Polyformal resin, resin composition, cured product, film, coating liquid composition, prepreg, and electronic substrate

Abstract

Provided is a polyformal resin containing a structural unit represented by formula (UN1) and a terminal structure having a vinyl group, the terminal structure being present at both ends. In formula (UN1): Ux is a single bond or a divalent group; R1 and R2 are each independently substituents; m is 0, 1, 2, 3, or 4; n is 0, 1, 2, 3, or 4; and * represents a binding site.

Description

Polyformal resins, resin compositions, cured products, films, coating compositions, prepregs, and electronic substrates.

[0001] The present invention relates to polyformal resins, resin compositions, cured products, films, coating compositions, prepregs, and electronic substrates.

[0002] Next-generation high-speed communication technologies, known as 5G or 6G, possess features such as "high speed and large capacity," "massive simultaneous connections," and "ultra-low latency." These next-generation high-speed communication technologies are being introduced into various communication networks in fields such as electrical and electronic equipment, mobility (including automobiles), and healthcare, bringing about transformations in the economy and society. Electronic circuit boards and semiconductor package substrates (hereinafter referred to as electronic boards), which are used in electronic devices such as these communication devices, also face various challenges in improving the performance of electronic devices. One major challenge is that, with the increase in the amount of information transmitted, the frequencies used for communication are becoming higher. Due to the higher frequencies, the transmission loss, which is the rate at which electrical signal energy is lost when it is converted into unwanted energy such as heat energy, increases in the materials used in conventional electronic boards, resulting in energy loss problems and heat generation problems from the board.

[0003] Transmission loss consists of two elements: 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, in order to reduce transmission loss in electronic substrates 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 tendency to lower the roughness of the interface between the substrate and the metal wiring, and consequently, insulating materials are required to have greater adhesion to metal foils and metal plating.

[0004] Furthermore, electronic substrate materials are required to possess various properties in addition to reducing transmission loss. For example, high heat resistance to withstand high-temperature solder reflow and low thermal expansion to suppress warping of the substrate due to the difference in thermal expansion coefficients between the copper circuit and the insulating layer are required. When electronic substrate materials are used as insulating materials for coating and molding onto a substrate, the required properties include high solvent solubility, low solution viscosity, and filler dispersibility. Moreover, the required properties for electronic substrate materials used to form thin films used when laminating wiring layers include high solvent solubility, low viscosity, filler dispersibility, or minimal change in dielectric properties under operating conditions such as temperature and humidity.

[0005] As insulating materials, thermoplastic resins such as liquid crystal polymers, polyphenylene ethers (PPE), polyimides, or fluororesins, as well as thermosetting resins such as epoxy resins, maleimide resins, or PPE, have been improved and developed for various applications, including electronic circuit boards. In electronic circuit board applications, thermosetting PPE is mainly used. However, the dielectric properties of PPE are currently unsatisfactory for application to next-generation high-speed communication technologies such as 5G or 6G. Therefore, there is a need for materials that can be applied to next-generation high-speed communication technologies such as 5G or 6G.

[0006] Patent Document 1 discloses a radical polymerizable monomer having an epoxy group and a predetermined molecular structure as one of the compounds included in a photochromic curable composition.

[0007] Patent Document 2 discloses a (meth)acrylic acetal resin having a predetermined molecular structure as a component included in a negative-type photosensitive composition.

[0008] Patent Document 3 discloses a water-soluble polysaccharide substituted with a substituent having a predetermined molecular structure as a component included in an orientation film composition.

[0009] International Publication No. 2009 / 075388, Japanese Patent Publication No. 2010-113141, Japanese Patent Publication No. 2004-206102

[0010] Incidentally, polyformal resins, for example, have excellent optical properties such as a low photoelastic coefficient and low birefringence, and their application in various fields of polymer material utilization is being considered, including, for example, optical memory discs, optical discs, and optical lenses. However, all polyformal resins that have been considered for application in fields of polymer material utilization are thermoplastic resins, and thermosetting polyformal resins have not been considered until now.

[0011] None of the above-mentioned Patent Documents 1, 2, and 3 describe polyformal resins for use as electronic substrate materials, nor do they describe or suggest the properties required for polyformal resins for use as electronic substrate materials (for example, dielectric properties and thermal properties).

[0012] The object of the present invention is to provide a polyformal resin having low dielectric properties and capable of reducing dielectric loss tangent, a resin composition containing the resin, a cured product, a film, a coating composition, a prepreg, and an electronic substrate.

[0013] As a result of diligent research, the inventors have found that by using a cured polyformal resin having a specific structural unit and an end structure with vinyl groups as curable groups at both ends, it is possible to obtain a material with low dielectric properties and low dielectric loss tangent that can be used as an electronic substrate material. Furthermore, they have found that the polyformal resin has excellent solvent solubility, and that the solvent-dissolved polyformal resin can be easily impregnated into a fibrous substrate. In other words, the gist of the present invention lies in the following [Configuration 1] to [Configuration 18].

[0014] [Configuration 1] A polyformal resin comprising a structural unit represented by the following formula (UN1) and an end structure having a vinyl group, wherein the end structure is present at both ends.

[0015]

[0016] (In the above formula (UN1), R １ and R ２is, independently of each other, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming 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-forming 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-forming carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming 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-forming atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group, m is 0, 1, 2, 3, or 4, n is 0, 1, 2, 3, or 4, R １ When there are a plurality of R １ they may be the same as or different from each other, and when there are a plurality of R ２ they may be the same as or different from each other. Ux is (i) a single bond, (ii) a substituted or unsubstituted divalent bridged cycloaliphatic hydrocarbon group having 4 to 28 carbon atoms, 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-forming carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring-forming carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring-forming carbon atoms, a group represented by -C(R ３ )(R ４ )-, -S-, -SO-, -SO ２ -, -O-, and -CO-, or (iii) a divalent group formed by linking two or more groups selected from the group of (ii), and R ３ and R ４ ​​Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and * represents a bond.

[0017] [Configuration 2] A polyformal resin according to Configuration 1, wherein the end structure includes at least one end structure selected from the group consisting of end structures represented by the following formulas (ME1-A1), (ME1-A2), (ME1-A3), and (ME2).

[0018]

[0019] (In the above formulas (ME1-A1), (ME1-A2), and (ME1-A3), R １１ Rx is a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted ring-forming C3-C10 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, p is 0, 1, or 2, Rx is a substituted or unsubstituted C1-C10 alkylene group, a substituted or unsubstituted ring-forming C3-C10 cycloalkylene group, a substituted or unsubstituted ring-forming C6-C14 arylene group, or -CO-, in formulas (ME1-A1), (ME1-A2), (ME1-A3), and (ME2), * represents a bond.

[0020] [Configuration 3] A polyformal resin according to Configuration 2, wherein the end structure represented by formula (ME1-A1) or formula (ME1-A2) is an end structure represented by the following formulas (ME11), (ME12), (ME13), (ME14), or (ME15).

[0021]

[0022] (In formulas (ME11), (ME12), (ME13), (ME14), and (ME15), * indicates a coupling.)

[0023] [Configuration 4] A polyformal resin according to any one of Configurations 1 to 3, further comprising a structural unit represented by the following formula (UN10).

[0024]

[0025] (In the above formula (UN10), R １Ｚ and R ２Ｚ Each of these is independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted ring-forming C6-C14 aryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted ring-forming C3-C20 cycloalkoxy group, a substituted or unsubstituted ring-forming C6-C14 aryloxy group, a substituted or unsubstituted C7-C20 aralkyl group, a substituted or unsubstituted C7-C20 aralkyloxy group, a substituted or unsubstituted ring-forming C5-C14 heteroaryl group, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxyl group, m Ｚ n is 0, 1, 2, 3, or 4. Ｚ is 0, 1, 2, 3, or 4, and R １Ｚ If multiple R １Ｚ They are either identical or different from each other, R ２Ｚ If multiple R ２Ｚ These are either identical or different from each other, and Uz is (i) a single bond, or (ii) a substituted or unsubstituted divalent cross-linked aliphatic hydrocarbon group having 4 to 28 carbon atoms, 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, -C(R ３Ｚ) (Caution ４Ｚ The groups represented by -, -S-, -SO-, -SO ２ A group selected from the group consisting of -, -O-, and -CO-, or (iii) a divalent group formed by linking two or more groups selected from the group in (ii), R ３Ｚ and R ４Ｚ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and * represents a bond.

[0026] [Configuration 5] A polyformal resin according to any one of Configurations 1 to 4, wherein the polyformal resin is represented by the following formula (PF-X).

[0027]

[0028] (In the above formula (PF-X), R １ , R ２ Ux, m, and n are each independently R in formula (UN1). １ , R ２ , is synonymous with Ux, m, and n, and R １Ｚ , R ２Ｚ , Uz, m Ｚ , and n Ｚ Each of these independently corresponds to R in the above formula (UN10). １Ｚ , R ２Ｚ , Uz, m Ｚ , and n Ｚ This is synonymous, where T is the number of repetitions of the structural unit represented by the above formula (UN1), and R １ and R １Ｚ They are either identical or different from each other, R ２ and R ２Ｚ Ux and Uz are either identical or different from each other, ME Ａ１ and ME Ａ２ Each of these is independently the terminal structure, ME Ａ１ and ME Ａ２ (They are either identical or different to each other.)

[0029] [Configuration 6] A polyformal resin according to any one of Configurations 1 to 3, wherein the structural unit represented by formula (UN1) is at least one structural unit selected from the group consisting of structural units represented by the following formulas (UN1A) and (UN1B).

[0030]

[0031]

[0032] [(In the above formula (UN1A), 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３ ) (Caution ４ It is a group represented by )-, R １Ａ , R １Ｂ , R １Ｃ , R １Ｄ , R ２Ａ , R ２Ｂ , R ２Ｃ , and R ２Ｄ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, R ３ and R ４ R in the above formula (UN1) is ３ and R ４ This is synonymous, and * is a coupling.) (In the above formula (UN1B), R １１Ｄ and R １２ＡEach is independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and R １１Ａ , R １１Ｂ , R １１Ｃ , R １２Ｂ , R １２Ｃ , and R １２Ｄ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, and * represents a bond.

[0033] [Configuration 7] A polyformal resin according to Configuration 6, wherein the structural unit represented by formula (UN1A) or formula (UN1B) and the terminal structure are directly bonded together.

