Resin, resin composition, cured object, film, coating fluid composition, prepreg, electronic substrate, and method for producing resin

Abstract

Provided is a resin comprising a polycarbonate structural unit represented by formula (UN1) and a terminal structure having a vinyl group (with the proviso that any polycarbonate structural unit represented by formula (A1) and any terminal structure represented by formula (A2) are excluded). [In formula (UN1), Ux is a single bond or a divalent group, R1 and R2 are each independently a substituent, n is 0, 1, 2, 3, or 4, m is 0, 1, 2, 3, or 4, and * indicates a linking bond. Symbol * in formula (A1) indicates a linking bond and symbol * in formula (A2) indicates a linking bond to the repeating unit located at an end of the resin.]

Description

Resin, resin composition, cured product, film, coating composition, prepreg, electronic substrate, and method for producing resin

[0001] The present invention relates to a resin, a resin composition, a cured product, a film, a coating composition, a prepreg, an electronic substrate, and a method for producing the resin.

[0002] Next-generation high-speed communication technologies, known as 5G or 6G, boast features such as "high speed, large capacity," "multiple simultaneous connections," and "ultra-low latency." They are being introduced into various communication networks in fields such as electrical and electronic equipment, mobility (e.g., automobiles), and healthcare, bringing about economic and social transformation. The electronic circuit boards and semiconductor package substrates (hereinafter referred to as "electronic boards") used in these communication devices and other electronic devices also face various challenges in improving their performance. One major challenge is the increasing frequency used in communication due to the increase in information communication volume. As frequencies increase, materials used in conventional electronic boards experience increased transmission loss, which is the rate at which electrical signal energy is lost due to the conversion of unnecessary energy such as heat energy, resulting in energy loss and heat generation from the board. Transmission loss consists of two components: conductor loss and dielectric loss. Dielectric loss is proportional to the square root of the dielectric constant (Dk) and the dielectric loss tangent (Df) of the dielectric. Therefore, to reduce transmission loss in electronic boards and other devices using insulating materials, it is necessary to reduce the dielectric constant and dielectric loss tangent of the insulating material. Furthermore, in order to reduce conductor loss, there is a trend toward reducing the roughness of the interface between the substrate and the metal wiring. Therefore, insulating materials are required to have better adhesion to metal foils and metal plating. Electronic substrate materials are required to have not only reduced transmission loss but also various other properties. Examples include high heat resistance to withstand high-temperature solder reflow and low thermal expansion to prevent substrate warpage due to the difference in thermal expansion coefficient between the copper circuit and the insulating layer. Furthermore, when used as an insulating material for coating and molding onto a substrate, the properties required of the electronic substrate material include high solvent solubility, low solution viscosity, and filler dispersibility. Furthermore, the properties required of electronic substrate materials used to form thin films used in lamination molding of wiring layers include high solvent solubility, low viscosity, filler dispersibility, and minimal change in dielectric properties under the usage environment, such as temperature and humidity.As insulating materials, thermoplastic resins such as liquid crystal polymers, polyphenylene ether (PPE), polyimides, and fluororesins, as well as thermosetting resins such as epoxy resins, maleimide resins, and PPE, have been improved and developed for various applications, including electronic substrates. Thermosetting PPE is primarily used for electronic substrate applications. However, the dielectric properties of PPE are currently insufficient for application to next-generation high-speed communication technologies such as 5G and 6G. Among these resins, polycarbonate resin has been used as a material for molded products in various industrial fields due to its excellent mechanical, thermal, electrical, and transparency properties. However, for use in the above-mentioned high-frequency electronic substrates, typical bisphenol A polycarbonates have poor solubility in organic solvents and solution stability, making them difficult to apply to insulating coating solutions for fine wiring or to mold thin insulating films.

[0003] For example, Patent Document 1 describes a polycarbonate resin having a functional group capable of undergoing a crosslinking reaction and having a predetermined molecular structure as a resin used in a photosensitive layer.

[0004] Furthermore, Patent Document 2 describes a soluble thermoplastic graft polycarbonate obtained by a predetermined manufacturing method.

[0005] Furthermore, Patent Document 3 describes a curable polycarbonate resin or polyarylate resin having at least one reactive group selected from the group consisting of a (meth)acryloyloxy group, a vinylbenzyl ether group, and an allyl ether group as a terminal structure and having a predetermined molecular structure.

[0006] International Publication No. 1997 / 020878 Japanese Patent Application Laid-Open No. 55-50009 International Publication No. 2022 / 038893

[0007] Patent Documents 1 and 2 neither describe nor suggest the properties (for example, dielectric properties and thermal properties) required for polycarbonate resins to be used as electronic substrate materials.

[0008] Patent Document 3 describes the properties required for polycarbonate resins or polyarylate resins for use as insulating layers in electronic substrates. When comparing the dielectric constant and the dielectric loss tangent, lowering the dielectric loss tangent has a significant effect on reducing transmission loss. Therefore, it is advantageous to use a resin with a low dielectric loss tangent. However, the resin disclosed in Patent Document 3 leaves room for further improvement in terms of sufficiently lowering the dielectric loss tangent.

[0009] An object of the present invention is to provide a resin capable of reducing the dielectric loss tangent, a resin composition containing the resin, a cured product, a film, a coating composition, a prepreg, an electronic substrate, and a method for producing the resin.

[0010] As a result of extensive research, the present inventors have found that a resin having a specific structural unit has dielectric properties that allow it to be used as an electronic substrate material, and also has a reduced dielectric loss tangent. That is, the gist of the present invention resides in the following [Configuration 1] to [Configuration 16].

[0011] [Configuration 1] A resin containing a polycarbonate structural unit represented by the following formula (UN1) and a terminal structure having a vinyl group (however, excluding the polycarbonate structural unit represented by the following formula (A1) and the terminal structure represented by the following formula (A2)).

[0012]

[0013]

[0014] [(In the formula (UN1), R １ and R ２are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group; n is 0, 1, 2, 3, or 4; m is 0, 1, 2, 3, or 4; R １ If there are multiple R １ are the same or different from each other, R ２ If there are multiple R ２ are the same or different, Ux is (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -C(R ３ ) (R ４ )- groups represented by —S—, —SO—, —SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), R ３ and R ４are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, and * represents a bond. (The * in the formula (A1) represents a bond, and the * in the formula (A2) represents a bond to a repeating unit located at an end of the resin.)

[0015] [Configuration 2] The resin according to Configuration 1, wherein the terminal structure is a terminal structure represented by the following formula (ME1):

[0016]

[0017] (In the formula (ME1), R １１ represents a hydrogen atom, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; q is 0, 1, or 2; provided that when q is 0, benzene ring A has a vinyl group; when q is 1, benzene ring B has a vinyl group; when q is 2, only the benzene ring B farthest from benzene ring A has a vinyl group; and * represents a bond.

[0018] [Configuration 3] The resin according to Configuration 1 or 2, wherein the terminal structure includes at least one terminal structure selected from the group consisting of terminal structures represented by the following formulas (ME11), (ME12), (ME13), and (ME14):

[0019]

[0020] (In the formulae (ME11), (ME12), (ME13), and (ME14), * represents a bond.)

[0021] [Configuration 4] The resin according to any one of Configurations 1 to 3, wherein the polycarbonate structural unit represented by formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formulas (UN11) and (UN12):

[0022]

[0023]

[0024] [(In the formula (UN11), Ux is a single bond, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, or —C(R ３ ) (R ４ )-, and R １５１ , R １５２ , R １５３ , R １５４ , R １５５ , R １５６ , R １５７ , and R １５８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; R ３ and R ４ represents R in the formula (UN1). ３ and R ４ and * is a bond.) (In the formula (UN12), R ２１４ and R ２１５ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R ２１１ , R ２１２ , R ２１３ , R ２１６ , R ２１７ , and R ２１８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * represents a bond.

[0025] [Configuration 5] The resin according to Configuration 4, wherein the polycarbonate structural unit represented by formula (UN11) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulas (UN111), (UN112), (UN113), (UN114), (UN115), (UN116), and (UN117), and the polycarbonate structural unit represented by formula (UN12) is a polycarbonate structural unit represented by the following formula (UN121).

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034] (In the formula (UN111), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ５１ , R ５２ , and R ５３ are each independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, * is a bond, and in the formulae (UN112) to (UN115), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ * is a bond, and in the formula (UN116), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R１５８ is synonymous with R ３１ and R ４１ are each independently a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, * is a bond, and in the formula (UN117), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ３２ is a substituted or unsubstituted alkyl group having 1 carbon atom, R ４２ is a substituted or unsubstituted alkyl group having 13 to 22 carbon atoms, ４２ represents a linear alkyl group, * represents a bond, and in the formula (UN121), R ２１２ , R ２１４ , R ２１５ , and R ２１７ are each independently R in formula (UN12). ２１２ , R ２１４ , R ２１５ , and R ２１７ and * is a bond.)

[0035] [Configuration 6] The resin according to any one of Configurations 1 to 5, wherein the polycarbonate structural unit represented by formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulas (UN111-TMC-1), (UN111-TMC-2), (UN112-CH), (UN116-CH), (UN121-CH), (UN113-BP-1), (UN113-BP-2), (UN115-BP), (UN116-BP), (UN114-CDE-1), (UN114-CDE-2), and (UN117-LL).

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] (In the formulae (UN111-TMC-1), (UN111-TMC-2), (UN112-CH), (UN116-CH), (UN121-CH), (UN113-BP-1), (UN113-BP-2), (UN115-BP), (UN116-BP), (UN114-CDE-1), (UN114-CDE-2), and (UN117-LL), * represents a bond.)

[0042] [Configuration 7] In the resin according to any one of Configurations 1 to 6, １ A resin having a number average molecular weight calculated from a H-NMR spectrum of 500 or more and 20,000 or less.

[0043] [Configuration 8] A method for producing the resin according to any one of Configurations 1 to 7, comprising a step of interfacially polycondensing a bischloroformate monomer or bischloroformate oligomer represented by the following formula (M-UN1), from which the polycarbonate structural unit represented by formula (UN1) is derived, a bisphenol compound, and a phenol compound represented by the following formula (M-ME1), from which formula (ME1) is derived.

[0044]

[0045]

[0046] (In the formula (M-UN1), Ux, R １ , R ２ , m, and n each independently represent Ux, R in formula (UN1). １ , R ２ , m, and n; １Ａ represents the average number of mers, and n １Ａ is 1.0 or more and 10 or less, and in the formula (M-ME1), R １１represents a hydrogen atom, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and q is 0, 1, or 2, provided that when q is 0, benzene ring A has a vinyl group, when q is 1, benzene ring B has a vinyl group, and when q is 2, only the benzene ring B farthest from benzene ring A has a vinyl group.

[0047] [Configuration 9] A resin composition comprising the resin according to any one of Configurations 1 to 7 and a radical polymerization initiator.

[0048] [Configuration 10] A cured product obtained by curing the resin composition according to Configuration 9.

[0049] [Configuration 11] The cured product according to Configuration 10, wherein the cured product has a relative dielectric constant Dk of 2.85 or less at a frequency of 10 GHz as measured by a resonator perturbation method using a split cylinder resonator.

[0050] [Configuration 12] The cured product according to Configuration 10 or 11, wherein the cured product has a dielectric loss tangent Df of 0.00300 or less at a frequency of 10 GHz as measured by a resonator perturbation method using a split cylinder resonator.

[0051] [Configuration 13] A film comprising the cured product according to any one of Configurations 10 to 12.

[0052] [Configuration 14] A coating composition comprising the resin composition according to Configuration 9 and a non-halogenated solvent, wherein the resin composition is dissolved in the non-halogenated solvent.

[0053] [Configuration 15] A prepreg comprising the coating composition according to Configuration 14 and a fibrous substrate, wherein the fibrous substrate is impregnated with the coating composition, and the coating composition is a semi-cured product or a fully cured product.

[0054] [Configuration 16] An electronic substrate comprising the prepreg according to Configuration 15 and copper foil.

[0055] According to one aspect of the present invention, it is possible to provide a resin capable of reducing the dielectric loss tangent, a resin composition containing the resin, a cured product, a film, a coating composition, a prepreg, an electronic substrate, and a method for producing the resin.

[0056] 1 is a graph showing the evaluation results of the temperature dependence of dielectric properties (relative dielectric constant (Dk)) in one embodiment of the example, comparative example 1, and reference example 1. FIG. 2 is a graph showing the evaluation results of the temperature dependence of dielectric properties (dielectric loss tangent (Df)) in one embodiment of the example, comparative example 1, and reference example 1.

[0057] [Resin] One aspect of the resin according to this embodiment includes a polycarbonate structural unit represented by the following formula (UN1) and a terminal structure having a vinyl group (however, excluding a polycarbonate structural unit represented by the following formula (A1) and a terminal structure represented by the following formula (A2)).

[0058]

[0059]

[0060] [(In the formula (UN1), R １ and R ２ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group; n is 0, 1, 2, 3, or 4; m is 0, 1, 2, 3, or 4; R １ If there are multiple R １ are the same or different from each other, R ２ If there are multiple R ２are the same or different, Ux is (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -C(R ３ ) (R ４ )-, a group represented by —S—, —SO—, —SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), R ３ and R ４ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, and * represents a bond. (The * in the formula (A1) represents a bond, and the * in the formula (A2) represents a bond to a repeating unit located at an end of the resin.)

[0061] In this specification, the term "resin" refers to both homopolymers and copolymers, and when the resin is specified as a copolymer, it is referred to as a copolymer. Furthermore, a polycarbonate structural unit may be referred to as a PC structural unit, and a polycarbonate polymer may be referred to as a PC polymer.

[0062] In one aspect of the resin according to this embodiment, Ux in formula (UN1) represents a single bond, a substituted or unsubstituted alkylene group having 1 to 28 ring carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, or —C(R ３ ) (R ４ )- is also preferred.

