Electrically Doped Organic Semiconductors for OLEDs

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Solution Overview

Problem

Current organic semiconducting materials for OLEDs face challenges in achieving low operational voltage, high efficiency, and good thermal characteristics while being air stable and reproducible for mass production, particularly with the use of strong reductive n-dopants like W2(hpp)4, which are costly and difficult to handle safely.

Innovation Solution

Development of electrically doped semiconducting materials comprising metal salts and specific xanthene matrix compounds with nitrogen-containing heterocyclic substituents, such as lithium salts, to enhance charge injection and stability in organic electronic devices, with optimized additive content and layer thickness.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If strong reductive n-dopants like W2(hpp)4 are used for electrical doping, then charge injection efficiency is improved, but handling safety and manufacturing cost deteriorate

Engineering Contradiction:
Improvecharge injection efficiencyVSAvoidhandling safety and manufacturing cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive, air-sensitive strong reductive dopants (W2(hpp)4) with inexpensive, air-stable metal salt additives (lithium salts). These metal salts can be handled in ambient conditions without special precautions, eliminating the need for costly inert atmosphere equipment and specialized handling procedures while maintaining effective electrical doping performance

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

Solution Approach 2:

The invention changes the chemical nature of the dopant from strong reductive agents to metal salt additives, fundamentally altering the doping mechanism. This parameter change enables the system to achieve effective charge injection through metal coordination with the xanthene matrix rather than through strong reduction, thereby improving safety and manufacturability

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If metal salt additives are used for electrical n-doping, then air stability is improved, but doping efficiency deteriorates

Engineering Contradiction:
Improveair stabilityVSAvoiddoping efficiency
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent creates a composite system where metal salt additives (lithium salts) are combined with specifically designed xanthene matrix compounds containing nitrogen-containing heterocyclic substituents. This composite material approach enables the metal salts to achieve effective doping efficiency through coordination interactions with the nitrogen atoms in the xanthene matrix, overcoming the limitation of using metal salts alone

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The xanthene matrix is functionally differentiated by incorporating nitrogen-containing heterocyclic substituents at specific positions. These localized nitrogen sites serve as coordination centers for metal salt additives, creating localized high-efficiency doping zones within the matrix that enhance overall doping efficiency while maintaining air stability

Inventive Principle:
Principle #3Local quality

3Reliability

If xanthene matrices with nitrogen-containing heterocyclic substituents are used, then electrical properties are improved, but molecular complexity increases

Engineering Contradiction:
Improveelectrical propertiesVSAvoidmolecular complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The xanthene matrix molecule is segmented into distinct functional modules: the core xanthene structure providing electron transport capability, and nitrogen-containing heterocyclic substituents (pyridyl, quinolinyl groups) providing coordination sites for metal salts. This modular segmentation allows each part to perform its specific function while keeping the overall molecular design systematic and controllable

Inventive Principle:
Principle #1Segmentation

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 proposed solution enables efficient charge injection and improved performance in OLEDs with reduced operational voltage and enhanced power efficiency, as demonstrated by experimental results showing effective charge transport and stability with the use of nitrogen-containing xanthene matrices and metal additives.

Implementation Method 1

electrically doped semiconducting material comprising i) at least one electrical dopant selected from metal salts and ii) at least one matrix compound of formula 1

Methodology Applied
Scientific EffectElectron transfer: Redox Reactions

Implementation Method 2

at least one matrix compound of formula 1 wherein A and A′ are independently selected from C1-C20 heteroaryl group comprising at least one sp2 hybridized nitrogen atom

Methodology Applied
Scientific EffectCoordination bonding: Chemical Bonding

Data Source

PatentUS10862052B2Electrically doped organic semiconducting material and organic light emitting device comprising it
Publication Date: 2020.12.08 NOVALED GMBH
  • US10862052B2 patent drawing
  • US10862052B2 patent drawing
  • US10862052B2 patent drawing

AI summary

The invention relates to electrically doped semiconducting material comprising iii) at least one electrical dopant selected from metal salts consisting of at least one metal cation and at least one anion and iv) at least one matrix compound of formula 1wherein each of R1, R2, R1, R2′ is independently selected from H, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl or both substituents on the same aromatic ring of the xanthene skeleton are hydrocarbyl groups linked with each other to form together an anelated divalent C2-C10 hydrocarbyl group and A and A′ are independently selected from C1-C20 heteroaryl group comprising at least one sp2 hybridized nitrogen atom as well as an electronic device and a compound.