All-polymer solar cells based on PTACs/P3HT blends with large open-circuit voltage

Dyes and Pigments

Volumn 99, Issue 3, 2013, Pages 1065-1071

  Kang, Hongwei ^a,b   Zheng, Yu Qing ^c   Jiang, Wei ^a   Xiao, Chengyi ^a,b   Wang, Jie Yu ^c   Pei, Jian ^c   Wang, Zhaohui ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c PEKING UNIVERSITY   (China)

Author keywords

All polymer solar cells; Blending; D A conjugated polymers; Electron acceptor; Large open circuit voltage; Perylene esters

Indexed keywords

ALL-POLYMER SOLAR CELLS; ELECTRON ACCEPTOR; ELECTRON-DEFICIENT; LUMO ENERGY LEVELS; PERYLENES; POWER CONVERSION EFFICIENCIES; STILLE COUPLING; THIOPHENE DERIVATIVES;

BLENDING; ELECTRON TRANSITIONS; OPEN CIRCUIT VOLTAGE; POLYCYCLIC AROMATIC HYDROCARBONS; SOLAR CELLS;

POLYMER BLENDS;

EID: 84883878094     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.08.017     Document Type: Article

References (58)

1. G. Li, V. Shrotriya, J. Huang, Y. Yao, T. Moriarty, and K. Emery High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends Nat Mater 4 2005 864 868
2. L. Huo, S. Zhang, X. Guo, F. Xu, Y. Li, and J. Hou Replacing alkoxy groups with alkylthienyl groups: a feasible approach to improve the properties of photovoltaic polymers Angew Chem Int Ed 50 2011 9697 9702
3. X. Gong Toward high performance inverted polymer solar cells Polymer 53 2012 5437 5448
4. Z. Tan, W. Zhang, Z. Zhang, D. Qian, Y. Huang, and J. Hou High-performance inverted polymer solar cells with solution-processed titanium chelate as electron-collecting layer on ITO electrode Adv Mater 24 2012 1476 1481
5. X. Li, W.C.H. Choy, L. Huo, F. Xie, W.E.I. Sha, and B. Ding Dual plasmonic nanostructures for high performance inverted organic solar cells Adv Mater 24 2012 3046 3052
6. G. Li, R. Zhu, and Y. Yang Polymer solar cells Nat Photonics 6 2012 153 161
7. T.-Y. Chu, J. Lu, S. Beaupré, Y. Zhang, J.-R. Pouliot, and S. Wakim 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
8. Y. Liang, Z. Xu, J. Xia, S.T. Tsai, Y. Wu, and G. Li For the bright future-bulk heterojunction polymer solar cells with power conversion efficiency of 7.4% Adv Mater 22 2010 E135 E138
9. X. Zhan, Z. Tan, B. Domercq, Z. An, X. Zhang, and S. Barlow A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells J Am Chem Soc 129 2007 7246 7247 (Pubitemid 46980790)
10. P. Sonar, J.P.F. Lim, and K.L. Chan Organic non-fullerene acceptors for organic photovoltaics Energy Environ Sci 4 2011 1558 1574
11. J.E. Anthony Small-molecule, non-fullerene acceptors for polymer solar cells Chem Mater 23 2011 583 590
12. G. Ren, E. Ahmed, and S.A. Jenekhe Non-fullerene acceptor-based bulk heterojunction polymer solar cells: engineering the nanomorphology via processing additives Adv Energy Mater 1 2011 946 953
13. M. Schubert, D. Dolfen, J. Frisch, S. Roland, R. Steyrleuthner, and B. Stiller Influence of aggregation on the performance of all-polymer solar cells containing low-bandgap naphthalenediimide copolymers Adv Energy Mater 2 2012 369 380
14. E. Zhou, J. Cong, Q. Wei, K. Tajima, C. Yang, and K. Hashimoto All-polymer solar cells from perylene diimide based copolymers: material design and phase separation control Angew Chem Int Ed 50 2011 2799 2803
15. C.R. McNeill Morphology of all-polymer solar cells Energy Environ Sci 5 2012 5653 5667
16. Z. Tan, E. Zhou, X. Zhan, X. Wang, Y. Li, and S. Barlow Efficient all-polymer solar cells based on blend of tris(thienylenevinylene)- substituted polythiophene and poly[perylene diimide-altbis(dithienothiophene)] Appl Phys Lett 93 2008 073309
17. J. Hou, H. Chen, S. Zhang, G. Li, and Y. Yang Synthesis, characterization, and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole J Am Chem Soc 130 2008 16144 16145
18. M.C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, and A.J. Heeger Design rules for donors in bulk-heterojunction solar cells-towards 10% energy-conversion efficiency Adv Mater 18 2006 789 794
