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KR-20260065907-A - Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device

KR20260065907AKR 20260065907 AKR20260065907 AKR 20260065907AKR-20260065907-A

Abstract

A resin composition comprising a resin (A) having a terminal group represented by formula (T1) and also having a terminal backbone, a compound (B) having a number average molecular weight of 400 or less having a polymerizable carbon-carbon unsaturated double bond, and a thermosetting compound (C) having a number average molecular weight greater than 400 (provided that compound (B) and compound (C) are not compounds corresponding to resin (A). In formula (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 parts. A cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device using the above resin composition.

Inventors

  • 미야모토 마코토
  • 히가시타 가즈유키
  • 후타무라 게이스케
  • 호리에 시게루
  • 히다 겐지

Assignees

  • 미츠비시 가스 가가쿠 가부시키가이샤

Dates

Publication Date
20260511
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 compound (B) having a number average molecular weight of 400 or less and having a polymerizable carbon-carbon unsaturated double bond, and A resin composition comprising a thermosetting compound (C) having a number average molecular weight greater than 400 (provided that the compound (B) and the compound (C) are not compounds corresponding to resin (A). (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 having an equivalent weight of a polymerizable carbon-carbon unsaturated double bond of the above compound (B) of 50 to 400 g/eq.
  4. In Article 1 or Article 2, A resin composition having a number average molecular weight of the compound (B) of 100 to 400, and the number of polymerizable carbon-carbon unsaturated double bonds in one molecule of the compound (B) of 1 or 2.
  5. In Article 1 or Article 2, A resin composition in which the polymerizable carbon-carbon unsaturated double bond in the above compound (B) is at least one selected from the group consisting of vinyl group, (meth)allyl group, (meth)acryloyl group, vinylene group, and maleimide group.
  6. In Article 1 or Article 2, A resin composition comprising at least one compound (B) selected from the group consisting of divinylbenzene, acenaphthylene, dicyclopentadiene-type difunctional (meth)acrylate, 1,2-bis(4-vinylphenyl)ethane, 4-tert-butylstyrene, and 4-methylstyrene.
  7. In Article 1 or Article 2, A resin composition comprising at least one selected from the group consisting of the compound (C), which is a compound having a number average molecular weight greater than 400, 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, an epoxy compound, a phenol compound, a benzoxazine compound, and a cyanate ester compound. (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.)
  8. In Article 1 or Article 2, A resin composition comprising at least one compound (C) 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, an epoxy compound, a phenol compound, a benzoxazine compound, a cyanate ester compound, and a polyfunctional (meth)acrylate compound other than a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end, wherein the compound has a number average molecular weight greater than 400. (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.)
  9. In Article 1 or Article 2, A resin composition comprising at least one selected from the group consisting of the compound (C), which is a compound having a number average molecular weight greater than 400, 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 (M0), 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.)
  10. In Article 1 or Article 2, For 100 parts by mass of the above resin (A), 5 to 500 parts by mass of the above compound (B), and Comprising 10 to 1000 parts by mass of the above compound (C), Resin composition.
  11. In Article 1, The above resin (A) comprises a resin represented by formula (T1-1), and The equivalent weight of the polymerizable carbon-carbon unsaturated double bond of the above compound (B) is 50 to 400 g/eq., and The number average molecular weight of the above compound (B) is 100 to 400, and the number of polymerizable carbon-carbon unsaturated double bonds in one molecule of the above compound (B) is 1 or 2, and The above compound (C) is a compound having a number average molecular weight greater than 400, comprising at least one selected from the group consisting of maleimide compounds, polymers having constituent units represented by formula (V), polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends, epoxy compounds, phenol compounds, benzoxazine compounds, and cyanate ester compounds, and A compound comprising 5 to 500 parts by mass of the compound (B) and 10 to 1000 parts by mass of the compound (C), with respect to 100 parts by mass of the resin (A). 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.)
  12. In Article 11, A resin composition comprising at least one compound (B) selected from the group consisting of divinylbenzene, acenaphthylene, dicyclopentadiene-type difunctional (meth)acrylate, 1,2-bis(4-vinylphenyl)ethane, 4-tert-butylstyrene, and 4-methylstyrene.
  13. In Article 11, A resin composition comprising at least one selected from the group consisting of the compound (C), which is a compound having a number average molecular weight greater than 400, 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 (M0), 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.)
  14. In Article 1, Article 2, Article 11, Article 12, or Article 13, Additionally, a resin composition comprising an elastomer.
  15. In Article 1, Article 2, Article 11, Article 12, or Article 13, Additionally, a resin composition comprising a flame retardant.
  16. In Article 1, Article 2, Article 11, Article 12, or Article 13, Additionally, a resin composition comprising a filler.
  17. In Article 16, A resin composition having a filler content of 10 to 1600 parts by mass relative to 100 parts by mass of resin solids in the resin composition.
  18. In Article 1, Article 2, Article 11, Article 12, or Article 13, 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, 11, 12, or 13.

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 have become 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, the term “∼” 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, a notation that does not indicate substitution or non-substitution includes a group (atomic group) that has substituents, along with a group (atomic group) that does not have substituents. For example, "alkyl group" includes not only an alkyl group that does not have substituents (non-substituted alkyl group) but also an alkyl group that has substituents (substituted alkyl group). In this specification, a notation that does not indicate substitution or non-substitution is preferred to be non-substituted. In this specification, "(meth)allyl group" represents either allyl or metaallyl, "(meth)acrylate" represents either acrylate or methacrylate, "(meth)acryl" represents either acrylic or methacryl, and "(meth)acryloyl" represents either acryloyl or methacryloyl. In this specification, the term "process" is used not only for independent processes but also for processes that cannot be clearly distinguished from other processes, provided that the intended function of the process is achieved. In cases where the measurement methods, etc. described in the standards set forth in this specification differ by 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 is intended to include a resin (A) having a terminal group represented by formula (T1) and also having a terminal backbone, a compound (B) having a number average molecular weight of 400 or less having a polymerizable carbon-carbon unsaturated double bond, a thermosetting compound (C) having a number average molecular weight greater than 400, 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 relative permittivity and permittivity 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 (hereinafter simply referred to as “resin having a terminal skeleton (A)” or “resin (A)”), a compound (B) having a number average molecular weight of 400 or less having a polymerizable carbon-carbon unsaturated double bond (hereinafter simply referred to as “compound (B)”), and a thermosetting compound (C) having a number average molecular weight greater than 400 (hereinafter simply referred to as “thermosetting compound (C)” or “compound (C)”) (however, the compound (B) and the compound (C) are not compounds corresponding to resin (A)). [Chemical Formula 25] (In Equation (T1), Ma represents a hydrocarbon group having 1 to 12 carbon at