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KR-20260068093-A - Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device

KR20260068093AKR 20260068093 AKR20260068093 AKR 20260068093AKR-20260068093-A

Abstract

A resin composition comprising a resin (A) having terminal groups represented by formula (T1) and also having a terminal skeleton, a thermosetting compound (B) other than the resin (A), and an inorganic filler (C) having functional groups. A cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and a semiconductor device using the resin composition.

Inventors

  • 미야모토 마코토
  • 고바야시 다카시
  • 히가시타 가즈유키
  • 하세베 게이이치

Assignees

  • 미츠비시 가스 가가쿠 가부시키가이샤

Dates

Publication Date
20260513
Application Date
20240912
Priority Date
20230913

Claims (20)

  1. A resin (A) having a terminal group represented by formula (T1) and also having a terminal skeleton, and A thermosetting compound (B) other than the above resin (A), and Comprising an inorganic filler (C) having functional groups, Resin composition. (In Equation (T1), Ma represents a hydrocarbon group having 1 to 12 carbon atoms that may each be independently substituted with a halogen atom, and x represents an integer from 0 to 4. * indicates a bonding position with other sites.)
  2. In Article 1, A resin composition comprising the above resin (A), wherein the resin is represented by the formula (T1-1). (In Equation (T1-1), R is a group containing the constituent unit represented by Equation (Tx). Ma represents a hydrocarbon group having 1 to 12 carbon atoms that may each be independently substituted with a halogen atom. x is an integer from 0 to 4.) (In Equation (Tx), n, o, and p are the average number of repeating units, n represents a number greater than 0 and less than or equal to 20, o and p each independently represent numbers from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms that may be substituted with a halogen atom. x represents an integer from 0 to 4. Constituent units (a), (b), and (c) are each bonded to constituent units (a), (b), (c) or other groups in *, and each constituent unit may be bonded randomly.)
  3. In Article 1 or Article 2, A resin composition comprising at least one selected from the group consisting of the thermosetting compound (B), a maleimide compound, a polymer having a constituent unit represented by formula (V), a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end, a (meth)allyl compound, a (meth)acrylate compound, a compound having an indan backbone having a carbon-carbon unsaturated double bond at the end other than the resin (A), an epoxy compound, a phenol compound, an oxetane resin, a benzoxazine compound, a cyanate ester compound, and a compound having a vinylene group. (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.)
  4. In Article 1 or Article 2, A resin composition comprising at least one selected from the group consisting of the thermosetting compound (B), the compound represented by formula (M0), the compound represented by formula (M1), the compound represented by formula (M3), the compound represented by formula (M4), the compound represented by formula (M5), a polymer having a constituent unit represented by formula (V), and the compound represented by formula (OP). (In formula (MO), R 51 each independently represents a hydrogen atom, a C1-C8 alkyl group, or a phenyl group, R 52 each independently represents a hydrogen atom or a methyl group, and n 1 represents an integer greater than or equal to 1.) (In formula (M1), RM1 , RM2 , RM3 , and RM4 each independently represent a hydrogen atom or an organic group. RM5 and RM6 each independently represent a hydrogen atom or an alkyl group. ArM represents a divalent aromatic group. A is a 4- to 6-membered ring alicyclic group. RM7 and RM8 each independently represent an alkyl group. mx is 1 or 2, and lx is 0 or 1. RM9 and RM10 each independently represent a hydrogen atom or an alkyl group. RM11 , RM12 , RM13 , and RM14 each independently represent a hydrogen atom or an organic group. RM15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, or a carbon atom having 1 to 10 carbon atoms Represents an alkylthio group, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer from 0 to 3. nx represents an integer from 1 to 20.) (In formula (M3), R 55 each independently represents a hydrogen atom, a C1-C8 alkyl group, or a phenyl group, and n 5 represents an integer from 1 to 10.) (In formula (M4), R 56 each independently represents a hydrogen atom, a methyl group, or an ethyl group, and R 57 each independently represents a hydrogen atom or a methyl group.) (In formula (M5), R 58 each independently represents a hydrogen atom, a C1-C8 alkyl group, or a phenyl group, R 59 each independently represents a hydrogen atom or a methyl group, and n 6 represents an integer greater than or equal to 1.) (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.) (In formula (OP), X represents an aromatic group, -(YO) n1- represents a polyphenylene ether structure, n1 represents an integer from 1 to 100, and n2 represents an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2).) (In formulas (Rx-1) and (Rx-2), R1 , R2 , and R3 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. Mc each independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.)
  5. In Article 1 or Article 2, With respect to 100 parts by mass of the resin solid content in the above resin composition, A composition comprising 1 to 90 parts by mass of the resin (A) and 5 to 90 parts by mass of the thermosetting compound (B), Resin composition.
  6. In Article 1 or Article 2, A resin composition in which the functional group of the inorganic filler (C) is at least one selected from the group consisting of an amino group and an organic group including a carbon-carbon unsaturated bond.
  7. In Article 1 or Article 2, A resin composition in which the functional group of the above-mentioned inorganic filler (C) is at least one selected from the group consisting of organic groups including carbon-carbon unsaturated bonds.
  8. In Article 1 or Article 2, A resin composition in which the functional group of the above-mentioned inorganic filler (C) is an organic group comprising at least one of CH 2 = C(X)- (where X is a hydrogen atom or a methyl group).
