Resin composition for low dielectric materials, film for laminated substrates, laminated substrate, method for manufacturing a resin composition for low dielectric materials, method for manufacturing a film for laminated substrates, and method for manufacturing a laminated substrate.

Abstract

Provided are: a resin composition which has a low dielectric constant, a low dielectric loss tangent, high transparency, high solubility and high heat resistance and which can be advantageously used as a low dielectric material; a film for a layered substrate, which is obtained using the resin; a layered substrate; and methods for producing these. The present invention is: a resin composition for a low dielectric material, the composition containing a triazine compound having a specific repeating unit; a film for a layered substrate; a layered substrate; a method for producing a resin composition for a low dielectric material; a method for producing a film for a layered substrate; and a method for producing a layered substrate.

Description

[Technical Field]

[0001] The present invention relates to a resin composition for low dielectric materials containing a triazine compound for use as a low dielectric material in electronic devices and the like, a film for laminated substrates, a laminated substrate, a method for producing a resin composition for low dielectric materials, a method for producing a film for laminated substrates, and a method for producing a laminated substrate. This application claims priority based on Japanese Patent Application No. 2021-050694, filed in Japan on March 24, 2021, and the contents of that application are incorporated herein by reference. [Background technology]

[0002] Among resin materials, aromatic polyethers are widely used in the automotive and machinery sectors as so-called engineering resins because they have excellent heat resistance and relatively good mechanical strength. Furthermore, development is underway to create novel structures that offer even better engineering resins, achieving both superior heat resistance and thermal stability.

[0003] Patent Document 1 discloses polymers containing alicyclic and triazine structures, as well as transparent materials containing such polymers. This technology aims to provide polymers having a triazine structure that can be used in transparent materials with high heat resistance.

[0004] Meanwhile, as society's communication infrastructure transitions to 5G, high-frequency electromagnetic waves such as microwaves and millimeter waves used in electronic devices are attracting attention, and research into their applications in the communications field and vehicle radar is progressing. Devices using high-frequency electromagnetic waves require low dielectric constant and low dielectric loss tangent for components such as substrates, resonators, filters, and antennas. At the same time, the materials used for these components must also possess a variety of mechanical properties, such as physical strength and thermal properties. Currently, materials that satisfy these properties include resin materials with added ceramic fillers. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Patent No. 5759302 [Overview of the project] [Problems that the invention aims to solve]

[0006] On the other hand, research is underway on organic materials, particularly resin materials, that possess excellent properties for application in electronic devices and components in the high-frequency range. Among these, materials with low dielectric properties and materials with low dielectric loss tangents, which can be used in insulating components and printed circuit boards, are in particularly high demand.

[0007] The inventors searched for resin materials with excellent properties, specifically those with low dielectric properties and low dielectric loss tangents. As a result, they discovered that triazine compounds with a specific structure possess not only excellent mechanical and thermal properties, but also excellent properties as low dielectric constant and low dielectric loss tangent materials, leading to the completion of the present invention.

[0008] This invention has been made in view of the above circumstances, and aims to provide a resin composition that can be suitably used as a low dielectric material because it has a low dielectric constant, a low dielectric loss tangent, high transparency, high solubility, and high heat resistance, as well as a film for laminated substrates using the same, a laminated substrate, and a method for manufacturing the same. [Means for solving the problem]

[0009] To solve the above problems, the present invention has the following aspects. [1] A resin composition for low dielectric materials comprising a triazine compound having repeating units represented by the following general formula (1). [ka] [In formula (1), n ​​is an integer of 2 or more, and R represents a linear, branched, or cyclic aliphatic group, a linear, branched, or cyclic aliphatic oxy group, a linear, branched, or cyclic aliphatic secondary amino group, an aromatic group or a substituted aromatic group, an aromatic oxy group or a substituted aromatic oxy group, an aromatic secondary amino group or a substituted aromatic secondary amino group, a fluorinated aliphatic group, a fluorinated aliphatic oxy group, a fluorinated aliphatic secondary amino group, a fluorinated aromatic group, a fluorinated aromatic oxy group, or a fluorinated aromatic secondary amino group. Ar represents a linear, branched, or cyclic aliphatic group, or a divalent aromatic group having a fluorinated linear, branched, or cyclic aliphatic group.] [2] The resin composition for low dielectric materials, wherein the triazine compound is represented by any of the following general formulas (2) to (4) in the general formula (1) and Ar is represented by any of the following general formulas (5) to (15) in the general formula (1). [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [3] The resin composition for low dielectric materials comprising a triazine compound having an average degree of polymerization of the repeating unit represented by n in the general formula (1) of 2 to 600. [4] The triazine compound has a dielectric constant (D k ) is 2.7 or less, and / or dielectric loss tangent (D f The resin composition for low dielectric materials, wherein the ratio of ) is 0.004 or less. [5] The resin composition for low dielectric materials, wherein the triazine compound has a glass transition temperature of 160°C or higher. [6] The resin composition for low dielectric materials comprising the triazine compound and an epoxy resin, a bismaleimide resin, or a cyanate resin. [7] The resin composition for low dielectric materials, further comprising an inorganic filler, a modifier, or a flame retardant. [8] The resin composition for low dielectric materials used in equipment that transmits and receives high-frequency electromagnetic waves with a frequency of 0.1 to 500 GHz. [9] A resin composition for low dielectric materials used in printed circuit boards, flexible printed circuit boards, encapsulants for electronic components, resist inks, conductive pastes, insulating materials, or insulating boards.

[10] A film for a laminated substrate having an insulating material comprising the resin composition for low dielectric material described above on at least one surface.

[11] A laminated substrate comprising two or more of the aforementioned laminated substrate films.

[12] A method for producing the resin composition for low dielectric materials, A method for producing a resin composition for low dielectric materials, comprising mixing a compound represented by the following general formula (16) and a compound represented by the following general formula (17), and polymerizing them to obtain a triazine compound represented by the following general formula (18). [ka] [ka] [ka] [In formulas (16), (17), and (18), n is an integer greater than or equal to 2, and R represents a linear, branched, or cyclic aliphatic group, a linear, branched, or cyclic aliphatic oxy group, a linear, branched, or cyclic aliphatic secondary amino group, an aromatic group or a substituted aromatic group, an aromatic oxy group or a substituted aromatic oxy group, an aromatic secondary amino group or a substituted aromatic secondary amino group, a fluorinated aliphatic group, a fluorinated aliphatic oxy group, a fluorinated aliphatic secondary amino group, a fluorinated aromatic group, a fluorinated aromatic oxy group, or a fluorinated aromatic secondary amino group. Ar represents a linear, branched, or cyclic aliphatic group, or a divalent aromatic group having a fluorinated linear, branched, or cyclic aliphatic group.]

[13] A method for producing a resin composition for a low dielectric material used as an insulating material between layers of a laminated substrate, A method for producing the resin composition for low dielectric materials, comprising mixing the triazine compound, epoxy resin, bismaleimide resin or cyanate resin, a curing accelerator, and an organic solvent.

[14] A method for producing the resin composition for low dielectric materials, further comprising mixing an inorganic filler, a modifier, or a flame retardant.

[15] A method for manufacturing a laminated substrate film, comprising applying an insulating material containing the resin composition for low dielectric material described above to at least one surface of a resin film.

[16] A method for manufacturing a laminated substrate, comprising stacking two or more of the aforementioned films for the laminated substrate.

[0010] Furthermore, the present invention also has the following embodiments in another aspect. [1A] A resin composition for low dielectric materials comprising a triazine compound having repeating units represented by the following general formula (1A). [ka] [In formula (1A), n is an integer of 2 or more, and R represents a linear, branched, or cyclic aliphatic group, a linear, branched, or cyclic aliphatic oxy group, a linear, branched, or cyclic aliphatic secondary amino group, an aromatic group or a substituted aromatic group, an aromatic oxy group or a substituted aromatic oxy group, an aromatic secondary amino group or a substituted aromatic secondary amino group, a fluorinated aliphatic group, a fluorinated aliphatic oxy group, a fluorinated aliphatic secondary amino group, a fluorinated aromatic group, a fluorinated aromatic oxy group, or a fluorinated aromatic secondary amino group. Ar represents a linear, branched, or cyclic aliphatic group, or a divalent aromatic group having a fluorinated linear, branched, or cyclic aliphatic group.] [2A] The resin composition for low dielectric materials wherein the triazine compound is a compound represented by the following general formula (2A), or Ar in formula (1A) is represented by the following general formula (11A) and R is represented by any of the following general formulas (3A) to (5A). [ka] [In formula (2A), R1 represents a structure represented by one of the following general formulas (3A) to (5A). R2 represents a structure represented by one of the following general formulas (6A) to (10A) or (12A).] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [3A] The resin composition for low dielectric materials comprising a triazine compound having an average degree of polymerization of the repeating unit represented by n in the general formula (1A) of 2 to 100. [4A] The triazine compound has dielectric constant D k The dielectric loss tangent D is 2.7 or less. f The resin composition for low dielectric materials, wherein the ratio is 0.004 or less. [5A] The resin composition for low dielectric materials, wherein the triazine compound has a glass transition temperature of 160°C or higher. [6A] The resin composition for low dielectric materials comprising the triazine compound and the epoxy resin. [7A] The resin composition for low dielectric materials, further comprising an inorganic filler, a modifier, or a flame retardant. [8A] A resin composition for the low dielectric material described above, used in equipment that transmits and receives high-frequency electromagnetic waves with a frequency of 0.1 to 500 GHz. [9A] A resin composition for low dielectric materials used in printed circuit boards, flexible printed circuit boards, encapsulants for electronic components, resist inks, conductive pastes, insulating materials, or insulating boards. [10A] A film for a laminated substrate having an insulating material comprising the resin composition for low dielectric material described above on at least one surface. [11A] A laminated substrate comprising two or more of the above-mentioned films for laminated substrates. [12A] A method for producing a resin composition for low dielectric materials, comprising mixing a compound represented by the following general formula (13A) and a compound represented by the following general formula (14A) and polymerizing them to obtain a triazine compound represented by the following general formula (15A). [ka] [ka] [ka] [In formulas (13A), (14A), and (15A), R represents a linear, branched, or cyclic aliphatic group, a linear, branched, or cyclic aliphatic oxy group, a linear, branched, or cyclic aliphatic secondary amino group, an aromatic group or a substituted aromatic group, an aromatic oxy group or a substituted aromatic oxy group, an aromatic secondary amino group or a substituted aromatic secondary amino group, a fluorinated version of the above aliphatic group, a fluorinated version of the above aliphatic oxy group, a fluorinated version of the above aliphatic secondary amino group, a fluorinated version of the above aromatic group, a fluorinated version of the above aromatic oxy group, or a fluorinated aromatic secondary amino group. Ar represents a linear, branched, or cyclic aliphatic group, or a divalent aromatic group having a fluorinated linear, branched, or cyclic aliphatic group.] [13A] A method for producing a resin composition for a low dielectric material used as an insulating material between layers of a laminated substrate, comprising mixing the triazine compound, epoxy resin, curing accelerator and organic solvent. [14A] A method for producing the resin composition for low dielectric materials, further comprising mixing an inorganic filler, a modifier, or a flame retardant. [15A] A method for manufacturing a laminated substrate film, comprising applying an insulating material containing the resin composition for low dielectric material described above to at least one surface of a resin film. [16A] A method for manufacturing a laminated substrate, comprising stacking two or more of the aforementioned films for the laminated substrate. [Effects of the Invention]

[0011] According to the present invention, a resin composition that can be suitably used as a low dielectric material due to its low dielectric constant, low dielectric loss tangent, high transparency, high solubility, and high heat resistance, as well as a film for laminated substrates using the same, a laminated substrate, and a method for manufacturing the same, can be obtained. [Modes for carrying out the invention]

[0012] The resin composition for low dielectric materials and the method for producing the same according to the present invention will be described below with reference to embodiments. However, the present invention is not limited to the following embodiments.

[0013] (Resin composition for low dielectric materials) The resin composition for low dielectric materials of this embodiment contains a specific triazine compound. Here, a low dielectric material is a material with a low dielectric constant and / or a low dielectric loss tangent. That is, it is a low dielectric constant material or a low dielectric loss tangent material, but hereinafter it will be collectively referred to as a "low dielectric material." The definitions of the measurement conditions for dielectric constant and dielectric loss tangent will be described later. Low dielectric materials are materials used in electronic devices or electronic components where a low dielectric constant and / or a low dielectric loss tangent is required. Parts where a low dielectric constant and / or a low dielectric loss tangent is required are, for example, parts where insulation is required, such as insulating parts such as insulating plates and insulating parts of printed circuit boards. Printed circuit boards also include flexible printed circuit boards. The compounds contained in the material of this embodiment have a low dielectric constant and / or a low dielectric loss tangent, especially at high frequencies, so it is preferable to use them in electronic components and electronic devices, especially high-frequency compatible electronic components and electronic devices.

