The New Synthesis of Novel Organic Light-Emitting Material Spirobifluorene by Ullman Coupling

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: Applied Mechanics and Materials (Volumes 204-208)
• Pages: 4051-4054
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.204-208.4051
• Online since: October 2012
• Authors: Ya Zhou Lou, Xiao Xia Sun, Ying Chun Li
• Keywords: 2,7-dibromo-9,9′-spirobifluorene, Organic Light-Emmitting, Ullman 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) 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. (b) Chien, Y.-Y.; Wong, K.-T.; Chou, P.-T.; Cheng, Y.-M. Chem. Commun. 2002, 2874. (c) 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. (d) 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. (e) 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. (f) Wu, C.-C.; Lin, Y.-T.; Wong, K.-T.; Chen, R.-T.; Chien, Y.-Y. AdV. Mater. 2004, 16, 61. (g) Su, H.-J.; Wu, F.-I.; Shu, C.-F. Macromolecules 2004, 37, 7197. (h) 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.

[3] (a) Saragi, T. P. I.; Fuhrmann-Lieker, T.; Salbeck, J. Synth. Met. 2005, 148, 267. (b) 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. (c) Saragi, T. P. I.; Fuhrmann-Lieker, T.; Salbeck, J. AdV. Funct. Mater. 2006, 16, 966. (d) Heredia, D.; Natera, J.; Gervaldo, M.; Otero, L.; Fungo, F.; Lin, C. Y.; Wong, K. T. Org. Lett. 2009, 12, 12. (e) 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] Bacher, A.; Erdelen, C. H.; Paulus, W.; Ringsdorf, H.; Schimdt, H.- W.; Schuhmacher P. Macromolecules, 1999, 32, 4551.

[6] Jacob, P.; Callery, P. S.; Shulgin, A. T.; Catagnoli, N. J. Org. Chem. 1976, 41, 3627