WO2021131803A1 - 組成物、熱伝導シート、熱伝導シート付きデバイス - Google Patents

組成物、熱伝導シート、熱伝導シート付きデバイス Download PDF

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Publication number
WO2021131803A1
WO2021131803A1 PCT/JP2020/046333 JP2020046333W WO2021131803A1 WO 2021131803 A1 WO2021131803 A1 WO 2021131803A1 JP 2020046333 W JP2020046333 W JP 2020046333W WO 2021131803 A1 WO2021131803 A1 WO 2021131803A1
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Prior art keywords
group
heat conductive
conductive sheet
composition
compound
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PCT/JP2020/046333
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English (en)
French (fr)
Japanese (ja)
Inventor
林　大介
誠一 人見
輝樹 新居
慶太 高橋
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Fujifilm Corp
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Fujifilm Corp
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Priority to CN202080089029.5A priority Critical patent/CN114846086B/zh
Priority to EP20905695.1A priority patent/EP4082785A4/en
Priority to JP2021567245A priority patent/JP7343613B2/ja
Publication of WO2021131803A1 publication Critical patent/WO2021131803A1/ja
Priority to US17/849,191 priority patent/US20220325163A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/14—Solid materials, e.g. powdery or granular
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    • 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
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    • H10W40/251—Organics

