WO2024029406A1 - Composition de revêtement isolant à faible constante diélectrique, produit durci de celle-ci et dispositif d'affichage - Google Patents

Composition de revêtement isolant à faible constante diélectrique, produit durci de celle-ci et dispositif d'affichage Download PDF

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WO2024029406A1
WO2024029406A1 PCT/JP2023/027213 JP2023027213W WO2024029406A1 WO 2024029406 A1 WO2024029406 A1 WO 2024029406A1 JP 2023027213 W JP2023027213 W JP 2023027213W WO 2024029406 A1 WO2024029406 A1 WO 2024029406A1
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dielectric constant
coating composition
insulating coating
group
low dielectric
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PCT/JP2023/027213
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Japanese (ja)
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大輔 平野
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信越化学工業株式会社
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    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

Definitions

  • the present invention relates to a low dielectric constant insulating coating composition, a cured product thereof, and a display device.
  • a bismaleimide resin composition has been proposed that provides a cured product that has a low dielectric constant and a low dielectric loss tangent, has excellent heat resistance and toughness, and has good workability (Patent Document 1).
  • Patent Document 1 a bismaleimide resin composition has been proposed that provides a cured product that has a low dielectric constant and a low dielectric loss tangent, has excellent heat resistance and toughness, and has good workability.
  • curable compositions that can be used as encapsulants for white LEDs that require heat resistance include compounds that have three or more silicon-bonded hydrogen atoms in one molecule and two alkenyl groups in one molecule.
  • a curable composition containing as essential components an organosiloxane having one or more organosiloxanes and a hydrosilylation catalyst has been proposed (Patent Document 2). This curable composition is said to be able to provide a cured product with high hardness, mechanical strength, and crack resistance, and excellent light transmittance in a short wavelength region and gas barrier properties.
  • this document makes no mention of the dielectric properties of the cured product.
  • JP 2021-181532 Publication Japanese Patent Application Publication No. 2020-026502
  • the conventional technology has a problem in that it is not possible to obtain a cured product that has both low dielectric properties (low dielectric constant and low dielectric loss tangent) and high mechanical strength. Therefore, the present invention has been made to solve the above problems, and provides a low dielectric constant insulating coating composition whose cured product has high mechanical strength and low dielectric constant and dielectric loss tangent.
  • the purpose is to provide
  • the present invention provides a low dielectric constant insulating coating composition containing the following (A), (B) and (C).
  • A An addition reaction product of an organosilicon compound represented by the following formula (1) and an organosilicon compound represented by the following formula (2), which has three or more SiH groups in one molecule.
  • reactant (In the formula, R 1 is independently a substituted or unsubstituted divalent hydrocarbon group having 1 to 12 carbon atoms.)
  • R 2 is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms, and R 3 is a single bond or an unsubstituted divalent hydrocarbon group having 1 to 4 carbon atoms.
  • B an organosiloxane compound having two or more alkenyl groups in one molecule
  • C Hydrosilylation reaction catalyst
  • the low dielectric constant insulating coating composition of the present invention can provide a low dielectric constant insulating coating composition that provides a cured product with high mechanical strength and low dielectric constant and dielectric loss tangent.
  • the relative dielectric constant (value of the ratio to the dielectric constant of vacuum) is also simply referred to as "permittivity.”
  • R 1 may be a phenylene group
  • R 2 may be a methyl group or a phenyl group.
  • the organosilicon compound represented by the above formula (1) and the organosilicon compound represented by the above formula (2) are easily available, and component (A), which is an addition reaction product thereof, can be obtained efficiently. I can do it.
  • the above (B) is a compound represented by the following formula (3).
  • R 4 is independently an unsubstituted or substituted monovalent hydrocarbon group
  • R 5 is independently a methyl group or a phenyl group
  • a is an integer from 0 to 50
  • b is an integer from 0 to 100.
  • R 5 is a phenyl group
  • b is 1 to 100.
  • the arrangement order of the siloxane units in parentheses is arbitrary.
