Imide/amide based π-conjugated polymers for organic electronics

Progress in Polymer Science

Volumn 38, Issue 12, 2013, Pages 1815-1831

  Pron, Agnieszka ^a   Leclerc, Mario ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

Conjugated polymers; BHJ solar cells; Donor acceptor polymers; OFET; Organic electronics

Indexed keywords

BHJ SOLAR CELLS; BULK HETEROJUNCTION (BHJ); DONOR-ACCEPTOR POLYMERS; DONOR-ACCEPTORS; ORGANIC ELECTRONICS;

HETEROJUNCTIONS; ORGANIC FIELD EFFECT TRANSISTORS;

SOLAR CELLS;

EID: 84887407711     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2013.08.007     Document Type: Review

References (68)

1. Anonymous. Solarmer Energy Inc. www.solarmer.com/ [accessed August 2013].
2. J. Li, Y. Zhao, H.S. Tan, Y. Guo, A. DiC, G. Yu, Y. Liu, M. Lin, S.H. Lim, Y. Zhou, H. Su, and B.S. Ong A stable solution-processed polymer semiconductor with record high-mobility for printed transistors Sci Rep 754 2012 1 9
3. F. Wudl, M. Kabayashi, and A.J. Heeger Poly(isothianaphthene) J Org Chem 49 1984 3382 3384
4. E.E. Havinga, W. TenHoeve, and H. Wynberg A new class of small band gap organic polymer conductors Polym Bull 29 1992 119 126
5. S.H. Park, A. Roy, S. Beaupre, S. Cho, N. Coates, J.S. Moon, D. Moses, M. Leclerc, K. Lee, and A.J. Heeger Bulk heterojunction solar cells with internal quantum efficiency approaching 100% Nat Photon 3 2009 297 302
6. x as the anode interfacial layer Adv Mater 23 2011 2226 2230
7. I. Osaka, M. Shimawaki, H. Mori, I. Doi, E. Miyazaki, T. Koganezawa, and K. Takimiya Synthesis and characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer J Am Chem Soc 134 2012 3498 3507
8. M. Wang, X. Hu, P. Liu, W. Li, X. Gong, F. Huang, and Y. Cao Donor-acceptor conjugated polymer based on naphtho[1,2-c:5,6-c]bis[1,2,5] thiadiazole for high-performance polymer solar cells J Am Chem Soc 133 2011 9638 9641
9. Z. He, C. Zhong, X. Huang, W.Y. Wong, H. Wu, L. Chen, S. Su, and Y. Cao Simultaneous enhancement of open-circuit voltage, short-circuit current density, and fill factor in polymer solar cells Adv Mater 23 2011 4636 4643
10. X. Guo, F.S. Kim, M.J. Seger, S.A. Jenekhe, and M.D. Watson Naphthalene diimide-based polymer semiconductors: synthesis structure-property correlations, and n-channel and ambipolar field-effect transistors Chem Mater 24 2012 1434 1442
11. C.E. Small, S. Chen, J. Subbiah, C.M. Amb, S.W. Tsang, T.H. Lai, J.R. Reynolds, and F. So High-efficiency inverted dithienogermole-thienopyrrolodione- based polymer solar cells Nat Photon 6 2012 115 120
12. C.B. Nielsen, M. Turbiez, and I. McCulloch Recent advances in the development of semiconducting DPP-containing polymers for transistor applications Adv Mater 25 2013 1859 1880
13. A. Pron, P. Berrouard, and M. Leclerc Thieno[3,4-c]pyrrole-4,6-dione- based polymers for optoelectronic applications Macromol Chem Phys 214 2013 7 16
14. Q.T. Zhang, and J.M. Tour Low optical bandgap polythiophenes by an alternating donor/acceptor repeat unit strategy J Am Chem Soc 119 1997 5065 5066
15. Q.T. Zhang, and J.M. Tour Alternating donor/acceptor repeat units in polythiophenes intramolecular charge transfer for reducing band gaps in fully substituted conjugated polymers J Am Chem Soc 120 1998 5355 5362
16. P. Berrouard, F. Grenier, J.R. Pouliot, E. Gagnon, C. Tessier, and M. Leclerc Synthesis and characterization of 5-octylthieno[3,4-c]pyrrole-4,6-dione derivatives as new monomers for conjugated copolymers Org Lett 13 2010 38 41
17. M. Pomerantz Planar 2,2′-bithiophenes with 3,3′- and 3,3′,4,4′-substituents. A computational study Tetrahedron Lett 44 2003 1563 1565
