Annealing-induced changes in the molecular orientation of poly-3-hexylthiophene at buried interfaces

Journal of Physical Chemistry C

Volumn 117, Issue 29, 2013, Pages 15213-15220

  Dhar, Purnim ^a   Khlyabich, Petr P ^a   Burkhart, Beate ^a   Roberts, Sean T ^a   Malyk, Sergey ^a   Thompson, Barry C ^a   Benderskii, Alexander V ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED BACKBONES; ELECTRON TRANSFER RATES; MOLECULAR ORGANIZATION; ORGANIC PHOTOVOLTAICS; ORGANIC SEMICONDUCTING MATERIALS; PHOTO-VOLTAIC EFFICIENCY; POLY-3-HEXYLTHIOPHENE; VIBRATIONAL SUM-FREQUENCY GENERATIONS;

ANNEALING; CARRIER MOBILITY; ELECTRONIC PROPERTIES; FIELD EFFECT TRANSISTORS; MOLECULAR ORIENTATION; POLYMER FILMS; SUBSTRATES; THIOPHENE;

INTERFACES (MATERIALS);

EID: 84880813274     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp404846r     Document Type: Article

References (73)

1. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; de Leeuw, D. M. Two-Dimensional Charge Transport in Self-Organized, High-Mobility Conjugated Polymers Nature 1999, 401, 685-688
2. Kline, J. R.; McGehee, M. D.; Toney, M. F. Highly Oriented Crystals at the Buried Interface in Polythiophene Thin-Film Transistors Nat. Mater. 2006, 5, 222-228
3. Tada, A.; Geng, Y.; Nakamura, M.; Wei, Q.; Hashimoto, K.; Tajima, K. Interfacial Modification of Organic Photovoltaic Devices by Molecular Self-Organization Phys. Chem. Chem. Phys. 2012, 14, 3713-3724
4. Beaujuge, P. M.; Fréchet, J. M. J. Molecular Design and Ordering Effects in Π-Functional Materials for Transistor and Solar Cell Applications J. Am. Chem. Soc. 2011, 133, 20009-20029
5. Walter, S. R.; Youn, J.; Emery, J. D.; Kewalramani, S.; Hennek, J. W.; Bedzyk, M. J.; Facchetti, A.; Marks, T. J.; Geiger, F. M. In-Situ Probe of Gate Dielectric-Semiconductor Interfacial Order in Organic Transistors: Origin and Control of Large Performance Sensitivities J. Am. Chem. Soc. 2012, 134, 11726-11733
6. Horowitz, G. Organic Thin Film Transistors: From Theory to Real Devices J. Mater. Res. 2004, 19, 1946-1962
7. Anglin, T. C.; O'Brien, D. B.; Massari, A. M. Monitoring the Charge Accumulation Process in Polymeric Field-Effect Transistors Via in Situ Sum Frequency Generation J. Phys. Chem. C 2010, 114, 17629-17637
8. Anglin, T. C.; Speros, J. C.; Massari, A. M. Interfacial Ring Orientation in Polythiophene Field-Effect Transistors on Functionalized Dielectrics J. Phys. Chem. C 2011, 115, 16027-16036
9. Holcombe, T. W.; Norton, J. E.; Rivnay, J.; Woo, C. H.; Goris, L.; Piliego, C.; Griffini, G.; Sellinger, A.; Brédas, J.-L.; Salleo, A.; Fréchet, J. M. J. Steric Control of the Donor/Acceptor Interface: Implications in Organic Photovoltaic Charge Generation J. Am. Chem. Soc. 2011, 133, 12106-12114
10. Brédas, J.-L.; Norton, J. E.; Cornil, J.; Coropceanu, V. Molecular Understanding of Organic Solar Cells: The Challenges Acc. Chem. Res. 2009, 42, 1691-1699
