Resin composition, prepreg, resin sheet, metal foil-clad laminate, and printed circuit board

Patent metadata

Field	Value
Publication number	US-10676579-B2
Application number	US-201615737504-A
Country	US
Kind code	B2
Filing date	Jul 4, 2016
Priority date	Jul 6, 2015
Publication date	Jun 9, 2020
Grant date	Jun 9, 2020

Abstract

It is intended to provide a resin composition that serves as a raw material for a printed circuit board excellent in heat resistance after moisture absorption and is excellent in moldability. The resin composition of the present invention contains a maleimide compound, a silane compound having a carbon-carbon unsaturated bond and a hydrolyzable group or a hydroxy group, a silane compound having an epoxy skeleton and a hydrolyzable group or a hydroxy group, and an inorganic filler.

First claim

The invention claimed is:

1. A resin composition comprising:
a maleimide compound,
a silane compound having a carbon-carbon unsaturated bond and a hydrolyzable group or a hydroxy group,
a silane compound having an epoxy skeleton and a hydrolyzable group or a hydroxy group, and
an inorganic filler;
wherein the silane compound having an epoxy skeleton and a hydrolyzable group or a hydroxy group is a compound represented by the following formula (D):

where:
R 10 represents the hydrolyzable group or the hydroxy group; R 11 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; when a plurality of R 10 or R 11 are present, the plurality of R 10 or R 11 are the same as or different from each other; R 12 represents an alkylene group having 1 to 10 carbon atoms; and m represents an integer of 1 to 3.

2. The resin composition according to claim 1 , wherein the resin composition comprises, as the silane compound having a carbon-carbon unsaturated bond and a hydrolyzable group or a hydroxy group, a silane compound having a styrene skeleton and a hydrolyzable group or a hydroxy group, and/or a silane compound having a (meth)acryl skeleton and a hydrolyzable group or a hydroxy group.

3. The resin composition according to claim 2 , wherein the resin composition comprises, as the silane compound having a carbon-carbon unsaturated bond and a hydrolyzable group or a hydroxy group, a silane compound having a styrene skeleton and a hydrolyzable group or a hydroxy group.

4. The resin composition according to claim 2 , wherein the resin composition comprises, as the silane compound having a styrene skeleton and a hydrolyzable group or a hydroxy group, a compound represented by the following formula (A):

wherein
R 8 represents the hydrolyzable group or the hydroxy group;
R 9 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms;
when a plurality of R 8 or R 9 are present, the plurality of R 8 or R 9 are the same as or different from each other; and
k represents an integer of 1 to 3.

5. The resin composition according to claim 2 , wherein the resin composition comprises, as the silane compound having a (meth)acryl skeleton and a hydrolyzable group or a hydroxy group, a compound represented by the following formula (C):

wherein R 13 represents the hydrolyzable group or the hydroxy group; R 14 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; when a plurality of R 13 or R 14 are present, the plurality of R 13 or R 14 are the same as or different from each other; R 15 represents a hydrogen atom or a methyl group; R 16 represents an alkylene group having 2 to 10 carbon atoms; and j represents an integer of 1 to 3.

6. The resin composition according to claim 1 , further comprising an alkenyl-substituted nadimide.

7. The resin composition according to claim 6 , wherein the resin composition comprises, as the alkenyl-substituted nadimide, a compound represented by the following formula (1):

wherein each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R 2 represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or a group represented by the following formula (2) or (3):

wherein R 3 represents a methylene group, an isopropylidene group, or a substituent represented by CO, O, S, or SO 2 , and

wherein each R 4 independently represents an alkylene group having 1 to 4 carbon atoms, or a cycloalkylene group having 5 to 8 carbon atoms.

8. The resin composition according to claim 6 , wherein the resin composition comprises, as the alkenyl-substituted nadimide, a compound represented by the following formula (4) and/or (5):

9. The resin composition according to claim 1 , wherein the resin composition comprises, as the maleimide compound, at least one compound selected from the group consisting of bis(4-maleimidophenyl)methane, 2,2-bis{4-(4-maleimidophenoxy)-phenyl}propane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, polytetramethylene oxide-bis(4-maleimidobenzoate), and a maleimide compound represented by the following formula (6):

wherein each R 5 independently represents a hydrogen atom or a methyl group, and n 1 represents an integer of 1 or larger.

10. The resin composition according to claim 1 , further comprising a cyanate ester compound.

11. The resin composition according to claim 10 , wherein the resin composition comprises, as the cyanate ester compound, a compound represented by the following formula (7) and/or (8):

wherein each R 6 independently represents a hydrogen atom or a methyl group, and n 2 represents an integer of 1 or larger, and

wherein each R 7 independently represents a hydrogen atom or a methyl group, and n 3 represents an integer of 1 or larger.

12. The resin composition according to claim 1 , wherein the inorganic filler comprises at least one selected from the group consisting of silica, alumina, and aluminum nitride.

13. The resin composition according to claim 1 , wherein the content of the inorganic filler in the resin composition is 100 to 1100 parts by mass based on 100 parts by mass in total of resins and components that form resins by polymerization in the resin composition.

14. The resin composition according to claim 1 , wherein the inorganic filler is surface-treated in advance with the silane compound having a carbon-carbon unsaturated bond and a hydrolyzable group or a hydroxy group, and the silane compound having an epoxy skeleton and a hydrolyzable group or a hydroxy group.

15. A metal foil-clad laminate comprising the resin composition according to claim 1 , wherein the metal foil-clad laminate comprises:
a metal foil disposed on one side or both sides of at least one of:
a prepreg comprising a base material impregnated or coated with the resin composition, and
a resin sheet comprising a support coated with the resin composition;

wherein the metal foil-clad laminate comprises a cured product of the resin composition contained in at least one of the prepreg and the resin sheet.

16. A printed circuit board comprising an insulating layer and a conductor layer formed on a surface of the insulating layer, wherein the insulating layer comprises a resin composition according to claim 1 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Tomizawa Katsuya
• Takano Yoichi
• ITO Meguru
• Shiga Eisuke

Classifications

• B32B15/082

  comprising vinyl resins; comprising acrylic resins · CPC title

• C08L35/00 Primary

  Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers · CPC title

• C08F2/44

  Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers · CPC title

• C08J2361/00

  Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers · CPC title

• B32B27/00

  Layered products comprising {a layer of} synthetic resin {(fibrous or filamentary layer made of a synthetic resin B32B5/02; particulate layer made of a synthetic resin B32B5/16; foamed layer made of a synthetic resin B32B5/18)} · CPC title