The Synthesis of Novel Organic Light-Emitting Material 2,7-Dibromo-2′,3′,6′,7′-Tetra(2-Methylbutyloxy)spirobifluorene

Abstract:

A mide, simple and efficient synthetic procedure for the preparation of 2,7-dibromo-2′,3′,6′,7′-tetra(2-methylbutyloxy)spirobifluorene and key intermediates, tetra(2-methlbutyloxy)biphenyl ，2-bromo-4,5,3′,4′-tetra(2-methylbutyloxy)biphenyl, 2,7-Dibromo-2′,6,3′,7′--tetra(2-methylbutyloxy)biphenyl-9-Fluorenol, has been developed. The procedure described herein offers several advantages, including high product yields, easy purification, and large scale production. Ether protected 2,7-dibromo-9,9′-spirobifluorene has good solubility in organic aolvents to permit an appropriate coating process, ability to achieve various colors so as to make full color display elements possible.

• Periodical: Advanced Materials Research (Volumes 287-290)
• Pages: 270-275
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.287-290.270
• Online since: July 2011
• Authors: Xiao Xia Sun, Ying Chun Li, Xi Mei Liu, Xiao Xiao Zhuang, Ya Zhou Lou
• Keywords: 2,7-dibromo-9,9′-spirobifluorene, Organic Light-Emmitting, Suzuki Coupling

References

[1] (a) Geng, Y.; Trajkovska, A.; Katsis, D.; Ou, J. J.; Culligan, S. W.; Chen, S. H. J. Am. Chem. Soc., 2002, 124, 8337; (b) Scherf, U.; List, E. J. W. Adv. Mater., 2002, 14, 477; (c) Geng, Y.; Culligan, S. W.; Trajkovska, A.; Wallace, J. U.; Chen, S. H. Chem. Mater., 2003, 15, 542; (d) Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Jenekhe, S. A. Chem. Mater., 2004, 16, 4556; (e) Li, J. Y.; Ziegler, A.; Wegner, G. Chem. Eur. J., 2005, 11, 4450; (f) Tang, W; Ke, L.; Tan, L.; Lin, T.; Kietzke, T.; Chen, Z. K. Macromolecules, 2007, 40, 6164; (g) Grisorio, R.; Piliego, C.; Cosma, P.; Fini, P.; Mastrorilli, P.; Gigli, G.; Suranna, G. P.; Nobile, C. F. J. Polym. Sci. Part A: Polym. Chem., 2009, 47, 2093. (h) Li, H.; Wang, L.; Zhao, B.; Shen, P.; Tan S. J. Polym. Sci. Part A: Polym. Chem., 2009, 47, 3296; (i) Jeong, E; Kim, S. H.; Jung, I. H.; Xia, Y.; Lee, K.; Suh, H.; Shim, H.-K.; Woo, H. Y. J. Polym. Sci. Part A: Polym. Chem., 2009, 47, 3467.

[2] (a) Wu, R.; Schumn, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem.1996, 61, 6906. (b) Yu, W..-L.; Pei, J.; Hung, W.; Heeger, A. J. AdV. Mater.2000, 12, 828. (c) 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. (d) Wu, C. C.; Lin, Y. T.; Chiang, H. H.; Cho, T. Y.; Chen, C. W.; Wong, K. T.; Liao, Y. L.; Lee, G. H.; Peng, S. M. Appl. Phys. Lett. 2002, 81, 577. (e) Chien, Y.-Y.; Wong, K.-T.; Chou, P.-T.; Cheng, Y.-M. Chem. Commun. 2002, 2874. (f) Wu, C.-C.; Liu, T.-L.; Hung, W.-Y.; Lin, Y.-T.; Wong, K.-T.; Chen, R.-T.; Chen, Y.-M.; Chien, Y.-Y. J. Am. Chem. Soc. 2003,125, 3710. (g) Mu¨ller, C. D.; Falcou, A.; Reckefuss, N.; Rojehn, M.; Eiederhirn, V.; Rudati, P.; Frohne, H.; Nuyken, O.; Becker, H.; Meerholtz, K. Nature 2003 421, 829. (h) Schneider, D.; Rabe, T.; Riedl, T.; Dobbertin, T.; Kro¨ger, M.; Becker, E.; Weimann, T.; Wang, J.; Hinze, P. Appl. Phys. Lett. 2004, 85, 1659. (i) Wu, C.-C.; Lin, Y.-T.; Wong, K.-T.; Chen, R.-T.; Chien, Y.-Y. AdV. Mater. 2004, 16, 61.(j) Su, H.-J.; Wu, F.-I.; Shu, C.-F. Macromolecules 2004, 37, 7197. (k) Wu, Y.; Li, J.; Fu, Y.; Bo, Z. Org. Lett. 2004, 6, 3485. (l) Cao, X.-Y.; Zhang, W.; Zi, H.; Pei, J. Org. Lett. 2004, 6, 4845. (m) Cheun, C. H.; Tao, Y. T.; Wu, F. I.; Shu, C. F. Appl. Phys. Lett. 2004, 85, 4609. (n) Fungo, F.; Wong, K.-T.; Ku, S.-Y.; Hung, Y.-Y.; Bard, A. J. J. Phys. Chem. B 2005, 109, 3984. (o) Oyston, S.; Wang, C.; Hughes, G.; Batsanov, A. S.; Perepichka, I. F.; Bryce, M. R.; Ahn, J. H.; Pearson, C.; Petty, M. C. J. Mater. Chem. 2005, 15, 194. (p) Wong, K.-T.; Chen, R.-T.; Fang, F.-C.; Wu, C.-C.; Lin, Y.-T. Org. Lett. 2005, 7, 1979.

