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Phosphonate functionalized oxadiazole derivative as an efficient electron transporting material for solution-processed blue electrophosphorescent devicesJianhong Lü, Zhihua Ma, Bin Meng, Dan Sui, Baohua Zhang, Zhiyuan Xie, Xiabin Jing, Fosong Wang, Junqiao Ding, and Lixiang Wang »View Author Affiliations
Jianhong Lü,1,2
Zhihua Ma,1,2
Bin Meng,1
Dan Sui,1
Baohua Zhang,1
Zhiyuan Xie,1
Xiabin Jing,1
Fosong Wang,1
Junqiao Ding,1,3
and Lixiang Wang1,4
1State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China 2Graduate School of the Chinese Academy of Sciences, Beijing 100039, China |
Optics Express, Vol. 19, Issue S6, pp. A1241-A1249 (2011)
http://dx.doi.org/10.1364/OE.19.0A1241
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Abstract
An efficient electron transporting material, P-OXD (1,3-bis[(4-(4-diethylphosphoryl-butyl-phenyl))-1,3,4-oxidiazol-2-yl]phenylene), has been synthesized and thoroughly characterized. Due to its alcohol-soluble nature, P-OXD can be spin-coated atop the light emitting layer to form high quality film without dissolving the underlying layer. As a consequence, the double-layer blue electrophosphorescent device has been successfully fabricated, giving a peak luminous efficiency of 10.5 cd/A, and a maximum brightness of 8200 cd/m2 with the Commission Internationale de L’Eclairage (CIE) coordinates of (0.16, 0.33). The promising results indicate that P-OXD has a potential application in solution-processed multilayer polymer light-emitting diodes.
© 2011 OSA
OCIS Codes
(160.4890) Materials : Organic materials
(230.0250) Optical devices : Optoelectronics
(230.3670) Optical devices : Light-emitting diodes
ToC Category:
Light-Emitting Diodes
History
Original Manuscript: July 27, 2011
Revised Manuscript: September 14, 2011
Manuscript Accepted: September 14, 2011
Published: November 7, 2011
Virtual Issues
Organic Light-Emitting Diodes (2011) Optics Express
Citation
Jianhong Lü, Zhihua Ma, Bin Meng, Dan Sui, Baohua Zhang, Zhiyuan Xie, Xiabin Jing, Fosong Wang, Junqiao Ding, and Lixiang Wang, "Phosphonate functionalized oxadiazole derivative as an efficient electron transporting material for solution-processed blue electrophosphorescent devices," Opt. Express 19, A1241-A1249 (2011)
http://www.opticsinfobase.org/oe/abstract.cfm?URI=oe-19-S6-A1241
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References
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- R. Yang, Y. Xu, X.-D. Dang, T.-Q. Nguyen, Y. Cao, and G. C. Bazan, “Conjugated oligoelectrolyte electron transport/injection layers for organic optoelectronic devices,” J. Am. Chem. Soc.130(11), 3282–3283 (2008). [CrossRef] [PubMed]
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- L. Chen, J. Ding, Y. Cheng, L. Wang, X. Jing, and F. Wang, “Twofold terminal post-functionalization of acetylacetone with hole- and electron-transporting fragments,” Tetrahedron Lett.51(35), 4612–4616 (2010). [CrossRef]
- B. Zhang, C. Qin, J. Ding, L. Chen, Z. Xie, Y. Cheng, and L. Wang, “High-performance all-polymer white-light-emitting diodes using polyfluorene containing phosphonate groups as an efficient electron-injection layer,” Adv. Funct. Mater.20(17), 2951–2957 (2010). [CrossRef]
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- V. E. Choong, M. G. Mason, C. W. Tang, and Y. G. Gao, “Investigation of the interface formation between calcium and tris-(8-hydroxy quinoline) aluminum,” Appl. Phys. Lett.72(21), 2689–2691 (1998). [CrossRef]
