Polymers, compositions, cured products, laminates, and electronic components

Abstract

To provide a polymer that has a low dielectric constant and a low loss tangent, and to provide a composition and a laminate that have a low dielectric constant and a low loss tangent and are excellent in curability, adhesiveness, and heat resistance in a well-balanced manner.SOLUTION: A polymer having a repeating structural unit represented by Formula (1) and having a group Y represented by Formula (a) at a terminal: X's are each independently -O-, -S-, or -N(R3)-, R3 is a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group obtained by substituting a part of the hydrocarbon group or the halogenated hydrocarbon group with at least one selected from an oxygen atom and a sulfur atom, R1 is a divalent organic group, and R2 is a divalent unsubstituted or substituted pyrimidine ring; Y is a group containing an ethylenically unsaturated double bond having 3 to 50 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] One embodiment of the present invention relates to a polymer, a composition, a cured product, a laminate, or an electronic component. [Background technology]

[0002] In recent years, in the field of information and communications, the signal bandwidth of information and communications equipment has been increasing in frequency in order to achieve high-speed, large-capacity transmission. To accommodate this increase in frequency, there is an increasing demand for low-dielectric and low-dielectric-tangent materials for the insulators used in printed wiring boards and semiconductor packages.

[0003] As materials that can accommodate this trend toward higher frequencies, polyolefin resin, styrene resin, fluororesin, polyphenylene ether resin, vinylbenzyl ether resin, or compositions using polyphenylene ether resin have been proposed (Patent Documents 1 to 6). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 7-188362 [Patent Document 2] Japanese Patent Application Laid-Open No. 2004-83680 [Patent Document 3] Patent No. 3414556 [Patent Document 4] Japanese Patent Application Laid-Open No. 2003-306591 [Patent Document 5] Patent No. 5649773 [Patent Document 6] Japanese Patent Application Laid-Open No. 2017-200997 Summary of the Invention [Problem to be solved by the invention]

[0005] However, although conventional materials such as the compositions described in Patent Documents 1 to 6 are somewhat excellent in terms of low dielectric constant and low dielectric dissipation factor, they do not necessarily satisfy all of the requirements for properties necessary for electronic materials, such as heat resistance, chemical resistance, and adhesiveness. For example, compositions using polyphenylene ether resins and fluororesins have low dielectric constants, low dielectric dissipation factors, and excellent heat resistance, but do not have sufficient adhesion to low-roughening copper foils.Furthermore, the composition described in Patent Document 6 has room for improvement in terms of chemical resistance and low dielectric properties.

[0006] One embodiment of the present invention provides a polymer having a low dielectric constant and a low dielectric dissipation factor, and also provides a composition and a laminate having a low dielectric constant and a low dielectric dissipation factor, as well as a well-balanced excellent curability, adhesiveness, and heat resistance. [Means for solving the problem]

[0007] As a result of extensive research into solving the above problems, the present inventors have found that the above problems can be solved by the following configuration example. An example of the configuration of the present invention is as follows.

[0008] [1] Having a repeating structural unit represented by the following formula (1): A polymer having a group Y represented by the following formula (a) at its terminal.

[0009] [ka] [In formula (1), each X is independently -O-, -S-, or -N(R 3 )- and R 3 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a portion of the hydrocarbon group or halogenated hydrocarbon group is substituted with at least one atom selected from an oxygen atom and a sulfur atom, and R 1 is a divalent organic group, and R 2 is a divalent unsubstituted or substituted nitrogen-containing heteroaromatic ring.

[0010] [ka] [In formula (a), Y represents a group containing an ethylenically unsaturated double bond having 3 to 50 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 50 carbon atoms, an unsubstituted or substituted aliphatic hydrocarbon group having 6 to 50 carbon atoms, or an unsubstituted nitrogen-containing heteroaromatic ring, and when the aromatic hydrocarbon group or the aliphatic hydrocarbon group has a substituent, the substituent is a group other than a hydroxy group.]

[0011] [2] R in the formula (1) 1 The polymer according to [1], wherein the divalent organic group represented by the following formula (2-1) contains a group represented by the following formula (2-1):

[0012] [ka] [In formula (2-1), Ar1 and Ar2 each independently represent an unsubstituted or substituted aromatic hydrocarbon group, and L represents a single bond, -O-, -S-, -N(R 8 )-, -C(O)-, -C(O)-O-, -C(O)-NH-, -S(O)-, -S(O)2-, -P(O)- or a divalent organic group, and R 8 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms; y represents an integer of 0 to 5; when y is 2 or greater, a plurality of Ar1s and Ls may be the same or different; R 6 and R 7 are each independently a single bond, a methylene group, or an alkylene group having 2 to 4 carbon atoms.

[0013] [3] The polymer according to [2], wherein Ar1 and Ar2 in the formula (2-1) are each independently an aromatic hydrocarbon group having an allyl group.

[0014] [4] The polymer according to any one of [1] to [3], which has a weight average molecular weight in terms of polystyrene of 1,000 to 500,000.

[0015] [5] The polymer according to any one of [1] to [4], and a curable compound (B) other than the polymer.

[0016] [6] The composition according to [5], wherein the curable compound (B) comprises at least one compound selected from the group consisting of vinyl compounds, maleimide compounds, allyl compounds, acrylic compounds, methacrylic compounds, thiol compounds, oxazine compounds, cyanate compounds, epoxy compounds, oxetane compounds, methylol compounds, benzocyclobutene compounds, propargyl compounds, and silane compounds.

[0017] [7] The composition according to [5] or [6], further comprising an antioxidant.

[0018] [8] A cured product obtained by curing the composition according to any one of [5] to [7].

[0019] [9] a substrate; and a cured product layer formed using the composition according to any one of [5] to [7].

[0020]

[10] An electronic component having the cured product according to [8] or the laminate according to [9]. [Effects of the Invention]

[0021] According to one embodiment of the present invention, a polymer having a low dielectric constant and a low dielectric dissipation factor can be provided, and a composition and a laminate having a low dielectric constant and a low dielectric dissipation factor, as well as a well-balanced excellent curability, adhesiveness, and heat resistance can be obtained. DETAILED DESCRIPTION OF THE INVENTION

[0022] Preferred embodiments of the present invention will be described in detail below. It should be understood that the present invention is not limited to the embodiments described below, but also includes various modifications that are implemented within the scope of the present invention.

[0023] In this specification, a numerical range stated using "to" means that the numerical values ​​before and after "to" are included as the lower limit and upper limit.

[0024] Hereinafter, a polymer, a composition, a cured product, a laminate, or an electronic component according to one embodiment of the present invention will be described in detail.

[0025] <Polymer> A polymer according to one embodiment of the present invention (hereinafter also referred to as "polymer (A)") has a repeating structural unit represented by the following formula (1), and has a group Y (terminal group Y) represented by the following formula (a) at its terminal.

[0026] [ka] [In formula (1), Each X is independently -O-, -S- or -N(R 3 )-. R 3 is a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a portion of such a hydrocarbon group or halogenated hydrocarbon group is substituted with at least one atom selected from an oxygen atom and a sulfur atom. R 1 is a divalent organic group. R 2 is a divalent unsubstituted or substituted nitrogen-containing heteroaromatic ring.

[0027] [ka] [In formula (a), Y represents a group containing an ethylenically unsaturated double bond having 3 to 50 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 50 carbon atoms, an unsubstituted or substituted aliphatic hydrocarbon group having 6 to 50 carbon atoms, or an unsubstituted nitrogen-containing heteroaromatic ring, and when the aromatic hydrocarbon group or the aliphatic hydrocarbon group has a substituent, the substituent is a group other than a hydroxy group.]

[0028] R 1The divalent organic group represented by the formula (2-1) preferably contains a group represented by the formula (2-1) below.

[0029] [ka] [In formula (2-1), Ar1 and Ar2 each independently represent an unsubstituted or substituted aromatic hydrocarbon group. L is a single bond, -O-, -S-, -N(R 8 )-, -C(O)-, -C(O)-O-, -C(O)-NH-, -S(O)-, -S(O)2-, -P(O)-, or a divalent organic group [R 8 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms. y is an integer of 0 to 5. When y is 2 or more, the plurality of Ar1's and L's may be the same or different. R 6 and R 7 are each independently a single bond, a methylene group, or an alkylene group having 2 to 4 carbon atoms.

[0030] The aromatic hydrocarbon groups represented by Ar1 and Ar2 are each independently preferably aromatic hydrocarbon groups having 6 to 30 carbon atoms, more preferably a phenyl group, a naphthyl group, or an anthryl group, and particularly preferably a phenyl group or a naphthyl group.

[0031] The aromatic hydrocarbon groups represented by Ar1 and Ar2 may each have 1 to 8 substituents. The number of substituents that the aromatic hydrocarbon groups represented by Ar1 and Ar2 each have is preferably 0 to 8, more preferably 0 to 4, and even more preferably 0 to 2, from the viewpoint of enabling the synthesis of polymer (A) with good polymerization reactivity.

[0032] The substituents in Ar1 and Ar2 are not particularly limited, and examples thereof include an allyl group, a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphate group, a hydroxy group, a primary to tertiary amino group, a salt of a carboxy group, a salt of a sulfonic acid group, a salt of a phosphonic acid group, a salt of a phosphate group, a salt of a hydroxy group, or a salt of a primary to tertiary amino group. Of these, an allyl group is preferred.

[0033] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0034] Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms include a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, and a monovalent aromatic hydrocarbon group.

[0035] Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and n-pentyl groups; alkenyl groups such as ethenyl, propenyl, butenyl, and pentenyl groups; and alkynyl groups such as ethynyl, propynyl, butynyl, and pentynyl groups.

[0036] Examples of the monovalent alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; polycyclic cycloalkyl groups such as a norbornyl group and an adamantyl group; monocyclic cycloalkenyl groups such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group; and polycyclic cycloalkenyl groups such as a norbornenyl group.

[0037] Examples of the monovalent aromatic hydrocarbon group include aryl groups such as a phenyl group, a tolyl group, a xylyl group, a naphthyl group, and an anthryl group; and aralkyl groups such as a benzyl group, a phenethyl group, a phenylpropyl group, and a naphthylmethyl group.

[0038] Examples of the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms include groups in which some or all of the hydrogen atoms of the monovalent hydrocarbon group having 1 to 20 carbon atoms have been substituted with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0039] Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, and an octyloxy group.

[0040] Examples of the alkylthio group having 1 to 20 carbon atoms include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, a butylthio group, a pentylthio group, a hexylthio group, and an octylthio group.

[0041] The substituent (R) in the secondary amino group (-NHR) and the tertiary amino group (-NR2) is not particularly limited, and examples thereof include monovalent hydrocarbon groups having 1 to 20 carbon atoms. Specific examples include the groups exemplified below as substituents in the nitrogen-containing heteroaromatic ring.

