WO2020045560A1 - Composition, produit durci, corps stratifié et dispositif électronique - Google Patents

Composition, produit durci, corps stratifié et dispositif électronique Download PDF

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Publication number
WO2020045560A1
WO2020045560A1 PCT/JP2019/033877 JP2019033877W WO2020045560A1 WO 2020045560 A1 WO2020045560 A1 WO 2020045560A1 JP 2019033877 W JP2019033877 W JP 2019033877W WO 2020045560 A1 WO2020045560 A1 WO 2020045560A1
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compound
liquid crystal
polymerizable
inorganic filler
composition
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PCT/JP2019/033877
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English (en)
Japanese (ja)
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研人 氏家
和宏 滝沢
國信　隆史
武 藤原
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Jnc株式会社
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/08—Ingredients agglomerated by treatment with a binding agent

Definitions

  • One embodiment of the present invention relates to a composition, a cured product, a laminate, and an electronic device.
  • Patent Literature 1 discloses a heat dissipating member in which an organic material and an inorganic material are combined, wherein the inorganic materials are connected with a silane coupling agent and a polymerizable liquid crystal compound.
  • the heat dissipating member used in the chip package and various materials constituting it have been studied.
  • the heat dissipating member described in Patent Document 1 has room for improvement in terms of thermal conductivity and adhesion to an adherend such as a metal, a metal compound, or a semiconductor layer.
  • An embodiment of the present invention provides a composition capable of forming a cured product having excellent heat conductivity and excellent adhesion to an adherend such as a metal, a metal compound, or a semiconductor layer, and a use thereof.
  • the content of the inorganic filler is 150 to 4500 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound;
  • the content ratio of the polymerizable liquid crystal compound to the non-liquid crystal polymerizable compound is 20:80 to 95: 5; Composition.
  • At least one polymerizable compound selected from a bifunctional or higher functional polymerizable liquid crystal compound and a bifunctional or higher functional non-liquid crystalline polymerizable compound or at least a part thereof is cured.
  • R a1 is each independently a polymerizable group represented by the following formula (2-1) or (2-2);
  • any -CH 2 - is -O-, -CO-, -COO-, -OCO-.
  • -CH CH- or -C ⁇ C-;
  • Z is each independently a single bond or alkylene having 1 to 22 carbon atoms;
  • m1 is an integer of 1 to 6.
  • R b is each independently hydrogen, halogen, —CF 3 or alkyl having 1 to 5 carbons, and q is 0 or 1.
  • the inorganic filler is at least one selected from boron nitride, aluminum nitride, boron nitride carbon, boron carbide, graphite, carbon fiber, carbon nanotube, alumina, cordierite, zinc oxide, zirconium oxide, and titanium oxide.
  • the present composition a cured product having excellent heat conductivity and adhesion to an adherend such as a metal, a metal compound, or a semiconductor layer can be obtained. It can be easily formed. Furthermore, the present composition can easily form a cured product having excellent chemical stability, hardness, mechanical strength, and the like. For this reason, the present composition is suitably used for, for example, a heat radiating substrate, a heat radiating plate (surface heat sink), a heat radiating sheet, a heat radiating coating, a heat radiating adhesive, a heat radiating insulating substrate with electrodes, a heat conductive electronic substrate, and the like. You.
  • FIG. 1 is a schematic diagram when a tensile test sample is prepared in an example.
  • FIG. 2 is a schematic cross-sectional schematic diagram when a tensile test using the tensile test sample obtained in FIG. 1 is performed.
  • the composition includes an inorganic filler, a bifunctional or higher functional polymerizable liquid crystal compound, a bifunctional or higher functional non-liquid crystalline polymerizable compound, and a curing agent capable of curing the polymerizable liquid crystal compound and the non-liquid crystalline polymerizable compound.
  • the content of the inorganic filler is 150 to 4500 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound, and the ratio of the content of the polymerizable liquid crystal compound to the content of the non-liquid crystal polymerizable compound (polymerization (Mass of non-liquid crystalline polymerizable compound): 20:80 to 95: 5.
  • the inorganic filler is not particularly restricted but includes, for example, nitrides, carbides, carbon materials, silicate compounds and metal oxides.
  • the inorganic filler one kind may be used, or two or more kinds having different kinds, particle diameters, shapes and the like may be used.
  • the inorganic filler for example, alumina, magnesia, beryllia, silica, titanium oxide, zirconium oxide, zinc oxide, iron oxide, ferrite, copper oxide, cerium oxide, yttrium oxide, tin oxide, holmium oxide, bismuth oxide, cobalt oxide, Metal oxides such as calcium oxide; silicate compounds such as mullite and cordierite; nitrides such as boron nitride, aluminum nitride, silicon nitride and boron nitride; carbides such as boron carbide and silicon carbide; diamond, graphite, Carbon materials such as carbon fiber, carbon nanotube, and graphene; hydroxides such as magnesium hydroxide and aluminum hydroxide; silicon, gold, silver, copper, platinum, iron, tin, lead, nickel, aluminum, magnesium, tungsten, and molybdenum , Stainless and other metals; glass And the like; cloth made of carbon fibers or glass fibers; in
  • boron nitride, aluminum nitride, boron nitride carbon, boron carbide, graphite, carbon fiber, carbon nanotube, alumina, cordierite, etc. from the viewpoint that a composition having more excellent thermal conductivity can be easily obtained.