[0034] [Configuration 8] A polyformal resin according to Configuration 4, wherein the structural unit represented by formula (UN10) is at least one structural unit selected from the group consisting of structural units represented by the following formulas (UN11) and (UN12).

[0035]

[0036]

[0037] [(In the above formula (UN11), Uz 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３Ｚ ) (Caution ４Ｚis a group represented by -, 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-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, and R ３Ｚ and R ４Ｚ are synonymous with R ３Ｚ and R ４Ｚ in the above formula (UN10), and * is a bond. ) (In the above formula (UN12), R ２１４ and R ２１５ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and 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-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, and * is a bond. ) ] [

[0038] [ [Configuration 9] In the polyformaldehyde resin according to Configuration 8, a polyformaldehyde resin in which the structural unit represented by the above formula (UN11) or the above formula (UN12) is directly bonded to the terminal structure. [

[0039] [ [Configuration 10] In the polyformaldehyde resin according to any one of Configurations 1 to 9, １ [ a polyformaldehyde resin having a number average molecular weight calculated from the 1H-NMR spectrum of 500 or more and 15,000 or less. [

[0040] [ [Configuration 11] A resin composition comprising the polyformaldehyde resin according to any one of Configurations 1 to 10 and a radical polymerization initiator. [

[0041] [Configuration 12] A cured product obtained by curing the resin composition described in Configuration 11.

[0042] [Configuration 13] A cured product according to Configuration 12, wherein the relative permittivity Dk at a frequency of 10 GHz, measured by a resonator perturbation method using a split cylinder resonator, is 2.80 or less.

[0043] [Configuration 14] A cured product according to Configuration 12 or Configuration 13, wherein the dielectric loss tangent Df at a frequency of 10 GHz, measured by a resonator perturbation method using a split cylinder resonator, is 0.00500 or less.

[0044] [Configuration 15] A film comprising the cured product described in any one of Configurations 12 to 14.

[0045] [Configuration 16] A coating liquid composition comprising the resin composition described in Configuration 11 and a non-halogenated solvent, wherein the resin composition is dissolved in the non-halogenated solvent.

[0046] [Configuration 17] A prepreg comprising the coating liquid composition described in Configuration 16 and a fibrous substrate, wherein the fibrous substrate is impregnated with the coating liquid composition, and the coating liquid composition is either semi-cured or fully cured.

[0047] [Configuration 18] An electronic substrate comprising the prepreg described in Configuration 17 and copper foil.

[0048] According to one aspect of the present invention, a polyformal resin having low dielectric properties and capable of reducing dielectric loss tangent, a resin composition containing the resin, a cured product, a film, a coating composition, a prepreg, and an electronic substrate can be provided.

[0049] [Resin] The polyformal resin according to this embodiment comprises a structural unit represented by the following formula (UN1) and an end structure having a vinyl group, with the end structure having both ends. In this specification, the polyformal resin is a concept that encompasses polyformal oligomers.

[0050]

[0051] (In the above formula (UN1), R １ and R ２is, independently of each other, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming 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-forming 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-forming carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming 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-forming atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group, m is 0, 1, 2, 3, or 4, n is 0, 1, 2, 3, or 4, and R １ When there are a plurality of R １ they may be the same as or different from each other, and when there are a plurality of R ２ they may be the same as or different from each other. Ux is (i) a single bond, (ii) a substituted or unsubstituted divalent bridged cycloaliphatic hydrocarbon group having 4 to 28 carbon atoms, 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-forming carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring-forming carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring-forming carbon atoms, a group represented by -C(R ３ )(R ４ ), -S-, -SO-, -SO ２ -, -O-, and -CO-, or (iii) a divalent group formed by linking two or more groups selected from the group of (ii), and R ３ and R ４ ​​Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and * represents a bond.

[0052] In this specification, the term "polyformal resin" is a concept that includes both homopolymers and copolymers, and when specifying that the polyformal resin is a copolymer, it is referred to as a copolymer.

[0053] In one embodiment of the polyformal resin according to this embodiment, Ux in formula (UN1) is a single bond, a substituted or unsubstituted divalent cross-linked aliphatic hydrocarbon group having 4 to 28 carbon atoms, 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, or -C(R ３ ) (Caution ４ It is also preferable that the group be represented by )-.

[0054] In one embodiment of the polyformal resin according to this embodiment, Ux in formula (UN1) is also preferably a single bond, substituted or unsubstituted divalent cross-linked aliphatic hydrocarbon group having 4 to 28 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 carbon atoms forming a ring, or a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring.

[0055] In one embodiment of the polyformal resin according to this embodiment, if Ux in formula (UN1) is a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring-forming carbon atoms, it is also preferable that Ux is a group represented by the following formula (Ux-A).

[0056]

[0057] (In the above formula (UX-A), q １ q is an integer between 3 and 26. ２ is 0, 1, 2, or 3, and q２ When R is 1, 2, or 3, １００ R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. １００ If multiple R １００ (These are either identical or different from each other, and * represents a combination.)

[0058] In the above formula (UX-A), q １ It is also preferable that it be an integer between 5 and 15, an integer between 5 and 12, or an integer between 5 and 10.

[0059] In the above formula (UX-A), q ２ It is also preferable that it be 0, and it is also preferable that it be 3.

[0060] In the above formula (UX-A), q ２ It is also preferable that q be 0. In the above formula (UX-A), q ２ It is also preferable that it be 3.

[0061] In the above formula (UX-A), R １００ It is also preferable that the alkyl group is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0062] In one embodiment of the polyformal resin according to this embodiment, it is also preferable that m and n in formula (UN1) are independently 1, 2, or 3.

[0063] In one embodiment of the polyformal resin according to this embodiment, when n and m in formula (UN1) are independently 1, 2, or 3, then R in formula (UN1) １ and R ２ These may each be 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-forming carbon atoms.

[0064] In one embodiment of the polyformal resin according to this embodiment, when n and m in formula (UN1) are independently 1, 2, or 3, then R in formula (UN1) １ and R ２ Each of these elements may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0065] In the polyformal resin according to this embodiment, the end structures having vinyl groups are present at both ends of the polyformal resin. In one embodiment of the polyformal resin according to this embodiment, it is preferable that the structural unit represented by formula (UN1) and the end structures having vinyl groups are directly bonded. In one embodiment, it is preferable that the end structures having vinyl groups in the polyformal resin according to this embodiment are bonded to the repeating units of the structural unit represented by formula (UN1) located at the ends of the resin.

[0066] In one embodiment of the polyformal resin according to this embodiment, the end structure (i.e., the end structure having a vinyl group) preferably includes at least one end structure selected from the group consisting of end structures represented by the following formulas (ME1-A1), (ME1-A2), (ME1-A3), and (ME2).

[0067]

[0068] (In the above formulas (ME1-A1), (ME1-A2), and (ME1-A3), R １１Rx is a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted ring-forming C3-C10 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, p is 0, 1, or 2, Rx is a substituted or unsubstituted C1-C10 alkylene group, a substituted or unsubstituted ring-forming C3-C10 cycloalkylene group, a substituted or unsubstituted ring-forming C6-C14 arylene group, or -CO-, in formulas (ME1-A1), (ME1-A2), (ME1-A3), and (ME2), * represents a bond.

[0069] In one embodiment of the polyformal resin according to this embodiment, it is also preferable that Rx in formulas (ME1-A1), (ME1-A2), and (ME1-A3) be a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

[0070] In one embodiment of the polyformal resin according to this embodiment, it is also preferable that p in formulas (ME1-A1), (ME1-A2), and (ME1-A3) is 0 or 1.

[0071] In one embodiment of the polyformal resin according to this embodiment, R in formulas (ME1-A1), (ME1-A2), and (ME1-A3) １１ It is also preferable that this is a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C1-C10 alkoxy group.

[0072] In one embodiment of the polyformal resin according to this embodiment, the end structure having a vinyl group preferably includes at least one end structure selected from the group consisting of end structures represented by formulas (ME1-A1), (ME1-A2), and (ME2).

[0073] In one embodiment of the polyformal resin according to this embodiment, it is also preferable that the end structure represented by formula (ME1-A1) or formula (ME1-A2) be an end structure represented by the following formulas (ME11), (ME12), (ME13), (ME14), or (ME15). That is, it is also preferable that the end structure represented by formula (ME1-A1) be an end structure represented by the following formulas (ME11), (ME12), (ME13), or (ME14), and that the end structure represented by formula (ME1-A2) be an end structure represented by the following formula (ME15).

[0074]

[0075] (In formulas (ME11), (ME12), (ME13), (ME14), and (ME15), * indicates a coupling.)

[0076] The terminal structures represented by formulas (ME11), (ME13), and (ME14) correspond to the case where Rx in formula (ME1-A1) is an unsubstituted C1 alkylene group (i.e., a methylene group) and p is 0. The terminal structure represented by formula (ME12) corresponds to the case where Rx in formula (ME1-A1) is an unsubstituted C1 alkylene group (methylene group), p is 1, and R １１ This corresponds to the case where is an unsubstituted carbon-1 alkoxy group (i.e., a methoxy group). The terminal structure represented by formula (ME15) corresponds to the case where Rx in formula (ME1-A2) is an unsubstituted carbon-1 alkylene group (methylene group) and p is 0.

[0077] In one embodiment of the polyformal resin according to this embodiment, the end structure having a vinyl group is preferably an end structure represented by formula (ME11), formula (ME13), or formula (ME14).

[0078] In one embodiment of the polyformal resin according to this embodiment, if the terminal structure having a vinyl group is a terminal structure represented by formula (ME14), the vinyl group may be substituted at the ortho position (o), the meta position (m), or the para position (p) with respect to the linking group (i.e., the methylene group) that connects to the structural unit located at the end of the polyformal resin according to this embodiment. In one embodiment where the terminal structure having a vinyl group is a terminal structure represented by formula (ME14), it may be one type of terminal structure in which the vinyl group is substituted at the ortho position, one type of terminal structure in which the vinyl group is substituted at the meta position, or a combination of two types of terminal structures: one in which the vinyl group is substituted at the para position and one in which the vinyl group is substituted at the meta position (i.e., both the terminal structure in which the vinyl group is substituted at the para position and the terminal structure in which the vinyl group is substituted at the meta position). In the case of the terminal structure represented by formula (ME14), for example, if only one type of terminal structure exists in which the vinyl group is substituted at the para position, the terminal structure represented by formula (ME14) in this case is the same as the terminal structure represented by formula (ME11), and if only one type of terminal structure exists in which the vinyl group is substituted at the meta position, the terminal structure represented by formula (ME14) in this case is the same as the terminal structure represented by formula (ME13). In the case of a combination of the two types of terminal structures, one in which the vinyl group is substituted at the para position and the other in which the vinyl group is substituted at the meta position, both the terminal structures represented by (ME11) and formula (ME13) exist.