[0063] In one aspect of the resin according to the present embodiment, it is also preferable that n and m in formula (UN1) are each independently 1, 2, or 3.

[0064] In one aspect of the resin according to this embodiment, when n and m in formula (UN1) are each independently 1, 2, or 3, R １ and R ２ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0065] In one aspect of the resin according to the present embodiment, the terminal structure having a vinyl group is present at both terminals of the resin or at one terminal of the resin. The terminal structure having a vinyl group in the resin according to one aspect of the present embodiment is bonded to a repeating unit located at the terminal of the resin.

[0066] In one aspect of the resin according to this embodiment, it is also preferable that the terminal structure having a vinyl group does not include a terminal structure represented by the following formula (A2). That is, in one aspect of the resin according to this embodiment, it is also preferable that the terminal structure having a vinyl group does not include a terminal structure represented by the following formula (A2). The terminal structure represented by the following formula (A2) contains an ester group, which is a highly polar structure. According to the Clausius-Mossotti equation, a highly polar structure increases the relative permittivity and therefore deteriorates the dielectric properties. Furthermore, a highly polar structure also deteriorates the dielectric loss tangent (i.e., increases the dielectric loss tangent). Therefore, in order to exhibit low dielectric properties, the terminal structure having a vinyl group is preferably a low-polarity skeleton such as styrene or naphthalene, rather than a terminal structure having a highly polar structure such as the following formula (A2).

[0067]

[0068] (In the formula (A2), * represents a bond to a repeating unit located at the end of the resin.)

[0069] In one aspect of the resin according to this embodiment, the terminal structure having a vinyl group is also preferably a terminal structure represented by the following formula (ME1).

[0070]

[0071] (In the formula (ME1), R １１represents a hydrogen atom, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; q is 0, 1, or 2; provided that when q is 0, benzene ring A has a vinyl group; when q is 1, benzene ring B has a vinyl group; when q is 2, only the benzene ring B farthest from benzene ring A has a vinyl group; and * represents a bond.

[0072] One embodiment of the formula (ME1) is represented by the following formula (ME1-A1), formula (ME1-A2), or formula (ME1-A3).

[0073]

[0074] (In the formulas (ME1-A1), (ME1-A2), and (ME1-A3), R １１ represents R in formula (ME1). １１ and * represents a bond.)

[0075] In one aspect of the resin according to this embodiment, it is also preferable that the terminal structure having a vinyl group includes at least one terminal structure selected from the group consisting of terminal structures represented by the following formulae (ME1-1), (ME1-2), and (ME1-3). The following formulae (ME1-1), (ME1-2), and (ME1-3) correspond to the terminal structures having a vinyl group when q is 0, q is 1, and q is 2 in the formula (ME1), respectively. That is, the following formulae (ME1-2) and (ME1-3) are the same as the formulae (ME1-A2) and (ME1-A3).

[0076]

[0077] (In the formulas (ME1-1), (ME1-2), and (ME1-3), R １１ represents R in formula (ME1). １１ and * indicates a bond.)

[0078] In one aspect of the resin according to this embodiment, it is also preferable that the terminal structure having a vinyl group includes at least one terminal structure selected from the group consisting of terminal structures represented by the following formulas (ME11), (ME12), (ME13), and (ME14):

[0079]

[0080] (In the formulae (ME11), (ME12), (ME13), and (ME14), * represents a bond.)

[0081] In one aspect of the resin according to this embodiment, it is also preferable that the terminal structure having a vinyl group includes at least one terminal structure selected from the group consisting of terminal structures represented by formula (ME11), formula (ME12), and formula (ME13). In one aspect of the resin according to this embodiment, it is also preferable that the terminal structure having a vinyl group includes any one terminal structure selected from the group consisting of terminal structures represented by formula (ME11), formula (ME12), and formula (ME13).

[0082] In one aspect of the resin according to this embodiment, the resin does not include a resin containing both the polycarbonate structural unit represented by formula (A1) and the terminal structure represented by formula (A2). That is, in one aspect of the resin according to this embodiment, a resin containing both the polycarbonate structural unit represented by formula (A1) and the terminal structure represented by formula (A2) is excluded.

[0083] In one aspect of the resin according to the present embodiment, it is also preferable that the polycarbonate structural unit represented by formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formulas (UN11) and (UN12) below:

[0084]

[0085]

[0086] [(In the formula (UN11), Ux is a single bond, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, or —C(R ３ ) (R ４ )-, and R １５１ , R １５２ , R １５３ , R １５４ , R １５５ , R １５６ , R １５７ , and R １５８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; R ３ and R ４ are each independently R in formula (UN1). ３ and R ４ and * is a bond.) (In the formula (UN12), R ２１４ and R ２１５ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R ２１１ , R ２１２ , R ２１３ , R ２１６ , R ２１７ , and R ２１８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * represents a bond.

[0087] In one aspect of the resin according to this embodiment, Ux in formula (UN11) represents a single bond, a substituted or unsubstituted alkylene group having 1 to 28 ring carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, or —C(R ３ ) (R ４ )- is also preferred.

[0088] In one aspect of the resin according to this embodiment, R １５１ , R １５４ , R １５６ , and R １５７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0089] In one aspect of the resin according to this embodiment, R １５１ ~R １５８ may be a hydrogen atom.

[0090] In one aspect of the resin according to this embodiment, R １５１ , R １５４ , R １５６ , and R １５７ In one aspect of the resin according to this embodiment, R in formula (UN11) is preferably not a hydrogen atom. １５２ and R １５３ and at least one of R １５５ and R １５８ At least one of R is a hydrogen atom, １５１ , R １５４ , R １５６ , and R １５７ is also preferably not a hydrogen atom.

[0091] In one aspect of the resin according to this embodiment, —C(R ３ ) (R ４ One embodiment of the group represented by —C(R ３１ ) (R ４１ It is also preferred that the group is represented by —C(R ３１ ) (R４１ )-, in which R ３１ and R ４１ are each independently a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms.

[0092] In one aspect of the resin according to this embodiment, —C(R ３ ) (R ４ One embodiment of the group represented by —C(R ３２ ) (R ４２ It is also preferred that the group is represented by —C(R ３２ ) (R ４２ )-, in which R ３２ is a substituted or unsubstituted alkyl group having 1 carbon atom, and R ４２ is a substituted or unsubstituted alkyl group having 13 to 22 carbon atoms, provided that R ４２ is a straight chain alkyl group.

[0093] In one aspect of the resin according to this embodiment, R ２１２ and R ２１７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0094] In one aspect of the resin according to this embodiment, R ２１１ ~R ２１３ , R ２１６ ~R ２１８ In one aspect of the resin according to this embodiment, R in formula (UN12) is preferably not a hydrogen atom. ２１１ , R ２１３ , R ２１６ , and R ２１８ is a hydrogen atom, and R in the formula (UN12) ２１２ and R ２１７ is also preferably not a hydrogen atom.

[0095] In one aspect of the resin according to the present embodiment, the polycarbonate structural unit represented by formula (UN1) is also preferably at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulas (UN111), (UN112), (UN113), (UN114), (UN115), (UN116), (UN117), and (UN121):

[0096] In one aspect of the resin according to the present embodiment, the polycarbonate structural unit represented by formula (UN11) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulas (UN111), (UN112), (UN113), (UN114), (UN115), (UN116), and (UN117), and it is also preferable that the polycarbonate structural unit represented by formula (UN12) is a polycarbonate structural unit represented by the following formula (UN121).

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] (In the formula (UN111), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ５１ , R ５２ , and R ５３are each independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, * is a bond, and in the formulae (UN112) to (UN115), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ * is a bond, and in the formula (UN116), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ３１ and R ４１ are each independently a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, * is a bond, and in the formula (UN117), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ３２ is a substituted or unsubstituted alkyl group having 1 carbon atom, R ４２ is a substituted or unsubstituted alkyl group having 13 to 22 carbon atoms, ４２ represents a linear alkyl group, * represents a bond, and in the formula (UN121), R ２１２ , R ２１４ , R ２１５ , and R ２１７ are each independently R in formula (UN12). ２１２ , R ２１４ , R ２１５ , and R ２１７ and * is a bond.)

[0106] In one aspect of the resin according to the present embodiment, it is also preferable that the polycarbonate structural unit represented by formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulae (UN111-TMC-1), (UN111-TMC-2), (UN112-CH), (UN116-CH), (UN121-CH), (UN113-BP-1), (UN113-BP-2), (UN115-BP), (UN116-BP), (UN114-CDE-1), (UN114-CDE-2), and (UN117-LL).

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] (In the formulae (UN111-TMC-1), (UN111-TMC-2), (UN112-CH), (UN116-CH), (UN121-CH), (UN113-BP-1), (UN113-BP-2), (UN115-BP), (UN116-BP), (UN114-CDE-1), (UN114-CDE-2), and (UN117-LL), * represents a bond.)

[0113] One aspect of the resin according to this embodiment includes at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN11) and formula (UN12), and a terminal structure having a vinyl group.

[0114] In one aspect of the resin according to the present embodiment, which includes at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN11) and formula (UN12) and a terminal structure having a vinyl group, it is preferable that the polycarbonate structural unit represented by formula (UN11) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN111), formula (UN112), formula (UN113), formula (UN114), formula (UN115), formula (UN116), and formula (UN117). In one aspect of the resin according to the present embodiment, which includes at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN11) and formula (UN12) and a terminal structure having a vinyl group, the polycarbonate structural unit represented by formula (UN12) is preferably a polycarbonate structural unit represented by formula (UN121).

[0115] In one aspect of the resin according to the present embodiment, which includes at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN11) and formula (UN12) and a terminal structure having a vinyl group, the terminal structure having a vinyl group does not include the terminal structure represented by formula (A2). That is, in one aspect of the resin, the terminal structure having a vinyl group excludes the terminal structure represented by formula (A2).

[0116] In one aspect of the resin according to the present embodiment, which comprises at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN11) and formula (UN12) and a terminal structure having a vinyl group, the resin does not comprise a resin comprising a polycarbonate structural unit represented by formula (A1) and a terminal structure represented by formula (A2). That is, in one aspect of the resin, resins comprising a polycarbonate structural unit represented by formula (A1) and a terminal structure represented by formula (A2) are excluded from the resin.

[0117] In one aspect of the resin according to the present embodiment, which comprises at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN11) and formula (UN12) and a terminal structure having a vinyl group, it is also preferable that the terminal structure having a vinyl group is a terminal structure represented by formula (ME1), and it is also preferable that the terminal structure has at least one terminal structure selected from the group consisting of terminal structures represented by formula (ME1-1), formula (ME1-2), and formula (ME1-3), and it is also preferable that the terminal structure has at least one terminal structure selected from the group consisting of terminal structures represented by formula (ME11), formula (ME12), formula (ME13), and formula (ME14).

[0118] In one aspect of the resin according to the present embodiment, the resin includes at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the formula (UN11) and the formula (UN12), and a terminal structure having a vinyl group. In this resin, the polycarbonate structural unit represented by the formula (UN11) is selected from the group consisting of polycarbonate structural units represented by the formula (UN111-TMC-1), the formula (UN111-TMC-2), the formula (UN112-CH), the formula (UN116-CH), the formula (UN113- It is also preferable that the polycarbonate structural unit represented by formula (UN112) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN113-BP-2), formula (UN115-BP), formula (UN116-BP), formula (UN114-CDE-1), formula (UN114-CDE-2), and formula (UN117-LL), and it is also preferable that the polycarbonate structural unit represented by formula (UN12) is formula (UN121-CH).

[0119] The resin according to this embodiment preferably has a low amount of terminal hydroxyl groups. The amount of terminal hydroxyl groups refers to the hydroxyl groups derived from the remaining bisphenol and the hydroxyl groups derived from the polymer terminals. When the amount of terminal hydroxyl groups increases, the low dielectric properties tend to decrease because a highly polar structure increases the relative dielectric constant according to the Clausius-Mossotti equation. Furthermore, a highly polar structure tends to increase the dielectric loss tangent.

[0120] From this viewpoint, the resin according to this embodiment preferably has a terminal hydroxyl group content of 6000 ppm or less, which may be, by mass, 3000 ppm or less, 1000 ppm or less, 900 ppm or less, 800 ppm or less, 700 ppm or less, 600 ppm or less, 500 ppm or less, 400 ppm or less, 300 ppm or less, 215 ppm or less, 200 ppm or less, 100 ppm or less, or 50 ppm or less.

[0121] The method for calculating the amount of terminal hydroxyl groups is as follows: １ The molar ratio of each structure (structural unit) of the polycarbonate is calculated by H-NMR. The respective structures refer to the main structure, the sub-structure, the terminal structure having a vinyl group, and the hydroxyl group terminal structure. An example of a terminal structure having a vinyl group is the formula (ME1) described above. An example of a hydroxyl group terminal structure is the following formula (ME-UN1) from which the structural unit represented by the formula (UN1) is derived. When the resin according to this embodiment is produced by an interfacial polycondensation method, some catalyst-derived terminal polycarbonate (for example, diethylamine-terminated polycarbonate derived from triethylamine) is also produced. The mass ratio is calculated from the calculated molar ratio and the molecular weight of each structure, and the amount of hydroxyl groups in the mass of the entire polymer is calculated using ppm by mass.

[0122]

[0123] (In the formula (ME-UN1), Ux, R １ , R ２ , m, and n each independently represent Ux, R in formula (UN1). １ , R ２ * is a bond to a repeating unit located at the end of the resin.)

[0124] [Copolymer] The resin according to this embodiment may be a copolymer. One aspect of the resin according to this embodiment is a copolymer including a polycarbonate structural unit represented by formula (UN1) and a terminal structure having a vinyl group. Another aspect of the resin according to this embodiment is a copolymer including at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formula (UN11) and formula (UN12) and a terminal structure having a vinyl group.

[0125] In the copolymer according to this embodiment, specific examples of the terminal structure having a vinyl group are as described above in the section on resins.

