Imidazole Compounds for OLED Host Materials

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Solution Overview

Problem

There is a need for new hole transport materials, electron/exciton blocker materials, and matrix materials for organic light-emitting diodes (OLEDs) that provide improved efficiency, stability, and spectral characteristics, particularly for devices with phosphorescence emitters like green or blue emitters, while maintaining low operational voltage and long operational lifetimes.

Innovation Solution

The development of specific compounds of formula II', which can be used as host materials, hole transport layers, emitting layers, or electron blocking layers in OLEDs, incorporating arylen and heteroarylen groups that enhance charge carrier conductivity and compatibility with phosphorescent emitters, thereby improving the performance and stability of OLEDs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional hole transport materials are used in OLEDs, then the device can operate, but the efficiency and stability are insufficient

Engineering Contradiction:
ImprovestabilityVSAvoidefficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent modifies the molecular structure of hole transport materials by introducing specific substituents (R1-R6) at defined positions on the imidazo[1,2-a]imidazole core, changing chemical parameters to simultaneously improve efficiency and stability. The systematic variation of substituents allows optimization of both performance metrics without compromising either.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining the imidazo[1,2-a]imidazole core with various aromatic substituents (aryl and heteroarylen groups). This composite approach allows the material to exhibit both high efficiency and stability by integrating complementary properties from different molecular components.

Inventive Principle:
Principle #40Composite materials

2Reliability

If different materials are used for hole/exciton blocker and matrix material, then functional performance can be optimized, but the production process becomes more complex

Engineering Contradiction:
Improvefunctional performanceVSAvoidproduction process complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent designs compound formula II' to perform multiple functions simultaneously: it serves as both the hole/exciton blocker and the matrix material in the OLED light-emitting layer. This multi-functionality simplifies the production process by reducing the number of different materials that need to be handled, deposited, and integrated, while maintaining optimized functional performance.

Inventive Principle:
Principle #6Universality (Multi-functionality)

3Illumination intensity

If phosphorescence emitters like green or blue emitters are used, then spectral characteristics are improved, but operational lifetime decreases

Engineering Contradiction:
Improvespectral characteristicsVSAvoidoperational lifetime
Core Design Contradiction:
Illumination intensityVSDuration of action of stationary object

Solution Approach 1:

The compound of formula II' acts as an intermediary host material that mediates between the phosphorescence emitter and the device structure. It provides a stable environment for the phosphorescence emitter to operate, protecting it from degradation while maintaining the desired spectral characteristics. The host-guest interaction allows the phosphorescence emitter to function at optimal performance without direct exposure to harsh conditions.

Inventive Principle:
Principle #24Intermediary (Mediator)

Data Source

PatentEP3640252B14h-imidazo[1,2-a]imidazoles for electronic applications
Publication Date: 2022.03.16 UDC IRELAND
  • EP3640252B1 patent drawing
  • EP3640252B1 patent drawing
  • EP3640252B1 patent drawing

AI summary

The present invention relates to compounds of formula (I), a process for their production and their use in electronic devices, especially electroluminescent devices. When used as host material for phosphorescent emitters in electroluminescent devices, the compounds of formula (I) may provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.