  9. In Article 1 or Article 2, A resin composition in which the functional group of the above-mentioned inorganic filler (C) is at least one selected from the group consisting of vinyl group, allyl group, and (meth)acryloyl group.
  10. In Article 1 or Article 2, A resin composition in which the above-mentioned inorganic filler (C) is surface-treated with a silane coupling agent having carbon-carbon unsaturated bonds.
  11. In Article 1 or Article 2, A resin composition comprising one or more inorganic fillers (C) selected from the group consisting of silica, aluminum hydroxide, talc, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate.
  12. In Article 1 or Article 2, A resin composition in which the above-mentioned inorganic filler (C) comprises silica.
  13. In Article 1 or Article 2, A resin composition having a content of the inorganic filler (C) of 10 to 1600 parts by mass per 100 parts by mass of resin solids in the resin composition.
  14. In Article 1, The above resin (A) comprises a resin represented by formula (T1-1), and The thermosetting compound (B) comprises at least one selected from the group consisting of a maleimide compound, a polymer having a constituent unit represented by formula (V), a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end, a (meth)allyl compound, a (meth)acrylate compound, a compound having an indan backbone having a carbon-carbon unsaturated double bond at the end other than the resin (A), an epoxy compound, a phenol compound, an oxetane resin, a benzoxazine compound, a cyanate ester compound, and a compound having a vinylene group. With respect to 100 parts by mass of the resin solid content in the above resin composition, The above resin (A) comprises 1 to 90 parts by mass and the above thermosetting compound (B) comprises 5 to 90 parts by mass, The functional group of the above-mentioned inorganic filler (C) is at least one selected from the group consisting of vinyl groups, allyl groups, and (meth)acryloyl groups, and The above inorganic filler (C) is surface-treated with a silane coupling agent having carbon-carbon unsaturated bonds, and The above inorganic filler (C) comprises one or more selected from the group consisting of silica, aluminum hydroxide, talc, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate, and A resin composition having a content of the inorganic filler (C) of 10 to 1600 parts by mass per 100 parts by mass of resin solids in the resin composition. (In Equation (T1-1), R is a group containing the constituent unit represented by Equation (Tx). Ma represents a hydrocarbon group having 1 to 12 carbon atoms that may each be independently substituted with a halogen atom. x is an integer from 0 to 4.) (In Equation (Tx), n, o, and p are the average number of repeating units, n represents a number greater than 0 and less than or equal to 20, o and p each independently represent numbers from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms that may be substituted with a halogen atom. x represents an integer from 0 to 4. Constituent units (a), (b), and (c) are each bonded to constituent units (a), (b), (c) or other groups in *, and each constituent unit may be bonded randomly.) (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.)
  15. In Article 14, A resin composition comprising at least one selected from the group consisting of the thermosetting compound (B), the compound represented by formula (M0), the compound represented by formula (M1), the compound represented by formula (M3), the compound represented by formula (M4), the compound represented by formula (M5), a polymer having a constituent unit represented by formula (V), and the compound represented by formula (OP). (In formula (MO), R 51 each independently represents a hydrogen atom, a C1-C8 alkyl group, or a phenyl group, R 52 each independently represents a hydrogen atom or a methyl group, and n 1 represents an integer greater than or equal to 1.) (In formula (M1), RM1 , RM2 , RM3 , and RM4 each independently represent a hydrogen atom or an organic group. RM5 and RM6 each independently represent a hydrogen atom or an alkyl group. ArM represents a divalent aromatic group. A is a 4- to 6-membered ring alicyclic group. RM7 and RM8 each independently represent an alkyl group. mx is 1 or 2, and lx is 0 or 1. RM9 and RM10 each independently represent a hydrogen atom or an alkyl group. RM11 , RM12 , RM13 , and RM14 each independently represent a hydrogen atom or an organic group. RM15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, or a carbon atom having 1 to 10 carbon atoms Represents an alkylthio group, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer from 0 to 3. nx represents an integer from 1 to 20.) (In formula (M3), R 55 each independently represents a hydrogen atom, a C1-C8 alkyl group, or a phenyl group, and n 5 represents an integer from 1 to 10.) (In formula (M4), R 56 each independently represents a hydrogen atom, a methyl group, or an ethyl group, and R 57 each independently represents a hydrogen atom or a methyl group.) (In formula (M5), R 58 each independently represents a hydrogen atom, a C1-C8 alkyl group, or a phenyl group, R 59 each independently represents a hydrogen atom or a methyl group, and n 6 represents an integer greater than or equal to 1.) (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.) (In formula (OP), X represents an aromatic group, -(YO) n1- represents a polyphenylene ether structure, n1 represents an integer from 1 to 100, and n2 represents an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2).) (In formulas (Rx-1) and (Rx-2), R1 , R2 , and R3 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. Mc each independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.)
  16. In Article 1, Article 2, Article 14, or Article 15, Additionally, a resin composition comprising an elastomer.
  17. In Article 1, Article 2, Article 14, or Article 15, Additionally, a resin composition comprising a flame retardant.
  18. In Article 1, Article 2, Article 14, or Article 15, Additionally, a resin composition comprising a curing accelerator.
  19. In Article 18, A resin composition having a content of 0.1 to 0.8 parts by mass of the curing accelerator per 100 parts by mass of the resin solid content in the resin composition.
  20. A cured product of the resin composition described in claim 1, 2, 14, or 15.

