Arylamine Hole Injection Layer for OLED Efficiency

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Solution Overview

Problem

Current organic electroluminescent devices face challenges in achieving high luminous efficiency, low driving voltage, and long lifetime due to limitations in hole and electron injection/transport performances, stability, and durability of thin-film materials, particularly with materials like NPD which have low heat resistance and electron blocking performance.

Innovation Solution

The development of organic electroluminescent devices utilizing specific arylamine compounds doped with electron acceptors, such as trisbromophenylamine hexachloroantimony, tetracyanoquinodimethane, and radialene derivatives, in the hole injection layer, combined with anthracene or pyrimidine ring structure compounds in the electron transport layer, to enhance hole injectability, electron blocking, and stability, thereby improving carrier balance and efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If NPD is used as hole transport material, then hole transportability is improved, but heat resistance deteriorates due to low glass transition point (96°C)

Engineering Contradiction:
Improvehole transportabilityVSAvoidheat resistance
Core Design Contradiction:
SpeedVSTemperature

Solution Approach 1:

The patent modifies the chemical structure of hole transport materials by introducing specific molecular structures (carbazole, dibenzofuran, dibenzothiophene, indole units) with appropriate glass transition points (Tg ≥ 100°C). This changes the thermal and electrical parameters simultaneously to achieve both high hole mobility and heat resistance, resolving the contradiction between hole transportability and temperature stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite hole transport materials containing multiple functional units (carbazole, dibenzofuran, dibenzothiophene, indole) in specific combinations. These composite molecular structures synergistically provide both excellent hole transport properties and high thermal stability, overcoming the limitations of single-structure materials like NPD.

Inventive Principle:
Principle #40Composite materials

2Device complexity

If conventional hole injection/transport materials are used, then device structure is simplified, but luminous efficiency and power efficiency deteriorate due to poor carrier balance

Engineering Contradiction:
Improvedevice structureVSAvoidluminous efficiency
Core Design Contradiction:
Device complexityVSUse of energy by moving object

Solution Approach 1:

The patent optimizes the HOMO levels of hole transport materials to be in the range of 5.8-6.5 eV and electron mobility to be ≤10^-6 cm²/Vs, creating ideal parameter combinations for carrier balance. These parameter optimizations enable efficient charge injection and transport, significantly improving luminous efficiency and power efficiency while maintaining device structure simplicity.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If materials with low heat resistance are used, then ease of manufacture is improved, but device lifetime deteriorates due to thermal decomposition

Engineering Contradiction:
Improveease of manufactureVSAvoiddevice lifetime
Core Design Contradiction:
Ease of manufactureVSDuration of action of stationary object

Solution Approach 1:

The patent specifies that hole transport materials must have glass transition points Tg ≥ 100°C and electron mobility ≤10^-6 cm²/Vs. These parameter requirements ensure high thermal stability and resistance to thermal decomposition during device operation, thereby extending device lifetime while maintaining ease of manufacture through conventional fabrication processes.

Inventive Principle:
Principle #35Parameter changes

4Speed

If materials with low electron blocking performance are used, then hole injectability is improved, but luminous efficiency deteriorates due to poor carrier balance

Engineering Contradiction:
Improvehole injectabilityVSAvoidluminous efficiency
Core Design Contradiction:
SpeedVSUse of energy by moving object

Solution Approach 1:

The patent optimizes the electron mobility of hole transport materials to be ≤10^-6 cm²/Vs, creating ideal electron blocking performance. This parameter optimization prevents excessive electron injection into the hole transport layer, maintaining carrier balance and improving luminous efficiency while preserving excellent hole injectability through appropriate HOMO level selection (5.8-6.5 eV).

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

This approach results in devices with low turn-on voltage, high luminous efficiency, high power efficiency, and extended lifetime by optimizing hole and electron transport performances and stability, effectively addressing the limitations of existing materials.

Implementation Method 1

it has been proposed that hole injectability can be improved by p-doping materials such as trisbromophenylamine hexachloroantimony, radialene derivatives, and F4-TCNQ into a material commonly used for the hole injection layer or the hole transport layer

Methodology Applied
Scientific Effectp-doping: Dopants

Implementation Method 2

In an organic EL device, charges injected from both electrodes recombine in a light emitting layer to cause emission

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Implementation Method 3

there have been attempts to use triplet excitons for further improvements of luminous efficiency, and the use of a phosphorescence-emitting compound has been examined

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 4

Devices that use light emission caused by thermally activated delayed fluorescence (TADF) have also been developed

Methodology Applied
Scientific EffectThermally activated delayed fluorescence:

Data Source

PatentEP3229284B1Organic electroluminescent element
Publication Date: 2022.08.31 HODOGAYA CHEMICAL CO LTD
  • EP3229284B1 patent drawingFigure 1
  • EP3229284B1 patent drawing
  • EP3229284B1 patent drawing

AI summary

[Object] An organic electroluminescent device having low driving voltage, high luminous efficiency, and a long lifetime is provided by combining various materials for an organic electroluminescent device, which are excellent, as materials for an organic electroluminescent device having high luminous efficiency and high durability, in hole and electron injection/transport performances, electron blocking ability, stability in a thin-film state and durability, so as to allow the respective materials to effectively reveal their characteristics. [Means of Realizing the Object] In the organic electroluminescent device having at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole injection layer includes an arylamine compound of the following general formula (1) and an electron acceptor. In the formula, Ar1 to Ar4 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.