Azomethine-Lithium Complex Electron Injection Layer for OLEDs

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Solution Overview

Problem

Current OLED technologies face challenges in achieving improved performance, particularly in electron injection, with existing materials like LiF requiring severe deposition conditions and having limitations in handling and deposition processes.

Innovation Solution

Development of novel compounds with specific structural formulas that can be used as electron injection layers, offering comparable or better performance to LiF without the need for severe deposition conditions, and can be deposited using various methods such as vacuum sublimation, organic vapor phase deposition, or solution processing, allowing for easier handling and lower temperature processing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If LiF is used as electron injection layer, then electron injection performance is improved, but deposition conditions become severe and handling difficulty increases

Engineering Contradiction:
Improveelectron injection performanceVSAvoiddeposition conditions
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent changes the chemical composition parameters from inorganic LiF to organic compounds (such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline and its derivatives), which fundamentally alters the deposition temperature range from high (severe) to low (mild conditions), while preserving the electron injection function

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs organic compounds that can be deposited as thin films and serve as single-use electron injection layers, replacing the need for severe deposition conditions associated with inorganic materials like LiF, thereby simplifying the manufacturing process

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Reliability

If LiF is used as electron injection layer, then electron injection performance is improved, but handling difficulty increases

Engineering Contradiction:
Improveelectron injection performanceVSAvoidhandling
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent transitions from inorganic LiF to organic compounds, changing the physical and chemical parameters such as volatility, solubility, and thermal stability, which enable easier handling through solution processing and vacuum deposition at low temperatures

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the mechanical deposition process required for LiF with chemical vapor deposition or solution-based methods using organic compounds, eliminating the need for severe mechanical or thermal processing conditions

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Ease of manufacture

If conventional electron injection materials are used, then device fabrication is simpler, but voltage drift increases and device lifetime decreases

Engineering Contradiction:
Improvefabrication simplicityVSAvoiddevice lifetime
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent employs composite structures where organic compounds are used in combination with dopants (such as alkali metals or alkaline earth metals) to create electron injection layers that maintain fabrication simplicity while achieving reduced voltage drift and enhanced device lifetime through optimized electronic properties

Inventive Principle:
Principle #40Composite materials

4Reliability

If LiF is used as electron injection layer, then electron injection performance is improved, but processing temperature must be high

Engineering Contradiction:
Improveelectron injection performanceVSAvoiddeposition temperature
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent fundamentally changes the material composition from inorganic LiF to organic compounds, which shifts the deposition temperature parameter from high (above 600°C for LiF) to low (below 150°C for organic compounds), enabling electron injection performance without severe thermal conditions

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 novel compounds provide improved electron injection performance with reduced voltage drift and increased device lifetime compared to inorganic injectors, enabling more efficient and stable OLED device manufacturing.

Implementation Method 1

Embodiments of the compounds can be deposited by vacuum sublimation at temperatures significantly below that required for LiF (FIG. 13) e.g. below about 250° C.

Methodology Applied
Scientific EffectVacuum sublimation: Sublimation

Implementation Method 2

In addition to vacuum sublimation, embodiments of the compounds can be deposited by the organic vapour phase deposition (OVPD) process described inter alia by Universal Display Corporation in which organic films are deposited using an inert carrier gas to transfer films of organic material onto a cooled substrate

Methodology Applied
Scientific EffectOrganic vapor phase deposition: Physical Vapour Deposition

Data Source

PatentUS8883325B2Electroluminescent device using azomethine-lithium-complex as electron injection layer
Publication Date: 2014.11.11 MERCK PATENT GMBH
  • US8883325B2 patent drawing
  • US8883325B2 patent drawing
  • US8883325B2 patent drawing

AI summary

In OLEDs, improved efficiency is obtained by compounds which can form inter alia electron injection layers of the formula (I)whereinR1 is a 1-5 ring aryl (including polycyclic), aralkyl or heteroaryl group which is optionally substituted with one or more C1-C4 alkyl, alkoxy or cyano;R2 and R3 together form a 1-5 ring aryl (including polycyclic), aralkyl or heteroaryl group which is optionally substituted with C1-C4 alkyl, alkoxy or cyano;R4 is hydrogen, C1-C4 alkyl or aryl; andAr is monocyclic, bicyclic or tricyclic aryl or heteroaryl which is optionally substituted with one or more C1-C4-alkyl or alkoxy groups, or an oligomer thereof.