  • Such component (B) can be easily obtained.
  • the present invention also provides a cured product obtained by curing the above-mentioned low dielectric constant insulating coating composition.
  • the cured product of the present invention has excellent mechanical strength, low dielectric constant and low dielectric loss tangent.
  • the cured product of the present invention preferably has a dielectric constant of 3.0 or less at 10 GHz and a dielectric loss tangent of 0.01 or less.
  • a cured product with such low dielectric constant insulation is useful as an insulating material, coating material, or sealing material with low transmission loss in the high frequency range.
  • the present invention provides a display device characterized by having a layer made of the above-mentioned cured product.
  • the cured product used has high mechanical strength, low dielectric constant and dielectric loss tangent, and also has transparency, so the display device has high reliability.
  • the low dielectric constant insulating coating composition of the present invention has high mechanical strength, low dielectric constant, and low dielectric loss tangent of the obtained cured product, and therefore is suitable for electronic devices and electrical devices with low transmission loss in the high frequency range. It is useful as a coating material.
  • the present invention is a low dielectric constant insulating coating composition containing the following (A), (B), and (C).
  • A An addition reaction product of an organosilicon compound represented by the following formula (1) and an organosilicon compound represented by the following formula (2), which has three or more SiH groups in one molecule.
  • reactant (In the formula, R 1 is independently a substituted or unsubstituted divalent hydrocarbon group having 1 to 12 carbon atoms.)
  • R 2 is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms, and R 3 is a single bond or an unsubstituted divalent hydrocarbon group having 1 to 4 carbon atoms.
  • B an organosiloxane compound having two or more alkenyl groups in one molecule
  • C Hydrosilylation reaction catalyst
  • the low dielectric constant insulating coating composition of the present invention is an addition-curing silicone composition containing the following components (A) to (C).
  • the low dielectric constant insulating coating composition of the present invention can be prepared by mixing the following components (A) to (C) and, if necessary, other components by a conventionally known method. Each component will be explained in detail below.
  • Component (A) in the low dielectric constant insulating coating composition of the present invention functions as a crosslinking agent by causing a hydrosilylation reaction with component (B) described below.
  • Component (A) is an addition reaction product of an organosilicon compound represented by the following formula (1) and an organosilicon compound represented by the following formula (2), and has an SiH group (hydrosilyl group) in one molecule.
  • ) is an addition reaction product having three or more.
  • R 1 is independently a substituted or unsubstituted divalent hydrocarbon group having 1 to 12 carbon atoms.
  • R 2 is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms
  • R 3 is a single bond or an unsubstituted divalent hydrocarbon group having 1 to 4 carbon atoms. .
  • organosilicon compound represented by the above formula (2) has three alkenyl groups in one molecule but does not have a siloxane bond, so it is an organosiloxane compound having two or more alkenyl groups in one molecule. It is clearly distinguished from a certain component (B).
  • the divalent hydrocarbon group having 1 to 12 carbon atoms represented by R 1 includes methylene group, ethylene group, n-propylene group, n-butylene group, n-pentylene group, n-hexylene group, cyclohexylene group, Examples include alkylene groups such as n-octylene groups, arylene groups such as phenylene groups and naphthylene groups, and those in which some or all of the hydrogen atoms of these groups are substituted with halogen atoms such as fluorine, bromine, and chlorine. and R 1 is particularly preferably a phenylene group.
  • the monovalent hydrocarbon group having 1 to 12 carbon atoms represented by R 2 includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group.
  • alkyl groups such as octyl groups, cycloalkyl groups such as cyclohexyl groups, alkenyl groups such as vinyl groups, allyl groups, and propenyl groups, aryl groups such as phenyl groups, tolyl groups, xylyl groups, and naphthyl groups, benzyl groups, and phenyl groups.
  • Examples include aralkyl groups such as ethyl group and phenylpropyl group, and those in which some or all of the hydrogen atoms of these groups are substituted with halogen atoms such as fluorine, bromine, chlorine, etc., and R 2 is methyl or A phenyl group is preferred, and a phenyl group is particularly preferred.
