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Aromatic substituents for prohibiting side-chain packing and π-π stacking in tin-cored tetrahedral stilbenoids

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Abstract

Tetrahedral structures comprising Sn-cored materials with five different types of substituents were synthesized. For the substituents, we employed methyl and tert-butyl as aliphatic groups, and naphthyl and phenyl as aromatic groups. The bandgap is in the range of 3.28 – 3.56 eV. The All the compounds with substituents showed bathochromical photoluminescence characteristics and exhibited aggregation-induced emission characteristics. Specifically, the compounds with aromatic substituents prohibited side-chain packing and π-π stacking. The energy levels of the highest occupied and lowest unoccupied molecular orbitals were measured to be 5.5 – 5.75 and 2.0 – 2.37 eV, respectively. The maximum luminance efficiencies and power efficiencies of the Sn-cored compound-based organic light-emitting diodes (OLEDs) were 0.38 – 0.71 cd/A and 0.15 – 0.28 lm/W. Therefore, it is expected that Sn-cored compounds with a tetrahedral structure, especially those containing aromatic substituents, can be used as an active material in blue OLEDs for prohibiting side-chain packing and π-π stacking.

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References

  1. H. Sasabe and J. Kido, J. Mater. Chem. C 1, 1699 (2013).

    Article  Google Scholar 

  2. J. Wang, F. Zhang, J. Zhang, W. Tang, A. Tang, H. Peng, Z. Xu, F. Teng, and Y. Wang, J. Photoch. Photobio. C 17, 69 (2013).

    Article  Google Scholar 

  3. J. H. Kim, J.-Y. Cho, J. Park, B. K. Lee, K.-H. Baek, H. Lee, and L.-M. Do, Electron. Mater. Lett. 10, 27 (2014).

    Article  Google Scholar 

  4. G.-P. Kim, B.-M. Park, and H.-J. Chang, Electron. Mater. Lett. 10, 491 (2014).

    Article  Google Scholar 

  5. N.-C. Seong, Y.-M. Jeon, T.-H. Lim, J.-W. Kim, C.-W. Lee, E.-J. Lee, J.-G. Jang, H.-J. Jang, J.-Y. Lee, and M.-S. Gong, Synthetic Met. 157, 421 (2007).

    Article  Google Scholar 

  6. L. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong, and J. Kido, Adv. Mater. 23, 926 (2011).

    Article  Google Scholar 

  7. K. S. Choi, H. Jo, K. Park, S. Y. Kim, B. H. Koo, K. Hong, and J.-L. Lee, J. Phys. Chem. C 115, 9767 (2011).

    Article  Google Scholar 

  8. Y. Wei and C.-T. Chen, J. Am. Chem. Soc. 129, 7478 (2007).

    Article  Google Scholar 

  9. H.-C. Yeh, R.-H. Lee, L.-H. Chan, T.-Y. J. Lin, C.-T. Chen, E. Balasubramaniam, and Y.-T. Tao, Chem. Mater. 13, 2788 (2001).

