WO2023032724A1 - 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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Publication number
WO2023032724A1
WO2023032724A1 PCT/JP2022/031482 JP2022031482W WO2023032724A1 WO 2023032724 A1 WO2023032724 A1 WO 2023032724A1 JP 2022031482 W JP2022031482 W JP 2022031482W WO 2023032724 A1 WO2023032724 A1 WO 2023032724A1
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Prior art keywords
dielectric constant
insulating coating
coating composition
component
low dielectric
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PCT/JP2022/031482
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English (en)
Japanese (ja)
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栄一 田部井
寛人 大和田
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信越化学工業株式会社
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Priority to JP2023545457A priority Critical patent/JPWO2023032724A1/ja
Publication of WO2023032724A1 publication Critical patent/WO2023032724A1/fr

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    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
    • H01B3/22—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils hydrocarbons
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes

Definitions

  • the present invention relates to a low dielectric constant insulating coating composition, a cured product thereof, and a display device.
  • Patent Document 1 a polycyclic hydrocarbon skeleton-containing compound having two addition-reactive carbon-carbon double bonds in one molecule and three or more silicon-bonded hydrogen atoms in one molecule. and a hydrosilylation catalyst as essential components.
  • the present invention aims to provide a low dielectric constant insulating coating composition which has a low dielectric constant and a low dielectric loss tangent in a cured product obtained by curing, and has excellent workability when applied to a substrate. aim.
  • the present inventors have conducted intensive studies to achieve the above object, and have found that a curable silicone composition containing a specific component containing a polycyclic hydrocarbon skeleton has excellent workability and a low dielectric constant.
  • the present invention was completed by discovering that a cured product having a low dielectric constant and a low dielectric loss tangent can be obtained. That is, the present invention provides a low dielectric constant insulating coating composition, a cured product thereof, and a display device as described below.
  • R is independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms or an alkoxy group having 1 to 6 carbon atoms.
  • a compound having two silicon-bonded hydrogen atoms in one molecule represented by (b) an addition reaction product with a polycyclic hydrocarbon having two addition-reactive carbon-carbon double bonds in one molecule, and an addition-reactive carbon-carbon double bond in one molecule; an addition reaction product having at least two in A low dielectric constant insulating coating composition comprising (B) a compound having 3 or more silicon-bonded hydrogen atoms in one molecule and (C) a hydrosilylation reaction catalyst.
  • the polycyclic hydrocarbon of (b) is 5-vinylbicyclo[2.2.1]hept-2-ene, 6-vinylbicyclo[2.2.1]hept-2-ene, or a combination of the two.
  • the low dielectric constant insulating coating composition according to [1].
  • the component (B) contains 1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5,7,9-pentamethylcyclopentasiloxane, or a mixture of both [1] or [2 ].
  • the component (B) is 5-vinylbicyclo[2.2.1]hept-2-ene, 6-vinylbicyclo[2.2.1]hept-2-ene or a mixture of both; including addition reaction products with 1,3,5,7-tetramethylcyclotetrasiloxane, 1,3,5,7,9-pentamethylcyclopentasiloxane, or mixtures of both [1]-[3]
  • the low dielectric constant insulating coating composition according to any one of .
  • [5] A cured product of the low dielectric constant insulating coating composition according to any one of [1] to [4].
  • the low dielectric constant insulating coating composition of the present invention has a viscosity suitable for coating on a substrate, is excellent in workability, and the obtained cured product has a low dielectric constant and a low dielectric loss tangent. It is useful as a coating material for electronic and electrical devices with low transmission loss in the high frequency range.
  • the component is (a) the following general formula (1):
  • R is independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms or an alkoxy group having 1 to 6 carbon atoms.
  • a compound having two silicon-bonded hydrogen atoms in one molecule represented by (b) an addition reaction product with a polycyclic hydrocarbon having two addition-reactive carbon-carbon double bonds in one molecule, and an addition-reactive carbon-carbon double bond in one molecule; is an addition reaction product having at least two in
  • ⁇ (a) component> (a) A compound having two silicon-bonded hydrogen atoms (hereinafter sometimes referred to as "SiH") represented by the above general formula (1) in one molecule is a reaction raw material for component (A). .
  • SiH silicon-bonded hydrogen atoms
  • R is the above monovalent hydrocarbon group, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl Alkyl groups such as group, sec-hexyl group; Cycloalkyl groups such as cyclopentyl group and cyclohexyl group; Aryl groups such as phenyl group and o-, m-, p-tolyl group; Aralkyl groups such as benzyl group and 2-phenylethyl group groups; alkenyl groups such as vinyl group, allyl group, 1-butenyl group and 1-hexenyl group; alkenylaryl groups such as p-vinylphenyl group; and one or more hydrogen atoms bonded to carbon atoms in these groups is substituted with a halogen atom, a cyano group, an epoxy
  • R is the alkoxy group
  • examples of the case where R is the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group.
  • the above R is preferably a group other than an alkenyl group and an alkenylaryl group, and in particular, the component (a) in which all of the Rs are methyl groups is easy to industrially produce. is preferred due to its availability.
  • addition-reactive means It means the ability to undergo the addition of a hydrogen atom (known as a hydrosilylation reaction).
