Classifications

• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
  • H05K1/00—Printed circuits
  • H05K1/02—Details
  • H05K1/03—Use of materials for the substrate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
  • C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
  • C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
  • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
  • C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
  • C08G2650/46—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen
  • C08G2650/48—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen containing fluorine, e.g. perfluropolyethers
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers

Definitions

• the present disclosure relates to fluorine-containing polyether compounds.
• Non-Patent Document 1 discloses poly(perfluoroalkylene aryl ether) having a specific structure by polymerizing 1,6-bis(4-fluorophenyl)perfluorohexane with bisphenol AF, bisphenol A or resorcinol. It is stated that the obtained
• Non-Patent Document 1 The highest glass transition temperature of the poly(perfluoroalkylene aryl ether) disclosed in Non-Patent Document 1 is only 95°C. Therefore, a fluorine-containing polyether compound with higher heat resistance is desired.
• An object of the present disclosure is to provide a fluorine-containing polyether compound that exhibits sufficiently low dielectric constant and dielectric loss tangent, and has both a very high glass transition temperature and high solubility.
• a fluorine-containing polyether compound having a repeating unit represented by formula (1) is provided.
• n is an integer of 1 to 8
• Ph is a phenylene group
• X 1 represents a heterocyclic ring or a hydrocarbon ring.
• One or both of the two phenylene groups represented by Ph, and X 1 The represented heterocycle or hydrocarbon ring may be condensed with each other, and the phenylene group, heterocycle and hydrocarbon ring may have a substituent.
• X 1 is an optionally substituted aromatic heterocyclic ring, an optionally substituted aromatic hydrocarbon ring, or an optionally substituted It preferably represents an aliphatic hydrocarbon ring.
• X 1 preferably represents at least one selected from the group consisting of rings represented by the following formulas.
• the average degree of polymerization of the repeating unit represented by formula (1) is preferably 2-300.
• a fluorine-containing polyether compound having a repeating unit represented by formula (2) is provided.
• Formula (2) (In formula ( 2 ), n is an integer of 1 to 8, and X2 represents a polycyclic aromatic hydrocarbon ring which may have a substituent.)
• the polycyclic aromatic hydrocarbon ring is at least one selected from the group consisting of biphenyl ring, terphenyl ring, quarterphenyl ring, naphthalene ring, anthracene ring, tetracene ring and pentacene ring. is preferred.
• the average degree of polymerization of the repeating unit represented by formula (2) is preferably 2-300.
• a low dielectric substance containing the fluorine-containing polyether compound is provided.
• a semiconductor package substrate, flexible printed circuit board or rigid printed circuit board containing the fluorine-containing polyether compound is provided.
• the fluorinated polyether compound of the present disclosure has a repeating unit represented by formula (1).
• n is an integer of 1 to 8
• Ph is a phenylene group
• X 1 represents a heterocyclic ring or a hydrocarbon ring.
• One or both of the two phenylene groups represented by Ph, and X 1 The represented heterocycle or hydrocarbon ring may be condensed with each other, and the phenylene group, heterocycle and hydrocarbon ring may have a substituent.
• n represents an integer from 1 to 8. n is preferably an integer of 4 to 8, more preferably 4, 6 or 8.
• Ph represents a phenylene group.
• a phenylene group may or may not have a substituent.
• substituents include halogen atoms such as fluorine atoms, alkyl groups such as methyl groups, and halogenated alkyl groups such as trifluoromethyl groups.
• X 1 represents a heterocyclic ring or a hydrocarbon ring.
• the heterocycle or hydrocarbon ring represented by X 1 is a ring having at least two bonds that bond to two phenylene groups, at least one bond that bonds to one of the two phenylene groups and two phenylene groups. It may be a ring having at least one carbon-carbon bond shared with another or a ring having at least two carbon-carbon bonds shared with two phenylene groups.
• the heterocycle or hydrocarbon ring represented by X 1 is a ring having at least two bonds that bond to two phenylene groups, or at least one bond that bonds to one of two phenylene groups and two Rings having at least one carbon-carbon bond shared with the other of the phenylene groups are preferred.