  • an insulating inorganic filler increases reliability such as a longer life.
  • a carbon material as a conductor or Although it is preferable not to use some oxides and the like which are semiconductors, a conductive inorganic filler may be used as long as the desired insulating property can be maintained.
  • h-BN hexagonal boron nitride
  • graphite graphite
  • h-BN hexagonal boron nitride
  • graphite graphite
  • h-BN has a low dielectric constant and a high insulating property. This is preferred when the composition is used for applications requiring insulation.
  • a plate-like filler such as h-BN or graphite because the plate-like structure can be oriented along a mold or the like during molding or curing.
  • the type, shape, size, etc. of the inorganic filler can be appropriately selected according to the purpose.
  • Examples of the shape of the inorganic filler include plate, sphere, amorphous, fibrous, rod, and tubular shapes.
  • the average particle size of the inorganic filler is preferably from 0.1 to 600 ⁇ m, more preferably from 1 to 200 ⁇ m, from the viewpoint that a heat radiation member having more excellent thermal conductivity can be easily obtained.
  • the average particle size in the present specification is a median size based on a particle size distribution measurement by a laser diffraction / scattering method.
  • the average particle size, when the shape of the filler is plate-like refers to the average value of the length of the long side, when the shape of a fiber or rod, the average value of the fiber length or the length of the rod. That means.
  • the bifunctional or higher functional polymerizable liquid crystal compound (hereinafter, also simply referred to as “polymerizable liquid crystal compound”) is not particularly limited, and may be a trifunctional or higher functional or tetrafunctional or higher compound.
  • the polymerizable liquid crystal compound a compound having two or more of the following Ra1 is preferable.
  • the polymerizable liquid crystal compound used in the present composition may be one type or two or more types.
  • the “liquid crystal compound” refers to a compound that exhibits a liquid crystal phase such as a nematic phase or a smectic phase.
  • the polymerizable liquid crystal compound When the polymerizable liquid crystal compound is a polycyclic compound, it tends to be a compound having high heat resistance, and when the linearity is high, there is little elongation or fluctuation due to heat between the inorganic fillers, and the phonon conduction of heat is efficiently performed. It is preferable because it can be transmitted. Compounds that are polycyclic and have high linearity often exhibit liquid crystallinity as a result, and liquid crystalline compounds are preferable because of their excellent thermal conductivity.
  • the compound (1) represented by the formula (1) is preferable in that the composition and the cured product can be easily obtained.
  • the compound (1) has high polymerization reactivity, a wide liquid crystal phase temperature range, good miscibility, etc., and becomes uniform when mixed with other liquid crystal compounds or polymerizable compounds.
  • the compound (1) means a compound represented by the formula (1), and may also mean at least one kind of the compound represented by the formula (1).
  • the compounds represented by other formulas have the same notation.
  • M1 is an integer of 1 to 6, preferably an integer of 2 to 6, and more preferably an integer of 2 to 4.
  • Terminal group R a1 R a1 is each independently a polymerizable group represented by the following formula (2-1) or (2-2). “R a1 is independently of each other” means that two R a1 of the compound (1) may be the same or different.
  • R a1 is independently of each other means that two R a1 of the compound (1) may be the same or different.
  • the groups represented by these symbols may be the same or different.
  • R b is each independently hydrogen, halogen, —CF 3 or alkyl having 1 to 5 carbons, and q is 0 or 1.
  • the alkyl having 1 to 5 carbon atoms in R b is preferably alkyl having 1 to 3 carbon atoms, and more preferably methyl.
  • R b is preferably hydrogen from the viewpoint of easy synthesis of the compound (1).
  • q is preferably 0.
  • Ring structure A A is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7- Diyl, bicyclo [2.2.2] oct-1,4-diyl or bicyclo [3.1.0] hex-3,6-diyl,
  • any -CH 2 - may be replaced by -O-
  • any hydrogen may be halogen, cyano, carbon It may be replaced by an alkyl having 1 to 10 carbon atoms or an alkyl halide having 1 to 10 carbon atoms.
  • any -CH 2 -is -O-,- CO-, -COO-, -OCO-, -CH CH- or -C ⁇ C- may be substituted.
  • arbitrary means "at least one", but usually, in consideration of the stability of the compound, a structure that is difficult to adopt based on common sense in the art, for example, where oxygen and oxygen are adjacent to each other. It is preferable not to include -OO-.
  • the phrase “arbitrary hydrogen may be replaced by halogen, alkyl having 1 to 10 carbons or alkyl halide having 1 to 10 carbons” is described, for example, in 1,4-phenylene. It means an embodiment in which at least one of the hydrogens at the 2,3,5,6-position is replaced by a substituent such as fluorine or methyl, and when the substituent is "an alkyl halide having 1 to 10 carbon atoms".
  • Embodiments include examples such as 2-fluoroethyl and 3-fluoro-5-chlorohexyl.
  • a 6-membered ring and a condensed ring containing the 6-membered ring are basically regarded as rings, and for example, a 3-membered ring, 4-membered ring and 5-membered ring alone are not regarded as rings.
  • a condensed ring such as a naphthalene ring or a fluorene ring is regarded as one ring.
