Benzimidazole Derivatives for OLED Efficiency and Lifetime

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Solution Overview

Problem

There is a need for benzimidazole derivatives that can improve the efficiency, operating voltage, and lifetime of organic electroluminescent devices while maintaining excellent color purity, processability, and solubility, and be cost-effective with consistent quality across a broad temperature range.

Innovation Solution

The development of specific benzimidazole derivatives with defined structural formulas, which serve as matrix, hole transport, or electron transport materials in organic electroluminescent devices, enhancing device performance through improved material properties and film formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If conventional materials are used in organic electroluminescent devices, then device structure is simple, but lifetime is short and efficiency is low

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

Solution Approach 1:

The patent employs composite material design by combining benzimidazole core structure with various functional groups (carbazole, triphenylene, dibenzofuran) to create materials that simultaneously achieve long lifetime, high efficiency, and appropriate device complexity. The composite molecular structures integrate multiple aromatic systems that work synergistically to improve device performance.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent systematically varies molecular parameters including substituent types (aryl, heteroaryl groups), substitution patterns (positions on benzimidazole ring), and molecular weight ranges (500-2000 g/mol) to optimize the balance between lifetime, efficiency, and processability. This parameter optimization enables tuning of material properties for specific device applications.

Inventive Principle:
Principle #35Parameter changes

2Use of energy by moving object

If materials with high efficiency are used, then energy conversion is improved, but operating voltage increases

Engineering Contradiction:
Improveenergy efficiencyVSAvoidoperating voltage
Core Design Contradiction:
Use of energy by moving objectVSStress or pressure

Solution Approach 1:

The patent introduces local functional groups with specific electronic properties (electron-donating or electron-withdrawing groups) at strategic positions on the benzimidazole core. This local modification of electronic structure allows optimization of charge transport and energy levels, achieving high efficiency while controlling operating voltage through localized electronic effects rather than global structural changes.

Inventive Principle:
Principle #3Local quality

3Manufacturing precision

If compounds with high color purity are developed, then device color quality improves, but manufacturing complexity increases

Engineering Contradiction:
Improvecolor purityVSAvoidmanufacturing simplicity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent achieves color purity through segmentation of the molecular structure into distinct functional modules: the benzimidazole core provides structural stability, while peripheral aromatic groups (carbazole, triphenylene, dibenzofuran) control optical properties. This modular segmentation allows independent optimization of color characteristics without complicating the overall synthesis pathway, as each module can be introduced through standardized coupling reactions.

Inventive Principle:
Principle #1Segmentation

4Ease of manufacture

If materials with good solubility are used, then processability is improved, but film formation quality may deteriorate

Engineering Contradiction:
Improvesolubility and processabilityVSAvoidfilm formation quality
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent introduces solubilizing side chains and flexible linker groups as intermediary elements between the rigid aromatic core and the solvent environment. These intermediary groups enhance solubility by improving solvent interaction, while their controlled flexibility and length are optimized to maintain proper molecular packing and film morphology during device fabrication, thus balancing processability with film quality.

Inventive Principle:
Principle #24Intermediary (Mediator)

Data Source

PatentUS20230139809A1Benzimidazole derivatives
Publication Date: 2023.05.04 MERCK PATENT GMBH
  • US20230139809A1 patent drawing
  • US20230139809A1 patent drawing
  • US20230139809A1 patent drawing

AI summary

The invention relates to benzimidazole derivatives which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.