Anthraquinone Dichroic Dye for Liquid Crystal Solubility

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Solution Overview

Problem

Azo dichroic dyes used in guest-host type liquid crystal devices have low light resistance, while anthraquinone dyes have poor solubility in host liquid crystals, making it difficult to achieve a balance between solubility and order parameter.

Innovation Solution

A liquid crystal composition incorporating a dichroic dye with a phenyl group substituted at the 3-, 4-, and 5-positions of an anthraquinone skeleton, combined with liquid crystalline substituents, which increases the order parameter and solubility without compromising light resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If anthraquinone dyes are used to achieve high light resistance, then light resistance is improved, but solubility in host liquid crystal deteriorates

Engineering Contradiction:
Improvelight resistanceVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent applies local quality by introducing liquid crystalline substituents at specific positions (R1-R7) on the anthraquinone dye molecule. These substituents are strategically placed to enhance solubility in the liquid crystal host without compromising the core anthraquinone structure that provides light resistance. The substituent structure is designed with specific molecular weight and polarity characteristics to optimize local interaction with the liquid crystal matrix.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates a composite molecular structure by combining the anthraquinone core with liquid crystalline substituent groups. This composite approach results in a dichroic dye that exhibits both the high light resistance of anthraquinone and the enhanced solubility characteristics of liquid crystalline materials. The composite structure allows the dye to function effectively as both a coloring agent and a liquid crystal modifier.

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If liquid crystalline substituent is introduced to increase solubility, then solubility is improved, but order parameter deteriorates

Engineering Contradiction:
ImprovesolubilityVSAvoidorder parameter
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by carefully controlling the molecular weight, polarity, and structural characteristics of the liquid crystalline substituents. The substituent parameters are optimized to achieve a balance: they are large enough to enhance solubility through improved compatibility with the liquid crystal host, but structured in a way that maintains the overall molecular anisotropy and ordering of the liquid crystal phase. The substituent design includes specific alkyl chain lengths and aromatic group configurations that preserve liquid crystal ordering.

Inventive Principle:
Principle #35Parameter changes

3Quantity of substance

If dichroic dye concentration is increased to improve coloring, then coloring performance is improved, but viscosity increases

Engineering Contradiction:
Improvedichroic dye concentrationVSAvoidviscosity
Core Design Contradiction:
Quantity of substanceVSForce

Solution Approach 1:

The patent applies local quality by designing the dichroic dye molecule with specific local structural features that prevent aggregation. The liquid crystalline substituents are positioned to create steric hindrance and maintain molecular spacing, while the core anthraquinone structure provides the necessary optical properties. This local structural optimization allows higher dye concentrations without proportional increases in viscosity.

Inventive Principle:
Principle #3Local quality

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 solution enhances the solubility and order parameter of the dichroic dye, suppressing viscosity increase even at high concentrations, and maintains high light resistance, suitable for use in liquid crystal devices.

Implementation Method 1

In guest-host type liquid crystal devices, a dichroic dye is dissolved in a liquid crystal, and coloring and decoloring are switched by change in alignment of the dichroic dye synchronized with the movement of the liquid crystal due to an electric field

Methodology Applied
Scientific EffectGuest-host effect:

Implementation Method 2

a dichroic dye is dissolved in a liquid crystal, and coloring and decoloring are switched by change in alignment of the dichroic dye

Methodology Applied
Scientific EffectDichroism: Dichroic Filter

Data Source

PatentUS7722784B2Liquid crystal composition, liquid crystal device, reflection display material, light modulating material, and anthraquinone compound
Publication Date: 2010.05.25 FUJIFILM CORP
  • US7722784B2 patent drawing
  • US7722784B2 patent drawing
  • US7722784B2 patent drawing

AI summary

The liquid crystal composition of the present invention contains a compound represented by the following Formula (1) and a liquid crystal. In Formula (1), at least one among R1 to R7 is a liquid crystalline substituent, and those among R1 to R7 that are not a liquid crystalline substituent each independently represent a hydrogen atom or a substituent. X and Y each independently represent an alkyl group, a halogen atom, an alkoxy group, or an alkylthio group. Z represents an alkyl group having 3 or more carbon atoms, an acyl group, or an aryl group. A represents an oxygen atom, a sulfur atom, or a nitrogen atom. n represents 0 or 1. The liquid crystal device, reflection display material, and light modulating material of the invention contain the liquid crystal composition.