[0126] In the copolymer according to this embodiment, the repeating units are not necessarily consecutive. One aspect of the copolymer according to this embodiment is a block copolymer, an alternating copolymer, or a random copolymer.

[0127] When the copolymer according to this embodiment contains a plurality of polycarbonate structural units represented by the formula (UN1), the plurality of polycarbonate structural units represented by the general formula (UN1) may be the same or different from one another.

[0128] One aspect of the copolymer according to the present embodiment has a polycarbonate structural unit represented by the formula (UN1) and a polycarbonate structural unit represented by the following formula (UN2), and the polycarbonate structural unit represented by the formula (UN1) and the polycarbonate structural unit represented by the following formula (UN2) are different from each other.

[0129]

[0130] (In the formula (UN2), R ６ and R ７are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group; r is 0, 1, 2, 3, or 4; s is 0, 1, 2, 3, or 4; R ６ If there are multiple R ６ are the same or different from each other, R ７ If there are multiple R ７ are the same or different, Uy is (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -C(R ３ ) (R ４ )-, a group represented by —S—, —SO—, —SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), R ３ and R ４ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, and * represents a bond.

[0131] In one aspect of the copolymer according to this embodiment, the polycarbonate structural unit represented by the general formula (UN2) is a structural unit represented by at least one selected from the group consisting of polycarbonate structural units represented by the formulas (UN11) and (UN12). When the copolymer according to this embodiment contains a plurality of polycarbonate structural units represented by the formula (UN11), the plurality of polycarbonate structural units represented by the general formula (UN11) may be the same as or different from one another. When the copolymer according to this embodiment contains a plurality of polycarbonate structural units represented by the formula (UN12), the plurality of polycarbonate structural units represented by the general formula (UN12) may be the same as or different from one another.

[0132] In one aspect of the copolymer according to the present embodiment, when the copolymer contains a polycarbonate structural unit represented by formula (UN1) and a polycarbonate structural unit represented by formula (UN2) that is different from the polycarbonate structural unit represented by formula (UN1), the polycarbonate structural unit represented by general formula (UN1) is a polycarbonate structural unit represented by formula (UN11) or formula (UN12). In one aspect of the copolymer according to the present embodiment, when the copolymer contains a polycarbonate structural unit represented by formula (UN1) and a polycarbonate structural unit represented by formula (UN2) that is different from the polycarbonate structural unit represented by formula (UN1), the polycarbonate structural unit represented by general formula (UN2) is a polycarbonate structural unit represented by formula (UN11) or formula (UN12).

[0133] In one aspect of the copolymer according to the present embodiment, when the copolymer contains a polycarbonate structural unit represented by formula (UN1) and a polycarbonate structural unit represented by formula (UN2) that is different from the polycarbonate structural unit represented by formula (UN1), the polycarbonate structural unit represented by formula (UN1) is a polycarbonate structural unit represented by formula (UN111), (UN112), (UN113), (UN114), (UN115), (UN116), (UN117), or (UN121), and the polycarbonate structural unit represented by formula (UN2) is a polycarbonate structural unit represented by formula (UN111), (UN112), (UN113), (UN114), (UN115), (UN116), (UN117), or (UN121).

[0134] In one aspect of the copolymer according to the present embodiment, when the copolymer contains a polycarbonate structural unit represented by formula (UN1) and a polycarbonate structural unit represented by formula (UN2) that is different from the polycarbonate structural unit represented by formula (UN1), the polycarbonate structural unit represented by formula (UN1) is a polycarbonate structural unit represented by formula (UN111-TMC-1), formula (UN111-TMC-2), formula (UN112-CH), formula (UN116-CH), formula (UN121-CH), formula (UN113-BP-1), formula (UN113-BP-2), formula (UN115-BP), formula (UN116-BP), formula (UN114- The polycarbonate structural unit represented by formula (UN2) is a polycarbonate structural unit represented by formula (UN111-TMC-1), formula (UN111-TMC-2), formula (UN112-CH), formula (UN116-CH), formula (UN121-CH), formula (UN113-BP-1), formula (UN113-BP-2), formula (UN115-BP), formula (UN116-BP), formula (UN114-CDE-1), formula (UN114-CDE-2), or formula (UN117-LL).

[0135] (Dielectric Properties) There are various methods for evaluating dielectric properties. One commonly used method is the cavity resonator perturbation method (hereinafter referred to as the cavity resonance method), which uses an electric field along the sample to evaluate dielectric properties. However, the electric field at both ends of the sample is deflected outside the sample. Because no known quantitative explanation for this imperfection has been established, it is common to calculate the dielectric constant assuming that the electric field passes through the entire sample. Therefore, even though the electric field is not applied at both ends of the sample, the dielectric constant is measured as low because the dielectric properties are calculated assuming that the electric field is applied throughout the sample. On the other hand, the split cylinder resonator perturbation method (hereinafter referred to as the split cylinder method), which uses a circular electric field along the sample surface, does not produce errors due to the deflection of the electric field at both ends of the sample, which occurs in the cavity resonance method. Therefore, the split cylinder method outputs dielectric properties closer to the true value than the cavity resonance method.

[0136] The dielectric constant Dk of the resin according to one aspect of this embodiment is preferably 2.85 or less, more preferably 2.80 or less, more preferably 2.75 or less, more preferably 2.70 or less, even more preferably 2.65 or less, even more preferably 2.60 or less, and even more preferably 2.50 or less. In this specification, the dielectric constant Dk of the resin is a value measured at room temperature (23°C) and a frequency of 10 GHz using a split cylinder resonator.

[0137] Furthermore, the dielectric loss tangent Df of the resin according to one aspect of this embodiment is preferably 0.02000 or less, more preferably 0.00700 or less, more preferably 0.00500 or less, more preferably 0.00350 or less, more preferably 0.00300 or less, even more preferably 0.00250 or less, even more preferably 0.00200 or less, and even more preferably 0.00140 or less. In particular, from the viewpoint of achieving a low dielectric loss tangent, the dielectric loss tangent Df of the resin according to one aspect of this embodiment is more preferably 0.00300 or less. In this specification, the dielectric loss tangent Df of the resin is a value measured at room temperature (23°C) and a frequency of 10 GHz using a split cylinder resonator. When the relative permittivity Dk and dielectric loss tangent Df of the resin according to this embodiment are equal to or less than the upper limit of the above range, the loss of electrical signals in the electronic board can be reduced when the resin according to this embodiment is used as an electronic board material. Furthermore, one of the characteristics required for electronic circuit board materials is that the resin according to this embodiment exhibits small changes in its dielectric properties (dielectric constant Dk and dielectric loss tangent Df) under different temperature environments (for example, environments ranging from 30°C to 150°C).

[0138] (Number average molecular weight) of the resin according to one aspect of this embodiment １ The number average molecular weight Mn calculated from the H-NMR spectrum is preferably 500 or more and 20,000 or less, more preferably 500 or more and 15,000 or less, even more preferably 500 or more and 10,000 or less, and still more preferably 500 or more and 8,000 or less. In this specification, the number average molecular weight Mn is determined by dissolving the resin in methylene dichloride as a solvent to prepare a solution, and measuring the molecular weight Mn using a nuclear magnetic resonance spectrometer. １ The H-NMR spectrum is measured to determine the composition ratio of each monomer component of the obtained resin, and the chromaticity is derived from the obtained composition ratio. Specifically, it can be measured by the method described in the Examples section.

[0139] (Thermal Expansion Coefficient) Since the resin according to this embodiment preferably has a low thermal expansion coefficient, the thermal expansion coefficient of the resin according to one aspect of this embodiment at temperatures from 40°C to 100°C is preferably 160 [ppm / K] or less, preferably 150 [ppm / K] or less, preferably 120 [ppm / K] or less, more preferably 115 [ppm / K] or less, even more preferably 100 [ppm / K] or less, even more preferably 90 [ppm / K] or less, and even more preferably 80 [ppm / K] or less. The thermal expansion coefficient (thermal expansion coefficient) can be measured by the method described in the Examples section.

[0140] (Glass Transition Temperature (Tg)) The resin according to this embodiment preferably has a glass transition temperature (Tg) of 80° C. or higher, more preferably 100° C. or higher, even more preferably 120° C. or higher, even more preferably 150° C. or higher, and even more preferably 170° C. or higher. The glass transition temperature can be measured by the method described in the Examples section.

[0141] (Explanation of Substituents, etc.) In the resin according to this embodiment, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0142] In the resin according to this embodiment, examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, butyl, sec-butyl, tert-butyl, various pentyl groups, and various hexyl groups. In this specification, when the term "various" is added to the name of a substituent, this term includes linear and branched groups, and the same applies hereinafter. In the resin according to this embodiment, a linear alkyl group may be referred to as a "linear alkyl group." In the resin according to this embodiment, examples of the substituted alkyl group include a trifluoromethyl group. In the resin according to this embodiment, the number of carbon atoms in the alkyl group is preferably, for example, 1 to 28, 1 to 20, 1 to 18, 1 to 10, or 1 to 5.

[0143] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0144] In the resin according to this embodiment, examples of the alkylene group include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a hexamethylene group. In the resin according to this embodiment, the number of carbon atoms in the alkylene group is preferably, for example, 1 to 28, 1 to 20, 1 to 18, 1 to 10, or 1 to 5.

[0145] In the resin according to this embodiment, examples of the alkylidene group include an ethylidene group and an isopropylidene group. In the resin according to this embodiment, the alkylidene group preferably has 2 to 28, 2 to 20, 2 to 18, 2 to 10, or 2 to 5 carbon atoms.

[0146] In the resin according to this embodiment, examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, various pentyloxy groups, various hexyloxy groups, etc. In the resin according to this embodiment, the number of carbon atoms in the alkoxy group is, for example, 1 to 20, 1 to 18, 1 to 10, or 1 to 5.

[0147] In the resin according to this embodiment, examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, and a norbornyl group. In the resin according to this embodiment, the cycloalkyl group also includes bridged ring cycloalkyl groups such as bicycloalkyl groups and tricycloalkyl groups. In the resin according to this embodiment, the number of ring carbon atoms of the cycloalkyl group is preferably, for example, 3 to 26, 3 to 20, or 6 to 20.

[0148] In the resin according to this embodiment, examples of the cycloalkylene group include a cyclopentanediyl group, a cyclohexanediyl group, a cyclooctanediyl group, and an adamantanediyl group. In the resin according to this embodiment, the cycloalkylene group also includes bridged ring cycloalkylene groups such as a bicycloalkylene group and a tricycloalkylene group. In the resin according to this embodiment, the number of ring carbon atoms of the cycloalkylene group is, for example, preferably 5 to 15, or 5 to 10.

[0149] In the resin according to this embodiment, examples of the cycloalkylidene group include a cyclohexylidene group, a 3,5,5-trimethylcyclohexylidene group, and a 2-adamantylidene group. In the resin according to this embodiment, the cycloalkylidene group also includes bridged-ring cycloalkylidene groups such as a bicycloalkylidene group and a tricycloalkylidene group. In the resin according to this embodiment, the number of ring carbon atoms of the cycloalkylidene group is preferably, for example, 3 to 26, 5 to 15, or 5 to 10.

[0150] In the resin according to this embodiment, the cycloalkoxy group may be, for example, a group in which the cycloalkyl group moiety is the cycloalkyl group described above, i.e., a group in which Arx of the group represented by -O-Arx is the cycloalkyl group described above. In the resin according to this embodiment, the cycloalkoxy group preferably has 3 to 20 ring carbon atoms, or 6 to 20 ring carbon atoms.

[0151] In the resin according to this embodiment, examples of the alkenyl group include ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), butenyl, pentenyl, and hexenyl groups. In the resin according to this embodiment, the number of carbon atoms in the alkenyl group is preferably 2 to 10, or 2 to 6, for example.

[0152] In the resin according to this embodiment, examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, and a 3-hexynyl group. In the resin according to this embodiment, the number of carbon atoms in the alkynyl group is preferably, for example, 2 to 10, or 2 to 6.

[0153] In the resin according to this embodiment, examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. In the resin according to this embodiment, examples of the substituted aryl group include a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a dichlorophenyl group, and a methylnaphthyl group. In the resin according to this embodiment, the number of ring carbon atoms of the aryl group is preferably 6 to 20, for example, 6 to 14, or 6 to 10.

[0154] In the resin according to this embodiment, examples of the arylene group include a phenylene group, a naphthylene group, an anthracenediyl group, a biphenylene group, and a terphenyldiyl group. In one aspect of the resin according to this embodiment, the number of ring carbon atoms of the arylene group is preferably, for example, 6 to 20, 6 to 14, or 6 to 10.

[0155] In the resin according to this embodiment, examples of the aryloxy group include a phenoxy group and a naphthyloxy group. In the resin according to this embodiment, examples of the substituted aryloxy group include a tolyloxy group. In the resin according to this embodiment, the number of ring carbon atoms of the aryloxy group is, for example, preferably 6 to 14, or 6 to 10.

[0156] In the resin according to this embodiment, examples of the aralkyl group include a phenylmethyl group and a phenylethyl group. In the resin according to this embodiment, the number of carbon atoms in the aralkyl group is preferably, for example, 7 to 20, or 7 to 15.

[0157] In the resin according to this embodiment, the aralkyloxy group may be, for example, an aralkyl group moiety, i.e., an aralkyl group in the group represented by -O-Ary, where Ary is the aralkyl group. In the resin according to this embodiment, the number of carbon atoms in the aralkyloxy group is preferably, for example, 7 to 20 or 7 to 15.

