N-acyl-dithieno[3,2-b:2',3'-d]pyrrole-based low bandgap copolymers affording improved open-circuit voltages and efficiencies in polymer solar cells

Solar Energy Materials and Solar Cells

Volumn 136, Issue , 2015, Pages 70-77

  Kesters, Jurgen ^a   Verstappen, Pieter ^a   Vanormelingen, Wouter ^a   Drijkoningen, Jeroen ^a   Vangerven, Tim ^a   Devisscher, Dries ^a   Marin, Lidia ^a   Champagne, Benoît ^b   Manca, Jean ^a   Lutsen, Laurence ^a   Vanderzande, Dirk ^a   Maes, Wouter ^a  

^a HASSELT UNIVERSITY   (Belgium)

^b UNIVERSITY OF NAMUR   (Belgium)

Author keywords

Dithieno 3,2 b:2 ,3 d pyrrole; Fluorination; Low bandgap copolymers; N acylation; Organic photovoltaics; Quinoxaline

Indexed keywords

ACYLATION; AROMATIC COMPOUNDS; COPOLYMERS; EFFICIENCY; ENERGY GAP; FLUORINATION; HETEROJUNCTIONS; OPEN CIRCUIT VOLTAGE; POLYMERS;

BULK HETEROJUNCTION; INTERLAYER MATERIALS; LOW BAND-GAP COPOLYMERS; ORGANIC PHOTOVOLTAICS; POLYMER SOLAR CELLS; POWER CONVERSION EFFICIENCIES; QUINOXALINES; SOLAR CELL EFFICIENCIES;

SOLAR CELLS;

EID: 84921656813     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2014.12.037     Document Type: Article

References (78)

