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)

1.
Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China

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 (T_d) 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 (T_g) 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).
- Organic light-emitting diodes,
- Triphenylamine,
- Spiro(fluorene-9,9'-xanthene),
- Star-burst,
- Blue-emitting materials
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
1. [1]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
2. [2]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan 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
3. [3]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
4. [4]
  Yan Xin , Yunnian Ge , Zezhong Li , Qiaobao Zhang , Huajun Tian . Research Progress on Modification Strategies of Organic Electrode Materials for Energy Storage Batteries. Acta Physico-Chimica Sinica, 2024, 40(2): 2303060-0. doi: 10.3866/PKU.WHXB202303060
5. [5]
  Hao Chen , Dongyue Yang , Gang Huang , Xinbo Zhang . Progress on Liquid Organic Electrolytes of Li-O₂ Batteries. Acta Physico-Chimica Sinica, 2024, 40(7): 2305059-0. doi: 10.3866/PKU.WHXB202305059
6. [6]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei 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
7. [7]
  Jiaxuan Zuo , Kun Zhang , Jing Wang , Xifei Li . Nucleation Regulation and Mechanism of Precursors for Nickel Cobalt Manganese-based Cathode Materials in Lithium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100009-0. doi: 10.3866/PKU.WHXB202404042
8. [8]
  Chenyue Huang , Hongfei Zheng , Ning Qin , Canpei Wang , Liguang Wang , Jun Lu . Single-Crystal Nickel-Rich Cathode Materials: Challenges and Strategies. Acta Physico-Chimica Sinica, 2024, 40(9): 2308051-0. doi: 10.3866/PKU.WHXB202308051
9. [9]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
10. [10]
  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
11. [11]
  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
12. [12]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying 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
13. [13]
  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
14. [14]
  Jianbao Mei , Bei Li , Shu Zhang , Dongdong Xiao , Pu Hu , Geng Zhang . Enhanced Performance of Ternary NASICON-Type Na_3.5−xMn_0.5V_1.5−xZr_x (PO₄)₃/C Cathodes for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(12): 2407023-0. doi: 10.3866/PKU.WHXB202407023
15. [15]
  Hong Yan , Wenfeng Wang , Keyin Ye , Yaofeng Yuan . Organic Electrochemistry and Its Integration into Chemistry Teaching. University Chemistry, 2025, 40(5): 301-310. doi: 10.12461/PKU.DXHX202407027
16. [16]
  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
17. [17]
  Xichen YAO , Shuxian WANG , Yun WANG , Cheng WANG , Chuang ZHANG . Oxygen reduction performance of self?supported Fe/N/C three-dimensional aerogel catalyst layers. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1387-1396. doi: 10.11862/CJIC.20240384
18. [18]
  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
19. [19]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
20. [20]
  Xiaohang JIN , Qi LIU , Jianping LANG . Room‑temperature solid‑state synthesis, structure, and third‑order nonlinear optical properties of phosphine‑ligand‑protected silver thiolate clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1505-1512. doi: 10.11862/CJIC.20250125

Get Citation

PDF

XML

Metrics

PDF Downloads(825)
Abstract views(2521)
HTML views(83)

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