[0079] In one embodiment of the polyformal resin according to this embodiment, the end structure having a vinyl group is also preferably the end structure represented by the formula (ME2).

[0080] In one embodiment of the polyformal resin according to this embodiment, it is preferable to further include a structural unit represented by the following formula (UN10).

[0081]

[0082] (In the above formula (UN10), R １Ｚ and R ２ＺEach of these is independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted ring-forming C6-C14 aryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted ring-forming C3-C20 cycloalkoxy group, a substituted or unsubstituted ring-forming C6-C14 aryloxy group, a substituted or unsubstituted C7-C20 aralkyl group, a substituted or unsubstituted C7-C20 aralkyloxy group, a substituted or unsubstituted ring-forming C5-C14 heteroaryl group, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxyl group, m Ｚ n is 0, 1, 2, 3, or 4. Ｚ is 0, 1, 2, 3, or 4, and R １Ｚ If multiple R １Ｚ They are either identical or different from each other, R ２Ｚ If multiple R ２Ｚ These are either identical or different from each other, and Uz is (i) a single bond, or (ii) a substituted or unsubstituted divalent cross-linked aliphatic hydrocarbon group having 4 to 28 carbon atoms, 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, -C(R ３Ｚ ) (Caution ４Ｚ The groups represented by -, -S-, -SO-, -SO ２ A group selected from the group consisting of -, -O-, and -CO-, or (iii) a divalent group formed by linking two or more groups selected from the group in (ii), R ３Ｚ and R ４ＺEach of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and * represents a bond.

[0083] In one embodiment of the polyformal resin according to this embodiment, Uz in formula (UN10) is a single bond, a substituted or unsubstituted divalent cross-linked aliphatic hydrocarbon group having 4 to 28 carbon atoms, 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, or -C(R ３Ｚ ) (Caution ４Ｚ It is also preferable that the group be represented by )-.

[0084] In one embodiment of the polyformal resin according to this embodiment, Uz in formula (UN10) is also preferably a single-bonded, substituted or unsubstituted divalent cross-linked aliphatic hydrocarbon group having 4 to 28 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 carbon atoms forming a ring, or a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring.

[0085] In one embodiment of the polyformal resin according to this embodiment, the m in formula (UN10) Ｚ and n Ｚ It is also preferable that each of these be independently 1, 2, or 3.

[0086] In one embodiment of the polyformal resin according to this embodiment, the m in formula (UN10) Ｚ and n Ｚ However, when each is independently 1, 2, or 3, R in formula (UN10) １Ｚ and R ２Ｚ These may each be 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-forming carbon atoms.

[0087] In one embodiment of the polyformal resin according to this embodiment, it is preferable that the structural unit represented by formula (UN10) and the terminal structure are directly bonded together.

[0088] One embodiment of the polyformal resin according to this embodiment is also preferably a resin represented by the following formula (PF-X).

[0089]

[0090] (In the above formula (PF-X), R １ , R ２ Ux, m, and n are each independently R in formula (UN1). １ , R ２ , is synonymous with Ux, m, and n, and R １Ｚ , R ２Ｚ , Uz, m Ｚ , and n Ｚ Each of these independently corresponds to R in the above formula (UN10). １Ｚ , R ２Ｚ , Uz, m Ｚ , and n Ｚ This is synonymous, where T is the number of repetitions of the structural unit represented by the above formula (UN1), and R １ and R １Ｚ They are either identical or different from each other, R ２ and R ２Ｚ Ux and Uz are either identical or different from each other, ME Ａ１ and ME Ａ２ Each of these is independently the terminal structure, ME Ａ１ and ME Ａ２ (They are either identical or different to each other.)

[0091] The number of T in the above formula (PF - X) is not particularly limited. The number of T is, for example, １ One example is a numerical range that satisfies the range of 500 or more and 15,000 or less for the number-average molecular weight Mn calculated from the H-NMR spectrum.

[0092] In one embodiment of the polyformal resin according to this embodiment, the resin represented by formula (PF-X) is also preferably the resin represented by the following formula (PF-X1).

[0093]

[0094] (In the above formula (PF-X1), R １ , R ２ Ux, m, n, R １Ｚ , R ２Ｚ , Uz, m Ｚ , n Ｚ , T, ME Ａ１ , and ME Ａ２ Each of these independently corresponds to R in the above formula (PF-X). １ , R ２ Ux, m, n, R １Ｚ , R ２Ｚ , Uz, m Ｚ , n Ｚ , T, ME Ａ１ , and ME Ａ２ (This is synonymous with...)

[0095] In one embodiment of the polyformal resin according to this embodiment, it is preferable that the structural unit represented by formula (UN1) is at least one structural unit selected from the group consisting of structural units represented by the following formulas (UN1A) and (UN1B).

[0096]

[0097]

[0098] [(In the above formula (UN1A), 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３ ) (Caution ４It is a group represented by )-, R １Ａ , R １Ｂ , R １Ｃ , R １Ｄ , R ２Ａ , R ２Ｂ , R ２Ｃ , and R ２Ｄ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, R ３ and R ４ R in the above formula (UN1) is ３ and R ４ This is synonymous, and * is a coupling.) (In the above formula (UN1B), R １１Ｄ and R １２Ａ Each is independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and R １１Ａ , R １１Ｂ , R １１Ｃ , R １２Ｂ , R １２Ｃ , and R １２Ｄ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, and * represents a bond.

[0099] In one embodiment of the polyformal resin according to this embodiment, Ux in formula (UN1A) is a single bond, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３ ) (Caution ４ It is also preferable that the group be represented by )-.

[0100] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ ~R １Ｄ , and R ２Ａ ~R ２Ｄ These may each be independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group.

[0101] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ , R １Ｄ , R ２Ｂ , and R ２Ｃ These may each be independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group.

[0102] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ , R １Ｄ , R ２Ｂ , and R ２Ｃ These may each be independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0103] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ ~R １Ｄ , and R ２Ａ ~R ２Ｄ These may all be hydrogen atoms.

[0104] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ ~R １Ｄ , and R ２Ａ ~R ２Ｄ It is also preferable that it is not a hydrogen atom.

[0105] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ｂ and R １Ｃ At least one of the following, and R２Ａ and R ２Ｄ At least one of them is a hydrogen atom, R １Ａ , R １Ｄ , R ２Ｂ , and R ２Ｃ It is also preferable that it is not a hydrogen atom.

[0106] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ and R １Ｄ At least one of the following, and R ２Ｂ and R ２Ｃ At least one of them is a hydrogen atom, R １Ｂ , R １Ｃ , R ２Ａ , and R ２Ｄ It is also preferable that all of them are hydrogen atoms.

[0107] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ ~R １Ｄ At least one of the following, and R ２Ａ ~R ２Ｄ At least one of them is a substituted or unsubstituted C1-C20 alkyl group, and the remaining R is not a substituted or unsubstituted C1-C20 alkyl group. １Ａ ~R １Ｄ and R ２Ａ ~R ２Ｄ It is also preferable that all of them are hydrogen atoms.

[0108] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1A) １Ａ ~R １Ｄ At least one of the following, and R ２Ａ ~R ２Ｄ If at least one of them is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms may also preferably be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0109] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1B) １１Ｂ and R １２Ｃ These may each be independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group.

[0110] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1B) １１Ａ ~R １１Ｃ , R １２Ｂ ~R １２Ｄ It is also preferable that it is not a hydrogen atom.

[0111] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN1B) １１Ａ , R １１Ｃ , R １２Ｂ , and R １２Ｄ These are all hydrogen atoms, and R in formula (UN1B) １１Ｂ and R １２Ｃ It is also preferable that it is not a hydrogen atom.

[0112] In one embodiment of the polyformal resin according to this embodiment, it is also preferable that the structural unit represented by formula (UN1A) or formula (UN1B) and the terminal structure are directly bonded together.

[0113] In one embodiment of the polyformal resin according to this embodiment, it is preferable that the structural unit represented by formula (UN10) is at least one structural unit selected from the group consisting of structural units represented by the following formulas (UN11) and (UN12).

[0114]

[0115]

[0116] [(In the above formula (UN11), Uz 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３Ｚ ) (Caution ４Ｚ It is a group represented by )-, R １５１ , R １５２ , R １５３ , R １５４ , R １５５ , R １５６ , R １５７ , and R １５８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, R ３Ｚ and R ４Ｚ R in the above formula (UN10) is ３Ｚ and R ４Ｚ This is synonymous, and * is a coupling.) (In the above formula (UN12), R ２１４ and R ２１５ Each is independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and R ２１１ , R ２１２ , R ２１３ , R ２１６ , R ２１７ , and R ２１８Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, and * represents a bond.

[0117] In one embodiment of the polyformal resin according to this embodiment, Uz in formula (UN11) is a single bond, a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３Ｚ ) (Caution ４Ｚ It is also preferable that the group be represented by )-.

[0118] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５１ ~R １５８ These may each be independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group.

[0119] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５１ , R １５４ , R １５６ , and R １５７ These may each be independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group.

[0120] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５１ , R １５４ , R １５６ , and R １５７These may each be independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0121] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５１ ~R １５８ These may all be hydrogen atoms.

[0122] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５１ ~R １５８ It is also preferable that it is not a hydrogen atom.

[0123] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５２ and R １５３ At least one of the following, and R １５５ and R １５８ At least one of them is a hydrogen atom, R １５１ , R １５４ , R １５６ , and R １５７ It is also preferable that it is not a hydrogen atom.

[0124] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５１ and R １５４ At least one of the following, and R １５６ and R １５７ At least one of them is a hydrogen atom, R １５２ , R １５３ , R １５５ , and R １５８ It is also preferable that all of them are hydrogen atoms.

