Photovoltaic properties of poly(benzothiadiazole-thiophene-co-bithiophene) as donor in polymer solar cells

Solar Energy Materials and Solar Cells

Volumn 95, Issue 2, 2011, Pages 704-711

  Zhao, Guangjin ^a,b   He, Youjun ^a   He, Chang ^a   Fan, Haijun ^a   Zhao, Yun ^a   Li, Yongfang ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b STATE GRID HENAN ELECTRIC POWER RESEARCH INSTITUTE   (China)

Author keywords

Additives; Conjugated polymer photovoltaic materials; Low bandgap conjugated polymers; Polymer solar cells; Thermal annealing

Indexed keywords

ACTIVE LAYER; BENZOTHIADIAZOLES; BITHIOPHENES; BUTYRIC ACIDS; CONJUGATED POLYMER PHOTOVOLTAIC MATERIALS; D-A COPOLYMERS; DENSITY FUNCTIONAL THEORY METHODS; EFFICIENCY IMPROVEMENT; ELECTRON ACCEPTOR; ELECTRON DONORS; LOW BAND GAP CONJUGATED POLYMERS; METHYL ESTERS; OLIGOTHIOPHENES; PHOTOVOLTAIC PROPERTY; POLYMER SOLAR CELLS; POWER CONVERSION EFFICIENCIES; SIDE CHAINS; SPECTROSCOPIC PROPERTY; STRUCTURE AND PROPERTIES; THERMAL-ANNEALING; THIOPHENE MONOMERS; WEIGHT RATIOS;

ABSORPTION SPECTROSCOPY; ADDITIVES; ANNEALING; CONJUGATED POLYMERS; CONVERSION EFFICIENCY; DENSITY FUNCTIONAL THEORY; ENERGY GAP; ESTERS; FATTY ACIDS; ORGANIC POLYMERS; PHOTOVOLTAIC EFFECTS; SOLAR CELLS; SOLAR POWER GENERATION; THIOPHENE;

FUNCTIONAL POLYMERS;

EID: 78650704207     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2010.10.007     Document Type: Article

References (61)