  • Examples of the unsubstituted divalent hydrocarbon group having 1 to 4 carbon atoms represented by R 3 include alkylene groups such as methylene group, ethylene group, n-propylene group, and n-butylene group.
  • R 3 is a single bond, it represents an organosilicon compound in which a vinyl group is directly bonded to a silicon atom.
  • R3 a single bond, a methylene group, or an ethylene group is particularly preferable.
  • organosilicon compound represented by the above formula (1) Preferred specific examples of the organosilicon compound represented by the above formula (1) are shown below, but the invention is not limited thereto. Further, the organosilicon compounds represented by the above formula (1) can be used alone or in combination of two or more.
  • component (A) which is an addition reaction product between the organosilicon compound represented by the above formula (1) and the organosilicon compound represented by the above formula (2), include a compound represented by the following unit formula: can be mentioned. (In the formula, n is an integer from 1 to 10.)
  • component (A) can be used singly or in combination of two or more of the compounds represented by the above unit formula.
  • compounds represented by the above unit formula, where n is 1 are referred to as compound N 1
  • compounds represented by the above unit formula, where n is 2 are referred to as compound N 2
  • compounds where n is 3 are referred to as compound N 3
  • k is a compound N k
  • the molar fraction of each compound in a mixture consisting of compounds N 1 , N 2 , N 3 , N 4 ...N k compounds N 1 , N 2 , N 3 , N
  • the amount of each compound when the total amount of 4 ...N k is 1 mole) is preferably in the following range.
  • F N1 :F N2 :F N3 50-60:20-30:5-15 (mol%)
  • F Nk represents the molar fraction of compound N k .
  • the total molar fraction of the remaining compounds N 4 or higher (N 4 to N k ) can be 5 to 15 (mol %). It is preferable to use such component (A) because it improves the mechanical strength of the cured product.
  • Component (A) in the low dielectric constant insulating coating composition of the present invention preferably contains an excess amount of the compound represented by the above formula (1) with respect to 1 mole of the compound represented by the above formula (2). can be obtained by mixing more than 3 moles and less than 30 moles, more preferably more than 4.5 moles and less than 15 moles, and subjecting both to a hydrosilylation reaction in the presence of a catalyst.
  • any known catalyst can be used.
  • Platinum-based catalysts include platinum group metal catalysts such as palladium-based catalysts and rhodium-based catalysts.
  • addition reaction conditions, purification conditions, use of solvent, etc. are not particularly limited, and known methods may be used.
  • the component (A) in the low dielectric constant insulating coating composition of the present invention may consist of one type of compound or a combination (mixture) of two or more types of compounds.
  • SiH groups can be added to one molecule for each compound by selecting an appropriate combination of measurement methods (for example, 1 H-NMR and GPC, etc.). It can be confirmed that there are three or more.
  • Component (B) in the low dielectric constant insulating coating composition of the present invention is an organosiloxane compound having two or more alkenyl groups in one molecule.
  • Component (B) undergoes an addition reaction with component (A) in the presence of (C) a hydrosilylation catalyst described below.
  • a hydrosilylation catalyst described below.
  • the organosiloxane compound linear, branched, or cyclic organopolysiloxanes can be used.
  • component (B) include, but are not limited to, dimethylsiloxane/methylvinylsiloxane copolymer with trimethylsiloxy groups endblocked at both molecular chain ends, dimethylsiloxane/diphenylsiloxane/methylvinylsiloxane endblocked with trimethylsiloxy groups at both molecular chain ends. Examples include copolymers, dimethylsiloxane/diphenylsiloxane copolymers with dimethylvinylsiloxy groups endblocked at both molecular chain ends, and component (B) can be used alone or in combination of two or more.
