Synthesis and photovoltaic properties of n-type conjugated polymers alternating 2,7-carbazole and arylene diimides

Solar Energy Materials and Solar Cells

Volumn 103, Issue , 2012, Pages 157-163

  Hu, Xiaolian ^a   Zuo, Lijian ^a   Pan, Hongbin ^a   Hao, Feng ^a   Pan, Junying ^a   Fu, Lei ^a   Shi, Minmin ^a   Chen, Hongzheng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

2,7 Carbazole; Arylene diimides; N type polymers; Polymer solar cells

Indexed keywords

2 ,7-CARBAZOLE; ACTIVE LAYER; ALTERNATING COPOLYMERIZATION; ARYLENE; DIIMIDE; ELECTRON-ACCEPTING; ELECTRON-DONATING; FILL FACTOR; NAPHTHALENE DIIMIDE; PERYLENEDIIMIDES; PHOTOVOLTAIC PERFORMANCE; PHOTOVOLTAIC PROPERTY; POLYMER SOLAR CELLS; POWER CONVERSION EFFICIENCIES; SEMICONDUCTIVE; VISIBLE REGION;

CONVERSION EFFICIENCY; CYCLIC VOLTAMMETRY; MONOMERS; NANOSTRUCTURED MATERIALS; NAPHTHALENE; OPEN CIRCUIT VOLTAGE; PHOTOVOLTAIC EFFECTS; POLYCYCLIC AROMATIC HYDROCARBONS; POLYMER BLENDS; SOLAR CELLS;

COPOLYMERS;

EID: 84860992877     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2012.04.041     Document Type: Article

References (40)