18. Y. Zou, A. Najari, P. Berrouard, S. Beaupré, B. RédaAïch, Y. Tao, and M.A. Leclerc Thieno[3,4-c]pyrrole-4,6-dione- based copolymer for efficient solar cells J Am Chem Soc 132 2010 5330 5331
19. 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
20. C. Piliego, T.W. Holcombe, J.D. Douglas, C.H. Woo, P.M. Beaujuge, and J.M.J. Fréchet Synthetic control of structural order in N-alkylthieno[3,4-c]pyrrole-4,6-dione-based polymers for efficient solar cells J Am Chem Soc 132 2010 7595 7597
21. Z. Li, S.W. Tsang, X. Du, L. Scoles, G. Robertson, Y. Zhang, F. Toll, Y. Tao, J. Lu, and J. Ding Alternating copolymers of cyclopenta[2,1-b;3,4-b′] dithiophene and thieno[3,4-c]pyrrole-4,6-dione for high-performance polymer solar cells Adv Funct Mater 21 2011 3331 3336
22. C.M. MacNeill, E.D. Peterson, R.E. Noftle, D.L. Carroll, and R.C. Coffin A cyclopentadithiophene/thienopyrroledione-based donor-acceptor copolymer for organic solar cells Synt Met 161 2011 1137 1140
23. T.Y. Chu, J. Lu, S. Beaupré, Y. Zhang, J.R. Pouliot, S. Wakim, J. Zhou, M. Leclerc, Z. Li, J. 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% J Am Chem Soc 133 2011 4250 4253
24. C.M. Amb, S. Chen, K.R. Graham, J. Subbiah, C.E. Small, F. So, and J.R. Reynolds Dithienogermole as a fused electron donor in bulk heterojunction solar cells J Am Chem Soc 133 2011 10062 10065
25. H. Meng, and F.A. Wudl Robust low band gap processable n-type conducting polymer based on poly(isothianaphthene) Macromolecules 34 2001 1810 1816
26. W.A. Braunecker, Z.R. Owczarczyk, A. Garcia, N. Kopidakis, R.E. Larsen, S.R. Hammond, D.S. Ginley, and D.C. Olson Benzodithiophene and imide-based copolymers for photovoltaic applications Chem Mater 24 2012 1346 1356
27. H. Meng, D. Tucker, S. Chaffins, Y. Chen, R. Helgeson, B. Dunn, and F. Wudl An unusual electrochromic device based on a new low-bandgap conjugated polymer Adv Mater 15 2003 146 149
28. G. Sonmez, H. Meng, and F. Wudl Very stable low band gap polymer for charge storage purposes and near-infrared applications Chem Mater 15 2003 4923 4929
29. M.C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A.J. Heeger, and C.J. Brabec Design rules for donors in bulk-heterojunction solar cells - towards 10% energy-conversion efficiency Adv Mater 18 2006 789 794
30. J.D. Douglas, G. Griffini, T.W. Holcombe, E.P. Young, O.P. Lee, M.S. Chen, and J.M.J. Fréchet Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics Macromolecules 45 2012 4069 4074
31. Y. Wu, Y. Jing, X. Guo, S. Zhang, M. Zhang, L. Huo, and J. Hou A thieno[3,4-f]isoindole-5,7-dione based copolymer for polymer solar cells Polym Chem 4 2013 536 541
32. H. Li, S. Sun, T. Salim, S. Bomma, A.C. Grimsdale, and Y.M. Lam Conjugated polymers based on dicarboxylic imide-substituted isothianaphthene and their applications in solar cells J Polym Sci A: Polym Chem 50 2012 250 260
33. F. Dierschke, J. Jacob, and K. Müllen A hybrid polymer of polyaniline and phthalimide dyes Synth Met 156 2006 433 443
34. X. Guo, F.S. Kim, S.A. Jenekhe, and M.D. Watson Phthalimide-based polymers for high performance organic thin-film transistors J Am Chem Soc 131 2009 7206 7207
35. H. Xin, X. Guo, F.S. Kim, G. Ren, M.D. Watson, and S.A. Jenekhe Efficient solar cells based on a new phthalimide-based donor-acceptor copolymer semiconductor: morphology, charge-transport, and photovoltaic properties J Mater Chem 19 2009 5303 5310
