A Low‐Bandgap Poly(2,7‐Carbazole) Derivative for Use in High‐Performance Solar Cells

Advanced MaterialsVolume 19, Issue 17 p. 2295-2300 Communication A Low-Bandgap Poly(2,7-Carbazole) Derivative for Use in High-Performance Solar Cells† N. Blouin, N. Blouin Canada Research Chair on Electroactive and Photoactive Polymers, Département de Chimie, Université Laval, Quebec City, QC G1K 7P4 (Canada)Search for more papers by this authorA. Michaud, A. Michaud Canada Research Chair on Electroactive and Photoactive Polymers, Département de Chimie, Université Laval, Quebec City, QC G1K 7P4 (Canada)Search for more papers by this authorM. Leclerc, M. Leclerc [email protected] Canada Research Chair on Electroactive and Photoactive Polymers, Département de Chimie, Université Laval, Quebec City, QC G1K 7P4 (Canada)Search for more papers by this author N. Blouin, N. Blouin Canada Research Chair on Electroactive and Photoactive Polymers, Département de Chimie, Université Laval, Quebec City, QC G1K 7P4 (Canada)Search for more papers by this authorA. Michaud, A. Michaud Canada Research Chair on Electroactive and Photoactive Polymers, Département de Chimie, Université Laval, Quebec City, QC G1K 7P4 (Canada)Search for more papers by this authorM. Leclerc, M. Leclerc [email protected] Canada Research Chair on Electroactive and Photoactive Polymers, Département de Chimie, Université Laval, Quebec City, QC G1K 7P4 (Canada)Search for more papers by this author First published: 26 July 2007 https://doi.org/10.1002/adma.200602496Citations: 1,177 † This work was supported by discovery and strategic grants from the Natural Sciences and Engineering Research Council (NSERC) of Canada. N.B. thanks NSERC for a Ph.D. Canada Graduate Scholarships (CGS D). The authors gratefully acknowledge David Gendron for the synthesis of some intermediate compounds. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Polymeric materials are promising for solar cell applications. High-molecular-weight and soluble poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di- 2-thienyl-2',1',3'-benzothiadiazole)] is synthesized by either a Stille or Suzuki coupling reaction. Electrochemical and optical characterization of this thermally and air-stable polymeric material is reported, and bulk heretojunction polymer/fullerene photovoltaic devices are fabricated. REFERENCES 1a C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Funct. Mater. 2001, 11, 15. 1b C. Winder, N. S. Saridifti, J. Mater. Chem. 2004, 14, 1077. 2 H. Hoppe, N. S. Sariciftci, J. Mater. Res. 2004, 19, 1924. 3 K. M. Coakley, M. D. McGehee, Chem. Mater. 2004, 16, 4533. 4a M. M. Wienk, J. M. K. Wiljan, J. H. Verhees, J. Knol, J. C. Hummelen, P. A. van Hal, R. A. J. Janssen, Angew. Chem. Int. Ed. 2003, 42, 337. 4b S. E. Shaheen, C. J. Brabec, N. S. Sariciftci, F. Padinger, T. Fromherz, J. C. Hummelen, Appl. Phys. Lett. 2001, 78, 841. 5 W. Ma, C. Yang, X. Gong, K. Lee, A. J. Heeger, Adv. Funct. Mater. 2005, 15, 1617. 6a M. Reyes-Reyes, K. Kim, D. L. Carroll, Appl. Phys. Lett. 2005, 87, 083506. 6b G. Li, V. Shrotriya, J. Huang, Y. Yao, T. Moriarty, K. Emery, Y. Yang, Nat. Mater. 2005, 4, 864. 7 J. Hou, Z. Tan, Y. Yan, Y. He, C. Yang, Y. Li, J. Am. Chem. Soc. 2006, 128, 4911. 8a M. Svensson, F. Zhang, S. C. Veenstra, W. J. H. Verhees, J. C. Hummelen, J. M. Kroon, O. Inganäs, M. R. Andersson, Adv. Mater. 2003, 15, 988. 8b O. Inganäs, M. Svensson, F. Zhang, A. Gadisa, N. K. Persson, X. Wang, M. R. Andersson, Appl. Phys. A 2004, 79, 31. 8c F. Zhang, K. G. Jespersen, C. Björström, M. Svensson, M. R. Andersson, V. Sundström, K. Magnusson, E. Moons, A. Yartsev, O. Inganäs, Adv. Funct. Mater. 