[0158] In the resin according to this embodiment, the heteroaryl group contains at least one heteroatom as a ring-forming atom. For example, the heteroaryl group may contain one, two, or three heteroatoms as ring-forming atoms. The heteroatoms contained in the heteroaryl group as ring-forming atoms are one or more atoms selected from the group consisting of nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms. When the heteroaryl group contains multiple heteroatoms as ring-forming atoms, the multiple heteroatoms may be the same or different. In the resin according to this embodiment, examples of the heteroaryl group include pyrrolyl, imidazolyl, furyl, thienyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolyl, benzofuranyl, benzothienyl, quinolyl, isoquinolyl, phenanthrolinyl, and acridinyl groups. In the resin according to this embodiment, the heteroaryl group preferably has 5 to 20 ring atoms, 5 to 14 ring atoms, or 5 to 10 ring atoms.

[0159] In the resin according to this embodiment, examples of the monovalent aromatic hydrocarbon group include the aryl group. In the resin according to this embodiment, examples of the divalent aromatic hydrocarbon group include a divalent group derived by removing one hydrogen atom from the aryl ring of the aryl group.

[0160] In the resin according to this embodiment, the monovalent alicyclic hydrocarbon group may be, for example, a saturated or unsaturated alicyclic group. The alicyclic group may have, for example, 3 to 20 carbon atoms, preferably 3 to 12 carbon atoms, and more preferably 4 to 8 carbon atoms. Specific examples of the saturated or unsaturated alicyclic group include cycloalkyl groups, which are saturated alicyclic groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl, and cycloalkenyl groups, which are unsaturated alicyclic groups such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl. The unsaturated alicyclic group does not contain an aromatic group. In the resin according to this embodiment, the divalent alicyclic hydrocarbon group may be, for example, a divalent group derived by removing one hydrogen atom from the ring of the saturated or unsaturated alicyclic group.

[0161] In the resin according to this embodiment, examples of the monovalent chain aliphatic hydrocarbon group include the alkyl groups described above.

[0162] In the resin according to this embodiment, the divalent chain aliphatic hydrocarbon group is, for example, a divalent group derived by removing one hydrogen atom from the alkyl chain of the alkyl group.

[0163] In the resin according to this embodiment, the chain aliphatic hydrocarbon group includes a linear aliphatic hydrocarbon group and a branched aliphatic hydrocarbon group.

[0164] In this specification, when referring to "substituted or unsubstituted," the substituents may bond to each other to form a monocycle, a fused ring, or not bond to each other. Here, when referring to "substituted or unsubstituted," the substituents may bond to each other to form a monocycle or a fused ring, and this also includes cases where the substituents bond to each other to form a multi-membered ring. This multi-membered ring is preferably a two-membered ring (bicyclo), a three-membered ring (tricyclo), or a four-membered ring (tetracyclo). For example, when referring to a "substituted or unsubstituted" group (a cycloalkyl group, a cycloalkylene group, a cycloalkylidene group) derived from a cycloalkane, examples of when the substituents bond to each other to form a multi-membered ring include monovalent or divalent groups derived from a bicycloalkane, a tricycloalkane, and a tetracycloalkane.

[0165] In this specification, the substituents in the "substituted" part of "substituted or unsubstituted" are preferably at least one substituent selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, an aryloxy group, and a halogen atom, each independently. Specific examples of these substituents include the same groups as the specific examples described above. Furthermore, in this specification, "unsubstituted" in the "substituted or unsubstituted" part means that the group is not substituted with the substituent and is bonded to a hydrogen atom.

[0166] In this specification, among specific examples of compounds, Me may represent a methyl group, Ph may represent a phenyl group, and tBu may represent a tert-butyl group.

[0167] In this specification, the preferred provisions can be adopted arbitrarily, and it can be said that a combination of preferred provisions is more preferred.

[0168] [Method for Producing Resin] The resin according to this embodiment can be produced by a known method for producing a polycarbonate resin, such as an interfacial polycondensation method or a melt transesterification method.

[0169] The interfacial polycondensation method is a method for obtaining a polycarbonate resin by converting a monomer such as a bisphenol compound into an alkali salt in the presence of an inert organic solvent and an aqueous alkali solution, and then polycondensing the salt with phosgene or a compound capable of forming a carbonate bond at the interface.The melt transesterification method involves, for example, a transesterification reaction between a carbonate ester and a monomer such as a bisphenol or a diol compound.

[0170] The resin production method according to this embodiment preferably produces a polycarbonate resin by an interfacial polycondensation method. In the case of the interfacial polycondensation method, the polycarbonate resin according to this embodiment can be produced by copolymerizing a bisphenol compound with phosgene and a chloroformate. Specifically, the resin production method according to this embodiment includes a step of interfacially polycondensing a bischloroformate monomer or bischloroformate oligomer represented by the following formula (M-UN1), from which the polycarbonate structural unit represented by the formula (UN1) is derived, a bisphenol compound, and a phenol compound represented by the following formula (M-ME1), from which the formula (ME1) is derived.

[0171]

[0172]

[0173] (In the formula (M-UN1), Ux, R １ , R ２ , m, and n each independently represent Ux, R in formula (UN1). １ , R ２ , m, and n; １Ａ represents the average number of mers, and n １Ａ is 1.0 or more and 10 or less, and in the formula (M-ME1), R １１ represents a hydrogen atom, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and q is 0, 1, or 2, provided that when q is 0, benzene ring A has a vinyl group, when q is 1, benzene ring B has a vinyl group, and when q is 2, only the benzene ring B farthest from benzene ring A has a vinyl group.

[0174] That is, in the formula (M-ME1), R １１ and q each independently represent R in formula (ME1). １１ and q.

[0175] One embodiment of the formula (M-ME1) is represented by the following formula (M-ME1-A1), formula (M-ME1-A2), or formula (M-ME1-A3).

[0176]

[0177] (In the formulas (M-ME1-A1), (M-ME1-A2), and (M-ME1-A3), R １１ has the same meaning as formula (M-ME1) above.

[0178] Examples of bisphenol compounds include bis(hydroxyphenyl)alkane dihydric phenols, bis(hydroxyphenyl)cycloalkane dihydric phenols, dihydroxybiphenyl compounds, dihydroxybenzene compounds, dihydroxynaphthalene compounds, bis(4-hydroxyphenyl)oxide, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, bis(4-hydroxyphenyl)ether, bis(3-fluoro-4-hydroxyphenyl)ether, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxy-3-methylphenyl)sulfone, bis(4-hydroxyphenyl)sulfoxide, and 4,4'-dihydroxybenzophenone.

[0179] Examples of bis(hydroxyphenyl)alkane dihydric phenols include bis(4-hydroxyphenyl)methane, bis(4-hydroxy-3-methylphenyl)methane, 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)-methane, 1,1-bis(4-hydroxyphenyl)-1,1-diphenylmethane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)-1-phenylmethane, 1,1-bis(4-hydroxyphenyl)-1-phenylmethane, and bis(3-chloro-4-hydroxyphenyl). Methane, bis(3,5-dibromo-4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,2-bis(4-hydroxyphenyl)ethane, 2-(4-hydroxy-3-methylphenyl)-2-(4-hydroxyphenyl)-1-phenylethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 1,1-bis(2-tert-butyl-4-hydroxy-3-methylphenyl)ethane, 1-phenyl-1,1-bis(3-fluoro-4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)ethane 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxy-3-phenylphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-2-methylphenyl)propane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)propane, 2,2-bis(3-chloro-4-hydroxyphenyl)propane 2,2-bis(3-hydroxyphenyl)propane, 2,2-bis(3-fluoro-4-hydroxyphenyl)propane, 2,2-bis(3-bromo-4-hydroxyphenyl)propane, 2,2-bis(3,5-difluoro-4-hydroxyphenyl)propane, 2,2-bis(3,5-dichloro-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 2,2-bis(3-bromo-4-hydroxy-5-chlorophenyl)propane, 2,2-bis(3-hydroxyphenyl)hexafluoropropane, 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 1,1-bis(2-butyl-4-hydroxy-5-methylphenyl)butane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)butane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)isobutane, 1,1-bis(2-tert-amyl-4-hydroxy-5-methylphenyl)butane, 2,2-bis(4-hydroxy-3-methylphenyl)butane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(3,5-dichlorophenyl) Examples of suitable hydroxyphenyls include 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 4,4-bis(4-hydroxyphenyl)heptane, and 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)heptane, 1,1-bis(4-hydroxy-3,5-dimethylphenyl)octadecane, 1,1-bis(4-hydroxy-3,5-dimethylphenyl)eicosane, and 1,1-bis(4-hydroxy-3,5-dimethylphenyl)docosane.

[0180] Examples of bis(hydroxyphenyl)cycloalkane dihydric phenols include 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-cyclohexane),

[0033] Examples of the cyclohexyl ester include 1,1-bis(3-phenyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-phenylphenyl)cyclohexane, 2,2'-methylenebis(6-cyclohexyl-p-cresol), 1,1-bis(4-hydroxyphenyl)cyclododecane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclododecane, and 1,1-bis(4-hydroxy-3,5-dimethylphenyl)cyclododecane.

[0181] Examples of dihydroxybiphenyl compounds include 4,4'-dihydroxybiphenyl, 3,3'-difluoro-4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-3,3'-dimethylbiphenyl, 4,4'-dihydroxy-2,2'-dimethylbiphenyl, 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl, 2,2',3,3',5,5'-hexamethyl-4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-2,2',5,5'-dimethylbiphenyl, and 4,4'-dihydroxy-3,3'-dicyclohexylbiphenyl.

[0182] The phenol compound represented by formula (M-ME1) is a terminal stopper. It is also preferable that the phenol compound represented by formula (M-ME1) is at least one selected from the group consisting of the following formulas (M-ME1-1), (M-ME1-2), and (M-ME1-3). The following formulas (M-ME1-1), (M-ME1-2), and (M-ME1-3) correspond to the phenol compounds in formula (M-ME1) when q is 0, when q is 1, and when q is 2, respectively. That is, the following formulas (M-ME1-2) and (M-ME1-3) are the same as the above formulas (M-ME1-A2) and (M-ME1-A3).

[0183]

[0184] (In the formulas (M-ME1-1), (M-ME1-2), and (M-ME1-3), R １１ are R in the formula (M-ME1), respectively. １１ is synonymous with

[0185] As the terminal terminator, the phenol compound represented by the formula (M-ME1) may be used alone, or the phenol compound represented by the formula (M-ME1) may be used in combination with a terminal terminator having no vinyl group. When the phenol compound represented by the formula (M-ME1) is represented by the formula (M-ME1-1), specific examples of the phenol compound represented by the formula (M-ME1) include, but are not limited to, 3-vinylphenol, 4-vinylphenol, 2-methoxy-4-vinylphenol, and vinylnaphthol.

[0186] Examples of the vinyl-free end terminator that can be used in combination include monohydric phenols such as phenol, p-cresol, p-tert-butylphenol, p-tert-octylphenol, p-cumylphenol, p-nonylphenol, m-pentadecylphenol, and p-tert-amylphenol.

[0187] Examples of acid binders used in interfacial polycondensation include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, and cesium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; weak alkali metal salts such as sodium carbonate and potassium carbonate; weak alkaline earth metal salts such as calcium acetate; and organic bases such as pyridine. Preferred acid binders for interfacial polycondensation include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide. These acid binders can also be used as mixtures. The proportion of the acid binder used can be appropriately adjusted taking into account the stoichiometric ratio (equivalents) of the reaction. Specifically, 1 equivalent or more of the acid binder can be used per mole of the total hydroxyl groups of the dihydric phenol raw material, and preferably 1 to 10 equivalents of the acid binder can be used.

[0188] Examples of solvents used in interfacial polycondensation include aromatic hydrocarbons such as toluene, ketones such as cyclohexanone, and halogenated hydrocarbons such as methylene chloride. Among these, methylene chloride is preferred because of its high solubility.

[0189] Suitable catalysts for use in interfacial polycondensation include, for example, tertiary amines such as trimethylamine, triethylamine, tributylamine, N,N-dimethylcyclohexylamine, pyridine, N,N-diethylaniline, and N,N-dimethylaniline; quaternary ammonium salts such as trimethylbenzylammonium chloride, triethylbenzylammonium chloride, tributylbenzylammonium chloride, trioctylmethylammonium chloride, tetrabutylammonium chloride, and tetrabutylammonium bromide; and quaternary phosphonium salts such as tetrabutylphosphonium chloride and tetrabutylphosphonium bromide. Furthermore, a small amount of an antioxidant such as sodium sulfite or a hydrosulfite salt may be added to the reaction system, if necessary.

[0190] [Insulating Material] One aspect of the insulating material according to this embodiment contains the resin according to this embodiment.

[0191] [Resin Composition] The resin composition according to this embodiment contains the resin according to this embodiment.

[0192] One aspect of the resin composition according to this embodiment includes the resin according to this embodiment and a radical polymerization initiator.

[0193] Examples of the radical polymerization initiator include peroxides, azo initiators, and redox initiators that combine an oxidizing agent and a reducing agent. In one aspect of the resin composition according to this embodiment, the content of the radical polymerization initiator is 0.01 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the resin according to this embodiment.

[0194] [Cured Product] The cured product according to this embodiment contains the resin according to this embodiment.

[0195] One aspect of the cured product according to this embodiment is obtained by subjecting the resin composition according to this embodiment to a curing reaction. One aspect of the cured product according to this embodiment is a completely cured product.

[0196] One aspect of the cured product according to the present embodiment is a cured product obtained by curing intermolecular bonds of the resin according to the present embodiment. The cured product according to the present embodiment can be obtained by curing intermolecular bonds of the resin according to the present embodiment by curing terminal structures having vinyl groups, which serve as reactive terminal groups, possessed by the resin according to the present embodiment contained in the resin composition according to the present embodiment.

[0197] The conditions for the curing reaction include, for example, a temperature of 50° C. or higher and 300° C. or lower, and a time of 0.1 hour or higher and 50 hours or lower, under reduced pressure, normal pressure, or increased pressure.

