Evaluation of heterocycle-modified pentathiophene-based molecular donor materials for solar cells

ACS Applied Materials and Interfaces

Volumn 6, Issue 8, 2014, Pages 5798-5809

  Yu, Qing Cai ^a   Fu, Wei Fei ^b   Wan, Jun Hua ^a,c   Wu, Xiao Feng ^a   Shi, Min Min ^b   Chen, Hong Zheng ^b  

^a HANGZHOU NORMAL UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c FUDAN UNIVERSITY   (China)

Author keywords

cycle extension; diketopyrrolopyrrole; heterocycle modified pentathiophene; organic solar cell; solution processable small molecule; structure property relationship

Indexed keywords

AROMATIC COMPOUNDS; ATOMS; CRYSTALLIZATION; ELECTRIC PROPERTIES; ELECTRONIC STRUCTURE; MOLECULES; NITROGEN; SOLAR CELLS; SULFUR; SYNTHESIS (CHEMICAL);

CYCLE EXTENSION; DIKETOPYRROLOPYRROLES; ORGANIC SOLAR CELL; PENTATHIOPHENE; SMALL MOLECULES; STRUCTURE PROPERTY RELATIONSHIPS;

INTERNATIONAL TRADE;

EID: 84899575570     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am5006223     Document Type: Article

References (68)