[0042] The cations constituting the cationic moieties in the salts of the carboxyl group, the salts of the sulfonic acid group, the salts of the phosphonic acid group, the salts of the phosphoric acid group, and the salts of the hydroxyl group are not particularly limited, and include Na + Examples of known cations include: The anion constituting the anion moiety in the salt of the amino group is not particularly limited, and may be Cl - Examples of known anions include:

[0043] In view of the fact that a cured product with a high crosslink density can be easily obtained, Ar1 and Ar2 may each independently be an aromatic hydrocarbon group having an allyl group.

[0044] The divalent organic group for L is preferably a divalent organic group having 1 to 20 carbon atoms, and examples thereof include a methylene group, an alkylene group having 2 to 20 carbon atoms, a halogenated methylene group, a halogenated alkylene group having 2 to 20 carbon atoms, a divalent cardo structure, or a group represented by the following formula (L1):

[0045] [ka] [In formula (L1), R c is an unsubstituted or substituted divalent alicyclic hydrocarbon group having 5 to 30 ring members.

[0046] Examples of the alkylene group having 2 to 20 carbon atoms for L include an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, a sec-butylene group, a neopentylene group, a 4-methyl-pentane-2,2-diyl group, a nonane-1,9-diyl group, and a decane-1,1-diyl group.

[0047] Examples of the halogenated methylene group for L include groups in which some or all of the hydrogen atoms of a methylene group have been substituted with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0048] Examples of the halogenated alkylene group having 2 to 20 carbon atoms for L include groups in which some or all of the hydrogen atoms of the alkylene group having 2 to 20 carbon atoms have been substituted with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0049] An example of the divalent cardo structure in L is a divalent group derived from fluorene represented by the following formula (L2) (that is, a group obtained by removing two hydrogen atoms from a compound having a fluorene skeleton).

[0050] [ka] [In formula (L2), R8 and R9 each independently represent a hydrogen atom, a fluorine atom, or a monovalent chain hydrocarbon group having 1 to 20 carbon atoms, and k independently represents an integer of 0 to 4.]

[0051] Examples of the divalent cardo structure include structures derived from compounds represented by the following formula:

[0052] [ka]

[0053] R c Examples of the unsubstituted or substituted divalent alicyclic hydrocarbon group having 5 to 30 ring members represented by the formula (I) include an unsubstituted or substituted monocyclic alicyclic hydrocarbon group having 5 to 15 ring members, an unsubstituted or substituted monocyclic fluorinated alicyclic hydrocarbon group having 5 to 15 ring members, an unsubstituted or substituted polycyclic alicyclic hydrocarbon group having 7 to 30 ring members, and an unsubstituted or substituted polycyclic fluorinated alicyclic hydrocarbon group having 7 to 30 ring members.

[0054] Examples of the unsubstituted or substituted monocyclic alicyclic hydrocarbon group having 5 to 15 ring members include a cyclopentane-1,1-diyl group, a cyclohexane-1,1-diyl group, a 3,3,5-trimethylcyclohexane-1,1-diyl group, a cyclopentene-3,3-diyl group, a cyclohexene-3,3-diyl group, a cyclooctane-1,1-diyl group, a cyclodecane-1,1-diyl group, a cyclododecane-1,1-diyl group, and groups in which some or all of the hydrogen atoms of these groups have been substituted with a monovalent chain hydrocarbon group having 1 to 20 carbon atoms.

[0055] Examples of the unsubstituted or substituted monocyclic fluorinated alicyclic hydrocarbon group having 5 to 15 ring members include groups in which some or all of the hydrogen atoms of the groups exemplified as the monocyclic alicyclic hydrocarbon group having 5 to 15 ring members have been substituted with fluorine atoms.

[0056] Examples of the unsubstituted or substituted polycyclic alicyclic hydrocarbon group having 7 to 30 ring members include norbornane, norbornene, adamantane, tricyclo[5.2.1.0 2,6 ] Decane, Tricyclo[5.2.1.0 2,6 ]heptane, pinane, camphane, decalin, nortricyclane, perhydroanthracene, perhydroazulene, cyclopentanohydrophenanthrene, bicyclo[2.2.2]-2-octene, and other polycyclic alicyclic hydrocarbons by removing two hydrogen atoms bonded to one carbon atom; and groups in which some or all of the hydrogen atoms of these groups have been substituted with monovalent chain hydrocarbon groups having 1 to 20 carbon atoms.

[0057] Examples of the unsubstituted or substituted fluorinated polycyclic alicyclic hydrocarbon group having 7 to 30 ring members include groups in which some or all of the hydrogen atoms of the groups exemplified as the polycyclic alicyclic hydrocarbon group having 7 to 30 ring members have been substituted with fluorine atoms.

[0058] -N(R 8 )-R in 8 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, and examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms and the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms include the monovalent hydrocarbon groups having 1 to 20 carbon atoms and the monovalent halogenated hydrocarbon groups having 1 to 20 carbon atoms exemplified above for Ar1, respectively.

[0059] From the viewpoint of structural stability of the polymer (A), L is preferably a single bond, -O-, -S-, -C(O)-, -S(O)-, -S(O)2-, -C(O)-NH-, -C(O)-O-, a methylene group, an alkylene group having 2 to 5 carbon atoms, a halogenated methylene group, a halogenated alkylene group having 2 to 10 carbon atoms, or a divalent cardo structure. From the same viewpoint, y is preferably 0 to 4, and more preferably 0 to 3.

[0060] R 6 and R 7Examples of the alkylene group having 2 to 4 carbon atoms in R include an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, and a sec-butylene group. 6 and R 7 are each independently preferably a single bond, a methylene group, or an ethylene group, from the viewpoint of enabling the synthesis of polymer (A) with good polymerization reactivity.

[0061] R 1Examples of monomers that can be used as raw materials for the portion containing the formula (I) include dihydroxyphenyl compounds such as hydroquinone, resorcinol, catechol, and phenylhydroquinone; 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-allylphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-phenylphenyl)propane, 4,4'-(1,3-dimethylbutylidene)bisphenol, and 1,1-bis(4-hydroxyphenyl) )-nonane, bis(4-hydroxyphenyl)sulfone, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-methyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 4,4'-cyclododecylidenebisphenol, 4,4'-decylidenebisphenol, and other bisphenol compounds; and diol compounds such as Priplast 1901, 1838, 3186, 3192, 3197, and 3199 (manufactured by Croda Japan Co., Ltd.). These monomers may be used alone or in combination of two or more.

[0062] R 2 represents a divalent unsubstituted or substituted nitrogen-containing heteroaromatic ring. Specific examples of the nitrogen-containing heteroaromatic ring include a pyrrole ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a phthalazine ring, a quinazoline ring, a naphthyridine ring, a carbazole ring, an acridine ring, and a phenazine ring.

[0063] As the nitrogen-containing heteroaromatic ring, a pyrimidine ring is preferred from the viewpoints that the polymer (A) can be synthesized with good polymerization reactivity and that the polymer (A) having excellent solubility in various organic solvents can be easily obtained.

[0064] The positions of the two bonds bonded to the nitrogen-containing heteroaromatic ring (the bonds bonded to X) are not particularly limited, but meta positions are preferred from the viewpoint of synthesizing the polymer (A) with good polymerization reactivity.

[0065] Examples of the substituent in the nitrogen-containing heteroaromatic ring include a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a group in which such a hydrocarbon group or halogenated hydrocarbon group is partially substituted with at least one atom selected from an oxygen atom and a sulfur atom, a nitro group, a cyano group, an amino group, and a salt of an amino group.

[0066] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0067] Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms include a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, and a monovalent aromatic hydrocarbon group.

[0068] Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and n-pentyl groups; alkenyl groups such as ethenyl, propenyl, butenyl, and pentenyl groups; and alkynyl groups such as ethynyl, propynyl, butynyl, and pentynyl groups.

[0069] Examples of the monovalent alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; polycyclic cycloalkyl groups such as a norbornyl group and an adamantyl group; monocyclic cycloalkenyl groups such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group; and polycyclic cycloalkenyl groups such as a norbornenyl group.

[0070] Examples of the monovalent aromatic hydrocarbon group include aryl groups such as a phenyl group, a tolyl group, a xylyl group, a naphthyl group, and an anthryl group; and aralkyl groups such as a benzyl group, a phenethyl group, a phenylpropyl group, and a naphthylmethyl group.

[0071] Examples of the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms include groups in which some or all of the hydrogen atoms of the monovalent hydrocarbon group having 1 to 20 carbon atoms have been substituted with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0072] Specific examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms or the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms partially substituted with at least one atom selected from oxygen atoms and sulfur atoms include groups in which the hydrocarbon group or halogenated hydrocarbon group is partially substituted with -O-, -S-, an ester group, or a sulfonyl group.

[0073] The amino group is not particularly limited, and may be a primary amino group (-NH2), a secondary amino group (-NHR), or a tertiary amino group (-NR2). The substituent (R) in the secondary amino group and tertiary amino group is not particularly limited, and examples thereof include the above-mentioned monovalent hydrocarbon groups having 1 to 20 carbon atoms. The anion constituting the anion moiety in the salt of the amino group is not particularly limited, and may be Cl - Examples of known anions include:

[0074] As the substituent on the nitrogen-containing heteroaromatic ring, from the viewpoints of enabling the synthesis of polymer (A) with good polymerization reactivity and improving the solubility of the monomers serving as raw materials for polymer (A), a halogen atom, a monovalent hydrocarbon group having 1 to 6 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 6 carbon atoms, a nitro group, a cyano group, an amino group, or a salt of an amino group is preferred, and a fluorine atom, a chlorine atom, a methyl group, a nitro group, a cyano group, a tert-butyl group, a phenyl group, or a primary amino group is more preferred.

[0075] R 2Examples of the monomers that can be used as raw materials for the portion containing -phenyl-4,6-dichloropyrimidine, 2-methylthio-4,6-dichloropyrimidine, 2-methylsulfonyl-4,6-dichloropyrimidine, 5-methyl-4,6-dichloropyrimidine, 2-amino-4,6-dichloropyrimidine, 5-amino-4,6-dichloropyrimidine, 2,5-diamino-4,6-dichloropyrimidine, 4-amino-2,6-dichloropyrimidine, 5-methoxy-4,6- pyrimidine compounds such as dichloropyrimidine, 5-methoxy-2,4-dichloropyrimidine, 2-methyl-4,6-dichloropyrimidine, 6-methyl-2,4-dichloropyrimidine, 5-methyl-2,4-dichloropyrimidine, 5-nitro-2,4-dichloropyrimidine, 4-amino-2-chloro-5-fluoropyrimidine, 2-methyl-5-amino-4,6-dichloropyrimidine, and 5-bromo-4-chloro-2-methylthiopyrimidine; pyridazine compounds such as 3,6-dichloropyridazine, 3,5-dichloropyridazine, and 4-methyl-3,6-dichloropyridazine; and pyrazine compounds such as 2,3-dichloropyrazine, 2,6-dichloropyrazine, 2,5-dibromopyrazine, 2,6-dibromopyrazine, 2-amino-3,5-dibromopyrazine, and 5,6-dicyano-2,3-dichloropyrazine. These monomers may be used alone or in combination of two or more.

