Crosslinked p-Dopant Layers for Organic Electronics

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Solution Overview

Problem

The production of highly efficient and long-lasting p-conducting hole-conducting layers in organic electronics is challenging due to issues with dopant washing out or segregation, and the limited selection of solvents in wet processes, which restricts the structural complexity and electrical fine adjustment of layer sequences.

Innovation Solution

The method involves using functionalized p-dopants that crosslink with each other and functionalized hole conductors through chemical reactions, forming covalent bonds to create a stable, crosslinked layer that is resistant to leaching and foreign substances, allowing for a broader selection of solvents and improved layer structure control.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional p-dopants are used in wet processes, then the production process is simple, but the dopants leach or segregate from the layer

Engineering Contradiction:
Improveproduction process simplicityVSAvoiddopant stability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent applies preliminary action by functionalizing the p-dopant molecules with crosslinkable groups before deposition. This pre-prepared functionalization enables subsequent crosslinking that prevents dopant leaching and segregation, resolving the reliability issue while maintaining manufacturing simplicity.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent creates a composite structure by combining the p-dopant with hole conductor materials through crosslinking. This composite approach forms a stable integrated layer where the dopant is chemically bound to the matrix, preventing segregation while maintaining ease of manufacture through solution processing.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If orthogonal solvents are used in subsequent processing steps, then underlying layers are protected from dissolution, but the selection of solvents and processable organic substances is restricted

Engineering Contradiction:
Improvelayer integrityVSAvoidsolvent selection freedom
Core Design Contradiction:
Stability of the object's compositionVSAdaptability or versatility

Solution Approach 1:

The crosslinkable functional groups are introduced into the p-dopant and hole conductor before layer deposition. After deposition, crosslinking is activated to create a chemically resistant network, enabling subsequent processing with diverse solvents without requiring orthogonal solvent selection.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent changes the chemical state of the layer from uncrosslinked to crosslinked, fundamentally altering its properties. The crosslinked network provides chemical inertness that allows free selection of solvents for subsequent layers, resolving the contradiction between layer stability and solvent versatility.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If p-dopants are used to increase conductivity, then hole-conducting efficiency improves, but the dopants wash out or segregate during processing

Engineering Contradiction:
Improveconductivity efficiencyVSAvoiddopant retention
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The p-dopants are pre-functionalized with crosslinkable groups that enable covalent bonding to the hole conductor matrix. This preliminary preparation ensures that once crosslinked, the dopants remain firmly embedded in the layer, maintaining high conductivity efficiency while preventing washout and segregation.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent creates a composite material system where the p-dopant and hole conductor are chemically integrated through crosslinking. This composite structure ensures the dopant remains embedded in the matrix, maintaining conductivity efficiency while preventing substance loss during processing.

Inventive Principle:
Principle #40Composite materials

4Reliability

If crosslinking is implemented to prevent dopant leaching, then layer stability improves, but the process complexity increases

Engineering Contradiction:
Improvelayer stabilityVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The crosslinkable functional groups are pre-installed on the p-dopant and hole conductor molecules before deposition. The crosslinking step itself remains simple, requiring only standard photolithography or thermal treatment, thus improving layer stability without significantly increasing process complexity.

Inventive Principle:
Principle #10Preliminary action

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

This approach results in mechanically stable and chemically inert layers with enhanced shelf life and conductivity, minimizing diffusion between layers and enabling more complex layer structures without dissolving underlying layers, thus improving the reliability and processability of organic electronic components.

Implementation Method 1

The functionalized p-dopants can crosslink with each other and/or with functionalized hole conductors through a chemical reaction. Crosslinking, here and below, refers to the formation of covalent bonds between the functionalized p-dopants and/or between the functionalized p-dopants and the functionalized hole conductors.

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentEP3472876B1Cross-linking p-dopant for p-doping organic hole conductors
Publication Date: 2024.04.17 MERCK PATENT GMBH
  • EP3472876B1 patent drawingFigure 1~2
  • EP3472876B1 patent drawingFigure 3A~3F
  • EP3472876B1 patent drawing

AI summary

The invention relates to a method for producing cross-linked hole-conducting electric layers by converting functionalized p-dopants. The functionalized p-dopants are organic metal complexes which comprise at least one central atom and organic ligands, wherein the central atom is selected from a metal of the groups 6-15 of the periodic table, and at least one of the organic ligands is selected from the following formulas I-V, in which E independently of one another is oxygen, sulfur, selenium, or N(E1)x, and each Rv has at least one functionalizing group selected from the group RF comprising -OH, -COOH, -NH2, -NHR`, halogen, C2-C40-alkenyl, - dienyl, -alkinyl, -alkenyloxy, -dienyloxy, -alkinyloxy, acrylic acid, oxetan, oxiran, silane, acrylic acid, anhydride, and cyclobutane or consists of said groups, and G = C(RF)uHvFw where u+v+w = 3 and n = 1 - 4.