Polycarbonate resin, insulating material, and electronic substrate

Abstract

Provided is a polycarbonate resin having a structure represented by formula (1). In formula (1), X1, X2, X3, and X4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, provided that at least one selected from the group consisting of X1, X2, X3, and X4 is not a hydrogen atom, and R1 is a linear alkyl group having 12 to 24 carbon atoms.

Description

Polycarbonate resin, insulating materials and electronic substrates

[0001] The present invention relates to a polycarbonate resin, an insulating material, and an electronic substrate.

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

[0003] For example, Patent Document 1 describes an aromatic polycarbonate resin containing 1 to 13 mol % of carbonate structural units derived from a dihydroxy compound having a predetermined structure. Furthermore, for example, Patent Document 2 describes a polycarbonate polymer containing structural units in which a methyl group and a long-chain alkyl group are bonded to carbon atoms connecting phenyl groups of bisphenol.

[0004] JP 2018-203972 A JP 6-128371 A

[0005] Polycarbonate resins used as electronic substrate materials are required to have improved dielectric properties by further reducing the relative permittivity and dielectric loss tangent, as well as improved heat resistance. However, Patent Documents 1 and 2 do not describe or suggest the properties (e.g., dielectric properties and heat resistance) required of polycarbonate resins for use as electronic substrate materials.

[0006] An object of the present invention is to provide a polycarbonate resin having improved dielectric properties and heat resistance, to provide an insulating material containing the polycarbonate resin, and to provide an electronic substrate containing the polycarbonate resin.

[0007] As a result of extensive research, the present inventors have found that polycarbonate resins having specific structures can improve dielectric properties and heat resistance. That is, the gist of the present invention resides in the following [Configuration 1] to [Configuration 17].

[0008] [Configuration 1] A polycarbonate resin having a structure represented by the following formula (1):

[0009]

[0010] (In the formula (1), X １ , X ２ , X ３ and X ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １ , X ２ , X ３ and X ４ at least one selected from the group consisting of is not a hydrogen atom, R １ is a linear alkyl group having 12 to 24 carbon atoms, and * indicates a bond.

[0011] [Configuration 2] X in the formula (1) １ and X ３ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0012] [Configuration 3] X in the formula (1) １ and X ３ is a methyl group.

[0013] [Configuration 4] X in the formula (1) １ , X ２ , X ３ and X ４ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0014] [Configuration 5] X in the formula (1) １ , X ２ , X ３and X ４ is a methyl group.

[0015] [Configuration 6] The polycarbonate resin according to any one of Configurations 1 to 5, further having a structure represented by the following formula (11), wherein the structure represented by the formula (1) and the structure represented by the formula (11) are different:

[0016]

[0017] (In the formula (11), X １１ , X １２ , X １３ and X １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １１ , X １２ , X １３ and X １４ at least one selected from the group consisting of is not a hydrogen atom, R １１ is a linear alkyl group having 12 to 24 carbon atoms, １ The number of carbon atoms in the linear alkyl group L １ And, R １１ The number of carbon atoms in the linear alkyl group L １１ and * indicates a bond.)

[0018] [Configuration 7] R １ The number of carbon atoms in the linear alkyl group L １ is R １１ The number of carbon atoms in the linear alkyl group L １１ The difference in the number of carbon atoms is smaller than L １１ -L １ is 1 or more and 4 or less.

[0019] [Configuration 8] The polycarbonate resin according to Configuration 6 or 7, further having a structure represented by the following formula (12), wherein the structure represented by the formula (1), the structure represented by the formula (11), and the structure represented by the formula (12) are different from each other:

[0020]

[0021] (In the formula (12), X １５ , X １６ , X １７ and X １８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １５ , X １６ , X １７ and X １８ at least one selected from the group consisting of is not a hydrogen atom, R １２ is a linear alkyl group having 12 to 24 carbon atoms, １ The number of carbon atoms in the linear alkyl group L １ And, R １１ The number of carbon atoms in the linear alkyl group L １１ And, R １２ The number of carbon atoms in the linear alkyl group L １２ and * indicates a bond.)

[0022] [Configuration 9] R １１ The number of carbon atoms in the linear alkyl group L １１ is R １２ The number of carbon atoms in the linear alkyl group L １２ The difference in the number of carbon atoms is smaller than L １２ -L １１ is 1 or more and 4 or less.

[0023] [Configuration 10] R １ The number of carbon atoms in the linear alkyl group L １ is R １１ The number of carbon atoms in the linear alkyl group L １１ Smaller, R １１ The number of carbon atoms in the linear alkyl group L １１ is R １２ The number of carbon atoms in the linear alkyl group L １２ The difference in the number of carbon atoms is smaller than L １２ -L １ is 2 or more and 8 or less.

[0024] [Configuration 11] The polycarbonate resin according to any one of Configurations 1 to 10, further comprising a structure represented by the following formula (3), wherein the structure represented by formula (1) and the structure represented by formula (3) are different:

[0025]

[0026] (In the formula (3), Y is: (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 ring carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 ring carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted bicycloalkylene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted bicycloalkylidene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylidene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), p and q are each independently 0, 1, 2, 3, or 4, and R ２ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, and a plurality of R ２ If there are multiple R ２ are the same or different, and * indicates a bond.)

[0027] [Configuration 12] A polycarbonate resin having a structure represented by the following formula (2):

[0028]

[0029] (In the formula (2), R ３ is a linear alkyl group having 12 to 24 carbon atoms, and R ４ is a linear alkyl group having 1 to 6 carbon atoms, and * indicates a bond.

[0030] [Configuration 13] The polycarbonate resin according to Configuration 12, further comprising a structure represented by the following formula (3), wherein the structure represented by the formula (2) and the structure represented by the formula (3) are different:

[0031]

[0032] (In the formula (3), Y is: (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 ring carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 ring carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted bicycloalkylene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted bicycloalkylidene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylidene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), p and q are each independently 0, 1, 2, 3, or 4, and R ２is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, and a plurality of R ２ If there are multiple R ２ are the same or different, and * indicates a bond.)

[0033] [Configuration 14] The polycarbonate resin according to Configuration 11 or 13, wherein Y in the formula (3) is a 1,1-cyclododecylidene group, a 1,1-cyclohexylidene group, or a 3,3,5-trimethyl-1,1-cyclohexylidene group.

[0034] [Configuration 15] R in the formula (3) ２ is a methyl group, and p and q are each independently 1 or 2, or R ２ is a cyclohexyl group, and p and q are 1.

[0035] [Configuration 16] An insulating material comprising the polycarbonate resin according to any one of Configurations 1 to 15.

[0036] [Configuration 17] An electronic substrate comprising the polycarbonate resin according to any one of Configurations 1 to 15.

[0037] According to one aspect of the present invention, it is possible to provide a polycarbonate resin having improved dielectric properties and heat resistance, to provide an insulating material containing the polycarbonate resin, and to provide an electronic substrate containing the polycarbonate resin.

[0038] [First embodiment] [Polycarbonate resin] The polycarbonate resin according to this embodiment has a structure represented by the following formula (1). The polycarbonate resin according to this embodiment is an aromatic polycarbonate resin. Furthermore, the polycarbonate resin according to this embodiment is preferably a thermoplastic aromatic polycarbonate resin. In this specification, the polycarbonate resin may be abbreviated as PC resin.

[0039]

[0040] (In the formula (1), X １ , X ２ , X ３ and X ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １ , X ２ , X ３ and X ４ at least one selected from the group consisting of is not a hydrogen atom, R １ is a linear alkyl group having 12 to 24 carbon atoms, and * indicates a bond.

[0041] In one aspect of the PC resin according to this embodiment, R １ is a straight chain alkyl group, and R １ The number of carbon atoms in the linear alkyl group L １ is 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, or 18 or more. １ is a straight chain alkyl group, and R １ The number of carbon atoms in the linear alkyl group L １ is 23 or less, 22 or less, 21 or less, or 20 or less.

[0042] In one aspect of this embodiment, the PC resin according to this embodiment is a polymerizable compound represented by the formula (1) R １ The number of carbon atoms in the linear alkyl group L １ may have two or more different structures, or may have three or more different structures.

[0043] In one aspect of the PC resin according to this embodiment, X in formula (1) １ and X ３ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0044] In one aspect of the PC resin according to this embodiment, X in formula (1) １ and X ３ is a methyl group.

[0045] In one aspect of the PC resin according to this embodiment, X in formula (1) １ , X ２ , X ３ and X ４ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0046] In one aspect of the PC resin according to this embodiment, X in formula (1) １ , X ２ , X ３ and X ４ is a methyl group.

[0047] The PC resin according to this embodiment is a polymer. The PC resin according to this embodiment may be a homopolymer or a copolymer. When the PC resin according to this embodiment is a copolymer, the repeating units (for example, the structures represented by the formulas) are not necessarily continuous. One aspect of the polycarbonate resin according to this embodiment is a block copolymer, another aspect is an alternating copolymer, and yet another aspect is a random copolymer.

[0048] In one aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 5 mol % or more and 100 mol % or less of the structure represented by formula (1) among all repeating units. In one aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 10 mol % or more, 15 mol % or more, 20 mol % or more, 25 mol % or more, 30 mol % or more, 35 mol % or more, or 40 mol % or more of the structure represented by formula (1) among all repeating units. In one aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 90 mol % or less, 80 mol % or less, 70 mol % or less, 60 mol % or less, 50 mol % or less, or 45 mol % or less of the structure represented by formula (1) among all repeating units. In this specification, the proportion of each structure in the resin is １ It can be determined by H-NMR analysis.

[0049] The PC resin according to this embodiment may further have a structure represented by the following formula (11): In the PC resin according to this embodiment, the structure represented by the formula (1) is different from the structure represented by the formula (11).

[0050]

[0051] (In the formula (11), X １１ , X １２ , X １３ and X １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １１ , X １２ , X １３ and X １４ at least one selected from the group consisting of is not a hydrogen atom, R １１ is a linear alkyl group having 12 to 24 carbon atoms, １ The number of carbon atoms in the linear alkyl group L １ And, R １１ The number of carbon atoms in the linear alkyl group L １１and * indicates a bond.)

[0052] In one aspect of the PC resin according to this embodiment, R １１ is a straight chain alkyl group, and R １１ The number of carbon atoms in the linear alkyl group L １１ is 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, or 18 or more. １１ is a straight chain alkyl group, and R １１ The number of carbon atoms in the linear alkyl group L １１ is 23 or less, 22 or less, 21 or less, or 20 or less.

[0053] In one aspect of the PC resin according to this embodiment, R １ The number of carbon atoms in the linear alkyl group L １ is R １１ The number of carbon atoms in the linear alkyl group L １１ The difference in the number of carbon atoms is smaller than L １１ -L １ is between 1 and 4.

[0054] In one aspect of the PC resin according to this embodiment, X in formula (11) １１ and X １３ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0055] In one aspect of the PC resin according to this embodiment, X in formula (11) １１ and X １３ is a methyl group.

[0056] In one aspect of the PC resin according to this embodiment, X in formula (11) １１ , X １２ , X １３ and X １４ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0057] In one aspect of the PC resin according to this embodiment, X in formula (11) １１ , X １２ , X １３and X １４ is a methyl group.

[0058] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (1) as a repeating unit and the structure represented by formula (11) as a repeating unit in a total amount of 5 mol % or more and 100 mol % or less.

[0059] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (1) as a repeating unit and the structure represented by formula (11) as a repeating unit in a total amount of 10 mol % or more, 15 mol % or more, 20 mol % or more, 25 mol % or more, 30 mol % or more, 35 mol % or more, or 40 mol % or more.

[0060] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (1) as a repeating unit and the structure represented by formula (11) as a repeating unit in a total amount of 90 mol % or less, 80 mol % or less, 70 mol % or less, 60 mol % or less, or 50 mol % or less.

[0061] The PC resin according to this embodiment may further have a structure represented by formula (12) below. That is, the PC resin according to this embodiment also preferably includes the structure represented by formula (1), the structure represented by formula (11), and the structure represented by formula (12) below. In the PC resin according to this embodiment, the structure represented by formula (1), the structure represented by formula (11), and the structure represented by formula (12) below are different.

[0062]

[0063] (In the formula (12), X １５ , X １６ , X １７ and X １８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X１５ , X １６ , X １７ and X １８ at least one selected from the group consisting of is not a hydrogen atom, R １２ is a linear alkyl group having 12 to 24 carbon atoms, １ The number of carbon atoms in the linear alkyl group L １ And, R １１ The number of carbon atoms in the linear alkyl group L １１ And, R １２ The number of carbon atoms in the linear alkyl group L １２ and * indicates a bond.)

[0064] In one aspect of the PC resin according to this embodiment, R １２ is a straight chain alkyl group, and R １２ The number of carbon atoms in the linear alkyl group L １２ is 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, or 18 or more. １２ is a straight chain alkyl group, and R １２ The number of carbon atoms in the linear alkyl group L １２ is 23 or less, 22 or less, 21 or less, or 20 or less.

[0065] In one aspect of the PC resin according to this embodiment, R １１ The number of carbon atoms in the linear alkyl group L １１ is R １２ The number of carbon atoms in the linear alkyl group L １２ The difference in the number of carbon atoms is smaller than L １２ -L １１ is between 1 and 4.