[0014] The triazine compound contained in the resin composition of this embodiment has a repeating unit represented by the following general formula (1). [ka]

[0015] Here, in formula (1), n ​​is an integer of 2 or more, and R represents a linear, branched, or cyclic aliphatic group, a linear, branched, or cyclic aliphatic oxy group, a linear, branched, or cyclic aliphatic secondary amino group, an aromatic group or a substituted aromatic group, an aromatic oxy group or a substituted aromatic oxy group, an aromatic secondary amino group or a substituted aromatic secondary amino group, a fluorinated aliphatic group, a fluorinated aliphatic oxy group, a fluorinated aliphatic secondary amino group, a fluorinated aromatic group, a fluorinated aromatic oxy group, or a fluorinated aromatic secondary amino group. Here, a substituent broadly refers to a group of a different group from the group (atomic group) to which it is bonded, and which can be bonded by replacing some of the atoms (preferably hydrogen) of the group to which it is bonded. An aromatic group broadly refers to a group that contains the structure of an aromatic compound or a partially substituted compound. An aliphatic group broadly refers to a group that contains the structure of an organic compound that does not have aromaticity or a partially substituted compound. In the formula, n represents the number of repeating units of the structure represented by formula (1), and is an integer of 2 or more. As will be described later, the average degree of polymerization (n) of the triazine compounds contained in the resin composition for low dielectric materials of this embodiment is the average degree of polymerization, and the value of the average degree of polymerization is preferably 2 to 600. Examples of the above aliphatic groups include those with 1 to 14 carbon atoms. Specifically, examples of the above aliphatic groups include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, cyclobutyl group, cyclopentyl group, or cyclohexyl group. Examples of aliphatic oxy groups include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, cyclobutoxy group, cyclopentyloxy group, or cyclohexyloxy group. Examples of aliphatic secondary amino groups include dimethylamino group, diethylamino group, methylethylamino group, dipropylamino group, methylpropylamino group, dibutylamino group, methylbutylamino group, N-methylcyclohexylamino group, dicyclohexylamino group, pyrrolidino group, piperidino group, or morpholino group. Aromatic groups with 6 to 18 carbon atoms are preferred. Specifically, examples of aromatic groups include phenyl, methylphenyl, dimethylphenyl, cumenyl, mesityl, tert-butylphenyl, or naphthyl groups. Examples of aromatic oxy groups include phenoxy, methylphenoxy, dimethylphenoxy, or naphthoxy groups. Examples of aromatic secondary amino groups include N-methylanilino and diphenylamino groups. Examples of fluorinated aromatic groups include trifluoromethylphenyl, bistrifluoromethylphenyl, trifluoromethylphenoxy, bistrifluoromethylphenoxy, N-methyltrifluoromethylanilino, or trifluoromethyldiphenylamino groups. Ar represents a linear, branched, or cyclic aliphatic group, or a divalent aromatic group having a fluorinated linear, branched, or cyclic aliphatic group. Aliphatic groups include methyl, trifluoromethyl, methylene, ethylene, trimethylene, tetramethylene, propylene, butylene, pentylene, hexylene, cyclopentalene, cyclohexylene, isopropylidene, cyclopentylidene, cyclohexylidene, methylcyclohexylidene, dimethylcyclohexylidene, trimethylcyclohexylidene, cyclooctylidene, cyclododecylidene, and hexafluoroisopropylidene.

[0016] In other words, the resin containing the triazine compound of this embodiment is an aliphatic group-containing triazine resin when R is an aliphatic group, and a fluorinated aliphatic group-containing triazine resin when R is an aliphatic group that has been fluorinated. The degree to which R is fluorinated can be broadly selected, ranging from one carbon bond site in R to all carbon bond sites other than those bonded to the target group. For example, if R is a methyl group, 1 to 3 of the hydrogen atoms of the methyl group may be substituted with fluorine, but 2 to 3 are preferred. Note that R in formula (1) may be the same substituent or different substituents. The above-described chemical structure of the triazine compound contained in the resin composition of this embodiment can be measured by infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (NMR), for example. 1 H-NMR, 13 C-NMR, 19 It can be identified by 1F-NMR or elemental analysis, etc.

[0017] Examples of arylene groups of Ar can be appropriately selected from various divalent aromatic residues obtained by abstracting a total of two hydrogen atoms or other substituents from the aromatic ring in various aromatic compounds or aromatic ring-containing compounds. For example, various aromatic residues obtained by abstracting two phenolic hydroxyl groups from various divalent phenols can be cited. Examples of arylene groups can be appropriately selected from various phenylene groups, naphthylene groups, and biphenylene groups. Other alkyl groups or aryl groups may be bonded to Ar.

[0018] In this embodiment, the triazine compound is one in which R in the following general formula (1) represents a structure represented by any of the following general formulas (2) to (4). Alternatively, Ar may be a compound represented by a structure represented by any of the following general formulas (5) to (15).

[0019] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0020] Here, for the compound represented by the general formula (16) with R substituted, formula (2) is sometimes represented as DCPT, formula (3) as DCPpT, and formula (4) as DCHAT. Regarding the structure of Ar mentioned above, for divalent bisphenol (HO-Ar-OH) having OH groups at both ends of formulas (5) to (15), formula (5) is sometimes represented as BisA, formula (6) as BisZ, formula (7) as BisP3MZ, formula (8) as BisPHTG, formula (9) as BisPCDE, formula (10) as HPTM5I, formula (11) as BisC, formula (12) as BisTMP, formula (13) as BisCHP, formula (14) as BisAF, and formula (15) as BPFL. When R and Ar of these structures are used in the resin composition for low dielectric materials of this embodiment, a resin composition for low dielectric materials can be obtained that contains a triazine compound with particularly low dielectric constant, low dielectric loss tangent, high transparency, high solubility, and high heat resistance.

[0021] In this embodiment, the triazine compound preferably has an average degree of polymerization of the repeating unit represented by n in the general formula (1) of 2 to 600. When the average degree of polymerization of the repeating unit represented by n is 2 to 600, a compound with a suitable molecular weight can be obtained for use as a resin composition for low dielectric materials. Furthermore, an average degree of polymerization of 2 to 300 is also preferable. Alternatively, the average degree of polymerization may be 2 to 100. The molecular weight of the triazine compound of the present embodiment is, as a guide, when R in the above formulas (2) to (4) is used, the number average molecular weight M n is 3×10 3 to 40×10 4 , and the weight average molecular weight M w is 6×10 3 to 80×10 4 is preferably. The molecular weight of the compound of the present embodiment can be measured using gel permeation chromatography (GPC) or the like. From this molecular weight and the structure of the above-described compound, the average degree of polymerization can be determined.

[0022] The triazine compound of the present embodiment may have a dielectric constant (D k ) of 2.7 or less and / or a dielectric tangent (D f ) of 0.006 or less. Also, it is preferable that the dielectric tangent (D f ) is 0.004 or less. Here, the dielectric constant (D k ) and the dielectric tangent (D f ) are values measured with an existing dielectric property measuring device. As the existing dielectric property measuring device, for example, a cavity resonator type can be used. Also, the triazine compound of the present embodiment preferably has a dielectric constant (D k ) of 2.6 or less, and more preferably a dielectric tangent (D f ) of 0.003 or less.

[0023] The triazine compound of the resin composition for a low dielectric material of the present embodiment preferably has a glass transition temperature of 160°C or higher, and more preferably 200°C or higher. Also, it is preferable that the 5% thermal decomposition temperature is 340 to 500°C. The glass transition temperature of the triazine compound of the resin composition for a low dielectric material of the present embodiment can be measured using differential scanning calorimetry (DSC), thermomechanical analysis (TMA), dynamic viscoelasticity measurement (DMA), etc. The 5% thermal decomposition temperature of the resin composition for low dielectric materials in this embodiment is obtained by measuring the weight loss temperature. The weight loss temperature can be measured using, for example, thermogravimetric analysis (TGA).

[0024] The resin composition for low dielectric materials of this embodiment may also preferably contain the triazine compound and an epoxy resin, bismaleimide resin, or cyanate resin. By including an epoxy resin, bismaleimide resin, or cyanate resin, a resin composition for low dielectric materials with excellent heat resistance and dielectric properties can be obtained.

[0025] While there are no particular limitations on the epoxy resin, examples of epoxy resins that yield cured products with excellent heat resistance include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, bisphenol sulfide type epoxy resin, biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, polyhydroxynaphthalene type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolac type epoxy resin, triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin, dicyclopentadiene-phenol addition reaction type epoxy resin, phenol aralkyl type epoxy resin, biphenyl aralkyl type epoxy resin, biphenyl novolac type epoxy resin, and naphthol novolac. Epoxy resins such as naphthol aralkyl epoxy resins, naphthol-phenol copolymer novolac epoxy resins, naphthol-cresol copolymer novolac epoxy resins, biphenyl-modified phenol epoxy resins (polyvalent phenol epoxy resins in which a phenol skeleton and a biphenyl skeleton are linked by a bismethylene group), biphenyl-modified naphthol epoxy resins (polyvalent naphthol epoxy resins in which a naphthol skeleton and a biphenyl skeleton are linked by a bismethylene group), alkoxy-group-containing aromatic ring-modified novolac epoxy resins (compounds in which a glycidyl group-containing aromatic ring and an alkoxy-group-containing aromatic ring are linked by formaldehyde), phenylene ether epoxy resins, naphthylene ether epoxy resins, aromatic hydrocarbon formaldehyde resin-modified phenol resin epoxy resins, or xanthene epoxy resins may be used. These may be used individually or in combination of two or more types. The bismaleimide resin is not particularly limited, but in terms of obtaining a cured product with excellent heat resistance, for example, diphenylmethane-type bismaleimide resin, metaphenylene-type bismaleimide resin, bisphenol A diphenyl ether-type bismaleimide resin, diphenyl ether-type bismaleimide resin, diphenyl sulfone-type bismaleimide resin, diphenoxybenzene-type bismaleimide resin, and aniline novolac-type bismaleimide resin may be used. These may be used individually or in combination of two or more types. While the cyanate resin is not particularly limited, for example, bisphenol A type cyanate resin, tetramethylbisphenol F type cyanate resin, hexafluorobisphenol A type cyanate resin, bisphenol E type cyanate resin, bisphenol M type cyanate resin, novolac type cyanate resin, and cyclopentadienylbisphenol type cyanate resin may be used, as they yield cured products with excellent heat resistance. These may be used individually or in combination of two or more types.

[0026] The resin composition for low dielectric materials of this embodiment may further preferably contain an inorganic filler, a modifier, or a flame retardant. As inorganic fillers, for example, fused silica, crystalline silica, alumina, silicon nitride, aluminum hydroxide, or magnesium hydroxide may be used. As a modifier, various thermosetting resins and thermoplastic resins can be appropriately selected, but for example, phenoxy resin, polyamide resin, polyimide resin, polyetherimide resin, polyethersulfone resin, polyphenylene ether resin, polyphenylene sulfide resin, polyester resin, polystyrene resin, or polyethylene terephthalate resin, cycloolefin resin, fluororesin, etc. may be used. Flame retardants can be appropriately selected from, for example, halogen compounds, phosphorus-containing compounds, nitrogen-containing compounds, and inorganic flame retardants. Examples include halogen compounds such as tetrabromobisphenol A type epoxy resin and brominated phenol novolac type epoxy resin; trimethyl phosphate, triethyl phosphate, tributyl phosphate, tri-2-ethylhexyl phosphate, tributoxyethyl phosphate, triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate. Phosphorus-containing compounds including phosphate esters such as xylenyl diphenyl phosphate, 2-ethylhexyl diphenyl phosphate, tris(2,6-dimethylphenyl) phosphate, and resorcinol diphenyl phosphate; condensed phosphate ester compounds such as ammonium polyphosphate, polyphosphate amide, red phosphorus, guanidine phosphate, and dialkylhydroxymethylphosphonate; nitrogen-containing compounds such as melamine; inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide, zinc borate, or calcium borate; etc. may also be used.

[0027] The resin composition for low dielectric materials of this embodiment is preferably used in equipment that transmits and receives high-frequency electromagnetic waves with a frequency of 0.1 to 500 GHz. Specifically, the resin composition for low dielectric materials of this embodiment is preferably used in equipment that transmits and receives microwave or millimeter-wave electromagnetic waves. Here, microwaves generally refer to electromagnetic waves with frequencies of 0.25 to 100 GHz, and millimeter waves refer to electromagnetic waves with frequencies of 30 to 300 GHz, and it is even more preferable to use it in equipment that transmits and receives these. The resin composition for low dielectric materials of this embodiment can be suitably used in equipment that uses electromagnetic waves with frequencies such as 60 GHz used in wireless LANs and 75 to 79 GHz used in vehicle radar. The resin composition for low dielectric materials of this embodiment has a sufficiently low dielectric constant and dielectric loss tangent, making it particularly suitable for use with high-frequency electromagnetic waves.

[0028] The resin composition for low dielectric materials of this embodiment is preferably used in printed circuit boards, flexible printed circuit boards, encapsulants for electronic components, resist inks, conductive pastes, insulating materials, or insulating boards. The resin composition for low dielectric materials of this embodiment has sufficiently low dielectric constant and dielectric loss tangent, making it suitable for use in these components. Furthermore, it is particularly suitable for use in these components in equipment that uses high-frequency electromagnetic waves. More specifically, it can be used as a resin composition for copper-clad laminates, an interlayer insulating material for build-up printed circuit boards, or a build-up film. It can also be used as a resin composition for encapsulating electronic components, a resin composition for resist inks, a binder for friction materials, a conductive paste, a resin casting material, an adhesive, or a coating material such as an insulating paint.

[0029] The resin composition for low dielectric materials of this embodiment is preferably used as an insulating material between layers of a laminated substrate. In this case, the resin composition is preferably prepared by mixing the triazine compound, epoxy resin, bismaleimide resin or cyanate resin, a curing accelerator and an organic solvent, as described in the manufacturing method later.

[0030] (Film for laminated substrates) The laminated substrate film of this embodiment has an insulating material containing the resin composition for the low dielectric material on at least one surface. Multiple of these laminated substrate films can be laminated together to form a laminated substrate described later. The film for the laminated substrate consists of a film layer, described later, and an insulating layer having an insulating material. The insulating layer is provided on at least one surface of the film layer by a manufacturing method described later.

[0031] The film layer can be constructed using appropriately selected film materials, such as resin films or metal films. Specifically, it can be formed using polyethylene, polypropylene, polyvinyl chloride, polycycloolefin, polyethylene terephthalate (PET), polyethylene naphthalate, polycarbonate, polyimide, release paper, copper foil, aluminum foil, etc.

