Crosslinkable Fluorene Compounds for LED Interlayers

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Solution Overview

Problem

Current electroluminescent devices face limitations in achieving efficient charge transport and long-term stability, particularly in the interlayers of multilayer LEDs, where improved hole injection and electron blocking are needed to enhance device efficiency and lifetime.

Innovation Solution

Development of novel 2,7-di(arylamino)fluorene compounds with crosslinkable moieties at the 9-position, which are used to create oligomers and polymers that form efficient hole injecting/transporting or electron blocking interlayers, offering reduced ionization potential and improved conductivity, along with the ability to form solvent-resistant films.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorene polymers are used in electroluminescent devices, then device fabrication is straightforward, but device efficiency and lifetime are insufficient due to poor charge transport and stability

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

Solution Approach 1:

The patent employs composite material design by incorporating crosslinkable moieties (vinyl, epoxy, or oxetane groups) into the fluorene polymer backbone. This creates a composite structure combining the charge transport capabilities of fluorene polymers with the stability and solvent resistance of crosslinked networks, thereby improving device lifetime while maintaining manageable structural complexity through systematic functional group integration

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies parameter changes by modifying the chemical structure of fluorene polymers to include crosslinkable functional groups at the 9-position. This structural parameter change enables post-polymerization crosslinking, which transforms the material properties to achieve superior stability and charge transport efficiency, directly addressing the reliability issue without requiring complete redesign of the polymer synthesis process

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If crosslinkable moieties are incorporated into fluorene compounds, then solvent resistance and film stability improve, but synthesis complexity increases

Engineering Contradiction:
Improvefilm solvent resistanceVSAvoidsynthesis complexity
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by separating the polymerization and crosslinking processes into distinct stages. The fluorene polymer is first synthesized with pendant crosslinkable groups, then subsequently crosslinked under controlled conditions. This segmentation allows each process to be optimized independently, improving solvent resistance while managing synthesis complexity through process decoupling

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent implements preliminary action by pre-installing crosslinkable functional groups (vinyl, epoxy, or oxetane) on the fluorene polymer chains during polymer synthesis. These pre-positioned groups are then activated for crosslinking after film formation, allowing the polymer to achieve both processability during fabrication and stability in the final device, thereby balancing manufacture ease with composition stability

Inventive Principle:
Principle #10Preliminary 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

The compounds demonstrate enhanced hole injecting/transporting or electron blocking properties, leading to improved device efficiency and extended lifetime, with the ability to form crosslinked, solvent-resistant films suitable for use in electronic devices like LEDs.

Implementation Method 1

crosslinkable substituted fluorene compounds... compounds are capable of being crosslinked to form solvent resistant films

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Data Source

PatentUS7956350B2Crosslinkable substituted fluorene compounds
Publication Date: 2011.06.07 SUMITOMO CHEM CO LTD
  • US7956350B2 patent drawing
  • US7956350B2 patent drawing
  • US7956350B2 patent drawing

AI summary

Novel 2,7-di(arylamino)-substituted fluorenes that are further substituted at the 9-position with one or more crosslinkable moieties, oligomers or polymers formed by crosslinking of said crosslinkable moieties, methods for their preparation, and use thereof in forming solvent resistant films having use as interlayers in electronic devices, especially electroluminescent devices.