Dihydroquinoline Photochromic Compounds for Dichroic Performance

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Solution Overview

Problem

Existing photochromic compounds do not meet the desired performance standards in terms of photochromic properties and dichroic properties, such as fade rate, change in optical density, sensitivity, and absorption ratio, and there is a need for compounds with improved characteristics.

Innovation Solution

Development of photochromic compounds with a dihydroquinoline core structure represented by Formulas (Ia) and (IIa), incorporating various substituents such as aryl, heteroaryl, and linking groups to enhance photochromic and dichroic properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing photochromic compounds are used, then the basic photochromic function is provided, but the photochromic properties and dichroic properties do not meet desired performance standards

Engineering Contradiction:
Improvephotochromic properties and dichroic propertiesVSAvoidperformance standards compliance
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by systematically varying the chemical structure parameters of photochromic compounds, specifically modifying the dihydroquinoline core structure with different substituents (aryl, heteroaryl groups) and linking groups to optimize photochromic and dichroic properties. This includes changing molecular weight, substituent positions, and chemical composition to achieve desired fade rates, optical density changes, and absorption ratios

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by creating photochromic compounds that integrate multiple functional groups and structural elements within a single molecular framework. The dihydroquinoline core is combined with various aryl and heteroaryl substituents to produce a composite molecular structure that simultaneously provides both photochromic and dichroic properties, achieving enhanced performance in eyewear lenses

Inventive Principle:
Principle #40Composite materials

2Reliability

If photochromic compounds with improved properties are developed, then photochromic and dichroic properties are enhanced, but the complexity of compound structure increases

Engineering Contradiction:
Improvephotochromic and dichroic propertiesVSAvoidcompound structure
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the photochromic compound into distinct functional modules: a dihydroquinoline core structure, various aryl substituents, heteroaryl groups, and linking groups. This modular approach allows systematic optimization of photochromic and dichroic properties while maintaining structural organization and facilitating selective modification of specific functional regions

Inventive Principle:
Principle #1Segmentation

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 photochromic compounds exhibit improved photochromic properties and dichroic properties, including enhanced fade rate, optical density change, sensitivity, and absorption ratio, making them suitable for applications in eyewear lenses and other optical devices.

Implementation Method 1

Photochromic compounds and materials, in response to certain wavelengths of electromagnetic radiation (or 'actinic radiation'), typically undergo a transformation from one form or state to another form, with each form having a characteristic or distinguishable absorption spectrum associated therewith.

Methodology Applied
Scientific EffectPhotochromism: Photochromism

Implementation Method 2

the efficiency at which the photochromic compound absorbs radiation required to activate the photochromic compound (sometimes designated as chromaticity)

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

Data Source

PatentUS12404448B2Dihydroquinoline photochromic compounds
Publication Date: 2025.09.02 TRANSITIONS OPTICAL INC
  • US12404448B2 patent drawing
  • US12404448B2 patent drawing
  • US12404448B2 patent drawing

AI summary

The present invention relates to a photochromic compound having a core fused ring structure represented by at least one of the following Formula (Ia) or Formula (IIa), (Ia) (IIa) Independently for each of Formula (Ia) and Formula (IIa): R1 is in each case independently selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —SO2R5, or —C(O)—XR5, where, X is selected from a single bond, —N(R5)—, or —O—, and R5 in each case is independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and B and B′ are each independently selected from substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. The present invention also relates to photochromic compositions and articles including such photochromic compounds.