[0066] In one aspect of the PC resin according to this embodiment, R １ The number of carbon atoms in the linear alkyl group L １ is R １１ The number of carbon atoms in the linear alkyl group L １１ Smaller, R １１ The number of carbon atoms in the linear alkyl group L １１ is R １２ The number of carbon atoms in the linear alkyl group L１２ The difference in the number of carbon atoms is smaller than L １２ -L １ is between 2 and 8.

[0067] In one aspect of the PC resin according to this embodiment, X in formula (12) １５ and X １７ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0068] In one aspect of the PC resin according to this embodiment, X in formula (12) １５ and X １７ is a methyl group.

[0069] In one aspect of the PC resin according to this embodiment, X in formula (12) １５ , X １６ , X １７ and X １８ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0070] In one aspect of the PC resin according to this embodiment, X in formula (12) １５ , X １６ , X １７ and X １８ is a methyl group.

[0071] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (1) as a repeating unit, the structure represented by formula (11) as a repeating unit, and the structure represented by formula (12) as a repeating unit in a total amount of 5 mol % or more and 100 mol % or less.

[0072] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (1) as a repeating unit, the structure represented by formula (11) as a repeating unit, and the structure represented by formula (12) as a repeating unit in a total amount of 10 mol % or more, 15 mol % or more, 20 mol % or more, 25 mol % or more, 30 mol % or more, 35 mol % or more, or 40 mol % or more.

[0073] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (1) as a repeating unit, the structure represented by formula (11) as a repeating unit, and the structure represented by formula (12) as a repeating unit in a total amount of 90 mol % or less, 80 mol % or less, 70 mol % or less, 60 mol % or less, or 50 mol % or less.

[0074] The PC resin according to this embodiment may further have a structure represented by the following formula (3). That is, the PC resin according to this embodiment also preferably includes the structure represented by the formula (1) and the structure represented by the formula (3). The structure represented by the formula (1) and the structure represented by the formula (3) are different.

[0075]

[0076] (In the formula (3), Y is: (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 ring carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 ring carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted bicycloalkylene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted bicycloalkylidene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylidene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), p and q are each independently 0, 1, 2, 3, or 4, and R ２is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, and a plurality of R ２ If there are multiple R ２ are the same or different, and * indicates a bond.)

[0077] In one aspect of the PC resin according to this embodiment, the number of repeating units of the structure represented by formula (3) is greater than the number of repeating units of the structure represented by formula (1).

[0078] In one aspect of the PC resin according to this embodiment, the number of repeating units of the structure represented by formula (3) is smaller than the number of repeating units of the structure represented by formula (1).

[0079] The PC resin according to this embodiment preferably includes a structure represented by the formula (1), a structure represented by the formula (11), and a structure represented by the formula (3). The structure represented by the formula (11) and the structure represented by the formula (3) are different from each other.

[0080] The PC resin according to this embodiment preferably includes a structure represented by the formula (1), a structure represented by the formula (11), a structure represented by the formula (12), and a structure represented by the formula (3). The structure represented by the formula (12) and the structure represented by the formula (3) are different.

[0081] In one aspect of the PC resin according to this embodiment, Y in the formula (3) is a 1,1-cyclododecylidene group, a 1,1-cyclohexylidene group, or a 3,3,5-trimethyl-1,1-cyclohexylidene group.

[0082] In one aspect of the PC resin according to this embodiment, p and q in the formula (3) are each independently 1 or 2.

[0083] In one aspect of the PC resin according to this embodiment, p and q in the formula (3) are each 2.

[0084] In one aspect of the PC resin according to this embodiment, R ２ is a methyl group, and p and q are each independently 1 or 2, or R ２ is a cyclohexyl group, and p and q are 1.

[0085] In one aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 10 mol % or more and 95 mol % or less of the structure represented by formula (3) among all repeating units. In one aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 20 mol % or more, 30 mol % or more, 40 mol % or more, 50 mol % or more, or 55 mol % or more of the structure represented by formula (3) among all repeating units. In one aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 90 mol % or less, 85 mol % or less, 80 mol % or less, 75 mol % or less, 70 mol % or less, 65 mol % or less, or 60 mol % or less of the structure represented by formula (3).

[0086] In one aspect of the PC resin according to this embodiment, the structure represented by formula (3) includes at least one structure selected from the group consisting of a structure represented by formula (30) below and a structure represented by formula (31) below:

[0087]

[0088]

[0089] (In the formulas (30) and (31), Y has the same meaning as Y in the formula (3), and R ２１ , R ２２ , R ２３ and R ２４ are each independently R in formula (3). ２ and * indicates a bond.)

[0090] In one aspect of the PC resin according to this embodiment, R ２ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 10 ring carbon atoms.

[0091] In one aspect of the PC resin according to this embodiment, R in the formula (30) and the formula (31) ２１ , R ２２ , R ２３ and R ２４ are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 10 ring carbon atoms.

[0092] The PC resin according to this embodiment may be a polycarbonate resin having a structure represented by the following formula (2).

[0093]

[0094] (In the formula (2), R ３ is a linear alkyl group having 12 to 24 carbon atoms, and R ４ is a linear alkyl group having 1 to 6 carbon atoms, and * indicates a bond.

[0095] In one aspect of the PC resin according to this embodiment, R ３ is a straight chain alkyl group, and R ３ The number of carbon atoms in the linear alkyl group L ３ is 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, or 18 or more. ３ is a straight chain alkyl group, and R ３ The number of carbon atoms in the linear alkyl group L ３ is 23 or less, 22 or less, 21 or less, or 20 or less.

[0096] In one aspect of this embodiment, the PC resin according to this embodiment is a polymer having R ３ The number of carbon atoms in the linear alkyl group L ３ may have two or more different structures, or may have three or more different structures.

[0097] In one aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 5 mol % or more and 100 mol % or less of the structure represented by formula (2) among all repeating units. In another aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 10 mol % or more, 15 mol % or more, 20 mol % or more, 25 mol % or more, 30 mol % or more, 35 mol % or more, or 40 mol % or more of the structure represented by formula (2) among all repeating units. In another aspect of this embodiment, the PC resin according to this embodiment contains, as repeating units, 90 mol % or less, 80 mol % or less, 70 mol % or less, 60 mol % or less, 50 mol % or less, or 45 mol % or less of the structure represented by formula (2).

[0098] In one aspect of the PC resin according to this embodiment, R ４ is a straight chain alkyl group, and R ４ The number of carbon atoms in the linear alkyl group L ４ is 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

[0099] The PC resin according to this embodiment also preferably includes a structure represented by the formula (2) and a structure represented by the formula (3). The structure represented by the formula (2) and the structure represented by the formula (3) are different from each other.

[0100] In one aspect of the PC resin according to this embodiment, the number of repeating units of the structure represented by formula (3) is greater than the number of repeating units of the structure represented by formula (2).

[0101] In one aspect of the PC resin according to this embodiment, the number of repeating units of the structure represented by formula (3) is smaller than the number of repeating units of the structure represented by formula (2).

[0102] The PC resin according to this embodiment may further have a structure represented by the following formula (21): In the PC resin according to this embodiment, the structure represented by the formula (2) is different from the structure represented by the following formula (21).

[0103]

[0104] (In the formula (21), R ４ is R in the formula (2). ４ is synonymous with R ３１ is a linear alkyl group having 12 to 24 carbon atoms, ３ The number of carbon atoms in the linear alkyl group L ３ And, R ３１ The number of carbon atoms in the linear alkyl group L ３１ and * indicates a bond.)

[0105] In one aspect of the PC resin according to this embodiment, R ３１ is a straight chain alkyl group, and R ３１ The number of carbon atoms in the linear alkyl group L ３１ is 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, or 18 or more. ３１ is a straight chain alkyl group, and R ３１ The number of carbon atoms in the linear alkyl group L ３１ is 23 or less, 22 or less, 21 or less, or 20 or less.

[0106] In one aspect of the PC resin according to this embodiment, R ３ The number of carbon atoms in the linear alkyl group L ３ is R ３１ The number of carbon atoms in the linear alkyl group L ３１ The difference in the number of carbon atoms is smaller than L ３１ -L ３ is between 1 and 4.

[0107] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (2) as a repeating unit and the structure represented by formula (21) as a repeating unit in a total amount of 5 mol % or more and 100 mol % or less.

[0108] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (2) as a repeating unit and the structure represented by formula (21) as a repeating unit in a total amount of 10 mol % or more, 15 mol % or more, 20 mol % or more, 25 mol % or more, 30 mol % or more, 35 mol % or more, or 40 mol % or more.

[0109] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (2) as a repeating unit and the structure represented by formula (21) as a repeating unit in a total amount of 90 mol % or less, 80 mol % or less, 70 mol % or less, 60 mol % or less, or 50 mol % or less.

[0110] The PC resin according to this embodiment may further have a structure represented by formula (22) below. That is, the PC resin according to this embodiment also preferably includes the structure represented by formula (2), the structure represented by formula (21), and the structure represented by formula (22) below. In the PC resin according to this embodiment, the structure represented by formula (2), the structure represented by formula (21), and the structure represented by formula (22) below are different.

[0111]

[0112] (In the formula (22), R ４ is R in the formula (2). ４ is synonymous with R ３２ is a linear alkyl group having 12 to 24 carbon atoms, ３ The number of carbon atoms in the linear alkyl group L ３ And, R ３１ The number of carbon atoms in the linear alkyl group L ３１ And, R ３２The number of carbon atoms in the linear alkyl group L ３２ and * indicates a bond.)

[0113] In one aspect of the PC resin according to this embodiment, R ３２ is a straight chain alkyl group, and R ３２ The number of carbon atoms in the linear alkyl group L ３２ is 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, or 18 or more. ３２ is a straight chain alkyl group, and R ３２ The number of carbon atoms in the linear alkyl group L ３２ is 23 or less, 22 or less, 21 or less, or 20 or less.

[0114] Multiple R ４ If there are multiple R ４ are the same or different from each other.

[0115] In one aspect of the PC resin according to this embodiment, R ３１ The number of carbon atoms in the linear alkyl group L ３１ is R ３２ The number of carbon atoms in the linear alkyl group L ３２ The difference in the number of carbon atoms is smaller than L ３２ -L ３１ is between 1 and 4.

[0116] In one aspect of the PC resin according to this embodiment, R ３ The number of carbon atoms in the linear alkyl group L ３ is R ３１ The number of carbon atoms in the linear alkyl group L ３１ Smaller, R ３１ The number of carbon atoms in the linear alkyl group L ３１ is R ３２ The number of carbon atoms in the linear alkyl group L ３２ The difference in the number of carbon atoms is smaller than L ３２ -L ３ is between 2 and 8.

[0117] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (2) as a repeating unit, the structure represented by formula (21) as a repeating unit, and the structure represented by formula (22) as a repeating unit in a total amount of 5 mol % or more and 100 mol % or less.

[0118] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (2) as a repeating unit, the structure represented by formula (21) as a repeating unit, and the structure represented by formula (22) as a repeating unit in a total amount of 10 mol % or more, 15 mol % or more, 20 mol % or more, 25 mol % or more, 30 mol % or more, 35 mol % or more, or 40 mol % or more.

[0119] In one aspect of this embodiment, the PC resin according to this embodiment contains, among all repeating units, the structure represented by formula (2) as a repeating unit, the structure represented by formula (21) as a repeating unit, and the structure represented by formula (22) as a repeating unit in a total amount of 90 mol % or less, 80 mol % or less, 70 mol % or less, 60 mol % or less, or 50 mol % or less.

[0120] The PC resin according to this embodiment also preferably includes a structure represented by the formula (2), a structure represented by the formula (21), and a structure represented by the formula (3). The structure represented by the formula (21) and the structure represented by the formula (3) are different.

[0121] The PC resin according to this embodiment preferably includes a structure represented by the formula (2), a structure represented by the formula (21), a structure represented by the formula (22), and a structure represented by the formula (3). The structure represented by the formula (22) and the structure represented by the formula (3) are different.

[0122] In one aspect of this embodiment, the PC resin according to this embodiment may be in a form that does not include a terminal structure having a vinyl group. In one aspect of this embodiment, the PC resin according to this embodiment may be in a form that does not include a terminal structure having at least one group selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, a vinylbenzyl ether group, and an allyl ether group.

[0123] (Reduced Viscosity) In one aspect of this embodiment, the reduced viscosity of the polycarbonate resin is 1.70 dL / g or less. However, in this specification, the reduced viscosity of the resin is the reduced viscosity of a solution containing methylene chloride as a solvent and the resin as a solute at a concentration of 0.5 g / dL at a temperature of 20°C. In one aspect of this embodiment, the reduced viscosity of the polycarbonate resin is 0.80 dL / g or less, 0.78 dL / g or less, or 0.75 dL / g or less. In one aspect of this embodiment, the reduced viscosity of the polycarbonate resin is 0.30 dL / g or more, 0.35 dL / g or more, or 0.40 dL / g or more.

