Aromatic Compounds for OLED Hole Transport

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Solution Overview

Problem

Current organic electronic devices, particularly OLEDs, face challenges in improving performance metrics such as lifetime, efficiency, and operating voltage, with a need for materials that exhibit high glass transition temperature, low crystallization tendency, and high refractive index, especially for hole-transporting layers and phosphorescent emitters.

Innovation Solution

Development of aromatic compounds containing amino groups, bridged amino groups, and carbazole groups, specifically designed for use in OLEDs as hole transport materials and matrix materials, which enhance device performance by offering high lifetime, efficiency, and low operating voltage while maintaining a low crystallization tendency and high refractive index.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of moving object

If conventional hole transport materials and matrix materials are used in OLEDs, then the device structure is simple and manufacturing is easier, but the lifetime is short, efficiency is low, and operating voltage is high

Engineering Contradiction:
Improvedevice lifetimeVSAvoidoperating voltage
Core Design Contradiction:
Duration of action of moving objectVSLoss of energy

Solution Approach 1:

The patent modifies the molecular structure of hole transport materials and matrix materials by introducing specific aromatic ring systems, heteroatoms, and substituent groups to optimize electronic properties. This changes the HOMO/LUMO energy levels, charge mobility, and optical properties of the materials, enabling simultaneous improvement in device lifetime and reduction in operating voltage through precise molecular design

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops composite material systems combining hole transport materials with specific matrix materials that have complementary properties. The hole transport layer uses compounds with high hole mobility while the emitting layer matrix material provides appropriate triplet energy levels and good stability, creating a synergistic effect that improves both lifetime and efficiency without requiring high operating voltage

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If materials with high refractive index are used, then light outcoupling is improved, but the tendency to crystallization increases which reduces device stability

Engineering Contradiction:
Improvelight outcoupling efficiencyVSAvoidcrystallization resistance
Core Design Contradiction:
Illumination intensityVSStability of the object's composition

Solution Approach 1:

The patent introduces bulky substituent groups (such as tert-butyl groups, adamantyl groups, or large aromatic substituents) at specific positions on the molecular core. These local structural modifications increase molecular volume and reduce packing efficiency, thereby suppressing crystallization tendency. At the same time, the core structure maintains high electron density and polarizability to ensure high refractive index for improved light outcoupling

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent optimizes the glass transition temperature (Tg) of the materials by adjusting molecular weight, chain flexibility, and intermolecular interactions. By achieving Tg > 100°C through molecular design, the materials maintain amorphous state at operating temperatures, preventing crystallization while preserving high refractive index properties for enhanced light extraction

Inventive Principle:
Principle #35Parameter changes

3Productivity

If materials are optimized for high efficiency, then luminescence efficiency improves, but the device complexity increases

Engineering Contradiction:
Improveluminescence efficiencyVSAvoidmaterial structure complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent designs hole transport materials that simultaneously perform multiple functions: charge transport, exciton blocking, and optical waveguiding. The same molecular structure provides high hole mobility through aromatic amine groups while maintaining appropriate HOMO/LUMO levels for efficient charge injection and exciton confinement, reducing the need for separate functional layers and simplifying overall device structure

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

Solution Approach 2:

The patent uses modular molecular design where a core aromatic structure (such as triphenylene, perylene, or carbazole) serves as the functional backbone, and various substituent groups can be attached to tune specific properties. This segmentation allows independent optimization of charge transport, optical properties, and thermal stability without requiring complete redesign of the molecular structure

Inventive Principle:
Principle #1Segmentation

Data Source

PatentUS20240383851A1Materials for electronic devices
Publication Date: 2024.11.21 MERCK PATENT GMBH
  • US20240383851A1 patent drawing
  • US20240383851A1 patent drawing
  • US20240383851A1 patent drawing

AI summary

The present application relates to compounds of formula (I), to processes for preparation thereof, and to the use thereof in electronic devices.