Perylene Dye Compounds for Electrowetting Photo-Stability

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Solution Overview

Problem

Existing electrowetting display devices face challenges in achieving photo-stability and suitable color properties for their dye compounds, which affect the display quality and longevity due to degradation from ultraviolet light exposure.

Innovation Solution

Development of new dye compounds with a perylene backbone molecular structure or derivatives of thioxanthene, where the S atom is replaced with N or O, offering improved photo-stability and tunable color options by incorporating specific alkyl, aryl, and other functional groups, enhancing their performance in electrowetting elements.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing dye compounds are used in electrowetting display devices, then the device can operate with basic color display, but the dye degrades under ultraviolet light exposure leading to poor photo-stability and reduced display longevity

Engineering Contradiction:
Improvephoto-stabilityVSAvoiddisplay longevity
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent applies parameter changes by modifying the molecular structure of dye compounds through chemical substitution. Specifically, it replaces hydrogen atoms at the 2 and 7 positions of the perylene backbone with electron-withdrawing groups (such as cyano, carbonyl, or carboxyl groups). This chemical modification changes the electronic parameters of the dye molecule, enhancing its resistance to photo-degradation under ultraviolet light while maintaining its color display functionality, thereby resolving the contradiction between photo-stability and display longevity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by creating hybrid dye molecules that combine the core perylene structure with various functional groups (cyano, carbonyl, carboxyl). This composite approach integrates the beneficial properties of different molecular components: the perylene backbone provides the base color and structural stability, while the attached functional groups enhance photo-stability and tune the optical properties. This composite molecular design directly addresses the degradation issue while preserving display performance.

Inventive Principle:
Principle #40Composite materials

2Reliability

If dye compounds are modified to improve photo-stability, then longevity is enhanced, but the complexity of dye synthesis and selection increases

Engineering Contradiction:
Improvephoto-stabilityVSAvoiddye synthesis complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the dye molecule into distinct functional modules: a core perylene backbone and detachable functional groups at specific positions. This modular segmentation allows independent optimization of each component - the perylene core provides the base color while functional groups can be selectively added to enhance photo-stability. This segmentation simplifies the design process compared to creating entirely new molecular structures, as it involves systematic substitution rather than de novo synthesis.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent uses parameter changes through systematic chemical substitution at defined positions (2 and 7) of the perylene backbone. By focusing modifications on specific positions rather than random structural changes, the synthesis process becomes more predictable and scalable. The electron-withdrawing groups are introduced through standard organic synthesis techniques, making the process manageable. This targeted parameter modification approach balances improved photo-stability with controlled synthesis complexity.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If conventional dye compounds are used, then manufacturing is simpler and cost-effective, but the color properties and switching performance are insufficient for high-quality display

Engineering Contradiction:
Improvemanufacturing simplicityVSAvoidcolor property precision
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent applies local quality by introducing specific functional groups at specific positions (2 and 7) of the perylene backbone. Rather than uniformly modifying the entire molecule, the modification is localized to these particular positions, which are known to affect the HOMO-LUMO gap and thus the color properties. This localized modification approach allows precise tuning of color characteristics while maintaining the overall simplicity of the dye structure and synthesis process.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes through the systematic introduction of electron-withdrawing groups that modify the electronic parameters of the dye molecule. These changes in electronic structure directly influence the absorption spectrum and color properties. By controlling which groups are introduced and at which positions, the patent achieves precise control over color characteristics while using well-established synthetic methods, thus balancing manufacturing simplicity with color property precision.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3397695B1Dye compounds for an electrowetting element
Publication Date: 2021.06.30 AMAZON TECH INC
  • EP3397695B1 patent drawingFigure 1~2
  • EP3397695B1 patent drawingFigure 3
  • EP3397695B1 patent drawing

AI summary

An electrowetting element comprising a first fluid comprising a dye compound having the general formula (A).