Triazine Compounds with Bulky Groups for OLEDs

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Solution Overview

Problem

There is a need for organic semiconductor materials and layers with improved electron mobility and electrochemical stability to enhance the performance of organic electronic devices, such as OLEDs, particularly for increased lifetime at higher current density and efficiency while maintaining low operating voltage and power consumption.

Innovation Solution

The development of triazine compounds with specific structural features, such as those represented by formula 1, which are used as a matrix material in organic semiconductor layers to increase charge mobility and stability, thereby improving luminance efficiency, voltage characteristics, and lifetime.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional organic semiconductor materials are used, then device structure is simple, but electron mobility is low and electrochemical stability is insufficient

Engineering Contradiction:
Improveelectrochemical stabilityVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent employs composite molecular structures combining triazine core units with various aromatic substituents (carbazole, triphenylamine, fluorene groups) to create organic semiconductor materials that achieve both high electron mobility and electrochemical stability. The composite nature of these molecules allows integration of electron-transporting triazine cores with stabilizing aromatic moieties, resolving the contradiction between simplicity and performance.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent introduces specific functional groups at particular positions of the triazine core structure to locally enhance electron mobility while maintaining overall molecular stability. For example, substituting carbazole or triphenylamine groups at specific positions of the triazine ring provides localized electron transport pathways without compromising the global structural stability of the molecule.

Inventive Principle:
Principle #3Local quality

2Duration of action of moving object

If conventional organic materials are used, then manufacturing is simple, but lifetime at higher current density is short

Engineering Contradiction:
Improvedevice lifetimeVSAvoidmaterial synthesis complexity
Core Design Contradiction:
Duration of action of moving objectVSEase of manufacture

Solution Approach 1:

The patent segments the organic semiconductor material into modular components: a triazine core unit providing electron transport capability, and separate aromatic substituent units (carbazole, triphenylamine, fluorene) that can be independently synthesized and then coupled to the core. This segmentation allows optimization of each module's properties and simplifies the overall synthesis process despite the complexity of the final molecule.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent systematically varies molecular parameters such as the type of aromatic substituent, the number of substituents, and their positions on the triazine core to optimize device lifetime at high current density. By changing these molecular parameters, the patent achieves extended device lifetime while maintaining manageable synthesis complexity through established organic synthesis methods.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If conventional materials are used, then power consumption may be low, but luminance efficiency is insufficient

Engineering Contradiction:
Improveluminance efficiencyVSAvoidpower consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent employs triazine-based organic semiconductor materials that enable rapid electron transport through the device, allowing electrons to quickly reach the emission layer and recombine with holes to generate light. This 'rushing through' of electrons reduces non-radiative recombination losses and improves luminance efficiency. The high electron mobility of the triazine derivatives ensures fast charge transport, improving productivity in terms of light output per unit time.

Inventive Principle:
Principle #21Skipping (Rushing through)

Solution Approach 2:

The patent optimizes the LUMO energy level parameter of the organic semiconductor material by selecting appropriate triazine derivatives and substituents. This parameter change enables better energy level alignment with the emission layer, improving electron injection efficiency and reducing energy losses, thereby achieving higher luminance efficiency at acceptable power consumption levels.

Inventive Principle:
Principle #35Parameter changes

4Reliability

If conventional organic materials are used, then device operation is simple, but voltage characteristics are poor

Engineering Contradiction:
Improvevoltage characteristicsVSAvoidmolecular design complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent systematically adjusts the HOMO and LUMO energy level parameters of the organic semiconductor material by selecting different triazine derivatives and aromatic substituents. This parameter optimization improves voltage characteristics by achieving better energy level matching between layers, reducing operating voltage, and improving electron injection efficiency, while the modular molecular design keeps the complexity manageable.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS11530201B2Triazine compounds substituted with bulky groups
Publication Date: 2022.12.20 NOVALED GMBH
  • US11530201B2 patent drawing
  • US11530201B2 patent drawing
  • US11530201B2 patent drawing

AI summary

The present invention relates to a triazine compound according to formula 1: suitable for use as a layer material for electronic devices, and to an organic semiconductor layer comprising at least one compound according to formula 1, as well as to an organic electronic device comprising at least one organic semiconductor layer, and a method of manufacturing the same.