Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B15/00—Layered products comprising a layer of metal
  • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
  • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
  • C08F22/36—Amides or imides
  • C08F22/40—Imides, e.g. cyclic imides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/013—Fillers, pigments or reinforcing additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
  • H05K1/00—Printed circuits
  • H05K1/02—Details
  • H05K1/03—Use of materials for the substrate
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/10—Encapsulations, e.g. protective coatings characterised by their shape or disposition
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials

Definitions

• thermosetting resin compositions prepregs, resin films, laminates, printed wiring boards, and semiconductor packages.
• maleimide compounds with indan rings has been proposed as a material for printed wiring boards that require low transmission loss (see, for example, Patent Document 1).
• thermosetting resin composition that can exhibit low dielectric constant, low thermal expansion, and high adhesion to conductors, as well as to provide prepregs, resin films, laminates, printed wiring boards, and semiconductor packages obtained using the thermosetting resin composition.
• thermosetting resin composition disclosed herein can achieve the above-mentioned objective.
• thermosetting resin composition comprising: (A) a maleimide resin having an indane skeleton; (B) a polyfunctional maleimide resin; and (C) a maleimide resin not having an indane skeleton.
• component (A) is a bismaleimide resin containing an indane skeleton.
• component (B) is an aromatic maleimide resin having three or more N-substituted maleimide groups.
• thermosetting resin composition according to any one of [1] to [3] above, wherein the component (B) is a maleimide resin represented by the following general formula (B-1): (In the formula, X b-1 is a divalent hydrocarbon group having 1 to 20 carbon atoms (but does not contain an indane skeleton), and n b-1 is an integer of 2 to 5.) [5] The thermosetting resin composition according to any one of the above [1] to [4], wherein the component (C) has an aliphatic hydrocarbon group.
• thermosetting resin composition according to any one of the above [1] to [5], wherein the component (C) has an N-substituted maleimide group directly bonded to an aromatic ring substituted with an aliphatic hydrocarbon group.
• component (C) is a maleimide resin represented by the following general formula (C-1):
• Xc1 is a group represented by the following general formula (C-1-1), (C-1-2) or (C-1-3).
• each R c1 is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• Each R c2 is independently a halogen atom.
• p1 is an integer of 1 to 4.
• p2 is an integer of 0 to 3, with the proviso that p1+p2 ⁇ 4.
• R c3 and R c4 each independently represent an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• R c5 and R c6 each independently represent a halogen atom.
• At least one of q1 and q2 is an integer of 1 to 4, and the other is an integer of 0 to 4.
• q3 and q4 each independently represent an integer of 0 to 3, with the proviso that q1 + q3 ⁇ 4 and q2 + q4 ⁇ 4.
• Xc2 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond.
• R c7 to R c10 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• R c11 to R c14 are each independently a halogen atom.
• r1 to r4 are each independently an integer of 0 to 4, with the proviso that at least one of r1 to r4 is an integer of 1 to 4.
• r5 to r8 are each independently an integer of 0 to 4, with the proviso that r1 + r5 ⁇ 4, r2 + r6 ⁇ 4, r3 + r7 ⁇ 4, and r4 + r8 ⁇ 4.
• Xc3 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond.
• thermosetting resin composition according to any one of the above [1] to [8], further comprising (E) an inorganic filler.
• a prepreg comprising the thermosetting resin composition according to any one of [1] to [10] above or a semi-cured product of the thermosetting resin composition.
• a resin film comprising the thermosetting resin composition according to any one of [1] to [10] above or a semi-cured product of the thermosetting resin composition.
• a laminate comprising a cured product of the thermosetting resin composition according to any one of [1] to [10] above and a metal foil.
• a printed wiring board having a cured product of the thermosetting resin composition according to any one of [1] to [10] above.
• a semiconductor package comprising the printed wiring board according to [14] above and a semiconductor element.
• thermosetting resin composition that can exhibit low dielectric constant, low thermal expansion, and high adhesion to conductors, as well as to provide prepregs, resin films, laminates, printed wiring boards, and semiconductor packages obtained using the thermosetting resin composition.
• the upper or lower limit of the numerical range may be replaced with the values shown in the examples.
• the lower and upper limits of a numerical range may be arbitrarily combined with the lower or upper limit of another numerical range.
• the numerical values AA and BB at both ends are included in the numerical range as the lower and upper limits, respectively.
• the description "10 or more” means 10 and a numerical value exceeding 10, and the same applies when the numerical values are different.
• the description "10 or less” means 10 and a numerical value less than 10, and the same applies when the numerical values are different.
• each component and material exemplified in this disclosure may be used alone or in combination of two or more.
• the content of each component in the resin composition means the total amount of the multiple substances present in the resin composition when multiple substances corresponding to each component are present in the resin composition, unless otherwise specified.
• the term "resin component” refers to all components among the solid contents constituting the resin composition, excluding inorganic compounds such as inorganic fillers described below.
• the term “solid content” refers to components other than the organic solvent described below, and components that are liquid at 25° C. are also considered to be solid content.
• the expression "containing XX” described in the present disclosure means that it may be in either an embodiment that XX is contained in a reacted state when XX is capable of reacting, or that XX is simply contained.
• dielectric constant means relative permittivity. Any combination of the descriptions in this disclosure is also included in this disclosure and this embodiment.
• the cured product of the thermosetting resin composition has an excellent dielectric constant.
• the indane skeleton contained in the component (A) preferably has a divalent group represented by the following general formula (A-1).
