Large work function shift of organic semiconductors inducing enhanced interfacial electron transfer in organic optoelectronics enabled by porphyrin aggregated nanostructures
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- 作者：Maria Vasilopoulou (1)
Antonios M. Douvas (1)
Dimitra G. Georgiadou (1)
Vassilios Constantoudis (1)
Dimitris Davazoglou (1)
Stella Kennou (2)
Leonidas C. Palilis (3)
Dimitra Daphnomili (4)
Athanassios G. Coutsolelos (4)
Panagiotis Argitis (1) - 关键词：porphyrins ; OLEDs ; OPVs ; aggregates
- 刊名：Nano Research
- 出版年：2014
- 出版时间：May 2014
- 年：2014
- 卷：7
- 期：5
- 页码：679-693
- 全文大小：
- 参考文献：1. Elemans, J.; Van Hameren, R.; Nolte, R. J. M.; Rowan, A. E. Molecular materials by self-assembly of porphyrins, phthalocyanines, and perylenes. / Adv. Mater. 2006, / 18, 1251-266. CrossRef
2. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. A field guide to foldamers. / Chem. Rev. 2001, / 101, 3893-011. CrossRef
3. Hartgerink, J. D.; Beniash, E.; Stupp, S. I. Self-assembly and mineralization of peptide-amphiphile nanofibers. / Science 2001, / 294, 1684-688. CrossRef
4. Wang, Z. C.; Li, Z. Y.; Medforth, C. J.; Shelnutt, J. A. Self-assembly and self-metallization of porphyrin nanosheets. / J. Am. Chem. Soc. 2007, / 129, 2440-441. CrossRef
5. Shimizu, T.; Masuda, M.; Minamikawa, H. Supramolecular nanotube architectures based on amphiphilic molecules. / Chem. Rev. 2005, / 105, 1401-443. CrossRef
6. He, Y.; Ye, T.; Borguet, E. Porphyrin self-assembly at electrochemical interfaces: Role of potential modulated surface mobility. / J. Am. Chem. Soc. 2002, / 124, 11964-1970. CrossRef
7. Takahashi, R.; Kobuke, Y. Hexameric macroring of gable-porphyrins as a light-harvesting antenna mimic. / J. Am. Chem. Soc. 2003, / 125, 2372-373. CrossRef
8. Johnson, D. G.; Niemczyk, M. P.; Minsek, D. W.; Wiederrecht, G. P.; Svec, W. A.; Gaines, G. L.; Wasielewski, M. R. Photochemical electron transfer in chlorophyll-porphyrin-quinone triads: The role of the porphyrin-bridging molecule. / J. Am. Chem. Soc. 1993, / 115, 5692-701. CrossRef
9. Grimsdale, A. C.; Mullen, K. The chemistry of organic nanomaterials. / Angew. Chem., Int. Ed. 2005, / 44, 5592-629. CrossRef
10. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. About supramolecular assemblies of pi-conjugated systems. / Chem. Rev. 2005, / 105, 1491-546. CrossRef
11. Minari, T.; Seto, M.; Nemoto, T.; Isoda, S.; Tsukagoshi, K.; Aoyagi, Y. Molecular-packing-enhanced charge transport in organic field-effect transistors based on semiconducting porphyrin crystals. / Appl. Phys. Lett. 2007, / 91, 123501. CrossRef
12. Wu, L.; Feng, L. Y.; Ren, J. S.; Qu, X. G. Electrochemical detection of dopamine using porphyrin-functionalized graphene. / Biosens. Bioelectron. 2012, / 34, 57-2. CrossRef
13. Ng, K. K.; Lovell, J. F.; Vedadi, A.; Hajian, T.; Zheng, G. Self-assembled porphyrin nanodiscs with structure-dependent activation for phototherapy and photodiagnostic applications. / ACS Nano 2013, / 7, 3484-490. CrossRef
14. Lazarides, T.; Sazanovich, I. V.; Simaan, A. J.; Kafentzi, M. C.; Delor, M.; Mekmouche, Y.; Faure, B.; Reglier, M.; Weinstein, J. A.; Coutsolelos, A. G. et al. Visible light-driven O2 reduction by a porphyrin-laccase system. / J. Am. Chem. Soc. 2013, / 135, 3095-103. CrossRef
