Pyrromethene-Boron Complex Compounds for Organic EL Devices

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Solution Overview

Problem

Conventional organic electroluminescence devices have low luminous efficiency and color purity, and are prone to concentration quenching and thermal decomposition, limiting their practical application.

Innovation Solution

A pyrromethene-boron complex compound is developed, which can be used as a dopant in the emitting layer of organic electroluminescence devices, offering high luminous efficiency, improved color purity, and resistance to concentration quenching and thermal decomposition, even at elevated temperatures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional organic materials are used in organic EL devices, then the devices can be manufactured with simple processes, but the luminous efficiency and color purity remain low

Engineering Contradiction:
Improvemanufacturing simplicityVSAvoidluminous efficiency
Core Design Contradiction:
Ease of manufactureVSLoss of energy

Solution Approach 1:

The patent modifies the molecular structure of pyrromethene compounds by introducing specific substituents (fluoroalkoxy groups at positions 2 and 6, and aryl groups at positions 1 and 5) to change the electronic and optical parameters of the material. This structural parameter change enables the compound to achieve high luminous efficiency and color purity while maintaining ease of manufacture through existing organic EL fabrication processes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite dopant system by combining the specifically substituted pyrromethene compound with a host material in the emitting layer. This composite material approach allows the pyrromethene-boron complex to function as an efficient luminescent dopant that improves luminous efficiency and color purity without complicating the manufacturing process

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If doping concentration is increased to improve luminous efficiency, then more light is emitted, but concentration quenching occurs and reduces efficiency

Engineering Contradiction:
Improveluminous efficiencyVSAvoidresistance to concentration quenching
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent changes the molecular parameters of the pyrromethene compound by introducing bulky aryl groups (such as phenyl, naphthyl, or anthryl groups) at positions 1 and 5, and fluoroalkoxy groups at positions 2 and 6. These parameter changes increase the molecular volume and optimize the electronic structure, allowing the compound to maintain high luminous efficiency even at elevated doping concentrations by reducing intermolecular interactions that cause concentration quenching

Inventive Principle:
Principle #35Parameter changes

3Productivity

If operating temperature is elevated to improve device performance, then efficiency may increase, but thermal decomposition occurs and shortens device lifespan

Engineering Contradiction:
Improvedevice performanceVSAvoiddevice lifespan
Core Design Contradiction:
ProductivityVSDuration of action of stationary object

Solution Approach 1:

The patent introduces fluoroalkoxy groups (such as CF3CH2O- or C2F5O-) at positions 2 and 6 of the pyrromethene skeleton. The fluorine substitution increases the thermal stability of the compound by strengthening the B-O bond and reducing molecular flexibility. This parameter change allows the material to withstand elevated operating temperatures without thermal decomposition, thereby extending device lifespan while maintaining performance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a thermally stable composite emitting layer by combining the fluorinated pyrromethene-boron complex with a suitable host material. This composite structure provides thermal protection through the stable host-guest interaction, preventing decomposition of the pyrromethene dopant at elevated temperatures and thus extending device operational life

Inventive Principle:
Principle #40Composite materials

4Ease of operation

If conventional pyrromethene compounds are used, then the basic emitting function is achieved, but color purity and luminous efficiency are insufficient

Engineering Contradiction:
Improveemitting functionVSAvoidcolor purity
Core Design Contradiction:
Ease of operationVSManufacturing precision

Solution Approach 1:

The patent precisely modifies the molecular parameters of the pyrromethene compound by substituting hydrogen atoms with specific groups at defined positions: aryl groups (phenyl, naphthyl, anthryl) at positions 1 and 5, and fluoroalkoxy groups at positions 2 and 6. These parameter changes tune the HOMO-LUMO energy gap and molecular orbital distribution, resulting in narrowed emission bandwidth and improved color purity while maintaining the basic emitting function

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 pyrromethene-boron complex compound enhances the performance of organic electroluminescence devices by maintaining high luminous efficiency and color purity, reducing concentration quenching, and preventing thermal decomposition, thereby extending the device's lifespan and efficiency.

Implementation Method 1

An organic electroluminescence device (hereinafter referred to as an 'organic EL device') utilizing an organic substance... When an electric field is applied between the both electrodes, electrons are injected from the cathode and holes are injected from the anode, these electrons are then recombined with the holes in the emitting layer, thereby to cause an excited state, and energy is discharged as light when the excited state is returned to the ground state.

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Implementation Method 2

The invention also aims at providing a pyrromethene-boron complex compound which has a high volatility, can be deposited at a lower temperature, and is hardly thermally-decomposed even if heated for a long period of time.

Methodology Applied
Scientific EffectThermal stability:

Data Source

PatentUS8778510B2Pyrromethene-boron complex compounds and organic electroluminescent elements using same
Publication Date: 2014.07.15 IDEMITSU KOSAN CO LTD
  • US8778510B2 patent drawing
  • US8778510B2 patent drawing
  • US8778510B2 patent drawing

AI summary

A pyrromethene-boron complex compound represented by the following formula (1);wherein Z1 and Z2 are independently a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group, at least one of Z1 and Z2 is an alkoxy group substituted with a fluorine atom or an aryloxy group substituted with a fluorine atom or a fluoroalkyl group, and Z1 and Z2 may form a ring.