Fluorinated Aromatic Compound for Optical Resins

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Solution Overview

Problem

Current thermosetting resins used in optical and electronic equipment lack sufficient transparency, heat resistance, and mechanical properties, particularly in high-temperature applications, and fluorinated polyimide optical waveguides are brittle and expensive to produce.

Innovation Solution

A fluorinated aromatic compound with at least two carbon-carbon unsaturated bonds is developed, which can be used to create a curable material that forms a cured product with enhanced transparency, heat resistance, and mechanical properties through a condensation reaction involving specific aromatic compounds and HF elimination agents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If an aromatic epoxy resin is used to achieve heat resistance, then heat resistance is improved, but transparency in the near ultraviolet region deteriorates

Engineering Contradiction:
Improveheat resistanceVSAvoidtransparency in near ultraviolet region
Core Design Contradiction:
TemperatureVSIllumination intensity

Solution Approach 1:

The invention changes the chemical structure parameters of the epoxy resin by introducing fluorinated aromatic groups and controlling the aromatic ring content (0.1-5 mmol/g) to achieve both heat resistance and near-ultraviolet transparency. This parameter optimization resolves the contradiction between thermal stability and optical transparency.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite epoxy resin system combining fluorinated aromatic structures with aliphatic chains, achieving synergistic effects that provide both high heat resistance (glass transition temperature ≥100°C) and excellent near-ultraviolet transparency, resolving the trade-off between these two properties.

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If an alicyclic epoxy resin is used to achieve transparency in the near ultraviolet region, then transparency is improved, but heat resistance deteriorates

Engineering Contradiction:
Improvetransparency in near ultraviolet regionVSAvoidheat resistance
Core Design Contradiction:
Illumination intensityVSTemperature

Solution Approach 1:

The invention modifies the epoxy resin composition by controlling the aromatic ring content within 0.1-5 mmol/g and introducing fluorinated structures, which enhances heat resistance while preserving near-ultraviolet transparency. The glass transition temperature is raised to ≥100°C without sacrificing optical properties.

Inventive Principle:
Principle #35Parameter changes

3Temperature

If a fluorinated polyimide is used to achieve heat resistance and transparency, then heat resistance and transparency are improved, but mechanical properties deteriorate due to brittleness

Engineering Contradiction:
Improveheat resistanceVSAvoidmechanical properties
Core Design Contradiction:
TemperatureVSStrength

Solution Approach 1:

The invention develops a composite epoxy resin system incorporating fluorinated aromatic structures with flexible aliphatic chains. This composite structure provides both high heat resistance (Tg ≥100°C) and improved mechanical flexibility, resolving the brittleness issue of fluorinated polyimides while maintaining optical transparency.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention introduces fluorinated aromatic groups at specific concentrations (0.1-5 mmol/g) to provide localized heat resistance and transparency enhancement, while the bulk polymer matrix maintains flexibility and mechanical toughness through aliphatic chain structures.

Inventive Principle:
Principle #3Local quality

4Illumination intensity

If a silicone resin is used to achieve transparency and light resistance, then transparency and light resistance are improved, but reliability deteriorates due to large thermal expansion coefficient and gas permeability

Engineering Contradiction:
ImprovetransparencyVSAvoidthermal expansion coefficient and gas permeability
Core Design Contradiction:
Illumination intensityVSReliability

Solution Approach 1:

The invention changes the chemical composition parameters by incorporating fluorinated aromatic epoxy structures that reduce thermal expansion coefficient and gas permeability compared to silicone resins, while maintaining excellent transparency and light resistance. The aromatic structures provide dimensional stability and barrier properties.

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 fluorinated aromatic compound enables the production of a cured product that is excellent in optical characteristics, heat resistance, and mechanical properties, making it suitable for use in optical members and as a crosslinking aid for fluorinated elastomers, improving both chemical and heat resistance.

Implementation Method 1

a step of subjecting an aromatic compound represented by the following formula (a1) and a fluorinated aromatic compound represented by the following formula (a2) to a condensation reaction in the presence of a HF elimination agent

Methodology Applied
Scientific EffectCondensation reaction:

Implementation Method 2

when heated or irradiated with light, it will be cured by a reaction of the crosslinkable functional groups one another

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Data Source

PatentUS10087128B2Fluorinated aromatic compound, method for its production, curable material, its cured product, and optical member
Publication Date: 2018.10.02 AGC INC
  • US10087128B2 patent drawing
  • US10087128B2 patent drawing
  • US10087128B2 patent drawing

AI summary

To provide a novel fluorinated aromatic compound having at least two carbon-carbon unsaturated bonds, a method for its production, a curable material comprising the fluorinated aromatic compound, a cured product thereof, and an optical member. The fluorinated aromatic compound is represented by formula (A), wherein n is an integer of 0 to 6, a is an integer of 0 to 5, b is an integer of 0 to 4, c is an integer of 0 to 4, a+c+n is 2 to 6, a+b is 2 to 9, Z is a single bond, —O—, —S—, —CO—, —C(CH3)2—, —C(CF3)2—, —SO—, or —SO2—, Rf1 is a C1-8 fluoroalkyl group, Y1 and Y2 are each independently a group represented by formula (1) (s is 0 or 1, and R1, R2, R3, and R4 are each independently a hydrogen atom or a fluorine atom), and F in the aromatic ring indicates that hydrogen atoms in the aromatic ring are all substituted by fluorine atoms.