[0076] In the formula (1), each X is independently -O-, -S-, or -N(R 3 )-. When X is -O-, it is preferable in terms of flexibility, solubility, and heat resistance. 3 )- is preferable in terms of adhesion and the like.

[0077] R 3is a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a portion of such a hydrocarbon group or halogenated hydrocarbon group is substituted with at least one atom selected from an oxygen atom and a sulfur atom. R 3 In the above, examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms and the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms include the monovalent hydrocarbon group having 1 to 20 carbon atoms and the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms exemplified for Ar1. 3 Specific examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms or the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms partially substituted with at least one atom selected from oxygen atoms and sulfur atoms include groups in which the hydrocarbon group or halogenated hydrocarbon group is partially or entirely substituted with an ester group or a sulfonyl group.

[0078] R 3 As the group, a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms is preferred from the viewpoint of enabling the synthesis of polymer (A) with good polymerization reactivity. In addition, in formula (1), R 1 Both Xs on both sides are -N(R 3 )-, then two R 3 may be the same or different.

[0079] The polymer (A) may generally have other structural units as needed in addition to the repeating units represented by the formula (1). Thus, the repeating units represented by the formula (1) are bonded to each other, or to the other structural units or the terminal group Y represented by the formula (a). When the polymer (A) has a plurality of repeating units represented by formula (1), a plurality of R 1 may be the same or different. This means that R 2 and similarly for other repeating units.

[0080] Examples of the monomer that derives the other structural units include compounds that derive structural units containing a carbonate bond, a thiocarbonate bond, or a selenocarbonate bond, such as diphenyl carbonate, diphenyl thiocarbonate, diphenyl selenocarbonate, phosgene, thiophosgene, and selenophosgene; dihydroxy compounds such as benzene dimethanol and cyclohexane dimethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, and bis(fluorophenyl)anthrylphosphine oxide; and dihalides of dicarboxylic acids such as phthalic acid dichloride, isophthalic acid dichloride, and terephthalic acid dichloride. These monomers may be used alone or in combination of two or more.

[0081] The terminal group Y (terminal structure) of the polymer (A) is represented by the following formula (a).

[0082] [ka] [In formula (a), Y represents a group containing an ethylenically unsaturated double bond having 3 to 50 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 50 carbon atoms, an unsubstituted or substituted aliphatic hydrocarbon group having 6 to 50 carbon atoms, or an unsubstituted nitrogen-containing heteroaromatic ring, and when the aromatic hydrocarbon group or the aliphatic hydrocarbon group has a substituent, the substituent is a group other than a hydroxy group.]

[0083] The terminal group Y is bonded to the main chain terminal of the polymer (A), and specifically forms the terminal portion of the polymer (A) represented by the following formula (a1) or (a2). 1 , R 2 and the ends at X (e.g., Ar1, Ar2 and R 2 The substituent in X is -N(R 3 )-R in 3 ) is a group different from the groups constituting the group.

[0084] [ka] [In formula (a1) and formula (a2), Y has the same meaning as Y in the formula (a). X, R 1 and R 2 represents X and R in the formula (1). 1 and R 2 is synonymous with. X' is a single bond, -O-, -S- or -N(R 3 )-. R 3 is R in the formula (1) 3 is equivalent to

[0085] In order to improve the dielectric properties, the terminal group Y is preferably an aromatic or aliphatic hydrocarbon group or a nitrogen-containing heteroaromatic ring with low polarization, and when it further contains an ethylenically unsaturated double bond, the crosslink density can be improved, and therefore heat resistance and curability can be expected.

[0086] Examples of the group containing an ethylenically unsaturated double bond having 3 to 50 carbon atoms include aromatic ring-containing groups such as a 3-isopropenylphenyl group, a 4-isopropenylphenyl group, a 2-allylphenyl group, a 2-methoxy-4-allylphenyl group, a 4-(1-propenyl)-2-methoxyphenyl group, a 4-vinylbenzyl group, a 3-vinylbenzyl group, and a 2-vinylbenzyl group, an allyl group, an acryl group, a methacryl group, and a methallyl group.

[0087] Examples of aromatic hydrocarbon groups having 6 to 50 carbon atoms include aryl groups such as phenyl, biphenyl, tolyl, xylyl, naphthyl, and anthryl; and aralkyl groups such as benzyl, phenethyl, phenylpropyl, and naphthylmethyl.

[0088] Examples of the aliphatic hydrocarbon group having 6 to 50 carbon atoms include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; polycyclic cycloalkyl groups such as a norbornyl group and an adamantyl group; monocyclic cycloalkenyl groups such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group; and polycyclic cycloalkenyl groups such as a norbornenyl group.

[0089] The unsubstituted nitrogen-containing heteroaromatic ring includes the R 2 Examples of the rings include the same rings as those exemplified in

[0090] The substituents in the unsubstituted or substituted aromatic hydrocarbon group having 6 to 50 carbon atoms, the unsubstituted or substituted aliphatic hydrocarbon group having 6 to 50 carbon atoms, and the unsubstituted nitrogen-containing heteroaromatic ring are groups other than a hydroxy group, and specific examples include the same groups as those exemplified as the substituents in Ar1. The substituent is not particularly limited, and examples thereof include an allyl group, a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphate group, a primary to tertiary amino group, a salt of a carboxy group, a salt of a sulfonic acid group, a salt of a phosphonic acid group, a salt of a phosphate group, and a salt of a primary to tertiary amino group. Of these, an allyl group is preferred.

[0091] R in the formula (1) 1 or R 2 In addition to the monomer that gives the above, at least one monomer for forming the terminal group Y selected from the group consisting of a monohydric phenol, a monovalent amine, a monovalent thiol, a monovalent aromatic, a monovalent aliphatic halide, a monovalent acid halide, and a monovalent acid anhydride is used as a raw material and reacted to obtain a polymer (A) whose ends are capped with the terminal group Y. When synthesizing a polymer (A) in which the terminal group Y contains a double bond, for example, R 1 The monomers that are the raw materials for the part containing R 2During polymerization with the monomer that is the raw material for the portion containing R, the double bonds in the monomer that forms the terminal group Y react with each other to prevent gelation. 1 The monomers that are the raw materials for the part containing R 2 After polymerization with the monomer that is the raw material for the portion containing the group Y, a monomer for forming the terminal group Y may be added and reacted.

[0092] Examples of the monomer for forming the terminal group Y include monohydric phenol compounds such as t-butylphenol, nonylphenol, 4-isopropenylphenol, 4-vinylphenol, 2-allylphenol, isoeugenol, tocotrienol, α-tocophenol, 4-hydroxyphenylmaleimide, and 2-phenylphenol; monovalent amine compounds such as 4-hexylaniline and diallylamine; monovalent thiol compounds such as 1-octanethiol; monovalent aliphatic halides such as allyl chloride, 4-(chloromethyl)styrene, and 3-(chloromethyl)styrene; monovalent acid halides such as acrylic chloride, methacrylic chloride, crotonoyl chloride, and cinnamoyl chloride; and monovalent acid anhydrides such as acrylic anhydride, crotonic anhydride, and methacrylic anhydride. These monomers may be used alone or in combination of two or more.

[0093] The content of the repeating unit represented by the formula (1) in the polymer (A) is preferably 30 mol% or more, more preferably 50 mol% or more, even more preferably 60 mol% or more, and is preferably 99.5 mol% or less, more preferably 98 mol% or less, even more preferably 95 mol% or less.

[0094] <Sequence of each repeating unit> Examples of the polymer (A) having the repeating unit represented by formula (1) and the terminal group Y represented by formula (a) include polymers having a combination of these repeating units in the main chain, and specific examples include polymers represented by the following formulas (3) or (4). Here, the "main chain" refers to the relatively longest connecting chain in the polymer.

[0095] [ka]

[0096] In the above formula, R 1 , R 2 , X, Y and X′ are R in the formulas (1), (a), (a1) and (a2). 1 , R 2 , X, Y and X′ are synonymous with each other. n is an integer of 0 to 100, and more preferably 2 to 30. In the above formula, a plurality of R 1 , R 2 , X, Y and X' may be the same or different.

[0097] <Method for synthesizing polymer (A)> The method for synthesizing the polymer (A) is not particularly limited, and known methods can be used. 1 and a monomer serving as a raw material for the portion containing R 2 The monomers that form the other structural units and the monomers that form the terminal group Y can be synthesized by heating them together in an organic solvent with an alkali metal or an alkali metal compound. 1 and a monomer serving as a raw material for the portion containing R 2 After polymerizing the monomers that are the raw materials for the portion containing the monomer, the mixture may be heated and mixed to cause a reaction.

[0098] Alkali metals and alkali metal compounds When a compound having a hydroxy group, such as a phenol compound, is used as a raw material in the synthesis of polymer (A), the alkali metal and alkali metal compound react with the compound having a hydroxy group to form an alkali metal salt. Examples of such alkali metals and alkali metal compounds include: Alkali metals such as lithium, sodium, and potassium; Alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; Alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; Alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate; Examples include alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate. Of these, alkali metal carbonates are preferred, with potassium carbonate being more preferred.

[0099] When a compound having a hydroxy group is used in synthesizing the polymer (A), the amount of alkali metal and alkali metal compound used is such that the lower limit of the ratio of the number of moles of alkali metal atoms to the number of moles of hydroxy groups in all compounds used in synthesizing the polymer (A) is preferably 1, more preferably 1.1, and even more preferably 1.2, and the upper limit of said ratio is preferably 3, more preferably 2, and even more preferably 1.8.

[0100] Organic solvents Examples of the organic solvent include: ether solvents such as tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, anisole, phenetole, diphenyl ether, dialkoxybenzene, and trialkoxybenzene; Nitrogen-containing solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinone; ester solvents such as gamma-butyrolactone; sulfur-containing solvents such as sulfolane, dimethyl sulfoxide, diethyl sulfoxide, dimethyl sulfone, diethyl sulfone, diisopropyl sulfone, and diphenyl sulfone; ketone solvents such as benzophenone, 2-heptanone, cyclohexanone, and methyl ethyl ketone; Halogenated solvents such as methylene chloride, chloroform, and chlorobenzene; Examples of the solvent include aromatic hydrocarbon solvents such as benzene, toluene, and xylene. Among these organic solvents, 2-heptanone, cyclohexanone, N-methyl-2-pyrrolidone, toluene, and xylene are preferred, and N-methyl-2-pyrrolidone, 2-heptanone, and cyclohexanone are more preferred.

[0101] The lower limit of the reaction temperature during the synthesis is preferably 50°C, more preferably 80°C, and the upper limit is preferably 300°C, more preferably 200°C. The lower limit of the reaction time in the synthesis is preferably 1 hour, more preferably 2 hours, and even more preferably 3 hours, and the upper limit is preferably 100 hours, more preferably 50 hours, and even more preferably 24 hours.

