Dibenzothiophene Liquid Crystal Compounds with Flexible Side Chains

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Solution Overview

Problem

Existing liquid crystal compounds with rigid dibenzothiophene rings have high dielectric anisotropy and birefringence but poor solubility and are prone to crystallization at low temperatures, limiting their application in display devices.

Innovation Solution

A new liquid crystal compound is developed with cyclopropyl, cyclopentyl, or 2-tetrahydrofuryl groups as chain end groups, enhancing solubility and stability by incorporating these groups into the dibenzothiophene-class molecules, which improves low-temperature stability and expands application ranges.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If rigid dibenzothiophene ring structure is used in liquid crystal compounds, then dielectric anisotropy and birefringence are improved, but solubility deteriorates and crystallization occurs at low temperatures

Engineering Contradiction:
Improvedielectric anisotropyVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The rigid dibenzothiophene core is segmented by introducing flexible side chains at positions 2 and 6, creating a molecular structure where the rigid core provides optical properties while the flexible chains provide solubility. This segmentation allows independent optimization of different molecular regions for conflicting properties.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Different regions of the molecule are assigned different properties: the central dibenzothiophene ring provides high dielectric anisotropy and birefringence, while the terminal alkyl or alkoxy groups provide flexibility and solubility. This local differentiation resolves the contradiction between rigid core benefits and overall molecular solubility.

Inventive Principle:
Principle #3Local quality

2Reliability

If rigid dibenzothiophene ring structure is used in liquid crystal compounds, then dielectric anisotropy and birefringence are improved, but low-temperature stability deteriorates due to crystallization

Engineering Contradiction:
ImprovebirefringenceVSAvoidlow-temperature stability
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The molecule is divided into a rigid dibenzothiophene core for optical properties and flexible terminal chains for thermal stability. This segmentation prevents crystallization at low temperatures while maintaining high birefringence, extending the liquid crystal phase temperature range.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

By changing the length and type of side chains (alkyl vs alkoxy, different carbon numbers), the patent optimizes the liquid crystal phase stability at low temperatures while preserving the core's optical anisotropy properties. This parameter adjustment resolves the temperature stability issue.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If rigid dibenzothiophene ring structure is used in liquid crystal compounds, then optical anisotropy is improved, but ease of manufacture deteriorates due to poor solubility

Engineering Contradiction:
Improveoptical anisotropyVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The terminal groups are designed with specific local qualities (alkoxy vs alkyl, different chain lengths) to enhance solubility without affecting the core's optical properties. This local modification makes the compounds easier to handle and process during manufacturing while maintaining high optical anisotropy.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

By adjusting parameters such as side chain length and composition, the patent optimizes both optical performance and manufacturability. The flexible chains improve solubility for easier processing while the rigid core maintains high optical anisotropy, resolving the manufacturing difficulty.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3670503B1Compound, liquid crystal medium containing same, and use thereof
Publication Date: 2023.10.18 SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
  • EP3670503B1 patent drawingFigure 1
  • EP3670503B1 patent drawing
  • EP3670503B1 patent drawing

AI summary

The present invention discloses a compound of which a structural formula thereof is represented as the following formula I: The compound disclosed by the present invention can be used as a liquid crystal compound and overcomes the problem that solubility of the traditional dibenzothiophene-class liquid crystals is poor, and thus can be better applied to the liquid crystal material field. The present invention further discloses a liquid crystal medium containing the compound and an application thereof.