1. Roncali, J. Molecular Bulk Heterojunctions: an Emerging Approach to Organic Solar Cells Acc. Chem. Res. 2009, 42, 1719-1730
2. Walker, B.; Kim, C.; Nguyen, T.-Q. Small Molecule Solution-Processed Bulk Heterojunction Solar Cells Chem. Mater. 2011, 23, 470-482
3. Chen, Y. S.; Wan, X. J.; Long, G. High Performance Photovoltaic Applications Using Solution-Processed Small Molecules Acc. Chem. Res. 2013, 46, 2645-2655
4. Lin, Y.; Li, Y. F.; Zhan, X. W. Small Molecule Semiconductors for High-Efficiency Organic Photovoltaics Chem. Soc. Rev. 2012, 41, 4245-4272
5. Li, Y.; Guo, Q.; Li, Z.; Pei, J.; Tian, W.J Solution Processable D-A Small Molecules for Bulk-Heterojunction Solar Cells Energy Environ. Sci. 2010, 3, 1427-1436
6. Mishra, A.; Bauerle, P. Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology Angew. Chem., Int. Ed. 2012, 51, 2020-2067
7. Zhou, J.; Zuo, Y.; Wan, X. J.; Long, G.; Zhang, Q.; Ni, W.; Liu, Y.; Li, Z.; He, G.; Li, C.; Kan, B.; Li, M.; Chen, Y. S. Solution-Processed and High-Performance Organic Solar Cells Using Small Molecules with a Benzodithiophene Unit J. Am. Chem. Soc. 2013, 135, 8484-8487
8. Kyaw, A. K.; Wang, D. H.; Gupta, V.; Zhang, J.; Chand, S.; Bazan, G. C.; Heeger, A. J. Efficient Solution-Processed Small-Molecule Solar Cells with Inverted Structure Adv. Mater. 2013, 25, 2397-2402
9. Zhou, J.; Wan, X. J.; Liu, Y.; Zuo, Y.; Li, Z.; He, G.; Long, G.; Ni, W.; Li, C.; Su, X.; Chen, Y. S. 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
10. Liu, Y.; Chen, C. C.; Hong, Z.; Gao, J.; Michael Yang, Y.; Zhou, H.; Dou, L.; Li, G.; Yang, Y. Solution-Processed Small-Molecule Solar Cells: Breaking the 10% Power Conversion Efficiency Sci. Rep. 2013, 3, 3356
11. 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
12. Li, W. W.; Kelchtermances, M.; Wienki, M. M.; Janssen, R. A. J. Effect of Structure on The Solubility and Photovoltaic Properties of Bis- Diketopyrrolopyrrole Molecules J. Mater. Chem. A 2013, 1, 15150-15157
13. Yang, X.; Veenstra, S. C.; Verhees, W.; Wienk, J. H.; Janssen, M. M.; Kroon, R. A. J.; Michels, J. M.; Loos, M. A. J.; Nanoscale, J. Morphology of High-Performance Polymer Solar Cells Nano Lett. 2005, 5, 579-583
14. Zhou, H.; Yang, L.; You, W. Rational Design of High Performance Conjugated Polymers for Organic Solar Cells Macromolecules 2012, 45, 607-632
15. McCulloch, I.; Ashraf, R. S.; Biniek, L.; Bronstein, H.; Combe, C.; Donaghey, J. E.; James, D. I.; Nielsen, C. B.; Schroeder, B. C.; Zhang, W. Design of Semiconducting Indacenodithiophene Polymers for High Performance Transistors and Solar Cells Acc. Chem. Res. 2012, 45, 714-722
16. Facchetti, A. π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications Chem. Mater. 2011, 23, 733-758
17. Zhou, J.; Wan, X. J.; Liu, Y.; Long, G.; Wang, F.; Li, Z.; Zuo, Y.; Li, C.; Chen, Y. S. A Planar Small Molecule with Dithienosilole Core for High Efficiency Solution-Processed Organic Photovoltaic Cells Chem. Mater. 2011, 23, 4666-4668
18. Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Solution-Processed Small-Molecule Solar Cells with 6.7% Efficiency Nat. Mater. 2011, 11, 44-48
19. 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. (Camb.) 2012, 48, 573-575
20. Patra, D.; Huang, T. Y.; Chiang, C. C.; Maturana, R. O.; Pao, C. W.; Ho, K. C.; Wei, K. H.; Chu, C. W. 2-Alkyl-5-thienyl-substituted Benzo[1,2- b:4,5- b ′]dithiophene-Based Donor Molecules for Solution-Processed Organic Solar Cells ACS Appl. Mater. Interfaces 2013, 5, 9494-9500