• R a1 represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 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 cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group.
• n1 represents an integer of 0 to 3.
• R a2 to R a4 each independently represent an alkyl group having 1 to 10 carbon atoms. * represents a bonding site.
• component (A) is preferably a bismaleimide resin containing an indane skeleton, and more preferably an aromatic bismaleimide resin containing an indane skeleton.
• the aromatic bismaleimide resin containing an indane skeleton preferably has an N-substituted maleimide group, more preferably has an N-substituted maleimide group directly bonded to an aromatic ring, and even more preferably has an N-substituted maleimide group in which the nitrogen atom of the N-substituted maleimide group is directly bonded to an aromatic ring.
• an aromatic bismaleimide resin represented by the following general formula (A-2) is preferred.
• R a1 to R a4 and n1 are the same as those in the general formula (A-1).
• Each R a5 independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 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 cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a nitro group, a hydroxyl group, or a mercapto group.
• Each n2 independently represents an integer of 0 to 4, and n3 represents a number of 0.95 to 10.0.
• the aromatic bismaleimide resin represented by the general formula (A-2) is preferably an aromatic bismaleimide resin represented by the following general formula (A-3) or an aromatic bismaleimide resin represented by the following general formula (A-4) from the viewpoints of dielectric constant (Dk), adhesion to conductors, solvent solubility, and ease of manufacture.
• Dk dielectric constant
• R a1 to R a5 , n1 and n3 are the same as those in the general formula (A-2).
• R a1 to R a4 , n1 and n3 are the same as those in the general formula (A-2).
• component (A) There are no particular limitations on the method for producing component (A), and known methods can be used as reference or adapted.
• the component (A) may be an addition reaction product with an amine compound such as a monoamine compound or a diamine compound, or may not be an addition reaction product.
• the addition reaction product may be an addition reaction product between a maleimide resin containing an indane skeleton and a monoamine compound, an addition reaction product between a maleimide resin containing an indane skeleton and a diamine compound, or an addition reaction product between a maleimide resin containing an indane skeleton and a monoamine compound and a diamine compound.
• Examples of the monoamine compound include monoamine compounds having an acidic substituent, such as o-aminophenol, m-aminophenol, p-aminophenol, o-aminobenzoic acid, m-aminobenzoic acid, p-aminobenzoic acid, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 3,5-dihydroxyaniline, and 3,5-dicarboxyaniline.
• an acidic substituent such as o-aminophenol, m-aminophenol, p-aminophenol, o-aminobenzoic acid, m-aminobenzoic acid, p-aminobenzoic acid, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 3,5-di
• diamine compound examples include 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylpropane, 2,2'-bis(4,4'-diaminodiphenyl)propane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 3,3'-dimethyl-4,4'-diaminodiphenylethane, 3,3'-diethyl-4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylether, 4,4'-diaminodiphenylthioe, and the like.
• aromatic diamine compounds in which an amino group is bonded to an aromatic hydrocarbon group such as 3,3'-dihydroxy-4,4'-diaminodiphenylmethane, 2,2',6,6'-tetramethyl-4,4'-diaminodiphenylmethane, 3,3'-dichloro-4,4'-diaminodiphenylmethane, 3,3'-dibromo-4,4'-diaminodiphenylmethane, 2,2',6,6'-tetrachloro-4,4'-diaminodiphenylmethane, and 2,2',6,6'-tetrabromo-4,4'-diaminodiphenylmethane; siloxane diamines.
• the content of component (A) in the thermosetting resin composition of this embodiment is not particularly limited, but from the viewpoints of dielectric constant, heat resistance and moldability, it is preferably 10 to 90 parts by mass, more preferably 15 to 85 parts by mass, even more preferably 20 to 80 parts by mass, and particularly preferably 30 to 70 parts by mass, relative to 100 parts by mass of the resin component in the resin composition of this embodiment.
• the content of component (A) is equal to or more than the lower limit, the dielectric constant, heat resistance and moldability tend to be improved, and when the content is equal to or less than the upper limit, the decrease in low thermal expansion properties tends to be suppressed.
• the component (B) is a polyfunctional maleimide resin. However, the component (B) does not contain an indane skeleton. By including the component (B) in the thermosetting resin composition of the present embodiment, the low thermal expansion property, which tends to be reduced by the component (A), is improved.
• the term "polyfunctional” as used herein means that there are three or more maleimide groups.
• Component (B) is preferably a maleimide resin having three or more N-substituted maleimide groups, and more preferably an aromatic maleimide resin having three or more N-substituted maleimide groups.
• the maleimide resin having three or more N-substituted maleimide groups preferably has an N-substituted maleimide group directly bonded to an aromatic ring, more preferably has an N-substituted maleimide group in which the nitrogen atom of the maleimide group is directly bonded to an aromatic ring, and is preferably a maleimide resin represented by the following general formula (B-1): (In the formula, X b-1 is a divalent hydrocarbon group having 1 to 20 carbon atoms (but does not contain an indane skeleton), and n b-1 is an integer of 2 to 5.)
• Examples of the divalent hydrocarbon group having 1 to 20 carbon atoms represented by X b-1 in general formula (B-1) include divalent aliphatic hydrocarbon groups such as an alkylene group having 1 to 5 carbon atoms and an alkylidene group having 2 to 5 carbon atoms, and divalent hydrocarbon groups containing an aromatic hydrocarbon group represented by the following general formula (B-2), etc.
