Furan-Based Bismaleimide Resin for Low-CTE Heat-Resistant Curing

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Solution Overview

Problem

Existing bismaleimide resins used in electronic materials face challenges in achieving high heat resistance while maintaining a low coefficient of thermal expansion (CTE) and low dielectric constant, which hinders the development of high-speed signal transmission in microelectronics.

Innovation Solution

A compound represented by Formula (1) is synthesized through the reaction of 2,5-bis(aminomethyl)tetrahydrofuran or 2,5-bis(aminomethyl)furan with maleic anhydride, forming a cured product with a low CTE and excellent heat resistance, using specific solvents and catalysts under controlled reaction conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If conventional bismaleimide resins are used to ensure heat resistance, then heat resistance is maintained, but the coefficient of thermal expansion becomes too high for high-speed signal transmission

Engineering Contradiction:
Improveheat resistanceVSAvoidcoefficient of thermal expansion
Core Design Contradiction:
TemperatureVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical structure parameters of the bismaleimide compound by introducing specific aromatic ring structures (Formula 1) with particular substituent patterns. This structural parameter change results in a cured product that simultaneously achieves high heat resistance (Tg ≥ 150°C) and low coefficient of thermal expansion (CTE ≤ 100 ppm/°C), resolving the contradiction between these two properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining maleimide groups with specific aromatic ring systems containing oxygen atoms. This composite structural approach allows the cured resin to exhibit both excellent heat resistance and low thermal expansion, as the aromatic rings provide structural rigidity while the overall molecular architecture controls thermal properties

Inventive Principle:
Principle #40Composite materials

2Speed

If the dielectric constant of substrate material is reduced to enable high-speed signal transmission, then signal transmission speed improves, but heat resistance may be compromised

Engineering Contradiction:
Improvesignal transmission speedVSAvoidheat resistance
Core Design Contradiction:
SpeedVSTemperature

Solution Approach 1:

The patent optimizes the molecular structure parameters of the bismaleimide compound (Formula 1) to achieve a balance between dielectric properties and thermal properties. The specific aromatic ring structure with oxygen atoms contributes to lower dielectric constant while the crosslinked network structure maintains high heat resistance, enabling both fast signal transmission and thermal stability

Inventive Principle:
Principle #35Parameter changes

3Temperature

If maleimide compounds with high heat resistance are developed, then heat resistance improves, but the coefficient of thermal expansion remains too high

Engineering Contradiction:
Improveheat resistanceVSAvoidcoefficient of thermal expansion
Core Design Contradiction:
TemperatureVSObject-affected harmful factors

Solution Approach 1:

The invention systematically changes the structural parameters of maleimide compounds by incorporating specific aromatic ring systems with oxygen atoms in predetermined positions. This parameter optimization achieves a breakthrough where the cured product simultaneously attains high heat resistance (Tg ≥ 150°C) and low coefficient of thermal expansion (CTE ≤ 100 ppm/°C), overcoming the traditional trade-off between these properties

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

The compound achieves a low CTE and maintains excellent heat resistance, suitable for applications in insulating materials and semiconductor packaging, with a glass transition temperature above 150°C and CTE below 100 ppm/°C.

Implementation Method 1

A compound represented by Formula (1) is synthesized through the reaction of 2,5-bis(aminomethyl)tetrahydrofuran or 2,5-bis(aminomethyl)furan with maleic anhydride

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

forming a cured product with a low CTE and excellent heat resistance

Methodology Applied
Scientific EffectCuring: Phase Change

Data Source

PatentUS20250376465A1Compound, composition, cured product, and method for producing compound
Publication Date: 2025.12.11 MITSUBISHI GAS CHEM CO INC
  • US20250376465A1 patent drawing
  • US20250376465A1 patent drawing
  • US20250376465A1 patent drawing

AI summary

To provide a compound represented by Formula (1): wherein the dotted line portions each independently represent *—CH—CH2— or *—C═CH—, and * is bonded to the side near the oxygen atom contained in the ring.