Highly-efficiency red-emitting platinum (II) complexes containing 4′-diarylamino-1-phenylisoquinoline ligands in polymer light-emitting diodes: Synthesis, structure, photoelectron and electroluminescence

Dyes and Pigments

Volumn 86, Issue 2, 2010, Pages 166-173

  Hu, Zhengyong ^a   Wang, Yafei ^a   Shi, Danyan ^a   Tan, Hua ^a   Li, Xiaoshuang ^a   Wang, Lei ^c   Zhu, Weiguo ^a,b   Cao, Yong ^c  

^a XIANGTAN UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^c SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Electroluminescence; Phosphorescence; Photoluminescence; Platinum (II) complex; Polymer light emitting devices; Synthesis

Indexed keywords

ANCILLARY LIGANDS; DOUBLE LAYERS; EXTERNAL QUANTUM EFFICIENCY; FUNCTIONALIZED; HETEROLEPTIC; HOST MATRICES; MOLECULAR GEOMETRIES; MORPHOLOGICAL STABILITY; OXADIAZOLES; PLATINUM (II) COMPLEX; PLATINUM COMPLEXES; POLYMER LIGHT-EMITTING DIODES; SINGLE CRYSTAL X-RAY DIFFRACTION;

CHELATION; COMPLEXATION; CURRENT DENSITY; DICHLOROMETHANE; ELECTROLUMINESCENCE; LIGANDS; LIGHT; LIGHT EMISSION; LIGHT EMITTING DIODES; PHOSPHORESCENCE; PHOTOLUMINESCENCE; PLATINUM;

PLATINUM COMPOUNDS;

FLUORESCENCE; INORGANIC COMPOUND; LUMINESCENCE; MORPHOLOGY; SYNTHESIS; THERMAL STABILITY;

EID: 76449101546     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.12.014     Document Type: Article

References (40)

