New alkylselenyl substituted benzodithiophene-based solution-processable 2D π-conjugated polymers for bulk heterojunction polymer solar cell applications

Solar Energy Materials and Solar Cells

Volumn 122, Issue , 2014, Pages 136-145

  Chakravarthi, Nallan ^a   Kranthiraja, Kakaraparthi ^a   Song, Myungkwan ^b   Gunasekar, Kumarasamy ^a   Jeong, Pyeongsu ^c   Moon, Sang Jin ^c   Suk Shin, Won ^c   Kang, In Nam ^d   Lee, Jae Wook ^e   Jin, Sung Ho ^a  

^a Pusan National University   (South Korea)

^b Korea Institute of Material Science   (South Korea)

^c Korea Research Institute of Chemical Technology   (South Korea)

^d The Catholic University of Korea   (South Korea)

^e Dong A University   (South Korea)

Author keywords

Additive; Bulk heterojunction polymer solar cells; Field effect transistors; Morphology

Indexed keywords

BENZODITHIOPHENE; BULK HETEROJUNCTION; DONOR-ACCEPTORS; ELECTRON RICH MOIETIES; FIELD EFFECTS; HIGH POWER CONVERSION; PHENYL RINGS; POLYMER SOLAR CELLS;

ADDITIVES; FIELD EFFECT TRANSISTORS; MORPHOLOGY; SOLAR CELLS; THIN FILMS;

HETEROJUNCTIONS;

EID: 84890932421     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2013.11.019     Document Type: Article

References (56)

