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US-12617986-B2 - Resin composition, cured product, sheet-like laminate material, resin sheet, printed wiring board, and semiconductor device

US12617986B2US 12617986 B2US12617986 B2US 12617986B2US-12617986-B2

Abstract

Resin compositions including: (A) a naphthol aralkyl type epoxy resin having a weight-average molecular weight (Mw) of 1,000 or more and an epoxy equivalent of 350 g/eq. or more; and (B) a curing agent, in which (B) the curing agent includes an active ester type curing agent are useful for preparing cured products, sheet lamination materials, resin sheets, printed wiring boards, and semiconductor devices, and for methods for producing printed wiring boards or semiconductor devices.

Inventors

  • Kenji Kawai

Assignees

  • AJINOMOTO CO., INC.

Dates

Publication Date
20260505
Application Date
20240429
Priority Date
20201009

Claims (19)

  1. 1 . A method for producing an insulating layer on an inner layer substrate, comprising: (I) laminating a resin sheet on said inner layer substrate so as to bond a resin composition layer of said resin sheet with said inner layer substrate, and (II) curing said resin composition layer, thereby forming said insulating layer; wherein said resin composition layer comprises a resin composition comprising (A) at least one naphthol aralkyl epoxy resin having a weight-average molecular weight (Mw) of 1,000 or more and an epoxy equivalent of 350 g/eq or more; and (B) at least one curing agent, wherein (B) said curing agent comprises (B-1) an active ester curing agent; and the insulating layer has a dielectric loss tangent less than 0.005 measured at a frequency of 5.8 GHz and a temperature of 23° C.
  2. 2 . The method according to claim 1 , wherein said component (A) comprises a compound represented by formula (A1) wherein Ar1 is an optionally substituted arylene group having 6 to 20 carbon atoms; each Ra independently represents a hydrogen atom, a monovalent group having an epoxy group, or an alkyl group having 1 to 12 carbon atoms, in which at least one Ra is the monovalent group having an epoxy group, and at least one Ra is the alkyl group having 1 to 12 carbon atoms; Rb and Rc each independently represent a monovalent group having an epoxy group, an alkyl group having 1 to 12 carbon atoms, an allyl group, or an aryl group having 6 to 10 carbon atoms; Rd represents a hydrogen atom, a monovalent group having an epoxy group, an alkyl group having 1 to 12 carbon atoms, an allyl group, or an aryl group having 6 to 10 carbon atoms; each R1 independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; n represents an integer of 2 to 50; mb represents an integer of 0 to 6; and mc represents an integer of 0 to 5.
  3. 3 . The method according to claim 2 , wherein said component (A) comprises a compound represented by formula (A2) wherein Ra and n are the same as Ra and n respectively, in formula (A1).
  4. 4 . The method according to claim 2 , wherein n is 4 or more, and at least two Ra are an alkyl group having 1 to 6 carbon atoms.
  5. 5 . The method according to claim 1 , wherein said component (B-1) comprises at least one selected from the group consisting of a dicyclopentylene structure and a naphthalene structure.
  6. 6 . The method according to claim 1 , wherein said component (B) further comprises (B-2) a curing agent other than the active ester curing agent.
  7. 7 . The method according to claim 6 , wherein said component (B-2) comprises a phenol curing agent comprising a triazine skeleton.
  8. 8 . The method according to claim 6 , wherein said component (B-2) is present in an amount which is less than that of said component (B-1).
  9. 9 . The method according to claim 1 , wherein said component (B-1) is present in an amount of 3 to 50% by mass relative to 100% by mass of nonvolatile components in said resin composition.
  10. 10 . The method according to claim 1 , wherein said component (A) is present in an amount of 5 to 70% by mass relative to 100% by mass of nonvolatile components in said resin composition.
  11. 11 . The method according to claim 1 , wherein said component (B) is present in an amount of 3 to 70% by mass relative to 100% by mass of nonvolatile components in said resin composition.
  12. 12 . The method according to claim 1 , wherein said resin composition further comprises: (C) at least one inorganic filler.
  13. 13 . The method according to claim 12 , wherein said component (C) is present in an amount of 40% or more by mass relative to 100% by mass of nonvolatile components in the resin composition.
  14. 14 . The method according to claim 1 , wherein said resin composition further comprises: (D) a thermoplastic resin.
  15. 15 . The method according to claim 1 , wherein a glass transition temperature of said insulating layer is higher than 145° C.
  16. 16 . A laminate comprising an inner layer substrate and an insulating layer bonded on said inner layer substrate, wherein said insulating layer is produced by the method according to claim 1 .
  17. 17 . The laminate according to claim 16 , wherein said insulating layer has a glass transition temperature higher than 145° C.
  18. 18 . A printed wiring board, comprising the laminate according to claim 16 .
  19. 19 . A semiconductor device, comprising the printed wiring board according to claim 18 .