1. Peyratout C.S., Aldridge T.K., Crites D.K., and McMillin D.R. DNA-binding studies of a bifunctional platinum complex that is a luminescent intercalator. Inorganic Chemistry 34 17 (1995) 4484-4489
2. Wang A.H.J., Nathans J., Van Der Marel G.A., Van Boom J.H., and Rich A. Molecular structure of a double helical DNA fragment intercalator complex between deoxy CpG and a terpyridine platinum compound. Nature 276 (1978) 471-474
3. Houlding V.H., and Frank A.J. Cooperative excited-state behavior in platinum(II) Magnus-type double-salt materials. Active and inactive photosensitizers for hydrogen production in aqueous suspension. Inorganic Chemistry 24 22 (1985) 3664-3668
4. 2 from aqueous media and spectroscopic analysis of the catalyst. Journal of Physical Chemistry B 101 19 (1997) 3806-3810
5. Anbalagan V., and Srivastava T.S. Spectral and photochemical behaviour of mononuclear and dinuclear α-diimine complexes of Pt(II) and Pd(II) with catechol derivatives. Journal of Photochemistry and Photobiology A: Chemistry 89 2 (1995) 113-119
6. Roundhill D.M., Gray H.B., and Che C.M. Pyrophosphito-bridged diplatinum chemistry. Accounts of Chemical Research 22 2 (1989) 55-61
7. Nocera D.G. Chemistry of the multielectron excited state. Accounts of Chemical Research 28 5 (1995) 209-217
8. Paw W., Cummings S.D., Mansour M.A., Connick W.B., Geiger D.K., and Eisenberg R. Luminescent platinum complexes: tuning and using the excited state. Coordination Chemistry Reviews 171 1 (1998) 125-150
9. Hissler M., McGarrah J.E., Connick W.B., Geiger D.K., Cummings S.D., and Eisenberg R. Platinum diimine complexes: towards a molecular photochemical device. Coordination Chemistry Reviews 208 1 (2000) 115-137
10. McGarrah J.E., Kim Y.J., Hissler M., and Eisenberg R. Toward a Molecular Photochemical Device: a triad for photo induced charge separation based on a platinum diimine bis(acetylide) chromophore. Inorganic Chemistry 40 18 (2001) 4510-4511
11. James E.M., and Eisenberg R. Dyads for photo induced charge separation based on platinum diimine bis(acetylide) chromophores: synthesis, luminescence and transient absorption studies. Inorganic Chemistry 42 14 (2003) 4355-4365
12. Baldo M.A., O'Brien D.F., You Y., Shoustikov A., Sibley S., Thompson M.E., et al. Highly efficient phosphorescent emission from organic electroluminescent devices. Nature 395 (1998) 151-154
13. Kwong R.C., Sibley S., Dubovoy T., Baldo M.A., Forrest S.R., and Thompson M.E. Efficient, saturated red organic light emitting devices based on phosphorescent platinum(II) porphyrins. Chemistry of Materials 11 12 (1999) 3709-3713
14. Cleave V., Yahioglu G., Barny P.L., Friend R.H., and Tessler N. Harvesting singlet and triplet energy in polymer LEDs. Advanced Materials 11 4 (1999) 285-288
15. Baldo M.A., Lamansky S., Burrows P.E., Thompson M.E., and Forrest S.R. Very high-efficiency green organic light-emitting devices based on electrophosphorescence. Applied Physics Letters 75 1 (1999) 4-6
16. Cocchi M., Kalinowski J., Fattori V., Williams J.A.G., and Murphy L. Color-variable highly efficient organic electrophosphorescent diodes manipulating molecular exciton and excimer emissions. Applied Physics Letters 94 7 (2009) 073309-1-073309-3
17. Cocchi M., Kalinowski J., Virgili D., and Williams J.A.G. Excimer-based red/near-infrared organic light-emitting diodes with very high quantum efficiency. Applied Physics Letters 92 11 (2008) 113302-1-113302-3
18. Furuta P.T., Deng L., Garon S., Thompson M.E., and Frchet J.M.J. Platinum-functionalized random copolymers for use in solution-processible, efficient, near-White organic light-emitting diodes. Journal of the American Chemical Society 126 47 (2004) 15388-15389
19. Kavitha J.S., Chang Y., Chi Y., Yu J.K., Hu Y.H., Chou P.T., et al. In search of high-performance platinum(II) phosphorescent materials for the fabrication of red electroluminescent devices. Advanced Functional Materials 15 2 (2005) 223-229
20. Hu Z.Y., Luo C.P., Wang L., Huang F.L., Zhu K.M., Wang Y.F., et al. Highly efficient saturated red electrophosphorescence from isoquinoline-based iridium complex containing triphenylamine units in polymer light-emitting devices. Chemical Physics Letters 441 4-6 (2007) 277-281