Description

Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device The present invention relates to a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed circuit board, and a semiconductor device. Recently, the high integration and miniaturization of semiconductor devices used in mobile terminals, electronic devices, and communication equipment have been accelerating. Along with this, technologies that enable high-density mounting of semiconductor devices are required, and improvements are also needed for printed circuit boards, which occupy a crucial position in this process. Meanwhile, the applications of electronic devices and the like continue to diversify and expand. In response to this, the various characteristics required for printed circuit boards, the metal foil-clad laminates and prepregs used therein, and others are becoming more diverse and stringent. To obtain improved printed circuit boards while considering these required characteristics, various materials and processing methods have been proposed. One such example is the development of improved resin materials that constitute prepregs and resin composite sheets. Patent Document 1 discloses a resin having an isopropenphenyl group at the end and also having a terminal backbone, as a preferred material for semiconductor encapsulating materials and printed circuit boards. Figure 1 shows the NMR chart of the resin obtained in Synthesis Example 1. Hereinafter, a form for carrying out the present invention (hereinafter simply referred to as "the present embodiment") will be described in detail. Furthermore, the following present embodiment is provided as an example to explain the present invention, and the present invention is not limited to the present embodiment. Additionally, in this specification, "∼" is used to mean including the numerical values described before and after it as lower and upper limits. In this specification, various physical properties and characteristic values are defined as being at 23°C unless specifically described otherwise. In the notation of a group (atomic group) in this specification, notations that do not specify substitution or non-substitution include both groups (atomic groups) that do not have substituents and groups (atomic groups) that have substituents. For example, "alkyl group" includes not only alkyl groups that do not have substituents (non-substituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups). In this specification, for notations that do not specify substitution or non-substitution, non-substitution is preferred. In this specification, "(meth)allyl group" represents both allyl and metaallyl, or either; "(meth)acrylate" represents both acrylate and methacrylate, or either; "(meth)acryl" represents both acryl and methacryl, or either; and "(meth)acryloyl" represents both acryloyl and methacryloyl, or either. In this specification, the term "process" is used not only for independent processes but also for cases where the process cannot be clearly distinguished from other processes, provided that the intended function of the process is achieved. In cases where measurement methods, etc. described by the standards in this specification differ from year to year, unless specifically stated otherwise, they shall be based on the standards as of January 1, 2023. In the present specification, the term "resin solids" refers to components excluding fillers and solvents, and includes resin (A), thermosetting compound (B), and other components, elastomers or resin additive components (additives such as curing accelerators, flame retardants, etc.) that are blended as needed. In this specification, the terms dielectric constant and dielectric constant are used interchangeably. The resin composition of the present embodiment is characterized by comprising a resin (A) having a terminal group represented by formula (T1) and also having a terminal skeleton (in this specification, it may be simply referred to as “resin (A)”), a thermosetting compound (B) other than the resin (A) (in this specification, it may be simply referred to as “thermosetting compound (B)”), and an inorganic filler (C) having a functional group (in this specification, it may be simply referred to as “inorganic filler (C)”). [Chemical Formula 24] (In Equation (T1), Ma represents a hydrocarbon group having 1 to 12 carbon atoms that may each be independently substituted with a halogen atom, and x represents an integer from 0 to 4. * indicates a bonding position with other sites.) By configuring it in this way, a resin composition is obtained that can provide a cured product with excellent moisture absorption, heat resistance, and chemical resistance while maintaining low dielectric properties (Dk and/or Df). The inventors have discovered the possibility that a resin (A) having an indan