Vinylbenzyl Active Ester Resin for Low-Loss Heat-Resistant Substrates

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Solution Overview

Problem

Current thermosetting resin compositions for semiconductor package substrates face challenges in achieving both high heat resistance and low dielectric loss tangent while maintaining a low dielectric constant, especially when subjected to high-speed, high-frequency signals.

Innovation Solution

A monofunctional phenolic compound with vinylbenzyl groups is used to produce an active ester resin, which includes a vinylbenzyl-modified aryloxycarbonyl group, forming a cured product with enhanced dielectric properties and heat resistance when incorporated into a thermosetting resin composition.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If an active ester compound is used as a curing agent for epoxy resins to achieve low dielectric constant and low dielectric loss tangent, then dielectric properties are improved, but heat resistance is insufficient

Engineering Contradiction:
Improvedielectric loss tangentVSAvoidheat resistance
Core Design Contradiction:
Loss of energyVSTemperature

Solution Approach 1:

The invention modifies the chemical structure of the phenolic compound by introducing vinylbenzyl groups at specific positions (using compounds with formulas (1) or (2) where R1 is vinylbenzyl group and R2 is hydrogen, alkyl, or aryl group). This structural parameter change in the raw material leads to an active ester resin with both low dielectric loss tangent (3.0×10^-3 or less at 10 GHz) and high heat resistance (160°C or more), simultaneously improving both contradictory properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure by combining vinylbenzyl-modified phenolic compound with active ester groups. The resulting active ester resin integrates the low dielectric properties of traditional active ester compounds with the high heat resistance of vinylbenzyl-modified phenolic structures, achieving a material that satisfies both low dielectric loss tangent and high heat resistance requirements.

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If multiple techniques are combined to achieve low dielectric constant and low dielectric loss tangent, then dielectric properties are improved, but device complexity increases

Engineering Contradiction:
Improvedielectric loss tangentVSAvoidcomposition complexity
Core Design Contradiction:
Loss of energyVSDevice complexity

Solution Approach 1:

The invention merges multiple functional characteristics into a single active ester resin molecule. By incorporating vinylbenzyl groups into the phenolic compound structure before forming the active ester, the resin simultaneously achieves low dielectric constant, low dielectric loss tangent, and high heat resistance in one material system, eliminating the need for complex multi-component formulations.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The vinylbenzyl-modified active ester resin serves multiple functions simultaneously: it acts as both the resin base and the curing agent, provides low dielectric properties, maintains high heat resistance, and ensures reliable curing performance. This multi-functionality simplifies the overall composition compared to combining multiple separate techniques.

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

3Volume of moving object

If semiconductor package substrates are made thinner to reduce size, then compactness is improved, but warpage increases during packaging

Engineering Contradiction:
Improvesubstrate thicknessVSAvoidwarpage resistance
Core Design Contradiction:
Volume of moving objectVSStability of the object's composition

Solution Approach 1:

The invention changes the thermal and mechanical parameters of the resin material through vinylbenzyl modification. The resulting active ester resin exhibits high heat resistance (160°C or more) and appropriate thermal expansion characteristics, enabling thin substrates to maintain dimensional stability and resist warpage during the packaging process while achieving the required thinness for compact designs.

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 resulting cured product exhibits improved heat resistance and dielectric properties, specifically a heat resistance of 160°C or more and a low dielectric loss tangent of 3.0×10−3 or less at 10 GHz, making it suitable for electronic components like semiconductor package substrates.

Implementation Method 1

A monofunctional phenolic compound including one or more vinylbenzyl groups, and a method for producing the active ester resin

Methodology Applied
Scientific EffectChemical bonding: Chemical Bonding

Data Source

PatentUS12017980B2Monofunctional phenolic compound, active ester resin and method for producing the same, and thermosetting resin composition and cured product thereof
Publication Date: 2024.06.25 DIC CORP
  • US12017980B2 patent drawing
  • US12017980B2 patent drawing
  • US12017980B2 patent drawing

AI summary

Provided are a monofunctional phenolic compound used for producing an active ester resin capable of forming a cured product having excellent dielectric properties and excellent heat resistance, an active ester resin and a method for producing the active ester resin, and a thermosetting resin composition and a cured product of the thermosetting resin composition. Specifically, provided are a monofunctional phenolic compound including one or more vinylbenzyl groups and an active ester resin including a vinylbenzyl structure attached to a terminal group of the molecular chain and derived from the monofunctional phenolic compound. The vinylbenzyl structure preferably includes a vinylbenzyl-modified aryloxycarbonyl group.