21. He, M.; Li, J.; Sorensen, M. L.; Zhang, F.; Hancock, R. R.; Fong, H. H.; Pozdin, V. A.; Smilgies, D.-M.; Malliaras, G. G. Alkylsubstituted Thienothiophene Semiconducting Materials: Structure-Property Relationships J. Am. Chem. Soc. 2009, 131, 11930-11938
22. Peng, Q.; Huang, Q.; Hou, X.; Chang, P.; Xu, J.; Deng, S. Enhanced Solar Cell Performance by Replacing Benzodithiophene with Naphthodithiophene in Diketopyrrolopyrrole-Based Copolymers Chem. Commun. (Camb.) 2012, 48, 11452-11454
23. 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
24. Loser, S.; Miyauchi, H.; Hennek, J. W.; Smith, J.; Huang, C.; Facchetti, A.; Marks, T. J. A "Zig-Zag" Naphthodithiophene Core for Increased Efficiency in Solution-Processed Small Molecule Solar Cells Chem. Commun. (Camb.) 2012, 48, 8511-8513
25. Guerrero, A.; Loser, S.; Garcia-Belmonte, G.; Bruns, C. J.; Smith, J.; Miyauchi, H.; Stupp, S. I.; Bisquert, J.; Marks, T. J. Solution-Processed Small Molecule: Fullerene Bulk-Heterojunction Solar Cells: Impedance Spectroscopy Deduced Bulk and Interfacial Limits to Fill-Factors Phys. Chem. Chem. Phys. 2013, 15, 16456-62
26. Moulé, A. J.; Tsami, A.; Bünnagel, T. W.; Forster, M.; Kronenberg, N. M.; Scharber, M.; Koppe, M.; Morana, M.; Brabec, C. J.; Meerholz, K. Two Novel Cyclopentadithiophene-Based Alternating Copolymers as Potential Donor Components for High-Efficiency Bulk-Heterojunction-Type Solar Cells Chem. Mater. 2008, 20, 4045-4050
27. Horie, M.; Kettle, J.; Yu, C.-Y.; Majewski, L. A.; Chang, S.-W.; Kirkpatrick, J.; Tuladhar, S. M.; Nelson, J.; Saunders, B. R.; Turner, M. L. Cyclopentadithiophene-Benzothiadiazole Oligomers and Polymers; Synthesis, Characterisation, Field-Effect Transistor and Photovoltaic Characteristics J. Mater. Chem. 2012, 22, 381
28. Li, Y.; Zou, J.; Yip, H.-L.; Li, C.-Z.; Zhang, Y.; Chueh, C.-C.; Intemann, J.; Xu, Y.; Liang, P.-W.; Chen, Y.; Jen, A. K. Y. Side-Chain Effect on Cyclopentadithiophene/Fluorobenzothiadiazole-Based Low Band Gap Polymers and Their Applications for Polymer Solar Cells Macromolecules 2013, 46, 5497-5503
29. Hou, J. H.; Chen, H.-Y.; Zhang, S.; Li, G.; Yang, Y. 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. 2008, 130, 16144-16145
30. Beaujuge, P. M.; Pisula, W.; Tsao, H. N.; Ellinger, S.; Mùllen, K.; Reynolds, J. R. Tailoring Structure- Property Relationships in Dithienosilole-Benzothiadiazole Donor-Acceptor Copolymers J. Am. Chem. Soc. 2009, 131, 7514-7515.
31. Chu, T. Y.; Lu, J.; Beaupre, S.; Zhang, Y.; Pouliot, J. R.; Wakim, S.; Zhou, J.; Leclerc, M.; Li, Z.; Ding, J.; Tao, Y. 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. 2011, 133, 4250-4253
32. Liu, J.; Zhang, R.; Osaka, I.; Mishra, S.; Javier, A. E.; Smilgies, D.-M.; Kowalewski, T.; McCullough, R. D. Transistor Paint: Environmentally Stable N -Alkyldithienopyrrole and Bithiazole-Based Copolymer Thin-Film Transistors Show Reproducible High Mobilities without Annealing Adv. Funct. Mater. 2009, 19, 3427-3434
33. Zhou, E.; Cong, J.; Tajima, K.; Hashimoto, K. Synthesis and Photovoltaic Properties of Donor-Acceptor Copolymers Based on 5,8-Dithien-2-yl-2,3- diphenylquinoxaline Chem. Mater. 2010, 22, 4890-4895
34. Wunsch, B. H.; Rumi, M.; Tummala, N. R.; Risko, C.; Kang, D.-Y.; Steirer, K. X.; Gantz, J.; Said, M.; Armstrong, N. R.; Brédas, J.-L.; Bucknall, D.; Marder, S. R. Structure-Processing-Property Correlations in Solution-Processed, Small-Molecule, Organic Solar Cells J. Mater. Chem. C 2013, 1, 5250-5260