1. H.-Y. Chen, J. Hou, S. Zhang, Y. Liang, G.W. Yang, Y. Yang, L. Yu, Y. Wu, and G. Li Polymer solar cells with enhanced open-circuit voltage and efficiency Nat. Photonics 3 2009 649 653
2. Y. Liang, Z. Xu, J. Xia, S.-T. Tsai, Y. Wu, G. Li, C. Ray, and L. Yu For the bright future - bulk heterojunction polymer solar cells with power conversion efficiency of 7.4% Adv. Mater. 22 2010 E135 E138
3. J. Chen, and Y. Cao Development of novel conjugated donor polymers for high-efficiency bulk heterojunction photovoltaic devices Acc. Chem. Res. 42 2009 1709 1718
4. C.J. Brabec, N.S. Sariciftci, and J.C. Hummelen Plastic solar cells Adv. Funct. Mater. 11 2001 15 26 (Pubitemid 33046405)
5. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, and A.J. Heeger Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions Science 270 1995 1789 1791 (Pubitemid 126635480)
6. F.C. Krebs, J. Fyenbo, and M. Jørgensen Product integration of compact rol-to-roll processed polymer solar cell modules: methods and manufacture using flexographic printing, slot-die coating and rotary screen printing J. Mater. Chem. 20 2010 8994 9001
7. H.J. Son, W. Wang, T. Xu, Y. Liang, Y. Wu, G. Li, and L. Yu Synthesis of fluorinated polytheinothiophene-co-benzodithiophenes and effect of fluorination on the photovoltaic properties J. Am. Chem. Soc. 133 2011 1885 1894
8. A. Fachetti π-Conjugated polymers for organic electronics and photovoltaic applications Chem. Mater. 23 2011 733 758
9. W. Nie, C.M. MacNeill, Y. Li, R.E. Noftle, D.L. Carroll, and R.C. Coffin A soluble high molecular weight copolymer of benzo[1,2-b:4,5-b']dithiophene and benzoxadiazole for efficient organic photovoltaics Macromol. Rapid Commun. 32 2011 1163 1168
10. H. Hoppe, and N.S. Sariciftci Organic solar cells: an overview J. Mater. Res. 19 2004 1924 1945
11. G. Li, R. Zhu, and Y. Yang Polymer solar cells Nat. Photonics 6 2012 153 161
12. L. Duo, J. Gao, E. Richard, J. You, C.-C. Chen, K.C. Cha, Y. He, G. Li, and Y. Yang Systematic investigation of benzodithiophene- and diketopyrrole-based low-bandgap polymers designed for single junction and tandem, polymer solar cells J. Am. Chem. Soc. 134 2012 10071 10079
13. L. Dou, J. You, J. Yang, C.-C. Chen, Y. He, S. Murase, T. Moriarty, K. Emery, G. Li, and Y. Yang Tandem polymer solar cells featuring a spectrally matched low bandgap polymer Nat. Photonics 6 2012 180 185
14. H. Zhou, L. Yang, and W. You Rational design of high performance conjugated polymers for organic solar cells Macromolecules 45 2012 607 632
15. Y.-J. Cheng, S.-H. Yang, and C.-S. Hsu Synthesis of conjugated polymers for organic solar cell applications Chem. Rev. 109 2009 5868 5923
16. J.L. Delgado, P.-A. Bouit, S. Filippone, Ma.Á. Herranz, and N. Martin Organic photovoltaics: a chemical approach Chem. Commun. 46 2010 4853 4865
17. Y. He, and Y. Li Fullerene derivative acceptors for high performance polymer solar cells Phys. Chem. Chem. Phys. 13 2011 1970 1983
18. Y. Li Molecular design of photovoltaic material for polymer solar cells: toward suitable electronic energy levels and broad absorption Acc. Chem. Res. 45 2012 723 733
19. P.-L.T. Boudreault, A. Najari, and M. Leclerc Processable low-bandgap polymer for photovoltaic applications Chem. Mater. 23 2011 456 469
20. H.X. Zhou, L.Q. Yang, S.B. Liu, and W. You A tale of current and voltage: interplay of band gap and energy levels of conjugated polymers in bulk heterojunction solar cells Macromolecules 43 2010 10390 10396
21. J. Yuan, X. Huang, F. Zhang, J. Lu, Z. Zhai, C. Di, Z. Jiang, and W. Ma Design of benzodithiophene-diketopyrrole based donor-acceptor copolymers for efficient organic field effect transistors and polymer solar cells J. Mater. Chem. 22 2012 22734 22742
22. S. Beapuré, A. Pron, S.H. Drouin, A. Najari, L.G. Mercier, A. Robiaille, and M. Leclerc Thieno-, furo-, and selenophene[3,4-c]pyrrole-4,6- dione copolymers: effect of the heteroatom on the electrooptical properties Macromolecules 45 2012 6906 6914
23. P. Sista, B. Xue, M. Wilson, N. Holmes, R.S. Kularatne, H. Nguyen, P.C. Dastoor, W. Belcher, K. Poole, B.G. Janesko, M.C. Biewer, and M.C. Stefan Influence of the alkyl substituents spacing on the solar cell performance of benzodithiophene semiconducting polymers Macromolecules 45 2012 772 780
24. H.-Y. Chen, S.-C. Yeh, C.-T. Chen, and C.-T. Chen Comparison of thiophene- and selenophene-bridged donor-acceptor low band-gap copolymers used in bulk-heterojunction organic photovoltaics J. Mater. Chem. 22 2012 21549 21559
25. T. Yamamoto, T. Ikai, M. Kuzuba, T. Kuwabara, K. Maeda, K. Takahashi, and S. Kanoh Synthesis and characterization of thieno[3,4-b]thiophene-based copolymers bearing 4-substituted phenyl ester pendants: facile fine-tuning of HOMO energy levels Macromolecules 44 2008 6659 6662
26. J. Hou, M.-H. Park, S. Zhang, Y. Yao, L.-M. Chen, J.-H. Li, and Y. Yang Bandgap and molecular energy level control of conjugated polymer photovoltaic materials based on benzo[1,2-b:4,5-b']dithiophene Macromolecules 41 2008 6012 6018
27. Y. Zou, A. Najari, P. Berrouard, S. Beaupré, B.R. Aïch, Y. Tao, and M. Leclerc A thieno[3,4-c]pyrrole-4,6-dione-based copolymer for eficient solar cells J. Am. Chem. Soc. 132 2010 5330 5331
28. L. Huo, S. Zhang, X. Guo, F. Xu, Y. Li, and J. Hou Replacing alkoxy groups with alkylthienyl groups: a feasible approach to improve the properties of photovoltaic polymers Angew. Chem. - Int. Ed. 50 2011 9697 9702
