Cyclic Phosphine Oxide Derivatives for OLED Efficiency

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Solution Overview

Problem

Organic electroluminescent devices (OLEDs), particularly those exhibiting triplet emission, face challenges in efficiency, operating voltage, and service life, with existing materials not adequately addressing these issues.

Innovation Solution

Development of specific cyclic phosphine oxide and sulfone derivatives as matrix materials, electron transport materials, or hole blocking materials that enhance the performance of OLEDs by improving efficiency, reducing operating voltage, and extending service life.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If phosphorescent metal-organic complexes are used as emitting materials in OLEDs, then triplet emission is achieved, but efficiency, operating voltage, and service life are insufficient

Engineering Contradiction:
Improveservice lifeVSAvoidefficiency
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The patent modifies the chemical structure of matrix materials by introducing specific substituents (Ar1, Ar2, Ar3) and heteroatoms (N, O, S) to change the electronic and optical parameters of the material, thereby improving triplet emission efficiency and device performance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent combines phosphorescent metal-organic complexes with specifically designed organic matrix materials containing cyclic phosphine oxide or sulfone groups to create a composite emitting layer that achieves both high efficiency and long service life

Inventive Principle:
Principle #40Composite materials

2Power

If conventional matrix materials are used in phosphorescent OLEDs, then device operation is possible, but operating voltage remains high

Engineering Contradiction:
Improveoperating voltageVSAvoidperformance stability
Core Design Contradiction:
PowerVSReliability

Solution Approach 1:

The patent changes the HOMO-LUMO energy levels and electron mobility parameters of the matrix material through strategic molecular design, resulting in reduced operating voltage while maintaining stable device performance

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If existing organic semiconductors are used in OLEDs, then basic device function is achieved, but material selection is limited

Engineering Contradiction:
Improvematerial choiceVSAvoiddevice performance
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent develops a series of compounds with core structures that can serve multiple functions (emitting material, matrix material, electron transport material, hole blocking material) depending on substitution patterns, providing versatile material options for different device requirements

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

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 these compounds in OLEDs results in devices with high efficiency, low operating voltage, and extended service life, making them suitable for various applications in organic electroluminescent devices.

Implementation Method 1

electron transport materials

Methodology Applied
Scientific EffectElectron transport: Conduction (electrical)

Implementation Method 2

hole blocking materials

Methodology Applied
Scientific EffectHole blocking: Electrical Resistance

Data Source

PatentEP3877373B15,6-diphenyl-5,6-dihydro-dibenz[c,e][1,2]azaphosphorine and 6-phenyl-6h-dibenzo[c,e][1,2]thiazine-5,5-dioxide derivatives and related compounds as organic electroluminescent materials for oleds
Publication Date: 2023.01.11 MERCK PATENT GMBH
  • EP3877373B1 patent drawing
  • EP3877373B1 patent drawing
  • EP3877373B1 patent drawing

AI summary

The invention relates to 5,6-diphenyl-5,6-dihydro- dibenz[c,e][1,2 ]azaphosphorin and 6-phenyl-6H-dibenzo[c,e] [1,2]thiazin-5,5 dioxide derivatives and similar compounds of the formula (1) as organic electroluminescent materials for use in organic electroluminescent devices, such as, for example, in organic light-emitting diodes (OLEDs), wherein, for the symbols used: Z is the same or different in each occurrence PAr2 or S(=0); E is the same or different in each occurrence O or S if the symbol Z, to which this E binds, represents PAr2 and O if the symbol Z,, to which this E binds, represents S(=0); L is selected from the group comprising NAr2, O, S, S(=O)2, P(=O)Ar2, -X=X- or -C(=O)-NAr2; the remaining symbols are defined in the claims. The invention relates to synthetic examples of compounds according to the invention, to the production of OLEDs which contain said exemplary compounds, and to the results of said electroluminescent devices.