11. Ratcliff, E. L.; Zacher, B.; Armstrong, N. R. Selective Interlayers and Contacts in Organic Photovoltaic Cells J. Phys. Chem. Lett. 2011, 2, 1337-1350
12. Yi, Y.; Coropceanu, V.; Brédas, J.-L. Exciton-Dissociation and Charge-Recombination Processes in Pentacene/C60 Solar Cells: Theoretical Insight into the Impact of Interface Geometry J. Am. Chem. Soc. 2009, 131, 15777-15783
13. Mou, W. W.; Ohmura, S.; Shimojo, F.; Nakano, A. Molecular Control of Photoexcited Charge Transfer and Recombination at a Quaterthiophene/Zinc Oxide Interface Appl. Phys. Lett. 2012, 100, 203306 1-5
14. Chen, Z.; Shen, Y. R.; Somorjai, G. A. Studies of Polymer Surfaces by Sum Frequency Generation Vibrational Spectroscopy Annu. Rev. Phys. Chem. 2002, 53, 437-465
15. Chen, Z. Investigating Buried Polymer Interfaces Using Sum Frequency Generation Vibrational Spectroscopy Prog. Polym. Sci. 2010, 35, 1376-1402
16. Wang, H.-F.; Gan, W.; Lu, R.; Rao, Y.; Wu, B.-H. Quantitative Spectral and Orientational Analysis in Surface Sum Frequency Generation Vibrational Spectroscopy (SFG-Vs) Int. Rev. Phys. Chem. 2005, 24, 191-256
17. Gautam, K. S.; Schwab, A. D.; Dhinojwala, A.; Zhang, D.; Dougal, S. M.; Yeganeh, M. S. Molecular Structure of Polystyrene at Air/Polymer and Solid/Polymer Interfaces Phys. Rev. Lett. 2000, 85, 3854-3857
18. Shen, Y. R. Surface Properties Probed by Second-Harmonic and Sum-Frequency Generation Nature 1989, 337, 519-525
19. Zhuang, X.; Miranda, P. B.; Kim, D.; Shen, Y. R. Mapping Molecular Orientation and Conformation at Interfaces by Surface Nonlinear Optics Phys. Rev. B 1999, 59, 12632-12640
20. Jayathilake, H. D.; Zhu, M. H.; Rosenblatt, C.; Bordenyuk, A. N.; Weeraman, C.; Benderskii, A. V. Rubbing-Induced Anisotropy of Long Alkyl Side Chains at Polyimide Surfaces J. Chem. Phys. 2006, 125, 064706 1-9
21. Bordenyuk, A. N.; Jayathilake, H.; Benderskii, A. V. Coherent Vibrational Quantum Beats as a Probe of Langmuir-Blodgett Monolayers J. Phys. Chem. B 2005, 109, 15941-15949
22. Harp, G. P.; Gautam, K. S.; Dhinojwala, A. Probing Polymer/Polymer Interfaces J. Am. Chem. Soc. 2002, 124, 7908-7909
23. Lu, X.; Li, D.; Kristalyn, C. B.; Han, J.; Shephard, N.; Rhodes, S.; Xue, G.; Chen, Z. Directly Probing Molecular Ordering at the Buried Polymer/Metal Interface Macromolecules 2009, 42, 9052-9057
24. Wilson, P. T.; Briggman, K. A.; Wallace, W. E.; Stephenson, J. C.; Richter, L. J. Selective Study of Polymer/Dielectric Interfaces with Vibrationally Resonant Sum Frequency Generation Via Thin-Film Interference Appl. Phys. Lett. 2002, 80, 3084-3086
25. Ye, H.; Abu-Akeel, A.; Huang, J.; Katz, H. E.; Gracias, D. H. Probing Organic Field Effect Transistors in Situ During Operation Using SFG J. Am. Chem. Soc. 2006, 128, 6528-6529
26. Ye, H.; Huang, J.; Park, J.-R.; Katz, H. E.; Gracias, D. H. Correlations between SFG Spectra and Electrical Properties of Organic Field Effect Transistors J. Phys. Chem. C 2007, 111, 13250-13255