• the structure represented by -Ph-X 1 -Ph- is represented by Ph
• a condensed ring formed by condensing at least one of the phenylene groups represented by X 1 with the heterocyclic ring or hydrocarbon ring represented by X 1 is included. Therefore, in the present disclosure, the phenylene group represented by Ph includes not only the residue resulting from removing two hydrogen atoms from benzene, but also removing one hydrogen atom and condensing with another ring Also included are residues derived from benzene forming part of a polycycle. Structures containing such condensed rings (structures represented by —Ph—X 1 —Ph—) include, for example, the following structures.
• the heterocyclic ring is preferably a ring formed by carbon atoms and atoms other than carbon atoms. Atoms other than carbon atoms are preferably nitrogen atoms, oxygen atoms or sulfur atoms, and more preferably nitrogen atoms. That is, the heterocyclic ring is preferably a nitrogen-containing heterocyclic ring.
• the number of atoms other than carbon atoms in the ring is preferably 1-3, more preferably 3.
• the heterocycle may be an aliphatic heterocycle or an aromatic heterocycle.
• an aromatic heterocycle is preferred.
• heterocycles may be monocyclic or polycyclic.
• the heterocyclic ring is preferably a monocyclic ring, more preferably a monocyclic aromatic heterocyclic ring, and even more preferably a monocyclic nitrogen-containing aromatic heterocyclic ring.
• the number of ring members of the heterocyclic ring is not particularly limited, but is preferably 3 to 12, more preferably 5 or more, more preferably 9 or less, still more preferably 6 or less.
• Heterocyclic rings include furan ring, thiophene ring, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, pyrazole ring, 1,2,3-oxadiazole ring, 1,2,4 -oxadiazole ring, 1,3,4-oxadiazole ring, furazane ring, 1,2,3-thiadiazole ring, 1,2,4-thiadiazole ring, 1,3,4-thiadiazole ring, 1,2 ,3-triazole ring, 1,2,4-triazole ring, tetrazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring and the like.
• 1,3,5-triazine ring is particularly preferable.
• a heterocyclic ring may or may not have a substituent.
• substituents include halogen atoms such as a fluorine atom, alkyl groups such as a methyl group, halogenated alkyl groups such as a trifluoromethyl group, and aryl groups such as a phenyl group.
• the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring.
• An aliphatic hydrocarbon ring may be a saturated or unsaturated hydrocarbon ring having no aromatic character.
• Hydrocarbon rings may be monocyclic or polycyclic.
• the polycyclic hydrocarbon ring may be a condensed ring.
• the number of carbon atoms in the hydrocarbon ring is preferably 3 to 30, more preferably 5 or more, still more preferably 6 or more, more preferably 20 or less, still more preferably 14 or less.
• hydrocarbon ring monocyclic saturated hydrocarbon rings such as cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclononane ring, cyclodecane ring, cycloundecane ring, cyclododecane ring; monocyclic non-aromatic unsaturated hydrocarbon rings such as cyclopropene ring, cyclobutene ring, cyclopropene ring, cyclohexene ring, cycloheptene ring, cyclooctene ring; Polycyclic non-aromatic hydrocarbon rings such as norbornene ring, norbornadiene ring, decahydronaphthalene ring, bicycloundecane ring, and spirobicyclopentane ring; Benzene ring
• the hydrocarbon ring may or may not have a substituent.
• substituents include halogen atoms such as a fluorine atom, alkyl groups such as a methyl group, halogenated alkyl groups such as a trifluoromethyl group, and aryl groups such as a phenyl group.
• heterocyclic ring or hydrocarbon ring represented by X 1 at least one selected from the group consisting of rings represented by the following formulas is preferable.
• the wavy line represents the bonding position with the phenylene group represented by Ph
• the dashed line represents the carbon-carbon bond shared with the phenylene group represented by Ph.
• the glass transition temperature of the fluorine-containing polyether compound having a repeating unit represented by formula (1) is preferably 100 to 400°C, more preferably 110°C or higher, still more preferably 120°C or higher. It is preferably 300° C. or lower, more preferably 250° C. or lower.
• the glass transition temperature is a value measured by thermomechanical analysis (TMA), differential scanning calorimetry (DSC) or dynamic viscoelasticity measurement (DMA).
