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KR-20260066133-A - Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, printed circuit board, and semiconductor device

KR20260066133AKR 20260066133 AKR20260066133 AKR 20260066133AKR-20260066133-A

Abstract

A resin composition comprising a resin (A) represented by formula (T1-1), a thermosetting compound (B) other than the resin (A), and an inorganic filler (C), wherein the parameter β calculated from formula (β) in the resin (A) is 0.20 or greater and 3.00 or less. In formula (T1-1), R comprises an indan skeleton. The parentheses in formula (β) represent the integral value between corresponding chemical shift values in 1H -NMR. 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
  • 고바야시 다카시
  • 후타무라 게이스케
  • 하세베 게이이치

Assignees

  • 미츠비시 가스 가가쿠 가부시키가이샤

Dates

Publication Date
20260512
Application Date
20240912
Priority Date
20230913

Claims (20)

  1. A resin (A) represented by formula (T1-1), and A thermosetting compound (B) other than the above resin (A), and A resin composition comprising an inorganic filler (C), In the above resin (A), the parameter β calculated from equation (β) is 0.20 or more and 3.00 or less, 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.) (The value inside the parentheses in Equation (β) represents the integral between the corresponding chemical shift values in 1H -NMR.)
  2. In Article 1, A resin composition in which the parameter α calculated from the formula (α) in the above resin (A) is 0.55 or more and 1.00 or less. (The value inside the parentheses in Equation (α) represents the integral between the corresponding chemical shift values in 1H -NMR.)
  3. In Article 2, The parameter α calculated from the above equation (α) is 0.60 or greater and 1.00 or less, and A resin composition having a parameter β calculated from the above formula (β) of 0.40 or more and 3.00 or less.
  4. In any one of paragraphs 1 to 3, A resin composition having 1.1 ≤ n + o + p ≤ 20.0 in the constituent unit represented by the above formula (Tx).
  5. In any one of paragraphs 1 to 3, A resin composition having a number average molecular weight of the above resin (A) of 400 to 3000.
  6. In any one of paragraphs 1 to 3, A resin composition having a weight average molecular weight of the above resin (A) of 500 to 6000.
  7. In any one of paragraphs 1 to 3, A resin composition having a functional group equivalent of the above resin (A) of 200 g/eq. or more and 750 g/eq. or less.
  8. In any one of paragraphs 1 to 3, A resin composition having a ratio of the weight-average molecular weight of the resin (A) to the number-average molecular weight of the resin (A), Mw/Mn, of 1.1 to 3.0.
  9. In any one of paragraphs 1 to 3, 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.)
  10. In any one of paragraphs 1 to 3, 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 (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.)
  11. In any one of paragraphs 1 to 3, 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.
  12. In any one of paragraphs 1 to 3, A resin composition having at least one inorganic filler (C) selected from the group consisting of an epoxy group, an amino group, and an organic group comprising a carbon-carbon unsaturated bond.
  13. In any one of paragraphs 1 to 3, A resin composition in which the above-mentioned inorganic filler (C) has an organic group comprising CH 2 =C(X)- (where X is a hydrogen atom or a methyl group).
  14. In any one of paragraphs 1 to 3, A resin composition comprising at least one inorganic filler (C) selected from the group consisting of vinyl groups, allyl groups, and (meth)acryloyl groups.
  15. In any one of paragraphs 1 to 3, A resin composition in which the above-mentioned inorganic filler (C) is surface-treated with a silane coupling agent having carbon-carbon unsaturated bonds.
  16. In any one of paragraphs 1 to 3, 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.
  17. In any one of paragraphs 1 to 3, A resin composition in which the above-mentioned inorganic filler (C) comprises silica.
  18. In any one of paragraphs 1 to 3, 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.
  19. In Article 1, The parameter α calculated from the above equation (α) is 0.60 or greater and 1.00 or less, and The parameter β calculated from the above equation (β) is 0.40 or greater and 3.00 or less, and In the constituent unit represented by the above equation (Tx), 1.1 ≤ n + o + p ≤ 20.0, and The number average molecular weight of the above resin (A) is 400 to 3000, and The weight average molecular weight of the above resin (A) is 500 to 6000, and The functional group equivalent of the above resin (A) is 200 g/eq. or more and 750 g/eq. or less, and The ratio of the weight-average molecular weight of the resin (A) to the number-average molecular weight of the resin (A), Mw/Mn, is 1.1 to 3.0, 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 above inorganic filler (C) comprises at least one type selected from the group consisting of vinyl groups, allyl groups, acryloyl groups, and methacryloyl 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 (V), Ar represents an aromatic hydrocarbon linker. * indicates a bonding position.)
  20. In Article 19, 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 (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.)

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 resin obtained in Synthesis Example 3. 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) represented by formula (T1-1), 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 a resin composition comprising a resin (A) represented by formula (T1-1) (in this specification, simply referred to as “resin (A)”), a thermosetting compound (B) other than the resin (A) (in this specification, simply referred to as “thermosetting compound (B)”), and an inorganic filler (C), wherein the parameter β calculated from formula (β) in the resin (A) is 0.20 or higher and 3.00 or lower. [Chemical Formula 21] (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.) [Chemical Formula 22] (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 +