solar cell polymers developed via fine-tuning of structural and electronic properties. J Am Chem Soc 131:7792–7799

    Article  PubMed  CAS  Google Scholar 

  24. Dou L, Gao J, Richard E, You J, Chen C, Cha KC (2012) Y. He Y, G. Li, Y. Yang, systematic investigation of benzodithiophene and diketopyrrolopyrrole-based low-bandgap polymers designed for single junction and tandem polymer solar cells. J. Am. Chem Soc 134:10071–10079

    Article  CAS  Google Scholar 

  25. Jespersen KG, Beenken WJD, Zaushitsyn Y, Yartsev A, Andersson M, Pullerits T, Sundstrom V (2004) The electronic states of polyfluorene copolymers with alternating donor-acceptor units. J Chem Phys 121:12613–12617

    Article  PubMed  CAS  Google Scholar 

  26. Lee SK, Seo JH, Cho NS, Cho S (2012) Effect of side chain position on solar cell performance in cyclopentadithiophene-based copolymers. Thin Solid Films 520:5438–5441

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge the support by Basic Science Research Program through National Research Foundation of Korea (NRF) funded by the Ministry of Education (2012R1A6A1029029). NRF funded by the Ministry of Science, ICT & Future Planning (2013 M3C8A3075845), and Samsung Research Funding Center of Samsung Electronics under Project Number SRFC-MA1401-05.

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Correspondence to Chinna Bathula.

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Bathula, C., Badgujar, S., Belavagi, N.S. et al. Synthesis, Characterization and Optoelectronic Properties of Benzodithiophene Based Copolymers for Application in Solar Cells. J Fluoresc 26, 371–376 (2016). https://doi.org/10.1007/s10895-015-1724-9

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  • DOI: https://doi.org/10.1007/s10895-015-1724-9

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