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KR-20260066135-A - Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device

KR20260066135AKR 20260066135 AKR20260066135 AKR 20260066135AKR-20260066135-A

Abstract

A resin composition comprising a resin (A) having a terminal group represented by formula (T1) and also having a terminal backbone, a maleimide compound (B) and/or a cyanate ester compound (C), and a compound (D) having a polymerizable carbon-carbon unsaturated double bond at a terminal other than that of 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 sites. 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
  • 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 maleimide compound (B) and/or cyanate ester compound (C), Compound (D) having a polymerizable carbon-carbon unsaturated double bond at a terminal other than the resin (A), 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, With respect to 100 parts by mass of the above resin (A), A total of 10 to 1,000 parts by mass of the maleimide compound (B) and/or the cyanate ester compound (C), and Comprising 10 to 1000 parts by mass of the above compound (D), Resin composition.
  3. In Article 1 or Article 2, A resin composition having a mass ratio of (B + C)/(D), which is the total content (B + C) of the maleimide compound (B) and the cyanate ester compound (C) and the mass ratio of the compound (D), of (B + C) to 0.1 to 10.
  4. In Article 1 or Article 2, A resin composition in which the sum of the amount of maleimide groups (EqB) of the maleimide compound (B) and the amount of functional groups (EqD) of the compound (D) (EqB + EqD), and the amount of isopropenyl groups (EqA) of the resin (A) satisfy the relationship EqB + EqD ≥ EqA.
  5. In Article 1 or Article 2, A resin composition comprising at least the maleimide compound (B).
  6. In Article 1 or Article 2, A resin composition comprising both the maleimide compound (B) and the cyanate ester compound (C), wherein the content of the cyanate ester compound (C) is 0.5 to 60 parts by mass relative to the total content (B + C) of the maleimide compound (B) and the cyanate ester compound (C) of 100 parts by mass.
  7. 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.)
  8. In Article 5, A resin composition comprising one or more selected from the group consisting of the maleimide compound (B) represented by formula (M0), the compound represented by formula (M1), the compound represented by formula (M3), the compound represented by formula (M4), and the compound represented by formula (M5). (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.)
  9. In Article 1 or Article 2, A resin composition comprising the above compound (D), which is a compound represented by the formula (OP). (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 resin composition comprising the above compound (D), a polyphenylene ether compound having a group represented by formula (Rx-1) at the terminal end, and a polyphenylene ether compound having a group represented by formula (Rx-2) at the terminal end. (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.)
  11. In Article 1 or Article 2, A resin composition comprising the above compound (D), a polymer having a constituent unit represented by formula (V). (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.)
  12. In Article 1 or Article 2, A resin composition comprising the above compound (D), wherein the compound (D) comprises a (meth)acrylate compound other than a polyphenylene ether compound having a polymerizable carbon-carbon unsaturated double bond at the terminal end.
  13. In Article 1, With respect to 100 parts by mass of the above resin (A), A total of 10 to 1,000 parts by mass of the maleimide compound (B) and/or the cyanate ester compound (C), and The above compound (D) comprises 10 to 1000 parts by mass, The mass ratio of the total content (B + C) of the maleimide compound (B) and the cyanate ester compound (C) to the compound (D), (B + C)/(D), is 0.1 to 2, and The sum of the amount of maleimide groups (EqB) of the maleimide compound (B) and the amount of functional groups (EqD) of the compound (D) (EqB + EqD), and the amount of isopropenyl groups (EqA) of the resin (A) satisfy the relationship EqB + EqD ≥ EqA, and The above resin (A) comprises a resin represented by formula (T1-1), and The maleimide compound (B) comprises one or more selected from the group consisting of the compound represented by formula (M0), the compound represented by formula (M1), the compound represented by formula (M3), the compound represented by formula (M4), and the compound represented by formula (M5), and The above compound (D) comprises a compound represented by formula (OP) and/or a polymer having a constituent unit represented by formula (V), 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 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 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.) (In Equation (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.)
  14. In Article 13, A resin composition comprising both the maleimide compound (B) and the cyanate ester compound (C), wherein the content of the cyanate ester compound (C) is 0.5 to 60 parts by mass relative to the total content (B + C) of the maleimide compound (B) and the cyanate ester compound (C) of 100 parts by mass.
  15. In Article 13, A resin composition comprising the above compound (D), a polyphenylene ether compound having a group represented by formula (Rx-1) at the terminal end, and a polyphenylene ether compound having a group represented by formula (Rx-2) at the terminal end. (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 13, Article 14, or Article 15, Additionally, a resin composition comprising an elastomer.
  17. In Article 1, Article 2, Article 13, Article 14, or Article 15, Additionally, a resin composition comprising a flame retardant.
  18. In Article 1, Article 2, Article 13, Article 14, or Article 15, Additionally, a resin composition comprising a filler.
  19. In Article 18, 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.
  20. In Article 1, Article 2, Article 13, Article 14, or Article 15, Additionally, a resin composition comprising a curing accelerator.

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 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. Figure 2 shows the NMR chart of the indan compound (IC-1) obtained in Synthesis Example 6. Figure 3 shows the NMR chart of the indancyanate compound obtained in Synthesis Example 6. 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 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 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” includes not only independent processes but also 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 a resin (A) having a terminal group represented by formula (T1) and also having a terminal backbone, a maleimide compound (B) and/or a cyanide ester compound (C), a compound (D) having a polymerizable carbon-carbon unsaturated double bond at a terminal other than the resin (A), 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 (hereinafter simply referred to as “resin having a terminal skeleton (A)” or “resin (A)”), a maleimide compound (B) and/or a cyanate ester compound (C), and a compound (D) having a polymerizable carbon-carbon unsaturated double bond at a terminal other than the resin (A) (hereinafter simply referred to as “compound (D)”). [Chemical Formula 24] (In Equation (T1), Ma represents a hydrocarbon group having 1 to 12 carbon atoms that may each be independently substituted w