Fluorinated Metal Complex Hole Injection Layer for OLED Stability

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Solution Overview

Problem

There is a need to improve the performance of semiconductor materials and electronic devices, particularly in achieving stable operating voltage over time, by enhancing the characteristics of hole injection layers and semiconductor layers, and to provide hole injection layers that enable efficient injection into adjacent layers with a HOMO level further away from the vacuum level, while also being suitable for mass production through vacuum thermal evaporation.

Innovation Solution

A compound represented by Formula I, comprising a metal coordinated with a charge-neutral ligand, is used to form a hole injection layer, which is non-emissive and has a specific molecular structure suitable for deposition under conditions conducive to mass production, thereby improving the operating voltage stability and efficiency of electronic devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional hole injection layers with metal complexes are used, then hole injection is achieved, but operating voltage stability deteriorates over time

Engineering Contradiction:
Improveoperating voltage stabilityVSAvoiddevice lifetime
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent changes the chemical parameters of the hole injection layer by introducing compounds with specific structural features (triazine or pyrimidine rings with electron-donating groups) and controlled metal complex concentrations (0.1-10 wt%), which improves operating voltage stability while maintaining device lifetime

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite hole injection layer combining organic matrix materials (such as mCP, TCTA, or TAPC) with metal complexes (Alq3, Bpy-OXD, or Bpy-OXD2) in optimized ratios, achieving both stable operating voltage and long device lifetime through synergistic effects

Inventive Principle:
Principle #40Composite materials

2Productivity

If hole injection layers with deeper HOMO levels are used, then injection efficiency into adjacent layers improves, but manufacturing complexity increases

Engineering Contradiction:
Improveinjection efficiencyVSAvoidlayer structure complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent adjusts the HOMO level parameter of the hole injection layer by selecting compounds with specific molecular structures (containing triazine or pyrimidine rings with electron-donating substituents), enabling efficient injection into adjacent layers with deeper HOMO levels without increasing manufacturing complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops universal hole injection layer compounds that can interface with multiple different adjacent layer materials having various HOMO levels, making the solution broadly applicable across different OLED architectures without requiring complex customization

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

3Ease of operation

If complex metal complex compositions are used to improve hole injection, then injection performance improves, but ease of manufacture deteriorates

Engineering Contradiction:
Improvehole injection performanceVSAvoiddeposition process simplicity
Core Design Contradiction:
Ease of operationVSEase of manufacture

Solution Approach 1:

The patent optimizes the concentration parameter of metal complexes in the hole injection layer to 0.1-10 wt%, which maintains good hole injection performance while ensuring the materials can be deposited using conventional vacuum thermal evaporation processes without requiring complex deposition 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 use of the compound in the hole injection layer significantly enhances the operating voltage stability and efficiency of electronic devices, such as OLEDs, by ensuring balanced hole and electron injection, and allows for mass production through suitable deposition conditions.

Implementation Method 1

It is also objective to provide a hole injection layer comprising compounds which may be deposited through vacuum thermal evaporation under conditions suitable for mass production

Methodology Applied
Scientific EffectVacuum thermal evaporation: Evaporation

Data Source

PatentUS20230247896A1Compound of Formula (I), a Semiconductor Material Comprising at Least One Compound of Formula (I), a Semiconductor Layer Comprising at Least One Compound of Formula (I) and an Electronic Device Comprising at Least One Compound of Formula (I)
Publication Date: 2023.08.03 NOVALED GMBH
  • US20230247896A1 patent drawing
  • US20230247896A1 patent drawing
  • US20230247896A1 patent drawing

AI summary

The present invention relates to compound represented by Formula (I) wherein M is a metal; L is a charge-neutral ligand, which coordinates to the metal M; n is an integer selected from 1 to 4, which corresponds to the oxidation number of M; m is an integer selected from 0 to 2; R1, R2 and R3 are substituents, wherein at least one R1, R2 and/or R3 is selected from a substituted C2 to C24 heteroaryl group, wherein at least one substituent is selected from halogen, F, Cl, CN, partially or fully fluorinated C1 to C6 alkyl, partially or fully fluorinated C1 to C6 alkoxy. The present invention also relates to a semiconductor material comprising at least one compound of formula (I), an semiconductor layer comprising at least one compound of formula (I) and an electronic device comprising at least one compound of formula (I). Exemplary compounds are e.g. metal complexes of 3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridin-4-yl)pentane-2,4-dione, such as e.g. tris(((Z)-4-oxo-3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridin-4-yl)pent-2-en-2-yl)oxy)iron and bis(((Z)-4-oxo-3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridin-4-yl)pent-2-en-2-yl)oxy)copper.