Hydrazone Polymerizable Compound UV Stability

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing methods for producing polymerizable compounds with a hydrazone and benzothiazole moiety suffer from discoloration and reduction in aligning property when exposed to ultraviolet light, affecting the quality of liquid crystal displays.

Innovation Solution

A method involving the reaction of specific compounds represented by General Formula (I-B-a) and (I-B-b) in the presence of a base, with controlled reaction conditions and solvents, to produce a polymerizable compound that maintains stability under UV light exposure.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If a polymerizable compound with a hydrazone moiety and benzothiazole moiety is produced using conventional methods (reacting 2-hydrazino-benzothiazole with alkyl halide in the presence of a base), then the yield and ease of synthesis are improved, but discoloration and reduction of aligning property occur when the retardation film is irradiated with ultraviolet light for a long period

Engineering Contradiction:
Improveease of synthesisVSAvoidaligning property stability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of the polymerizable compound by introducing specific substituents (aromatic hydrocarbon groups, heterocyclic groups) at defined positions on the benzothiazole and hydrazone moieties. This structural modification resolves the contradiction by maintaining ease of synthesis through conventional coupling reactions while dramatically improving UV light resistance and aligning property stability, eliminating the discoloration problem of prior art compounds.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining multiple functional moieties (benzothiazole, hydrazone, aromatic hydrocarbon groups, heterocyclic groups, and polymerizable groups) into a single integrated compound. This composite structure achieves both the desired ease of manufacture through modular synthesis and superior reliability under UV irradiation, as the various moieties work synergistically to prevent discoloration while maintaining aligning properties.

Inventive Principle:
Principle #40Composite materials

2Productivity

If a polymerizable compound with a hydrazone moiety and benzothiazole moiety is produced using conventional methods, then productivity is improved, but discoloration occurs and aligning property is reduced when the film is irradiated with ultraviolet light

Engineering Contradiction:
ImproveproductivityVSAvoiddiscoloration
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical parameters of the polymerizable compound by incorporating specific aromatic hydrocarbon groups and heterocyclic groups at defined positions. This structural change maintains high productivity through efficient conventional synthesis methods while eliminating the harmful discoloration effect under UV irradiation, as the modified structure is inherently more resistant to photodegradation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the potential harm of UV irradiation-induced discoloration into a benefit by designing a molecular structure that is inherently resistant to UV degradation. The specific arrangement of aromatic hydrocarbon groups, heterocyclic groups, and the hydrazone-benzothiazole core creates a stable structure that not only prevents discoloration but also enhances overall compound stability, turning the challenge of UV resistance into a design advantage.

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

3Ease of manufacture

If a polymerizable compound with a hydrazone moiety and benzothiazole moiety is produced using conventional methods, then ease of synthesis is improved, but the quality of display products is greatly reduced due to unevenness in brightness and unnatural colors

Engineering Contradiction:
Improveease of synthesisVSAvoiddisplay quality
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent changes the structural parameters of the polymerizable compound by introducing specific aromatic hydrocarbon groups and heterocyclic groups at defined positions on the molecular framework. This modification maintains ease of synthesis through conventional coupling reactions while dramatically improving display quality by preventing the brightness unevenness and color distortion problems that occur with conventional compounds under UV irradiation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent designs a composite molecular structure integrating multiple functional groups (benzothiazole, hydrazone, aromatic hydrocarbon groups, heterocyclic groups, and polymerizable groups) that work synergistically. This composite approach preserves the ease of synthesis through modular construction while ensuring high manufacturing precision in display products by eliminating optical defects such as brightness unevenness and color distortion.

Inventive Principle:
Principle #40Composite materials

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 produced polymerizable compound prevents discoloration and maintains aligning property stability when irradiated with UV light, enhancing the quality of optical materials like optical compensation films.

Implementation Method 1

when the optically anisotropic body using the polymerizable liquid crystal composition is irradiated with ultraviolet light for a long period, discoloration does not easily occur

Methodology Applied
Scientific EffectAbsorption (EM radiation): Absorption (EM radiation)

Implementation Method 2

a polymer having uniform alignment by aligning a polymerizable composition including a polymerizable compound in a liquid crystal state and then carrying out polymerization

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Data Source

PatentUS10927087B2Method for producing polymerizable compound
Publication Date: 2021.02.23 SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
  • US10927087B2 patent drawing
  • US10927087B2 patent drawing
  • US10927087B2 patent drawing

AI summary

The polymerizable compound has a hydrazone moiety. The present invention also provides a polymerizable composition in which discoloration and reduction of aligning property do not easily occur. Furthermore, the present invention provides a polymer obtained by polymerizing a polymerizable composition containing a compound obtained by the production method and an optically anisotropic body using the polymer. The present invention provides a method for producing a polymerizable compound including a step of reacting a compound represented by General Formula (I-B-a) with a compound represented by General Formula (I-B-b) to obtain a compound represented by General Formula (I-C), and provides a composition which contains a compound obtained by this production method.