[0124] (Dielectric Properties) There are various methods for evaluating dielectric properties. One commonly used method is the cavity resonator perturbation method (hereinafter referred to as the cavity resonance method), which uses an electric field along the sample to evaluate dielectric properties. However, the electric field at both ends of the sample is deflected outside the sample. Because no known quantitative explanation for this imperfection has been established, it is common to calculate the dielectric constant assuming that the electric field passes through the entire sample. Therefore, even though the electric field is not applied at both ends of the sample, the dielectric constant is measured as low because the dielectric properties are calculated assuming that the electric field is applied throughout the sample. On the other hand, the split cylinder resonator perturbation method (hereinafter referred to as the split cylinder method), which uses a circular electric field along the sample surface, does not produce errors due to the deflection of the electric field at both ends of the sample, which occurs in the cavity resonance method. Therefore, the split cylinder method outputs dielectric properties closer to the true value than the cavity resonance method.

[0125] The dielectric constant Dk of the polycarbonate resin according to one aspect of this embodiment is preferably 2.80 or less, more preferably 2.75 or less, more preferably 2.70 or less, even more preferably 2.65 or less, even more preferably 2.60 or less, still more preferably 2.50 or less, and even more preferably 2.48 or less. In this specification, the dielectric constant Dk of the resin is a value measured at room temperature (23°C) and a frequency of 10 GHz using a split cylinder resonator.

[0126] Furthermore, the dielectric loss tangent Df of the polycarbonate resin according to one aspect of this embodiment is preferably 0.02000 or less, preferably 0.00700 or less, preferably 0.00500 or less, preferably 0.00350 or less, preferably 0.00300 or less, preferably 0.00250 or less, more preferably 0.00200 or less, even more preferably 0.00140 or less, even more preferably 0.00120 or less, and even more preferably 0.00100 or less. In this specification, the dielectric loss tangent Df of the resin is a value measured using a split cylinder resonator at room temperature (23°C) and a frequency of 10 GHz. When the relative permittivity Dk and dielectric loss tangent Df of the polycarbonate resin according to this embodiment are below the upper limit of the above range, the loss of electrical signals in the electronic substrate can be reduced when the polycarbonate resin according to this embodiment is used as an electronic substrate material.

[0127] (Viscosity Average Molecular Weight) From the viewpoint of solution viscosity, the viscosity average molecular weight Mv of the polycarbonate resin according to one aspect of this embodiment is preferably 500 or more and 100,000 or less, more preferably 1,000 or more and 80,000 or less, even more preferably 1,000 or more and 70,000 or less, and even more preferably 1,000 or more and 50,000 or less. In this specification, the viscosity average molecular weight Mv is calculated by dissolving the resin in methylene chloride as a solvent to prepare a solution, measuring the intrinsic viscosity [η] of this solution at 20°C using an Ubbelohde viscometer, and then using the following Schnell formula: [η] = 1.23 × 10－５ Mv ０．８３

[0128] (Glass Transition Temperature (Tg)) The polycarbonate 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, and even more preferably 150° C. or higher. The glass transition temperature can be measured by the method described in the Examples section.

[0129] (Explanation of Substituents, etc.) In the polycarbonate resin according to this embodiment, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0130] In the polycarbonate resin according to this embodiment, examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, butyl, sec-butyl, tert-butyl, various pentyl groups, and various hexyl groups. In this specification, when the term "various" is added to the name of a substituent, this term includes linear and branched groups, and the same applies hereinafter. In the polycarbonate resin according to this embodiment, examples of the substituted alkyl group include trifluoromethyl. In the polycarbonate 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, 1 to 6, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

[0131] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0132] In the polycarbonate resin according to this embodiment, examples of the alkylene group include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a hexamethylene group. In the polycarbonate 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.

[0133] In the polycarbonate resin according to this embodiment, examples of the alkylidene group include an ethylidene group and an isopropylidene group. In the polycarbonate resin according to this embodiment, the number of carbon atoms in the alkylidene group is preferably, for example, 2 to 28, 2 to 20, 2 to 18, 2 to 10, or 2 to 5.

[0134] In the polycarbonate resin according to this embodiment, examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, various pentyloxy groups, various hexyloxy groups, etc. In the polycarbonate 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.

[0135] In the polycarbonate resin according to this embodiment, examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, and a norbornyl group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the cycloalkyl group is preferably, for example, 3 to 26, 3 to 20, or 6 to 20.

[0136] In the polycarbonate resin according to this embodiment, examples of the cycloalkylene group include a cyclopentanediyl group, a cyclohexanediyl group, and a cyclooctanediyl group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the cycloalkylene group is, for example, preferably 5 to 15, or 5 to 10.

[0137] In the polycarbonate resin according to this embodiment, examples of the cycloalkylidene group include a cyclohexylidene group, a cyclododecylidene group, and a 3,5,5-trimethylcyclohexylidene group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the cycloalkylidene group is preferably, for example, 3 to 26, 5 to 15, or 5 to 10.

[0138] In the polycarbonate resin according to this embodiment, the bicycloalkylene group may, for example, be a bicyclo[2.2.1]heptanediyl group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the bicycloalkylene group is preferably, for example, 4 to 15, 7 to 15, or 10 to 15.

[0139] In the polycarbonate resin according to this embodiment, examples of the bicycloalkylidene group include a bicyclo[2.2.1]heptylidene group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the bicycloalkylidene group is preferably, for example, 4 to 15, 7 to 10, or 10 to 15.

[0140] In the polycarbonate resin according to this embodiment, examples of the tricycloalkylene group include an adamantanediyl group and a tricyclodecanediyl group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the tricycloalkylene group is preferably, for example, 5 to 15, 8 to 15, or 10 to 15.

[0141] In the polycarbonate resin according to this embodiment, examples of the tricycloalkylidene group include an adamantylidene group and a tricyclodecylidene group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the tricycloalkylidene group is preferably, for example, 5 to 15, 8 to 15, or 10 to 15.

[0142] In the polycarbonate resin according to this embodiment, the cycloalkoxy group may be, for example, a group in which the cycloalkyl group moiety is the cycloalkyl group described above, i.e., a group in which Arx of the group represented by -O-Arx is the cycloalkyl group described above. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the cycloalkoxy group is, for example, preferably 3 to 20, or 6 to 20.

[0143] In the polycarbonate resin according to this embodiment, examples of the alkenyl group include ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), butenyl, pentenyl, and hexenyl groups. In the polycarbonate 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.

[0144] In the polycarbonate resin according to this embodiment, examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, and a 3-hexynyl group. In the polycarbonate 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.

[0145] In the polycarbonate resin according to this embodiment, examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. In the polycarbonate resin according to this embodiment, examples of the substituted aryl group include a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a dichlorophenyl group, and a methylnaphthyl group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the aryl group is preferably, for example, 6 to 20, 6 to 14, or 6 to 10.

[0146] In the polycarbonate resin according to this embodiment, examples of the arylene group include a phenylene group, a naphthylene group, an anthracenediyl group, a biphenylene group, and a terphenyldiyl group. In one aspect of the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the arylene group is preferably, for example, 6 to 20, 6 to 14, or 6 to 10.

[0147] In the polycarbonate resin according to this embodiment, examples of the aryloxy group include a phenoxy group and a naphthyloxy group. In the polycarbonate resin according to this embodiment, examples of the substituted aryloxy group include a tolyloxy group. In the polycarbonate resin according to this embodiment, the number of ring carbon atoms of the aryloxy group is, for example, preferably 6 to 14, or 6 to 10.

[0148] In the polycarbonate resin according to this embodiment, examples of the aralkyl group include a phenylmethyl group and a phenylethyl group. In the polycarbonate 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.

[0149] In the polycarbonate resin according to this embodiment, the aralkyloxy group may be, for example, an aralkyl group moiety, i.e., an aralkyl group in the group represented by -O-Ary, where Ary is the aralkyl group. In the polycarbonate 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.

[0150] In the polycarbonate resin according to this embodiment, the heteroaryl group contains at least one heteroatom as a ring-forming atom. For example, the heteroaryl group may contain one, two, or three heteroatoms as ring-forming atoms. The heteroatoms contained in the heteroaryl group as ring-forming atoms are one or more atoms selected from the group consisting of nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms. When the heteroaryl group contains multiple heteroatoms as ring-forming atoms, the multiple heteroatoms may be the same or different. In the polycarbonate resin according to this embodiment, examples of the heteroaryl group include pyrrolyl, imidazolyl, furyl, thienyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolyl, benzofuranyl, benzothienyl, quinolyl, isoquinolyl, phenanthrolinyl, and acridinyl groups. In the polycarbonate resin according to this embodiment, the heteroaryl group preferably has 5 to 20 ring atoms, 5 to 14 ring atoms, or 5 to 10 ring atoms.

[0151] In the polycarbonate resin according to this embodiment, examples of the monovalent aromatic hydrocarbon group include the aryl group. In the polycarbonate resin according to this embodiment, examples of the divalent aromatic hydrocarbon group include a divalent group derived by removing one hydrogen atom from the aryl ring of the aryl group.

[0152] In the polycarbonate resin according to this embodiment, the monovalent alicyclic hydrocarbon group may be, for example, a saturated or unsaturated alicyclic group. The alicyclic group may have, for example, 3 to 20 carbon atoms, preferably 3 to 12 carbon atoms, and more preferably 4 to 8 carbon atoms. Specific examples of the saturated or unsaturated alicyclic group include cycloalkyl groups, which are saturated alicyclic groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl, and cycloalkenyl groups, which are unsaturated alicyclic groups such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl. The unsaturated alicyclic group does not contain an aromatic group. In the polycarbonate resin according to this embodiment, the divalent alicyclic hydrocarbon group may be, for example, a divalent group derived by removing one hydrogen atom from the ring of the saturated or unsaturated alicyclic group.

[0153] In the polycarbonate resin according to this embodiment, examples of the monovalent chain aliphatic hydrocarbon group include the alkyl groups described above.

[0154] In the polycarbonate resin according to this embodiment, the divalent chain aliphatic hydrocarbon group is, for example, a divalent group derived by removing one hydrogen atom from the alkyl chain of the alkyl group.

[0155] In the polycarbonate resin according to this embodiment, the chain aliphatic hydrocarbon group includes a linear aliphatic hydrocarbon group and a branched aliphatic hydrocarbon group.

[0156] In this specification, when referring to "substituted or unsubstituted," the substituents may bond to each other to form a monocycle, a fused ring, or not bond to each other. Here, when referring to "substituted or unsubstituted," the substituents may bond to each other to form a monocycle or a fused ring, and this also includes cases where the substituents bond to each other to form a multi-membered ring. This multi-membered ring is preferably a two-membered ring (bicyclo), a three-membered ring (tricyclo), or a four-membered ring (tetracyclo). For example, when referring to a "substituted or unsubstituted" group (a cycloalkyl group, a cycloalkylene group, a cycloalkylidene group) derived from a cycloalkane, examples of when the substituents bond to each other to form a multi-membered ring include monovalent or divalent groups derived from a bicycloalkane, a tricycloalkane, and a tetracycloalkane.

[0157] In this specification, the substituents in the "substituted" part of "substituted or unsubstituted" are preferably at least one substituent selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, an aryloxy group, and a halogen atom, each independently. Specific examples of these substituents include the same groups as the specific examples described above. Furthermore, in this specification, "unsubstituted" in the "substituted or unsubstituted" part means that the group is not substituted with the substituent and is bonded to a hydrogen atom.

[0158] In the present specification, in specific examples of compounds, D may represent a deuterium atom, Me may represent a methyl group, Ph may represent a phenyl group, and tBu may represent a tert-butyl group.

[0159] In this specification, the preferred provisions can be adopted arbitrarily, and it can be said that a combination of preferred provisions is more preferred.

[0160] [Method for producing polycarbonate resin] (Dihydric phenol compound) The polycarbonate resin according to this embodiment can be preferably produced using a dihydric phenol compound (ma) represented by the following formula (MA1). The structure represented by the formula (1) is derived from the dihydric phenol compound (ma). Therefore, this embodiment also provides the use of the dihydric phenol compound (ma) represented by the following formula (MA1) for producing the polycarbonate resin according to this embodiment. In this specification, the dihydric phenol compound may be referred to as a bisphenol.

[0161]

[0162] (In the formula (MA1), X １ , X ２ , X ３ , X ４ , and R １ are X in the formula (1), respectively. １ , X ２ , X ３ , X ４ , and R １ is synonymous with

[0163] The dihydric phenol compound (ma) represented by the formula (MA1) can be produced by condensing a phenol (mp) with a ketone represented by the following formula (MK1).

[0164]

[0165] (In the formula (MK1), R １ is R in the formula (1). １ is synonymous with

[0166] In the method for producing a PC resin according to this embodiment, the ketones represented by formula (MK1) may be used singly, in a mixture of two or more, or in a mixture of three or more. The ketones represented by formula (MK1) can be produced by oxidizing the corresponding olefins. Alternatively, the ketones represented by formula (MK1) can be produced by mixing two or more or three or more olefins to obtain an olefin mixture, and then oxidizing this olefin mixture.

[0167] In the method for producing a PC resin according to this embodiment, the olefins corresponding to the ketones represented by the formula (MK1) are represented by the following formula (MOL1).