[0032] The thickness of the film for the laminated substrate in this embodiment is not particularly limited, but can be selected from a range of 10 to 150 μm, and is preferably in the range of 25 to 50 μm.

[0033] The laminated substrate film of this embodiment may further have a protective film on its surface. The protective film prevents dust and other debris from adhering to the surface of the film layer and insulating layer before use, and prevents scratches from occurring, thereby preventing a decrease in performance such as insulation before use. The constituent material of the protective film may be selected from the same materials as those used for the film layer described above. The thickness of the protective film may be in the range of 1 to 40 μm. Furthermore, the film for the laminated substrate and the protective film may be treated with a matte finish, corona treatment, or release treatment. Furthermore, when the laminated substrate is a conductive laminated substrate or a build-up printed circuit board, and a conductive layer made of a conductor such as metal is laminated with the insulating layer, the combination of the conductive layer and the insulating layer may constitute the film for the laminated substrate.

[0034] The resin composition for low dielectric materials of this embodiment has excellent physical properties, heat resistance, low dielectric constant, and low dielectric loss tangent, and is therefore extremely useful as an insulating material between layers of laminated substrate films in a laminated substrate comprising two or more laminated substrate films. In particular, it is preferable that such an insulating material is manufactured using the resin composition for low dielectric materials and epoxy resin, bismaleimide resin, or cyanate resin as essential components, and further, if necessary, by blending in organic solvents and curing accelerators described later.

[0035] (Laminated substrate) The laminated substrate of this embodiment comprises two or more of the laminated substrate films. Preferably, the laminated substrate is formed by laminating the laminated substrate films. The laminated substrate film may be an intermediate layer or a base layer in the laminated substrate. It may also be used as a layer on which circuits are formed or as a layer on which circuits are not formed. Circuit formation can be carried out by metal plating or the like.

[0036] Furthermore, the laminated substrate of this embodiment can also be a conductive laminated substrate. For example, it can be a laminated substrate comprising an insulating layer made of a prepreg containing the resin composition for low dielectric material and a conductive layer. The insulating prepreg is formed by impregnating a fibrous substrate such as glass cloth, glass nonwoven fabric, aramid paper, aramid cloth, glass mat, or glass roving cloth with the resin composition for low dielectric material to form the insulating layer. The conductive layer can be formed of a metal, such as copper.

[0037] Furthermore, the laminated substrate of this embodiment can also be a build-up printed circuit board type laminated substrate. A build-up printed circuit board type laminated substrate can also be formed by alternately forming an insulating layer made of a resin composition for low dielectric material and a conductive layer plated thereon on a wiring board. The composition and other configurations of the insulating layer and conductive layer can be arbitrarily selected from those described above.

[0038] (Other configurations) The resin composition for low dielectric materials of this embodiment can be used by appropriately mixing in components conventionally known as materials for low dielectric materials. As mentioned above, the resin composition for low dielectric materials in this embodiment has high affinity with epoxy resins, bismaleimide resins, or cyanate resins, and therefore, by mixing it with thermosetting resin-based materials, it can be expected to improve dielectric and thermal properties.

[0039] (Effects of resin compositions for low dielectric materials) The resin composition for low dielectric materials of this embodiment is suitable for use as a low dielectric material because the triazine-containing compound has a low dielectric constant, low dielectric loss tangent, high transparency, high solubility, and high heat resistance. Furthermore, the triazine-containing compound of this embodiment is suitable for use as a printed circuit board because it has a low dielectric constant, low dielectric loss tangent, high transparency, high solubility, and high heat resistance. While very few conventionally known polymer materials achieve both a glass transition temperature of over 200°C and a dielectric loss tangent of less than 0.003, these can be achieved within the preferred range of this embodiment. Furthermore, the triazine-containing compound of this embodiment is particularly suitable for use as a constituent material for high-frequency electronic components and electronic devices because it has a low dielectric constant at high frequencies, a low dielectric loss tangent, high transparency, high solubility, and high heat resistance.

[0040] (Method for manufacturing resin compositions for low dielectric materials) The method for producing the resin composition for low dielectric materials of this embodiment involves mixing a compound represented by the following general formula (16) and a compound represented by the following general formula (17), and polymerizing them to obtain a triazine compound represented by the following general formula (18).

[0041] [ka] [ka] [ka]

[0042] Here, in formulas (16), (17), and (18), n is an integer of 2 or more, and R represents a linear, branched, or cyclic aliphatic group, a linear, branched, or cyclic aliphatic oxy group, a linear, branched, or cyclic aliphatic secondary amino group, an aromatic group or a substituted aromatic group, an aromatic oxy group or a substituted aromatic oxy group, an aromatic secondary amino group or a substituted aromatic secondary amino group, a fluorinated aliphatic group, a fluorinated aliphatic oxy group, a fluorinated aliphatic secondary amino group, a fluorinated aromatic group, a fluorinated aromatic oxy group, or a fluorinated aromatic secondary amino group. Ar represents a linear, branched, or cyclic aliphatic group, or a divalent aromatic group having a fluorinated linear, branched, or cyclic aliphatic group. In the formula, n represents the number of repeating units of the structure represented by formula (18), and is not particularly limited as long as it is an integer of 2 or more.

[0043] The compound of formula (16) is a dichloride in which both ends of the triazine ring of the monomer constituting the compound of formula (18) are substituted with chlorine. The compound of formula (17) is a bisphenol in which both ends of the Ar group of formula (18) are substituted with OH groups.

[0044] The specific manufacturing process involves, for example, mixing the compounds of formula (16) and formula (17), heating them in the presence of an alkali metal compound and an organic solvent to polymerize them and obtain the triazine compound of formula (18).

[0045] Any alkali metal compound can be used as long as it is capable of neutralizing the hydrogen chloride produced by the polymerization of formula (16) and formula (17). Examples of such alkali metal compounds include alkali metal carbonates, bicarbonates, hydroxides, etc., with hydroxides being particularly preferred. Examples of alkali metals include lithium, sodium, potassium, rubidium, or cesium, with sodium or potassium being preferred. Such alkali metal compounds can include sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium hydroxide, or potassium hydroxide, with sodium hydroxide or potassium hydroxide being particularly suitable. These alkali metal compounds may be used individually or in combination of two or more.

[0046] The aforementioned organic solvent can be any solvent that can facilitate the polymerization reaction. Specific examples of organic solvents include, for example, aliphatic compounds, aromatic compounds, and their derivatives, with substituents such as nitro groups, cyano groups, and halogen elements. Specific examples of such organic solvents include nitrobenzene, benzonitrile, methylene chloride, chloroform, 1,4-dioxane, and tetrahydrofuran (THF). These various neutral solvents may be used individually or in combination of two or more.

[0047] A phase transfer catalyst (PTC) may be added to the compound of formula (17) during the reaction. Specific examples of PTCs include quaternary ammonium salts, quaternary phosphonium salts, or crown ethers having alkyl chains. Examples of quaternary ammonium salts include tetrabutylammonium bromide (TBAB) and cetyltrimethylammonium bromide (CTMAB).

[0048] The polymerization temperature can be adjusted as appropriate depending on the compound, additives, and solvent used, but it can usually be carried out at 10 to 100°C. For example, if R in the compound of formula (1) has the structure represented by formula (2), polymerization can be carried out at 20 to 35°C. The polymerization reaction time can also be adjusted as appropriate depending on the components used and the polymerization temperature, but it is usually about 0.1 to 20 hours. For example, if R in the compound of formula (1) has the structure represented by formula (3) or (4), polymerization is preferably carried out at 80 to 100°C.

[0049] As an example of a specific manufacturing process, first, an aqueous solution of an alkali metal compound and PTC are added to the compound of formula (16). Then, the compound of formula (17) and an organic solvent are added. These are vigorously stirred at the polymerization temperature and allowed to react for a sufficient amount of time. After the polymerization reaction is completely finished, the triazine compound of formula (18) is recovered with methanol. After this, further steps such as washing with methanol, drying under reduced pressure, and / or reprecipitation with an organic solvent may be performed.

[0050] (Other additives in the manufacturing process) When the resin composition for low dielectric materials of this embodiment is a resin composition for low dielectric materials used as an insulating material between layers of a laminated substrate, it is preferable that this resin composition for low dielectric materials be manufactured by mixing a triazine compound, an epoxy resin, a bismaleimide resin or a cyanate resin, a curing accelerator and an organic solvent. By manufacturing the resin composition for low dielectric materials with a curing accelerator, the curing reaction proceeds rapidly, making it easy to manufacture as an insulating material. In particular, when the insulating material is used as an insulating layer on the surface of a laminated substrate film, as described later, the insulating layer is formed quickly, making it suitable for industrial manufacturing. By being manufactured by mixing with organic solvents, the resin composition for low dielectric materials becomes a so-called varnish during manufacturing, making it easy to apply to other components as an insulating material. In particular, when the insulating material is used as an insulating layer on the surface of a laminated substrate film, as described later, the coating properties are good when applying it to the surface of the film to form an insulating layer.

[0051] As a curing accelerator, any compound capable of accelerating the curing of the aforementioned compound can be used as appropriate, for example, imidazoles, tertiary amines, tertiary phosphines, or acid anhydrides may be used. The amount added can be appropriately adjusted depending on the composition of the compound, but it is preferably in the range of 0.01 to 2% by mass relative to the total mass of the resin composition for low dielectric materials.

[0052] As the organic solvent, any solvent capable of dissolving the compound and forming a varnish can be appropriately selected. For example, known organic solvents such as alcoholic solvents, ketones, acetate esters, carbitols, aromatic hydrocarbons, dimethylformamide, dimethylacetamide, or N-methylpyrrolidone can be used. Among these, propylene glycol monomethyl ether acetate or methyl ethyl ketone can be preferably used. The amount added can be appropriately adjusted depending on the composition of the compound, but to achieve a varnish-like consistency, it is preferable that the non-volatile content be in the range of 50 to 70% by mass relative to the total mass of the resin composition for low dielectric materials.

[0053] The resin composition for low dielectric materials in this embodiment may also be manufactured by further mixing in an inorganic filler, a modifier, or a flame retardant. Inorganic fillers can include, for example, fused silica, crystalline silica, alumina, silicon nitride, aluminum hydroxide, or magnesium hydroxide. When resin compositions for low dielectric materials are used in applications such as conductive pastes and conductive films, conductive fillers such as silver powder or copper powder can be used as inorganic fillers. Examples of modifiers that can be used include phenoxy resin, polyamide resin, polyimide resin, polyetherimide resin, polyethersulfone resin, polyphenylene ether resin, polyphenylene sulfide resin, polyester resin, polystyrene resin, or polyethylene terephthalate resin, cycloolefin resin, fluororesin, etc. Flame retardants can include, for example, halogen compounds, phosphorus-containing compounds, nitrogen-containing compounds, or inorganic flame retardants.

[0054] (Method of manufacturing film for laminated substrates) The method for manufacturing a laminated substrate film according to this embodiment involves applying an insulating material containing a resin composition for low dielectric materials to at least one surface of a resin film. Specifically, the above manufacturing method involves applying a varnish-like resin composition for low dielectric materials, as described above, to at least one surface of a resin film. Then, the organic solvent is evaporated by heating or blowing hot air to form an insulating layer, thereby enabling the manufacturing process.

[0055] Here, it is preferable that the resin composition for the low dielectric material has a non-volatile content of 30 to 60% by mass, excluding volatile components such as organic solvents. This range is particularly favorable for the coating properties of the compound onto films and for the moldability of films for laminated substrates.

[0056] The thickness of the insulating layer formed is preferably greater than or equal to the thickness of the conductive layer of the circuit board on which the laminated substrate is installed, as will be described later. If the thickness of the conductive layer of the circuit board is usually in the range of 5 to 70 μm, then the thickness of the resin composition layer is preferably 10 to 100 μm.

[0057] (Method of manufacturing a laminated substrate) The manufacturing method of the laminated substrate of this embodiment involves stacking two or more of the aforementioned films for the laminated substrate. When manufacturing a printed circuit board using the laminated substrate of this embodiment, if the film for the laminated substrate is protected by a protective film, these can be removed, and then the layer can be laminated to one or both sides of the circuit board so that it is in direct contact with the circuit board, for example by vacuum lamination. The lamination method may be batch or continuous with a roll. The film and circuit board may also be heated (preheated) before lamination as necessary.

[0058] When manufacturing a conductive laminated substrate, it may be formed by the following procedure. That is, the resin composition for low dielectric material, which has been adjusted to a varnish-like state as described above, is impregnated into a fibrous substrate, and an insulating layer of prepreg, which is a cured product, is obtained by heating at a heating temperature corresponding to the type of solvent used, preferably 50 to 170°C. The fibrous substrate can be paper, glass cloth, glass nonwoven fabric, aramid paper, aramid cloth, matted glass, or glass roving cloth. In this case, it is generally preferable to adjust the mixing ratio of the resin composition for low dielectric material and the fibrous substrate so that the resin content in the prepreg is 20 to 60% by mass. The obtained prepregs are laminated, and a film of a material that will become a conductive layer, such as copper foil, is then layered on top and heated and pressed to obtain the desired conductive plate laminate substrate. Specifically, the heating and pressing method is performed under pressure of 1 to 10 MPa at a temperature of 170 to 250°C. Furthermore, it is preferable to perform the heating and pressing for 10 minutes to 3 hours.

[0059] When using a film for laminated substrates as a build-up printed circuit board, the laminated substrate and printed circuit board may be formed by the following procedure. Specifically, a resin composition for low dielectric material is applied to a wiring board with a circuit formed on it using a spray coating method or a curtain coating method, and then cured. Next, holes such as predetermined through-holes are drilled as needed, then the surface is treated with a roughening agent and washed with hot water to form irregularities, and then plated with a metal such as copper. The plating method is preferably electroless plating or electrolytic plating. As the roughening agent, an oxidizing agent, alkali, or organic solvent can be used. By sequentially repeating these operations as desired, an insulating layer and a conductor layer of a predetermined circuit pattern are alternately built up to form a build-up substrate. However, it is preferable to drill through-holes after forming the outermost insulating layer. Furthermore, it is possible to create a roughened surface and omit the plating process by heating and pressing the resin-coated copper foil, which has been partially cured with the resin composition on copper foil, onto a wiring board with a circuit formed on it at 170-250°C, thereby producing a build-up substrate.