1. G. Dennler, M.C. Scharber, and C.J. Brabec Polymer-fullerene bulk-heterojunction solar cells Advanced Materials 21 2009 1323 1338
2. F.C. Krebs, T.D. Nielsen, J. Fyenbo, M. Wadstrom, and M.S. Pedersen Manufacture, integration and demonstration of polymer solar cells in a lamp for the Lighting Africa initiative Energy & Environmental Science 3 2010 512 525
3. S. Gunes, H. Neugebauer, and N.S. Sariciftci Conjugated polymer-based organic solar cells Chemical Reviews 107 2007 1324 1338 (Pubitemid 46736541)
4. M. Helgesen, R. Sondergaard, and F.C. Krebs Advanced materials and processes for polymer solar cell devices Journal of Materials Chemistry 20 2010 36 60
5. P.T. Boudreault, A. Najari, and M. Leclerc Processable low-bandgap polymers for photovoltaic applications Chemistry of Materials 23 2011 456 469
6. E. Bundgaard, and F.C. Krebs Large-area photovoltaics based on low band gap copolymers of thiophene and benzothiadiazole or benzo-bis(thiadiazole) Solar Energy Materials & Solar Cells 91 2007 1019 1025 (Pubitemid 46635040)
7. H.Y. Chen, J.H. Hou, S.Q. Zhang, Y.Y. Liang, G.W. Yang, L.P. Yu, Y Yang, Y. Wu, and G. Li Polymer solar cells with enhanced open-circuit voltage and efciency Nature Photonics 3 2009 649 653
8. Y.Y. Liang, Z. Xu, J.B. Xia, S.T. Tsai, Y. Wu, G. Li, C. Ray, and L.P. Yu For the bright future - bulk heterojunction polymer solar cells with power conversion efficiency of 7.4% Advanced Materials 22 2010 E135 138
9. T.Y. Chu, J.P. Lu, S. Beaupré, Y.G. Zhang, J.R. Pouliot, S. Wakim, J.Y. Zhou, M. Leclerc, Z. Li, J.F. Ding, and Y. Tao 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% Journal of the American Chemical Society 133 2011 4250 4253
10. H.X. Zhou, L.Q. Yang, A.C. Stuart, S.C. Price, S.B. Liu, and W. You Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7% efficiency Angewandte Chemie-International Edition 50 2011 2995 2998
11. L.J. Huo, S.Q. Zhang, X. Guo, F. Xu, Y.F. Li, and J.H. Hou Replacing alkoxy groups with alkylthienyl groups: a feasible approach to improve the properties of photovoltaic polymers Angewandte Chemie-International Edition 50 2011 9697 9702
12. 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)
13. X.N. Yang, J. Loos, S.C. Veenstra, W.J.H. Verhees, M.M. Wienk, J.M. Kroon, M.A.J. Michels, and R.A.J. Janssen Nanoscale morphology of high-performance polymer solar cells Nano Letters 5 2005 579 583 (Pubitemid 40609723)
14. G.J. Zhao, Y.J. He, Z. Xu, J.H. Hou, M.J. Zhang, J. Min, H.Y. Chen, M.F. Ye, Z.R. Hong, Y. Yang, and Y.F. Li Effect of carbon chain length in the substituent of PCBM-like molecules on their photovoltaic properties Advanced Functional Materials 20 2010 1480 1487
15. X.W. Zhan, Z.A. Tan, B. Domercq, Z.S. An, X. Zhang, S. Barlow, Y.F. Li, D.B. Zhu, B. Kippelen, and S.R. Marder A high-mobility electron-transport polymer with broad absorption and its use in all-polymer solar cells and field-effect transistors Journal of the American Chemical Society 129 2007 7246 7247 (Pubitemid 46980790)
16. F. Würthner Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures Chemical Communications 14 2004 1564 1579 (Pubitemid 39089105)
17. H. Langhals, O. Krotz, K. Polborn, and P. Mayer A novel fluorescent dye with strong, anisotropic solid-state fluorescence, small stokes shift, and high photostability Angewandte Chemie 117 2005 2479 2480
18. M.M. Shi, H.Z. Chen, J.Z. Sun, J. Ye, and M. Wang Excellent ambipolar photoconductivity of PVK film doped with fluoroperylene diimide Chemical Physics Letters 381 2003 666 671
19. H.Z. Chen, M.M. Ling, X. Mo, M.M. Shi, M. Wang, and Z. Bao Air stable n-channel organic semiconductors for thin film transistors based on fluorinated derivatives of perylene diimides Chemistry of Materials 19 2007 816 824 (Pubitemid 46408950)
20. M.M. Shi, H.Z. Chen, and M. Wang Influences of different fluorinated substituents on electron mobility of perylene diimides Acta Chimica Sinica 64 2006 721 726 (Pubitemid 44663010)
21. X.L. Hu, M.M. Shi, L.J. Zuo, L. Fu, S.L. Dai, and H.Z. Chen Synthesis and energy levels of perylene diimide derivatives with the substitutions of secondary amino groups at bay positions Acta Chimica Sinica 69 2011 673 679