  • the compound (1) When the compound (1) has at least one 1,4-phenylene, the compound tends to have a large orientational order parameter and a large magnetization anisotropy. When the compound (1) has at least two 1,4-phenylenes, the temperature range of the liquid crystal phase is wide, and the compound tends to have a higher clearing point. When the compound (1) has a group in which at least one hydrogen on the 1,4-phenylene ring is substituted with cyano, halogen, —CF 3 or —OCF 3 , the compound tends to have a high dielectric anisotropy. is there. When the compound (1) has at least two 1,4-cyclohexylenes, the compound tends to have a high clearing point and a low viscosity.
  • Preferred A is, for example, 1,4-cyclohexylene, 1,4-cyclohexenylene, 2,2-difluoro-1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 2,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene , 2,3,5-trifluoro-1,4-phenylene, pyridine-2,5-diyl, 3-fluoropyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridazine-3,6-diyl , Naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7-diyl, 9-methyl
  • 1,4-cyclohexylene and 1,3-dioxane-2,5-diyl is preferably trans rather than cis. Since 2-fluoro-1,4-phenylene and 3-fluoro-1,4-phenylene are structurally identical, the latter is not illustrated. This rule also applies to the relationship between 2,5-difluoro-1,4-phenylene and 3,6-difluoro-1,4-phenylene.
  • More preferred A is, for example, 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene , 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, and 2,6-difluoro-1,4-phenylene.
  • Particularly preferred A is 1,4-cyclohexylene and 1,4-phenylene.
  • .Binding group Z Z is each independently a single bond or an alkylene having 1 to 22 carbon atoms, preferably a single bond or an alkylene having 1 to 10 carbon atoms,
  • Particularly preferred Z is a single bond,-(CH 2 ) 2 -,-(CH 2 ) 2 O-, -O (CH 2 ) 2- , -COO- or -OCO-.
  • Compound (1) may be optically active or optically inactive.
  • the compound (1) may have an asymmetric carbon or may have an axial asymmetry.
  • the configuration of the asymmetric carbon may be R or S.
  • the asymmetric carbon may be located at either R a1 or A.
  • it tends to be a compound having excellent compatibility with other components.
  • the compound (1) has axial asymmetry, the compound tends to have a large twist inducing force. Further, the light-irradiating property may be any.
  • Compound (1) can also be represented by the following formula (1-a) or (1-b).
  • Y is alkylene having 1 to 10 carbon atoms in which -CH 2- at one or both terminals is replaced by -O-.
  • m is an integer of 1 to 6, preferably an integer of 2 to 6, and more preferably an integer of 2 to 4.
  • two Ps are preferably the same group, and two Ys are also preferably the same group, and both sides of-(AZ) m -are bilaterally symmetric. Is preferred.
  • “-ZY-” in the formula (1-b) has the same meaning as Z in the formula (1).
  • Examples of preferable compound (1) include the following compounds (a-1) to (g-7).
  • * indicates an asymmetric carbon
  • R a, P and Y are independently the same as R a, P and Y in the formula (1-a) and (1-b).
  • a is each independently an integer of 1 to 20.
  • X is a halogen, an alkyl having 1 to 10 carbons, or an alkyl fluoride having 1 to 10 carbons.
  • Compound (1) can be synthesized by combining known methods in synthetic organic chemistry. Methods for introducing desired end groups, ring structures and linking groups into starting materials are described in, for example, Houben-Wyle, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart, Organic Syntheses, John. Wily & Sons, Inc.), Organic Reactions, John Wily & Sons Inc., Comprehensive Organic Synthesis, Pergamon Press, New Laboratory Chemistry Course (Maruzen) It is described in. Further, JP-A-2006-265527 may be referred to.
  • the content of the polymerizable liquid crystal compound in the present composition is preferably 1 to 35% by mass, more preferably 2 to 30% by mass based on 100% by mass of the present composition.
  • the content of the polymerizable liquid crystal compound is in the above range, it is possible to easily form a cured product excellent in thermal conductivity and adhesion to an adherend such as a metal, a metal compound or a semiconductor layer in a well-balanced manner.
  • the curing agent is not particularly limited as long as the polymerizable liquid crystal compound and the non-liquid crystalline polymerizable compound can be cured.
  • acid anhydride-based curing agents for example, acid anhydride-based curing agents, amine-based curing agents, phenol-based curing agents, and mercaptan-based curing agents And imidazole.
  • the polymerizable liquid crystal compound can be easily cured, and a cured product excellent in thermal conductivity and adhesion to an adherend such as a metal, a metal compound or a semiconductor layer can be easily formed.
  • an amine-based curing agent is preferable.
  • the curing agent one type may be used, or two or more types may be used.
  • amine-based curing agent a commonly used compound can be used without any particular limitation, and a commercially available compound may be used. Among them, a bifunctional or higher polyfunctional curing agent is preferable from the viewpoint of curability, and a polyfunctional curing agent having a rigid skeleton is more preferable from the viewpoint of thermal conductivity.
  • diamines are preferable because the polymerizable liquid crystal compound can be cured without impairing the liquid crystallinity of the polymerizable liquid crystal compound.
  • amine curing agent examples include diethylenetriamine, triethylenetetramine, tetraethylenepentamine, o-xylenediamine, m-xylenediamine, p-xylenediamine, trimethylhexamethylenediamine, 2-methylpentamethylenediamine, and diethylaminopropyl.
  • examples of the amine-based curing agent include a compound (2) represented by the following formula (2). JZ- (XZ) m1 -J (2)
  • J is each independently an amino group
  • m1 is an integer of 1 to 6.