[0102] For the purpose of suppressing gelation of the polymerization solution, the lower limit of the reaction temperature when the monomer for forming the terminal group Y is added after polymerization is preferably 0°C, more preferably 10°C, and the upper limit is preferably 130°C, more preferably 110°C. The lower limit of the reaction time when the monomer for forming the terminal group Y is added after polymerization and reacted is preferably 1 hour, more preferably 2 hours, and even more preferably 3 hours, and the upper limit is preferably 48 hours, more preferably 24 hours, and even more preferably 10 hours.

[0103] [Physical properties of polymer (A)] The lower limit of the polystyrene-equivalent weight average molecular weight (Mw) of the polymer (A) is preferably 1,000, more preferably 2,000, even more preferably 3,000, and particularly preferably 5,000, and the upper limit is preferably 500,000, more preferably 100,000, even more preferably 50,000, more preferably 30,000, and particularly preferably 15,000. The polymer (A) having an Mw within the above range is preferred because it has a good balance of excellent adhesion, heat resistance, impregnation into glass cloth, moldability such as resin flow, and the like. In the present invention, Mw is a value measured by gel permeation chromatography (GPC) under the conditions described in the following examples.

[0104] The dielectric loss tangent (tanδ) of the polymer (A) is preferably less than 0.0030, more preferably 0.0020 or less, and even more preferably 0.0012 or less, from the viewpoint of being able to reduce transmission loss when a composition containing the polymer (A) is prepared, and the lower limit is not particularly limited, but is preferably 0.0005 or more. Specifically, the dielectric loss tangent can be measured by the method described in the examples below.

[0105] ≪Composition≫ The composition according to one embodiment of the present invention (hereinafter also referred to as "the composition") is not particularly limited as long as it contains the polymer (A), but it preferably contains a curable compound (B) other than the polymer (A). The composition may further contain other components such as a curing aid.

[0106] <Polymer (A)> The polymer (A) used in the present composition may be one type or two or more types, and the present composition may also be a mixture of two or more types of polymer (A). When two or more types of polymers (A) are used, polymers (A) having different molecular weights within the molecular weight range of the polymer (A) can be mixed depending on the desired physical properties, for example.

[0107] The content of polymer (A) in the present composition is, for example, preferably 0.05% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and is preferably 99.95% by mass or less, more preferably 90% by mass or less, even more preferably 80% by mass or less, when the total solid content in the present composition is taken as 100% by mass. It is preferable that the content of the polymer (A) is within the above range, since the adhesiveness, heat resistance, curability and electrical properties of the cured product obtained from the present composition can be further improved.

[0108] <Curable compound (B)> The curable compound (B) (hereinafter also referred to as "compound (B)") is a compound other than the polymer (A), which is cured by irradiation with heat or light (e.g., visible light, ultraviolet light, near-infrared light, far-infrared light), and may require a curing aid, as described below. Examples of such compounds (B) include vinyl compounds, maleimide compounds, allyl compounds, acrylic compounds, methacrylic compounds, thiol compounds, oxazine compounds, cyanate compounds, epoxy compounds, oxetane compounds, methylol compounds, benzocyclobutene compounds, propargyl compounds, and silane compounds. Among these, at least one of vinyl compounds, maleimide compounds, and allyl compounds is particularly preferred in terms of compatibility with the polymer (A), reactivity, etc. The compound (B) may be used alone or in combination of two or more.

[0109] Examples of the vinyl compound include compounds represented by the following formulas (b-1-1) to (b-1-5). Further examples of the vinyl compound include styrene-based thermoplastic elastomers, such as styrene-butadiene-styrene copolymer (SBS), hydrogenated styrene-butadiene-styrene copolymer (SEBS), styrene-isoprene-styrene copolymer (SIS), hydrogenated styrene-isoprene-styrene copolymer, styrene-butadiene elastomer (SBR), tert-butylstyrene, and 2-vinyl-4,6-diamino-1,3,5-triazine, and other compounds containing a vinyl group. Further examples of the vinyl compound include TA100 (manufactured by Mitsubishi Gas Chemical Company, Inc.) and ULL-950S (manufactured by LONZA).

[0110] [ka] [In formulas (b-1-2) and (b-1-4), n independently represents 1 to 5000. In formula (b-1-5), l, m, and n independently represent 1 to 5000.]

[0111] Examples of the maleimide compound include compounds represented by the following formulas (b-2-1) to (b-2-8).

[0112] [ka] [In formulas (b-2-4), (b-2-5), (b-2-7) and (b-2-8), n is independently an integer of 1 to 50.]

[0113] Examples of the allyl compound include compounds represented by the following formulas (b-3-1) to (b-3-6).

[0114] [ka]

[0115] Examples of the acrylic compound include compounds represented by the following formulas (b-4-1) to (b-4-7).

[0116] [ka] [In formulas (b-4-1), (b-4-2), (b-4-3) and (b-4-6), n is independently 1 to 50. In formula (b-4-3), m is 1 to 50. In formula (b-4-6), R is a divalent hydrocarbon group having 1 to 20 carbon atoms.]

[0117] Examples of the methacrylic compound include bisphenol A type epoxy methacrylate, phenol novolac type epoxy methacrylate, trimethylolpropane methacrylate, dipentaerythritol hexamethacrylate, and SA-9000 (manufactured by Sabic).

[0118] Examples of the thiol compound include 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(2-(3-sulfanylbutanoyloxy)ethyl)-1,3,5-triazinane-2,4,6-trione, 2-(dibutylamino)-1,3,5-triazine-4,6-dithiol, and 6-diallylamino-1,3,5-triazine-2,4-dithiol.

[0119] Examples of the silane compound include KF-99 (manufactured by Shin-Etsu Chemical Co., Ltd.) and KF-9901 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0120] Examples of the oxazine compound include compounds represented by the following formulas (b-5-1) to (b-5-5).

[0121] [ka]

[0122] Examples of the cyanate compound include compounds represented by the following formulas (b-6-1) to (b-6-7).

[0123] [ka] [In formulas (b-6-6) and (b-6-7), n is independently an integer of 0 to 30.]

[0124] Examples of the epoxy compound include compounds represented by the following formulas (b-7-1) to (b-7-5). Further examples of the epoxy compounds include polyglycidyl ether of dicyclopentadiene-phenol polymer, liquid phenol novolac epoxy compounds, cresol novolac epoxy compounds, epoxidized styrene-butadiene block copolymers, 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, XER-81 (manufactured by JSR Corporation, epoxy group-containing NBR particles), and JP-100 (manufactured by Nippon Soda Co., Ltd.).

[0125] [ka] [In formula (b-7-5), n is 0 to 5000.]

[0126] Examples of the oxetane compound include compounds represented by the following formulas (b-8-1) to (b-8-3).

[0127] [ka] [In formulas (b-8-1) and (b-8-2), n is each independently an integer of 0 to 30.]

[0128] Examples of the methylol compound include the methylol compounds described in JP-A-2006-178059 and JP-A-2012-226297. Specific examples include melamine-based methylol compounds such as polymethylolated melamine, hexamethoxymethylmelamine, hexaethoxymethylmelamine, hexapropoxymethylmelamine, and hexabutoxymethylmelamine; glycoluril-based methylol compounds such as polymethylolated glycoluril, tetramethoxymethylglycoluril, and tetrabutoxymethylglycoluril; and guanamine-based methylol compounds such as methylolated guanamine compounds such as 3,9-bis[2-(3,5-diamino-2,4,6-triazaphenyl)ethyl]-2,4,8,10-tetraoxospiro[5.5]undecane and 3,9-bis[2-(3,5-diamino-2,4,6-triazaphenyl)propyl]-2,4,8,10-tetraoxospiro[5.5]undecane, and compounds in which all or part of the active methylol groups in the compounds have been alkyl-etherified.

[0129] Examples of the benzocyclobutene compound include the compounds described in JP-A-2005-60507.

[0130] Examples of the propargyl compound include compounds represented by the following formulae (b-9-1) and (b-9-2).

[0131] [ka]

[0132] [Content of Compound (B)] The content of compound (B) in the present composition is, for example, preferably 0.05% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and is preferably 99.95% by mass or less, more preferably 90% by mass or less, even more preferably 80% by mass or less, when the total solid content in the present composition is taken as 100% by mass. It is preferable that the content of compound (B) is within the above range, since the strength, heat resistance, and chemical resistance of the cured product obtained from the present composition can be further improved.

[0133] Furthermore, when the total solid content of the polymer (A) and the compound (B) in the composition is taken as 100% by mass, the content of the compound (B) is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 10% by mass or more, and is preferably 99% by mass or less, more preferably 95% by mass or less, even more preferably 90% by mass or less. It is preferable that the content of compound (B) is within the above range, since the toughness, heat resistance, and chemical resistance of the cured product obtained from the present composition can be further improved.

[0134] <Other ingredients> In addition to the polymer (A) and the compound (B), the present composition may further contain other components within the range that does not impair the effects of the present invention. Examples of the other components include curing aids, solvents, polymerization inhibitors for increasing stability, antioxidants, inorganic fillers, organic fillers, adhesion aids, lubricants, flame retardants, antibacterial agents, colorants, release agents, foaming agents, and polymers other than polymer (A). These other components may be used singly or in combination of two or more.

[0135] [Curing aid] The present composition may contain a curing aid, if necessary. Examples of the curing aid include polymerization initiators such as thermal or photoradical initiators, cationic curing agents, and anionic curing agents.

[0136] Examples of thermal radical initiators include organic peroxides such as dicumyl peroxide, 1,1-di(t-butylperoxy)cyclohexane, di(t-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3, and benzoyl peroxide; and azo compounds such as azobisbutyronitrile, 1,1'-azobis(1-acetoxy-1-phenylethane), 2,2'-azobis(2,4-dimethylvaleronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), dimethyl-2,2'-azobis(isobutyrate), and 2,2'-azobis(2-methylbutyronitrile).

[0137] Examples of cationic curing agents include diallyliodonium salts with BF, PF, or SbF as a counter anion, such as SP70, SP172, and CP66 manufactured by ADEKA CORPORATION, CI2855 and CI2823 manufactured by Nippon Soda Co., Ltd., and SI100 and SI150 manufactured by Sanshin Chemical Industry Co., Ltd.; trialkylsulfonium salts; phosphonium salts such as butyltriphenylphosphonium thiocyanate; and boron trifluoride.

[0138] Examples of the anionic curing agent include imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-methylimidazolium isocyanurate, 2,4-diamino-6-[2-methylimidazoline-(1)]-ethyl-S-triazine, and 2,4-diamino-6-[2-ethyl-4-methylimidazoline-(1)]-ethyl-S-triazine; phosphorus compounds such as triphenylphosphine; and amine compounds such as 4,4'-diaminodiphenylmethane.

[0139] Furthermore, examples of the curing aid when a silane compound is used as compound (B) include platinum black, platinic chloride, chloroplatinic acid, reaction products of chloroplatinic acid with monohydric alcohols, complexes of chloroplatinic acid with olefins, platinum group metal catalysts such as platinum-based catalysts such as platinum bisacetoacetate; palladium-based catalysts; and rhodium-based catalysts; zinc benzoate; and zinc octoate.