27. Anglin, T. C.; Sohrabpour, Z.; Massari, A. M. Nonlinear Spectroscopic Markers of Structural Change During Charge Accumulation in Organic Field-Effect Transistors J. Phys. Chem. C 2011, 115, 20258-20266
28. Thompson, B. C.; Fréchet, J. M. J. Polymer-Fullerene Composite Solar Cells Angew. Chem. Intl. Ed. 2008, 47, 58-77
29. Bao, Z.; Dodabalapur, A.; Lovinger, A. J. Soluble and Processable Regioregular Poly(3-Hexylthiophene) for Thin Film Field-Effect Transistor Applications with High Mobility Appl. Phys. Lett. 1996, 69, 4108-4110
30. Dang, M. T.; Hirsch, L.; Wantz, G. P3HT:PCBM, Best Seller in Polymer Photovoltaic Research Adv. Mater. 2011, 23, 3597-3602
31. Prosa, T. J.; Winokur, M. J.; Moulton, J.; Smith, P.; Heeger, A. J. X-Ray Structural Studies of Poly(3-Alkylthiophenes): An Example of an Inverse Comb Macromolecules 1992, 25, 4364-4372
32. Melis, C.; Colombo, L.; Mattoni, A. Self-Assembling of Poly(3-Hexylthiophene) J. Phys. Chem. C 2010, 115, 576-581
33. Maillard, A.; Rochefort, A. Structural and Electronic Properties of Poly(3-Hexylthiophene) Π-Stacked Crystals Phys. Rev. B 2009, 79, 115207 1-7
34. Meille, S. V.; Romita, V.; Caronna, T.; Lovinger, A. J.; Catellani, M.; Belobrzeckaja, L. Influence of Molecular Weight and Regioregularity on the Polymorphic Behavior of Poly(3-Decylthiophenes) Macromolecules 1997, 30, 7898-7905
35. Liu, F.; Gu, Y.; Jung, J. W.; Jo, W. H.; Russell, T. P. On the Morphology of Polymer-Based Photovoltaics J. Polym. Sci., Part B 2012, 50, 1018-1044
36. Ma, W.; Yang, C.; Gong, X.; Lee, K.; Heeger, A. J. Thermally Stable, Efficient Polymer Solar Cells with Nanoscale Control of the Interpenetrating Network Morphology Adv. Func. Mater. 2005, 15, 1617-1622
37. Tsoi, W. C.; Spencer, S. J.; Yang, L.; Ballantyne, A. M.; Nicholson, P. G.; Turnbull, A.; Shard, A. G.; Murphy, C. E.; Bradley, D. D. C.; Nelson, J.; Kim, J.-S. Effect of Crystallization on the Electronic Energy Levels and Thin Film Morphology of P3HT:PCBM Blends Macromolecules 2011, 44, 2944-2952
38. Verploegen, E.; Mondal, R.; Bettinger, C. J.; Sok, S.; Toney, M. F.; Bao, Z. Effects of Thermal Annealing Upon the Morphology of Polymer-Fullerene Blends Adv. Func. Mater. 2010, 20, 3519-3529
39. Li, G.; Shrotriya, V.; Huang, J.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. High-Efficiency Solution Processable Polymer Photovoltaic Cells by Self-Organization of Polymer Blends Nat. Mater. 2005, 4, 864-868
40. Grigorian, S.; Joshi, S.; Pietsch, U. Temperature-Dependent Structural Properties of P3HT Films IOP Conf. Ser.: Mater. Sci. Eng. 2010, 14, 012007 1-8
41. Jouane, Y.; Colis, S.; Schmerber, G.; Leuvrey, C.; Dinia, A.; Leveque, P.; Heiser, T.; Chapuis, Y.-A. Annealing Treatment for Restoring and Controlling the Interface Morphology of Organic Photovoltaic Cells with Interfacial Sputtered Zno Films on P3HT:PCBM Active Layers J. Mater. Chem. 2012, 22, 1606-1612
42. Yang, X.; Loos, J.; Veenstra, S. C.; Verhees, W. J. H.; Wienk, M. M.; Kroon, J. M.; Michels, M. A. J.; Janssen, R. A. J. Nanoscale Morphology of High-Performance Polymer Solar Cells Nano Lett. 2005, 5, 579-583
