Azo Compound Curable Composition for High-Resolution Color Filters

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Solution Overview

Problem

Conventional pigment dispersion methods for producing color filters, particularly for solid state imaging devices, face challenges in achieving high resolution due to issues with pigment particle size causing color unevenness, low light fastness and heat resistance of dyes, solubility problems, and difficulties in controlling the thickness and development properties of dye-based curable compositions.

Innovation Solution

Development of an azo compound with a 1,3,4-thiadiazolyl group that offers excellent light and heat fastness, high molar extinction coefficient, and improved development suitability, incorporated into a curable composition to form a color filter with reduced thickness and enhanced spectral properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a pigment dispersion method is used to produce a color filter, then light fastness and heat resistance are improved, but resolution and color uniformity deteriorate due to coarse pigment particles causing color unevenness

Engineering Contradiction:
Improvelight fastnessVSAvoidresolution
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The invention changes the chemical structure parameters of the coloring material by introducing specific substituents (electron-withdrawing groups like -NO2, -CN, -CF3 and electron-donating groups like -NMe2, -OMe) at defined positions relative to the azo group. This structural parameter optimization enables achieving both high light fastness and high resolution simultaneously by enhancing the dye's inherent stability while maintaining fine pattern capability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite curable composition integrating the specifically structured azo compound with photopolymerizable components (acrylates, epoxies) and photoinitiators. This composite formulation allows the dye to be embedded in a cured matrix that locks in the color pattern at high resolution while the dye structure itself provides the light and heat fastness properties.

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If a dye is used as a coloring material to achieve high resolution, then resolution is improved, but light fastness and heat resistance deteriorate

Engineering Contradiction:
ImproveresolutionVSAvoidlight fastness
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The invention fundamentally changes the dye's molecular parameters by positioning electron-withdrawing groups at para or ortho positions relative to the azo group and electron-donating groups at meta positions. This specific parameter arrangement creates a push-pull electronic structure that enhances both the dye's stability (light/heat fastness) and its ability to form fine patterns (resolution).

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention applies different functional groups at different local positions around the azo chromophore: electron-withdrawing groups at para/ortho positions and electron-donating groups at meta positions. This local differentiation of chemical properties optimizes both the stability and resolution characteristics in their respective molecular regions, which collectively manifest as improved overall performance.

Inventive Principle:
Principle #3Local quality

3Manufacturing precision

If the layer thickness is reduced to achieve high resolution in solid state imaging devices, then resolution is improved, but the required molar extinction coefficient increases making it difficult to achieve desired absorption

Engineering Contradiction:
ImproveresolutionVSAvoidmolar extinction coefficient
Core Design Contradiction:
Manufacturing precisionVSQuantity of substance

Solution Approach 1:

The invention changes the optical parameters of the dye by optimizing the chromophore structure with specific substituent combinations that dramatically increase the molar extinction coefficient. The push-pull electronic structure created by the strategically placed electron-withdrawing and electron-donating groups enhances the dye's light absorption intensity, allowing thin layers to achieve the required absorption for high-resolution imaging applications.

Inventive Principle:
Principle #35Parameter changes

4Quantity of substance

If a large amount of dye is added to achieve desired absorption, then absorption is improved, but curability, heat resistance after curing, and development properties deteriorate

Engineering Contradiction:
ImproveabsorptionVSAvoidcurability
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The invention changes the concentration parameter by demonstrating that the optimized dye structure achieves high absorption with minimal concentration (0.01-10 wt%). The enhanced molar extinction coefficient means far less dye is needed compared to conventional dyes, preserving the curable composition's functionality while achieving the required optical density for high-resolution applications.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The azo compound-based curable composition enables the production of color filters with improved fastness, resolution, and reduced thickness, while maintaining high sensitivity and transmittance, addressing the limitations of traditional dye-based compositions.

Implementation Method 1

desirable absorption properties in terms of color reproducibility; high molar extinction coefficient

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Implementation Method 2

curable composition comprising at least one azo compound of the present invention

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS8101325B2Azo compound, curable composition, color filter, and method of producing the same
Publication Date: 2012.01.24 FUJIFILM CORP
  • US8101325B2 patent drawing
  • US8101325B2 patent drawing
  • US8101325B2 patent drawing

AI summary

An azo compound represented by Formula (I), Formula (II), or Formula (III):wherein R1 and R2 each independently represent a hydrogen atom or a substituent; D1 and D2 each independently represent a coupler residue; Z1 and Z2 each independently represent —C(R3)═ or —N═; and R3 represents a hydrogen atom or a substituent.