[0060] (Method of manufacturing encapsulating materials for electronic components, etc.) To prepare the resin composition for low dielectric materials of this embodiment as an encapsulant for electronic components, one method involves pre-mixing the resin composition for low dielectric materials, epoxy resin, bismaleimide resin, or cyanate resin, other coupling agents and / or release agents as needed, and other additives and inorganic fillers, and then thoroughly mixing them using an extruder, kneader, rolls, etc., until uniform. When used as a tape-type encapsulant for semiconductors, one method involves heating the resin composition obtained by the above method to produce a semi-cured sheet, forming an encapsulant tape, placing this encapsulant tape on a semiconductor chip, heating it to 100-150°C to soften and mold it, and then completely curing it at 170-250°C.

[0061] To prepare the resin composition for low dielectric materials of this embodiment as a resist ink, one method is to add the resin composition for low dielectric materials, epoxy resin, bismaleimide resin or cyanate resin, and further organic solvents, pigments, talc, and fillers to form a resist ink composition, then apply it to a printed circuit board using a screen printing method, and finally cure the resist ink. Examples of organic solvents used here include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, cyclohexanone, dimethyl sulfoxide, dimethylformamide, dioxolane, tetrahydrofuran, propylene glycol monomethyl ether acetate, or ethyl lactate.

[0062] When the resin composition for low dielectric materials of this embodiment is used as an insulating material, for example, as an insulating material between layers of a semiconductor, one method is to prepare the composition by blending the resin composition for low dielectric materials, epoxy resin, a curing accelerator, and a silane coupling agent, and then applying this to a silicon substrate by spin coating or the like. In this case, since the cured coating film will be in direct contact with the semiconductor, it is preferable to bring the coefficient of thermal expansion of the insulating material close to that of the semiconductor so that cracks do not occur due to differences in coefficient of thermal expansion in high-temperature environments.

[0063] When the resin composition for low dielectric materials of this embodiment is used as a conductive paste, examples include dispersing fine conductive particles in the resin composition for low dielectric materials to create a composition for an anisotropic conductive film, or creating a paste resin composition for circuit connections or an anisotropic conductive adhesive that is liquid at room temperature.

[0064] (Other aspects of this embodiment) Another aspect of this embodiment is that the triazine compound in this embodiment may be a compound represented by the general formula (2A) described above. Here, in formula (2A), R1 represents a structure represented by any of the general formulas (3A) to (5A). R2 represents a structure represented by any of the general formulas (6A) to (10A) or (12A). Also, the Ar in formula (1A) may be a compound represented by formula (11A).

[0065] Another aspect is that the method for producing the resin composition for low dielectric materials in this embodiment involves mixing the compound represented by the general formula (13A) and the compound represented by the general formula (14A) and polymerizing them to obtain a triazine compound represented by the general formula (15A). In this case, the compound of formula (13A) is a dichloride in which both ends of the triazine ring are substituted with chlorine from the monomer constituting the compound of formula (1A). The compound of formula (14A) is a diol in which both ends of the Ar group of formula (1A) are substituted with OH groups. The compound of formula (2A) may also be produced by configuring R in formula (13A) as R1 in formula (2A) and formula (14A) as a diol in which a benzene ring and an OH group are bonded to both ends of R2. [Examples]

[0066] Examples are shown below. However, the present invention is not limited to these examples.

[0067] (Test conditions) The following instruments were used for the synthesis of the samples and the analysis of the synthesized samples. (1) GPC: Tosoh Corporation High-Speed ​​GPC System HLC-8220GPC (Column: Tosoh TSKgel (α-M), Column Temperature: 45°C, Eluent: N-methyl-2-pyrrolidone (NMP) (containing 0.01 mol / L lithium bromide) or tetrahydrofuran (THF), Calibration Curve: Standard polystyrene, Column Flow Rate: 0.2 mL / min) (2) Infrared spectrum (FT-IR): FT / IR-4200, manufactured by JASCO Corporation (3) Nuclear Magnetic Resonance Spectroscopy (NMR): JASCO JNM-ECA500 (4) Thermogravimetric analysis (TGA): Hitachi High-Tech Science Co., Ltd. TG / DTA7300, heating rate 10°C / min (5) Differential scanning calorimetry (DSC): Hitachi High-Tech Science Corporation DSC7000, heating rate 20°C / min (6) Thermomechanical analysis (TMA): Hitachi High-Tech Science Co., Ltd. TMA7100, heating rate 10°C / min (7) Dynamic viscoelasticity measurement (DMA): Hitachi High-Tech Science Co., Ltd. DMS7100, heating rate 2°C / min (8) UV-Vis spectrophotometer: Shimadzu Corporation UV-1800 (10) Refractive index measurement: Metricon Model 2010 / M PRISM COUPLER (11) Dielectric constant and dielectric loss tangent measurement: Dielectric constant and dielectric loss tangent measuring device (cavity resonator type) manufactured by AET Co., Ltd., TE mode and TM mode (10 GHz, 20 GHz) All reagents were commercially available and purified by conventional methods as needed. All reaction solvents were dried and purified by conventional methods as needed.

[0068] (Manufacturing of resin compositions) Among the compounds of formula (1) above, R is of formula (2) and Ar is, The triazine compound of formula (5) (DCPT-BisA, Example 1), The triazine compound of formula (6) (DCPT-BisZ, Example 2), The triazine compound of formula (7) (DCPT-BisP3MZ, Example 3), The triazine compound of formula (8) (DCPT-BisPHTG, Example 4), The triazine compound of formula (9) (DCPT-BisPCDE, Example 5), The triazine compound of formula (10) (DCPT-HPTM5I, Example 6), The triazine compound of formula (11) (DCPT-BisC, Example 7), The triazine compound of formula (12) (DCPT-BisTMP, Example 8), The triazine compound of formula (13) (DCPT-BisCHP, Example 9), The triazine compound represented by formula (14) (DCPT-BisAF, Example 10) Triazine compound of formula (15) (DCPG-BPFL, Example 11) We prepared it.

[0069] Furthermore, among the compounds of formula (1) above, R is formula (3) and Ar is, The triazine compound of formula (5) (DCPpT-BisA, Example 12), The triazine compound of formula (8) (DCPpT-BisPHTG, Example 13), The triazine compound of formula (12) (DCPpT-BisTMP, Example 14), Triazine compound of formula (14) (DCPpT-BisAF, Example 15) We prepared it.

[0070] Furthermore, among the compounds of formula (1) above, R is formula (4) and Ar is, The triazine compound of formula (5) (DCHAT-BisA, Example 16), The triazine compound of formula (8) (DCHAT-BisPHTG, Example 17), The triazine compound of formula (9) (DCHAT-BisPCDE, Example 18), We prepared it.

[0071] (Synthesis of DCPT) The triazine dichloride (DCPT) used in each example was synthesized as follows. In a three-necked flask (500 mL), cyanuric chloride (18.44 g, 0.100 mol) and anhydrous tetrahydrofuran (THF, 200 mL) were placed, and a stirring bar, dropping funnel, nitrogen inlet tube, and thermometer were attached. The mixture was cooled to -10°C. While stirring this THF solution, phenylmagnesium bromide THF solution (1 mol / L, 100 mL, 0.100 mol) was slowly added dropwise from the dropping funnel, taking care not to raise the temperature of the reaction solution. After stirring at -10°C for 2 hours, the mixture was stirred at room temperature for 12 hours. THF was removed from the reaction solution using an evaporator, and the remaining solid was dissolved in chloroform (200 mL) and washed with distilled water. Anhydrous sodium sulfate was added to the chloroform layer and stirred to remove water. Chloroform was removed from the filtrate obtained by suction filtration to obtain the crude product. After purification by sublimation, recrystallization was performed using dry hexane, and white needle-shaped crystals were obtained by drying under reduced pressure at 40°C.

[0072] The synthesized compound yielded 13.1 g, had a yield of 58%, and a melting point of 120°C. The analysis results for this compound using the aforementioned instrument are as follows: FT-IR(KBr,cm -1 ):3047(Ar-H), 1527(C=N), 1258(CN), 770(C-Cl) 1 H-NMR(CDCl3,ppm):8.50(d,2H,o-Ar-H), 7.66(t,1H,p-Ar-H), 7.53(t,2H,m-Ar-H) 13 C-NMR(CDCl3,ppm):175.0, 172.2, 134.9, 132.8, 130.1, 129.2 Elemental analysis (C9H5N3Cl2): Calculated values ​​were C, 47.82%; H, 2.23%; N, 18.59%. Measured values ​​were C, 48.11%; H, 2.43%; N, 18.68%.

[0073] (Synthesis of DCPpT) The triazine dichloride (DCPpT) used in each example was synthesized as follows. In a three-necked flask (300 mL), cyanuric chloride (18.44 g, 0.100 mol) and anhydrous dichloromethane (150 mL) were added, and a dropping funnel, nitrogen inlet tube, and thermometer were attached. The mixture was cooled to 0°C. While stirring this dichloromethane solution, a solution of piperidine (8.52 g, 0.100 mol) dissolved in anhydrous dichloromethane (50 mL) was added dropwise at 0°C, and the mixture was stirred for 2 hours. Next, a solution of N,N-diisopropylethylamine (12.92 g, 0.100 mol) dissolved in dichloromethane (50 mL) was added dropwise while maintaining a temperature of 0-5°C to prevent the reaction solution temperature from rising, and the mixture was stirred for 1 hour. The reaction solution was divided three times with distilled water (300 mL), and anhydrous sodium sulfate was added to the organic layer and stirred. Sodium sulfate was removed by suction filtration, and dichloromethane was removed from the filtrate using an evaporator to obtain a pale yellow crude product. Recrystallization was performed using a hexane / chloroform mixed solvent to obtain white granular crystals, which were then dried under reduced pressure at 40°C.

[0074] The synthesized compound yielded 10.72 g, had a yield of 46%, and a melting point of 90-91°C. The analysis results for this compound using the aforementioned instrument are as follows: FT-IR (KBr, cm) -1 ):2940-2860(CH), 1552(C=N), 1170(CN), 842(C-Cl) 1 H-NMR (CDCl3, ppm): 3.82(t,4H,CH2), 1.74-1.70(m,2H,CH2), 1.67-1.63(m,4H,CH2) 13 C-NMR(CDCl3,ppm):170.2, 163.6, 45.4,25.7, 24.3 Elemental analysis (C8H 10 N4Cl2): Calculated values ​​were C, 41.22%; H, 4.32%; N: 24.04%, while measured values ​​were C, 41.01%; H, 4.68%; N: 24.30%.

[0075] (Synthesis of DCHAT) The triazine dichloride (DCHAT) used in each example was synthesized as follows. 18.44 g, 0.100 mol cyanuric chloride and 50 mL of anhydrous THF were added to a 300 mL three-necked flask. A dropping funnel, nitrogen inlet tube, and thermometer were attached, and the mixture was cooled to 0°C. A solution of dicyclohexylamine (18.13 g, 0.100 mol) dissolved in 30 mL of THF was added dropwise at 0°C, and the mixture was stirred for 2 hours. A solution of sodium carbonate (5.30 g, 0.050 mol) dissolved in 30 mL of distilled water was added dropwise at 0-5°C, taking care not to raise the temperature of the reaction solution, and the mixture was stirred for 1 hour. The reaction solution was separated with saturated brine, and anhydrous sodium sulfate was added to the organic layer and stirred to dehydrate. The crude product was obtained by removing THF from the filtrate obtained by suction filtration. Recrystallization was performed twice using a hexane / chloroform mixed solvent, and the resulting white columnar crystals were dried under reduced pressure at 50°C.

[0076] The synthesized compound yielded 11.3 g, had a yield of 34%, and a melting point of 167-168°C. The analysis results for this compound using the aforementioned instrument are as follows: FT-IR (KBr, cm) -1 ):2923(CH), 1562(C=N), 1227(CN), 793(C-Cl) 13 C-NMR (CDCl3,ppm): 169.0, 164.0, 56.8, 29.7, 26.1, 25.4. Elemental analysis (C 15 H 22 N4Cl2): The calculated values ​​were C, 54.72%; H, 6.73%; N, 17.02%, while the measured values ​​were C, 54.68%; H, 6.56%; N, 17.17%.

[0077] (Example 1) The polymer DCPT-BisA from Example 1 was synthesized as follows. Bisphenol A (BisA) (0.571 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed in a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and stirred. A solution of DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous dichloromethane (5.0 mL) was added to the round-bottom flask and vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in THF and poured into methanol to reprecipitation. After recovering the polymer, it was dried under reduced pressure at 100 °C for 12 hours.

[0078] The synthesized compound had a yield of 0.68 g, a yield of 71%, a logarithmic viscosity of 0.94 dL / g (at 30°C in a 0.5 g / dL N-methyl-2-pyrrolidone solution), a number-average molecular weight (Mn) of 82,000, a weight-average molecular weight (Mw) of 279,000, a molecular weight distribution (Mw / Mn) of 3.4, and an average degree of polymerization (n) of 214.

