Cross-linkable Ionic Compounds for OLED Dopant Stability

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Solution Overview

Problem

Existing organic light-emitting devices (OLEDs) face challenges in achieving long-term stability and efficiency due to non-radiative decay mechanisms and dopant migration, which affect the operational lifetime and performance, especially with phosphorescent materials.

Innovation Solution

The development of cross-linkable ionic compounds with reactive functional groups that can be used as conductivity dopants, allowing for cross-linking with host charge transport compounds to form stable organic layers, reducing dopant migration and enhancing the structural integrity of OLEDs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional conductivity dopants are used in OLEDs, then the device can achieve initial conductivity, but dopant migration occurs leading to reduced operational lifetime and performance degradation

Engineering Contradiction:
Improveoperational lifetimeVSAvoiddopant stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies preliminary action by introducing reactive functional groups (vinyl, acrylate, epoxide, oxetane, norbornene, trifluoroethylene, benzocyclobutene, siloxane, maleimide, cyanate ester, ethynyl, nadimide, phenylethynyl, biphenylene, phthalonitrile, or boronic acid) into the dopant molecular structure before device operation. These pre-installed reactive groups enable subsequent cross-linking with host charge transport compounds under operational conditions, transforming the dopant from a migratory species into a fixed, cross-linked component of the organic layer, thereby preventing dopant migration and extending operational lifetime

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent employs composite materials by creating a cross-linked network structure where dopant molecules with reactive functional groups form covalent bonds with host charge transport compounds. This composite structure integrates the dopant into the host matrix through chemical bonding, forming a stable, unified material system that prevents phase separation and dopant migration while maintaining electrical conductivity functionality

Inventive Principle:
Principle #40Composite materials

2Use of energy by moving object

If phosphorescent materials are used to enhance light emission, then device efficiency improves, but non-radiative decay mechanisms increase leading to reduced operational lifetime

Engineering Contradiction:
Improvelight emission efficiencyVSAvoidoperational lifetime
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent applies preliminary action by pre-equipping dopant molecules with reactive functional groups that will later form cross-links with phosphorescent host materials. This preliminary structural preparation enables the dopant to become chemically anchored to the phosphorescent emitting layer, preventing dopant migration that would otherwise cause quenching of phosphorescence and non-radiative decay, thereby preserving both efficiency and operational lifetime

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent applies preliminary anti-action by introducing cross-linkable functional groups that proactively prevent harmful dopant migration before it can occur. This preventive chemical bonding approach counteracts the natural tendency of dopants to migrate and cause non-radiative decay in phosphorescent OLEDs, thereby protecting the operational lifetime while maintaining the efficiency benefits of phosphorescent materials

Inventive Principle:
Principle #9Preliminary anti-action

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 approach results in improved operational lifetimes and consistent performance of OLEDs, particularly with phosphorescent materials, by preventing dopant leakage into the emissive layer and enhancing the stability of the organic layers.

Implementation Method 1

cross-linking with host charge transport compounds to form stable organic layers

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentUS9184394B2Cross linkable ionic compounds
Publication Date: 2015.11.10 UNIVERSAL DISPLAY CORP
  • US9184394B2 patent drawing
  • US9184394B2 patent drawing
  • US9184394B2 patent drawing

AI summary

Ionic compounds comprising: (a) a cationic radical of a charge transporting compound which has one or more reactive groups; and (b) a counter anion. The ionic compound may have the following formula:The reactive functional groups on the cation allow the ionic compound to cross-link with a host charge transport compound. Such ionic compounds may have various properties, such as thermodynamic stability, hole injection/transport capabilities, electrochemical durability, and/or solubility in organic solvents that allows them to be useful in organic electronic devices. Also provided are electronic devices made using the ionic compounds of the present invention, and methods of making an electronic device.