Additive-assisted control over phase-separated nanostructures by manipulating alkylthienyl position at donor backbone for solution-processed, non-fullerene, all-small-molecule solar cells

ACS Applied Materials and Interfaces

Volumn 6, Issue 6, 2014, Pages 3853-3862

  Huang, Jianhua ^a   Wang, Xue ^a,b   Zhang, Xin ^a   Niu, Zhixiao ^a,b   Lu, Zhenhuan ^a   Jiang, Bo ^a   Sun, Yuxi ^b   Zhan, Chuanlang ^a   Yao, Jiannian ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b QUFU NORMAL UNIVERSITY   (China)

Author keywords

alkylthienyl position; all small molecule solar cell; donor backbone; non fullerene; phase separated nanostructure; solution processed

Indexed keywords

FULLERENES; SOLAR CELLS;

ALKYLTHIENYL POSITION; DIKETOPYRROLOPYRROLES; DONOR BACKBONE; NON-FULLERENE; PERYLENEDIIMIDES; POWER CONVERSION EFFICIENCIES; SMALL MOLECULES; SOLUTION-PROCESSED;

MOLECULES;

EID: 84896992237     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am406050j     Document Type: Article

References (62)

1. Chen, J. W.; Cao, Y. Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices Acc. Chem. Res. 2009, 42, 1709-1718
2. Cheng, Y. J.; Yang, S. H.; Hsu, C. S. Synthesis of Conjugated Polymers for Organic Solar Cell Applications Chem. Rev. 2009, 109, 5868-5923
3. Yip, H.-L.; Jen, A. K. Y. Recent Advances in Solution-Processed Interfacial Materials for Efficient and Stable Polymer Solar Cells Energy Environ. Sci. 2012, 5, 5994-6011
4. Zhou, H.; Yang, L.; You, W. Rational Design of High Performance Conjugated Polymers for Organic Solar Cells Macromolecules 2012, 45, 607-632
5. Zhou, J.; Wan, X.; Liu, Y.; Zuo, Y.; Li, Z.; He, G.; Long, G.; Ni, W.; Li, C.; Su, X.; Chen, Y. Small Molecules Based on Benzo[1,2-b:4,5-b′] dithiophene Unit for High-Performance Solution-Processed Organic Solar Cells J. Am. Chem. Soc. 2012, 134, 16345-16351
6. Zhou, J.; Zuo, Y.; Wan, X.; Long, G.; Zhang, Q.; Ni, W.; Liu, Y.; Li, Z.; He, G.; Li, C.; Kan, B.; Li, M.; Chen, Y. Solution-Processed and High-Performance Organic Solar Cells Using Small Molecules with a Benzodithiophene Unit J. Am. Chem. Soc. 2013, 135, 8484-8487
7. Lin, Y.; Li, Y.; Zhan, X. Small Molecule Semiconductors for High-Efficiency Organic Photovoltaics Chem. Soc. Rev. 2012, 41, 4245-4272
8. Demeter, D.; Jeux, V.; Leriche, P.; Blanchard, P.; Olivier, Y.; Cornil, J.; Po, R.; Roncali, J. Tuning of the Photovoltaic Parameters of Molecular Donors by Covalent Bridging Adv. Funct. Mater. 2013, 23, 4854-4861
9. Dutta, P.; Yang, W.; Eom, S. H.; Lee, W. H.; Kang, I. N.; Lee, S. H. Development of Naphtho[1,2- b:5,6- b ′]dithiophene Based Novel Small Molecules for Efficient Bulk-Heterojunction Organic Solar Cells Chem. Commun. 2012, 48, 573-575
10. Hou, Q.; Chen, Y.; Zhen, H.; Ma, Z.; Hong, W.; Shi, G.; Zhang, F. A Triphenylamine-Based Four-Armed Molecule for Solution-Processed Organic Solar Cells with High Photo-Voltage J. Mater. Chem. A 2013, 1, 4937-4940
