Photoactive Compound Nitro Phosphonate UV Sensitivity

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Solution Overview

Problem

Conventional photoactive compounds used in photosensitive resin compositions have low photoinitiation efficiency, particularly in thick films with high pigment concentrations, and do not adequately satisfy mechanical strength and critical dimension requirements, while also being expensive and having storage stability issues.

Innovation Solution

A photoactive compound with an oxime ester structure incorporating nitro and phosphonate groups is developed, enhancing UV light absorptivity, solubility, and compatibility with binder resins, thereby improving sensitivity and high-temperature process characteristics.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional photopolymerization initiators are used, then the photosensitive resin composition can be fabricated, but the photoinitiation efficiency is low and sensitivity is insufficient, especially in thick films with high pigment concentrations

Engineering Contradiction:
Improvephotoinitiation efficiencyVSAvoidsensitivity
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent modifies the molecular structure of photopolymerization initiators by introducing specific chemical groups (such as carbazole, triphenylamine, or xanthene groups combined with phosphine oxide or phosphonate groups) to change their light absorption characteristics and radical generation efficiency. This structural parameter change enables the initiator to achieve high photoinitiation efficiency and sensitivity simultaneously, particularly in thick films with high pigment concentrations where conventional initiators fail.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If the amount of photopolymerization initiator is increased to improve sensitivity, then sensitivity improves, but the cost increases and storage stability deteriorates

Engineering Contradiction:
ImprovesensitivityVSAvoidstorage stability
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent develops photopolymerization initiators with specific molecular structures (combining electron-donating groups like carbazole or triphenylamine with electron-withdrawing phosphine oxide or phosphonate groups) that inherently provide high photoinitiation efficiency. This allows the use of smaller amounts of initiator (0.1-10 wt% based on total composition) to achieve the required sensitivity, thereby maintaining storage stability and reducing cost while meeting performance requirements.

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If early developed oxime derivative compounds are used to achieve good color characteristics, then color stability improves, but photoinitiation efficiency becomes low and UV light absorption is inefficient

Engineering Contradiction:
Improvecolor stabilityVSAvoidphotoinitiation efficiency
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent creates composite molecular structures by combining photostable aromatic groups (carbazole, triphenylamine, xanthene) with high-efficiency photoinitiation groups (phosphine oxide, phosphonate). This composite structure integrates the color stability of aromatic compounds with the high photoinitiation efficiency of phosphorus-containing groups, achieving both good color characteristics and high photoinitiation efficiency simultaneously.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent modifies the chemical structure of oxime derivatives by introducing specific substituents that enhance both color stability and photoinitiation efficiency. The combination of electron-donating aromatic groups with electron-withdrawing phosphorus groups creates a push-pull electronic structure that optimizes both light absorption for color stability and radical generation for photoinitiation efficiency.

Inventive Principle:
Principle #35Parameter changes

4Ease of manufacture

If conventional photopolymerization initiators are used, then the composition can be processed, but the turn around time is long and productivity is reduced

Engineering Contradiction:
ImproveprocessabilityVSAvoidturn around time
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent develops photopolymerization initiators with optimized molecular structures that exhibit high absorption coefficients at wavelengths matching common UV light sources (365 nm, 385 nm). This parameter optimization enables rapid light absorption and fast radical generation, significantly reducing the exposure time required for complete polymerization and thus reducing turn around time while maintaining ease of manufacture.

Inventive Principle:
Principle #35Parameter changes

5Manufacturing precision

If photopolymerization initiators with high radical generation efficiency are used, then sensitivity improves, but compatibility with binder resin and solubility deteriorate

Engineering Contradiction:
ImprovesensitivityVSAvoidsolubility and compatibility
Core Design Contradiction:
Manufacturing precisionVSStability of the object's composition

Solution Approach 1:

The patent introduces solubilizing groups (such as alkoxy, hydroxy, or carboxy groups) and compatibility-enhancing aromatic structures into the photopolymerization initiator molecules. These structural modifications improve solubility in common resins and compatibility with binder materials while maintaining the high radical generation efficiency provided by the phosphine oxide or phosphonate groups, achieving a balance between sensitivity and processability.

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 new compound achieves improved sensitivity, solubility, and chemical resistance, enabling efficient UV light absorption and effective pattern formation even in thick films, with enhanced mechanical properties and reduced material costs.

Implementation Method 1

a photoactive compound is substance which is decomposed by absorbed light and formed to generate atoms or molecules having activity chemically

Methodology Applied
Scientific EffectPhotodissociation: Photodissociation

Implementation Method 2

a photoactive compound from which the radicals, from among the acids, bases, and radicals, are generated may be used with acryl groups, generating polymerization along with the radicals

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Implementation Method 3

The photosensitive resin composition is being used in photocurable ink, photosensitive printing sheets, various photoresists, color filter photoresists for LCDs, photoresists for resin black matrices, and transparent photosensitizers because it can be radiated by light, can be polymerized, and hardened

Methodology Applied
Scientific EffectPhoto-oxidation: Photo-oxidation

Data Source

PatentEP2397903B1Photoactive compound and photosensitive resin composition containing the same
Publication Date: 2014.07.30 LG CHEM LTD
  • EP2397903B1 patent drawing
  • EP2397903B1 patent drawing
  • EP2397903B1 patent drawing

AI summary

The present invention relates to a photoactive compound of a novel structure represented by Chemical Formula 1 below and a photosensitive resin composition comprising the same. The photoactive compound of the present invention comprises a nitro group and a phosphonate structure and thus exhibits excellent sensitivity through efficient absorption for UV light, excellent compatibility between the photoactive compound and the alkali-soluble binder resin, and an improved solubility of the photosensitive resin composition. Furthermore, the photosensitive resin composition of the present invention has excellent residual film thickness and mechanical strength characteristics and heat-resistant, chemical-resistant, and development-resistant properties. Accordingly, the photosensitive resin composition of the present invention is advantageous in hardening the column spacers of liquid crystal displays, an overcoat, and passivation materials and also advantageous in a high-temperature process characteristic. In Chemical Formula 1, R1 and R2, R3, and A are defined as follows.