  • Component (B) preferably has 0.10 to 0.90 mol, more preferably 0.20 to 0.50 mol of alkenyl groups such as vinyl groups per 100 g. Since such component (B) has sufficient alkenyl groups capable of addition reaction (crosslinking), the cured product provided by this component has high hardness and high strength. Furthermore, the viscosity of component (B) at 25° C. is preferably 5 to 3000 mPa ⁇ s, more preferably 10 to 2000 mPa ⁇ s. Component (B) exhibits good fluidity at room temperature, is easy to prepare as a composition, has appropriate viscosity when applied to a substrate, and has excellent workability. In the present invention, the viscosity at 25° C. may be measured using a B-type rotational viscometer in accordance with JIS-K7117-1:1999.
  • Component (B) is preferably a compound represented by the following formula (3), that is, a linear organopolysiloxane.
  • R 4 is independently an unsubstituted or substituted monovalent hydrocarbon group
  • R 5 is independently a methyl group or a phenyl group
  • a is an integer from 0 to 50
  • b is an integer from 0 to 100.
  • R 5 is a phenyl group
  • b is 1 to 100.
  • the arrangement order of the siloxane units in parentheses is arbitrary.
  • Examples of the unsubstituted or substituted monovalent hydrocarbon group represented by R 4 include aliphatic unsaturated groups and monovalent hydrocarbon groups other than aliphatic unsaturated groups, such as methyl group, ethyl group, Alkyl groups having 1 to 6 carbon atoms such as propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group; carbon atoms such as chloromethyl group and 3,3,3-trifluoropropyl group Examples include haloalkyl groups having 1 to 4 atoms; aryl groups having 6 to 10 carbon atoms such as phenyl and tolyl groups; alkenyl groups such as vinyl and allyl groups. Among these, alkyl groups having 1 to 6 carbon atoms, phenyl groups, and vinyl groups are preferred, and methyl groups are particularly preferred.
  • a is an integer of 0 to 50, preferably 1 to 10, more preferably 1 to 7, and even more preferably 2 to 4.
  • b is an integer from 0 to 100, preferably from 0 to 50, more preferably from 1 to 10, even more preferably from 2 to 4.
  • R 5 is a phenyl group, and b is 1 to 100.
  • the siloxane units in parentheses can be arranged in any order.
  • the organopolysiloxane represented by formula (3) can be produced by, for example, hydrolyzing and condensing a bifunctional silane such as dichlorodiphenylsilane or dialkoxydiphenylsilane, or simultaneously with aliphatic unsaturation. It is obtained by capping the ends with group-containing siloxane units.
  • the blending amount of component (B) can be such that the molar ratio of SiH groups to aliphatic unsaturated groups in the composition (SiH groups/aliphatic unsaturated groups) is 0.5 or more and 5 or less, The amount is preferably 0.8 or more and 2 or less. When the molar ratio (SiH group/aliphatic unsaturated group) is 0.5 or more and 5 or less, the composition of the present invention can be sufficiently cured.
  • the hydrosilylation reaction catalyst which is component (C) of the present invention can be the same as that used in the preparation of component (A) above.
  • the amount of component (C) added to the low dielectric constant insulating coating composition of the present invention is 1 to 500 ppm as platinum group metal atoms based on the mass of the entire composition from the viewpoint of accelerating the reaction and preventing coloring of the cured product.
  • the amount is preferably about 1 to 100 ppm, and even more preferably 2 to 12 ppm.
  • components (A) to (C) In addition to the above-mentioned components (A) to (C), components such as an antioxidant and an inorganic filler may be added to the low dielectric constant insulating coating composition, if necessary.
  • the addition-reactive carbon-carbon double bond in the component (B) may remain unreacted, and it may be exposed to the air. Oxidation due to the oxygen inside may cause the cured product to become discolored. Therefore, such coloring can be prevented by adding an antioxidant to the low dielectric constant insulating coating composition of the present invention, if necessary.
  • antioxidants can be used, such as 2,6-di-t-butyl-4-methylphenol, 2,5-di-t-amylhydroquinone, and 2,5-di-t-amylhydroquinone.
  • t-Butylhydroquinone 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis(4- ethyl-6-t-butylphenol) and the like. These can be used alone or in combination of two or more.
