P-terphenyl Charge Transporter Solubility

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Solution Overview

Problem

Current electrophotographic photoconductors face challenges with poor solubility of charge transporting agents in organic solvents, leading to inadequate durability and sensitivity, particularly in organic photoconductor systems.

Innovation Solution

A p-terphenyl compound with specific substituents, represented by general formulas (1), (2), and (3), is developed to enhance solubility in organic solvents, allowing for the creation of electrophotographic photoconductors with improved drift mobility, sensitivity, and durability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional charge transporting agents are used in organic photoconductors, then the photoconductor can be manufactured, but the solubility in organic solvents is poor leading to inadequate durability and sensitivity

Engineering Contradiction:
Improvedurability and sensitivityVSAvoidsolubility in organic solvents
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure of p-terphenyl compounds by introducing specific substituent groups (such as alkoxy, alkyl, aryl, or heteroaryl groups) at designated positions. This structural parameter change enhances the solubility of the charge transporting agent in organic solvents while preserving its charge transport functionality, thereby resolving the contradiction between manufacturability and performance durability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite charge transporting materials by combining p-terphenyl core structures with various functional substituent groups. This composite approach allows the molecule to simultaneously achieve good solubility in organic solvents (due to the substituent groups) and maintain high charge transport efficiency (due to the p-terphenyl core), thus resolving the contradiction between ease of manufacture and reliability

Inventive Principle:
Principle #40Composite materials

2Reliability

If inorganic photoconductive materials such as selenium, zinc oxide, or cadmium sulfide are used, then charging and exposure functions are achieved, but toxicity and durability problems occur

Engineering Contradiction:
ImprovedurabilityVSAvoidtoxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces persistent inorganic photoconductive materials with organic p-terphenyl compounds that can be designed for specific applications. These organic compounds offer comparable functional performance without the long-term environmental persistence and toxicity issues of inorganic materials like cadmium sulfide and selenium, thus resolving the contradiction between durability and harmful factors

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent transitions from inorganic material composition to organic molecular structure by modifying the chemical parameters of the photoconductive material. This fundamental parameter change eliminates the toxicity inherent in inorganic materials while maintaining the essential charging and exposure functions through the designed organic p-terphenyl structure

Inventive Principle:
Principle #35Parameter changes

3Reliability

If inorganic photoconductive materials such as silicon are used, then photoconductive function is achieved, but hard production conditions and high cost are required

Engineering Contradiction:
Improvephotoconductive functionVSAvoidproduction conditions and cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive inorganic silicon-based photoconductors with organic p-terphenyl compounds that can be synthesized through more accessible chemical routes. These organic materials eliminate the need for stimulative gas processing and specialized handling equipment, significantly reducing production complexity and cost while maintaining photoconductive functionality

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent substitutes the complex mechanical and chemical processing required for silicon photoconductor manufacturing with a more straightforward organic synthesis approach. Instead of requiring stimulative gas environments and precise mechanical handling, the organic p-terphenyl compounds can be processed through conventional solution-based methods, resolving the contradiction between functional reliability and manufacturing ease

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

4Reliability

If charge transporting agents with satisfactory sensitivity are used, then photoconductor performance is improved, but compatibility with resin and solubility are poor

Engineering Contradiction:
ImprovesensitivityVSAvoidcompatibility with resin and solubility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies local quality modification by introducing specific substituent groups at particular positions on the p-terphenyl molecule. The core structure maintains high charge transport efficiency (sensitivity), while the substituent groups (such as alkoxy or alkyl groups) provide enhanced solubility and resin compatibility, thus resolving the contradiction between sensitivity and manufacturability

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates composite molecular structures combining the p-terphenyl charge transport core with functional substituent groups that provide both solubility and resin compatibility. This composite approach allows the material to simultaneously achieve satisfactory sensitivity (from the core) and good compatibility with resins and solvents (from the substituents), resolving the contradiction between reliability and ease of manufacture

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 p-terphenyl compound achieves high solubility in organic solvents, resulting in electrophotographic photoconductors with excellent drift mobility and photoconductor characteristics, ensuring high sensitivity and durability.

Implementation Method 1

a p-terphenyl compound having improved solubility in an organic solvent and useful as a charge transporting agent used in an electrophotographic photoconductor

Methodology Applied
Scientific EffectCharge transport: Conduction (electrical)

Data Source

PatentUS7799492B2P-terphenyl compound and photosensitive body for electrophotography using such compound
Publication Date: 2010.09.21 HODOGAYA CHEMICAL CO LTD
  • US7799492B2 patent drawing
  • US7799492B2 patent drawing
  • US7799492B2 patent drawing

AI summary

The present invention provides p-terphenyl compounds represented by the following general formula (1) and (2):and an electrophotographic photoconductor containing the compound. According to the invention, a charge transporting agent having improved solubility in an organic solvent and an electrophotographic photoconductor excellent in drift mobility and having high sensitivity and high durability are provided.