Phenazine Electrochromic Compound for Full-Color Displays

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Solution Overview

Problem

Existing electrochromic materials lack an absorption peak in the wavelength region of 540 nm or more in their colored state, limiting their application in full-color displays and other applications requiring various color tones.

Innovation Solution

An organic compound with a phenazine derivative structure, featuring alkoxy or aryloxy groups as substituents at specific positions, which shifts the absorption peak to 540 nm or more in the colored state while maintaining high transparency in the neutral state through steric hindrance and electronic interactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing electrochromic materials are used, then the basic electrochromic function is achieved, but the absorption peak does not extend to 540 nm or more in the colored state, limiting color tone variety

Engineering Contradiction:
Improvecolor tone varietyVSAvoidabsorption wavelength range
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent modifies the molecular structure parameters of the phenazine derivative by introducing specific substituents (alkoxy groups at positions 2 and 7, aryloxy groups at positions 3 and 6) to shift the absorption peak wavelength from below 540 nm to 540 nm or more in the colored state, thereby expanding the color tone variety while maintaining electrochromic functionality

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure by combining the phenazine core with multiple different substituent groups (alkoxy and aryloxy groups) at specific positions, resulting in a compound that achieves both the desired long-wavelength absorption and high transparency properties

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If the conjugation length is increased to shift absorption to visible region, then the compound is colored by oxidation or reduction, but the absorption peak does not reach 540 nm or more

Engineering Contradiction:
Improveabsorption wavelengthVSAvoidcolor application range
Core Design Contradiction:
Illumination intensityVSAdaptability or versatility

Solution Approach 1:

The patent optimizes the conjugation length parameter by strategic substitution on the phenazine ring, achieving a balanced conjugation system that produces absorption peaks at 540 nm or more in the colored state, enabling full-color display applications

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If materials with various color tones are developed, then full-color displays and broad applications become possible, but existing materials lack absorption peaks in the 540 nm or more region

Engineering Contradiction:
Improveapplication rangeVSAvoidabsorption peak position
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent precisely controls the absorption peak position parameter through systematic modification of the phenazine derivative structure, specifically introducing alkoxy groups at positions 2 and 7 and aryloxy groups at positions 3 and 6, which shifts the absorption peak to 540 nm or more in the colored state while maintaining high transparency in the neutral state, thereby enabling broad application range including full-color displays

Inventive Principle:
Principle #35Parameter changes

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 compound achieves a long-wavelength absorption peak in the colored state and improved transparency in the neutral state, enabling broader applications in displays and optical filters.

Implementation Method 1

an electrochromic property in which the optical absorption property (such as a coloration state and/or an optical transmittance) is changed by an electrochemical oxidation-reduction reaction

Methodology Applied
Scientific EffectElectrochemical oxidation-reduction reaction: Redox Reactions

Implementation Method 2

by oxidation in the case of an anodic EC compound or by reduction in the case of a cathodic EC compound, the conjugation length of the above compound is increased as compared to that thereof obtained before oxidation or reduction is performed, so that the wavelength region at which light is absorbed is shifted to a visible light region

Methodology Applied
Scientific EffectConjugation length change:

Data Source

PatentUS11319483B2Organic compound, electrochromic element containing the same, optical filter, lens unit, imaging device, and window material
Publication Date: 2022.05.03 CANON KK
  • US11319483B2 patent drawing
  • US11319483B2 patent drawing
  • US11319483B2 patent drawing

AI summary

An organic compound represented by the following general formula is provided.In the above formula (1), R11 to R15 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an acyl group, or a halogen atom provided that at least one of R11, R13, and R15 represents the alkoxy group or the aryloxy group; and R11 to R15 may form a ring structure therebetween. R5 and R6 each independently represent an alkyl group, an aryl group, or an aralkyl group. In addition, R21 to R24 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an acyl group, or a halogen atom and may form a ring structure therebetween. The above groups except the acyl group may be substituted when necessary.