• the divalent hydrocarbon group having 1 to 20 carbon atoms does not contain an indane skeleton.
• Examples of the alkylene group having 1 to 5 carbon atoms include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, etc.
• an alkylene group having 1 to 5 carbon atoms an alkylene group having 1 to 3 carbon atoms is preferable, an alkylene group having 1 or 2 carbon atoms is more preferable, and a methylene group is even more preferable.
• the alkylidene group having 2 to 5 carbon atoms is preferably an alkylidene group having 2 to 4 carbon atoms, more preferably an alkylidene group having 2 or 3 carbon atoms, and further preferably an isopropylidene group.
• Ar b-1 is a divalent aromatic hydrocarbon group
• X b-2 and X b-3 are each independently a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms. * represents a bonding site.
• Examples of the divalent aromatic hydrocarbon group represented by Ar b-1 in the general formula (B-2) include a phenylene group, a naphthylene group, a biphenylene group, and an anthranylene group. Of these, a biphenylene group is preferable.
• Examples of the biphenylene group include a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, and a 3,3'-biphenylene group. Of these, a 4,4'-biphenylene group is preferable.
• Examples of the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by X b-2 and X b-3 in the general formula (B-2) include the same alkylene groups having 1 to 5 carbon atoms and alkylidene groups having 2 to 5 carbon atoms as exemplified as X b-1 in the general formula (B-1). Among these, a methylene group is preferred.
• X b-1 in general formula (B-1) is preferably an aliphatic hydrocarbon group, more preferably an alkylene group having 1 to 5 carbon atoms, and even more preferably a methylene group.
• n b-1 is an integer of 2 to 5, preferably an integer of 2 to 4, and more preferably 2 or 3.
• the content of component (B) in the thermosetting resin composition of this embodiment is not particularly limited, but is preferably 5 to 60 parts by mass, more preferably 10 to 55 parts by mass, even more preferably 10 to 50 parts by mass, and particularly preferably 15 to 40 parts by mass, relative to 100 parts by mass of the resin component in the resin composition of this embodiment.
• the content of component (B) is equal to or more than the lower limit, low thermal expansion tends to be improved, and when the content is equal to or less than the upper limit, a decrease in adhesion to the conductor tends to be suppressed.
• the thermosetting resin composition of the present embodiment contains a maleimide resin that does not contain an indane skeleton as component (C).
• component (C) the "adhesion to a conductor” that tends to decrease due to component (B) is improved.
• Rz 0.1 ⁇ m
• the component (C) may be any maleimide resin that does not contain an indane skeleton and is different from the component (B), but is preferably an aromatic bismaleimide resin, that is, an aromatic bismaleimide resin that does not contain an indane skeleton.
• the component (C) preferably has an aliphatic hydrocarbon group, and more preferably has an N-substituted maleimide group directly bonded to the aromatic ring substituted with the aliphatic hydrocarbon group. Furthermore, the component (C) more preferably has two N-substituted maleimide groups, and even more preferably has two N-substituted maleimide groups directly bonded to an aromatic ring substituted with an aliphatic hydrocarbon group.
• component (C) is a maleimide resin represented by the following general formula (C-1).
• Xc1 is a group represented by the following general formula (C-1-1), (C-1-2) or (C-1-3).
• each R c1 is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• Each R c2 is independently a halogen atom.
• p1 is an integer of 1 to 4.
• p2 is an integer of 0 to 3, with the proviso that p1+p2 ⁇ 4.
• R c3 and R c4 each independently represent an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• R c5 and R c6 each independently represent a halogen atom.
• At least one of q1 and q2 is an integer of 1 to 4, and the other is an integer of 0 to 4.
• q3 and q4 each independently represent an integer of 0 to 3, with the proviso that q1 + q3 ⁇ 4 and q2 + q4 ⁇ 4.
• Xc2 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond.
• R c7 to R c10 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• R c11 to R c14 are each independently a halogen atom.
• r1 to r4 are each independently an integer of 0 to 4, with the proviso that at least one of r1 to r4 is an integer of 1 to 4.
• r5 to r8 are each independently an integer of 0 to 4, with the proviso that r1 + r5 ⁇ 4, r2 + r6 ⁇ 4, r3 + r7 ⁇ 4, and r4 + r8 ⁇ 4.
• Xc3 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond.
• examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R c1 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, etc.
• R c1 is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and more preferably a methyl group or an ethyl group.
• halogen atom represented by R c2 examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• p1 is an integer of 1 to 4, and from the viewpoint of availability, is preferably an integer of 1 or 2, and more preferably 1. When p1 is an integer of 2 or more, multiple R c1 may be the same or different.
• p2 is an integer of 0 to 3, preferably 0 or 1, and more preferably 0. When p2 is an integer of 2 or more, multiple R c2 may be the same or different. However, p1+p2 ⁇ 4, and preferably p1+p2 ⁇ 2.
• examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R c3 and R c4 include the same as the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R c1 .
• the aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably a methyl group or an ethyl group.
• Examples of the halogen atom represented by R c5 and R c6 include the same as the halogen atom represented by R c2 . At least one of q1 and q2 is an integer of 1 to 4, and the other is an integer of 0 to 4.
• q1 is preferably an integer of 1 to 2, and more preferably 1.
• multiple R c3s may be the same as or different from each other.
• q2 is preferably an integer of 1 to 4, and more preferably an integer of 1 to 2, and even more preferably 1.
• multiple R c4s may be the same as or different from each other.
