Charge versus Energy Transfer Effects in High-Performance Perylene Diimide Photovoltaic Blend Films

ACS Applied Materials and Interfaces

Volumn 7, Issue 44, 2015, Pages 24876-24886

  Singh, Ranbir ^a   Shivanna, Ravichandran ^b   Iosifidis, Agathaggelos ^c   Butt, Hans Jürgen ^d   Floudas, George ^c   Narayan, K S ^b   Keivanidis, Panagiotis E ^e  

^a ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

^c UNIVERSITY OF IOANNINA   (Greece)

^d MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^e CYPRUS UNIVERSITY OF TECHNOLOGY   (Cyprus)

Author keywords

charge transfer; energy transfer; excimer dissociation; fullerene free OPVs; nonfullerene acceptors; perylene diimide; self assembly

Indexed keywords

CHARGE TRANSFER; ENERGY TRANSFER; EXCITED STATES; PHOTOVOLTAIC EFFECTS; POLYCYCLIC AROMATIC HYDROCARBONS; POLYMERS; SELF ASSEMBLY; X RAY SCATTERING;

ENERGY TRANSFER EFFECTS; EXCIMERS; FULLERENE FREE; NONFULLERENE ACCEPTORS; NONRADIATIVE ENERGY TRANSFER; ORGANIC PHOTOVOLTAIC DEVICES; PERYLENEDIIMIDES; THIENO[3 ,4-B]THIOPHENE;

QUENCHING;

EID: 84947086951     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b08224     Document Type: Article

References (66)

1. Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Plastic Solar Cells Adv. Funct. Mater. 2001, 11, 15-26 10.1002/1616-3028(200102)11:1<15::AID-ADFM15>3.3.CO;2-1
2. Dou, L.; You, J.; Hong, Z.; Xu, Z.; Li, G.; Street, R. A.; Yang, Y. 25th Anniversary Article: A Decade of Organic/Polymeric Photovoltaic Research Adv. Mater. 2013, 25, 6642-6671 10.1002/adma.201302563
3. He, Z. C.; Zhong, C. M.; Su, S. J.; Xu, M.; Wu, H. B.; Cao, Y. Enhanced Power-Conversion Efficiency in Polymer Solar Cells Using an Inverted Device Structure Nat. Photonics 2012, 6, 593-597 10.1038/nphoton.2012.190
4. Scharber, M. C.; Muhlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. L. Design Rules for Donors in Bulk-Heterojunction Solar Cells-Towards 10% Energy-Conversion Efficiency Adv. Mater. 2006, 18, 789-794 10.1002/adma.200501717
5. Service, R. F. Outlook Brightens for Plastic Solar Cells Science 2011, 332, 293-293 10.1126/science.332.6027.293
6. Lin, Y.; Zhan, X. Non-Fullerene Acceptors for Organic Photovoltaics: An Emerging Horizon Mater. Horiz. 2014, 1, 470-488 10.1039/C4MH00042K
7. Li, H.; Earmme, T.; Ren, G.; Saeki, A.; Yoshikawa, S.; Murari, N. M.; Subramaniyan, S.; Crane, M. J.; Seki, S.; Jenekhe, S. A. Beyond Fullerenes: Design of Nonfullerene Acceptors for Efficient Organic Photovoltaics J. Am. Chem. Soc. 2014, 136, 14589-14597 10.1021/ja508472j
8. Kwon, O. K.; Park, J.-H.; Park, S. K.; Park, S. Y. Soluble Dicyanodistyrylbenzene-Based Non-Fullerene Electron Acceptors with Optimized Aggregation Behavior for High-Efficiency Organic Solar Cells Adv. Energy Mater. 2015, 5, 1400929 10.1002/aenm.201400929
9. Holliday, S.; Ashraf, R. S.; Nielsen, C. B.; Kirkus, M.; Röhr, J. A.; Tan, C.-H.; Collado-Fregoso, E.; Knall, A.-C.; Durrant, J. R.; Nelson, J.; McCulloch, I. A Rhodanine Flanked Nonfullerene Acceptor for Solution-Processed Organic Photovoltaics J. Am. Chem. Soc. 2015, 137, 898-904 10.1021/ja5110602
10. McAfee, S. M.; Topple, J. M.; Hill, I. G.; Welch, G. C. Key Components to the Recent Performance Increases of Solution Processed Non-Fullerene Small Molecule Acceptors J. Mater. Chem. A 2015, 3, 16393 10.1039/C5TA04310G
11. Tang, C. W. Two-Layer Organic Photovoltaic cell Appl. Phys. Lett. 1986, 48, 183-185 10.1063/1.96937
12. Schmidt-Mende, L.; Fechtenkotter, A.; Mullen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Self-organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics Science 2001, 293, 1119-1122 10.1126/science.293.5532.1119
13. Keivanidis, P. E.; Howard, I. A.; Friend, R. H. Intermolecular Interactions of Perylene Diimides in Photovoltaic Blends of Fluorene Copolymers: Disorder Effects on Photophysical Properties, Film Morphology and Device Efficiency Adv. Funct. Mater. 2008, 18, 3189-3202 10.1002/adfm.200800356
14. Kamm, V.; Battagliarin, G.; Howard, I. A.; Pisula, W.; Mavrinskiy, A.; Li, C.; Muellen, K.; Laquai, F. Polythiophene:Perylene Diimide Solar Cells-the Impact of Alkyl-Substitution on the Photovoltaic Performance Adv. Energy Mater. 2011, 1, 297-302 10.1002/aenm.201000006
15. 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 10.1002/adma.201301167
16. 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 10.1002/adma.201001402
17. Tasios, N.; Grigoriadis, C.; Hansen, M. R.; Wonneberger, H.; Li, C.; Spiess, H. W.; Müllen, K.; Floudas, G. Self-Assembly, Dynamics, and Phase Transformation Kinetics of Donor-Acceptor Substituted Perylene Derivatives J. Am. Chem. Soc. 2010, 132, 7478 10.1021/ja102150g
18. Jancy, B.; Asha, S. K. Hydrogen-Bonding-Induced Conformational Change from J to H Aggregate in Novel Highly Fluorescent Liquid-Crystalline Perylenebisimides Chem. Mater. 2008, 20, 169-181 10.1021/cm702497y
19. Singh, T. B.; Erten, S.; Guenes, S.; Zafer, C.; Turkmen, G.; Kuban, B.; Teoman, Y.; Sariciftci, N. S.; Icli, S. Soluble Derivatives of Perylene and Naphthalene Diimide for n-Channel Organic Field-effect Transistors Org. Electron. 2006, 7, 480-489 10.1016/j.orgel.2006.06.010
