Trisphenol Compound Single Bond Connectivity for Resist Solubility

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Solution Overview

Problem

Trisphenol compounds used in photosensitive resist materials face challenges with sensitivity, resolution, heat resistance, and storage stability, necessitating improvements in their structure for enhanced solubility and performance.

Innovation Solution

A trisphenol compound with a phenylalkylidene group bonded to the phenyl nucleus and hydroxyphenyl group, offering improved solubility and heat resistance, is developed, allowing for better performance in photosensitive resist applications and other materials like aromatic polycarbonate resins and epoxy resins.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If conventional trisphenol structures (e.g., TrisP-PA with 2,2-propylidene group) are used, then heat resistance is achieved, but solubility in organic solvents is insufficient

Engineering Contradiction:
Improveheat resistanceVSAvoidsolubility in organic solvents
Core Design Contradiction:
TemperatureVSEase of manufacture

Solution Approach 1:

The patent changes the bonding group parameter from 2,2-propylidene to single bond, and modifies substituent parameters (R groups) to achieve both improved solubility and heat resistance. Specifically, compounds with single bond connectivity and specific R group configurations (formula 1) demonstrate enhanced solubility in organic solvents while maintaining high glass transition temperatures (heat resistance).

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures combining phenylalkylidene groups with hydroxyphenyl groups in specific configurations. The trisphenol compounds with single bond connectivity and strategically placed substituents form a composite structure that integrates both solubility-enhancing and heat-resistant characteristics.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If conventional trisphenol structures are used, then material stability is maintained, but sensitivity and resolution in photosensitive resist are insufficient

Engineering Contradiction:
Improvestorage stabilityVSAvoidresolution
Core Design Contradiction:
Stability of the object's compositionVSManufacturing precision

Solution Approach 1:

The patent modifies molecular parameters including bonding connectivity (to single bond) and substituent types to simultaneously improve sensitivity and resolution while maintaining storage stability. The specific formula 1 structures with controlled R groups achieve this balance.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If trisphenol structure is modified to improve solubility, then heat resistance may deteriorate, but the invention achieves both improvements

Engineering Contradiction:
ImprovesolubilityVSAvoidheat resistance
Core Design Contradiction:
Ease of manufactureVSTemperature

Solution Approach 1:

The patent successfully changes multiple parameters simultaneously: bonding group (to single bond), substituent types (R groups), and molecular configuration. These coordinated parameter changes in formula 1 compounds produce both improved solubility and enhanced heat resistance (higher glass transition temperatures).

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS8816135B2Trisphenol compound
Publication Date: 2014.08.26 HONSHU CHEM INDAL
  • US8816135B2 patent drawing
  • US8816135B2 patent drawing
  • US8816135B2 patent drawing

AI summary

A trisphenol compound is expressed by formula (1), wherein R represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms, phenyl group or hydroxyl group; R1 represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms, or phenyl group; R2 represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms; R3 represents a hydrogen atom or alkyl group with 1 to 8 carbon atoms; a represents 0, 1, 2, or 3; b represents 1 or 2; and c and d represent 0, 1, 2, 3, or 4; where the sum of b and c is 5 or less; R's may be either the same or different when a is 2 or more; R1's may be either the same or different when c is 2 or more; and R2's may be either the same or different when d is 2 or more.