• the average degree of polymerization of the repeating unit represented by formula (1) is preferably 500 or less, more preferably 400 or less, and further It is preferably 300 or less, may be 2 or more, or may be 3 or more.
• the average degree of polymerization is obtained by calculation from the number average molecular weight of the fluorine-containing polyether compound of the present disclosure.
• the number average molecular weight (Mn) of the fluorine-containing polyether compound having the repeating unit represented by formula (1) is preferably 2,000 or more, more preferably 1, in terms of standard polystyrene by gel permeation chromatography (GPC). 10,000 or more, preferably 500,000 or less, and more preferably 300,000 or less.
• the molecular weight distribution (Mw/Mn) of the fluorine-containing polyether compound having the repeating unit represented by formula (1) is preferably 2 or more and preferably 5 or less in terms of standard polystyrene by gel permeation chromatography (GPC). and more preferably 4 or less.
• the logarithmic viscosity ⁇ inh of the fluorine-containing polyether compound having repeating units represented by formula (1) is preferably 0.3 dL/g or more, more preferably 0.5 dL/g or more.
• the logarithmic viscosity ⁇ inh is obtained by dissolving a fluorine-containing polyether compound in N-methyl-2-pyrrolidone (NMP) or the like as a solvent to prepare a solution having a solution concentration of 0.5 g/dL. It can be calculated by measuring the solution viscosity at 30° C. and using the following formula.
• Logarithmic viscosity ⁇ inh ln (solution viscosity/solvent viscosity)/solution concentration
• a fluorine-containing polyether compound having a repeating unit represented by formula (1) is obtained by polymerizing a dihydroxy compound (11) represented by formula (11) and an active aromatic compound (12) represented by formula (12). It can be suitably produced by
• Formula (12) (In formula (12), n is the same as formula (1), and Z is a halogen atom or a nitro group.)
• Polymerization of the dihydroxy compound (11) and the active aromatic compound (12) can be carried out in the presence of a base.
• the base include carbonates such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, cesium carbonate, and cesium hydrogencarbonate; hydroxides such as sodium hydroxide, potassium hydroxide, and cesium hydroxide; sodium fluoride; Examples include fluoride compounds such as potassium fluoride and cesium fluoride.
• Solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2- imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethylsulfoxide (DMSO), sulfolane, dimethylsulfone, diphenylsulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, etc. be done.
• DMF N,N-dimethylformamide
• DMAc N,N-dimethylacetamide
• NMP N-methyl-2-pyrrolidone
• TMU tetramethylurea
• DI 1,3-dimethyl-2- imidazolidone
• DMPU N,N'-dimethylpropyleneurea
• An azeotropic solvent such as toluene, o-xylene, m-xylene and p-xylene is used to remove water generated by polymerization of the dihydroxy compound (11) and the active aromatic compound (12) in the presence of a base.
• the polymerization temperature is preferably 50-250°C, more preferably 150-220°C.
• the polymerization time is preferably 0.1 to 50 hours, more preferably 1 to 36 hours.
• the average degree of polymerization of the repeating unit represented by formula (1) is adjusted by changing the molar ratio of the dihydroxy compound (11) and the active aromatic compound (12), the polymerization temperature, the polymerization time, the concentration of the polymerization solution, and the like. can do.
• the fluorine-containing polyether compound of the present disclosure has a repeating unit represented by formula (2).
• Formula (2) (In formula ( 2 ), n is an integer of 1 to 8, and X2 represents a polycyclic aromatic hydrocarbon ring which may have a substituent.)
• n represents an integer from 1 to 8. n is preferably an integer of 4 to 8, more preferably 4, 6 or 8.
• X2 represents a polycyclic aromatic hydrocarbon ring.
• the polycyclic aromatic hydrocarbon ring represented by X 2 is a ring formed by removing two hydrogen atoms from a polycyclic aromatic hydrocarbon in which two or more aromatic rings are condensed, or two or more aromatic It is a ring formed by removing two hydrogen atoms from a polycyclic aromatic hydrocarbon in which rings are linked by single bonds.
• the polycyclic aromatic hydrocarbon ring is directly bonded to two adjacent oxygen atoms.
• the number of carbon atoms in the polycyclic aromatic hydrocarbon ring is preferably 8 to 30, more preferably 10 or more, more preferably 26 or less, still more preferably 22 or less.