[0079] This polymer was dissolved in N,N-dimethylacetamide (DMAc) and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 40 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3058(Ar-H), 2968(CH), 1560(C=N), 1211(CO), 1173(CN) Elemental analysis (C 24 H 19 N3O2) n Calculated values: C, 75.57%; H, 5.02%; N, 11.02%; Measured values: C, 75.23%; H, 5.18%; N, 10.84% Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, dichloromethane, benzonitrile, γ-butyrolactone, and cyclopentanone. 5% weight loss temperature: 411°C (in air), 419°C (in nitrogen) 10% weight loss temperature: 420°C (in air), 428°C (in nitrogen) Carbonization yield: 33% (in nitrogen, 800°C) Glass transition temperature (Tg): 184°C (DSC), 178°C (TMA), 175°C (DMA), Coefficient of thermal expansion (CTE): 87 ppm / °C Cutoff wavelength: 321nm, transmittance at 400nm: 84% Average refractive index (n): 1.634 (d line), birefringence (Δn): 0.001 (d line), dielectric constant calculated from refractive index (ε): 2.67 (ε=n 2 ) Dielectric constant (Dk): 2.69 (TE mode, 10 GHz), 2.69 (TM mode, 10 GHz), 2.68 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.003 (TE mode, 10 GHz), 0.003 (TM mode, 10 GHz), and 0.003 (TE mode, 20 GHz).

[0080] (Example 2) The polymer DCPT-BisZ of Example 2 was synthesized as follows. 4,4'-cyclohexylidenebisphenol (BisZ) (0.671 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed in a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and the mixture was stirred. A solution of DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous dichloromethane (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and poured into methanol to reprecipitation. After recovering the polymer, it was dried under reduced pressure at 100 °C for 12 hours.

[0081] The synthesized compound had a yield of 0.95 g, a yield of 90%, and a logarithmic viscosity of 1.02 dL / g (at 30°C in a 0.5 g / dL tetrahydrofuran solution).

[0082] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 57 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3057(Ar-H), 2951(CH), 1560(C=N), 1211(CO), 1173(CN) 1 H-NMR(CDCl3,ppm):8.21(d,2H,Ar-H), 7.46(t,1H,Ar-H), 7.35(m,6H,Ar-H), 7.17(d,4H,Ar-H), 2.32(t,4H,CH2), 1.62(m,4H,CH2), 1.54(t,2H,CH2) 13C-NMR(CDCl3,ppm):175.74, 172.96, 149.74, 146.03, 134.55, 133.29, 129.24, 128.61, 128.41, 121.30, 46.09, 37.57, 26.44, 22.98 Elemental analysis (C 27 H 23 N3O2) n Calculated values: C, 76.94%; H, 5.50%; N, 9.97%; Measured values: C, 76.59%; H, 5.86%; N, 10.10% Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, and cyclopentanone. 5% weight loss temperature: 411°C (in air), 421°C (in nitrogen) 10% weight loss temperature: 420°C (in air), 429°C (in nitrogen) Carbonization yield: 25% (in nitrogen, 800°C) Glass transition temperature (Tg): 201°C (DSC), 180°C (TMA), 181°C (DMA), Coefficient of thermal expansion (CTE): 75 ppm / °C Cutoff wavelength: 319nm, transmittance at 400nm: 83% Average refractive index (n): 1.633 (d line), birefringence (Δn): 0.001 (d line), dielectric constant calculated from refractive index (ε): 2.67 (ε=n 2 ) Dielectric constant (Dk): 2.65 (TE mode, 10 GHz), 2.68 (TM mode, 10 GHz), 2.63 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.002 (TE mode, 10 GHz), 0.002 (TM mode, 10 GHz), and 0.003 (TE mode, 20 GHz).

[0083] (Example 3) The polymer DCPT-BisP3MZ of Example 3 was synthesized as follows. 4-[1-(4-hydroxyphenol)-3-methylcyclohexyl]phenol (BisP3MZ) (0.706 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed in a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and stirred. A solution of DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous dichloromethane (5.0 mL) was added to the round-bottom flask and vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and poured into methanol to reprecipitation. After recovering the polymer, it was dried under reduced pressure at 100 °C for 12 hours.

[0084] The synthesized compound had a yield of 0.76 g, a yield of 70%, a logarithmic viscosity of 0.92 dL / g (at 30°C in a 0.5 g / dL N-methyl-2-pyrrolidone solution), a number-average molecular weight (Mn) of 72,000, a weight-average molecular weight (Mw) of 144,000, a molecular weight distribution (Mw / Mn) of 2.0, and an average degree of polymerization (n) of 165.

[0085] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 70 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3056(Ar-H), 2949(CH), 1560(C=N), 1211(CO), 1173(CN) 1 H-NMR(CDCl3,ppm):8.19(m,2H,Ar-H), 7.44(t,3H,Ar-H), 7.35(m,2H,Ar-H), 7.23(m,4H,Ar -H), 7.13(m,2H,Ar-H), 2.65(q,2H,CH2), 1.89-1.53(m,6H,CH2,CH3), 1.03-0.97(m,4H,CH2) 13 C-NMR(CDCl3,ppm):175.65, 173.00, 149.88, 143.19, 134.54, 133.32, 129.2 6, 128.61, 127.47, 121.58, 46.65, 46.34, 37.16, 35.20, 28.74, 23.10, 22.90 Elemental analysis (C 28 H 25 N3O2) n Calculated values: C, 77.21%; H, 5.79%; N, 9.65%; Measured values: C, 76.61%; H, 5.82%; N, 9.66% Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, cyclohexanone, and cyclopentanone. 5% weight loss temperature: 397°C (in air), 416°C (in nitrogen) 10% weight loss temperature: 416°C (in air), 426°C (in nitrogen), Carbonization yield: 18% (in nitrogen, 800°C) Glass transition temperature (Tg): 225°C (DSC), 226°C (TMA), 221°C (DMA), Coefficient of thermal expansion (CTE): 99 ppm / °C Cutoff wavelength: 323nm, transmittance at 400nm: 81%, average refractive index (n): 1.617 (d line), birefringence (Δn): 0.002 (d line), dielectric constant calculated from refractive index (ε): 2.61 (ε=n 2 ) Dielectric constant (Dk): 2.62 (TE mode, 10 GHz), 2.61 (TM mode, 10 GHz), 2.61 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.003 (TE mode, 10 GHz), 0.003 (TM mode, 10 GHz), and 0.003 (TE mode, 20 GHz).

[0086] (Example 4) The polymer DCPT-BisPHTG of Example 4 was synthesized as follows. 4-[1-(4-hydroxyphenol)-3,5,5-trimethylcyclohexyl]phenol (BisPHTG) (0.776 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were added to a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and the mixture was stirred. A solution of DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous dichloromethane (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and reprecipitated by pouring it into methanol. After recovering the polymer, it was dried under reduced pressure at 100 °C for 12 hours.

[0087] The synthesized compound had a yield of 0.95 g, a yield of 82%, a logarithmic viscosity of 1.84 dL / g (at 30°C in a 0.5 g / dL N-methyl-2-pyrrolidone solution), a number-average molecular weight (Mn) of 264,000, a weight-average molecular weight (Mw) of 422,000, and a molecular weight distribution (Mw / Mn) of 1.6.

[0088] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150 °C for 12 hours to obtain a colorless, transparent cast film (thickness 60 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3056(Ar-H), 2949(CH), 1560(C=N), 1211(CO), 1173(CN) 1H-NMR(CDCl3,ppm):8.18-8.03(m,2H,Ar-H), 7.44(m,3H,Ar-H), 7.29(m,4H,Ar-H), 7.14(m,4H,Ar-H), 2.74(d,1H,CH) , 2.54(d,1H,CH), 2.08-2.04(m,2H,CH2), 1.44(d,1H,CH), 1.26(t,1H,CH), 1.04-0.91(m,7H,CH,CH3), 0.51(s,3H,CH3) Elemental analysis (C 30 H 29 N3O2) n Calculated values: C, 77.73%; H, 6.30%; N, 9.07%; Measured values: C, 77.60%; H, 6.40%; N, 8.95% Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, and cyclopentanone. 5% weight loss temperature: 407°C (in air), 421°C (in nitrogen) 10% weight loss temperature: 420°C (in air), 431°C (in nitrogen), Carbonization yield: 18 (in nitrogen, 800°C) Glass transition temperature (Tg): 243°C (DSC), 243°C (TMA), 246°C (DMA), Coefficient of thermal expansion (CTE): 76 ppm / °C Cutoff wavelength: 319nm, transmittance at 400nm: 80% Average refractive index (n): 1.598 (d line), birefringence (Δn): 0.008 (d line), dielectric constant calculated from refractive index (ε): 2.55 (ε=n 2 ) Dielectric constant (Dk): 2.55 (TE mode, 10 GHz), 2.57 (TM mode, 10 GHz), 2.53 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.002 (TE mode, 10 GHz), 0.002 (TM mode, 10 GHz), and 0.002 (TE mode, 20 GHz).

[0089] (Example 5) The polymer DCPT-BisPCDE of Example 5 was synthesized as follows. 4,4'-cyclododecylidenebisphenol (BisPCDE) (0.881 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed in a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and stirred. A solution of DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous dichloromethane (5.0 mL) was added to the round-bottom flask and the reaction was carried out by vigorous stirring at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and reprecipitated by pouring it into methanol. After recovering the polymer, it was dried under reduced pressure at 100 °C for 12 hours.

[0090] The synthesized compound had a yield of 1.03 g, a yield of 81%, a logarithmic viscosity of 0.91 dL / g (at 30°C in a 0.5 g / dL N-methyl-2-pyrrolidone solution), a number-average molecular weight (Mn) of 166,000, a weight-average molecular weight (Mw) of 332,000, and a molecular weight distribution (Mw / Mn) of 2.0.

[0091] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 54 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3059(Ar-H), 2936(CH), 1560(C=N), 1211(CO), 1173(CN) 1 H-NMR(CDCl3,ppm):8.16(d,2H,Ar-H), 7.47(t,1H,Ar-H), 7.33(t,2H,Ar-H), 7.27(d ,4H,Ar-H), 7.16(d,4H,Ar-H), 2.13(m,4H,CH2), 1.38(m,14H,CH2), 1.04(m,4H,CH2) 13C-NMR(CDCl3,ppm):175.5, 173.2, 149.9, 147.2, 134.6, 133.3, 129.2, 128.8, 128.6, 121.0, 48.3, 33.5, 26.6, 26.3, 22.3, 22.1, 20.2 Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, and cyclopentanone. 5% weight loss temperature: 383°C (in air), 404°C (in nitrogen) 10% weight loss temperature: 408°C (in air), 417°C (in nitrogen), Carbonization yield: 18 (in nitrogen, 800°C) Glass transition temperature (Tg): 239°C (DSC), 243°C (TMA), 240°C (DMA), Coefficient of thermal expansion (CTE): 76 ppm / °C Cutoff wavelength: 321nm, transmittance at 400nm: 85% Average refractive index (n): 1.599 (d line), birefringence (Δn): 0.010 (d line), dielectric constant calculated from refractive index (ε): 2.56 (ε=n 2 ) Dielectric constant (Dk): 2.62 (TE mode, 10 GHz), 2.63 (TM mode, 10 GHz), 2.60 (TE mode, 20 GHz) Dielectric loss tangent (Df): 0.002 (TE mode, 10 GHz), 0.002 (TM mode, 10 GHz), 0.002 (TE mode, 20 GHz) That was the case.

[0092] (Example 6) The polymer DCPT-HPTM5I of Example 6 was synthesized as follows. 3-(4-hydroxyphenyl)-1,1,3-trimethyl-5-indanol (HPTM5I) (0.671 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed in a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and the mixture was stirred. A solution of DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous nitrobenzene (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours and then at 100°C for 12 hours.

[0093] The synthesized compound had a yield of 0.93 g, a yield rate of 88%, a logarithmic viscosity of 0.62 dL / g (at 30°C in a 0.5 g / dL N-methyl-2-pyrrolidone solution), a number-average molecular weight (Mn) of 135,000, a weight-average molecular weight (Mw) of 283,500, and a molecular weight distribution (Mw / Mn) of 2.1.

[0094] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 160°C for 12 hours to obtain a colorless, transparent cast film (thickness 40 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3066(Ar-H), 2957(CH), 1560(C=N), 1211(CO), 1173(CN) 1 H-NMR(CDCl3,ppm):8.29-8.12(m,2H,Ar-H), 7.44(t,1H,Ar-H), 7.34-7.22(m,5H,Ar-H), 7.16-7.06 (m,4H,Ar-H), 2.40(d,1H,CH), 2.27(d,1H,CH), 1.72(s,3H,CH3), 1.37(s,3H,CH3), 1.08(s,3H,CH3) 13C-NMR(CDCl3,ppm):175.7, 173.1, 151.1, 149.9, 149.8, 149.7, 148.2, 134.6, 133.2, 129.2, 128.6, 127.8, 123.6, 121.1, 120.6, 118.3, 59.6, 50.6, 42.7, 31.0, 30.7, 30.3 Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, γ-butyrolactone, cyclohexanone, and cyclopentanone. 5% weight loss temperature: 418°C (in air), 438°C (in nitrogen) 10% weight loss temperature: 429°C (in air), 446°C (in nitrogen) Carbonization yield: 33% (in nitrogen, 800°C) Glass transition temperature (Tg): 206°C (DSC), 203°C (TMA), 201°C (DMA), Coefficient of thermal expansion (CTE): 85 ppm / °C Cutoff wavelength: 322nm, transmittance at 400nm: 79% Average refractive index (n): 1.613 (d line), birefringence (Δn): 0.001 (d line), dielectric constant calculated from refractive index (ε): 2.60 (ε=n 2 ) Dielectric constant (Dk): 2.60 (TE mode, 10 GHz), 2.63 (TM mode, 10 GHz), 2.60 (TE mode, 20 GHz) Dielectric loss tangent (Df): 0.004 (TE mode, 10 GHz), 0.004 (TM mode, 10 GHz), 0.004 (TE mode, 20 GHz) That was the case.