  • X in the formula (2) is preferably the same group as A in the formula (1), and Z in the formula (2) is preferably the same group as Z in the formula (1).
  • M1 in the above is preferably an integer of 2 to 6, more preferably an integer of 2 to 4.
  • the compound (2) is more preferably a compound (2-1) represented by the following formula (2-1).
  • JZXZ 1 -XZJ (2-1) [J, X and Z in the formula (2-1) have the same meanings as J, X and Z in the formula (2), and Z 1 in the formula (2-1) is Synonymous with Z. ]
  • the compound (2-1) is preferably a compound in which Z is a single bond, a compound in which X is 1,4-phenylene, and a compound in which Z 1 is a group represented by — (CH 2 ) n —. preferable.
  • the compound in which n in Z 1 is an even number has a bilaterally symmetric structure and is hardly bent. Therefore, a composition and a cured product obtained using the compound tend to have higher thermal conductivity. Because it is, it is desirable.
  • the amount of the curing agent used is based on 1 mol of the functional group capable of reacting with the curing agent in the component (a) capable of reacting with the curing agent contained in the composition.
  • a mole of a functional group capable of reacting with the component (a) is preferably 0.6 to 1.8, more preferably 0.8 to 1.4.
  • the component (a) includes the polymerizable liquid crystal compound and the following non-liquid crystal polymerizable compound, and the component (b) includes a curing agent.
  • Non-liquid crystalline polymerizable compound contains a bifunctional or higher functional non-liquid crystalline polymerizable compound (hereinafter, also simply referred to as “non-liquid crystalline polymerizable compound”).
  • the non-liquid crystalline polymerizable compound is a compound other than the polymerizable liquid crystal compound, and has a polymerizable group but refers to a compound which does not exhibit a liquid crystal phase such as a nematic phase or a smectic phase by itself.
  • the non-liquid crystalline polymerizable compound may be a compound having three or more functions or four or more functions. One type of non-liquid crystalline polymerizable compound may be used, or two or more types may be used.
  • the non-liquid crystalline polymerizable compound is not particularly limited, for example, a compound having a group capable of reacting with a polymerizable group of the polymerizable liquid crystal compound or a compound having a group capable of reacting with a reactive group of the curing agent
  • a compound having a group capable of reacting with a reactive group of the curing agent is preferable, and a compound having R a is more preferable.
  • non-liquid crystalline polymerizable compound examples include vinyl derivatives, styrene derivatives, (meth) acrylic acid derivatives, sorbic acid derivatives, fumaric acid derivatives, itaconic acid derivatives, polyglycidyl ether of polyether, diglycidyl ether of bisphenol A, Epoxy compounds such as diglycidyl ether of bisphenol F and diglycidyl ether of biphenol are exemplified.
  • the non-liquid crystalline polymerizable compound may be synthesized by a known method in synthetic organic chemistry, or a commercially available product may be used.
  • the amount of the non-liquid crystalline polymerizable compound in the present composition is not particularly limited, but is preferably such that the ratio described in the column of the amount of the curing agent is used.
  • the content ratio of the polymerizable liquid crystal compound to the non-liquid crystal polymerizable compound is from 20:80 to 95: 5, preferably 20:80 to 95: 5.
  • the ratio is from 80 to 90:10, more preferably from 25:75 to 80:20.
  • the ratio of the content of the polymerizable liquid crystal compound to the content of the non-liquid crystalline polymerizable compound is within the above range, a cured product having excellent thermal conductivity and adhesion to an adherend such as a metal, a metal compound, or a semiconductor layer can be easily obtained. Can be formed.
  • the composition preferably contains a coupling agent from the viewpoint that a cured product having more excellent thermal conductivity can be obtained.
  • a coupling agent may be added when the inorganic filler, the polymerizable liquid crystal compound, and the curing agent are mixed, but a cured product having more excellent thermal conductivity can be obtained.
  • at least a part of the coupling agent to be used is preferably used as the composite material A previously bonded to the inorganic filler.
  • the inorganic filler is bonded to one end of the coupling agent, and the coupling agent is used. It is also preferable to use in the form of a composite material B having a polymerizable compound bonded to the other end.
  • the polymerizable compound is the polymerizable liquid crystal compound or the non-liquid crystal polymerizable compound.
  • the coupling agent is not particularly limited, and known coupling agents such as a silane coupling agent, a titanate coupling agent, and an aluminate coupling agent can be used. preferable. One type of coupling agent may be used, or two or more types may be used.
  • the coupling agent is a compound having at least two reactive groups, and includes a reactive group capable of binding to an inorganic filler and a reactive group capable of binding two or more coupling agents to each other, or a polymerizable compound.
  • a reactive group capable of binding to a functional group (eg, oxiranyl group) of the polymerizable compound Preferably has a reactive group capable of binding to a functional group (eg, oxiranyl group) of the polymerizable compound.
  • the reactive group examples include a hydrolyzable group such as an alkoxy group, an amino group, a ureido group, an oxiranyl group, an oxetanyl group, a carboxy group, an acid anhydride group, a mercapto group, an isocyanate group, an imidazole group, a vinyl group, And an ethylenically unsaturated bonding group such as a (meth) acryloyl group.
