Diaroyl Carbazole Sensitizers for Photoresist Curing

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Solution Overview

Problem

Current photoinitiators and sensitizing agents, such as benzophenone and thioxanthone derivatives, do not demonstrate satisfactory sensitizing effects when combined with carbazolyl oxime ester, and some compounds like eosin and anthocyanin can reduce photocuring efficiency due to phenolic hydroxyl or anilino groups, leading to a lack of ideal sensitizing agents for improving exposure sensitivity and resolution in photocurable compositions.

Innovation Solution

The development of novel diaroyl carbazole compounds, which, when used in specific ratios with carbazolyl oxime ester, form a photoinitiator composition that significantly enhances sensitizing effects, particularly in photoresists, by employing a Friedel-Crafts acylation reaction to synthesize these compounds and mixing them with carbazolyl oxime ester photoinitiators.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional sensitizing agents (benzophenone, thioxanthone derivatives) are used with carbazolyl oxime ester, then the photoinitiator system can be formed, but the sensitizing effect is not satisfactory and photocuring efficiency is reduced

Engineering Contradiction:
Improvesensitizing effectVSAvoidphotocuring efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent modifies the molecular structure of carbazole by introducing specific substituents (fluorine atoms, alkyl groups, alkoxy groups) at defined positions to create diaroyl carbazole compounds with optimized photophysical properties. This structural parameter change enables the sensitizing agent to effectively transfer energy to the carbazolyl oxime ester photoinitiator, resolving the insufficient sensitizing effect while maintaining high photocuring efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite photoinitiator system consisting of carbazolyl oxime ester (primary photoinitiator) combined with diaroyl carbazole compounds (sensitizing agents). This composite approach leverages the complementary photophysical properties of both components, where the diaroyl carbazole absorbs light and transfers energy to the oxime ester, achieving synergistic sensitizing effect that conventional single agents cannot provide

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If pigment content is increased to improve color saturation and hiding power, then the visual performance is improved, but light energy utilization rate is reduced due to absorption by pigment

Engineering Contradiction:
Improvecolor saturationVSAvoidlight energy utilization rate
Core Design Contradiction:
Illumination intensityVSUse of energy by moving object

Solution Approach 1:

The patent develops diaroyl carbazole sensitizing agents with optimized absorption spectra and energy transfer efficiency. These compounds are designed to absorb light in regions that complement the pigment absorption, and efficiently transfer energy to the photoinitiator. This parameter optimization allows the system to maintain high light energy utilization rate even when pigment content is increased for better color saturation and hiding power

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 diaroyl carbazole compounds show a substantial sensitizing effect when combined with carbazolyl oxime ester, achieving higher sensitivity and improved photocuring efficiency, especially in photoresists, with optimal results at specific molar ratios, surpassing the performance of previous sensitizing agents.

Implementation Method 1

UV photocuring technique is widely used in the fields of coatings, printing inks and electronic device manufacturing. Photoinitiators and co-initiators such as sensitizing agents are key factors affecting curing efficiency.

Methodology Applied
Scientific EffectPhotocuring: Photopolymerisation

Implementation Method 2

the light energy utilization rate in the curing process is reduced due to the absorption by pigment

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentUS12172962B2Diaroyl carbazole compound and use thereof as sensitising agent
Publication Date: 2024.12.24 IGM (ANQING) HIGH TECH DEV CO LTD
  • US12172962B2 patent drawing
  • US12172962B2 patent drawing
  • US12172962B2 patent drawing

AI summary

Provided in the present invention is a novel diaroyl carbazole compound, used together with a carbazolyl oxime ester photoinitiator to show a significant synergistic initiation effect in a photoresist composition; the best sensitising effect is shown when the molar ratio of the diaroyl carbazole compound and the carbazolyl oxime ester photoinitiator is 0.1-1.4.