[0140] When an oxazine compound is used as compound (B), examples of the curing aid include phenol and its derivatives, cyanate esters, Bronsted acids such as p-toluenesulfonic acid, aromatic amine compounds such as adipic acid, p-toluenesulfonic acid esters, 4,4'-diaminodiphenyl sulfone, and melamine, bases such as 2-ethyl-4-methylimidazole, boron trifluoride, and Lewis acids.

[0141] When the present composition contains a curing aid, the content of the curing aid is preferably within a range that allows the present composition to be cured well and a cured product to be obtained. Specifically, the content of the curing aid is preferably 0.000001 part by mass or more, more preferably 0.001 part by mass or more, and preferably 20 parts by mass or less, more preferably 10 parts by mass or less, per 100 parts by mass of the total solid content of the polymer (A) and the compound (B).

[0142] [solvent] The composition may contain a solvent, if necessary. Examples of the solvent include amide solvents such as N,N-dimethylformamide, ester solvents such as γ-butyrolactone and butyl acetate, ketone solvents such as cyclopentanone, cyclohexanone, methyl ethyl ketone and 2-heptanone, ether solvents such as 1,2-methoxyethane, anisole and tetrahydrofuran, polyfunctional solvents such as 1-methoxy-2-propanol and propylene glycol methyl ether acetate, sulfone solvents such as dimethyl sulfoxide, methylene chloride, benzene, toluene, xylene, and trialkoxybenzene (number of carbon atoms in the alkoxy group: 1 to 4).

[0143] When the present composition contains a solvent, the content of the solvent in the present composition is not particularly limited, but is, for example, preferably 0 parts by mass or more and 2000 parts by mass or less, more preferably 0 parts by mass or more and 1000 parts by mass or less, relative to 100 parts by mass of the total solid content of the polymer (A) and the compound (B). When the polymer (A) or the compound (B) has high solubility in the solvent, the content of the solvent in the composition may be 50 parts by mass or more and 200 parts by mass or less.

[0144] [Polymerization inhibitor] Examples of the polymerization inhibitor include quinones such as hydroquinone, methylhydroquinone, p-benzoquinone, chloranil, and trimethylquinone, and aromatic diols.

[0145] When the present composition contains a polymerization inhibitor, the content of the polymerization inhibitor is, for example, preferably 0.000001 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the total solid content of the polymer (A) and the compound (B).

[0146] [Antioxidants] Examples of the antioxidant include hindered phenol compounds, phosphorus compounds, sulfur compounds, metal compounds, and hindered amine compounds. Among these, hindered phenol compounds are preferred.

[0147] The hindered phenol compound is preferably a compound having a molecular weight of 500 or more. Examples of the hindered phenol compound having a molecular weight of 500 or more include triethylene glycol-bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-3,5-triazine, pentaerythritol tetrakis[3-(3,5-t-butyl-4-hydroxyphenyl)propionate], 1,1,3-tris[2-methyl-4-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy]-5-t-butylphenyl]butanol, and the like. methylpropanol, 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, N,N-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, tris-(3,5-di-t-butyl-4-hydroxybenzyl)-isocyanurate, 3,9-bis[2-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, 2,6-di-tert-butyl-p-cresol (BHT), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione [manufactured by ADEKA Corporation, AO-020], 4,4',4''-(1-methylpropanyl-3-ylidene)tris(6-tert-butyl-m-cresol) [manufactured by ADEKA Corporation, AO-030], 6,6'-di-tert-butyl-4,4'-butylidenedi-m-cresol [manufactured by ADEKA Corporation, AO-040], and 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene [manufactured by ADEKA Corporation, AO-330]. .

[0148] Examples of hindered amine compounds include 2,2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl [ADEKA CORPORATION, Adeka STAB LA-7RD], IRGASTAB UV 10 (4,4'-[1,10-dioxo-1,10-decanediyl)bis(oxy)]bis[2,2,6,6-tetramethyl]-1-piperidinyloxy) (CAS. 2516-92-9), TINUVIN 123 (4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl) (all manufactured by BASF), FA-711HM, FA-712HM (2,2,6,6-tetramethylpiperidinyl methacrylate, manufactured by Showa Denko Materials Co., Ltd.), TINUVIN 111FDL, TINUVIN 144, TINUVIN 152, TINUVIN 161FDL, TINUVIN 171FDL, TINUVIN 181FDL, TINUVIN 191FDL, TINUVIN 201FDL, TINUVIN 211FDL, TINUVIN 221FDL, TINUVIN 231FDL, TINUVIN 244, TINUVIN 252, TINUVIN 261FDL, TINUVIN 271FDL, TINUVIN 281FDL, TINUVIN 291FDL, TINUVIN 301FDL, TINUVIN 311FDL, TINUVIN 321FDL, TINUVIN 331FDL, TINUVIN 341FDL, TINUVIN 351FDL, TINUVIN 361FDL, TINUVIN 371FDL, TINUVIN 381FDL, TINUVIN 391FDL, TINUVIN 4 292, TINUVIN 765, TINUVIN 770DF, TINUVIN 5100, SANOL LS-2626, CHIMASSORB 119FL, CHIMASSORB 2020 FDL, CHIMASSORB 944 FDL, TINUVIN 622 LD (all manufactured by BASF), LA-52, LA-57, LA-62, LA-63P, LA-68LD, LA-77Y, LA-77G, LA-81, LA-82 (1,2,2,6,6-pentamethyl-4-piperidyl methacrylate), and LA-87 (all manufactured by ADEKA Corporation).

[0149] When the present composition contains an antioxidant, the content of the antioxidant is, for example, preferably 0.001 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the total solid content of the polymer (A) and the compound (B).

[0150] [Inorganic filler] Examples of the inorganic filler include silicas such as natural silica, fused silica, and amorphous silica, white carbon, titanium white, aerosil, alumina, talc, natural mica, synthetic mica, clay, barium sulfate, E-glass, A-glass, C-glass, L-glass, D-glass, S-glass, and M-glass G20.

[0151] When the composition contains an inorganic filler, the content of the inorganic filler is, for example, preferably 0.1 to 300 parts by mass per 100 parts by mass of the total solid content of the polymer (A) and the compound (B). The inorganic filler may be dispersed in the solvent by the polymer (A).

[0152] [Organic filler] Examples of the organic filler include fluorine-based resins or fluorine-based particles such as polytetrafluoroethylene (PTFE), polyperfluoroalkoxy resins, polyethylene fluoride propylene resins, and polytetrafluoroethylene-polyethylene copolymers; polystyrene resins or particles; rubber-like resins or particles such as polybutadiene and styrene-butadiene resins; and hollow particles having a shell of divinylbenzene or divinylbiphenyl.

[0153] When the composition contains an organic filler, the content of the organic filler is, for example, preferably 0.1 to 300 parts by mass per 100 parts by mass of the total solid content of the polymer (A) and the compound (B). The organic filler may be in a state of being dispersed in the solvent by the polymer (A).

[0154] [Physical properties of the composition] The resin flow amount of the present composition is preferably 0% or more, more preferably 10% or more, and is preferably 25% or less, more preferably 20% or less. When the resin flow amount is within the above range, the thickness uniformity of prepregs, copper-clad laminates, etc. obtained using the present composition is good. Specifically, the resin flow amount is measured by the method described in the examples below.

[0155] [Method for preparing the present composition] The composition can be prepared, for example, by uniformly mixing the polymer (A), the compound (B), and the other components described above. In this case, the order of mixing, mixing conditions, etc. are not particularly limited, and a conventionally known mixer may be used for mixing.

[0156] ≪Cured product≫ A cured product according to one embodiment of the present invention (hereinafter also referred to as "the present cured product") is a cured product of the present composition described above, and is obtained by curing the present composition described above. The present cured product may be, for example, a partially cured product of the present composition obtained by drying the solvent from the present composition.

[0157] The method for curing the present composition is not particularly limited, but typically includes a method of thermal curing by heating or a method of photocuring by irradiation with light. These methods can also be used in combination. In the case of thermal curing, the heating temperature is preferably 50° C. or higher, more preferably 100° C. or higher, even more preferably 120° C. or higher, and preferably 250° C. or lower, more preferably 220° C. or lower. The heating time is preferably 0.1 hours or longer, more preferably 0.5 hours or longer, and preferably 36 hours or shorter, more preferably 5 hours or shorter. In the case of photocuring, examples of the light to be irradiated include visible light, ultraviolet light, near infrared light, and far infrared light.

[0158] Glass transition temperature (Tg) The lower limit of the Tg of the present cured product is preferably 100°C, more preferably 110°C, and the upper limit is, for example, 300°C. When the Tg is within the above range, melt molding can be carried out more easily, and a cured product having excellent heat resistance can be easily obtained. Tg was measured by preparing a test piece (width: 3 mm x length: 1 cm) and using a dynamic viscoelasticity measuring device (Seiko Instruments Inc., model number "EXSTAR4000"), measuring from 50°C to 300°C at a heating rate of 10°C / min and 1 Hz under nitrogen, and then measuring again at a heating rate of 10°C / min and 1 Hz up to 300°C, and the tan δ at this time was taken as the glass transition temperature (Tg). When two or more tan δ values ​​existed, the lowest value was taken as Tg.

[0159] The dielectric loss tangent (tan δ) of the cured product is preferably 0.0025 or less, more preferably 0.0018 or less, and even more preferably 0.0015 or less, from the viewpoint of reducing transmission loss, and although there is no particular lower limit, it is preferably 0.0005 or more. Specifically, the dielectric loss tangent can be measured by the method described in the examples below.

[0160] The shape of the cured product is not particularly limited and may be any shape suitable for the application or purpose, for example, a film. For example, the composition can be melt-molded or cast to obtain a film-like cured product. The thickness of the film is not particularly limited and may be appropriately selected depending on the desired application, but is, for example, 10 μm or more, preferably 30 μm or more, and for example, 2 mm or less, preferably 1 mm or less.

[0161] <Laminate> A laminate according to one embodiment of the present invention (hereinafter also referred to as "the present laminate") has, for example, a substrate and a cured layer formed using the present composition. The present laminate may have two or more substrate layers, may have two or more cured product layers, or may have other conventionally known layers other than the substrate and the cured product layer. When the present laminate has two or more substrate layers, cured product layers, or other layers, these may be the same layer (plate) or different layers (plates).

[0162] The present laminate may be a prepreg obtained by impregnating a substrate such as glass cloth, aramid nonwoven fabric, or polyester nonwoven fabric with the present composition and curing it.

[0163] From the viewpoint of adhesiveness and practicality, the substrate may be an inorganic substrate, a metal substrate, a resin substrate, etc. The substrate may also be a prepreg. Examples of the inorganic substrate include inorganic substrates containing silicon, silicon carbide, silicon nitride, alumina, glass, gallium nitride, and the like as components. Examples of the metal substrate include metal substrates containing copper, aluminum, gold, silver, nickel, palladium, and the like. Examples of the resin substrate include resin substrates containing liquid crystal polymer, polyimide, polyphenylene sulfide, polyether ether ketone, polyamide (nylon), polyethylene terephthalate, polyethylene naphthalate, cycloolefin polymer, polyolefin, and the like.