1. Y.-J. Chen, S.-H. Yang, and C.-S. Hsu Synthesis of conjugated polymers for organic solar cell applications Chem. Rev. 109 2009 5868 5923
2. G. Dennler, M.C. Scharber, and C. Brabec Polymer-fullerene bulk-heterojunction solar cells Adv. Mater. 21 2009 1323 1338
3. J.W. 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. Y.F. Li, and Y.P. Zou Conjugated polymer photovoltaic materials with broad absorption band and high charge carrier mobility Adv. Mater. 20 2008 2952 2958
5. M. Jørgensen, K. Norrman, and F.C. Krebs Stability/degradation of polymer solar cells Sol. Energy Mater. Sol. Cells 92 2008 686 714
6. H.-Y. Chen, J.H. Hou, S.Q. Zhang, Y.Y. Liang, G.W. Yang, Y. Yang, L.P. Yu, Y. Wu, and G. Li Polymer solar cells with enhanced open-circuit voltage and efficiency Nat. Photonics 3 2009 649 653
7. 60 bisadduct: a new acceptor for high performance polymer solar cells J. Am. Chem. Soc. 132 2010 1377 1382
8. 60 bisadduct by device optimization Adv. Mater. 22 2010 4355 4358 DOI: 10.1002/adma.201001339
9. Y.J. He, G.J. Zhao, B. Peng, and Y.F. Li High yield synthesis, electrochemical and photovoltaic properties of indene-C70 bisadduct Adv. Funct. Mater. 20 2010 3383 3389
10. F.C. Krebs, S.A. Gevorgyan, and J. Alstrup A roll-to-roll process to flexible polymer solar cells: model studies, manufacture and operational stability studies J. Mater. Chem. 19 2009 5442 5451
11. J.-Y. Jung, Z.Y. Guo, S.-W. Jee, H.-D. Um, K.-T. Park, and J.-H. Lee A strong antireflective solar cell prepared by tapering silicon nanowires Opt. Express 18 2010 A286 A292
12. F.C. Krebs, T.D. Nielsen, J. Fyenbo, M. Wadsrøm, and M.S. Pedersen Manufacture, integration and demonstration of polymer solar cells in a lamp for the "Lighting Africa" initiative Energy Environ. Sci. 3 2010 512 525
13. F.C. Krebs, T. Tromholt, and M. Jørgensen Upscaling of polymer solar cell fabricating using full roll-to-roll processing Nanoscale 2 2010 873 886
14. F.C. Krebs, J. Fyenbo, and M. Jørgensen Production integration of compact roll-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 89949001
15. W.L. Ma, C.Y. Yang, X. Gong, K.H. Lee, and A.J. Heeger Thermal stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology Adv. Funct. Mater. 15 2005 1617 1622
16. G. Li, V. Shrotriya, J. Huang, Y. Yao, T. Moriarity, K. Emery, and Y. Yang High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends Nat. Mater. 4 2005 864 868
17. J.H. Hou, H.-Y. Chen, S.Q. Zhang, G. Li, and Y. Yang Synthesis, characterization, and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole J. Am. Chem. Soc. 130 2008 16144 16145
18. Y.P. Zou, A. Najari, P. Berrouard, S. Beaupre, B.R. Aich, Y. Tao, and M. Leclerc A thieno[3,4-c]pyrrole-4,6-dione-based copolymer for efficient solar cells J. Am. Chem. Soc. 132 2010 5231 5330
19. M.M. Wienk, M. Turbiez, J. Gilot, and R.A.J. Janssen Narrow-bandgap diketo-pyrrolo-pyrrole polymer solar cells: the effect of processing on the performance Adv. Mater. 20 2008 2556 2560
20. E.J. Zhou, S.P. Yamakawa, K. Tajima, C.H. Yang, and K. Hashimoto Synthesis and photovoltaic properties of diketopyrrolopyrrole-based donoracceptor copolymers Chem. Mater. 21 2009 4055 4061
21. J. Peet, J.Y. Kim, N.E. Coates, W.L. Ma, D. Moses, A.J. Heeger, and G.C. Bazan Efficiency enhancement in low-bandgap polymer solar cells by processing with alkane dithiols Nat. Mater. 6 2007 497 500
22. L.J. Huo, H.-Y. Chen, J.H. Hou, T.L. Chen, and Y. Yang Low band gap dithieno[3,2-b:2′,3′-d]silole-containing polymers, synthesis, characterization and photovoltaic application Chem. Commun. 2009 5570 5572
23. E.G. Wang, L. Wang, L.F. Lan, C. Luo, W.L. Zhuang, J.B. Peng, and Y. Cao High-performance polymer heterojunction solar cells of a polysilafluorene derivative Appl. Phys. Lett. 92 2008 (Art. No. 033307)
