journal article·2024-05-21Open access

Novel Yellow Aromatic Imine Derivative Incorporating Oxazolone Moiety for Color Resist Applications

Sunwoo Park, Sangwook Park, Seyoung Oh, Yeongjae Heo, Hayoon Lee, Jongwook Park

Applied Sciences· Volume 14· Issue 11

Abstract

A novel aromatic imine derivative, 2′-(1,4-phenylene)bis[4-[(4-methoxyphenyl)methylene]-5(4H)-oxazolone] (PBMBO), was designed and synthesized as a yellow colorant additive for green color filters used in image sensors. The optical and thermal properties of the newly developed material were evaluated both in solution and within color filter film conditions. PBMBO demonstrated a molar extinction coefficient of 2.24 × 104 L/mol·cm in solution, surpassing that of the commercially employed yellow colorant MBIQO by a factor of 1.82. Color resist (CR) films incorporating PBMBO exhibited outstanding optical characteristics, displaying 0.03% transmittance at 435 nm, 99.3% transmittance at 530 nm, and a sharp slope within the 400 to 550 nm range. The decomposition temperature of PBMBO was 303 °C, indicating relatively superior thermal stability compared to MBIQO. Consequently, PBMBO emerges as a highly promising candidate for a yellow colorant additive in imaging sensor color filters, owing to its exceptional optical and thermal stability. Its potential applications are anticipated to extend across various fields of organic semiconductors.
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Research context

OpenAlex topics: Synthesis and properties of polymers · Epoxy Resin Curing Processes · Synthesis of Tetrazole Derivatives

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Integrated Engineering, Department of Chemical Engineering, Kyung Hee University, Youngin 17104, Republic of Korea

Funding

Gyeonggi Province

References (32)

Show source-provided references
1. Plasmonic color filters for CMOS image sensor applications10.1021/nl302110z ↗
2. LCD-based color filter films fabricated by a pigment-based colorant photo resist inks and printing technology10.1016/j.tsf.2006.07.159 ↗
3. Nanostructured Color Filters for CMOS Image Sensors10.1109/LPT.2023.3268350 ↗
4. Zollinger, H. (2003). Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments, John Wiley & Sons.
5. Development of color resists containing novel dyes for liquid crystal displays
6. Miyamichi, A., Ono, A., Kagawa, K., Yasutomi, K., and Kawahito, S. (2019). Plasmonic Color Filter Array with High Color Purity for CMOS Image Sensors. Sensors, 19.10.3390/s19081750 ↗
7. Recent Advances on Quantum-Dot-Enhanced Liquid-Crystal Displays10.1109/JSTQE.2017.2649466 ↗
8. Going beyond the limit of an LCD’s color gamut10.1038/lsa.2017.43 ↗
9. Dyeing and fastness properties of benzodifuranones, naphthodifuranones and naphthofuranonepyrrolidones10.1111/j.1478-4408.2002.tb00369.x ↗
10. The synthesis and properties of naphthodifuranones and naphthofuranonepyrrolidones10.1016/S0143-7208(00)00093-0 ↗
11. The synthesis of red dyes based on diketo-pyrrolo-pyrrole chromophore to improve heat stability and solubility for colour filter fabrication10.1016/j.dyepig.2019.108053 ↗
12. Synthesis and characterization of metal phthalocyanine bearing carboxylic acid anchoring groups for nanoparticle dispersion and their application to color filters10.1016/j.dyepig.2020.108737 ↗
13. Development of dimeric triarylmethine derivatives with improved thermal and photo stability for color filters10.1016/j.dyepig.2017.05.035 ↗
14. The synthesis and application of thermally stable dyes for ink-jet printed LCD color filters10.1016/j.dyepig.2008.09.006 ↗
15. Facile synthesis and characterization of novel coronene chromophores and their application to LCD color filters10.1016/j.dyepig.2011.11.009 ↗
16. Synthesis and characterization of thermally stable dyes with improved optical properties for dye-based LCD color filters10.1039/c2nj20938a ↗
17. Park, S., Kang, Y., Kwon, H., Kim, H., Kang, S., Lee, H., Yoon, C., and Park, J. (2022). Novel Yellow Azo Pyridone Derivatives with Different Halide Atoms for Image-Sensor Color Filters. Molecules, 27.10.3390/molecules27196601 ↗
18. Surface modification of organic pigment particles for microencapsulated electrophoretic displays10.1016/j.dyepig.2011.06.003 ↗
19. Preparation, Particle Characterizations and Application of Nano-Pigment Suspension10.1080/03602559.2010.512335 ↗
20. Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety10.1016/j.dyepig.2014.06.026 ↗
21. Microwave-assisted synthesis and photochromic properties of new azo-imidazoles10.1016/j.dyepig.2017.04.053 ↗
22. Multi-functional colorimetric chemosensor for naked eye recognition of Cu2+, Zn2+ and Co2+ using new hybrid azo-pyrazole/pyrrolinone ester hydrazone dye10.1016/j.dyepig.2021.109795 ↗
23. The photochromic switchable imidazoles: Their genesis, development, synthesis, and characterization10.1016/j.dyepig.2022.110322 ↗
24. Gonciarz, A., Pich, R., Bogdanowicz, K.A., Jewloszewicz, B., Przybył, W., Dysz, K., Dylong, A., Kwak, A., Kaim, A., and Iwan, A. (2019). UV–Vis Absorption Properties of New Aromatic Imines and Their Compositions with Poly({4,8-bis[(2-Ethylhexyl)oxy]Benzo[1,2-b:4,5-b′]Dithiophene-2,6-diyl}{3-Fluoro-2-[(2-Ethylhexyl)Carbonyl]Thieno[3,4-b]Thiophenediyl}). Materials, 12.10.3390/ma12244191 ↗
25. Ribeiro, A.I., Vieira, B., Alves, C., Silva, B., Pinto, E., Cerqueira, F., Silva, R., Remião, F., Shvalya, V., and Cvelbar, U. (2023). Halochromic Silk Fabric as a Reversible pH-Sensor Based on a Novel 2-Aminoimidazole Azo Dye. Polymers, 15.10.3390/polym15071730 ↗
26. Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors10.1021/acssensors.2c01687 ↗
27. The synthesis, structure and spectroscopic properties of novel oxazolone-, pyrazolone- and pyrazoline-containing heterocycle chromophores10.1016/j.dyepig.2008.08.010 ↗
28. Synthesis and Linear and Nonlinear Optical Properties of Three Push–Pull Oxazol-5(4H)-one Compounds10.1021/acs.joc.5b01636 ↗
29. Synthesis and characterization of new green and orange region emitting anthracene based oxazol-5-one dyes10.1016/j.dyepig.2017.05.049 ↗
30. Linear and nonlinear absorption properties of hemicyanine dyes containing 5-(4H)-oxazolone as heterocyclic ring10.1016/j.dyepig.2022.110772 ↗
31. Park, S., Godi, M., Khairnar, N., Dae, S., Kwon, H., Park, S., Lee, H., Lee, K., and Park, J. (2024). Enhanced Optical and Thermal Properties of a Novel Yellow Quinophthalone Derivative for Color Filter Colorants in Image Sensors. Phys. Status Solidi A-Appl. Mat.10.1002/pssa.202300888 ↗
32. Park, S., Jillella, R., Kwon, H., Park, S., Lee, H., Lee, K., and Park, J. (2024). Enhancement of Optical and Chemical Resistance Properties with a Novel Yellow Quinophthalone Derivative for Image Sensor Colorants. Molecules, 29.10.3390/molecules29051100 ↗