Ammonium Salt Acid Generator Synthesis for High Purity Lithography

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Solution Overview

Problem

Current methods for producing acid generators in resist compositions for lithography techniques face challenges in achieving high yield while minimizing impurities, which affects the improvement of lithography properties in pattern formation.

Innovation Solution

A method involving the reaction of a primary, secondary, or tertiary ammonium salt compound with a nitrogen-containing compound to produce a second ammonium salt compound with a higher pKa value, followed by salt exchange with a sulfonium or iodonium cation to enhance the hydrophobicity and purity of the acid generator.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional methods are used to produce acid generators, then production can proceed with standard processes, but impurities are generated and yield is reduced

Engineering Contradiction:
Improvepurity of acid generatorVSAvoidyield of acid generator
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent applies preliminary action by performing a salt exchange reaction before final product isolation. The ammonium salt compound undergoes salt exchange with a quaternary ammonium salt to convert to a sulfonate salt form, which has better solubility and purity characteristics. This preliminary transformation enables subsequent easy purification and high-yield isolation of the acid generator without compromising purity

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent changes the chemical parameters of the acid generator by converting between different salt forms (ammonium salt to sulfonate salt). This parameter change in the counterion structure improves solubility in organic solvents and enhances purity while maintaining high yield through controlled crystallization and filtration processes

Inventive Principle:
Principle #35Parameter changes

2Reliability

If the resist composition uses high purity acid generators, then lithography properties improve, but production complexity increases

Engineering Contradiction:
Improvelithography propertiesVSAvoidproduction process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent uses an ammonium salt compound as an intermediary in the synthesis pathway. This intermediate form allows for easy purification through salt exchange reactions and provides a clean starting point for producing the final acid generator. The intermediary step simplifies the overall process by enabling straightforward separation and purification operations

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent extracts the acid generator from complex reaction mixtures through selective crystallization and filtration. By controlling the solubility characteristics of different salt forms, the desired acid generator is extracted in high purity form, leaving impurities in the mother liquor or as separate phases that can be easily removed

Inventive Principle:
Principle #2Taking out (Extraction)

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

This approach enables the production of acid generators with minimal impurities, improving lithography properties and increasing the yield, thereby enhancing the formation of resist patterns with improved resolution and sensitivity.

Implementation Method 1

reacting a first ammonium salt compound containing a first ammonium cation which is a primary, secondary or tertiary ammonium cation with a nitrogen-containing compound having a lone pair to obtain a second ammonium salt compound

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

salt exchange with a sulfonium or iodonium cation to enhance the hydrophobicity and purity of the acid generator

Methodology Applied
Scientific EffectIon Exchange: Ion Exchange

Data Source

PatentUS9075304B2Method of producing ammonium salt compound, method of producing compound, and compound, polymeric compound, acid generator, resist composition and method of forming resist pattern
Publication Date: 2015.07.07 TOKYO OHKA KOGYO CO LTD
  • US9075304B2 patent drawing
  • US9075304B2 patent drawing
  • US9075304B2 patent drawing

AI summary

A method of producing an ammonium salt compound, including reacting a first ammonium salt compound containing a first ammonium cation which is a primary, secondary or tertiary ammonium cation with a nitrogen-containing compound having a lone pair to obtain a second ammonium salt compound which contains a conjugated acid of the nitrogen-containing compound, the conjugated acid of the nitrogen-containing compound having a larger pKa than the pKa of the first ammonium cation; and a method of producing a compound, including a step of salt exchange between the ammonium salt compound obtained by the aforementioned production method and a sulfonium cation or iodonium cation which has a higher hydrophobicity than the hydrophobicity of the conjugated acid of the nitrogen-containing compound.