Polyimide Precursor Polymer for High-Resolution Patterning

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Solution Overview

Problem

Current photosensitive resin compositions for semiconductor devices face challenges in achieving high resolution and fine pattern formation without impairing mechanical strength, adhesiveness, and heat resistance, particularly in high-density mounting technologies like three-dimensional lamination, due to limitations in solubility and swelling issues during development.

Innovation Solution

A tetracarboxylic acid diester compound is used to produce a polymer of a polyimide precursor that enhances solubility in organic solvents, allowing for high contrast dissolution and reduced swelling, and is incorporated into a negative photosensitive resin composition with a polymerizable unsaturated bonding group for improved resolution and chemical resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If a polyamic acid with ester bond is used as photosensitive polyimide, then the post-curing temperature can be reduced, but the resolution in patterning deteriorates due to poor solubility in alkaline aqueous developer

Engineering Contradiction:
Improvepost-curing temperatureVSAvoidresolution in patterning
Core Design Contradiction:
TemperatureVSManufacturing precision

Solution Approach 1:

The patent changes the chemical structure parameters of the polyimide precursor by introducing specific side groups (carboxyl, hydroxyl, or amine groups) at defined positions relative to the imide ring. This structural modification enables the resin to be soluble in alkaline aqueous developers while maintaining the ability to form high-resolution patterns and endure reduced post-curing temperatures.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite resin system combining polyamic acid with specific side groups (carboxyl, hydroxyl, or amine) that provides both photosensitivity and enhanced solubility in alkaline developers. This composite structure allows simultaneous achievement of high resolution patterning and low-temperature curing.

Inventive Principle:
Principle #40Composite materials

2Temperature

If an already imidated solvent-soluble resin is used, then the post-curing temperature is lowered, but the solubility in alkaline aqueous developer is insufficient for high resolution patterning

Engineering Contradiction:
Improvepost-curing temperatureVSAvoidsolubility in alkaline aqueous developer
Core Design Contradiction:
TemperatureVSQuantity of substance

Solution Approach 1:

The patent modifies the chemical parameters of already imidated resins by introducing specific ionizable side groups (carboxyl, hydroxyl, or amine groups) at controlled positions. This increases the resin's interaction with alkaline aqueous developers, enhancing solubility for high-resolution patterning while preserving low-temperature curing capability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces specific functional groups at localized positions (side groups at defined positions relative to imide rings) to create regions of enhanced alkaline solubility without compromising the overall structural integrity or curing properties of the polyimide resin.

Inventive Principle:
Principle #3Local quality

3Shape

If high aspect ratio patterns are formed, then the film thickness and pattern dimension requirements are met, but the resolution performance is compromised due to swelling during development

Engineering Contradiction:
Improveaspect ratio of patternVSAvoidresolution performance
Core Design Contradiction:
ShapeVSManufacturing precision

Solution Approach 1:

The patent changes the hydrophobicity parameters of the polyimide resin by introducing polar side groups (carboxyl, hydroxyl, or amine groups) that enhance affinity for alkaline aqueous developers. This reduces swelling during development, allowing high aspect ratio patterns to be formed with maintained resolution performance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the potential harm of reduced solubility (which causes swelling and poor resolution) into a benefit by strategically introducing side groups that enhance alkaline solubility. This increased solubility prevents swelling during development, enabling simultaneous achievement of high aspect ratio and high resolution.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 solution enables the formation of fine patterns with excellent mechanical strength, adhesiveness, and chemical resistance, while maintaining high resolution and reducing swelling during development, thus addressing the limitations of existing technologies.

Implementation Method 1

enhances solubility in organic solvents, allowing for high contrast dissolution

Methodology Applied
Scientific EffectSolubility enhancement: Solvation

Implementation Method 2

negative photosensitive resin composition with a polymerizable unsaturated bonding group

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP3315504B1Tetracarboxylic acid diester compound, polymer of polyimide precursor and method for producing same, negative photosensitive resin composition, patterning process, and method for forming cured film
Publication Date: 2021.09.01 SHIN ETSU CHEMICAL CO LTD
  • EP3315504B1 patent drawing
  • EP3315504B1 patent drawing
  • EP3315504B1 patent drawing

AI summary

The present invention provides a tetracarboxylic acid diester compound represented by the following general formula (1), wherein, X1 represents a tetravalent organic group, and R1 represents a group represented by the following general formula (2), wherein, the dotted line represents a bonding, Y1 represents an organic group with a valency of k+1, Rs represents a group containing at least one silicon atom, "k" represents 1, 2 or 3, and "n" represents 0 or 1. There can be provided a tetracarboxylic acid diester compound which can lead a polymer of a polyimide precursor capable of using a base resin of a negative photosensitive resin composition which is capable of forming a fine pattern and giving high resolution, a polymer of a polyimide precursor obtained by using the tetracarboxylic acid diester compound and a method for producing the same.