  • this antioxidant when using this antioxidant, its blending amount is not particularly limited, but it is usually 1 to 10,000 ppm, particularly 10 to 10,000 ppm, based on the total mass of components (A) and (B). It is preferable to add about 1,000 ppm. By incorporating the amount within the above range, the antioxidant ability is fully exhibited, and a cured product with excellent optical properties without coloration, cloudiness, oxidative deterioration, etc. can be obtained.
  • Inorganic filler The viscosity of the low dielectric constant insulating coating composition of the present invention, the hardness of the cured product obtained from the low dielectric constant insulating coating composition of the present invention, etc. can be adjusted, the strength can be improved, and the dispersion of the phosphor can be controlled. To improve the quality, inorganic fillers such as nanosilica, fused silica, crystalline silica, titanium oxide, nanoalumina, alumina, etc. may be added.
  • the blending amount is preferably 5 to 500 parts by mass, more preferably 10 to 200 parts by mass, based on the total of 100 parts by mass of components (A) and (B). .
  • the low dielectric constant insulating coating composition of the present invention is easy to handle, and the hardness and strength of the cured product thereof are desirable.
  • the low dielectric constant insulating coating composition of the present invention may contain an adhesion improver.
  • the adhesion improver include a silane coupling agent, an oligomer thereof, and a polysiloxane having the same reactive group as the silane coupling agent.
  • the adhesion improver is preferably a compound represented by the following formula (4) or a silane coupling agent having an allyl isocyanurate structure as an organic functional group.
  • s is an integer from 1 to 3
  • t is an integer from 0 to 3
  • u is an integer from 0 to 3, provided that s+t+u is an integer from 4 to 5.
  • the arrangement order of the siloxane units is arbitrary.
  • Examples of the silane coupling agent having an allyl isocyanurate structure as an organic functional group include a compound represented by the following formula (5).
  • R and R' in the formula shall be applied only to the following formula.
  • at least one R' is an allyl group, and the others are hydrogen atoms, alkyl groups, cycloalkyl groups, aryl groups, heteroaryl groups, non-aromatic heterocyclic rings, (CH 2 ) 3 Si(OR ) 3 or an allyl group
  • R is an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a non-aromatic heterocyclic ring, or an allyl group.
  • R in the above formula is preferably a C1-4 alkyl group, more preferably a methyl group or an ethyl group.
  • R' is preferably (CH 2 ) 3 Si(OR) 3 or an allyl group.
  • silane coupling agent having an allyl isocyanurate structure examples include X-12-1290 (manufactured by Shin-Etsu Chemical Co., Ltd.) and compounds represented by the following formula.
  • adhesion improver examples include those represented by the following formulas, but are not limited thereto.
  • the adhesion improver may be a commercially available product.
  • the adhesion improver is an optional component that is added to the low dielectric constant insulating coating composition of the present invention and its cured product to improve the adhesion to the substrate.
  • the base material refers to metal materials such as gold, silver, copper, and nickel, ceramic materials such as aluminum oxide, aluminum nitride, and titanium oxide, and polymeric materials such as silicone resin and epoxy resin.
  • the adhesion improvers can be used alone or in combination of two or more.
  • the blending amount is preferably 1 to 30 parts by mass, more preferably 1 to 10 parts by mass, based on the total of 100 parts by mass of components (A) and (B). be. With such a blending amount, the low dielectric constant insulating coating composition of the present invention and its cured product effectively improve the adhesion to the substrate, and are less likely to be colored.
  • reaction control agents such as 1-ethynylcyclohexanol and 3,5-dimethyl-1-hexyn-3-ol can be added.
  • a light stabilizer to impart resistance to photodeterioration caused by light energy such as sunlight and fluorescent lamps.
  • a hindered amine stabilizer that captures radicals generated by photooxidative deterioration is suitable, and when used in combination with an antioxidant, the antioxidant effect is further improved.
  • Specific examples of the light stabilizer include bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, 4-benzoyl-2,2,6,6-tetramethylpiperidine, and the like.