[0198] In one aspect of the cured product according to this embodiment, the dielectric constant Dk at a frequency of 10 GHz measured by a resonator perturbation method using a split cylinder resonator is preferably 2.85 or less. In the cured product according to this embodiment, the dielectric constant Dk is preferably 2.80 or less, more preferably 2.75 or less, more preferably 2.70 or less, even more preferably 2.65 or less, even more preferably 2.60 or less, and even more preferably 2.50 or less. In this specification, the dielectric constant Dk of the cured product is a value measured at room temperature (23°C) and a frequency of 10 GHz using a split cylinder resonator.

[0199] In one aspect of the cured product according to this embodiment, the dielectric loss tangent Df at a frequency of 10 GHz, as measured by a resonator perturbation method using a split cylinder resonator, is preferably 0.02000 or less, more preferably 0.00700 or less, more preferably 0.00500 or less, more preferably 0.00350 or less, more preferably 0.00300 or less, even more preferably 0.00250 or less, even more preferably 0.00200 or less, and even more preferably 0.00140 or less. In particular, from the viewpoint of achieving a low dielectric loss tangent, the dielectric loss tangent Df of the cured product according to one aspect of this embodiment is more preferably 0.00300 or less. In this specification, the dielectric loss tangent Df of the cured product is a value measured at room temperature (23°C) and a frequency of 10 GHz using a split cylinder resonator.

[0200] [Coating composition] The resin according to this embodiment may be contained in a coating composition. The coating composition according to this embodiment contains the resin according to this embodiment. The coating composition according to this embodiment may be referred to as a varnish.

[0201] One aspect of the coating composition according to the present embodiment contains the resin according to the present embodiment and an organic solvent. One aspect of the coating composition according to the present embodiment contains the resin composition according to the present embodiment and an organic solvent.

[0202] The organic solvent for the coating liquid composition can be appropriately selected taking into consideration the solubility of materials such as the resin according to this embodiment, the drying speed after molding, the effect of the solvent remaining on the molded product, and hazards (fire or health hazards).

[0203] Examples of organic solvents used in the coating composition according to this embodiment include cyclic ethers (such as tetrahydrofuran (THF), dioxane, and dioxolane), cyclic ketones (such as cyclohexanone, cyclopentanone, and cycloheptanone), aromatic hydrocarbons (such as toluene, xylene, and chlorobenzene), ketones (such as methyl ethyl ketone (MEK) and methyl isobutyl ketone (MIBK)), halogenated hydrocarbons (such as dichloromethane and chloroform), esters (such as ethyl acetate, isopropyl acetate, isobutyl acetate, and butyl acetate), ethers (such as ethylene glycol dimethyl ether and ethylene glycol monoethyl ether), amides (such as N,N-dimethylformamide (DMF) and dimethylacetamide (DMAc)), and aprotic polar solvents (such as dimethyl sulfoxide (DMSO)).

[0204] In the coating liquid composition of the present embodiment, in consideration of the environment and safety, the organic solvent is preferably an organic solvent other than halogenated hydrocarbons, i.e., a non-halogenated solvent, and more preferably at least one solvent selected from the group consisting of toluene, cyclohexanone, methyl ethyl ketone, tetrahydrofuran, dioxolane, and cyclopentanone.

[0205] One aspect of the coating composition according to the present embodiment contains the resin according to the present embodiment and a non-halogen-based solvent. One aspect of the coating composition according to the present embodiment contains the resin composition according to the present embodiment and the non-halogen-based solvent, and the resin composition according to the present embodiment is dissolved in the non-halogen-based solvent.

[0206] The coating composition according to the present embodiment may be applied in a solution state, i.e., as a coating composition, directly onto a core material made of a polyimide or epoxy resin. In this case, an inorganic filler such as silica may be dispersed in the coating composition. Suitable solvents for dispersing the inorganic filler in the coating composition include, for example, toluene, cyclohexanone, and MEK.

[0207] In one aspect of the coating composition according to this embodiment, in addition to the resin according to this embodiment, at least one of another thermosetting resin and a thermoplastic resin may be mixed. Examples of thermosetting resins include maleimide resin, polyphenylene ether (PPE), epoxy resin, phenoxy resin, melamine-based resin, and silicone-based resin. Examples of thermoplastic resins include liquid crystal polymer, PPE, polyimide, styrene-butadiene copolymer (elastomer), and fluororesin. In particular, the inclusion of an elastomer can impart flexibility.

[0208] One aspect of the coating liquid composition according to this embodiment may contain a flame retardant. Examples of the flame retardant include halogen-based flame retardants, phosphorus-based flame retardants, nitrogen compounds, and silicone-based flame retardants. Preferred phosphorus-based flame retardants include organic phosphorus-based flame retardants and reactive organic phosphorus-based flame retardants. These flame retardants may be additive-type, or may have a reactive group in part of the flame retardant and react with the resin according to this embodiment.

[0209] [Film] One aspect of the film according to the present embodiment contains the resin according to the present embodiment. One aspect of the film according to the present embodiment contains the resin composition according to the present embodiment. One aspect of the film according to the present embodiment is made of the cured product according to the present embodiment. Specifically, one aspect of the film according to the present embodiment is made of a cured product obtained by subjecting the resin composition according to the present embodiment to a curing reaction.

[0210] One aspect of the film according to this embodiment can be produced by thermoforming the resin or resin composition according to this embodiment (e.g., melt extrusion molding, etc.) into a film, or by solution-casting the coating composition according to this embodiment. When a thin film (e.g., a thickness of several μm to several tens of μm) is desired for the film according to this embodiment, solution casting is preferred. Furthermore, for purposes such as reducing thermal expansion, the coating composition according to this embodiment may be impregnated into a fibrous substrate such as glass cloth, or a coating composition in which an inorganic filler such as silica is dispersed may be formed into a film. A film obtained by impregnating a fibrous substrate such as glass cloth with the resin according to this embodiment may be referred to as a prepreg. Furthermore, for purposes such as improving dielectric properties and adjusting the modulus of elasticity, a coating composition containing a known thermoplastic resin other than the resin according to this embodiment may be used to form a film. Furthermore, when forming a film using the coating composition according to this embodiment by solution casting, the degree of curing can be controlled by adjusting the heating temperature, thereby changing the modulus of elasticity of the film.

[0211] One aspect of the sheet according to this embodiment contains the resin according to this embodiment.

[0212] When the resin according to this embodiment is used as a sheet, it can be made into a sheet by impregnating a substrate or the like with the above-mentioned coating liquid composition (varnish).

[0213] [Prepreg] One aspect of the prepreg according to this embodiment contains the resin according to this embodiment.

[0214] One aspect of the prepreg according to the present embodiment comprises the coating composition according to the present embodiment and a fibrous substrate, the fibrous substrate being impregnated with the coating composition, and the coating composition being a semi-cured or fully cured product. In this specification, a semi-cured product means that the curing reaction of the resin composition in the coating composition has partially progressed to the extent that the fluidity of the coating composition according to the present embodiment has been lost, and the coating composition is in a state ranging from uncured to not yet fully cured, i.e., the resin is in the so-called B-stage.

[0215] In one aspect of the prepreg according to the present embodiment, examples of the fibrous base material include glass cloth, polyester cloth, glass nonwoven fabric, aramid nonwoven fabric, glass paper, pulp paper, and combinations thereof.

[0216] One aspect of the prepreg according to this embodiment can be produced by impregnating or coating a fibrous substrate with a coating composition, followed by heat drying, etc. By heat drying, the solvent in the coating composition is removed by heating.

[0217] The prepreg according to the present embodiment may be used in one piece or in a laminate of two or more pieces.

[0218] [Electronic Substrate] One aspect of the electronic substrate according to this embodiment contains the resin according to this embodiment. In one aspect of the electronic substrate according to this embodiment, the insulating material, resin composition, cured product, coating composition, film, sheet, and prepreg according to this embodiment are used as electronic substrate materials to form the electronic substrate according to this embodiment. This electronic substrate material has excellent low dielectric properties. When the resin or resin composition according to this embodiment is used as an electronic substrate material, this electronic substrate material can provide a composition for a coating liquid that has high solvent solubility and low solution viscosity characteristics for coating molding.

[0219] One aspect of the electronic substrate according to the present embodiment includes the prepreg according to the present embodiment and a copper foil. The electronic substrate according to the present embodiment may include a copper clad laminate (CCL) in which copper foil is laminated on at least one surface of one or more laminated prepregs according to the present embodiment.

[0220] Electronic substrates are used for a variety of purposes, including servers, automotive applications, base stations, antennas for smartphones, and transmission boards. They can be broadly divided into semiconductor substrates and electronic circuit boards. (1) Semiconductor Substrates: Semiconductor substrates are substrates for forming wiring layers that handle the input and output of electrical signals to and from chips such as logic ICs, memory, and sensors. This wiring layer is a connection layer for connecting identical or different types of chips in parallel or stacked configurations. Examples of chip types include FC-CSP (flip chip-chip scale package), FC-BGA (flip chip-ball grid array), and FO-WLP (fan-out-wafer level package), as well as interposers for connecting multiple semiconductor chips. (2) Electronic Circuit Boards: Electronic circuit boards are substrates formed with wiring layers for connecting multiple electronic components, such as semiconductors and capacitors. Electronic circuit boards are sometimes referred to as printed wiring boards. Types of electronic circuit boards include multilayer boards (rigid and flexible) with stacked wiring.

[0221] [Bonding Film] One aspect of the bonding film according to this embodiment contains the resin according to this embodiment. In one aspect, the bonding film according to this embodiment has a resin composition layer made of the resin composition according to this embodiment. One aspect of the bonding film according to this embodiment comprises a resin composition layer made of the resin composition according to this embodiment and a release film in contact with at least one surface of the resin composition layer, and it is preferable that the resin composition layer is in a B-stage state (i.e., in a semi-cured state). In one aspect, the bonding film according to this embodiment may comprise a resin composition layer between two release films. Required properties of this bonding film include low dielectric properties and high adhesion.

[0222] [Interlayer insulating film] One aspect of the interlayer insulating film according to this embodiment contains the resin according to this embodiment. A package substrate is disposed between an IC chip and a motherboard included in a personal computer or smartphone. This package substrate is a component that protects the IC chip and transmits signals to the motherboard. An interlayer insulating film is provided to maintain insulation between circuits on this package substrate. Required properties of the interlayer insulating film include low dielectric properties, low thermal expansion, high adhesion to copper, high solvent solubility, and high dispersibility of inorganic fillers.

[0223] One aspect of the interlayer insulating film according to this embodiment contains the resin composition according to this embodiment. In one aspect of the interlayer insulating film according to this embodiment, various components that can be contained in the interlayer insulating film include resin, organic solvent, inorganic filler, curing accelerator, organic filler, and adhesion promoter. Resins that can be contained in the interlayer insulating film include the resin according to this embodiment, as well as general thermosetting and thermoplastic resins other than the resin according to this embodiment. The component responsible for achieving low dielectric properties and low thermal expansion is resin, and the component responsible for achieving low dielectric tangent and low thermal expansion is spherical silica gel, an inorganic filler, although this increases the dielectric constant. The use of adhesion promoters is also effective in improving adhesion to copper, but this depends on the properties of the resin.

[0224] Next, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to these examples and various modifications and applications are possible within the scope of the present invention.

[0225] [Production Examples: Preparation of Oligomers] <Production Example 1: Synthesis of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane Oligomer> 75.8 g (224 mmol) of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (OCTMC) was suspended in 1080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto. A solution prepared by dissolving 44.0 g (435 mmol) of triethylamine in 120 mL of methylene chloride was added dropwise to this solution at a temperature in the range of 5°C to 15°C. Next, after stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite were added to the residual liquid, and the mixture was washed. The resulting solution was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 0.92 mol / L, a solids concentration of 0.223 kg / L, and an average number of monomers of 1.06. Hereinafter, the resulting oligomer (bischloroformate) according to Production Example 1 will be referred to as OCTMC-CF.

[0226] <Production Example 2: Synthesis of 1,1-bis-(4-hydroxy-3-methylphenyl)-cyclododecane oligomer (bischloroformate)> The oligomer according to Production Example 2 was produced in the same manner as in Production Example 1, except that 85.2 g (224 mmol) of 1,1-bis-(4-hydroxy-3-methylphenyl)-cyclododecane (OCCDE) was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane. The chloroformate concentration of the resulting solution was 0.84 mol / L, the solid concentration was 0.218 kg / L, and the average number of monomers was 1.04. Hereinafter, the resulting oligomer according to Production Example 2 will be referred to as OCCDE-CF.

[0227] <Production Example 3: Synthesis of 1,1-bis-(4-hydroxy-3-cyclohexylphenyl)-cyclohexane oligomer (bischloroformate)> The oligomer according to Production Example 3 was produced in the same manner as in Production Example 1, except that 96.9 g (224 mmol) of 1,1-bis-(4-hydroxy-3-cyclohexylphenyl)-cyclohexane (CHZ) was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane. The chloroformate concentration of the resulting solution was 0.84 mol / L, the solid concentration was 0.218 kg / L, and the average number of monomers was 1.04. Hereinafter, the obtained oligomer according to Production Example 3 will be referred to as CHZ-CF.

[0228] <Production Example 4: Synthesis of 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl oligomer (bischloroformate)> The oligomer according to Production Example 4 was produced in the same manner as in Production Example 1, except that 54.3 g (224 mmol) of 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (TMBP) was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane. The chloroformate concentration of the resulting solution was 0.59 mol / L, the solid concentration was 0.115 kg / L, and the average number of monomers was 1.08. Hereinafter, the obtained oligomer according to Production Example 4 will be referred to as TMBP-CF.

[0229] <Production Example 5: Synthesis of 1,1-bis-(3,5-dimethyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane oligomer (bischloroformate)> The oligomer according to Production Example 5 was produced in the same manner as in Production Example 1, except that 82.1 g (224 mmol) of 1,1-bis-(3,5-dimethyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (TMTMC) was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane. The chloroformate concentration of the resulting solution was 0.86 mol / L, the solid concentration was 0.225 kg / L, and the average number of monomers was 1.08. Hereinafter, the resulting oligomer according to Production Example 5 will be referred to as TMTMC-CF.

