DCPD-Derived Polyether for Low-K Non-Flammable Epoxy Curing

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Solution Overview

Problem

Epoxy resin materials used in electronics face challenges due to high flammability and high dielectric constant, limiting their application in semiconductor packaging and optoelectronics, while existing aromatic polyethers lack sufficient reactive groups for curing and modifying epoxy resins effectively.

Innovation Solution

A DCPD-derived polyether is synthesized through a method involving reactions with 4,4′-difluorobenzophenone, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and phenol, incorporating a phosphorus group to serve as both an epoxy resin curing agent and self-curing agent, achieving low-k, non-flammable, and thermally stable properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If epoxy resin is used for coating and semiconductor packaging, then solvent resistance and ease of processing are improved, but flammability increases and dielectric constant increases

Engineering Contradiction:

Improveease of processingVSAvoidflammability

Core Design Contradiction:

Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent creates a composite material by incorporating phosphorus-containing cyclic compounds into the epoxy resin system. This composite approach combines the processing advantages of epoxy resin with the flame-retarding properties of phosphorus compounds, achieving both ease of manufacture and reduced flammability simultaneously

Inventive Principle:

Principle #40Composite materials

2Ease of manufacture

If epoxy resin is used for coating and semiconductor packaging, then solvent resistance and ease of processing are improved, but dielectric constant increases

Engineering Contradiction:

Improveease of processingVSAvoiddielectric constant

Core Design Contradiction:

Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent develops a composite material system where phosphorus-containing cyclic compounds are integrated with epoxy resin. This composite structure reduces the overall dielectric constant while preserving the processing advantages of epoxy, addressing both ease of manufacture and dielectric constant requirements

Inventive Principle:

Principle #40Composite materials

3Temperature

If aromatic polyether is used as epoxy resin toughener, then thermal stability and ductility are improved, but reactivity with epoxy resin deteriorates due to scarcity of reacting groups

Engineering Contradiction:

Improvethermal stabilityVSAvoidreactivity

Core Design Contradiction:

TemperatureVSAdaptability or versatility

Solution Approach 1:

The patent introduces phosphorus-containing cyclic compounds with specific local reactive groups that can interact with epoxy resin. This localized reactivity enhancement allows the material to maintain its inherent thermal stability while gaining the adaptability and reactivity needed for effective epoxy modification

Inventive Principle:

Principle #3Local quality

4Object-affected harmful factors

If phosphorus-based structure is used to render cured product flame-retarding, then flammability is improved, but dielectric constant deteriorates due to production of high-polarity secondary alcohol

Engineering Contradiction:

ImproveflammabilityVSAvoiddielectric constant

Core Design Contradiction:

Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The patent employs phosphorus-containing cyclic compounds that undergo ring-opening reactions to produce carboxylic acid groups instead of high-polarity secondary alcohols. This chemical parameter change in the reaction pathway maintains flame-retarding properties while reducing dielectric constant by avoiding the formation of highly polar alcohol groups

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 DCPD-derived polyether exhibits a V-0 rating in flammability tests, high thermal stability, and a dielectric constant less than 2.7, making it suitable for high-frequency substrates and printed circuit boards with improved mechanical strength and processability.

Implementation Method 1

ring-opening reactions of the epoxy resin is accompanied by transesterification which takes place in the presence of an active ester

Methodology Applied

Scientific EffectRing-opening reaction:

Implementation Method 2

ring-opening reactions of the epoxy resin is accompanied by transesterification which takes place in the presence of an active ester

Methodology Applied

Scientific EffectTransesterification:

Implementation Method 3

The phosphorus-based structure renders a cured product flame-retarding

Methodology Applied

Scientific EffectFlame retardancy:

Implementation Method 4

The hydroxyl group of the structure serves as an epoxy resin curing agent

Methodology Applied

Scientific EffectCuring reaction:

Implementation Method 5

dicyclopentadiene (DCPD) is easy to process because it is a high-rigidity aliphatic dicyclic compound and a promising green material

Methodology Applied

Scientific EffectThermal stability:

Data Source

PatentUS10711103B2DCPD-derived polyether and method of producing the same

Publication Date: 2020.07.14 NAT CHUNG SHAN INST SCI & TECH

AI summary

A low-k, non-flammable dicyclopentdiene (DCPD)-derived polyether and a method of producing the same are introduced. Incorporation of a phosphorus group and a DCPD derivative into a low-k, non-flammable dicyclopentdiene (DCPD)-derived polyether enable the DCPD-derived polyether to not only serve as an epoxy resin curing agent but also cure itself such that the cured product not only features satisfactory thermal properties and low-k characteristics but is also non-flammable.