43. Zen, A.; Pflaum, J.; Hirschmann, S.; Zhuang, W.; Jaiser, F.; Asawapirom, U.; Rabe, J. P.; Scherf, U.; Neher, D. Effect of Molecular Weight and Annealing of Poly(3-Hexylthiophene)s on the Performance of Organic Field-Effect Transistors Adv. Func. Mater. 2004, 14, 757-764
44. Steim, R.; Kogler, F. R.; Brabec, C. J. Interface Materials for Organic Solar Cells J. Mater. Chem. 2010, 20, 2499-2512
45. Ma, H.; Yip, H.-L.; Huang, F.; Jen, A. K. Y. Interface Engineering for Organic Electronics Adv. Func. Mater. 2010, 20, 1371-1388
46. Chen, L.-M.; Xu, Z.; Hong, Z.; Yang, Y. Interface Investigation and Engineering-Achieving High Performance Polymer Photovoltaic Devices J. Mater. Chem. 2010, 20, 2575-2598
47. Agranovich, V. M.; Gartstein, Y. N.; Litinskaya, M. Hybrid Resonant Organic-Inorganic Nanostructures for Optoelectronic Applications Chem. Rev. 2011, 111, 5179-5214
48. 2 Nanorod Bulk Heterojunction Solar Cells J. Am. Chem. Soc. 2009, 131, 3644-3649
49. Kim, K. D.; Song, C. K. Low Voltage Pentacene Thin Film Transistors Employing a Self-Grown Metal-Oxide as a Gate Dielectric Appl. Phys. Lett. 2006, 88, 233508 1-3
50. Chua, L.-L.; Zaumseil, J.; Chang, J.-F.; Ou, E. C. W.; Ho, P. K. H.; Sirringhaus, H.; Friend, R. H. General Observation of N-Type Field-Effect Behaviour in Organic Semiconductors Nature 2005, 434, 194-199
51. Cannon, J. P.; Bearden, S. D.; Gold, S. A. Characterization of Conjugated Polymer/Anodic Aluminum Oxide Nanocomposites Fabricated Via Template Wetting Composites A: Appl. Sci. Manufact. 2010, 41, 836-841
52. Qi, D.; Kwong, K.; Rademacher, K.; Wolf, M. O.; Young, J. F. Optical Emission of Conjugated Polymers Adsorbed to Nanoporous Alumina Nano Lett. 2003, 3, 1265-1268
53. 3 as a Capping Layer for Polymer Based Transistors Org. Electronics 2007, 8, 407-414
54. Tsoi, W. C.; James, D. T.; Kim, J. S.; Nicholson, P. G.; Murphy, C. E.; Bradley, D. D. C.; Nelson, J.; Kim, J.-S. The Nature of in-Plane Skeleton Raman Modes of P3HT and Their Correlation to the Degree of Molecular Order in P3HT:PCBM Blend Thin Films J. Am. Chem. Soc. 2011, 133, 9834-9843
55. Gao, Y.; Grey, J. K. Resonance Chemical Imaging of Polythiophene/ Fullerene Photovoltaic Thin Films: Mapping Morphology-Dependent Aggregated and Unaggregated Cî-C Species J. Am. Chem. Soc. 2009, 131, 9654-9662
56. Lagutchev, A.; Hambir, S. A.; Dlott, D. D. Nonresonant Background Suppression in Broadband Vibrational Sum-Frequency Generation Spectroscopy J. Phys. Chem. C 2007, 111, 13645-13647
57. Stiopkin, I. V.; Jayathilake, H. D.; Weeraman, C.; Benderskii, A. V. Temporal Effects on Spectroscopic Line Shapes, Resolution, and Sensitivity of the Broad-Band Sum Frequency Generation J. Chem. Phys. 2010, 132, 234503 1-9
58. Curtis, A. D.; Asplund, M. C.; Patterson, J. E. Use of Variable Time-Delay Sum-Frequency Generation for Improved Spectroscopic Analysis J. Phys. Chem. C 2011, 115, 19303-19310