1. C.J. Brabec, S. Gowrisanker, J.J.M. Halls, D. Laird, S. Jia, and S.P. Williams Polymer-fullerene bulk-heterojunction solar cells Adv. Mater. 22 2010 3839 3856
2. M. Jørgensen, K. Norrman, S.A. Gevorgyan, T. Tromholt, B. Andreasen, and F.C. Krebs Stability of polymer solar cells Adv. Mater. 24 2012 580 612
3. Y. Li Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption Acc. Chem. Res. 45 2012 723 733
4. A. Mishra, and P. Baüerle Small molecule organic semiconductors on the move: promises for future solar energy technology Angew. Chem. Int. Ed. 51 2012 2020 2067
5. S. Lizin, S. Van Passel, E. De Schepper, W. Maes, L. Lutsen, J. Manca, and D. Vanderzande Life cycle analyses of organic photovoltaics: a review Energy Environ. Sci. 6 2013 3136 3149
6. th Anniversary article: a decade of organic/polymeric photovoltaic research Adv. Mater. 25 2013 6642 6671
7. K. Vandewal, S. Himmelberger, and A. Salleo Structural factors that affect the performance of organic bulk heterojunction solar cells Macromolecules 46 2013 6379 6387
8. th Anniversary article: bulk heterojunction solar cells: understanding the mechanism of operation Adv. Mater. 26 2014 10 28
9. Y. Chen, X. Wan, and G. Long High performance photovoltaic applications using solution-processed small molecules Acc. Chem. Res. 46 2014 2645 2655
10. R. Søndergaard, M. Hösel, D. Angmo, T.T. Larsen-Olsen, and F.C. Krebs Roll-to-roll fabrication of polymer solar cells Mater. Today 15 2012 36 49
11. Z.C. He, C.M. Zhong, S.J. Su, M. Xu, H.B. Wu, and Y. Cao Enhanced power-conversion efficiency in polymer solar cells using an inverted device structure Nat. Photonics 6 2012 591 595
12. K.H. Hendriks, G.H.L. Heintges, V.S. Gevaerts, M.M. Wienk, and R.A.J. Janssen High-molecular-weight regular alternating diketopyrrolopyrrole-based terpolymers for efficient organic solar cells Angew. Chem. Int. Ed. 52 2013 8341 8344
13. I. Osaka, T. Kakara, N. Takemura, T. Koganezawa, and K. Takimiya Naphtadithiophene-naphthobisthiadiazole copolymers for solar cells: alkylation drives the polymer backbone flat and promotes efficiency J. Am. Chem. Soc. 135 2013 8834 8837
14. Y. Deng, J. Liu, J. Wang, L. Liu, W. Li, H. Tian, X. Zhang, Z. Xie, Y. Geng, and F. Wang Dithienocarbazole and isoindigo based amorphous low bandgap conjugated polymers for efficient polymer solar cells Adv. Mater. 26 2014 471 476
15. M. Zhang, X. Guo, S. Zhang, and J. Hou Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers Adv. Mater. 26 2014 1118 1123
16. A.K.K. Kyaw, D.H. Wang, D. Wynands, J. Zhang, T.-Q. Nguyen, G.C. Bazan, and A.J. Heeger Improved light harvesting and improved efficiency by insertion of an optical spacer (ZnO) in solution-processed small-molecule solar cells Nano Lett. 13 2013 3796 3801
17. Y. Liu, Y. Yang, C.-C. Chen, Q. Chen, L. Dou, Z. Hong, G. Li, and Y. Yang Solution-processed small molecules using different electron linkers for high-performance solar cells Adv. Mater. 25 2013 4657 4662
18. V.S. Gevaerts, E.M. Herzig, M. Kirkus, K.H. Hendriks, M.M. Wienk, J. Perlich, P. Müller-Buschbaum, and R.A.J. Janssen Influence of the position of the side chain on crystallization and solar cell performance of DPP-based small molecules Chem. Mater. 26 2014 916 926
19. D. Liu, M. Xiao, Z. Du, Y. Yan, L. Han, V.A.L. Roy, M. Sun, W. Zhu, C.S. Lee, and R. Yang Solution-processed, indacenodithiophene-based, small-molecule organic field effect transistors and solar cellsm J. Mater. Chem. C 2 2014 7523 7530
20. B. Kan, Q. Zhang, M. Li, X. Wan, W. Ni, G. Long, Y. Wang, X. Yang, H. Feng, and Y. Chen Solution-processed organic solar cells based on dialkylthiol-substituted benzodithiophene unit with efficiency near 10% J. Am. Chem. Soc. 136 2014 15529 15532
21. Y. Liu, J. Zhao, Z. Li, C. Mu, W. Ma, H. Hu, K. Jiang, H. Lin, H. Ade, H. Yan, Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells. Nat. Commun. http://dx.doi.org/:10.1038/ncomms6293
