Organic Semiconductor Compounds for Thermal Stability

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Solution Overview

Problem

There is a need for organic electronic devices with transparent, thermally stable, and dopable semiconducting materials that can efficiently transfer charge and energy, while maintaining high conductivity and ease of synthesis.

Innovation Solution

The development of a semiconducting layer using specific organic compounds with a formula that allows for n-doping, featuring a wide electronic band gap and high glass transition temperature, ensuring high thermal stability and transparency, which can be synthesized cost-effectively and used in various organic electronic devices such as OLEDs and field-effect transistors.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional organic semiconducting materials are used, then the device can be manufactured, but the thermal stability and conductivity are insufficient

Engineering Contradiction:
Improvethermal stabilityVSAvoidease of synthesis
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure parameters of organic semiconducting materials by introducing specific dibenzacridine core structures with varying substituents (R1-R6 groups), achieving enhanced thermal stability (glass transition temperature Tg > 100°C) while maintaining synthetic accessibility through established organic synthesis methods

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite organic semiconducting materials combining dibenzacridine core structures with various aromatic substituents (phenyl, naphthyl, thiophen, etc.), achieving a balance between thermal stability, electrical conductivity, and ease of synthesis by selecting appropriate substituent groups

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If transparent organic semiconducting materials are used, then the device transparency is improved, but the conductivity and charge carrier mobility are reduced

Engineering Contradiction:
ImprovetransparencyVSAvoidconductivity
Core Design Contradiction:
Illumination intensityVSReliability

Solution Approach 1:

The patent applies local quality by designing specific regions of the molecule with different functions: the dibenzacridine core provides structural stability and appropriate band gap for transparency, while specific substituent groups (such as electron-donating or electron-withdrawing groups) are introduced at localized positions to enhance charge carrier mobility and conductivity without compromising overall transparency

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent optimizes the HOMO-LUMO energy gap parameter to maintain transparency in the visible range while introducing dopable groups that can accept or donate electrons, enabling high conductivity when doped. The glass transition temperature is raised above 100°C to ensure thermal stability during device operation

Inventive Principle:
Principle #35Parameter changes

3Temperature

If high glass transition temperature materials are used, then the thermal stability is improved, but the charge carrier mobility is reduced

Engineering Contradiction:
Improveglass transition temperatureVSAvoidcharge carrier mobility
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent carefully balances the glass transition temperature parameter (raising it above 100°C for thermal stability) while optimizing molecular packing and intermolecular interactions through substituent selection to maintain adequate charge carrier mobility. The molecular structure is designed to allow sufficient molecular motion for charge transport while maintaining structural order for high Tg

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2312663B1Organic electronic device comprising an organic semiconducting material
Publication Date: 2014.10.15 NOVALED GMBH
  • EP2312663B1 patent drawingFigure 1
  • EP2312663B1 patent drawing
  • EP2312663B1 patent drawing

AI summary

The present invention relates to an organic electronic device comprising an organic semiconducting material comprising at least one compound according to the following formula: wherein R1-4 are independently selected from H, halogen, CN, substituted or unsubstituted C1-C20-alkyl or heteroalkyl, C6-C20-aryl or C5-C20-heteroaryl, C1-C20-alkoxy or C6-C20-aryloxy.