20. Jiang, W.; Xiao, C.; Hao, L.; Wang, Z.; Ceymann, H.; Lambert, C.; Di Motta, S.; Negri, F. Localization/Delocalization of Charges in Bay-Linked Perylene Bisimides Chem.-Eur. J. 2012, 18, 6764-6775 10.1002/chem.201103954
21. Singh, R.; Giussani, E.; Mroz, M. M.; Fonzo, F. D.; Fazzi, D.; Cabanillas-González, J.; Oldridge, L.; Vaenas, N.; Kontos, A. G.; Falaras, P.; Grimsdale, A. C.; Jacob, J.; Müllen, K.; Keivanidis, P. E. On the Role of Aggregation Effects in the Performance of Perylene-Diimide based Solar Cells Org. Electron. 2014, 15, 1347-1361 10.1016/j.orgel.2014.03.044
22. Chen, Z. J.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L. D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Photoluminescence and Conductivity of Self-assembled pi-pi Stacks of Perylene Bisimide Dyes Chem.-Eur. J. 2007, 13, 436-449 10.1002/chem.200600889
23. Chellappan, K. V.; Kandappa, S. K.; Rajaram, S.; Narayan, K. S. Ferroelectric Polymer Matrix for Probing Molecular Organization in Perylene Diimides J. Phys. Chem. Lett. 2015, 6, 224-229 10.1021/jz5023976
24. Hartnett, P. E.; Timalsina, A.; Matte, H. S. S. R.; Zhou, N.; Guo, X.; Zhao, W.; Facchetti, A.; Chang, R. P. H.; Hersam, M. C.; Wasielewski, M. R.; Marks, T. J. Slip-Stacked Perylenediimides as an Alternative Strategy for High Efficiency Nonfullerene Acceptors in Organic Photovoltaics J. Am. Chem. Soc. 2014, 136, 16345-16356 10.1021/ja508814z
25. Shoaee, S.; Deledalle, F.; Tuladhar, P. S.; Shivanna, R.; Rajaram, S.; Narayan, K. S.; Durrant, J. R. A Comparison of Charge Separation Dynamics in Organic Blend Films Employing Fullerene and Perylene Diimide Electron Acceptors J. Phys. Chem. Lett. 2015, 6, 201-205 10.1021/jz502385n
26. Gehrig, D. W.; Roland, S.; Howard, I. A.; Kamm, V.; Mangold, H.; Neher, D.; Laquai, F. d. r. Efficiency-Limiting Processes in Low-Bandgap Polymer:Perylene Diimide Photovoltaic Blends J. Phys. Chem. C 2014, 118, 20077-20085 10.1021/jp503366m
27. Shivanna, R.; Shoaee, S.; Dimitrov, S.; Kandappa, S. K.; Rajaram, S.; Durrant, J. R.; Narayan, K. S. Charge Generation and Transport in Efficient Organic Bulk Heterojunction Solar Cells with a Perylene Acceptor Energy Environ. Sci. 2014, 7, 435-441 10.1039/C3EE42484G
28. Ye, T.; Singh, R.; Butt, H.-J.; Floudas, G.; Keivanidis, P. E. Effect of Local and Global Structural Order on the Performance of Perylene Diimide Excimeric Solar Cells ACS Appl. Mater. Interfaces 2013, 5, 11844-11857 10.1021/am4035416
29. Chen, Z.; Baumeister, U.; Tschierske, C.; Wüerthner, F. Effect of Core Twisting on Self-Assembly and Optical Properties of Perylene Bisimide Dyes in Solution and Columnar Liquid Crystalline Phases Chem.-Eur. J. 2007, 13, 450-465 10.1002/chem.200600891
30. 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 10.1021/jp907633g
31. Lindquist, R. J.; Lefler, K. M.; Brown, K. E.; Dyar, S. M.; Margulies, E. A.; Young, R. M.; Wasielewski, M. R. Energy Flow Dynamics within Cofacial and Slip-Stacked Perylene-3,4-dicarboximide Dimer Models of -Aggregates J. Am. Chem. Soc. 2014, 136, 14912-14923 10.1021/ja507653p
32. Fischer, D.; Naundorf, G.; Klöpffer, D. Light Absorption by Pyrene Single Crystals Between 4 and 300K: A Search for the Ground-to Excimer State Absorption Z. Naturforsch., A: Phys. Sci. 1973, 10.1515/zna-1973-0620
33. Singh, R.; Aluicio-Sarduy, E.; Kan, Z.; Ye, T.; MacKenzie, R. C. I.; Keivanidis, P. E. Fullerene-free Organic Solar Cells with an Efficiency of 3.7% Based on a Low-Cost Geometrically Planar Perylene Diimide Monomer J. Mater. Chem. A 2014, 2, 14348-14353 10.1039/C4TA02851A
34. Aluicio-Sarduy, E.; Singh, R.; Kan, Z.; Ye, T.; Baidak, A.; Calloni, A.; Berti, G.; Duò, L.; Iosifidis, A.; Beaupré, S.; Leclerc, M.; Butt, H.-J.; Floudas, G.; Keivanidis, P. E. Elucidating the Impact of Molecular Packing and Device Architecture on the Performance of Nanostructured Perylene Diimide Solar Cells ACS Appl. Mater. Interfaces 2015, 7, 8687-8698 10.1021/acsami.5b00827