  • the component (b) is (i) those in which an addition-reactive carbon-carbon double bond is formed between two adjacent carbon atoms among the carbon atoms forming the polycyclic skeleton of the polycyclic hydrocarbon; (ii) hydrogen atoms bonded to carbon atoms forming the polycyclic skeleton of the polycyclic hydrocarbon are replaced by addition-reactive carbon-carbon double bond-containing groups, or (iii) of the carbon atoms forming the polycyclic skeleton of the polycyclic hydrocarbon, an addition-reactive carbon-carbon double bond is formed between two adjacent carbon atoms, and the polycyclic Any hydrogen atom bonded to a carbon atom forming the hydrocarbon polycyclic skeleton may be replaced by an addition-reactive carbon-carbon double bond-containing group.
  • Structural formula (x) below: 5-vinylbicyclo[2.2.1]hept-2-ene represented by Structural formula (y) below: 6-vinylbicyclo[2.2.1]hept-2-ene represented by Combinations of both are included. (Hereinafter, when there is no need to distinguish between these three substances, they may be collectively referred to as "vinylnorbornene.")
  • the substitution position of the vinyl group of the vinylnorbornene may be either cis configuration (exo type) or trans configuration (endo type). Since there is no difference between the two configurations, a combination of isomers of both configurations may be used.
  • Component (A) is the above component (b) having two addition-reactive carbon-carbon double bonds in one molecule, per 1 mol of the component (a) having two SiH in one molecule.
  • the (A) component thus obtained is derived from the component (a) in addition to the addition-reactive carbon-carbon double bond derived from the component (b) (specifically, R in the general formula (1) can contain addition-reactive carbon-carbon double bonds (derived from There are two. If there are too many addition-reactive carbon-carbon double bonds, the cured product obtained by curing the composition of the present invention tends to crack.
  • hydrosilylation reaction catalyst all conventionally known catalysts can be used.
  • platinum group metal catalysts such as palladium catalysts and rhodium catalysts.
  • the addition reaction conditions, the use of solvents, etc. are not particularly limited, and may be as usual.
  • component (A) As described above, in the preparation of component (A), an excess molar amount of component (b) is used with respect to component (a), so component (A) is derived from the structure of component (b). It has two addition-reactive carbon-carbon double bonds in one molecule. Furthermore, component (A) has a residue derived from component (a) above, which residue is derived from the structure of component (b) above but does not have an addition-reactive carbon-carbon double bond. It may also include structures joined by divalent residues of polycyclic hydrocarbons.
  • component (A) for example, the following general formula (4): YX-(Y'-X) p -Y (4) (Wherein, X is the divalent residue of the compound of component (a) above, Y is the monovalent residue of the polycyclic hydrocarbon of component (b) above, and Y′ is the residue of the above (b ) is a divalent residue of the component and p is an integer from 0 to 10, preferably from 0 to 5)
  • X is the divalent residue of the compound of component (a) above
  • Y is the monovalent residue of the polycyclic hydrocarbon of component (b) above
  • Y′ is the residue of the above (b ) is a divalent residue of the component
  • p is an integer from 0 to 10, preferably from 0 to 5
  • the value of p which is the number of repeating units represented by (Y'-X), can be adjusted by adjusting the excess molar amount of the component (b) to be reacted with respect to 1 mol of the component (a). can be set by
  • Y in the general formula (4) includes, for example, the following structural formula: (hereinafter, if it is not necessary to distinguish between these six groups, they are collectively referred to as "NB groups", and the six types of structures are referred to as “NB” without distinguishing may be abbreviated).
  • Y′ in the general formula (4) include the following structural formula: A bivalent residue represented by is included.
  • the asymmetric divalent residue represented by the above structural formula is not limited to the left-right direction as described above, and the above structural formula substantially represents each of the above structures on paper. It also shows the structure rotated 180 degrees.
  • Suitable specific examples of the component (A) represented by the general formula (4) are shown below, but are not limited thereto. (The meaning of "NB” is as described above, and “Me” in the formula represents a methyl group (the same applies hereinafter).)
  • the (A) component of the present invention can be used singly or in combination of two or more.
  • the component (B) is a compound having 3 or more SiH in one molecule.
  • the SiH in the component (B) is added to the addition-reactive carbon-carbon double bond that the component (A) has at least two in one molecule by a hydrosilylation reaction to form a cured product with a three-dimensional network structure. give.
  • the (B) component is, for example, the following general formula (5):
  • R 1 is independently a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group other than an alkenyl group, having 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms, and q is 3 to 10 , preferably an integer of 3 to 8, r is an integer of 0 to 7, preferably 0 to 2, and the sum of q + r is an integer of 3 to 10, preferably 3 to 6)
  • a cyclic siloxane compound represented by is mentioned.
  • R 1 in the general formula (5) is an unsubstituted or substituted monovalent hydrocarbon group other than an alkenyl group
  • R 1 in the general formula (5) is an unsubstituted or substituted monovalent hydrocarbon group other than an alkenyl group
  • R 1 in the general formula (5) is an unsubstituted or substituted monovalent hydrocarbon group other than an alkenyl group
  • R 1 in the general formula (5) is an unsubstituted or substituted monovalent hydrocarbon group other than an alkenyl group
  • R 1 in the general formula (5) examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert- Alkyl groups such as butyl group, pentyl group, isopentyl group, hexyl group and sec-hexyl group; Cycloalkyl groups such as cyclopentyl group and cyclohexyl group; Aryl groups such as phenyl group and
  • R 1 is preferably a methyl group, and in particular, component (B) in which all R 1 are methyl groups is easy to industrially produce and readily available.
