π-Extended Narrow-Bandgap Diketopyrrolopyrrole-Based Oligomers for Solution-Processed Inverted Organic Solar Cells

Advanced Energy Materials

Volumn 4, Issue 17, 2014, Pages

  Shin, Woong ^a   Yasuda, Takuma ^a,b   Hidaka, Yu ^a   Watanabe, Go ^c   Arai, Ryota ^d   Nasu, Keiro ^a   Yamaguchi, Takahiro ^c   Murakami, Wakako ^d   Makita, Kengo ^d   Adachi, Chihaya ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c KITASATO UNIVERSITY   (Japan)

^d RICOH COMPANY LTD   (Japan)

Author keywords

Diketopyrrolopyrrole; Donor acceptor pairs; Film morphology; Oligomers; Organic solar cells

Indexed keywords

BUTYRIC ACID; ENERGY DISPERSIVE SPECTROSCOPY; ENERGY GAP; HALL MOBILITY; HETEROJUNCTIONS; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; HOLE MOBILITY; LIGHT ABSORPTION; MOLECULAR ORBITALS; MOLECULES; MORPHOLOGY; OLIGOMERS; SYNTHESIS (CHEMICAL);

BULK-HETEROJUNCTION DEVICES; DIKETOPYRROLOPYRROLES; DONOR-ACCEPTOR PAIRS; ENERGY DISPERSIVE X RAY SPECTROSCOPY; FILM MORPHOLOGY; HIGHEST OCCUPIED MOLECULAR ORBITAL ENERGY LEVELS; INVERTED ORGANIC SOLAR CELLS; SMALL-MOLECULE ORGANIC SOLAR CELLS;

ORGANIC SOLAR CELLS;

EID: 84916943055     PISSN: 16146832     EISSN: 16146840     Source Type: Journal    
DOI: 10.1002/aenm.201400879     Document Type: Article

References (62)

