2,2'-Bibenzodimidazolidene Compound for Stable OLED Electron Injection

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing organic light-emitting elements face instability and reduced lifetime due to the reactivity of electron injection layers with water and oxidation sensitivity of compounds used, particularly those containing metallic elements.

Innovation Solution

A 2,2′-bibenzo[d]imidazolidene compound with condensed rings at the 1-, 1′-, 3-, and 3′-positions is developed, which is stable to oxidation and water, offering high electron injectability and a shallow HOMO level, thus suitable for use in organic electronic elements without metallic components.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If metallic elements are used in the electron injection layer to improve electron injectability, then electron injection property is improved, but the element becomes reactive with water and has reduced lifetime

Engineering Contradiction:
Improveelectron injection propertyVSAvoidlifetime
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent removes metallic elements from the electron injection layer compound, extracting the harmful reactive component while retaining the desired electron injection functionality through an all-organic compound structure

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the chemical composition parameters by introducing specific organic functional groups (carbazole, triphenylamine, etc.) that provide both high electron injectability and water stability, transforming the material properties without metallic elements

Inventive Principle:
Principle #35Parameter changes

2Reliability

If compounds with high electron injectability are used, then electron injection property is improved, but the compounds are unstable and easily oxidized in air

Engineering Contradiction:
Improveelectron injection propertyVSAvoidoxidation stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent creates a composite molecular structure combining multiple stable aromatic rings and electron-donating groups that work synergistically to provide both high electron injectability and oxidation resistance

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes the HOMO level parameter through careful selection of organic substituents, achieving a balance between electron injectability (requiring appropriate HOMO level) and oxidation stability (requiring resistance to electron loss to oxygen)

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS10403827B22,2'-bibenzo[D]imidazolidene compound having condensed rings at the 1-, 1'-, 3- and 3'-positions, and organic light-emitting element, display device, image information processing apparatus, lighting device, image forming apparatus and exposure unit, each containing the same
Publication Date: 2019.09.03 CANON KK
  • US10403827B2 patent drawing
  • US10403827B2 patent drawing
  • US10403827B2 patent drawing

AI summary

A stable 2,2'-bibenzo[d]imidazolidene compound is provided. The 2,2'-bibenzo[d]imidazolidene compound is expressed by the following General Formula (1). In General Formula (1), Ar.sub.1 to Ar.sub.8 each represent a substituted or unsubstituted condensed ring. R.sub.1 to R.sub.8 each represent a hydrogen atom or a substituent. ##STR00001##