Methoxyaryl Self-Assembled Monolayer for Work Function Tuning

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Solution Overview

Problem

Existing organic electronic devices face challenges in matching the work functions of metal or metal oxide electrodes with organic electronic materials, and there is a need for suitable self-assembled monolayers to improve adhesion and compatibility between these layers.

Innovation Solution

A self-assembled monolayer comprising a moiety of formula (I) is used, where R1 can be methyl or fluorinated methyl, R2 is —CH2—, Ar1 is para-phenylene, and X1 includes sulfur or selenium-based functional groups, to modify metal or metal oxide surfaces, thereby adjusting their work functions and improving adhesion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If metal or metal oxide electrodes are used in organic electronic devices, then good electrical conductivity is achieved, but matching the work function with organic electronic materials becomes difficult

Engineering Contradiction:
Improvework function compatibilityVSAvoidwork function adaptability
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

A self-assembled monolayer (SAM) comprising compounds of formula (I) is introduced as an intermediary between the metal electrode and the organic electronic material. The SAM modifies the surface properties of the metal electrode, including its work function, to achieve better compatibility with the organic material. The sulfur or selenium-based functional groups in the compound form strong bonds with the metal surface, while the aromatic core and alkyl/alkenyl chains provide the necessary electronic and steric properties for work function adjustment.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The work function of the metal electrode is adjusted by changing the chemical composition and structure of the surface layer. By selecting different compounds of formula (I) with varying R1 groups (methyl, fluorinated methyl), R2 groups (—CH2—, —CF2—), and X1 groups (sulfur, selenium derivatives), the electronic properties of the electrode surface can be tuned to match different organic electronic materials.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If the properties of organic electronic materials are adapted by changing composition, then work function matching is improved, but such adaptation is more difficult for metal electrodes

Engineering Contradiction:
Improvework function matchingVSAvoidease of modification
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

Instead of modifying the bulk metal electrode composition, a surface layer (SAM) is applied as an intermediary. This approach allows work function adjustment without changing the fundamental metal electrode structure or requiring complex alloying processes. The SAM can be deposited through simple immersion or vapor deposition methods, making the modification process easier and more versatile.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The electrode system becomes a composite structure consisting of the metal substrate and the organic self-assembled monolayer. This composite approach combines the advantages of both materials: the excellent electrical conductivity of the metal with the tunable electronic properties of the organic compound, achieving work function matching that would be difficult to obtain by modifying the metal alone.

Inventive Principle:
Principle #40Composite materials

3Reliability

If self-assembled monolayers are used to modify metal electrodes, then work function compatibility is improved, but adhesion between adjacent layers may be affected

Engineering Contradiction:
Improvework function compatibilityVSAvoidadhesion between layers
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The compound of formula (I) is designed with different parts having different functions: the sulfur or selenium-based X1 group provides strong bonding to the metal surface for good adhesion, while the aromatic core and terminal groups (R1, R2) provide the necessary electronic properties for work function adjustment. This local differentiation of properties allows simultaneous achievement of good adhesion and work function compatibility.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The self-assembled monolayer acts as a composite interface layer that simultaneously provides adhesion to the metal substrate and compatibility with the organic electronic material. The multi-component structure of the compound (metal-binding group + aromatic core + terminal groups) enables it to fulfill multiple functions: anchoring to the metal, adjusting work function, and providing good interfacial contact with the organic layer.

Inventive Principle:
Principle #40Composite materials

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 self-assembled monolayer enhances the surface properties of metal or metal oxide electrodes, leading to improved charge injection and transport, and controlled wettability, facilitating the deposition of further layers and enhancing the performance of organic electronic devices.

Implementation Method 1

a self-assembled monolayer comprising a moiety of formula (I)

Methodology Applied
Scientific EffectSelf-assembly: Self-Assembly

Implementation Method 2

the metal (or metal oxide) electrodes may be covered with a self-assembled monolayer (SAM) of suitable molecules

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentUS10164191B2Methoxyaryl surface modifier and organic electronic devices comprising such methoxyaryl surface modifier
Publication Date: 2018.12.25 FLEXENABLE TECH LTD
  • US10164191B2 patent drawing
  • US10164191B2 patent drawing
  • US10164191B2 patent drawing

AI summary

The present invention relates to a methoxyaryl surface modifier. In addition the present invention also relates to organic electronic devices comprising such methoxyaryl surface modifier.