  • a hydrolyzable group such as an alkoxy group, an amino group, a ureido group, an oxiranyl group, an oxetanyl group, a carboxy group, an acid anhydride group, a mercapto group, an isocyanate group, an imidazole group, a vinyl group, and an ethylenically unsaturated bonding group such as a (meth) acryloyl group.
  • the combination of a reactive group capable of binding two or more types of coupling agents or a combination of a functional group of the polymerizable compound and a reactive group capable of binding to the functional group is not particularly limited.
  • an oxiranyl group may be used. Examples include amino groups, vinyl groups, (meth) acryloyl groups, carboxy groups or acid anhydride groups and amino groups, and imidazole groups and oxiranyl groups. Among these, a combination in which the structure after the reaction becomes a structure having high heat resistance is more preferable.
  • a coupling agent having an amino group examples include Silaace (trade name) S310, S320, S330, and S360 manufactured by JNC, and KBM-903 and KBE-903 manufactured by Shin-Etsu Chemical Co., Ltd. .
  • the amount of the coupling agent to be used is not particularly limited, but is preferably 0.1 to 10% by mass relative to 100% by mass of the present composition from the viewpoint that a cured product having more excellent thermal conductivity can be obtained. More preferably, it is 0.5 to 5% by mass.
  • the reaction amount of the coupling agent with respect to the inorganic filler mainly varies depending on the size of the inorganic filler, the reactivity of the coupling agent used, and the like. It is preferable to couple as many coupling agents as possible to the inorganic filler, and the number of reactive groups that react with the reactive groups of the coupling agent is equal to the number of reactive groups of the inorganic filler. It is preferable to use a coupling agent so as to increase the amount slightly.
  • the coupling amount of the coupling agent with respect to 100 parts by mass of the inorganic filler is preferably 0.1 part by mass or more, from the viewpoint that the composition and the cured product having excellent thermal stability and durability can be easily obtained. It is preferably from 0.3 to 50 parts by mass, particularly preferably from 0.5 to 25 parts by mass.
  • the composition includes an inorganic filler, a polymerizable liquid crystal compound, a curing agent, a non-liquid crystal polymerizable compound, and other components other than the coupling agent, such as a non-polymerizable compound, a polymerization initiator, a solvent, a stabilizer, and an adhesive.
  • An imparting agent and an organic filler may be included.
  • Each of these other components may be used alone or in combination of two or more.
  • the composition may include a non-polymerizable compound.
  • a non-polymerizable compound is not particularly limited as long as it is a compound that does not react with the inorganic filler, the polymerizable liquid crystal compound, the curing agent, the non-liquid crystal polymerizable compound, and the coupling agent, but does not decrease the film-forming property and the mechanical strength.
  • Compounds are preferred, and more preferably high molecular compounds.
  • the polymer compound include a polyolefin resin, a polyvinyl resin, a silicone resin, and a wax.
  • the non-polymerizable compound may be a liquid crystal compound having no polymerizable group.
  • non-polymerizable liquid crystal compounds are described in LiquiCryst, LCI Publisher GmbH, Hamburg, Germany, which is a database of liquid crystal compounds.
  • a composition containing a non-polymerizable liquid crystal compound is polymerized, for example, a composite material of a polymer of compound (1) and a non-polymerizable liquid crystal compound can be obtained.
  • a composite material includes an embodiment in which a non-polymerizable liquid crystal compound is present in a polymer network such as a polymer dispersed liquid crystal.
  • a liquid crystal compound having characteristics such that there is no fluidity in a temperature range in which a cured product obtained from the present composition is used is desirable.
  • the composition may include a polymerization initiator.
  • a polymerization initiator a photoradical polymerization initiator, a photocationic polymerization initiator, a thermal radical polymerization initiator, or the like may be used according to the components contained in the present composition and a desired polymerization method.
  • a thermal radical polymerization initiator is preferable since the inorganic filler tends to absorb ultraviolet rays.
  • Preferred initiators for thermal radical polymerization include, for example, benzoyl peroxide, diisopropylperoxydicarbonate, t-butylperoxy-2-ethylhexanoate, t-butylperoxypivalate, di-t-butylperoxide Oxide (DTBP), t-butylperoxydiisobutyrate, lauroyl peroxide, dimethyl 2,2'-azobisisobutyrate (MAIB), azobisisobutyronitrile (AIBN), and azobiscyclohexanecarbonitrile (ACN) Can benzoyl peroxide, diisopropylperoxydicarbonate, t-butylperoxy-2-ethylhexanoate, t-butylperoxypivalate, di-t-butylperoxide Oxide (DTBP), t-butylperoxydiisobutyrate, lauroyl peroxide, dimethyl 2,
  • the composition may include a solvent.
  • Preferred solvents include, for example, benzene, toluene, xylene, mesitylene, hexane, heptane, octane, nonane, decane, tetrahydrofuran, ⁇ -butyrolactone, N-methylpyrrolidone, dimethylformamide, dimethylsulfoxide, cyclohexane, methylcyclohexane, cyclopentanone , Cyclohexanone, and propylene glycol methyl ether acetate (PGMEA).
  • the amount of the solvent used is not particularly limited, and may be determined for each individual case in consideration of polymerization efficiency, solvent cost, energy cost, and the like.
  • Stabilizers may be added to the composition to facilitate handling of the composition.
  • the stabilizer is not particularly limited as long as the effects of the present invention are not impaired, and examples thereof include an antioxidant, a copper damage inhibitor, a metal deactivator, an antioxidant, an antifoaming agent, an antistatic agent, and a weathering agent. No. As these stabilizers, known stabilizers can be used without limitation.
