Hexacyclic Heteroaromatic Compounds for OLEDs

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Solution Overview

Problem

Current organic electroluminescent devices, particularly those exhibiting phosphorescence, face challenges in efficiency, operating voltage, and lifetime, with existing matrix and transport materials lacking in color purity and processability, and requiring improvements for broader temperature range performance.

Innovation Solution

Development of specific heteroaromatic compounds with defined structures that serve as matrix, hole conductor, or electron transport materials, enhancing device efficiency, reducing operating voltage, and improving color purity, while being easily processable and stable over a broad temperature range.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If indolizine derivatives are used as matrix materials, then the device can achieve basic phosphorescent emission, but the lifetime and efficiency of the device are insufficient

Engineering Contradiction:
Improvedevice lifetimeVSAvoiddevice efficiency
Core Design Contradiction:
Duration of action of stationary objectVSReliability

Solution Approach 1:

The patent modifies the molecular structure of indolizine derivatives by introducing additional ring structures (fused rings) to change the physical and chemical parameters of the material. This structural parameter change leads to improved device lifetime and efficiency while maintaining phosphorescent emission properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops composite hexacyclic heteroaromatic compounds that combine multiple structural elements (indolizine core with additional fused rings). These composite structures provide synergistic effects that simultaneously improve both device lifetime and efficiency, resolving the contradiction between these two parameters.

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If conventional matrix materials are used, then the device can operate, but the color purity is insufficient

Engineering Contradiction:
Improvecolor purityVSAvoidmaterial structure complexity
Core Design Contradiction:
Illumination intensityVSDevice complexity

Solution Approach 1:

The patent introduces specific heteroatoms (N, O, S) at particular positions within the hexacyclic structure to locally modify the electronic properties and optical characteristics. This localized structural modification enhances color purity without requiring complete redesign of the entire molecular structure.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The complex hexacyclic structure can be viewed as segmented building blocks (indolizine core plus additional fused rings) that can be systematically designed and assembled. This segmentation approach allows for controlled optimization of color purity while managing structural complexity through modular design.

Inventive Principle:
Principle #1Segmentation

3Power

If existing transport materials are used, then the device can function, but the operating voltage is too high

Engineering Contradiction:
Improveoperating voltageVSAvoidprocessability
Core Design Contradiction:
PowerVSEase of manufacture

Solution Approach 1:

The patent modifies the HOMO-LUMO energy levels and charge transport properties of the matrix materials through structural optimization. By changing molecular parameters such as electron affinity and ionization potential, the device operating voltage is reduced while maintaining good processability through appropriate solvent selection and film formation characteristics.

Inventive Principle:
Principle #35Parameter changes

4Use of energy by moving object

If phosphorescent emitters are used to improve energy efficiency, then the quantum efficiency increases, but the device lifetime decreases

Engineering Contradiction:
Improveenergy efficiencyVSAvoiddevice lifetime
Core Design Contradiction:
Use of energy by moving objectVSDuration of action of stationary object

Solution Approach 1:

The patent uses optimized matrix materials as intermediaries between the phosphorescent emitter and the electrodes. These matrix materials facilitate efficient energy transfer to the emitter while providing stable operational conditions that extend device lifetime, thus mediating between high energy efficiency and long lifetime requirements.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

By adjusting the triplet energy level, LUMO level, and other key parameters of the matrix material through structural modification, the patent creates optimal energy level alignment with phosphorescent emitters. This parameter optimization enables high quantum efficiency while reducing degradation mechanisms that limit device lifetime.

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 these compounds leads to significant improvements in the lifetime, efficiency, and operating voltage of organic electroluminescent devices, particularly in red-, yellow-, and green-phosphorescing OLEDs, with excellent color purity and processability, enabling high-performance electronic devices at a lower cost.

Implementation Method 1

electron transport materials

Methodology Applied
Scientific EffectElectron transport: Conduction (electrical)

Implementation Method 2

hole conductor materials

Methodology Applied
Scientific EffectHole conduction: Conduction (electrical)

Implementation Method 3

organometallic complexes which exhibit phosphorescence

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 4

exhibit elevated oxidation stability

Methodology Applied
Scientific EffectOxidation stability: Oxidation

Data Source

PatentUS11535619B2Hexacyclic heteroaromatic compounds for electronic devices
Publication Date: 2022.12.27 MERCK PATENT GMBH
  • US11535619B2 patent drawing
  • US11535619B2 patent drawing
  • US11535619B2 patent drawing

AI summary

The invention relates to heteroaromatic compounds, particularly for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention and to electronic devices containing same.