[0164] The cured product layer can be formed, for example, by curing using the method described in the section on cured products. The thickness of the cured material layer is not particularly limited, but is, for example, 1 μm to 3 mm.

[0165] ≪Applications≫ The polymer (A), the composition, the cured product, and the laminate are suitable for use as structural materials in the transportation industry, such as the aircraft and automobile industries, and as electrical and electronic materials in the electrical and electronics industry. Specifically, they can be used in, for example, encapsulants for electrical and electronic components, interlayer insulating films, and stress-relief primers; laminate applications (e.g., prepregs, copper-clad laminates, (multilayer) printed wiring boards, interlayer adhesives, solder resists, and solder pastes); adhesive applications (e.g., adhesive sheets for forming insulating layers, thermally conductive adhesives, and adhesive sheets); structural adhesives and prepregs used in various structural materials; various coatings; optical component applications (e.g., optical films such as wave plates and retardation plates; various specialty lenses such as conical lenses, spherical lenses, and cylindrical lenses; and lens arrays); and insulating films for printed wiring boards.

[0166] <Electronic Components> An electronic component according to one embodiment of the present invention comprises the present cured product or present laminate. The electronic component may comprise two or more present cured products or two or more present laminates, or may comprise one or more present cured products and one or more present laminates. When two or more present cured products or present laminates are present, they may be the same or different.

[0167] Examples of the electronic components include circuit boards, semiconductor packages, and display substrates. The present cured product (cured film) can be used for these electronic components as prepregs, copper-clad laminates, printed wiring boards, adhesive sheets for forming insulating layers, surface protective films, rewiring layers, or planarizing films. Because the present cured product can maintain its insulating properties even under high temperature and high humidity conditions, the electronic components can protect circuit patterns from external environments such as dust, heat, and humidity, and have excellent insulation reliability between circuit patterns, enabling them to operate stably for many years.

[0168] For example, a rewiring layer can be formed by filling metal between the patterns of the cured product (cured film) by plating or the like, and if necessary, stacking more cured products (cured films) and repeating the metal filling process, thereby producing an electronic component having a substrate and a rewiring layer including metal wiring and an insulating film. [Example]

[0169] The present invention will be specifically described below based on examples, but the present invention is not limited to the following examples.

[0170] [Synthesis Example 1] 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (86.92 g), 4,6-dichloropyrimidine (47.58 g), isopropenylphenol (10.67 g), and potassium carbonate (50.66 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (64.00 g) was added. The mixture was reacted at 130°C for 6 hours under a nitrogen atmosphere. After the reaction was completed, the mixture was diluted with N-methyl-2-pyrrolidone (368.0 g). After filtering to remove salts, the resulting solution was poured into methanol (19.4 kg). The precipitated solid was filtered, washed with a small amount of methanol, and then filtered again. The solid was then dried under reduced pressure at 120°C for 12 hours using a vacuum dryer to obtain a polymer represented by the following formula (1) (yield: 122.0 g, 90%).

[0171] [ka]

[0172] [Synthesis Example 2] A polymer represented by the following formula (2) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (62.08 g), isopropenylphenol (2.170 g), 4,6-dichloropyrimidine (30.99 g), and potassium carbonate (38.83 g). (Yield: 80.08 g, 90%)

[0173] [ka]

[0174] [Synthesis Example 3] The polymer shown in the following formula (3) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (86.92 g), 4,6-dichloropyrimidine (47.58 g), 2-allylphenol (10.67 g), and potassium carbonate (59.66 g). (Yield: 121.9 g, 90%)

[0175] [ka]

[0176] [Synthesis Example 4] 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (86.92 g), 4,6-dichloropyrimidine (47.58 g), and potassium carbonate (59.66 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (64.00 g) was added. The mixture was reacted at 130°C for 6 hours under a nitrogen atmosphere. After the reaction, allyl bromide (10.67 g) was added dropwise to the vessel while it was cooled to 10°C, and the mixture was reacted at 70°C for 6 hours. The resulting reaction solution was diluted with N-methyl-2-pyrrolidone (368.0 g), and the salt was removed from the diluted solution by filtration. The resulting solution was then poured into methanol (19.40 kg). The precipitated solid was filtered off, washed with a small amount of methanol, and recovered by filtration again. The solid was then dried under reduced pressure at 120°C for 12 hours using a vacuum dryer to obtain a polymer represented by the following formula (4) (yield: 121.9 g, yield: 90%).

[0177] [ka]

[0178] [Synthesis Example 5] 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (71.13 g), 4,6-dichloropyrimidine (29.79 g), and potassium carbonate (39.27 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (64.00 g) was added. The mixture was reacted at 130°C for 6 hours under a nitrogen atmosphere. After the reaction, the vessel was cooled to 10°C, and methacryloyl chloride (6.094 g) was added dropwise, followed by a reaction at 50°C for 6 hours. The resulting reaction solution was diluted with N-methyl-2-pyrrolidone (368.0 g), and the salt was removed from the diluted solution by filtration. The resulting solution was then poured into methanol (19.40 kg). The precipitated solid was filtered off, washed with a small amount of methanol, and recovered by filtration again. The solid was then dried under reduced pressure at 120°C for 12 hours using a vacuum dryer to obtain a polymer represented by the following formula (5) (yield: 92.30 g, 90%).

[0179] [ka]

[0180] [Synthesis Example 6] A polymer represented by the following formula (6) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (58.98 g), 2,2'-diallylbisphenol A (3.084 g), 2-phenylphenol (2.764 g), 4,6-dichloropyrimidine (30.99 g), and potassium carbonate (37.317 g). The polymer was synthesized in the same manner as in Synthesis Example 1, and a polymer represented by the following formula (6) was obtained (yield: 77.04 g, 90%).

[0181] [ka]

[0182] [Synthesis Example 7] A polymer represented by the following formula (7) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (51.26 g), isopropenylphenol (7.834 g), 4,6-dichloropyrimidine (34.10 g), and potassium carbonate (35.93 g) (yield: 68.70 g, 90%).

[0183] [ka]

[0184] [Synthesis Example 8] A polymer represented by the following formula (8) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (51.27 g), isopropenylphenol (7.83 g), 4,6-dichloro-2-phenylpyrimidine (51.51 g), and potassium carbonate (35.93 g). (Yield: 86.10 g, 90%)

[0185] [ka]

[0186] [Synthesis Example 9] A polymer represented by the following formula (9) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (58.98 g), 4-chloropyrimidine (1.145 g), 4,6-dichloropyrimidine (29.34 g), and potassium carbonate (37.31 g) (yield: 77.00 g, 90%).

[0187] [ka]

[0188] [Synthesis Example 10] A polymer represented by the following formula (10) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (46.56 g), 4,6-dichloropyrimidine (21.45 g), and potassium carbonate (22.80 g) (yield: 70.00 g, 90%).

[0189] [ka]

[0190] [Synthesis Example 11] Synthesis was performed in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (56.237 g, 181.15 mmol), 4,6-dichloropyrimidine (26.959 g, 180.97 mmol), and potassium carbonate (33.800 g, 244.56 mmol), to obtain a polymer for dielectric tangent evaluation represented by the formula (10) and having a weight-average molecular weight Mw of 50,000 (yield: 70 g, 90%).

[0191] [Synthesis Example 12] 2,2-bis(4-hydroxy-3-methylphenyl)propane (26.43 g), 4,6-dichloro-2-phenylpyrimidine (17.08 g), and potassium carbonate (19.23 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (42.50 g) was added. The mixture was reacted at 100°C for 6 hours under a nitrogen atmosphere. After the reaction, the vessel was cooled to 10°C, and m,p-(chloromethyl)styrene (11.53 g) was added dropwise, followed by a reaction at 100°C for 4 hours. The resulting reaction solution was diluted with N-methyl-2-pyrrolidone (55.0 g), and the salt was removed from the diluted solution by filtration. The resulting solution was then poured into methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, and recovered by filtration again. The solid was then dried under reduced pressure at 60°C for 12 hours using a vacuum dryer to obtain a polymer represented by the following formula (11) (yield: 44.10 g, 90%).

[0192] [ka]

[0193] [Synthesis Example 13] A polymer represented by the following formula (12) was obtained (yield: 46.55 g, 90%) in the same manner as in Synthesis example 12, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (33.85 g), 4,6-dichloro-2-phenylpyrimidine (16.66 g), m,p-chloromethylstyrene (8.680 g), potassium carbonate (18.66 g), and N-methyl-2-pyrrolidone (42.50 g).

[0194] [ka]

[0195] [Synthesis Example 14] A polymer represented by the following formula (13) was obtained in the same manner as in Synthesis example 12, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (37.84 g), 4,6-dichloro-2-phenylpyrimidine (33.31 g), m,p-chloromethylstyrene (17.36 g), potassium carbonate (37.31 g), and N-methyl-2-pyrrolidone (181.4 g) (yield: 89.30 g, 90%).

[0196] [ka] (13)

[0197] [Synthesis Example 15] A polymer represented by the following formula (14) was obtained in the same manner as in Synthesis example 12, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 4,6-dichloro-2-phenylpyrimidine (13.50 g), m,p-(chloromethyl)styrene (16.96 g), potassium carbonate (18.66 g), and N-methyl-2-pyrrolidone (78.28 g). (Yield: 39.69 g, 88%)

[0198] [ka]

[0199] [Synthesis Example 16] A polymer represented by the following formula (15) was obtained in a yield of 37.91 g (90%) in the same manner as in Synthesis example 12, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 4,6-dichloro-2-phenylpyrimidine (19.81 g), m,p-(chloromethyl)styrene (5.087 g), potassium carbonate (18.66 g), and N-methyl-2-pyrrolidone (78.28 g).

[0200] [ka]

[0201] [Synthesis Example 17] A polymer represented by the following formula (16) was obtained in a yield of 40.55 g (90%) in the same manner as in Synthesis example 12, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (26.43 g), 4,6-dichloro-2-phenylpyrimidine (17.08 g), potassium carbonate (19.23 g), and N-methyl-2-pyrrolidone (42.50 g).

[0202] [ka]

[0203] [Synthesis Example 18] A polymer represented by the following formula (17) was obtained (yield: 76.44 g, 89%) in the same manner as in Synthesis example 14, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (37.84 g), 4,6-dichloro-2-phenylpyrimidine (33.31 g), potassium carbonate (37.31 g), and N-methyl-2-pyrrolidone (181.4 g).

[0204] [ka] (17)

[0205] [Synthesis Example 19] A polymer represented by the following formula (18) was obtained (yield: 45.05 g, 90%) in the same manner as in Synthesis example 17, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (33.85 g), 4,6-dichloro-2-phenylpyrimidine (16.65 g), potassium carbonate (18.65 g), and N-methyl-2-pyrrolidone (50.5 g).

