Cyanobenzene Delayed Fluorescent Material for OLED Efficiency

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Solution Overview

Problem

Current delayed fluorescent materials for light emitting devices have limitations in achieving high light emission efficiency and short delayed fluorescence lifetime, with challenges in improving durability and generalizing chemical structures for practical use.

Innovation Solution

A cyanobenzene compound with a specific structure, including substituted ring-fused indol-1-yl groups and donor groups, is developed to enhance light emission efficiency and reduce delayed fluorescence lifetime, integrated into organic light emitting devices with a host material and additional delayed fluorescent materials for improved performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If conventional delayed fluorescent materials are used, then light emission efficiency can be improved by utilizing both excited singlet and triplet states, but the delayed fluorescence lifetime remains too long for practical application

Engineering Contradiction:
Improvelight emission efficiencyVSAvoiddelayed fluorescence lifetime
Core Design Contradiction:
Use of energy by moving objectVSLoss of time

Solution Approach 1:

The patent applies parameter changes by systematically varying the molecular structure of cyanobenzene compounds, specifically introducing different donor groups at the 2-position and modifying substituents at positions 3, 4, and 5. This structural parameter optimization enables simultaneous achievement of high light emission efficiency (2.7×10^2 cd/A) and short delayed fluorescence lifetime (6.0 μs), resolving the contradiction between these two parameters.

Inventive Principle:
Principle #35Parameter changes

2Use of energy by moving object

If the molecular structure of delayed fluorescent materials is modified to improve light emission efficiency, then emission performance increases, but durability and stability deteriorate

Engineering Contradiction:
Improvelight emission efficiencyVSAvoiddevice durability
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent employs composite material design by combining the cyanobenzene core structure with specifically selected donor groups (such as carbazol-9-yl) and aromatic substituents. This composite molecular structure achieves both high light emission efficiency and excellent device durability (operating lifetime exceeding 1000 hours at 100 cd/m²), as the synergistic combination of structural elements provides both optical performance and structural stability.

Inventive Principle:
Principle #40Composite materials

3Use of energy by moving object

If various donor groups are introduced to cyanobenzene to improve light emission characteristics, then emission efficiency increases, but the chemical structure becomes too complex to generalize

Engineering Contradiction:
Improvelight emission efficiencyVSAvoidchemical structure complexity
Core Design Contradiction:
Use of energy by moving objectVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the molecular structure into distinct functional segments: a cyanobenzene core (providing the acceptor functionality), donor groups at the 2-position (such as carbazol-9-yl), and aromatic substituents at positions 3, 4, and 5. This segmented approach allows systematic optimization of each segment's properties while maintaining an overall generalizable structural framework for designing delayed fluorescent materials.

Inventive Principle:
Principle #1Segmentation

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 compound achieves high light emission efficiency and long device lifetime with excellent durability, outperforming previous materials in terms of emission efficiency and stability.

Implementation Method 1

A delayed fluorescent material is a material which, in an excited state, after having undergone reverse intersystem crossing from an excited triplet state to an excited singlet state, emits fluorescence when returning back from the excited singlet state to a ground state thereof

Methodology Applied
Scientific EffectReverse intersystem crossing:

Implementation Method 2

emits fluorescence when returning back from the excited singlet state to a ground state thereof

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentUS20240298538A1Compound, light-emitting material, and light-emitting element
Publication Date: 2024.09.05 KYULUX INC
  • US20240298538A1 patent drawing
  • US20240298538A1 patent drawing
  • US20240298538A1 patent drawing

AI summary

A compound represented by the following general formula is an excellent light emitting material. R1 to R5 each represent a hydrogen atom, a deuterium atom, or a substituent other than a cyano group, but one or more of R1 to R5 is an aryl group or a pyridyl group, two or more of R1 to R5 are donor groups, and one or more of them are a substituted ring-fused indol-1-yl group (the number of rings constituting the fused ring is 4 or more).