Indenocarbazole Compounds for OLED Matrix Materials

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Solution Overview

Problem

There is a need for alternative compounds with improved performance data, particularly in terms of operating voltage, power efficiency, and lifetime, for use in organic electroluminescent devices, specifically as matrix materials for phosphorescent emitting layers, as existing compounds containing carbazole, indenocarbazole, and electron-deficient heteroaromatic rings do not meet the desired standards.

Innovation Solution

A compound of formula (I) featuring an indenocarbazole group connected to an electron-deficient six-membered heteroaromatic ring via its N atom and carrying a carbazole substituent bonded via one of its carbon atoms, which exhibits excellent performance when used in organic electroluminescent devices, specifically achieving enhanced lifetime and power efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing compounds containing carbazole, indenocarbazole, and electron-deficient heteroaromatic rings are used as matrix materials in phosphorescent emitting layers, then the basic functionality is achieved, but the performance data (lifetime, power efficiency, operating voltage) do not meet the desired standards

Engineering Contradiction:
Improvedevice lifetimeVSAvoidperformance optimization
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by systematically varying the substitution patterns on the carbazole and indenocarbazole groups, changing the type of electron-deficient heteroaromatic rings (pyridine, pyrimidine, triazine), and modifying the positions of attachment to optimize the balance between lifetime, power efficiency, and operating voltage. This is evident in the multiple compounds of formula (I) with different R1-R6 substituents and heteroaryl group variations

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by combining indenocarbazole groups with carbazole groups and electron-deficient heteroaromatic rings in specific molecular architectures. The compounds of formula (I) represent composite molecular structures that integrate multiple functional moieties to achieve synergistic effects, improving both lifetime and power efficiency simultaneously

Inventive Principle:
Principle #40Composite materials

2Duration of action of stationary object

If compounds with improved lifetime are developed, then device longevity increases, but the complexity of molecular design and synthesis increases

Engineering Contradiction:
Improvedevice lifetimeVSAvoidmolecular structure complexity
Core Design Contradiction:
Duration of action of stationary objectVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the molecular structure into distinct functional segments: indenocarbazole core groups, carbazole substituent groups, and electron-deficient heteroaromatic ring groups. This modular approach allows independent optimization of each segment's properties while maintaining overall molecular functionality, managing complexity through systematic structuring

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent implements local quality by assigning specific functional roles to different parts of the molecule: the indenocarbazole groups provide structural framework and charge transport, the carbazole groups contribute to hole transport and stability, while the electron-deficient heteroaromatic rings enhance electron transport and adjust energy levels. Each local region is optimized for its specific function to achieve overall performance improvement

Inventive Principle:
Principle #3Local quality

3Loss of energy

If compounds with improved power efficiency are developed, then energy utilization increases, but the operating voltage may increase

Engineering Contradiction:
Improvepower efficiencyVSAvoidoperating voltage
Core Design Contradiction:
Loss of energyVSUse of energy by moving object

Solution Approach 1:

The patent applies parameter changes by systematically adjusting the electron-deficiency of the heteroaromatic rings (comparing pyridine, pyrimidine, and triazine with increasing electron-deficiency), varying the substitution patterns on carbazole and indenocarbazole groups, and modifying the positions of group attachments. These parameter variations allow optimization of the balance between power efficiency and operating voltage by tuning energy levels and charge transport properties

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS9985220B2Materials for electronic devices
Publication Date: 2018.05.29 MERCK PATENT GMBH
  • US9985220B2 patent drawing
  • US9985220B2 patent drawing
  • US9985220B2 patent drawing

AI summary

The present application relates to a compound of a formula (I) which contains an indenocarbazole group, a carbazole group and an electron-deficient group bonded to the indenocarbazole group. The compound is suitable for use in electronic devices, in particular in organic electroluminescent devices.