35. Dittmer, J. J.; Marseglia, E. A.; Friend, R. H. Electron Trapping in Dye/Polymer Blend Photovoltaic Cells Adv. Mater. 2000, 12, 1270-1274 10.1002/1521-4095(200009)12:17<1270::AID-ADMA1270>3.0.CO;2-8
36. Di Donato, E.; Fornari, R. P.; Di Motta, S.; Li, Y.; Wang, Z.; Negri, F. n-Type Charge Transport and Mobility of Fluorinated Perylene Bisimide Semiconductors J. Phys. Chem. B 2010, 114, 5327-5334 10.1021/jp101040r
37. Mizoshita, N.; Tani, T.; Inagaki, S. Highly Conductive Organosilica Hybrid Films Prepared from a Liquid-Crystal Perylene Bisimide Precursor Adv. Funct. Mater. 2011, 21, 3291-3296 10.1002/adfm.201100444
38. Takada, T.; Ashida, A.; Nakamura, M.; Fujitsuka, M.; Majima, T.; Yamana, K. Photocurrent Generation Enhanced by Charge Delocalization over Stacked Perylenediimide Chromophores Assembled within DNA J. Am. Chem. Soc. 2014, 136, 6814-6817 10.1021/ja501535z
39. 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 10.1021/jz301047d
40. Ie, Y.; Sakurai, T.; Jinnai, S.; Karakawa, M.; Okuda, K.; Mori, S.; Aso, Y. Three-Dimensional Electron-Accepting Compounds Containing Perylene bis(dicarboximide)s as n-Type Organic Photovoltaic Materials Chem. Commun. 2013, 49, 8386-8388 10.1039/c3cc43925a
41. Ramanan, C.; Kim, C. H.; Marks, T. J.; Wasielewski, M. R. Excitation Energy Transfer within Covalent Tetrahedral Perylenediimide Tetramers and Their Intermolecular Aggregates J. Phys. Chem. C 2014, 118, 16941-16950 10.1021/jp500475c
42. Chen, W.; Yang, X.; Long, G.; Wan, X.; Chen, Y.; Zhang, Q. A Perylene Diimide (PDI)-Based Small Molecule with Tetrahedral Configuration as a Non-Fullerene Acceptor for Organic Solar Cells J. Mater. Chem. C 2015, 3, 4698-4705 10.1039/C5TC00865D
43. Liu, Y.; Mu, C.; Jiang, K.; Zhao, J.; Li, Y.; Zhang, L.; Li, Z.; Lai, J. Y. L.; Hu, H.; Ma, T.; Hu, R.; Yu, D.; Huang, X.; Tang, B. Z.; Yan, H. A Tetraphenylethylene Core-Based 3D Structure Small Molecular Acceptor Enabling Efficient Non-Fullerene Organic Solar Cells Adv. Mater. 2015, 27, 1015-1020 10.1002/adma.201404152
44. Liu, S.-Y.; Wu, C.-H.; Li, C.-Z.; Liu, S.-Q.; Wei, K.-H.; Chen, H.-Z.; Jen, A. K.-Y. A Tetraperylene Diimides Based 3D Nonfullerene Acceptor for Efficient Organic Photovoltaics Adv. Sci. 2015, 10.1002/advs.201500014
45. Chen, Y.; Zhang, X.; Zhan, C.; Yao, J. In-Depth Understanding of Photocurrent Enhancement in Solution-Processed Small-Molecule:Perylene Diimide Non-Fullerene Organic Solar Cells Phys. Status Solidi A 2015, 212, 1961 10.1002/pssa.201532102
46. Zhao, J.; Li, Y.; Lin, H.; Liu, Y.; Jiang, K.; Mu, C.; Ma, T.; Lai, J. Y. L.; Yan, H. et al. High-Efficiency Non-Fullerene Organic Solar Cells Enabled by a Difluorobenzothiadizole-Based Donor Polymer Combined with a Properly Matched Small Molecule Acceptor Energy Environ. Sci. 2015, 8, 520-525 10.1039/C4EE02990A
47. Wu, C.-H.; Chueh, C.-C.; Xi, Y.-Y.; Zhong, H.-L.; Gao, G.-P.; Wang, Z.-H.; Pozzo, L.-D.; Wen, T.-C.; Jen, A. K.-Y. Influence of Molecular Geometry of Perylene Diimide Dimers and Polymers on Bulk Heterojunction Morphology Toward High-Performance Nonfullerene Polymer Solar Cells Adv. Funct. Mater. 2015, 25, 5326 10.1002/adfm.201501971
48. Sun, D.; Meng, D.; Cai, Y.; Fan, B.; Li, Y.; Jiang, W.; Huo, L.; Sun, Y.; Wang, Z. Non-Fullerene-Acceptor-Based Bulk-Heterojunction Organic Solar Cells with Efficiency over 7% J. Am. Chem. Soc. 2015, 137, 11156 10.1021/jacs.5b06414
49. Lu, Z.; Jiang, B.; Zhang, X.; Tang, A.; Chen, L.; Zhan, C.; Yao, J. Perylene-Diimide Based Non-Fullerene Solar Cells with 4.34% Efficiency through Engineering Surface Donor/Acceptor Compositions Chem. Mater. 2014, 26, 2907-2914 10.1021/cm5006339
