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KR-20260066134-A - Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device

KR20260066134AKR 20260066134 AKR20260066134 AKR 20260066134AKR-20260066134-A

Abstract

A resin composition comprising a resin (A) having a terminal group represented by formula (T1) and also having a terminal backbone, a thermoplastic elastomer (B), and at least one thermosetting compound (C) selected from the group consisting of compounds having a carbon-carbon unsaturated double bond polymerizable at a terminal other than the resin (A), maleimide compounds, and cyanate ester compounds, wherein the thermoplastic elastomer (B) comprises a hydrogenated butadiene monomer unit and/or a hydrogenated isoprene monomer unit. 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 sites. A cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device using the resin composition.

Inventors

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

Assignees

  • 미츠비시 가스 가가쿠 가부시키가이샤

Dates

Publication Date
20260512
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 thermoplastic elastomer (B) and, It comprises at least one thermosetting compound (C) selected from the group consisting of compounds having a polymerizable carbon-carbon unsaturated double bond at a terminal other than the resin (A), maleimide compounds, and cyanate ester compounds, and A resin composition in which the above thermoplastic elastomer (B) comprises hydrogenated butadiene monomer units and/or hydrogenated isoprene monomer units. (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 having a hydrogenation rate of 70% or more of the above thermoplastic elastomer (B).
  3. In Article 1 or Article 2, A resin composition in which the above thermoplastic elastomer (B) comprises styrene monomer units and hydrogenated butadiene monomer units and/or hydrogenated isoprene monomer units.
  4. In Article 1 or Article 2, A resin composition having a number average molecular weight of 2,000 or more of the above thermoplastic elastomer (B).
  5. In Article 1 or Article 2, A resin composition comprising the above thermoplastic elastomer (B) in a ratio of 2.5 to 50 parts by mass per 100 parts by mass of resin solids in the resin composition.
  6. In Article 1 or Article 2, 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.)
  7. In Article 1 or Article 2, A resin composition comprising the above resin (A) in a ratio of 1 to 90 parts by mass per 100 parts by mass of resin solids in the above resin composition.
  8. In Article 1 or Article 2, A resin composition comprising at least one selected from the group consisting of the thermosetting compound (C), 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 a terminal skeleton having a carbon-carbon unsaturated double bond at the end other than the resin (A), and a cyanate ester compound. (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 thermosetting compound (C), 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, A composition comprising 5 to 90 parts by mass of the thermosetting compound (C) per 100 parts by mass of the resin solid content in the resin composition, Resin composition.
  11. In Article 1, The hydrogenation rate of the above thermoplastic elastomer (B) is 70% or more, and The above thermoplastic elastomer (B) comprises styrene monomer units, hydrogenated butadiene monomer units and/or hydrogenated isoprene monomer units, and The number average molecular weight of the above thermoplastic elastomer (B) is 2,000 or more, and The above thermoplastic elastomer (B) is included in a ratio of 2.5 to 50 parts by mass per 100 parts by mass of resin solids in the resin composition, The above resin (A) comprises a resin represented by formula (T1-1), and The above resin (A) is included in a ratio of 1 to 90 parts by mass per 100 parts by mass of resin solids in the above resin composition, The thermosetting compound (C) 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), and a cyanate ester compound. A composition comprising 1 to 90 parts by mass of the thermosetting compound (C) per 100 parts by mass of the resin solid content in the resin composition, 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 selected from the group consisting of the thermosetting compound (C), 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.)
  13. In Article 1, Article 2, Article 11, or Article 12, Additionally, a resin composition comprising a flame retardant.
  14. In Article 1, Article 2, Article 11, or Article 12, Additionally, a resin composition comprising a filler.
  15. In Article 14, 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.
  16. In Article 1, Article 2, Article 11, or Article 12, Additionally, a resin composition comprising a curing accelerator.
  17. In Article 16, 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.
  18. A cured product of the resin composition described in claim 1, 2, 11, or 12.
  19. A prepreg formed of a resin composition described in claim 1, claim 2, claim 11 or claim 12.
  20. A metal foil coated laminate comprising at least one layer formed of prepreg as described in claim 19 and a metal foil disposed on one or both sides of the layer formed of prepreg.

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, metal foil-clad laminates and prepregs used therein, etc., are becoming more diverse and stringent. In order to obtain improved printed circuit boards while taking these required characteristics into account, various materials and processing methods have been proposed. One such example is the development of improved resin materials that constitute prepregs or 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 an example for explaining the present invention, and the present invention is not limited to the present embodiment. In addition, 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, notations that do not specify substitution or non-substitution include groups (atomic groups) that have substituents, along with groups (atomic groups) that do not 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 the present specification, (meth)allyl group represents either allyl and methalyl, or either (meth)acrylate represents either acrylate or methacrylate, (meth)acryl represents either acryl or methacryl, and (meth)acryloyl represents either acryloyl or methacryloyl. In this specification, the term “process” is included not only in independent processes but also in cases where the process 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 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 is intended to include resin (A), thermoplastic elastomer (B), and thermosetting compound (C), and other components and 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 comprises a resin (A) having a terminal group represented by formula (T1) and also having a terminal backbone (in this specification, it may be simply referred to as “resin (A)”), a thermoplastic elastomer (B), and at least one thermosetting compound (C) selected from the group consisting of a compound having a carbon-carbon unsaturated double bond polymerizable at a terminal other than the resin (A), a maleimide compound, and a cyanate ester compound (in this specification, it may be simply referred to as “thermosetting compound (C)”), wherein the thermoplastic elastomer (B) comprises a hydrogenated butadiene monomer unit and/or a hydrogenated isoprene monomer unit. [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, it is possible to provide a resin composition that