11. Huang, J.; Jia, H.; Li, L.; Lu, Z.; Zhang, W.; He, W.; Jiang, B.; Tang, A.; Tan, Z.; Zhan, C.; Li, Y.; Yao, J. Fine-Tuning Device Performances of Small Molecule Solar Cells via the More Polarized DPP-Attached Donor Units Phys. Chem. Chem. Phys. 2012, 14, 14238-14242
12. Kang, S. J.; Ahn, S.; Kim, J. B.; Schenck, C.; Hiszpanski, A. M.; Oh, S.; Schiros, T.; Loo, Y. L.; Nuckolls, C. Using Self-Organization to Control Morphology in Molecular Photovoltaics J. Am. Chem. Soc. 2013, 135, 2207-2212
13. Kim, J.; Ko, H. M.; Cho, N.; Paek, S.; Lee, J. K.; Ko, J. Efficient Small Molecule Organic Semiconductor Containing Bis-dimethylfluorenyl Amino Benzo[ b ]thiophene for High Open Circuit Voltage in High Efficiency Solution Processed Organic Solar Cell RSC Adv. 2012, 2, 2692-2695
14. Lam, S. L.; Liu, X.; Zhao, F.; Lee, C. L.; Kwan, W. L. Manipulating Open-Circuit Voltage in an Organic Photovoltaic Device via a Phenylalkyl Side Chain Chem. Commun. 2013, 49, 4543-4545
15. Lee, O. P.; Yiu, A. T.; Beaujuge, P. M.; Woo, C. H.; Holcombe, T. W.; Millstone, J. E.; Douglas, J. D.; Chen, M. S.; Frechet, J. M. Efficient Small Molecule Bulk Heterojunction Solar Cells with High Fill Factors via Pyrene-Directed Molecular Self-Assembly Adv. Mater. 2011, 23, 5359-5363
16. Li, P.; Tong, H.; Ding, J.; Xie, Z.; Wang, L. Small Molecules Based on 2,7-Carbazole for Efficient Solution-Processed Organic Solar Cells J. Mater. Chem. A 2013, 1, 8805-8812
17. Li, Z.; Dong, Q.; Li, Y.; Xu, B.; Deng, M.; Pei, J.; Zhang, J.; Chen, F.; Wen, S.; Gao, Y.; Tian, W. Design and Synthesis of Solution Processable Small Molecules Towards High Photovoltaic Performance J. Mater. Chem. 2011, 21, 2159-2166
18. Liu, J.; Sun, Y.; Moonsin, P.; Kuik, M.; Proctor, C. M.; Lin, J.; Hsu, B. B.; Promarak, V.; Heeger, A. J.; Nguyen, T. Q. Tri-Diketopyrrolopyrrole Molecular Donor Materials for High-Performance Solution-Processed Bulk Heterojunction Solar Cells Adv. Mater. 2013, 25, 5898-5903
19. Liu, Y.; Yang, Y. M.; Chen, C. C.; Chen, Q.; Dou, L.; Hong, Z.; Li, G.; Yang, Y. Solution-Processed Small Molecules Using Different Electron Linkers for High-Performance Solar Cells Adv. Mater. 2013, 25, 4657-4662
20. Pan, J. Y.; Zuo, L. J.; Hu, X. L.; Fu, W. F.; Chen, M. R.; Fu, L.; Gu, X.; Shi, H. Q.; Shi, M. M.; Li, H. Y.; Chen, H. Z. Star-Shaped D-A Small Molecules Based on Diketopyrrolopyrrole and Triphenylamine for Efficient Solution-Processed Organic Solar Cells ACS Appl. Mater. Interfaces 2013, 5, 972-980
21. Ripaud, E.; Rousseau, T.; Leriche, P.; Roncali, J. Unsymmetrical Triphenylamine-Oligothiophene Hybrid Conjugated Systems as Donor Materials for High-Voltage Solution-Processed Organic Solar Cells Adv. Energy Mater. 2011, 1, 540-545
22. Schulz, G. L.; Mastalerz, M.; Ma, C.-Q.; Wienk, M.; Janssen, R.; Bäuerle, P. Synthesis and Photovoltaic Performance of Pyrazinoquinoxaline Containing Conjugated Thiophene-Based Dendrimers and Polymers Macromolecules 2013, 46, 2141-2151
