New Yellow Azo Pyridone Derivatives with Enhanced Thermal Stability for Color Filters in Image Sensors

Abstract

Two new yellow azo pyridone derivatives, (E)-6-hydroxy-1-(3-methoxypropyl)-4-methyl-2-oxo-5-(p-tolyldiazenyl)-1,2-dihydropyridine-3-carbonitrile (APY-M) and 5,5′-((1E,1′E)-(methylenebis(4,1-phenylene))bis(diazene-2,1-diyl))bis(6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile) (APY-D), were designed and synthesized as yellow colorants for image sensors. The properties of these new compounds were evaluated in both solution and color filter film forms, focusing on their optical and thermal characteristics. The molar extinction coefficient values of APY-M and APY-D in solution were found to be 2.7 × 105 and 3.0 × 105 L/mol·cm, respectively. The transmittance of the newly synthesized compounds met commercial requirements, showing values below 0.21% at 435 nm and above 97.1% at 530 nm. APY-D exhibited a molar extinction coefficient value in solution that was 1.15 times higher than that of the commercially used yellow colorant Disperse Yellow 241. Both newly synthesized compounds satisfied the decomposition temperature requirement of over 230 °C, which is essential for the color filter manufacturing process in image sensors. In particular, APY-D, with its dimeric structure and increased molecular weight, demonstrated enhanced thermal stability, with a 50 °C increase in decomposition temperature compared to Disperse Yellow 241. Color filter films for image sensors were fabricated using the new compounds, and their thermal resistance was evaluated. APY-D maintained its transmittance due to the enhanced thermal stability provided by its dimer structure and increased molecular weight. Consequently, APY-D is anticipated to be a promising candidate for use as a yellow colorant in image sensors, owing to its excellent optical and thermal properties.