1. S. B. Darling, F. You, RSC Adv. 2013, 3, 17633.
2. National Renewable Energy Laboratory (NREL), Best Research-Cell Efficiencies: http://www.nrel.gov/ncpv/images/efficiency-chart.jpg (accessed June 2014).
3. a) L. Dou, J. You, Z. Hong, Z. Xu, G. Li, R. A. Street, Y. Yang, Adv. Mater. 2013, 25, 6642;
4. b) A. Mishra, P. Bäuerle, Angew. Chem. Int. Ed. 2012, 51, 2020;
5. c) H. J. Son, B. Carsten, I. H. Jung, L. Yu, Energy Environ. Sci. 2012, 5, 8158;
6. d) P. M. Beaujuge, J. M. J. Fréchet, J. Am. Chem. Soc. 2011, 133, 20009;
7. e) B. Walker, C. Kim, T.-Q. Nguyen, Chem. Mater. 2010, 23, 470.
8. a) X. Guo, N. Zhou, S. J. Lou, J. Smith, D. B. Tice, J. W. Hennek, R. P. Ortiz, J. T. L. Navarrete, S. Li, J. Strzalka, L. X. Chen, R. P. H. Chang, A. Facchetti, T. J. Marks, Nat. Photonics 2013, 7, 825;
9. b) Z. He, C. Zhong, S. Su, M. Xu, H. Wu, Y. Cao, Nat. Photonics 2012, 6, 593;
10. c) C. Cabanetos, A. El Labban, J. A. Bartelt, J. D. Douglas, W. R. Mateker, J. M. J. Fréchet, M. D. McGehee, P. M. Beaujuge, J. Am. Chem. Soc. 2013, 135, 4656;
11. d) J. You, L. Dou, K. Yoshimura, T. Kato, K. Ohya, T. Moriarty, K. Emery, C.-C. Chen, J. Gao, G. Li, Y. Yang, Nat. Commun. 2013, 4, 1446.
12. M. P. Nikiforov, B. Lai, W. Chen, S. Chen, R. D. Schaller, J. Strazalka, J. Maser, S. B. Darling, Energy Environ. Sci. 2013, 6, 1513.
13. a) Y. Liu, C.-C. Chen, Z. Hong, J. Gao, Y. Yang, H. Zhou, L. Dou, G. Li, Y. Yang, Sci. Rep. 2013, 3, 3356;
14. b) J. Zhou, Y. Zuo, X. Wan, G. Long, Q. Zhang, W. Ni, Y. Liu, Z. Li, G. He, C. Li, B. Kan, M. Li, Y. Chen, J. Am. Chem. Soc. 2013, 135, 8484;
15. c) J. Zhou, X. Wan, Y. Liu, Y. Zuo, Z. Li, G. He, G. Long, W. Ni, C. Li, X. Su, Y. Chen, J. Am. Chem. Soc. 2012, 134, 16345;
16. d) V. Gupta, A. K. K. Kyaw, D. H. Wang, S. Chand, G. C. Bazan, A. J. Heeger, Sci. Rep. 2013, 3, 1965;
17. e) A. K. K. Kyaw, D. H. Wang, V. Gupta, J. Zhang, S. Chand, G. C. Bazan, A. J. Heeger, Adv. Mater. 2013, 25, 2397.
18. a) Y. Sun, G. C. Welch, W. L. Leong, C. J. Takacs, G. C. Bazan, A. J. Heeger, Nat. Mater. 2012, 11, 44;
19. b) X. Liu, Y. Sun, L. A. Perez, W. Wen, M. F. Toney, A. J. Heeger, G. C. Bazan, J. Am. Chem. Soc. 2012, 134, 20609;
20. c) C. J. Takacs, Y. Sun, G. C. Welch, L. A. Perez, X. Liu, W. Wen, G. C. Bazan, A. J. Heeger, J. Am. Chem. Soc. 2012, 134, 16597;
21. d) T. S. Van der Poll, J. A. Love, T.-C. Nguyen, G. C. Bazan, Adv. Mater. 2012, 24, 3646.
22. a) J. Zhou, X. Wan, Y. Liu, G. Long, F. Wang, Z. Li, Y. Zuo, C. Li, Y. Chen, Chem. Mater. 2011, 23, 4666;
23. b) Y. Liu, X. Wan, F. Wang, J. Zhou, G. Long, J. Tian, Y. Chen, Adv. Mater. 2011, 23, 5387;
24. c) Y. Liu, X. Wan, F. Wang, J. Zhou, G. Long, J. Tian, J. You, Y. Yang, Y. Chen, Adv. Energy Mater. 2011, 1, 771;
25. d) Z. Li, G. He, X. Wan, Y. Liu, J. Zhou, G. Long, Y. Zuo, M. Zhang, Y. Chen, Adv. Energy Mater. 2012, 2, 74;
26. e) G. He, Z. Li, X. Wan, Y. Liu, J. Zhou, G. Long, M. Zhang, Y. Chen, J. Mater. Chem. 2012, 22, 9173.
27. R. Fitzner, E. Mene-Osteritz, A. Mishra, G. Schulz, E. Reinold, M. Weil, C. Körner, H. Ziehlke, C. Elschner, K. Leo, M. Riede, M. Pfeiffer, C. Uhrich, P. Bäuerle, J. Am. Chem. Soc. 2012, 134, 11064.
28. a) B. Walker, A. B. Tamayo, X.-D. Dang, P. Zalar, J. H. Seo, A. Garcia, M. Tantiwiwat, T.-C. Nguyen, Adv. Funct. Mater. 2009, 19, 3063;
29. b) J. Liu, B. Walker, A. Tamayo, Y. Zhang, T.-C. Nguyen, Adv. Funct. Mater. 2013, 23, 47;