• the number of rings in the polycyclic aromatic hydrocarbon ring is preferably 2 to 8, more preferably 6 or less, still more preferably 5 or less.
• Polycyclic aromatic hydrocarbon rings include biphenyl ring, terphenyl ring, quarterphenyl ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, tetracene ring, chrysene ring, pyrene ring, triphenylene ring, pentacene ring, and benzopyrene. rings, perylene rings, and the like.
• the polycyclic aromatic hydrocarbon ring is preferably at least one selected from the group consisting of biphenyl ring, terphenyl ring, quarterphenyl ring, naphthalene ring, anthracene ring, tetracene ring and pentacene ring.
• the polycyclic aromatic hydrocarbon ring may or may not have a substituent.
• substituents include halogen atoms such as a fluorine atom, alkyl groups such as a methyl group, halogenated alkyl groups such as a trifluoromethyl group, and aryl groups such as a phenyl group.
• the glass transition temperature of the fluorine-containing polyether compound having a repeating unit represented by formula (2) is preferably 96 to 400°C, more preferably 100°C or higher, preferably 300°C or lower, and more preferably. is below 250°C.
• the glass transition temperature is a value measured by thermomechanical analysis (TMA), differential scanning calorimetry (DSC) or dynamic viscoelasticity measurement (DMA).
• the average degree of polymerization of the repeating unit represented by formula (2) is preferably 500 or less, more preferably 400 or less, and further It is preferably 300 or less, may be 2 or more, or may be 3 or more.
• the average degree of polymerization is obtained by calculation from the number average molecular weight of the fluorine-containing polyether compound of the present disclosure.
• the number average molecular weight (Mn) of the fluorine-containing polyether compound having the repeating unit represented by formula (2) is preferably 2,000 or more, more preferably 1, in terms of standard polystyrene by gel permeation chromatography (GPC). 10,000 or more, preferably 500,000 or less, and more preferably 300,000 or less.
• the molecular weight distribution (Mw/Mn) of the fluorine-containing polyether compound having the repeating unit represented by formula (2) is preferably 2 or more and preferably 5 or less in terms of standard polystyrene by gel permeation chromatography (GPC). and more preferably 4 or less.
• the logarithmic viscosity ⁇ inh of the fluorine-containing polyether compound having repeating units represented by formula (2) is preferably 0.3 dL/g or more, more preferably 0.5 dL/g or more.
• the logarithmic viscosity ⁇ inh is obtained by dissolving a fluorine-containing polyether compound in N-methyl-2-pyrrolidone (NMP) or the like as a solvent to prepare a solution having a solution concentration of 0.5 g/dL. It can be calculated by measuring the solution viscosity at 30° C. and using the following formula.
• Logarithmic viscosity ⁇ inh ln (solution viscosity/solvent viscosity)/solution concentration
• a fluorine-containing polyether compound having a repeating unit represented by formula (2) is obtained by polymerizing a dihydroxy compound (21) represented by formula (21) and an active aromatic compound (22) represented by formula (22). It can be suitably produced by
• Formula (22) (In formula (22), n is the same as formula (2), and Z is a halogen atom or a nitro group.)
• Polymerization of the dihydroxy compound (21) and the active aromatic compound (22) can be carried out in the presence of a base.
• the base include carbonates such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, cesium carbonate, and cesium hydrogencarbonate; hydroxides such as sodium hydroxide, potassium hydroxide, and cesium hydroxide; sodium fluoride; Examples include fluoride compounds such as potassium fluoride and cesium fluoride.
• Solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2- imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethylsulfoxide (DMSO), sulfolane, dimethylsulfone, diphenylsulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, etc. be done.
• DMF N,N-dimethylformamide
• DMAc N,N-dimethylacetamide
• NMP N-methyl-2-pyrrolidone
• TMU tetramethylurea
• DI 1,3-dimethyl-2- imidazolidone
• DMPU N,N'-dimethylpropyleneurea
• An azeotropic solvent such as toluene, o-xylene, m-xylene and p-xylene is used to remove water generated by polymerization of the dihydroxy compound (21) and the active aromatic compound (22) in the presence of a base.
• the polymerization temperature is preferably 50-250°C, more preferably 150-220°C.