[0168]

[0169] (In the formula (MOL1), R １ is R in the formula (1). １ is synonymous with

[0170] Examples of the phenols (mp) include cresol (2-methylphenol), 2,6-dimethylphenol, 2-cyclohexylphenol, and 2,6-dicyclohexylphenol. The phenols (mp) may be used alone or in combination of two or more.

[0171] In the PC resin production method according to this embodiment, the dihydric phenol compound (ma) can be produced by condensing a phenol (mp) with a ketone represented by the following formula (MK11), or can be produced by condensing a phenol (mp) with a ketone represented by the following formula (MK12).

[0172]

[0173] (In the formula (MK11), R １１ is R in the formula (11). １１ In the formula (MK12), R １２ is R in the formula (12). １２ is synonymous with

[0174] The ketones represented by the formula (MK11) and the ketones represented by the formula (MK12) can be produced by oxidizing the corresponding olefins, respectively.

[0175] In the PC resin production method according to this embodiment, the olefins corresponding to the ketones represented by the formula (MK11) are represented by the following formula (MOL11), and the olefins corresponding to the ketones represented by the formula (MK12) are represented by the following formula (MOL12).

[0176]

[0177] (In the formula (MOL11), R １１ is R in the formula (11). １１ and in the formula (MOL12), R １２ is R in the formula (12). １２ is synonymous with

[0178] In the PC resin production method according to this embodiment, the dihydric phenol compound (ma) may be a compound represented by the following formula (MA11), or a compound represented by the following formula (MA12).

[0179]

[0180] (In the formula (MA11), X １１ , X １２ , X １３ , X １４ and R １１ are the X in the formula (11), respectively. １１ , X １２ , X １３ , X １４ and R １１ In the formula (MA12), X １５ , X １６ , X １７ , X １８ and R １２ are the X in the formula (12), respectively. １５ , X １６ , X １７ , X １８ and R １２ is synonymous with

[0181] The structure represented by formula (11) is derived from the compound represented by formula (MA11). The compound represented by formula (MA11) can be produced by condensing a phenol (mp) with a ketone represented by formula (MK11). The structure represented by formula (12) is derived from the compound represented by formula (MA12). The compound represented by formula (MA12) can be produced by condensing a phenol (mp) with a ketone represented by formula (MK12).

[0182] The method for producing a polycarbonate resin (PC resin production method) according to this embodiment preferably includes a polymerization step of polymerizing a polycarbonate resin using the compound represented by formula (MA1). The method for producing a PC resin according to this embodiment also preferably includes a polymerization step of polymerizing a polycarbonate resin using the compound represented by formula (MA1) and at least one compound selected from the group consisting of the compound represented by formula (MA11) and the compound represented by formula (MA12). In the method for producing a PC resin according to this embodiment, it is also preferable that the polymerization step is carried out in the absence of the compound represented by formula (MA1) and phosgene.

[0183] The polycarbonate resin according to this embodiment can be produced using a dihydric phenol compound (mb) represented by the following formula (MA2). The structure represented by the formula (2) is derived from the dihydric phenol compound (mb). Therefore, this embodiment also provides use of the dihydric phenol compound (mb) represented by the following formula (MA2) for producing the polycarbonate resin according to this embodiment.

[0184]

[0185] (In the formula (MA2), R ３ and R ４ are R in the formula (2), respectively. ３ and R ４ is synonymous with

[0186] The dihydric phenol compound (mb) represented by the formula (MA2) can be produced by condensing a phenol (mp) with a ketone represented by the following formula (MK2).

[0187]

[0188] (In the formula (MK2), R ３ and R ４ are R in the formula (2), respectively. ３ and R ４ is synonymous with

[0189] In the method for producing a PC resin according to this embodiment, the ketones represented by formula (MK2) may be used singly, in a mixture of two or more, or in a mixture of three or more. The ketones represented by formula (MK2) can be produced by oxidizing the corresponding olefins. Alternatively, the ketones represented by formula (MK2) can be produced by mixing two or more, or three or more, olefins to obtain an olefin mixture, and then oxidizing this olefin mixture.

[0190] In the method for producing a PC resin according to this embodiment, the olefins corresponding to the ketones represented by the formula (MK2) are represented by the following formula (MOL2).

[0191]

[0192] (In the formula (MOL2), R ３ is R in the formula (2). ３ and r is 0, 1, 2, 3, 4, or 5.

[0193] In the PC resin production method according to this embodiment, the dihydric phenol compound (mb) can be produced by condensing a phenol (mp) with a ketone represented by the following formula (MK21), or can be produced by condensing a phenol (mp) with a ketone represented by the following formula (MK22).

[0194]

[0195] (In the formula (MK21), R ４ and R ３１ are R in the formula (21), respectively. ４ and R ３１ In the formula (MK22), R ４ and R ３２ are R in the formula (22), respectively. ４ and R ３２ is synonymous with

[0196] The ketones represented by the formula (MK21) and the ketones represented by the formula (MK22) can be produced by oxidizing the corresponding olefins, respectively.

[0197] In the PC resin production method according to this embodiment, the olefins corresponding to the ketones represented by the formula (MK21) are represented by the following formula (MOL21), and the olefins corresponding to the ketones represented by the formula (MK22) are represented by the following formula (MOL22).

[0198]

[0199] (In the formula (MOL21), R ３１ is R in the formula (21). ３１ and in formula (MOL22), R ３２ is R in the formula (22). ３２ and r is 0, 1, 2, 3, 4, or 5.

[0200] In the PC resin production method according to this embodiment, the dihydric phenol compound (mb) may be a compound represented by the following formula (MA21), or a compound represented by the following formula (MA22).

[0201]

[0202] (In the formula (MA21), R ４ and R ３１ are R in the formula (21), respectively. ４ and R ３１ In the formula (MA22), R ４ and R ３２are R in the formula (22), respectively. ４ and R ３２ is synonymous with

[0203] In the formula (MA21) and the formula (MA22), R ４ can also be expressed by the following formula (MA23).

[0204]

[0205] (In the formula (MA23), r is 0, 1, 2, 3, 4, or 5, and * represents a bond.)

[0206] The structure represented by formula (2) is derived from the compound represented by formula (MA2). The compound represented by formula (MA2) can be produced by condensing 2,6-dimethylphenol with a ketone represented by formula (MK2). The structure represented by formula (21) is derived from the compound represented by formula (MA21). The compound represented by formula (MA21) can be produced by condensing 2,6-dimethylphenol with a ketone represented by formula (MK21). The structure represented by formula (22) is derived from the compound represented by formula (MA22). The compound represented by formula (MA22) can be produced by condensing 2,6-dimethylphenol with a ketone represented by formula (MK22).

[0207] The PC resin production method according to this embodiment also preferably includes a polymerization step of polymerizing a polycarbonate resin using the compound represented by formula (MA2). The PC resin production method according to this embodiment also preferably includes a polymerization step of polymerizing a polycarbonate resin using the compound represented by formula (MA2) and at least one compound selected from the group consisting of the compound represented by formula (MA21) and the compound represented by formula (MA22). In the PC resin production method according to this embodiment, it is also preferable that the polymerization step is carried out in the absence of the compound represented by formula (MA2) and phosgene.

[0208] The PC resin containing the structure represented by formula (1) or the structure represented by formula (2) as a repeating unit can be produced by a known method for producing a polycarbonate resin, using, for example, a dihydric phenol compound (ma) represented by formula (MA1) or a dihydric phenol compound (mb) represented by formula (MA2) as the dihydric phenol compound. Examples of the method for producing a PC resin according to this embodiment include the following production methods (P1-1), (P1-2), and (P1-3).

[0209] <Production Method (P1-1)> The production method (P1-1) is an interfacial polymerization method (phosgene method) in which a dihydric phenol compound and a carbonate precursor such as phosgene are reacted in the presence of an organic solvent inert to the reaction and an aqueous alkaline compound solution, and then a polymerization catalyst such as a tertiary amine or a quaternary ammonium salt is added to carry out polymerization.

[0210] <Production Method (P1-2)> Production method (P1-2) is a melt polymerization method (transesterification method) in which a dihydric phenol compound and a carbonic acid diester are subjected to a transesterification reaction in a molten state without using a solvent, by adding a basic catalyst.

[0211] <Production Method (P1-3)> Production method (P1-3) is a pyridine method in which a dihydric phenol compound is dissolved in pyridine or a mixed solution of pyridine and an inert solvent, and phosgene is introduced to directly produce the compound.

[0212] In the above reaction, at least one additive selected from the group consisting of a molecular weight regulator (terminal terminator) and a branching agent may be used as needed.

[0213] The method for producing a PC resin according to this embodiment is preferably the following production method (P1-4): <Production method (P1-4)> Production method (P1-4) is a method for producing an aromatic polycarbonate resin, comprising a step of interfacially polycondensing a dihydric phenol compound and a polycarbonate oligomer in the presence of a water-insoluble organic solvent and an aqueous alkaline compound solution, wherein the dihydric phenol compound comprises at least one selected from the group consisting of the dihydric phenol compound (ma) represented by formula (MA1) above and the dihydric phenol compound (mb) represented by formula (MA2) above.

[0214] Specifically, in the case of the interfacial polymerization method of production methods (P1-1) or (P1-4), the PC resin according to this embodiment can be produced by dissolving a pre-produced polycarbonate oligomer described below in a water-insoluble organic solvent (e.g., methylene chloride), adding an alkaline compound aqueous solution of a dihydric phenol compound (e.g., sodium hydroxide aqueous solution), and using a tertiary amine (e.g., triethylamine) or a quaternary ammonium salt (e.g., trimethylbenzylammonium chloride) as a polymerization catalyst, and optionally in the presence of a terminal terminator (a monohydric phenol such as p-tert-butylphenol). Furthermore, in the case of the above interfacial polymerization method, the PC resin according to this embodiment can also be produced by copolymerizing a dihydric phenol with phosgene, a carbonate ester, or a chloroformate.

[0215] Polycarbonate oligomers can be produced by reacting a dihydric phenol compound with a carbonate precursor (e.g., phosgene, triphosgene, etc.) in an organic solvent such as methylene chloride, chlorobenzene, chloroform, etc. When producing a polycarbonate oligomer using a transesterification method, it can also be produced by reacting a dihydric phenol compound with a carbonate precursor such as diphenyl carbonate.

[0216] In the PC resin production method according to this embodiment, the dihydric phenol includes at least one selected from the group consisting of a dihydric phenol compound (ma) represented by the formula (MA1) and a dihydric phenol compound (mb) represented by the formula (MA2). In one aspect of the PC resin production method according to this embodiment, the dihydric phenol further includes a dihydric phenol compound (md) represented by the following formula (MD3). The dihydric phenol compound (md) is a compound different from the dihydric phenol compound (ma) and the dihydric phenol compound (mb). The structure represented by the formula (3) is derived from the dihydric phenol compound (md).

[0217]

[0218] (In the formula (MD3), Y, p, q and R ２ respectively represent Y, p, q and R in the formula (3). ２ is synonymous with

[0219] In the method for producing a PC resin according to this embodiment, the dihydric phenol compound (md) may be used alone or in combination of two or more.

[0220] In the method for producing a PC resin according to this embodiment, the dihydric phenol compound (md) alone can be used as the dihydric phenol compound for producing the polycarbonate oligomer. In this case, in the interfacial polycondensation reaction step, the dihydric phenol compound (md) may be used in combination with at least one selected from the group consisting of the dihydric phenol compound (ma) and the dihydric phenol compound (mb), or the dihydric phenol compound (ma) alone or the dihydric phenol compound (mb) alone may be used.

[0221] (Organic Solvent) In the PC resin production method according to this embodiment, examples of organic solvents inert to the reaction include chlorinated hydrocarbons (dichloromethane (methylene chloride), chloroform, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,1,2-tetrachloroethane, 1,1,2,2-tetrachloroethane, pentachloroethane, or chlorobenzene), acetophenone, and toluene. These organic solvents may be used alone or in combination of two or more. In the PC resin production method according to this embodiment, methylene chloride is preferred as the organic solvent.

[0222] (Alkaline Compound) Examples of the alkaline compound contained in the alkaline compound aqueous solution include alkali metal compounds and alkaline earth metal compounds. Examples of the alkali metal compound include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, and sodium bicarbonate. Examples of the alkaline earth metal compound include magnesium hydroxide, calcium hydroxide, and calcium acetate. In the PC resin production method according to this embodiment, the alkali compound is preferably sodium hydroxide or potassium hydroxide. In the PC resin production method according to this embodiment, one type of alkali compound may be used alone, or two or more types may be used in combination.

[0223] (Polymerization Catalyst) In the PC resin production method according to this embodiment, at least one selected from the group consisting of quaternary ammonium salts, quaternary phosphonium salts, and tertiary amines can be used as the polymerization catalyst. Examples of quaternary ammonium salts include trimethylbenzyl ammonium chloride, triethylbenzyl ammonium chloride, tributylbenzyl ammonium chloride, trioctylmethyl ammonium chloride, tetrabutyl ammonium chloride, and tetrabutyl ammonium bromide. Examples of quaternary phosphonium salts include tetrabutyl phosphonium chloride and tetrabutyl phosphonium bromide. Examples of tertiary amines include triethylamine, tributylamine, N,N-dimethylcyclohexylamine, pyridine, and dimethylaniline.