- R. Yang, Y. Xu, X.-D. Dang, T.-Q. Nguyen, Y. Cao, and G. C. Bazan, “Conjugated oligoelectrolyte electron transport/injection layers for organic optoelectronic devices,” J. Am. Chem. Soc.130(11), 3282–3283 (2008). [CrossRef] [PubMed]
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- L. Chen, J. Ding, Y. Cheng, L. Wang, X. Jing, and F. Wang, “Twofold terminal post-functionalization of acetylacetone with hole- and electron-transporting fragments,” Tetrahedron Lett.51(35), 4612–4616 (2010). [CrossRef]
- C. Duan, L. Wang, K. Zhang, X. Guan, and F. Huang, “Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)23(14), 1665–1669 (2011). [CrossRef] [PubMed]
- C. Zhong, C. Duan, F. Huang, H. Wu, and Y. Cao, “Materials and devices toward fully solution processable organic light-emitting diodes,” Chem. Mater.23(3), 326–340 (2011). [CrossRef]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
- R. J. Holmes, S. R. Forrest, Y. J. Tung, R. C. Kwong, J. J. Brown, S. Garon, and M. E. Thompson, “Blue organic electrophosphorescence using exothermic host-guest energy transfer,” Appl. Phys. Lett.82(15), 2422–2424 (2003). [CrossRef]
- M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, and S. R. Forrest, “Highly efficient phosphorescent emission from organic electroluminescent devices,” Nature395(6698), 151–154 (1998). [CrossRef]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
- Q. T. Le, L. Yan, Y. G. Gao, M. G. Mason, D. J. Giesen, and C. W. Tang, “Photoemission study of aluminum/tris-(8-hydroxyquinoline) aluminum and aluminum/LiF/tris-(8-hydroxyquinoline) aluminum interfaces,” J. Appl. Phys.87(1), 375–379 (2000). [CrossRef]
- V. E. Choong, M. G. Mason, C. W. Tang, and Y. G. Gao, “Investigation of the interface formation between calcium and tris-(8-hydroxy quinoline) aluminum,” Appl. Phys. Lett.72(21), 2689–2691 (1998). [CrossRef]
- T. V. Pho, P. Zalar, A. Garcia, T.-Q. Nguyen, and F. Wudl, “Electron injection barrier reduction for organic light-emitting devices by quinacridone derivatives,” Chem. Commun. (Camb.)46(43), 8210–8212 (2010). [CrossRef] [PubMed]
- C. V. Hoven, A. Garcia, G. C. Bazan, and T.-Q. Nguyen, “Recent Applications of conjugated polyelectrolytes in optoelectronic devices,” Adv. Mater. (Deerfield Beach Fla.)20(20), 3793–3810 (2008). [CrossRef]
- R. J. Holmes, S. R. Forrest, Y. J. Tung, R. C. Kwong, J. J. Brown, S. Garon, and M. E. Thompson, “Blue organic electrophosphorescence using exothermic host-guest energy transfer,” Appl. Phys. Lett.82(15), 2422–2424 (2003). [CrossRef]
- Q. T. Le, L. Yan, Y. G. Gao, M. G. Mason, D. J. Giesen, and C. W. Tang, “Photoemission study of aluminum/tris-(8-hydroxyquinoline) aluminum and aluminum/LiF/tris-(8-hydroxyquinoline) aluminum interfaces,” J. Appl. Phys.87(1), 375–379 (2000). [CrossRef]
- X. Gong, S. Wang, D. Moses, G. C. Bazan, and A. J. Heeger, “Multilayer polymer light-emitting diodes: White-light emission with high efficiency,” Adv. Mater. (Deerfield Beach Fla.)17(17), 2053–2058 (2005). [CrossRef]
- C. Duan, L. Wang, K. Zhang, X. Guan, and F. Huang, “Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)23(14), 1665–1669 (2011). [CrossRef] [PubMed]
- X. Xu, B. Han, J. Chen, J. Peng, H. Wu, and Y. Cao, “2,7-Carbazole-1,4-phenylene Copolymers with polar side chains for cathode modifications in polymer light-emitting diodes,” Macromolecules44(11), 4204–4212 (2011). [CrossRef]
- X. Gong, S. Wang, D. Moses, G. C. Bazan, and A. J. Heeger, “Multilayer polymer light-emitting diodes: White-light emission with high efficiency,” Adv. Mater. (Deerfield Beach Fla.)17(17), 2053–2058 (2005). [CrossRef]