[0095] (Example 7) The polymer DCPT-BisC of Example 7 was synthesized as follows. A triazine compound was synthesized similarly to that in Example 6, using BisC instead of HPTM5I.

[0096] The synthesized compound had a yield of 78%, a logarithmic viscosity of 1.00 dL / g (at 30°C in a 0.5 g / dL chloroform solution), a number-average molecular weight (Mn) of 138,000, a weight-average molecular weight (Mw) of 262,000, and a molecular weight distribution (Mw / Mn) of 1.9, as determined by GPC (THF).

[0097] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 29 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3057(Ar-H), 2967(CH), 1560(C=N), 1211(CO), 1173(CN) 1 H-NMR(CDCl3,ppm):8.20(d,2H,Ar-H), 7.46(t,1H,Ar-H), 7.35(t,2H,Ar-H), 7.15(m,4H,Ar-H), 7.07(d,2H,Ar-H), 2.19(s,6H,CH3), 1.73(s,6H,CH3) 13 C-NMR(CDCl3,ppm):175.8, 173.0, 148.7, 148.3, 134.7, 133.2, 129.8, 129.7, 129.2, 128.6, 125.6, 121.2, 42.5, 31.2, 16.8 Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), nitrobenzene, benzonitrile, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, and cyclopentanone. 5% weight loss temperature: 401°C (in air), 411°C (in nitrogen); 10% weight loss temperature: 414°C (in air), 419°C (in nitrogen); Carbonization yield: 26% (in nitrogen, 800°C). Glass transition temperature (Tg): 170°C (DSC), 169°C (TMA), 166°C (DMA); Coefficient of thermal expansion (CTE): 93 ppm / °C (range from 50°C to 100°C) Cutoff wavelength: 311nm, transmittance at 400nm: 77% Average refractive index (n): 1.620 (d-line), birefringence (Δn): 0.0018 (d-line), dielectric constant (ε) calculated from refractive index: 2.62 (ε = n 2 ) Dielectric constant (Dk) by cavity resonator: 2.59 (TE mode, 10 GHz), 2.60 (TE mode, 20 GHz) Dielectric tangent (Df): 0.001 (TE mode, 10 GHz), 0.002 (TE mode, 20 GHz) It was as follows.

[0098] (Example 8) The polymer of Example 8, DCPT - BisTMP was synthesized as follows. Using BisTMP instead of HPTM5I of Example 6, a triazine compound was synthesized in the same manner.

[0099] The synthesized compound had a yield of 76%, a logarithmic viscosity of 1.12 dL / g (in a chloroform solution of 0.5 g / dL at 30 °C), a number average molecular weight (Mn) of 184,000 by GPC (THF), a weight average molecular weight (Mw) of 313,000, and a molecular weight distribution (Mw / Mn) of 1.7.

[0100] This polymer was dissolved in chloroform and cast on a glass plate. It was dried under reduced pressure at 150 °C for 12 hours to obtain a colorless and transparent cast film (film thickness 56 μm). For this example, the analysis results using the aforementioned equipment were FT - IR (film, cm -1 ): 3051 (Ar - H), 2923 (C - H), 1560 (C = N), 1211 (C - O), 1173 (C - N) 1 H - NMR (CDCl3, ppm): 8.19 (d, 2H, Ar - H), 7.47 (t, 1H, Ar - H), 7.35 (t, 2H, Ar - H), 6.99 (s, 4H, Ar - H), 2.13 (s, 12H, CH3), 1.71 (s, 6H, CH3) 13C-NMR(CDCl3,ppm):175.9, 172.7, 148.0, 147.5, 134.8, 133.1, 129.4, 129.2, 128.5, 127.2, 42.3, 31.2, 16.9 Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), nitrobenzene, benzonitrile, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, and cyclopentanone. 5% weight loss temperature: 383°C (in air), 406°C (in nitrogen); 10% weight loss temperature: 396°C (in air), 413°C (in nitrogen); Carbonization yield: 18% (in nitrogen, 800°C) Glass transition temperature (Tg): 212°C (DSC), 208°C (TMA), 209°C (DMA); Coefficient of thermal expansion (CTE): 67 ppm / °C (range from 50°C to 100°C) Cutoff wavelength: 314nm, transmittance at 400nm: 84% Average refractive index (n): 1.591 (d line), birefringence (Δn): 0.0022 (d line), dielectric constant calculated from refractive index (ε): 2.53 (ε=n 2 ) Dielectric constant (Dk) due to cavity resonator: 2.50 (TE mode, 10 GHz), 2.51 (TM mode, 10 GHz), 2.51 (TE mode, 20 GHz) Dielectric loss tangent (Df): 0.002 (TE mode, 10 GHz), 0.002 (TM mode, 10 GHz), 0.002 (TE mode, 20 GHz) That was the case.

[0101] (Example 9) The polymer DCPT-BisCHP of Example 9 was synthesized as follows. In Example 6, a triazine compound was synthesized similarly, using BisCHP instead of HPTM5I.

[0102] The synthesized compound had a yield of 76%, a logarithmic viscosity of 0.49 dL / g (at 30°C in a 0.5 g / dL chloroform solution), a number-average molecular weight (Mn) of 59,000, a weight-average molecular weight (Mw) of 124,000, a molecular weight distribution (Mw / Mn) of 2.1, and an average degree of polymerization (n) of 10⁸, as determined by GPC (THF).

[0103] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 115 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1 ):3051(Ar-H), 2851(CH), 1560(C=N), 1211(CO), 1173(CN) 1 H-NMR(CDCl3,ppm):8.24(d,2H,Ar-H), 7.54-7.35(m,3H,Ar-H), 7.19-6.99(m,5H,Ar-H), 6.73-6.65(m,1H,Ar-H), 2.64(m,2H,CH), 1.74-1.58(m,16H,CH2), 1.31-1.13(m,10H,CH2) 13 C-NMR(CDCl3,ppm):175.7, 173.5, 148.3, 147.4, 138.8, 134.7, 133.1, 129.2, 128.6, 125.9, 125.2, 121.3, 43.0, 37.8, 33.6, 31.3, 26.9, 26.1 Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, benzonitrile, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, cyclohexanone, and cyclopentanone. 5% weight loss temperature: 413°C (in air), 415°C (in nitrogen); 10% weight loss temperature: 422°C (in air), 423°C (in nitrogen); Carbonization yield: 9% (in nitrogen, 800°C) Glass transition temperature (Tg): 161°C (DSC), 153°C (TMA), 146°C (DMA); Coefficient of thermal expansion (CTE): 91 ppm / °C (range from 50°C to 100°C) Cutoff wavelength: 318nm, transmittance at 400nm: 82% Average refractive index (n): 1.590 (d line), birefringence (Δn): 0.0003 (d line), dielectric constant calculated from refractive index (ε): 2.53 (ε=n 2 ) Dielectric constant (Dk) due to cavity resonator: 2.51 (TE mode, 10 GHz), 2.53 (TM mode, 10 GHz), 2.55 (TE mode, 20 GHz), Dielectric loss tangent (Df): 0.005 (TE mode, 10 GHz), 0.005 (TM mode, 10 GHz), 0.004 (TE mode, 20 GHz) That was the case.

[0104] (Example 10) The polymer DCPT-BisAF of Example 10 was synthesized as follows. 2,2-bis(4-hydroxyphenyl)hexafluoropropane (BisAF) (0.841 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed in a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and the mixture was stirred. A solution of DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous dichloromethane (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours and then at 120 °C for 12 hours.

[0105] The synthesized compound had a yield of 1.02 g, a yield rate of 83%, a logarithmic viscosity of 1.21 dL / g (at 30°C in a 0.5 g / dL N-methyl-2-pyrrolidone solution), a number-average molecular weight (Mn) of 257,000, a weight-average molecular weight (Mw) of 771,000, and a molecular weight distribution (Mw / Mn) of 3.0.

[0106] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 120°C for 12 hours to obtain a colorless, transparent cast film (thickness 80 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: 1 H-NMR(CDCl3,ppm):8.24(d,2H,Ar-H), 7.55-7.51(m,5H,Ar-H), 7.41(t,2H,Ar-H), 7.33(d,4H,Ar-H) 13 C-NMR(CDCl3,ppm):176.1, 172.5, 152.3, 134.2, 133.7, 131.6, 131.0, 129.3, 128.8, 121.6 Elemental analysis (C 24 H 13 F6N3O2) n Calculated values: C, 58.90%; H, 2.68%; N, 8.60%; Measured values: C, 58.42%; H, 2.88%; N, 8.15% Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, γ-butyrolactone, cyclohexanone, and cyclopentanone. 5% weight loss temperature: 404°C (in air), 404°C (in nitrogen) 10% weight loss temperature: 414°C (in air), 412°C (in nitrogen) Carbonization yield: 41% (in nitrogen, 800°C) Glass transition temperature (Tg): 202°C (DSC), 202°C (TMA), 199°C (DMA), Coefficient of thermal expansion (CTE): 64 ppm / °C Cutoff wavelength: 321nm, transmittance at 400nm: 84% Average refractive index (n): 1.570 (d line), birefringence (Δn): 0.0004 (d line), dielectric constant calculated from refractive index (ε): 2.46 (ε=n 2 ) Dielectric constant (Dk): 2.52 (TE mode, 10 GHz), 2.52 (TM mode, 10 GHz), 2.53 (TE mode, 20 GHz) Dielectric tangent (Df): 0.002 (TE mode, 10 GHz), 0.003 (TM mode, 10 GHz), 0.003 (TE mode, 20 GHz).

[0107] (Example 11) The polymer of Example 11, DCPT-BPFL, was synthesized as follows. A 1M aqueous sodium hydroxide solution (5.1 mL) and cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) were placed in a eggplant flask (100 mL) together with a stir bar and stirred. A solution of 9,9-bis(4-hydroxyphenyl)fluorene (BPFL) (0.876 g, 2.50 mmol) and DCPT (0.565 g, 2.50 mmol) dissolved in dehydrated nitrobenzene (5.0 mL) was added to the eggplant flask, and the mixture was vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added for neutralization, and the mixture was poured into methanol (250 mL) to precipitate the polymer, which was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours and at 180 °C for 12 hours.

[0108] The synthesized compound had a yield of 0.52 g, a yield rate of 42%, and an inherent viscosity of 1.25 dL / g (in a 0.5 g / dL N-methyl-2-pyrrolidone solution at 30 °C).

[0109] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 180 °C for 12 hours to obtain a colorless and transparent cast film (film thickness 74 μm). For this example, the analysis results using the aforementioned equipment were Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile Glass transition temperature (Tg): 247 °C (DSC), 270 °C (TMA), 264 °C (DMA) Cutoff wavelength: 325 nm, transmittance at 400 nm: 83% Average refractive index (n): 1.670 (d line), birefringence (Δn): 0.0003 (d line), dielectric constant calculated from refractive index (ε): 2.79 (ε=n 2 ) Dielectric constant (Dk): 2.78 (TE mode, 10 GHz), 2.80 (TM mode, 10 GHz), 2.78 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.002 (TE mode, 10 GHz), 0.003 (TM mode, 10 GHz), and 0.003 (TE mode, 20 GHz).

[0110] (Example 12) The polymer DCPpT-BisA of Example 12 was synthesized as follows. In a round-bottom flask (100 mL), bisphenol A (0.571 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed together with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and the mixture was stirred. A solution of DCPpT (0.583 g, 2.50 mmol) dissolved in anhydrous benzonitrile (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at 80°C for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and reprecipitated by pouring it into methanol. After recovering the polymer, it was dried under reduced pressure at 150°C for 12 hours.

[0111] The synthesized compound had a yield of 0.49 g, a yield of 51%, and a logarithmic viscosity of 0.53 dL / g (at 30°C in a 0.5 g / dL chloroform solution).

[0112] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 52 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: FT-IR (film, cm) -1):3038(Ar-H), 2935(CH), 1560(C=N), 1211(CO), 1173(CN) 1 H-NMR(CDCl3,ppm):7.20(d,4H,Ar-H), 7.06(d,4H,Ar-H), 3.62(t,4H,CH2), 1.67-1.61(m,8H,CH2,CH3), 1.51(m,4H,CH2) 13 C-NMR(CDCl3,ppm):172.3, 166.3, 150.1, 147.5, 127.6, 121.3, 44.8, 42.5, 31.1, 25.8, 24.6 Solubility: Soluble in chloroform, dichloromethane, benzonitrile, and cyclohexanone. 5% weight loss temperature: 352°C (in air), 405°C (in nitrogen) 10% weight loss temperature: 386°C (in air), 413°C (in nitrogen) Carbonization yield: 27% (in nitrogen, 800°C) Glass transition temperature (Tg): 178°C (DSC), 183°C (TMA), 171°C (DMA), Coefficient of thermal expansion (CTE): 104 ppm / °C Cutoff wavelength: 286nm, transmittance at 400nm: 83% Average refractive index (n): 1.604 (d line), birefringence (Δn): 0.003 (d line), dielectric constant calculated from refractive index (ε): 2.57 (ε=n 2 ) Dielectric constant (Dk): 2.55 (TE mode, 10 GHz), 2.60 (TM mode, 10 GHz), 2.66 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.003 (TE mode, 10 GHz), 0.003 (TM mode, 10 GHz), and 0.004 (TE mode, 20 GHz).

[0113] (Example 13) The polymer DCPpT-BisPHTG of Example 13 was synthesized as follows. BisPHTG (0.776 g, 2.50 mmol) and 1 M sodium hydroxide aqueous solution (5.1 mL) were placed in a round-bottom flask (100 mL) with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added and the mixture was stirred. A solution of DCPpT (0.583 g, 2.50 mmol) dissolved in anhydrous nitrobenzene (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at 80°C for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and poured into methanol to reprecipitation. After recovering the polymer, it was dried under reduced pressure at 180°C for 12 hours.

