Arylcyclobutene Curing in Air with Hindered Phenol Antioxidants

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Solution Overview

Problem

Arylcyclobutene-based materials, used as low dielectric constant materials in electronics, face challenges in curing stability and oxidation resistance when exposed to oxygen-containing environments, leading to undesirable degradation in key properties such as dielectric constant, water uptake, and transmittance.

Innovation Solution

Incorporating hindered phenol antioxidants into arylcyclobutene-based formulations allows for curing in oxygen-containing environments like air without significant degradation, using a composition comprising a curable arylcyclobutene material and an antioxidant compound with hindered phenol functionality, and optionally including acid functionality and photoactive compounds for aqueous development and imaging.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If arylcyclobutene-based materials are cured in oxygen-containing environments, then the curing process can be simplified and productivity improved, but the material suffers from oxidation degradation leading to worsened dielectric constant, water uptake, and transmittance properties

Engineering Contradiction:
Improvecuring process efficiencyVSAvoidmaterial property stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

A hindered phenol antioxidant compound is introduced as an intermediary substance between the arylcyclobutene-based material and oxygen in the curing environment. The antioxidant preferentially reacts with oxygen or free radicals, protecting the BCB material from oxidation while allowing the curing process to proceed in air, thus resolving the contradiction between simplified curing and property stability

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The chemical composition parameter of the formulation is changed by incorporating hindered phenol antioxidants. This parameter change enables the material system to tolerate oxygen exposure during curing, transforming the curing environment from requiring strict nitrogen atmosphere to allowing air curing, thereby improving productivity without sacrificing reliability

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If traditional antioxidants are used in BCB formulations, then shelf-life stability is improved, but compatibility issues arise with adhesion promoters and the material still degrades during air curing

Engineering Contradiction:
Improveshelf-life stabilityVSAvoidoxidation degradation during curing
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The chemical structure parameter of the antioxidant is specifically changed to hindered phenol functionality. This structural parameter change provides dual benefits: maintaining shelf-life stability through antioxidant activity and preventing oxidation degradation during air curing, while avoiding compatibility issues with adhesion promoters that plague traditional antioxidants

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 method enables curing in air with minimal impact on dielectric constant, water uptake, and transmittance, maintaining key properties comparable to nitrogen-cured samples, while avoiding compatibility issues with adhesion promoters.

Implementation Method 1

curing the composition by heating in an oxidizing environment... arylcyclobutene-based formulations can be cured in oxygen containing environments such as air without unacceptable degradation in key properties... hindered phenol containing antioxidants are used

Methodology Applied
Scientific EffectOxidation resistance: Oxidation

Implementation Method 2

photoactive compound which initiates the desired chemical changes (for example, photocure or photodeactivation of a dissolution inhibitor)... exposed (preferably imagewise exposed) to activating radiation for the photoactive compound

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS8143324B2Benzocyclobutene based polymer formulations and methods for processing such formulations in oxidative environments
Publication Date: 2012.03.27 DOW GLOBAL TECHNOLOGIES LLC
  • US8143324B2 patent drawing
  • US8143324B2 patent drawing
  • US8143324B2 patent drawing

AI summary

The use of hindered phenol containing anti-oxidants enable arylcyclobutene-based formulations to be cured in oxygen containing environments such as air without unacceptable degradation in key properties of dielectric constant, water uptake, or transmittance.