24. R.P. Qin, W.W. Li, C.H. Li, C. Du, C. Veit, H.-F. Schleiermacher, M. Andersson, Z.S. Bo, Z.P. Liu, O. Inganas, U. Wuerfel, and F.L. Zhang A planar copolymer for high efficiency polymer solar cells J. Am. Chem. Soc. 131 2009 14612 14613
25. N. Blouin, A. Michaud, D. Gendron, S. Wakim, E. Blair, R. Neagu-Plesu, M. Belletete, G. Durocher, Y. Tao, and M. Leclerc Toward a rational design of poly(2,7-Carbazole) derivatives for solar cells J. Am. Chem. Soc. 130 2008 732 743
26. S.H. Park, A. Roy, S. Beaupr, S. Cho, N. Coates, J.S. Moon, D. Moses, M. Leclerc, K.H. Lee, and A.J. Heeger Bulk heterojunction solar cells with internal quantum efficiency approaching 100% Nat. Photonics 3 2009 297 303
27. C.-P. Chen, S.-H. Chan, T.-C. Chao, C. Ting, and B.-T. Ko Low-bandgap poly(thiophene-phenylene-thiophene) derivatives with broaden absorption spectra for use in high-performance bulk-heterojunction polymer solar cells J. Am. Chem. Soc. 130 2008 12828 12833
28. A. Gadisas, W. Mammo, M.L. Andersson, S. Admassie, F.L. Zhang, M.R. Andersson, and O. Ingans A new donoracceptordonor polyfluorene copolymer with balanced electron and hole mobility Adv. Funct. Mater. 17 2007 3836 3842
29. E.J. Zhou, M. Nakamura, T. Nishizawa, Y. Zhang, Q.S. Wei, K. Tajima, C.H. Yang, and K. Hashimoto Synthesis and photovoltaic properties of a novel low band gap polymer based on N-substituted dithieno[3,2-b:2′,3′-d] pyrrole Macromolecular 41 2008 8302 8305
30. G. Li, Y. Yao, H.C. Yang, V. Shrotriya, G.W. Yang, and Y. Yang "Solvent annealing" effect in polymer solar cells based on poly(3-hexylthiophene) and methanofullerenes Adv. Funct. Mater. 17 2007 1636 1644
31. Y. Zhao, Z.Y. Xie, Y. Qu, Y.H. Geng, and L.X. Wang Solvent-vapor treatment induced performance enhancement of poly(3-hexylthiophene): methanofullerene bulk-heterojunction photovoltaic cells Appl. Phys. Lett. 90 2007 (Art. No. 043504)
32. F. Padinger, R.S. Rittberger, and N.S. Sariciftci Effects of postproduction treatment on plastic solar cells Adv. Funct. Mater. 13 2003 85 88
33. C.-J. Ko, Y.-K. Lin, and F.-C. Chen Microwave annealing of polymer photovoltaic devices Adv. Mater. 19 2007 3520 3523
34. Y. Yao, J.H. Hou, Z. Xu, G. Li, and Y. Yang Effects of solvent mixtures on the nanoscale phase separation in polymer solar cells Adv. Funct. Mater. 18 2008 1783 1789
35. W.L. Wang, H.B. Wu, C.Y. Yang, C. Luo, Y. Zhang, J.W. Chen, and Y. Cao High-efficiency polymer photovoltaic devices from regioregular-poly(3- hexylthiophene-2,5-diyl) and [6,6]-phenyl-C61-butyric acid methyl ester processed with oleic acid surfactant Appl. Phys. Lett. 90 2007 (Art. No. 183512)
36. 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
37. M. Dante, A. Garcia, and T.-Q. Nguyen Three-dimensional nanoscale organization of highly efficient low band-gap conjugated polymer bulk heterojunction solar cells J. Phys. Chem. C 113 4 2009 1596 1600
38. Y.J. He, X. Wang, J. Zhang, and Y.F. Li Low bandgap polymers by copolymerization of thiophene with benzothiadiazole Macromol. Rapid Commun. 30 2009 45 51
39. S.H. Vosko, L. Wilk, and M. Nusair Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis Can. J. Phys. 58 1980 1200 1211
40. A.D. Becke Density-functional thermochemistry. 3. The role of exact exchange J. Chem. Phys. 98 1993 5648 5652
41. A.D. Becke Density-functional exchange-energy approximation with correct asymptotic behavior Phys. Rev. A 38 1988 3098 3100
42. C. Lee, W. Yang, and R.G. Parr Development of the ColleSalvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 37 1988 785 789
