Heterocycle-Containing Polymer Precursor for Fast Cyclization

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Solution Overview

Problem

The cyclization rate of polyimide precursors in existing resin compositions is slow, which hinders the efficient formation of cured films for semiconductor devices.

Innovation Solution

A method involving the halogenation of dicarboxylic acid or its derivative using a halogenating agent, followed by reaction with diamine, where the molar ratio of the halogenating agent to water is adjusted to 2.10 times or less of the total molar amount of dicarboxylic acid and its derivative, to achieve a faster cyclization rate.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If existing resin compositions are used for polyimide precursor, then the polyimide precursor can be obtained, but the cyclization rate is slow

Engineering Contradiction:
Improvecyclization rateVSAvoidtime for cyclization reaction
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The invention changes the chemical structure parameters of the polyimide precursor by introducing specific heterocyclic structures (pyridine, pyrimidine, triazine rings) into the repeating units. This structural modification fundamentally alters the cyclization behavior, enabling the cyclization reaction to proceed at a significantly faster rate compared to conventional polyimide precursors, thus resolving the contradiction between obtaining the precursor and achieving fast cyclization.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If polyimide precursor is used before cyclization, then solubility is improved, but cyclization rate becomes slow

Engineering Contradiction:
Improvesolubility of polyimide precursorVSAvoidcyclization rate
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The invention modifies the chemical parameters of the polyimide precursor by incorporating heterocyclic aromatic rings into the polymer backbone structure. This structural change maintains the solubility advantages of the precursor form while simultaneously enabling rapid cyclization, thus resolving the contradiction between ease of manufacture and productivity.

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If conventional polyimide precursor structure is used, then the precursor can be applied to substrate, but the cyclization reaction is slow

Engineering Contradiction:
Improveapplicability to substrateVSAvoidcyclization reaction time
Core Design Contradiction:
Ease of operationVSLoss of time

Solution Approach 1:

The invention changes the chemical composition parameters of the polyimide precursor by introducing heterocyclic structures that facilitate faster cyclization. The modified precursor maintains its ability to be applied to substrates in the same manner as conventional precursors, but the cyclization reaction proceeds much more rapidly, thus resolving the contradiction between ease of operation and time loss.

Inventive Principle:
Principle #35Parameter changes

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 results in a heterocycle-containing polymer precursor with a rapid cyclization rate, ensuring consistent and efficient formation of cured films with improved properties for semiconductor devices.

Implementation Method 1

halogenating dicarboxylic acid or dicarboxylic acid derivative by using a halogenating agent

Methodology Applied
Scientific EffectHalogenation reaction: Chemical Bonding

Implementation Method 2

performing reaction with diamine

Methodology Applied
Scientific EffectCondensation reaction: Chemical Bonding

Implementation Method 3

heated to cyclize the polyimide precursor and to form a cured film

Methodology Applied
Scientific EffectCyclization reaction: Chemical Bonding

Data Source

PatentEP3392292B1Method for producing heterocycle-containing polymer precursor, heterocycle-containing polymer precursor, and use for same
Publication Date: 2023.06.28 FUJIFILM CORP
  • EP3392292B1 patent drawingFigure 1
  • EP3392292B1 patent drawing
  • EP3392292B1 patent drawing

AI summary

There are provided a method of manufacturing a heterocycle-containing polymer precursor having a fast cyclization rate, a heterocycle-containing polymer precursor, a composition, a cured film, a method of manufacturing a cured film, and a semiconductor device. There is provided a method of manufacturing a heterocycle-containing polymer precursor using dicarboxylic acid or dicarboxylic acid derivative and diamine as raw materials, including: halogenating the dicarboxylic acid or the dicarboxylic acid derivative by using a halogenating agent and performing reaction with diamine; and adjusting a difference between a molar amount of the halogenating agent and a molar amount of water included in a reaction system before reaction of the halogenating agent to become 2.10 times or less of a total molar amount of the dicarboxylic acid and the dicarboxylic acid derivative as the raw materials.