Novel Fluorene Compounds for OLED Hole-Transport Layers

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Solution Overview

Problem

Current OLEDs face challenges in achieving improved performance metrics such as power efficiency, lifetime, and operating voltage, particularly due to limitations in hole-transport materials that increase voltage with thicker layers and lack of suitable matrix materials for phosphorescent dopants.

Innovation Solution

Development of novel organic compounds with specific structural formulas that serve as hole-transport materials, exciton-blocking materials, or matrix materials in OLEDs, enhancing charge-carrier mobility and stability, allowing for thicker layers with minimal voltage increase and improved efficiency and lifetime.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the layer thickness of the hole-transport layer is increased, then the performance of OLEDs is improved, but the operating voltage increases

Engineering Contradiction:
ImproveOLED performanceVSAvoidoperating voltage
Core Design Contradiction:
ReliabilityVSUse of energy by stationary object

Solution Approach 1:

The patent changes the chemical structure parameters of hole-transport materials by introducing specific substituents (e.g., dibenzofuran, dibenzothiophene groups) and modifying molecular weight, which fundamentally alters the material's charge carrier mobility characteristics. This enables thicker layers to be used without the proportional voltage increase that would otherwise occur

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material strategies by combining different functional groups (aromatic hydrocarbons with heterocyclic groups) to create new hole-transport materials that exhibit synergistic properties, achieving both high charge carrier mobility and suitability for thicker layer configurations

Inventive Principle:
Principle #40Composite materials

2Length of stationary object

If novel hole-transport materials with high charge-carrier mobility are used, then thicker hole-transport layers can be achieved, but the complexity of material synthesis increases

Engineering Contradiction:
Improvehole-transport layer thicknessVSAvoidmaterial synthesis
Core Design Contradiction:
Length of stationary objectVSEase of manufacture

Solution Approach 1:

The patent segments the hole-transport material structure into distinct functional modules (core aromatic hydrocarbon units with specific heterocyclic substituents), allowing systematic design and synthesis while maintaining high charge carrier mobility. This modular approach facilitates controlled synthesis of thicker-layer-appropriate materials

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent systematically varies molecular parameters (substituent types, positions, and combinations) to optimize charge carrier mobility for thicker layers, while the methodical approach to structural modification actually streamlines the synthesis process by building upon established chemical transformations

Inventive Principle:
Principle #35Parameter changes

3Duration of action of stationary object

If compounds with high thermal stability and high glass-transition temperature are used, then OLED lifetime is improved, but the difficulty of processing these compounds increases

Engineering Contradiction:
ImproveOLED lifetimeVSAvoidcompound processing
Core Design Contradiction:
Duration of action of stationary objectVSEase of manufacture

Solution Approach 1:

The patent optimizes the balance between thermal stability parameters (glass-transition temperature, molecular weight) and processing characteristics by selecting specific aromatic hydrocarbon cores and substituent combinations. This enables compounds to achieve high lifetime performance while remaining processable through conventional OLED manufacturing techniques

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces specific local structural features (such as dibenzofuran or dibenzothiophene groups at particular positions) that locally enhance thermal stability without compromising overall processability, allowing the material to exhibit high glass-transition temperature while maintaining suitable solubility and deposition characteristics

Inventive Principle:
Principle #3Local quality

Data Source

PatentUS9595681B2Compounds and organic electroluminescent devices
Publication Date: 2017.03.14 MERCK PATENT GMBH
  • US9595681B2 patent drawing
  • US9595681B2 patent drawing
  • US9595681B2 patent drawing

AI summary

The present invention concerns particular fluorenes, the use of the compound in an electronic device, and an electronic device containing at least one of these compounds. The present invention further concerns a method for producing the compound and a formulation and composition containing one or more of the compounds.