Aryl-Substituted Dithiolene Metal Complexes for Colorless IR Absorption

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current colorless infrared (IR) absorbers used in security printing and other applications face challenges with chemical and boiling water fastness, light stability, and colorlessness, particularly in high-end applications like banknote printing.

Innovation Solution

Development of specific metal complexes of dithiolenes with aryl or heteroaryl substituted imidazolidine-2-chalcogenone-4,5-dithione ligands, which provide enhanced chemical resistance, light stability, and heat stability while maintaining colorlessness, suitable for security printing and laser-welding of plastics.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional IR absorbers are used in security printing, then IR absorption function is achieved, but visible coloration and poor chemical fastness occur

Engineering Contradiction:
Improvechemical fastnessVSAvoidvisible coloration
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the chemical structure of dithiolene metal complexes by introducing specific aryl and heteroaryl substituents at positions 1 and 3 of the imidazolidine-2-chalcogenone-4,5-dithione ligand. This structural parameter change transforms the electronic properties of the complex, shifting the absorption maximum to the IR region (700-1200 nm) while minimizing visible absorption, thereby achieving both colorlessness and improved chemical fastness simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining metal centers (Ni, Pd, Pt) with specifically substituted dithiolene ligands. The aryl and heteroaryl groups at positions 1 and 3 of the ligand work synergistically with the metal-dithiolene core to enhance chemical stability while maintaining optimal IR absorption properties and colorlessness

Inventive Principle:
Principle #40Composite materials

2Reliability

If existing IR absorbers are used, then IR absorption is achieved, but light stability and heat stability are insufficient

Engineering Contradiction:
Improvelight stability and heat stabilityVSAvoidchemical stability
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent optimizes the ligand structure by introducing aryl and heteroaryl substituents at positions 1 and 3, which changes the electronic distribution and bonding characteristics of the complex. This parameter change enhances the complex's resistance to photodegradation and thermal decomposition, improving light stability and heat stability while maintaining chemical stability

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If conventional dithiolene complexes are used, then IR absorption is achieved, but colorlessness is compromised

Engineering Contradiction:
Improvevisible absorptionVSAvoidIR absorption performance
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent precisely adjusts the substitution pattern on the dithiolene ligand, placing aryl and heteroaryl groups at positions 1 and 3. This parameter change modifies the HOMO-LUMO energy gap and electronic transitions, shifting absorption to the IR region while minimizing visible absorption, thereby achieving superior colorlessness without compromising IR absorption performance

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 exhibit excellent fastness to chemicals, boiling water, and light, ensuring minimal visible absorption in the visible spectrum, making them ideal for high-end applications such as banknote printing and IR-readable bar codes.

Implementation Method 1

an infrared absorbing material that comprises transition element atoms or ions whose infrared absorption is a consequence of electronic transitions within the d-shell of the transition element

Methodology Applied
Scientific EffectElectronic transitions within d-shell: Absorption (EM radiation)

Data Source

PatentEP2643416B1The use of aryl or heteroaryl substituted dithiolene metal complexes as IR absorbers
Publication Date: 2019.08.07 BASF SE
  • EP2643416B1 patent drawing
  • EP2643416B1 patent drawing
  • EP2643416B1 patent drawing

AI summary

The present invention relates to the use of specific metal complexes of dithiolenes with aryl or heteroarylsubstituted imidazolidine-2-chalcogenone-4,5-dithione ligands as colourless IR absorbers.