23. Shen, S.; Jiang, P.; He, C.; Zhang, J.; Shen, P.; Zhang, Y.; Yi, Y.; Zhang, Z.; Li, Z.; Li, Y. Solution-Processable Organic Molecule Photovoltaic Materials with Bithienyl-benzodithiophene Central Unit and Indenedione End Groups Chem. Mater. 2013, 25, 2274-2281
24. Shin, W.; Yasuda, T.; Watanabe, G.; Yang, Y. S.; Adachi, C. Self-Organizing Mesomorphic Diketopyrrolopyrrole Derivatives for Efficient Solution-Processed Organic Solar Cells Chem. Mater. 2013, 25, 2549-2556
25. Tamayo, A. B.; Walker, B.; Nguyen, T. Q. A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells J. Phys. Chem. C 2008, 112, 11545-11551
26. Wang, H.-Y.; Gao, J.; Gu, L.-J.; Wan, J.-H.; Wei, W.; Liu, F. Structural Modification of Thieno[3,4-c]pyrrole-4,6-dione: Structure-Property Relationships and Application in Solution-Processed Small-Molecule Organic Solar Cells J. Mater. Chem. A 2013, 1, 5875-5885
27. Ye, D.; Li, X.; Yan, L.; Zhang, W.; Hu, Z.; Liang, Y.; Fang, J.; Wong, W.-Y.; Wang, X. Dithienosilole-Bridged Small Molecules with Different Alkyl Group Substituents for Organic Solar Cells Exhibiting High Open-Circuit Voltage J. Mater. Chem. A 2013, 1, 7622-7629
28. Zeng, S.; Yin, L.; Ji, C.; Jiang, X.; Li, K.; Li, Y.; Wang, Y. D-π-A-π-D Type Benzothiadiazole-Triphenylamine Based Small Molecules Containing Cyano on the π-Bridge for Solution-Processed Organic Solar Cells with High Open-Circuit Voltage Chem. Commun. 2012, 48, 10627-10629
29. Kyaw, A. K. K.; Wang, D. H.; Gupta, V.; Leong, W. L.; Ke, L.; Bazan, G. C.; Heeger, A. J. Intensity Dependence of Current-Voltage Characteristics and Recombination in High-Efficiency Solution-Processed Small-Molecule Solar Cells ACS Nano 2013, 7, 4569-4577
30. 60 Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells J. Am. Chem. Soc. 2010, 132, 1377-1382
31. Anctil, A.; Babbitt, C. W.; Raffaelle, R. P.; Landi, B. J. Material and Energy Intensity of Fullerene Production Environ. Sci. Technol. 2011, 45, 2353-2359
32. Sonar, P.; Fong Lim, J. P.; Chan, K. L. Organic Non-Fullerene Acceptors for Organic Photovoltaics Energy Environ. Sci. 2011, 4, 1558-1574
33. Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Rylene and Related Diimides for Organic Electronics Adv. Mater. 2011, 23, 268-284
34. Moore, J. R.; Albert-Seifried, S.; Rao, A.; Massip, S.; Watts, B.; Morgan, D. J.; Friend, R. H.; McNeill, C. R.; Sirringhaus, H. Polymer Blend Solar Cells Based on a High-Mobility Naphthalenediimide-Based Polymer Acceptor: Device Physics, Photophysics and Morphology Adv. Energy Mater. 2011, 1, 230-240
35. Zhou, E.; Cong, J.; Wei, Q.; Tajima, K.; Yang, C.; Hashimoto, K. All-Polymer Solar Cells from Perylene Diimide Based Copolymers: Material Design and Phase Separation Control Angew. Chem., Int. Ed. 2011, 50, 2799-2803
36. Zhou, Y.; Yan, Q.; Zheng, Y.; Wang, J.; Zhao, D.; Pei, J. New Polymer Acceptors for Organic Solar Cells: the Effect of Regio-Regularity and Device Configuration J. Mater. Chem. A 2013, 1, 6609-6613
