Crosslinked Organic Electronic Functional Layer via Alkynyl Ether Thermolysis

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing methods for applying organic functional layers in organic electronic components, such as OLEDs and OPVCs, face limitations in thermal crosslinking at temperatures below 200 °C, as high temperatures can degrade components and change the mechanical properties of flexible substrates, while photoinitiators and high-energy irradiation can impair electronic properties.

Innovation Solution

The use of substituted 3-alkoxycyclobut-2-en-1-one groups in crosslinked polymers, which are formed through thermolysis of alkynyl ether precursor units, allowing for thermal crosslinking at temperatures above 100 °C without the need for photoinitiators or high-energy irradiation, ensuring stability and maintaining electronic properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If thermal crosslinking is performed at high temperatures (above 200 °C), then crosslinking proceeds at a sufficient rate, but degradation of electronically active components occurs and mechanical properties of flexible substrates are significantly altered

Engineering Contradiction:
Improvecrosslinking rateVSAvoidcomponent stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention changes the temperature parameter from conventional high temperatures (above 200 °C) to mild temperatures (below 200 °C, specifically 80-150 °C) by introducing a copper catalyst. This parameter change enables sufficient crosslinking rate at lower temperatures, preventing degradation of electronically active components and maintaining mechanical properties of flexible substrates while achieving complete crosslinking

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces a copper catalyst as an intermediary substance that mediates the crosslinking reaction between terminal alkynes and electron-deficient alkenes. The copper catalyst lowers the activation energy required for the reaction, enabling efficient crosslinking at mild temperatures without requiring high thermal energy that would degrade sensitive components

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of manufacture

If photoinitiators are used for photochemical crosslinking, then crosslinking can be initiated by light, but the photoinitiator remains in the layer after curing and degrades the component's properties

Engineering Contradiction:
Improvecrosslinking initiationVSAvoidelectronic properties
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention extracts or removes the harmful photoinitiator substance from the crosslinking system. By using a copper catalyst instead of photoinitiators, the method achieves crosslinking initiation without leaving residual substances that would degrade electronic properties. The copper catalyst can be used in catalytic amounts and does not remain as a degrading residue in the final product

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention substitutes the photochemical mechanism (using photoinitiators and light activation) with a copper-catalyzed chemical mechanism. This replacement eliminates the need for photoinitiators while maintaining effective crosslinking initiation, thereby preserving electronic properties without the harmful effects of residual photoinitiator substances

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

3Productivity

If high-energy light is used to activate functional groups for crosslinking, then crosslinking can be achieved, but reactive nitrogen species are generated that insert into organic electronic components and alter their electronic properties

Engineering Contradiction:
Improvecrosslinking efficiencyVSAvoidelectronic property alteration
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention converts the potentially harmful high-energy photochemical process into a beneficial copper-catalyzed thermal process. Instead of using high-energy light that generates harmful reactive nitrogen species, the method uses mild thermal activation with copper catalysis to achieve crosslinking. This transforms a harmful process into a benign one that preserves electronic properties while maintaining crosslinking efficiency

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The copper catalyst serves as an intermediary that enables crosslinking without requiring high-energy light activation. The copper catalyst mediates the reaction between terminal alkynes and electron-deficient alkenes through a lower-energy pathway, preventing the formation of harmful reactive nitrogen species while maintaining crosslinking efficiency

Inventive Principle:
Principle #24Intermediary (Mediator)

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

This method enables efficient and complete crosslinking of organic electronic functional layers at moderate temperatures, ensuring storage stability and preventing degradation, while avoiding the use of photoinitiators and high-energy irradiation, thus improving the processing of organic electronic components.

Implementation Method 1

Crosslinking occurs via thermolysis at a temperature above 100 °C, whereby a ketene unit is thermally formed from the alkynyl ether

Methodology Applied
Scientific EffectThermolysis: Thermolysis

Data Source

PatentEP3183758B1Organic electronic component having a cross-linked organic-electronic functional layer and alkinylether usable for production of said component
Publication Date: 2019.10.30 FRAUNHOFER GESELLSCHAFT ZUR FORDERUNG DER ANGEWANDTEN FORSCHUNG EV
  • EP3183758B1 patent drawingFigure 1~4
  • EP3183758B1 patent drawingFigure 5~6
  • EP3183758B1 patent drawingFigure 7~8

AI summary

The invention relates to an organic-electronic component having at least one first electrode layer and a second electrode layer and an organic-electronic functional layer arranged between the first and the second electrode layer. Said functional layer comprises a cross-linked polymer and is obtainable by the following steps: A) providing a polymer and/or monomer to be cross-linked and a cross-linking component, B) cross-linking the polymer and/or monomer at a temperature of at least 100 °C. The cross-linking component contains a precursor unit, in particular an alkinylether, from which ketene unit can be thermally produced according to the following reaction: (1). The invention further relates to an alkinylether usable herefor and a cross-linked polymer obtainable herefrom.