Phenoxazine Derivatives for Blue OLED Host and Transport

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current OLEDs, particularly blue-emitting ones, face challenges in achieving improved performance metrics such as lifetime, efficiency, and operating voltage, with existing materials lacking in thermal stability and exhibiting unsatisfactory color properties and emission bands.

Innovation Solution

Compounds with an aromatic or heteroaromatic ring system linked para to the oxygen atom of a phenoxazine compound are developed, which serve as effective blue emitters, hole-transport materials, and matrix materials, enhancing the performance of OLEDs by offering improved color depth, narrow emission bands, and increased efficiency and lifetime.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If conventional blue-emitting OLED materials are used, then the device can emit blue light, but the lifetime and efficiency are insufficient

Engineering Contradiction:
ImproveOLED lifetimeVSAvoidOLED efficiency
Core Design Contradiction:
Duration of action of stationary objectVSLoss of energy

Solution Approach 1:

The patent modifies the molecular structure of phenoxazine derivatives by introducing specific substituents (Ar groups at positions 2 and 7, and Ar' groups at positions 3 and 6) to optimize the HOMO-LUMO energy gap and emission characteristics. This structural parameter change enables deep-blue emission with improved lifetime and efficiency simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite molecular design combining phenoxazine core with aromatic substituents (Ar and Ar' groups), creating a composite emitter material that integrates the advantages of different structural motifs to achieve both long lifetime and high efficiency in blue emission

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If existing emitter compounds are used, then the OLED can operate, but the color properties and emission band width are unsatisfactory

Engineering Contradiction:
Improvecolor propertiesVSAvoidemission band width
Core Design Contradiction:
Illumination intensityVSManufacturing precision

Solution Approach 1:

The patent introduces specific aromatic substituents (Ar and Ar' groups) at defined positions on the phenoxazine core to locally modify the electron distribution and energy levels, thereby optimizing the emission spectrum for deep-blue color with narrow bandwidth

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent designs molecules with balanced electron-hole recombination dynamics through the phenoxazine core structure, enabling efficient radiative decay with controlled non-radiative pathways to achieve narrow emission bands and pure blue color

Inventive Principle:
Principle #15Dynamics

3Stability of the object's composition

If conventional materials are used in OLEDs, then the device structure can be maintained, but thermal stability is insufficient

Engineering Contradiction:
Improvethermal stabilityVSAvoidoperational stability
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent increases thermal stability by designing rigid phenoxazine core structures with extended aromatic systems and strategic substituents, raising the glass transition temperature and decomposition temperature to ensure operational stability under device working 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

These compounds significantly improve the performance of OLEDs by providing better color properties, efficiency, and operational stability, making them suitable for use in organic electroluminescent devices as emitters, hole-transport materials, and matrix materials.

Implementation Method 1

Blue-fluorescent emitters known from the prior art are a multiplicity of compounds... the present invention relates to compounds which are suitable for use in electronic devices, such as, for example, OLEDs, and which can be employed, in particular, as blue emitters

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 2

there is also a need for alternative hole-transport materials... these compounds are very suitable as hole-transport and hole-injection materials and as matrix materials

Methodology Applied
Scientific EffectCharge carrier transport: Conduction (electrical)

Implementation Method 3

to be capable of sublimation without decomposition... For compounds which are processed by vacuum evaporation, the alkyl groups preferably have not more than four C atoms

Methodology Applied
Scientific EffectSublimation: Sublimation

Data Source

PatentEP3334732B1Phenoxazine derivatives for organic electroluminescent devices
Publication Date: 2024.03.06 MERCK PATENT GMBH
  • EP3334732B1 patent drawing
  • EP3334732B1 patent drawing
  • EP3334732B1 patent drawing

AI summary

The present invention relates to the compounds of the formulae (1) and (2) and to organic electroluminescent devices, in particular blue- emitting devices, in which these compounds are used as host material or dopant in the emitting layer and/or as hole-transport material and/ or as electron-transport material.