Organometallic Red Emitters Preventing Aggregation in OLEDs

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current organic light emitting devices (OLEDs) face challenges in achieving stable and efficient red emission, with existing compounds often experiencing aggregation and self-quenching issues that affect device lifetime and efficiency.

Innovation Solution

The development of organometallic compounds featuring a phenylquinoline or phenylisoquinoline ligand with a bulky substituent and a two-carbon atom linker, which enhances stability and prevents aggregation, leading to improved red emission characteristics.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional organic emissive materials are used in OLEDs, then the devices can be fabricated with cost advantages and flexibility, but the materials suffer from aggregation and self-quenching issues that reduce device lifetime and efficiency

Engineering Contradiction:
Improvedevice lifetimeVSAvoidaggregation and self-quenching
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent introduces bulky substituents at specific positions on the ligand structure (such as the 6-position of phenylquinoline or phenylisoquinoline) to create localized steric hindrance. This local structural modification prevents aggregation at molecular interfaces while maintaining the overall emissive properties of the material, thereby resolving the self-quenching issue without sacrificing device lifetime

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs organometallic complexes comprising a metal center (such as iridium or platinum) coordinated with specially designed organic ligands featuring bulky substituents. This composite structure combines the photophysical properties of the metal complex with the steric protection of the bulky organic groups, achieving both high efficiency and long device lifetime by preventing aggregation

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If existing red emissive compounds are used, then the OLEDs can achieve red emission, but the compounds exhibit aggregation and self-quenching that affect efficiency and stability

Engineering Contradiction:
Improvered emission efficiencyVSAvoidemission stability
Core Design Contradiction:
Illumination intensityVSStability of the object's composition

Solution Approach 1:

The bulky substituents are pre-installed on the ligand structure before the material is used in the OLED device. This preliminary structural design creates steric barriers that prevent molecular aggregation and self-quenching before they can occur during device operation, thereby maintaining both high emission efficiency and stable composition throughout the device lifetime

Inventive Principle:
Principle #9Preliminary anti-action

Solution Approach 2:

The patent modifies the molecular parameters of the emissive compounds by introducing bulky groups that change the steric parameters and molecular packing characteristics. This parameter change prevents aggregation while maintaining the photophysical parameters necessary for efficient red emission, achieving both high efficiency and stability

Inventive Principle:
Principle #35Parameter changes

3Reliability

If organometallic compounds with bulky substituents are synthesized, then aggregation is prevented and device lifetime is improved, but the synthesis complexity increases

Engineering Contradiction:
Improvedevice lifetimeVSAvoidsynthesis complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The synthesis is divided into discrete, modular steps: first synthesizing the core phenylquinoline or phenylisoquinoline ligand, then introducing the bulky substituent in a separate step, and finally coordinating the metal center. This segmentation of the synthesis process makes the complex molecule accessible through standard organic synthesis techniques, managing synthesis complexity while achieving the desired aggregation prevention

Inventive Principle:
Principle #1Segmentation

4Reliability

If the ligand structure is modified to prevent aggregation, then device lifetime improves, but the evaporation temperature and solubility need to be optimized

Engineering Contradiction:
Improvedevice lifetimeVSAvoidevaporation temperature and solubility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The bulky substituents are specifically designed to modify the physical parameters of the compound. The steric bulk prevents aggregation (improving lifetime) while the chemical nature of the substituent groups (such as alkyl or aryl groups) is selected to optimize solubility in common OLED fabrication solvents and to achieve appropriate evaporation temperatures for vacuum deposition processes

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

These compounds provide stable, narrow, and efficient red emission, increasing device lifetime and efficiency by preventing self-quenching and maintaining red emission properties while improving evaporation temperature and solubility.

Implementation Method 1

These compounds may be used in OLEDs to provide devices with improved lifetime and color. In particular, these compounds may be especially useful as stable, narrow and efficient red emissive compounds.

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Data Source

PatentUS9190621B2Materials for organic light emitting diode
Publication Date: 2015.11.17 UNIVERSAL DISPLAY CORP
  • US9190621B2 patent drawing
  • US9190621B2 patent drawing
  • US9190621B2 patent drawing

AI summary

Organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, via two carbon atoms. These compounds also comprise a substituent other than hydrogen and deuterium on the quinoline, isoquinoline or linker. These compounds may be used as red emitters in phosphorescent OLEDs. In particular, these compounds may provide stable, narrow and efficient red emission.