  • component (B) for example, one or two of the above vinylnorbornenes and 1,3,5,7-tetramethylcyclotetrasiloxane are hydrosilylated to obtain SiH in one molecule.
  • the component (B) can be used singly or in combination of two or more.
  • the composition of the present invention contains a component having hydrogen atoms bonded to silicon atoms other than component (B) and/or an addition-reactive carbon-carbon dihydrogen atom bonded to silicon atoms other than component (A).
  • a component with a double bond can be included. Therefore, the amount of hydrogen atoms bonded to silicon atoms in the present composition per mol of addition-reactive carbon-carbon double bonds bonded to silicon atoms in the present composition is usually 0.5 to 3.0. mol, preferably 0.8 to 2.0 mol.
  • the amount of component (B) to be added to the low dielectric constant insulating coating composition of the present invention is the addition reactive carbon-carbon double bond in component (A).
  • the amount of SiH in component (B) is generally 0.5 to 3.0 mol, preferably 0.8 to 2.0 mol, per 1 mol.
  • the hydrosilylation reaction catalyst which is the component (C) of the present invention is the same as described in ⁇ Preparation of the component (A)> above.
  • the amount of component (C) is not particularly limited as long as it is an effective amount as a catalyst. It is preferable to add an amount of about 1 to 500 ppm, particularly about 2 to 100 ppm. By setting the blending amount within the above range, the time required for the curing reaction becomes appropriate, and problems such as coloring of the cured product do not occur.
  • the low dielectric constant insulating coating composition of the present invention may optionally contain other components within a range that does not impair the objects and effects of the present invention.
  • the addition-reactive carbon-carbon double bond in the component (A) may remain unreacted.
  • antioxidant all conventionally known ones can be used.
  • the amount to be blended is not particularly limited as long as it is an effective amount as an antioxidant. , usually 10 to 10,000 ppm, preferably 100 to 1,000 ppm. By setting the blending amount within the above range, the antioxidant ability is fully exhibited, and a cured product having excellent optical properties without causing coloration, white turbidity, deterioration due to oxidation, etc., can be obtained.
  • ⁇ Viscosity/hardness modifier> In order to adjust the viscosity of the low dielectric constant insulating coating composition of the present invention or the hardness of the cured product obtained from the low dielectric constant insulating coating composition of the present invention, it has an alkenyl group or SiH bonded to a silicon atom.
  • the blending amount thereof is such that the alkenyl groups and the above (A) SiH in the above component (B) is usually 0.5 to 3.0 mol, preferably 0.8 to 2.0 mol, per 1 mol of the total amount of addition-reactive carbon-carbon double bonds possessed by the component. It is preferable to use a molar amount.
  • the blending amounts thereof are the same as the above SiH and the SiH possessed by the component (B).
  • the viscosity of the low dielectric constant insulating coating composition of the present invention at 25°C is preferably 10 to 10,000 mPa ⁇ s, more preferably 30 to 3,000 mPa ⁇ s. Within such a range, workability is excellent.
  • the viscosity in the present invention indicates the viscosity measured at 25°C with a rotational viscometer according to JIS K 7117-1:1999.
  • addition reaction controllers such as 1-ethynylcyclohexanol and 3,5-dimethyl-1-hexyn-3-ol can be blended.
  • an inorganic filler such as fumed silica may be blended to improve strength within a range that does not affect transparency, and if necessary, dyes, pigments, flame retardants, etc. may be blended. good too.
  • a light stabilizer to impart resistance to photodegradation due to light energy such as sunlight.
  • Hindered amine-based stabilizers that capture radicals generated by photo-oxidative deterioration are suitable as the light stabilizer, and the antioxidant effect is further improved by using them together with antioxidants.
  • Specific examples of light stabilizers include bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate and 4-benzoyl-2,2,6,6-tetramethylpiperidine.
  • the total amount of components (A), (B) and (C) is preferably 50 to 100% by mass, more preferably 80 to 100% by mass. Preferably, it is more preferably 90 to 100% by mass. Also, the low dielectric constant insulating coating composition of the present invention can be produced by uniformly mixing the components described above.
  • the curing conditions for the low-dielectric-constant insulating coating composition of the present invention vary depending on the amount thereof, and are not particularly limited, but the conditions of 60 to 180° C. and 10 to 300 minutes are usually preferred.
  • 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 such a range, high-frequency dielectric properties are excellent.
  • 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.
  • the cured product obtained by curing the low dielectric constant insulating coating composition of the present invention has transparency, it is suitable for use in display devices.
  • platinum-vinylsiloxane complex an amount of 20 ppm relative to the total mass of (A) and (B) as platinum metal atoms
  • 1-ethynylcyclohexanol 0.03 parts by mass were uniformly mixed
  • a composition having a viscosity of 50 mPa ⁇ s was obtained. This composition was poured into a metal frame with a thickness of 0.3 mm and heated at 150° C. for 2 hours to obtain a cured product.
  • a methyl silicone resin-based curable composition (trade name: KER-2300, manufactured by Shin-Etsu Chemical Co., Ltd., viscosity: 5,000 mPa s) was added to 0 in the same manner as in Example 1. It was poured into a metal frame with a thickness of 0.3 mm and heated at 150° C. for 2 hours to obtain a cured product.
  • compositions of Examples 1 to 3 had suitable viscosities when applied to substrates and were excellent in workability.
  • the cured products obtained in Examples 1 to 3 had a relative dielectric constant of 3.0 or less at 10 GHz and a dielectric loss tangent of 0.01 or less, indicating excellent high-frequency dielectric properties.
  • the methyl-based silicone resin of Comparative Example 1 had a large dielectric loss tangent and did not satisfy the high frequency characteristics.