15. Leininger, S.; Olenyuk, B.; Stang, P. J. Self-assembly of discrete cyclic nanostructures mediated by transition metals. / Chem. Rev. 2000, / 100, 853-07. CrossRef
16. Hoang, M. H.; Kim, Y.; Kim, M.; Kim, K. H.; Lee, T. W.; Nguyen, D. N.; Kim, S. J.; Lee, K.; Lee, S. J.; Choi, D. H. Unusually high-performing organic field-effect transistors based on π-extended semiconducting porphyrins. / Adv. Mater. 2012, / 24, 5363-367. CrossRef
17. Burrows, P. E.; Forrest, S. R.; Sibley, S. P.; Thompson, M. E. Color-tunable organic light-emitting devices. / Appl. Phys. Lett. 1996, / 69, 2959-961. CrossRef
18. Borek, C.; Hanson, K.; Djurovich, P. I.; Thompson, M. E.; Aznavour, K.; Bau, R.; Sun, Y. R.; Forrest, S. R.; Brooks, J.; Michalski, L. et al. Highly efficient, near-infrared electrophosphorescence from a Pt-metalloporphyrin complex. / Angew. Chem., Int. Ed. 2007, / 46, 1109-112. CrossRef
19. Ostrowski, J. C.; Susumu, K.; Robinson, M. R.; Therien, M. J.; Bazan, G. C. Near-infrared electroluminescent light-emitting devices based on ethyne-bridged porphyrin fluorophores. / Adv. Mater. 2003, / 15, 1296-300. CrossRef
20. Shao, Y.; Yang, Y. Efficient organic heterojunction photovoltaic cells based on triplet materials. / Adv. Mater. 2005, / 17, 2841-844. CrossRef
21. Perez, M. D.; Borek, C.; Djurovich, P. I.; Mayo, E. I.; Lunt, R. R.; Forrest, S. R.; Thompson, M. E. Organic photovoltaics using tetraphenylbenzoporphyrin complexes as donor layers. / Adv. Mater. 2009, / 21, 1517-520. CrossRef
22. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Polymer photovoltaic cells: Enhanced efficiencies via a network of internal donor-acceptor heterojunctions. / Science 1995, / 270, 1789-791. CrossRef
23. VanSlyke, S. A.; Chen, C. H.; Tang, C. W. Organic electroluminescent devices with improved stability. / Appl. Phys. Lett. 1996, / 69, 2160-162. CrossRef
24. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Bredas, J. L.; Logdlund, M. et al. Electroluminescence in conjugated polymers. / Nature 1999, / 397, 121-28. CrossRef
25. Chen, H. Y.; Hou, J. H.; Zhang, S. Q.; Liang, Y. Y.; Yang, G. W.; Yang, Y.; Yu, L. P.; Wu, Y.; Li, G. Polymer solar cells with enhanced open-circuit voltage and efficiency. / Nat. Photonics 2009, / 3, 649-53. CrossRef
26. Green, M. A.; Emery, K.; Hishikawa, Y.; Warta, W.; Dunlop, E. D. Solar cell efficiency tables (version 41). / Prog. Photovoltaics 2013, / 21, 1-1. CrossRef
27. Ma, H.; Yip, H. L.; Huang, F.; Jen, A. K. Y. Interface engineering for organic electronics. / Adv. Funct. Mater. 2010, / 20, 1371-388. CrossRef
28. Sessolo, M.; Bolink, H. J. Hybrid organic-inorganic light-emitting diodes. / Adv. Mater. 2011, / 23, 1829-845. CrossRef
29. Vandewal, K.; Tvingstedt, K.; Gadisa, A.; Inganas, O.; Manca, J. V. On the origin of the open-circuit voltage of polymer-fullerene solar cells. / Nat. Mater. 2009, / 8, 904-09. CrossRef
30. Yuan, Y. B.; Reece, T. J.; Sharma, P.; Poddar, S.; Ducharme, S.; Gruverman, A.; Yang, Y.; Huang, J. S. Efficiency enhancement in organic solar cells with ferroelectric polymers. / Nat. Mater. 2011, / 10, 296-02. CrossRef