- R. J. Holmes, S. R. Forrest, Y. J. Tung, R. C. Kwong, J. J. Brown, S. Garon, and M. E. Thompson, “Blue organic electrophosphorescence using exothermic host-guest energy transfer,” Appl. Phys. Lett.82(15), 2422–2424 (2003). [CrossRef]
- C. V. Hoven, A. Garcia, G. C. Bazan, and T.-Q. Nguyen, “Recent Applications of conjugated polyelectrolytes in optoelectronic devices,” Adv. Mater. (Deerfield Beach Fla.)20(20), 3793–3810 (2008). [CrossRef]
- C. Duan, L. Wang, K. Zhang, X. Guan, and F. Huang, “Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)23(14), 1665–1669 (2011). [CrossRef] [PubMed]
- C. Zhong, C. Duan, F. Huang, H. Wu, and Y. Cao, “Materials and devices toward fully solution processable organic light-emitting diodes,” Chem. Mater.23(3), 326–340 (2011). [CrossRef]
- F. Huang, H. Wu, and Y. Cao, “Water/alcohol soluble conjugated polymers as highly efficient electron transporting/injection layer in optoelectronic devices,” Chem. Soc. Rev.39(7), 2500–2521 (2010). [CrossRef] [PubMed]
- F. Huang, P.-I. Shih, C.-F. Shu, Y. Chi, and A. K. Y. Jen, “Highly efficient polymer white-light-emitting diodes based on lithium salts doped electron transporting layer,” Adv. Mater. (Deerfield Beach Fla.)21(3), 361–365 (2009). [CrossRef]
- F. Huang, Y.-H. Niu, Y. Zhang, J.-W. Ka, M. S. Liu, and A. K. Y. Jen, “A conjugated, neutral surfactant as electron-injection material for high-efficiency polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)19(15), 2010–2014 (2007). [CrossRef]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
- G. Hughes and M. R. Bryce, “Electron-transporting materials for organic electroluminescent and electrophosphorescent devices,” J. Mater. Chem.15(1), 94–107 (2005). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- X. H. Yang, F. Jaiser, S. Klinger, and D. Neher, “Blue polymer electrophosphorescent devices with different electron-transporting oxadiazoles,” Appl. Phys. Lett.88(2), 021107 (2006). [CrossRef]
- F. Huang, P.-I. Shih, C.-F. Shu, Y. Chi, and A. K. Y. Jen, “Highly efficient polymer white-light-emitting diodes based on lithium salts doped electron transporting layer,” Adv. Mater. (Deerfield Beach Fla.)21(3), 361–365 (2009). [CrossRef]
- F. Huang, Y.-H. Niu, Y. Zhang, J.-W. Ka, M. S. Liu, and A. K. Y. Jen, “A conjugated, neutral surfactant as electron-injection material for high-efficiency polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)19(15), 2010–2014 (2007). [CrossRef]
- A. P. Kulkarni, C. J. Tonzola, A. Babel, and S. A. Jenekhe, “Electron transport materials for organic light-emitting diodes,” Chem. Mater.16(23), 4556–4573 (2004). [CrossRef]
- H. Jiang, P. Taranekar, J. R. Reynolds, and K. S. Schanze, “Conjugated polyelectrolytes: synthesis, photophysics, and applications,” Angew. Chem. Int. Ed. Engl.48(24), 4300–4316 (2009). [CrossRef] [PubMed]
- L. Chen, J. Ding, Y. Cheng, L. Wang, X. Jing, and F. Wang, “Twofold terminal post-functionalization of acetylacetone with hole- and electron-transporting fragments,” Tetrahedron Lett.51(35), 4612–4616 (2010). [CrossRef]
- C. S. Wang, G. Y. Jung, A. S. Batsanov, M. R. Bryce, and M. C. Petty, “New electron-transporting materials for light emitting diodes: 1,3,4-oxadiazole-pyridine and 1,3,4-oxadiazole-pyrimidine hybrids,” J. Mater. Chem.12(2), 173–180 (2002). [CrossRef]
- F. Huang, Y.-H. Niu, Y. Zhang, J.-W. Ka, M. S. Liu, and A. K. Y. Jen, “A conjugated, neutral surfactant as electron-injection material for high-efficiency polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)19(15), 2010–2014 (2007). [CrossRef]
- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- X. H. Yang, F. Jaiser, S. Klinger, and D. Neher, “Blue polymer electrophosphorescent devices with different electron-transporting oxadiazoles,” Appl. Phys. Lett.88(2), 021107 (2006). [CrossRef]
- F. So and D. Kondakov, “Degradation mechanisms in small-molecule and polymer organic light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)22(34), 3762–3777 (2010). [CrossRef] [PubMed]
- A. P. Kulkarni, C. J. Tonzola, A. Babel, and S. A. Jenekhe, “Electron transport materials for organic light-emitting diodes,” Chem. Mater.16(23), 4556–4573 (2004). [CrossRef]
- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- R. J. Holmes, S. R. Forrest, Y. J. Tung, R. C. Kwong, J. J. Brown, S. Garon, and M. E. Thompson, “Blue organic electrophosphorescence using exothermic host-guest energy transfer,” Appl. Phys. Lett.82(15), 2422–2424 (2003). [CrossRef]
- Q. T. Le, L. Yan, Y. G. Gao, M. G. Mason, D. J. Giesen, and C. W. Tang, “Photoemission study of aluminum/tris-(8-hydroxyquinoline) aluminum and aluminum/LiF/tris-(8-hydroxyquinoline) aluminum interfaces,” J. Appl. Phys.87(1), 375–379 (2000). [CrossRef]
- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- F. Huang, Y.-H. Niu, Y. Zhang, J.-W. Ka, M. S. Liu, and A. K. Y. Jen, “A conjugated, neutral surfactant as electron-injection material for high-efficiency polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)19(15), 2010–2014 (2007). [CrossRef]
- Q. T. Le, L. Yan, Y. G. Gao, M. G. Mason, D. J. Giesen, and C. W. Tang, “Photoemission study of aluminum/tris-(8-hydroxyquinoline) aluminum and aluminum/LiF/tris-(8-hydroxyquinoline) aluminum interfaces,” J. Appl. Phys.87(1), 375–379 (2000). [CrossRef]
- V. E. Choong, M. G. Mason, C. W. Tang, and Y. G. Gao, “Investigation of the interface formation between calcium and tris-(8-hydroxy quinoline) aluminum,” Appl. Phys. Lett.72(21), 2689–2691 (1998). [CrossRef]
- K. Meerholz, “Device physics: enlightening solutions,” Nature437(7057), 327–328 (2005). [CrossRef] [PubMed]
- X. Gong, S. Wang, D. Moses, G. C. Bazan, and A. J. Heeger, “Multilayer polymer light-emitting diodes: White-light emission with high efficiency,” Adv. Mater. (Deerfield Beach Fla.)17(17), 2053–2058 (2005). [CrossRef]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
- X. H. Yang, F. Jaiser, S. Klinger, and D. Neher, “Blue polymer electrophosphorescent devices with different electron-transporting oxadiazoles,” Appl. Phys. Lett.88(2), 021107 (2006). [CrossRef]
- T. V. Pho, P. Zalar, A. Garcia, T.-Q. Nguyen, and F. Wudl, “Electron injection barrier reduction for organic light-emitting devices by quinacridone derivatives,” Chem. Commun. (Camb.)46(43), 8210–8212 (2010). [CrossRef] [PubMed]
- R. Yang, Y. Xu, X.-D. Dang, T.-Q. Nguyen, Y. Cao, and G. C. Bazan, “Conjugated oligoelectrolyte electron transport/injection layers for organic optoelectronic devices,” J. Am. Chem. Soc.130(11), 3282–3283 (2008). [CrossRef] [PubMed]
- C. V. Hoven, A. Garcia, G. C. Bazan, and T.-Q. Nguyen, “Recent Applications of conjugated polyelectrolytes in optoelectronic devices,” Adv. Mater. (Deerfield Beach Fla.)20(20), 3793–3810 (2008). [CrossRef]
- F. Huang, Y.-H. Niu, Y. Zhang, J.-W. Ka, M. S. Liu, and A. K. Y. Jen, “A conjugated, neutral surfactant as electron-injection material for high-efficiency polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)19(15), 2010–2014 (2007). [CrossRef]
- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, and S. R. Forrest, “Highly efficient phosphorescent emission from organic electroluminescent devices,” Nature395(6698), 151–154 (1998). [CrossRef]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
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- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- I. D. Parker, Y. Cao, and C. Y. Yang, “Lifetime and degradation effects in polymer light-emitting diodes,” J. Appl. Phys.85(4), 2441–2447 (1999). [CrossRef]
- X. Xu, B. Han, J. Chen, J. Peng, H. Wu, and Y. Cao, “2,7-Carbazole-1,4-phenylene Copolymers with polar side chains for cathode modifications in polymer light-emitting diodes,” Macromolecules44(11), 4204–4212 (2011). [CrossRef]
- C. S. Wang, G. Y. Jung, A. S. Batsanov, M. R. Bryce, and M. C. Petty, “New electron-transporting materials for light emitting diodes: 1,3,4-oxadiazole-pyridine and 1,3,4-oxadiazole-pyrimidine hybrids,” J. Mater. Chem.12(2), 173–180 (2002). [CrossRef]
- T. V. Pho, P. Zalar, A. Garcia, T.-Q. Nguyen, and F. Wudl, “Electron injection barrier reduction for organic light-emitting devices by quinacridone derivatives,” Chem. Commun. (Camb.)46(43), 8210–8212 (2010). [CrossRef] [PubMed]
- T. Beissel, R. E. Powers, T. N. Parac, and K. N. Raymond, “Coordination number incommensurate cluster formation. 8. Dynamic isomerization of a supramolecular tetrahedral M4L6 cluster,” J. Am. Chem. Soc.121(17), 4200–4206 (1999). [CrossRef]
- B. Zhang, C. Qin, J. Ding, L. Chen, Z. Xie, Y. Cheng, and L. Wang, “High-performance all-polymer white-light-emitting diodes using polyfluorene containing phosphonate groups as an efficient electron-injection layer,” Adv. Funct. Mater.20(17), 2951–2957 (2010). [CrossRef]
- T. Beissel, R. E. Powers, T. N. Parac, and K. N. Raymond, “Coordination number incommensurate cluster formation. 8. Dynamic isomerization of a supramolecular tetrahedral M4L6 cluster,” J. Am. Chem. Soc.121(17), 4200–4206 (1999). [CrossRef]
- H. Jiang, P. Taranekar, J. R. Reynolds, and K. S. Schanze, “Conjugated polyelectrolytes: synthesis, photophysics, and applications,” Angew. Chem. Int. Ed. Engl.48(24), 4300–4316 (2009). [CrossRef] [PubMed]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- H. Jiang, P. Taranekar, J. R. Reynolds, and K. S. Schanze, “Conjugated polyelectrolytes: synthesis, photophysics, and applications,” Angew. Chem. Int. Ed. Engl.48(24), 4300–4316 (2009). [CrossRef] [PubMed]
- F. Huang, P.-I. Shih, C.-F. Shu, Y. Chi, and A. K. Y. Jen, “Highly efficient polymer white-light-emitting diodes based on lithium salts doped electron transporting layer,” Adv. Mater. (Deerfield Beach Fla.)21(3), 361–365 (2009). [CrossRef]
- M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, and S. R. Forrest, “Highly efficient phosphorescent emission from organic electroluminescent devices,” Nature395(6698), 151–154 (1998). [CrossRef]
- F. Huang, P.-I. Shih, C.-F. Shu, Y. Chi, and A. K. Y. Jen, “Highly efficient polymer white-light-emitting diodes based on lithium salts doped electron transporting layer,” Adv. Mater. (Deerfield Beach Fla.)21(3), 361–365 (2009). [CrossRef]
- M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, and S. R. Forrest, “Highly efficient phosphorescent emission from organic electroluminescent devices,” Nature395(6698), 151–154 (1998). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- F. So and D. Kondakov, “Degradation mechanisms in small-molecule and polymer organic light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)22(34), 3762–3777 (2010). [CrossRef] [PubMed]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- Q. T. Le, L. Yan, Y. G. Gao, M. G. Mason, D. J. Giesen, and C. W. Tang, “Photoemission study of aluminum/tris-(8-hydroxyquinoline) aluminum and aluminum/LiF/tris-(8-hydroxyquinoline) aluminum interfaces,” J. Appl. Phys.87(1), 375–379 (2000). [CrossRef]