22. G. Ren, P.-T. Wu, and S.A. Jenekhe Enhanced performance of bulk heterojunction solar cells using block copoly(3-alkylthiophene)s Chem. Mater. 22 2010 2020 2026
23. G. Ren, P.-T. Wu, and S.A. Jenekhe Solar cells based on block copolymer semiconductor nanowires: effects of nanowire aspect ratio ACS Nano 5 2011 376 384
24. C. Cabanetos, A.E. Labban, J.A. Bartelt, J.D. Douglas, W.R. Mateker, J.M.J. Fréchet, M.D. McGehee, and P.M. Beaujuge Linear side chains in benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione polymers direct self-assembly and solar cell performance J. Am. Chem. Soc. 135 2013 4656 4659
25. L. Luyao, and L. Yu Understanding low bandgap polymer PTB7 and optimizing polymer solar cells of it Adv. Mater. 26 2014 4413 4430
26. J. Kesters, S. Kudret, S. Bertho, N. Van den Brande, M. Defour, B. Van Mele, H. Penxten, L. Lutsen, J. Manca, D. Vanderzande, and W. Maes Enhanced intrinsic stability of the bulk heterojunction active layer blend of polymer solar cells by varying the polymer side chain pattern Org. Electron. 15 2014 549 562
27. 71BM solar cells J. Phys. Chem. C. 118 2014 9918 9929
28. H.-C. Chen, Y.-H. Chen, C.-C. Liu, Y.-C. Chien, S.-W. Chou, and P.-T. Chou Prominent short-circuit currents of fluorinated quinoxaline-based copolymer solar cells with a power conversion efficiency of 8.0% Chem. Mater. 24 2012 4766 4772
29. H.-C. Chen, Y.-H. Chen, C.-H. Liu, Y.-H. Hsu, Y.-C. Chien, W.-T. Chuang, C.-Y. Cheng, C.-L. Liu, S.-W. Chou, S.-H. Tung, and P.-T. Chou Fluorinated thienyl-quinoxaline-based D-π-A-type copolymer toward efficient polymer solar cells; synthesis, characterization, and photovoltaic properties, Polym Chem 4 2013 3411
30. J.-H. Kim, C.E. Song, H.U. Kim, A.C. Grimsdale, S.-J. Moon, W.S. Shin, S.K. Choi, and D.-H. Hwang High open circuit voltage solution-processed tandem organic photovoltaic cells employing a bottom cell using a new medium band gap semiconducting polymer Chem. Mater. 25 2013 2722 2732
31. M. Zhang, X. Guo, S. Zhang, and J. Hou Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers Adv. Mater. 26 2013 1118 1123
32. K. Ogowa, and S.C. Rasmussen A simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles: fused-ring building blocks for new conjugated polymeric systems J. Org. Chem. 68 2003 2921 2928
33. G. Koeckelberghs, L. De Cremer, W. Vanormelingen, W. Dehaen, T. Verbiest, A. Persoons, and C. Samyn Improved synthesis of N-alkyl substituted dithieno[3,2-b:2′,3′-d]pyrroles Tetrahedron 61 2005 687 691
34. K. Ogowa, and S.C. Rasmussen N-functionalized poly(dithieno[3,2-b:2′,3′-d]pyrrole)s: Highly fluorescent materials with reduced band gaps Macromolecules 39 2006 1771 1778
35. K.R. Radke, K. Ogowa, and S.C. Rasmussen Highly fluorescent oligothiophenes through the incorporation of cental dithieno[3,2-b:2′,3′-d]pyrrole units Org. Lett. 7 2005 5253 5256
36. J. Liu, R. Zhang, G. Sauvé, T. Kowalewski, and R.D. McCullough Highly disordered polymer field effect transistors: N-alkyl dithieno[3,2-b:2′,3′-d]pyrrole-based copolymers with surprisingly high charge carrier mobilities J. Am. Chem. Soc. 130 2008 13167 13176
37. W. Zhang, J. Li, B. Zhang, J. Qin, Z. Lu, Y.F. Poon, M.B. Chan-Park, and C.M. Li Semiconducting polymers containing dithieno[3,2-b:2′,3′-d]pyrrole for organic thin-film transistors Macromolecules 41 2008 8953 8955
38. X. Zhan, Z. Tan, E. Zhou, Y. Li, R. Misra, A. Grant, B. Domercq, X.-H. Zhang, Z. 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 field-effect transistors J. Mater. Chem. 19 2009 5794 5803
39. X. Zhang, T.T. Steckler, R.R. Dasari, S. Ohira, W.J. Potscavage, S.P. Tiwari, S. Coppeé, S. Ellinger, S. Barlow, J.-L. Brédas, B. Kippelen, J.R. Reynolds, and S.R. Marder Dithienopyrrole-based donor-acceptor copolymers: low band-gap materials for charge transport, photovoltaics and electrochromism J. Mater. Chem. 20 2010 123 134
40. S.C. Rasmussen, and S.J. Evenson Dithieno[3,2-b:2′,3′-d]pyrrole-based materials: Synthesis and application to organic electronics Prog. Polym. Sci. 38 2013 1773 1804
