Diamine Derivative OLED Blue Dopant Synthesis

Solution Overview

Problem

Current organic electronic devices face inefficiencies and stability issues due to the limitations of materials used in their organic material layers, particularly in hole injecting, hole transporting, electron injecting, electron transporting, and light emitting functions, which affect their performance in terms of efficiency, operating voltage, lifetime, and color purity.

Innovation Solution

A novel diamine derivative is developed, which can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material, and is used to form organic material layers in devices such as organic light emitting devices, offering improved efficiency, lower operating voltage, increased lifetime, and higher stability. The diamine derivative is synthesized through a method involving a palladium catalyst and specific arylamine compounds, including germanium and deuterium groups, to enhance its properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional diamines are used in OLED manufacturing, then the device structure is simple and manufacturing process is easy, but the color purity is insufficient and lifetime is short

Engineering Contradiction:
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the chemical structure of diamine compounds by introducing specific substituents (fluoro, cyano, trifluoromethyl groups) at defined positions to optimize HOMO/LUMO energy levels and improve device performance and stability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite diamine structures by combining electron-withdrawing groups with aromatic diamine cores, resulting in materials that exhibit both improved color purity and extended device lifetime while maintaining compatibility with existing OLED architectures

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional diamines are used in OLEDs, then the manufacturing process is straightforward, but the color purity and device performance are insufficient

Engineering Contradiction:
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent optimizes the HOMO and LUMO energy levels of diamine compounds through systematic substitution, achieving improved color purity and device performance while maintaining compatibility with standard OLED manufacturing processes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces specific functional groups at strategically positioned locations on the diamine molecular structure to enhance electron withdrawal and improve color purity without requiring changes to the overall manufacturing approach

Inventive Principle:
Principle #3Local quality

3Productivity

If conventional diamines are used, then the synthesis process is simple, but the electron withdrawal capability is insufficient leading to poor device performance

Engineering Contradiction:
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent systematically varies the types and positions of electron-withdrawing substituents to optimize the electron withdrawal capability of diamine compounds, thereby improving device performance while controlling molecular complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses aromatic diamine cores as intermediary structures that mediate between the electron-withdrawing substituents and the overall device function, enabling enhanced electron withdrawal capability through well-defined molecular architectures

Inventive Principle:
Principle #24Intermediary (Mediator)

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 novel diamine derivative enhances the efficiency, reduces operating voltage, and increases the stability of organic electronic devices, particularly in blue light emitting applications, while maintaining high color purity and efficiency, thus addressing the limitations of existing materials.

Implementation Method 1

The diamine derivative is synthesized through a method involving a palladium catalyst and specific arylamine compounds

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

electric energy is converted to light energy by means of an organic material

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentEP1996540B1New diamine derivatives, preparation method thereof and organic electronic device using the same
Publication Date: 2015.07.08
  • EP1996540B1 patent drawingFigure 1
  • EP1996540B1 patent drawing
  • EP1996540B1 patent drawing

AI summary

The present invention relates to a novel diamine derivative, a method for preparation thereof, and an organic electronic device using the same. The diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can be used as a light emitting material as used alone, and also serve as a light emitting host, or a light emitting dopant, in particular, a blue light emitting dopant. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.