Description

REFERENCES TO RELATED APPLICATIONS This application is a divisional application of U.S. application Ser. No. 17/496,382, filed on Oct. 7, 2021, which claims priority to Japanese Patent Application No. 2020-171474, filed on Oct. 9, 2020, which is incorporated herein by reference in its entirety. BACKGROUND OF THE INVENTION Field of the Invention The present invention relates to resin compositions. The present invention further relates to cured products, sheet lamination materials, resin sheets, printed wiring boards, and semiconductor devices, and methods for producing printed wiring boards or semiconductor devices, all being obtained by using this resin composition. Discussion of the Background Japanese Patent Application Laid-open No. 2020-055890, which is incorporated herein by reference in its entirety, discloses, as the resin material used for a multi-layered printed wiring board, a resin material containing an epoxy compound having a naphthalene skeleton, an inorganic filler, and a curing agent. A resin material like this can be used to form an insulating layer in the multi-layered printed wiring board. SUMMARY OF THE INVENTION Accordingly, it is one object of the present invention to provide novel resin compositions capable of producing a cured product that is low in the roughness and excellent in adhesion to a conductor (hereinafter, this is called “conductor adhesion”). It is another object of the present invention to provide novel cured products, sheet lamination materials, resin sheets, printed wiring boards, and semiconductor devices, and methods for producing printed wiring boards or semiconductor devices, all of which being obtained by using such a resin composition. These and other objects, which will become apparent during the following detailed description, have been achieved by the inventors' discovery that these objects could be achieved by using a resin composition having the composition described below. Thus, the present invention includes the following embodiments. (1) A resin composition comprising,(A) at least one naphthol aralkyl type epoxy resin having a weight-average molecular weight (Mw) of 1,000 or more and an epoxy equivalent of 350 g/eq. or more, and(B) at least one curing agent, Wherein (B) the curing agent comprises (B-1) an active ester type curing agent. (2) The resin composition according to (1), whereinthe component (A) comprises a compound represented by the following formula (A1): wherein: Ar1 is an optionally substituted arylene group having 6 to 20 carbon atoms;each Ra independently represents a hydrogen atom, a monovalent group having an epoxy group, or an alkyl group having 1 to 12 carbon atoms, in which at least one Ra is the monovalent group having an epoxy group, and at least one Ra is the alkyl group having 1 to 12 carbon atoms;Rb and Rc each independently represent a monovalent group having an epoxy group, an alkyl group having 1 to 12 carbon atoms, an allyl group, or an aryl group having 6 to 10 carbon atoms;Rd represents a hydrogen atom, a monovalent group having an epoxy group, an alkyl group having 1 to 12 carbon atoms, an allyl group, or an aryl group having 6 to 10 carbon atoms;each R1 independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms;n represents an integer of 2 to 50;mb represents an integer of 0 to 6; andmc represents an integer of 0 to 5.(3) The resin composition according to (2), whereinthe component (A) comprises a compound represented by the following formula (A2): wherein Ra and n are the same as Ra and n, respectively, in the formula (A1). (4) The resin composition according to (2) or (3), wherein n is 4 or more, and at least two Ra are an alkyl group having 1 to 6 carbon atoms.(5) The resin composition according to any one of (1) to (4), wherein the component (B) further comprises (B-2) a curing agent other than the active ester type curing agent.(6) The resin composition according to (5), wherein the component (B-2) is present in an amount which less than that of the component (B-1).(7) The resin composition according to any one of (1) to (6), wherein the component (B-1) is present in an amount of 3 to 50% by mass relative to 100% by mass of nonvolatile components in the resin composition.(8) The resin composition according to any one of (1) to (7), wherein the component (A) is present in an amount of 5 to 70% by mass relative to 100% by mass of nonvolatile components in the resin composition.(9) The resin composition according to any one of (1) to (8), wherein the component (B) is present in an amount of 3 to 70% by mass relative to 100% by mass of nonvolatile components in the resin composition.(10) The resin composition according to any one of (1) to (9), wherein the resin composition further comprises: (C) an inorganic filler.(11) The resin composition according to (10), wherein the component (C) is present in an amount of 40% or more by mass relative to 100% by mass of nonvolatile components in the res