Carbazole Derivative Host Material for Organic EL Efficiency and Lifetime

Solution Overview

Problem

Current organic electroluminescent devices face challenges in achieving high emission efficiency and stability, particularly for blue devices, with existing technologies limiting their efficiency and lifetime.

Innovation Solution

A material represented by a specific general formula is introduced for organic electroluminescent devices, which includes a carbazole backbone with a tert-butyl group, used as a host or electron blocking layer, enhancing hole injection properties and heat resistance, and combined with thermally activated delayed fluorescence or phosphorescence materials in the light emitting layer.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If phosphorescent organic EL device uses triplet excitons for emission, then internal quantum efficiency can be enhanced up to 100%, but device lifetime is limited and practical blue devices have not been developed

Engineering Contradiction:
Core Design Contradiction:
Use of energy by moving objectVSDuration of action of stationary object

Solution Approach 1:

The patent introduces a novel carbazole derivative compound (Formula 1) with specific molecular structure parameters - including tert-butyl groups at positions 2 and 6, and aromatic heterocyclic groups (X1, X2) that can be oxygen, sulfur, or nitrogen-containing groups. These parameter changes in molecular structure optimize both the efficiency and lifetime by controlling triplet exciton utilization and stabilizing the material against degradation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material strategy by combining the carbazole backbone with various aromatic heterocyclic groups (X1, X2) and substituent groups (Ar1, Ar2). This composite structure allows optimization of both efficiency (through triplet exciton management) and lifetime (through enhanced molecular stability), resolving the contradiction between high efficiency phosphorescent emission and device durability

Inventive Principle:
Principle #40Composite materials

2Use of energy by moving object

If delayed fluorescence organic EL device utilizes TTF mechanism, then internal quantum efficiency can be enhanced up to 40%, but efficiency is low as compared with phosphorescent organic EL device

Engineering Contradiction:
Core Design Contradiction:
Use of energy by moving objectVSProductivity

Solution Approach 1:

The patent modifies molecular parameters by introducing specific heterocyclic groups (X1, X2) and substituents (Ar1, Ar2) on the carbazole backbone to optimize the energy levels and facilitate efficient triplet-to-singlet conversion, achieving higher emission efficiency than conventional TTF devices while maintaining delayed fluorescence mechanism

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The carbazole derivative compound acts as an intermediary material in the light-emitting layer that mediates between triplet excitons and singlet excitons, enabling more efficient energy conversion and higher emission efficiency compared to direct TTF mechanisms in conventional delayed fluorescence devices

Inventive Principle:
Principle #24Intermediary (Mediator)

3Device complexity

If carbazole backbone materials are used for hole transport and host material, then device structure is simplified, but emission efficiency and driving stability need improvement

Engineering Contradiction:
Core Design Contradiction:
Device complexityVSReliability

Solution Approach 1:

The patent optimizes the carbazole derivative compound parameters including molecular weight, glass transition temperature, and HOMO/LUMO energy levels by selecting specific substituents (Ar1, Ar2) and heterocyclic groups (X1, X2). These parameter changes enhance driving stability and emission efficiency while maintaining the material's dual functionality as hole transport and host material, avoiding increased device complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The carbazole derivative compound (Formula 1) is designed to perform multiple functions simultaneously: hole transport, host material for light-emitting dopants, and stability enhancer. This multi-functionality simplifies device structure by reducing the number of separate layers and materials needed while improving overall driving stability through optimized molecular properties

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 material achieves high emission efficiency and long lifetime characteristics, reducing driving voltage and improving heat resistance, resulting in a practically useful organic EL device with improved stability and efficiency.

Implementation Method 1

materials having a carbazole backbone are known as the material for transporting holes (hole transport material)

Methodology Applied
Scientific EffectCharge transport: Conduction (electrical)

Implementation Method 2

The TADF mechanism utilizes a phenomenon in which reverse intersystem crossing occurs from the triplet exciton to the singlet exciton in a material having a small energy difference between the singlet level and the triplet level

Methodology Applied
Scientific EffectThermally activated delayed fluorescence: Fluorescence

Implementation Method 3

reverse intersystem crossing occurs from the triplet exciton to the singlet exciton

Methodology Applied
Scientific EffectReverse intersystem crossing:

Implementation Method 4

in the phosphorescent organic EL device that uses emission caused by triplet excitons, the internal quantum efficiency can be enhanced up to 100% when intersystem crossing efficiently occurs from singlet excitons

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 5

intersystem crossing efficiently occurs from singlet excitons

Methodology Applied
Scientific EffectIntersystem crossing:

Implementation Method 6

When a voltage is applied to an organic EL device, holes and electrons are injected from the anode and the cathode, respectively, into the light emitting layer. Then, the injected holes and electrons are recombined in the light emitting layer to thereby generate excitons

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS20240224800A1Material for organic electroluminescent elements, and organic electroluminescent element
Publication Date: 2024.07.04
  • US20240224800A1 patent drawing
  • US20240224800A1 patent drawing
  • US20240224800A1 patent drawing

AI summary

Provided is an organic EL device having low-voltage drivability, high emission efficiency, and a long lifetime. An organic EL device having a low voltage, high emission efficiency, and a long lifetime can be obtained by using a material for an organic electroluminescent device represented by the following general formula (1), wherein Ar1 is a group represented by the general formula (2) or the like, “*” represents a bonding site, some or all hydrogen atoms in the compounds represented by the general formula (1), the general formula (2), and the like are optionally replaced by deuterium atoms, and n represents an integer of 0 to 1.