Spiro-functionalized ligand with supramolecular steric hindrance to control π-π interaction in the iridium complex for high-performance electrophosphorescent devices

Journal of Physical Chemistry Letters

Volumn 1, Issue 1, 2010, Pages 272-276

  Xie, Ling Hai ^a   Zhu, Rui ^a   Qian, Yan ^a   Liu, Ran Ran ^a   Chen, Shu Fen ^a   Lin, Jian ^a   Huang, Wei ^a  

^a NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Macromolecules; Soft matter

Indexed keywords

DOPANT CONCENTRATIONS; ELECTROPHOSPHORESCENT DEVICES; FUNCTIONALIZED LIGANDS; HOMOLEPTIC; HOST GUEST INTERACTIONS; IR COMPLEXES; IRIDIUM COMPLEX; SOFT MATTER; SPECTRAL STABILITY; SPIROBIFLUORENE; STERIC HINDRANCES; SUPRAMOLECULAR ARCHITECTURES; SUPRAMOLECULAR INTERACTIONS; THREE-DIMENSIONAL (3D); TURN ON VOLTAGE;

COMPLEXATION; DRUG INTERACTIONS; FUNCTIONAL POLYMERS; INTERNET PROTOCOLS; IRIDIUM; IRIDIUM COMPOUNDS; LIGHT EMISSION; LIGHT EMITTING DIODES; MACROMOLECULES; OPTOELECTRONIC DEVICES; ORGANIC LIGHT EMITTING DIODES (OLED); PHOSPHORESCENCE; SUPRAMOLECULAR CHEMISTRY;

THREE DIMENSIONAL;

EID: 77149150970     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz900105v     Document Type: Article

References (26)

1. Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices. Nature 1998, 395 (6698), 151-154.
2. Sun, Y. R.; Giebink, N. C.; Kanno, H.; Ma, B. W.; Thompson, M. E.; Forrest, S. R. Management of Singlet and Triplet Excitons for Efficient White Organic Light-Emitting Devices. Nature 2006, 440 (7086), 908-912.
3. Kang, D. M.; Kang, J. W.; Park, J. W.; Jung, S. O.; Lee, S. H.; Park, H. D.; Kim, Y. H.; Shin, S. C.; Kim, J. J.; Kwon, S. K. Iridium Complexes with Cyclometalated 2-Cycloalkenylpyridine Ligands As Highly Efficient Emitters for Organic Light-Emitting Diodes. Adv. Mater. 2008, 20 (10), 2003-2007.
4. Gao, Z. Q.; Mi, B. X.; Tam, H. L.; Cheah, K. W.; Chen, C. H.; Wong, M. S.; Lee, S. T.; Lee, C. S. High Efficiency and Small Roll-off Electrophosphorescence from a New Iridium Complex with Well-Matched Energy Levels. Adv. Mater. 2008, 20 (4),774-778.
5. Huang, J. S.; Watanabe, T.; Ueno, K.; Yang, Y. Highly Efficient Red-Emission Polymer Phosphorescent Light-Emitting Diodes Based on Two Novel Tris(1-phenylisoquinolinato-C2, N)iridium(III) Derivatives. Adv. Mater. 2007, 19 (5), 739-743.
6. You, Y. M.; Park, S. Y. Inter-Ligand Energy Transfer and Related Emission Change in the Cyclometalated Heteroleptic Iridium Complex: Facile and Efficient Color Tuning over the Whole Visible Range by the Ancillary Ligand Structure. J. Am. Chem. Soc. 2005, 127 (36), 12438-12439.
7. Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razzaq, F.; Lee, H. E.; Adachi, C.; Burrows, P.E.; Forrest, S. R.; Thompson, M. E. Highly Phosphorescent Bis-Cyclometalated Iridium Complexes: Synthesis, Photophysical Characterization, and Use in Organic Light Emitting Diodes. J. Am. Chem. Soc. 2001, 123 (18),4304-4312.
8. Xie, L. H.; Ling, Q. D.; Hou, X. Y.; Huang, W. An Effective Friedel-Crafts Postfunctionalization of Poly(N-vinylcarbazole) to Tune Carrier Transportation of Supramolecular Organic Semiconductors Based on π-Stacked Polymers for Nonvolatile Flash Memory Cell. J. Am. Chem. Soc. 2008, 130 (7),2120-2121.
9. Lo, S. C.; Male, N. A. H.; Markham, J. P. J.; Magennis, S. W.; Burn, P. L.; Salata, O. V.; Samuel, I. D. W. Green Phosphorescent Dendrimer for Light-Emitting Diodes. Adv. Mater. 2002,14 (13-14), 975-979.
10. Lo, S. C.; Burn, P. L. Development of Dendrimers: Macromolecules for Use in Organic Light-Emitting Diodes and Solar Cells. Chem. Rev. 2007, 107 (4), 1097-1116.
11. Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razzaq, F.; Kwong, R.; Tsyba, I.; Bortz, M.; Mui, B.; Bau, R.; Thompson, M. E. Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes. Inorg. Chem. 2001, 40 (7),1704-1711.
12. Ionkin, A. S.; Marshall, W. J.; Wang, Y. Syntheses, Structural Characterization, and First Electroluminescent Properties of Mono-cyclometalated Platinum(II) Complexes with Greater than Classical π-π Stacking and Pt-Pt Distances. Organometallics 2005, 24 (4), 619-627.
13. Tam, A. Y. Y.; Wong, K. M. C.; Wang, G. X.; Yam, V. W. W. Luminescent Metallogels of Platinum(II) Terpyridyl Complexes: Interplay of Metal 3 3 3 Metal, π-π and Hydrophobic-Hydrophobic Interactions on Gel Formation. Chem. Commun. 2007,20,2028-2030.
14. Kolosov, D.; Adamovich, V.; Djurovich, P.; Thompson, M. E.; Adachi, C. 1,8-Naphthalimides in Phosphorescent Organic LEDs: The Interplay between Dopant, Exciplex, and Host Emission. J. Am. Chem. Soc. 2002, 124 (33), 9945-9954.
15. Zhao, Q.; Li, L.; Li, F. Y.; Yu, M. X.; Liu, Z. P.; Yi, T.; Huang, C. H. Aggregation-Induced Phosphorescent Emission (AIPE) of Iridium(III) Complexes. Chem. Commun. 2008, 6, 685-687.
16. Xie, H. Z.; Liu, M. W.; Wang, O. Y.; Zhang, X. H.; Lee, C. S.; Hung, L. S.; Lee, S. T.; Teng, P. F.; Kwong, H. L.; Zheng, H.; Che, C. M. Reduction of Self-Quenching Effect in Organic Electro-phosphorescence Emitting Devices via the Use of Sterically Hindered Spacers in Phosphorescence Molecules. Adv. Mater. 2001,13 (16),1245-1248.
17. Zhou, G. J.; Wong, W. Y.; Yao, B.; Xie, Z.; Wang, L. Multi-functional Metallophosphors with Anti-Triplet-Triplet Annihilation Properties for Solution-Processable Electroluminescent Devices. J. Mater. Chem. 2008, 18 (15), 1799-1809.
18. Yao, J. H.; Zhen, C. G.; Loh, K. P.; Chen, Z. K. Novel Iridium Complexes As High-Efficiency Yellow and Red Phosphorescent Light Emitters for Organic Light-Emitting Diodes. Tetrahedron 2008, 64 (48), 10814-10820.
19. Velusamy, M.; Thomas, K. R. J.; Chen, C. H.; Lin, J. T.; Wen, Y. S.; Hsieh, W. T.; Lai, C. H.; Chou, P. T. Synthesis, Structure and Electroluminescent Properties of Cyclometalated Iridium Complexes Possessing Sterically Hindered Ligands. Dalton Trans. 2007, 28, 3025-3034.
20. You, Y.; An, C. G.; Kim, J. J.; Park, S. Y. A Deep Red Phosphorescent Ir(III) Complex for Use in Polymer LightEmitting Diodes: Role of the Arylsilyl Substituents. J. Org. Chem. 2007, 72 (16), 6241-6246.
21. Su, H. C.; Fang, F. C.; Hwu, T. Y.; Hsieh, H. H.; Chen, H. F.; Lee, G. H.; Peng, S. M.; Wong, K. T.; Wu, C. C. Highly Efficient Orange and GreenSolid-StateLight-Emitting Electrochemical CellsBasedon CationicIr-III Complexeswith EnhancedSteric Hindrance. Adv. Funct. Mater. 2007, 17 (6), 1019-1027.
22. Xie, L. H.; Hou, X. Y.; Hua, Y. R.; Huang, Y. Q.; Zhao, B. M.; Liu, F.; Peng, B.; Wei, W.; Huang, W. An Effective Strategy to Tune Supramolecular Interaction via a Spiro-bridged Spacer in Oligothiophene-S,S-dioxides and Their Anomalous Photoluminescent Behavior. Org. Lett. 2007, 9 (9), 1619-1622.
23. Bettington, S.; Tavasli, M.; Bryce, M. R.; Batsanov, A. S.; Thompson, A. L.; Al Attar, H. A.; Dias, F. B.; Monkman, A. P. Bridged Diiridium Complexes for Electrophosphorescent OLEDs: Synthesis, X-ray Crystal Structures, Photophysics, and Devices. J. Mater. Chem. 2006, 16 (11), 1046-1052.
24. Low, P. J.; Paterson, M. A. J.; Yufit, D. S.; Howard, J. A. K.; Cherryman, J. C.; Tackley, D. R.; Brook, R.; Brown, B. Towards an Understanding of Structure-Property Relationships in Hole-Transport Materials: The Influence of Molecular Conformation on Oxidation Potential in Poly(aryl) Amines. J. Mater. Chem. 2005, 15 (23), 2304-2315.
25. Ono, K.; Joho, M.; Saito, K.; Tomura, M.; Matsushita, Y.; Naka, S.; Okada, H.; Onnagawa, H. Synthesis and Electroluminescence Properties of fac-Tris(2-phenylpyridine)iridium Derivatives Containing Hole-Trapping Moieties. Eur. J. Inorg. Chem. 2006, 18, 3676-3683.
26. Huang, K. W.; Wu, H. Z.; Shi, M.; Li, F. Y.; Yi, T.; Huang, C. H. Reply toComment on 'Aggregation-Induced Phosphorescent Emission (AIPE) of Iridium(III) Complexes': Origin of the Enhanced Phosphorescence. Chem. Commun. 2009, 10, 1243-1245.