Citation: XIAO Lixin, HU Shuangyuan, KONG Sheng, CHEN Zhijian, QU Bo, NG Qihuang. Synthesis of Poly(9,9-diallylfluorene) and the Mechanism of Its Single Green Emission[J]. Acta Physico-Chimica Sinica, ;2011, 27(04): 977-982. doi: 10.3866/PKU.WHXB20110325 shu

Synthesis of Poly(9,9-diallylfluorene) and the Mechanism of Its Single Green Emission

1.
State Key Laboratory for Mesoscopic Physics, School of Physics, Peking University, Beijing 100871, P. R. China

Received Date: 19 November 2010
Available Online: 15 February 2011
Fund Project: 国家自然科学基金(10934001, 60907015, 10821062) (10934001, 60907015, 10821062)国家重点基础研究发展规划项目(973) (2007CB307000, 2009CB930504)资助 (973) (2007CB307000, 2009CB930504)

Poly(9,9-diallylfluorene) (PAF) with single green emission was synthesized through polymerization of allyl substituted 2,7-dibromofluorene in the presence of NiCl₂ as the catalyst. PAF shows deep blue fluorescence at 403 nm in solution and 456 nm in solid film state. The organic electroluminescence device (OLED) gives a green emission with the peak at 532 nm by using PAF as the emitter with a structure of ITO/PEDOT:PSS/PAF/LiF/Al (ITO: indium tin oxides; PEDOT: poly(3,4- ethylenedioxythiophene); PSS: poly(styrenesulfonate)). The photoluminescence (PL) of the PAF film red- shifted after thermal anealing, the original peak of blue emission decreased and a new peak of green emissioin increased. However, there is no change in the chemical structure based on the Fourier transform infrared (FT-IR) spectra of PAF after thermal annealing under vacuum. Moreover, there is no change on the PL spectra of PAF before and after the evaporation of metal cathode. It can be deduced that the single green emisson of PAF based OLED is original from the inter-chain aggregation which can be confirmed from their atomic force microscopy (AFM) images.
- Polymer,
- Diallylfluorene,
- Green emission,
- Inter-chain aggregation,
- Organic light-emitting device
1. [1]
  
