Substituted Hydroxyquinoline Metal Complexes for OLEDs

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Solution Overview

Problem

Existing organic electronic devices using hydroxyquinoline compounds face issues with mutagenicity and poor processability, affecting their efficiency, lifetime, and environmental safety, particularly in electron-transport layers.

Innovation Solution

Development of novel metal complexes with specific branched or cyclic alkyl or alkoxy groups attached to the quinoline ring, which reduce mutagenicity and improve processability, maintaining or enhancing electronic performance characteristics such as efficiency and lifetime.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If hydroxyquinoline compounds are used in electron-transport layers, then electron-transporting properties are improved, but mutagenic effects and carcinogenic effects increase

Engineering Contradiction:
Improveelectron-transporting propertiesVSAvoidmutagenic effects
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the chemical structure of hydroxyquinoline compounds by introducing specific substituents (branched or cyclic alkyl/alkoxy groups at positions 2 or 7 of the quinoline ring) to change the molecular parameters. This structural modification maintains the electron-transporting capability while reducing mutagenic and carcinogenic effects, as demonstrated by the AMES test results showing the new compounds are not mutagenic up to 5000 µg/plate

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining the hydroxyquinoline core with specific alkyl or alkoxy substituent groups. These composite structures (compounds of formulae 1-3) achieve a balance between maintaining desired electron-transport properties and reducing harmful biological effects through the synergistic combination of different molecular components

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional hydroxyquinoline compounds are used, then electron-transport function is achieved, but processability is poor

Engineering Contradiction:
Improveelectron-transport functionVSAvoidprocessability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent changes physical parameters of the hydroxyquinoline compounds by introducing alkyl or alkoxy substituents, which modify intermolecular interactions and improve solubility and processability. The new compounds can be processed from solution or by vapor deposition, unlike conventional compounds that exhibit poor processability, while maintaining the essential electron-transport function in OLED electron-transport layers

Inventive Principle:
Principle #35Parameter changes

3Productivity

If existing electron-transport materials are used, then device efficiency is maintained, but environmental friendliness decreases

Engineering Contradiction:
Improvedevice efficiencyVSAvoidenvironmental friendliness
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the chemical composition parameters of electron-transport materials by replacing conventional hydroxyquinoline structures with substituted variants (formulae 1-3) that have reduced environmental toxicity. The new compounds maintain efficient electron-transport performance in OLEDs while showing reduced mutagenic and carcinogenic effects, thereby improving environmental friendliness without sacrificing device efficiency

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS11005049B2Metal complexes
Publication Date: 2021.05.11 MERCK PATENT GMBH
  • US11005049B2 patent drawing
  • US11005049B2 patent drawing
  • US11005049B2 patent drawing

AI summary

The present invention relates to metal complexes, to compositions and formulations comprising these complexes, and to devices comprising the complexes or compositions.