35. Weidelener, M.; Wessendorf, C. D.; Hanisch, J.; Ahlswede, E.; Gotz, G.; Linden, M.; Schulz, G.; Mena-Osteritz, E.; Mishra, A.; Bauerle, P. Dithienopyrrole-Based Oligothiophenes for Solution-Processed Organic Solar Cells Chem. Commun. (Camb.) 2013, 49, 10865-10867
36. Park, J. K.; Kim, C.; Walker, B.; Nguyen, T.-Q.; Seo, J. H. Morphology Control of Solution Processable Small Molecule Bulk Heterojunction Solar Cells via Solvent Additives RSC Adv. 2012, 2, 2232
37. Li, J.; Tan, H.-S.; Chen, Z.-K.; Goh, W.-P.; Wong, H.-K.; Ong, K.-H.; Liu, W.; Li, C. M.; Ong, B. S. Dialkyl-Substituted Dithienothiophene Copolymers as Polymer Semiconductors for Thin-Film Transistors and Bulk Heterojunction Solar Cells Macromolecules 2011, 44, 690-693
38. Huang, X. B.; Zhu, C. L.; Zhang, S. M.; Li, W. W.; Guo, Y. L.; Zhan, X. W.; Liu, Y. Q.; Bo, Z. S. Porphyrin-Dithienothiophene π-Conjugated Copolymers: Synthesis and Their Applications in Field-Effect Transistors and Solar Cells Macromolecules 2008, 41, 6895-6902
39. Patil, A. V.; Lee, W.-H.; Lee, E.; Kim, K.; Kang, I.-N.; Lee, S.-H. Synthesis and Photovoltaic Properties of a Low-Band-Gap Copolymer of Dithieno[3,2- b:2′,3′- d ]thiophene and Dithienylquinoxaline Macromolecules 2011, 44, 1238-1241
40. Polander, L. E.; Tiwari, S. P.; Pandey, L.; Seifried, B. M.; Zhang, Q.; Barlow, S.; Risko, C.; Brédas, J.-L.; Kippelen, B.; Marder, S. R. Solution-Processed Molecular Bis(naphthalene diimide) Derivatives with High Electron Mobility Chem. Mater. 2011, 23, 3408-3410
41. Shinamura, S.; Osaka, I.; Miyazaki, E.; Nakao, A.; Yamagishi, M.; Takeya, J.; Takimiya, K. Linear- and Angular-Shaped Naphthodithiophenes: Selective Synthesis, Properties, and Application to Organic Field-Effect Transistors J. Am. Chem. Soc. 2011, 133, 5024-5035
42. Chen, Y.-L.; Chang, C.-Y.; Cheng, Y.-J.; Hsu, C.-S. Synthesis of a New Ladder-Type Benzodi(cyclopentadithiophene) Arene with Forced Planarization Leading to an Enhanced Efficiency of Organic Photovoltaics Chem. Mater. 2012, 24, 3964-3971
43. Kim, J.; Han, A. R.; Seo, J. H.; Oh, J. H.; Yang, C. β-Alkyl substituted Dithieno[2,3- d;2′,3′- d ′]benzo[1,2- b;4,5- b ′]dithiophene Semiconducting Materials and Their Application to Solution-Processed Organic Transistors Chem. Mater. 2012, 24, 3464-3472
44. Zeng, Z.; Li, Y.; Deng, J. F.; Huang, Q.; Peng, Q. Synthesis and Photovoltaic Performance of Low Band Bap Copolymers Based on Diketopyrrolopyrrole and Tetrathienoacene with Different Conjugated Bridges J. Mater. Chem. A 2014, 2, 653-662
45. Xiao, K.; Liu, Y.; Qi, T.; Zhang, W.; Wang, F.; Gao, J.; Qiu, W.; Ma, Y.; Cui, G.; Chen, S. A Highly π-Stacked Organic Semiconductor for Field-Effect Transistors Based on Linearly Condensed Pentathienoacene J. Am. Chem. Soc. 2005, 127, 13281-13286
46. Qu, S.; Tian, H. Diketopyrrolopyrrole (DPP)-Based Materials for Organic Photovoltaics Chem. Commun. (Camb.) 2012, 48, 3039-3051
47. 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
48. 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
49. 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
50. Mei, J. G.; Graham, K. R.; Stalder, R.; Tiwari, S. P.; Cheun, H.; Shim, J.; Yoshio, M.; Nuckolls, C.; Kippelen, B.; Castellano, R. K.; Reynolds, J. R. Self-Assembled Amphiphilic Diketopyrrolopyrrole-Based Oligothiophenes for Field-Effect Transistors and Solar Cells Chem. Mater. 2011, 23, 2285-2288
51. Qian, G.; Qi, J.; Davey, J. A.; Wright, J. S.; Wang, Z. Y. Family of Diazapentalene Chromophores and Narrow-Band-Gap Polymers: Synthesis, Halochromism, Halofluorism, and Visible-Near-Infrared Photodetectivity Chem. Mater. 2012, 24, 2364-2372