  • antioxidants include hydroquinone, 4-ethoxyphenol and 3,5-di-t-butyl-4-hydroxytoluene (BHT).
  • Japanese Patent Application Laid-Open No. 5-48265 discloses The addition of copper inhibitors or metal deactivators as mentioned is preferred.
  • the copper damage inhibitor (trade name) include Mark ZS-27 and Mark CDA-16 manufactured by ADEKA Corporation; SANKO-EPOCLEAN manufactured by Sanko Chemical Industry Co., Ltd .; and Irganox MD1024 manufactured by BASF Corporation. preferable.
  • the added amount of the copper harm inhibitor is preferably based on 100 parts by mass of the total amount of the organic component contained in the composition, from the viewpoint that the organic component in the portion in contact with the metal in the cured product can be prevented from deteriorating. Is 0.1 to 3 parts by mass.
  • the composition may include an organic filler, and examples of the organic filler include fibers made of polyvinyl formal, polyvinyl butyral, polyester, polyamide, polyimide, and the like.
  • the present composition can be prepared by mixing an inorganic filler, a polymerizable liquid crystal compound, a non-liquid crystal polymerizable compound, a curing agent, and other components used if necessary.
  • the mixing method at this time is not particularly limited, for example, weighed so that the mixing ratio of the inorganic filler and the polymerizable liquid crystal compound is in the above range, mixed in an agate mortar or the like, using a biaxial roll or the like A method of mixing is used.
  • the inorganic filler when preparing the present composition, use a composite material A in which an inorganic filler and a coupling agent are bonded in advance, or bond the inorganic filler to one end of the coupling agent in advance. It is preferable to use a composite material B in which a polymerizable compound is bonded to the other end of the coupling agent.
  • the inorganic filler and the coupling agent are mixed in the presence of a solvent, stirred using a stirrer or the like, and then dried. After the solvent is dried, it is kept under vacuum conditions or the like using a vacuum dryer or the like. If necessary, a solvent is added after the holding, a sonication treatment, a centrifugal separation, and the like are performed to thereby remove a coupling agent attached to the solid content (unbound). This purification step may be performed a plurality of times. Further, the purified composite material may be dried using an oven or the like.
  • the solvent is not particularly limited, but is preferably a solvent capable of dissolving the coupling agent, and is preferably a solvent capable of dispersing the inorganic filler.
  • the time for mixing and stirring the inorganic filler and the coupling agent is not particularly limited, and may be, for example, 1 minute to 24 hours.
  • the drying conditions are not particularly limited as long as the solvent used is dried, and may be appropriately set according to the solvent used.
  • the conditions for holding under vacuum conditions or the like are preferably, for example, conditions under which dehydration condensation is performed.
  • the holding temperature is preferably 20 to 150 ° C.
  • the holding time is 1 minute. ⁇ 24 hours.
  • the method for bonding the coupling agent and the polymerizable compound bonded to the inorganic filler is not particularly limited, and a known method can be used, but the following method is preferable.
  • the coupling agent combined with the inorganic filler and the polymerizable compound are mixed using an agate mortar or the like, and then kneaded using a biaxial roll or the like. Thereafter, if necessary, separation and purification (removal of the polymerizable compound not bound to the coupling agent) is performed by sonication and centrifugation.
  • the present composition contains an inorganic filler in advance and at least one polymerizable compound selected from a polymerizable liquid crystal compound and a non-liquid crystal polymerizable compound. It is preferable to use a composite material X coated with a compound or a cured product in which at least a part of the compound has been cured, and the inorganic filler is added in advance to a first polymerizable compound (polymerizable liquid crystal compound or non-liquid crystal polymerizable compound) or at least the same.
  • the second polymerizable compound (a polymerizable liquid crystal compound or a non-liquid crystalline polymerizable compound; however, the first polymerizable compound is used at the time of curing, molding, or the like using the composite material X partially covered with a cured product. That is, when a polymerizable liquid crystal compound is used as the first polymerizable compound, the second polymerizable compound is a non-liquid crystal polymerizable compound.) More preferably.
  • an inorganic filler alone may be used, but the composite material A may be used, or the composite material B may be used. .
  • a curing agent When producing such a composite material X, it is preferable to use a curing agent together with the first polymerizable compound.
  • coating includes not only the case where the entire surface of the inorganic filler is covered but also the case where a part of the surface of the inorganic filler is covered.
  • the method for coating the inorganic filler (composite material A or composite material B) with the polymerizable compound or a cured product in which at least a part thereof is cured is not particularly limited, and a known method can be used. preferable.
  • the inorganic filler, the first polymerizable compound, and the curing agent are stirred using a disperser or the like at a temperature of preferably 60 to 140 ° C, more preferably 70 to 125 ° C, for about 5 minutes to 1 hour.
  • the inorganic filler (composite material A or composite material B) can be covered with a cured product obtained by curing at least a part of the polymerizable compound.
  • the cured product according to one embodiment of the present invention is obtained by curing the present composition.
  • the curing may be performed in a solvent or without a solvent.
  • the composition containing the solvent may be applied to the substrate by, for example, a spin coating method, and then the solvent may be removed before curing.
  • the curing method may be appropriately selected depending on the components to be used, the desired application, and the like, and may be heat curing, light curing, or after heating to a suitable temperature after light curing. It may be cured.