[0125] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN11) １５１ ~R １５４ At least one of the following, and R １５５ ~R １５８ At least one of them is a substituted or unsubstituted C1-C20 alkyl group, and the remaining R is not a substituted or unsubstituted C1-C20 alkyl group. １５１ ~R１５４ and R １５５ ~R １５８ It is also preferable that all of them are hydrogen atoms.

[0126] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN12) ２１２ and R ２１７ These may each be independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group.

[0127] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN12) ２１１ ~R ２１３ , R ２１６ ~R ２１８ It is also preferable that it is not a hydrogen atom.

[0128] In one embodiment of the polyformal resin according to this embodiment, R in formula (UN12) ２１１ , R ２１３ , R ２１６ , and R ２１８ These are all hydrogen atoms, and R in formula (UN12) ２１２ and R ２１７ It is also preferable that it is not a hydrogen atom.

[0129] In one embodiment of the polyformal resin according to this embodiment, it is preferable that the structural unit represented by formula (UN11) or formula (UN12) and the terminal structure are directly bonded together.

[0130] In one embodiment of the polyformal resin according to this embodiment, it is preferable that all groups described as "substituted or unsubstituted" are unsubstituted groups.

[0131] In one embodiment of the polyformal resin according to this embodiment, the resin represented by formula (PF-X) is also preferably the resin represented by the following formula (PF-X1A).

[0132]

[0133] (In the above formula (PF-X1A), R １Ａ ~R１Ｄ , R ２Ａ ~R ２Ｄ Ux is independently R in formula (UN1A) １Ａ ~R １Ｄ , R ２Ａ ~R ２Ｄ , synonymous with Ux, R １５１ ~R １５４ , R １５５ ~R １５８ Uz is independently R in the above formula (UN11). １５１ ~R １５４ , R １５５ ~R １５８ , synonymous with Uz, and Ux and Uz are either identical or different from each other, T, ME Ａ１ , and ME Ａ２ These are, independently, T and ME in the above formula (PF-X) Ａ１ , and ME Ａ２ (This is synonymous with...)

[0134] (Copolymer) The polyformal resin according to this embodiment may be a copolymer. One embodiment of the polyformal resin according to this embodiment is a copolymer comprising a structural unit represented by formula (UN1) and an end structure having a vinyl group, wherein the end structure is present at both ends.

[0135] In the polyformal copolymer according to this embodiment, specific examples of terminal structures having vinyl groups are as described in the section on resins above.

[0136] In the polyformal copolymer according to this embodiment, each repeating unit is not necessarily continuous. One embodiment of the copolymer according to this embodiment is a block copolymer, an alternating copolymer, or a random copolymer.

[0137] When the polyformal copolymer according to this embodiment contains a plurality of structural units represented by formula (UN1), the plurality of structural units represented by formula (UN1) may be identical or different from each other. When the copolymer according to this embodiment contains a plurality of structural units represented by formula (UN1), the structural units that are different from the structural units represented by formula (UN1) are structural units represented by the following formula (UN2).

[0138] One embodiment of the polyformal resin according to this embodiment is a copolymer comprising a structural unit represented by formula (UN1), a structural unit represented by the following formula (UN2), and an end structure having a vinyl group, wherein the end structure is present at both ends.

[0139]

[0140] (In the above formula (UN2), R ６ and R ７ Each of these is independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted ring-forming C6-C14 aryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted ring-forming C3-C20 cycloalkoxy group, a substituted or unsubstituted ring-forming C6-C14 aryloxy group, a substituted or unsubstituted C7-C20 aralkyl group, a substituted or unsubstituted C7-C20 aralkyloxy group, a substituted or unsubstituted ring-forming C5-C14 heteroaryl group, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxyl group, and r is 0, 1, 2, 3, or 4. s is 0, 1, 2, 3, or 4, and R ６ If multiple R ６ They are either identical or different from each other, R ７ If multiple R ７ Uy is either identical or different from each other, (i) a single bond, or (ii) a substituted or unsubstituted divalent cross-linked aliphatic hydrocarbon group having 4 to 28 carbon atoms, 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, -C(R ３ｙ) (Caution ４ｙ The groups represented by -, -S-, -SO-, -SO ２ A group selected from the group consisting of -, -O-, and -CO-, or (iii) a divalent group formed by linking two or more groups selected from the group in (ii), R ３ｙ and R ４ｙ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and * represents a bond.

[0141] In one embodiment of the copolymer according to this embodiment, the structural unit represented by formula (UN2) is a structural unit selected from the group consisting of structural units represented by formula (UN1A) and formula (UN1B). When the copolymer according to this embodiment contains a plurality of structural units represented by formula (UN1A), the plurality of structural units represented by formula (UN1A) are either identical or different from one another. When the copolymer according to this embodiment contains a plurality of structural units represented by formula (UN1B), the plurality of structural units represented by the general formula (UN1B) are either identical or different from one another.

[0142] In one embodiment of the copolymer according to this embodiment, if it includes a structural unit represented by formula (UN1) and a structural unit represented by formula (UN2) that is different from the structural unit represented by formula (UN1), then the structural unit represented by general formula (UN1) is the structural unit represented by formula (UN1A) or formula (UN1B).

[0143] In one embodiment of the copolymer according to this embodiment, it is also preferable that it further includes a structural unit represented by formula (UN10). When the copolymer according to this embodiment includes a plurality of structural units represented by formula (UN10), the plurality of structural units represented by formula (UN10) may be identical or different from one another.

[0144] (Dielectric Properties) There are various methods for evaluating dielectric properties. A commonly used method is the cavity resonator perturbation method (hereinafter referred to as the cavity resonance method), which evaluates dielectric properties using an electric field along the sample. However, the electric field deviates outside the sample at both ends. Since there is no known quantitative explanation for this imperfection, it is customary to calculate the relative permittivity assuming that the electric field passes through the entire sample. Therefore, even though no electric field is applied at both ends of the sample, the dielectric properties are calculated assuming that an electric field is applied throughout, resulting in a low measured relative permittivity. On the other hand, the split cylinder resonator perturbation method (hereinafter referred to as the split cylinder method), which measures using a circular electric field along the surface of the sample, does not produce errors due to the deviation of the electric field at both ends of the sample that occurs in the cavity resonance method. Therefore, the split cylinder method outputs dielectric properties that are closer to the true value than the cavity resonance method.

[0145] The relative permittivity Dk of the polyformal resin according to one aspect of this embodiment is preferably 2.80 or less, preferably 2.75 or less, preferably 2.70 or less, more preferably 2.65 or less, even more preferably 2.60 or less, even more preferably 2.58 or less, even more preferably 2.56 or less, and still most preferably 2.55 or less. The lower limit of the relative permittivity Dk in the resin is not particularly limited and may be, for example, 2.20 or more. In this specification, the relative permittivity Dk of the resin is the value measured in a split-cylinder resonator at room temperature (23°C) and a frequency of 10 GHz.

[0146] Furthermore, the dielectric loss tangent Df of the polyformal resin according to one aspect of this embodiment is preferably 0.00500 or less, preferably 0.00450 or less, preferably 0.00400 or less, preferably 0.00350 or less, more preferably 0.00320 or less, even more preferably 0.00310 or less, even more preferably 0.00300 or less, and still more preferably 0.00250 or less. The lower limit of the dielectric loss tangent Df in the resin is not particularly limited and may be, for example, 0.00010 or more. In particular, from the viewpoint of achieving a low dielectric loss tangent, the dielectric loss tangent Df of the polyformal resin according to one aspect of this embodiment is more preferably 0.00350 or less. In this specification, the dielectric loss tangent Df of the resin is the value measured in a split cylinder resonator at room temperature (23°C) and a frequency of 10 GHz.

[0147] Because the relative permittivity Dk and dielectric loss tangent Df of the polyformal resin according to this embodiment are below the upper limit of the above range, when the polyformal resin according to this embodiment is used as an electronic substrate material, the loss of electrical signals within the electronic substrate can be reduced.

[0148] (Number average molecular weight) Polyformal 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 15,000 or less, more preferably 500 or more and 12,000 or less, even more preferably 500 or more and 10,000 or less, and even more preferably 500 or more and 8,000 or less.

[0149] In this specification, the number-average molecular weight Mn is determined by preparing a solution by dissolving the resin in methylene chloride as a solvent, and then using a nuclear magnetic resonance apparatus. １ The 1H-NMR spectrum is measured to determine the composition ratio of each monomer component in the resulting resin, and the composition ratio is derived from the obtained composition ratio. Specifically, it can be measured by the method described in the Examples section.

[0150] (Thermal Expansion Coefficient) In this embodiment, a low thermal expansion coefficient is preferable for the polyformal resin. Therefore, the thermal expansion coefficient of the polyformal resin according to one aspect of this embodiment from a temperature of 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, even more preferably 80 [ppm / K] or less, and still most preferably 70 [ppm / K] or less. The thermal expansion coefficient can be measured by the method described in the Examples section.

[0151] (Glass transition temperature (Tg)) The polyformal 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 still more preferably 170°C or higher. The glass transition temperature can be measured by the method described in the Examples section.

[0152] (Explanation of substituents, etc.) In the polyformal resin according to this embodiment, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0153] In the polyformal resin according to this embodiment, examples of alkyl groups include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, butyl groups, sec-butyl groups, tert-butyl groups, various pentyl groups, and various hexyl groups. In this specification, when "various" is attached to the name of a substituent, "various" indicates that it includes linear and all branched groups, and the same applies hereinafter. In the polyformal resin according to this embodiment, examples of substituted alkyl groups include trifluoromethyl groups. In the polyformal 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.

[0154] In this specification, the numerical range expressed using "AA to BB" means a range that includes the numerical value AA, which is written before "AA to BB", as the lower limit, and the numerical value BB, which is written after "AA to BB", as the upper limit.

[0155] In the polyformal resin according to this embodiment, the divalent cross-linked cyclic aliphatic hydrocarbon group is a group having a skeleton in which two or more monocyclic hydrocarbons are cross-linked, and examples include dicyclic, trimer, and tetramer forms of cycloalkylene groups. Examples of divalent cross-linked cyclic aliphatic hydrocarbon groups include, specifically, the bicycloalkanediyl group, tricycloalkanediyl group, bicycloalkylidene group, and tricycloalkylidene group described later. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the divalent cross-linked cyclic aliphatic hydrocarbon group is preferably 4 to 28, 4 to 20, 4 to 16, or 4 to 12, 5 to 28, 5 to 20, 5 to 16, or 5 to 12.

