Fluorinated OLED Ligands for Wavelength Tuning

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Solution Overview

Problem

Current organic light-emitting diodes (OLEDs) face challenges in fine-tuning emission wavelength and stability, particularly in achieving saturated colors and efficient operation, as existing materials lack the necessary precision and durability.

Innovation Solution

The development of fluorinated alkyl groups in OLED ligands, specifically 9,9-difluoro-9H-fluorene, 9,9-difluoro-10,10-dimethyl-9,10-dihydrophenanthrene, and 9,9,10,10-tetrafluoro-9,10-dihydrophenanthrene compounds, which act as phosphorescent emitters, allowing for improved wavelength tuning and stability in OLEDs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional organic materials are used in OLEDs, then fabrication cost is reduced, but emission wavelength tuning precision and device stability deteriorate

Engineering Contradiction:
Improveemission wavelength tuning precisionVSAvoiddevice stability
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent applies parameter changes by systematically modifying the chemical structure of organic compounds through fluorine substitution at different positions (e.g., 2,7-difluoro-9H-fluorene, 2,7,9-trifluoro-9H-fluorene) and varying alkyl chain lengths/branches to precisely tune emission wavelengths across the visible spectrum while maintaining device stability. This structural parameter optimization enables independent control of optical properties without sacrificing material reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by combining fluorinated aromatic cores with various alkyl substituents and coordinating ligands (such as cyclometalating ligands and N^C ligands) to create complex organometallic emitters. These composite structures integrate the photostability of fluorinated aromatics with the tunable emissive properties of metal complexes, achieving both precision wavelength control and enhanced device stability.

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If fluorinated alkyl groups are incorporated in OLED ligands, then emission wavelength tuning capability is improved, but device complexity increases

Engineering Contradiction:
Improveemission wavelength tuning capabilityVSAvoidmolecular structure complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the molecular structure into distinct functional modules: fluorinated aromatic cores (e.g., fluorene, dibenzofuran, xanthene) for photostability, alkyl substituent groups for steric control and solubility, and coordinating ligands for metal chelation. This modular segmentation allows independent optimization of each component to achieve wavelength tuning without proportionally increasing overall molecular complexity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent implements local quality by placing fluorine atoms at specific positions (2,7-positions of fluorene; 2,7-positions of dibenzofuran) and introducing alkyl groups at predetermined locations to locally modify electronic and steric properties. This localized functionalization enables precise wavelength tuning through targeted electronic effects without requiring global structural complexity throughout the entire molecule.

Inventive Principle:
Principle #3Local quality

3Use of energy by moving object

If phosphorescent emitters are used in OLEDs, then external quantum efficiency is improved, but material stability and operational lifetime deteriorate

Engineering Contradiction:
Improveexternal quantum efficiencyVSAvoidmaterial stability
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent applies the inert atmosphere principle by incorporating fluorinated aromatic hydrocarbon frameworks that create a chemically inert and photostable environment around the phosphorescent metal center. The fluorinated rings (e.g., 2,7-difluoro-9H-fluorene, 2,7-difluorodibenzofuran) resist oxidation and degradation, protecting the sensitive phosphorescent emitters from environmental damage while maintaining high external quantum efficiency through efficient triplet state utilization.

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

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

These compounds enhance the external quantum efficiency and enable the production of various green, yellow, and red emitters, offering better stability and cost-effective OLED fabrication processes.

Implementation Method 1

The present disclosure provides 9,9-difluoro-9H-fluorene, 9,9-difluoro-10,10-dimethyl-9,10-dihydrophenanthrene, 9,9,10,10-tetrafluoro-9,10-dihydrophenanthrene and analogs that when used as emitters in OLEDs provide more opportunities for fine-tuning the emission wavelength and improve stability of the OLEDs

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 2

OLEDs make use of thin organic films that emit light when voltage is applied across the device

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS20240417415A1Organic electroluminescent materials and devices
Publication Date: 2024.12.19 UNIVERSAL DISPLAY CORP
  • US20240417415A1 patent drawing
  • US20240417415A1 patent drawing
  • US20240417415A1 patent drawing

AI summary

Provided are a compound having a metal M and a first ligand LA comprising the structure ofwhere the compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature.