Thermally Stable Organic Compound for Red-Region Photoelectric Conversion

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Solution Overview

Problem

Existing organic photoelectric conversion elements have low photoelectric conversion efficiency in the red region due to limited optical absorption and are prone to thermal degradation, as they typically have absorption bands in shorter wavelengths and low glass transition temperatures.

Innovation Solution

A thermally stable organic compound with an absorption band in the long wavelength region, represented by a specific chemical formula, is developed, featuring an electron-donating skeleton and electron-withdrawing substituents that enhance absorption and stability, allowing for efficient photoelectric conversion across the visible spectrum.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If an organic compound with low molecular weight is used, then the flexibility and ease of processing are improved, but the optical absorption band shifts to shorter wavelengths, reducing photoelectric conversion efficiency in the red region

Engineering Contradiction:
Improveease of processingVSAvoidphotoelectric conversion efficiency
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent changes the molecular structure parameters by introducing specific electron-donating groups (Ar1, Ar2) and electron-withdrawing groups (Q) connected by a conjugated cyclic structure (A). This structural parameter change extends the conjugation length and optimizes the HOMO-LUMO energy gap, shifting the absorption band to longer wavelengths (red region) while maintaining low molecular weight for ease of processing

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining electron-donating aromatic/heteroaromatic groups with electron-withdrawing groups through a conjugated cyclic linker. This composite structure synergistically enhances both the optical absorption in the red region and the overall photoelectric conversion efficiency while keeping the molecule relatively small

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If the glass transition temperature is low, then the flexibility and processability are improved, but the compound is prone to crystallization under thermal load, degrading device performance

Engineering Contradiction:
ImproveflexibilityVSAvoidthermal stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent modifies the molecular parameters by introducing bulky aryl and heteroaryl groups that increase molecular volume and reduce packing efficiency. This structural modification raises the glass transition temperature to 100°C or higher, preventing crystallization under thermal load during device fabrication while maintaining the amorphous state for flexibility

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent designs the organic compound to form a stable amorphous phase that acts as a disposable, non-crystalline matrix. This amorphous structure can be processed once during device fabrication and then remains stable throughout operation, resisting crystallization even under subsequent thermal exposure

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Device complexity

If the absorption band is limited to shorter wavelengths, then the molecular structure is simpler, but the photoelectric conversion efficiency in the red region is low

Engineering Contradiction:
Improvemolecular structure complexityVSAvoidphotoelectric conversion efficiency
Core Design Contradiction:
Device complexityVSProductivity

Solution Approach 1:

The patent optimizes molecular parameters by carefully selecting and positioning electron-donating groups (Ar1, Ar2 with 6-18 carbon atoms) and electron-withdrawing groups (Q) around a central cyclic structure (A). This parameter optimization extends the π-conjugation system to achieve red region absorption without excessive molecular complexity, balancing structure and function

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by placing specific functional groups at strategic positions around the cyclic core structure. The electron-donating and electron-withdrawing groups are positioned to maximize conjugation and charge transfer while maintaining overall molecular symmetry and preventing excessive complexity

Inventive Principle:
Principle #3Local quality

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 organic compound achieves high absorption coefficients and thermal stability, enabling efficient conversion of light into electrical energy across the entire visible spectrum while maintaining performance under high temperatures, thus improving the efficiency and reliability of organic photoelectric conversion elements.

Implementation Method 1

Photoelectric conversion elements are operable to receive external light and convert the energy of the light into electrical energy

Methodology Applied
Scientific EffectPhotoelectric conversion: Photovoltaic Effect

Implementation Method 2

the optical absorption band of an organic compound depends greatly on the size of the molecule of the compound

Methodology Applied
Scientific EffectOptical absorption: Absorption (EM radiation)

Data Source

PatentUS10903433B2Organic compound, and photoelectric conversion element and imaging device using the organic compound
Publication Date: 2021.01.26 CANON KK
  • US10903433B2 patent drawing
  • US10903433B2 patent drawing
  • US10903433B2 patent drawing

AI summary

An organic compound represented by the following formula [1] has a high absorption coefficient in a long wavelength region and is thermally stable.In formula [1], Ar1 and Ar2 each represent a group independently selected from the group consisting of aryl group and heterocyclic groups, and A represents a cyclic structure. m represents an integer of 0 to 2. Q represents a structure represented by one of the following formulas [1-1] and [1-2], wherein n represents an integer of 0 to 2, and when n is 2, the two R4's may be the same as or different from each other, and the two R5's may be the same as or different from each other.