[0230] <Production Example 6: Synthesis of 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)-methane oligomer (bischloroformate)> The oligomer according to Production Example 6 was produced in the same manner as in Production Example 1, except that 57.4 g (224 mmol) of 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)-methane (TMBPF) was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane. The chloroformate concentration of the resulting solution was 1.13 mol / L, the solid concentration was 0.222 kg / L, and the average number of monomers was 1.04. Hereinafter, the resulting oligomer according to Production Example 6 will be referred to as TMBPF-CF.

[0231] <Production Example 7: Synthesis of 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane oligomer (bischloroformate)> The oligomer of Production Example 7 was produced in the same manner as in Production Example 1, except that 63.7 g (224 mmol) of 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane (TMBA) was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane. The chloroformate concentration of the resulting solution was 1.05 mol / L, the solid concentration was 0.223 kg / L, and the average number of monomers was 1.05. Hereinafter, the obtained oligomer of Production Example 7 will be referred to as TMBA-CF.

[0232] <Production Example 8: Synthesis of 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)-cyclododecane oligomer (bischloroformate)> The oligomer according to Production Example 8 was produced in the same manner as in Production Example 1, except that 85.2 g (224 mmol) of 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)-cyclododecane (TMCDE) was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane. The chloroformate concentration of the resulting solution was 0.78 mol / L, the solid concentration was 0.216 kg / L, and the average number of monomers was 1.04. Hereinafter, the obtained oligomer according to Production Example 8 will be referred to as TMCDE-CF.

[0233] Synthesis Example 1 (Production of PC Polymer) 224 mL of OCTMC-CF from Production Example 1, 331 mL of methylene chloride, 23.2 g of 2,2'-methylenebis(6-cyclohexyl-p-cresol), and 4.05 g of 4-vinylphenol were added to a reaction vessel equipped with a mechanical stirrer, stirring blades, and baffles, and the mixture was stirred to ensure thorough mixing, yielding a methylene chloride solution (M1). Hereinafter, 2,2'-methylenebis(6-cyclohexyl-p-cresol) may be referred to as MBCC, and 4-vinylphenol may be referred to as 4-VP. Furthermore, 185 mL of 2.0 N aqueous sodium hydroxide solution (19.8 g of sodium hydroxide) was cooled to below room temperature, and then 0.203 g of sodium hydrosulfite and 0.159 g of benzyltripropylammonium chloride were added and completely dissolved to prepare an aqueous sodium hydroxide solution (SH1). The entire amount of the aqueous sodium hydroxide solution (SH1) was added to this methylene chloride solution (M1), and an aqueous triethylamine solution (7% by volume, 6.8 mL) was added while stirring, and stirring was continued for 1 hour. The reaction mixture obtained after stirring was diluted with 0.54 L of methylene chloride and 0.01 L of water and washed (first wash). After this first wash, the lower layer was separated and further washed once with 0.20 L of water, once with 0.20 L of 0.03 N hydrochloric acid, and three times with 0.20 L of water (second wash). After this second wash, the resulting methylene chloride solution was concentrated and added dropwise to methanol with stirring, and the resulting reprecipitate was filtered and dried to obtain a PC polymer (PC-1) having the following structure.

[0234] (Identification of PC polymer) The structure and composition of the PC polymer (PC-1) thus obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １The number average molecular weight calculated from the H-NMR spectrum was 3,956, and the compositional ratio (molar percentage) of the repeating unit [OCTMC] derived from the oligomer OCTMC-CF of Production Example 1, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [4-VP] derived from the end-terminator 4-VP was [OCTMC]:[MBCC]:[4-VP]=51:31:18 (mol %).

[0235]

[0236] Synthesis Example 2 (Production of PC Polymer) A PC polymer (PC-2) having the following structure was obtained in the same manner as in Synthesis Example 1, except that 3-vinylphenol (10.1 g) was used instead of 4-VP. 3-Vinylphenol may hereinafter be referred to as 3-VP.

[0237] (Identification of PC polymer) The structure and composition of the PC polymer (PC-2) thus obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,569, and the compositional ratio (molar percentage) of the repeating unit [OCTMC] derived from the oligomer OCTMC-CF of Production Example 1, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCTMC]:[MBCC]:[3-VP]=47:16:37 (mol %).

[0238]

[0239] Synthesis Example 3 (Production of PC Polymer) A PC polymer (PC-3) having the following structure was obtained in the same manner as in Synthesis Example 2, except that OCCDE-CF obtained in Production Example 2 was used instead of OCTMC-CF.

[0240] (Identification of PC polymer) The structure and composition of the PC polymer (PC-3) thus obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １The number average molecular weight calculated from the H-NMR spectrum was 1,652, and the compositional ratio (molar percentage) of the repeating unit [OCCDE] derived from the oligomer OCCDE-CF of Production Example 2, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCCDE]:[MBCC]:[3-VP]=43:20:37 (mol %).

[0241]

[0242] Synthesis Example 4 (Production of PC Polymer) A PC polymer (PC-4) having the following structure was obtained in the same manner as in Synthesis Example 2, except that CHZ-CF obtained in Production Example 3 was used instead of OCTMC-CF.

[0243] (Identification of PC polymer) The structure and composition of the PC polymer (PC-4) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,668, and the compositional ratio (molar percentage) of the repeating unit [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [CHZ]:[MBCC]:[3-VP]=43:18:39 (mol %).

[0244]

[0245] Synthesis Example 5 (Production of PC Polymer) A PC polymer (PC-5) having the following structure was obtained in the same manner as in Synthesis Example 4, except that 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl was used instead of MBCC and 2-methoxy-4-vinylphenol (2.36 g) was used instead of 3-VP. 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl will hereinafter be referred to as TMBP, and 2-methoxy-4-vinylphenol will hereinafter be referred to as 2M4-VP.

[0246] (Identification of PC polymer) The structure and composition of the PC polymer (PC-5) thus obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units. MeO in the PC polymer means a methoxy group. The same applies to the following PC polymers. １ The number average molecular weight calculated from the H-NMR spectrum was 10,333, and the compositional ratio (molar percentage) of the repeating unit [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating unit [TMBP] derived from the raw material monomer TMBP, and the structural unit [2M4-VP] derived from the end terminator 2M4-VP was [CHZ]:[TMBP]:[2M4-VP]=56:37:7 (mol %).

[0247]

[0248] Synthesis Example 6 (Production of PC Polymer) A PC polymer (PC-6) having the following structure was obtained in the same manner as in Synthesis Example 2, except that 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)methane was used instead of MBCC. 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)methane may be referred to as TMBPF hereinafter.

[0249] (Identification of PC polymer) The structure and composition of the PC polymer (PC-6) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,300, and the compositional ratio (molar percentage) of the repeating unit [OCTMC] derived from the oligomer OCTMC-CF of Production Example 1, the repeating unit [TMBPF] derived from the raw material monomer TMBPF, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCTMC]:[TMBPF]:[3-VP]=41:20:39 (mol %).

[0250]

[0251] Synthesis Example 7 Production of PC Polymer A PC polymer (PC-7) having the following structure was obtained in the same manner as in Synthesis Example 6, except that OCCDE-CF obtained in Production Example 2 was used instead of OCTMC-CF.

[0252] (Identification of PC polymer) The structure and composition of the PC polymer (PC-7) thus obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,523, and the compositional ratio (molar percentage) of the repeating unit [OCCDE] derived from the oligomer OCCDE-CF of Production Example 2, the repeating unit [TMBPF] derived from the raw material monomer TMBPF, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCCDE]:[TMBPF]:[3-VP]=45:18:37 (mol %).

[0253]

[0254] Synthesis Example 8 (Production of PC Polymer) A PC polymer (PC-8) having the following structure was obtained in the same manner as in Synthesis Example 7, except that the amount of 3-VP used in Synthesis Example 7 was changed to 3.73 g.

[0255] (Identification of PC polymer) The structure and composition of the PC polymer (PC-8) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 3,390, and the compositional ratio (molar percentage) of the repeating unit [OCCDE] derived from the oligomer OCCDE-CF of Production Example 2, the repeating unit [TMBPF] derived from the raw material monomer TMBPF, and the structural unit [3-VP] derived from the end-terminator 3-VP was [OCCDE]:[TMBPF]:[3-VP]=49:33:18 (mol %).

[0256]

[0257] Synthesis Example 9 (Production of PC Polymer) A PC polymer (PC-9) having the following structure was obtained in the same manner as in Synthesis Example 7, except that 2,2',3,3',5,5'-hexamethyl-4,4'-dihydroxybiphenyl was used instead of TMBPF. 2,2',3,3',5,5'-hexamethyl-4,4'-dihydroxybiphenyl may hereinafter be referred to as HMBP.

[0258] (Identification of PC polymer) The structure and composition of the PC polymer (PC-9) thus obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,620, and the compositional ratio (molar percentage) of the repeating unit [OCCDE] derived from the oligomer OCCDE-CF of Production Example 2, the repeating unit [HMBP] derived from the raw material monomer HMBP, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCCDE]:[HMBP]:[3-VP]=51:13:36 (mol %).

[0259]

[0260] Synthesis Example 10 (Production of PC Polymer) A PC polymer (PC-10) having the following structure was obtained in the same manner as in Synthesis Example 4, except that TMBPF was used instead of MBCC and 4-VP (1.72 g) was used instead of 3-VP.

[0261] (Identification of PC polymer) The structure and composition of the PC polymer (PC-10) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 8,004, and the compositional ratio (molar percentage) of the repeating unit [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating unit [TMBPF] derived from the raw material monomer TMBPF, and the structural unit [4-VP] derived from the end-terminator 4-VP was [CHZ]:[TMBPF]:[4-VP]=55:36:9 (mol %).

[0262]

[0263] Synthesis Example 11 (Production of PC Polymer) A PC polymer (PC-11) having the following structure was obtained in the same manner as in Synthesis Example 10, except that 3-VP (8.45 g) was used instead of 4-VP.

[0264] (Identification of PC polymer) The structure and composition of the PC polymer (PC-11) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,814, and the compositional ratio (molar percentage) of the repeating unit [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating unit [TMBPF] derived from the raw material monomer TMBPF, and the structural unit [3-VP] derived from the end terminator 3-VP was [CHZ]:[TMBPF]:[3-VP]=48:18:34 (mol %).

[0265]

[0266] Synthesis Example 12 (Production of PC Polymer) A PC polymer (PC-12) having the following structure was obtained in the same manner as in Synthesis Example 11, except that the amount of 3-VP used in Synthesis Example 11 was changed to 1.72 g.

[0267] (Identification of PC polymer) The structure and composition of the PC polymer (PC-12) thus obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 8,421, and the composition ratio (molar percentage) of the repeating units [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating units [TMBPF] derived from the raw material monomer TMBPF, and the structural units [3-VP] derived from the end-terminator 3-VP was [CHZ]:[TMBPF]:[3-VP]=55:37:8 (mol %).

[0268]

[0269] Synthesis Example 13 (Production of PC Polymer) A PC polymer (PC-13) having the following structure was obtained in the same manner as in Synthesis Example 10, except that 2M4-VP was used instead of 4-VP.

[0270] (Identification of PC polymer) The structure and composition of the PC polymer (PC-13) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 8,261, and the compositional ratio (molar percentage) of the repeating unit derived from the oligomer CHZ-CF[CHZ] of Production Example 3, the repeating unit [TMBPF] derived from the raw material monomer TMBPF, and the structural unit [2M4-VP] derived from the end terminator 2M4-VP was [CHZ]:[TMBPF]:[2M4-VP]=54:37:9 (mol %).

[0271]

[0272] Synthesis Example 14 (Production of PC Polymer) A PC polymer (PC-14) having the following structure was obtained in the same manner as in Synthesis Example 4, except that 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)octadecane was used instead of MBCC. 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)octadecane may hereinafter be referred to as TMP18.

[0273] (Identification of PC polymer) The structure and composition of the PC polymer (PC-14) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 2,128, and the compositional ratio (molar percentage) of the repeating unit [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating unit [TMP18] derived from the raw material monomer TMP18, and the structural unit [3-VP] derived from the end terminator 3-VP was [CHZ]:[TMP18]:[3-VP]=45:21:34 (mol %).

[0274]

[0275] Synthesis Example 15 (Production of PC Polymer) A PC polymer (PC-15) having the following structure was obtained in the same manner as in Synthesis Example 14, except that the amount of 3-VP used in Synthesis Example 14 was changed to 1.19 g.

[0276] (Identification of PC polymer) The structure and composition of the PC polymer (PC-15) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 9,398, and the compositional ratio (molar percentage) of the repeating unit [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating unit [TMP18] derived from the raw material monomer TMP18, and the structural unit [3-VP] derived from the end terminator 3-VP was [CHZ]:[TMP18]:[3-VP]=52:38:10 (mol %).

[0277]

[0278] Synthesis Example 16 Production of PC Polymer A PC polymer (PC-16) having the following structure was obtained in the same manner as in Synthesis Example 14, except that TMBP-CF obtained in Production Example 4 was used instead of CHZ-CF and 4-VP was used instead of 3-VP.

[0279] (Identification of PC polymer) The structure and composition of the PC polymer (PC-16) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,983, and the compositional ratio (molar percentage) of the repeating unit [TMBP] derived from the oligomer TMBP-CF of Production Example 4, the repeating unit [TMP18] derived from the raw material monomer TMP18, and the structural unit [4-VP] derived from the end terminator 4-VP was [TMBP]:[TMP18]:[4-VP]=46:24:30 (mol %).

[0280]

[0281] Synthesis Example 17 (Production of PC Polymer) A PC polymer (PC-17) having the following structure was obtained in the same manner as in Synthesis Example 16, except that the amount of 4-VP used in Synthesis Example 17 was changed to 11.0 g.