36. H. Xin, X. Guo, G. Ren, M.D. Watson, and S.A. Jenekhe Efficient phthalimide copolymer-based bulk heterojunction solar cells: how the processing additive influences nanoscale morphology and photovoltaic properties Adv Eng Mater 2 2012 575 582
37. 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
38. G. Zhang, Y. Fu, Q. Zhang, Z. Xie, and Synthesis Photovoltaic properties of conjugated copolymers with benzo[1,2-b:4,5-b′]dithiophene and bis(thiophene)phthalimide units Macromol Chem Phys 211 2010 2596 2601
39. J.Y. Lee, K.W. Song, J.R. Ku, T.H. Sung, and D.K. Moon Development of DA-type polymers with phthalimide derivatives as electron withdrawing units and a promising strategy for the enhancement of photovoltaic properties Sol Energy Mater Sol Cells 95 2011 3377 3384
40. D. Chen, Y. Zhao, C. Zhong, S. Gao, G. Yu, Y. Liu, and J. Qin Effect of polymer chain conformation on field-effect transistor performance: synthesis and properties of two arylene imide based D-A copolymers J Mater Chem 22 2012 14639 14644
41. X. Guo, and M.D. Watson Pyromellitic diimide-based donor-acceptor poly(phenylene ethynylene)s Macromolecules 44 2011 6711 6716
42. J.A. Letizia, M.R. Salata, C.M. Tribout, A. Facchetti, M.A. Ratner, and T.J. Marks n-Channel polymers by design: optimizing the interplay of solubilizing substituents crystal packing, and field-effect transistor characteristics in polymeric bithiophene-imide semiconductors J Am Chem Soc 130 2008 9679 9694
43. J.A. Letizia, J. Rivnay, A. Facchetti, M.A. Ratner, and T.J. Marks Variable temperature mobility analysis of n-channel, p-channel, and ambipolar organic field-effect transistors Adv Funct Mater 20 2010 50 58
44. X. Guo, R.P. Ortiz, Y. Zheng, Y. Hu, Y.Y. Noh, K.J. Baeg, A. Facchetti, and T.J. Marks Bithiophene-imide-based polymeric semiconductors for field-effect transistors: synthesis, structure-property correlations charge carrier polarity, and device stability J Am Chem Soc 133 2011 1405 1418
45. H. Usta, A. Facchetti, and T.J. Marks n-Channel semiconductor materials design for organic complementary circuits Acc Chem Res 44 2011 501 510
46. N. Zhou, X. Guo, R.P. Ortiz, S. Li, S. Zhang, R.P.H. Chang, A. Facchetti, and T.J. Marks Bithiophene imide and benzodithiophene copolymers for efficient inverted polymer solar cells Adv Mater 24 2012 2242 2248
47. X. Guo, N. Zhou, S.J. Lou, J.W. Hennek, R. PonceOrtiz, M.R. Butler, P.L.T. Boudreault, J. Strzalka, P.O. Morin, M. Leclerc, J.T. LópezNavarrete, M.A. Ratner, L.X. Chen, R.P.H. Chang, A. Facchetti, and T.J. Marks Bithiopheneimide-dithienosilole/dithienogermole copolymers for efficient solar cells: information from structure-property-device performance correlations and comparison to thieno[3,4-c]pyrrole-4,6-dione analogues J Am Chem Soc 134 2012 18427 18439
48. J. Mei, K.R. Graham, R. Stalder, and J.R. Reynolds Synthesis of isoindigo-based oligothiophenes for molecular bulk heterojunction solar cells Org Lett 12 2010 660 663
49. K.R. Graham, J. Mei, R. Stalder, J.W. Shim, H. Cheun, F. Steffy, F. So, B. Kippelen, and J.R. Reynolds Polydimethylsiloxane as a macromolecular additive for enhanced performance of molecular bulk heterojunction organic solar cells ACS Appl Mater Interfaces 3 2011 1210 1215
50. K.R. Graham, P.M. Wieruszewski, R. Stalder, M.J. Hartel, J. Mei, F. So, and J.R. Reynolds Improved performance of molecular bulk-heterojunction photovoltaic cells through predictable selection of solvent additives Adv Funct Mater 22 2012 4801 4813
51. M. Yang, X. Chen, Y. Zou, C. Pan, B. Liu, and H. Zhong A solution-processable D-A-D small molecule based on isoindigo for organic solar cells J Mater Sci 48 2013 1014 1020