[0114] The synthesized compound had a yield of 1.08 g, a yield rate of 92%, a logarithmic viscosity of 0.86 dL / g (at 30°C in a 0.5 g / dL chloroform solution), a number-average molecular weight (Mn) of 103,000, a weight-average molecular weight (Mw) of 206,000, and a molecular weight distribution (Mw / Mn) of 2.0.

[0115] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 77 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: 1 H -NMR(CDCl3,ppm):7.32(d,2H,Ar-H), 7.18(d,2H,Ar-H), 7.02(m,4H,Ar-H), 3.54~3.38(m,4H,C H2), 2.68-2.42(d,2H,CH2), 2.00(m,2H,CH2), 1.49~0.86(m,15H,CH,CH2,CH3), 0.35(d,3H,CH3) Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, cyclohexanone, and cyclopentanone. 5% weight loss temperature: 340°C (in air), 407°C (in nitrogen) 10% weight loss temperature: 360°C (in air), 417°C (in nitrogen) Carbonization yield: 17% (in nitrogen, 800°C) Glass transition temperature (Tg): 236°C (DSC), 246°C (TMA), 233°C (DMA) Coefficient of thermal expansion (CTE): 79 ppm / °C Cutoff wavelength: 288nm, transmittance at 400nm: 86% Average refractive index (n): 1.578 (d line), birefringence (Δn): 0.004 (d line), dielectric constant calculated from refractive index (ε): 2.49 (ε=n 2 ) Dielectric constant (Dk): 2.54 (TE mode, 10 GHz), 2.53 (TM mode, 10 GHz), 2.52 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.002 (TE mode, 10 GHz), 0.002 (TM mode, 10 GHz), and 0.002 (TE mode, 20 GHz).

[0116] (Example 14) The polymer DCPpT-BisTMP used in Example 14 was synthesized as follows. A triazine compound was synthesized similarly to that in Example 13, using BisTMP instead of BisPHTG.

[0117] The synthesized compound had a yield of 78%, a logarithmic viscosity of 0.48 dL / g (at 30°C in a 0.5 g / dL chloroform solution), a number-average molecular weight (Mn) of 37,000, a weight-average molecular weight (Mw) of 59,000, a molecular weight distribution (Mw / Mn) of 1.6, and an average degree of polymerization (n) of 78.

[0118] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 67 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: Solubility: Soluble in benzonitrile, tetrahydrofuran (THF), 1,4-dioxane, chloroform, dichloromethane, and cyclohexanone. 5% weight loss temperature: 380 °C (in air), 399 °C (in nitrogen); 10% weight loss temperature: 395 °C (in air), 406 °C (in nitrogen); Carbonization yield: 17% (in nitrogen, 800 °C) Glass transition temperature (Tg): 201 °C (DSC), 205 °C (TMA), 199 °C (DMA) Coefficient of thermal expansion (CTE): 80 ppm / °C Cut-off wavelength: 294 nm Average refractive index (n): 1.571 (d-line), birefringence (Δn): 0.002 (d-line), dielectric constant (ε) calculated from refractive index: 2.47 (ε = n 2 ) Dielectric constant (Dk): 2.55 (TE mode, 10 GHz), 2.50 (TE mode, 20 GHz) Dielectric loss tangent (Df): 0.002 (TE mode, 10 GHz), 0.002 (TE mode, 20 GHz).

[0119] (Example 15) The polymer of Example 15, DCPpT-BisAF was synthesized as follows. BisAF (0.841 g, 2.50 mmol) and 1 M aqueous sodium hydroxide solution (5.1 mL) were placed in a eggplant flask (100 mL) together with a stir bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% based on the monomer) was added and stirred. A solution of DCPpT (0.583 g, 2.50 mmol) dissolved in dehydrated nitrobenzene (5.0 mL) was added to the eggplant flask, and the mixture was vigorously stirred at 80 °C for 18 hours. After the reaction, acetic acid was added for neutralization, and the mixture was poured into methanol (250 mL) to precipitate the polymer, which was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and poured into methanol for reprecipitation. After the polymer was recovered, it was dried under reduced pressure at 150 °C for 12 hours.

[0120] The synthesized compound had a yield of 1.15 g, a yield rate of 93%, a logarithmic viscosity of 0.47 dL / g (at 30°C in a 0.5 g / dL chloroform solution), a number-average molecular weight (Mn) of 80,000, a weight-average molecular weight (Mw) of 160,000, a molecular weight distribution (Mw / Mn) of 2.0, and an average degree of polymerization (n) of 161.

[0121] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 150°C for 12 hours to obtain a colorless, transparent cast film (thickness 73 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: 1 H-NMR(CDCl3,ppm):7.40(d,4H,Ar-H), 7.22(d,4H,Ar-H), 3.62(t,4H,CH2), 1.63(t,2H,CH2), 1.53(m,4H,CH2) 13 C-NMR(CDCl3,ppm):171.9, 166.1, 152.6, 131.3, 130.3, 121.6, 44.9, 25.7, 24.5 FT-IR (film, cm) -1 ):2934(Ar-H), 1598(C=N), 1376(CN), 1240(CF), 1179(CO) Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), nitrobenzene, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, benzonitrile, and cyclohexanone. 5% weight loss temperature: 346°C (in air), 390°C (in nitrogen) 10% weight loss temperature: 371°C (in air), 400°C (in nitrogen) Carbonization yield: 36% (in nitrogen, 800°C) Glass transition temperature (Tg): 184°C (DSC), 188°C (TMA), 194°C (DMA) Coefficient of thermal expansion (CTE): 79 ppm / °C Cutoff wavelength: 288nm, transmittance at 400nm: 88% Average refractive index (n): 1.544 (d line), birefringence (Δn): 0.003 (d line), dielectric constant calculated from refractive index (ε): 2.38 (ε=n 2 ) Dielectric constant (Dk): 2.41 (TE mode, 10 GHz), 2.42 (TM mode, 10 GHz), 2.37 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.002 (TE mode, 10 GHz), 0.002 (TM mode, 10 GHz), and 0.002 (TE mode, 20 GHz).

[0122] (Example 16) The polymer DCHAT-BisA of Example 16 was synthesized as follows. In a 100 mL round-bottom flask, 0.571 g of bisphenol A (2.50 mmol) and 5.1 mL of 1 M sodium hydroxide aqueous solution were added with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and the mixture was stirred. A solution of DCHAT (0.823 g, 2.50 mmol) dissolved in anhydrous nitrobenzene (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at 100 °C for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and poured into methanol to reprecipitation. After recovering the polymer, it was dried under reduced pressure at 150 °C for 12 hours.

[0123] The synthesized compound had a yield of 1.12 g, a yield of 92%, and a logarithmic viscosity of 0.57 dL / g (at 30°C in a 0.5 g / dL chloroform solution).

[0124] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 180°C for 12 hours to obtain a colorless, transparent cast film (thickness 140 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: Elemental analysis (C 30 H 36 N4O2)n : Calculated value C, 74.35%; H, 7.49%; N: 11.56%, Measured value C, 73.61%; H, 6.80%; N: 11.38% Solubility: Soluble in o-dichlorobenzene, chloroform, dichloromethane 5% weight loss temperature: 388 °C (in air), 402 °C (in nitrogen); 10% weight loss temperature: 404 °C (in air), 412 °C (in nitrogen); Carbonization yield: 27% (in nitrogen, 800 °C) Glass transition temperature (Tg): 211 °C (DSC), 181 °C (TMA), 201 °C (DMA) Coefficient of thermal expansion (CTE): 99 ppm / °C Cut-off wavelength: 291 nm, Transmittance at 400 nm: 87% Average refractive index (n): 1.577 (d line), Birefringence (Δn): 0.004 (d line), Dielectric constant (ε) calculated from refractive index: 2.49 (ε = n 2 ) Dielectric constant (Dk): 2.59 (TE mode, 10 GHz), 2.60 (TM mode, 10 GHz), 2.56 (TE mode, 20 GHz) Dielectric tangent (Df): 0.004 (TE mode, 10 GHz), 0.004 (TM mode, 10 GHz), 0.005 (TE mode, 20 GHz).

[0125] (Example 17) The polymer of Example 17, DCHAT-BisPHTG was synthesized as follows. Using BisPHTG instead of BisA in Example 16, a triazine compound was synthesized in the same manner.

[0126] The synthesized compound had a yield of 83% and a logarithmic viscosity of 0.71 dL / g (in a 0.5 g / dL chloroform solution at 30 °C). The number average molecular weight (Mn) by GPC (THF) was 65,000, the weight average molecular weight (Mw) was 104,000, the molecular weight distribution (Mw / Mn) was 1.6, and the average degree of polymerization (n) was 114.

[0127] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 180°C for 12 hours to obtain a colorless, transparent cast film (thickness 96 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: Solubility: Soluble in N-methyl-2-pyrrolidone (NMP), nitrobenzene, benzonitrile, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, cyclohexanone, and cyclopentanone. 5% weight loss temperature: 372°C (in air), 406°C (in nitrogen) 10% weight loss temperature: 392°C (in air), 416°C (in nitrogen) Carbonization yield: 19% (in nitrogen, 800°C) Glass transition temperature (Tg): 263°C (DSC), 260°C (TMA), 260°C (DMA) Coefficient of thermal expansion (CTE): 62 ppm / °C Cutoff wavelength: 288nm, transmittance at 400nm: 80% Average refractive index (n): 1.559 (d line), birefringence (Δn): 0.010 (d line), dielectric constant calculated from refractive index (ε): 2.43 (ε=n 2 ) Dielectric constant (Dk): 2.50 (TE mode, 10 GHz), 2.54 (TM mode, 10 GHz), 2.47 (TE mode, 20 GHz) The dielectric loss tangent (Df) was 0.006 (TE mode, 10 GHz), 0.005 (TM mode, 10 GHz), and 0.006 (TE mode, 20 GHz).

[0128] (Example 18) The polymer DCHAT-BisPCDE of Example 18 was synthesized as follows. A triazine compound was synthesized similarly to that in Example 16, using BisPCDE instead of BisA.

[0129] The synthesized compound had a yield of 72% and a logarithmic viscosity of 0.57 dL / g (at 30°C in a 0.5 g / dL chloroform solution). The number-average molecular weight (Mn) determined by GPC (THF) was 75,000, the weight-average molecular weight (Mw) was 120,000, the molecular weight distribution (Mw / Mn) was 1.6, and the average degree of polymerization (n) was 123.

[0130] This polymer was dissolved in chloroform and cast onto a glass plate. It was dried under reduced pressure at 180°C for 12 hours to obtain a colorless, transparent cast film (thickness 95 μm). Regarding this example, the analysis results using the aforementioned equipment are as follows: Solubility: Soluble in nitrobenzene, benzonitrile, tetrahydrofuran (THF), 1,4-dioxane, o-dichlorobenzene, chloroform, dichloromethane, and cyclopentanone. 5% weight loss temperature: 336°C (in air), 410°C (in nitrogen) 10% weight loss temperature: 353°C (in air), 417°C (in nitrogen) Carbonization yield: 18% (in nitrogen, 800°C) Glass transition temperature (Tg): 258°C (DSC), 247°C (TMA), 252°C (DMA) Coefficient of thermal expansion (CTE): 49 ppm / °C Cutoff wavelength: 284nm, transmittance at 400nm: 82% Average refractive index (n): 1.563 (d line), birefringence (Δn): 0.010 (d line), dielectric constant calculated from refractive index (ε): 2.44 (ε=n 2 ) Dielectric constant (Dk): 2.27 (TE mode, 10 GHz), 2.37 (TM mode, 10 GHz), 2.42 (TE mode, 20 GHz) Dielectric loss tangent (Df): 0.003 (TE mode, 10 GHz), 0.006 (TM mode, 10 GHz), 0.007 (TE mode, 20 GHz) That was the case.

[0131] [Example of a sample exam] Below, we show a reference test using a reference example as another aspect of this embodiment.

[0132] The polymers in Reference Examples 1 to 18 were synthesized using the same methods as those described in Examples 1 to 18 above. The synthesis results for Reference Examples 1 to 18 are shown in the table below.

[0133] (Reference example 19) The polymer DCPT-BPFL in Reference Example 19 was synthesized as follows. In a round-bottom flask (100 mL), 5.1 mL of 1 M sodium hydroxide aqueous solution and cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) were added with a stirring bar and stirred. A solution of 9,9-bis(4-hydroxyphenyl)fluorene (BPFL) (0.876 g, 2.50 mmol) and DCPT (0.565 g, 2.50 mmol) dissolved in anhydrous nitrobenzene (5.0 mL) was added to the round-bottom flask and vigorously stirred at room temperature for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the solution was poured into methanol (250 mL) to precipitate the polymer. The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours and then at 180°C for 12 hours. (Reference example 20) The polymer DCHAT-BisAF in Reference Example 20 was synthesized as follows. In a round-bottom flask (100 mL), bisphenol AF (0.841 g, 2.50 mmol) and 5.1 mL of 1 M sodium hydroxide aqueous solution were added with a stirring bar and dissolved. Cetyltrimethylammonium bromide (CTMAB, 0.277 g, 0.760 mmol) (30 mol% relative to the monomer) was added as a phase transfer catalyst and the mixture was stirred. A solution of DCHAT (0.823 g, 2.50 mmol) dissolved in anhydrous nitrobenzene (5.0 mL) was added to the round-bottom flask and the mixture was vigorously stirred at 100 °C for 18 hours. After the reaction, acetic acid was added to neutralize the mixture, and the polymer was precipitated by pouring it into methanol (250 mL). The polymer was recovered by suction filtration and dried under reduced pressure at room temperature for 6 hours. The obtained polymer was dissolved in chloroform and poured into methanol to reprecipitation. After recovering the polymer, it was dried under reduced pressure at 150 °C for 12 hours.

