Fluorinated Diketone Ligands for OLED Efficiency and Lifetime

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Solution Overview

Problem

Current organic electroluminescent devices, particularly phosphorescent OLEDs, face challenges with non-saturated blue color, short device lifetime, high operating voltage, and efficiency roll-off at high brightness, which are not adequately addressed by existing ancillary ligands.

Innovation Solution

Development of metal complexes with partially fluorine-substituted diketone ancillary ligands, specifically mono-fluorine or dual-fluorine substitutions, to fine-tune emission wavelength, reduce voltage, and enhance efficiency and device performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If phosphorescent emitters are used to achieve high internal quantum efficiency, then efficiency is improved, but device lifetime becomes short

Engineering Contradiction:
Improveinternal quantum efficiencyVSAvoiddevice lifetime
Core Design Contradiction:
Use of energy by moving objectVSDuration of action of stationary object

Solution Approach 1:

The patent applies parameter changes by systematically varying the fluorine substitution patterns (mono-fluorine at positions 3, 5, or 7; dual-fluorine combinations) on the ancillary ligand structure. These structural parameter modifications tune the photophysical properties of the phosphorescent emitter, optimizing both efficiency and stability. The fluorine substitution alters electron distribution and molecular packing, thereby improving device lifetime while maintaining high internal quantum efficiency.

Inventive Principle:
Principle #35Parameter changes

2Device complexity

If conventional ancillary ligands are used, then device structure is simple, but emission wavelength tuning capability is insufficient

Engineering Contradiction:
Improveligand structure complexityVSAvoidemission wavelength tuning
Core Design Contradiction:
Device complexityVSAdaptability or versatility

Solution Approach 1:

The patent applies local quality by introducing fluorine atoms at specific positions (3, 5, or 7) on the ancillary ligand structure. This localized substitution strategy allows precise tuning of emission wavelengths without requiring complete structural redesign. Different fluorine positions provide different tuning effects, enabling fine control over emission color while maintaining the overall simplicity of the ligand framework.

Inventive Principle:
Principle #3Local quality

3Ease of manufacture

If existing ligand structures are used, then manufacturing is straightforward, but operating voltage remains high

Engineering Contradiction:
Improvefabrication simplicityVSAvoidoperating voltage
Core Design Contradiction:
Ease of manufactureVSUse of energy by stationary object

Solution Approach 1:

The patent applies parameter changes by modifying the electronic properties of the ancillary ligand through fluorine substitution. The fluorine atoms alter the HOMO-LUMO energy levels and charge distribution, which improves charge injection and transport efficiency. This results in reduced operating voltage while maintaining ease of device fabrication through conventional vacuum deposition methods.

Inventive Principle:
Principle #35Parameter changes

4Use of energy by moving object

If phosphorescent emitters are used to achieve high efficiency, then internal quantum efficiency is improved, but efficiency roll-off occurs at high brightness

Engineering Contradiction:
Improveinternal quantum efficiencyVSAvoidbrightness efficiency
Core Design Contradiction:
Use of energy by moving objectVSProductivity

Solution Approach 1:

The patent applies parameter changes through fluorine substitution on the ancillary ligand, which modifies the molecular packing and aggregation behavior of the phosphorescent emitter. This structural modification reduces concentration quenching and triplet-triplet annihilation effects at high exciton densities, thereby suppressing efficiency roll-off and maintaining high brightness efficiency.

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 new metal complexes effectively improve emission wavelength tuning, reduce operating voltage, increase efficiency, and prolong device lifetime, providing better performance compared to previous ligand structures.

Implementation Method 1

In 1997, Forrest and Thompson reported phosphorescent OLED, which uses triplet emission from heave metal containing complexes as the emitter. As a result, both singlet and triplets can be harvested, achieving 100% IQE.

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 2

Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triplet gap that makes the transition from triplet back to singlet possible. In the TADF device, the triplet excitons can go through reverse intersystem crossing to generate singlet excitons, resulting in high IQE.

Methodology Applied
Scientific EffectThermally activated delayed fluorescence:

Data Source

PatentUS11993617B2Organic luminescent material having an ancillary ligand with a partially fluorine-substituted substituent
Publication Date: 2024.05.28 BEIJING SUMMER SPROUT TECH CO LTD
  • US11993617B2 patent drawing
  • US11993617B2 patent drawing
  • US11993617B2 patent drawing

AI summary

Provided is an organic light-emitting material having an ancillary ligand with partially fluorinated substituents. The organic light-emitting material is a metal complex having a diketone ancillary ligand with partially fluorinated substituents and may be used as a light-emitting material in an organic electroluminescent device. These new types of metal complex can fine-tune the emission wavelength more effectively, reduce voltage, improve efficiency, prolong lifetimes, and provide better device performance. Further provided are an organic electroluminescent device and a compound formulation.