[0224] (Branching Agent) Examples of branching agents that can be used in the PC resin production method according to this embodiment include phloroglucin, pyrogallol, 1,1,1-tris(4-hydroxyphenyl)methane, 1,1,1-tris(4-hydroxyphenyl)ethane, 1,1,1-tris(4-hydroxyphenyl)propane, 1,1,1-tris(3-methyl-4-hydroxyphenyl)ethane, 4,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)-2-heptene, 4,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)-2-prop ... (4-hydroxyphenyl)heptane, 2,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)-3-heptene, 1,3,5-tris(2-hydroxyphenyl)benzene, 1,3,5-tris(4-hydroxyphenyl)benzene, tris(4-hydroxyphenyl)-phenylmethane, 2,2-bis[4,4-bis(4-hydroxyphenyl)cyclohexyl]propane, 2,4-bis(4-hydroxyphenylisopropyl)phenol, 2,6-bis(2-hydroxy-5-methyl)methane 2-(4-hydroxyphenyl)-2-(2,4-dihydroxyphenyl)propane, α,α',α"-tris(4-hydroxyphenyl)-1,3,5-triisopropylbenzene, 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methylphenol, hexakis[4-(4-hydroxyphenylisopropyl)phenyl]-o-terephthalic acid ester, tetrakis(4-hydroxyphenyl)methane, tetrakis[4-(4-hydroxyphenylisopropyl)phenyl]-o-terephthalic acid ester [phenylisopropyl)phenoxy]methane, 1,4-bis[(4',4"-dihydroxytriphenyl)methyl]benzene, 2,4-dihydroxybenzoic acid, trimesic acid, cyanuric acid chloride, 3,3-bis(3-methyl-4-hydroxyphenyl)-2-oxo-2,3-dihydroindole, 3,3-bis(4-hydroxyaryl)oxindole [=isatin bisphenol], 5-chloroisatin, 5,7-dichloroisatin, 5-bromoisatin, and phloroglyside.

[0225] (End Capper) In the method for producing a PC resin according to this embodiment, an end capper (molecular weight regulator) can be used to adjust the molecular weight of the PC resin. As the end capper, a monohydric phenol can be used. Examples of monohydric phenols that can be used in the method for producing a PC resin according to this embodiment include phenol, α-naphthol, β-naphthol, o-cresol, m-cresol, p-cresol, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol, p-ethylphenol, p-propylphenol, p-butylphenol, p-pentylphenol, p-hexylphenol, p-heptylphenol, p-octylphenol, p-cumylphenol, p-nonylphenol, m-pentadecylphenol, p-decylphenol, p-undecylphenol, p-dodecylphenol, p-isopropylphenol, p-tert-butylphenol, 2,6-dimethyl-p-tert-butylphenol, 2-tert-amyl-4-methylphenol, 3-methyl-6-tert-butylphenol, Examples of such an amine include phenol, 2-methyl-4,6-di-tert-butylphenol, 2,4-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol, 4-tert-octylphenol, 4-tert-amylphenol, 2,4,6-tri-tert-butylphenol, p-phenylphenol, 2,6-di-tert-butyl-4-phenylphenol, 2,6-di-sec-butyl-4-methylphenol, o-anisole, m-anisole, p-anisole, o-chlorophenol, m-chlorophenol, p-chlorophenol, o-bromophenol, m-bromophenol, p-bromophenol, p-ethoxyphenol, o-aminophenol, m-aminophenol, p-aminophenol, p-cyanophenol, p-nitrophenol, 3-methyl-6-isopropylphenol, and 2-methyl-5-isopropylphenol. In the method for producing a PC resin according to this embodiment, the monohydric phenol may be used alone or in combination of two or more kinds.

[0226] In the method for producing a PC resin according to this embodiment, preferred end terminators are p-tert-butylphenol and p-phenylphenol. By using p-tert-butylphenol as the end terminator in the method for producing a PC resin according to this embodiment, a PC resin having an end group represented by the following formula (T1) can be produced.

[0227]

[0228] (In the formula (T1), * represents a bond to a repeating unit located at the terminal of the PC resin.)

[0229] (Antioxidant) In the method for producing a PC resin according to this embodiment, an antioxidant may be present in the reaction system to prevent oxidation of the dihydric phenol compound. Examples of the antioxidant include hydrosulfite.

[0230] (Reduced Viscosity) The reduced viscosity of the PC resin according to this embodiment can be adjusted to a predetermined range by various methods, such as selecting the reaction conditions and adjusting the amounts of the end-capping agent and branching agent used. Furthermore, the obtained PC resin can be subjected to at least one of physical and chemical treatments, as appropriate, to obtain a PC resin with a predetermined reduced viscosity. Examples of physical treatments include mixing and fractionation. Examples of chemical treatments include polymer reaction, crosslinking, and partial decomposition.

[0231] (Effects of this embodiment) According to this embodiment, it is possible to provide a polycarbonate resin having improved dielectric properties and heat resistance.

[0232] In the PC resin according to this embodiment, R in the structure represented by formula (1) １ and R in the structure represented by formula (2). ３ When the number of carbon atoms in the linear alkyl groups as R is 12 or more, the relative dielectric constant Dk can be reduced. １ and R in the structure represented by formula (2). ３The greater the number of carbon atoms in the linear alkyl group as R in the structure represented by formula (1), the lower the dielectric loss tangent Df tends to be. １ and R in the structure represented by formula (2). ３ The smaller the number of carbon atoms in the linear alkyl group as R is, the higher the glass transition temperature Tg and the more likely it is that the heat resistance will be improved. １ and R in the structure represented by formula (2). ３ When the number of carbon atoms in the linear alkyl groups as the olefins is 24 or less, the dielectric loss tangent Df can be reduced without significantly reducing the glass transition temperature Tg.

[0233] In the PC resin according to this embodiment, R in the structure represented by formula (1) １ The carbon atom to which R is bonded (hereinafter, sometimes referred to as the central carbon atom) has a methyl group as an alkyl group. ４ is a linear alkyl group having 1 to 6 carbon atoms. １ In the case where a hydrogen atom is bonded to the carbon atom (central carbon atom) to which R is bonded instead of an alkyl group, or ３ The carbon atom to which R is bonded (the central carbon atom) ４ In the case where a hydrogen atom is bonded to the central carbon atom instead of a linear alkyl group having 1 to 6 carbon atoms as R, the hydrogen atom bonded to the central carbon atom is at the benzyl position relative to the two aromatic rings and is tertiary, so it is easily abstracted by radicals. Therefore, PC resins in which a hydrogen atom is bonded to the central carbon atom instead of an alkyl group are susceptible to deterioration such as oxidation during thermoforming. On the other hand, the PC resin according to this embodiment has an alkyl group such as a methyl group bonded to the central carbon atom instead of a hydrogen atom, so radical generation is suppressed and deterioration during thermoforming can be suppressed. Note that R １ or R ３Bisphenols (sometimes referred to as dihydric phenol compounds) in which, in addition to a linear alkyl group having 12 to 24 carbon atoms as the bisphenol, a long-chain alkyl group (an alkyl group having 7 or more carbon atoms) is further bonded to the central carbon atom are difficult to synthesize. This is because the steric hindrance of the ketones, which are the raw materials for synthesizing the bisphenol, makes it difficult for the condensation reaction between the ketones and phenols to proceed.

[0234] In the PC resin according to this embodiment, the ortho position (X １ , X ２ , X ３ and X ４ At least one of the ortho positions (positions (a) and (b)) is a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group, and the ortho position of the phenol in the structure represented by formula (2) is a methyl group. Thus, in the PC resin according to this embodiment, the presence of a substituent at the ortho position of the phenol suppresses molecular mobility and reduces the dielectric dissipation factor Df. By selecting a methyl group, which is the least sterically bulky alkyl group, as the substituent at the ortho position of the phenol, it is possible to suppress a decrease in reactivity due to steric hindrance during the synthesis reaction of the PC resin and to prevent polymer structural abnormalities (such as an increase in terminal hydroxyl groups) caused by incomplete reaction. Even if all ortho positions of the phenol are substituted with alkyl groups, as in the structure represented by formula (2), if all the alkyl groups are methyl groups, it is possible to suppress a decrease in reactivity due to steric hindrance during the synthesis reaction of the PC resin and to prevent polymer structural abnormalities (such as an increase in terminal hydroxyl groups) caused by incomplete reaction. Furthermore, by substituting all with methyl groups in this way to increase symmetry, the glass transition temperature Tg is increased and heat resistance is improved.

[0235] [Second Embodiment] [Electronic Substrate] One aspect of the electronic substrate according to this embodiment includes the polycarbonate resin according to the first embodiment. According to this embodiment, it is possible to provide an electronic substrate including the polycarbonate resin having improved dielectric properties and heat resistance.

[0236] One aspect of the electronic substrate according to this embodiment contains the electronic substrate material according to this embodiment.

[0237] Electronic substrates are used for a variety of purposes, including servers, automotive applications, base stations, antennas for smartphones, and transmission boards. Electronic substrates can be broadly categorized into semiconductor substrates and electronic circuit boards. (1) Semiconductor Substrates: Semiconductor substrates are substrates for forming wiring layers that handle the input and output of electrical signals to and from chips such as logic ICs, memory, and sensors. This wiring layer is a connection layer for connecting identical or different types of chips in parallel or stacked configurations. Examples of chip types include FC-CSP (flip chip-chip scale package), FC-BGA (flip chip-ball grid array), and FO-WLP (fan-out-wafer level package), as well as packages using interposers to connect multiple semiconductor chips. (2) Electronic Circuit Boards: Electronic circuit boards are substrates formed with wiring layers for connecting multiple electronic components, such as semiconductors and capacitors. Electronic circuit boards are sometimes referred to as printed wiring boards. Types of electronic circuit boards include multilayer boards (rigid boards and flexible boards) with stacked wiring.

[0238] [Electronic Substrate Material] The electronic substrate material according to this embodiment is used in the form of a coating composition (varnish), film, or sheet to form the electronic substrate according to this embodiment. That is, this coating composition (varnish), film, and sheet include the electronic substrate material according to this embodiment. The electronic substrate material according to this embodiment is excellent in low dielectric properties, low thermal expansion coefficient, and high heat resistance. The electronic substrate material according to this embodiment can provide a composition for a coating liquid that has high solvent solubility and low solution viscosity characteristics for coating molding.

[0239] The electronic substrate material according to this embodiment contains a first resin.

[0240] <First Resin> In one aspect of the electronic board material according to the present embodiment, the first resin is at least one resin selected from the group consisting of polycarbonate, polyester, and polyester polycarbonate. In the electronic board material according to the present embodiment, the first resin is the polycarbonate resin according to the first embodiment.

[0241] <Inorganic Filler> The electronic substrate material according to this embodiment may further contain an inorganic component. In one aspect of the electronic substrate material according to this embodiment, the inorganic component preferably contains at least one component selected from the group consisting of an inorganic filler, glass fiber, and glass cloth. In this embodiment, the inorganic filler is preferably at least one filler selected from the group consisting of silica, boron nitride, aluminum nitride, silicon nitride, silicon carbide, zinc oxide, titanium oxide, aluminum oxide, magnesium oxide, aluminum hydroxide, and magnesium hydroxide. The silica used as the inorganic filler is preferably at least one silica selected from the group consisting of spherical silica, pulverized silica, hollow silica, and fumed silica.

[0242] <Thermoplastic Resin (Third Resin)> The electronic substrate material according to this embodiment may further contain a thermoplastic resin (this thermoplastic resin may be referred to as a third resin). The third resin is a thermoplastic resin different from the first resin. As the third resin, for example, a known thermoplastic resin may be used.

[0243] In one aspect of the electronic board material according to the present embodiment, the content of the first resin in the electronic board material is 50 mass % or more.

[0244] [Insulating Material] One aspect of the insulating material according to this embodiment includes the polycarbonate resin according to the first embodiment. According to this embodiment, it is possible to provide an insulating material including a polycarbonate resin having improved dielectric properties and heat resistance. The insulating material according to this embodiment can be used as an electronic substrate material.

[0245] [Coating composition] The electronic substrate material according to this embodiment may be contained in a coating composition. The coating composition according to this embodiment contains the electronic substrate material, and the electronic substrate material is specifically the PC resin according to the first embodiment. The coating composition according to this embodiment may also be called a varnish. The coating composition according to this embodiment contains the electronic substrate material and an organic solvent. During the molding step of molding an electronic substrate using the coating composition, the solvent in the coating composition is removed by heating.

[0246] The organic solvent for the coating liquid composition can be appropriately selected taking into consideration the solubility of materials such as the PC resin according to the first embodiment, the drying speed after molding, the effect of the solvent remaining on the molded product, and hazards (fire or health hazards).