• Each of q3 and q4 is independently an integer of 0 to 3, preferably 0 or 1, and more preferably 1.
• q3 is an integer of 2 or more
• multiple R c5s may be the same as or different from each other.
• q4 is an integer of 2 or more, multiple R c6s may be the same as or different from each other.
• examples of the alkylene group having 1 to 5 carbon atoms represented by Xc2 include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, etc.
• the alkylene group is preferably an alkylene group having 1 to 3 carbon atoms, more preferably a methylene group.
• Examples of the alkylidene group having 2 to 5 carbon atoms represented by Xc2 include an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group, an isopentylidene group, etc. Among these, an isopropylidene group is preferable.
• Xc2 is preferably an alkylene group having 1 to 5 carbon atoms, more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably a methylene group, among the above options.
• examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R c7 to R c10 include the same as the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R c1 .
• the aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably a methyl group or an ethyl group.
• Examples of the halogen atom represented by R c11 to R c14 include the same as the halogen atom represented by R c2 .
• Each of r1 to r4 is independently an integer of 0 to 4.
• At least one of r1 to r4 is an integer of 1 to 4, preferably 1 or 2, and more preferably 1.
• Each of r5 to r8 independently represents an integer of 0 to 4, and preferably 0 or 1.
• r4+r8 ⁇ 4 preferably r4+r8 ⁇ 2.
• examples of the alkylene group having 1 to 5 carbon atoms represented by X c3 include the same as the alkylene group having 1 to 5 carbon atoms represented by X c2 , and the preferred examples are also the same.
• examples of the alkylidene group having 2 to 5 carbon atoms represented by X c3 include the same as the alkylidene group having 2 to 5 carbon atoms represented by X c2 , and the preferred examples are also the same.
• X c3 is preferably an alkylidene group having 2 to 5 carbon atoms, more preferably an isopropylidene group.
• X c1 is preferably a group represented by the general formula (C-1-2) above.
• a maleimide resin represented by the following structural formula is particularly preferable.
• the content of the (C) component in the thermosetting resin composition of the present embodiment is not particularly limited, but is preferably 1 to 40 parts by mass, more preferably 2 to 35 parts by mass, even more preferably 3 to 30 parts by mass, and particularly preferably 5 to 25 parts by mass, relative to 100 parts by mass of the resin component in the resin composition of the present embodiment, and may be 10 to 25 parts by mass, 15 to 25 parts by mass, or may be 5 to 20 parts by mass.
• the adhesion to the conductor and the dielectric constant (Dk) tend to be excellent, and when the content is equal to or less than the upper limit, the increase in the dielectric constant (Dk) tends to be suppressed.
• thermosetting resin composition of the present embodiment may further contain a crosslinking agent (D) (hereinafter, sometimes referred to as component (D)).
• component (D) crosslinking agent
• compatibility with each component is improved and the dielectric constant (Dk) tends to be further reduced.
• component (D) include polyphenylene ether, modified polyphenylene ether, conjugated diene polymers, and modified conjugated diene polymers. Among these, modified conjugated diene polymers are preferred.
• the modified polyphenylene ether may be a compound in which a functional group is introduced into polyphenylene ether.
• the functional group may be an amino group, an epoxy group, a carboxyl group, a styryl group, an acryl group, a methacryl group, etc., and among these, from the viewpoint of dielectric constant (Dk) and compatibility, an acryl group and a methacryl group are preferred, and a methacryl group is more preferred. That is, the modified polyphenylene ether is preferably a methacryl-modified polyphenylene ether.
• the modified polyphenylene ether may have the functional group at the end of the polymer chain or inside the polymer chain, but it is preferable that the functional group is at the end of the polymer chain, and more preferably at both ends of the polymer chain.
• conjugated diene compound that is a monomer component of the conjugated diene polymer examples include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 2-phenyl-1,3-butadiene, and 1,3-hexadiene.
• the conjugated diene polymer may be a polymer of one kind of conjugated diene compound, or a copolymer of two or more kinds of conjugated diene compounds.
• conjugated diene polymer from the viewpoints of compatibility with other resins and dielectric constant (Dk), a conjugated diene polymer having a vinyl group in the side chain is preferred.
• the number of side chain vinyl groups that the conjugated diene polymer has in one molecule is not particularly limited, but from the viewpoints of compatibility with other resins and dielectric constant (Dk), it is preferably 2 or more, more preferably 5 or more, and even more preferably 10 or more.
• the upper limit of the number of side chain vinyl groups that the conjugated diene polymer has in one molecule is not particularly limited, but may be, for example, 100 or less, 80 or less, or 60 or less.
• conjugated diene polymers examples include polybutadiene having a vinyl group, polyisoprene having a vinyl group, etc.
• polybutadiene having a vinyl group is preferred, and polybutadiene having a 1,2-vinyl group derived from 1,3-butadiene is more preferred.
• a polybutadiene homopolymer having a 1,2-vinyl group derived from 1,3-butadiene is preferred.
• the 1,2-vinyl group derived from 1,3-butadiene contained in the conjugated diene polymer is a vinyl group contained in a structural unit represented by the following formula (d1).
• the content of the structural unit having a 1,2-vinyl group relative to all structural units derived from butadiene constituting the polybutadiene [hereinafter, may be referred to as the "vinyl group content"] is not particularly limited, but from the viewpoints of compatibility with other resins, dielectric constant (Dk) and heat resistance, it is preferably 50 mol% or more, more preferably 70 mol% or more, and even more preferably 85 mol% or more.
