Crosslinkable Electroactive Compounds for OLED Stability

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Solution Overview

Problem

There is a continuing need for improved electroactive materials in organic electronic devices, such as OLEDs, to enhance performance and longevity, particularly in terms of light emission and charge transport.

Innovation Solution

The development of novel electroactive compounds with specific structural formulas (e.g., Formula I, II, III) that include aryl groups, spiro or adamantyl linking groups, and crosslinkable substituents, which can be used to form layers in organic electronic devices, offering improved hole transport and electroluminescent properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If conventional organic electroactive materials are used in OLEDs, then device fabrication is straightforward, but device lifetime and stability are limited

Engineering Contradiction:
Improvedevice lifetimeVSAvoidfabrication complexity
Core Design Contradiction:
Duration of action of stationary objectVSEase of manufacture

Solution Approach 1:

The patent applies preliminary action by incorporating crosslinkable groups into the electroactive material structure before device assembly. These groups enable post-deposition crosslinking through UV irradiation or thermal treatment, which enhances device lifetime and stability without complicating the initial fabrication process. The crosslinking occurs after the device is assembled, allowing straightforward manufacturing followed by stability enhancement.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent changes the chemical parameter of the electroactive material by introducing crosslinkable functional groups (vinyl, epoxysilane, azide, alkyne) that can undergo chemical transformation. This parameter change from simple organic molecules to crosslinkable compounds enables improved device lifetime while maintaining ease of manufacture through solution processing and post-deposition crosslinking.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If electroactive materials with improved stability are developed, then device performance is enhanced, but material complexity increases

Engineering Contradiction:
Improvedevice stabilityVSAvoidmaterial structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies composite materials by combining electroactive functional groups with crosslinkable functional groups within the same molecule. This creates a composite structure where the electroactive portion maintains device performance while the crosslinkable portion provides stability. The modular design allows selection from various crosslinkable groups (vinyl, epoxysilane, azide, alkyne) without fundamentally changing the electroactive core structure.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies local quality by placing crosslinkable groups at specific locations on the electroactive molecule (such as on aromatic rings or as side chain substituents) rather than throughout the entire structure. This localized approach provides stability enhancement at key positions while maintaining the electroactive properties of the core structure, thus improving reliability without excessive complexity.

Inventive Principle:
Principle #3Local quality

3Adaptability or versatility

If crosslinkable groups are incorporated into electroactive materials, then air tolerance and processing flexibility improve, but synthesis complexity increases

Engineering Contradiction:
Improveprocessing flexibilityVSAvoidsynthesis complexity
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by separating the synthesis of the core electroactive structure from the introduction of crosslinkable groups. The electroactive core can be synthesized using conventional methods, and then crosslinkable groups are introduced in subsequent steps or through coupling reactions. This segmented approach allows independent optimization of electroactive properties and crosslinking capability, improving processing flexibility while managing synthesis complexity.

Inventive Principle:
Principle #1Segmentation

Data Source

PatentUS9685613B2Electroactive materials
Publication Date: 2017.06.20 LG CHEM LTD
  • US9685613B2 patent drawing
  • US9685613B2 patent drawing
  • US9685613B2 patent drawing

AI summary

There is disclosed a compound having Formula IIn Formula I:Ar1 through Ar4 are the same or different and are aryl groups;L is a spiro group, an adamantyl group, bicyclic cyclohexyl, deuterated analogs thereof, or substituted derivatives thereof;R1 is the same or different at each occurrence and is D, F, alkyl, aryl, alkoxy, silyl, or a crosslinkable group, where adjacent R1 groups can be joined together to form an aromatic ring;R2 is the same or different at each occurrence and is H, D, or halogen;a is the same or different at each occurrence and is an integer from 0-4; andn is an integer greater than 0.