Light-emitting dyes derived from bifunctional chromophores of diarylamine and oxadiazole: Synthesis, crystal structure, photophysics and electroluminescence

Dyes and Pigments

Volumn 88, Issue 3, 2011, Pages 333-343

  He, Ze ^a   Kan, Chi Wai ^b   Ho, Cheuk Lam ^a   Wong, Wai Yeung ^a   Chui, Chung Hin ^b,c   Tong, Ka Lap ^a   So, Shu Kong ^a   Lee, Tik Ho ^a   Leung, Louis M ^a   Lin, Zhenyang ^d  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^c CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^d HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Arylamine; Bipolar molecules; Crystal structures; Electroluminescence; Organic synthesis; Oxadiazole

Indexed keywords

ARYL AMINES; ARYL RINGS; BIFUNCTIONAL; BIFUNCTIONAL MOLECULES; BIPOLAR MOLECULES; DENSITY FUNCTIONALS; DEVICE STRUCTURES; DIARYLAMINES; ELECTROLUMINESCENT PROPERTIES; ELECTRON TRANSPORTING; HOLE TRANSPORTING; LUMINESCENT COMPOUNDS; MORPHOLOGICAL STABILITY; ORGANIC LIGHT-EMITTING DEVICES; ORGANIC SYNTHESIS; OXADIAZOLE RINGS; OXADIAZOLES; PHOTOPHYSICAL; PHOTOPHYSICS; ROOM TEMPERATURE; THEORETICAL CALCULATIONS; TRIARYLAMINES; TUNABLE COLOR;

CHROMOPHORES; COMPLEXATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTROCHEMICAL PROPERTIES; ELECTROCHEMISTRY; ELECTROLUMINESCENCE; ELECTRONIC PROPERTIES; LIGHT; LIGHT EMISSION; MOLECULES;

SYNTHESIS (CHEMICAL);

EID: 77957850960     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2010.08.001     Document Type: Article

References (40)