• the upper limit of the vinyl group content there is no particular limit to the upper limit of the vinyl group content, and it may be 100 mol% or less, 95 mol% or less, or 90 mol% or less.
• the structural unit having a 1,2-vinyl group a structural unit represented by the above formula (d1) is preferable.
• the polybutadiene having a 1,2-vinyl group is preferably a 1,2-polybutadiene homopolymer.
• the number average molecular weight (Mn) of the conjugated diene polymer is not particularly limited, but from the viewpoints of compatibility with other resins, dielectric constant (Dk) and heat resistance, it is preferably 400 to 3,000, more preferably 600 to 2,000, and even more preferably 800 to 1,500.
• the modified conjugated diene polymer is a polymer obtained by modifying the above-mentioned conjugated diene polymer.
• the thermosetting resin composition of the present embodiment contains a modified conjugated diene polymer, and thus tends to have good heat resistance and low thermal expansion properties while also easily achieving an excellent dielectric constant (Dk).
• the modified conjugated diene polymer is preferably a modified conjugated diene polymer obtained by modifying a conjugated diene polymer having a vinyl group in the side chain with a maleimide compound having two or more N-substituted maleimide groups.
• conjugated diene polymer having a vinyl group in the side chain for example, those described above for the conjugated diene polymer can be used, and the preferred embodiments are also the same.
• the conjugated diene polymer having a vinyl group in the side chain may be used alone or in combination of two or more kinds.
• maleimide compound having two or more N-substituted maleimide groups for example, any of the maleimide compounds having two or more N-substituted maleimide groups described above for the maleimide compound in component (A) can be used, and preferred embodiments are also the same.
• maleimide compound having two or more N-substituted maleimide groups examples include aliphatic hydrocarbon group-containing maleimides such as N,N'-ethylene bismaleimide, N,N'-hexamethylene bismaleimide, bis(4-maleimidocyclohexyl)methane, and 1,4-bis(maleimidomethyl)cyclohexane; N,N'-(1,3-phenylene)bismaleimide, N,N'-[1,3-(2-methylphenylene)]bismaleimide, N,N'-[1,3-(4-methylphenylene)]bismaleimide, N,N'-(1,4-phenylene)bismaleimide, bis(4-maleimidophenyl)methane, bis(3-methyl-4-maleimidophenyl)methane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, bis( Examples of aromatic hydrocarbon group
• 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide is more preferable.
• the maleimide compound having two or more N-substituted maleimide groups may be used alone or in combination of two or more.
• the modified conjugated diene polymer preferably has a substituent in a side chain obtained by reacting a side chain vinyl group of a conjugated diene polymer having a vinyl group in the side chain with an N-substituted maleimide group of a maleimide compound having two or more N-substituted maleimide groups [hereinafter, this may be referred to as a "maleimide compound-derived substituent"].
• the substituent derived from a maleimide compound is preferably a group containing a structure represented by the following general formula (d2) or (d3), as a structure derived from a maleimide compound having two or more N-substituted maleimide groups:
• X d1 is a divalent group obtained by removing two N-substituted maleimide groups from a maleimide compound having two or more N-substituted maleimide groups
• * d1 is a moiety that bonds to a carbon atom derived from a side chain vinyl group of a conjugated diene polymer having a vinyl group in its side chain
• * d2 is a moiety that bonds to another atom.
• the modified conjugated diene polymer preferably has a maleimide compound-derived substituent and a vinyl group in the side chain.
• the vinyl group contained in the modified conjugated diene polymer is preferably a 1,2-vinyl group derived from 1,3-butadiene.
• the number average molecular weight (Mn) of the modified conjugated diene polymer is not particularly limited, but from the viewpoints of compatibility with other resins, dielectric constant (Dk), low thermal expansion and heat resistance, it is preferably 700 to 6,000, more preferably 800 to 5,000, and even more preferably 1,000 to 2,500.
• the modified conjugated diene polymer can be produced by reacting a conjugated diene polymer having a vinyl group in the side chain with a maleimide compound having two or more N-substituted maleimide groups.
• the method of reacting a conjugated diene polymer having a vinyl group in a side chain with a maleimide compound having two or more N-substituted maleimide groups is not particularly limited.
• a modified conjugated diene polymer can be obtained by charging a conjugated diene polymer having a vinyl group in a side chain, a maleimide compound having two or more N-substituted maleimide groups, a reaction catalyst, and an organic solvent into a reaction vessel, and reacting the mixture while heating, keeping the mixture warm, stirring, etc., as necessary.
• the ratio (M m /M v ) of the number of moles (M m ) of N-substituted maleimide groups in the maleimide compound having two or more N-substituted maleimide groups to the number of moles (M v ) of side chain vinyl groups in the conjugated diene polymer having a vinyl group in the side chain is not particularly limited, but is preferably 0.001 to 0.5, more preferably 0.005 to 0.1, and even more preferably 0.008 to 0.05, from the viewpoints of compatibility of the resulting modified conjugated diene polymer with other resins and suppression of gelation of the product during the reaction.
• the content of the (D) component in the thermosetting resin composition is not particularly limited, but from the viewpoint of the dielectric constant (Dk) and compatibility, it is preferably 1 to 40 mass%, more preferably 3 to 30 mass%, even more preferably 5 to 25 mass%, particularly preferably 5 to 20 mass%, and most preferably 8 to 15 mass% relative to the total amount of the resin components of the thermosetting resin composition.
