Adamantane Derivative Resin for Optical Semiconductor Sealing

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Solution Overview

Problem

Existing sealing materials for optical semiconductors, such as bisphenol A epoxy resin, face issues with light absorption and inadequate heat resistance, while adamantane derivatives offer promising optical and heat resistance properties but require complex reaction pathways to produce cyclic ether compounds efficiently.

Innovation Solution

A cyclic ether compound with an adamantane derivative, represented by a specific general formula, is produced by reacting an adamantane derivative with a compound having a cyclic ether group, and a resin composition containing this derivative and an epoxy resin curing agent is used to create a sealing agent for optical semiconductors, enhancing transparency, heat resistance, and dielectric properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If bisphenol A epoxy resin is used for sealing LED, then heat resistance is achieved, but light absorption occurs and the resin turns yellow due to aromatic components

Engineering Contradiction:
Improveheat resistanceVSAvoidlight absorption and yellowing
Core Design Contradiction:
TemperatureVSObject-affected harmful factors

Solution Approach 1:

The invention extracts and removes the problematic aromatic ring structure from the epoxy resin molecule through hydrogenation, while retaining the desirable heat resistance properties. This is achieved by converting the aromatic rings in bisphenol A epoxy resin into saturated alicyclic structures, eliminating light absorption while preserving thermal stability.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the chemical structure parameter of the epoxy resin by hydrogenating the aromatic rings to alicyclic structures. This structural transformation modifies the resin's optical properties (reducing light absorption) while maintaining its thermal properties (heat resistance), thus resolving the contradiction between heat resistance and light transparency.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If aromatic rings in epoxy resin are hydrogenated to improve light resistance, then light absorption is reduced, but heat resistance becomes insufficient to withstand LED operating temperatures

Engineering Contradiction:
Improvelight resistanceVSAvoidheat resistance
Core Design Contradiction:
Object-affected harmful factorsVSTemperature

Solution Approach 1:

The invention creates a composite molecular structure combining hydrogenated alicyclic epoxy resin with adamantane derivatives. This composite approach synergistically combines the light resistance of hydrogenated structures with the enhanced heat resistance of adamantane cages, achieving both improved optical and thermal performance simultaneously.

Inventive Principle:
Principle #40Composite materials

3Temperature

If adamantane diols are reacted with cyclic ether group-containing compounds to produce cyclic ether compounds, then heat resistance and light resistance are achieved, but the reaction yield is low due to low reactivity of adamantane diols

Engineering Contradiction:
Improveheat resistanceVSAvoidreaction yield
Core Design Contradiction:
TemperatureVSProductivity

Solution Approach 1:

The invention changes the reaction parameters by using alternative adamantane derivatives (such as adamantane carboxylic acids or esters) instead of adamantane diols as starting materials. This substitution fundamentally alters the reaction pathway and conditions, enabling high-yield production of cyclic ether compounds with adamantane structures while maintaining the desired heat and light resistance properties.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If complex reaction pathways are used to obtain cyclic ether compounds at high yield, then productivity is improved, but device complexity increases and industrial applicability is reduced

Engineering Contradiction:
Improvereaction yieldVSAvoidreaction pathway complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention segments the synthesis process into simple, modular steps starting from readily available adamantane derivatives. Instead of using complex multi-step pathways, the method employs straightforward reactions (such as esterification or condensation) that can be easily controlled and scaled, achieving high yields while maintaining process simplicity and industrial feasibility.

Inventive Principle:
Principle #1Segmentation

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 resin composition exhibits excellent optical characteristics, long-term heat resistance, and adhesive properties, making it suitable for optical semiconductors, electronic circuits, and other applications, while simplifying the production process of adamantane derivatives.

Implementation Method 1

reacting an adamantane derivative with a compound having a cyclic ether group

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

the bisphenol A epoxy resin absorbs light and turns yellow

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentUS8022151B2Adamantane derivative, method for producing the same, resin composition containing the adamantane derivative and use thereof
Publication Date: 2011.09.20 OSAKA ORGANIC CHEM INDS
  • US8022151B2 patent drawing
  • US8022151B2 patent drawing
  • US8022151B2 patent drawing

AI summary

Provided are: an adamantane derivative represented by the following general formula (I) giving a cured product excellent in optical characteristics such as transparency and light resistance, durabilities such as heat resistance, and electrical characteristics such as dielectric constant; a method of producing the adamantane derivative; a resin composition containing the adamantane derivative and an epoxy resin curing agent; and a sealing agent for an optical semiconductor using the resin composition:where: Y represents a group selected from a hydrocarbon group, a hydroxyl group, a carboxyl group, and an ═O group formed by two Y's being combined together; Z represents a cyclic ether group; n represents an integer of 0 or more; and p represents an integer of 2 to 4 and q represents an integer of 0 to 14, while satisfying 2≦p+q≦16.