37. Ahmed, E.; Ren, G.; Kim, F. S.; Hollenbeck, E. C.; Jenekhe, S. A. Design of New Electron Acceptor Materials for Organic Photovoltaics: Synthesis, Electron Transport, Photophysics, and Photovoltaic Properties of Oligothiophene-Functionalized Naphthalene Diimides Chem. Mater. 2011, 23, 4563-4577
38. Bloking, J. T.; Han, X.; Higgs, A. T.; Kastrop, J. P.; Pandey, L.; Norton, J. E.; Risko, C.; Chen, C. E.; Brédas, J.-L.; McGehee, M. D.; Sellinger, A. Solution-Processed Organic Solar Cells with Power Conversion Efficiencies of 2.5% using Benzothiadiazole/Imide-Based Acceptors Chem. Mater. 2011, 23, 5484-5490
39. Brunetti, F. G.; Gong, X.; Tong, M.; Heeger, A. J.; Wudl, F. Strain and Hückel Aromaticity: Driving Forces for a Promising New Generation of Electron Acceptors in Organic Electronics Angew. Chem., Int. Ed. 2010, 49, 532-536
40. Howard, I. A.; Laquai, F.; Keivanidis, P. E.; Friend, R. H.; Greenham, N. C. Perylene Tetracarboxydiimide as an Electron Acceptor in Organic Solar Cells: A Study of Charge Generation and Recombination J. Phys. Chem. C 2009, 113, 21225-21232
41. Jiang, B.; Zhang, X.; Zhan, C.; Lu, Z.; Huang, J.; Ding, X.; He, S.; Yao, J. Benzodithiophene Bridged Dimeric Perylene Diimide Amphiphiles as Efficient Solution-Processed Non-Fullerene Small Molecules Polym. Chem. 2013, 4, 4631-4638
42. Kamm, V.; Battagliarin, G.; Howard, I. A.; Pisula, W.; Mavrinskiy, A.; Li, C.; Mullen, K.; Laquai, F. Polythiophene:Perylene Diimide Solar Cells-the Impact of Alkyl-Substitution on the Photovoltaic Performance Adv. Energy Mater. 2011, 1, 297-302
43. Li, H.; Kim, F. S.; Ren, G.; Hollenbeck, E. C.; Subramaniyan, S.; Jenekhe, S. A. Tetraazabenzodifluoranthene Diimides: Building Blocks for Solution-Processable n-Type Organic Semiconductors Angew. Chem., Int. Ed. 2013, 52, 5513-5517
44. Lu, Z.; Zhang, X.; Zhan, C.; Jiang, B.; Chen, L.; Yao, J. Impact of Molecular Solvophobicity vs. Solvophilicity on Device Performances of Dimeric Perylene Diimide Based Solution-Processed Non-Fullerene Organic Solar Cells Phys. Chem. Chem. Phys. 2013, 15, 11375-11385
45. Schwenn, P. E.; Gui, K.; Nardes, A. M.; Krueger, K. B.; Lee, K. H.; Mutkins, K.; Rubinstein-Dunlop, H.; Shaw, P. E.; Kopidakis, N.; Burn, P. L.; Meredith, P. A Small Molecule Non-fullerene Electron Acceptor for Organic Solar Cells Adv. Energy Mater. 2011, 1, 73-81
46. Zhou, T.; Jia, T.; Kang, B.; Li, F.; Fahlman, M.; Wang, Y. Nitrile-Substituted QA Derivatives: New Acceptor Materials for Solution-Processable Organic Bulk Heterojunction Solar Cells Adv. Energy Mater. 2011, 1, 431-439
47. Zhou, Y.; Dai, Y.; Zheng, Y.; Wang, X.; Wang, J.; Pei, J. Non-Fullerene Acceptors Containing Fluoranthene-Fused Imides for Solution-Processed Inverted Organic Solar Cells Chem. Commun. 2013, 49, 5802-5804