41. K.M. Noone, E. Strein, N.C. Anderson, P.-T. Wu, S.A. Jenekhe, and D.S. Ginger Broadband absorbing bulk heterojunction photovoltaics using low-bandgap solution-processed quantum dots Nano Lett. 10 2010 2635 2639
42. W. Yue, Y. Zhao, S. Shao, H. Tian, Z. Xie, Y. Geng, and F. Wang Novel NIR-absorbing conjugated polymers for efficient polymer solar cells: effect of alkyl chain length on device performance J. Mater. Chem. 19 2009 2199 2206
43. E. Zhou, Q. Wei, S. Yamakawa, Y. Zhang, K. Tajima, C. Yang, and K. Hashimoto Diketopyrrolopyrrole-based semiconducting polymer for photovoltaic device with photocurrent response wavelengths up to 1.1 μm Macromolecules 43 2010 821 826
44. E. Zhou, J. Cong, L. Tajima, C. Yang, and K. Hashimoto Synthesis and photovoltaic properties of donor-acceptor copolymer based on dithienopyrrole and thienopyrroledione Macromol. Chem. Phys. 212 2011 305 310
45. X. Hu, M. Shi, L. Zuo, Y. Nan, Y. Liu, L. Fu, and H. Chen Synthesis, characterization, and photovoltaic property of a low band gap polymer alternating dithienopyrrole and thienopyrroledione units Polymer 52 2011 2559 2564
46. X. Zhang, J.W. Shim, S.P. Tiwari, Q. Zhang, J.E. Norton, P.-T. Wu, S. Barlow, S.A. Jenekhe, B. Kippelen, J.-L. Brédas, and S.R. Marder Dithienopyrrole-quinoxaline/pyridopyrazine donor-acceptor polymers: synthesis and electrochemical, optical, charge-transport, and photovoltaic properties J. Mater. Chem. 21 2011 4971 4982
47. E. Zhou, J. Cong, K. Tajima, C. Yang, and K. Hashimoto Conjugated polymers based on 1,3-dithien-2-yl-thieno[3,4-c]pyrrole-4,6-dione: Synthesis, characterization, and solvent effects on photovoltaic performance J. Phys. Chem. B 116 2012 2608 2614
48. B. Burkhart, P.P. Khlyabich, and B.C. Thompson Solar cells based on semi-random P3HT analogues containing dithienopyrrole: influence of incorporating a strong donor J. Photon. Energy 2 2012 021002
49. Z. Li, D. Zhou, L. Li, Y. Li, Y. He, J. Liu, and Q. Peng Synthesis and characterization of copolymers based on benzotriazoles and different atom-bridged dithiophenes for efficient solar cells Polym. Chem. 4 2013 2496 2505
50. V. Tamilavan, M. Song, S. Kim, R. Agneeswari, J.-W. Kang, and M.H. Hyun Polymer 54 2013 3198 3205
51. W. Yue, T.T. Larsen-Olsen, X. Hu, M. Shi, H. Chen, M. Hinge, P. Fojan, F.C. Krebs, and D. Yu Synthesis and photovoltaic properties from inverted geometry cells and roll-to-roll coated large area cells from dithienopyrrole-based donor-acceptor polymers J. Mater. Chem. A 1 2013 1785 1793
52. Y. Geng, J. Cong, K. Tajima, Q. Zeng, and E. Zhou Synthesis and properties of D-A copolymers based on dithienopyrrole and benzothiadiazole with various numbers of thienyl units as spacers Polym. Chem. 5 2014 6797 6803
53. K.H. Hendriks, W. Li, M.M. Wienk, and R.A.J. Janssen Small-bandgap semiconducting polymers with high near-infrared photoresponse J. Am. Chem. Soc. 136 2014 12130 12136
54. M. Weidelener, C.D. Wessendorf, J. Hanisch, E. Ahlswede, G. Götz, M. Lindén, G. Schulz, E. Mena-Osteritz, A. Mishra, and P. Baüerle Dithienopyrrole-based oligothiophenes for solution-processed organic solar cells Chem. Commun. 49 2013 10865 10867
55. L.G. Mercier, A. Mishra, Y. Ishigaki, F. Henne, G. Schulz, and P. Baüerle Acceptor-donor-acceptor oligormers containing dithieno[3,2-b:2′,3′-d]pyrrole and thieno[2,3-c]pyrrole-4,6-dione units for solution-processed organic solar cells Org. Lett. 16 2014 2642 2645
56. H.-I. Lu, C.-W. Lu, Y.-C. Lee, H.-W. Lin, L.-Y. Lin, F. Lin, J.-H. Chang, C.-I. Wu, and K.-T. Wong New molecular donors with dithienopyrrole as electron-donating group for efficient small molecule organic solar cells Chem. Mater. 26 2014 4361 4367
57. A.M. Poe, A.M. Della Pelle, A.V. Subrahmanyam, W. White, G. Wantz, and S. Thayumanavan Small molecule BODIPY dyes as non-fullerene acceptors in bulk heterojunction organic photovoltaics Chem. Commun. 50 2014 2913 2915