[0156] In the polyformal resin according to this embodiment, examples of alkylene groups include methylene groups, ethylene groups, trimethylene groups, tetramethylene groups, and hexamethylene groups. In the polyformal 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.

[0157] In the polyformal resin according to this embodiment, examples of alkylidene groups include ethylidene groups and isopropylidene groups. In the polyformal resin according to this embodiment, the number of carbon atoms in the alkylidene group is preferably 2 to 28, 2 to 20, 2 to 18, 2 to 10, or 2 to 5.

[0158] In the polyformal resin according to this embodiment, examples of alkoxy groups include methoxy groups, ethoxy groups, propoxy groups, isopropoxy groups, butoxy groups, isobutoxy groups, sec-butoxy groups, tert-butoxy groups, various pentyloxy groups, and various hexyloxy groups. In the polyformal 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.

[0159] In the polyformal resin according to this embodiment, examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the cycloalkyl group is preferably, for example, 3 to 26, 3 to 20, or 6 to 20.

[0160] In the polyformal resin according to this embodiment, examples of cycloalkylene groups include cyclopentanediyl groups, cyclohexanediyl groups, and cyclooctanediyl groups. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the cycloalkylene group is preferably, for example, 5 to 15 or 5 to 10.

[0161] In the polyformal resin according to this embodiment, examples of cycloalkylidene groups include cyclohexylidene groups, 3,5,5-trimethylcyclohexylidene groups, and cyclododecylene groups. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the cycloalkylidene group is preferably, for example, 3 to 26, 5 to 15, 5 to 12, or 5 to 10.

[0162] In the polyformal resin according to this embodiment, examples of bicycloalkanediyl groups include bicyclopentanediyl groups, bicyclohexanediyl groups, bicyclooctanediyl groups, and bicyclodecanediyl groups. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the bicycloalkanediyl group is preferably, for example, 4 to 28, 4 to 20, 4 to 16, or 4 to 12.

[0163] In the polyformal resin according to this embodiment, examples of the tricycloalkanediyl group include the tricyclohexanediyl group, the tricyclooctanediyl group, the adamantanediyl group, and the tricyclodecanediyl group. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the tricycloalkanediyl group is preferably, for example, 5 to 28, 5 to 20, 5 to 16, or 5 to 12.

[0164] In the polyformal resin according to this embodiment, examples of bicycloalkylidene groups include bicyclohexylidene groups, bicyclooctylidene groups, and bicyclodecylidene groups. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the bicycloalkanediyl group is preferably, for example, 4 to 28, 4 to 20, 4 to 16, or 4 to 12.

[0165] In the polyformal resin according to this embodiment, examples of the tricycloalkylidene group include tricyclohexylidene, tricyclooctylidene, adamantanecylidene, and tricyclodecylidene. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the tricycloalkylidene group is preferably, for example, 5 to 28, 5 to 20, 5 to 16, or 5 to 12.

[0166] In the polyformal resin according to this embodiment, the cycloalkoxy group can be, for example, the cycloalkyl group moiety is the cycloalkyl group, that is, Arx of the group represented by -O-Arx is the cycloalkyl group. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the cycloalkoxy group is preferably 3 to 20 or 6 to 20.

[0167] In the polyformal resin according to this embodiment, examples of alkenyl groups include ethenyl groups (vinyl groups), 1-propenyl groups, 2-propenyl groups (allyl groups), butenyl groups, pentenyl groups, and hexenyl groups. In the polyformal resin according to this embodiment, the number of carbon atoms in the alkenyl group is preferably, for example, 2 to 10 or 2 to 6.

[0168] In the polyformal resin according to this embodiment, examples of alkynyl groups include ethynyl groups, 1-propynyl groups, 2-propynyl groups, 1-butynyl groups, and 3-hexynyl groups. In the polyformal 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.

[0169] In the polyformal resin according to this embodiment, examples of aryl groups include phenyl groups, biphenyl groups, naphthyl groups, anthryl groups, and phenanthryl groups. In the polyformal resin according to this embodiment, examples of substituted aryl groups include 2-methylphenyl groups, 3-methylphenyl groups, 4-methylphenyl groups, 4-ethylphenyl groups, dichlorophenyl groups, and methylnaphthyl groups. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the aryl group is preferably 6 to 20, for example, 6 to 14, or 6 to 10.

[0170] In the polyformal resin according to this embodiment, examples of arylene groups include phenylene groups, naphthylene groups, anthracenediyl groups, biphenylene groups, and terphenyldiyl groups. In one embodiment of the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the arylene group is preferably, for example, 6 to 20, 6 to 14, or 6 to 10.

[0171] In the polyformal resin according to this embodiment, examples of aryloxy groups include phenoxy groups and naphthyloxy groups. In the polyformal resin according to this embodiment, examples of substituted aryloxy groups include tolyloxy groups. In the polyformal resin according to this embodiment, the number of ring-forming carbon atoms of the aryloxy group is preferably 6 to 14 or 6 to 10.

[0172] In the polyformal resin according to this embodiment, examples of aralkyl groups include phenylmethyl groups and phenylethyl groups. In the polyformal 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.

[0173] In the polyformal resin according to this embodiment, the aralkyloxy group can be, for example, the aralkyl group moiety being the aralkyl group, that is, the Ary in the group represented by -O-Ary being the aralkyl group. In the polyformal 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.

[0174] In the polyformal 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 included 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 identical or different from each other. Examples of heteroaryl groups in the polyformal resin according to this embodiment include pyrrolyl, imidazolyl, furyl, thienyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, triazinyl, indolyl, benzofuranyl, benzothienyl, quinolyl, isoquinolyl, phenanthrolinyl, and acridinyl groups. In the polyformal resin according to this embodiment, the number of ring-forming atoms of the heteroaryl group is preferably 5 to 20, 5 to 14, or 5 to 10.

[0175] In the polyformal resin according to this embodiment, an example of a monovalent aromatic hydrocarbon group is the aryl group. In the polyformal resin according to this embodiment, an example of a divalent aromatic hydrocarbon group is a divalent group derived by removing one hydrogen atom from the aryl ring of the aryl group.

[0176] In the polyformal resin according to this embodiment, the monovalent cyclic aliphatic hydrocarbon group is, for example, a saturated or unsaturated alicyclic group, and the number of carbon atoms in the alicyclic group is, for example, 3 to 20, preferably 3 to 12, and more preferably 4 to 8. Specific examples of saturated or unsaturated alicyclic groups include cycloalkyl groups, which are saturated alicyclic groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl groups, and cycloalkenyl groups, which are unsaturated alicyclic groups such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. Note that unsaturated alicyclic groups do not include aromatic groups. In the polyformal resin according to this embodiment, the divalent cyclic aliphatic hydrocarbon group is, for example, a divalent group derived by removing one hydrogen atom from the ring of the saturated or unsaturated alicyclic group.

[0177] In the polyformal resin according to this embodiment, the monovalent linear aliphatic hydrocarbon group is, for example, the alkyl group mentioned above.

[0178] In the polyformal resin according to this embodiment, the divalent linear aliphatic hydrocarbon group is, for example, a divalent group derived by removing one hydrogen atom from the alkyl chain of the alkyl group.

[0179] In the polyformal resin according to this embodiment, the chain-like aliphatic hydrocarbon group includes a linear aliphatic hydrocarbon group and a branched aliphatic hydrocarbon group.

[0180] In this specification, when we refer to a "substituted or unsubstituted" group, the substituents can either bond to each other to form a monocycle, bond to each other to form a fused ring, or not bond to each other. Here, the case where substituents bond to each other to form a monocycle or a fused ring includes cases where substituents bond to each other to form a multi-membered ring group. The multi-membered ring is preferably a two-membered ring (bicyclo), a three-membered ring (tricyclo), or a four-membered ring (tetracyclo). For example, examples of cases where substituents in the "substituted or unsubstituted" case of a group derived from cycloalkanes (cycloalkyl groups, cycloalkylene groups, cycloalkylidene groups) bond to each other to form a multi-membered ring include monovalent or divalent groups derived from bicycloalkanes, tricycloalkanes, and tetracycloalkanes.

[0181] In this specification, the substituent referred to as "substituted" in "substituted or unsubstituted" is preferably at least one substituent independently selected from the group consisting of alkyl groups, cycloalkyl groups, alkoxy groups, aryl groups, aryloxy groups, and halogen atoms. Specific examples of these substituents include the same groups as those described above. Furthermore, in this specification, "unsubstituted" in "substituted or unsubstituted" means that the substituent is not substituted and a hydrogen atom is bonded to it.

[0182] In this specification, in specific examples of compounds, Me may represent a methyl group, Ph may represent a phenyl group, and tBu may represent a tert-butyl group.

[0183] In this specification, any provision deemed preferable may be adopted at will, and any combination of preferred provisions is considered more preferable.

[0184] [Method for producing the resin] The method for producing the polyformal resin according to this embodiment is not particularly limited. In one embodiment of the polyformal resin according to this embodiment, a preferred method for production includes, for example, a step (P1) of reacting a bisphenol compound represented by the following formula (M-UN1) derived from the structural unit represented by formula (UN1) with a halide methylene to obtain a polyformal resin precursor, and a step (P2) of reacting the polyformal resin precursor with a compound derived from a terminal structure having a vinyl group.

[0185] In this specification, a polyformal resin that does not have an end structure having vinyl groups introduced is referred to as a polyformal resin precursor, and a resin that has an end structure having vinyl groups at both ends introduced is referred to as a polyformal resin.

[0186]

[0187] (In the above formula (M-UN1), Ux, R １ , R ２ , m, and n are Ux, R in formula (UN1), respectively. １ , R ２ (This is synonymous with m and n.)

[0188] In step P1, a bisphenol compound represented by formula (M-UN1), from which the structural unit represented by formula (UN1) is derived, is reacted with a methylene halogen in a solvent, usually in the presence of an alkali. The reaction between the bisphenol compound represented by formula (M-UN1) and the methylene halogen forms a formal structure. This formal structure increases the molecular weight, yielding a polyformal resin precursor that serves as a precursor to the polyformal resin according to one aspect of this embodiment.

[0189] Methylene halides are represented by the formula CH ２ X ２ The compound is represented by the formula (where X represents a halogen atom). Examples of methylene halides include methylene chloride, methylene bromide, and methylene iodide. Among these, methylene chloride is preferred as the methylene halide.