52. R. Stalder, J. Mei, J. Subbiah, C. Grand, L.A. Estrada, F. So, and J.R. Reynolds n-Type conjugated polyisoindigos Macromolecules 44 2011 6303 6310
53. R. Stalder, J. Mei, and J.R. Reynolds Isoindigo-based donor-acceptor conjugated polymers Macromolecules 43 2010 8348 8352
54. B. Liu, Y. Zou, B. Peng, B. Zhao, K. Huang, Y. He, and C. Pan Low bandgap isoindigo-based copolymers: design, synthesis and photovoltaic applications Polym Chem 2 2011 1156 1162
55. Z. Ma, E. Wang, M.E. Jarvid, P. Henriksson, O. Inganas, F. Zhang, and M.R. Andersson Synthesis and characterization of benzodithiophene-isoindigo polymers for solar cells J Mater Chem 22 2012 2306 2314
56. K. Cao, Z. Wu, S. Li, B. Sun, G. Zhang, and Q. Zhang A low bandgap polymer based on isoindigo and bis(dialkylthienyl)benzodithiophene for organic photovoltaic applications J Polym Sci A: Polym Chem 51 2013 94 100
57. C. Hu, Y. Fu, S. Li, Z. Xie, and Q. Zhang Synthesis and photovoltaic properties of new conjugated polymers based on syn- and anti-benzodifuran Polym Chem 3 2012 2949 2955
58. E. Wang, Z. Ma, Z. Zhang, P. Henriksson, O. Inganas, F. Zhang, and M.R. Andersson An isoindigo-based low band gap polymer for efficient polymer solar cells with high photo-voltage Chem Commun 47 2011 4908 4910
59. K. Vandewal, Z. Ma, J. Bergqvist, Z. Tang, E. Wang, P. Henriksson, K. Tvingstedt, M.R. Andersson, F. Zhang, and O. Inganäs Quantification of quantum efficiency and energy losses in low bandgap polymer:fullerene solar cells with high open-circuit voltage Adv Funct Mater 22 2012 3480 3490
60. T. Lei, Y. Cao, Y. Fan, C.J. Liu, S.C. Yuan, and J. Pei High-performance air-stable organic field-effect transistors: isoindigo-based conjugated polymers J Am Chem Soc 133 2011 6099 6101
61. Z. Ma, E. Wang, K. Vandewal, M.R. Andersson, and F. Zhang Enhance performance of organic solar cells based on an isoindigo-based copolymer by balancing absorption and miscibility of electron acceptor Appl Phys Lett 99 2011 143302 143303
62. E. Wang, Z. Ma, Z. Zhang, K. Vandewal, P. Henriksson, O. Inganäs, F. Zhang, and M.R. Andersson An easily accessible isoindigo-based polymer for high-performance polymer solar cells J Am Chem Soc 133 2011 14244 14247
63. T. Lei, Y. Cao, X. Zhou, Y. Peng, J. Bian, and J. Pei Systematic investigation of isoindigo-based polymeric field-effect transistors: design strategy and impact of polymer symmetry and backbone curvature Chem Mater 24 2012 1762 1770
64. J. Mei, D.H. Kim, A.L. Ayzner, M.F. Toney, and Z. Bao Siloxane-terminated solubilizing side chains: bringing conjugated polymer backbones closer and boosting hole mobilities in thin-film transistors J Am Chem Soc 133 2011 20130 20133
65. Y. Deng, Y. Chen, X. Zhang, H. Tian, C. Bao, D. Yan, Y. Geng, and F. Wang Donor-acceptor conjugated polymers with dithienocarbazoles as donor units: effect of structure on semiconducting properties Macromolecules 45 2012 8621 8627
66. R.S. Ashraf, A.J. Kronemeijer, D.I. James, H. Sirringhaus, and I. McCulloch A new thiophene substituted isoindigo based copolymer for high performance ambipolar transistors Chem Commun 48 2012 3939 3941
67. Y. Koizumi, M. Ide, A. Saeki, C. Vijayakumar, B. Balan, M. Kawamotov, and S. Seki Thienoisoindigo-based low-band gap polymers for organic electronic devices Polym Chem 4 2013 484 494
68. G.W.P. VanPruissen, F. Gholamrezaie, M.M. Wienk, and R.A.J. Janssen Synthesis and properties of small band gap thienoisoindigo based conjugated polymers J Mater Chem 22 2012 20387 20393