Metal Complex Hole Injection Layer for OLED Voltage 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 and enhancing the characteristics of hole injection layers in organic light-emitting diodes (OLEDs), with a focus on compounds that can be deposited through vacuum thermal evaporation suitable for mass production.

Innovation Solution

A compound represented by Formula (I) is introduced, comprising a metal coordinated with a charge-neutral ligand, where the compound is designed to form a hole injection layer with specific substituents that improve the HOMO level positioning and deposition properties, enabling efficient hole injection and emission characteristics.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional hole injection materials are used in OLEDs, then the device can operate, but the operating voltage stability over time is insufficient

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

Solution Approach 1:

The patent modifies the chemical structure of hole injection materials by introducing specific substituents (electron-withdrawing groups like CF3, CN, or halogens at positions 3 and 5 of the phenyl ring) to adjust electronic parameters such as HOMO level and electron affinity. This structural parameter change improves both operating voltage stability and device lifetime by optimizing charge injection characteristics.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs composite molecular structures combining specific aromatic cores (phenyl, naphthyl, or anthryl groups) with coordinated metal centers and tailored substituents. This composite approach creates hole injection materials with optimized electronic properties that simultaneously enhance voltage stability and extend device operational lifetime.

Inventive Principle:
Principle #40Composite materials

2Reliability

If hole injection layer characteristics are improved for better performance, then operating voltage improves, but manufacturing complexity increases

Engineering Contradiction:
Improveoperating voltageVSAvoiddeposition process complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent optimizes molecular weight and structural parameters of hole injection materials to ensure they can be deposited via vacuum thermal evaporation at practical rates. The specific substituent patterns and molecular designs balance performance improvement with manufacturability by controlling volatility and deposition characteristics.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If compounds with improved HOMO level positioning are used, then hole injection efficiency improves, but deposition conditions become more restrictive

Engineering Contradiction:
Improvehole injection efficiencyVSAvoiddeposition conditions
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent carefully adjusts molecular parameters including substituent types, positions, and combinations to achieve optimal HOMO levels for efficient hole injection while maintaining appropriate vapor pressure for vacuum thermal evaporation. The electron-withdrawing substituents are strategically positioned to tune electronic properties without compromising deposition feasibility.

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 compound enhances the stability of operating voltage and lifetime of OLEDs by optimizing the hole injection process, allowing for mass production through suitable deposition conditions, with minimal emissive contribution to the visible spectrum.

Implementation Method 1

provide a hole injection layer which may be deposited through vacuum thermal evaporation

Methodology Applied
Scientific EffectVacuum thermal evaporation: Evaporation

Data Source

PatentUS20230242562A1Compound 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
  • US20230242562A1 patent drawing
  • US20230242562A1 patent drawing
  • US20230242562A1 patent drawing

AI summary

The present invention relates to a compound of 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 C6 to C24 aryl group, wherein at least one substituent of the substituted C6 to C24 aryl group is selected from CN or partially or fully fluorinated C1 to C12 alkyl. 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 4-(2,4-dioxopent-3-yl)-2,3,5,6-tetrafluorobenzonitrile, such as e.g. Fe, Al and Cu complexes thereof.