[0190] Examples of alkalis include alkali metal compounds. For example, an alkali may be at least one selected from the group consisting of alkali metal hydroxides, carbonides, and bicarbonates. Specifically, examples of alkalis include alkali metal hydroxides such as potassium hydroxide and sodium hydroxide; alkali metal carbonides such as potassium carbonate and sodium carbonate; and alkali metal bicarbonates such as sodium bicarbonate. Among these, alkali metal hydroxides are preferred.

[0191] Examples of solvents include aprotic polar solvents. Examples of aprotic polar solvents include at least one selected from the group consisting of N-methyl-2-pyrrolidone, dimethylformamide, dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, sulfolane, dimethyl sulfoxide, and acetonitrile.

[0192] In step P2, a polyformal resin according to one embodiment of this product is obtained by reacting the polyformal resin precursor obtained in step P1 with a compound derived from a terminal structure having a vinyl group in a solvent in the presence of an alkali. Examples of the alkali and solvent include the alkali and solvent exemplified in step P1, respectively.

[0193] The compound derived from the terminal structure having a vinyl group is preferably a compound derived from at least one terminal structure selected from the group consisting of terminal structures represented by formula (ME1-A1), formula (ME1-A2), formula (ME1-A3), and formula (ME2). The compound derived from the terminal structure represented by formula (ME1-A1), formula (ME1-A2), formula (ME1-A3), or formula (ME2) is preferably a compound represented by the following formulas (M-ME1-A1), formula (M-ME1-A2), formula (M-ME1-A3), or formula (M-ME2).

[0194]

[0195] (In the above formulas (M-ME1-A1), (M-ME1-A2), and (M-ME1-A3), R １１ , p, and Rx are each independently R in formulas (ME1-A1), (ME1-A2), and (ME1-A3). １１ , p, and Rx are synonymous, and in the above formulas (M-ME1-A1), (M-ME1-A2), (M-ME1-A3), and (M-ME2), X Ａ (It is a halogen atom.)

[0196] One embodiment of the halogen atom in formulas (M-ME1-A1), (M-ME1-A2), (M-ME1-A3), and (M-ME2) is a chlorine atom, a bromine atom, or an iodine atom.

[0197] [Insulating Material] One embodiment of the insulating material according to this embodiment contains a polyformal resin according to this embodiment.

[0198] [Resin Composition] The resin composition according to this embodiment contains the polyformal resin according to this embodiment.

[0199] One embodiment of the resin composition according to this embodiment includes the polyformal resin according to this embodiment and a radical polymerization initiator.

[0200] Examples of radical polymerization initiators include peroxides, azo initiators, and redox initiators that combine an oxidizing agent and a reducing agent. In one embodiment 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 polyformal resin according to this embodiment.

[0201] [Cured product] The cured product according to this embodiment contains the polyformal resin according to this embodiment.

[0202] One embodiment of the cured product according to this embodiment is obtained by curing the resin composition according to this embodiment. One embodiment of the cured product according to this embodiment is a fully cured product.

[0203] One embodiment of the cured product according to this embodiment is a cured product obtained by curing the intermolecular structure of the polyformal resin according to this embodiment. The cured product according to this embodiment is obtained by curing the intermolecular structure of the polyformal resin according to this embodiment, which is contained in the resin composition according to this embodiment and has a vinyl group that serves as a reactive end group, thereby curing the intermolecular structure of the polyformal resin according to this embodiment.

[0204] Examples of conditions for the curing reaction include, for example, conditions under reduced pressure, normal pressure, or pressurized conditions, with a temperature of 50°C or higher and 300°C or lower, and a duration of 0.1 hours or more and 50 hours or less.

[0205] In one embodiment of the cured product according to this embodiment, the relative permittivity Dk at a frequency of 10 GHz, measured by the resonator perturbation method using a split cylinder resonator, is preferably 2.80 or less. In one embodiment of the cured product according to this embodiment, the relative permittivity Dk is preferably 2.75 or less, preferably 2.70 or less, more preferably 2.65 or less, even more preferably 2.60 or less, even more preferably 2.58 or less, even more preferably 2.56 or less, and still most preferably 2.55 or less. The lower limit of the relative permittivity Dk in the cured product is not particularly limited and may be, for example, 2.20 or more. In this specification, the relative permittivity Dk of the cured product is the value measured at room temperature (23°C) and a frequency of 10 GHz using a split cylinder resonator.

[0206] In one embodiment of the cured product according to this embodiment, the dielectric loss tangent Df at a frequency of 10 GHz, measured by the resonator perturbation method using a split-cylinder resonator, is preferably 0.00500 or less. In one embodiment of the cured product according to this embodiment, the dielectric loss tangent Df is preferably 0.00450 or less, preferably 0.00400 or less, preferably 0.00350 or less, more preferably 0.00320 or less, even more preferably 0.00310 or less, even more preferably 0.00300 or less, and still more preferably 0.00250 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 0.00350 or less. The lower limit of the dielectric loss tangent Df in the cured product is not particularly limited and may be, for example, 0.00010 or more. In this specification, the dielectric loss tangent Df of the cured product is the value measured at room temperature (23°C) and a frequency of 10 GHz using a split-cylinder resonator.

[0207] [Coating Liquid Composition] The polyformal resin according to this embodiment may be contained in the coating liquid composition. The coating liquid composition in this embodiment contains the polyformal resin according to this embodiment. The coating liquid composition according to this embodiment may be referred to as varnish.

[0208] One embodiment of the coating liquid composition according to this embodiment contains the polyformal resin according to this embodiment and an organic solvent. Another embodiment of the coating liquid composition according to this embodiment contains the resin composition according to this embodiment and an organic solvent.

[0209] The organic solvent for the coating liquid composition can be appropriately selected considering the solubility of the material such as the polyformal resin according to this embodiment, the drying speed after molding, the effect of residue on the molded product, and the hazards (fire or health hazards).

[0210] Examples of organic solvents used in the coating liquid 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)).

[0211] In the coating liquid composition of this embodiment, considering environmental and safety aspects, 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.

[0212] One embodiment of the coating liquid composition according to this embodiment contains the polyformal resin according to this embodiment and a non-halogenated solvent. Another embodiment of the coating liquid composition according to this embodiment contains the resin composition according to this embodiment and a non-halogenated solvent, wherein the resin composition according to this embodiment is dissolved in the non-halogenated solvent.

[0213] The coating composition according to this embodiment may be applied in solution form, that is, directly onto a core material made of polyimide or epoxy resin, etc., as a coating composition. In this case as well, 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.

[0214] One embodiment of the coating liquid composition according to this embodiment may use a mixture of at least one of other thermosetting resins and thermoplastic resins in addition to the polyformal resin according to this embodiment. Examples of thermosetting resins include maleimide resin, polyphenylene ether (PPE), epoxy resin, phenoxy resin, melamine resin, or silicone resin. Examples of thermoplastic resins include liquid crystal polymer, PPE, polyimide, styrene-butadiene copolymer (elastomer), or fluororesin. In particular, the inclusion of an elastomer can impart flexibility.

[0215] One embodiment of the coating composition according to this embodiment may contain a flame retardant. Examples of flame retardants include halogen-based flame retardants, phosphorus-based flame retardants, nitrogen compounds, and silicone-based flame retardants. Preferred phosphorus-based flame retardants include organophosphorus-based flame retardants and reactive organophosphorus-based flame retardants. These flame retardants may be additives, or they may have reactive groups in part and react with the polyformal resin according to this embodiment.

[0216] [Film] One embodiment of the film according to this embodiment contains a polyformal resin according to this embodiment. One embodiment of the film according to this embodiment contains a resin composition according to this embodiment. One embodiment of the film according to this embodiment consists of a cured product according to this embodiment. Specifically, one embodiment of the film according to this embodiment consists of a cured product obtained by curing the resin composition according to this embodiment.

[0217] One embodiment of the film according to this embodiment can be manufactured by thermoforming (e.g., melt extrusion molding) the polyformal resin or resin composition according to this embodiment into a film, or by solution casting the coating liquid composition according to this embodiment into a film. When it is desired to obtain a thin film (e.g., a film thickness of several μm to several tens of μm) as the film according to this embodiment, it is preferable to manufacture the film by solution casting. Furthermore, for purposes such as reducing thermal expansion, the coating liquid composition according to this embodiment may be impregnated into a fibrous substrate such as glass cloth, or an inorganic filler such as silica may be dispersed in the coating liquid composition before film formation. A film formed by impregnating a fibrous substrate such as glass cloth with the polyformal resin according to this embodiment may be called a prepreg. Furthermore, for purposes such as improving dielectric properties and adjusting the elastic modulus, a coating liquid composition containing a known thermoplastic resin other than the polyformal resin according to this embodiment may be used when film formation. In addition, when film formation by solution casting using the coating composition according to this embodiment, it is possible to control the degree of curing by adjusting the heating temperature and change the elastic modulus of the film.

[0218] One embodiment of the sheet according to this embodiment contains the polyformal resin according to this embodiment.

[0219] When using the polyformal resin according to this embodiment as a sheet, it can be formed into a sheet by impregnating a substrate or the like with the aforementioned coating composition (varnish).

[0220] [Prepreg] One embodiment of the prepreg according to this embodiment contains the polyformal resin according to this embodiment.

[0221] One embodiment of the prepreg according to this embodiment comprises a coating liquid composition according to this embodiment and a fibrous substrate, wherein the fibrous substrate is impregnated with the coating liquid composition, and the coating liquid composition is either semi-cured or fully cured. In this specification, semi-cured means that the curing reaction of the resin composition in the coating liquid composition has partially progressed to the extent that the fluidity of the coating liquid composition according to this embodiment is lost, and is in a state from uncured to just before fully cured, which is the so-called B stage of the resin.

[0222] In one embodiment of the prepreg according to this embodiment, the fibrous base material can be, for example, glass cloth, polyester cloth, glass nonwoven fabric, aramid nonwoven fabric, glass paper, pulp paper, or combinations thereof.

[0223] One embodiment of the prepreg according to this embodiment can be produced by impregnating or coating a fibrous substrate with a coating composition and then heating and drying it. During heating and drying, the solvent in the coating composition is removed by heat.

[0224] The prepreg according to this embodiment may be used as a single sheet or as two or more sheets stacked together.