43. A. De Nicola, Y. Liu, K.S. Schanze, and R. Ziessel One-pot synthesis of 2,5-diethynyl-3,4-dibutylthiophene substituted multitopic bipyridine ligands: redox and photophysical properties of their ruthenium(II) complexes Chem. Commun. 2003 288 289
44. S. Goeb, A.D. Nicola, and R. Ziessel Oligomeric ligands incorporating multiple 5,5 ′-diethynyl-2,2′-bipyridine moieties bridged and end-capped by 3,4-dibutylthiophene units J. Org. Chem. 70 2005 1518 1529
45. A.B. Bryce, J.M. Charnochk, R.A.D. Pattrichk, and A.R. Lennie EXAFS and density functional study of gold(I) thiosulfate complex in aqueous solution J. Phys. Chem. A 107 2003 2516 2523
46. Q.J. Pan, and H.-X. Zhang Ab initio study on luminescence and aurophilicity of a dinuclear [(AuPH3)(2)(i-nmt)] complex (i-mnt=isomer- malononitriledithiolate) Eur. J. Inorg. Chem. 2003 4202 4210
47. K. Naito, M. Sakurai, and S. Egusa Molecular design, syntheses, and physical properties of nonpolymeric amorphous dyes for electron transport J. Phys. Chem. A 101 1997 2350 2357
48. M.E. Casida, C. Jamorski, K.C. Casida, and D.R. Salahub Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: characterization and correction of the time-dependent local density approximation ionization threshold J. Chem. Phys. 108 1998 4439 4449
49. R.E. Stratmann, and G.E. Scuseria An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules J. Chem. Phys. 109 1998 8218 8224
50. N.N. Matsuzawa, A. Ishitani, D.A. Doxon, and T. Uda Time-dependent density functional theory calculations of photoabsorption spectra in the vacuum ultraviolet region J. Phys. Chem. A 105 2001 4953 4962 (Pubitemid 35361964)
51. M. Cossi, G. Scalmani, N. Regar, and V. Barone New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution J. Chem. Phys. 117 2002 43 54
52. V. Barone, M. Cossi, and J. Tomasi A new definition of cavities for the computation of solvation free energies by the polarizable continuum model J. Chem. Phys. 107 1997 3210 3221
53. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven Jr., K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03. revision C.02 2004 Gaussian, Inc. Wallingford, CT
54. T. Liu, J.-S. Gao, B.-H. Xia, X. Zhou, and H.-X. Zhang Theoretical studies on the electronic structures and optical properties of the oligomers involving bipyridyl, thiophenyl and ethynyl groups Polymer 48 2007 502 511
55. L. Yang, J.-K. Feng, A.-M. Ren, and J.-Z. Sun The electronic structure and optical properties of carbazole-based conjugated oligomers and polymers: a theoretical investigation Polymer 47 2006 1397 1404
56. G.J. Zhao, G.L. Wu, C. He, F.-Q. Bai, H.X. Xi, H.-X. Zhang, and Y.F. Li Solution-processable multi-armed organic molecules containing triphenylamine and DCM moieties: synthesis and photovoltaic properties J. Phys. Chem. C 113 2009 2636 2642
57. Z.Y. Ge, T. Hayakawa, S. Ando, M. Ueda, T. Akiike, H. Miyamoto, T. Kajita, and M.-A. Kakimoto Solution-processible bipolar triphenylamine- benzimidazole derivatives for highly efficient single-layer organic light-emitting diodes Chem. Mater. 20 2008 2532 2537 (Pubitemid 351568952)
58. M.M. Mandoc, W. Veurman, L.J.A. Koster, B. de Boer, and P.W.M. Blom Origin of the reduced fill factor and photocurrent in MDMO-PPV:PCNEPV all-polymer solar cells Adv. Funct. Mater. 17 2007 2167 2173
59. G.G. Malliaras, J.R. Salem, P.J. Brock, and C. Scott Electrical characteristics and efficiency of single-layer organic light-emitting diodes Phys. Rev. B 58 1998 R13 411R13 414
60. V.D. Mihailetchi, J.K.J. van Duren, P.W.M. Blom, J.C. Hummelen, R.A.J. Janssen, J.M. Kroon, M.T. Rispens, W.J.H. Verhees, and M.M. Wienk Electron transport in a methanofullerene Adv. Funct. Mater. 13 2003 43 46
61. X. Yang, and J. Loos Toward high-performance polymer solar cells: the importance of morphology control Macromolecules 40 2007 1353 1362