31. Forrest, S. R. The path to ubiquitous and low-cost organic electronic appliances on plastic. / Nature 2004, / 428, 911-18. CrossRef
32. Brabec, C. J.; Gowrisanker, S.; Halls, J. J. M.; Laird, D.; Jia, S. J.; Williams, S. P. Polymer-fullerene bulk-heterojunction solar cells. / Adv. Mater. 2010, / 22, 3839-856. CrossRef
33. Veldman, D.; Meskers, S. C. J.; Janssen, R. A. J. The energy of charge-transfer states in electron donor-acceptor blends: Insight into the energy losses in organic solar cells. / Adv. Funct. Mater. 2009, / 19, 1939-948. CrossRef
34. Haque, S. A.; Koops, S.; Tokmoldin, N.; Durrant, J. R.; Huang, J. S.; Bradley, D. D. C.; Palomares, E. A multilayered polymer light-emitting diode using a nanocrystalline metal-oxide film as a charge-injection electrode. / Adv. Mater. 2007, / 19, 683-87. CrossRef
35. Bolink, H. J.; Coronado, E.; Orozco, J.; Sessolo, M. Efficient polymer light-emitting diode using air-stable metal oxides as electrodes. / Adv. Mater. 2009, / 21, 79-2. CrossRef
36. Kabra, D.; Lu, L. P.; Song, M. H.; Snaith, H. J.; Friend, R. H. Efficient single-layer polymer light-emitting diodes. / Adv. Mater. 2010, / 22, 3194-198. CrossRef
37. Lee, B. R.; Choi, H.; SunPark, J.; Lee, H. J.; Kim, S. O.; Kim, J. Y.; Song, M. H. Surface modification of metal oxide using ionic liquid molecules in hybrid organic-inorganic optoelectronic devices. / J. Mater. Chem. 2011, / 21, 2051-053. CrossRef
38. Li, Y.; Zhang, D. Q.; Duan, L.; Zhang, R.; Wang, L. D.; Qiu, Y. Elucidation of the electron injection mechanism of evaporated cesium carbonate cathode interlayer for organic light-emitting diodes. / Appl. Phys. Lett. 2007, / 90, 12119. CrossRef
39. Huang, J. S.; Xu, Z.; Yang, Y. Low-work-function surface formed by solution-processed and thermally deposited nanoscale layers of cesium carbonate. / Adv. Funct. Mater. 2007, / 17, 1966-973. CrossRef
40. Fang, J. F.; Wallikewitz, B. H.; Gao, F.; Tu, G. L.; Muller, C.; Pace, G.; Friend, R. H.; Huck, W. T. S. Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes. / J. Am. Chem. Soc. 2011, / 133, 683-85. CrossRef
41. Hoven, C. V.; Yang, R. Q.; Garcia, A.; Crockett, V.; Heeger, A. J.; Bazan, G. C.; Nguyen, T. Q. Electron injection into organic semiconductor devices from high work function cathodes. / Proc. Natl. Acad. Sci. U.S.A. 2008, / 105, 12730-2735. CrossRef
42. Shao, Y.; Bazan, G. C.; Heeger, A. J. Long-lifetime polymer light-emitting electrochemical cells. / Adv. Mater. 2007, / 19, 365-70. CrossRef
43. Jin, Y.; Bazan, G. C.; Heeger, A. J.; Kim, J. Y.; Lee, K. Improved electron injection in polymer light-emitting diodes using anionic conjugated polyelectrolyte. / Appl. Phys. Lett. 2008, / 93, 123304. CrossRef
44. Marcilla, R.; Mecerreyes, D.; Winroth, G.; Brovelli, S.; Yebra, M. D. R.; Cacialli, F. Light-emitting electrochemical cells using polymeric ionic liquid/polyfluorene blends as luminescent material. / Appl. Phys. Lett. 2010, / 96, 43308. CrossRef
45. Xiao, L. X.; Xing, X.; Chen, Z. J.; Qu, B.; Lan, H. L.; Gong, Q. H.; Kido, J. Highly efficient electron-transporting/injecting and thermally stable naphthyridines for organic electrophosphorescent devices. / Adv. Funct. Mater. 2013, / 23, 1323-330. CrossRef