  • the thermal curing is performed, for example, at a temperature of preferably 50 to 350 ° C., more preferably 60 to 300 ° C., and even more preferably 70 to 250 ° C., for 5 seconds to 10 hours, preferably 1 minute to 5 hours, more preferably Can be carried out by heating for about 5 minutes to 1 hour.
  • the curing may be performed in two or more stages, for example, after pre-curing by heating at a temperature of preferably 60 to 140 ° C., more preferably 70 to 125 ° C. for about 5 minutes to 1 hour.
  • a method of curing by the following compression molding may be used.
  • the light curing can be performed, for example, by irradiating light so that the integrated illuminance is preferably 10 to 2000 mJ / cm 2 , more preferably 50 to 500 mJ / cm 2 .
  • the laminate according to one embodiment of the present invention includes a layer of a cured product of the present composition (hereinafter, also simply referred to as a “cured product layer”) and a metal, metal compound, or semiconductor layer (hereinafter, simply referred to as a “metal-related layer”). ").).
  • the cured product layer contained in the laminate may be a single layer or two or more layers. Further, the number of metal-related layers contained in the laminate may be one, or two or more. When two or more cured product layers are included, these cured product layers may be the same or different. The same applies when two or more metal-related layers are included.
  • the laminate may include other conventionally known layers such as an adhesive layer, but the cured product layer has excellent adhesion with a metal-related layer, and thus has a cured product layer and a metal-related layer. It is preferable that other layers are not included between them.
  • the metal-related layer examples include metal layers made of copper, aluminum, nickel, gold, alloys of these metals, metal compound layers made of oxides, nitrides, and the like of these metals, silicon, GaAs, GaN, and SiC. And a semiconductor layer made of germanium oxide or the like, and specifically, a metal electrode, a semiconductor chip, or the like. Further, the metal-related layer may be a layer in which a plurality of metal-related layers are provided on a predetermined substrate (for example, a plurality of electrodes provided on a substrate).
  • the shape of the metal-related layer is not particularly limited, and examples thereof include a plate shape and a rod shape.
  • the thickness of the metal-related layer is also not particularly limited, and may be a thickness known as a metal-related layer to be laminated with the cured product layer, specifically, a metal electrode, a semiconductor chip, or the like, and preferably 0.1 ⁇ m to 10 mm. It is.
  • the laminate includes a joined body in which a metal-related layer, a cured product layer, and a metal-related layer are laminated in this order.
  • the method for producing the joined body is not particularly limited, but the composition is applied to one surface of one metal-related layer or two metal-related layers, and the metal-related layer, the cured product layer, Are preferably arranged so as to form a joined body laminated in this order, and compression-molded.
  • the temperature during compression molding is usually from room temperature to 350 ° C., preferably from room temperature to 300 ° C., more preferably from 50 ° C. to 250 ° C., and the time is usually from 5 seconds to 10 hours, preferably from 1 minute to 5 hours. And more preferably 5 minutes to 1 hour, and the pressure is usually 0.01 to 30 MPa, preferably 0.1 to 5 MPa.
  • the laminate and the joined body can be manufactured by heating at a relatively low temperature. After hardening in this way, it is preferable to gradually cool to suppress stress strain and the like. After cooling, reheating may be performed to alleviate strain and the like.
  • the thickness of the laminated body may be appropriately changed depending on the application, but in order to increase the thermal conductivity in the thickness direction of the laminated body, a thinner one is preferable. , Preferably 5 to 2000 ⁇ m, more preferably 10 to 1000 ⁇ m, and particularly preferably 15 to 500 ⁇ m.
  • the cured product and the cured product layer have high thermal conductivity, and the coefficient of thermal expansion takes a value from negative to positive depending on the type of organic material and inorganic filler used, the mixing ratio, curing conditions, etc., and the chemical stability.
  • the mechanical strength includes Young's modulus, tensile strength, tear strength, bending strength, flexural modulus, impact strength and the like.
  • the cured product and the laminate are useful for a heat dissipation substrate, a heat dissipation plate (a planar heat sink), a heat dissipation sheet, a heat dissipation film, a heat dissipation coating, a heat dissipation adhesive, a heat dissipation insulating substrate with electrodes, a heat conductive electronic substrate, and the like. It is.
  • An electronic device includes the cured product or the laminate, and an electronic device having a heat generating portion. It is preferable that the cured product or the laminate is disposed on the electronic device so as to contact the heat generating portion.
  • the term “contact” means that the cured product or the laminate may directly contact the heat-generating portion, or may contact via an adhesive layer or the like.
  • the cured product or the laminate may be any of a heat-radiating substrate, a heat-radiating plate (a planar heat sink), a heat-radiating sheet, a heat-radiating film, a heat-radiating coating, a heat-radiating adhesive, a heat-radiating insulating substrate with electrodes, and a heat-conductive electronic substrate. It may be.
  • the electronic device includes, for example, a semiconductor element. Since the cured product or the laminate contains a cured product obtained from the present composition, it has high heat resistance in addition to high thermal conductivity. For this reason, it is particularly effective when the electronic device includes a power semiconductor made of silicon, silicon carbide, gallium nitride, gallium oxide, diamond, or the like that requires a more efficient heat radiation mechanism for high power among semiconductor elements. It is. Examples of electronic devices equipped with these power semiconductors include a main conversion element of a high-power inverter, an uninterruptible power supply, a variable voltage variable frequency control device of an AC motor, a control device of a railway vehicle, a hybrid car, an electric car, and the like. Electric transport equipment and IH cookers are included.