    Article  Google Scholar 

  10. S. Wang, W. J. Oldham, R. A. Hudack, and G. C. Bazan, J. Am. Chem. Soc. 122, 5695 (2000).

    Article  Google Scholar 

  11. S.-K. Kim, Y.-I. Park, I.-N. Kang, and J.-W. Park, J. Mater. Chem. 17, 4670 (2007).

    Article  Google Scholar 

  12. S. Liu, F. He, H. Wang, H. Xu, C. Wang, F. Li, and Y. Ma, J. Mater. Chem. 18, 4802 (2008).

    Article  Google Scholar 

  13. S.-C. Lo and P. L. Burn, Chem. Rev. 107, 1097 (2007).

    Article  Google Scholar 

  14. P. Furuta, J. Brooks, M. E. Thompson, and J. M. J. Fréchet, J. Am. Chem. Soc. 125, 13165 (2003).

    Article  Google Scholar 

  15. X.-M. Liu, C. He, X.-T. Hao, L.-W. Tan, Y. Li, and K. S. Ong, Macromolecules 37, 5965 (2004).

    Article  Google Scholar 

  16. Q. He, H. Huang, Q. Sun, H. Lin, J. Yang, and F. Bai, Polym. Advan. Technol. 15, 43 (2004).

    Article  Google Scholar 

  17. Y.-Y. Lyu, J. Kwak, W. S. Jeon, Y. Byun, H. S. Lee, D. Kim, C. Lee, and K. Char, Adv. Funct. Mater. 19, 420 (2009).

    Article  Google Scholar 

  18. Y. Park, K. S. Choi, S. Y. Kim, H. Jo, and K. Park, Displays 33, 55 (2012).

    Article  Google Scholar 

  19. Z. Zhao, S. Chen, X. Shen, F. Mahtab, Y. Yu, P. Lu, J. W. Lam, H. S. Kwok, and B. Z. Tang, Chem. Commun. 46, 686 (2010).

    Article  Google Scholar 

  20. W. Z. Yuan, P. Lu, S. Chen, J. W. Lam, Z. Wang, Y. Liu, H. S. Kwok, Y. Ma, and B. Z. Tang, Adv. Mater. 22, 2159 (2010).

    Article  Google Scholar 

  21. Y. Hong, J. W. Y. Lam, and B. Z. Tang, Chem. Soc. Rev. 40, 5361 (2011).

    Article  Google Scholar 

  22. R. Hu, N. L. Leung, and B. Z. Tang, Chem. Soc. Rev. 43, 4494 (2014).

    Article  Google Scholar 

  23. J. Mei, Y. Hong, J. W. Lam, A. Qin, Y. Tang, and B. Z. Tang, Adv. Mater. 26, 5429 (2014).

    Article  Google Scholar 

  24. C. Kim, T. P. Nguyen, Q. V. Le, J.-M. Jeon, H. W. Jang, and S. Y. Kim, Adv. Funct. Mater. 25, 4512 (2015).

    Article  Google Scholar 

  25. K. Guo, Z. Gao, J. Cheng, Y. Shao, X. Lu, and H. Wang, Dyes Pigments 115, 166 (2015).

    Article  Google Scholar 

  26. C. Liu, W. He, G. Shi, H. Luo, S. Zhang, and Z. Chi, Dyes Pigments 112, 154 (2015).

    Article  Google Scholar 

  27. K. C. Kwon, C. Kim, Q. V. Le, S. Gim, J.-M. Jeon, J. Y. Ham, J.-L. Lee, H. W. Jang, and S. Y. Kim, ACS Nano 9, 4146 (2015).

    Article  Google Scholar 

  28. Z. Zhang, Y. Zhao, R. Zhang, L. Zhang, W. Cheng, and Z. H. Ni, Dyes Pigments 118, 95 (2015).

    Article  Google Scholar 

  29. H. Shi, W. Zhang, X. Dong, X. Wu, Y. Wu, L. Fang, Y. Miao, and H. Wang, Dyes Pigments 104, 34 (2014).

    Article  Google Scholar 

  30. L. Chen, Y. Jiang, H. Nie, P. Lu, H. H. Y. Sung, I. D. Williams, H. S. Kwok, F. Huang, A. Qin, Z. Zhao, and B. Z. Tang, Adv. Funct. Mater. 24, 3621 (2014).

    Article  Google Scholar 

  31. C. Y. Lee, Q. V. Le, C. Kim, and S. Y. Kim, Phys. Chem. Chem. Phys. 17, 9369 (2015).

    Article  Google Scholar 

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Correspondence to Kwangyong Park or Soo Young Kim.

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Kim, C., Yoon, MJ., Hong, S.H. et al. Aromatic substituents for prohibiting side-chain packing and π-π stacking in tin-cored tetrahedral stilbenoids. Electron. Mater. Lett. 12, 388–398 (2016). https://doi.org/10.1007/s13391-016-6002-8

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  • DOI: https://doi.org/10.1007/s13391-016-6002-8

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