Spiro Chiral Tetradentate Pt/Pd CPL Complexes Without Chiral Resolution

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Solution Overview

Problem

Existing cyclometalated platinum (II) and palladium (II) complexes for circularly polarized luminescence materials suffer from low chemical and thermal stability, racemization issues, and difficulty in achieving optically pure chiral configurations, hindering their application in stable and efficient OLED devices.

Innovation Solution

A central chirality induced spiro chiral tetradentate cyclometalated platinum (II) and palladium (II) complex-based material is developed, utilizing a central chiral fragment to autonomously induce a twisted quadrilateral configuration, enhancing chemical and thermal stability without the need for chiral resolution.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Device complexity

If bidentate cyclometalated platinum (II) and palladium (II) complexes are used, then the molecular structure is simple, but the luminescent quantum efficiency is reduced due to low rigidity and easy twisting/vibration of ligands

Engineering Contradiction:
Improvemolecular structure complexityVSAvoidluminescent quantum efficiency
Core Design Contradiction:
Device complexityVSLoss of energy

Solution Approach 1:

The patent employs a tetradentate ligand system with asymmetric coordination geometry around the metal center, creating a rigid chiral structure that prevents ligand twisting and vibration while maintaining optical activity. The asymmetric arrangement of donor atoms in the tetradentate ligand framework provides structural rigidity that suppresses non-radiative decay pathways, thereby improving luminescent quantum efficiency without excessive complexity.

Inventive Principle:
Principle #4Asymmetry

Solution Approach 2:

The patent pre-establishes a rigid tetradentate ligand framework with predetermined chiral configuration before metal coordination. This preliminary structural arrangement ensures that the complex achieves high rigidity and optical purity directly upon formation, eliminating the need for subsequent chiral resolution steps and maintaining high luminescent efficiency from the outset.

Inventive Principle:
Principle #10Preliminary action

2Loss of energy

If tridentate ligand-based cyclometalated platinum (II) and palladium (II) complexes are used, then the luminescence quantum efficiency is improved due to enhanced molecular rigidity, but the chemical and thermal stability is reduced and racemization occurs

Engineering Contradiction:
Improveluminescence quantum efficiencyVSAvoidchemical and thermal stability
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent utilizes a tetradentate ligand system with asymmetric coordination geometry that creates a rigid chiral structure resistant to racemization. The asymmetric arrangement of donor atoms provides both the rigidity needed for high luminescent efficiency and the structural stability required for chemical and thermal reliability, resolving the contradiction between these properties.

Inventive Principle:
Principle #4Asymmetry

Solution Approach 2:

The patent combines multiple donor atom types within a single tetradentate ligand framework to create a composite coordination environment around the metal center. This composite structure provides both rigidity for luminescent efficiency and multiple stabilizing interactions for chemical and thermal stability, achieving both goals simultaneously.

Inventive Principle:
Principle #40Composite materials

3Reliability

If conventional chiral ligands are used to achieve optically pure CPL, then the circularly polarized luminescence is achieved, but the preparation cost increases due to difficulty in obtaining optically pure chiral configurations

Engineering Contradiction:
Improveoptical purityVSAvoidpreparation cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent employs a tetradentate ligand system that self-assembles around the metal center to form an optically active complex with high enantiomeric excess. The ligand framework inherently provides the chiral environment needed for CPL without requiring external chiral auxiliaries or complex resolution procedures, making the synthesis process simpler and more cost-effective while maintaining high optical purity.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent pre-establishes the chiral configuration within the tetradentate ligand structure before metal coordination. This preliminary chiral arrangement is built into the ligand synthesis itself, eliminating the need for subsequent chiral resolution steps and reducing preparation costs while ensuring optically pure CPL activity.

Inventive Principle:
Principle #10Preliminary action

4Use of energy by moving object

If existing cyclometalated complexes are used, then the heavy atom effect enables full utilization of singlet and triplet excitons, but the chemical and thermal stability is insufficient for stable OLED device operation

Engineering Contradiction:
Improveexciton utilization efficiencyVSAvoidchemical and thermal stability
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent combines a tetradentate ligand framework with a cyclometalated metal center to create a composite complex that maintains the heavy atom effect for efficient exciton utilization while the tetradentate ligand provides structural rigidity and stability. This composite structure resolves the contradiction by integrating the beneficial properties of both ligand types without their individual drawbacks.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The asymmetric tetradentate ligand coordination geometry creates a rigid chiral structure that enhances both the heavy atom effect for exciton utilization and the structural stability for device operation. The asymmetric arrangement provides steric protection around the metal center, improving chemical and thermal stability while maintaining the orbital overlap needed for efficient triplet exciton utilization.

Inventive Principle:
Principle #4Asymmetry

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 material achieves high chemical and thermal stability, enabling the production of optically pure circularly polarized luminescence with reduced preparation costs and maintaining the chiral properties under various conditions.

Implementation Method 1

a central chirality induced spiro chiral tetradentate cyclometalated platinum (II) and palladium (II) complex-based circularly polarized luminescence material

Methodology Applied
Scientific EffectCentral chirality:

Implementation Method 2

Spiro chiral metal complex molecules can autonomously induce a whole tetradentate ligand to coordinate with metal ions in a less sterically hindered manner by means of a central chiral fragment

Methodology Applied
Scientific EffectSpiro chirality:

Implementation Method 3

Cyclometalated platinum (II) and palladium (II) complex-based phosphorescent material can fully utilize all of singlet and triplet excitons generated by electroexcitation due to its heavy atom effect, so that its maximum theoretical quantum efficiency can be up to 100%

Methodology Applied
Scientific EffectHeavy atom effect:

Implementation Method 4

Circularly polarized luminescence (CPL) is a phenomenon that chiral luminescence materials are excited and emit left-handed or right-handed circularly polarized light

Methodology Applied
Scientific EffectCircularly polarized luminescence:

Data Source

PatentEP4306521B1Central chirality induced spiro chiral tetradentate cyclometalated platinum (II) and palladium (II) complex-based circularly polarized luminescence material and application thereof
Publication Date: 2026.04.15 ZHEJIANG HUAXIAN PHOTOELECTRICITY TECHNOLOGY CO LTD
  • EP4306521B1 patent drawingFigure 1~2(F)
  • EP4306521B1 patent drawingFigure 3(A)~4(F)
  • EP4306521B1 patent drawingFigure 5(A)~6

AI summary

Disclosed are a central chirality induced spiro chiral tetradentate cyclometalated platinum (II) and palladium (II) complex-based circularly polarized luminescence material and an application thereof. Spiro chiral metal complex molecules can be autonomously induced by a whole tetradentate ligand to coordinate with metal ions in a less sterically hindered manner by means of a central chiral fragment La in the tetradentate ligand, to form an optically pure spiro chiral metal complex-based circularly polarized luminescence material, without need for chiral resolution. Moreover, the material has high chemical stability and thermal stability, and has important applications in circularly polarized luminescence devices.