Novel Oxime Ester Photoactive Compound for LCD Resins

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Solution Overview

Problem

Conventional oxime ester-based photopolymerization initiators have low photoinitiation efficiency, are inefficient in UV absorption, and fail to meet the requirements for forming fine patterns with high pigment concentration or thick coatings, particularly in liquid crystal display devices, due to inadequate sensitivity and mechanical strength.

Innovation Solution

A novel photoactive compound with an oxime ester structure that efficiently absorbs UV light at 365 nm, improving sensitivity and thermal processing characteristics, is developed, comprising specific alkyl and phenyl groups, and is incorporated into a photosensitive resin composition with an alkali-soluble binder and polymerizable compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional oxime ester-based photopolymerization initiators are used, then the photosensitive resin composition can be formed, but the photoinitiation efficiency is low and UV absorption is inefficient

Engineering Contradiction:
Improvephotoinitiation efficiencyVSAvoidexposure time
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent modifies the molecular structure of oxime ester-based photopolymerization initiators by changing chemical parameters (introducing specific substituents R1, R2, R3, X, Y, A, n, m) to enhance UV absorption efficiency and photoinitiation performance at 365 nm wavelength

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite photoactive compound combining oxime ester structure with specific alkyl groups, phenyl groups, and heterocyclic rings to achieve both high UV absorption efficiency and good solubility in photosensitive resin compositions

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If conventional oxime ester-based photopolymerization initiators are used, then the basic photopolymerization function is achieved, but sensitivity and mechanical strength are insufficient for fine patterns

Engineering Contradiction:
Improvepattern formation qualityVSAvoidsensitivity
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent introduces specific functional groups (carbazole, pyridine, triazine) at specific positions in the molecular structure to locally enhance UV absorption capability at 365 nm while maintaining overall molecular compatibility with the photosensitive resin system

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent optimizes molecular parameters (substituents R1-R3, X, Y, A, n, m) to adjust the absorption spectrum to match the 365 nm light source, thereby improving sensitivity and pattern formation precision

Inventive Principle:
Principle #35Parameter changes

3Temperature

If conventional oxime ester-based photopolymerization initiators are used, then the composition can be processed, but thermal processing characteristics and heat resistance are inadequate

Engineering Contradiction:
Improveheat resistanceVSAvoidthermal processing characteristics
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent modifies the molecular structure by introducing stable heterocyclic rings (carbazole, pyridine, triazine) and specific substituent patterns that enhance thermal stability while maintaining photopolymerization activity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining the reactive oxime ester group with thermally stable aromatic and heterocyclic frameworks to simultaneously achieve good photoinitiation efficiency and thermal processing resistance

Inventive Principle:
Principle #40Composite materials

4Strength

If conventional oxime ester-based photopolymerization initiators are used, then the basic curing function is achieved, but residual film ratio and mechanical strength are insufficient

Engineering Contradiction:
Improvemechanical strengthVSAvoidresidual film ratio
Core Design Contradiction:
StrengthVSManufacturing precision

Solution Approach 1:

The patent optimizes the molecular weight, substituent types, and structural configuration of the photopolymerization initiator to control the degree of polymerization and crosslinking density, thereby improving mechanical strength and reducing residual film

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops a composite photopolymerization system where the enhanced photoactive compound works synergistically with the photosensitive resin and polymerizable compounds to achieve optimal mechanical properties and pattern quality

Inventive Principle:
Principle #40Composite materials

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 novel photoactive compound enhances sensitivity, residual film ratio, mechanical strength, heat resistance, and chemical resistance, enabling faster exposure times and reduced material costs, while maintaining excellent thermal processing characteristics for applications in liquid crystal display devices.

Implementation Method 1

a photoactive compound that has a high UV absorption rate

Methodology Applied
Scientific EffectUV light absorption: Absorption (EM radiation)

Implementation Method 2

Photosensitive resin compositions are currently used in the production of photocurable inks, photosensitive printing plates, a variety of photoresists, including color filter photoresists for LCDs

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS8252507B2Photoactive compound and photosensitive resin composition comprising the same
Publication Date: 2012.08.28 LG CHEM LTD
  • US8252507B2 patent drawing
  • US8252507B2 patent drawing
  • US8252507B2 patent drawing

AI summary

A novel photoactive compound is provided. The photoactive compound has a structure represented by Formula 1:wherein R1, R2, R3, A, X, Y, n and m are as defined in the specification.The photoactive compound efficiently absorbs UV light. Accordingly, the photoactive compound has an improved ability to generate radicals and is efficiently photopolymerized with unsaturated bonds. Further provided is a photosensitive resin composition comprising the photoactive compound. The photosensitive resin composition has good sensitivity because it efficiently absorbs UV light. In addition, the photosensitive resin composition has excellent characteristics in terms of residual film ratio, mechanical strength and resistance to heat, chemicals and development. Therefore, the photosensitive resin composition is advantageously used in curing materials for column spacers, overcoats and passivation films of liquid crystal display devices. In addition, the photosensitive resin composition has excellent thermal processing characteristics.