  • the total amount of components (A), (B) and (C) is preferably 50 to 100% by mass, more preferably 80 to 100% by mass. It is preferably 90 to 100% by mass, and more preferably 90 to 100% by mass. Further, the low dielectric constant insulating coating composition of the present invention can be produced by uniformly mixing the above-mentioned components.
  • the low dielectric constant insulating coating composition of the present invention contains the above components, but hitherto such compositions have shown excellent mechanical strength and low dielectric property values (permittivity and dielectric loss tangent) as described below. It was not known or predicted that it would give a cured product with this combination.
  • Patent Document 2 describes a compound having three or more hydrogen atoms bonded to a silicon atom in one molecule, an organosiloxane having two or more alkenyl groups in one molecule, and a hydrosilylation catalyst.
  • a curable composition containing the above is described, and its use is as a curable composition that can be used as an encapsulant for white LEDs that require heat resistance.
  • this curable composition has high hardness, mechanical strength, and crack resistance, and can provide a cured product with excellent light transmittance in the short wavelength region and gas barrier properties. No mention is made of the dielectric properties of the cured product.
  • a cured product with a low dielectric constant is obtained by curing a composition containing a silsesquioxane having an epoxy group and a curing agent (Japanese Unexamined Patent Publication No. 2007-332211). 3) Due to the low dielectric constant material made by dispersing a solid additive in a silicone polymer (having a structure in which a space is formed at the interface between the silicone polymer and the solid additive), the cured product has a higher dielectric strength than conventional materials. Realizes a low dielectric constant (Japanese Patent Application Laid-Open No. 2010-003761).
  • the key to achieving low dielectric characteristics in the GHz band is to reduce polarization from within the structure.
  • the dielectric constant is expressed by the Clausius-Mossotti equation below, in which molar polarizability and molar volume are factors. For this reason, it is important to reduce the polarization and increase the molar volume in order to lower the dielectric constant.
  • Dielectric constant [1+2( ⁇ Pm/ ⁇ Vm)]/[1-( ⁇ Pm/ ⁇ Vm)] (Pm: molar polarizability of the atomic group, Vm: molar volume of the atomic group)
  • the dielectric loss tangent (tan ⁇ ) is a delay in dielectric response to an alternating current electric field, and in the GHz band, dipole orientation relaxation is the main factor. Therefore, in order to reduce the dielectric loss tangent, a method of eliminating the dipole (creating a nearly non-polar structure) can be considered. Therefore, from the viewpoint of low dielectric properties, the coating is required to reduce polarization in its structure and to reduce dipoles as much as possible (to make the structure nearly non-polar).
  • the addition-curable curable composition described in Patent Document 2 has a low dielectric constant insulation property because silanol groups derived from SiH groups (which cause polarization) may remain and reduce the dielectric loss tangent. It was completely unexpected that a coating composition would be obtained. Moreover, since the above-mentioned curable composition provides a cured product with high hardness, mechanical strength, and crack resistance, it was completely unexpected that the coating would have a high density and a low dielectric constant. The present invention was achieved for the first time when the present inventors discovered that, contrary to such predictions, the cured product obtained by curing can have both high mechanical strength and low relative dielectric constant and dielectric loss tangent. .
  • the low dielectric constant insulating coating composition of the present invention is cured to obtain the cured product of the present invention.
  • the cured product has excellent mechanical strength, low dielectric constant, and low dielectric loss tangent.
  • the curing conditions for the low dielectric constant insulating coating composition of the present invention are not particularly limited, but preferably conditions are 60 to 180°C and 5 to 180 minutes.
  • the cured product obtained by curing the low dielectric constant insulating coating composition of the present invention preferably has a dielectric constant of 3.0 or less at 10 GHz and a dielectric loss tangent of 0.01 or less. Within this range, high frequency dielectric properties are excellent.
  • the relative permittivity and dielectric loss tangent of the cured product at 10 GHz can be measured by the cavity resonator method in accordance with JIS C2565.