• the content of the (D) component is equal to or more than the lower limit, the dielectric constant (Dk) and compatibility tend to be good.
• the content of the (D) component is equal to or less than the upper limit, the heat resistance, moldability, and processability tend to be good.
• thermosetting resin composition of the present embodiment By including an inorganic filler (E) (hereinafter sometimes referred to as component (E)) in the thermosetting resin composition of the present embodiment, it is possible to improve the low thermal expansion coefficient, heat resistance, and flame retardancy.
• component (E) inorganic filler
• the (E) component is not particularly limited, but includes silica, alumina, titanium oxide, mica, beryllia, barium titanate, potassium titanate, strontium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay (calcined clay, etc.), molybdic acid compounds (zinc molybdate, etc.), talc, aluminum borate, silicon carbide, etc.
• the (E) component may be used alone or in combination of two or more.
• silica from the viewpoint of thermal expansion coefficient, heat resistance and flame retardancy, silica, alumina, mica, and talc are preferred, silica and alumina are more preferred, and silica is even more preferred.
• examples of silica include crushed silica, fumed silica, and fused silica (fused spherical silica).
• the shape and particle size of component (E) are not particularly limited, but the particle size is preferably 0.01 to 20 ⁇ m, more preferably 0.1 to 10 ⁇ m, even more preferably 0.2 to 1 ⁇ m, and particularly preferably 0.3 to 0.8 ⁇ m.
• particle size refers to the average particle size, and is the particle size at the point corresponding to 50% volume when a cumulative frequency distribution curve is calculated based on particle size, with the total volume of the particles being 100%.
• the particle size of component (E) can be measured using a particle size distribution measuring device using a laser diffraction scattering method.
• the content of the component (E) in the thermosetting resin composition is not particularly limited, but from the viewpoints of the thermal expansion coefficient, heat resistance, and flame retardancy, the content of the component (E) in the thermosetting resin composition is preferably 1 to 50 vol%, more preferably 3 to 30 vol%, further preferably 5 to 20 vol%, and particularly preferably 5 to 15 vol%, based on the total solid content of the thermosetting resin composition.
• a coupling agent may be used in combination as necessary in order to improve the dispersibility of the (E) component and the adhesion between the (E) component and the organic component in the thermosetting resin composition.
• the coupling agent is not particularly limited, and for example, a silane coupling agent or a titanate coupling agent may be appropriately selected and used.
• the coupling agent may be used alone or in combination of two or more types.
• the amount of the coupling agent used is also not particularly limited.
• the so-called integral blending method may be used in which the coupling agent is added after the component (E) is blended into the thermosetting resin composition, but it is preferable to use an inorganic filler that has been surface-treated in advance with a coupling agent by a dry or wet method. By adopting this method, the characteristics of the component (E) can be more effectively expressed.
• component (E) when component (E) is used in this embodiment, in order to improve the dispersibility of component (E) in the thermosetting resin composition, component (E) may be used as a slurry in which it is dispersed in an organic solvent beforehand, if necessary.
• organic solvent include the same organic solvents as those described below.
• the (F) curing accelerator may include amine-based curing accelerators, imidazole-based curing accelerators, phosphorus-based curing accelerators, organometallic salts, acid catalysts, organic peroxides, etc.
• imidazole-based curing accelerators are not classified as amine-based curing accelerators.
• the curing accelerators may be used alone or in combination of two or more.
• the curing accelerator preferably includes at least one selected from the group consisting of imidazole-based curing accelerators and organic peroxides.
• imidazole-based curing accelerator examples include imidazole compounds such as methylimidazole, phenylimidazole, and 2-undecylimidazole; and isocyanate-masked imidazoles such as an addition reaction product of hexamethylene diisocyanate resin and 2-ethyl-4-methylimidazole.
• organic peroxide examples include dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butylperoxyisopropyl monocarbonate, and ⁇ , ⁇ '-bis(t-butylperoxy)diisopropylbenzene.
• thermosetting resin composition of the present embodiment contains the component (F)
• the content of the component (F) is not particularly limited, but in any case, it is preferably 0.01 to 3 parts by mass, more preferably 0.05 to 2.5 parts by mass, still more preferably 0.1 to 2.5 parts by mass, and particularly preferably 0.5 to 2.5 parts by mass, relative to 100 parts by mass of the resin components in the thermosetting resin composition.
• the content of the curing accelerator (F) is within the above range, better heat resistance, storage stability, and moldability tend to be obtained.
• thermosetting resin composition of the present embodiment preferably further contains, as other components, at least one selected from the group consisting of a flame retardant, a flame retardant assistant, an antioxidant, an adhesion improver, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a colorant, and a lubricant.
• the thermosetting resin composition may contain components other than those described above.
• thermosetting resin composition of the present embodiment contains these other components (flame retardants, flame retardant assistants, antioxidants, adhesion improvers, heat stabilizers, antistatic agents, UV absorbers, pigments, colorants, lubricants, and other components), the content of each of these other components is not particularly limited, and may be, for example, 0.01 parts by mass or more, 10 parts by mass or less, 5 parts by mass or less, 1 part by mass or less, or none at all, relative to 100 parts by mass of the resin component in the thermosetting resin composition.
• the thermosetting resin composition of the present embodiment may be a so-called "varnish" containing an organic solvent, from the viewpoint of facilitating handling and facilitating production of a prepreg or a resin film described below.
