Benzotriazole Derivatives for OLED Hole-Blocking and Electron Transport

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Solution Overview

Problem

Existing organic electroluminescent devices face challenges with materials that lack stability and sufficient hole-blocking capabilities, leading to low electron-transporting capability and durability issues, particularly with materials like TAZ and BCP, which have low electron-transporting efficiency and thermal stability.

Innovation Solution

The use of novel benzotriazole derivatives as electron-transporting, hole-blocking, or injection layers in organic electroluminescent devices, which exhibit high electron injection and migration rates, excellent hole-blocking power, and stability in thin-film form, enhancing the devices' efficiency and durability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If TAZ is used as electron-transporting material to achieve high hole-blocking capability, then hole-blocking power is improved, but electron-transporting capability deteriorates

Engineering Contradiction:
Improvehole-blocking capabilityVSAvoidelectron-transporting capability
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention modifies the molecular structure of TAZ by introducing electron-withdrawing groups (such as fluorine atoms at positions 4 and 5 of the phenyl ring) to change the electronic parameters of the material. This structural modification optimizes the balance between hole-blocking capability and electron-transporting capability, allowing the material to achieve both high hole-blocking power and sufficient electron mobility.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If BCP is used as hole-blocking material to achieve high hole-blocking power, then hole-blocking capability is improved, but thermal stability deteriorates

Engineering Contradiction:
Improvehole-blocking capabilityVSAvoidthermal stability
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The invention creates a composite material system by combining the benzotriazole derivative (providing hole-blocking capability) with electron-transporting materials. This composite approach allows the device to achieve both high hole-blocking power and improved thermal stability, as the benzotriazole-based compound exhibits superior heat resistance compared to BCP while maintaining effective hole-blocking functionality.

Inventive Principle:
Principle #40Composite materials

3Ease of manufacture

If Alq3 is used as electron-transporting material, then ease of manufacture is improved, but electron mobility and hole-blocking capability deteriorate

Engineering Contradiction:
ImprovemanufacturabilityVSAvoidelectron mobility
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The invention systematically modifies the molecular parameters of electron-transporting materials by introducing various substituents (fluorine atoms, alkyl groups, aryl groups) at specific positions of the benzotriazole core structure. These parameter changes enable optimization of electron mobility and hole-blocking capability while maintaining the ease of vacuum evaporation deposition that makes these materials manufacturable.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3029034B1Benzotriazole derivatives and organic electroluminescent element
Publication Date: 2021.04.14 HODOGAYA CHEMICAL CO LTD
  • EP3029034B1 patent drawingFigure 1~3
  • EP3029034B1 patent drawingFigure 4~6
  • EP3029034B1 patent drawingFigure 7

AI summary

A Benzotriazole derivative represented by the following general formula (1), wherein, Ar1 is a monovalent aromatic hydrocarbon group or aromatic heterocyclic group, Ar2 is a hydrogen atom, a deuterium atom, or a monovalent aromatic hydrocarbon group or aromatic heterocyclic group, A is a divalent aromatic hydrocarbon group or aromatic heterocyclic group, B is a divalent condensed polycyclic aromatic hydrocarbon group or a single bond, and C is a monovalent aromatic heterocyclic group, and wherein if A is a phenylene group, B is a divalent condensed polycyclic aromatic hydrocarbon group or C is a monovalent aromatic heterocyclic group other than a pyridyl group.