[0134] (Test example 1: Synthesis of reference examples 1-6 and 10) The resin compositions of Reference Examples 1-6 and 10 were obtained using the synthesis method described above. The synthesis results are shown in Table 1. The yield is the value after the reprecipitation. Logarithmic viscosity (η) inh The values ​​were measured at 30°C in a 0.5 g / dL NMP solution. The logarithmic viscosity of the resin composition obtained from BisZ in CH2Cl2 solvent was similarly measured in a THF solution. The number-average molecular weight Mn and weight-average molecular weight Mw were measured using GPC (standard polystyrene equivalent, THF solvent).

[0135] [Table 1]

[0136] As shown in Table 1, for each reference example, the resin composition after reprecipitation purification was successfully obtained in a yield of 40% or more. While there were differences in yield depending on whether nitrobenzene or CH2Cl2 was used as the organic solvent for each reference example, many reference examples showed yields of 80-90% or more depending on the choice. Furthermore, the logarithmic viscosity was 0.3-1.2 dL / g, and the Mn content was 70,000-250,000, indicating the acquisition of high molecular weight compounds.

[0137] (Test Example 2: Solubility of Compounds 1-6 and 10 in Reference Examples) Tables 2 and 3 show the results of solubility tests conducted on compounds 1-6 and 10 at room temperature or after heating. Solubility was measured at 10 mg / 5.0 mL. ++: It was soluble at room temperature. +: It dissolved when heated. +-: Only a portion dissolved. -: It was insoluble.

[0138] [Table 2] [Table 3]

[0139] Each of the reference examples demonstrated that the compounds are stable, soluble in certain organic solvents, and exhibit excellent processability, including purification by reprecipitation and film formation by solution casting.

[0140] (Test Example 3: Thermal properties of compounds from Reference Examples 1-6 and 10) Tables 4 and 5 show the results of examining the thermal properties of compounds 1-6 and 10 using the thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), thermomechanical analysis (TMA), and dynamic viscoelastic analysis (DMA) described above. Table 4 T 5% is the 5% weight loss temperature, T 10% The 10% weight loss temperature is the value measured by TGA in nitrogen or air at a heating rate of 10°C / min. Char yield is the carbonization yield, expressed as weight % in nitrogen at 800°C. The glass transition temperature (Tg) in Table 5 is the value measured by DSC in nitrogen at a heating rate of 20°C / min, by TMA in nitrogen at a heating rate of 10°C / min, and by DMA in nitrogen at a heating rate of 2°C / min. The coefficient of thermal expansion (CTE) is the value measured by TMA at 100-150°C.

[0141] [Table 4] [Table 5]

[0142] The results in Table 4 show that both 5% and 10% thermal decomposition in nitrogen occurred at temperatures above 390°C, indicating high thermal stability. As shown in Table 5, all of the reference examples had a glass transition temperature (DSC measurement) of 180°C or higher, and for reference examples 2 to 5, it was 200°C or higher under certain conditions, demonstrating high heat resistance.

[0143] (Test Example 4: Optical and dielectric properties of compounds 1-6 and 10 from Reference Examples) Tables 6, 7, and 8 show the results of examining the optical and dielectric properties of the compounds in Reference Examples 1-6 and 10 under the above instrument conditions. Table 6 shows the refractive index (n) values ​​for film-like samples with a film thickness (d) of 40-70 μm. The refractive index (n) within the film plane is measured in TE mode. TE ), TM mode allows refractive index (n) outside the film surface TM The Δn was measured at the F line (486 nm), d line (588 nm), and C line (656 nm). d It is birefringence, V d n is the Abbe number. ave is n ave =[(2n TE 2 +n TM 2 ) / 3] 1 / 2 The average refractive index is obtained by n TE and n TM This measurement was taken at wavelength d. ε is the dielectric constant, where ε = n ave 2 This is what was obtained. Table 7 shows the dielectric constant (D) measured by a cavity resonator. k ) and dielectric loss tangent (D f The values ​​shown are for ). Measurements were taken at 10GHz and 20GHz in TE mode, and at 10GHz in TM mode. Table 8 shows the cutoff wavelength (λ) determined by the ultraviolet-visible absorption spectrum. cutoff ), the wavelength (λ) that 80% of the light was transmitted 80% ), transmittance at 400nm (T 400 ) was shown.

[0144] [Table 6] [Table 7] [Table 8]

[0145] Table 6 shows that in all of the reference examples 1-6 and 10, the dielectric constant calculated from the average refractive index is 2.7 or less. In Table 7, all of the reference examples 1-6 and 10 are D. k (Dielectric constant) is 2.7 or less, D f The dielectric loss tangent was found to be 0.03 or less, indicating that it is sufficiently low. Although not shown in the table, in Reference Example 19, where the Ar in formula (1) does not contain an aliphatic group, the dielectric loss tangent (Df) was 0.0024 (TE mode, 10 GHz) and 0.0025 (TE mode, 20 GHz), and values ​​of 0.003 or less were observed, but the dielectric constant (D k The value was 2.76 (TE mode, 10GHz), which was higher than reference examples 1-6 and 10.

[0146] (Test Example 5: Synthesis of Reference Examples 12, 13, and 15 using DCPpT) As the compound of formula (13A), R1 in formula (2A) was replaced with formula (4A), and the polymerization temperature was 80°C. Reference Examples 12, 13, and 15 were synthesized using the synthesis method described above. The synthesis results are shown in Table 9. The explanation of the table is the same as in Test Example 1. For Reference Example 12, the yield was 0.49 g, the yield rate was 51%, and the logarithmic viscosity was 0.53 dL / g (at 30°C, in a 0.5 g / dL chloroform solution). For Reference Example 13, the yield was 1.08 g, the yield rate was 95%, and the logarithmic viscosity was 0.86 dL / g (at 30°C, in a 0.5 g / dL chloroform solution).

[0147] [Table 9]

[0148] As shown in Table 9, resin compositions were successfully obtained in yields of 40% or more for each reference example. Reference Examples 13 and 15 showed yields of 90% or more by selecting nitrobenzene as the organic solvent. In all reference examples, it was shown that high molecular weight compounds were obtained.

[0149] (Test Example 6: Solubility of compounds from Reference Examples 12, 13, and 15) Table 10 shows the results of examining the solubility of each reference compound at room temperature or after heating. Solubility was measured at 10 mg / 5.0 mL. The explanation of the table is the same as in Test Example 2.

[0150] [Table 10]

[0151] Each of the reference examples demonstrated that the compounds are stable, soluble in certain organic solvents, and exhibit excellent properties for reprecipitation purification and molding processes.

[0152] (Test Example 7: Thermal properties of compounds from Reference Examples 12, 13, and 15) For each example compound, the thermal properties were examined using the thermogravimetric and differential scanning calorimetry methods described above, and the results are shown in Tables 11 and 12. The explanation of the tables is the same as in Test Example 3.

[0153] [Table 11] [Table 12]

[0154] The results in Table 11 show that both 5% and 10% thermal decomposition occurred in N2 at temperatures above 340°C, indicating high thermal stability. As shown in Table 12, all of the reference examples had a glass transition temperature of 160°C or higher, and reference example 9 had a glass transition temperature of 230°C or higher, demonstrating high heat resistance.

[0155] (Test Example 8: Optical and dielectric properties of compounds from Reference Examples 12, 13, and 15) Tables 13 and 14 show the results of examining the optical and dielectric properties of each example compound under the above instrument conditions. Furthermore, Table 15 shows the transmittance for examples 13 and 15. The explanation of the tables is the same as for test example 4.

[0156] [Table 13] [Table 14] [Table 15]

[0157] In Tables 13 and 14, all of the reference examples 12, 13, and 15 are D. k (Dielectric constant) is 2.6 or less, D f The dielectric loss tangent was found to be 0.004 or less, indicating that it is sufficiently low.

[0158] (Example Test 9: Reference Examples 16 and 20 using DCHAT) As the compound of formula (13A), R1 in formula (2A) was replaced with formula (5A), and polymerization was carried out at the polymerization temperature of 65 to 100°C as shown in the table. Reference Examples 16 and 20 were synthesized using the synthesis method described above. The synthesis results are shown in Table 15. The explanation of the table is the same as in Test Example 1.

[0159] [Table 16]

[0160] As shown in Table 16, resin compositions were successfully obtained in yields of 60% or more for each reference example. Reference Example 16 showed a yield of 90% or more and yielded a high molecular weight product by selecting nitrobenzene as the organic solvent.

[0161] (Test Example 10: Solubility of compounds from Reference Examples 16 and 20) Table 17 shows the results of examining the solubility of each reference compound at room temperature or after heating. Solubility was measured at 10 mg / 5.0 mL. The explanation of the table is the same as in Test Example 2.

[0162] [Table 17]

[0163] (Test Example 11: Thermal properties of the compound in Reference Example 16) Tables 18 and 19 show the results of examining the thermal properties of the compound in Reference Example 16 by performing the thermogravimetric analysis, differential scanning calorimetry, thermomechanical analysis, and dynamic viscoelasticity measurements described above. The explanation of the tables is the same as in Test Example 3.

[0164] [Table 18] [Table 19]

[0165] The results in Table 18 show that both 5% and 10% thermal decomposition in nitrogen occurred at temperatures above 380°C, indicating high thermal stability. As shown in Table 19, Reference Example 16 exhibited high heat resistance, with a glass transition temperature of 180°C or higher.

[0166] (Test Example 12: Optical and dielectric properties of the compound in Reference Example 16) Tables 20, 21, and 22 show the results of examining the optical and dielectric properties of the compound in Reference Example 16 under the above instrument conditions. The explanation of the tables is the same as in Test Example 4.

[0167] [Table 20] [Table 21] [Table 22]

[0168] In Tables 20 and 21, Reference Example 16 is D k The dielectric constant (ε) was shown to be 2.7 or less, which is sufficiently low. [Industrial applicability]

[0169] According to the present invention, a resin composition and a method for producing the same can be obtained that are suitable for use as a low dielectric material because they have a low dielectric constant, a low dielectric loss tangent, high transparency, high solubility, and high heat resistance.

Claims

1. The compound comprises a triazine compound having repeating units represented by the following general formula (1), Further comprising epoxy resin, bismaleimide resin, or cyanate resin, The aforementioned triazine compound is The number-average molecular weight Mn is 3 × 10 ３ ~40 x 10 ４ And, Weight-average molecular weight Mw is 6 × 10 ３ ~80 x 10 ４ And, Measurements of the cavity resonator (TE mode, 20 GHz) showed that the dielectric constant (Dk) was 2.7 or less, or the dielectric loss tangent (Df) was 0.004 or less. A resin composition for low dielectric materials having a glass transition temperature of 160°C or higher, as determined by differential scanning calorimetry (DSC). 【Chemistry 1】 [In equation (1), n ​​is an integer between 2 and 600, R is expressed by one of the following general equations (2) to (4), and Ar is expressed by one of the following general equations (7), (10), (13), or (15).] 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】

2. A resin composition for low dielectric materials according to claim 1, further comprising an inorganic filler, a modifier, or a flame retardant.

3. A resin composition for low dielectric materials according to claim 1 or 2, used in equipment that transmits and receives high-frequency electromagnetic waves having a frequency of 0.1 to 500 GHz.

4. A resin composition for low dielectric materials according to any one of claims 1 to 3, for use in printed circuit boards, flexible printed circuit boards, encapsulants for electronic components, resist inks, conductive pastes, insulating materials, or insulating boards.

5. A film for a laminated substrate having at least one surface an insulating material comprising the resin composition for low dielectric materials described in any one of claims 1 to 4.

6. A laminated substrate comprising two or more laminated substrate films as described in claim 5.

7. A method for producing a resin composition for low dielectric materials according to any one of claims 1 to 4, A method for producing a resin composition for low dielectric materials, comprising mixing a compound represented by the following general formula (16) and a compound represented by the following general formula (17), and polymerizing them to obtain a triazine compound represented by the following general formula (18). 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 [In formulas (16), (17), and (18), n is an integer of 2 or more, and R represents a linear, branched, or cyclic aliphatic group, a linear, branched, or cyclic aliphatic oxy group, a linear, branched, or cyclic aliphatic secondary amino group, an aromatic group or a substituted aromatic group, an aromatic oxy group or a substituted aromatic oxy group, an aromatic secondary amino group or a substituted aromatic secondary amino group, a fluorinated version of the above aliphatic group, a fluorinated version of the above aliphatic oxy group, a fluorinated version of the above aliphatic secondary amino group, a fluorinated version of the above aromatic group, a fluorinated version of the above aromatic oxy group, or a fluorinated aromatic secondary amino group. Ar represents a linear, branched, or cyclic aliphatic group, or a divalent aromatic group having a fluorinated linear, branched, or cyclic aliphatic group.]

8. A method for producing a resin composition for a low dielectric material used as an insulating material between layers of a laminated substrate, comprising mixing the triazine compound, epoxy resin, bismaleimide resin or cyanate resin, a curing accelerator and an organic solvent, according to claim 7.

9. A method for producing a resin composition for a low dielectric material according to claim 8, further comprising mixing an inorganic filler, a modifier, or a flame retardant.

10. A method for manufacturing a laminated substrate film, comprising applying an insulating material containing a resin composition for low dielectric materials, manufactured by the method for manufacturing a resin composition for low dielectric materials according to claim 8 or 9, to at least one surface of a resin film.

11. A method for manufacturing a laminated substrate, comprising stacking two or more laminated substrate films manufactured by the method for manufacturing a laminated substrate film according to claim 10.

12. A resin composition for low dielectric materials according to any one of claims 1 to 4, for use in resin compositions for copper-clad laminates, interlayer insulating materials for build-up printed circuit boards, build-up films, resin compositions for encapsulants of electronic components, resin compositions for resist inks, binders for friction materials, conductive pastes, resin casting materials, adhesives, insulating paints, or coating materials.

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