Imidazophenanthridine Ligand Bond Stabilization for OLEDs

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Solution Overview

Problem

The stability of imidazophenanthridine ligands in organic light-emitting diodes (OLEDs) is limited due to weak bonds caused by polycyclic ring strain and electronic structure, leading to reduced device lifetime for both iridium and platinum-based blue-emitting complexes.

Innovation Solution

A strategy to improve the stability of imidazophenanthridine ligands by addressing a weak bond identified through computational theory, mass spec fragmentation analysis, and photooxidative studies, which involves modifying the ligand structure to enhance bond stability in the triplet excited state.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If imidazophenanthridine ligands are used in OLEDs, then deep blue emission and high photoluminescent quantum yield are achieved, but device lifetime is reduced due to weak bonds caused by polycyclic ring strain

Engineering Contradiction:
Improvedeep blue emissionVSAvoiddevice lifetime
Core Design Contradiction:
Illumination intensityVSReliability

Solution Approach 1:

The patent modifies the imidazophenanthridine ligand structure by changing chemical parameters - specifically replacing certain atoms or groups in the polycyclic framework to reduce ring strain and strengthen weak bonds. This structural parameter change allows maintaining deep blue emission properties while improving bond stability and device lifetime.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite ligand structures by combining imidazophenanthridine core with additional stabilizing groups or modifications. These composite structures maintain the desired optical properties for deep blue emission while incorporating structural elements that strengthen weak bonds and reduce ring strain effects.

Inventive Principle:
Principle #40Composite materials

2Productivity

If imidazophenanthridine ligands are used for phosphorescence emission, then high efficiency is achieved, but stability is limited due to electronic structure and weak bonds

Engineering Contradiction:
Improvephosphorescence efficiencyVSAvoidligand stability
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent changes the electronic structure parameters of the imidazophenanthridine ligand by modifying chemical groups or atomic composition. These parameter changes strengthen weak bonds caused by ring strain while preserving the electronic properties necessary for efficient phosphorescence emission.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the harmful effect of ring strain and weak bonds into a benefit by strategically modifying the ligand structure. The modifications stabilize the previously weak bonds while maintaining or enhancing the phosphorescence efficiency, effectively turning a structural weakness into a stabilized configuration that supports high efficiency.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 modified imidazophenanthridine ligands exhibit improved stability and extended device lifetime in OLEDs, maintaining high photoluminescent quantum yield and efficiency while providing deep blue emission.

Implementation Method 1

Phosphorescence may be referred to as a 'forbidden' transition because the transition requires a change in spin states... Phosphorescence from triplets can be enhanced over fluorescence by confining, preferably through bonding, the organic molecule in close proximity to an atom of high atomic number. This phenomenon, called the heavy atom effect, is created by a mechanism known as spinorbit coupling.

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 2

Phosphorescence from triplets can be enhanced over fluorescence by confining, preferably through bonding, the organic molecule in close proximity to an atom of high atomic number. This phenomenon, called the heavy atom effect, is created by a mechanism known as spinorbit coupling.

Methodology Applied
Scientific EffectSpin-orbit coupling:

Implementation Method 3

A strategy to improve the stability of imidazophenanthridine ligands by addressing a weak bond identified through computational theory, mass spec fragmentation analysis, and photooxidative studies, which involves modifying the ligand structure to enhance bond stability in the triplet excited state.

Methodology Applied
Scientific EffectBond stabilization:

Data Source

PatentEP3741768B1Stabilized imidazophenanthridine materials
Publication Date: 2022.12.07 UNIVERSAL DISPLAY CORP
  • EP3741768B1 patent drawingFigure 1
  • EP3741768B1 patent drawingFigure 2
  • EP3741768B1 patent drawingFigure 3A

AI summary

Imidazophenanthridine ligands and metal complexes are provided. The compounds exhibit improved stability through a linking substitution that links a nitrogen bonded carbon of an imidizole ring to a carbon on the adjacent fused aryl ring. The compounds may be used in organic light emitting devices, particularly as emissive dopants, providing devices with improved efficiency, stability, and manufacturing. In particular, the compounds provided herein may be used in blue devices having high efficiency.