Cerium Complexes for Organic Electronics Doping

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Solution Overview

Problem

Current organic semiconductor materials face challenges with volatility, high absorption coefficients, unstable evaporation rates, and high production costs, limiting the effectiveness of known p-dopants and electron transport materials in organic electronic components.

Innovation Solution

Development and use of cerium-ethylenediamine ketone-like and cerium-salen-like complexes as p-dopants and electron transport materials, which exhibit excellent thermal stability, low absorption, and high doping efficiency, suitable for both vacuum and solvent-based processing in organic electronic components.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If known p-dopants and electron transport materials are used in organic semiconductor materials, then doping efficiency is achieved, but volatility, high absorption coefficient, unstable evaporation rate, and high production costs occur

Engineering Contradiction:
Improvedoping efficiencyVSAvoidvolatility, high absorption coefficient, unstable evaporation rate, high production costs
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the molecular structure of dopant materials through the introduction of bulky substituent groups (such as triisopropylsilyl groups) and specific ligand designs (β-diketonate and aminopyridine ligands). These structural parameter changes reduce volatility and improve thermal stability while maintaining doping efficiency, directly resolving the contradiction between doping performance and material stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by creating complex molecular structures that combine multiple functional components: cerium centers coordinated with specific organic ligands (β-diketonates and aminopyridines), and incorporation of bulky hydrophobic substituents. This composite approach achieves both high doping efficiency and reduced volatility/absorption, resolving the technical contradiction between performance and stability.

Inventive Principle:
Principle #40Composite materials

2Reliability

If known electron acceptors are used for p-doping, then hole generation in semiconductor matrix occurs, but too high absorption coefficient and parasitic absorption increase

Engineering Contradiction:
Improvehole generation capabilityVSAvoidhigh absorption coefficient, parasitic absorption
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies local quality by designing electron acceptor molecules with localized electron-accepting centers (cerium atoms with specific coordination geometries) surrounded by bulky hydrophobic substituent groups. This local differentiation allows the molecule to maintain high electron-accepting capability at the cerium center while the peripheral groups reduce overall absorption coefficient and parasitic absorption, resolving the contradiction between hole generation and absorption characteristics.

Inventive Principle:
Principle #3Local quality

3Reliability

If conventional doping materials are used, then conductivity is improved, but thermal stability of doped layers deteriorates

Engineering Contradiction:
Improveelectrical conductivityVSAvoidthermal stability of doped layers
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by modifying the thermal stability parameters of doping materials through the introduction of rigid ligand frameworks (β-diketonates and aminopyridines) and bulky substituent groups that increase molecular weight and reduce volatility. These parameter changes enable the material to maintain both high electrical conductivity through effective doping and superior thermal stability, resolving the contradiction between conductivity and thermal stability.

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 cerium complexes demonstrate improved conductivity, reduced parasitic absorption, and enhanced thermal stability of doped layers, making them suitable for a wide range of organic and hybrid optoelectronic components with lower production costs.

Implementation Method 1

For p-type doping, strong electron acceptors (p-dopants) are used, which remove an electron from the HOMO of the semiconductor matrix (p-doping), leaving a hole. In other words, with p-doping, the LUMO of the dopant must be below the HOMO energy of the matrix. The dopant acts as an acceptor, leaving a mobile hole (SOMO) in the matrix.

Methodology Applied
Scientific EffectElectron transfer:

Implementation Method 2

They are fundamentally suitable for both processing methods for organic electronic components: vacuum deposition (vapor deposition) and solvent-based processing (solution processing).

Methodology Applied
Scientific EffectVacuum deposition: Physical Vapour Deposition

Implementation Method 3

many of these cerium(IV) complexes can be easily evaporated in a vacuum and sometimes exhibit high thermal stability. Thus, they are fundamentally suitable for both processing methods for organic electronic components: vacuum deposition (vapor deposition) and solvent-based processing (solution processing).

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentEP4244910B1Cerium-ethylenediamine ketone-type and cerium-salen-type complexes and use thereof in organic electronics
Publication Date: 2024.12.11 CREDOXYS GMBH
  • EP4244910B1 patent drawing
  • EP4244910B1 patent drawing
  • EP4244910B1 patent drawing

AI summary

The present invention relates to an electronically doped semiconductor material and to an electronic component comprising cerium-ethylenediamine ketone-type and cerium-salen-type complexes. The invention also relates to the use of the cerium-ethylenediamine ketone-type and cerium-salen-type complexes as electron acceptors, especially as p-dopants and electron transport materials in organic-electronic components. The invention further relates to novel cerium-ethylenediamine ketone-type and cerium-salen-type complexes.