[0247] Examples of organic solvents used in the coating composition according to this embodiment include cyclic ethers (such as tetrahydrofuran (THF), dioxane, and dioxolane), cyclic ketones (such as cyclohexanone, cyclopentanone, and cycloheptanone), aromatic hydrocarbons (such as toluene, xylene, and chlorobenzene), ketones (such as methyl ethyl ketone (MEK) and methyl isobutyl ketone (MIBK)), halogenated hydrocarbons (such as dichloromethane and chloroform), esters (such as ethyl acetate, isopropyl acetate, isobutyl acetate, and butyl acetate), ethers (such as ethylene glycol dimethyl ether and ethylene glycol monoethyl ether), amides (such as N,N-dimethylformamide (DMF) and dimethylacetamide (DMAc)), and aprotic polar solvents (such as dimethyl sulfoxide (DMSO)).

[0248] In the coating liquid composition of the present embodiment, in consideration of the environment and safety, the organic solvent is preferably an organic solvent other than halogenated hydrocarbons, i.e., a non-halogenated solvent, and more preferably at least one solvent selected from the group consisting of toluene, cyclohexanone, methyl ethyl ketone, tetrahydrofuran, dioxolane, and cyclopentanone.

[0249] One aspect of the coating liquid composition according to this embodiment contains an electronic substrate material and a non-halogen-based solvent.

[0250] One aspect of the coating liquid composition according to this embodiment contains the PC resin according to the first embodiment and a non-halogen-based solvent.

[0251] The concentration of the PC resin according to the first embodiment in the coating composition according to this embodiment may be any concentration that provides an appropriate viscosity for the intended use of the coating composition, and is preferably 0.1% by mass or more and 40% by mass or less. The concentration of the PC resin according to the first embodiment in the coating composition according to this embodiment is more preferably 1% by mass or more, and even more preferably 5% by mass or more. The concentration of the PC resin according to the first embodiment in the coating composition according to this embodiment is more preferably 35% by mass or less, and even more preferably 30% by mass or less. When the concentration of the PC resin according to the first embodiment in the coating composition according to this embodiment is 40% by mass or less, the viscosity does not become too high and the coatability is good. When the concentration of the PC resin according to the first embodiment in the coating composition according to this embodiment is 0.1% by mass or more, the viscosity can be maintained at an appropriate level, and a homogeneous film can be obtained. Furthermore, when the concentration is 0.1% by mass or more, the drying time after application of the coating composition can be shortened, and a film with a desired thickness can be easily formed.

[0252] The electronic substrate material according to this embodiment may be applied in solution, i.e., as a coating composition, directly onto a core material made of polyimide, epoxy resin, or the like. In this case, an inorganic filler such as silica may be dispersed in the coating composition. Suitable solvents for dispersing the inorganic filler in the coating composition include, for example, toluene, cyclohexanone, and MEK.

[0253] [Film] One aspect of the film according to this embodiment contains the PC resin according to the first embodiment.

[0254] One aspect of the film according to this embodiment contains the electronic substrate material according to this embodiment.

[0255] The film according to this embodiment can be produced by thermoforming (e.g., melt extrusion molding) or solution casting the electronic substrate material according to this embodiment. When a thin film (e.g., a few μm to a few tens of μm) is desired, solution casting is preferred. Furthermore, for the purpose of reducing thermal expansion, the electronic substrate material may be impregnated into a fibrous substrate such as glass cloth, or an electronic substrate material in a state where an inorganic filler such as silica is dispersed may be formed into a film. The fibrous substrate is preferably at least one substrate selected from the group consisting of glass cloth, polyester cloth, glass nonwoven fabric, aramid nonwoven fabric, glass paper, and pulp paper. One type of fibrous substrate may be used alone, or two or more types may be used in combination.

[0256] Furthermore, it may be used when forming an electronic substrate material containing a known thermoplastic resin as a third resin into a film for the purpose of improving dielectric properties, adjusting the elastic modulus, etc. Furthermore, when the electronic substrate material according to this embodiment has a crosslinked moiety, when the electronic substrate material having the crosslinked moiety is used to form a film by solution casting, it is also possible to add a curing material to the electronic substrate material and adjust the heating temperature to control the degree of crosslinking and change the elastic modulus of the film, etc.

[0257] One aspect of the film according to this embodiment is a resin film obtained by filming the PC resin according to the first embodiment. The electronic board material according to this embodiment may be a copper-clad laminate (CCL) formed by laminating copper foil on one or both sides of this PC resin film. An adhesive layer may be disposed between the PC resin film and the copper foil. This copper-clad laminate is preferably a flexible CCL having flexibility and bendability. Another aspect of the film according to this embodiment is a film (sometimes referred to as a prepreg) obtained by impregnating a fibrous substrate such as glass cloth with the PC resin according to the first embodiment. The electronic board material according to this embodiment may be a copper-clad laminate (CCL) formed by laminating copper foil on both sides of this film (prepreg). This copper-clad laminate is preferably a rigid CCL, which is harder than a flexible CCL. The PC resin according to the first embodiment may be impregnated into a fibrous substrate using the coating liquid composition according to this embodiment. The electronic board according to this embodiment preferably includes this copper-clad laminate.

[0258] [Sheet] One aspect of the sheet according to this embodiment contains the PC resin according to the first embodiment.

[0259] One aspect of the sheet according to this embodiment contains the electronic substrate material according to this embodiment.

[0260] When the electronic substrate material according to this embodiment is used as a sheet, the substrate or the like can be impregnated with the coating liquid composition (varnish) to form the sheet.

[0261] [Bonding Film] One aspect of the bonding film according to this embodiment contains the PC resin according to the first embodiment. In one aspect, the bonding film according to this embodiment has a layer containing the PC resin according to the first embodiment (hereinafter, sometimes referred to as a PC resin layer). This PC resin layer may be a resin composition layer. One aspect of the bonding film according to this embodiment includes a PC resin layer and a release film in contact with at least one surface of the PC resin layer, and the PC resin layer is preferably in a B-stage state (i.e., in a semi-cured state). In one aspect, the bonding film according to this embodiment may include a PC resin layer between two release films. Required properties of this bonding film include low dielectric properties and high adhesion.

[0262] [Interlayer insulating film] One aspect of the interlayer insulating film according to this embodiment contains the PC resin according to the first embodiment. A package substrate is disposed between an IC chip and a motherboard included in a personal computer or smartphone. This package substrate is a component that protects the IC chip and transmits signals to the motherboard. An interlayer insulating film is provided to maintain insulation between the circuits of this package substrate. Required properties of the interlayer insulating film include low dielectric properties, low thermal expansion, high adhesion to copper, high solvent solubility, and high dispersibility of inorganic fillers.

[0263] In one aspect of the interlayer insulating film according to this embodiment, various components that can be contained in the interlayer insulating film include resin, organic solvent, inorganic filler, curing accelerator, organic filler, and adhesion promoter. Resins that can be contained in the interlayer insulating film include the PC resin according to the first embodiment, as well as general thermosetting and thermoplastic resins other than the PC resin according to the first embodiment. The component responsible for achieving low dielectric properties and low thermal expansion is resin, and the component responsible for achieving low dielectric tangent and low thermal expansion is spherical silica gel, an inorganic filler, although this increases the dielectric constant. The use of adhesion promoters is also effective in improving adhesion to copper, but this depends on the properties of the resin.

[0264] Next, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to these examples and various modifications and applications are possible within the scope of the present invention.

[0265] [Production Examples and Synthesis Examples] [Production Example: Preparation of Ketones] <Production Example 1> In a 5-liter flask were added olefin mixture OM1 (243 g), dimethylacetamide (DMA) (2900 mL), and water (424 mL), and the mixture was heated and stirred to homogenize. ２ (6.20 g) and CuCl (84.5 g) were added, and the mixture was stirred at 50°C for 24 hours under an oxygen stream to obtain a reaction product. The olefin mixture OM1 was prepared by mixing 1-eicosene, 1-docosene, and 1-tetracosene in a mass ratio of 53:39:4. A mixed solvent containing ethyl acetate and hexane in a mass ratio of 1:9, and water were added to the reaction product, and the mixture was filtered under heated conditions to obtain a reaction liquid. The obtained reaction liquid was washed with saturated aqueous sodium bicarbonate and brine, and then dried over anhydrous magnesium sulfate. The extract after washing and drying was concentrated and then purified using a silica gel column to obtain methyl alkyl ketone A2024 according to Production Example 1.

[0266] Production Example 2 Methyl hexadecyl ketone AO18 according to Production Example 2 was synthesized in the same manner as in Production Example 1, except that the olefin mixture OM1 in Production Example 1 was changed to 1-octadecene.

[0267] [Production Example: Preparation of Bisphenol] <Production Example 3> A reaction flask was equipped with a Dean-Stark. Methyl alkyl ketone A2024 (5 parts by mass) according to Production Example 1, 2,6-dimethylphenol (15 parts by mass), p-toluenesulfonic acid (0.3 parts by mass), 1-dodecanethiol (0.3 parts by mass), and toluene (36 parts by mass) were mixed in this reaction flask, and the mixture was stirred for 18 hours under heating and reflux while distilling off the generated water. After stirring, NaHCO ３ After adding the aqueous solution, the organic layer was extracted with ethyl acetate. ２ SO ４The mixture was dried at 750°C, filtered, and concentrated. After concentration, 15.1 parts by mass of an orange viscous solid was obtained as a crude product. The target compound was separated from the orange viscous solid using a silica gel column, and the separated compound was dried under reduced pressure to obtain 2.9 parts by mass of bisphenol TMP2024 having the following structure. １ H-NMR was measured and it was confirmed that it had the following structure: In the following structural formula of bisphenol TMP2024, n was 18, 20, or 22. Bisphenol TMP2024 was a mixture of bisphenols with n=18, bisphenols with n=20, and bisphenols with n=22.

[0268]

[0269] <Production Example 4> Bisphenol BisP2024 according to Production Example 4 was synthesized in the same manner as in Production Example 3, except that 2,6-dimethylphenol in Production Example 3 was changed to phenol. In Production Example 4, 3.0 parts by mass of bisphenol BisP2024 was obtained. １ H-NMR was measured and it was confirmed that it had the following structure: n in the following structural formula of bisphenol BisP2024 was 18, 20, or 22. Bisphenol BisP2024 was a mixture of bisphenols with n=18, bisphenols with n=20, and bisphenols with n=22.

[0270]

[0271] <Production Example 5> Bisphenol TMP18 according to Production Example 5 was synthesized in the same manner as in Production Example 3, except that methyl alkyl ketone A2024 in Production Example 3 was changed to methyl hexadecyl ketone AO18. In Production Example 5, 3.0 parts by mass of bisphenol TMP18 was obtained. １ H-NMR was measured and it was confirmed that the structure was as follows.

[0272]

[0273] [Production Example: Preparation of Oligomer] <Production Example 6>: Synthesis of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane bischloroformate 75.8 g (224 mmol) of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane was suspended in 1080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution of 44.0 g (435 mmol) of triethylamine dissolved in 120 mL of methylene chloride was added dropwise thereto at a temperature in the range of 5°C to 15°C. Next, after stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. The remaining liquid was washed with 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite. The oligomer was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 1,1-bis-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane oligomer having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 0.92 mol / L, a solid concentration of 0.220 kg / L, and an average number of monomers of 1.04. Hereinafter, the oligomer obtained in Production Example 6 will be referred to as OCTMC-CF.

[0274] <Production Example 7>: Synthesis of 1,1-bis-(3,5-dimethyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane oligomer (bischloroformate) 82.1 g (224 mmol) of 1,1-bis-(3,5-dimethyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane was suspended in 1080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution of 44.0 g (435 mmol) of triethylamine dissolved in 120 mL of methylene chloride was added dropwise thereto at a temperature in the range of 5°C to 15°C. Next, after stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. The remaining liquid was washed with 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite. The oligomer was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 1,1-bis-(3,5-dimethyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane oligomer having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 0.86 mol / L, a solid concentration of 0.225 kg / L, and an average number of monomers of 1.08. Hereinafter, the oligomer obtained in Production Example 7 will be referred to as TMBPTMC-CF.

[0275] <Production Example 8>: Synthesis of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclododecane oligomer (bischloroformate) 85.2 g (224 mmol) of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclododecane was suspended in 1,080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution of 44.0 g (435 mmol) of triethylamine dissolved in 120 mL of methylene chloride was added dropwise thereto at a temperature in the range of 5°C to 15°C. Next, after stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. The remaining liquid was washed with 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite. The oligomer was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclododecane oligomer having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 0.86 mol / L, a solid concentration of 0.222 kg / L, and an average number of monomers of 1.03. Hereinafter, the oligomer obtained in Production Example 8 will be referred to as OCCDE-CF.

[0276] <Production Example 9>: Synthesis of 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)cyclododecane oligomer (bischloroformate) 91.5 g (mmol) of 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)cyclododecane was suspended in 1,080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution of 44.0 g (435 mmol) of triethylamine dissolved in 120 mL of methylene chloride was added dropwise thereto at a temperature in the range of 5°C to 15°C. Next, after stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. The remaining liquid was washed with 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite. The oligomer was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 1,1-bis-(4-hydroxy-3,5-dimethylphenyl)cyclododecane oligomer having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 0.78 mol / L, a solid concentration of 0.216 kg / L, and an average number of monomers of 1.05. Hereinafter, the oligomer obtained in Production Example 9 will be referred to as TMBPCDE-CF.

