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Synthesis and Characterization of Swallow-Tail Perylene Bisimide as Organic Phosphor for Hybrid LED

Hybrid LED용 유기 형광체로서의 Swallow-Tail Perylene Bisimide 제조 및 특성 연구

  • Jung, Sung Bong (Department of LED Convergence Lighting for Shipbuilding, Pukyong National University) ;
  • Jeong, Yeon Tae (Department of LED Convergence Lighting for Shipbuilding, Pukyong National University)
  • 정성봉 (부경대학교 LED융합공학전공) ;
  • 정연태 (부경대학교 LED융합공학전공)
  • Received : 2018.09.18
  • Accepted : 2018.10.08
  • Published : 2019.01.01

Abstract

Although perylene bisimide derivatives have advantages such as excellent thermal stability and high luminance efficiency, they have poor solubility characteristics in organic solvents. In this research, in order to improve the solubility characteristics, we prepared perylene bisimide derivatives (1C) and (2C) with swallow-tail substituted imide, which is known to lead to excellent solubility. The structures and properties of swallow-tail perylene bisimide (1C) and (2C) were analyzed by $^1H-NMR$, FT-IR, UV/Vis spectroscopy, and thermogravimetric analysis (TGA). The maximum absorption wavelengths of (1C) and (2C) in the UV/Vis spectrum were 558 nm and 556 nm, respectively, and the maximum emission wavelengths were 602 nm and 600 nm, respectively. In the TGA, (1C) demonstrated good thermal stability with less than 5 wt% weight loss up to $242^{\circ}C$. In the solubility test, (1C) and (2C) exhibited solubilities of more than 5 wt% in chloroform, ethyl acetate, and dimethylformamide, but not in methanol. When the compounds (1C) and (2C) were mixed with PMMA (polymethyl methacrylate), thin films showed peaks at 679 nm and 677 nm, respectively, in the photoluminescence spectra. (1C) was found to be a possible candidate as red organic phosphor for hybrid LEDs.

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Fig. 1. Synthetic pathway to N,N'-Bis(swallow-tail)-1,6,7,12-tetraphenoxyperylene-3,4,9,10-tetracarboxylic diimide; (ⅰ) ammonium acetate, sodium cyanoborohydride, metanol, 56 h, (ⅱ) zinc acetate, imidazole, 160℃, 5 h, and (ⅲ) phenol, potassium carbonate, DMF, 90℃, 24 h.

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Fig. 2. TGA thermograms of swallow-tail perylene bisimide.

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Fig. 3. UV/Vis absorptions and PL spectra of 1B and 2B in chloroform.

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Fig. 4. UV/Vis absorptions and PL spectra of 1C and 2C in chloroform.

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Fig. 5. PL spectra of (a) 1C and (b) 2C in blended thin films with PMMA.

Table 1. Solubility of swallow-tail perylene bisimide in organic solvents.

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Table 2. Color difference values of 1C and 2C in PMMA film.

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Acknowledgement

Grant : 조선.해양플랜트.해양환경 LED융합조명 핵심기술개발 전문 인력양성

Supported by : 산업통상자원부

References

  1. B. H. Jeong, N. O. Kim, D. G. Kim, G. G. Oh, G. B. Cho, and K. Y. Lee, J. Korean Inst. Illum. Electr. Install. Eng., 23, 23 (2009).
  2. Y. J. Sim, I. T. Kim, and A. S. Choi, J. Korean Inst. Illum. Electr. Install. Eng., 29, 1 (2015). [DOI: https://doi.org/10.5207/JIEIE.2015.29.1.001]
  3. N. J. Findlay, J. Bruckbauer, A. R. Inigo, B. Breig, S. Arumugam, D. J. Wallis, R. W. Martin, and P. J. Skabara, Adv. Mater., 26, 7290 (2014). [DOI: https://doi.org/10.1002/adma.201402661] https://doi.org/10.1002/adma.201402661
  4. E. Kozma and M. Catellani, Dyes Pigm., 98, 160 (2013). [DOI: https://doi.org/10.1016/j.dyepig.2013.01.020] https://doi.org/10.1016/j.dyepig.2013.01.020
  5. D. Dasgupta, A. M. Kendhale, M. G. Debije, J. ter Schiphorst, I. K. Shishmanova, G. Portale, and A.P.H.J. Schenning, ChemistryOpen, 3, 138 (2014). [DOI: https://doi.org/10.1002/open.201402011] https://doi.org/10.1002/open.201402011
  6. A. Wicklein, A. Lang, M. Muth, and M. Thelakkat, J. Am. Chem. Soc., 131, 14442 (2009). [DOI: https://doi.org/10.1021/ja905260c] https://doi.org/10.1021/ja905260c
  7. H. Langhals, R. Ismael, and O. Yuruk, Tetrahedron, 56, 5435 (2000). [DOI: https://doi.org/10.1016/S0040-4020(00)00452-X] https://doi.org/10.1016/S0040-4020(00)00452-X
  8. C. A. Fuller and C. E. Finlayson, Phys. Chem. Chem. Phys., 19, 31781 (2017). [DOI: https://doi.org/10.1039/C7CP05039A] https://doi.org/10.1039/C7CP05039A
  9. S. M. Lee and Y. T. Jeong, J. Korean Inst. Electr. Electron. Mater. Eng., 30, 48 (2017). [DOI: https://doi.org/10.4313/JKEM.2017.30.1.48] https://doi.org/10.4313/JKEM.2017.30.1.48
  10. M. J. Jung, J. W. Lim, I. J. Park, and Y. S. Lee, Appl. Chem. Eng., 21, 317 (2010).
  11. G. S. Padilha, V. M. Giacon, and J. R. Bartoli, Polimeros, 27, 195 (2017). [DOI: https://doi.org/10.1590/0104-1428.12516] https://doi.org/10.1590/0104-1428.12516