JP-2026076048-A - Propenyl resins, compositions, cured products, printed circuit boards, semiconductor encapsulation materials, and build-up films.

Abstract

[Problem] To provide a propenyl-based resin, resin composition, and cured product thereof that can achieve a high degree of both excellent heat resistance and low modulus of elasticity during curing. [Solution] A propenyl resin containing a propenyl compound represented by general formula (1) (wherein M1 and M2 each independently represent a divalent organic group, n is an integer from 0 to 9, m is an integer from 1 to 10, n+m is an integer from 1 to 10, and R1 and R2 each independently represent a predetermined aromatic hydrocarbon group having a propenyl group). [Selection Diagram] Figure 1

Inventors

• 猪狩 匡人

Assignees

• ＤＩＣ株式会社

Dates

Publication Date

20260511

Application Date

20241023

Claims (9)

1. A propenyl resin containing a propenyl compound represented by the following general formula (1). (In general formula (1), Each M1 independently represents a divalent organic group. M2 represents a divalent organic group. n is an integer from 0 to 9. m is an integer between 1 and 10. n+m is an integer from 1 to 10. R1 and R2 are each independently aromatic hydrocarbon groups represented by the following general formula (2): In general formula (2), R3 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. p is 0, 1, 2, 3, or 4. * represents the bond that connects to the oxygen atom in general formula (1).
2. The propenyl resin according to claim 1, wherein M1 or M2 is any of the groups representing the following structures (i) to (iv).
3. The propenyl resin according to claim 1, wherein the softening point of the propenyl resin is 50°C or higher and 100°C or lower.
4. A resin composition comprising a propenyl resin according to any one of claims 1 to 3 and a maleimide resin.
5. The resin composition according to claim 4, wherein, when measured by differential scanning calorimeter (DSC), the exothermic peak of the resin composition is located at 175°C or below.
6. A cured product of the resin composition described in claim 4.
7. A printed circuit board comprising the resin composition described in claim 4.
8. A semiconductor encapsulation material comprising the resin composition described in claim 4.
9. A build-up film comprising the resin composition described in claim 4.

Description

This invention relates to propenyl resins, compositions, cured products, printed circuit boards, semiconductor encapsulation materials, and build-up films. In recent years, with increasing demands for energy conservation and CO2 emission reduction, the adoption of power semiconductors is expanding in the fields of new energy power conversion and electric vehicles (EVs). Traditionally, Si-based devices have been used in power semiconductors, but recently, SiC-based devices have been attracting attention due to their high conversion efficiency and the possibility of miniaturization and weight reduction. Because SiC-based devices can operate at high temperatures, next-generation power semiconductor encapsulants require high heat resistance to ensure reliable operation at high temperatures. Until now, epoxy resins have been used as semiconductor encapsulants due to their excellent balance of various physical properties such as heat resistance and moisture resistance. However, in order to achieve even higher heat resistance, research is underway to explore the combined use or replacement of resins with higher heat resistance (Tg), such as maleimide resins, benzoxazine resins, and cyanate resins. Patent Document 1 proposes a composition containing a maleimide compound and a propenyl group-containing resin as a composition that yields a cured product with excellent heat resistance. However, while Patent Document 1 mentions the excellent heat resistance of the resin composition during curing, it does not evaluate the elastic modulus at all. Japanese Patent Publication No. 2019-019149 Figure 1 shows the MALDI-TOFMS spectrum of the propenyl resin (1) of Example 1.Figure 2 is the GPC chart of the propenyl resin (1) of Example 1.Figure 3 shows the 1H -NMR spectrum of the propenyl resin (1) of Example 1.Figure 4 shows the 13C -NMR spectrum of the propenyl resin (1) of Example 1.Figure 5 shows the MALDI-TOFMS spectrum of the propenyl resin (2) of Example 2.Figure 6 is the GPC chart of the propenyl resin (2) of Example 2.Figure 7 shows the 1H -NMR spectrum of the propenyl resin (2) of Example 2.Figure 8 shows the 13C -NMR spectrum of the propenyl resin (2) of Example 2.Figure 9 shows the MALDI-TOFMS spectrum of the propenyl resin (3) of Example 3.Figure 10 is the GPC chart of the propenyl resin (3) of Example 3.Figure 11 shows the 1H -NMR spectrum of the propenyl resin (3) of Example 3.Figure 12 shows the 13C -NMR spectrum of the propenyl resin (3) of Example 3.Figure 13 shows the FD-MS spectrum of the propenyl compound-containing mixture (1) of Comparative Example 1.Figure 14 shows the 1H -NMR spectrum of the propenyl compound-containing mixture (1) of Comparative Example 1.Figure 15 shows the 13C -NMR spectrum of the propenyl compound-containing mixture (1) of Comparative Example 1. The following describes embodiments of the present invention. These descriptions are illustrative and not intended to limit the invention in any way. In this invention, two or more embodiments can be arbitrarily combined. [term] In this specification, "reaction raw material" refers to a compound used to obtain a target compound through a chemical reaction such as combination or decomposition, and which partially constitutes the chemical structure of the target compound. Substances that act as aids to chemical reactions, such as solvents and catalysts, are excluded. Specifically in this specification, "reaction raw material" refers to a precursor for obtaining the target propenyl resin through a chemical reaction. In this specification, "organic group" refers to a group whose chemical structure is formed by an organic compound containing one or more carbon atoms being transformed into a 1- to 4-valent group. In other words, an "organic group" refers to an atomic group obtained by removing one to four hydrogen atoms from an organic compound containing one or more carbon atoms. Therefore, the organic group may contain one or more atoms selected from the group consisting of hydrogen atoms, nitrogen atoms, oxygen atoms, halogen atoms, sulfur atoms, and phosphorus atoms, in addition to carbon atoms. In this specification, "linking group" refers to a bond or group of atoms used to link structural units together, and includes divalent organic groups, single bonds, -O-, -S-, -C(=O)-, -S(=O)-, -S(=O) ²- , or -N( R₀ )-. R₀ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. In this specification, "aromatic hydrocarbon group" refers to any hydrocarbon group having an n-valent (e.g., monovalent to tetravalent) aromatic ring, such as an aryl group or an aralkyl group, or a group obtained by removing n-1 arbitrary hydrogen atoms from the aryl group or aralkyl group. Aromatic hydrocarbon groups with a valency of 2 or more are preferably groups obtained by removing 1 to 3 arbitrary hydrogen atoms from an aryl group or an aralkyl group. Examples of the aromatic rings include monocyclic aromatic rings, fused aromatic rings, and ring-aggreg