Fluorene Hole-Transport Compounds for Thick-Layer OLEDs

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Solution Overview

Problem

Current OLED technologies face challenges in achieving improved performance metrics such as power efficiency, lifetime, and operating voltage, with a need for novel hole-transport and matrix materials that enable thicker layers without significant increases in operating voltage and maintain high thermal stability.

Innovation Solution

Development of specific organic compounds with tailored structures, such as those described by the general formula (1), which are suitable for use as hole-transport materials, hole-injection materials, or matrix materials in OLEDs, offering high charge-carrier mobility and stability, allowing for thicker layers with minimal increase in operating voltage.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If the layer thickness of hole-transport material is increased, then the device can accommodate thicker layers for improved structural stability, but the operating voltage increases and performance deteriorates

Engineering Contradiction:
Improvedevice lifetimeVSAvoidoperating voltage
Core Design Contradiction:
Duration of action of stationary objectVSUse of energy by moving object

Solution Approach 1:

The patent changes the molecular structure parameters of the hole-transport material by introducing specific fluorene substituents at positions 2, 3, or 4 of the triphenylene core. This structural parameter change results in improved charge-carrier mobility, which allows thicker layers to be used without a proportional increase in operating voltage, thus resolving the contradiction between layer thickness and voltage.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite molecular structures combining triphenylene cores with fluorene substituents to create hole-transport materials that exhibit superior charge-carrier mobility. This composite approach enables the material to maintain low operating voltages even when used in thicker layers, addressing the performance deterioration issue.

Inventive Principle:
Principle #40Composite materials

2Productivity

If conventional hole-transport materials are used, then the device structure is simple, but the charge-carrier mobility is insufficient leading to higher operating voltages

Engineering Contradiction:
Improvecharge-carrier mobilityVSAvoidmolecular structure complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies local quality by introducing fluorene substituents at specific positions (2, 3, or 4) of the triphenylene core. This localized modification at specific molecular positions enhances charge-carrier mobility in the hole-transport layer without requiring complex overall device structure, thus improving productivity while keeping device complexity manageable.

Inventive Principle:
Principle #3Local quality

3Reliability

If materials with high thermal stability are used, then the device can operate at higher temperatures improving reliability, but the material selection is limited

Engineering Contradiction:
Improvethermal stabilityVSAvoidmaterial selection flexibility
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The triphenylene-based compounds with fluorene substituents exhibit universal applicability as hole-transport materials that simultaneously provide high thermal stability and high charge-carrier mobility. These compounds can be used in various OLED configurations (fluorescent and phosphorescent) and device architectures, thus improving reliability while maintaining material selection flexibility through a single versatile molecular platform.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Data Source

PatentUS11997922B2Compounds and organic electronic devices
Publication Date: 2024.05.28 MERCK PATENT GMBH
  • US11997922B2 patent drawing
  • US11997922B2 patent drawing
  • US11997922B2 patent drawing

AI summary

The present invention relates to certain fluorenes, to the use of the compounds in an electronic device, and to an electronic device comprising at least one of these compounds. The present invention furthermore relates to a process for the preparation of the compounds and to a formulation and composition comprising one or more of the compounds.