Tolan Liquid Crystal Compound Light Fastness

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Solution Overview

Problem

Current liquid crystal compounds used in optically anisotropic bodies and reflective films, particularly those with a tolan skeleton, exhibit inadequate light fastness, necessitating the use of additional ultraviolet absorbers for protection, which complicates production and reduces efficiency.

Innovation Solution

A compound represented by General Formula (1) with an asymmetric molecular structure and specific substituents, such as a fluoroalkyl group or alkoxy group, exhibiting liquid crystallinity and improved light fastness, is developed, allowing for the creation of a composition that can be cured to form optically anisotropic bodies and reflective films without the need for additional UV absorbers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a tolan compound with an ester group is used as a liquid crystal compound, then the compound can be applied to produce optically anisotropic bodies and reflective films, but the light fastness of the compound is insufficient

Engineering Contradiction:
Improvelight fastnessVSAvoidproduction complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the molecular structure parameters of the liquid crystal compound by replacing the ester group with a carboxylic acid group and introducing specific substituents (fluoroalkyl, alkoxy, or alkyl groups) at defined positions on the aromatic rings. This structural parameter change fundamentally improves light fastness while maintaining liquid crystallinity and optical properties, eliminating the need for additional UV absorbers and simplifying the overall production process.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining a tolan skeleton with carboxylic acid functionality and specific substituents. This composite approach within the molecular structure achieves both the desired liquid crystal properties and enhanced light fastness, replacing the need for separate protective additives and reducing production complexity.

Inventive Principle:
Principle #40Composite materials

2Reliability

If an adjuvant such as an ultraviolet absorber is blended with the liquid crystal compound to impart light fastness, then the light fastness is improved, but the production process becomes more complex and less efficient

Engineering Contradiction:
Improvelight fastnessVSAvoidproduction efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent merges the light fastness function directly into the liquid crystal compound molecule itself by incorporating a carboxylic acid group and stabilizing substituents. This consolidation eliminates the need for separate ultraviolet absorber additives, streamlining the production process and improving productivity while maintaining excellent light fastness properties.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The liquid crystal compound becomes self-protecting against UV degradation through its inherent carboxylic acid structure and stabilizing substituents. The molecule serves its own protective function without requiring external adjuvants, thereby simplifying production and enhancing productivity by removing additional processing steps.

Inventive Principle:
Principle #25Self-service

3Reliability

If a liquid crystal compound with excellent light fastness is used, then additional ultraviolet absorbers are not required, but such compounds have been difficult to develop with sufficient light fastness

Engineering Contradiction:
Improvelight fastnessVSAvoidcompound performance
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent successfully achieves the desired compound performance by systematically changing molecular parameters: replacing the ester group with a carboxylic acid group, specifying particular substituents (fluoroalkyl, alkoxy, or alkyl) at defined positions, and maintaining the tolan skeleton. These parameter changes deliver both excellent light fastness and proper liquid crystal properties in a single compound, meeting all performance requirements without additional additives.

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 compound achieves excellent light fastness, enhancing the performance of optically anisotropic bodies and reflective films by maintaining stability under light exposure without requiring additional protective agents, thus simplifying production and improving their optical properties.

Implementation Method 1

A compound (hereinafter also simply referred to as liquid crystal compound) that exhibits liquid crystallinity can be applied to various uses. For example, the liquid crystal compound is applied to production of an optically anisotropic body typified by a retardation film, or to production of a reflective film by immobilizing a cholesteric liquid crystalline phase.

Methodology Applied
Scientific EffectLiquid crystallinity: Liquid Crystals

Implementation Method 2

The compound achieves excellent light fastness, enhancing the performance of optically anisotropic bodies and reflective films by maintaining stability under light exposure without requiring additional protective agents

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentUS10907099B2Compound, composition, cured object, optically anisotropic body, and reflective film
Publication Date: 2021.02.02 FUJIFILM CORP
  • US10907099B2 patent drawing
  • US10907099B2 patent drawing
  • US10907099B2 patent drawing

AI summary

An object of the present invention is to provide a compound (particularly, a liquid crystal compound having excellent light fastness) which has excellent light fastness and can be used for an optically anisotropic body, a reflective film obtained by immobilizing a cholesteric liquid crystalline phase, or the like.Another object of the present invention is to provide a composition containing the above-mentioned compound (particularly, a liquid crystal compound having excellent light fastness); and a cured object, an optically anisotropic body, and a reflective film, which are obtained by curing the above-mentioned composition.The compound of the present invention is represented by General Formula (1).