DOI QR코드

DOI QR Code

Bis(3,5-dibromophenyl)dimethylsilane: A useful synthon for organosilicon chemistry

  • Lee, Jong-Dae (Department of Chemistry, College of Natural Sciences, Chosun University)
  • 투고 : 2021.12.24
  • 심사 : 2022.03.28
  • 발행 : 2022.03.31

초록

The diarylsilyl compound, C14H12Br4Si, was prepared from the reaction of 3,5-dibromophenyllithium with dimethyldichlorosilane, (CH3)2SiCl2, at -78 ℃, can be a good synthon for derivatization to produce efficient host materials for organic light emitting diodes (OLEDs). Crystal structure analysis shows a slight deviation from ideal tetrahedral symmetry around the Si atom, whose conformation is effective in ensuring the maximum separation of the two phenyl rings and the two methyl substituents. The directions of the two aromatic rings are almost perpendicular to each other. The molecule exists as a monomer in the solid state.

키워드

참고문헌

  1. Tao, Y. T., Wang, Q., Shang, Y., Yang, C. L., Ao, L., Qin, J. G., Ma, D. G., and Shuai, G., "Multifunctional bipolar triphenylamine/oxadiazole derivatives: highly efficient blue fluorescence, red phosphorescence host and two-color based white OLEDs", Chemical Communications, no. 1, pp. 77-79, 2009.
  2. Ho, M. H., Balaganesan, B., Chu, T. Y., Chen, T. M., and Chen, C. H., "A morphologically stable host material for efficient phosphorescent green and red organic light emitting devices", Thin Solid Films, vol. 517, no. 2, pp. 943-947, 2008. https://doi.org/10.1016/j.tsf.2008.07.005
  3. Tsuboi, T., Murayama, H., Yeh, S. -J., Wu, M. -F., and Chen, C. -T., "Photoluminescence characteristics of blue phosphorescent Ir3+-compounds FIrpic and FIrN4 doped in mCP and SimCP", Optical Materials, vol. 31, no. 2, pp. 366-371, 2008. https://doi.org/10.1016/j.optmat.2008.05.010
  4. Ren, X., Li, J., Holmes, R. J., Djurovich, P. I., Forrest, S. R., and Thompson, M. E., "Ultrahigh Energy Gap Hosts in Deep Blue Organic Electrophosphorescent Devices", Chemistry of Materials, vol. 16, no. 23, pp. 4743-4747, 2004. https://doi.org/10.1021/cm049402m
  5. Holmes, R. J., D'Andrade, B. W., Forrest, S. R., Ren, X., Li, J., and Thompson, M. E., "Efficient, deep-blue organic electrophosphorescence by guest charge trapping", Applied Physics Letters, vol. 83, no. 18, 2003.
  6. Yeh, H. -C., Chien, C. -H., Shih, P. -I., Yuan, M. -C., and Shu, C. -F., "Polymers Derived from 3,6-Fouorene and Tetraphenylsilane Derivatives: Solution-Processable Host Materials for Green Phosphorescent OLEDs", Macromolecules, vol. 41, no. 11, pp. 3801-3807, 2008. https://doi.org/10.1021/ma800391e
  7. Wu, M. T., Yeh, S. J., Chen, C. T., Murayama, H., Tsuboi, T., Li, W. S., Chao, I., Liu, S. W., and Wang, J. K., "The quest for high-performance host materials for electrophosphorescent blue dopants, Advance Functional Materials, vol. 17, no. 12, pp. 1887-1895, 2007. https://doi.org/10.1002/adfm.200600800
  8. Lin, J. -J., Liao, W. -S., Huang, H. -J., Wu, F. -I., and Cheng, C. -H., "A Highly Efficient Host/Dopant Combination for Blue Organic Electrophosphorescence Devices", Advanced Functional Materials, vol. 18, no. 3, pp. 485-491, 2008. https://doi.org/10.1002/adfm.200700537
  9. SMART and SAINT ; Bruker Analytical X-Ray Division: Madison, WI, 2002.
  10. G. M. Sheldrick, SHELXTL-PLUS Software Package; Bruker Analytical X-Ray Division: Madison, WI, 2002.
  11. Langer, J., Gorls, H., and Westerhausen, M., "Phenylcalcium iodides with silyl substituents in para-position", Inorganic Chemistry Communications, vol. 10, no. 8, pp. 853-855, 2007. https://doi.org/10.1016/j.inoche.2007.03.032
  12. Bohme, U., Beyer, C., and Rheinwald, G., "Bis(p-bromophenyl)dimethylsilane", Acta Crystallographica Section E, vol. 63, no. 8, p. o3486, 2007. https://doi.org/10.1107/S1600536807033077
  13. Bohme, U., Gunther, B., and Schwarzer, A., "Formation of a silicon-containing macrocycle with a pyridoxalimine Schiff base ligand", Acta Crystallographic Section C, vol. 64, no. 12, pp. o630-o632, 2008. https://doi.org/10.1107/S1600536807065476
  14. Han, W. -S., Son, H. -J., Wee, K. -R., Min, K. -T., Kwon, S., Suh, I. -H., Choi, S. -H., Jung, D. H., and Kang, S. O., "Silicon-Based blue Phosphorescence Host Materials: Structure and Photophysical Property Relationship on Methyl/Phenylsilanes Adorned with 4-(N-Carbazolyl)phenyl Groups and Optimization of Their Electroluminescence by Peripheral 4-(N-Carbazolyl)phenyl Numbers", The Journal of Physical Chemistry C, vol. 113, no. 45, pp. 19686-19693, 2009. https://doi.org/10.1021/jp907104j
  15. Wang, P., Yue, Z., Zhang, J., and Feng, S. -Y., "Bis[4-(2-isopropyl-2H-tetrazol-5-yl) phenyl]dimethylsilane", Acta Crystallographica Section E, vol. 67, no. 2, p. o368, 2011. https://doi.org/10.1107/S160053681100033X