Red-Emitting Organic Compound for OLEDs

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Solution Overview

Problem

Existing organic electroluminescence elements lack compounds that emit light in the red region with high luminous efficiency and good sublimability, as compounds with high emission intensity often suffer from poor sublimation due to high planarity and symmetry, and those emitting in the red region have weak emission intensity.

Innovation Solution

An organic compound with a specific basic skeleton that emits light in the red region, characterized by a narrow band gap and deep Lowest Unoccupied Molecular Orbital (LUMO) level, is synthesized using a reaction scheme involving diketone, acetone, fluoranthenyl amine, and fluoranthenyl boronic acid ester derivatives, with substituents like phenyl groups to suppress concentration quenching and enhance sublimability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If compounds with high emission intensity are used, then light emission performance is improved, but sublimability deteriorates due to high planarity and symmetry

Engineering Contradiction:
Improveemission intensityVSAvoidsublimability
Core Design Contradiction:
Illumination intensityVSEase of manufacture

Solution Approach 1:

The patent introduces asymmetric substituents (such as phenyl groups at specific positions) on the fluoranthenyl core structure to break the high symmetry of the base compound. This asymmetry reduces intermolecular interactions while maintaining red-region emission, thereby improving sublimability without sacrificing emission intensity

Inventive Principle:
Principle #4Asymmetry

Solution Approach 2:

The patent applies specific substituents at strategically selected positions on the molecular structure to locally modify intermolecular interaction characteristics. This localized modification allows the compound to maintain good sublimability in specific regions while preserving overall emission properties

Inventive Principle:
Principle #3Local quality

2Illumination intensity

If compounds with high planarity and symmetry are used, then emission intensity is improved, but sublimation performance deteriorates

Engineering Contradiction:
Improveemission intensityVSAvoidsublimation performance
Core Design Contradiction:
Illumination intensityVSStability of the object's composition

Solution Approach 1:

The patent strategically introduces asymmetric substituents on the fluoranthenyl core to reduce molecular symmetry, which decreases intermolecular stacking interactions and improves sublimation performance while maintaining the compound's red-region emission capability

Inventive Principle:
Principle #4Asymmetry

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 red light emission with high quantum yield and good sublimability without decomposition, enabling the production of organic electroluminescence elements with high luminous efficiency and durability.

Implementation Method 1

Electrons and holes are injected from the pair of electrodes to generate excitons of a light-emitting organic compound in the organic compound layer, so that the organic electroluminescence elements emit light when the excitons are returned to the ground state

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Implementation Method 2

the organic compound according to the present invention has good sublimability

Methodology Applied
Scientific EffectSublimation: Sublimation

Data Source

PatentEP2665691B1Organic compound, organic electroluminescence element, and image display device
Publication Date: 2020.02.12 CANON KK
  • EP2665691B1 patent drawingFigure 1
  • EP2665691B1 patent drawing
  • EP2665691B1 patent drawing

AI summary

The present invention provides an organic electroluminescence element having a high luminous efficiency. An organic electroluminescence element includes an anode, a cathode, and at least one organic compound layer disposed between the anode and the cathode, wherein at least one of the at least one the organic compound layer contains an organic compound shown in Claim 1.