Organic Charge-Transporting Material for OLED Heat Resistance

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Solution Overview

Problem

Existing organic electroluminescent devices face challenges with charge transportability, heat resistance, and amorphous nature due to limitations in polymer materials like polyaniline and 1,3-dihydroimidazol-2-one derivatives, which affect light-emission efficiency and device longevity.

Innovation Solution

A novel organic compound with a 1,3-dihydroimidazol-2-one structure and urea bond, offering improved heat resistance, amorphous nature, and charge transportability, is developed, allowing for the formation of high-brightness, long-life organic electroluminescent devices using a wet film-forming method.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If polymer materials like polyaniline are used to increase charge transportability, then charge transportability is improved, but heat resistance deteriorates and degradation occurs during continuous driving

Engineering Contradiction:
Improvecharge transportabilityVSAvoidheat resistance
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent changes the chemical structure parameters by introducing a 1,3-dihydroimidazol-2-one core with urea bonds and aromatic substituents, transforming the material from a polymer to a small molecule compound. This structural parameter change simultaneously improves charge transportability through the urea bond's electron delocalization and heat resistance through the aromatic ring's thermal stability, resolving the contradiction between these two properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining the 1,3-dihydroimidazol-2-one core, urea bonding units, and aromatic hydrocarbon groups. This composite structure integrates the charge-transporting capability of the urea bond with the thermal stability of aromatic rings, achieving both improved charge transportability and heat resistance without the degradation issues of polymer materials.

Inventive Principle:
Principle #40Composite materials

2Reliability

If 1,3-dihydroimidazol-2-one derivatives are used to improve charge transportability, then charge transportability is improved, but heat resistance and amorphous nature deteriorate

Engineering Contradiction:
Improvecharge transportabilityVSAvoidheat resistance and amorphous nature
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent modifies the molecular parameters by incorporating rigid aromatic hydrocarbon groups (such as phenyl, naphthyl, or anthryl groups) as substituents on the 1,3-dihydroimidazol-2-one core. This parameter change increases the glass transition temperature and enhances the amorphous nature of the material, thereby improving heat resistance and compositional stability while preserving the charge transportability provided by the urea bond structure.

Inventive Principle:
Principle #35Parameter changes

3Use of energy by moving object

If phosphorescent emission is utilized to increase light-emission efficiency, then light-emission efficiency is improved, but sufficient luminance and lifetime are not obtained

Engineering Contradiction:
Improvelight-emission efficiencyVSAvoidlifetime
Core Design Contradiction:
Use of energy by moving objectVSDuration of action of stationary object

Solution Approach 1:

The patent changes the energy level parameters of the charge-transporting material by optimizing the HOMO and LUMO levels through selective substitution on the 1,3-dihydroimidazol-2-one core. This parameter optimization improves electron injection efficiency and charge carrier mobility, enabling sufficient luminance and extended device lifetime when used in conjunction with phosphorescent emitters, thereby resolving the limitation of insufficient operational duration.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS8022617B2Organic compound, charge-transporting material, composition for charge-transporting material and organic electroluminescent device
Publication Date: 2011.09.20 MITSUBISHI CHEM CORP
  • US8022617B2 patent drawing
  • US8022617B2 patent drawing
  • US8022617B2 patent drawing

AI summary

An organic compound having excellent heat resistance, an excellent amorphous nature, an excellent ability to transport charges, highly excited singlet and triplet states, and excellent solubility in an organic solvent is an organic compound represented by Formula (I):wherein Ar1 represents an optionally-substituted aromatic hydrocarbon group, an optionally-substituted aromatic heterocyclic group, or an optionally-substituted alkyl group; Ar2 represents an optionally-substituted aromatic hydrocarbon group or an optionally-substituted aromatic heterocyclic group; R1 and R2 each represent a hydrogen atom or a substituent, and R1 and R2 may be bonded to each other to form a ring; and Q is represented by Formula (I-1) or (I-2):wherein Ar3 to Ar5 each represent an optionally-substituted aromatic hydrocarbon group or an optionally-substituted aromatic heterocyclic group, and Ar3 and Ar4 may be bonded to each other to form a ring.