21. Xu Z.W., Li Y., Ma X.M., Gao X.D., and Tian H. Synthesis and properties of iridium complexes based 1,3,4-oxadiazoles derivatives. Tetrahedron 64 8 (2008) 1860-1867
22. Xia Z.Y., Xiao Xiao X., Su J.H., Chang C.S., Chen C.H., Li D.L., et al. Low driving voltage and efficient orange-red phosphorescent organic light-emitting devices based on a benzotriazole iridium complex. Synthetic Metals 159 17-18 (2009) 1782-1785
23. Wong W.Y., He Z., So S.K., Tong K.L., and Lin Z.Y. A multifunctional platinum-based triplet emitter for OLED applications. Organometallics 24 16 (2005) 4079-4082
24. Zhu WG, Liu J, Luo CP, Hu ZY, Zhu MX. Zhongguo Faming Zhuanli, ZL 200510032482.XA; 2005 (in Chinese).
25. Liang B., Jiang C.Y., Chen Z., Zhang X.J., Shi H.H., and Cao Y. New iridium complex as high-efficiency red phosphorescent emitter in polymer light-emitting devices. Journal of Materials Chemistry 16 (2006) 1281-1286
26. Patil N.M., Kelkar A.A., Nabi Z., and Chaudhari R.V. Novel CuI/tributyl phosphine catalyst system for amination of aryl chlorides. Chemical Communications 19 (2003) 2460-2461
27. Cockburn B.N., Howe D.V., Keating T., Johnson B.F.G., and Lewis J. Reactivity of co-ordinated ligands. Part XV. Formation of complexes containing Group V donor atoms and metal-carbon bonds. Journal of the Chemical Society Dalton Transactions 4 (1973) 404-410
28. Chassot L., Müller E., and Von Zelewsky A. cis-Bis(2-phenylpyridine)platinum(II) (CBPPP): a simple molecular platinum compound. Inorganic Chemistry 23 25 (1984) 4249-4253
29. Ghedini M., Pucci D., Crispini A., and Barberio G. Oxidative addition to cyclometalated azobenzene platinum(II) complexes: a route to octahedral liquid crystalline materials. Organometallics 18 11 (1999) 2116-2124
30. Lamansky S., Djurovich P., Murphy D., Abdel-Razzaq F., Kwong R., Tsyba I., et al. Synthesis and characterization of phosphorescent cyclometalated iridium complexes. Inorganic Chemistry 40 7 (2001) 1704-1711
31. Lamansky S., Djurovich P., Murphy D., Abdel-Razzaq F., Lee H.E., Adachi C., et al. Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes. Journal of the American Chemical Society 123 18 (2001) 4304-4312
32. Su Y.J., Huang H.L., Li C.L., Chien C.H., Tao Y.T., Chou P.T., et al. Highly efficient red electrophosphorescent devices based on iridium isoquinoline complexes: remarkable external quantum efficiency over a wide range of current. Advanced Materials 15 11 (2003) 884-888
33. Colombo M.G., Hauser A., and Gudel H.U. Evidence for strong mixing between the LC and MLCT excited states in bis(2-phenylpyridinato-C2, N')(2,2′-bipyridine)iridium(III). Inorganic Chemistry 32 14 (1993) 3088-3092
34. Schmid B., Garces F.O., and Watts R.J. Synthesis and characterizations of cyclometalated iridium(III) solvento complexes. Inorganic Chemistry 33 1 (1994) 9-14
35. Zhou G.J., Wong W.Y., Poon S.Y., Ye C., and Lin Z.Y. Symmetric versus unsymmetric platinum(II) bis(aryleneethynylene)s with distinct electronic structures for optical power limiting/optical transparency trade-off optimization. Advanced Functional Materials 19 4 (2009) 531-544
36. Evans R.C., Douglas P., and Winscom C.J. Coordination complexes exhibiting room temperature phosphorescence: evaluation of their suitability as triplet emitters in organic light emitting diodes. Coordination Chemistry Reviews 250 15-16 (2006) 2093-2126
37. He Z., Wong W.Y., Yu X., Kwok H.S., and Lin Z. Phosphorescent platinum(II) complexes derived from multifunctional chromophores: synthesis, structures, photophysics, and electroluminescence. Inorganic Chemistry 45 26 (2006) 10922-10937
38. Bronstein H.A., Finlayson C.E., Kirov K.R., Friend R.H., and Williams C.K. Investigation into the phosphorescence of a series of regioisomeric iridium(III) complexes. Organometallics 27 13 (2008) 2980-2989
39. Thelakkat M., and Schmidt H.W. Synthesis and properties of novel derivatives of 1,3,5-tris(diarylamino)benzenes for electroluminescent devices. Advanced Materials 10 3 (1998) 219-223
40. Baldo1 M.A., Thompson M.E., and Forrest S.R. Phosphorescent materials for application to organic light emitting devices. Pure and Applied Chemistry 71 11 (1999) 2095-2096