22. Y.G. Wen, and Y.Q. Liu Recent progress in n-channel organic thin-film transistors Advanced Materials 22 2010 1331 1345
23. H. Yan, Z. Chen, Y. Zheng, C. Newman, J.R. Quinn, F. Dötz, M. Kastler, and A. Facchetti A high-mobility electron-transporting polymer for printed transistors Nature 457 2009 679 686
24. W.S. Shin, H.H. Jeong, M.K. Kim, S.H. Jin, J.K. Lee, J.W. Lee, and Y.S. Gal Effects of functional groups at perylene diimide derivatives on organic photovoltaic device application Journal of Materials Chemistry 16 2006 384 390 (Pubitemid 43324456)
25. Y. Lu, H. Chen, F. Qiao, X. Hu, and S.C. Ng Synthesis, characterization and photovoltaic application of N,N-bisuorenyl substituted perylene bisimide Solar Energy Materials & Solar Cells 94 2010 2036 2041
26. X.Y. Guo, L.J. Bu, Y. Zhao, Z.Y. Xie, Y.H. Geng, and L.X. Wang Controlled phase separation for efcient energy conversion in dye/polymer blend bulk heterojunction photovoltaic cells Thin Solid Films 517 2009 4654 4657
27. J.L. Li, F. Dierschke, J.S. Wu, A.C. Grimsdale, and K. Müllen Poly(2,7-carbazole) and perylene tetracarboxydiimide: a promising donor/acceptor pair for polymer solar cells Journal of Materials Chemistry 16 2006 96 100 (Pubitemid 43324489)
28. Q.L. Zhang, A. Cirpan, T.P. Russell, and T. Emrick Donor acceptor poly(thiophene-block-perylene diimide) copolymers: synthesis and solar cell fabrication Macromolecules 42 2009 1079 1082
29. L.J. Bu, X.Y. Guo, B. Yu, Y. Qu, Z.Y. Xie, D.H. Yan, Y.H. Geng, and F.S. Wang Monodisperse co-oligomer approach toward nanostructured films with alternating donor acceptor lamellae Journal of the American Chemical Society 131 2009 13242 13243
30. X.W. Zhan, Z.A. Tan, E.J. Zhou, Y.F. Li, R. Misra, A. Grant, B. Domercq, X.H. Zhang, Z.S. An, X. Zhang, S. Barlow, B. Kippelen, and S.R. Marder Copolymers of perylene diimide with dithienothiophene and dithienopyrrole as electron-transport materials for all-polymer solar cells and eld-effect transistors Journal of Materials Chemistry 19 2009 5794 5803
31. J.A. Mikroyannidis, M.M. Stylianakis, G.D. Sharma, P. Balraju, and M.S. Roy A novel alternating phenylenevinylene copolymer with perylene bisimide units: synthesis, photophysical, electrochemical, and photovoltaic properties Journal of Physical Chemistry C 113 2009 7904 7912
32. E.J. Zhou, J.Z. Cong, Q.S. Wei, K. Tajima, C.H. Yang, and K. Hashimoto All-polymer solar cells from perylene diimide based copolymers: material design and phase separation control Angewandte Chemie-International Edition 50 2011 2799 2803
33. J. Chen, M.M. Shi, X.L. Hu, M. Wang, and H.Z. Chen Conjugated polymers based on benzodithiophene and arylene imides: extended absorptions and tunable electrochemical properties Polymer 51 2010 2897 2902
34. N. Blouin, A. Michaud, and M. Leclerc A low-bandgap poly(2,7-carbazole) derivative for use in high-performance solar cells Advanced Materials 19 2007 2295 2300 (Pubitemid 47409295)
35. J. Roncali Molecular engineering of the band gap of p-conjugated systems: facing technological applications Macromolecular Rapid Communications 28 2007 1761 1775 (Pubitemid 47411423)
36. Z.H. Chen, Y. Zheng, H. Yan, and A. Facchetti Naphthalenedicarboximide versus perylenedicarboximide-based copolymers. Synthesis and semiconducting properties in bottom-gate n-channel organic transistors Journal of the American Chemical Society 131 2009 8 9
37. Y.F. Wei, Q. Zhang, Y. Jiang, and J.S. Yu Novel low bandgap EDOT-naphthalene bisimides conjugated polymers: synthesis, redox, and optical properties Macromolecular Chemistry and Physics 210 2009 769 775
38. B.C. Thompson, and J.M. Frechet Polymer-fullerene composite solar cells Angewandte Chemie-International Edition 47 2008 58 77
39. L.M. Chen, Z. Hong, G. Li, and Y. Yang Recent progress in polymer solar cells: manipulation of polymer:fullerene morphology and the formation of efcient inverted polymer solar cells Advanced Materials 21 2009 1434 1449
40. P. Sonar, J.P.F. Lim, and K.L. Chan Organic non-fullerene acceptors for organic photovoltaics Energy & Environmental Science 4 2011 1558 1574