19. Roncal J. Macromol Molecular engineering of the band gap of p-conjugated systems: facing technological applications Rapid Commun 28 2007 1761 1775
20. C. Li, and H. Wonneberger Perylene imides for organic photovoltaics: yesterday, today, and tomorrow Adv Mater 24 2012 613 636
21. W.S. Shin, H.-H. Jeong, M.-K. Kim, S.-H. Jin, M.-R. Kim, and J.-K. Lee Effects of functional groups at perylene diimide derivatives on organic photovoltaic device application J Mater Chem 16 2006 384 390 (Pubitemid 43324456)
22. H. Choi, S. Paek, J. Song, C. Kim, N. Cho, and J. Ko Synthesis of annulated thiophene perylene bisimide analogues: their applications to bulk heterojunction organic solar cells Chem Commun 47 2011 5509 5511
23. E. Zhou, K. Tajima, C. Yang, and K. Hashimoto Band gap and molecular energy level control of perylene diimide-based donor-acceptor copolymers for all-polymer solar cells J Mater Chem 20 2010 2362 2368
24. R. Schmidt, M.M. Ling, J.H. Oh, M. Winkler, M. Könemann, and Z. Bao Core-fluorinated perylene bisimide dyes: air stable n-channel organic semiconductors for thin film transistors with exceptionally high on-to-off current ratios Adv Mater 19 2007 3692 3695 (Pubitemid 350134627)
25. R. Schmidt, J.H. Oh, Y.-S. Sun, M. Deppisch, A.-M. Krause, and K. Radacki High-performance air-stable n-channel organic thin film transistors based on halogenated perylene bisimide semiconductors J Am Chem Soc 131 2009 6215 6228
26. -1 J Am Chem Soc 135 2013 2338 2349
27. J.E. Anthony, A. Facchetti, M. Heeney, S.R. Marder, and X. Zhan N-type organic semiconductors in organic electronics Adv Mater 22 2010 3876 3892
28. A. Lv, S.R. Puniredd, J. Zhang, Z. Li, H. Zhu, and W. Jiang High mobility, air stable, organic single crystal transistors of an n-type diperylene bisimide Adv Mater 24 2012 2626 2630
29. M. Gsänger, J.H. Oh, M. Könemann, H.W. Höffken, A.M. Krause, and Z. Bao A crystal-engineered hydrogen-bonded octachloroperylene diimide with a twisted core: an n-channel organic semiconductor Angew Chem Int Ed 49 2010 740 743
30. L. Fan, W. Zhu, J. Li, and H. Tian Novel red-light emitting metal complex based on asymmetric perylene bisimide and 8-hydroxyquinoline dyads Synth Met 145 2004 203 210
31. C. Huang, S. Barlow, and S.R. Marder Perylene-3, 4, 9, 10-tetracarboxylic acid diimides: synthesis, physical properties, and use in organic electronics J Org Chem 76 2011 2386 2407
32. H. Qian, Z. Wang, W. Yue, and D. Zhu Exceptional coupling of tetrachloroperylene bisimide: combination of Ullmann reaction and C-H transformation J Am Chem Soc 129 2007 10664 10665 (Pubitemid 350067470)
33. H. Qian, F. Negri, C. Wang, and Z. Wang Fully conjugated tri(perylene bisimides): an approach to the construction of n-type graphene nanoribbons J Am Chem Soc 130 2008 17970 17976
34. Y. Zhen, C. Wang, and Z. Wang Tetrachloro-tetra(perylene bisimides): an approach towards N-type graphene nanoribbons Chem Commun 46 2010 1926 1928
35. H. Qian, C. Liu, Z. Wang, and D. Zhu S-heterocyclic annelated perylene bisimide: synthesis and co-crystal with pyrene Chem Commun 2006 4587 4589 (Pubitemid 44684549)
36. Y. Zhen, H. Qian, J. Xiang, J. Qu, and Z. Wang Highly regiospecific synthetic approach to monobay-functionalized perylene bisimide and di(perylene bisimide) Org Lett 11 2009 3084 3087
37. W. Jiang, Y. Li, W. Yue, Y. Zhen, J. Qu, and Z. Wang One-pot facile synthesis of pyridyl annelated perylene bisimides Org Lett 12 2010 228 231
38. Y. Zhen, W. Yue, Y. Li, W. Jiang, S. Di Motta, and E. Di Donato Chiral nanoribbons based on doubly-linked oligo-perylene bisimides Chem Commun 46 2010 6078 6080
39. F. Würthner Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures Chem Commun 2004 1564 1579 (Pubitemid 39089105)
40. W. Jiang, C. Xiao, L. Hao, Z. Wang, H. Ceymann, and C. Lambert Localization/delocalization of charges in bay-linked perylene bisimides Chem Eur J 18 2012 6764 6775