  (1) Burroughes, J. H.; Bradleyd, D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
2. [2]
  (2) Cao, H. Y.; Chen, Z. J.; Xiao, L. X.; Liu, Z. G.; Zheng, M. J.; Qu, B.; ng, Q. H. Spectroscopy and Spectra Analysis 2008, 28, 752.
3. [3]
  [曹华雨, 陈志坚, 肖立新, 刘振刚, 郑明杰, 曲波, 龚旗煌. 光谱学与光谱分析, 2008, 28, 752.]
4. [4]
  (3) Ohmori, Y.; Uchida, A.; Muro, K.; Yoshino, K. Jpn. J. Appl. Phys. 1991, 30, L1941.
5. [5]
  (4) Fukuda, K.; Sawaka, K.; Yoshino, J. J. Polym. Sci. Part A: Polym. Chem. 1993, 31, 2465.
6. [6]
  (5) Schluter, A. D. J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 1533.
7. [7]
  (6) Tao, S. L.; Peng, Z. K.; Zhang, X. H.; Wang, P. F.; Lee, C. S.; Lee, S. T. Adv. Funct. Mater. 2005, 15, 1716.
8. [8]
  (7) Gao, Z. Q.; Li, Z. H.; Xia, P. F.; Wong, M. S.; Cheah, K. W.; Chen, C. H. Adv. Funct. Mater. 2007, 17, 3194.
9. [9]
  (8) Wong, K. T.; Chien, Y. Y.; Chen, R. T.; Wang, C. F.; Lin, Y. T.; Chiang, H. H.; Hsieh, P. Y.; Wu, C. C.; Chou, C. H.; Su, Y. O.; Lee, G. H.; Peng, S. M. J. Am. Chem. Soc. 2002, 124, 11576.
10. [10]
  (9) Sun, G. N.; Xu, H.; Liu, X. D.; Liu, D. D.; Yang, B.; Tian, L. L.; Ma, Y. G. Acta Phys. -Chim. Sin. 2010, 26, 2529.
11. [11]
  [孙冠楠, 许海, 刘晓冬, 刘丹丹, 杨兵, 田雷蕾, 马於光. 物理化学学报, 2010, 26, 2529.]
12. [12]
  (10) Ma, T.; Jiang, Y. D.; Yu, J. S.; Lou, S. L.; Li, L.; Zhang, Q. Acta Phys. -Chim. Sin. 2008, 24, 977.
13. [13]
  [马涛, 蒋亚东, 于军胜, 娄双玲, 李璐, 张清. 物理化学学报, 2008, 24, 977.]
14. [14]
  (11) Abbel, R.; Schenning, A. P. H. J.; Meijer, E. W. J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 4215.
15. [15]
  (12) Li, F. S.; Chen, Z. J.; Qu, B.; Wei, W.; ng, Q. H. J. Phys. D: Appl. Phys. 2005, 38, 847.
16. [16]
  (13) Li, Y. B.; Teng, F.; Xu, Z.; Hou, Y. B.; Xu, X. Spectroscopy and Spectra Analysis 2005, 25, 1030.
17. [17]
  [李云白, 滕枫, 徐征, 侯延冰, 徐叙. 光谱学与光谱分析, 2005, 25, 1030.]
18. [18]
  (14) Kreenschmidt, M.; Klarner, G.; Fuhrer, T.; Ashenhurst, J.; Karg, S.; Chen, W. D.; Lee, V. Y.; Scott, J. C.; Miller, R. D. Macromolecules 1998, 31, 1099.
19. [19]
  (15) Kl?rner, G.; Lee, J.; Lee, V. Y.; Chan, E.; Chen, J. P.; Nelson, A.; Markiewicz, D.; Siemens, R.; Scott, J. C.; Miller, R. D. Chem. Mater. 1999, 11, 1800.
20. [20]
  (16) List, J. W.; Guentner, R.; Freitas, P. S.; Scherf, U. Adv. Mater. 2002, 14, 374.
21. [21]
  (17) Grisorio, R.; Suranna, G. P.; Mastrorilli, P.; Nobile, C. F. Adv. Funct. Mater. 2007, 17, 538.
22. [22]
  (18) Chi, C.; Im, C.; Enkelmann, V.; Ziegler, A.; Lieser, G.; Wegner, G. Chem. Eur. J. 2005, 11, 6833.
23. [23]
  (19) Craig, M. R.; Meijer, E. W. Appl. Phys. Lett. 2002, 80, 4489.
24. [24]
  (20) Liang, J.; Qian, Y.; Xie, L. H.; Shi, N. E.; Chen, S. F.; Deng, X. Y.; Huang, W. Acta Phys. -Chim. Sin. 2010, 26, 946.
25. [25]
  [梁婧, 钱妍, 解令海, 石乃恩, 陈淑芬, 邓先宇, 黄维. 物理化学学报, 2010, 26, 946.]
26. [26]
  (21) Zhang, L.; Lin, Z. Q.; Gu, J. F.; Yin, C. R.; Hou, X. Y.; Liu, F.; Liu, Y. Y.; Xie, L. H.; Chen, S. F.; Huang, W. Acta Phys. -Chim. Sin. 2010, 26, 1934.
27. [27]
  [张龙, 林宗琼, 顾菊芬, 殷成蓉, 侯晓雅, 刘烽, 刘玉玉, 解令海, 陈淑芬, 黄维. 物理化学学报, 2010, 26, 1934.]
28. [28]
  (22) Setayesh, S.; Grimsdale, A. C.; Weil, T.; Enkelmann, V.; Mullen, K.; Meghdadi, F.; List, E. J. W.; Leising, G. J. Am. Chem. Soc. 2001, 123, 946.
29. [29]
  (23) Jin, J. K.; Kwon, S. K.; Kim, Y. H.; Shin, D. C.; You, H.; Jung, H. T. Macromolecules 2009, 42, 6339.
30. [30]
  (24) Zhou, X. H.; Zhang, Y.; Xie, Y. Q.; Cao, Y.; Pei, J. Macromolecules 2006, 39, 3830.
31. [31]
  (25) Ranger, M.; Rondeau, D.; Leclerc, M. Macromolecules 1997, 30, 7686.
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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

Synthesis of Poly(9,9-diallylfluorene) and the Mechanism of Its Single Green Emission

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com