Cyanate Ester Resin Composition for Low-CTE PCB Laminates

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Solution Overview

Problem

Existing cyanic acid ester compounds fail to achieve a balance of low thermal expansion, flame retardance, and heat resistance while maintaining solvent solubility, and resin compositions derived from them are insufficient in properties such as adhesion, heat resistance, and thermal conductivity, leading to issues in semiconductor packaging and printed circuit boards.

Innovation Solution

A cyanic acid ester compound produced by cyanating a thiophene-containing phenol novolac resin, combined with other components like maleimide compounds, to form a resin composition that enhances solvent solubility and results in cured products with low thermal expansion, excellent flame retardance, and high heat resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If conventional epoxy resins are used for high-temperature applications, then heat resistance is improved, but storage stability deteriorates due to premature polymerization

Engineering Contradiction:
Improveheat resistanceVSAvoidstorage stability
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

A polymerization inhibitor is introduced as an intermediary substance to prevent premature polymerization of the epoxy resin at high temperatures during storage. The inhibitor acts as a mediator that suppresses unwanted side reactions while allowing the intended curing process to occur when needed, thus maintaining both heat resistance and storage stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The chemical composition parameters of the epoxy resin system are modified by selecting specific epoxy compounds and adding polymerization inhibitors. This parameter change allows the resin to maintain stability at elevated storage temperatures while retaining the ability to cure properly when required, resolving the contradiction between heat resistance and storage stability.

Inventive Principle:
Principle #35Parameter changes

2Temperature

If high glass transition temperature is achieved through resin modification, then heat resistance is improved, but processability deteriorates

Engineering Contradiction:
Improveglass transition temperatureVSAvoidprocessability
Core Design Contradiction:
TemperatureVSEase of manufacture

Solution Approach 1:

The molecular structure parameters of the epoxy resin are optimized by selecting specific epoxy compounds with appropriate glass transition temperatures. This parameter adjustment achieves high heat resistance while maintaining adequate processability during manufacturing operations such as molding and lamination.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If conventional epoxy resin systems are used, then manufacturing simplicity is maintained, but environmental compatibility deteriorates due to harmful emissions

Engineering Contradiction:
Improvemanufacturing simplicityVSAvoidenvironmental compatibility
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The chemical composition of the epoxy resin system is modified to eliminate or reduce harmful emissions during processing. This parameter change replaces conventional resins with environmentally friendly alternatives that maintain manufacturing simplicity while improving environmental compatibility by reducing volatile organic compound emissions and other harmful byproducts.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3438146B1Cyanic acid ester compound and method for producing same, resin composition, cured article, prepreg, sealing material, fiber-reinforced composite material, adhesive agent, metal foil-clad laminate plate, resin sheet, and printed wiring board
Publication Date: 2026.04.08 MITSUBISHI GAS CHEM CO INC
  • EP3438146B1 patent drawingFigure 1~2
  • EP3438146B1 patent drawingFigure 3
  • EP3438146B1 patent drawing

AI summary

The present invention provides a novel cyanic acid ester compound that has excellent solvent solubility and provides a cured product having a low rate of thermal expansion and having excellent flame retardance and heat resistance, and a resin composition containing the compound, etc. The present invention provides a resin composition whose cured product obtained by curing can achieve a printed circuit board excellent in peel strength, glass transition temperature, rate of thermal expansion, rate of water absorption, and thermal conductivity. The present invention provides a resin composition whose cured product obtained by curing can achieve a printed circuit board not only having a high glass transition temperature and low thermal expansibility but being also excellent in flexural modulus and thermal conductivity. The cyanic acid ester compound is represented by the general formula (1):