[0225] [Electronic Substrate] One embodiment of the electronic substrate according to this embodiment contains the polyformal resin according to this embodiment. In one embodiment 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. The electronic substrate material has excellent low dielectric properties. When the polyformal resin or resin composition according to this embodiment is used as an electronic substrate material, the electronic substrate material can provide a coating composition having high solvent solubility for coating molding and low solution viscosity characteristics.

[0226] One embodiment of the electronic substrate according to this embodiment comprises a prepreg according to this embodiment and copper foil. Another embodiment of the electronic substrate according to this embodiment may comprise a copper-clad laminate (CCL) in which copper foil is laminated on at least one side of one or more prepregs according to this embodiment that are laminated together. In one embodiment of the copper-clad laminate, the number of prepregs to be laminated is not particularly limited, for example, one to twenty. In one embodiment, the copper-clad laminate is obtained by using one prepreg, arranging copper foil on one or both sides of the one prepreg, and then heating and pressing it under predetermined molding conditions. In one embodiment, the copper-clad laminate is obtained by laminating two to twenty prepregs, arranging copper foil on one or both sides of the laminated prepregs, and then heating and pressing it under predetermined molding conditions. In one embodiment of the copper-clad laminate, the material of the copper foil may be copper or a copper alloy. The copper foil may be rolled copper foil or electrolytic copper foil. The thickness of the copper foil is not particularly limited and can be any thickness that is desired. For example, the thickness of the copper foil may be between 1 μm and 150 μm.

[0227] Electronic circuit boards are used in a variety of applications, including servers, automotive applications, base stations, antennas for smartphones, and transmission boards. They can be broadly classified into semiconductor boards and electronic circuit boards. (1) Semiconductor boards Semiconductor boards are substrates for forming wiring layers that handle the input and output of electrical signals to chips such as logic ICs, memory, and sensors. These wiring layers are connection layers used to connect identical or different types of chips in parallel or stacked. Examples of chip types include FC-CSP (flip-chip-chip-scale package), FC-BGA (flip-chip-ball grid array), FO-WLP (fan-out-wafer-level package), or interposers that connect multiple semiconductor chips. (2) Electronic circuit boards Electronic circuit boards are substrates on which wiring layers are formed to connect multiple electronic components such as semiconductors and capacitors. Electronic circuit boards are sometimes called printed wiring boards. Types of electronic circuit boards include multilayer boards (rigid and flexible) with stacked wiring.

[0228] [Bonding Film] One embodiment of the bonding film according to this embodiment contains the polyformal resin according to this embodiment. In one embodiment, the bonding film according to this embodiment has a resin composition layer made of the resin composition according to this embodiment. In one embodiment, 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, wherein the resin composition layer is preferably in a B-stage state (i.e., semi-cured state). In one embodiment, the bonding film according to this embodiment may have a resin composition layer between two release films. Required characteristics for this bonding film include low dielectric properties and high adhesion.

[0229] [Interlayer Insulating Film] One embodiment of the interlayer insulating film according to this embodiment contains the polyformal resin according to this embodiment. A package substrate is placed between the IC chip and the motherboard contained 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 present to maintain insulation between the circuits of this package substrate. Required characteristics 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.

[0230] In one embodiment of the interlayer insulating film according to this embodiment, various components that may be included in the interlayer insulating film include resins, organic solvents, inorganic fillers, curing accelerators, organic fillers, and adhesion promoters. Examples of resins that may be included in the interlayer insulating film include the polyformal resin according to this embodiment, as well as general thermosetting resins and thermoplastic resins other than the polyformal resin according to this embodiment. The component that plays a role in exhibiting low dielectric properties and low thermal expansion is the resin, and although the relative permittivity becomes high, the component that plays a role in exhibiting low dielectric loss tangent and low thermal expansion is the inorganic filler, spherical silica gel. To improve adhesion with copper, the use of adhesion promoters and the like is also effective, but this also depends on the properties of the resin.

[0231] Next, the present invention will be described in more detail with reference to examples and comparative examples. However, the present invention is not limited to these examples, and various modifications and applications are possible without departing from the spirit of the invention.

[0232] [Production Example: Synthesis of Polyformal Resin Precursors] <Production Example 1: Synthesis of Polyformal Resin Precursors Using 1,1-Bis-(4-Hydroxy-3-Methylphenyl)Cyclododecane> A mixed solution of 11.4 g (0.03 mol) of 1,1-bis-(4-Hydroxy-3-Methylphenyl)cyclododecane (hereinafter referred to as OCCDE), 4.3 g (0.066 mol) of potassium hydroxide, 1.7 g (0.02 mol) of methylene chloride, and 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone was stirred under nitrogen to homogenize it. Then, the reaction was carried out at 80°C for 3 hours to carry out polymerization. The resulting reaction mixture was diluted with 0.2 L of methylene chloride and 0.04 L of water and washed. The lower layer was separated and further washed with 0.4 L of water once, 0.2 L of 0.02 N hydrochloric acid once, and 0.2 L of water in that order. The obtained methylene chloride solution was added dropwise to methanol under stirring, and the resulting precipitate was filtered and dried to obtain a polyformal resin precursor (PF-P1) with the following structure. The polyformal resin precursor (PF-P1) thus obtained was then processed. １ Analysis using 1H-NMR spectroscopy confirmed that it is a polyformal resin precursor with the structure shown below. １ The number-average molecular weight calculated from the 1H-NMR spectrum was 1913.

[0233]

[0234] <Production Example 2: Synthesis of a polyformal resin precursor using 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane> A polyformal resin precursor (PF-P2) with the following structure was obtained by the same method as in Production Example 1, except that 8.8 g (0.03 mol) of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (hereinafter referred to as OCTMC) was used instead of OCCDE. The polyformal resin precursor (PF-P2) thus obtained was then processed １ Analysis using 1H-NMR spectroscopy confirmed that it is a polyformal resin precursor with the structure shown below. １The number-average molecular weight calculated from the 1H-NMR spectrum was 2045.

[0235]

[0236] [Synthesis Example 1] (Synthesis of Polyformal Resin) In a reaction vessel, under nitrogen, 2 g of the polyformal resin precursor (PF-P1) obtained in Production Example 1, 27 mL of methylene chloride, and 0.26 g of triethylamine were placed and cooled until the internal temperature reached 5°C. 0.25 g of methacrylate chloride was added dropwise, and after the addition was complete, the mixture was stirred at the same temperature for 1 hour and then at room temperature for 1 hour. Water (10 mL) was added to the resulting reaction solution and liquid-liquid extraction was performed. Furthermore, water (10 mL) was added to the organic layer for washing, followed by drying and filtration. The resulting crude material was dissolved in methylene chloride, then added dropwise to methanol under stirring, and the resulting reprecipitate was filtered and dried to obtain polyformal resin (PF-1) with the structure shown below. The polyformal resin (PF-1) thus obtained was then used １ Analysis using 1H-NMR spectroscopy confirmed that it is a polyformal resin with the following structure. １ The number-average molecular weight calculated from the 1H-NMR spectrum was 1985.

[0237]

[0238] [Synthesis Example 2] (Synthesis of Polyformal Resin) In a reaction vessel, under nitrogen, 31.5 g of the polyformal resin precursor (PF-P1) obtained in Production Example 1, 0.3 L of 1-methyl-2-pyrrolidone, 10.4 g of potassium carbonate, and 12.6 g of chloromethylstyrene (m,p mixture) were added and stirred until homogenized. The mixture was then reacted at 100°C for 3 hours. The resulting reaction mixture was added to 1.5 L of water, and the resulting precipitate was filtered and dried. The mixture was then washed with 2 L of methanol two to three times, and the resulting solid was filtered and dried to obtain polyformal resin (PF-2) with the structure shown below. The polyformal resin (PF-2) thus obtained was then used １ Analysis using 1H-NMR spectroscopy confirmed that it is a polyformal resin with the following structure. １The number average molecular weight calculated from the 1H-NMR spectrum was 2,797.

[0239]

[0240] [Synthesis Example 3] (Synthesis of polyformaldehyde resin) A polyformaldehyde resin (PF-3) having the following structure was obtained by producing it in the same manner as in Synthesis Example 2, except that the polyformaldehyde resin precursor (PF-P2) obtained in Production Example 2 was used instead of the polyformaldehyde resin precursor (PF-P1) obtained in Production Example 1. The polyformaldehyde resin (PF-3) thus obtained was １ Analyzed by 1H-NMR spectrum, it was confirmed that it was a polyformaldehyde resin having the following structure. Also, １ The number average molecular weight calculated from the 1H-NMR spectrum was 2,196.

[0241]

[0242] <Preparation of coating liquid composition containing polyformaldehyde resin and production of resin film> [Example 1] 1.5 g of polyformaldehyde resin (PF-1) was weighed into a sample tube with a screw cap, dissolved in 1.5 g of toluene to obtain a coating liquid composition. After adding 15 mg of dicumyl peroxide to the obtained coating liquid composition and completely dissolving it, a film of the coating liquid composition was cast on a polyimide film using an applicator. This was heated and dried 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 with a thickness of 50 μm to 150 μm.

[0243] [Example 2, Example 3] Resin films according to Example 2 (using polyformaldehyde resin (PF-2)) and Example 3 (using polyformaldehyde resin (PF-3)) were obtained in the same manner as in Example 1, except that polyformaldehyde resin (PF-2) or polyformaldehyde resin (PF-3) was used instead of polyformaldehyde resin (PF-1). The numbers related to the examples and the numbers related to the synthesis examples and polyformaldehyde resins respectively correspond.

[0244] [Comparative Example 1] An attempt was made to produce a resin film in the same manner as in Example 1, except that a polyformal resin precursor (PF-P1) was used instead of polyformal resin (PF-1). However, the coating composition did not heat-cur, and film production was not possible.

[0245] [Evaluation of the physical properties of polyformal resin] The physical properties of polyformal resin and resin film were evaluated by the following methods.

[0246] <Evaluation of Number-Average Molecular Weight (Mn)> A solution was prepared by dissolving the polyformal resin in methylene chloride as a deuterated solvent, and the solution was then measured using a JNM-ECA500 (manufactured by JEOL Ltd., 500 MHz). １ ¹H-NMR was measured, and the number-average molecular weight (Mn) of the obtained polyformal resin was calculated.

