Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Properties of Imidazole-p-phenothiazine Derivatives as Light-Emitting and Ambipolar Materials
Corresponding Author(s) : Xin Zhao
Asian Journal of Chemistry,
Vol. 26 No. 6 (2014): Vol 26 Issue 6
Abstract
Novel phenothiazine derivatives were designed and synthesized for application as electroluminescent materials. They were characterized by means of 1H, 13C NMR and FTIR. The optical, electrochemical and thermal properties were also investigated. The relationship between the chemical structure and the properties of these materials was evaluated. Due to the introduction of thiophene ring, these compounds exhibited efficient emission from blue to green and red shifs in absorption and photoluminescence spectra. With respect to thermal properties and the oxidation potentials, it can be turned by varying the conjugation length of compounds and the length of alkyl chains. Mostly, all four compounds had suited HOMO and LUMO energy levels which can be used not only hole-transporting but also electron-tansporting materials in organic light-emitting devices.
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References
C.W. Tang and S.A. van Slyke, Appl. Phys. Lett., 51, 913 (1987); doi:10.1063/1.98799.
L.S. Hung and C.H. Chen, Mater. Sci. Eng. Rep., 39, 143 (2002); doi:10.1016/S0927-796X(02)00093-1.
Y. Kijima, N. Asai and S. Tamura, Jpn. J. Appl. Phys., 38, 5274 (1999); doi:10.1143/JJAP.38.5274.
A. Saitoh, N. Yamada, M. Yashima, K. Okinaka, A. Senoo, K. Ueno, D. Tanaka and R. Yashiro, Technical Digest., 35, 150 (2004); doi:10.1889/1.1825781.
S.L. Lin, L.H. Chan, R.H. Lee, M.Y. Yen, W.J. Kuo, C.T. Chen and R. Jeng, Adv. Mater., 20, 3947 (2008); doi:10.1002/adma.200801023.
S.L. Gong, Y.B. Zhao, M. Wang, C.L. Yang, C. Zhong, J.G. Qin and D.G. Ma, Chem. Asian, 5, 2093 (2010); doi:10.1002/asia.201000206.
H.B. Xiao, H. Shen, Y.G. Lin, J.H. Su and H. Tian, Dyes Pigments, 73, 224 (2007); doi:10.1016/j.dyepig.2005.11.010.
C.H. Chen, W.S. Huang, M.Y. Lai, W.C. Tsao, J.T. Lin, Y.H. Wu, T.H. Ke, L.Y. Chen and C.C. Wu, Adv. Funct. Mater., 19, 2661 (2009); doi:10.1002/adfm.200900561.
Z.M. Hudson and S. Wang, Acc. Chem. Res., 42, 1584 (2009); doi:10.1021/ar900072u.
Y. Yuan, D. Li, X. Zhang, X. Zhao, Y. Liu, J. Zhang and Y. Wang, New J. Chem., 35, 1534 (2011); doi:10.1039/c1nj20072k.
Y. Zhang, S.-L. Lai, Q.-X. Tong, M.-F. Lo, T.-W. Ng, M.-Y. Chan, Z.-C. Wen, J. He, K.-S. Jeff, X.-L. Tang, W.-M. Liu, C.-C. Ko, P.-F. Wang and C.-S. Lee, Chem. Mater., 24, 61 (2012); doi:10.1021/cm201789u.
M.J. Kim, Y.J. Yu, J.H. Kim, Y.S. Jung, K.Y. Kay, S.B. Ko, C.-R. Lee, I.-H. Jang, Y.-U. Kwon and N.-G. Park, Dyes Pigments, 95, 134 (2012); doi:10.1016/j.dyepig.2012.04.002.
H. Padhy, J.H. Huang, D. Sahu, D. Patra, D. Kekuda, C.W. Chu and H.C. Lin, J. Polym. Sci., Part A Polym. Chem., 48, 4823 (2010); doi:10.1002/pola.24273.
G.Y. Sang, Y.P. Zou and Y.F. Li, PhysChemComm, 112, 12058 (2008).
H. Tian, X. Yang, J. Cong, R. Chen, C. Teng, J. Liu, Y. Hao, L. Wang and L. Sun, Dyes Pigments, 84, 62 (2010); doi:10.1016/j.dyepig.2009.06.014.
T.Y. Wu, M.H. Tsao, F.C. Chen, S.G. Su, C.W. Chang, H.P. Wang, Y.C. Lin and I.W. Sun, J. Iran. Chem. Soc., 7, 707 (2010); doi:10.1007/BF03246061.