OLED Hole-Transport Materials for Low-Barrier Hole Injection

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Solution Overview

Problem

Existing OLED materials face challenges in achieving efficient hole-injection due to the barrier created by the work function mismatch between common anode materials and hole-transport materials, leading to increased operating voltage and suboptimal performance.

Innovation Solution

Development of novel electron-acceptor compounds, specifically represented by formulas (3a) and (5a), which serve as p-dopants or main components in hole-transport layers, addressing the hole-injection barrier and enhancing charge-carrier balance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a p-dopant is used to improve hole-injection, then hole-injection properties are improved, but device complexity increases

Engineering Contradiction:
Improvehole-injection propertiesVSAvoiddevice complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent combines the hole-transport material and p-dopant into a single integrated compound structure. The electron-accepting unit is directly incorporated into the hole-transporting core, eliminating the need for separate doping components while maintaining both hole-transport and hole-injection functions simultaneously.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The compounds of formula (I) serve multiple functions within a single molecular structure: they act as hole-transporting materials, p-dopants, and hole-injection materials simultaneously. This multi-functionality resolves the contradiction by providing improved hole-injection properties without increasing device complexity, as one compound fulfills multiple roles that would traditionally require separate components.

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

2Reliability

If electron-acceptor compounds are used as main component, then hole-injection properties are improved, but light absorption in visible region increases

Engineering Contradiction:
Improvehole-injection propertiesVSAvoidlight absorption in visible region
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies local quality by designing the electron-accepting unit with specific substituents (such as fluoro, cyano, or trifluoromethyl groups) that are strategically positioned on the molecular structure. These localized modifications enhance electron-accepting capability for improved hole-injection while the overall molecular framework is designed to minimize broad visible light absorption, thus reducing the harmful effect on OLED emission characteristics.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent optimizes the molecular parameters of the electron-acceptor compounds, specifically adjusting the HOMO and LUMO energy levels through structural modifications. By changing these electronic parameters, the compounds achieve strong electron-accepting properties for effective hole-injection while their optical absorption spectrum is tuned to minimize overlap with the visible emission region, thereby reducing harmful light absorption.

Inventive Principle:
Principle #35Parameter changes

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 novel compounds improve OLED performance by reducing operating voltage, increasing efficiency, and extending device lifetime while minimizing light absorption in the visible region, thus optimizing charge-carrier mobility and injection.

Implementation Method 1

The present invention provides an electron-acceptor material as a p-dopant or as a main component in a hole-transporting layer selected from hole-injection layers, hole-transport layers and electron-blocking layers, for use in electronic devices

Methodology Applied
Scientific EffectElectron acceptance:

Implementation Method 2

For good performance data, good mobilities of the charge carriers in the hole-transport layers and good hole-injection properties are particularly crucial

Methodology Applied
Scientific EffectCharge-carrier transport: Conduction (electrical)

Implementation Method 3

The absolute value of the work function of commonly used transparent anode material indium-tin oxide is typically below the absolute value of the highest occupied molecular orbital (HOMO) energies of common hole-transport materials. Thus, there is a barrier for hole-injection into the hole-transport layer

Methodology Applied
Scientific EffectWork function matching:

Implementation Method 4

The materials should also exhibit appropriate morphologies (molecular planarity). Furthermore, the materials employed as electron-acceptor materials (for example as p-dopants or as main components in a hole-injection layer) in an OLED should absorb as little light as possible in the visible region (VIS region)

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentEP3765444B1Materials for organic electroluminescent devices
Publication Date: 2026.01.14 MERCK PATENT GMBH
  • EP3765444B1 patent drawing
  • EP3765444B1 patent drawing
  • EP3765444B1 patent drawing

AI summary

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.