50. Sharenko, A.; Gehrig, D.; Laquai, F.; Nguyen, T.-Q. The Effect of Solvent Additive on the Charge Generation and Photovoltaic Performance of a Solution-Processed Small Molecule:Perylene Diimide Bulk Heterojunction Solar Cell Chem. Mater. 2014, 26, 4109-4118 10.1021/cm5010483
51. Chen, Y.; Zhang, X.; Zhan, C.; Yao, J. Origin of Effects of Additive Solvent on Film-Morphology in Solution-Processed Nonfullerene Solar Cells ACS Appl. Mater. Interfaces 2015, 7, 6462-6471 10.1021/am507581w
52. Zang, Y.; Li, C.-Z.; Chueh, C.-C.; Williams, S. T.; Jiang, W.; Wang, Z.-H.; Yu, J.-S.; Jen, A. K. Y. Integrated Molecular, Interfacial, and Device Engineering towards High-Performance Non-Fullerene Based Organic Solar Cells Adv. Mater. 2014, 26, 5708-5714 10.1002/adma.201401992
53. Shivanna, R.; Rajaram, R.; Narayan, K. S. Interface Engineering for Efficient Fullerene-Free Organic Solar Cells Appl. Phys. Lett. 2015, 106, 123301 10.1063/1.4916216
54. Ye, L.; Sun, K.; Jiang, W.; Zhang, S.; Zhao, W.; Yao, H.; Wang, Z.; Hou, J. Enhanced Efficiency in Fullerene-Free Polymer Solar Cell by Incorporating Fine-designed Donor and Acceptor Materials ACS Appl. Mater. Interfaces 2015, 7, 9274-9280 10.1021/acsami.5b02012
55. Förster, T. Transfer Mechanisms of Electronic Excitation Discuss. Faraday Soc. 1959, 27, 7-17 10.1039/df9592700007
56. Engmann, S.; Bokel, F. A.; Herzing, A. A.; Ro, H. W.; Girotto, C.; Caputo, B.; Hoven, C. V.; Schaible, E.; Hexemer, A.; DeLongchamp, D. M.; Richter, L. J. Real-Time X-Ray Scattering Studies of Film Evolution in High Performing Small-Molecule-Fullerene Organic Solar Cells J. Mater. Chem. A 2015, 3, 8764-8771 10.1039/C5TA00935A
57. Atkins, P.; de Paula, J. Physical Chemistry, 9 th ed.; Macmillan Education: U.K., 2010.
58. Chi, C.; Im, C.; Enkelmann, V.; Ziegler, A.; Lieser, G.; Wegner, G. Monodisperse Oligofluorenes with Keto Defect as Models to Investigate the Origin of Green Emission From Polyfluorenes: Syntheis, Self-Assembly, and Photophysical Properties Chem.-Eur. J. 2005, 11, 6833-6845 10.1002/chem.200500275
59. Bednarz, M.; Malyshev, V. A.; Knoester, J. Low-Temperature Dynamics of Weakly Localized Frenkel Excitons in Disordered Linear Chains J. Chem. Phys. 2004, 120, 3827-3840 10.1063/1.1643720
60. Wiesenhofer, H.; Zojer, E.; List, E. J. W.; Scherf, U.; Bredas, J. L.; Beljonne, D. Molecular Origin of the Temperature-Dependent Energy Migration in a Rigid-Rod Ladder-Phenylene Molecular Host Adv. Mater. 2006, 18, 310-314 10.1002/adma.200501473
61. Wantz, G.; Hirsch, L.; Huby, N.; Vignau, L.; Barriere, A. S.; Parneix, J. P. Temperature-Dependent Electroluminescence Spectra of Poly(phenylene-vinylene) Derivatives-Based Polymer Light-Emitting Diodes J. Appl. Phys. 2005, 97, 034505 10.1063/1.1845580
62. Guha, S.; Rice, J. D.; Yau, Y. T.; Martin, C. M.; Chandrasekhar, M.; Chandrasekhar, H. R.; Guentner, R.; de Freitas, P. S.; Scherf, U. Temperature-Dependent Photoluminescence of Organic Semiconductors with Varying Backbone Conformation Phys. Rev. B: Condens. Matter Mater. Phys. 2003, 67, 125204 10.1103/PhysRevB.67.125204
63. Alamiry, M. A. H.; Harriman, A.; Mallon, L. J.; Ulrich, G.; Ziessel, R. Energy- and Charge-Transfer Processes in a Perylene-BODIPY-Pyridine Tripartite Array Eur. J. Org. Chem. 2008, 16, 2774-2782 10.1002/ejoc.200800159
64. Curutchet, C.; Mennucci, B.; Scholes, G. D.; Beljonne, D. oes Forster Theory Predict the Rate of Electronic Energy Transfer for a Model Dyad at Low Temperature? J. Phys. Chem. B 2008, 112, 3759-3766 10.1021/jp7106507
65. Rothberg, L. J.; Yan, M.; Papadimitrakopoulos, F.; Galvin, M. E.; Kwock, E. W.; Miller, T. M. Photophysics of Phenylenevinylene Polymers Synth. Met. 1996, 80, 41-58 10.1016/0379-6779(96)80202-5
66. Foster, S.; Finlayson, C. E.; Keivanidis, P. E.; Huang, Y.-S.; Hwang, I.; Friend, R. H.; Otten, M. B. J.; Lu, L.-P.; Schwartz, E.; Nolte, R. J. M.; Rowan, A. E. Improved Performance of Perylene-Based Photovoltaic Cells Using Polyisocyanopeptide Arrays Macromolecules 2009, 42, 2023-2030 10.1021/ma801959w