Citation: CHU Zeng-Ze, WANG Dan, ZHANG Chao, ZOU De-Chun. Synthesis and Optoelectronic Properties of Blue-Emitting Star-Burst Oli mers Based on Triphenylamine and Spiro(fluorene-9,9'-xanthene)[J]. Acta Physico-Chimica Sinica, ;2012, 28(08): 2000-2007. doi: 10.3866/PKU.WHXB201206071 shu

Synthesis and Optoelectronic Properties of Blue-Emitting Star-Burst Oli mers Based on Triphenylamine and Spiro(fluorene-9,9'-xanthene)

  • Received Date: 7 May 2012
    Available Online: 7 June 2012

    Fund Project: 国家自然科学基金(50833001) (50833001)国家重点基础研究发展规划项目(973) (2011CB933300)资助. (973) (2011CB933300)

  • Three star-burst conjugated oli mers based on triphenylamine (TPA), fluorene and spiro (fluorene-9,9'-xanthene) (SFX) have been synthesized via the Sonogashira cross-coupling reaction. These well-defined oli mers possess high decomposition temperatures (Td) at 417, 439, and 425 °C, respectively. Differential scanning calorimetry (DSC) demonstrates two oli mers which incorporate the SFX unit, TPA-SFX and TPA-SFXCz, possess higher glass transition temperatures (Tg) at 141 and 127 ° C, respectively, compared with 101 °C for TPA-F. The investigation of their optical properties shows TPA-SFX and TPA-SFXCz exhibit a single blue emission in film with emission peaks at 434 and 442 nm, respectively, whereas TPA-F shows a broad double-peak emission located at 424 and 455 nm, which implies the nonplanar TPA and spiro SFX moieties can effectively restrict the formation of aggregates or excimers. Electrochemical investigations show that these oli mers have relatively high HOMO levels at around -5.4 eV due to incorporation of the electron-rich TPA core. Electroluminescence (EL) devices with a configuration of ITO (indium tin oxide)/PEDOT:PSS (poly(3,4-ethylenedioxythiophene): poly (styrenesulfonate))/ oli mer/TPBI (1,3,5-tris(1-phenyl-1H -benzimidazol-2-yl)benzene)/LiF/Al were constructed using these oli mers as the emitter by spin-coating, with TPBI as the electron-transporting and hole-blocking layer. The device using TPA-SFX as the emitting layer exhibits bright blue emission with the maximum brightness and maximum current efficiency of 2680 cd·A-2 and 0.35 cd·A-1, and CIE color coordination of (0.17, 0.13).

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    1. [1]

      (1) Tang, C.W.; Vanslyke, S. A. Appl. Phys. Lett. 1987, 51, 913.doi: 10.1063/1.98799

    2. [2]

      (2) Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R.N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B.Nature 1990, 347, 539. doi: 10.1038/347539a0

    3. [3]

      (3) Friend, R. H.; Gymer, R.W.; Holmes, A. B.; Burroughes, J. H.;Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.;Bredas, J. L.; Logdlund, M.; Salaneck,W. R. Nature 1999, 397,121. doi: 10.1038/16393

    4. [4]

      (4) Muller, C. D.; Falcou, A.; Reckefuss, N.; Rojahn, M.;Wiederhirn, V.; Rudati, P.; Frohne, H.; Nuyken, O.; Becker, H.;Meerholz, K. Nature 2003, 421, 829. doi: 10.1038/nature01390

    5. [5]

      (5) Xiao, L. X.; Hu, S. Y.; Kong, S.; Chen, Z. J.; Qu, B.; ng, Q.H. Acta Phys. -Chim. Sin. 2011, 27, 977. [肖立新, 胡双元, 孔胜, 陈志坚, 曲波, 龚旗煌. 物理化学学报, 2011, 27, 977.]doi: 10.3866/PKU.WHXB20110325

    6. [6]

      (6) Mo, Y. Q.; Chang, X. Y.; Hu, S. J.; Han, S. H.;Wu, H. B.; Peng,J. B. Acta Phys. -Chim. Sin. 2011, 27, 1188. [莫越奇, 常学义,胡苏军, 韩绍虎, 吴宏滨, 彭俊彪. 物理化学学报, 2011, 27,1188.] doi: 10.3866/PKU.WHXB20110527

    7. [7]

      (7) Saragi, T. P. I.; Spehr, T.; Siebert, A.; Fuhrmann-Lieker, T.;Salbeck, J. Chem. Rev. 2007, 107, 1011. doi: 10.1021/cr0501341

    8. [8]

      (8) Jo, J. H.; Chi, C. Y.; Hoger, S.;Wegner, G.; Yoon, D. Y. Chem. Eur. J. 2004, 10, 2681. doi: 10.1002/chem.200305659

    9. [9]

      (9) Zhang, B. H.; Tan, G. P.; Lam, C. S.; Yao, B.; Ho, C. L.; Liu, L.H.; Xie, Z. Y.;Wong,W. Y.; Ding, J. Q.;Wang, L. X. Adv. Mater. 2012, 24, 1873. doi: 10.1002/adma.201104758

    10. [10]

      (10) Geng, Y. H.; Katsis, D.; Culligan, S.W.; Ou, J. J.; Chen, S. H.;Rothberg, L. J. Chem. Mater. 2002, 14, 463. doi: 10.1021/cm0109084

    11. [11]

      (11) Luo, J.; Zhou, Y.; Niu, Z. Q.; Zhou, Q. F.; Ma, Y. G.; Pei, J.J. Am. Chem. Soc. 2007, 129, 11314. doi: 10.1021/ja073466r

