Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed wiring board, and semiconductor device

Patent metadata

Field	Value
Publication number	US-2025257214-A1
Application number	US-202318846083-A
Country	US
Kind code	A1
Filing date	Mar 13, 2023
Priority date	Mar 14, 2022
Publication date	Aug 14, 2025
Grant date	—

Abstract

Provided are a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. The resin composition contains a resin (A) having a terminal group represented by Formula (T1) and having an indane skeleton, and a polyphenylene ether compound (B) having an unsaturated carbon-carbon double bond at a terminal, wherein a mass ratio of a content of the resin (A) to a content of the polyphenylene ether compound (B); i.e., resin (A)/polyphenylene ether compound (B) is 5/95 to 70/30. In Formula (T1), Mb each independently represents a hydrocarbon group having from 1 to 12 carbons which may be substituted with a halogen atom; y represents an integer of 0 to 4; and * represents a bonding position with another moiety.

First claim

1 . A resin composition comprising:
a resin (A) having a terminal group represented by Formula (T1) and having an indane skeleton; and a polyphenylene ether compound (B) having an unsaturated carbon-carbon double bond at a terminal, wherein a mass ratio of a content of the resin (A) to a content of the polyphenylene ether compound (B); i.e., resin (A)/polyphenylene ether compound (B) is 5/95 to 70/30;

in Formula (T1), Mb each independently represents a hydrocarbon group having from 1 to 12 carbons which may be substituted with a halogen atom; y represents an integer of 0 to 4; and * represents a bonding position with another moiety.

2 . The resin composition according to claim 1 , wherein the resin (A) contains a resin represented by Formula (T1-1);

in Formula (T1-1), R is a group containing structural units represented by Formula (Tx); Mb each independently represents a hydrocarbon group having from 1 to 12 carbons which may be substituted with a halogen atom; and y is an integer of 0 to 4; and

in Formula (Tx), n, o, and p each represent an average number of repeating units; n represents a number of more than 0 and 20 or less; o and p each independently represent a number of 0 to 20; 1.0≤n+o+p≤20.0; Ma each independently represents a hydrocarbon group having from 1 to 12 carbons which may be substituted with a halogen atom; x represents an integer of 0 to 4; structural units (a), (b), and (c) are each bonded to the structural unit (a), (b), or (c), or an additional group by *; and the structural units may be randomly bonded.

3 . The resin composition according to claim 1 , wherein the polyphenylene ether compound (B) contains a polyphenylene ether compound represented by Formula (OP);

in Formula (OP), X represents an aromatic group; —(Y—O) n1 — represents a polyphenylene ether structure; n1 represents an integer of 1 to 100; n2 represents an integer of 1 to 4; and Rx is a group represented by Formula (Rx-1) or Formula (Rx-2); and

in Formula (Rx-1) and Formula (Rx-2), R 1 , R 2 , and R 3 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group; * is a bonding site to an oxygen atom; Mc each independently represents a hydrocarbon group having from 1 to 12 carbons; z represents an integer of 0 to 4; and r represents an integer of 1 to 6.

4 . The resin composition according to claim 1 , wherein the polyphenylene ether compound (B) contains a polyphenylene ether compound represented by Formula (OP-1);

in Formula (OP-1), X represents an aromatic group; —(Y—O)n 2 - represents a polyphenylene ether structure; R 1 , R 2 , and R 3 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group; n 1 represents an integer of from 1 to 6; n 2 represents an integer of from 1 to 100; and n 3 represents an integer of from 1 to 4.

5 . The resin composition according to claim 1 , wherein the polyphenylene ether compound (B) has a number average molecular weight (Mn) of 500 to 3000 and a weight average molecular weight (Mw) of 800 to 6000.

6 . The resin composition according to claim 1 , wherein the resin (A) has a number average molecular weight (Mn) of 400 to 3000.

7 . The resin composition according to claim 1 , wherein the mass ratio of the content of the resin (A) to the content of the polyphenylene ether compound (B); i.e., resin (A)/polyphenylene ether compound (B) is 5/95 to 45/55.

8 . The resin composition according to claim 1 , which comprises substantially no polymerization inhibitor.

9 . The resin composition according to claim 1 , which further comprises an additional compound (C) other than the resin (A) and the polyphenylene ether compound (B).

10 . The resin composition according to claim 9 , wherein the additional compound (C) contains one or more selected from the group consisting of a maleimide compound, a cyanate ester compound, an epoxy compound, a phenol compound, a compound containing a (meth)allyl group, an oxetane resin, a benzoxazine compound, an arylcyclobutene resin, a polyamide resin, a polyimide resin, a perfluorovinyl ether resin, a compound having a styrene group other than the polyphenylene ether compound (B), a compound having an isopropenyl group other than the resin (A) having an indane skeleton, a polyfunctional (meth)acrylate compound other than the polyphenylene ether compound (B), an elastomer, and a petroleum resin.

11 . The resin composition according to claim 1 , wherein a total content of the resin (A) and the polyphenylene ether compound (B) is 40 parts by mass or more relative to 100 parts by mass of a resin solid content in the resin composition.

12 . The resin composition according to claim 1 , which further comprises a filler (D).

13 . The resin composition according to claim 12 , wherein a content of the filler (D) is from 10 to 1000 parts by mass relative to 100 parts by mass of a resin solid content in the resin composition.

14 . The resin composition according to claim 1 , wherein the resin (A) contains a resin represented by Formula (T1-1); the polyphenylene ether compound (B) contains a polyphenylene ether compound represented by Formula (OP); the polyphenylene ether compound (B) has a number average molecular weight (Mn) of 500 to 3000 and a weight average molecular weight (Mw) of 800 to 6000; the resin (A) has a number average molecular weight (Mn) of 400 to 3000; the mass ratio of the content of the resin (A) to the content of the polyphenylene ether compound (B); i.e., resin (A)/polyphenylene ether compound (B) is 5/95 to 45/55; a polymerization inhibitor is substantially not contained, and a total content of the resin (A) and the polyphenylene ether compound (B) is 40 parts by mass or more relative to 100 parts by mass of a resin solid content in the resin composition;

in Formula (T1-1), R is a group containing structural units represented by Formula (Tx); Mb each independently represents a hydrocarbon group having from 1 to 12 carbons which may be substituted with a halogen atom; and y is an integer of 0 to 4; and

in Formula (Tx), n, o, and p each represent an average number of repeating units; n represents a number of more than 0 and 20 or less; o and p each independently represent a number of 0 to 20; 1.0≤n+o+p≤20.0; Ma each independently represents a hydrocarbon group having from 1 to 12 carbons which may be substituted with a halogen atom; x represents an integer of 0 to 4; structural units (a), (b), and (c) are each bonded to the structural unit (a), (b), or (c), or an additional group by *; and the structural units may be randomly bonded; and

in Formula (OP), X represents an aromatic group; —(Y—O) n1 — represents a poly

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Itoh Syouichi
• Tadokoro Hiroaki
• Innan Susumu
• Miyamoto Makoto
• Futamura Keisuke

Classifications

• H05K1/0373

  containing additives, e.g. fillers (H05K1/036 takes precedence) · CPC title

• C08L45/00

  Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers (of cyclic anhydrides or imides C08L35/00; of cyclic esters of polyfunctional acids C08L31/00) · CPC title

• B32B2457/08

  PCBs, i.e. printed circuit boards · CPC title

• B32B15/20

  comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)} · CPC title

• B32B15/092

  comprising epoxy resins · CPC title