- V. E. Choong, M. G. Mason, C. W. Tang, and Y. G. Gao, “Investigation of the interface formation between calcium and tris-(8-hydroxy quinoline) aluminum,” Appl. Phys. Lett.72(21), 2689–2691 (1998). [CrossRef]
- H. Jiang, P. Taranekar, J. R. Reynolds, and K. S. Schanze, “Conjugated polyelectrolytes: synthesis, photophysics, and applications,” Angew. Chem. Int. Ed. Engl.48(24), 4300–4316 (2009). [CrossRef] [PubMed]
- R. J. Holmes, S. R. Forrest, Y. J. Tung, R. C. Kwong, J. J. Brown, S. Garon, and M. E. Thompson, “Blue organic electrophosphorescence using exothermic host-guest energy transfer,” Appl. Phys. Lett.82(15), 2422–2424 (2003). [CrossRef]
- M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, and S. R. Forrest, “Highly efficient phosphorescent emission from organic electroluminescent devices,” Nature395(6698), 151–154 (1998). [CrossRef]
- A. P. Kulkarni, C. J. Tonzola, A. Babel, and S. A. Jenekhe, “Electron transport materials for organic light-emitting diodes,” Chem. Mater.16(23), 4556–4573 (2004). [CrossRef]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
- R. J. Holmes, S. R. Forrest, Y. J. Tung, R. C. Kwong, J. J. Brown, S. Garon, and M. E. Thompson, “Blue organic electrophosphorescence using exothermic host-guest energy transfer,” Appl. Phys. Lett.82(15), 2422–2424 (2003). [CrossRef]
- J. Fang, B. H. Wallikewitz, F. Gao, G. Tu, C. Muller, G. Pace, R. H. Friend, and W. T. S. Huck, “Conjugated zwitterionic polyelectrolyte as the charge injection layer for high-performance polymer light-emitting diodes,” J. Am. Chem. Soc.133(4), 683–685 (2011). [CrossRef] [PubMed]
- C. S. Wang, G. Y. Jung, A. S. Batsanov, M. R. Bryce, and M. C. Petty, “New electron-transporting materials for light emitting diodes: 1,3,4-oxadiazole-pyridine and 1,3,4-oxadiazole-pyrimidine hybrids,” J. Mater. Chem.12(2), 173–180 (2002). [CrossRef]
- L. Chen, J. Ding, Y. Cheng, L. Wang, X. Jing, and F. Wang, “Twofold terminal post-functionalization of acetylacetone with hole- and electron-transporting fragments,” Tetrahedron Lett.51(35), 4612–4616 (2010). [CrossRef]
- C. Duan, L. Wang, K. Zhang, X. Guan, and F. Huang, “Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)23(14), 1665–1669 (2011). [CrossRef] [PubMed]
- L. Chen, J. Ding, Y. Cheng, L. Wang, X. Jing, and F. Wang, “Twofold terminal post-functionalization of acetylacetone with hole- and electron-transporting fragments,” Tetrahedron Lett.51(35), 4612–4616 (2010). [CrossRef]
- B. Zhang, C. Qin, J. Ding, L. Chen, Z. Xie, Y. Cheng, and L. Wang, “High-performance all-polymer white-light-emitting diodes using polyfluorene containing phosphonate groups as an efficient electron-injection layer,” Adv. Funct. Mater.20(17), 2951–2957 (2010). [CrossRef]
- X. Gong, S. Wang, D. Moses, G. C. Bazan, and A. J. Heeger, “Multilayer polymer light-emitting diodes: White-light emission with high efficiency,” Adv. Mater. (Deerfield Beach Fla.)17(17), 2053–2058 (2005). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
- X. Xu, B. Han, J. Chen, J. Peng, H. Wu, and Y. Cao, “2,7-Carbazole-1,4-phenylene Copolymers with polar side chains for cathode modifications in polymer light-emitting diodes,” Macromolecules44(11), 4204–4212 (2011). [CrossRef]