48. Kamm, V.; Battagliarin, G.; Howard, I. A.; Pisula, W.; Mavrinskiy, A.; Li, C.; Müllen, K.; Laquai, F. Polythiophene: Perylene Diimide Solar Cells-the Impact of Alkyl-Substitution on the Photovoltaic Performance Adv. Energy Mater. 2011, 1, 297-302
49. Rajaram, S.; Shivanna, R.; Kandappa, S. K.; Narayan, K. S. Nonplanar Perylene Diimides as Potential Alternatives to Fullerenes in Organic Solar Cells J. Phys. Chem. Lett. 2012, 3, 2405-2408
50. Zhang, X.; Lu, Z.; Ye, L.; Zhan, C.; Hou, J.; Zhang, S.; Jiang, B.; Zhao, Y.; Huang, J.; Zhang, S.; Liu, Y.; Shi, Q.; Liu, Y.; Yao, J. A Potential Perylene Diimide Dimer-Based Acceptor Material for Highly Efficient Solution-Processed Non-Fullerene Organic Solar Cells with 4.03% Efficiency Adv. Mater. 2013, 25, 5791-5797
51. Mikroyannidis, J. A.; Suresh, P.; Sharma, G. D. Synthesis of A Perylene Bisimide with Acetonaphthopyrazine Dicarbonitrile Terminal Moieties for Photovoltaic Applications Synth. Met. 2010, 160, 932-938
52. Sharenko, A.; Proctor, C. M.; van der Poll, T. S.; Henson, Z. B.; Nguyen, T. Q.; Bazan, G. C. A High-Performing Solution-Processed Small Molecule: Perylene Diimide Bulk Heterojunction Solar Cell Adv. Mater. 2013, 25, 4403-4406
53. Beaujuge, P. M.; Frechet, J. M. Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications J. Am. Chem. Soc. 2011, 133, 20009-20029
54. Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated Polymer-Based Organic Solar Cells Chem. Rev. 2007, 107, 1324-1338
55. Huang, J.; Zhan, C.; Zhang, X.; Zhao, Y.; Lu, Z.; Jia, H.; Jiang, B.; Ye, J.; Zhang, S.; Tang, A.; Liu, Y.; Pei, Q.; Yao, J. Solution-Processed DPP-Based Small Molecule that Gives High Photovoltaic Efficiency with Judicious Device Optimization ACS Appl. Mater. Interfaces 2013, 5, 2033-2039
56. 2-Fluorene Based D-A Copolymers Polym. Chem. 2012, 3, 2170-2177
57. Huo, L.; Zhang, S.; Guo, X.; Xu, F.; Li, Y.; Hou, J. Replacing Alkoxy Groups with Alkylthienyl Groups: A Feasible Approach to Improve the Properties of Photovoltaic Polymers Angew. Chem., Int. Ed. 2011, 50, 9697-9702
58. Takacs, C. J.; Sun, Y.; Welch, G. C.; Perez, L. A.; Liu, X.; Wen, W.; Bazan, G. C.; Heeger, A. J. Solar Cell Efficiency, Self-Assembly, and Dipole-Dipole Interactions of Isomorphic Narrow-Band-Gap Molecules J. Am. Chem. Soc. 2012, 134, 16597-16606
59. Huang, J.; Wang, X.; Zhan, C.; Zhao, Y.; Sun, Y.; Pei, Q.; Liu, Y.; Yao, J. Wide Band Gap Copolymers Based on Phthalimide: Synthesis, Characterization, and Photovoltaic Properties with 3.70% Efficiency Polym. Chem. 2013, 4, 2174-2180
60. Langford, J. I.; Wilson, A. J. C. Scherrer after Sixty Years: A Survey and Some New Results in the Determination of Crystallite Size J. Appl. Crystallogr. 1978, 11, 102-113
61. Nunzi, J. M. Organic Photovoltaic Materials and Devices C. R. Phys. 2002, 3, 523-542
62. Loser, S.; Bruns, C. J.; Miyauchi, H.; Ortiz, R. P.; Facchetti, A.; Stupp, S. I.; Marks, T. J. A Naphthodithiophene-Diketopyrrolopyrrole Donor Molecule for Efficient Solution-Processed Solar Cells J. Am. Chem. Soc. 2011, 133, 8142-8145