• the organic solvent is not particularly limited, but examples thereof include alcohol-based solvents such as ethanol, propanol, butanol, methyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether; ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ether-based solvents such as tetrahydrofuran; aromatic solvents such as toluene, xylene, and mesitylene; nitrogen-containing solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; sulfur-containing solvents such as dimethyl sulfoxide; and ester-based solvents such as ⁇ -but
• the solids concentration is preferably 30 to 90 mass%, more preferably 40 to 80 mass%, and even more preferably 45 to 60 mass%.
• the thermosetting resin composition is easy to handle, the impregnation into the substrate and the appearance of the produced prepreg are good, and the coating properties when made into a resin film are also good.
• thermosetting resin composition of this embodiment can be produced by mixing components (A) to (C) and the above components that can be used as necessary by a known method. At this time, each component may be dissolved or dispersed in the organic solvent while stirring.
• the mixing order, temperature, time, and other conditions are not particularly limited and can be set as desired.
• the prepreg of the present embodiment is a prepreg containing the thermosetting resin composition of the present embodiment or a semi-cured product of the thermosetting resin composition.
• the prepreg of this embodiment contains, for example, the thermosetting resin composition of this embodiment or a semi-cured product of the thermosetting resin composition and a sheet-like fiber substrate.
• the prepreg is formed using the thermosetting resin composition of this embodiment or a resin film described later and a sheet-like fiber substrate.
• the sheet-like fiber substrate is impregnated with the thermosetting resin composition of this embodiment or a resin film described later, and then heated and dried to semi-cure (B-stage) as necessary.
• the prepreg of this embodiment can be produced by heating and drying in a drying oven at 80 to 200 ° C. for 1 to 30 minutes to semi-cure (B-stage).
• B-stage refers to a state of B-stage defined in JIS K6900 (1994).
• the amount of the thermosetting resin composition used can be appropriately determined so that the solid content concentration derived from the thermosetting resin composition in the prepreg after drying is 30 to 90 mass %. By setting the solid content concentration in the above range, better moldability tends to be obtained when the laminate is made.
• the sheet-like fiber substrate of the prepreg As the sheet-like fiber substrate of the prepreg, a known one used in various laminates for electrical insulating materials is used.
• the material of the sheet-like fiber substrate may be inorganic fibers such as E glass, D glass, S glass, Q glass, etc.; organic fibers such as polyimide, polyester, tetrafluoroethylene, etc.; mixtures thereof, etc.
• These sheet-like fiber substrates have shapes such as woven fabric, nonwoven fabric, roving, chopped strand mat, or surfacing mat.
• the thickness of the sheet-like fiber substrate is not particularly limited, but may be 1 to 100 ⁇ m, 3 to 70 ⁇ m, or 5 to 35 ⁇ m.
• the resin film of the present embodiment is a resin film containing the thermosetting resin composition of the present embodiment or a semi-cured product of the thermosetting resin composition.
• the resin film of the present embodiment can be produced, for example, by applying a thermosetting resin composition containing an organic solvent, i.e., a varnish, to a support, drying by heating, and semi-curing (B-staging) as necessary.
• the thickness of the resin film is not particularly limited, but is preferably 1 to 100 ⁇ m, more preferably 3 to 70 ⁇ m, and even more preferably 5 to 35 ⁇ m.
• the support include a plastic film, a metal foil, and a release paper.
• the drying temperature and drying time may be appropriately determined depending on the amount of the organic solvent used, the boiling point of the organic solvent used, and the like, but a resin film can be suitably formed by drying at 50 to 200° C. for about 1 to 10 minutes.
• the laminate of the present embodiment is a laminate having a cured product of the thermosetting resin composition of the present embodiment or a cured product of the prepreg, and a metal foil.
• the laminate of the present embodiment can be produced, for example, by disposing a metal foil on one or both sides of a single prepreg of the present embodiment, or by disposing a metal foil on one or both sides of a laminate obtained by stacking two or more prepregs of the present embodiment, and then hot-pressing and molding.
• the prepreg of the present embodiment is C-staged.
• C-stage refers to bringing the prepreg into the C-stage state defined in JIS K6900 (1994).
• a laminate having a metal foil is sometimes called a metal-clad laminate.
• the metal of the metal foil is not particularly limited, but from the viewpoint of electrical conductivity, it may be copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, or an alloy containing one or more of these metal elements, with copper and aluminum being preferred, and copper being more preferred.
• the method for carrying out the hot-press molding is not particularly limited, but may be carried out, for example, under conditions of a temperature of 100 to 300° C., a pressure of 0.2 to 10 MPa, and a time of 0.1 to 5 hours. In addition, the hot-press molding may be carried out using a vacuum press or the like to maintain a vacuum state for 0.5 to 5 hours.
• the printed wiring board of this embodiment has one or more selected from the group consisting of the cured product of the thermosetting resin composition of this embodiment, the cured product of the prepreg of this embodiment, and the laminate of this embodiment.
• the printed wiring board of this embodiment can be manufactured by performing a circuit formation process by drilling, metal plating, etching of metal foil, etc., using one or more selected from the group consisting of the prepreg of this embodiment, the resin film of this embodiment, and the laminate of this embodiment by a known method.
• a multilayer printed wiring board can also be manufactured by further performing a multilayer adhesive process as necessary.
• the prepreg of this embodiment and the resin film of this embodiment are C-staged.
• the semiconductor package of the present embodiment is a semiconductor package having the printed wiring board of the present embodiment and a semiconductor element.
