Imide Derivative Hole Transport Layer for Low-Voltage Organic EL

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing organic electroluminescent (EL) devices require high voltages for sufficient luminance, leading to shortened device lifetime and increased power consumption, and current leakage issues due to unstable electron-receiving compounds like tetrafluorodicyanoquinodimethane, which also contaminate the apparatus during fabrication.

Innovation Solution

A novel imide derivative with electron-withdrawing groups, derived from pyromellitic acid, is used as a hole transporting or injecting layer material in organic EL devices, offering improved electron-receiving properties, heat resistance, and reduced scattering during film formation, allowing for low-voltage operation and extended device lifetime.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If high voltage is applied to obtain sufficient luminance, then luminance is improved, but device lifetime is shortened and power consumption increases

Engineering Contradiction:
ImproveluminanceVSAvoiddevice lifetime
Core Design Contradiction:
Illumination intensityVSDuration of action of stationary object

Solution Approach 1:

The patent changes the chemical parameters of the hole transporting material by introducing electron-receiving groups (imide structures with carbonyl and imine groups) to modify the electronic properties. This allows the material to efficiently transport holes at lower voltages, resolving the contradiction between luminance and device lifetime by enabling sufficient luminance output without high voltage stress that would otherwise degrade the device

Inventive Principle:
Principle #35Parameter changes

2Illumination intensity

If high voltage is applied to obtain sufficient luminance, then luminance is improved, but power consumption increases

Engineering Contradiction:
ImproveluminanceVSAvoidpower consumption
Core Design Contradiction:
Illumination intensityVSUse of energy by stationary object

Solution Approach 1:

The patent modifies the electronic parameters of the hole transporting layer by incorporating imide derivatives with strong electron-receiving capabilities. This changes the charge transport efficiency, allowing sufficient luminance to be achieved at lower operating voltages and reduced current densities, thereby decreasing power consumption while maintaining required luminance levels

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If electron-receiving compounds are used to improve hole injection, then hole injection efficiency is improved, but device stability deteriorates due to heat resistance issues

Engineering Contradiction:
Improvehole injection efficiencyVSAvoiddevice stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent changes the thermal and electronic parameters of the hole transporting material by selecting imide derivatives that possess both strong electron-receiving properties and high thermal stability. The rigid imide core structure with resonance-stabilized electron distribution provides heat resistance while maintaining efficient charge transport, thus improving hole injection without compromising device stability

Inventive Principle:
Principle #35Parameter changes

4Ease of manufacture

If low molecular weight electron-receiving compounds are used, then ease of deposition is improved, but apparatus contamination increases due to sublimation

Engineering Contradiction:
Improveease of depositionVSAvoidapparatus contamination
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent changes the molecular weight and intermolecular interaction parameters of the electron-receiving compound by designing imide derivatives with larger molecular structures and stronger intermolecular forces. This increases the sublimation temperature and reduces vapor pressure, allowing the material to be deposited by vacuum evaporation without excessive sublimation that would contaminate the apparatus, while still maintaining good film-forming properties

Inventive Principle:
Principle #35Parameter changes

5Ease of operation

If electron-receiving compounds are used to improve hole injection, then hole injection efficiency is improved, but device stability deteriorates due to handling instability

Engineering Contradiction:
Improvehole injection efficiencyVSAvoidhandling stability
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent changes the physical and chemical stability parameters of the electron-receiving compound by incorporating imide structures with rigid frameworks and strong intramolecular bonds. This provides thermal stability, oxidation resistance, and chemical inertness, making the material stable during handling, storage, and device fabrication while maintaining efficient hole injection performance

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 imide derivative enables organic EL devices to be driven at low voltages while maintaining long lifetimes and preventing contamination, thus enhancing the stability and efficiency of the devices.

Implementation Method 1

the imide derivatives have electron receiving properties and excel in heat resistance

Methodology Applied
Scientific EffectElectron receiving properties: Electron Paramagnetic Resonance

Implementation Method 2

these compounds form charge transfer complexes with amine derivatives of donor compounds

Methodology Applied
Scientific EffectCharge transfer complex formation: Redox Reactions

Implementation Method 3

a fluorescent material emits light by the recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Implementation Method 4

fabricating an organic EL device by vacuum deposition

Methodology Applied
Scientific EffectPhysical vapor deposition: Physical Vapour Deposition

Data Source

PatentUS8168327B2Imide derivative, material for organic electroluminescent device and organic electroluminescent device using the same
Publication Date: 2012.05.01 IDEMITSU KOSAN CO LTD
  • US8168327B2 patent drawing
  • US8168327B2 patent drawing
  • US8168327B2 patent drawing

AI summary

An imide derivative represented by the following formula (A):wherein Ra and Rb are each a hydrogen atom, a halogen atom, a cyano group, an alkyl group, a fluoroalkyl group or an aryl group; at least one of Ra and Rb is a fluoroalkyl group; and Rc and Rd are each a substituted or unsubstituted benzyl group, an aryl group, a heterocycle, a fluoroalkyl group or an imide group.