Organic Semiconductor Compound Tuning for Stable Low-Voltage OLEDs

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Solution Overview

Problem

Existing organic semiconductor materials in organic electronic devices, such as OLEDs, face challenges in achieving improved operating voltage, efficiency, lifetime, and thermal stability, particularly in terms of LUMO energy, dipole moment, and thermal properties.

Innovation Solution

The development of a compound of formula (I) with specific structural features, including various substituents and binding positions, enhances the performance of organic semiconductor layers by improving LUMO energy, dipole moment, and thermal stability, leading to better hole injection and processing properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional organic semiconductor materials are used in OLEDs, then the device structure and basic functionality are maintained, but the operating voltage, efficiency, lifetime, and thermal stability remain suboptimal

Engineering Contradiction:
Improvedevice performance and stabilityVSAvoidcompound structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by systematically modifying the molecular structure of organic semiconductor compounds through varying substituents (R1-R6) on the core heteroaryl framework. Different combinations of alkyl, aryl, and heteroaryl groups are introduced to optimize electronic properties including HOMO/LUMO energy levels, dipole moments, and thermal stability, thereby improving device performance without fundamentally changing the device architecture

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs composite material principles by creating complex organic semiconductor molecules that combine multiple functional groups and structural motifs within a single compound. The core heteroaryl structure is复合 with various substituents including electron-donating and electron-withdrawing groups, forming composite molecular structures that achieve synergistic effects for improved charge transport and thermal stability

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If the compound structure is optimized to improve LUMO energy and dipole moment, then hole injection and processing properties are enhanced, but the synthesis and manufacturing complexity increases

Engineering Contradiction:
Improveprocessing propertiesVSAvoidcompound structural features
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent systematically adjusts molecular parameters such as substituent types, positions, and configurations to optimize processing properties. By varying the core heteroaryl structure and attached groups, the invention tunes solubility, crystallinity, and thermal characteristics to enable solution processing and vacuum deposition, balancing manufacturing ease with structural complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention applies local quality by introducing specific functional groups at particular positions on the molecular framework. Different substituents are placed at specific locations (R1-R6 positions) to locally modify electronic and steric properties, enabling precise control over charge transport, packing behavior, and processing characteristics without redesigning the entire molecule

Inventive Principle:
Principle #3Local quality

3Temperature

If thermal stability is improved through compound design, then processing at elevated temperatures is enhanced, but the molecular structure becomes more complex

Engineering Contradiction:
Improvethermal stabilityVSAvoidmolecular structure
Core Design Contradiction:
TemperatureVSDevice complexity

Solution Approach 1:

The patent improves thermal stability by changing molecular parameters including increasing molecular weight through larger substituents, introducing rigid aromatic groups, and creating extended conjugation systems. These parameter changes raise the glass transition temperature and thermal decomposition temperature, enabling stable processing at elevated temperatures while managing structural complexity through systematic molecular design

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP4438584B1Compound of formula (i) and their use in an organic electronic device
Publication Date: 2025.11.12 NOVALED GMBH
  • EP4438584B1 patent drawingFigure 1~2
  • EP4438584B1 patent drawingFigure 3~4
  • EP4438584B1 patent drawingFigure 5~6

AI summary

The present invention relates to a compound and their use in organic electronic devices, an organic semiconductor layer comprising the compound, an organic electronic device comprising the organic semiconductor layer, and a display device comprising the organic electronic device.