• the polymerization time is preferably 0.1 to 50 hours, more preferably 1 to 36 hours.
• the average degree of polymerization of the repeating unit represented by formula (2) can be adjusted by changing the molar ratio of the dihydroxy compound (21) and the active aromatic compound (22), the polymerization temperature, the polymerization time, the concentration of the polymerization solution, etc. can be adjusted.
• the fluorinated polyether compound of the present disclosure exhibits sufficiently low dielectric constant and dielectric loss tangent, and has both a very high glass transition temperature and high solubility, so it can be suitably used as a low dielectric substance.
• the fluorine-containing polyether compound of the present disclosure exhibits sufficiently low dielectric constant and dielectric loss tangent, and has both a very high glass transition temperature and high solubility, so substrates such as semiconductor package substrates, flexible printed substrates, and rigid printed substrates can be suitably used as
• the fluorine-containing polyether compound of the present disclosure exhibits a sufficiently low dielectric constant and dielectric loss tangent, and has both a very high glass transition temperature and high solubility.
• TAB tape, COF tape, metal wiring, etc., metal wiring, cover base materials such as chip members such as IC chips, liquid crystal displays, organic electroluminescence displays, electronic paper, interlayer insulating films such as solar cells, bases It can be suitably used as a material for electronic components and electronic equipment such as base materials, adhesive sheets, prepregs and primers.
• the fluorine-containing polyether compound of the present disclosure has a particularly low dielectric constant and a low dielectric loss at high frequencies, so it is suitable as a material for electronic components and electronic devices that use high frequencies, especially microwaves of 3 to 30 GHz.
• it can be suitably used as a material for insulating plates of high-frequency circuits, insulating materials for connection parts, printed circuit boards, bases and antenna covers for high-frequency vacuum tubes, coaxial cables, coated wires such as LAN cables, and the like.
• it can be suitably used as a material for devices such as satellite communication devices and mobile phone base stations that use microwaves of 3 to 30 GHz.
• the printed circuit board is not particularly limited, but examples include printed wiring boards for electronic circuits such as mobile phones, various computers, and communication equipment.
• the coaxial cable is not particularly limited, for example, one having a structure in which an inner conductor, an insulating coating layer, an outer conductor layer and a protective coating layer are laminated in order from the core to the outer periphery can be mentioned.
• the fluorine-containing polyether compound of the present disclosure has a low dielectric constant and a low dielectric loss, and is excellent in heat resistance, solvent solubility, electrical insulation, colorless transparency and flexibility, and can be easily formed into a thin film. Therefore, it can be suitably used for interlayer insulating films, films, adhesive sheets, prepregs, primers, resist materials, and the like. Among others, it is suitable for interlayer insulating films and films.
• the film can be produced by molding the fluorinated polyether compound of the present disclosure by a known film molding method such as an extrusion molding method, a calender molding method, or a solution casting method. Furthermore, the film may be subjected to sandblasting, corona treatment, plasma treatment, etching treatment, or the like.
• GPC Tosoh Corporation high-speed GPC system HLC-8220GPC (column: Tosoh TSKgel ( ⁇ -M), column temperature: 45 ° C., detector: UV-8020, wavelength 254 nm, eluent: N-methyl- 2-pyrrolidone (NMP) (containing 0.01 mol/L lithium bromide), calibration curve: standard polystyrene, column flow rate: 0.2 mL/min)
• FT-IR Infrared spectrum
• FT/IR-4200 FT/IR-4200 manufactured by JASCO Corporation
• Nuclear magnetic resonance spectrum (NMR): BRUKER AC400P (4) Thermogravimetric measurement (TGA): TG/DTA7300 manufactured by Hitachi High-Tech Science Co., Ltd., heating rate 10 ° C./min
• DSC Differential scanning calorimetry
• DSC DSC7000 manufactured by Hitachi High-Tech Science Co., Ltd., heating rate 20 ° C./min
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature.
• the polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification.
• the polymer was vacuum dried at room temperature for 10 hours.
• the mixture was stirred at 170° C. for 24 hours.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature.
• the polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification.
• the polymer was vacuum dried at room temperature for 10 hours.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature. The polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification. The polymer was vacuum dried at room temperature for 10 hours.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature.
