Novel Acid Generator for Resist Composition Solubility

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Solution Overview

Problem

Current resist compositions using onium salt-based acid generators face challenges with low solubility in organic solvents, leading to deteriorated post-exposure stability and resist pattern shape due to highly hydrophobic cations, which also hinder the dissolution of resist films in alkali developing solutions.

Innovation Solution

A novel resist composition incorporating a specific acid generator compound represented by general formulas (b1-8) and (b1-9), which includes acid dissociable groups and anions, improves solubility and stability, enhancing the resist pattern formation process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Power

If onium salt-based acid generators with highly hydrophobic cations are used, then acid generation capability is improved, but solubility in organic solvents deteriorates and post-exposure stability is reduced

Engineering Contradiction:
Improveacid generation capabilityVSAvoidpost-exposure stability
Core Design Contradiction:
PowerVSReliability

Solution Approach 1:

The patent changes the chemical parameters of the acid generator by replacing traditional onium salts with compounds containing nitrogen-containing six-membered aromatic rings and specific side chains. This parameter change achieves both adequate solubility in organic solvents and sufficient acid generation capability, resolving the contradiction between power and reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining aromatic ring systems with specific side chains (containing ester groups and aromatic rings) to form acid generators that possess both hydrophilic character for solubility and functional groups for acid generation. This composite approach balances conflicting requirements.

Inventive Principle:
Principle #40Composite materials

2Power

If onium salt-based acid generators with highly hydrophobic cations are used, then acid generation capability is improved, but solubility in organic solvents deteriorates

Engineering Contradiction:
Improveacid generation capabilityVSAvoidsolubility in organic solvents
Core Design Contradiction:
PowerVSQuantity of substance

Solution Approach 1:

The patent modifies the molecular parameters by introducing nitrogen-containing aromatic rings and ester groups that enhance polarity and interact with organic solvents. This parameter change achieves adequate solubility while maintaining acid generation function through the aromatic ring structure.

Inventive Principle:
Principle #35Parameter changes

3Power

If onium salt-based acid generators with highly hydrophobic cations are used, then acid generation capability is improved, but dissolution of resist films in alkali developing solutions is hindered

Engineering Contradiction:
Improveacid generation capabilityVSAvoidhindrance to resist film dissolution
Core Design Contradiction:
PowerVSObject-generated harmful factors

Solution Approach 1:

The patent changes the charge distribution and molecular polarity parameters by using nitrogen-containing aromatic structures instead of highly hydrophobic cations. This creates a more balanced molecular character that allows adequate acid generation while enabling proper interaction with alkali developing solutions for effective resist film dissolution.

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 novel acid generator compound enhances the solubility of the resist composition in organic solvents, stabilizes the latent image, and improves the shape and resolution of resist patterns, addressing the limitations of existing onium salt-based acid generators.

Implementation Method 1

an acid generator that generates acid upon exposure

Methodology Applied
Scientific EffectPhotochemical reaction: Photodissociation

Implementation Method 2

a base resin that exhibits a changed solubility in an alkali developing solution under action of acid and an acid generator that generates acid upon exposure

Methodology Applied
Scientific EffectAcid dissociation:

Data Source

PatentUS7488568B2Resist composition, method of forming resist pattern, compound and acid generator
Publication Date: 2009.02.10 TOKYO OHKA KOGYO CO LTD
  • US7488568B2 patent drawing
  • US7488568B2 patent drawing
  • US7488568B2 patent drawing

AI summary

A resist composition including a base component (A) and an acid-generator component (B), the acid-generator component (B) including an acid generator (B1) including a compound represented by general formula (b1-8) shown below (wherein R401 represents an acid dissociable, dissolution inhibiting group; R41 to R43 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, an alkoxy group, a carboxy group or a hydroxyalkyl group; Q represents a divalent linking group or a single bond; and X− represents an anion) or an acid generator (B1′) including a compound represented by general formula (b1-9) shown below (wherein R402 and R403 each independently represents a hydrogen atom, an alkyl group or a halogenated alkyl group; R404 represents an alkyl group or a halogenated alkyl group, wherein R403 and R404 may be bonded to each other to form a ring structure; and X− represents an anion).