Thermosetting resin composition, and prepreg, insulating film with support, laminate plate, and printed wiring board, each obtained using same

Patent metadata

Field	Value
Publication number	US-10119047-B2
Application number	US-201514675023-A
Country	US
Kind code	B2
Filing date	Mar 31, 2015
Priority date	Mar 27, 2009
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

A thermosetting resin composition containing: (A) a resin composition having an unsaturated maleimide group, produced by reacting (a) a maleimide compound having at least two N-substituted maleimide groups per one molecule and (b) an amine compound having at least two primary amino groups per one molecule, in an organic solvent; (B) a thermosetting resin; and (C) a modified imidazole compound, such as an isocyanate-masked imidazole and an epoxy-masked imidazole, and a prepreg, an insulating film with a support, a laminate plate and a printed wiring board, each containing the same.

First claim

The invention claimed is:

1. A thermosetting resin composition comprising:
(A) a resin composition having an unsaturated maleimide group, which is a reaction product produced by reacting (a) a maleimide compound having at least two N-substituted maleimide groups per one molecule and (b) an amine compound having at least two primary amino groups per one molecule, wherein in producing said reaction product, the maleimide compound (a) and the amine compound (b) are used in a ration that satisfies the equivalent ration (T a /T b ) in a range of 1.0<T a /T b ≤10.0, where (T a /T b ) is the equivalent ratio of the equivalent (T a ) of the maleimide group in the maleimide compound (a) to the equivalent (T b ) of the —NH 2 group in the amine compound (b);
(B) a thermosetting resin;
(C) a modified imidazole compound represented by any one of the following general formulae (I) and (II):

wherein R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having from 1 to 20 carbon atoms or a phenyl group;
and A represents an alkylene group or an aromatic hydrocarbon group,

wherein R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having from 1 to 20 carbon atoms or a phenyl group;
and B represents a single bond, an alkylene group, an alkylidene group, an ether group or a sulfonyl group; and
(D) an amine compound having an acidic substituent represented by the following general formula (IV):

wherein R 1 each independently represent a hydroxyl group, a carboxyl group or a sulfonic acid group as the acidic substituent; R 2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having from 1 to 5 carbon atoms or a halogen atom; x represents an integer of from 1 to 5; and y represents an integer of from 0 to 4, provided that a sum of x and y is 5.

2. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises (E) an inorganic filler.

3. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises (F) a molybdenum compound.

4. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises (G) a phosphorus-containing compound that imparts flame retardancy.

5. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises (H) a compound that achieves chemical roughening.

6. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin (B) is at least one selected from the group consisting of an epoxy resin, a phenol resin, an unsaturated imide resin, a cyanate resin, an isocyanate resin, a benzoxazine resin, an oxetane resin, an amino resin, an unsaturated polyester resin, an allyl resin, a dicyclopentadiene resin, a silicone resin, a triazine resin and a melamine resin.

7. The thermosetting resin composition according to claim 2 , wherein the inorganic filler (E) is fused spherical silica and/or a metal hydrate that has a thermal decomposition temperature of 300° C. or more.

8. An insulating film with a support comprising a support having formed on a surface thereof a film containing the thermosetting resin composition according to claim 1 in a semi-cured state.

9. A prepreg comprising the thermosetting resin composition according to claim 1 that is coated on a reinforcing substrate in a form of a fiber sheet, and is rendered into a B-stage.

10. A laminate plate comprising at least one sheet of the insulating film with a support according to claim 8 .

11. A printed wiring board comprising the laminate plate according to claim 10 .

12. A laminate plate comprising at least one sheet of the prepreg according to claim 9 .

13. A printed wiring board comprising the laminate plate according to claim 12 .

14. A laminate plate comprising (i) at least one sheet of an insulating film with a support comprising a support having formed on a surface thereof a film containing the thermosetting resin composition according to claim 1 in a semi-cured state, and (ii) at least one sheet of a prepreg comprising said thermosetting resin composition that is coated on a reinforcing substrate in a form of a fiber sheet and is rendered into a B-stage.

15. A printed wiring board comprising the laminate plate according to claim 14 .

16. The thermosetting resin composition according to claim 1 , wherein said modified imidazole compound (C) is the compound represented by the general formula (I).

17. The thermosetting resin composition according to claim 1 , which contains 0.01 to 10 parts by mass of the modified imidazole compound (C) per 100 parts by mass of the thermosetting resin (B).

18. The thermosetting resin composition according to claim 1 , wherein said modified imidazole compound (C) is the compound represented by the general formula (II).

19. A resin varnish comprising the thermosetting resin composition according to claim 1 and an organic solvent therefore.

20. The thermosetting resin composition according to claim 1 , wherein said reaction product has been produced by reacting said maleimide compound and said amine compound in an organic solvent.

21. The thermosetting resin composition according to claim 1 , wherein the amine compound (D) is at least one selected from the group consisting of m-aminophenol, p-aminophenol, o-aminophenol, p-aminobenzoic acid, m-aminobenzoic acid, o-aminobenzoic acid, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 3,5-dihydroxyaniline and 3,5-dicarboxyaniline.

22. The thermosetting resin composition according to claim 1 , wherein the resin composition having an unsaturated maleimide group (A) and the amine compound (D) are used in a ratio that satisfies the equivalent ratio (T A /T D ) in a range of 1.0<(T A /T D )≤10.0, where (T A /T D ) is the equivalent ratio of the equivalent (T A ) of the maleimide group of the resin composition (A) to the equivalent (T D ) of the —NH 2 group in the amine compound (D).

Assignees

• Hitachi Chemical Co Ltd

Inventors

• Kotake Tomohiko
• Tsuchikawa Shinji
• Izumi Hiroyuki
• Miyatake Masato
• Takanezawa Shin
• Murai Hikari
• Irino Tetsurou

Classifications

• B32B2307/7265

  Non-permeable · CPC title

• C08L79/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• B32B2457/08

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

• B32B2264/102

  Oxide or hydroxide · CPC title

• B32B27/38

  comprising epoxy resins · CPC title