46. Su, S. J.; Chiba, T.; Takeda, T.; Kido, J. Pyridine-containing triphenylbenzene derivatives with high electron mobility for highly efficient phosphorescent OLEDs. / Adv. Mater. 2008, / 20, 2125-130. CrossRef
47. Yoon, S. M.; Lou, S. J.; Loser, S.; Smith, J.; Chen, L. X.; Facchetti, A.; Marks, T. J. Fluorinated copper phthalocyanine nanowires for enhancing interfacial electron transport in organic solar cells. / Nano Lett. 2012, / 12, 6315-321. CrossRef
48. Vasilopoulou, M.; Dimitrakis, P.; Georgiadou, D. G.; Velessiotis, D.; Papadimitropoulos, G.; Davazoglou, D.; Coutsolelos, A. G.; Argitis, P. Emergence of ambient temperature ferroelectricity in meso-tetrakis(1-methylpyridinium-4-yl)porphyrin chloride thin films. / Appl. Phys. Lett. 2013, / 103, 22908. CrossRef
49. Vasilopoulou, M.; Georgiadou, D. G.; Douvas, A. M.; Soultati, A.; Constantoudis, V.; Davazoglou, D.; Gardelis, S.; Palilis, L. C.; Fakis, M.; Kennou, S. et al. Porphyrin oriented self-assembled nanostructures for efficient exciton dissociation in high-performing organic photovoltaics. / J. Mater. Chem. A 2014, / 2, 182-92. CrossRef
50. Kasha, M.; Rawls, H. R.; Ashraf El-Bayoumi, M. The exciton model in molecular spectroscopy. / Pure Appl. Chem. 1965, / 11, 371-92. CrossRef
51. Gao, Y. N.; Zhang, X. M.; Ma, C. Q.; Li, X. Y.; Jiang, J. Z. Morphology-controlled self-assembled nanostructures of 5,15-di 4-(5-acetylsulfanylpentyloxy)phenyl porphyrin derivatives. Effect of Metal-Ligand coordination bonding on tuning the intermolecular interaction. / J. Am. Chem. Soc. 2008, / 130, 17044-7052. CrossRef
52. Panda, M. K.; Ladomenou, K.; Coutsolelos, A. G. Porphyrins in bio-inspired transformations: Light-harvesting to solar cell. / Coord. Chem. Rev. 2012, / 256, 2601-627. CrossRef
53. Yokoyama, D.; Sasabe, H.; Furukawa, Y.; Adachi, C.; Kido, J. Molecular stacking induced by intermolecular C-H…N hydrogen bonds leading to high carrier mobility in vacuum-deposited organic films. / Adv. Funct. Mater. 2011, / 21, 1375-382 CrossRef
54. Bohn, P. W. Aspects of structure and energy-transport in artificial molecular assemblies. / Annu. Rev. Phys. Chem. 1993, / 44, 37-0. CrossRef
55. Mooney, W. F.; Whitten, D. G. Energy- and electron-transfer quenching of surfactant trans-stilbenes in supported multilayers: The use of hydrophobic substrate chromophores to determine short-range distance dependence in assemblies. / J. Am. Chem. Soc. 1986, / 108, 5712-719. CrossRef
56. Maiti, N. C.; Ravikanth, M.; Mazumdar, S.; Periasamy, N. Fluorescence dynamics of noncovalently linked porphyrin dimers, and aggregates. / J. Phys. Chem. 1995, / 99, 17192-7197. CrossRef
57. Huijser, A.; Suijkerbuijk, B.; Gebbink, R.; Savenije, T. J.; Siebbeles, L. D. A. Efficient exciton transport in layers of self-assembled porphyrin derivatives. / J. Am. Chem. Soc. 2008, / 130, 2485-492. CrossRef
58. Zhou, H.; Zhang, Y.; Seifter, J.; Collins, S. D.; Luo, C.; Bazan, G. C.; Ngyen, T. Q.; Heeger, A. High-efficiency polymer solar cells enhanced by solvent treatment. / Adv. Mater., 2013, / 25, 1646-652. CrossRef