  • YX4000H a compound represented by the formula (1-12), manufactured by Mitsubishi Chemical Corporation, (trade name) jER YX4000H -"JER828”: manufactured by Mitsubishi Chemical Corporation, (trade name) jER828 (polymerizable oxiranyl compound)
  • “Curing agent 1” a compound represented by the formula (1-13) (4,4'-ethylenedianiline), manufactured by Tokyo Chemical Industry Co., Ltd.
  • “Curing agent 2” a compound represented by the formula (1-14) (4,4'-diaminodiphenylmethane), manufactured by Wako Pure Chemical Industries, Ltd.
  • Example 1 Put 7.2 g of PTX-25, 0.621 g of polymerizable liquid crystal, 1.534 g of YX4000H, and 0.625 g of curing agent 1 in a powder lab dispersion tester PWB type manufactured by Nippon Coke Industry Co., Ltd. While maintaining the temperature at 80 ° C., stirring was performed at 500 rotations for 10 minutes, then at 1000 rotations for 1 minute, then at 2,000 rotations for 1 minute, and further at 3000 rotations for 1 minute. Next, after the internal temperature became 60 ° C. or lower, the composition was taken out of the container.
  • ⁇ Measurement of thermal diffusivity and calculation of thermal conductivity> Using a sample for measuring thermal diffusivity, a multilayer sample is measured using an LFA467 HyperFlash thermal diffusivity device manufactured by NETZSCH Corporation, and heat including heat loss due to contact thermal resistance is measured using a multilayer sample analysis model (three layers). The diffusivity was calculated. In the multilayer sample analysis, the analysis was performed with the density of the cured product being 1.6 g / cm 3 and the specific heat being 1.0 J / g ⁇ K. The thermal conductivity of the cured product was calculated by multiplying the obtained thermal diffusivity by the density and the specific heat. Table 1 shows the results.
  • ⁇ Tensile test> A tensile test was performed as described below, and the tensile strength was confirmed. Using a tensile tester (manufactured by Tensilon, RTF-1310), the tensile test sample was pulled in the direction of the arrow in FIG. 2 at a speed of 1 mm / min, and the tensile strength (N) at break was measured. If it did not break, the detection limit (500N) or more was set. Table 1 shows the results. "E” in Table 1 indicates that the two aluminum plates were peeled off when the tensile test sample was fixed to the tensile test measuring instrument.
  • Examples 2-3 and Comparative Examples 1-3 A composition was prepared in the same manner as in Example 1 except that the types and amounts of the components were changed as shown in Table 1, and each sample was prepared from the composition and evaluated.
  • a predetermined amount of an inorganic filler By using a predetermined amount of an inorganic filler, a predetermined ratio of a bifunctional or higher functional polymerizable liquid crystal compound and a bifunctional or higher non-liquid crystalline polymerizable compound, and a curing agent, excellent adhesion to a metal, a metal compound or a semiconductor is obtained. Thus, a composition (cured product) having a high thermal conductivity could be obtained. On the other hand, when a bifunctional or higher functional polymerizable liquid crystal compound or a bifunctional or higher functional non-liquid crystalline polymerizable compound is not used, a composition having excellent adhesion to a metal, a metal compound or a semiconductor and having high thermal conductivity (Cured product) could not be obtained.

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Abstract

Des modes de réalisation de la présente invention concernent une composition, un produit durci, un corps stratifié et un dispositif électronique. La composition comprend : une charge inorganique ; un composé de cristaux liquides polymérisable ayant 2 groupes fonctionnels ou plus ; un composé de cristaux non liquides polymérisable ayant 2 groupes fonctionnels ou plus ; et un agent de durcissement qui est capable de durcir le composé de cristaux liquides polymérisable et le composé de cristaux non liquides polymérisable. La teneur en charge inorganique est de 150 à 4500 parties en masse par rapport à 100 parties en masse du composé de cristaux liquides polymérisable. Le rapport des quantités contenues de composé de cristaux liquides polymérisable et de composé de cristaux non liquides polymérisable (masse de composé de cristaux liquides polymérisable/masse de composé de cristaux non liquides polymérisable) est de 20/80 à 95/5.
PCT/JP2019/033877 2018-08-31 2019-08-29 Composition, produit durci, corps stratifié et dispositif électronique WO2020045560A1 (fr)

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WO2022092063A1 (fr) * 2020-10-30 2022-05-05 Jnc株式会社 Composition destinée à la formation d'une résine à faible constante diélectrique, élément à faible constante diélectrique et dispositif électronique l'utilisant
WO2022206509A1 (fr) * 2021-03-31 2022-10-06 华为技术有限公司 Matériau thermoconducteur et son procédé de fabrication, préimprégné, stratifié et carte de circuit imprimé
WO2023128067A1 (fr) * 2021-12-30 2023-07-06 솔루스첨단소재 주식회사 Composition de résine époxyde qui est stable à des températures élevées et encapsulant la comprenant

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WO2023128067A1 (fr) * 2021-12-30 2023-07-06 솔루스첨단소재 주식회사 Composition de résine époxyde qui est stable à des températures élevées et encapsulant la comprenant

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