[0277] <Production Example 10>: Synthesis of 2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane oligomer (bischloroformate) 87.9 g (224 mmol) of 2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane was suspended in 1,080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution of 44.0 g (435 mmol) of triethylamine dissolved in 120 mL of methylene chloride was added dropwise thereto at a temperature in the range of 5°C to 15°C. Next, after stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. The remaining liquid was washed with 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite. The oligomer was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane oligomer having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 0.84 mol / L, a solid concentration of 0.223 kg / L, and an average number of monomers of 1.03. Hereinafter, the oligomer obtained in Production Example 10 will be referred to as CHA-CF.

[0278] <Production Example 11>: Synthesis of 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane oligomer (bischloroformate) 96.9 g (224 mmol) of 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane was suspended in 1,080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution of 44.0 g (435 mmol) of triethylamine dissolved in 120 mL of methylene chloride was added dropwise thereto at a temperature in the range of 5°C to 15°C. Next, after stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. The remaining liquid was washed with 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite. The oligomer was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane oligomer having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 0.75 mol / L, a solid concentration of 0.221 kg / L, and an average number of monomers of 1.07. Hereinafter, the oligomer obtained in Production Example 11 will be referred to as CHZ-CF.

[0279] [Synthesis Examples: Synthesis of PC Polymer] [Synthesis Example 1] PC Polymer (PC-1) (Synthesis of PC Polymer) The oligomer OCTMC-CF (182 mL) according to Production Example 6 and methylene chloride (263 mL) were poured into a reaction vessel equipped with a mechanical stirrer, a stirring blade, and a baffle. To this was added p-tert-butylphenol (hereinafter referred to as PTBP) (0.176 g) as a terminal terminator, and the solution was stirred to ensure thorough mixing, yielding a methylene chloride solution (M1). After stirring, the methylene chloride solution (M1) was cooled until the temperature inside the reactor reached 10°C. A TMP2024 solution was also prepared separately. The TMP2024 solution was prepared by preparing 148 mL of 1.63 N aqueous potassium hydroxide (15.7 g of 86% potassium hydroxide), cooling it to below room temperature, and then adding hydrosulfite (0.22 g) as an antioxidant and bisphenol TMP2024 (30.8 g) and completely dissolving it. After cooling, the entire TMP2024 solution was added to the methylene chloride solution (M1), and 1.7 mL of aqueous triethylamine (7% by volume) was added with stirring. Stirring was continued for 2 hours. The reaction mixture obtained after stirring was diluted with 0.83 L of methylene chloride and 0.08 L of water and washed (first wash). After this first wash, the lower layer was separated and further washed (second wash) once with 0.23 L of water, once with 0.03 N hydrochloric acid, and three times with 0.23 L of water. After this second washing, the obtained methylene chloride solution (M2) was added dropwise to methanol with stirring, and the resulting reprecipitate was filtered and dried to obtain a PC polymer (PC-1) having the following structure.

[0280] (Identification of PC polymer) The PC polymer (PC-1) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.48 dL / g. The structure and composition of the PC polymer (PC-1) obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0281]

[0282] The PC polymer (PC-1) according to Synthesis Example 1 was a polymer containing repeating units [OCTMC-CF] derived from the oligomer OCTMC-CF and repeating units [TMP2024] derived from bisphenol TMP2024. The PC polymer (PC-1) contained, as repeating units [TMP2024], repeating units in which n in the chemical formula of the PC polymer (PC-1) was 18, repeating units in which n was 20, and repeating units in which n was 22. In the PC polymer (PC-1), the compositional ratio (molar ratio) of the repeating units [OCTMC-CF] to the repeating units [TMP2024] was 6:4 ([OCTMC]:[TMP2024]=6:4). In addition, when a repeating unit in which n is 18 is considered to have a structure represented by formula (1), a repeating unit in which n is 20 is considered to have a structure represented by formula (11), and a repeating unit in which n is 22 is considered to have a structure represented by formula (12), the difference in carbon number L １１ -L １ is 2, and the difference in the number of carbon atoms is L １２ -L １１ is 2, and the difference in the number of carbon atoms is L １２ -L １ But it was 4.

[0283] Synthesis Example 2 PC Polymer (PC-2) (Synthesis of PC Polymer) Synthesis Example 2 was carried out in the same manner as Synthesis Example 1, except that the oligomer OCTMC-CF in Synthesis Example 1 was changed to the oligomer TMBPTMC-CF (195 mL) of Production Example 7, to obtain a PC polymer (PC-2) having the following structure.

[0284] (Identification of PC polymer) The PC polymer (PC-2) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.47 dL / g. The structure and composition of the obtained PC polymer (PC-2) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0285]

[0286] The PC polymer (PC-2) according to Synthesis Example 2 was a polymer containing repeating units [TMBPTMC-CF] derived from the oligomer TMBPTMC-CF and repeating units [TMP2024] derived from bisphenol TMP2024. The PC polymer (PC-2) contained, as repeating units [TMP2024], repeating units in which n is 18, repeating units in which n is 20, and repeating units in which n is 22 in the chemical formula of the PC polymer (PC-2). In the PC polymer (PC-2), the composition ratio (molar ratio) of the repeating units [TMBPTMC-CF] to the repeating units [TMP2024] was 6:4 ([TMBPTMC-CF]:[TMP2024]=6:4). The difference in carbon number L in the PC polymer (PC-2) １１ -L １ , difference L １２ -L １１ , and the difference L １２ -L １ was the same as that of the PC polymer (PC-1) in Synthesis Example 1.

[0287] Synthesis Example 3 PC Polymer (PC-3) (Synthesis of PC Polymer) Synthesis Example 3 was carried out in the same manner as Synthesis Example 1, except that the oligomer OCTMC-CF in Synthesis Example 1 was changed to the oligomer OCCDE-CF (195 mL) of Production Example 8, to obtain a PC polymer (PC-3) having the following structure.

[0288] (Identification of PC polymer) The PC polymer (PC-3) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.58 dL / g. The structure and composition of the PC polymer (PC-3) obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0289]

[0290] The PC polymer (PC-3) according to Synthesis Example 3 was a polymer containing a repeating unit [OCCDE-CF] derived from the oligomer OCCDE-CF and a repeating unit [TMP2024] derived from bisphenol TMP2024. The PC polymer (PC-3) contained, as the repeating unit [TMP2024], a repeating unit in which n is 18 in the chemical formula of the PC polymer (PC-3), a repeating unit in which n is 20, and a repeating unit in which n is 22. In the PC polymer (PC-3), the composition ratio (molar ratio) of the repeating unit [OCCDE-CF] to the repeating unit [TMP2024] was 6:4 ([OCCDE-CF]:[TMP2024]=6:4). The difference in carbon number L in the PC polymer (PC-3) １１ -L １ , difference L １２ -L １１ , and the difference L １２ -L １ was the same as that of the PC polymer (PC-1) in Synthesis Example 1.

[0291] Synthesis Example 4 PC Polymer (PC-4) (Synthesis of PC Polymer) Synthesis Example 4 was carried out in the same manner as Synthesis Example 1, except that the oligomer OCTMC-CF in Synthesis Example 1 was changed to the oligomer TMBPCDE-CF (215 mL) of Production Example 9, to obtain a PC polymer (PC-4) having the following structure.

[0292] (Identification of PC polymer) The PC polymer (PC-4) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.59 dL / g. The structure and composition of the obtained PC polymer (PC-4) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0293]

[0294] The PC polymer (PC-4) according to Synthesis Example 4 was a polymer containing a repeating unit [TMBPCDE-CF] derived from the oligomer TMBPCDE-CF and a repeating unit [TMP2024] derived from the bisphenol TMP2024. The PC polymer (PC-4) contained, as the repeating unit [TMP2024], a repeating unit in which n is 18 in the chemical formula of the PC polymer (PC-4), a repeating unit in which n is 20, and a repeating unit in which n is 22. In the PC polymer (PC-4), the composition ratio (molar ratio) of the repeating unit [TMBPCDE-CF] to the repeating unit [TMP2024] was 6:4 ([TMBPCDE-CF]:[TMP2024]=6:4). The difference in carbon number L in the PC polymer (PC-4) １１ -L １ , difference L １２ -L １１ , and the difference L １２ -L １ was the same as that of the PC polymer (PC-1) in Synthesis Example 1.

[0295] Synthesis Example 5 PC Polymer (PC-5) (Synthesis of PC Polymer) Synthesis Example 5 was carried out in the same manner as Synthesis Example 1, except that the oligomer OCTMC-CF in Synthesis Example 1 was changed to the oligomer CHZ-CF (223 mL) of Production Example 11, to obtain a PC polymer (PC-5) having the following structure.

[0296] (Identification of PC polymer) The PC polymer (PC-5) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.54 dL / g. The structure and composition of the obtained PC polymer (PC-5) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0297]

[0298] The PC polymer (PC-5) according to Synthesis Example 5 was a polymer containing repeating units [CHZ-CF] derived from oligomer CHZ-CF and repeating units [TMP2024] derived from bisphenol TMP2024. The PC polymer (PC-5) contained, as repeating units [TMP2024], repeating units in which n is 18, repeating units in which n is 20, and repeating units in which n is 22 in the chemical formula of the PC polymer (PC-5). In the PC polymer (PC-5), the composition ratio (molar ratio) of the repeating units [CHZ-CF] and the repeating units [TMP2024] was 6:4 ([CHZ-CF]:[TMP2024]=6:4). The difference in carbon number L in the PC polymer (PC-5) １１ -L １ , difference L １２ -L １１ , and the difference L １２ -L １ was the same as that of the PC polymer (PC-1) in Synthesis Example 1.

[0299] Synthesis Example 6 PC Polymer (PC-6) (Synthesis of PC Polymer) Synthesis Example 6 was carried out in the same manner as Synthesis Example 1, except that the oligomer OCTMC-CF in Synthesis Example 1 was changed to the oligomer CHA-CF (199 mL) of Production Example 10, and that the bisphenol TMP2024 (30.8 g) in the preparation of the TMP2024 solution was changed to bisphenol TMP2024 (15.4 g) and 2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane (11.3 g), thereby obtaining a PC polymer (PC-6) having the following structure.

[0300] (Identification of PC polymer) The PC polymer (PC-6) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.75 dL / g. The structure and composition of the obtained PC polymer (PC-6) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0301]

[0302] The PC polymer (PC-6) according to Synthesis Example 6 was a polymer containing repeating units [CHA-CF] derived from bisphenol (2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane) in the oligomer CHA-CF and TMP2024 solution, and repeating units [TMP2024] derived from bisphenol TMP2024. The PC polymer (PC-6) contained, as repeating units [TMP2024], repeating units in which n is 18, repeating units in which n is 20, and repeating units in which n is 22 in the chemical formula of the PC polymer (PC-6). In the PC polymer (PC-6), the compositional ratio (molar ratio) of the repeating units [CHA-CF] to the repeating units [TMP2024] was 8:2 ([CHA-CF]:[TMP2024]=8:2). The difference in carbon number L in the PC polymer (PC-6) １１ -L １ , difference L １２ -L １１ , and the difference L １２ -L １ was the same as that of the PC polymer (PC-1) in Synthesis Example 1.

[0303] Synthesis Example 7 PC Polymer (PC-7) (Synthesis of PC Polymer) Synthesis Example 7 was carried out in the same manner as Synthesis Example 4, except that bisphenol TMP2024 in Synthesis Example 4 was changed to bisphenol TMP18 (28.5 g) of Production Example 5, to obtain a PC polymer (PC-7) having the following structure.

[0304] (Identification of PC polymer) The PC polymer (PC-7) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.50 dL / g. The structure and composition of the obtained PC polymer (PC-7) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0305]

[0306] The PC polymer (PC-7) according to Synthesis Example 7 was a polymer containing a repeating unit [TMBPCDE-CF] derived from the oligomer TMBPCDE-CF and a repeating unit [TMP18] derived from bisphenol TMP 18. In the PC polymer (PC-7), the composition ratio (molar ratio) of the repeating unit [TMBPCDE-CF] to the repeating unit [TMP18] was 6:4 ([TMBPCDE-CF]:[TMP18]=6:4).

[0307] Synthesis Example 8 PC Polymer (PC-8) (Synthesis of PC Polymer) Synthesis Example 8 was carried out in the same manner as Synthesis Example 5, except that bisphenol TMP2024 in Synthesis Example 5 was changed to bisphenol TMP18 (28.5 g) of Production Example 5, to obtain a PC polymer (PC-8) having the following structure.

[0308] (Identification of PC polymer) The PC polymer (PC-8) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.40 dL / g. The structure and composition of the obtained PC polymer (PC-8) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0309]

[0310] The PC polymer (PC-8) according to Synthesis Example 8 was a polymer containing repeating units [CHZ-CF] derived from oligomer CHZ-CF and repeating units [TMP18] derived from bisphenol TMP18. In the PC polymer (PC-8), the compositional ratio (molar ratio) of the repeating units [CHZ-CF] to the repeating units [TMP18] was 6:4 ([CHZ-CF]:[TMP18]=6:4).