29. J. Yuan, Z. Zhai, H. Dong, J. Li, Z. Jiang, Y. Li, and W. Ma Eficient polymer solar cells with a high open circuit voltage of 1 V Adv. Funct. Mater. 23 2013 885 892
30. Q. Peng, X. Liu, D. Su, G. Fu, J. Xu, and L. Dai Novel benzo[1,2-b:4,5-b']dithiophene-benzothiadiazole derivatives with variable side chains for high-performance solar cells Adv. Mater. 23 2011 4554 4558
31. -1 hole mobility in thin-film transistors J. Am. Chem. Soc. 133 2011 10364 10367
32. A. Patra, and M. Bendikov Polyselenophenes J. Mater. Chem. 20 2010 422 433
33. S.S. Zade, N. Zamoshchik, and M. Bendikov Oligo- and polyselenophenes: a theoretical study Chem.-Eur. J. 15 2009 8613 8624
34. S.S. Zade, and M. Bendikov From oligomers to polymer: convergence in the HOMO-LUMO gaps of conjugated oligomers Org. Lett. 8 2006 5243 5246 (Pubitemid 44861538)
35. H.A. Saadeh, L. Lu, F. He, J.E. Bullock, W. Wang, B. Carsten, and L. Yu Polyselenopheno[3,4-b]selenophene for highly efficient bulk heterojunction solar cells ACS Macro Lett. 1 2012 361 365
36. B. Kim, H.R. Yeom, M.H. Yun, J.Y. Kim, and C. Yang A selenophene analogue of PCDTBT: selective fine-tuning of LUMO to lower of the bandgap for efficient polymer solar cells Macromolecules 45 2012 8658 8664
37. Y.-S. Byun, J.-H. Kim, J.B. Park, I.-N. Kang, S.-H. Jin, and D.-H. Hwang Full donor-type conjugated polymers consisting of alkoxy- or alkylselenophene-substituted benzodithiophene and thiophene units for organic photovoltaic devices Synth. Met. 168 2013 23 30
38. K. Geese, M. Prehm, and C. Tschierske Bent-core mesogens with thiophene units J. Mater. Chem. 20 2010 9658 9665
39. J.S. Park, T.I. Ryu, M. Song, K.-J. Yoon, M.J. Lee, I.A. Shin, G.-D. Lee, J.W. Lee, Y.-S. Gal, and S.-H. Jin Synthesis and characterization of fluorene-based low-band gap copolymers containing propylenedioxythiophene and benzothiadiazole derivatives for bulk heterojunction photovoltaic cell applications J. Polym. Sci. Part A: Polym. Chem. 46 2008 6175 6184
40. S.P. Mishra, A.K. Palai, and M. Patri Synthesis and characterization of soluble narrow band gap conducting polymers based on diketopyrrolopyrrole and propylenedioxythiophenes Synth. Met. 160 2010 2422 2429
41. K. Pilgram, M. Zupan, and R. Skils Bromination of 2,1,3-benzothiadiazoles J. Heterocycl. Chem. 7 1970 629 633
42. R.J. Kline, M.D. McGhee, E.N. Kadnikova, J. Liu, and J.M.J. Fréchet Controlling the field effect mobility of regioregular polythiophene by changing the molecular weight Adv. Mater. 15 2003 1519 1522
43. S. Günes, H. Neugebauer, and N.S. Sariciftci Conjugated polymer-based organic solar cells Chem. Rev. 107 2007 1324 1338 (Pubitemid 46736541)
44. M. Jørgensen, K. Norrman, and F.C. Krebs Stability/degradation of polymer solar cells Sol. Energy Mater. Sol. Cells 92 2008 686 714
45. Y. Zhang, S.K. Hau, H.-L. Yip, Y. Sun, O. Acton, and A.K.-Y. Jen Efficient polymer solar cells based on the copolymers of benzodithiophene and thienopyrroledione Chem. Mater. 22 2010 2696 2698
46. D.M. de Leeuw, M.M.J. Simenon, A.R. Brown, and R.E.F. Einerhand Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices Synth. Met. 87 1997 53 59 (Pubitemid 127416144)
47. L. Huo, J. Hou, S. Zhang, H.-Y. Chen, and Y. Yang 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 2010 1500 1503
48. C.J. Brabec, C. Winder, N.S. Sariciftici, J.C. Hummelen, A. Dhanabalan, P.A. vanHal, and R.A.J. Janssen A low band-gap semiconducting polymer for photovoltaic and infrared emitting diodes Adv. Funct. Mater. 12 2002 709 712 (Pubitemid 35354532)
49. J.-L. Brédas, D. Beljonne, V. Coropceanu, and J. Cornil Charge-transfer and energy-transfer processes in π-conjugated oligomers and polymers: a molecular picture Chem. Rev. 104 2004 4971 5004
50. L. Zhang, K. Pei, M. Yu, Y. Huang, H. Zhao, M. Zeng, Y. Wang, and J. Gao Theoretical investigations on donor-acceptor conjugated copolymers based on naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole for organic solar cell applications J. Phys. Chem. C 116 2012 26154 26161
51. J.K. Lee, W.L. Ma, C.J. Brabec, J. Yuen, J.S. Moon, J.Y. Kim, K. Lee, G.C. Bazan, and A.J. Heeger Processing additives for improved efficiency from bulk heterojunction solar cells J. Am. Chem. Soc. 130 2008 3619 3623 (Pubitemid 351456066)
52. K. Lee, J.Y. Kim, S.H. Park, S.H. Kim, S. Cho, and A.J. Heeger Air-stable polymer electronic devices Adv. Mater. 19 2007 2445 2449 (Pubitemid 47481793)
53. B. Fan, R. Hany, J.-E. Moser, and F. Nüesch Enhanced cyanine solar cell performance upon oxygen doping Org. Electron. 9 2008 85 94 (Pubitemid 350245474)
54. M. Zhang, Y. Gu, X. Guo, F. Liu, S. Zhang, L. Huo., T.P. Russel, and J. Hou Efficient polymer solar cells based on benzothiadiazole and alkylphenyl substituted benzodithiophene with a power conversion efficiency over 8% Adv. Mater 25 2013 4944 4949
55. Q. Zheng, B.J. Jung, J. Sun, and H.E. Katz Ladder-type oligo-p-phenylene-containing copolymers with high open-circuit voltages and ambient photovoltaic activity J. Am. Chem. Soc. 132 2010 5394 5404
56. P.J. Brown, D.C. Thomas, A. Kohler, J.S. Wilson, J.-S. Kim, C.M. Ramsdale, H. Sirringhaus, and R.H. Friend Effect of interchain interactions on the absorption and emission of poly(3-hexylthiophene) Phys. Rev. B: Condens. Matter Mater. Phys. 67 2003 064203/1 064203/16