[0206] [ka]

[0207] [Synthesis Example 20] A polymer represented by the following formula (19) was obtained in the same manner as in Synthesis example 1, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 4,6-dichloro-2-phenylpyrimidine (29.25 g), 2-allylphenol (8.131 g), and potassium carbonate (24.31 g) (yield: 48.19 g, 90%).

[0208] [ka]

[0209] [Synthesis Example 21] A polymer represented by the following formula (20) was obtained in the same manner as in Synthesis example 5, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 4,6-dichloropyrimidine (16.57 g), potassium carbonate (18.65 g), N-methyl-2-pyrrolidone (64.00 g), and methacryloyl chloride (7.657 g) (yield: 34.71 g, 85%).

[0210] [ka]

[0211] [Synthesis Example 22] A polymer represented by the following formula (21) was obtained in the same manner as in Synthesis Example 1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (31.04 g), 2,2'-diallylbisphenol A (7.711 g), 4-chloropyrimidine (5.267 g), 4,6-dichloropyrimidine (21.33 g), and potassium carbonate (27.61 g).

[0212] [ka]

[0213] [Weight average molecular weight (Mw), number average molecular weight (Mn)] The weight average molecular weight (Mw) and number average molecular weight (Mn) of the polymers synthesized in Synthesis Examples 1 to 10 and 12 to 22 and SA-9000 used in the following Comparative Examples were measured using a GPC apparatus ("HLC-8320" manufactured by Tosoh Corporation) under the following conditions. The results are shown in Tables 1 and 2. Column: "TSKgel α-M" manufactured by Tosoh Corporation and "TSKgelguard column α" manufactured by Tosoh Corporation connected together Developing solvent: N-methyl-2-pyrrolidone Column temperature: 40℃ Flow rate: 1.0 mL / min Sample concentration: 0.75% by mass Sample injection volume: 50 μL Detector: Refractometer Standard material: Monodisperse polystyrene Concentration of the measurement sample: 0.1% by mass

[0214] <Dielectric loss tangent> Samples prepared by blending the polymers to be measured (the polymers synthesized in Synthesis Examples 1 to 10, 12 to 22, and SA-9000) with the polymer synthesized in Synthesis Example 11 at ratios of 90:10, 75:25, and 50:50, respectively, were spin-coated onto substrates and baked in an oven under nitrogen conditions at 100°C for 5 minutes and then at 250°C for 1 hour. The dielectric loss tangent of the resulting fired product was measured at 10 GHz using a cavity resonator method (TE mode resonator, dielectric constant measurement system, manufactured by AET Corporation). The dielectric loss tangent of the polymer being measured was calculated from the extrapolated value of the relationship between the obtained dielectric loss tangent result and the content ratio of the polymer being measured. The results are shown in Tables 1 and 2.

[0215] [Table 1]

[0216] <Polymer glass transition temperature (Tg)> A varnish for evaluation was prepared by mixing 100 parts by mass of the polymer to be measured (the polymers synthesized in Synthesis Examples 12 to 19 and SA-9000), 0.5 parts by mass of Percumyl D (NOF Corporation), and 100 parts by mass of toluene. The prepared varnish for evaluation was then applied to a copper foil (TQ-M4-VSP (Mitsui Kinzoku Co., Ltd.)) using a Baker-type applicator (gap: 75 μm) and dried at 100°C for 5 minutes to form a coating. A copper foil (TQ-M4-VSP (Mitsui Kinzoku Co., Ltd.)) was placed on the resulting coating, and the mixture was vacuum-pressed at 150°C for 5 minutes and then baked at 200°C under nitrogen for 2 hours to prepare a cured film with the copper foil. The prepared cured film with copper foil was immersed in a 40% by mass iron chloride solution, the copper foil was removed from the cured film with copper foil, washed with water, and dried at 80°C for 30 minutes to prepare a film for measuring the glass transition temperature (Tg). The results are shown in Table 2. A test piece (width: 3 mm × length: 1 cm) was cut out from the prepared Tg measurement film, and measured using a dynamic viscoelasticity measuring device (Seiko Instruments Inc., model number "EXSTAR4000") at a heating rate of 10°C / min from 50°C to 300°C at 1 Hz, and the tan δ at this time was taken as the glass transition temperature (Tg).

[0217] <Peel strength of polymer> A varnish for evaluation was prepared by mixing 100 parts by weight of the polymers to be measured (polymers synthesized in Synthesis Examples 12 to 19 and SA-9000), 0.5 parts by weight of Percumyl D (NOF Corporation), and 100 parts by weight of toluene. The prepared varnish for evaluation was then applied to a copper foil (TQ-M4-VSP (Mitsui Kinzoku Co., Ltd.)) using a Baker-type applicator (gap: 75 μm), heated at 100 ° C for 5 minutes, and then dried at 130 ° C for 5 minutes to form a coating. A copper foil (TQ-M4-VSP (Mitsui Kinzoku Co., Ltd.)) was placed on the resulting coating, vacuum-pressed at 150 ° C for 5 minutes, and then baked at 200 ° C for 2 hours under nitrogen to prepare a cured film with copper foil, which was used as a peel strength test sample. A test piece (width: 5 mm x length: 10 cm) was cut out from the prepared peel strength sample, and the cured film-coated copper foil (one copper foil and cured film laminated portion in the peel strength sample) was pulled at a 90-degree angle using an Instron 5567 manufactured by Instron Corporation at 500 mm / min, and the peel strength was measured in accordance with IPC-TM-650 2.4.9. The results are shown in Table 2.

[0218] [Table 2]

[0219] [Examples 1 to 14, 29 to 31 and Comparative Examples 1 to 7 and 18] The components listed in the column for composition type in Tables 3-1, 3-2, and 4 were mixed in a mixer rotor to the ratio (parts by mass) listed in the column for composition blend ratio in Tables 3-1, 3-2, and 4, and the concentration was adjusted with toluene to give a solids concentration of 50 parts by mass, thereby preparing the composition.

[0220] <Resin flow evaluation> The components listed in the "Composition Type" column in Tables 3-1, 3-2, and 4 were mixed in a mixer rotor to the ratios (parts by mass) listed in the "Composition Blend Ratio" column in Tables 3-1, 3-2, and 4, and 67% by mass of toluene was added to 100% by mass of this mixture to prepare a varnish. Glass cloth (Toyobo NE Glass, #1027) was immersed in the prepared varnish for 2 minutes, removed from the varnish, and then dried at 100°C for 5 minutes and then at 160°C for 10 minutes to prepare a prepreg. Copper foil (TQ-M4-VSP (Mitsui Kinzoku Co., Ltd., 10 x 10 cm)) was placed on both sides of the prepared prepreg (10 x 10 cm), and vacuum pressed at room temperature under 3 MPa. The temperature was then raised to 200°C at a rate of 10°C / min and held at 200°C for 2 hours to prepare a copper-clad laminate (10 x 10 cm). The resin that protruded from the prepared copper-clad laminate (10 x 10 cm) was cut off and the mass of the protruding resin was measured. The resin flow (%) was calculated using the following formula. Resin flow (%) = Resin mass protruding after pressing / Prepreg mass x 100

[0221] <Preparation of cured film> The compositions obtained in the above Examples and Comparative Examples were applied to copper foil (TQ-M4-VSP (manufactured by Mitsui Kinzoku Co., Ltd.)) using a Baker-type applicator (gap: 125 μm), and then dried at 100°C for 5 minutes. When the composition obtained in Example 4 or Comparative Example 2 was used, the coating was baked under nitrogen at 120°C for 1.5 hours, and then baked under nitrogen at 250°C for 3 hours. When the compositions obtained in the other Examples and Comparative Examples were used, the coating was baked under nitrogen at 120°C for 1.5 hours, and then baked under nitrogen at 180°C for 3 hours. The obtained cured film with the copper foil was immersed in a 40% by mass iron chloride solution, the copper foil was removed, and then the film was washed with water and dried in an oven at 80°C for 30 minutes to produce a cured film.

[0222] <Preparation of laminate> The compositions obtained in the above Examples and Comparative Examples were coated onto Kapton film (150EN-C, manufactured by DuPont-Toray Co., Ltd.) using a Baker-type applicator (gap: 12.5 μm) and dried at 100°C for 5 minutes. A 12 μm-thick copper foil (TQ-M4-VSP, manufactured by Mitsui Kinzoku Co., Ltd.) was placed on the coating film of the resulting laminate of coating film and Kapton film. The coating film and copper foil were then laminated together using a thermal laminator (VA-700, manufactured by Taisei Laminator Co., Ltd.) at 150°C and 0.3 m / min. When the composition obtained in Example 4 or Comparative Example 2 was used, the laminate was baked at 120°C under nitrogen for 1.5 hours, followed by baking at 250°C under nitrogen for 3 hours. When the compositions obtained in the other Examples and Comparative Examples were used, the laminate was baked at 120°C under nitrogen for 1.5 hours, followed by baking at 180°C under nitrogen for 3 hours.

[0223] <Dielectric loss tangent> Test pieces (width: 6 cm × length: 6 cm) were cut out from the prepared cured films, and the dielectric loss tangents of the test pieces at 10 GHz were measured using a cavity resonator method (TE mode resonator, dielectric constant measurement system, manufactured by AET Corporation). The results are shown in Tables 3-1, 3-2, and 4.

[0224] <Peel strength> Test pieces (width: 5 mm x length: 10 cm) were cut out from the prepared laminate, and the Kapton film with the cured film was pulled in a 90-degree direction at 500 mm / min using an Instron 5567 manufactured by Instron Corp., in accordance with IPC-TM-650 2.4.9, to measure the peel strength between the cured film and the copper foil. The results are shown in Tables 3-1, 3-2, and 4.

[0225] <Glass transition temperature (Tg)> Test pieces (width: 3 mm × length: 1 cm) were cut from the prepared cured films and measured using a dynamic viscoelasticity measuring device (Seiko Instruments Inc., "EXSTAR4000") at a heating rate of 10°C / min from 50°C to 300°C at 1 Hz, and the tan δ at this time was taken as the glass transition temperature (Tg). The results are shown in Tables 3-1, 3-2, and 4. When two or more tan δ values ​​existed, the lowest value was taken as Tg.