    12. [12]

      (12) Tang, S.; Liu, M.; Lu, P.; Xia, H.; Li, M.; Xie, Z. Q.; Shen, T. Z.;Gu, C.;Wang, H. P.; Yang, B.; Ma, Y. G. Adv. Funct. Mater.2007, 17, 2869. doi: 10.1002/adfm.200700175

    13. [13]

      (13) Vak, D. J.; Chun, C. M.; Lee, C. L.; Kim, J. J.; Kim, D. Y.J. Mater. Chem. 2004, 14, 1342. doi: 10.1039/b317028d

    14. [14]

      (14) Vak, D.; Jo, J.; Ghim, J.; Chun, C.; Lim, B.; Heeger, A. J.; Kim,D. Y. Macromolecules 2006, 39, 6433. doi: 10.1021/ma060683o

    15. [15]

      (15) Chen, Q.;Wang, J. X.;Wang, Q.; Bian, N.; Li, Z. H.;Yan, C. G.;Han, B. H. Macromolecules 2011, 44, 7987. doi: 10.1021/ma201626s

    16. [16]

      (16) Tseng, Y. H.; Shih, P. I.; Chien, C. H.; Dixit, A. K.; Shu, C. F.;Liu, Y. H.; Lee, G. H. Macromolecules 2005, 38, 10055. doi: 10.1021/ma051798f

    17. [17]

      (17) Xie, L. H.; Liu, F.; Tang, C.; Hou, X. Y.; Hua, Y. R.; Fan, Q. L.;Huang,W. Org. Lett. 2006, 8, 2787. doi: 10.1021/ol060871z

    18. [18]

      (18) Chu, Z. Z.;Wang, D.; Zhang, C.; Fan, X.; Tang, Y.W.; Chen, L.;Zou, D. C. Macromol. Rapid Commun. 2009, 30, 1745. doi: 10.1002/marc.200900268

    19. [19]

      (19) Chu, Z. Z.;Wang, D.; Zhang, C.;Wang, F. Z.;Wu, H.W.; Lv, Z.B.; Hou, S. C.; Fan, X.; Zou, D. C. Synth. Met. 2012, 162, 614.doi: 10.1016/j.synthmet.2012.02.009

    20. [20]

      (20) Poriel, C.; Cocherel, N.; Rault-Berthelot, J.; Vignau, L.; Jeannin,O. Chem. Eur. J. 2011, 17, 12631. doi: 10.1002/chem.201100790

    21. [21]

      (21) Juan, Z.; Swager, T. M. Adv. Polym. Sci. 2005, 177, 151.doi: 10.1007/b101377

    22. [22]

      (22) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605. doi: 10.1021/cr990257j

    23. [23]

      (23) Hu, X. D.; Su, L.; Liao, Q.; Zhen, C. G.; Chuai, Y. T.; Zou, D.C. Chem. J. Chin. Univ. 2005, 26, 1900. [胡小丹, 苏立,廖琪, 甄常刮, 啜玉涛, 邹德春. 高等学校化学学报, 2005,26, 1900.]

    24. [24]

      (24) Burn, P. L.; Lo, S. C.; Samuel, I. D.W. Adv. Mater. 2007, 19,1675. doi: 10.1002/adma.200601592

    25. [25]

      (25) Zeng, D. L.; Chen, J.W.; Chen, Z.; Zhu,W. H.; He, J.; Yu, F.;Huang, H.;Wu, H. R.; Liu, C.; Ren, S. J.; Du, J. P.; Sun, J.; Xu,E. J.; Cao, A.; Fang, Q. Macromol. Rapid Commun. 2007, 28,772. doi: 10.1002/marc.200600786

    26. [26]

      (26) Breen, C. A.; Rifai, S.; Bulovic, V.; Swager, T. M. Nano Lett.2005, 5, 1597. doi: 10.1021/nl050995p

    27. [27]

      (27) Pu, K. Y.; Chen, Y.; Qi, X. Y.; Qin, C. Y.; Chen, Q. Q.;Wang, H.Y.; Deng, Y.; Fan, Q. L.; Huang, Y. Q.; Liu, S. J.;Wei,W.; Peng,B.; Huang,W. J. Polym. Sci. Part A: Polym. Chem. 2007, 45,3776. doi: 10.1002/pola.22129

    28. [28]

      (28) Zhao, Z. J.; Li, J. H.; Chen, X. P.; Lu, P.; Yang, Y. Org. Lett.2008, 10, 3041. doi: 10.1021/ol801001h

    29. [29]

      (29) Zhao, Z. J.; Zhao, Y. X.; Lu, P.; Tian,W. J. J. Phys. Chem. C2007, 111, 6883. doi: 10.1021/jp0701946

    30. [30]

      (30) Roncali, J.; Leriche, P.; Cravino, A. Adv. Mater. 2007, 19, 2045.doi: 10.1002/adma.200700135

    31. [31]

      (31) Shirota, Y. J. Mater. Chem. 2000, 10, 1. doi: 10.1039/a908130e

    32. [32]

      (32) Shirota, Y. J. Mater. Chem. 2005, 15, 75. doi: 10.1039/b413819h

    33. [33]

      (33) Jiang, Y. H.;Wang, Y. C.; Hua, J. L.; Qu, S. Y.; Qian, S. Q.;Tian, H. J. Polym. Sci. Pol. Chem. 2009, 47, 4400. doi: 10.1002/pola.23493


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