Aromatic Amine Hole Transport Materials for OLEDs

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Solution Overview

Problem

Current organic electronic devices, particularly OLEDs, face challenges in achieving high performance, long lifetime, and low operating voltage due to limitations in hole-transporting materials and matrix materials, which require compounds with high glass transition temperature, stability, and conductivity.

Innovation Solution

Development of aromatic amines with specific aromatic or heteroaromatic ring systems on the amine nitrogen atom, suitable for use as hole transport materials and matrix materials in OLEDs, offering high efficiency, long lifetime, and low operating voltage, along with high glass transition temperature and stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If conventional hole-transporting materials are used, then device structure is simple, but device lifetime is short and efficiency is low

Engineering Contradiction:
Improvedevice lifetimeVSAvoidcompound structure complexity
Core Design Contradiction:
Duration of action of stationary objectVSDevice complexity

Solution Approach 1:

The patent employs composite aromatic amine structures combining multiple aromatic ring systems (e.g., dibenzofuran, dibenzothiophene, carbazole) with amine functional groups to create hole-transporting materials that achieve both extended device lifetime and maintained structural simplicity. The composite molecular architecture enables simultaneous optimization of stability and conductivity properties.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention introduces specific aromatic ring systems at particular positions within the molecular structure to enhance local stability and conductivity properties. By strategically placing electron-rich aromatic groups (dibenzofuran, dibenzothiophene) adjacent to the amine nitrogen, the material achieves improved hole transport and device lifetime without requiring complex overall molecular architecture.

Inventive Principle:
Principle #3Local quality

2Use of energy by moving object

If conventional matrix materials are used, then operating voltage is high, but synthesis is easier

Engineering Contradiction:
Improveoperating voltageVSAvoidsynthesis difficulty
Core Design Contradiction:
Use of energy by moving objectVSEase of manufacture

Solution Approach 1:

The patent modifies key molecular parameters of matrix materials by incorporating electron-rich aromatic ring systems and adjusting substituent patterns to reduce operating voltage. The systematic variation of aromatic groups (dibenzofuran vs. dibenzothiophene vs. carbazole) and their substitution patterns enables optimization of electrical properties while maintaining reasonable synthetic accessibility through established organic synthesis methods.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If aromatic amines with specific ring systems are used, then efficiency and lifetime improve, but glass transition temperature must be maintained high

Engineering Contradiction:
Improvedevice efficiencyVSAvoidglass transition temperature
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent maintains high glass transition temperature by incorporating rigid aromatic ring systems (dibenzofuran, dibenzothiophene, carbazole) as local structural elements within the molecule. These rigid aromatic segments provide thermal stability and maintain glass transition temperature while the overall molecular design preserves efficiency properties through appropriate functional group placement and aromaticity.

Inventive Principle:
Principle #3Local quality

Data Source

PatentUS20240083836A1Materials for electronic devices
Publication Date: 2024.03.14 MERCK PATENT GMBH
  • US20240083836A1 patent drawing
  • US20240083836A1 patent drawing
  • US20240083836A1 patent drawing

AI summary

The present application relates to compounds of a formula (I), (II) or (III), to processes for preparing such compounds, and to electronic devices comprising one or more such compounds, and to the use of such compounds in electronic devices.