  • the dielectric constant and dielectric loss tangent of a 0.3 mm thick cured product at 10 GHz may be measured using a cavity resonator dielectric constant measuring device (manufactured by AET Co., Ltd.).
  • the mechanical strength (hardness, elongation at cutting) of the cured product can be measured as follows. (Hardness) Using a cured product of a predetermined thickness, hardness (ShoreD) is measured at 23° C. according to ASTM D 2240. (Elongation at cutting) Measure at 23°C using a cured product of a predetermined thickness according to JIS-K-6249.
  • An insulating coating layer can be formed by applying the low dielectric constant insulating coating composition of the present invention to various substrates, parts, etc. directly or via another layer and curing the composition. Further, since the cured product obtained by curing the low dielectric constant insulating coating composition of the present invention has transparency, it is suitable for use as a display device.
  • Example 1 (A) Reaction product obtained in Synthesis Example 1: 75 parts by mass, (B-1) Organopolysiloxane having 0.22 mol of vinyl groups per 100 g and having a viscosity of 2,000 mPa ⁇ s at 25°C, represented by the average unit formula M Vi ⁇ 2 D 2 ⁇ 3 : 114 parts by mass, (B-2) Organopolysiloxane having a viscosity of 10 mPa ⁇ s at 25°C and having 0.50 mol of vinyl groups per 100 g, represented by the average unit formula M Vi 2 D 2 ⁇ : 9 parts by mass, (C) Platinum-vinylsiloxane complex: an amount of 3 ppm as platinum metal atoms based on the total mass of (A), (B-1) and (B-2), As an adhesion improver, a compound represented by the following formula (6): 2 parts by mass, A composition was obtained by mixing 0.07 parts by mass of 1-ethynylcyclohexanol
  • This composition was poured into metal frames with a thickness of 2 mm and 0.3 mm, and heated at 150° C. for 4 hours to obtain a cured product.
  • the SiH/Vi ratio (SiH group/aliphatic unsaturated group) in the above composition was 0.89.
  • Example 2 (A) Reaction product obtained in Synthesis Example 1: 75 parts by mass, (B-1) Organopolysiloxane having 0.22 mol of vinyl groups per 100 g and having a viscosity of 2,000 mPa ⁇ s at 25°C, represented by the average unit formula M Vi ⁇ 2 D 2 ⁇ 3 : 123 parts by mass, (C) Platinum-vinylsiloxane complex: an amount of 3 ppm as platinum metal atoms based on the total mass of (A) and (B-1), As an adhesion improver, a compound represented by the above formula (6): 2 parts by mass, A composition was obtained by mixing 0.07 parts by mass of 1-ethynylcyclohexanol as a reaction control agent. This composition was poured into metal frames with a thickness of 2 mm and 0.3 mm, and heated at 150° C. for 4 hours to obtain a cured product. The SiH/Vi ratio in the above composition was 0.97.
  • Example 1 As a silicone material whose substituent is a methyl group, a methyl silicone resin curable composition (trade name: KER-2300, manufactured by Shin-Etsu Chemical Co., Ltd., viscosity (25°C): 5,000 mPa ⁇ s) was used in Example 1. Similarly, it was poured into metal frames of 2 mm and 0.3 mm thickness, and heated at 150° C. for 2 hours to obtain a cured product.
  • KER-2300 manufactured by Shin-Etsu Chemical Co., Ltd., viscosity (25°C): 5,000 mPa ⁇ s
  • the compositions of Examples 1 and 2 had appropriate viscosity when applied to a substrate and were excellent in workability.
  • the cured products obtained in Examples 1 and 2 have high hardness and high strength, have a relative dielectric constant of 3.0 or less at 10 GHz, and a dielectric loss tangent of 0.01 or less, and have excellent high-frequency dielectric properties. That's what I found out.
  • a low dielectric constant insulating coating composition containing the following (A), (B) and (C).
  • A An addition reaction product of an organosilicon compound represented by the following formula (1) and an organosilicon compound represented by the following formula (2), which has three or more SiH groups in one molecule.
