Low Molecular Weight Cyclic Resist Compound for Fine Pattern Resolution

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Solution Overview

Problem

Conventional polymer-based resist materials face limitations in miniaturization due to roughness and yield decreases in fine pattern formation, and existing low molecular weight cyclic polyphenolic compounds have issues with heat resistance, solubility, sensitivity, and pattern shape quality.

Innovation Solution

A cyclic compound with a specific structural formula, capable of high solubility in safe solvents and high sensitivity, is developed, along with a composition and method for resist pattern formation, incorporating an acid generating agent, acid crosslinking agent, and acid diffusion controlling agent to improve pattern resolution and smoothness.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If polymer based resist materials are used, then the resist can form amorphous thin films, but the molecular weight is large (10,000 to 100,000) and molecular weight distribution is wide, causing roughness on fine pattern surface and making pattern dimension control difficult

Engineering Contradiction:
Improvepattern dimension controlVSAvoidmolecular weight distribution
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent segments the large polymer molecules into smaller cyclic compound units (molecular weight 500-5000). By using low molecular weight cyclic compounds as the base structure instead of high molecular weight polymers, the invention achieves better pattern dimension control while reducing molecular weight distribution width, directly resolving the contradiction between manufacturing precision and device complexity

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent changes the molecular weight parameter from the conventional 10,000-100,000 range down to 500-5000 for the cyclic compound. This parameter change improves pattern dimension control and reduces surface roughness while maintaining the necessary film-forming capabilities through controlled polymerization or self-assembly of the cyclic units

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If low molecular weight cyclic polyphenolic compounds are used, then resolution and roughness of resist pattern are improved to some extent, but heat resistance is not sufficient and shape of resulting resist pattern becomes poor

Engineering Contradiction:
Improveresolution and roughnessVSAvoidheat resistance and pattern shape
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent creates a composite material system combining low molecular weight cyclic polyphenolic compounds (for resolution and roughness improvement) with carefully selected solvents and additives (for heat resistance and pattern shape). The composite approach allows each component to contribute its strengths: the cyclic compound provides fine pattern resolution while the formulated composition maintains heat resistance and structural integrity

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes the molecular weight parameter within the 500-5000 range and controls the structural parameters of the cyclic compound (specific formula with R1, R2, R3, R4 substituents) to achieve a balance between resolution/roughness and heat resistance/pattern shape, moving away from the conventional high molecular weight polymers

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If conventional polymer based resist materials are used, then the material is available and easy to coat, but the yield decreases due to roughness and pattern dimension control difficulties in fine pattern lithography

Engineering Contradiction:
Improvecoating processVSAvoidyield
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

By segmenting the resist material into low molecular weight cyclic compounds (500-5000) that can still form continuous films through controlled assembly, the invention maintains ease of coating while dramatically improving yield through better pattern dimension control and reduced roughness in fine pattern lithography

Inventive Principle:
Principle #1Segmentation

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 cyclic compound achieves improved solubility, sensitivity, and pattern smoothness, enabling finer pattern formation with enhanced heat resistance and process stability, overcoming the limitations of conventional resist materials.

Implementation Method 1

irradiating a resist thin film made by coating a substrate with a solution of a polymer resist material such as polymethyl methacrylate, polyhydroxy styrene with an acid dissociation reactive group, or polyalkyl methacrylate with ultraviolet, far ultraviolet, electron beam, extreme ultraviolet (EUV), and X-ray

Methodology Applied
Scientific EffectPhotochemical reaction: Photodissociation

Implementation Method 2

incorporating an acid generating agent, acid crosslinking agent, and acid diffusion controlling agent to improve pattern resolution and smoothness

Methodology Applied
Scientific EffectCrosslinking reaction: Chemical Bonding

Implementation Method 3

incorporating an acid generating agent, acid crosslinking agent, and acid diffusion controlling agent to improve pattern resolution and smoothness

Methodology Applied
Scientific EffectDiffusion control: Diffusion

Data Source

PatentEP2743249B1Cyclic compound, method for producing same, composition, and method for forming resist pattern
Publication Date: 2019.07.24 MITSUBISHI GAS CHEM CO INC
  • EP2743249B1 patent drawing
  • EP2743249B1 patent drawing
  • EP2743249B1 patent drawing

AI summary

The present invention provides a cyclic compound having a molecular weight of 500 to 5000 and represented by the following formula (1), a method for producing the cyclic compound, a composition containing the cyclic compound, and a method for forming a resist pattern using the composition: wherein at least one of R0 is a monovalent group containing an iodine atom.