30. c) S. Loser, C. J. Bruns, H. Miyauchi, R. P. Ortiz, A. Facchetti, S. I. Stupp, T. J. Marks, J. Am. Chem. Soc. 2011, 133, 8142;
31. d) O. P. Lee, A. T. Yiu, P. M. Beaujuge, C. H. Woo, T. W. Holcombe, J. E. Millstone, J. D. Douglas, M. S. Chen, J. M. J. Fréchet, Adv. Mater. 2011, 23, 5359;
32. e) A. B. Tamayo, B. Walker, T.-Q. Nguyen, J. Phys. Chem. C 2008, 112, 11545;
33. f) A. B. Tamayo, X.-D. Dang, B. Walker, J. Seo, T. Kent, T.-C. Nguyen, Appl. Phys. Lett. 2009, 94, 103301;
34. g) J. Huang, C. Zhan, X. Zhang, Y. Zhao, Z. Lu, H. Jia, B. Jiang, J. Ye, S. Zhang, A. Tang, Y. Liu, Q. Pei, J. Yao, ACS Appl. Mater. Interfaces 2013, 5, 2033;
35. h) Y. Lin, L. Ma, Y. Li, Y. Liu, D. Zhu, X. Zhan, Adv. Energy Mater. 2013, 3, 1166.
36. W. Shin, T. Yasuda, G. Watanabe, Y. S. Yang, C. Adachi, Chem. Mater. 2013, 25, 2549.
37. The calculated oscillator strengths of all four oligomers are considerably larger than that (f = 0.96) of previously reported DPP-based small molecules, DPP-TP. [11]
38. a) A. K. K. Kyaw, D. H. Wang, V. Gupta, J. Zhang, S. Chand, G. C. Bazan, A. J. Heeger, Adv. Mater. 2013, 25, 2397;
39. b) A. K. K. Kyaw, X. W. Sun, C. Y. Jiang, G. Q. Lo, D. W. Zhao, D. L. Kwong, Appl. Phys. Lett. 2008, 93, 221107;
40. c) Y. Sun, J. H. Seo, C. J. Takacs, J. Seifter, A. J. Heeger, Adv. Mater. 2011, 23, 1679;
41. d) C.-H. Chou, W. L. Kwan, Z. Hong, L.-M. Chen, Y. Yang, Adv. Mater. 2011, 23, 1282;
42. e) F. C. Krebs, S. A. Gevorgyan, J. Alstrup, J. Mater. Chem. 2009, 19, 5442.
43. a) J. K. Lee, W. L. Ma, C. J. Brabec, J. Yuen, J. S. Moon, J. Y. Kim, K. Lee, G. C. Bazan, A. J. Heeger, J. Am. Chem. Soc. 2008, 130, 3619;
44. b) C. V. Hoven, X.-D. Dang, R. C. Coffin, J. Peet, T.-C. Nguyen, G. C. Bazan, Adv. Mater. 2010, 22, E63;
45. c) K. R. Graham, P. M. Wieruszewski, R. Stalder, M. J. Hartel, J. Mei, F. So, J. R. Reynolds, Adv. Mater. 2012, 22, 4801;
46. d) H.-C. Liao, C.-C. Ho, C.-Y. Chang, M.-H. Jao, S. B. Darling, W.-F. Su, Mater. Today 2013, 16, 326.
47. a) M. Campoy-Quiles, T. Ferenczi, T. Agostinelli, P. G. Etchegoin, Y. Kim, T. D. Anthopoulos, P. N. Stavrinou, D. D. C. Bradley, J. Nelson, Nat. Mater. 2008, 7, 158;
48. b) A. Tada, Y. Geng, Q. Wei, K. Hashimoto, K. Tajima, Nat. Mater. 2011, 10, 450;
49. c) M. D. Clark, M. L. Jespersen, R. J. Patel, B. J. Leever, ACS Appl. Mater. Interfaces 2013, 5, 4799.
50. a) B. Kippelen, J.-L. Brédas, Energy Environ. Sci. 2009, 2, 251;
51. b) T. M. Clarke, J. R. Durrant, Chem. Rev. 2010, 110, 6736.
52. W. Chen, M. P. Nikiforov, S. B. Darling, Energy Environ. Sci. 2012, 5, 8045.
53. a) M. A. Lampert, P. Mark, Current Injection in Solids, Academic Press, New York 1970;
54. b) N. F. Mott, D. Gurney, Electronic Processes in Ionic Crystals, Academic Press, New York 1970.
55. a) P. W. M. Blom, M. J. M. de Jong, J. J. M. Vleggaar, Appl. Phys. Lett. 1996, 68, 3308;
56. b) L. Bozano, S. A. Carter, J. C. Scott, G. G. Malliaras, P. J. Brock, Appl. Phys. Lett. 1999, 74, 1132;
57. c) Z. An, J. Yu, S. C. Jones, S. Barlow, S. Yoo, B. Domercq, P. Prins, L. D. A. Siebbeles, B. Kippelen, S. R. Marder, Adv. Mater. 2005, 17, 2580;
58. d) J. Y. Kim, T. Yasuda, Y. S. Yang, C. Adachi, Adv. Mater. 2013, 25, 2666.
59. B. D. Cullity, S. R. Stock, Elements of X-Ray Diffraction, 3rd ed., Prentice Hall, Upper Saddle River, NJ 2001.
60. W. L. Jorgensen, D. S. Maxwell, J. Tirado-Rives, J. Am. Chem. Soc. 1996, 118, 11225.
61. W. G. Hoover, Phys. Rev. A 1985, 31, 1695.
62. M. Parrinello, A. Rahman, J. Appl. Phys. 1981, 52, 7182.