Diels-Alder Crosslinkable Polymer for OLED Device Lifetime

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Solution Overview

Problem

Current crosslinkable polymer optoelectronic materials for solution-processed OLEDs have limitations in device lifetime and performance, necessitating the development of new high-performance charge transporting materials.

Innovation Solution

A crosslinkable polymer mixture based on a Diels-Alder reaction, comprising a conjugated polymer with conjugated diene and dienophile functional groups, which forms a three-dimensional insoluble and infusible network upon heating or acid catalysis, offering excellent solvent resistance and enabling efficient solution processing for multilayer optoelectronic devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional crosslinking methods (heating, illumination) are used to improve solvent resistance, then device lifetime is improved, but processing time and temperature increase

Engineering Contradiction:
Improvedevice lifetimeVSAvoidprocessing time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The patent changes the chemical parameters of the crosslinking reaction by introducing Diels-Alder reactive groups (conjugated diene and dienophile) that react at lower temperatures and shorter times compared to conventional crosslinking methods, thereby reducing processing time while maintaining device lifetime

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses a composite polymer structure combining conjugated diene units and dienophile units in the same polymer chain, enabling intramolecular crosslinking that proceeds faster and at lower temperatures than conventional intermolecular crosslinking methods

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If solution processing method is used to prepare multilayer devices, then manufacturing cost is reduced and large-area application is enabled, but interface miscibility and interface corrosion occur

Engineering Contradiction:
Improvemanufacturing costVSAvoidinterface corrosion
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent applies preliminary crosslinking action to the first layer before applying subsequent layers. The crosslinking groups in the first layer react to form a solvent-resistant network structure before the second layer is deposited, preventing solvent from the second layer from dissolving or corroding the first layer interface

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent inverts the conventional sequence by crosslinking the first layer in situ before depositing the second layer, rather than crosslinking after complete device assembly. This reversal prevents interface corrosion by establishing solvent resistance before subsequent solvent processing steps

Inventive Principle:
Principle #13The other way round (Inversion)

3Stability of the object's composition

If crosslinking groups are introduced to improve solvent resistance, then interface miscibility is prevented, but device lifetime is limited

Engineering Contradiction:
Improvesolvent resistanceVSAvoiddevice lifetime
Core Design Contradiction:
Stability of the object's compositionVSDuration of action of stationary object

Solution Approach 1:

The patent creates a composite polymer structure with conjugated diene and dienophile units that enable Diels-Alder crosslinking, forming a three-dimensional network that provides both excellent solvent resistance and enhanced device lifetime through improved interfacial stability

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent changes the chemical reactivity parameters by using Diels-Alder crosslinking groups that form stable crosslinked structures at lower temperatures and shorter times, improving both solvent resistance and device lifetime without the degradation issues associated with conventional high-temperature crosslinking

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 Diels-Alder reaction allows for the formation of a polymer film with enhanced optical and electrical properties, improved solvent resistance, and reduced processing time and temperature, facilitating the production of high-performance multilayer polymer optoelectronic devices with extended device lifetime.

Implementation Method 1

a crosslinkable mixture constructed based on a Diels-Alder reaction... the conjugated diene functional group and the dienophile functional group can undergo a Diels-Alder reaction

Methodology Applied
Scientific EffectDiels-Alder reaction: Chemical Bonding

Implementation Method 2

undergo a Diels-Alder reaction to crosslink... under heating or acid catalysis

Methodology Applied
Scientific EffectThermal activation: Heating

Data Source

PatentUS11292875B2Cross-linkable polymer based on Diels-Alder reaction and use thereof in organic electronic device
Publication Date: 2022.04.05 GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS LTD
  • US11292875B2 patent drawing
  • US11292875B2 patent drawing
  • US11292875B2 patent drawing

AI summary

Provided is a mixture which can be subjected to a Diels-Alder reaction, comprising polymer (I) and polymer (II), wherein the structures of the polymer (I) and the polymer (II) are as shown in (I),wherein x1, y1, x2, y2, z1 and z2 are percentage molar contents; said x1 is >0, x2 is >0, y1 is >0, y2 is >0, z1 is ≥0, and z2 is ≥0; x1+y1+z1=1, and x2+y2+z2=1; Ar1, Ar2, Ar2-1, Ar3, Ar4 and Ar4-1 are each independently selected from: an aryl, or heteroaryl group containing 5-40 ring atoms; R1 and R2 are each independently a linking group; D is a conjugated diene functional group, and A is a dienophilic functional group; and n1 is greater than 0, and n2 is greater than 0. The mixture for a Diels-Alder reaction has a very good optical performance.