• the semiconductor package of the present embodiment can be manufactured by mounting a semiconductor element such as a semiconductor chip or memory at a predetermined position on the printed wiring board of the present embodiment and sealing the semiconductor element with a sealing resin or the like.
• the resin composition, prepreg, resin film, laminate, printed wiring board, and semiconductor package of this embodiment can be suitably used in electronic devices that handle high-frequency signals of 10 GHz or more.
• the printed wiring board is useful as a printed wiring board for millimeter-wave radar.
• the number average molecular weight (Mn) was measured by the following method. (1. Method for measuring number average molecular weight (Mn)) The values were calculated from a calibration curve using standard polystyrene by gel permeation chromatography (GPC). The calibration curve was approximated by a third order equation using standard polystyrene: TSKstandard POLYSTYRENE (Type: A-2500, A-5000, F-1, F-2, F-4, F-10, F-20, F-40) [manufactured by Tosoh Corporation, trade name]. The measurement conditions for GPC are shown below.
• thermosetting resin composition (varnish) having a solids concentration of 55 mass %.
• the varnish obtained above was applied to a 15 ⁇ m thick glass woven fabric (NE Glass, manufactured by Asahi Kasei Corporation), and then heated and dried at 130 ° C. for 3 minutes to produce a prepreg with a solid content of about 75% by mass derived from the thermosetting resin composition.
• the surface roughness (Rz) is a value that is obtained as follows. First, a roughness curve is obtained by measurement using a shape analysis laser microscope "VK-X250" (manufactured by Keyence Corporation). A reference length is cut out from the obtained roughness curve in the direction of the average line, and in this cutout portion, the sum of the average value of the absolute values of the elevations of the highest to fifth peaks and the average value of the absolute values of the elevations of the lowest to fifth valleys is obtained, based on the average line. The value thus obtained is expressed in micrometers ( ⁇ m) to obtain Rz.
• the double-sided copper-clad laminate 1 or the double-sided copper-clad laminate 2 obtained in each example was evaluated according to the following methods. The results are shown in Table 2.
• Dk Dielectric Constant
• the outer copper foil of the double-sided copper-clad laminate 1 obtained in each example was removed by immersing it in a copper etching solution (a 10 mass% solution of ammonium persulfate, manufactured by Mitsubishi Gas Chemical Company, Inc.), and a test piece having a length of 60 mm and a width of 2 mm was cut out and used to measure the dielectric constant (Dk) by a cavity resonator perturbation method.
• a copper etching solution a 10 mass% solution of ammonium persulfate, manufactured by Mitsubishi Gas Chemical Company, Inc.
• the measurement equipment used was a vector network analyzer "N5222B” manufactured by Agilent Technologies, the cavity resonator was “CP129” (10 GHz band resonator) manufactured by Kanto Electronics Application Development Co., Ltd., and the measurement program was "CPMA-V2.” The measurement was performed under the conditions of a frequency of 10 GHz and a measurement temperature of 25°C.
• thermomechanical measuring device manufactured by TA Instruments Japan Co., Ltd., product name: Q400
• the measurement was performed twice under the conditions of a load of 0.05 N and a temperature rise rate of 10 ° C. / min in the temperature range of 50 to 280 ° C., and the thermal expansion coefficient was the average thermal expansion coefficient in the second measurement.
• the thermal expansion coefficient is the thermal expansion coefficient in the thickness direction of the test piece.
• the peel strength was measured using "EZ-Test/CE" manufactured by Shimadzu Corporation according to the following method.
• the copper foil of the double-sided copper-clad laminate 1 or 2 obtained in each example was processed into a 3 mm wide straight line by etching, and then dried under the condition of 105°C/hour to prepare a test piece.
• the copper foil was peeled off in a 90° direction using the test piece in accordance with JIS C6481 (1996), to measure the peel strength, which was used as an index of adhesion to the conductor.
• the pulling speed was 50 mm/min.
• the peel strength is 4.5 kN/m or more, and further if it is 5.0 kN/m or more, it can be said that the adhesiveness to the conductor is excellent.
• Polyfunctional maleimide resin a polyfunctional maleimide resin represented by the following structural formula: (In the formula, n b-1 is an integer from 2 to 5.)
• Maleimide resin C-2 not containing an indane skeleton a bismaleimide resin represented by the following structural formula: (In the formula, Xc1 is a group represented by general formula (C-1-2) or (C-1-3).) [Component (D)] Crosslinking agent: Modified conjugated diene polymer D-1 obtained in Production Example 1
• Imidazole-based curing accelerator E-1 Isocyanate masked imidazole "G8009L" (manufactured by Daiichi Kogyo Seiyaku Co., Ltd., product name)
• Organic peroxide E-2 ⁇ , ⁇ '-bis(t-butylperoxy)diisopropylbenzene
• thermosetting resin compositions (Examples 1 to 4) containing all of the components (A) to (C) achieved low dielectric constant, low thermal expansion, and high adhesion to the conductor.
• the adhesion to the conductor was significantly improved compared to Comparative Example 2, which means that the adhesion between the inner layer circuit and the insulating layer was significantly improved.
• the cured product of the thermosetting resin composition not containing the components (B) and (C) (Comparative Example 1) was unable to achieve low thermal expansion.
• thermosetting resin composition containing the components (A) and (B) but not the component (C) (Comparative Example 2) was able to achieve low thermal expansion, but had lower adhesion to the conductor than Example 2, which had the same total amount of maleimide resin.

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