Radically Curable Compound for High Heat Resistance

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Solution Overview

Problem

Current solder resist materials and photo-curable resins used in nanoimprint lithography lack the high heat resistance required for advanced electronic and display applications, particularly in thermal nanoimprint lithography where high-heat-resistant polymers are difficult to soften and photo-curable resins do not meet recent heat resistance standards.

Innovation Solution

A radically curable compound is developed by reacting a trifunctional phenol with a specific structure and (meth)acrylic acid halide, resulting in a cured product with high heat resistance, which can be easily produced and used as a solder resist or in nanoimprinting, offering high mechanical properties and water resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If thermal nanoimprint lithography is used to form fine structures, then low-cost nano-pattern formation is achieved, but polymer resins with high glass transition temperature cannot be softened and used

Engineering Contradiction:
Improveglass transition temperatureVSAvoidsoftening processability
Core Design Contradiction:
TemperatureVSEase of manufacture

Solution Approach 1:

The patent replaces thermal processing with photo-curing technology. Instead of heating polymer resins to their glass transition temperature to soften them for molding, the invention uses photopolymerization to cure the resin at room temperature or lower temperatures, thereby avoiding the limitation of high glass transition temperature materials in thermal nanoimprint lithography

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

Solution Approach 2:

The patent changes the curing mechanism from thermal to photo-induced. By using photo-curable resins with specific chemical structures (containing polymerizable unsaturated bonds and specific functional groups), the material can be cured at room temperature through light irradiation, fundamentally changing the processing temperature parameter from high (thermal) to low (photo-curing)

Inventive Principle:
Principle #35Parameter changes

2Temperature

If photo-curable resins are used for nanoimprint lithography, then room temperature imprinting is achieved, but the cured products do not have sufficient heat resistance for high-performance applications

Engineering Contradiction:
Improveheat resistanceVSAvoidperformance in high-heat applications
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent employs composite material design by combining specific phenolic structures (providing heat resistance) with polymerizable unsaturated bonds (enabling photo-curing). The cured product incorporates both aromatic rings from phenols for thermal stability and crosslinked polymer networks for mechanical strength, achieving high heat resistance (glass transition temperature of 400°C or more) while maintaining photo-curability

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent modifies the chemical structure of photo-curable resins by introducing specific functional groups (polymerizable unsaturated bonds combined with phenolic structures). This structural parameter change enables the resin to achieve high heat resistance after curing while still being curable by light at room temperature, thereby improving reliability in high-heat applications

Inventive Principle:
Principle #35Parameter changes

3Temperature

If epoxy (meth)acrylate resins with biphenyl skeleton are used, then high heat resistance is achieved, but the heat resistance is still insufficient for recent advanced applications

Engineering Contradiction:
Improveheat resistanceVSAvoidheat resistance level for advanced applications
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent changes the chemical structure by using phenolic hydroxyl groups combined with polymerizable unsaturated bonds, creating a new class of photo-curable resins. The resulting cured products achieve glass transition temperatures of 400°C or more, surpassing the heat resistance of conventional epoxy (meth)acrylate resins with biphenyl skeletons and meeting the requirements for advanced high-heat 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 cured product exhibits exceptionally high heat resistance, making it suitable for high-heat applications such as thermal nanoimprint lithography and display components, with a glass transition temperature of 400°C or more, doubling the heat resistance of existing materials.

Implementation Method 1

a cured product having a molecular structure represented by general formula (2) below, has very high heat resistance. The cured product is obtained by curing a compound having a structure provided by a reaction between a trifunctional phenol having a specific structure and a (meth)acrylic acid halide

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

photo-curable composition of the radical polymerization type, of which there is a wide choice of viable materials, have been commonly studied

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Data Source

PatentEP2878591B1Radically curable compound, method for producing radically curable compound, radically curable composition, cured product thereof, and composition for resist material
Publication Date: 2020.09.16 DIC CORP
  • EP2878591B1 patent drawingFigure 1
  • EP2878591B1 patent drawing
  • EP2878591B1 patent drawing

AI summary

Provided is a positive photoresist composition excellent in terms of heat resistance. A radically curable compound is represented by a general formula (1) below (where R1, R2, and R3 each independently represent an alkyl group having 1 to 8 carbon atoms; m and n each independently represent an integer of 1 to 4; p represents an integer of 0 to 4; X, Y, and Z each independently represent an acryloyloxy group, a methacryloyloxy group, or a hydroxy group, and at least one of X, Y, and Z represents an acryloyloxy group or a methacryloyloxy group; and t represents 1 or 2).