Imidazoazacyclo OLED Material for Light Extraction and Low Voltage

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Solution Overview

Problem

Current organic electroluminescent apparatuses face challenges in enhancing luminous efficiency, reducing driving voltage, and extending service life, primarily due to limitations in the thermal stability, light chemical stability, electrochemical stability, and refractive index of existing light extraction layer materials.

Innovation Solution

The development of an imidazoazacyclo compound with a specific structure, which exhibits low sublimation temperature, good light and electrical stability, high refractive index, and minimal refractive index variation across the visible light spectrum, enabling its application as an electron transmission material, hole barrier layer material, and light extraction layer material in OLEDs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If conventional light extraction layer materials are used, then the apparatus structure is simple, but the refractive index is low and external quantum efficiency is limited

Engineering Contradiction:
Improveexternal quantum efficiencyVSAvoidmaterial structure complexity
Core Design Contradiction:
Illumination intensityVSDevice complexity

Solution Approach 1:

The patent changes the molecular structure parameters of the light extraction layer material by introducing imidazoazacyclo core structures with specific substituents (R1-R6 groups), which directly increases the refractive index from conventional values below 1.85 to above 1.90, thereby improving external quantum efficiency without adding structural layers

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining imidazoazacyclo core with various aromatic hydrocarbon groups and heterocyclic groups, forming compounds with optimized optical properties that achieve high refractive index while maintaining processability and stability

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If existing light extraction materials are used, then the material selection is simple, but the refractive index varies hugely across red, green and blue wave bands

Engineering Contradiction:
Improverefractive index stabilityVSAvoidcolor band adaptability
Core Design Contradiction:
Stability of the object's compositionVSAdaptability or versatility

Solution Approach 1:

The patent optimizes molecular parameters by selecting specific core structures and substituent groups that provide balanced electron distribution, resulting in refractive indexes across red, green and blue bands that differ by less than 0.05, ensuring consistent optical performance across the visible spectrum

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces different substituent groups (R1-R6) at specific positions on the imidazoazacyclo core to locally adjust electron density and polarizability, achieving uniform refractive index characteristics across different wavelength regions through targeted molecular modification

Inventive Principle:
Principle #3Local quality

3Duration of action of stationary object

If compounds with improved triplet state energy level are used, then the service life is extended, but the glass-transition temperature and luminous efficiency need further improvement

Engineering Contradiction:
Improveservice lifeVSAvoidluminous efficiency
Core Design Contradiction:
Duration of action of stationary objectVSIllumination intensity

Solution Approach 1:

The patent combines imidazoazacyclo core with aromatic hydrocarbon groups and heterocyclic groups to create composite molecular structures that simultaneously achieve high triplet state energy levels (improving service life) and high refractive indexes (improving luminous efficiency through enhanced light extraction), resolving the trade-off between durability and efficiency

Inventive Principle:
Principle #40Composite materials

4Ease of manufacture

If polyphenylenediamine-based light extraction materials are used, then the material is easy to manufacture, but the refractive index is slightly low and red light extraction needs improvement

Engineering Contradiction:
Improvemanufacturing easeVSAvoidred light extraction efficiency
Core Design Contradiction:
Ease of manufactureVSIllumination intensity

Solution Approach 1:

The patent modifies the molecular parameters by replacing polyphenylenediamine structures with imidazoazacyclo cores and introducing specific aromatic and heterocyclic substituents, which increases the refractive index particularly in the red light region while maintaining vacuum sublimation deposition compatibility for ease of manufacture

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS12240861B2Imidazo nitrogen heterocyclic compound and application thereof
Publication Date: 2025.03.04 GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
  • US12240861B2 patent drawing
  • US12240861B2 patent drawing
  • US12240861B2 patent drawing

AI summary

The present invention relates to an imidazoazacyclo compound and an application thereof. The compound of the present invention has a structure as shown in a formula I. The imidazoazacyclo compound of the present invention has the advantages of low sublimation temperature, good light stability, electrical stability and thermal stability, high refractive index, small difference of refractive index in a visible light area and the like, and an apparatus prepared by the compound has the advantages of low voltage, long service life, high luminous efficiency and the like and can be used in an organic luminescent apparatus. In particular, as an electron transmission material, a hole barrier layer material and a light extraction layer material, the imidazoazacyclo compound has the probability of being applied to an AMOLED industry.