Electrochromic Organic Compound Stabilizing Absorption Spectrum

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Solution Overview

Problem

Existing electrochromic (EC) compounds exhibit significant temperature dependency in their absorption spectra, leading to unstable coloration and low absorbance, which limits their application in full-color displays and other uses.

Innovation Solution

An organic EC compound with a bulky structure composed of three aromatic rings, specifically denoted by general formula [1], is developed, which reduces the formation of associates and maintains the absorption spectrum primarily of monomers, thereby minimizing temperature-dependent changes and enhancing absorbance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If conventional cathodic EC compounds (viologen derivatives) are used, then the device can achieve electrochromic functionality, but the absorption spectrum changes significantly with temperature

Engineering Contradiction:
Improveabsorption spectrum stabilityVSAvoidtemperature dependency
Core Design Contradiction:
Stability of the object's compositionVSTemperature

Solution Approach 1:

The patent modifies molecular parameters by introducing bulky substituents (tetrafluorophenyl groups) at positions 2 and 6 of the pyridine rings. This structural parameter change increases steric hindrance, preventing associate formation and stabilizing the absorption spectrum against temperature variations.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining a bipyridinium core with bulky aromatic substituents. This composite structure leverages the electrochromic properties of the viologen core while the aromatic substituents provide steric protection against temperature-induced spectral shifts.

Inventive Principle:
Principle #40Composite materials

2Temperature

If compounds with extended conjugate structures are used to shift absorption wavelength, then the absorption wavelength increases, but the oscillator strength decreases leading to low absorbance

Engineering Contradiction:
Improveabsorption wavelengthVSAvoidabsorbance
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent applies local quality modification by placing electron-withdrawing fluorine atoms at specific positions (2 and 6) of the pyridine rings. This localized substitution enhances the electron deficiency of the pyridine rings, increasing oscillator strength and absorbance without extending the conjugate system.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent changes electronic parameters by introducing fluorine substituents that modify the electron distribution and HOMO-LUMO gap. This parameter change increases the molar extinction coefficient, thereby improving absorbance while maintaining the absorption wavelength in the desired range.

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 stable absorption spectrum with low temperature dependency and high absorbance, suitable for use in electrochromic devices, optical filters, and image pickup apparatuses, providing improved optical density and reduced transmittance.

Implementation Method 1

The electrochromic layer contains an electrochromic compound in which optical absorption properties (coloration state and optical transmittance) of a substance change due to an electrochemical oxidation-reduction reaction

Methodology Applied
Scientific EffectElectrochemical oxidation-reduction reaction: Redox Reactions

Implementation Method 2

EC materials are required that the light absorption wavelength (form of absorption spectrum) does not change greatly in accordance with the temperature during use

Methodology Applied
Scientific EffectAbsorption spectroscopy: Absorption Spectroscopy

Data Source

PatentUS11104844B2Organic compound, electrochromic device, optical filter, image pickup apparatus, window, and electrochromic mirror
Publication Date: 2021.08.31 CANON KK
  • US11104844B2 patent drawing
  • US11104844B2 patent drawing
  • US11104844B2 patent drawing

AI summary

An organic compound denoted by formula [1],where each of X1 and X2 is independently selected from an alkyl group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, each of R11 to R20 is independently selected from a hydrogen atom and a substituent, Y represents an alkyl group optionally having a substituent or an aryl group optionally having a substituent, and each of A1− and A2− independently represents a monovalent anion.