Formula I Organic Compound Thermal Stability

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Solution Overview

Problem

There is a need to improve the thermal properties and LUMO energy level of compounds of Formula (I) used in organic electronic devices, as well as to reduce their environmental impact and toxicity.

Innovation Solution

The development of a compound of Formula (I) with a specific metal ion (M) and ligand (L) structure, where the ligand contains at least one CF2R group and the negative charge is delocalized over the β-dicarbonyl group and aryl groups, enhancing thermal stability and suitable LUMO energy levels for organic electronic devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If compounds of Formula (I) are used in organic electronic devices, then charge injection efficiency is improved, but thermal stability and LUMO energy level need improvement

Engineering Contradiction:
Improvecharge injection efficiencyVSAvoidthermal stability
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent modifies the chemical structure of compounds by introducing specific substituents (CF2R groups at positions 5 and 6 of the pyridine ring) to change the LUMO energy level and thermal properties. This structural parameter change achieves both improved charge injection efficiency and enhanced thermal stability without compromising either property.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining a pyridine core with β-dicarbonyl ligands containing CF2R groups. This composite approach integrates multiple functional elements (electron-withdrawing CF2R groups for LUMO level adjustment, β-dicarbonyl for thermal stability) into a single molecule that simultaneously achieves both improved charge injection and thermal properties.

Inventive Principle:
Principle #40Composite materials

2Reliability

If compounds of Formula (I) are used in organic electronic devices, then device performance is improved, but environmental impact and toxicity increase

Engineering Contradiction:
Improvedevice performanceVSAvoidenvironmental impact and toxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent employs organic compounds with designed molecular structures that can be degraded or replaced more easily than traditional materials. The specific CF2R-substituted pyridine compounds are engineered to balance performance with reduced environmental persistence, allowing device functionality while minimizing long-term ecological impact.

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

Solution Approach 2:

By modifying molecular parameters (introducing CF2R groups), the patent adjusts the compound's environmental behavior while maintaining or improving device performance. The structural changes affect both electronic properties (LUMO level) and environmental properties (toxicity, degradability) simultaneously.

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 compounds of Formula (I) exhibit improved thermal properties, including melting point, weight loss in TGA, decomposition temperature, and rate onset temperature, while maintaining suitable LUMO energy levels for efficient charge injection in organic electronic devices, and potentially reducing environmental impact and toxicity.

Implementation Method 1

The negative charge in the compounds of Formula (I) may be delocalised partially or fully over the β-dicarbonyl group and optionally also over the aryl group(s)

Methodology Applied
Scientific EffectCharge delocalization:

Data Source

PatentEP4570808A1Compound of formula (i), organic electronic device comprising a compound of formula (i), display device comprising the organic electronic device as well as compounds of formula (i) for use in organic electronic devices
Publication Date: 2025.06.18 NOVALED GMBH
  • EP4570808A1 patent drawingFigure 1~2
  • EP4570808A1 patent drawingFigure 3~4
  • EP4570808A1 patent drawingFigure 5~6

AI summary

The present invention relates to a compound of formula (I) as well as to an organic electronic device comprising a semiconductor layer which comprises a compound of formula (I).