41. G. Golubkov, H. Weissman, E. Shirman, S.G. Wolf, I. Pinkas, and B. Rybtchinski Economical design in noncovalent nanoscale synthesis: diverse photofunctional nanostructures based on a single covalent building block Angew Chem Int Ed 48 2009 926 930
42. C. Xue, R. Sun, R. Annab, D. Abadi, and S. Jin Perylene monoanhydride diester: a versatile intermediate for the synthesis of unsymmetrically substituted perylene tetracarboxylic derivatives Tetrahedron Lett 50 2009 853 856
43. X. Mo, M.-M. Shi, J.-C. Huang, M. Wang, and H.-Z. Chen Synthesis, aggregation and photoconductive properties of alkoxycarbonyl substituted perylenes Dyes Pigm 76 2008 236 242 (Pubitemid 47034796)
44. A. Arnaud, J. Belleney, F. Boué, L. Bouteiller, G. Carrot, and V. Wintgens Aqueous supramolecular polymer formed from an amphiphilic perylene derivative Angew Chem Int Ed 43 2004 1718 1721 (Pubitemid 39257873)
45. Z. Yuan, Y. Xiao, and X. Qian A design concept of planar conjugated ladder oligomers of perylene bisimides and efficient synthetic strategy via regioselective photocyclization Chem Commun 46 2010 2772 2774
46. Y. Li, C. Wang, C. Li, S.D. Motta, F. Negri, and Z. Wang Synthesis and properties of ethylene-annulated di(perylene diimides) Org Lett 14 2012 5278 5281
47. S. Lu, J. Niu, W. Li, J. Mao, and J. Jiang Photophysics and morphology investigation based on perylenetetracarboxylate/polymer photovoltaic devices Solar Energy Mater Solar Cells 91 2007 261 265 (Pubitemid 44880114)
48. S. Alibert-Fouet, I. Seguy, J.-F. Bobo, P. Destruel, and H. Bock Liquid-crystalline and electron-deficient coronene oligocarboxylic esters and imides by twofold benzogenic Diels-Alder reactions on perylenes Chem Eur J 13 2007 1746 1753 (Pubitemid 46941930)
49. J. Kelber, H. Bock, O. Thiebaut, E. Grelet, and H. Langhals Room-temperature columnar liquid-crystalline perylene imido-diesters by a homogeneous one-pot imidification-esterification of perylene-3,4,9,10- tetracarboxylic dianhydride Eur J Org Chem 4 2011 707 712
50. Z. Yuan, Y. Xiao, Z. Li, and X. Qian Efficient synthesis of regioisomerically pure bis(trifluoromethyl)-substituted 3,4,9,10-perylene tetracarboxylic bis(benzimidazole) Org Lett 11 2009 2808 2811
51. J. Hou, H.-Y. Chen, S. Zhang, R.I. Chen, Y. Yang, and Y. Wu Synthesis of a low band gap polymer and its application in highly efficient polymer solar cells J Am Chem Soc 131 2009 15586 15587
52. Y.-Y. Cheng, S.-H. Yang, and C.-S. Hsu Synthesis of conjugated polymers for organic solar cell applications Chem Rev 109 2009 5868 5923
53. Cao Y, Lei T, Yuan J, Wang J.-Y, Pei, J. Dithiazolyl-benzothiadiazole- containing polymer acceptors: synthesis, characterization, and all-polymer solar cells. Polym Chem. doi: 10.1039/c3py00112a.
54. J. Clark, J.-F. Chang, F.C. Spano, R.H. Friend, and C. Silva Determining exciton bandwidth and film microstructure in polythiophene films using linear absorption spectroscopy Appl Phys Lett 94 2009 163306
55. J. Huang, Y. Zhao, W. He, H. Jia, Z. Lu, and B. Jiang Effects of structure-manipulated molecular stacking on solid-state optical properties and device performances Polym Chem 3 2012 2832 2841
56. E. Ahmed, S. Subramaniyan, F.S. Kim, H. Xin, and S.A. Jenekhe Benzobisthiazole-based donor acceptor copolymer semiconductors for photovoltaic cells and highly stable field-effect transistors Macromolecules 44 2011 7207 7219
57. J. Kim, Han A-R, J.H. Seo, J.H. Oh, and C. Yang β-Alkyl substituted dithieno[2,3-d;2',3'-d']benzo[1,2-b;4,5-b']dithiophene semiconducting materials andtheir application to solution-processed organic transistors Chem Mater 24 2012 3464 3472
58. Y.-C. Huang, C.-S. Tsao, C.-M. Chuang, C.-H. Lee, F.-H. Hsu, and H.-C. Cha Small- and wide-angle X-ray scattering characterization of bulk heterojunction polymer solar cells with different fullerene derivatives J Phys Chem C 116 2012 10238 10244