[0282] (Identification of PC polymer) The structure and composition of the PC polymer (PC-17) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 3,061, and the compositional ratio (molar percentage) of the repeating unit [TMBP] derived from the oligomer TMBP-CF of Production Example 4, the repeating unit [TMP18] derived from the raw material monomer TMP18, and the structural unit [4-VP] derived from the end terminator 4-VP was [TMBP]:[TMP18]:[4-VP]=54:26:20 (mol %).

[0283]

[0284] Synthesis Example 18 (Production of PC Polymer) A PC polymer (PC-18) having the following structure was obtained in the same manner as in Synthesis Example 16, except that 2M4-VP (1.29 g) was used instead of 4-VP.

[0285] (Identification of PC polymer) The structure and composition of the PC polymer (PC-18) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 18,145, and the composition ratio (molar percentage) of the repeating unit [TMBP] derived from the oligomer TMBP-CF of Production Example 4, the repeating unit [TMP18] derived from the raw material monomer TMP18, and the structural unit [2M4-VP] derived from the end terminator 2M4-VP was [TMBP]:[TMP18]:[2M4-VP]=54:42:4 (mol %).

[0286]

[0287] Synthesis Example 19 (Production of PC Polymer) A PC polymer (PC-19) having the following structure was obtained in the same manner as in Synthesis Example 9, except that OCTMC-CF obtained in Production Example 1 was used instead of OCCDE-CF.

[0288] (Identification of PC polymer) The structure and composition of the PC polymer (PC-19) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 3,454, and the compositional ratio (molar percentage) of the repeating unit [OCTMC] derived from the oligomer OCTMC-CF of Production Example 1, the repeating unit [HMBP] derived from the raw material monomer HMBP, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCTMC]:[HMBP]:[3-VP]=54:29:17 (mol %).

[0289]

[0290] Synthesis Example 20 (Production of PC Polymer) A PC polymer (PC-20) having the following structure was obtained in the same manner as in Synthesis Example 19, except that OCTMC was used instead of HMBP.

[0291] (Identification of PC polymer) The structure and composition of the PC polymer (PC-20) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,869, and the composition ratio (molar percentage) of the sum of the repeating units derived from the oligomer OCTMC-CF of Production Example 1 and the repeating units [OCTMC] derived from the raw material monomer OCTMC, and the structural units [3-VP] derived from the end terminator 3-VP was [OCTMC]:[3-VP]=87:13 (mol %).

[0292]

[0293] Synthesis Example 21 (Production of PC Polymer) A PC polymer (PC-21) having the following structure was obtained in the same manner as in Synthesis Example 20, except that CHZ was used instead of OCTMC.

[0294] (Identification of PC polymer) The structure and composition of the PC polymer (PC-21) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,727, and the compositional ratio (molar percentage) of the repeating unit [OCTMC] derived from the oligomer OCTMC-CF of Production Example 1, the repeating unit [CHZ] derived from the raw material monomer CHZ, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCTMC]:[CHZ]:[3-VP]=47:18:35 (mol %).

[0295]

[0296] Synthesis Example 22 (Production of PC Polymer) A PC polymer (PC-22) having the following structure was obtained in the same manner as in Synthesis Example 21, except that OCCDE-CF obtained in Production Example 2 was used instead of OCTMC-CF.

[0297] (Identification of PC polymer) The structure and composition of the PC polymer (PC-22) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 1,703, and the compositional ratio (molar percentage) of the repeating unit [OCCDE] derived from the oligomer OCCDE-CF of Production Example 2, the repeating unit [CHZ] derived from the raw material monomer CHZ, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCCDE]:[CHZ]:[3-VP]=46:17:37 (mol %).

[0298]

[0299] Synthesis Example 23 (Production of PC Polymer) A PC polymer (PC-23) having the following structure was obtained in the same manner as in Synthesis Example 2, except that TMTMC-CF obtained in Production Example 5 was used instead of OCTMC-CF.

[0300] (Identification of PC polymer) The structure and composition of the PC polymer (PC-23) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 3,916, and the compositional ratio (molar percentage) of the repeating unit [TMTMC] derived from the oligomer TMTMC-CF of Production Example 5, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [TMTMC]:[MBCC]:[3-VP]=54:28:18 (mol %).

[0301]

[0302] Synthesis Example 24 (Production of PC Polymer) A PC polymer (PC-24) having the following structure was obtained in the same manner as in Synthesis Example 23, except that TMBPF-CF obtained in Production Example 6 was used instead of TMTMC-CF and OCCDE was used instead of MBCC.

[0303] (Identification of PC polymer) The structure and composition of the PC polymer (PC-24) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 2,268, and the compositional ratio (molar percentage) of the repeating unit [TMBPF] derived from the oligomer TMBPF-CF of Production Example 6, the repeating unit [OCCDE] derived from the raw material monomer OCCDE, and the structural unit [3-VP] derived from the end terminator 3-VP was [TMBPF]:[OCCDE]:[3-VP]=51:24:25 (mol %).

[0304]

[0305] Synthesis Example 25 (Production of PC Polymer) A PC polymer (PC-25) having the following structure was obtained in the same manner as in Synthesis Example 24, except that OCTMC was used instead of OCCDE.

[0306] (Identification of PC polymer) The structure and composition of the PC polymer (PC-25) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 2919, and the compositional ratio (molar percentage) of the repeating unit [TMBPF] derived from the oligomer TMBPF-CF of Production Example 6, the repeating unit [OCTMC] derived from the raw material monomer OCTMC, and the structural unit [3-VP] derived from the end terminator 3-VP was [TMBPF]:[OCTMC]:[3-VP]=54:27:19 (mol %).

[0307]

[0308] Synthesis Example 26 (Production of PC Polymer) A PC polymer (PC-26) having the following structure was obtained in the same manner as in Synthesis Example 2, except that TMCDE-CF obtained in Production Example 8 was used instead of OCTMC-CF.

[0309] (Identification of PC polymer) The structure and composition of the PC polymer (PC-26) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 2,657, and the compositional ratio (molar percentage) of the repeating unit [TMCDE] derived from the oligomer TMCDE-CF of Production Example 8, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [TMCDE]:[MBCC]:[3-VP]=48:26:26 (mol %).

[0310]

[0311] Synthesis Example 27 (Production of PC Polymer) A PC polymer (PC-27) having the following structure was obtained in the same manner as in Synthesis Example 23, except that the amount of 3-VP used in Synthesis Example 23 was adjusted so as to decrease the molecular weight.

[0312] (Identification of PC polymer) The structure and composition of the PC polymer (PC-27) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 2,818, and the compositional ratio (molar percentage) of the repeating unit [TMTMC] derived from the oligomer TMTMC-CF of Production Example 5, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [TMTMC]:[MBCC]:[3-VP]=46:30:24 (mol %).

[0313]

[0314] Synthesis Example 28 (Production of PC Polymer) A PC polymer (PC-28) having the following structure was obtained in the same manner as in Synthesis Example 4, except that the amount of 3-VP used in Synthesis Example 4 was adjusted so as to increase the molecular weight.

[0315] (Identification of PC polymer) The structure and composition of the PC polymer (PC-28) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 4,468, and the compositional ratio (molar percentage) of the repeating unit [CHZ] derived from the oligomer CHZ-CF of Production Example 3, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [CHZ]:[MBCC]:[3-VP]=57:25:18 (mol %).

[0316]

[0317] Synthesis Example 29 (Production of PC Polymer) A PC polymer (PC-29) having the following structure was obtained in the same manner as in Synthesis Example 3, except that the amount of 3-VP used in Synthesis Example 3 was adjusted so as to increase the molecular weight.

[0318] (Identification of PC polymer) The structure and composition of the PC polymer (PC-29) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １ The number average molecular weight calculated from the H-NMR spectrum was 4,434, and the compositional ratio (molar percentage) of the repeating unit [OCCDE] derived from the oligomer OCCDE-CF of Production Example 2, the repeating unit [MBCC] derived from the raw material monomer MBCC, and the structural unit [3-VP] derived from the end terminator 3-VP was [OCCDE]:[MBCC]:[3-VP]=57:27:16 (mol %).

[0319]

[0320] Synthesis Example 30 (Production of PC Polymer) A PC polymer (PC-30) having the following structure was obtained in the same manner as in Synthesis Example 20, except that TMBA-CF obtained in Production Example 7 was used instead of OCTMC-CF, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)-propane was used instead of OCTMC, and methacrylic acid chloride was used instead of 3-VP. 2,2-bis(4-hydroxy-3,5-dimethylphenyl)-propane will hereinafter be referred to as TMBA, and methacrylic acid chloride will hereinafter be referred to as MA, in some cases.

[0321] (Identification of PC polymer) The structure and composition of the PC polymer (PC-30) obtained in this manner were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units: １The number average molecular weight calculated from the H-NMR spectrum was 1,628, and the compositional ratio (molar percentage) of the repeating units derived from the oligomer TMBA-CF of Production Example 7, the repeating units [TMBA] derived from the raw material monomer TMBA, and the structural units [MA] derived from the end terminator MA was [TMBA]:[MA]=70:30 (mol %).

[0322]

[0323] <Preparation of Coating Composition Comprising Polycarbonate and Fabrication of Resin Film (1)> [Example 1] A PC polymer (PC-1) (1.5 g) was weighed into a sample tube with a screw cap and dissolved in 1.5 g of toluene to obtain a coating composition. 15 mg of dicumyl peroxide was added to the obtained coating composition and completely dissolved, and then an applicator was used to cast a film of the coating composition onto a polyimide film. This was dried by heating in a dryer at 100°C for 1 hour and at 200°C for 3 hours to distill off the solvent, thereby obtaining a resin film according to Example 1 having a thickness of 50 μm to 150 μm.

[0324] [Examples 2 to 29] Resin films according to Examples 2 to 29 were obtained in the same manner as in Example 1, except that PC polymers (PC-2) to (PC-29) were used instead of the PC polymer (PC-1). The numbers according to the Examples correspond to the numbers according to the Synthesis Examples and the PC polymers, respectively.

[0325] Comparative Example 1 A resin film according to Comparative Example 1 was obtained in the same manner as in Example 1, except that the PC polymer (PC-30) was used instead of the PC polymer (PC-1).

[0326] [Reference Example 1] A polyphenylene ether (SA9000, manufactured by SABIC Corporation, number average molecular weight 2300) in which both ends of the molecular chain were methacrylic-modified was prepared. A resin film according to Reference Example 1 was obtained in the same manner as in Example 1, except that the prepared polyphenylene ether was used instead of the PC polymer (PC-1).

[0327] [Evaluation of Physical Properties of Polycarbonate Resin] The physical properties of the polycarbonate resin (PC polymer) and the resin film were evaluated by the following methods.

[0328] <Evaluation of number average molecular weight (Mn) and copolymerization ratio> A polycarbonate resin was dissolved in methylene dichloride as a heavy solvent to prepare a solution, and the solution was measured using JNM-ECA500 (manufactured by JEOL Ltd., 500 MHz). １ H-NMR was measured to determine the composition ratio of each monomer component of the resulting polycarbonate resin. The number average molecular weight (Mn) was calculated using the calculated composition ratio.

[0329] <Evaluation of Relative Dielectric Constant and Dielectric Loss Tangent> A square film measuring 60 mm in length and 60 mm in width was cut from the resin film and conditioned for 24 hours under conditions of room temperature 22±1°C and humidity 33±5%. Thereafter, the relative dielectric constant (Dk) and dielectric loss tangent (Df) were measured at a frequency of 10 GHz using a split cylinder resonator (manufactured by EMlabs) and a network analyzer (manufactured by Keysight Technologies). The temperature dependence of the dielectric properties (relative dielectric constant (Dk) and dielectric loss tangent (Df)) was also evaluated. The temperature dependence of the dielectric properties was further measured using an ESPEC SH-662 small environmental tester, where the temperature was changed and the relative dielectric constant (Dk) and dielectric loss tangent (Df) were measured at a frequency of 10 GHz. The results are shown in FIGS. 1 and 2. In the graph of FIG. 1, the vertical axis represents the relative dielectric constant (Dk) and the horizontal axis represents the temperature (°C) during measurement. In the graph of FIG. 2, the vertical axis represents the dielectric loss tangent (Df), and the horizontal axis represents the temperature (° C.) at the time of measurement.

[0330] <Evaluation of Solubility in Non-Halogenated Solvents (Toluene, Methyl Ethyl Ketone, or Cyclohexanone)> 2.0 g of any of the resin flakes from PC polymers (PC-1) to (PC-29), the resin flakes from Comparative Example 1 (PC polymer (PC-30)), or the resin flakes from Reference Example 1 (Polyphenylene Ether) and 2.0 g of toluene, methyl ethyl ketone (MEK), or cyclohexanone were added to a sample tube (resin flake concentration: 50% by mass), or 0.86 g of any of the resin flakes and 2.0 g of toluene, methyl ethyl ketone (MEK), or cyclohexanone were added (resin flake concentration: 30% by mass), and the mixture was stirred at room temperature to prepare a solution. After 24 hours, the appearance of the solution was visually confirmed. The results are shown in Table 1. A: No insoluble matter in a 50% by mass solution, transparent. B: White turbidity was visually observed in the 50% by mass solution, but no insoluble matter was found in the 30% by mass solution, and the solution was transparent. C: Insoluble matter was found in both the 30% by mass solution and the 5% by mass solution.