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Abstract

La présente invention possède une composition de revêtement isolant à faible constante diélectrique, dont un produit durci possède une faible constante diélectrique relative et une faible tangente de perte diélectrique, et présentant une excellente maniabilité lorsqu'il est appliqué sur un substrat. La présente invention fournit une composition de revêtement isolant à faible constante diélectrique contenant les éléments suivants : (A) un produit de réaction d'addition d' (a) un composé de formule (1) possédant deux atomes d'hydrogène dans chaque molécule, chacun des atomes d'hydrogène étant lié à un atome de silicium, et (b) un hydrocarbure polycyclique possédant deux doubles liaisons carbone-carbone réactives à l'addition dans chaque molécule ; (B) un composé possédant trois atomes d'hydrogène ou plus dans chaque molécule, chacun des atomes d'hydrogène étant lié à un atome de silicium ; et (C) un catalyseur d'hydrosilylation. (Dans la formule (1), R représente indépendamment un groupe hydrocarbure monovalent non substitué ou substitué possédant 1 à 12 atomes de carbone, ou un groupe alcoxy possédant 1 à 6 atomes de carbone).
PCT/JP2022/031482 2021-08-30 2022-08-22 Composition de revêtement isolant à faible constante diélectrique, produit durci de celle-ci et dispositif d'affichage WO2023032724A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005133073A (ja) * 2003-10-10 2005-05-26 Shin Etsu Chem Co Ltd 硬化性組成物
JP2018523737A (ja) * 2015-08-31 2018-08-23 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 低温硬化組成物、それから形成された硬化膜、および前記硬化膜を有する電子装置
JP2020193243A (ja) * 2019-05-24 2020-12-03 信越化学工業株式会社 付加硬化型シリコーン組成物、硬化物および光半導体素子

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005133073A (ja) * 2003-10-10 2005-05-26 Shin Etsu Chem Co Ltd 硬化性組成物
JP2018523737A (ja) * 2015-08-31 2018-08-23 サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. 低温硬化組成物、それから形成された硬化膜、および前記硬化膜を有する電子装置
JP2020193243A (ja) * 2019-05-24 2020-12-03 信越化学工業株式会社 付加硬化型シリコーン組成物、硬化物および光半導体素子

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