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).

  • 加载中
    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


  • 加载中
    1. [1]

      Yonghui ZHOURujun HUANGDongchao YAOAiwei ZHANGYuhang SUNZhujun CHENBaisong ZHUYouxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

    2. [2]

      Bing LIUHuang ZHANGHongliang HANChangwen HUYinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398

    3. [3]

      Yue Wu Jun Li Bo Zhang Yan Yang Haibo Li Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028

    4. [4]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

    5. [5]

      Peiran ZHAOYuqian LIUCheng HEChunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355

    6. [6]

      Aidang Lu Yunting Liu Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

    7. [7]

      Jianbao Mei Bei Li Shu Zhang Dongdong Xiao Pu Hu Geng Zhang . Enhanced Performance of Ternary NASICON-Type Na3.5-xMn0.5V1.5-xZrx(PO4)3/C Cathodes for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(12): 2407023-. doi: 10.3866/PKU.WHXB202407023

    8. [8]

      Shengbiao Zheng Liang Li Nini Zhang Ruimin Bao Ruizhang Hu Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096

    9. [9]

      Jinfeng Chu Yicheng Wang Ji Qi Yulin Liu Yan Li Lan Jin Lei He Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105

    10. [10]

      Jian Jin Jing Cheng Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010

    11. [11]

      Wendian XIEYuehua LONGJianyang XIELiqun XINGShixiong SHEYan YANGZhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050

    12. [12]

      Peng XUShasha WANGNannan CHENAo WANGDongmei YU . Preparation of three-layer magnetic composite Fe3O4@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 544-554. doi: 10.11862/CJIC.20230239

    13. [13]

      Xiufang Wang Donglin Zhao Kehua Zhang Xiaojie Song . “Preparation of Carbon Nanotube/SnS2 Photoanode Materials”: A Comprehensive University Chemistry Experiment. University Chemistry, 2024, 39(4): 157-162. doi: 10.3866/PKU.DXHX202308025

    14. [14]

      Li Jiang Changzheng Chen Yang Su Hao Song Yanmao Dong Yan Yuan Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002

    15. [15]

      . . University Chemistry, 2024, 39(9): 0-0.

    16. [16]

      Fan JIAWenbao XUFangbin LIUHaihua ZHANGHongbing FU . Synthesis and electroluminescence properties of Mn2+ doped quasi-two-dimensional perovskites (PEA)2PbyMn1-yBr4. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473

    17. [17]

      Fengmiao Yu Yang Sheng Chanyue Li Bao Li . The Three Lives of Aspirin. University Chemistry, 2024, 39(9): 115-121. doi: 10.12461/PKU.DXHX202402033

    18. [18]

      Pingwei Wu . Application of Diamond Software in Simplex Teaching. University Chemistry, 2024, 39(3): 118-121. doi: 10.3866/PKU.DXHX202311043

    19. [19]

      Baohua LÜYuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In2Se3(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105

    20. [20]

      Geyang Song Dong Xue Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030

Metrics
  • PDF Downloads(825)
  • Abstract views(2352)
  • HTML views(71)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return