Benzotriazole Metal Complexes for Orange-Red OLED Emission

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Solution Overview

Problem

There is a continuing need for electroluminescent compounds, especially orange or red emitters, with improved efficiency in organic light-emitting diodes (OLEDs).

Innovation Solution

The development of metal complexes comprising 2H-benzotriazole ligands, specifically designed to emit light in the orange or red spectrum, where the complexes include a metal with an atomic weight greater than 40, such as Ir or Pt, and are used in OLEDs, bioassays, and as catalysts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional electroluminescent compounds (anthracene, thiadiazole derivatives, coumarin derivatives) are used in OLEDs, then device structure is simple and ease of manufacture is good, but luminescence efficiency is insufficient especially in orange or red spectrum

Engineering Contradiction:
Improveease of manufactureVSAvoidluminescence efficiency
Core Design Contradiction:
Ease of manufactureVSLoss of energy

Solution Approach 1:

The patent employs composite material strategy by combining heavy metal centers (Ir, Pt, Rh, Os, Pd, Ru, Fe, Ni, Co) with benzotriazole-based organic ligands to create metal coordination compounds. This composite approach leverages the photophysical properties of both metal and organic components, where the metal center provides spin-orbit coupling for phosphorescence and the benzotriazole ligand provides structural stability and tunable electronic properties, achieving high luminescence efficiency in orange-red spectrum while maintaining manufacturability through established coordination chemistry synthesis routes

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies parameter changes by systematically varying the metal center (atomic weight > 40), the benzotriazole ligand substituents (R1-R6 groups), and coordination geometry to tune the emission wavelength into the orange-red region (>520 nm) while optimizing luminescence efficiency. The use of different metal ions with varying atomic weights and electron configurations allows precise control over phosphorescence lifetime and intensity, resolving the efficiency problem without sacrificing ease of manufacture

Inventive Principle:
Principle #35Parameter changes

2Loss of energy

If metal coordination compounds with benzotriazole ligands are synthesized through cyclometallation reactions, then luminescence efficiency is improved, but manufacturing process complexity increases

Engineering Contradiction:
Improveluminescence efficiencyVSAvoidmanufacturing process complexity
Core Design Contradiction:
Loss of energyVSDevice complexity

Solution Approach 1:

The patent applies preliminary action by pre-synthesizing the benzotriazole ligands with appropriate substituents (R1-R6 groups) before coordination to the metal center. This pre-functionalization of the organic ligand allows for systematic optimization of photophysical properties independent of metal coordination steps, simplifying the overall manufacturing process while maintaining high luminescence efficiency. The cyclometallation reaction then proceeds in a controlled manner to form the final active complex

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent segments the synthesis process into distinct stages: (1) preparation of benzotriazole ligands with tailored substituents, (2) cyclometallation reaction with metal salts to form coordination compounds, and (3) purification and characterization. This segmentation allows each step to be optimized independently, reducing overall manufacturing complexity while achieving the desired luminescence efficiency through systematic control of ligand-metal interactions

Inventive Principle:
Principle #1Segmentation

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 metal complexes exhibit enhanced luminescence efficiency, particularly in the orange or red range, with emission peaks above 520 nm, offering improved performance in OLEDs and other applications.

Implementation Method 1

These metal complexes exhibit enhanced luminescence efficiency, particularly in the orange or red range, with emission peaks above 520 nm

Methodology Applied
Scientific EffectPhosphorescence: Phosphorescence

Implementation Method 2

The organic active layer emits light through the light-transmitting electrical contact layer upon application of electricity across the electrical contact layers

Methodology Applied
Scientific EffectElectroluminescence: Electroluminescence

Data Source

PatentUS9362510B2Electroluminescent metal complexes with benzotriazoles
Publication Date: 2016.06.07 UDC IRELAND

AI summary

This invention relates to electroluminescent metal complexes with benzotriazoles of the formula (I), a process for their preparation, electronic devices comprising the metal complexes and their use in electronic devices, especially organic light emitting diodes (OLEDs), as oxygen sensitive indicators, as phosphorescent indicators in bioassays, and as catalysts.