Terphenyl Compound Structure for Photosensitive Layer Crystallization

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Solution Overview

Problem

The existing electrophotographic photosensitive members, particularly those containing terphenyl diamine, suffer from insufficient electrical characteristics and are prone to crystallization in the photosensitive layer, which affects their sensitivity and performance.

Innovation Solution

A terphenyl compound represented by general formula (1) is introduced, which includes specific alkyl and aryl groups that improve electrical characteristics and inhibit crystallization when used in the photosensitive layer, along with a method for producing this compound using a reaction between compounds represented by general formulas (a), (b), and (c) with a transition metal-containing catalyst and a ligand.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If terphenyl diamine is used as charge transport material, then charge transport function is provided, but electrical characteristics are insufficient and crystallization occurs in photosensitive layer

Engineering Contradiction:
Improveelectrical characteristicsVSAvoidcrystallization in photosensitive layer
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent modifies the molecular structure parameters of the terphenyl diamine compound by introducing specific substituents (R1-R6 groups) with controlled carbon atom counts and types (alkyl, aryl, heteroaryl). This structural parameter change optimizes both electrical characteristics and crystallization resistance in the photosensitive layer.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite hole transport material by combining terphenyl diamine core structure with various substituent groups (alkyl, aryl, heteroaryl). This composite molecular structure achieves both improved electrical characteristics and inhibition of crystallization through the synergistic effect of different functional groups.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional terphenyl diamine structure is used, then charge transport is achieved, but sensitivity of electrophotographic photosensitive member is insufficient

Engineering Contradiction:
ImprovesensitivityVSAvoidproduction yield
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent optimizes the molecular parameters of the terphenyl diamine compound by controlling the types and positions of substituent groups (R1-R6), particularly focusing on alkyl groups with 1-6 carbon atoms and aromatic rings. This parameter optimization enhances sensitivity while the provided synthesis method ensures acceptable production yield through controlled reaction conditions.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If existing hole transport material is used, then charge transport layer is formed, but electrical characteristics and exposure memory-inhibiting performance are insufficient

Engineering Contradiction:
Improveexposure memory-inhibiting performanceVSAvoidstructure of photosensitive layer
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent changes the molecular structure parameters of the hole transport material by introducing specific substituent patterns (R1-R6 groups with controlled carbon counts and types). This structural modification improves exposure memory-inhibiting performance while maintaining a relatively simple single-layer or multi-layer photosensitive layer configuration.

Inventive Principle:
Principle #35Parameter changes

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 terphenyl compound enhances the electrical characteristics and inhibits crystallization in the photosensitive layer, thereby improving the sensitivity and exposure memory-inhibiting performance of the electrophotographic photosensitive member.

Implementation Method 1

causing a reaction between a compound represented by general formula (a), a compound represented by general formula (b), and a compound represented by general formula (c) using a ligand represented by general formula (30) and a transition metal-containing catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11067909B2Terphenyl compound, electrophotographic photosensitive member, and method for producing terphenyl compound
Publication Date: 2021.07.20 KYOCERA DOCUMENT SOLUTIONS INC
  • US11067909B2 patent drawing
  • US11067909B2 patent drawing
  • US11067909B2 patent drawing

AI summary

A compound is represented by general formula (1). In general formula (1), R1 and R2 each represent, independently of one another, a hydrogen atom, a methyl group, or an ethyl group, and a sum of the number of carbon atoms of the chemical group represented by R1 and the number of carbon atoms of the chemical group represented by R2 is 2. R3 and R4 each represent, independently of one another, a hydrogen atom, a methyl group, or an ethyl group, and a sum of the number of carbon atoms of the chemical group represented by R3 and the number of carbon atoms of the chemical group represented by R1 is 2. A photosensitive layer of an electrophotographic photosensitive member contains at least a charge generating material, a hole transport material, and a binder resin. The hole transport material includes a compound represented by general formula (1)