[3] (a) Hosokawa, C.; Higashi, H.; Nakamura, H.; Kusumoto, T. Appl. Phys. Lett. 1995, 67, 3853. (b) Saragi, T. P. I.; Fuhrmann-Lieker, T.; Salbeck, J. Synth. Met. 2005, 148, 267. (c) Lin, H. W.; Ku, S. Y.; Su, H. C.; Huang, C. W.; Lin, Y. T.; Wong, K. T.; Wu, C. C. AdV. Mater. 2005, 17, 2489. (d) Saragi, T. P. I.; Fuhrmann-Lieker, T.; Salbeck, J. AdV. Funct. Mater. 2006, 16, 966. (e) Heredia, D.; Natera, J.; Gervaldo, M.; Otero, L.; Fungo, F.; Lin, C. Y.; Wong, K. T. Org. Lett. 2009, 12, 12. (f) Chi, L. C.; Hung, W. Y.; Chiu, H. C.; Wong, K. T. Chem. Commun. 2009, 3892.

DOI: 10.1002/adfm.200500361

[4] (a) Wu, C. C.; Liu, T. L.; Hung, W. Y.; Lin, Y. T.; Wong, K. T.; Chen, R. T.; Chen, Y. M.; Chien, Y. Y. J. Am. Chem. Soc. 2003, 25, 3710. (b) Spehr, T.; Pudzich, R.; Fuhrmann, T.; Salbeck, J. Org. Electron. 2003, 4, 61.

[5] (a) Wu, R.; Schumn, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem.1996, 61, 6906. (b) Yu, W. L.; Pei, J.; Huang, W.; Heeger, A. J. AdV. Mater. 2000, 12, 828. (c) 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. (d) Chien, Y. Y.; Wong, K. T.; Chou, P. T.; Cheng, Y. M. Chem. Commun. 2002, 2874. (e) Pei, J.; Ni, J.; Zhou, X. H.; Cao, X. Y.; Lai, Y. H. J. Org. Chem. 2002, 67, 4924. (f) Mu¨ller, C. D.; Falcou, A.; Reckefuss, N.; Rojehn, M.; Eiederhirn, V.; Rudati, P.; Frohne, H.; Nuyken, O.; Becker, H.; Meerholtz, K. Nature 2003, 421, 829. (g) Wu, C. C.; Lin, Y. T.; Wong, K. T.; Chen, R. T.; Chien, Y. Y. AdV. Mater. 2004, 16, 61. (h) Su, H. J.; Wu, F. I.; Shu, C. F. Macromolecules 2004, 37, 7197. (i) Wu, Y.; Li, J.; Fu, Y.; Bo, Z. Org. Lett. 2004, 6, 3485. (j) Cao, X. Y.; Zhang, W.; Zi, H.; Pei, J. Org. Lett. 2004, 6, 4845. (k) Wong, K. T.; Chen, R. T.; Fang, F. C.; Wu, C. C.; Lin, Y. T. Org. Lett. 2005, 7, 1979. (l) Lyu, Y. Y.; Kwak, J.; Jeon, W. S.; Byun, Y.; Lee, H. S.; Kim, D.; Lee, C.; Char, K. AdV. Func. Mater. 2009, 19, 420.

[6] Liu, B.; Bazan, G. C. J. Am. Chem. Soc. 2006, 128, 1188.

[7] Dougherty, T. K.; Lau, K. S. Y. J. Org. Chem. 1983, 48, 5273.