• the polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification.
• the polymer was vacuum dried at room temperature for 10 hours.
• the mixture was stirred at 170° C. for 24 hours.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature.
• the polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification.
• the polymer was vacuum dried at room temperature for 10 hours.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature.
• the polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification.
• the polymer was vacuum dried at room temperature for 10 hours.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature.
• the polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification.
• the polymer was vacuum dried at room temperature for 10 hours.
• the polymer After allowing to cool to room temperature, the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature. The polymer was dissolved in tetrahydrofuran (THF) and poured into a large amount of methanol for reprecipitation purification. The polymer was vacuum dried at room temperature for 10 hours. Yield of polymer: 0.93 g (yield: 69%) Logarithmic viscosity ( ⁇ inh ): 0.85 dL/g (NMP solution with a concentration of 0.5 g/dL, measured at 30°C) This polymer was dissolved in THF, cast on a glass plate, and dried under reduced pressure at room temperature for 6 hours, 50° C.
• THF tetrahydrofuran
• Example 10 Synthesis of fluorine-containing polyether (FPPFH-TMPBP) Instead of 4,4-dihydroxybiphenyl (BP) in Example 8, 4,4'-dihydroxy-2,2',3,3',5,5'- A polyether was synthesized by polymerizing at 190° C. for 24 hours using hexamethylbiphenyl (TMPBP).
• FPPFH-TMPBP fluorine-containing polyether
• BP 4,4-dihydroxybiphenyl
• TMPBP hexamethylbiphenyl
• Example 11 Synthesis of fluorine-containing polyether (FPPFH-BisTPM) Instead of 4,4-dihydroxybiphenyl (BP) in Example 8, 4,4-dihydroxytetraphenylmethane (BisTPM) was used and polymerized at 170°C for 12 hours. to synthesize polyethers.
• FPPFH-BisTPM fluorine-containing polyether
• BP 4,4-dihydroxybiphenyl
• BisTPM 4,4-dihydroxytetraphenylmethane
• Example 12 Synthesis of fluorinated polyether (FPPFH-TBISRX) Instead of 9,9-bis(4-hydroxyphenyl)fluorene (BPFL) in Example 6, spiro[fluorene-9,9′-xanthene]-3′,6 Using '-diol (TBISRX), polymerization was carried out at 190° C. for 4 hours to synthesize a polyether.
• FPPFH-TBISRX fluorinated polyether
• BPFL 9,9-bis(4-hydroxyphenyl)fluorene
• TBISRX 9,9-bis(4-hydroxyphenyl)fluorene
• FPPFB-BisA fluorine-containing polyether
• FPPFB 1,4-bis(4-fluorophenyl)perfluorobutane
• FPPFB-BisAF fluorine-containing polyether
• FPPFB 1,4-bis(4-fluorophenyl)perfluorobutane
• Example 15 Synthesis of fluorine-containing polyether (FPPFB-BPFL) Instead of FPPFH in Example 6, 1,4-bis(4-fluorophenyl)perfluorobutane (FPPFB) was used and polymerized at 190 ° C. for 6 hours to obtain a polyether. Ether was synthesized.
• Example 16 Synthesis of fluorine-containing polyether (FPPFB-TBISRX) Instead of FPPFH in Example 12, 1,4-bis(4-fluorophenyl)perfluorobutane (FPPFB) was used to polymerize at 190 ° C. for 4 hours to obtain a polyether. Ether was synthesized.
• Example 17 Synthesis of fluorine-containing polyether (FPPFB-BisPCDE) Instead of FPPFH in Example 4, 1,4-bis(4-fluorophenyl)perfluorobutane (FPPFB) was used and polymerized at 190 ° C. for 5 hours to obtain a polyether. Ether was synthesized.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature.
• the polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification.
• the polymer was vacuum dried at room temperature for 10 hours.
• the polymer was recovered with methanol, heated and washed with methanol, and dried under reduced pressure at room temperature. The polymer was dissolved in chloroform and poured into a large amount of methanol for reprecipitation purification. The polymer was vacuum dried at room temperature for 10 hours.

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• 2022
  • 2022-05-10 JP JP2023521211A patent/JP7710038B2/ja active Active
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