Carbazolyl-Substituted Phenyl Organic Compound for OLED Stability

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Solution Overview

Problem

Existing organic electroluminescent devices face challenges with unbalanced charge carrier recombination, low luminous efficiency, and insufficient durability due to inadequate hole-transporting and electron-transporting properties, especially when using materials with carbazolyl and pyridine rings, leading to poor performance in blue light-emitting and phosphorescence-emitting devices.

Innovation Solution

An organic compound with multiple partial structures represented by Formula (I) is developed, featuring a carbazolyl group, a linking group, and a six-membered aromatic heterocycle, which enhances both hole-transporting and electron-transporting properties, along with improved electrical oxidation/reduction durability and high triplet excitation levels, allowing for balanced charge transfer and increased stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If compounds with conjugated nitrogen atoms are used, then triplet excitation level is reduced, but durability against electrical oxidation/reduction deteriorates

Engineering Contradiction:
Improvetriplet excitation levelVSAvoiddurability against electrical oxidation/reduction
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent applies local quality by strategically positioning carbazolyl groups and pyridine/pyrimidine rings in specific spatial arrangements within the molecular structure. The carbazolyl groups (with nitrogen atoms) are positioned to provide high triplet excitation levels, while the pyridine/pyrimidine rings are positioned to provide durability against electrical oxidation/reduction. This localized functional distribution allows both requirements to be satisfied simultaneously without the nitrogen atoms conjugating in a way that would reduce triplet excitation.

Inventive Principle:
Principle #3Local quality

2Use of energy by moving object

If phosphorescence is used instead of fluorescence to increase luminous efficiency, then energy utilization is improved, but sufficient luminous efficiency is not practically achieved and durability is reduced

Engineering Contradiction:
Improveluminous efficiencyVSAvoiddurability
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent changes the molecular parameters by incorporating specific carbazolyl and pyridine/pyrimidine ring structures that inherently provide both high triplet excitation levels (necessary for phosphorescence) and high durability. By optimizing the molecular parameters such as the arrangement of nitrogen atoms and the conjugation structure, the material achieves practical phosphorescent luminous efficiency while maintaining excellent durability, overcoming the limitations of conventional phosphorescent materials.

Inventive Principle:
Principle #35Parameter changes

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 organic compound achieves high luminous efficiency, improved driving stability, and extended lifetime in organic electroluminescent devices, making it suitable for various applications including flat panel displays and electrophotographic photoreceptors.

Implementation Method 1

enhances both hole-transporting and electron-transporting properties, along with improved electrical oxidation/reduction durability

Methodology Applied
Scientific EffectCharge transport: Conduction (electrical)

Implementation Method 2

phosphorescence has been investigated to be used instead of fluorescence

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 3

fluorescence has been used

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentUS8178215B2Organic compound containing at least two carbazolyl-substituted phenyl structures; charge-transporting material and organic el element containing the compound
Publication Date: 2012.05.15 MITSUBISHI CHEM CORP
  • US8178215B2 patent drawing
  • US8178215B2 patent drawing
  • US8178215B2 patent drawing

AI summary

An organic compound and a charge-transporting material which are excellent in both a hole-transporting property and an electron-transporting property and have excellent electrical oxidation/reduction durability and a high triplet excitation level are provided, and an organic electroluminescent device which uses this organic compound and has high luminous efficiency and high driving stability and long lifetime is provided, wherein the organic compound has two or more partial structures represented by the following Formula (I):wherein Cz denotes a carbazolyl group; Z is as defined; and Q denotes a direct link connected to G present in a moiety represented by the following Formula (II):wherein B1 ring is a six-membered aromatic heterocycle containing n N atoms as a hetero atom; n is an integer of 1 to 3; G is as defined; and m is an integer of 3 to 5.