(Meth)acrylate Compound for High Refractive Index Optical Resins

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Solution Overview

Problem

Resin materials with high refractive indices face challenges in achieving both high transmittance and refractive index, particularly in applications requiring thin films for optical elements like microlenses, where existing compounds suffer from low transmittance due to their structural limitations.

Innovation Solution

A (meth)acrylate compound with a specific structural configuration, featuring a trivalent benzene with divalent phenylenes and aromatic hydrocarbon rings or heterocycles bonded in a twisted manner, incorporating acryloyloxy or methacryloyloxy groups to enhance refractive index while maintaining high transmittance, is developed.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If a resin material with high refractive index is used, then the refractive index is improved, but the transmittance deteriorates

Engineering Contradiction:
Improverefractive indexVSAvoidtransmittance
Core Design Contradiction:
Illumination intensityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the molecular structure parameters of the resin material. Specifically, it introduces a triazine ring-containing polymer structure with controlled aromatic ring substitutions and specific functional group arrangements (P1-P6 groups) to achieve a refractive index of 1.60 or higher while maintaining transmittance above 80% at 400nm wavelength. This structural parameter optimization resolves the contradiction between high refractive index and high transmittance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material design by combining multiple functional components within the polymer structure: triazine rings for refractive index enhancement, aromatic hydrocarbon rings or heterocycles for structural stability, and specific P1-P6 substituent groups for balancing optical properties. This composite molecular architecture achieves both high refractive index and high transmittance simultaneously.

Inventive Principle:
Principle #40Composite materials

2Length of stationary object

If the film thickness is reduced to micrometer order for optical elements, then the device complexity is reduced, but the transmittance deteriorates due to low transmittance material

Engineering Contradiction:
Improvefilm thicknessVSAvoidtransmittance
Core Design Contradiction:
Length of stationary objectVSObject-affected harmful factors

Solution Approach 1:

The patent uses parameter changes to optimize the material's intrinsic transmittance properties, achieving transmittance above 80% at 400nm wavelength. This enhanced material transmittance enables the use of micrometer-thick films while maintaining sufficient light transmission, thus reducing device complexity without sacrificing optical performance.

Inventive Principle:
Principle #35Parameter changes

3Illumination intensity

If aromatic rings and heterocycles are bonded in a twisted manner to enhance refractive index, then the refractive index is improved, but the synthesizability and compatibility deteriorate

Engineering Contradiction:
Improverefractive indexVSAvoidsynthesizability
Core Design Contradiction:
Illumination intensityVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by dividing the complex molecular structure into modular components: a core triazine ring, substitutable aromatic hydrocarbon rings or heterocycles, and standardized P1-P6 functional group positions. This modular segmentation facilitates systematic synthesis and improves manufacturability while maintaining the twisted bonding configuration necessary for high refractive index.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent optimizes structural parameters by controlling the types and positions of P1-P6 groups, which can be independently selected from specific chemical groups. This parameter control enables balanced optimization of synthesizability, compatibility, and refractive index without requiring complex non-modular structures.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS12066593B2(Meth)acrylate compound
Publication Date: 2024.08.20 CANON KK
  • US12066593B2 patent drawing
  • US12066593B2 patent drawing
  • US12066593B2 patent drawing

AI summary

The compound having a high refractive index characteristic and a high transmittance is a (meth)acrylate compound represented by the following general formula (1):in the general formula (1), X represents a phenylene group, Z1 to Z3 are selected from the group consisting of a phenyl group, a heteroaryl group, a phenylene group, a heteroarylene group, a phenylalkylene group having an alkylene group having 1 or more to 4 or less carbon atoms, and a heteroaralkylene group having an alkylene group having 1 or more to 4 or less carbon atoms, P1 to P3 are selected from the group consisting of an acryloyloxy group and a methacryloyloxy group, A is selected from the group consisting of an aryl group, a heteroaryl group, an arylene group, and a heteroarylene group, and “m” and “n” each represent 0 or 1, provided that when the “m” represents 0, the “n” represents 0.