  • reactant (In the formula, R 1 is independently a substituted or unsubstituted divalent hydrocarbon group having 1 to 12 carbon atoms.)
  • R 2 is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms, and R 3 is a single bond or an unsubstituted divalent hydrocarbon group having 1 to 4 carbon atoms.
  • R 4 is independently an unsubstituted or substituted monovalent hydrocarbon group
  • R 5 is independently a methyl group or a phenyl group
  • a is an integer from 0 to 50
  • b is an integer from 0 to 100.
  • R 5 is a phenyl group
  • b is 1 to 100.
  • the arrangement order of the siloxane units in parentheses is arbitrary.
  • [5] The cured product according to [4], which has a dielectric constant of 3.0 or less and a dielectric loss tangent of 0.01 or less at 10 GHz.
  • [6] A display device comprising a layer made of the cured product according to [4] or [5].

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Abstract

La présente invention est une composition de revêtement isolant à faible constante diélectrique contenant : (A) un produit d'addition de réaction d'un composé de silicium organique représenté par la formule (1) et d'un composé de silicium organique représenté par la formule (2), le produit d'addition de réaction ayant trois groupes SiH ou plus dans une molécule ; (B) un composé organosiloxane ayant deux groupes alcényle ou plus dans une molécule ; et (C) un catalyseur de réaction d'hydrosilylation. Une composition de revêtement isolant à faible constante diélectrique dans laquelle un produit durci obtenu par durcissement a une résistance mécanique élevée et une faible constante diélectrique et une tangente de dissipation est ainsi fournie. (Dans les formules, R1 est un groupe hydrocarboné en C1-12 divalent substitué ou non substitué indépendamment, R2 est un groupe hydrocarboné en C1-12 monovalent substitué ou non substitué, et R3 est une liaison simple ou un groupe hydrocarboné en C1-4 divalent non substitué).
PCT/JP2023/027213 2022-08-01 2023-07-25 Composition de revêtement isolant à faible constante diélectrique, produit durci de celle-ci et dispositif d'affichage WO2024029406A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000080280A (ja) * 1998-09-07 2000-03-21 Shin Etsu Chem Co Ltd 酸化亜鉛充填付加反応硬化型シリコーンゴム組成物及びその硬化物
JP2006152063A (ja) * 2004-11-26 2006-06-15 Jsr Corp 新規ポリカルボシランおよびその製造方法、膜形成用組成物、ならびに膜およびその形成方法
JP2020026502A (ja) * 2018-08-15 2020-02-20 信越化学工業株式会社 硬化性組成物、該組成物の硬化物、及び該硬化物を用いた半導体装置
WO2021240302A2 (fr) * 2020-05-28 2021-12-02 3M Innovative Properties Company Composition durcissable, produit de réaction obtenu à partir de celle-ci, et article électronique comprenant celle-ci
JP2022084508A (ja) * 2020-11-26 2022-06-07 信越化学工業株式会社 低誘電化剤、これを含む低誘電性樹脂組成物および樹脂の低誘電化方法、並びに低誘電化剤としての使用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000080280A (ja) * 1998-09-07 2000-03-21 Shin Etsu Chem Co Ltd 酸化亜鉛充填付加反応硬化型シリコーンゴム組成物及びその硬化物
JP2006152063A (ja) * 2004-11-26 2006-06-15 Jsr Corp 新規ポリカルボシランおよびその製造方法、膜形成用組成物、ならびに膜およびその形成方法
JP2020026502A (ja) * 2018-08-15 2020-02-20 信越化学工業株式会社 硬化性組成物、該組成物の硬化物、及び該硬化物を用いた半導体装置
WO2021240302A2 (fr) * 2020-05-28 2021-12-02 3M Innovative Properties Company Composition durcissable, produit de réaction obtenu à partir de celle-ci, et article électronique comprenant celle-ci
JP2022084508A (ja) * 2020-11-26 2022-06-07 信越化学工業株式会社 低誘電化剤、これを含む低誘電性樹脂組成物および樹脂の低誘電化方法、並びに低誘電化剤としての使用

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