Hexaazatriphenylene Organic Compound for Delayed Fluorescence

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Solution Overview

Problem

Existing organic light-emitting elements face challenges in achieving high luminous efficiency due to limitations in the materials used for light-emitting layers.

Innovation Solution

An organic compound represented by formula [1] is introduced, featuring a hexaazatriphenylene skeleton with electron-withdrawing properties and electron-donating substituents, which reduces the energy gap between singlet and triplet states, facilitating delayed fluorescence and improved luminous efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If conventional organic light-emitting materials are used, then the device can emit light, but the luminous efficiency is insufficient

Engineering Contradiction:
Improveluminous efficiencyVSAvoidenergy loss in light emission
Core Design Contradiction:
Use of energy by moving objectVSLoss of energy

Solution Approach 1:

The patent modifies the molecular structure of organic light-emitting materials by introducing specific substituents (formulae [2] to [18]) at defined positions (R1 to R6) on the hexaazatriphenylene core, thereby changing the energy gap between singlet and triplet states to enhance delayed fluorescence and improve luminous efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material design by combining the electron-withdrawing hexaazatriphenylene skeleton with electron-donating substituents (formulae [2] to [18]), creating a push-pull electronic structure that optimizes charge distribution and enhances luminous efficiency through improved exciton management

Inventive Principle:
Principle #40Composite materials

2Duration of action of stationary object

If existing light-emitting materials are used, then the device can operate, but the driving durability is limited

Engineering Contradiction:
Improvedriving durabilityVSAvoidoperational reliability
Core Design Contradiction:
Duration of action of stationary objectVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of the light-emitting material by defining specific substituent positions and types (formulae [2] to [18]) on the hexaazatriphenylene core, which stabilizes the material against degradation and improves both driving durability and operational reliability

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 use of the organic compound in organic light-emitting elements results in high luminous efficiency and superior driving durability, with a small energy difference between singlet and triplet states enabling the utilization of triplet excitons for delayed fluorescence.

Implementation Method 1

the energy gap between a singlet state and a triplet state is small, and thus the delayed fluorescence is enhanced

Methodology Applied
Scientific EffectDelayed fluorescence: Fluorescence

Implementation Method 2

triplet excitons can be utilized for delayed fluorescence emission through reverse intersystem crossing to singlet states

Methodology Applied
Scientific EffectIntersystem crossing:

Data Source

PatentUS12317746B2Organic compound, organic light-emitting element, display apparatus, photoelectric conversion apparatus, electronic apparatus, lighting device, and moving object
Publication Date: 2025.05.27 CANON KK
  • US12317746B2 patent drawing
  • US12317746B2 patent drawing
  • US12317746B2 patent drawing

AI summary

An organic compound represented by formula [1]:where in formula [1], R1 to R6 are each independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, and other substituents having a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, at least one of R1 to R6 is one of the other substituents, at least any one of R1 and R2 is a hydrogen atom or a hydrocarbon group, at least any one of R3 and R4 is a hydrogen atom or a hydrocarbon group, and at least any one of R5 and R6 is a hydrogen atom.