Curable Resin Composition for Low-Dielectric Heat-Resistant Packaging

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Solution Overview

Problem

Existing resin materials for semiconductor packages and 3D printing applications lack sufficient heat resistance, low dielectric loss tangent, and moisture resistance, leading to issues such as warpage, poor electrical properties, and moisture absorption, which are critical for advanced electronic components and 5G communication systems.

Innovation Solution

A curable resin composition comprising a compound represented by specific organic groups and a dehydrohalogenation reaction, producing a cured product with improved heat resistance, low dielectric properties, and enhanced curability, using a mixture with a polymerization inhibitor and polyphenylene ether compound.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If a phenolic hydroxyl group is used in the resin composition, then heat resistance is improved, but electrical properties deteriorate due to residual hydroxyl groups after curing

Engineering Contradiction:
Improveheat resistanceVSAvoidelectrical properties
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters by substituting phenolic hydroxyl groups with allyl groups, transforming the resin from a phenolic structure to an allyl ether structure. This parameter change allows the resin to maintain heat resistance while eliminating residual hydroxyl groups that harm electrical properties, as the allyl groups fully participate in curing reactions.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by specifically modifying the hydroxyl group locations with allyl substitutions at controlled positions (indicated by m and n parameters in the formula). This selective modification ensures that heat resistance is maintained at critical locations while electrical properties are improved by eliminating problematic residual groups.

Inventive Principle:
Principle #3Local quality

2Volume of moving object

If the PKG substrate thickness is reduced to meet size requirements, then device density is improved, but warpage increases due to low rigidity

Engineering Contradiction:
Improvesubstrate thicknessVSAvoidwarpage
Core Design Contradiction:
Volume of moving objectVSShape

Solution Approach 1:

The patent changes the material parameters by developing a resin composition with specifically controlled molecular weight distribution (Mn: 200-5000, Mw: 2000-5000) and chemical structure (allyl ether of phenol with controlled substitution patterns). These parameter changes result in a cured product with high rigidity and Tg equal to or higher than solder mounting temperature, enabling thin substrates to resist warpage during high-temperature processing.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If conventional epoxy resin is used for sealing material, then manufacturing ease is improved, but heat resistance deteriorates for high-temperature applications

Engineering Contradiction:
Improvemanufacturing easeVSAvoidheat resistance
Core Design Contradiction:
Ease of manufactureVSTemperature

Solution Approach 1:

The patent creates a composite material system by combining allyl ether of phenol with specific curing agents (amine compounds, carboxylic acid compounds, or their anhydrides). This composite approach maintains the ease of manufacturing through standard curing processes while achieving heat resistance suitable for SiC semiconductor applications and other high-temperature environments.

Inventive Principle:
Principle #40Composite materials

4Adaptability or versatility

If photocurable or thermosetting resins are used for 3D printing, then manufacturing versatility is improved, but moisture resistance deteriorates due to ester bonds and hydroxyl groups

Engineering Contradiction:
Improvemanufacturing versatilityVSAvoidmoisture resistance
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent changes the chemical composition parameters by eliminating ester bonds and hydroxyl groups from the resin structure, replacing them with ether bonds and allyl groups that do not hydrolyze. This parameter change maintains the versatility of 3D printing applications while dramatically improving moisture resistance, making the cured products suitable for structural members and electronic encapsulation in humid environments.

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 excellent heat resistance, low dielectric properties, and improved stability, suitable for sealing electronic components and 3D printing applications, addressing warpage and moisture absorption issues.

Implementation Method 1

a dehydrohalogenation reaction in the presence of a basic catalyst

Methodology Applied
Scientific EffectDehydrohalogenation reaction: Chemical Bonding

Implementation Method 2

a curing reaction, and thus, it cannot be said that the electrical properties are sufficient

Methodology Applied
Scientific EffectCuring reaction: Chemical Bonding

Implementation Method 3

A mixture containing the compound described in any one of the aforementioned items [1] to [5] and a polymerization inhibitor

Methodology Applied
Scientific EffectPolymerization inhibition:

Data Source

PatentUS12595334B2Compound, mixture, curable resin composition and cured product thereof, and method for producing compound
Publication Date: 2026.04.07 NIPPON KAYAKU CO LTD
  • US12595334B2 patent drawing
  • US12595334B2 patent drawing
  • US12595334B2 patent drawing

AI summary

A compound of formula 1:where X and Y are each a different optional organic group. When there is a plurality of X, each X in the plurality of X may be the same as or different from each other. When there is a plurality of Y, each Y in the plurality of Y may be the same as or different from each other. R represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group. When there is a plurality of R, each R in the plurality of R may be the same as or different from each other. Variable m is an integer of 0 to 3, n is a repeating unit and satisfies 1≤n≤20, and p is a repeating unit and satisfies 0≤p≤20.