- C. Zhong, C. Duan, F. Huang, H. Wu, and Y. Cao, “Materials and devices toward fully solution processable organic light-emitting diodes,” Chem. Mater.23(3), 326–340 (2011). [CrossRef]
- F. Huang, H. Wu, and Y. Cao, “Water/alcohol soluble conjugated polymers as highly efficient electron transporting/injection layer in optoelectronic devices,” Chem. Soc. Rev.39(7), 2500–2521 (2010). [CrossRef] [PubMed]
- T. V. Pho, P. Zalar, A. Garcia, T.-Q. Nguyen, and F. Wudl, “Electron injection barrier reduction for organic light-emitting devices by quinacridone derivatives,” Chem. Commun. (Camb.)46(43), 8210–8212 (2010). [CrossRef] [PubMed]
- B. Zhang, C. Qin, J. Ding, L. Chen, Z. Xie, Y. Cheng, and L. Wang, “High-performance all-polymer white-light-emitting diodes using polyfluorene containing phosphonate groups as an efficient electron-injection layer,” Adv. Funct. Mater.20(17), 2951–2957 (2010). [CrossRef]
- X. Xu, B. Han, J. Chen, J. Peng, H. Wu, and Y. Cao, “2,7-Carbazole-1,4-phenylene Copolymers with polar side chains for cathode modifications in polymer light-emitting diodes,” Macromolecules44(11), 4204–4212 (2011). [CrossRef]
- R. Yang, Y. Xu, X.-D. Dang, T.-Q. Nguyen, Y. Cao, and G. C. Bazan, “Conjugated oligoelectrolyte electron transport/injection layers for organic optoelectronic devices,” J. Am. Chem. Soc.130(11), 3282–3283 (2008). [CrossRef] [PubMed]
- Q. T. Le, L. Yan, Y. G. Gao, M. G. Mason, D. J. Giesen, and C. W. Tang, “Photoemission study of aluminum/tris-(8-hydroxyquinoline) aluminum and aluminum/LiF/tris-(8-hydroxyquinoline) aluminum interfaces,” J. Appl. Phys.87(1), 375–379 (2000). [CrossRef]
- I. D. Parker, Y. Cao, and C. Y. Yang, “Lifetime and degradation effects in polymer light-emitting diodes,” J. Appl. Phys.85(4), 2441–2447 (1999). [CrossRef]
- R. Yang, Y. Xu, X.-D. Dang, T.-Q. Nguyen, Y. Cao, and G. C. Bazan, “Conjugated oligoelectrolyte electron transport/injection layers for organic optoelectronic devices,” J. Am. Chem. Soc.130(11), 3282–3283 (2008). [CrossRef] [PubMed]
- X. H. Yang, F. Jaiser, S. Klinger, and D. Neher, “Blue polymer electrophosphorescent devices with different electron-transporting oxadiazoles,” Appl. Phys. Lett.88(2), 021107 (2006). [CrossRef]
- M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, and S. R. Forrest, “Highly efficient phosphorescent emission from organic electroluminescent devices,” Nature395(6698), 151–154 (1998). [CrossRef]
- T. V. Pho, P. Zalar, A. Garcia, T.-Q. Nguyen, and F. Wudl, “Electron injection barrier reduction for organic light-emitting devices by quinacridone derivatives,” Chem. Commun. (Camb.)46(43), 8210–8212 (2010). [CrossRef] [PubMed]
- B. Zhang, C. Qin, J. Ding, L. Chen, Z. Xie, Y. Cheng, and L. Wang, “High-performance all-polymer white-light-emitting diodes using polyfluorene containing phosphonate groups as an efficient electron-injection layer,” Adv. Funct. Mater.20(17), 2951–2957 (2010). [CrossRef]
- C. Duan, L. Wang, K. Zhang, X. Guan, and F. Huang, “Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)23(14), 1665–1669 (2011). [CrossRef] [PubMed]
- F. Huang, Y.-H. Niu, Y. Zhang, J.-W. Ka, M. S. Liu, and A. K. Y. Jen, “A conjugated, neutral surfactant as electron-injection material for high-efficiency polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)19(15), 2010–2014 (2007). [CrossRef]
- C. Zhong, C. Duan, F. Huang, H. Wu, and Y. Cao, “Materials and devices toward fully solution processable organic light-emitting diodes,” Chem. Mater.23(3), 326–340 (2011). [CrossRef]
Adv. Funct. Mater.
