Resist Composition with Brominated Acid Diffusion Control Agent

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Solution Overview

Problem

Current resist compositions for semiconductor and liquid crystal display element lithography, particularly with extreme ultraviolet (EUV) or electron beam (EB) exposure, face challenges in achieving high sensitivity and uniformity of resist patterns due to limited acid diffusion control, especially with reduced photon numbers compared to ArF or KrF excimer lasers.

Innovation Solution

A resist composition incorporating a base material component that changes solubility in a developing solution under acid action, combined with an acid diffusion control agent featuring a condensed cyclic group with bromine or iodine-containing hydrocarbon substituents, enhancing acid diffusion control and sensitivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If an acid diffusion control agent with a bicyclooctane skeleton is used, then uniformity of acid diffusion control is improved, but sensitivity of the resist composition deteriorates

Engineering Contradiction:
Improveuniformity of acid diffusion controlVSAvoidsensitivity of resist composition
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of the acid diffusion control agent by replacing the bicyclooctane skeleton with a camphor skeleton, which has different steric and electronic properties. This structural parameter change allows simultaneous achievement of uniform acid diffusion control and high sensitivity in EUV/EB lithography

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite acid diffusion control agent by combining the camphor skeleton with specific anion moieties (such as sulfonate, carboxylate, or phosphate groups) and organic cations. This composite structure enables both uniform diffusion control and enhanced sensitivity by optimizing the balance between hydrophobicity and acid-generating capability

Inventive Principle:
Principle #40Composite materials

2Measurement precision

If the resist pattern size is reduced to several tens of nanometers, then lithography resolution is improved, but critical dimension uniformity (CDU) deteriorates

Engineering Contradiction:
Improvelithography resolutionVSAvoidcritical dimension uniformity
Core Design Contradiction:
Measurement precisionVSManufacturing precision

Solution Approach 1:

The camphor-based acid diffusion control agent provides localized acid diffusion control at the nanometer scale, creating different acid diffusion characteristics in different regions of the resist film. This local quality control enables maintenance of CDU even at reduced pattern sizes by preventing excessive acid migration that would otherwise blur pattern edges

Inventive Principle:
Principle #3Local quality

3Loss of energy

If the number of photons is reduced in EUV/EB exposure, then energy consumption is reduced, but sensitivity of the resist composition deteriorates

Engineering Contradiction:
Improveenergy consumption in exposureVSAvoidsensitivity of resist composition
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The camphor-based acid diffusion control agent enhances the self-amplification capability of the chemical amplification resist system. By optimizing acid diffusion control, it enables more efficient acid-catalyzed deprotection reactions, allowing the resist to achieve high sensitivity with fewer incident photons in EUV/EB exposure

Inventive Principle:
Principle #25Self-service

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 resist composition achieves high sensitivity and improved critical dimension uniformity (CDU) for fine pattern formation, addressing the limitations of existing technologies by optimizing acid diffusion and solubility changes for EUV and EB exposure.

Implementation Method 1

a base material component (A) that exhibits changed solubility in a developing solution under the action of an acid

Methodology Applied
Scientific EffectSolubility change under acid action:

Implementation Method 2

an acid diffusion control agent component (D) that controls the diffusion of the acid generated upon exposure

Methodology Applied
Scientific EffectAcid diffusion control: Diffusion

Implementation Method 3

a resist composition that generates an acid upon exposure

Methodology Applied
Scientific EffectPhotoacid generation: Photodissociation

Data Source

PatentUS20240377734A1Resist composition, resist pattern forming method, compound, and acid diffusion control agent
Publication Date: 2024.11.14 TOKYO OHKA KOGYO CO LTD
  • US20240377734A1 patent drawing
  • US20240377734A1 patent drawing
  • US20240377734A1 patent drawing

AI summary

A resist composition containing a base material component (A) and a compound represented by General Formula (d0), in which Rd0 represents a condensed cyclic group in which an aromatic ring and an alicyclic ring are condensed, the alicyclic ring in the condensed cyclic group has a substituent, at least one of the substituents includes a hydrocarbon group having a bromine atom or a hydrocarbon group having an iodine atom, Yd0 represents a divalent linking group or a single bond, Yd0 is bonded to the alicyclic ring in the condensed cyclic group, Mm+ represents an m-valent organic cation, m represents an integer of 1 or more