Organic Semiconductor Compound for OLED Electron Transport

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Solution Overview

Problem

Current organic light-emitting diodes (OLEDs) face challenges in achieving balanced electron and hole injection, leading to inefficiencies and reduced lifespan, particularly at higher current densities and brightness levels, with a need for materials that enhance electron mobility and electrochemical stability while lowering operating voltage.

Innovation Solution

A compound of the formula A-(Cy)n-Pz-FL is developed, where A is a substituted or unsubstituted aryl or heteroaryl, Cy is a hydrocarbon group, Pz is fully substituted pyrazinylene, and FL is fluorenyl, specifically designed to form an organic semiconductor layer that improves electron transport and stability, excluding benzoxazolyl and carbazolyl to enhance device performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional organic semiconductor materials are used, then device structure is simple, but electron mobility is insufficient and electrochemical stability is poor

Engineering Contradiction:
Improveelectrochemical stabilityVSAvoidcompound structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent employs composite organic semiconductor materials combining multiple functional units (A, Cy, Pz, FL) in a single molecule. The compound structure A-(Cy)n-Pz-FL integrates electron-transporting moieties (Pz pyrazinylene, FL fluorenyl) with stabilizing groups (A aryl/heteroaryl, Cy hydrocarbon), creating a composite material that simultaneously achieves high electron mobility and electrochemical stability while maintaining reasonable structural complexity through systematic molecular design.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies local quality by assigning specific functional roles to different parts of the molecule: the Pz (pyrazinylene) and FL (fluorenyl) units provide electron transport capability, the A (aryl/heteroaryl) group enhances electrochemical stability, and the Cy (hydrocarbon) linker controls molecular packing. This localized functional distribution allows each segment to optimize its contribution to overall device performance.

Inventive Principle:
Principle #3Local quality

2Illumination intensity

If higher current density is applied to increase brightness, then illumination intensity improves, but device lifespan decreases

Engineering Contradiction:
ImprovebrightnessVSAvoiddevice lifespan
Core Design Contradiction:
Illumination intensityVSDuration of action of stationary object

Solution Approach 1:

The patent changes the chemical parameters of the organic semiconductor material by introducing electrochemically stable functional groups (Pz pyrazinylene, FL fluorenyml, A aryl/heteroaryl). These structural modifications alter the material's HOMO-LUMO energy levels and redox stability, enabling the device to operate at higher current densities without degradation. The modified material parameters allow sustained high brightness operation while extending device lifespan.

Inventive Principle:
Principle #35Parameter changes

3Use of energy by moving object

If operating voltage is reduced to lower power consumption, then energy efficiency improves, but electron transport capability may be compromised

Engineering Contradiction:
Improvepower consumptionVSAvoidelectron transport speed
Core Design Contradiction:
Use of energy by moving objectVSSpeed

Solution Approach 1:

The patent optimizes the energy level parameters of the organic semiconductor by carefully selecting and combining functional units with complementary HOMO and LUMO levels. The Pz (pyrazinylene) and FL (fluorenyml) units provide appropriate electron affinity, while the A (aryl/heteroaryl) group adjusts the HOMO level. This parameter optimization enables efficient electron injection at lower voltages while maintaining high electron transport speed through the optimized energy landscape and improved molecular packing.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP4299573A1Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and a method for preparing the organic electronic device
Publication Date: 2024.01.03 NOVALED GMBH
  • EP4299573A1 patent drawingFigure 1~2
  • EP4299573A1 patent drawingFigure 3
  • EP4299573A1 patent drawingFigure 4

AI summary

The present invention relates to a compound, an organic semiconducting material comprising the same, an organic electronic device comprising the same and a method for preparing the organic electronic device.