- T.-W. Lee, M.-G. Kim, S. H. Park, S. Y. Kim, O. Kwon, T. Noh, J.-J. Park, T.-L. Choi, J. H. Park, and B. D. Chin, “Designing a stable cathode with multiple layers to improve the operational lifetime of polymer light-emitting diodes,” Adv. Funct. Mater.19(12), 1863–1868 (2009). [CrossRef]
- B. Zhang, C. Qin, J. Ding, L. Chen, Z. Xie, Y. Cheng, and L. Wang, “High-performance all-polymer white-light-emitting diodes using polyfluorene containing phosphonate groups as an efficient electron-injection layer,” Adv. Funct. Mater.20(17), 2951–2957 (2010). [CrossRef]
Adv. Mater. (Deerfield Beach Fla.)
- F. Huang, Y.-H. Niu, Y. Zhang, J.-W. Ka, M. S. Liu, and A. K. Y. Jen, “A conjugated, neutral surfactant as electron-injection material for high-efficiency polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)19(15), 2010–2014 (2007). [CrossRef]
- X. Gong, S. Wang, D. Moses, G. C. Bazan, and A. J. Heeger, “Multilayer polymer light-emitting diodes: White-light emission with high efficiency,” Adv. Mater. (Deerfield Beach Fla.)17(17), 2053–2058 (2005). [CrossRef]
- F. So and D. Kondakov, “Degradation mechanisms in small-molecule and polymer organic light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)22(34), 3762–3777 (2010). [CrossRef] [PubMed]
- C. V. Hoven, A. Garcia, G. C. Bazan, and T.-Q. Nguyen, “Recent Applications of conjugated polyelectrolytes in optoelectronic devices,” Adv. Mater. (Deerfield Beach Fla.)20(20), 3793–3810 (2008). [CrossRef]
- C. Duan, L. Wang, K. Zhang, X. Guan, and F. Huang, “Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes,” Adv. Mater. (Deerfield Beach Fla.)23(14), 1665–1669 (2011). [CrossRef] [PubMed]
- F. Huang, P.-I. Shih, C.-F. Shu, Y. Chi, and A. K. Y. Jen, “Highly efficient polymer white-light-emitting diodes based on lithium salts doped electron transporting layer,” Adv. Mater. (Deerfield Beach Fla.)21(3), 361–365 (2009). [CrossRef]
Angew. Chem. Int. Ed. Engl.
- H. Jiang, P. Taranekar, J. R. Reynolds, and K. S. Schanze, “Conjugated polyelectrolytes: synthesis, photophysics, and applications,” Angew. Chem. Int. Ed. Engl.48(24), 4300–4316 (2009). [CrossRef] [PubMed]
Appl. Phys. Lett.
- X. H. Yang, F. Jaiser, S. Klinger, and D. Neher, “Blue polymer electrophosphorescent devices with different electron-transporting oxadiazoles,” Appl. Phys. Lett.88(2), 021107 (2006). [CrossRef]
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- C. S. Wang, G. Y. Jung, A. S. Batsanov, M. R. Bryce, and M. C. Petty, “New electron-transporting materials for light emitting diodes: 1,3,4-oxadiazole-pyridine and 1,3,4-oxadiazole-pyrimidine hybrids,” J. Mater. Chem.12(2), 173–180 (2002). [CrossRef]
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- M. Stoessel, G. Wittmann, J. Staudigel, F. Steuber, J. Blassing, W. Roth, H. Klausmann, W. Rogler, J. Simmerer, A. Winnacker, M. Inbasekaran, and E. P. Woo, “Cathode-induced luminescence quenching in polyfluorenes,” J. Appl. Phys.87(9), 4467–4475 (2000). [CrossRef]
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- I. D. Parker, Y. Cao, and C. Y. Yang, “Lifetime and degradation effects in polymer light-emitting diodes,” J. Appl. Phys.85(4), 2441–2447 (1999). [CrossRef]
- M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, and S. R. Forrest, “Highly efficient phosphorescent emission from organic electroluminescent devices,” Nature395(6698), 151–154 (1998). [CrossRef]
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