Synthesis and characterization of highly stable and efficient star-molecules

Dyes and Pigments

Volumn 96, Issue 3, 2013, Pages 705-713

  Huang, Hai Fang ^a   Xu, Shi Hua ^a   He, Yan Bo ^a   Zhu, Cai Cai ^a   Fan, He Liang ^a   Zhou, Xue Hua ^a   Gao, Xi Cun ^a   Dai, Yan Feng ^a  

^a NANCHANG UNIVERSITY   (China)

Author keywords

Efficient; High Tg; Stable; Star molecule; Suzuki coupling; Synthesis

Indexed keywords

EFFICIENT; HIGH-T; STABLE; STAR-MOLECULE; SUZUKI COUPLINGS;

BENZENE; MOLECULES; ORGANIC SOLVENTS; QUANTUM YIELD; STARS;

SYNTHESIS (CHEMICAL);

EID: 84870663732     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.11.014     Document Type: Article

References (55)

1. W. White, Z.W. Hudson, X.D. Feng, S.J. Han, Z.H. Lu, and S.N. Wang Linear and star-shaped benzimidazolyl derivatives: syntheses, photophysical properties and use as highly efficient electron transport materials in OLEDs Dalt Tran 39 2010 892 899
2. X.W. Li, and D.H. He Synthesis and optical properties of novel anthracene-based stilbene derivatives containing an 1,3,4-oxadiazole unit Dyes Pigm 93 2012 1422 1427
3. G.T. Lei, L.D. Wang, L. Duan, J.H. Wang, and Y. Qiu Highly efficient blue electrophosphorescent devices with a novel host material Synth.Met. 144 2004 249 252
4. K.J. Okumoto, and Y. Shirota Development of new hole-transporting amorphous molecular materials for organic electroluminescent devices and their charge- transport properties Mater Sci Eng B85 2001 135 139
5. J.Q. Ding, Q. Wang, L. Zhao, D.G. Ma, L.X. Wang, and X.B. Jing Design of star-shaped molecular architectures based on carbazole and phosphine oxide moieties: towards amorphous bipolar hosts with high triplet energy for efficient blue electrophosphorescent devices J Mater Chem 20 2010 8126 8133
6. Q.X. Tong, S.L. Lai, M.Y. Chan, Y.C. Zhou, H.L. Kwong, and C.S. Lee Highly efficient blue organic light-emitting device based on a nondoped electroluminescent material Chem Mater 20 2008 6310 6312
7. Z.J. Zhao, X.J. Xu, X.P. Wang, P. Lu, G. Yu, and Y.Q. Liu Synthesis and characterization of deep blue emitters from starburst carbazole/fluorene compounds Tetrahedron 64 2008 2658 2668
8. W. Jiang, L. Duan, J. Qiao, D.Q. Zhang, G.F. Dong, and L.D. Wang Novel star-shaped host materials for highly efficient solution-processed phosphorescent organic light-emitting diodes J Mater Chem 20 2010 6131 6137
9. S.J. Ren, D.L. Zeng, H.L. Zhong, Y.C. Wang, S.X. Qian, and Q. Fang Star-shaped donor-π-acceptor conjugated Oligomers with 1,3,5-Triazine core: convergent synthesis and multifunctional properties J Phys Chem B 114 2010 10374 10383
10. M. Thelakkat Star-shaped, dendrimeric and polymeric triarylamines as photoconductors and hole transport materials for electro-optical applications Macromol Mater Eng 287 2002 442 461
11. g triphenylamine-based starburst hole-transporting material for organic light-emitting devices Chem Mater 19 2007 5851 5855
12. M. Sonntag, K. Kreger, D. Hanft, and P. Strohriegl Novel star-shaped triphenylamine- based moleclar glasses and their use in OFETs Chem Mater 17 2005 3031 3039
13. S.L. Lai, Q.X. Tong, M.Y. Chan, T.W. Ng, M.F. Lo, and S.T. Lee Distinct electroluminescent properties of triphenylamine derivatives in blue organic light-emitting devices J Mater Chem 21 2011 1206 1211
14. Z.H. Zhao, H. Jin, Y.X. Zhang, Z.H. Shen, D.C. Zou, and X.H. Fan Synthesis and properties of dendritic emitters with a fluorinated starburst oxadiazole core and twisted carbazole dendrons Macromolecules 44 2011 1405 1413
15. W.B. Zhang, W.H. Jin, X.H. Zhou, and J. Pei Star-shaped oligo(p-phenylene)- functionalized truxenes asblue-light-emitting materials: synthesis and the structure-property relationship Tetrahedron 63 2007 2907 2914
