Negative Photosensitive Polyimide Resin for Low-k Relief Patterns

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Conventional negative photosensitive resin compositions face challenges in maintaining resolution and adhesion to mold resins, especially with focus depth shifts and high temperature storage tests, where voids form at the interface with the Cu layer, and they lack sufficient chemical resistance and low dielectric constants.

Innovation Solution

A negative photosensitive resin composition combining a polyimide precursor with an unsaturated double bond and a photopolymerization initiator having an oxime structure, along with specific solvent and silane coupling agents, to enhance adhesion, chemical resistance, and resolution, while suppressing void formation and achieving low dielectric constants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional negative photosensitive resin composition is used, then the basic insulating properties are maintained, but resolution deteriorates with focus depth shifts and adhesion to mold resin is insufficient

Engineering Contradiction:
ImproveresolutionVSAvoidadhesion to mold resin
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent uses a composite resin composition containing polyimide resin, cycloolefin resin, and silane coupling agent. The silane coupling agent acts as a bridge between the organic resin and inorganic mold resin, creating strong interfacial adhesion. The combination of polyimide (providing heat resistance) and cycloolefin (providing low dielectric constant and good adhesion) creates a composite material that simultaneously achieves resolution, adhesion, and electrical properties.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent modifies the chemical composition parameters of the resin by incorporating specific ratios of polyimide resin, cycloolefin resin, and silane coupling agent. The silane coupling agent content is controlled at 1-20 parts by mass per 100 parts of total resin, and the cycloolefin resin content is controlled at 10-80 parts by mass per 100 parts of polyimide resin. These parameter changes optimize both adhesion and resolution.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If conventional resin composition is used, then basic chemical resistance is maintained, but voids form at the interface with Cu layer during high temperature storage tests

Engineering Contradiction:
Improvechemical resistanceVSAvoidvoid formation at interface
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The silane coupling agent serves as an intermediary substance between the organic resin matrix and the inorganic Cu layer. It forms a chemical bond with both the resin and the metal surface, preventing void formation at the interface during high temperature storage. The silane groups react with hydroxyl groups on the Cu surface while the alkoxy groups remain in the resin matrix, creating a stable interfacial layer that eliminates voids.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the chemical composition by adding silane coupling agent (1-20 parts by mass per 100 parts of total resin) which fundamentally alters the interfacial chemistry between the resin and Cu layer. This compositional change prevents void formation while maintaining chemical resistance.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If conventional photosensitive resin is used, then basic insulating properties are achieved, but dielectric constant is not sufficiently low for high-speed signal transmission

Engineering Contradiction:
Improveinsulating propertiesVSAvoiddielectric constant
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent creates a composite material combining polyimide resin (providing excellent heat resistance and insulating properties) with cycloolefin resin (providing low dielectric constant). The cycloolefin resin content is controlled at 10-80 parts by mass per 100 parts of polyimide resin to achieve optimal balance between insulating properties and low dielectric constant, enabling high-speed signal transmission while maintaining thermal stability.

Inventive Principle:
Principle #40Composite materials

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 composition achieves improved resolution, adhesion to mold resins, and chemical resistance, reducing void formation at high temperature storage tests, and exhibits a low dielectric constant, suitable for semiconductor devices.

Implementation Method 1

a photopolymerization initiator having an oxime structure... when a 100 μM dimethyl sulfoxide solution of the (B) is irradiated at 100 mJ/cm2 is 3.0 to 30.0 μM

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Implementation Method 2

a polyimide precursor having an unsaturated double bond in the side chain

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentUS12174539B2Negative photosensitive resin composition, production method for polyimide, production method for cured relief pattern, and semiconductor device
Publication Date: 2024.12.24 ASAHI KASEI KOGYO KABUSHIKI KAISHA
  • US12174539B2 patent drawing
  • US12174539B2 patent drawing
  • US12174539B2 patent drawing

AI summary

To provide a negative photosensitive resin composition which exhibits satisfactory resolution even when shifts occur in focus depth, and which has satisfactory adhesion to a mold resin and exhibits a low dielectric constant; a method for producing a polyimide using the photosensitive resin composition; a method for producing a cured relief pattern; and a semiconductor device including the cured relief pattern.Disclosed is a negative photosensitive resin composition including a polyimide precursor having a structure represented by general formula (A1), (B) a photopolymerization initiator, and (C) a solvent.