Cyanobenzene Derivative Light-Emitting Material Efficiency

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Solution Overview

Problem

Existing organic electroluminescent devices using carbazole and indole structures as host materials for light-emitting layers do not consistently achieve high light emission efficiency, and the relationship between chemical structure and usefulness as light-emitting compounds is not well understood.

Innovation Solution

A cyanobenzene derivative with a carbazole or indole structure is used as a light-emitting material, specifically a compound represented by certain general formulas that include cyano groups, to enhance light emission efficiency in organic light-emitting devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a compound containing a carbazole structure and/or an indole structure is used as a host material of a light-emitting layer, then the device can be constructed with known materials, but the light emission efficiency is not necessarily high

Engineering Contradiction:
Improvelight emission efficiencyVSAvoidcompound structure variety
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent introduces specific parameter changes by incorporating cyano groups at defined positions (R1-R5) of the carbazole or indole core structure. This chemical parameter modification transforms ordinary host materials into efficient delayed fluorescent emitters, directly resolving the contradiction between using known material structures and achieving high light emission efficiency.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining carbazole or indole frameworks with cyano groups and various substituents (R1-R5). This composite approach integrates the structural stability of carbazole/indole with the optical properties of cyano groups, achieving both reliability in efficiency and versatility in molecular design.

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If various carbazole and indole compounds are studied as host materials, then material options increase, but the light emission efficiency remains inconsistent

Engineering Contradiction:
Improvematerial selection rangeVSAvoidlight emission efficiency
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent establishes specific parameter requirements for high efficiency: cyano groups must be present at least at one position among R1-R5, and R21-R28 must satisfy specific structural conditions. These parameter specifications filter the vast material selection range down to a focused set of high-performance compounds, ensuring consistent light emission efficiency.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent identifies and copies the successful structural pattern from PTL 1 (the carbazole-indole compound with good efficiency) into a generalized formula (1). By copying this proven structural motif and systematically varying substituents, the patent maintains high efficiency while exploring material versatility.

Inventive Principle:
Principle #26Copying

3Ease of manufacture

If the chemical structure of light-emitting compounds is not well understood, then material design flexibility is high, but predicting usefulness as light-emitting materials becomes difficult

Engineering Contradiction:
Improvematerial design flexibilityVSAvoidusefulness prediction accuracy
Core Design Contradiction:
Ease of manufactureVSMeasurement precision

Solution Approach 1:

The patent transforms material design from flexible but unpredictable to constrained but predictable by establishing specific parameter rules: cyano groups at R1-R5, specific structures for R21-R28, and defined relationships among substituents. These parameters enable accurate prediction of light-emitting usefulness while maintaining design flexibility within the established framework.

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 use of these cyanobenzene derivatives as light-emitting materials significantly enhances the light emission efficiency of organic electroluminescent devices, achieving high light emission with delayed fluorescent characteristics.

Implementation Method 1

the inventors have found a compound that is useful as a delayed fluorescent material in cyanobenzene derivatives containing a carbazole structure, an indole structure and the like

Methodology Applied
Scientific EffectDelayed fluorescence: Fluorescence

Implementation Method 2

An organic light-emitting device, such as an organic electroluminescent device (organic EL device)

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS10276803B2Organic light-emitting device, and light-emitting material and compound used therefor
Publication Date: 2019.04.30 KYULUX INC
  • US10276803B2 patent drawing
  • US10276803B2 patent drawing
  • US10276803B2 patent drawing

AI summary

An organic light-emitting device having a light-emitting layer containing a compound represented by the general formula below has a high light emission efficiency. In the general formula, at least one of R1 to R5 represents a cyano group, at least one of R1 to R5 represents a 9-carbazolyl group, a 1,2,3,4-tetrahydro-9-carbazolyl group, a 1-indolyl group or a diarylamino group, and the balance of R1 to R5 represents a hydrogen atom or a substituent.