[0331]

[0332] The polycarbonate resins according to Examples 1 to 29, which contain a specific polycarbonate structural unit represented by Formula (UN1) in their repeating units and a terminal structure having a specific vinyl group, exhibited lower dielectric dissipation factor Df than the polycarbonate resin according to Comparative Example 1 and the polyphenylene ether resin according to Reference Example 1, which is widely used as an electronic substrate material. Furthermore, the polycarbonate resins according to Examples 26 to 29 exhibited comparable or smaller changes in dielectric properties under different temperature environments, one of the properties required for electronic substrate materials, compared to Comparative Example 1 and Reference Example 1. Note that the relative dielectric constant (Dk) of Example 29 is not shown in Figure 1 because it was below the lower limit of the vertical axis. Therefore, it was confirmed that the resin according to one embodiment of the present invention is highly effective in reducing transmission loss and can achieve a low dielectric dissipation factor. The resin according to one embodiment of the present invention can be used as an electronic substrate material. Furthermore, the polycarbonate resins according to Examples 1 to 29 were well soluble in all of the non-halogenated solvents methyl ethyl ketone, cyclohexanone, and toluene at specific concentrations, demonstrating good solubility in multiple types of non-halogenated solvents. Therefore, the resin according to one aspect of the present invention is suitable for solution molding using non-halogenated solvents without impairing the dielectric properties.

[0333] <Evaluation of Glass Transition Temperature and Thermal Expansion Coefficient> A strip of film 40 mm long and 4 mm wide was cut out from the resin film and measured using a TMA (manufactured by Hitachi High-Tech Science, product name: TMA7100). The results are shown in Table 2. Measurement mode: Tensile Temperature conditions: -30°C to 320°C Heating rate: 5°C / min Data processing method: The coefficient of thermal expansion (CTE) was calculated from 40°C to 100°C, and the temperature at the inflection point was used as the glass transition temperature (Tg).

[0334]

[0335] It was confirmed that the polycarbonate resins according to the examples, which contain the polycarbonate structural unit represented by formula (UN1) in their repeating units and which contain a terminal structure having a vinyl group, have thermal properties that enable their use as electronic substrate materials.

[0336] [Additional Note] The gist of the present invention may also include the following configurations.

[0337] [Structure A1] A resin containing a polycarbonate structural unit represented by the following formula (UN1) and a terminal structure having a vinyl group (excluding the polycarbonate structural unit represented by the following formula (A1) and the terminal structure represented by the following formula (A2)).

[0338]

[0339]

[0340] [(In the formula (UN1), R １ and R ２ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group; n is 0, 1, 2, 3, or 4; m is 0, 1, 2, 3, or 4; R １ If there are multiple R １ are the same or different from each other, R ２ If there are multiple R ２are the same or different, Ux is (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -C(R ３ ) (R ４ )-, a group represented by —S—, —SO—, —SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), R ３ and R ４ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, and * represents a bond. (The * in the formula (A1) represents a bond, and the * in the formula (A2) represents a bond to a repeating unit located at an end of the resin.)

[0341] [Configuration A2] The resin according to Configuration A1, wherein the terminal structure is a terminal structure represented by the following formula (ME1):

[0342]

[0343] (In the formula (ME1), R １１ represents a hydrogen atom, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; q is 0, 1, or 2, provided that when q is 0, the benzene ring A has a vinyl group; and * represents a bond.

[0344] [Configuration A3] The resin according to Configuration A1 or A2, wherein the terminal structure includes at least one terminal structure selected from the group consisting of terminal structures represented by the following formulas (ME11), (ME12), (ME13), and (ME14):

[0345]

[0346] (In the formulae (ME11), (ME12), (ME13), and (ME14), * represents a bond.)

[0347] [Structure A4] The resin according to any one of Structures A1 to A3, wherein the polycarbonate structural unit represented by Formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by Formula (UN11) and Formula (UN12):

[0348]

[0349]

[0350] [(In the formula (UN11), Ux is a single bond, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, or —C(R ３ ) (R ４ )-, and R １５１ , R １５２ , R １５３ , R １５４ , R １５５ , R １５６ , R １５７ , and R １５８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; R ３ and R ４ represents R in the formula (UN1). ３ and R ４ and * is a bond.) (In the formula (UN12), R ２１４ and R ２１５ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R２１１ , R ２１２ , R ２１３ , R ２１６ , R ２１７ and R ２１８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * represents a bond.

[0351] [Structure A5] The resin according to Structure A4, wherein the polycarbonate structural unit represented by formula (UN11) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulas (UN111), (UN112), (UN113), (UN114), (UN115), (UN116), and (UN117), and the polycarbonate structural unit represented by formula (UN12) is a polycarbonate structural unit represented by the following formula (UN121).

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360] (In the formula (UN111), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ５１ , R ５２ , and R ５３are each independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, * is a bond, and in the formulae (UN112) to (UN115), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ * is a bond, and in the formula (UN116), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ３１ and R ４１ are each independently a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, * is a bond, and in the formula (UN117), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ３２ is a substituted or unsubstituted alkyl group having 1 carbon atom, R ４２ is a substituted or unsubstituted alkyl group having 13 to 22 carbon atoms, ４２ represents a linear alkyl group, * represents a bond, and in the formula (UN121), R ２１２ , R ２１４ , R ２１５ , and R ２１７ are each independently R in formula (UN12). ２１２ , R ２１４ , R ２１５ , and R ２１７ and * is a bond.)

[0361] [Structure A6] The resin according to any one of Structures A1 to A5, wherein the polycarbonate structural unit represented by Formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following Formulas (UN111-TMC-1), (UN111-TMC-2), (UN112-CH), (UN116-CH), (UN121-CH), (UN113-BP-1), (UN113-BP-2), (UN115-BP), (UN116-BP), (UN114-CDE), and (UN117-LL).

[0362]

[0363]

[0364]

[0365]

[0366]

[0367] [Configuration A7] In the resin according to any one of Configurations A1 to A6, １ A resin having a number average molecular weight calculated from a H-NMR spectrum of 500 or more and 20,000 or less.

[0368] [Configuration A8] A method for producing the resin according to any one of Configurations A1 to A7, comprising a step of interfacially polycondensing a bischloroformate monomer or bischloroformate oligomer represented by the following formula (M-UN1), from which the polycarbonate structural unit represented by formula (UN1) is derived, a bisphenol compound, and a phenol compound represented by the following formula (M-ME1), from which formula (ME1) is derived.

[0369]

[0370]

[0371] (In the formula (M-UN1), Ux, R １ , R ２ , m, and n are Ux and R in the formula (UN1), respectively.１ , R ２ , m, and n; １Ａ represents the average number of mers, and n １Ａ is 1.0 or more and 10 or less, and in the formula (M-ME1), R １１ is a hydrogen atom, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and q is 0, 1, or 2, provided that when q is 0, the vinyl group is present on the benzene ring A.

[0372] [Configuration A9] A resin composition comprising the resin according to any one of Configurations A1 to A7 and a radical polymerization initiator.

[0373] [Configuration A10] A cured product obtained by subjecting the resin composition according to Configuration A9 to a curing reaction.

[0374] [Configuration A11] The cured product according to configuration A10, wherein the cured product has a relative dielectric constant Dk of 2.85 or less at a frequency of 10 GHz as measured by a resonator perturbation method using a split cylinder resonator.

[0375] [Configuration A12] The cured product according to Configuration A10 or A11, wherein the cured product has a dielectric loss tangent Df of 0.00300 or less.

[0376] [Configuration A13] A film comprising the cured product according to any one of Configurations A10 to A12.

[0377] [Configuration A14] A coating liquid composition comprising the resin composition according to Configuration A9 and a non-halogenated solvent, wherein the resin composition is dissolved in the non-halogenated solvent.

[0378] [Configuration A15] A prepreg comprising the coating composition according to Configuration A14 and a fibrous substrate, wherein the fibrous substrate is impregnated with the coating composition, and the coating composition is in a semi-cured state or a fully cured state.

[0379] [Configuration A16] An electronic substrate comprising the prepreg according to Configuration A15 and copper foil.

Claims

The copolymer comprises a polycarbonate structural unit represented by the following formula (UN1) and a terminal structure having a vinyl group: Resin (excluding the polycarbonate structural unit represented by the following formula (A1) and the terminal structure represented by the following formula (A2)). [(In the formula (UN1), R １ and R ２ are each independently, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms; halogen atoms, nitro group, aldehyde groups, a cyano group, or is a carboxy group, n is 0, 1, 2, 3, or 4; m is 0, 1, 2, 3, or 4; R １ If there are multiple R １ are the same or different from each other, R ２ If there are multiple R ２ are the same or different from each other, Ux is, (i) is a single bond, (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms; -C(R ３ ) (R ４ )-, -S-, -SO-, -SO ２ -、 -O-, and a group selected from the group consisting of —CO—; (iii) a divalent group formed by linking two or more groups selected from the group (ii), R ３ and R ４ are each independently, a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, * represents a bond.) (In the formula (A1), * represents a bond, and in the formula (A2), * represents a bond to a repeating unit located at an end of the resin.) 　 The resin according to claim 1, The terminal structure is a terminal structure represented by the following formula (ME1): resin. (In the formula (ME1), R １１ teeth, hydrogen atoms, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, q is 0, 1, or 2; However, when q is 0, the benzene ring A has a vinyl group. When q is 1, the benzene ring B has a vinyl group; When q is 2, only the benzene ring B farthest from the benzene ring A has a vinyl group; * represents a bond.) 　 The resin according to claim 1 or 2, The terminal structure includes at least one terminal structure selected from the group consisting of terminal structures represented by the following formulas (ME11), (ME12), (ME13), and (ME14): resin. (In the formulae (ME11), (ME12), (ME13), and (ME14), * represents a bond.) 　 The resin according to any one of claims 1 to 3, The polycarbonate structural unit represented by formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by formulas (UN11) and (UN12): resin. [(In the formula (UN11), Ux, single bond, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, or -C(R ３ ) (R ４ )- is a group represented by R １５１ , R １５２ , R １５３ , R １５４ , R １５５ , R １５６ , R １５７ , and R １５８ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, R ３ and R ４ represents R in the formula (UN1). ３ and R ４ is synonymous with * is a bond.) (In the formula (UN12), R ２１４ and R ２１５ each independently represents a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R ２１１ , R ２１２ , R ２１３ , R ２１６ , R ２１７ , and R ２１８ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, * denotes a bond.) 　 The resin according to claim 4, The polycarbonate structural unit represented by formula (UN11) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulas (UN111), (UN112), (UN113), (UN114), (UN115), (UN116), and (UN117), The polycarbonate structural unit represented by the formula (UN12) is a polycarbonate structural unit represented by the following formula (UN121): resin. (In the formula (UN111), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ５１ , R ５２ , and R ５３ are each independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, * is a bond, In the formulae (UN112) to (UN115), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with * is a bond, In the formula (UN116), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ３１ and R ４１ are each independently a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, * is a bond, In the formula (UN117), R １５１ ~R １５８ are each independently R in formula (UN11). １５１ ~R １５８ is synonymous with R ３２ is a substituted or unsubstituted alkyl group having 1 carbon atom, R ４２ is a substituted or unsubstituted alkyl group having 13 to 22 carbon atoms, However, R ４２ is a straight chain alkyl group, * is a bond, In the formula (UN121), R ２１２ , R ２１４ , R ２１５ , and R ２１７ are each independently R in formula (UN12). ２１２ , R ２１４ , R ２１５ , and R ２１７ is synonymous with * is a bond.) 　 The resin according to any one of claims 1 to 5, The polycarbonate structural unit represented by formula (UN1) is at least one polycarbonate structural unit selected from the group consisting of polycarbonate structural units represented by the following formulas (UN111-TMC-1), (UN111-TMC-2), (UN112-CH), (UN116-CH), (UN121-CH), (UN113-BP-1), (UN113-BP-2), (UN115-BP), (UN116-BP), (UN114-CDE-1), (UN114-CDE-2), and (UN117-LL); resin. (In the formulae (UN111-TMC-1), (UN111-TMC-2), (UN112-CH), (UN116-CH), (UN121-CH), (UN113-BP-1), (UN113-BP-2), (UN115-BP), (UN116-BP), (UN114-CDE-1), (UN114-CDE-2), and (UN117-LL), * is a bond.) 　 The resin according to any one of claims 1 to 6, １ The number average molecular weight calculated from the H-NMR spectrum is 500 or more and 20,000 or less. resin. 　 A method for producing the resin according to any one of claims 1 to 7, comprising: The method includes a step of interfacially polycondensing a bischloroformate monomer or bischloroformate oligomer represented by the following formula (M-UN1), from which the polycarbonate structural unit represented by the formula (UN1) is derived, a bisphenol compound, and a phenol compound represented by the following formula (M-ME1), from which the formula (ME1) is derived: Resin manufacturing method. (In the formula (M-UN1), Ux, R １ , R ２ , m, and n each independently represent Ux, R in formula (UN1). １ , R ２ , m, and n; n １Ａ represents the average number of mers, and n １Ａ is equal to or greater than 1.0 and equal to or less than 10, In the formula (M-ME1), R １１ represents a hydrogen atom, a methoxy group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and q is 0, 1, or 2, provided that when q is 0, benzene ring A has a vinyl group, when q is 1, benzene ring B has a vinyl group, and when q is 2, only the benzene ring B farthest from benzene ring A has a vinyl group. 　 A composition comprising the resin according to any one of claims 1 to 7 and a radical polymerization initiator. Resin composition. 　 A resin composition obtained by subjecting the resin composition according to claim 9 to a curing reaction. cured product. 　 The cured product according to claim 10, The dielectric constant Dk at a frequency of 10 GHz measured by a resonator perturbation method using a split cylinder resonator is 2.85 or less. cured product. 　 The cured product according to claim 10 or 11, The dielectric loss tangent Df at a frequency of 10 GHz measured by a resonator perturbation method using a split cylinder resonator is 0.00300 or less. cured product. 　 The cured product according to any one of claims 10 to 12, film. 　 A resin composition comprising the resin composition according to claim 9 and a non-halogen-based solvent, The resin composition is dissolved in the non-halogen-based solvent. Coating liquid composition. 　 A coating composition comprising the coating liquid composition according to claim 14 and a fibrous substrate, the fibrous substrate is impregnated with the coating liquid composition, The coating liquid composition is a semi-cured product or a completely cured product. Prepreg. 　 The prepreg according to claim 15 and a copper foil are included. Electronic board.

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