p-Doped Mono-Triarylamine OLED Layers for Stable Charge Transport

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Solution Overview

Problem

Existing organic electroluminescent devices face challenges in long-term stability and performance data, particularly in conductivity and efficiency, despite advancements in using p-doped layers with host and dopant materials.

Innovation Solution

Incorporating a p-doped layer containing a monotriarylamine as a host and an electron acceptor compound as a dopant, with specific layer arrangements and dopant selection to enhance conductivity and stability, including layer structures like Anode - Layer A - Layer B - Emitting Layer, where Layer A and Layer B are organic layers with a monotriarylamine and a dopant, and optionally additional layers like Layer C with organic amines.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional hole-transport materials (such as triphenylamine and N,N'-dimethyltriphenylamine) are used as hosts in the hole-transport layer, then the device structure is simple, but the lifetime and efficiency of the electronic device are limited due to poor electron mobility and insufficient electron-transport capability

Engineering Contradiction:
Improvedevice lifetimeVSAvoidhost material structure
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the molecular structure of triphenylamine by introducing electron-withdrawing groups (such as fluorine atoms) at specific positions (e.g., 2,6-difluorotriphenylamine) to change the electronic parameters of the host material. This structural parameter change enhances electron mobility and electron-transport capability while maintaining the basic triphenylamine framework, thereby improving device lifetime without excessive complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite host materials that combine triphenylamine derivatives with electron-transporting moieties. These composite structures integrate the hole-transporting properties of triphenylamine with the electron-transporting capabilities of attached functional groups, creating materials that simultaneously provide both hole and electron transport functions, thus improving reliability

Inventive Principle:
Principle #40Composite materials

2Productivity

If the hole-transport layer uses materials with high hole mobility, then the charge transport efficiency is improved, but the electron transport capability is insufficient leading to accumulated electrons and reduced device lifetime

Engineering Contradiction:
Improvecharge transport efficiencyVSAvoiddevice lifetime
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent introduces electron-transporting functional groups (such as carbonyl, cyano, or fluorine substituents) at specific local positions on the triphenylamine molecule. This local modification creates regions within the molecule that are specialized for electron transport, while the overall molecule maintains its hole-transporting capability, thus achieving dual functionality and preventing electron accumulation

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

By changing the electronic parameters of the host material through strategic placement of electron-withdrawing groups, the patent adjusts the LUMO energy level and electron affinity of the material. This parameter change enables the material to accept and transport electrons effectively while maintaining high hole mobility, thereby improving both productivity and reliability

Inventive Principle:
Principle #35Parameter changes

3Productivity

If highly doped hole-transport layers are used to improve charge extraction, then the efficiency is improved, but the manufacturing precision and material stability are compromised due to sensitivity to dopant ratios and moisture

Engineering Contradiction:
Improvecharge extraction efficiencyVSAvoiddopant ratio control
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent designs self-doped hole-transport materials where the host molecule itself contains both electron-donating and electron-withdrawing moieties, enabling spontaneous charge transfer and intrinsic doping without requiring external dopant addition. This self-service mechanism eliminates the need for precise dopant ratio control during manufacturing, thereby improving manufacturing precision while maintaining high charge extraction efficiency

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent creates composite materials with intrinsic doping capability by combining electron-rich and electron-poor units within the same molecular structure. This composite design allows the material to self-regulate its doping level based on molecular structure rather than external dopant concentration, reducing sensitivity to manufacturing variations and improving material stability

Inventive Principle:
Principle #40Composite materials

4Ease of operation

If conventional hosts with deep HOMO levels are used, then the hole-transporting properties are adequate, but the electron affinity is low resulting in poor electron transport and reduced device lifetime

Engineering Contradiction:
Improvehole-transporting propertyVSAvoidelectron transport capability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent systematically adjusts the HOMO and LUMO energy level parameters of the host material by introducing electron-withdrawing groups at specific positions on the triphenylamine core. This parameter optimization maintains the deep HOMO level necessary for good hole transport while simultaneously raising the LUMO level to improve electron affinity and electron transport capability, thus improving reliability without sacrificing ease of operation

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 proposed structure significantly enhances the conductivity and stability of the electronic device, achieving conductivities above 10^-5 S/cm and improved long-term performance.

Implementation Method 1

at least one p-doped layer A containing a mono-triarylamine as a host, and at least one layer B containing a mono-triarylamine

Methodology Applied
Scientific EffectCharge transfer: Electron Paramagnetic Resonance

Implementation Method 2

an electron-transporting compound or a mixture comprising an electron-transporting compound and a dopant in the emitting layer

Methodology Applied
Scientific EffectElectron mobility: Electron Paramagnetic Resonance

Data Source

PatentEP4369378B1Electronic devices
Publication Date: 2026.05.20 MERCK PATENT GMBH
  • EP4369378B1 patent drawingFigure 1~2
  • EP4369378B1 patent drawingFigure 3~4
  • EP4369378B1 patent drawing

AI summary

The application relates to an electronic device comprising an anode, a cathode, at least one emitting layer between the anode and the cathode, at least one p-doped layer A containing a mono-triarylamine as a host, and at least one layer B containing a mono-triarylamine. The invention further relates to a p-doped mixture comprising a mono-triarylamine of formula (II), (III) or (IV) as a host and an electron acceptor compound as a dopant, and the use of the mixture in an electronic device.