1. C.W. Tang, S.A. VanSlyke, and C.H. Chen Electroluminescence of doped organic thin films J Appl Phys 65 1989 3610 3616
2. W. Lu, B.X. Mi, M.C.W. Chan, Z. Hui, C.M. Che, and N. Zhu Structural and spectroscopic studies on Pt⋯Pt and π-π interactions in luminescent multinuclear cyclometalated platinum(II) homologues tethered by oligophosphine auxiliaries J Am Chem Soc 126 2004 4958 4971 (Pubitemid 38781499)
3. Y. Ma, C.M. Che, H.Y. Chao, X. Zhou, W.H. Chan, and J. Shen High luminescence gold(I) and copper(I) complexes with a triplet excited state for use in light-emitting diodes Adv Mater 11 1999 852 857 (Pubitemid 129675820)
4. D.F. O'Brien, M.A. Baldo, M.E. Thompson, and S.R. Forrest Improved energy transfer in electrophosphorescent devices Appl Phys Lett 74 1999 442 444
5. Y. Shirota Organic materials for electronic and optoelectronic devices J Mater Chem 10 2000 1 25
6. K.T. Kamtekar, C. Wang, S. Bettington, A.S. Batsanov, I.F. Perepichka, and M.R. Bryce New electroluminescent bipolar compounds for balanced charge-transport and tuneable colour in organic light emitting diodes: triphenylamine-oxadiazole-fluorene triad molecules J Mater Chem 16 2006 3823 3835 (Pubitemid 44498084)
7. Y. Tao, Q. Wang, Y. Shang, C. Yang, A. Liang, and J. Qin Multifunctional bipolar triphenylamine/oxadiazole derivatives: highly efficient blue fluorescence, red phosphorescence host and two-color based white OLEDs Chem Commun 2009 77 79
8. Y. Tao, Q. Wang, C. Yang, Q. Wang, Z. Zhang, and T. Zou A simple carbazole/oxadiazole hybrid molecule: an excellent bipolar host for green and red phosphorescent OLEDs Angew Chem Int Ed 47 2008 8104 8107
9. Y. Tao, Q. Wang, L. Ao, C. Zhong, J. Qin, and C. Yang Molecular design of host materials based on triphenylamine/oxadiazole hybrids for excellent deep-red phosphorescent organic light-emitting diodes J Mater Chem 20 2010 1759 1765
10. N. Tamoto, C. Adachi, and K. Nagai Electroluminescence of 1,3,4-oxadiazole and triphenylamine-containing molecules as an emitter in organic multilayer light emitting diodes Chem Mater 9 1997 1077 1085 (Pubitemid 127471416)
11. W.Y. Wong, Z. He, S.K. So, K.L. Tong, and Z. Lin A multifunctional platinum-based triplet emitter for OLED applications Organometallics 24 2005 4079 4082 (Pubitemid 41173504)
12. W.Y. Wong, and C.L. Ho Functional metallophosphors for effective charge carrier injection/transport: new robust OLED materials with emerging applications J Mater Chem 19 2009 4457 4482
13. W.Y. Wong, and C.L. Ho Coord Chem Rev 253 2009 1709 1758
14. J. Lu, A.R. Hill, Y. Sun, A.S. Hay, T. Maindron, and J.P. Dodelet Synthesis and characterization of a blue light emitting polymer containing both hole and electron transporting units Chem Mater 11 1999 2501 2507 (Pubitemid 129687194)
15. Y.J. Bing, L.M. Leung, and G. Menglian Synthesis of efficient blue and red light emitting phenanthroline derivatives containing both hole and electron transporting properties Tetrahedron Lett 45 2004 6361 6363 (Pubitemid 39055828)
16. C. Adachi, T. Tsutsui, and S. Saito Blue light-emitting organic electroluminescent devices Appl Phys Lett 56 1990 799 801
17. A.R. Brown, D.D.C. Bradley, J.H. Burroughes, R.H. Friend, N.C. Greenham, and P.L. Burn Poly(p-phenylenevinylene) light-emitting diodes: enhanced electroluminescent efficiency through charge carrier confinement Appl Phys Lett 61 1992 2793 2795
18. Z. He, W.Y. Wong, X. Yu, H.S. Kwok, and Z. Lin Phosphorescent platinum(II) complexes derived from multifunctional chromophores: synthesis, structures, photophysics, and electroluminescence Inorg Chem 45 2006 10922 10937
19. M. Ichikawa, T. Kawaguchi, K. Kobayashi, T. Miki, K. Furukawa, and T. Koyama Bipyridyl oxadiazoles as efficient and durable electron-transporting and hole-blocking molecular materials J Mater Chem 16 2006 221 225 (Pubitemid 43324479)
20. U. Mitschke, and P. Bäuerle The electroluminescence of organic materials J Mater Chem 10 2000 1471 1507
21. P. Strohriegl, and J.V. Grazulevicius Charge-transporting molecular glasses Adv Mater 14 2002 1439 1452 (Pubitemid 35369260)
22. T.P. Bender, J.F. Graham, and J.M. Duff Effect of substitution on the electrochemical and xerographic properties of triarylamines: correlation to the Hammett parameter of the substituent and calculated HOMO energy level Chem Mater 13 2001 4105 4111
23. G. Casalbore-Miceli, A.D. Esposti, V. Fattori, G. Marconi, and C. Sabatini A correlation between electrochemical properties and geometrical structure of some triarylamines used as hole transporting materials in organic electroluminescent devices Phys Chem Chem Phys 6 2004 3092 3096
24. W.R. Dawson, and M.W. Windsor Fluorescence yields of aromatic compounds J Phys Chem 72 1968 3251 3260
25. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian03, revision B05 2003 Gaussian, Inc. Pittsburgh, PA
26. W.R. Wadt, and P.J. Hay Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi J. Chem Phys 82 1985 284 298
27. G. Schaftenaar Molden, version 3.5 1999 CAOS/CAMM Center Nijmegen Toernooiveld: Nijmegen, The Netherlands
28. G. Zhou, C.L. Ho, W.Y. Wong, Q. Wang, D. Ma, and L. Wang Manipulating charge-transfer character with electron-withdrawing main-group moieties for the color tuning of iridium electrophosphors Adv Funct Mater 18 2008 499 511 (Pubitemid 351346224)
29. G. Zhou, Q. Wang, C.L. Ho, W.Y. Wong, D. Ma, and L. Wang Robust tris-cyclometalated iridium(III) phosphors with ligands for effective charge carrier injection/transport: synthesis, redox, photophysical, and electrophosphorescent behavior Chem Asian J 3 2008 1830 1841
30. SAINT+, version 6.02a; Bruker analytical X-ray system 1998 Inc. Madison, WI
31. G.M. Sheldrick SADABS, empirical absorption correction program 1997 University of Göttingen Germany
32. G.M. Sheldrick SHELXTL™, Reference manual, version 5.1 1997 Madison, WI
33. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire Aryl-aryl bond formation: one century after the discovery of the Ullmann reaction Chem Rev 102 2002 1359 1369 (Pubitemid 35377647)
34. M. Martínez-Palau, E. Perea, F. López-Calahorra, and D. Velasco Synthesis of luminescent N-arylcarbazoles by copper bronze-mediated reaction Lett Org Chem 1 2004 231 237
35. A.A. Moroz, and M.S. Shvartsberg The Ullmann ether condensation Russ Chem Rev 43 1974 679 689
36. J.K. Stille The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles Angew Chem Int Ed 25 1986 508 524
37. P.J. Low, M.A.J. Paterson, A.E. Goeta, D.S. Yufit, J.A.K. Howard, and J.C. Cherryman The molecular structures and electrochemical response of "twisted" tetra(aryl)benzidenes J Mater Chem 14 2004 2516 2523
38. P.J. Low, M.A.J. Paterson, H. Puschmann, A.E. Goeta, J.A.K. Howard, and C. Lambert Crystal, molecular and electronic structure of N, N′-diphenyl-N, N′-bis(2,4-dimethylphenyl)-(1,1′-biphenyl)-4, 4′-diamine and the corresponding radical cation Chem Eur J 10 2004 83 91
39. X. Gong, P.K. Ng, and W.K. Chan Trifunctional light-emitting molecules based on rhenium and ruthenium bipyridine complexes Adv Mater 10 1998 1337 1340 (Pubitemid 128549402)
40. C.L. Ho, W.Y. Wong, G.J. Zhou, B. Yao, Z. Xie, and L. Wang Solution-processible multi-component cyclometalated iridium phosphors for high-efficiency orange-emitting OLEDs and their potential use as white light sources Adv Funct Mater 17 2007 2925 2936 (Pubitemid 350012701)