2006, 16, 667. 9 F. Zhang, W. Mammo, L. M. Andersson, S. Admassie, M. R. Andersson, O. Inganäs, Adv. Mater. 2006, 18, 2169. 10 F. Wang, J. Luo, K. Yang, J. Chen, F. Huang, Y. Cao, Macromolecules 2005, 38, 2253. 11a M. Leclerc, J. Polym. Sci. Part A 2001, 39, 2867. 11b L. Akcelrud, Prog. Polym. Sci. 2003, 28, 875. 12 M. C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A. J. Heeger, C. J. Brabec, Adv. Mater. 2006, 18, 789. 13 L. J. A. Koster, V. D. Mihailetchi, P. W. M. Blom, Appl. Phys. Lett. 2006, 88, 093511. 14 H. Hoegl, J. Phys. Chem. 1965, 69, 755. 15 J. V. Grazulevicius, P. Strohriegl, J. Pielichowski, K. Pielichowski, Prog. Polym. Sci. 2003, 28, 1297. 16 Y. Wang, Nature 1992, 356, 585. 17 J.-F. Morin, M. Leclerc, D. Adès, A. Siove, Macromol. Rapid Commun. 2005, 26, 761. 18a J. F. Morin, N. Drolet, Y. Tao, M. Leclerc, Chem. Mater. 2004, 16, 4619. 18b N. Drolet, J. F. Morin, N. Leclerc, S. Wakim, Y. Tao, M. Leclerc, Adv. Funct. Mater. 2005, 15, 1671. 19 J. Li, F. Dierschke, J. Wu, A. C. Grimsdale, K. Müllen, J. Mater. Chem. 2006, 16, 96. 20 N. Leclerc, A. Michaud, K. Sirois, J. F. Morin, M. Leclerc, Adv. Funct. Mater. 2006, 16, 1694. 21a J. F. Morin, M. Leclerc, Macromolecules 2001, 34, 4680. 21b J. F. Morin, M. Leclerc, Macromolecules 2002, 35, 8413. 22a A. Iraqi, I. Wataru, Chem. Mater. 2004, 16, 442. 22b Y. Fu, Z. Bo, Macromol. Rapid Commun. 2005, 26, 1704. 23a M. Leclerc, M. Ranger, F. Bélanger-Gariépy, Acta Crystallogr. Sect. C 1998, 54, 799. 23b M. Ranger, M. Leclerc, Macromolecules 1999, 32, 3306. 24 T. M. Fyles, R. Knoy, K. Mullen, M. Sieffert, Langmuir 2001, 17, 6669. 25a G. Zotti, G. Schiavon, S. Zecchin, J. F. Morin, M. Leclerc, Macromolecules 2002, 35, 2122. 25b F. Dierschke, A. C. Grimsdale, K. Müllen, Macromol. Chem. Phys. 2004, 205, 1147. 25c Y. Li, Y. Wu, S. Gardner, B. S. Ong, Adv. Mater. 2005, 17, 849. 26 G. Marzoni, W. L. Garbrecht, Synthesis 1987, 651. 27 A. R. Katritzky, B. Nowak-Wydra, C. M. Marson, Chem. Scr. 1987, 27, 477. 28 Y. Yoshida, Y. Sakakura, N. Aso, S. Okada, Y. Tanabe, Tetrahedron 1999, 55, 2183. 29 F. Dierschke, A. C. Grimsdale, K. Müllen, Synthesis 2003, 2470. 30 M. Ranger, D. Rondeau, M. Leclerc, Macromolecules 1997, 30, 7686. 31 U. Scherf, E. J. W. List, Adv. Mater. 2002, 14, 477. 32a I. Grosu, G. Ple, S. Mager, E. Mesaros, A. Dulau, C. Gego, Tetrahedron 1998, 54, 290. 32b A. N. Cammidge, K. V. L. Crepy, J. Org. Chem. 2003, 68, 683. 32c J. Clayden, Tetrahedron 2004, 60, 4335. 33a C. J. Brabec, C. Winder, N. S. Sariciftci, J. C. Hummelen, A. Dhanabalan, P. A. van Hal, R. A. J. Janssen, Adv. Funct. Mater. 2002, 12, 709. 33b C. Shi, Y. Yao, Y. Yang, Q. Pei, J. Am. Chem. Soc. 2006, 128, 8980. 33c Y. Yao, C. Shi, G. Li, V. Shrotriya, Q. Pei, Y. Yang, Appl. Phys. Lett. 2006, 89, 153507. 33d D. Mühlbacher, M. Scharber, M. Morana, Z. Zhu, D. Waller, R. Gaudiana, C. Brabec, Adv. Mater. 2006, 18, 2884. 34 C. Zhang, US Patent 2004 0229 925, 2004. 35 C. Towns, P. Wallace, I. Allen, T. Pounds, L. Murtagh, US Patent 2005 0014 926, 2005. 36 D. M. de Leeuw, M. M. J. Simenon, A. R. Brown, R. E. F. Einhard, Synth. Met. 1997, 87, 53. 37 B. C. Thompson, Y.-G. Kim, J. R. Reynolds, Macromolecules 2005, 38, 5359. 38 M. Lenes, L. J. A. Koster, V. D. Mihailetchi, P. W. M. Blom, Appl. Phys. Lett. 2006, 88, 243502. 39 C. Kitamura, S. Tanaka, Y. Yamashita, Chem. Mater. 1996, 8, 570. 40 A. J. Bard, L. R. Faulkner, Electrochemical Methods: Fundamentals and Applications, Wiley, New York 2001. 41 J. Rault-Berthelot, J. D. Angely, J. Simonet, New J. Chem. 1987, 11, 487. Citing Literature Volume19, Issue17September, 2007Pages 2295-2300 ReferencesRelatedInformation