58. S.J. Evenson, and S.C. Rasmussen N-acyldithieno[3,2-b:2′,3′-d]pyrroles: Second generation dithieno[3,2-b:2′,3′-d]pyrrole building blocks with stabilized energy levels Org. Lett. 12 2010 4054 4057
59. J. Warnan, C. Cabanetos, R. Bude, A. El Labban, L. Li, and P.M. Beaujuge Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltage>1 V Chem. Mater. 26 2014 2829 2835
60. 61-butyric acid ester cathode interlayers ACS Appl. Mater. Interfaces 5 2013 10995 11003
61. W. Vanormelingen, J. Kesters, P. Verstappen, J. Drijkoningen, J. Kudrjasova, S. Koudjina, V. Liégeois, B. Champagne, J. Manca, L. Lutsen, D. Vanderzande, and W. Maes Enhanced open-circuit voltage in polymer solar cells by dithieno[3,2-b:2′,3′-d]pyrrole N-acylation J. Mater. Chem. A 2 2014 7535 7545
62. D. Kitazawa, N. Watanabe, S. Yamamoto, and J. Tsukamoto Quinoxaline-based π-conjugated donor polymer for highly efficient organic thin-film solar cells Appl. Phys. Lett. 95 2009 053701
63. E. Wang, L. Hou, Z. Wang, S. Hellström, F. Zhang, O. Inganäs, and M.R. Andersson An easily synthesized blue polymer for high-performance polymer solar cells Adv. Mater. 22 2010 5240 5244
64. Y. Kim, H.R. Yeom, J.Y. Kim, and C. Yang High-efficiency polymer solar cells with a cost-effictive quinoxaline polymer through nanoscale morphology control induced by practical processing additives Energy Environ. Sci. 6 2013 1909 1916
65. W. Zhuang, H. Zhen, R. Kroon, Z. Tang, S. Hellström, L. Hou, E. Wang, D. Gedefaw, O. Inganäs, F. Zhang, and M.R. Andersson Molecular orbital energy level modulation through incorporation of selenium and fluorine into conjugated polymers for organic photovoltaic cells J. Mater. Chem. A 1 2013 13422 13425
66. Y. Zhang, J. Zou, H.-L. Yip, K.-S. Chen, D.F. Zeigler, Y. Sun, and A.K.-Y. Jen Indacenodithiophene and quinoxaline-based conjugated polymers for highly efficient polymer solar cells Chem Mater. 23 2011 2289 2291
67. L. Marin, L. Lutsen, D. Vanderzande, and W. Maes Quinoxaline derivatives with broadened absorption patterns Org. Biomol. Chem. 11 2013 5866 5876
68. G.K. Dutta, T. Kim, H. Choi, J. Lee, D.S. Kim, J.Y. Kim, and C. Yang Synthesis of fluorinated analogues of a practical polymer TQ for improved open-circuit voltages in polymer solar cells Polym. Chem. 5 2014 2540 2547
69. R.L. Danley, P.A. Caulfield, and S.R. Aubuchon A rapid-scanning differential scanning calorimeter Am. Lab. 40 2008 9 11
70. S. Wouters, F. Demir, L. Beenaerts, and G. Van Assche Calibration and performance of a fast-scanning DSC-Project RHC Thermochim. Acta 530 2012 64
71. J. Bard, and L.R. Faulkner Electrochemical Methods: Fundamentals and Applications second ed. 2001 Wiley
72. S. Trasatti The absolute electrode potential: an explanatory note Pure Appl. Chem. 58 1986 955 966
73. T. Ghoos, N. Van den Brande, M. Defour, J. Brassinne, C.-A. Fustin, J.-F. Gohy, S. Hoeppener, U.S. Schubert, W. Vanormelingen, L. Lutsen, D.J. Vanderzande, B. Van Mele, and W. Maes Amphiphilic N-methylimidazole-functionalized diblock copolythiophenes for organic photovoltaics Eur. Polym. J. 53 2014 206 214
74. H.J. Son, W. Wang, T. Xu, Y. Liang, Y. Wu, G. Li, and L. Yu Synthesis of fluorinated polythienothiopene-co-benzodithiophenes and effect of fluorination on the photovoltaic properties J. Am. Chem. Soc. 133 2011 1885 1894
75. Y. Zhao, N.E. Schultz, and D.G. Truhlar Exchange-correlation functional with broad accuracy for metallic and nonmetallic compounds, kinetics, and noncovalent interactions J. Chem. Phys. 123 2005 161103
76. J. Tomasi, B. Mennucci, and R. Cammi Quantum mechanical continuum solvation models Chem. Rev. 105 2005 2999 3093
77. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta Jr., F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.1 2009 Gaussian, Inc. Wallingford CT
78. G.J. Hedley, A.J. Ward, A. Alekseev, C.T. Howells, E.R. Martins, L.A. Serrano, G. Cooke, A. Ruseckas, and I.D.W. Samuel Determining the optimum morphology in high-performance polymer-fullerene organic photovoltaic cells Nat. Commun. 4 2013 2867