[0247] <Evaluation of Relative Permittivity and Dielectric Loss Tangent> A square film measuring 60 mm in length and 60 mm in width was cut from a resin film. After 24 hours of humidity control at room temperature of 22 ± 1°C and humidity of 33 ± 5%, the relative permittivity (Dk) and dielectric loss tangent (Df) were measured at a frequency of 10 GHz using a split cylinder resonator (EMlabs) and a network analyzer (Keysight Technologies). The obtained results are shown in Table 1.

[0248] <Evaluation of Glass Transition Temperature and Thermal Expansion Coefficient> Strips of film measuring 40 mm in length and 4 mm in width were cut from the resin film and measured using a TMA (thermomechanical analyzer) (manufactured by Hitachi High-Tech Science, product name: TMA7100). The results obtained are shown in Table 1. 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 for the glass transition temperature (Tg).

[0249] <Evaluation of solubility in non-halogenated solvent (toluene)> 2.0 g (50% by mass concentration) of any resin flake from the polyformal resins (PF-1) to (PF-3) according to Examples 1 to 3, and the polyformal resin precursor (PF-P1) according to Comparative Example 1, or 0.86 g (30% by mass concentration) of any of the aforementioned resin flakes, along with 2.0 g of toluene, were placed in a sample tube and stirred at room temperature to prepare a solution. After 24 hours, the appearance of the solution was visually inspected. The results obtained are shown in Table 1. A and B are within the acceptable range. A: No insoluble matter in the 50% by mass solution, and transparent. B: Visual turbidity was observed in the 50% by mass solution, and no insoluble matter in the 30% by mass solution, and transparent. C: Unsoluble matter was present in both the 30% by mass and 50% by mass solutions.

[0250] <Evaluation of Film Production Feasibility> Table 1 shows the results regarding the feasibility of producing a resin film in each example and comparative example. A is within the acceptable range. A: Resin film can be produced. F: Resin film cannot be produced.

[0251]

[0252] The polyformal resin precursor according to Comparative Example 1, which lacks a terminal structure containing vinyl groups, exhibits excellent solubility in toluene, but it was not possible to form a film, and therefore its dielectric and thermal properties could not be evaluated. Thus, it can be concluded that the polyformal resin precursor according to Comparative Example 1 does not exhibit thermosetting properties.

[0253] In contrast, the polyformal resins according to Examples 1 to 3, which contain the structural unit represented by formula (UN1) in the repeating unit and have vinyl group-containing terminal structures at both ends, exhibit excellent solubility in toluene. Furthermore, the cured products of the polyformal resins according to Examples 1 to 3 have a low dielectric constant and exhibit a low dielectric loss tangent, indicating excellent dielectric properties. Moreover, the polyformal resins according to Examples 1 to 3 can be found to have thermal properties suitable for use as electronic substrate materials.

[0254] From the above results, it was confirmed that the polyformal resin according to one aspect of the present invention has low dielectric properties and can reduce the dielectric loss tangent. Furthermore, it was confirmed that the polyformal resin according to one aspect of the present invention is suitable for solution molding using non-halogenated solvents.

Claims

1. A polyformaldehyde resin comprising a structural unit represented by the following formula (UN1) and a terminal structure having a vinyl group, and having the terminal structures at both ends. (In the above formula (UN1), １ R ２ and R １ 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-forming 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-forming 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-forming carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming 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-forming atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group, m is 0, 1, 2, 3, or 4, n is 0, 1, 2, 3, or 4, and when there are a plurality of １ R ２ the plurality of ２ R are the same as or different from each other, and when there are a plurality of ３ R ４ the plurality of ２ A group selected from the group consisting of -, -O-, and -CO-, or (iii) a divalent group formed by linking two or more groups selected from the group in (ii), R ３ and R ４ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and * represents a bond.

2. A polyformal resin according to claim 1, wherein the end structure includes at least one end structure selected from the group consisting of end structures represented by the following formulas (ME1-A1), (ME1-A2), (ME1-A3), and (ME2). (In the above formulas (ME1-A1), (ME1-A2), and (ME1-A3), R １１ Rx is a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted ring-forming C3-C10 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, p is 0, 1, or 2, Rx is a substituted or unsubstituted C1-C10 alkylene group, a substituted or unsubstituted ring-forming C3-C10 cycloalkylene group, a substituted or unsubstituted ring-forming C6-C14 arylene group, or -CO-, in formulas (ME1-A1), (ME1-A2), (ME1-A3), and (ME2), * represents a bond.

3. A polyformal resin according to claim 2, wherein the end structure represented by formula (ME1-A1) or formula (ME1-A2) is an end structure represented by the following formulas (ME11), (ME12), (ME13), (ME14), or (ME15). (In formulas (ME11), (ME12), (ME13), (ME14), and (ME15), * indicates a coupling.) 4. The polyformaldehyde resin according to any one of claims 1 to 3, further comprising a structural unit represented by the following formula (UN10): a polyformaldehyde resin. (In the above formula (UN10), R １Ｚ and R ２Ｚ 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-forming 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-forming 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-forming carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming 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-forming atoms, a halogen atom, a nitro group, an aldehyde group, a cyano group, or a carboxy group, and m Ｚ is 0, 1, 2, 3, or 4, and n Ｚ is 0, 1, 2, 3, or 4. When there are a plurality of R １Ｚ , the plurality of R １Ｚ are the same as or different from each other. When there are a plurality of R ２Ｚ , the plurality of R ２Ｚ are the same as or different from each other. Uz is (i) a single bond, (ii) a substituted or unsubstituted divalent bridged cycloaliphatic hydrocarbon group having 4 to 28 carbon atoms, 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-forming carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring-forming carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring-forming carbon atoms, a group represented by -C(R ３Ｚ )(R ４Ｚ )-, -S-, -SO-, -SO ２ A group selected from the group consisting of -, -O-, and -CO-, or (iii) a divalent group formed by linking two or more groups selected from the group in (ii), R ３Ｚ and R ４Ｚ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and * represents a bond.

5. A polyformal resin according to any one of claims 1 to 4, wherein the resin is represented by the following formula (PF-X). (In the above formula (PF-X), R １ , R ２ Ux, m, and n are each independently R in formula (UN1). １ , R ２ , is synonymous with Ux, m, and n, and R １Ｚ , R ２Ｚ , Uz, m Ｚ , and n Ｚ Each of these independently corresponds to R in the above formula (UN10). １Ｚ , R ２Ｚ , Uz, m Ｚ , and n Ｚ This is synonymous, where T is the number of repetitions of the structural unit represented by the above formula (UN1), and R １ and R １Ｚ They are either identical or different from each other, R ２ and R ２Ｚ Ux and Uz are either identical or different from each other, ME Ａ１ and ME Ａ２ Each of these is independently the terminal structure, ME Ａ１ and ME Ａ２ (They are either identical or different to each other.) 6. A polyformal resin according to any one of claims 1 to 3, wherein the structural unit represented by formula (UN1) is at least one structural unit selected from the group consisting of structural units represented by the following formulas (UN1A) and (UN1B). [(In the above formula (UN1A), 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３ ) (Caution ４ It is a group represented by )-, R １Ａ , R １Ｂ , R １Ｃ , R １Ｄ , R ２Ａ , R ２Ｂ , R ２Ｃ , and R ２Ｄ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, R ３ and R ４ R in the above formula (UN1) is ３ and R ４ This is synonymous, and * is a coupling.) (In the above formula (UN1B), R １１Ｄ and R １２Ａ Each is independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and R １１Ａ , R １１Ｂ , R １１Ｃ , R １２Ｂ , R １２Ｃ , and R １２Ｄ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, and * represents a bond.

7. A polyformal resin according to claim 6, wherein the structural unit represented by formula (UN1A) or formula (UN1B) and the terminal structure are directly bonded together.

8. A polyformal resin according to claim 4, wherein the structural unit represented by formula (UN10) is at least one structural unit selected from the group consisting of structural units represented by the following formulas (UN11) and (UN12). [(In the above formula (UN11), Uz 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 carbon atoms forming a ring, a substituted or unsubstituted cycloalkylidene group having 3 to 26 carbon atoms forming a ring, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkanediyl group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkanediyl group having 5 to 28 carbon atoms forming a ring, a substituted or unsubstituted bicycloalkylidene group having 4 to 28 carbon atoms forming a ring, a substituted or unsubstituted tricycloalkylidene group having 5 to 28 carbon atoms forming a ring, or -C(R ３Ｚ ) (Caution ４Ｚ It is a group represented by )-, R １５１ , R １５２ , R １５３ , R １５４ , R １５５ , R １５６ , R １５７ , and R １５８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, R ３Ｚ and R ４Ｚ R in the above formula (UN10) is ３Ｚ and R ４Ｚ This is synonymous, and * is a coupling.) (In the above formula (UN12), R ２１４ and R ２１５ Each is independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and R ２１１ , R ２１２ , R ２１３ , R ２１６ , R ２１７ , and R ２１８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C14 aryl group, and * represents a bond.

9. A polyformal resin according to claim 8, wherein the structural unit represented by formula (UN11) or formula (UN12) and the terminal structure are directly bonded together.

10. The polyformaldehyde resin according to any one of claims 1 to 9, １ wherein the number average molecular weight calculated from the 1H-NMR spectrum is 500 or more and 15000 or less, and the polyformaldehyde resin.

11. A resin composition comprising a polyformal resin according to any one of claims 1 to 10 and a radical polymerization initiator.

12. A cured product obtained by curing the resin composition described in claim 11.

13. A cured product according to claim 12, wherein the relative permittivity Dk at a frequency of 10 GHz, measured by a resonator perturbation method using a split cylinder resonator, is 2.80 or less.

14. A cured product according to claim 12 or claim 13, wherein the dielectric loss tangent Df at a frequency of 10 GHz, measured by a resonator perturbation method using a split cylinder resonator, is 0.00500 or less.

15. A film comprising a cured product according to any one of claims 12 to 14.

16. A coating liquid composition comprising the resin composition according to claim 11 and a non-halogenated solvent, wherein the resin composition is dissolved in the non-halogenated solvent.

17. A prepreg comprising the coating liquid composition described in claim 16 and a fibrous substrate, wherein the fibrous substrate is impregnated with the coating liquid composition, and the coating liquid composition is semi-cured or fully cured.

18. An electronic substrate comprising the prepreg described in claim 17 and copper foil.

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