Halogenated Perylene Diimide Compounds for Photoreceptor Charge Retention

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Solution Overview

Problem

Existing compounds with electron transporting structures have insufficient solubility in organic solvents and electrical properties, particularly affecting the residual potential property and potential retention rate of photoreceptors.

Innovation Solution

A compound with a perylene diimide skeleton containing halogen atoms and multiple polymerizable functional groups is introduced, enhancing electron transporting properties and solubility in organic solvents, allowing for improved mechanical strength and electrical properties in photoreceptors.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a compound with electron transporting structure is used in the protective layer, then the electrical properties (residual potential property and potential retention rate) are improved, but the solubility in organic solvents becomes insufficient

Engineering Contradiction:

Improveelectrical propertiesVSAvoidsolubility in organic solvents

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure of the electron transporting compound by introducing specific substituents (alkyl groups, alkoxy groups, aryloxy groups, heteroaryloxy groups, alkoxycarbonyl groups, dialkylamino groups, diarylamino groups, arylalkylamino groups, acyl groups, haloalkyl groups, alkylthio groups, arylthio groups, silyl groups, siloxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups) at defined positions (R1-R10) in the perylene diimide core structure. These structural parameter changes simultaneously enhance electron transporting capability and improve solubility in organic solvents by adjusting the balance between conjugation and steric effects.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining the electron transporting perylene diimide core with various functional side chains and substituents. This composite approach allows the molecule to exhibit both excellent electron transporting properties (from the conjugated core) and improved solubility (from the appropriate side chains), resolving the contradiction between electrical performance and processability.

Inventive Principle:

Principle #40Composite materials

2Strength

If a protective layer is formed to improve abrasion resistance, then the mechanical strength is improved, but the electron transporting capability may be compromised

Engineering Contradiction:

Improveabrasion resistanceVSAvoidelectron transporting capability

Core Design Contradiction:

StrengthVSReliability

Solution Approach 1:

The patent designs the protective layer compound to perform multiple functions simultaneously: the perylene diimide core provides electron transporting capability for maintaining electrical properties, while the polymerizable functional groups (acryloyl, methacryloyl, acrylamide, methacrylamide groups) provide mechanical strength through crosslinked polymer network formation. This multi-functional design eliminates the need to choose between protective layer functions.

Inventive Principle:

Principle #6Universality (Multi-functionality)

Solution Approach 2:

The protective layer is formed using a composite composition containing the electron transporting compound combined with polymerizable compounds (such as acrylates, methacrylates, acrylamides, or methacrylamides). This composite approach allows the protective layer to simultaneously achieve mechanical strength from the polymer network and electron transporting capability from the specialized compound, resolving the contradiction between protection and electrical function.

Inventive Principle:

Principle #40Composite materials

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The compound provides excellent electron transporting capability and solubility in organic solvents, resulting in photoreceptors with enhanced residual potential property and potential retention rate.

Implementation Method 1

A compound having two or more polymerizable functional groups in one molecule and having a perylene diimide skeleton into which a halogen atom has been introduced as an electron transporting structure

Methodology Applied

Scientific EffectElectron transport: Conduction (electrical)

Implementation Method 2

a photoreceptor obtained by forming a layer containing a compound having a chain-polymerizable functional group as a binder resin on the outermost layer of the photoreceptor and applying energy such as heat, light, radiation, and the like to the layer to polymerize the compound to form a cured resin layer

Methodology Applied

Scientific EffectPolymerization: Photopolymerisation

Data Source

PatentUS20250320211A1Compound, composition, and electrophotographic photoreceptor

Publication Date: 2025.10.16 MITSUBISHI CHEM CORP

AI summary

The present disclosure relates to a compound having two or more polymerizable functional groups in one molecule and represented by the following formula (1).