[0311] Synthesis Example 9 PC Polymer (PC-9) (Synthesis of PC Polymer) Synthesis Example 9 was carried out in the same manner as Synthesis Example 1, except that bisphenol TMP2024 in Synthesis Example 1 was changed to bisphenol BisP2024 (27.5 g) obtained in Production Example 4, to obtain a PC polymer (PC-9) having the following structure.

[0312] (Identification of PC polymer) The PC polymer (PC-9) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 0.58 dL / g. The structure and composition of the obtained PC polymer (PC-9) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer consisting of the following repeating units and composition ratio:

[0313]

[0314] The PC polymer (PC-9) according to Synthesis Example 9 was a polymer containing repeating units [OCTMC-CF] derived from oligomer OCTMC-CF and repeating units [BisP2024] derived from bisphenol BisP2024. The PC polymer (PC-9) contained, as repeating units [BisP2024], repeating units in which n in the chemical formula of the PC polymer (PC-9) was 18, repeating units in which n was 20, and repeating units in which n was 22. In the PC polymer (PC-9), the compositional ratio (molar ratio) of the repeating units [OCTMC-CF] to the repeating units [BisP2024] was 6:4 ([OCTMC-CF]:[BisP2024]=6:4).

[0315] Preparation of a Coating Composition Containing a PC Resin, and Fabrication of a Resin Film Example 1 A coating composition was obtained by weighing out 1.1 g of a PC polymer (PC-1) as a PC resin into a sample tube with a screw cap and dissolving it in 6 g of tetrahydrofuran. The resulting coating composition was cast onto a glass plate using an applicator with a gap of 500 μm to form a film of the coating composition. After air-drying for 1 hour, the film of the coating composition was dried under reduced pressure in a vacuum dryer at 50° C. for 8 hours, and then at 110° C. for 8 hours to remove the solvent, thereby obtaining a resin film according to Example 1 having a thickness of 50 μm to 100 μm.

[0316] Example 2 A resin film according to Example 2 was obtained in the same manner as in Example 1, except that the PC polymer (PC-2) was used instead of the PC polymer (PC-1).

[0317] Example 3 A resin film according to Example 3 was obtained in the same manner as in Example 1, except that the PC polymer (PC-3) was used instead of the PC polymer (PC-1).

[0318] Example 4 A resin film according to Example 4 was obtained in the same manner as in Example 1, except that the PC polymer (PC-4) was used instead of the PC polymer (PC-1).

[0319] Example 5 A resin film according to Example 5 was obtained in the same manner as in Example 1, except that the PC polymer (PC-5) was used instead of the PC polymer (PC-1).

[0320] Example 6 A resin film according to Example 6 was obtained in the same manner as in Example 1, except that the PC polymer (PC-7) was used instead of the PC polymer (PC-1).

[0321] Example 7 A resin film according to Example 7 was obtained in the same manner as in Example 1, except that the PC polymer (PC-8) was used instead of the PC polymer (PC-1).

[0322] Comparative Example 1 A resin film according to Comparative Example 1 was obtained in the same manner as in Example 1, except that the PC polymer (PC-9) was used instead of the PC polymer (PC-1).

[0323] [Evaluation of Physical Properties of PC Resin] The physical properties of the PC resin (PC polymer) were evaluated by the following methods. The evaluation results are shown in Table 1.

[0324] <Reduced Viscosity: [ηsp / C]> PC resin was dissolved in methylene chloride as a solvent to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] of this solution was measured using an Ubbelohde viscometer. The reduced viscosity [ηsp / C] of this methylene chloride solution was measured using the Ubbelohde viscometer at a temperature of 20±0.01°C. The flow time of the solvent alone was 72.4 seconds.

[0325] <Viscosity Average Molecular Weight: Mv> The viscosity average molecular weight (Mv) was calculated by dissolving a polycarbonate resin in methylene chloride as a solvent to prepare a polymer solution, measuring the intrinsic viscosity [η] of this solution at 20°C using an Ubbelohde viscometer, and then calculating the viscosity average molecular weight (Mv) using the following Schnell equation: [η] = 1.23 × 10 －５ Mv ０．８３ The intrinsic viscosity [η] was measured using a viscosity measuring device (manufactured by Rigo Co., Ltd., product name: RIGO AUTO VISCOMETER / VRM-052USPC). The polymer solution used for the measurement was prepared by adding 40 mL of methylene chloride to 200 mg of polycarbonate resin and dissolving it.

[0326] <Evaluation of Relative Dielectric Constant and Dielectric Loss Tangent> A square film measuring 60 mm in length and 60 mm in width was cut out from the resin film and conditioned for 24 hours under conditions of room temperature of 22±1°C and relative humidity of 33±5%. Thereafter, the relative dielectric constant Dk and dielectric loss tangent Df were measured at a frequency of 10 GHz using a split cylinder resonator (manufactured by EM Labs) and a network analyzer (manufactured by Keysight Technologies).

[0327] <Evaluation of Glass Transition Temperature> A strip of film 40 mm long and 4 mm wide was cut out from the resin film and measured using a TMA (manufactured by Hitachi High-Tech Science Corporation, product name: TMA7100). Measurement mode: Tensile Temperature conditions: -30°C to 320°C Heating rate: 5°C / min Data processing method: The temperature at the bending point was used as the glass transition temperature Tg.

[0328]

[0329] The dielectric properties and heat resistance of the PC resins according to Examples 1 to 7 were improved compared to the PC resin according to Comparative Example 1.

[0330] When Example 1 is compared with Comparative Example 1, the structure of the bisphenol used in the synthesis of the PC resin is different. The bisphenol TMP2024 used in the synthesis of the PC resin in Example 1 has a long-chain alkyl group (R １ or R in formula (2) ３ phenol ortho position of the monomer having (X in formula (1) １ ~X４ In the structure represented by formula (2), a methyl group is substituted at the phenol ortho-position of the monomer. On the other hand, the bisphenol BisP2024 used in the synthesis of the PC resin according to Comparative Example 1 does not have an alkyl group (methyl group) substituted at the phenol ortho-position. By having a structure similar to that of the PC resin according to Example 1, the dielectric loss tangent Df was significantly reduced and the Tg was increased compared to Comparative Example 1.

[0331] The comparison between Example 4 and Example 6, and the comparison between Example 5 and Example 7 also show that the structures of the bisphenols used in the synthesis of the PC resins are different. Bisphenol TMP2024 used in the synthesis of the PC resins in Examples 4 and 5 has a longer chain alkyl group (R in formula (1)) than bisphenol TMP18 used in the synthesis of the PC resins in Examples 6 and 7. １ or R in formula (2) ３ The PC resins according to Examples 4 and 5, which have a longer chain length, had a lower dielectric loss tangent Df. On the other hand, the PC resins according to Examples 6 and 7, which have a shorter chain length, had a higher Tg and improved heat resistance.

[0332] In a comparison between Example 1 and Example 2, and a comparison between Example 3 and Example 4, the structures of the oligomers used in the synthesis of the PC resins are different. In the oligomer OCTMC-CF used in the synthesis of the PC resin in Example 1 and the oligomer OCCDE-CF used in the synthesis of the PC resin in Example 3, one substituent is bonded to the benzene ring portion of the phenol (R in formula (3)). ２ The numbers p and q are 1. The oligomers OCTMC-CF and OCCDE-CF have a structure represented by formula (30), and the phenol ortho-position (R ２１ and R ２２) is an alkyl group (methyl group). In contrast, in the oligomer TMBPTMC-CF used in the synthesis of the PC resin in Example 2 and the oligomer TMBPCDE-CF used in the synthesis of the PC resin in Example 4, two substituents are bonded to the benzene ring portion of the phenol (R ２ The numbers p and q are 2. The oligomers OCTMC-CF and TMBPCDE-CF have a structure represented by formula (31), and the phenol ortho-position (R ２１ ~R ２４ In this PC copolymer having a repeating unit containing a structure represented by formula (1) or a repeating unit containing a structure represented by formula (2) and a repeating unit containing a structure represented by formula (3), the relative dielectric constant Dk and the dielectric loss tangent Df were lower and the glass transition temperature Tg was higher when the benzene ring moiety of the phenol in the structure represented by formula (3) was tetrasubstituted than when it was disubstituted.

Claims

1. A polycarbonate resin having a structure represented by the following formula (1): (In the formula (1), X １ , X ２ , X ３ and X ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １ , X ２ , X ３ and X ４ at least one selected from the group consisting of is not a hydrogen atom, R １ is a linear alkyl group having 12 to 24 carbon atoms, and * indicates a bond.

2. X in the formula (1) １ and X ３ and each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

3. X in the formula (1) １ and X ３ The polycarbonate resin according to claim 1 or 2, wherein is a methyl group.

4. X in the formula (1) １ , X ２ , X ３ and X ４ and each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

5. X in the formula (1) １ , X ２ , X ３ and X ４ The polycarbonate resin according to claim 4 , wherein is a methyl group.

6. The polycarbonate resin according to any one of claims 1 to 5, further comprising a structure represented by the following formula (11), wherein the structure represented by the formula (1) and the structure represented by the formula (11) are different from each other. (In the formula (11), X １１ , X １２ , X １３ and X １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １１ , X １２ , X １３ and X １４ at least one selected from the group consisting of is not a hydrogen atom, R １１ is a linear alkyl group having 12 to 24 carbon atoms, １ The number of carbon atoms in the linear alkyl group L １ And, R １１ The number of carbon atoms in the linear alkyl group L １１ and * indicates a bond.) 7. R １ The number of carbon atoms in the linear alkyl group L １ is R １１ The number of carbon atoms in the linear alkyl group L １１ The difference in the number of carbon atoms is smaller than L １１ -L １ The polycarbonate resin according to claim 6 , wherein is 1 or more and 4 or less.

8. The polycarbonate resin according to claim 6 or 7, further comprising a structure represented by the following formula (12), wherein the structure represented by the formula (1), the structure represented by the formula (11), and the structure represented by the formula (12) are different from each other. (In the formula (12), X １５ , X １６ , X １７ and X １８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, with the proviso that X １５ , X １６ , X １７ and X １８ at least one selected from the group consisting of is not a hydrogen atom, R １２ is a linear alkyl group having 12 to 24 carbon atoms, １ The number of carbon atoms in the linear alkyl group L １ And, R １１ The number of carbon atoms in the linear alkyl group L １１ And, R １２ The number of carbon atoms in the linear alkyl group L １２ and * indicates a bond.) 9. R １１ The number of carbon atoms in the linear alkyl group L １１ is R １２ The number of carbon atoms in the linear alkyl group L １２ The difference in the number of carbon atoms is smaller than L １２ -L １１ The polycarbonate resin according to claim 8 , wherein is 1 or more and 4 or less.

10. R １ The number of carbon atoms in the linear alkyl group L １ is R １１ The number of carbon atoms in the linear alkyl group L １１ Smaller, R １１ The number of carbon atoms in the linear alkyl group L １１ is R １２ The number of carbon atoms in the linear alkyl group L １２ The difference in the number of carbon atoms is smaller than １２ -L １ The polycarbonate resin according to claim 8 or claim 9, wherein is 2 or more and 8 or less.

11. The polycarbonate resin according to any one of claims 1 to 10, further comprising a structure represented by the following formula (3), wherein the structure represented by formula (1) and the structure represented by formula (3) are different: (In the formula (3), Y is: (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 ring carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 ring carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted bicycloalkylene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted bicycloalkylidene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylidene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), p and q are each independently 0, 1, 2, 3, or 4, and R ２ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, and a plurality of R ２ If there are multiple R ２ are the same or different, and * indicates a bond.) 12. A polycarbonate resin having a structure represented by the following formula (2): (In the formula (2), R ３ is a linear alkyl group having 12 to 24 carbon atoms, and R ４ is a linear alkyl group having 1 to 6 carbon atoms, and * indicates a bond.

13. The polycarbonate resin according to claim 12, further comprising a structure represented by the following formula (3), wherein the structure represented by the formula (2) and the structure represented by the formula (3) are different: (In the formula (3), Y is: (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 ring carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 ring carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted bicycloalkylene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted bicycloalkylidene group having 4 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted tricycloalkylidene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), p and q are each independently 0, 1, 2, 3, or 4, and R ２ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, and a plurality of R ２ If there are multiple R ２ are the same or different, and * indicates a bond.) 14. The polycarbonate resin according to claim 11 or 13, wherein Y in formula (3) is a 1,1-cyclododecylidene group, a 1,1-cyclohexylidene group, or a 3,3,5-trimethyl-1,1-cyclohexylidene group.

15. R in the formula (3) ２ is a methyl group, and p and q are each independently 1 or 2, or R ２ The polycarbonate resin according to any one of claims 11, 13 and 14, wherein is a cyclohexyl group, and p and q are 1.

16. An insulating material comprising the polycarbonate resin according to any one of claims 1 to 15.

17. An electronic substrate comprising the polycarbonate resin of any one of claims 1 to 15.

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