16. H. Huang, Q. Fu, S.Q. Zhuang, Y.K. Liu, J.S. Chen, and D.G. Ma Novel deep blue OLED emitter with 1,3,5-Tri(anthracen-10-yl)-benzene-centered starburst oligofluorenes J Phys Chem C 115 2011 4872 4878
17. S.L. Tao, Y.C. Zhou, C.S. Lee, X.H. Zhang, and S.T. Lee High-Efficient nondoped deep-blue-emitting organic electroluminescent device Chem Mater 22 2010 2138 2141
18. H.F. Chen, S.J. Yang, Z.H. Tsai, W.Y. Hung, T.C. Wang, and K.T. Wong 1,3,5-Triazine derivatives as new electron transport-type host materials for highly efficient green phosphorescent OLEDs J Mater Chem 19 2009 8112 8118
19. H.Q. Zhang, S.M. Wang, Y.Q. Li, B. Zhang, C.X. Du, and X.J. Wan Synthesis, characterization, and electroluminescent properties of star shaped donor-acceptor dendrimers with carbazole dendrons as peripheral branches and heterotriangulene as central core Tetrahedron 65 2009 4455 4463
20. W.J. Kuo, Y.H. Chen, R.J. Jeng, L.H. Chan, W.P. Lin, and Z.M. Yang Peripheral aryl- substituted pyrrole fluorophores for glassy blue-light-emitting diodes Tetrahedron 63 2007 7086 7096
21. g hole-injecting and hole-transporting material for organic light-emitting devices Chem Mater 23 2011 771 777
22. W. Jiang, L. Duan, J. Qiao, G.F. Dong, D.Q. Zhang, and L.D. Wang Novel carbazole/pyridine-based host material for solution-processed blue phosphorescent organic light-emitting devices Dyes Pigm 92 2012 891 896
23. H. Tanaka, S. Tokito, Y. Taga, and A. Okada Novel hole- transporting materials based on triphenylamine for organic eletroluminescent devices Chem Commun 1996 2175 2176
24. g carbazole derivatives as blue-emitting hole-transporting materials for electroluminescent devices Adv Funct Mater 13 2003 445 452
25. L.H. Chan, R.H. Lee, C.F. Hsieh, H.C. Yeh, and C.T. Chen Optimization of high- performance blue organic light-emitting diodes containing tetraphenylsilane molecular glass materials J Am Chem Soc 124 2002 6469 6479
26. D.E. Loy, B.E. Koene, and M.E. Thompson Thermally stable hole-transporting materials based upon a fluorene core Adv Funct Mater 12 2002 245 249
27. F. Steuber, J. Staudigel, M. Stössel, J. Simmerer, A. Winnacker, and H. Spreitzer white light emission from organic LEDs utilizing spiro compounds with high-temperature stability Adv Mater 12 2002 130 133
28. B.E. Koene, D.E. Loy, and M.E. Thompson Asymmetric triaryldiamines as thermally stable hole transporting layers for organic light-emitting devices Chem Mater 10 1998 2235 2250
29. Y.J. Lee, H.J. Lee, Y. Byun, S. Song, J.E. Kim, and D. Eom Study of thermal degradation of organic light emitting device structures by X-ray scattering Thin Solid Films. 515 2007 5674 5677
30. L. Long, M.Y. Zhang, S.H. Xu, X.H. Zhou, X.C. Gao, and Y.Z. Shang Cyclic arylamines functioning as advanced hole-transporting and emitting materials Synth Met 162 2012 448 452
31. V. Promarak, M. Ichikawa, T. Sudyoadsuk, S. Saengsuwan, S. Jungsuttiwong, and T. Keawin Thermally and electrochemically stable amorphous hole-transporting materials based on carbazole dendrimers for electroluminescent devices Thin Solid Films. 516 2008 2881 2888
32. J.H. Pan, Y.M. Chou, H.L. Chiu, and B.C. Wang Theoretical investigation of organic amines as hole transporting materials: correlation to the Hammett parameter of the substituent, ionization potential, and reorganization energy level Aust J Chem 62 2009 483 492
33. B. Wei, J.Z. Liu, Y. Zhang, J.H. Zhang, H.N. Peng, and H.L. Fang Stable, glassy, and versatile binaphthalene derivatives capable of efficient hole transport, hosting, and deep-blue light emission Adv Funct Mater 20 2010 2448 2458
34. Z.H. Li, and M.S. Wang Synthesis and functional properties of end-dendronized Oligo(9,9-diphenyl)fluorenes Org Lett 8 2006 1499 1502
35. J. Wu, H.Y. Li, L.C. Kang, D.P. Li, Q.L. Xu, and Y.C. Zhu Ruthenium(II) polypyridyl complexes based on bipyridine and two novel diimine ligands with carrier-transporting unit: synthesis, photoluminencence and redox properties J Organomet Chem 695 2010 2048 2056
36. J. Wang, C.J. Yang, H.N. Peng, Y.S. Deng, and X.C. Gao Synthesis of triphenylamine-modified arylates and ketones via Suzuki coupling reactions Synth Commun 41 2011 832 840
37. F.F. Yu, H.L. Fan, H.F. Huang, Q.Y. Cao, Y.F. Dai, and X.C. Gao Blue fluorescence from the ligand and yellow phosphorescence from the iridium complex: high-efficiency wet-processed white organic light-emitting device Inorg Chim Acta 390 2012 119 122
38. S.H. Xu, W.B. Liu, Y.B. He, H.L. Fan, G.J. Liu, and X.C. Gao Synthesis of three kinds of star-burst carbazol derivatives and their photoelectric performances Hua-xue Shi-Ji 32 2010 965 969
39. G.L. Feng, S.J. Ji, W.Y. Lai, and W. Huang Synthesis and optical properties of starburst carbazoles based on 9-Phenylcarbazole core Synlett 17 2006 2841 2845
40. H. Lee, J. Oh, H.Y. Chu, J.I. Lee, S.H. Kim, and Y.S. Yang Synthesis of regio-and stereoselective alkoxy-substituted spirobifluorene derivatives for blue light emitting materials Tetrahedron 59 2003 2773 2779
41. H.Y. Wang, G. Chen, X.P. Xu, and S.J. Ji Synthesis and characterization of triphenylamine-benzothiazole-based donor and acceptor materials Synth Met 160 2010 1065 1072
42. Y. You, C.G. An, D.S. Lee, J.J. Kim, and S.Y. Park Silicon-containing dendritic tris-cyclometalated Ir(III) complex and its electrophosphorescence in a polymer host J Mater Chem 16 2006 4706 4713
43. W. Wei, P.I. Djurovich, and M.E. Thompson Properties of fluorenyl silanes in organic light emitting diodes Chem Mater 22 5 2010 1724 1731
44. S. Ginagunta, P.Z. Zhang, P.E. Nikolaus, and L. Jurgen Synthesis of alkylated aminofluorenes by palladium-catalyzed substitution at halofluorenes J Org Chem 69 2004 987 990
45. D. Wang, J. Wang, H.L. Fan, H.F. Huang, Z.Z. Chu, and X.C. Gao Carbazole and arylamine functionalized iridium complexes for efficient electro-phosphorescent light-emitting diodes Inorg Chim Acta 370 2011 340 345
46. M. Neumann, and F. Vögtle 4,4'-Donor-substituierte und 6,6'-difunktionalisierte 2,2'-Bipyridine Chem Ber 122 1989 589 591
47. Gao XC, Liu LM. China Patent, 200520098133.3.
48. H.J. Xia, J.T. He, B. Xu, S.P. Wen, Y.W. Li, and W.J. Tian A facile convergent procedure for the preparation of triphenylamine-based dendrimers with truxene cores Tetrahedron 64 2008 5736 5742
49. M. Sonntag, and P. Strohriegl Synthesis and characterization of novel conjugated bisindenocarbazoles Tetrahedron 62 2006 8103 8108
50. V. Promarak, A. Punkvuang, T. Sudyoadsuk, S. Jungsuttiwong, S. Saengsuwan, and T. Keawin Synthesis and characterization of N-carbazole end-capped oligofluorene-thiophenes Tetrahedron 63 2007 8881 8890
51. K.M. Omer, S.Y. Ku, Y.C. Chen, K.T. Wong, and A.J. Bard Electrochemical behavior and electrogenerated chemiluminescence of star-shaped D-A compounds with a 1,3,5-Triazine core and substituted fluorene arms J Am Chem Soc 132 2010 10944 10952
52. R. Grisorio, A.D. Aquila, G. Romanazzi, G.P. Suranna, P. Mastrorilli, and P. Cosma Novel bifluorene based conjugated systems: synthesis and properties Tetrahedron 62 2006 627 634
53. J.F. Lee, Y.C. Chen, J.T. Lin, C.C. Wu, C.Y. Chen, and C.A. Dai Blue light-emitting and electron-transporting materials based on dialkyl- functionlized anthracene imidazophenanthrolines Tetrahedron 67 2011 1696 1702
54. R. Cristiano, E. Westphal, I.H. Bechtold, A.J. Bortoluzzi, and H. Gallardo Synthesis and optical/thermal properties of low molecular mass V-shaped materials based on 2,3-dicyanopyrazine Tetrahedron 63 2007 2851 2858
55. W.R. Dowson, and M.W. Windsor Fluorescence yields of aromatic compounds J Phys Chem 72 1968 3251