[0226] <Chemical resistance> The compositions obtained in the above Examples and Comparative Examples were applied to a copper foil (TQ-M4-VSP (manufactured by Mitsui Kinzoku Co., Ltd.)) using a Baker-type applicator (gap: 125 μm), followed by drying at 100° C. for 5 minutes. When the composition obtained in Example 4 or Comparative Example 2 was used, the coating was baked under nitrogen at 120° C. for 1.5 hours and then at 250° C. for 3 hours. When the composition obtained in the other Examples and Comparative Examples was used, the coating was baked under nitrogen at 120° C. for 1.5 hours and then at 180° C. for 3 hours to obtain a cured film with a copper foil, and the mass of the resulting cured film with a copper foil was measured. The mass of the copper foil before coating was weighed in advance, and the mass obtained by subtracting the mass of the copper foil from the mass of the obtained cured film with a copper foil was defined as the "mass of the cured film before immersion." The obtained cured film with copper foil was immersed in methyl ethyl ketone (1.5 L) at room temperature for 10 minutes, and then vacuum dried at 120°C for 3 hours, and the mass of the cured film with copper foil was measured. The mass obtained by subtracting the mass of the copper foil (preliminarily weighed) from the mass of the cured film with copper foil after vacuum drying was defined as the "mass of the cured film after immersion." The chemical resistance was evaluated by calculating the mass change rate using the following formula. A mass change rate of 90% or more was evaluated as ○, and a mass change rate of 90% or less was evaluated as ×. The results are shown in Tables 3-1, 3-2, and 4. Mass change rate (%)=mass of cured film after immersion x 100 / mass of cured film before immersion

[0227] <Appearance> The appearance of the produced cured films was visually observed, and cured films that had cracks were marked with "X", and cured films that had no cracks were marked with "O". The results are shown in Tables 3-1, 3-2, and 4.

[0228] <Impregnation test> A 5 cm x 7 cm x 95 μm thick glass cloth (Nitto Boseki Co., Ltd., #2116 type) was impregnated with the composition obtained in the above Examples or Comparative Examples and dried by heating at 160°C for 10 minutes to obtain a prepreg with a thickness of 110 μm. The obtained prepreg was observed in transmission mode at 300x magnification using a digital microscope (Keyence Corporation, VHX-6000) to observe voids between the glass cloth and the resin layer. In addition, the prepreg was bent 180° toward the long and short sides, and the presence or absence of resin powder falling off was visually observed. When no voids or powder fall-off were observed, the result was marked "○", and when voids or powder fall-off were observed, the result was marked "×". The results are shown in Tables 3-1, 3-2 and 4.

[0229] [Table 3-1]

[0230] [Table 3-2]

[0231] [Table 4]

[0232] The abbreviations used in Tables 3-1, 3-2 and 4 are explained below.

[0233] <Polymer> SA-9000: Sabic, end-modified polyphenylene ether

[0234] <Curable compound> SLK-1500: Shin-Etsu Chemical Co., Ltd., bismaleimide, number average molecular weight 1500 TAIC: Mitsubishi Chemical Corporation, triallyl isocyanurate Tufprene 912: Asahi Kasei Corporation, styrene butadiene styrene thermoplastic elastomer

[0235] <Other additives> Additive-1: Silica particles, Adma Fine (manufactured by Admatechs Co., Ltd., phenylaminosilane-modified particles, particle size 0.4 to 0.6 μm) Additive-2: Fluorine resin powder, Fluon+ EA-2000 (AGC Co., Ltd.)

[0236] <Initiator> DCP: Dicumyl peroxide, manufactured by Tokyo Chemical Industry Co., Ltd.

[0237] [Examples 15 to 28 and Comparative Examples 8 to 17] The components listed in the composition type column in Tables 5 and 6 were mixed in a mixer rotor to obtain the ratio (parts by mass) listed in the composition blending ratio column in Tables 5 and 6, and the concentration was adjusted with toluene to obtain a solids concentration of 30 parts by mass, thereby preparing a composition.

[0238] <Resin flow evaluation> The components listed in the "Composition Type" column in Tables 5 and 6 were mixed in a mixer rotor to the ratios (parts by mass) listed in the "Composition Blend Ratio" column in Tables 5 and 6, and 67% by mass of toluene was added to 100% by mass of this mixture to prepare a varnish. Glass cloth (Toyobo NE Glass, #1027) was immersed in the prepared varnish for 2 minutes, removed from the varnish, and then dried at 100°C for 5 minutes and then at 160°C for 10 minutes to prepare a prepreg. Copper foil (TQ-M4-VSP (Mitsui Kinzoku Co., Ltd., 10 x 10 cm)) was placed on both sides of the prepared prepreg (10 x 10 cm), and vacuum pressed at room temperature under 3 MPa. The temperature was then raised to 200°C at a rate of 10°C / min and held at 200°C for 2 hours to prepare a copper-clad laminate (10 x 10 cm). The resin that protruded from the prepared copper-clad laminate (10 x 10 cm) was cut off and the mass of the protruding resin was measured. The resin flow (%) was calculated using the following formula. Resin flow (%) = Resin mass protruding after pressing / Prepreg mass x 100

[0239] <Dielectric loss tangent> The compositions obtained in Examples 15 to 28 and Comparative Examples 8 to 17 were spin-coated onto a 3-inch quartz substrate, dried at 100°C for 5 minutes, and baked at 200°C for 2 hours under nitrogen to produce a dielectric loss tangent measurement substrate in which a cured film was formed on the quartz substrate. The dielectric loss tangent at 10 GHz of the quartz substrate before coating and the prepared dielectric loss tangent measurement substrate was measured using a cavity resonator method (TE mode resonator, dielectric constant measurement system, manufactured by AET Corporation). Based on the obtained results, the dielectric loss tangent of each composition was calculated using the following formula. The results are shown in Tables 5 and 6.

[0240] When a quartz substrate is used, the dielectric constant is Dk1, the dielectric dissipation factor is Df1, the thickness of the quartz substrate is t1, the dielectric constant is Dk2, the dielectric dissipation factor is Df2, and the thickness is t2 of the cured film, and when a dielectric dissipation factor measurement substrate is used, the dielectric constant is Dk3, the dielectric dissipation factor is Df3, and the thickness of the dielectric dissipation factor measurement substrate is t3, the dielectric constant (Dk2) and dielectric dissipation factor (Df2) of the cured film are calculated using the following formulas. Dk2 = [(Dk3 × t3) - (Dk1 × t1)] / t2 Df2=[(Dk3×Df3×t3)-(Dk1×Df1×t1)] / (Dk2×t2)

[0241] <Peel strength> The compositions obtained in Examples 15 to 28 and Comparative Examples 8 to 17 were applied to 18 μm-thick copper foil (CF-V9S-SV-18 (Fukuda Metal Foil & Powder Co., Ltd.)) using a Baker-type applicator (gap: 12.5 μm), and dried at 100°C for 5 minutes and then at 130°C for 5 minutes to form a coating film. An 18 μm-thick copper foil (CF-V9S-SV-18 (Fukuda Metal)) was placed on top of the formed coating film, pressed under vacuum at 150°C for 5 minutes, and then fired at 200°C for 2 hours under nitrogen to produce a laminate. The peel strength of the produced laminate was measured in the same manner as in Example 1. The results are shown in Tables 5 and 6.

[0242] <Glass transition temperature (Tg) and appearance> The compositions obtained in Examples 15 to 28 and Comparative Examples 8 to 17 were applied to copper foil (TQ-M4-VSP (manufactured by Mitsui Kinzoku Co., Ltd.)) using a Baker-type applicator (gap: 75 μm), dried at 100°C for 5 minutes, and baked at 200°C for 2 hours under nitrogen. The obtained cured film with the copper foil was immersed in a 40% by mass iron chloride solution, the copper foil was removed, the film was washed with water, and the film was dried in an oven at 80°C for 30 minutes to obtain a cured film. The glass transition temperature (Tg) and appearance of the obtained cured film were measured and evaluated in the same manner as in Example 1. The results are shown in Tables 5 and 6.

[0243] <Chemical resistance and impregnation test> Except for using the compositions obtained in Examples 15 to 28 and Comparative Examples 8 to 17, chemical resistance and impregnation tests were carried out in the same manner as in Example 1. The results are shown in Tables 5 and 6.

[0244] [Table 5]

[0245] [Table 6]

[0246] The abbreviations used in Tables 5 and 6 are explained below.

[0247] <Polymer> SA-9000: Sabic, end-modified polyphenylene ether

[0248] <Curable compound> TAIC: Mitsubishi Chemical Corporation, triallyl isocyanurate DVB960: Divinylbenzene (divinylbenzene 96% by mass), manufactured by Nippon Steel Chemical & Material Co., Ltd. BMI-3000: Designer Molecules, bismaleimide (bifunctional bismaleimide, Mw: approximately 3000) BMI-70: bis-(3-ethyl-5-methyl-4-maleimidophenyl)methane, manufactured by K.I. Chemical Co., Ltd.

[0249] <Antioxidants> Antioxidant-1: 2,2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl, manufactured by TCI Corporation Antioxidant-2: 3,5-di-tert-4-butylhydroxytoluene, manufactured by TCI Corporation Antioxidant-3: ADEKA Corporation, AO-30 (chemical name: 4,4',4''-(1-methylpropanyl-3-ylidene)tris(6-tert-butyl-m-cresol)

[0250] <Initiator> DCP: Dicumyl peroxide, manufactured by Tokyo Chemical Industry Co., Ltd.

Claims

1. It has a repeating structural unit represented by the following formula (1): A polymer having a group Y represented by the following formula (a) at its terminal: 【Chemistry 1】 In formula (1), each X is independently —O—, —S—, or —N(R 3 )- and R 3 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a portion of the hydrocarbon group or halogenated hydrocarbon group is substituted with at least one atom selected from an oxygen atom and a sulfur atom, and R 1 is a divalent organic group, and R 2 is a divalent unsubstituted or substituted pyrimidine ring; 【Chemistry 2】 In formula (a), Y is a group containing an ethylenically unsaturated double bond and having 3 to 50 carbon atoms.

2. R in the formula (1) 1 The polymer according to claim 1, wherein the divalent organic group represented by the formula (2-1) contains a group represented by the formula (2-1): 【Transformation 3】 In formula (2-1), Ar 1 and Ar 2 are each independently an unsubstituted or substituted aromatic hydrocarbon group, and L is a single bond, —O—, —S—, —N(R 8 )-, -C(O)-, -C(O)-O-, -C(O)-NH-, -S(O)-, -S(O) 2 -, -P(O)- or a divalent organic group, R 8 is a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms; y is an integer of 0 to 5; when y is 2 or more, a plurality of Ar 1 and L may be the same or different, R 6 and R 7 are each independently a single bond, a methylene group, or an alkylene group having 2 to 4 carbon atoms.

3. Ar in the formula (2-1) 1 and Ar 2 and each independently represent an aromatic hydrocarbon group having an allyl group.

4. The polymer according to any one of claims 1 to 3, having a weight average molecular weight in terms of polystyrene of 1,000 to 500,000.

5. The polymer according to any one of claims 1 to 4, and a curable compound (B) other than the polymer.

6. 6. The composition according to claim 5, wherein the curable compound (B) comprises at least one selected from the group consisting of vinyl compounds, maleimide compounds, allyl compounds, acrylic compounds, methacrylic compounds, thiol compounds, oxazine compounds, cyanate compounds, epoxy compounds, oxetane compounds, methylol compounds, benzocyclobutene compounds, propargyl compounds, and silane compounds.

7. The composition according to claim 5 or 6, further comprising an antioxidant.

8. A cured product which is a cured product of the composition according to any one of claims 5 to 7.

9. A substrate; A laminate having a cured product layer formed using the composition according to any one of claims 5 to 7.

10. An electronic component comprising the cured product according to claim 8 or the laminate according to claim 9.

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