Electrochromic Polycyclic Compounds for Ophthalmic Lenses

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Solution Overview

Problem

Current electrochromic compounds used in ophthalmic lenses face challenges in achieving a wide range of neutral colors, particularly blue to green, red, orange, and yellow, with compatibility issues among different compounds, and limited stability and solubility in conventional solvents.

Innovation Solution

Development of novel electrochromic polycyclic compounds with a five, six, or seven-membered ring containing at least two nitrogen atoms, incorporating an azine ring or azine moiety, which are colorless in the inactive state and colored in the activated state, with specific electrochemical properties and stability, allowing for a range of colors and improved compatibility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If multiple different electrochromic compounds are mixed to achieve a wide range of neutral colors, then the color range is improved, but the compatibility and stability of the composition deteriorates

Engineering Contradiction:
Improvecolor rangeVSAvoidcompatibility and stability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent divides the electrochromic system into multiple compound classes (oxidizing compounds and reducing compounds) with distinct functional roles. Each class is further segmented into specific compounds with controlled redox potentials, allowing independent optimization of color properties while maintaining overall system stability through structured compatibility rules.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent systematically varies the redox potential parameter across different electrochromic compounds to achieve desired color ranges. By controlling the redox potential differences between compounds (e.g., ensuring at least 0.1V difference between adjacent compounds in the sequence), the invention enables wide color coverage while maintaining compatibility through quantifiable parameter relationships.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If viologen compounds are used to achieve high molar absorption coefficient, then the absorption performance is improved, but the compatibility with other electrochromic compounds and long-term stability deteriorates

Engineering Contradiction:
Improvemolar absorption coefficientVSAvoidcompatibility and long-term stability
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent creates a universal electrochromic composition framework that can accommodate multiple compound types (viologens, phenazines, dihydrophenazines, etc.) within a single system. The composition is designed to work with both oxidizing and reducing compounds, allowing high absorption coefficient compounds like viologens to be used while maintaining overall system stability through the multi-functional design of the electrochromic device.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent introduces intermediary compounds with intermediate redox potentials that act as mediators between high-absorption compounds like viologens and other electrochromic materials. These intermediary compounds facilitate compatible electron transfer processes and prevent direct incompatible interactions between compounds with vastly different redox potentials, thereby maintaining long-term stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Speed

If electrochromic compounds are designed for fast colouring and fading rates, then the response speed is improved, but the long-term stability in the presence of oxygen deteriorates

Engineering Contradiction:
Improvecolouring and fading ratesVSAvoidlong-term stability
Core Design Contradiction:
SpeedVSReliability

Solution Approach 1:

The patent employs composite electrochromic compositions combining multiple compounds with complementary properties. Fast-response compounds (such as viologens with high absorption coefficients) are combined with more stable compounds that have good oxygen resistance. The composite structure allows the fast-response components to provide rapid coloration while the stable components maintain long-term durability and resistance to degradation by oxygen.

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 new compounds provide a broader range of colors, enhanced stability, and improved solubility, enabling the creation of high-quality ophthalmic lenses with desired tint options while maintaining long-term stability and compatibility.

Implementation Method 1

Electrochromism is a well-known physical phenomenon which is observed with certain classes of chemical compounds that reversibly change colour when a voltage is applied to them. The material undergoes reversible changes in optical properties by oxidation and reduction.

Methodology Applied
Scientific EffectElectrochromism: Electrochromism

Implementation Method 2

The material undergoes reversible changes in optical properties by oxidation and reduction.

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 3

The material undergoes reversible changes in optical properties by oxidation and reduction.

Methodology Applied
Scientific EffectReduction: Reduction

Data Source

PatentEP4461783A1Electrochromic compounds, compositions and optical articles containing them
Publication Date: 2024.11.13 ESSILOR INTERNATIONAL(COMPAGNIE GENERALE D OPTIQUE)
  • EP4461783A1 patent drawing
  • EP4461783A1 patent drawing
  • EP4461783A1 patent drawing

AI summary

The invention relates to a group of novel electrochromic compounds. More specifically, it relates to electrochromic polycyclic compounds comprising a five, six or seven-membered ring, wherein said polycyclic compounds contain at least two nitrogen atoms in their cyclic central core. It also relates to the use of these compounds as a variable transmittance medium for the manufacture of an optical article, such as an ophthalmic lens.