Copper(I) Complexes with Tridentate Ligands for OLED Stability

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Solution Overview

Problem

Current metal-organic emitters for OLEDs face challenges such as low long-term stability, thermal instability, sensitivity to water and oxygen, limited availability of important emission colors, manufacturing reproducibility issues, high current density efficiency, high luminance achievement, high material costs, and toxicity, along with complex and expensive synthesis processes.

Innovation Solution

Development of specific binuclear copper complexes with a structure that enhances the stability and efficiency of organic electroluminescent devices, including high emission quantum yields and short emission decay times, allowing for wide-ranging emission colors and easy handling due to improved redox stability, which can be processed from the gas phase with high purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional metal-organic emitters are used in OLEDs, then device efficiency can be achieved, but long-term stability and thermal stability are poor

Engineering Contradiction:
Improvelong-term stabilityVSAvoidservice life
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent changes the chemical parameters of the emitter material by developing new copper(I) complex compounds with specific ligand structures (combining N-heterocyclic carbene and pyridine moieties). This parameter change in molecular structure leads to improved thermal stability and redox stability, directly resolving the contradiction between achieving device efficiency and maintaining long-term stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite ligand structures that combine N-heterocyclic carbene and pyridine moieties coordinated to copper(I) centers. This composite molecular architecture provides synergistic effects where the NHC ligand contributes to thermal stability and the pyridine moiety enables efficient light emission, thus achieving both reliability and duration improvements.

Inventive Principle:
Principle #40Composite materials

2Use of energy by moving object

If triplet emitter materials are used to achieve high efficiency, then emission quantum yield increases, but material cost and synthesis complexity increase

Engineering Contradiction:
Improveemission quantum yieldVSAvoidsynthesis complexity
Core Design Contradiction:
Use of energy by moving objectVSEase of manufacture

Solution Approach 1:

The patent employs copper(I) complexes with relatively simple ligand structures that can be synthesized using conventional organic synthesis methods. Compared to rare-earth-based triplet emitters or complex organometallic compounds, these copper complexes use abundant metals and commercially available ligand precursors, significantly reducing material cost and simplifying manufacturing while maintaining high emission quantum yields.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Illumination intensity

If metal-organic emitters are used to achieve high luminance, then light emission efficiency improves, but thermal stability deteriorates

Engineering Contradiction:
ImproveluminanceVSAvoidthermal stability
Core Design Contradiction:
Illumination intensityVSTemperature

Solution Approach 1:

The patent modifies the thermal parameters of the emitter material through careful selection of ligand structures. The N-heterocyclic carbene ligand provides strong sigma-donation to the copper(I) center, creating a thermally stable complex that can withstand OLED operating temperatures. Simultaneously, the molecular structure is designed to maintain efficient photophysical properties for high luminance output, thus resolving the contradiction between thermal stability and luminance achievement.

Inventive Principle:
Principle #35Parameter changes

4Reliability

If conventional emitter materials are used, then device performance can be achieved, but manufacturing reproducibility is poor

Engineering Contradiction:
Improvedevice performanceVSAvoidmanufacturing reproducibility
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The copper(I) complexes described in the patent can be synthesized using conventional organic synthesis techniques with commercially available starting materials. The synthesis procedures are relatively straightforward and can be performed using standard laboratory equipment, enabling consistent production across different batches and manufacturers. This accessibility to conventional manufacturing methods directly improves manufacturing reproducibility while maintaining device performance.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 copper(I) complexes demonstrate improved stability, efficiency, and a wide range of achievable emission colors with high quantum yields, enabling the production of OLEDs with enhanced performance and simplified manufacturing, particularly through sublimation methods ensuring high purity and thermal stability.

Implementation Method 1

processed from the gas phase with high purity... can be processed from the gas phase with high purity... particularly through sublimation methods ensuring high purity

Methodology Applied
Scientific EffectSublimation: Sublimation

Implementation Method 2

The excited states then release their energy as bright light emission, e.g. B. in blue, green or red color... emission quantum yields... high emission quantum yields

Methodology Applied
Scientific EffectLuminescence: Luminescence

Data Source

PatentEP3204463B1Metal complexes with tridentate ligands for optoelectronic applications
Publication Date: 2019.04.17 CYNORA
  • EP3204463B1 patent drawingFigure 1~2
  • EP3204463B1 patent drawingFigure 3~4
  • EP3204463B1 patent drawingFigure 5~6

AI summary

The invention relates to metal complexes MLX of the following formula (A) and to the use thereof in optoelectronic components, in particular OLEDS, wherein M is selected from the group consisting of Cu, Ag, and Au; C(sp2) = sp2-hybridized carbon atom; A = a bridge with more than 1 and less than 6 (with respect to the shortest chain length) identical or different chain links k, where k = C(sp2)R, CR2, C=O, C=S, C=NR, O, N, NR, S, Se; wherein optionally one or more links of k are also part of an aromatic or aliphatic ring system as defined for C(sp2); E is selected from the group consisting of arsenic and phosphor; E' is selected from the group consisting of NR, PR, AsR, O, S, Se, or N as part of an imine system and, in the case of NR and N, optionally as a component of an aromatic or aliphatic ring system which can optionally be annelated with C(sp2) and/or A into a ring system such as quinoline or isoquinoline as defined for C(sp2); E" = either a chemically neutral group selected from the group consisting of C*R (carbene carbon), NR (imine nitrogen), NR2, PR2, AsR2, OR, SR, SeR, optionally as part of a neutral aromatic or heteroaromatic ring system or a single negatively charged group selected from NR, PR, AsR, O, S, Se, optionally as part of a anionic heteroaromatic ring system; and X is selected from the group consisting of Cl, Br, I, CN, OCN, SCN, alkinyl, and N3; where X is only present when E" = a chemically neutral group.