Skip to main content
SpringerLink
Log in

Synthesis and characteristics of metal-phthalocyanines tetra-substituted at non-peripheral (α) or peripheral (β) positions, and their applications in LCD color filters

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

Four metal-phthalocyanine dyes were synthesized to evaluate the variation of their properties with both the position of the substituents and the type of metal used for coordination. The substituent, ethyl 4-hydroxy-3-methoxybenzoate, was introduced at the non-peripheral (α) or the peripheral (β) position in order to improve the solubility of the phthalocyanine. Cu and Zn were chosen as coordination metals, both to increase thermal stability and to fine-tune the color of the complex. The resulting complexes were highly soluble in a range of organic solvents as well as industrial solvents, such as di(propylene glycol) methyl ether acetate, diethylene glycol monobutyl ether acetate, and propylene glycol methyl ether acetate. The solubility of the dyes substituted at the α-position was higher than that of β-substituted dyes. Structural analyses of the substituted phthalonitriles were achieved using 1H and 13C NMR spectroscopy, and high-resolution mass spectrometry. The structures of the dyes were confirmed by MALDI-TOF spectroscopy and FT-IR spectrophotometry. The optical properties and thermal stabilities of the dyes were estimated by UV–Vis spectrophotometry and thermogravimetric analysis. The synthesized dyes were cyan in color, and thus could be successfully applied in six-primary-color (RGBCMY) liquid crystal display (LCD) color filters in order to improve the color gamut. Dye-based color filters showing adequate optical spectra for LCD cyan color filters were manufactured. Appropriate compensating dyes were also required in order to cut off undesirable transmittance peaks.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Gu, D., Chen, Q., Shu, J., Tang, X., Gan, F., Shen, S., Liu, K., Xu, H.: Optical recording performance of thin films of phthalocyanine compounds. Thin Solid Films 257, 88–93 (1995)

    Article  CAS  Google Scholar 

  2. Guillaud, G., Simon, J., Germain, J.P.: Metallophthalocyanines: gas sensors, resistors and field effect transistors 1. Coord. Chem. Rev. 178–180(Part 2), 1433–1484 (1998)

    Article  Google Scholar 

  3. de la Torre, G., Vazquez, P., Agullo-Lopez, F., Torres, T.: Phthalocyanines and related compounds: organic targets for nonlinear optical applications. J. Mater. Chem. 8, 1671–1683 (1998)

    Article  Google Scholar 

  4. Pal, M., Ganesan, V.: Zinc phthalocyanine and silver/gold nanoparticles incorporated MCM-41 type materials as electrode modifiers. Langmuir 25, 13264–13272 (2009)

    Article  CAS  Google Scholar 

  5. Ranyuk, E., Cauchon, N., Klarskov, K., Guérin, B., van Lier, J.E.: Phthalocyanine-peptide conjugates: receptor-targeting bifunctional agents for imaging and photodynamic therapy. J. Med. Chem. 56, 1520–1534 (2013)

    Article  CAS  Google Scholar 

  6. Rand, B.P., Cheyns, D., Vasseur, K., Giebink, N.C., Mothy, S., Yi, Y., Coropceanu, V., Beljonne, D., Cornil, J., Brédas, J.-L., Genoe, J.: The impact of molecular orientation on the photovoltaic properties of a phthalocyanine/fullerene heterojunction. Adv. Funct. Mater. 22, 2987–2995 (2012)

    Article  CAS  Google Scholar 

  7. Choi, J., Kim, S.H., Lee, W., Yoon, C., Kim, J.P.: Synthesis and characterization of thermally stable dyes with improved optical properties for dye-based LCD color filters. New J. Chem. 36, 812 (2012)

    Article  CAS  Google Scholar 

  8. Yoon, C., Choi, J.-H., Kim, J.-P.: Synthesis and examination of polymers to improve pattern clarity and resistance properties of phthalocyanine color pixels in liquid crystal display. Bull. Korean Chem. Soc. 32, 1033–1036 (2011)

    Article  CAS  Google Scholar 

  9. Sabnis, R.W.: Color filter technology for liquid crystal displays. Displays 20, 119–129 (1999)

    Article  CAS  Google Scholar 

  10. Esenpınar, A.A., Bulut, M.: Synthesis and characterization of novel α- or β-tetra [6,7-dihexyloxy-3-(4-oxyphenyl)coumarin]-substituted metal-free and metallo phthalocyanines. Polyhedron 28, 3129–3137 (2009)

    Article  Google Scholar 

  11. Mbambisa, G., Nyokong, T.: Synthesis and electrochemical characterisation of a near infrared absorbing oxo vanadium (IV) octapentylthio-phthalocyanine. Polyhedron 27, 2799–2804 (2008)

    Article  CAS  Google Scholar 

  12. Liao, M.-S., Scheiner, S.: Electronic structure and bonding in metal phthalocyanines, Metal = Fe Co, Ni, Cu, Zn, Mg. J. Chem. Phys. 114, 9780 (2001)

    Article  CAS  Google Scholar 

  13. Kadish, K.M., Smith, K.M., Guilard, R.: The Porphyrin Handbook: Phthalocyanines: Properties and Materials, vol. 17, pp. 1–31. Elsevier, Boston (2003)

    Google Scholar 

Download references

Acknowledgments

This work was supported by the Industrial Strategic Technology Development Program (No. 10043048, Development of Hybrid Mill Base and Dyes for Color Filter with High Contrast Ratio and Brightness) funded by the Ministry of Trade, Industry and Energy (MOTIE, Republic of Korea) and a grant from the Fundamental R&D Program for Core Technology of Materials funded by the Ministry of Trade, Industry and Energy (MOTIE, Republic of Korea).

Author information

Authors and Affiliations

  1. Department of Materials Science and Engineering, Seoul National University, Seoul, 151-744, Republic of Korea

    Se Hun Kim, Jin Woong Namgoong, Sim Bum Yuk, Jeong Yun Kim & Jae Pil Kim

  2. ICT Textile & Apparel R&D Group, Korea Institute of Industrial Technology (KITECH), Ansan-Si, Gyeonggi-do, 426-910, Republic of Korea

    Woosung Lee

  3. Department of Chemistry, Sejong University, Seoul, 143-747, Republic of Korea

    Chun Yoon

Authors
  1. Se Hun Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jin Woong Namgoong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sim Bum Yuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jeong Yun Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Woosung Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Chun Yoon
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jae Pil Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jae Pil Kim.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kim, S.H., Namgoong, J.W., Yuk, S.B. et al. Synthesis and characteristics of metal-phthalocyanines tetra-substituted at non-peripheral (α) or peripheral (β) positions, and their applications in LCD color filters. J Incl Phenom Macrocycl Chem 82, 195–202 (2015). https://doi.org/10.1007/s10847-015-0514-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-015-0514-y

Keywords

Search

Navigation