Acridine Spiro Compounds for OLED Emission Efficiency

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Solution Overview

Problem

Current studies on acridine structure-having spiro compounds for organic electroluminescence elements have not thoroughly explored their potential as light-emitting materials, lacking a comprehensive understanding of their chemical structure's relationship to their usefulness and facing challenges in synthesis and application.

Innovation Solution

Development of specific acridine structure-having spiro compounds as dopants in the light-emitting layer of organic electroluminescence elements, utilizing a general formula that includes electron-donating and electron-withdrawing groups to enhance emission efficiency, and employing these compounds as thermally-activated delayed fluorescence materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If acridine structure-having spiro compounds are used as light-emitting materials in organic electroluminescence elements, then emission efficiency can be improved, but the synthesis difficulty increases and comprehensive understanding of structure-usefulness relationship is lacking

Engineering Contradiction:
Improveemission efficiencyVSAvoidsynthesis difficulty
Core Design Contradiction:
Loss of energyVSEase of manufacture

Solution Approach 1:

The patent systematically varies chemical structure parameters of acridine spiro compounds, including substituent types (electron-donating groups like phenyl, naphthyl; electron-withdrawing groups like carbonyl, cyano), substituent positions, and molecular configurations to establish structure-emission efficiency relationships. This parametric approach enables identification of optimal molecular structures that achieve high emission efficiency while maintaining reasonable synthesis feasibility

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops a universal design framework for acridine spiro compounds that can serve multiple functions: as dopants in light-emitting layers, as host materials, and as thermally-activated delayed fluorescence materials. The general formula (1) with defined substituent patterns provides a versatile platform for creating compounds with tailored emission characteristics across different device configurations

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Loss of information

If comprehensive studies on all acridine structure-having spiro compounds are conducted to establish structure-usefulness relationships, then the understanding of light-emitting material properties improves, but the time and resources required increase significantly

Engineering Contradiction:
Improvestructure-usefulness relationship understandingVSAvoidresearch time
Core Design Contradiction:
Loss of informationVSLoss of time

Solution Approach 1:

The patent segments the comprehensive study into systematic subsets based on chemical structure categories: compounds with specific electron-donating groups (phenyl, naphthyl, dibenzofuran), electron-withdrawing groups (carbonyl, cyano, carboxyl), and structural configurations (spiro-fused, spiro-connected). This segmentation enables focused investigation of structure-emission relationships without requiring exhaustive testing of all possible derivatives

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent performs preliminary structure-activity relationship analysis by evaluating representative compounds from each structural category before optimizing specific derivatives. This preliminary characterization of general structure-emission trends guides subsequent targeted synthesis and device fabrication, reducing overall research time by avoiding trial-and-error approaches

Inventive Principle:
Principle #10Preliminary action

3Loss of energy

If expensive rare metals are used to achieve high emission efficiency in organic electroluminescence elements, then emission performance improves, but the production cost increases

Engineering Contradiction:
Improveemission efficiencyVSAvoidproduction cost
Core Design Contradiction:
Loss of energyVSQuantity of substance

Solution Approach 1:

The patent replaces expensive rare metal complexes (such as iridium and platinum phosphorescent emitters) with organic acridine spiro compounds that achieve comparable or superior emission efficiency through thermally-activated delayed fluorescence mechanisms. These organic compounds are based on abundant elements (C, H, O, N) and can be synthesized cost-effectively, eliminating dependence on scarce precious metals while maintaining high external quantum efficiency

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent substitutes the phosphorescence mechanism based on heavy metal coordination chemistry with a purely organic thermally-activated delayed fluorescence mechanism. This substitution eliminates the need for rare metal centers and their associated coordination spheres, replacing them with organic molecular structures that utilize intramolecular charge transfer and reverse intersystem crossing processes to achieve efficient light emission

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 electroluminescence elements exhibit high emission efficiency and are cost-effective to produce, utilizing the acridine structure-having spiro compounds as valuable light-emitting materials without the need for expensive rare metals.

Implementation Method 1

employing these compounds as thermally-activated delayed fluorescence materials

Methodology Applied
Scientific EffectThermally-activated delayed fluorescence: Fluorescence

Implementation Method 2

organic electroluminescence element having a high emission efficiency

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentEP2733762B1Organic electroluminescence element and compound used therein
Publication Date: 2018.11.28 KYULUX INC
  • EP2733762B1 patent drawingFigure 1~2
  • EP2733762B1 patent drawingFigure 3~4
  • EP2733762B1 patent drawingFigure 5~6

AI summary

An organic electroluminescence element in which a compound represented by the general formula below is used in a light-emitting layer exhibits a high emission efficiency and is inexpensive to provide. At least one of R1 to R8 and R17 represent an electron-donating group and the others represent a hydrogen atom; at least one of R9 to R16 represent an electron-withdrawing group that does not have an unshared electron pair at the α-position thereof and the others represent a hydrogen atom; Z represents a single bond or >C=Y; Y represents O, S, C (CN) 2 or C(COOH)2; provided that when Z is a single bond, then at least one of R9 to R16 is an electron-withdrawing group that does not have an unshared electron pair at the α-position thereof.