Phenazine Derivative Near-Infrared Organic EL Device

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Solution Overview

Problem

Current near-infrared organic electroluminescent devices face challenges in achieving high efficiency due to unbalanced charge trapping and exciton quenching, with metal complexes being expensive and thermally activated delayed fluorescent materials not yet attaining satisfactory performance.

Innovation Solution

A phenazine derivative with a donor group linked via a 7-conjugated system is used as a light-emitting material, allowing for efficient near-infrared light emission by effectively utilizing triplet exciton energy through delayed fluorescence.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If metal complexes (platinum or iridium complexes) are used as room-temperature phosphorescent materials for near-infrared light emission, then external quantum efficiency is improved, but manufacturing cost increases and stable supply becomes difficult

Engineering Contradiction:
Improveexternal quantum efficiencyVSAvoidmanufacturing cost and supply stability
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive metal complexes with organic compounds containing only carbon, hydrogen, nitrogen, and other abundant elements. These organic light-emitting materials achieve comparable external quantum efficiency (2.8% at 890 nm) without relying on scarce noble metals, thereby reducing manufacturing cost and ensuring stable supply while maintaining high productivity in near-infrared light emission

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

Solution Approach 2:

The patent modifies the molecular structure parameters of the light-emitting material by designing specific organic compounds with electron-donating groups (such as amino groups) attached to the phenazine core. This structural parameter change enables the material to exhibit delayed fluorescence with high external quantum efficiency in the near-infrared region, replacing metal complexes without sacrificing performance

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If thermally activated delayed fluorescent materials are used for near-infrared light emission, then manufacturing cost is reduced, but light emission efficiency remains insufficient

Engineering Contradiction:
Improvemanufacturing costVSAvoidlight emission efficiency
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent optimizes the molecular structure parameters of thermally activated delayed fluorescent materials by introducing specific electron-donating groups (amino groups, alkoxy groups) at defined positions on the phenazine skeleton. This structural optimization extends the emission wavelength to the near-infrared region (peak at 680-950 nm) while maintaining high external quantum efficiency (up to 2.8% at 890 nm), thereby improving light emission efficiency without increasing manufacturing cost

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining the phenazine core (providing rigid backbone and electron-accepting properties) with electron-donating substituent groups. This composite structure achieves both thermal activation for delayed fluorescence and near-infrared emission with high efficiency, overcoming the limitations of previous single-structure materials

Inventive Principle:
Principle #40Composite materials

3Productivity

If triplet excitons are utilized for light emission in organic light emitting materials, then luminous efficiency is improved, but the complexity of managing triplet exciton dynamics increases

Engineering Contradiction:
Improveluminous efficiencyVSAvoidtriplet exciton management complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent designs organic light-emitting materials that automatically utilize triplet excitons for light emission through thermally activated delayed fluorescence mechanism. The molecular structure inherently facilitates reverse intersystem crossing from triplet to singlet state, enabling the material to self-manage triplet excitons without requiring complex external control systems or additional device layers, thereby improving luminous efficiency while maintaining device simplicity

Inventive Principle:
Principle #25Self-service

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 phenazine derivative-based organic EL device achieves high-efficiency near-infrared light emission by promoting reverse intersystem crossing and reducing energy wastage, leading to improved external quantum efficiency and reduced roll-off phenomena.

Implementation Method 1

the energy difference ΔEST between the excited singlet energy level ES1 and the excited triplet energy level ET1 is small and therefore reverse intersystem crossing from the excited triplet state to the excited singlet state readily occurs

Methodology Applied
Scientific EffectReverse intersystem crossing:

Implementation Method 2

thermally activated delayed fluorescent materials are known... the compound of the present invention includes a compound that emits delayed fluorescence

Methodology Applied
Scientific EffectDelayed fluorescence:

Implementation Method 3

organic electroluminescent devices (organic EL devices)... an organic light emitting device using the compound of the present invention as a light emitting material may realize high-efficiency near-infrared light emission

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS20240002352A1Compound, light-emitting material, delayed fluorescence material, and organic light-emitting element
Publication Date: 2024.01.04 KYULUX INC
  • US20240002352A1 patent drawing
  • US20240002352A1 patent drawing
  • US20240002352A1 patent drawing

AI summary

A high-efficiency near-infrared emitting organic EL device may be provided, using a compound represented by the following general formula. At least one of R1 to R4 is *-Ar-D, or R1 and R2, R2 and R3, or R3 and R4 bond to each other to form an aromatic ring having D. D represents a donor group, and Ar represents an arylene group.