Bispyrimidine Electron Transport Materials for OLED Stability

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Solution Overview

Problem

There is a need for new electron transport materials in organic light emitting devices to improve efficiency, stability, manufacturability, and spectral characteristics, as existing materials do not adequately address these requirements.

Innovation Solution

Compounds containing two pyrimidine moieties are developed as electron transporting materials, which can prevent holes or excitons from entering the electron transport layer, offering improved efficiency and durability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional electron transport materials are used in organic light emitting devices, then the devices can operate, but the efficiency, stability, and manufacturability are insufficient

Engineering Contradiction:
ImprovestabilityVSAvoidmanufacturability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure of electron transport materials by introducing specific pyrimidine derivatives with tailored substituents (Ar1, Ar2, R33) to optimize electronic properties. This structural parameter change enables simultaneous improvement in stability and manufacturability by achieving better material performance and processability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs composite molecular structures combining pyrimidine cores with various aromatic substituents (biaryl groups, naphthyl groups, etc.). These composite structures integrate the beneficial properties of different moieties to achieve enhanced stability while maintaining ease of manufacture through established synthesis routes

Inventive Principle:
Principle #40Composite materials

2Productivity

If existing electron transport materials are used, then device operation is achieved, but efficiency and spectral characteristics are not optimized

Engineering Contradiction:
Improveoperational efficiencyVSAvoidspectral characteristics
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent optimizes operational efficiency by changing key molecular parameters including HOMO-LUMO energy levels, electron mobility, and molecular packing. The specific pyrimidine derivative structures are designed to achieve optimal energy levels for efficient electron transport and improved device productivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces specific local structural features (pyrimidine rings with particular substituents at defined positions) that provide localized electronic properties. This local quality optimization enables fine-tuning of spectral characteristics and efficiency without requiring complete redesign of the entire molecular structure

Inventive Principle:
Principle #3Local quality

3Duration of action of stationary object

If conventional materials are used in electron transport layer, then basic device function is achieved, but durability is insufficient

Engineering Contradiction:
ImprovedurabilityVSAvoidmaterial stability
Core Design Contradiction:
Duration of action of stationary objectVSQuantity of substance

Solution Approach 1:

The patent enhances durability by modifying material parameters such as thermal stability, oxidative stability, and morphological stability. The pyrimidine derivative structures are specifically designed with substituents that improve these parameters, leading to enhanced durability during device operation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs small molecule pyrimidine derivatives that can be processed from solution, replacing less stable conventional materials. These materials offer improved durability while maintaining ease of processing, effectively replacing short-lived or unstable materials with more durable alternatives

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Data Source

PatentEP2651904B1Bispyrimidines for electronic applications
Publication Date: 2014.11.12 BASF SE
  • EP2651904B1 patent drawing
  • EP2651904B1 patent drawing
  • EP2651904B1 patent drawing

AI summary

The present invention relates to compounds of formula (I), or (II), a proc ess for their production and their use in electronic devices, especially electroluminescent devices. When used as electron transport material in electroluminescent devices, the compounds of formula I, or II may provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.