59. Ward, R. N.; Duffy, D. C.; Davies, P. B.; Bain, C. D. Sum-Frequency Spectroscopy of Surfactants Adsorbed at a Flat Hydrophobic Surface J. Phys. Chem. 1994, 98, 8536-8542
60. 4 Interface as Studied by Sum-Frequency Vibrational Spectroscopy Langmuir 1998, 14, 6722-6727
61. Weeraman, C.; Yatawara, A. K.; Bordenyuk, A. N.; Benderskii, A. V. Effect of Nanoscale Geometry on Molecular Conformation: Vibrational Sum-Frequency Generation of Alkanethiols on Gold Nanoparticles J. Am. Chem. Soc. 2006, 128, 14244-14245
62. Simpson, G. J.; Rowlen, K. L. An Shg Magic Angle: Dependence of Second Harmonic Generation Orientation Measurements on the Width of the Orientation Distribution J. Am. Chem. Soc. 1999, 121, 2635-2636
63. Wang, J.; Paszti, Z.; Even, M. A.; Chen, Z. Measuring Polymer Surface Ordering Differences in Air and Water by Sum Frequency Generation Vibrational Spectroscopy J. Am. Chem. Soc. 2002, 124, 7016-7023
64. Beaujuge, P. M.; Amb, C. M.; Reynolds, J. R. Spectral Engineering in Π-Conjugated Polymers with Intramolecular Donor-Acceptor Interactions Acc. Chem. Res. 2010, 43, 1396-1407
65. Bellamy, L. J. The Infrared Spectra of Complex Molecules, 3 rd ed.; Springer: New York, 1975; Vol. 1.
66. Korovyanko, O. J.; Österbacka, R.; Jiang, X. M.; Vardeny, Z. V.; Janssen, R. A. J. Photoexcitation Dynamics in Regioregular and Regiorandom Polythiophene Films Phys. Rev. B 2001, 64, 235122 1-6
67. Li, G.; Shrotriya, V.; Yao, Y.; Yang, Y. Investigation of Annealing Effects and Film Thickness Dependence of Polymer Solar Cells Based on Poly(3-Hexylthiophene) J. Appl. Phys. 2005, 98, 043704 1-5
68. Dannetun, P.; Boman, M.; Stafstrom, S.; Salaneck, W. R.; Lazzaroni, R.; Fredriksson, C.; Bredas, J. L.; Zamboni, R.; Taliani, C. The Chemical and Electronic Structure of the Interface between Aluminum and Polythiophene Semiconductors J. Chem. Phys. 1993, 99, 664-672
69. Logdlund, M.; Bredas, J. L. Theoretical Studies of the Interaction between Aluminum and Poly(P-Phenylenevinylene) and Derivatives J. Chem. Phys. 1994, 101, 4357-4364
70. Kaune, G.; Metwalli, E.; Meier, R.; Körstgens, V.; Schlage, K.; Couet, S.; Röhlsberger, R.; Roth, S. V.; Müller-Buschbaum, P. Growth and Morphology of Sputtered Aluminum Thin Films on P3HT Surfaces ACS Appl. Mater. Interf. 2011, 3, 1055-1062
71. Birgerson, J.; Fahlman, M.; Bröms, P.; Salaneck, W. R. Conjugated Polymer Surfaces and Interfaces: A Mini-Review and Some New Results Syn. Met. 1996, 80, 125-130
72. Burkhart, B.; Khlyabich, P. P.; Cakir Canak, T.; LaJoie, T. W.; Thompson, B. C. "Semi-Random" Multichromophoric rr-P3HT Analogues for Solar Photon Harvesting Macromolecules 2011, 44, 1242-1246
73. Malyk, S.; Shalhout, F. Y.; O'Leary, L. E.; Lewis, N. S.; Benderskii, A. V. Vibrational Sum Frequency Spectroscopic Investigation of the Azimuthal Anisotropy and Rotational Dynamics of Methyl-Terminated Si(111) Surfaces J. Phys. Chem. C 2012, 117, 935-944