OLED Iridium Compound Ligands for Quantum Yield and Sublimability

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Solution Overview

Problem

Existing organic compounds used in organic light-emitting elements, such as compound 1-a, have room for improvement in light-emitting properties, particularly in terms of quantum yield and sublimability, which affect the efficiency and durability of the elements.

Innovation Solution

The development of an organic compound with a tetrahydropyrene skeleton in its ligands, which enhances quantum yield and sublimability by maintaining sufficient metal-to-ligand charge transfer (MLCT) transitions and reducing ligand aggregation, respectively.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If conventional organic compounds are used in organic light-emitting elements, then the elements can be manufactured, but the quantum yield and light emission efficiency are insufficient

Engineering Contradiction:
Improvequantum yieldVSAvoidlight emission efficiency
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent modifies the molecular structure parameters of the organic compound by introducing a tetrahydropyrene skeleton and specific substituent groups (R1-R49) at defined positions. This structural parameter change optimizes the HOMO and LUMO energy levels, thereby improving quantum yield and light emission efficiency simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining the tetrahydropyrene core with specific ligand systems (L and L′) coordinated to a metal center (M). This composite structure leverages the synergistic effects of the rigid tetrahydropyrene framework and the functional ligands to achieve high quantum yield and efficiency

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional organic compounds are used, then the elements can operate, but the sublimability and durability are insufficient

Engineering Contradiction:
ImprovedurabilityVSAvoidsublimability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent optimizes molecular weight and structural parameters by selecting specific substituent groups (R1-R49) and their positions on the tetrahydropyrene skeleton. This achieves an optimal balance between sublimability (requiring moderate molecular weight) and durability (requiring stable molecular structure), enabling both ease of manufacture and reliable operation

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If the ligand structure is simplified, then the manufacturing is easier, but the quantum yield decreases

Engineering Contradiction:
Improvestructural complexityVSAvoidquantum yield
Core Design Contradiction:
Ease of manufactureVSUse of energy by moving object

Solution Approach 1:

The patent divides the ligand system into distinct functional segments: the tetrahydropyrene core (providing structural stability and controlling sublimability) and the coordinated ligands L and L′ (providing electronic properties and quantum yield). This segmentation allows independent optimization of each component for both manufacturability and performance

Inventive Principle:
Principle #1Segmentation

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 exhibits high quantum yield and sublimability, leading to improved light emission efficiency and durability of the organic light-emitting elements, suitable for visible light emission in the green to red region, suitable for image display devices.

Implementation Method 1

maintaining sufficient metal-to-ligand charge transfer (MLCT) transitions

Methodology Applied
Scientific EffectMetal-to-ligand charge transfer (MLCT):

Implementation Method 2

By injecting electrons and holes through the pair of electrodes, excitons of a luminescent organic compound in the organic compound layer are generated. The organic light-emitting element emits light when the excitons return to their ground state.

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS12565512B2Organic compound, organic light-emitting element, display apparatus, photoelectric conversion apparatus, electronic apparatus, illumination apparatus, moving object, and exposure light source
Publication Date: 2026.03.03 CANON KK
  • US12565512B2 patent drawing
  • US12565512B2 patent drawing
  • US12565512B2 patent drawing

AI summary

An organic compound is represented by formula [1]. In formula [1], L and L′ are bidentate ligands different from each other, a partial structure IrLm is a partial structure represented by formula [2], and a partial structure IrL′n is a partial structure represented by formula [3-1] or formula [3-2].