Ester-Amide Epoxy Curing Agent for Low Dielectric Loss

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Solution Overview

Problem

Existing epoxy materials used in semiconductor packaging suffer from significant data transmission loss due to high dielectric loss and compromised processability, particularly in desmear properties, hindering ultra-high-speed data transmission.

Innovation Solution

A novel curing agent with ester and amide groups in a benzene unit is developed, which improves both low dielectric loss characteristics and processability, specifically desmearability, through a multi-step synthesis process involving isophthaloyl chloride, phenol, and amino phenol reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If an active ester compound is used as a curing agent to lower dielectric loss, then dielectric loss characteristics are improved, but processability (desmear properties) is diminished

Engineering Contradiction:
Improvedielectric lossVSAvoidprocessability (desmear properties)
Core Design Contradiction:
Loss of energyVSEase of manufacture

Solution Approach 1:

The patent combines two different functional groups (ester group for low dielectric loss and amide group for processability) into a single curing agent molecule. This merging allows the curing agent to simultaneously provide both low dielectric loss characteristics and good desmear properties, resolving the contradiction between improving dielectric loss and maintaining processability

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The curing agent is designed as a composite molecular structure containing both ester and amide functional groups attached to a benzene unit. This composite structure integrates the beneficial properties of both functional groups, enabling the material to achieve low dielectric loss while maintaining excellent processability and desmearability

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If conventional curing agents are used to achieve processability, then desmear properties are maintained, but dielectric loss increases causing data transmission loss

Engineering Contradiction:
Improveprocessability (desmear properties)VSAvoiddielectric loss
Core Design Contradiction:
Ease of manufactureVSLoss of energy

Solution Approach 1:

The patent merges ester and amide functional groups into one curing agent molecule, allowing simultaneous achievement of low dielectric loss (from ester group) and good processability (from amide group), thereby resolving the trade-off between these two properties

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The dual-functional curing agent performs multiple roles: the ester group contributes to low dielectric loss for high-speed data transmission, while the amide group provides processability and desmear properties. This multi-functionality eliminates the need to choose between conflicting properties

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 curing agent enhances dielectric properties and processability, resulting in improved desmearability and solution dispersibility, suitable for insulating films and semiconductor packaging materials.

Implementation Method 1

a first step of the formation of an ester group by mixing isophthaloyl chloride with at least one of phenol and 2-allyl phenol

Methodology Applied
Scientific EffectEsterification reaction: Chemical Bonding

Implementation Method 2

a second step of the formation of an amide functional group by mixing a reaction product of the first step with at least one of m-amino phenol, p-amino phenol and o-amino phenol

Methodology Applied
Scientific EffectAmide formation reaction: Chemical Bonding

Implementation Method 3

a third step of the formation of an alkoxysilyl group by mixing a reaction product of the second step with 3-(triethoxysilyl) propyl isocyanate

Methodology Applied
Scientific EffectSilylation reaction: Chemical Bonding

Data Source

PatentUS20250388719A1Novel curing agent having ester and amide groups, method for preparing the same, epoxy composition, cured product, and article comprising the same
Publication Date: 2025.12.25 KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY
  • US20250388719A1 patent drawing
  • US20250388719A1 patent drawing
  • US20250388719A1 patent drawing

AI summary

The present disclosure relates to a novel curing agent having ester and amide groups simultaneously attached to a benzene unit exhibiting excellent low dielectric loss characteristics (low dissipation factor or low Df) and processability, a method for preparing the same, an epoxy composition, a cured product, and an article comprising the same. Excellent low dielectric loss and processability are achieved by the epoxy composition comprising the novel curing agent of the present disclosure and epoxy resin. Therefore, the epoxy composition comprising the novel curing agent of the present disclosure is suitable for use as an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an epoxy molding material, or the like due to these improved properties.