52. Bura, T.; Leclerc, N.; Bechara, R.; Lévêque, P.; Heiser, T.; Ziessel, R. Solar Cells: Triazatruxene-Diketopyrrolopyrrole Dumbbell-Shaped Molecules as Photoactive Electron Donor for High-Efficiency Solution Processed Organic Solar Cells Adv. Energy Mater. 2013, 3, 1109-1109
53. Eisenmenger, N. D.; Su, G. M.; Welch, G. C.; Takacs, C. J.; Bazan, G. C.; Kramer, E. J.; Chabinyc, M. L. Effect of Bridging Atom Identity on the Morphological Behavior of Solution-Processed Small Molecule Bulk Heterojunction Photovoltaics Chem. Mater. 2013, 25, 1688-1698
54. Mei, J. G.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors J. Am. Chem. Soc. 2013, 135, 6724-6746
55. Gevaerts, V. S.; Herzig, E. M.; Kirkus, M.; Hendriks, K. H.; Wienk, M. M.; Perlich, J.; Müller-Buschbaum, P.; Janssen, R. A. J. Influence of the Position of the Side Chain on Crystallization and Solar Cell Performance of DPP-Based Small Molecules Chem. Mater. 2014, 26, 916-926
56. Liu, X.; Sun, Y.; Perez, L. A.; Wen, W.; Toney, M. F.; Heeger, A. J.; Bazan, G. C. Narrow-Band-Gap Conjugated Chromophores with Extended Molecular Lengths J. Am. Chem. Soc. 2012, 134, 20609-20612
57. 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
58. Wan, J.-H.; Mao, L.-Y.; Li, Y.-B.; Li, Z.-F.; Qiu, H.-Y.; Wang, C.; Lai, G.-Q. Self-assembly of Novel Fluorescent Silole Derivatives into Different Supramolecular Aggregates: Fibre, Liquid Crystal and Monolayer Soft Matter 2010, 6, 3195-3201
59. Ding, L.; Li, H.-B.; Lei, T.; Ying, H.-Z.; Wang, R.-B.; Zhou, Y.; Su, Z.-M.; Pei, J. Alkylene-Chain Effect on Microwire Growth and Crystal Packing of π-Moieties Chem. Mater. 2012, 24, 1944-1949
60. Uhrich, C.; Schueppel, R.; Petrich, A.; Pfeiffer, M.; Leo, K.; Brier, E.; Kilickiran, P.; Baeuerle, P. Organic Thin-Film Photovoltaic Cells Based on Oligothiophenes with Reduced Bandgap Adv. Funct. Mater. 2007, 17, 2991-2999
61. Turbiez, M.; Frere, P.; Allain, M.; Videlot, C.; Ackermann, J.; Roncali, J. Design of Organic Semiconductors: Tuning the Electronic Properties of pConjugated Oligothiophenes with the 3,4-Ethylenedioxythiophene (EDOT) Building Block Chem.-Eur. J. 2005, 11, 3742-3752
62. 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
63. Shi, Q.; Cheng, P.; Li, Y. F.; Zhan, X. W. A Solution Processable D-A-D Molecule based on Thiazolothiazole for High Performance Organic Solar Cells Adv. Energy Mater. 2012, 2, 63-67
64. Shen, S.; Jiang, P.; He, C.; Zhang, J.; Shen, P.; Zhang, Y.; Yi, Y.; Zhang, Z.; Li, Z.; Li, Y. F. Solution-Processable Organic Molecule Photovoltaic Materials with Bithienyl-Benzodithiophene Central Unit and Indenedione End Groups Chem. Mater. 2013, 25, 2274-2281
65. Wang, H. Y.; Liu, F.; Bu, L.; Gao, J.; Wang, C.; Wei, W.; Russell, T. P. The Role of Additive in Diketopyrrolopyrrole-Based Small Molecular Bulk Heterojunction Solar Cells Adv. Mater. 2013, 25, 6519-6525
66. Graham, K. R.; Mei, J. G.; Stalder, R.; Shim, J. W.; Cheun, H.; Steffy, F.; So, F.; Kippelen, B.; Reynolds, J. R. Polydimethylsiloxane As a Macromolecular Additive for Enhanced Performance of Molecular Bulk Heterojunction Organic Solar Cells ACS Appl. Mater. Interfaces 2011, 3, 1210-1215
67. Kippelen, B.; Brédas, J.-L. Organic Photovoltaics Energy Environ. Sci. 2009, 2, 251
68. Wan, J. H.; Fang, W. F.; Li, Z. F.; Xiao, X. Q.; Xu, Z.; Deng, Y.; Zhang, L. H.; Jiang, J. X.; Qiu, H. Y.; Wu, L. B.; Lai, G. Q. Novel Ladder π-conjugated Materials-Sila-pentathienoacenes: Synthesis, Structure, and Electronic Properties Chem.-Asian J. 2010, 5, 2290-2296