Aromatic Amine Derivative for Organic EL Hole Transport

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Solution Overview

Problem

Organic electroluminescence (EL) devices face challenges with short lifetimes due to crystallization issues and high sublimation temperatures of hole transporting materials with many aromatic groups, leading to defects and non-uniform deposition, which affect efficiency and longevity.

Innovation Solution

A novel aromatic amine derivative with specific substituents, such as a dibenzofuran and terphenyl structure, is used as a hole injecting or transporting material, reducing intermolecular interaction and preventing crystallization, thereby improving yield and extending the lifetime of organic EL devices, especially those emitting blue light.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If hole transporting materials with many aromatic groups are used to elevate glass transition temperature, then thermal stability is improved, but crystallization occurs during thin film formation

Engineering Contradiction:
Improveglass transition temperatureVSAvoidcrystallization resistance
Core Design Contradiction:
TemperatureVSStability of the object's composition

Solution Approach 1:

The patent introduces asymmetry into the molecular structure by combining dibenzofuran (which has inherent asymmetry in its fused ring system) with terphenyl groups in non-symmetrical arrangements. This asymmetry disrupts the regular packing of molecules, preventing crystallization while maintaining the thermal stability provided by the aromatic groups. The asymmetrical structure ensures that molecules cannot align in a regular lattice pattern during thin film formation.

Inventive Principle:
Principle #4Asymmetry

Solution Approach 2:

The patent changes the molecular parameters by carefully selecting the number and arrangement of aromatic groups (dibenzofuran and terphenyl) to achieve an optimal balance. The compound contains a specific number of aromatic rings (8-12 benzene rings equivalent) to elevate Tg while incorporating structural features that prevent excessive intermolecular interaction and crystallization. This parameter optimization resolves the contradiction between thermal stability and crystallization resistance.

Inventive Principle:
Principle #35Parameter changes

2Temperature

If compounds with large number of aromatic groups are used to increase glass transition temperature, then thermal stability is improved, but sublimation temperature increases causing decomposition during vapor deposition

Engineering Contradiction:
Improveglass transition temperatureVSAvoiddecomposition resistance during vapor deposition
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent optimizes the molecular parameters by selecting a specific range of aromatic group quantities (8-12 benzene rings equivalent) and arranging them in a structure that balances thermal properties. The dibenzofuran-terphenyl combination provides sufficient Tg elevation while the specific molecular weight and structure keep sublimation temperature within acceptable ranges for vapor deposition, preventing decomposition during the deposition process.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining dibenzofuran units with terphenyl groups. This composite structure leverages the thermal stability of the fused ring dibenzofuran system while the terphenyl groups provide appropriate molecular weight and intermolecular interaction characteristics. The synergistic combination resolves the contradiction between achieving high Tg and maintaining compatibility with vapor deposition processes.

Inventive Principle:
Principle #40Composite materials

3Temperature

If symmetrical structure compounds are used to achieve high glass transition temperature, then thermal stability is improved, but crystallization occurs causing clogging of crucible outlet and reduction in device yields

Engineering Contradiction:
Improveglass transition temperatureVSAvoiddevice yield
Core Design Contradiction:
TemperatureVSProductivity

Solution Approach 1:

The patent fundamentally addresses the crystallization issue by introducing asymmetry into the molecular structure. The dibenzofuran-terphenyl combination creates an asymmetrical molecule that cannot pack efficiently in a crystalline lattice. This asymmetry prevents both local and long-range ordering during thin film formation, eliminating the clogging problem at the crucible outlet and reducing defects in the deposited films, thereby improving device yields.

Inventive Principle:
Principle #4Asymmetry

Solution Approach 2:

The patent applies local quality by creating regions of different molecular interactions within the compound. The dibenzofuran portion provides thermal stability through its rigid fused ring structure, while the terphenyl groups with their specific substitution patterns create local regions that disrupt overall molecular symmetry. This local structural differentiation prevents uniform crystallization while maintaining the desired thermal properties.

Inventive Principle:
Principle #3Local quality

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 aromatic amine derivative effectively prevents crystallization and enhances the stability and yield of organic EL devices, leading to a prolonged lifetime and improved performance, particularly in blue-light emitting devices.

Implementation Method 1

it hardly causes the crystallization of a molecule

Methodology Applied
Scientific EffectCrystallization prevention: Crystallisation

Data Source

PatentEP2295421B2Aromatic amine derivative and organic electroluminescent device using the same
Publication Date: 2016.04.06 IDEMITSU KOSAN CO LTD
  • EP2295421B2 patent drawing
  • EP2295421B2 patent drawing
  • EP2295421B2 patent drawing

AI summary

An aromatic amine derivative having a specific structure. An organic electroluminescence device which is composed of one or more organic thin film layers sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers especially a hole transporting layer, contains the aromatic amine derivative. The aromatic amine derivative has at least one substituted or unsubstituted dibenzofuran skeleton and at least one substituted or unsubstituted terphenylene skeleton. Because the molecules in the aromatic amine derivative hardly crystallize, organic electroluminescence devices improving their production yield and having prolonged lifetime are provided.