Asymmetric Polymerizable Liquid Crystal Compound for Film Durability

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Solution Overview

Problem

The solubility and durability of optically anisotropic films formed using polymerizable liquid crystal compounds are compromised due to variations in polymerization conditions and the type of polymerizable compound used, leading to issues with birefringence changes under high temperature and humidity exposure.

Innovation Solution

A polymerizable liquid crystal compound with an asymmetric structure, featuring a sterically hindered group in the aromatic ring and differing C log P values for the groups extending in the long-axis direction, improves solubility and durability by inhibiting moisture absorption and enhancing molecular packing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a polymerizable liquid crystal compound with conventional structure is used, then the optically anisotropic film can be formed, but the solubility is deteriorated and durability is compromised due to birefringence changes under high temperature and humidity

Engineering Contradiction:
Improvedurability of optically anisotropic filmVSAvoidsolubility of polymerizable liquid crystal compound
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies asymmetry by introducing a sterically hindered group at the para position of the aromatic ring in the liquid crystal compound structure. This asymmetric substitution creates different spatial environments for the polymerizable groups, improving molecular packing and solubility while maintaining the optically anisotropic properties necessary for film formation and durability

Inventive Principle:
Principle #4Asymmetry

Solution Approach 2:

The patent applies local quality by specifically modifying the aromatic ring structure with a sterically hindered group at the para position, while keeping other parts of the molecule intact. This localized structural modification targets the solubility and durability issues without affecting the overall liquid crystal properties and optical performance of the compound

Inventive Principle:
Principle #3Local quality

2Ease of manufacture

If the structure of liquid crystal compound is modified to improve solubility, then solubility becomes good, but the durability and birefringence stability under high temperature and humidity may be compromised

Engineering Contradiction:
Improvesolubility of polymerizable liquid crystal compoundVSAvoidbirefringence stability of optically anisotropic film
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The asymmetric substitution with a sterically hindered group improves solubility by preventing excessive molecular aggregation, while the rigid aromatic core and liquid crystalogenic groups maintain the molecular anisotropy necessary for stable birefringence. The asymmetric structure promotes uniform molecular orientation in the film, preserving optical stability

Inventive Principle:
Principle #4Asymmetry

Solution Approach 2:

The patent changes the structural parameters of the liquid crystal compound by introducing the sterically hindered group, which modifies the molecular volume, shape, and intermolecular interaction parameters. These parameter changes improve solubility while the liquid crystal phase behavior and optical properties are maintained through careful selection of the core structure

Inventive Principle:
Principle #35Parameter changes

3Reliability

If conventional polymerizable liquid crystal compounds are used, then the optically anisotropic film can be formed, but moisture absorption occurs leading to durability issues

Engineering Contradiction:
Improvedurability of optically anisotropic filmVSAvoidmoisture absorption
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent converts the potential harm of moisture absorption by designing a molecular structure where the sterically hindered group creates a hydrophobic environment around the polymerizable groups. This structural feature effectively repels moisture while the polymer network formed after curing provides additional barrier properties, transforming the challenge of moisture resistance into a design advantage

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 proposed compound achieves excellent solubility and durability for optically anisotropic films, maintaining birefringence stability even under high temperature and humidity conditions, as evidenced by improved retardation values and resistance to environmental changes.

Implementation Method 1

the solubility and durability of optically anisotropic films formed using polymerizable liquid crystal compounds are compromised due to variations in polymerization conditions and the type of polymerizable compound used, leading to issues with birefringence changes under high temperature and humidity exposure

Methodology Applied
Scientific EffectBirefringence: Birefringence

Data Source

PatentUS11225605B2Polymerizable liquid crystal compound, method for producing polymerizable liquid crystal compound, polymerizable liquid crystal composition, optically anisotropic film, optical film, polarizing plate, and image display device
Publication Date: 2022.01.18 FUJIFILM CORP
  • US11225605B2 patent drawing
  • US11225605B2 patent drawing
  • US11225605B2 patent drawing

AI summary

An object of the present invention is to provide a polymerizable liquid crystal compound having excellent solubility, which is used for the formation of an optically anisotropic film having excellent durability, a method for producing the same, a polymerizable liquid crystal composition, an optically anisotropic film, an optical film, a polarizing plate, and an image display device. The polymerizable liquid crystal compound of the embodiment of the present invention is a polymerizable liquid crystal compound represented by Formula (1), L1-SP1-A1-D3-G1-D1-Ar-D2-G2-D4-A2-SP2-L2 . . . (1) in Formula (1), the ClogP value of the group represented by L1-SP1-A1-D3-G1-D1 and the ClogP value of the group represented by L2-SP2-A2-D4-G2-D2 are different from each other, and at least one of the ClogP values is 3.3 or more.