59. Vasilopoulou, M.; Douvas, A. M.; Georgiadou, D. G.; Palilis, L. C.; Kennou, S.; Sygellou, L.; Soultati, A.; Kostis, I.; Papadimitropoulos, G.; Davazoglou, D. et al. The influence of hydrogenation and oxygen vacancies on Molybdenum oxides work function and gap states for application in organic optoelectronics. / J. Am. Chem. Soc. 2012, / 134, 16178-6187. CrossRef
60. Vasilopoulou, M.; Palilis, L. C.; Georgiadou, D. G.; Kennou, S.; Kostis, I.; Davazoglou, D.; Argitis, P. Barrierless hole injection through sub-bandgap occupied states in organic light emitting diodes using substoichiometric MoO( / x) anode interfacial layer. / Appl. Phys. Lett. 2012, / 100, 13311. CrossRef
61. Sessolo, M.; Bolink, H. Hybrid organic-inorganic light-emitting diodes / Adv. Mater. 2011, / 23, 1829-845. CrossRef
62. Zhang, Y.; Blom, P. W. M. Electron and hole transport in poly(fluorene-benzothiadiazole). / Appl. Phys. Lett. 2011, / 98, 143504. CrossRef - 作者单位：Maria Vasilopoulou (1)
Antonios M. Douvas (1)
Dimitra G. Georgiadou (1)
Vassilios Constantoudis (1)
Dimitris Davazoglou (1)
Stella Kennou (2)
Leonidas C. Palilis (3)
Dimitra Daphnomili (4)
Athanassios G. Coutsolelos (4)
Panagiotis Argitis (1)
1. Institute of Nanoscience and Nanotechnology (INN), National Center for Scientific Research “Demokritos- 153 10 Aghia Paraskevi Attikis, Athens, Greece
2. Department of Chemical Engineering, University of Patras, 26500, Patras, Greece
3. Departmen of Physics, University of Patras, 26500, Patras, Greece
4. Laboratory of Bioinorganic Chemistry, Chemistry Department, University of Crete, Voutes Campus, 71003, Heraklion, Crete, Greece - ISSN：1998-0000
文摘
We report on large work function shifts induced by the coverage of several organic semiconducting (OSC) films commonly used in organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs) with a porphyrin aggregated layer. The insertion between the organic film and the aluminum cathode of an aggregated layer based on the meso-tetrakis(1-methylpyridinium-4-yl) porphyrin chloride (porphyrin 1), with its molecules adopting a face-to-face orientation parallel to the organic substrate, results in a significant shift of the OSC work function towards lower values due to the formation of a large interfacial dipole and induces large enhancement of either the OLED or OPV device efficiency. OLEDs based on poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(1,4-benzo-2,1-3-thiadiazole)] (F8BT) and incorporating the porphyrin 1 at the cathode interface exhibited current efficiency values up to 13.8 cd/A, an almost three-fold improvement over the efficiency of 4.5 cd/A of the reference device. Accordingly, OPVs based on poly(3-hexylthiophene) (P3HT), [6,6]-phenyl-C61 butyric acid methyl ester (PC61BM) and porphyrin 1 increased their external quantum efficiencies to 4.4% relative to 2.7% for the reference device without the porphyrin layer. The incorporation of a layer based on the zinc meso-tetrakis (1-methylpyridinium-4-yl)porphyrin chloride (porphyrin 2), with its molecules adopting an edge-to-edge orientation, also introduced improvements, albeit more modest in all cases, highlighting the impact of molecular orientation.