Aryl Heteroaryl Compounds for Deep-Blue OLED Emitters

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Solution Overview

Problem

Current blue-emitting OLEDs face challenges in achieving deep-blue color coordinates, long lifetime, high efficiency, and optimal operating voltage, with existing compounds lacking in solubility for solution processing.

Innovation Solution

Development of compounds of formula (1) with specific aryl and heteroaryl groups, allowing for deep-blue emission, improved solubility in organic solvents, and suitable for use as emitters or matrix materials in OLEDs, employing transition metal-catalyzed coupling reactions and Suzuki coupling for synthesis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional blue-emitting compounds are used in OLEDs, then device structure and functional principle are maintained, but lifetime, efficiency, and colour coordinates of emitted light are insufficient

Engineering Contradiction:
ImprovelifetimeVSAvoidcompound performance
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies molecular parameters by introducing specific aryl and heteroaryl groups (Ar1-Ar5) with defined structural characteristics (6-60 aromatic ring atoms) to optimize the emitter compound's photophysical properties, achieving deep-blue emission with improved lifetime and efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining multiple aromatic ring systems (Ar1-Ar5) with specific structural features (condensed aryl groups, indenofluorene groups) to achieve synergistic effects that improve both color coordinates and device lifetime

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If deep-blue emission is achieved with narrow emission band, then colour-depth is improved, but solubility for solution processing deteriorates

Engineering Contradiction:
Improvecolour coordinatesVSAvoidsolubility
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent introduces specific local structural features (Ar1 with 10+ aromatic ring atoms, Ar2-Ar5 with 6-60 aromatic ring atoms) that locally enhance color purity while the overall molecular architecture maintains solubility through controlled substitution patterns and steric arrangements

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The emitter compound is segmented into distinct functional aromatic units (Ar1-Ar5) that can be independently optimized for color properties while maintaining overall molecular solubility through modular structural design

Inventive Principle:
Principle #1Segmentation

3Reliability

If improved lifetime and efficiency are achieved, then device performance is enhanced, but operating voltage optimization becomes more challenging

Engineering Contradiction:
ImprovelifetimeVSAvoidoperating voltage
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The emitter compound is designed to simultaneously fulfill multiple functions: achieving deep-blue emission, extending lifetime, maintaining efficiency, and optimizing operating voltage through integrated molecular design that coordinates electronic properties across the entire molecular structure

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 compounds achieve deep-blue color coordinates, extended lifetime, and enhanced efficiency in OLEDs, with good solubility for solution processing, improving performance and manufacturing feasibility.

Implementation Method 1

Blue-fluorescent emitters known from the prior art are a multiplicity of compounds, in particular arylamines containing one or more condensed aryl groups and/or indenofluorene groups

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 2

employing transition metal-catalyzed coupling reactions and Suzuki coupling for synthesis

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11365167B2Materials for organic electroluminescent devices
Publication Date: 2022.06.21 MERCK PATENT GMBH
  • US11365167B2 patent drawing
  • US11365167B2 patent drawing
  • US11365167B2 patent drawing

AI summary

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.