Definitions

  • the present invention relates to a composition, a heat conductive sheet, and a device with a heat conductive sheet.
  • Patent Document 1 describes a heat conductive material containing a cured product of a disk-shaped compound having one or more specific reactive functional groups and a crosslinkable compound having a group that reacts with the reactive functional group. There is.
  • an object of the present invention is to provide a composition capable of forming a heat conductive sheet having excellent peel strength. Another object of the present invention is to provide a heat conductive sheet formed by the above composition and a device with a heat conductive sheet.
  • a polymer compound which is at least one selected from the group consisting of a thermoplastic resin and rubber, and inorganic particles.
  • the polymer compound is at least one selected from the group consisting of polysulfone, polyethersulfone, polyetheretherketone, polyetherimide, modified polyphenylene ether, polycarbonate, acrylate polyarylate, liquid crystal polymer, polyimide and polyphenylene sulfide.
  • the composition according to [1] or [2] which comprises.
  • [4] The composition according to any one of [1] to [3], wherein the ratio of the content of the polymer compound to the content of the inorganic particles is 0.01 to 0.2 by mass ratio.
  • [5] The composition according to any one of [1] to [4], wherein the ratio of the content of the polymer compound to the content of the inorganic particles is 0.02 to 0.12 by mass ratio.
  • [6] The composition according to any one of [1] to [5], wherein the ratio of the content of the polymer compound to the content of the inorganic particles is 0.04 to 0.08 in terms of mass ratio.
  • content of the polymer compound is 3 to 10% by mass with respect to the total mass of the solid content contained in the composition.
  • inorganic particles are particles of an inorganic oxide or an inorganic nitride.
  • inorganic particles are boron nitride particles.
  • the present invention it is possible to provide a composition capable of forming a heat conductive sheet having excellent peel strength. Further, according to the present invention, it is possible to provide a heat conductive sheet formed by the above composition and a device with a heat conductive sheet.
  • the composition of the present invention the heat conductive sheet, and the device with the heat conductive sheet will be described in detail.
  • the numerical range represented by using “-” means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
  • the “content” of the component means the total content of the two or more kinds of components.
  • the description of "(meth) acryloyl group” means “one or both of acryloyl group and methacryloyl group”.
  • the description of "(meth) acrylamide group” means “one or both of an acrylamide group and a methacrylamide group”.
  • the type of substituent, the position of the substituent, and the number of substituents in the case of “may have a substituent” are not particularly limited.
  • the number of substituents may be, for example, one or two or more.
  • the substituent include a monovalent non-metal atomic group excluding a hydrogen atom, and for example, it can be selected from the following substituent group Y.
  • Substituent group Y Halogen atom (-F, -Br, -Cl, -I), hydroxyl group, amino group, carboxylic acid group and its conjugate base group, anhydride carboxylic acid group, cyanate ester group, unsaturated polymerizable group, oxylanyl group, oxetanyl group , Aziridinyl group, thiol group, isocyanate group, thioisocyanate group, aldehyde group, alkoxy group, allyloxy group, alkylthio group, arylthio group, alkyldithio group, aryldithio group, N-alkylamino group, N, N-dialkylamino group , N-arylamino group, N, N-diarylamino group, N-alkyl-N-arylamino group, acyloxy group, carbamoyloxy group, N-alkylcarbamoyloxy group,
  • these substituents may be bonded to each other or to a substituted group to form a ring, if possible.
  • Examples of the unsaturated polymerizable group include a (meth) acryloyl group, a (meth) acrylamide group, and a substituent represented by Q1 to Q7 below.
  • the bonding direction of the divalent group described in the present specification is not limited unless otherwise specified.
  • composition contains a disk-shaped compound, a polymer compound (hereinafter, also referred to as "specific polymer”) which is at least one selected from the group consisting of a thermoplastic resin and rubber, and inorganic particles. To do.
  • a polymer compound hereinafter, also referred to as "specific polymer” which is at least one selected from the group consisting of a thermoplastic resin and rubber, and inorganic particles.
  • the composition of the present invention contains a disk-shaped compound.
  • the disk-shaped compound is used as a raw material for forming a heat conductive sheet.
  • a disc-shaped compound means a compound having a disc-shaped structure at least partially.
  • the disc-like structure has at least a non-aromatic ring or an aromatic ring.
  • the disk-shaped compound can form a columnar structure by forming a stacking structure by ⁇ - ⁇ interaction between molecules.
  • Examples thereof include the triphenylene structure described in 2012, 51, 7990-7793 or JP-A-7-306317, and the tri-substituted benzene structure described in JP-A-2007-002220 and JP-A-2010-244038.
  • the disk-shaped compound may be a liquid crystal compound exhibiting liquid crystallinity or a non-liquid crystal compound exhibiting liquid crystallinity, but the liquid crystal compound is preferable because the thermal conductivity of the heat conductive sheet is more excellent. That is, as the disk-shaped compound, a disk-shaped liquid crystal compound is preferable.
  • disk-shaped compound examples include C.I. Destrade et al. , Mol. Crysr. Liq. Cryst. , Vol. 71, page 111 (1981); Chemical Society of Japan, Quarterly Review of Chemistry, No. 22, Chemistry of liquid crystal, Chapter 5, Chapter 10, Section 2 (1994); Kohne et al. , Angew, Chem. Int. Ed. , 23, 82 (1984); Zhang et al. , J. Am. Chem. Soc. , Vol. Examples thereof include compounds described in 116, 2655 (1994) and Japanese Patent No. 4592225.
  • the disk-shaped compound preferably has at least one of any of the substituents exemplified in the above-mentioned Substituent Group Y. More specifically, as the substituent, a hydroxyl group (-OH), a carboxylic acid group (-COOH), a carboxylic acid anhydride group, an amino group (-NH 2 ), a cyanate ester group (-OC ⁇ N), Examples thereof include a halogen atom, an isocyanate group, a cyano group, the unsaturated polymerizable group, an oxylanyl group, an oxetanyl group, an aziridinyl group, a thiol group, a thioisocyanate group, an aldehyde group, and a sulfo group.
  • substituent a hydroxyl group (-OH), a carboxylic acid group (-COOH), a carboxylic acid anhydride group, an amino group (-NH 2 ), a cyanate este
  • the heat conductive sheet formed by using the disk-shaped compound having three or more specific functional groups tends to have a high glass transition temperature and high heat resistance.
  • the upper limit of the number of the specific functional groups is not particularly limited, but is preferably 8 or less, and more preferably 6 or less.
  • a compound selected from the group consisting of the compounds represented by the following formulas (D1) to (D16) is preferable because the heat conductive sheet is more excellent in heat conductivity, and the formula (D4) is used.
  • the compound represented by (D16) or the compound represented by the formula (D16) is more preferable.
  • "-LQ” represents "-LQ”
  • "QL-" represents "QL-”.
  • L represents a divalent linking group.
  • the plurality of Ls may be the same or different.
  • the alkylene group preferably has 1 to 12 carbon atoms.
  • the number of carbon atoms of the alkenylene group is preferably 2 to 12.
  • the number of carbon atoms of the arylene group is preferably 10 or less.
  • the alkylene group, the alkenylene group, and the arylene group may further have a substituent.
  • the substituent is not particularly limited, but for example, an alkyl group (preferably having 1 to 6 carbon atoms), a halogen atom, a cyano, an alkoxy group (preferably having 1 to 6 carbon atoms), and an acyloxy group (preferably having 1 to 6 carbon atoms). Is preferable).
  • L is shown below.
  • the bond on the left side binds to the core of the compound represented by any of the formulas (D1) to (D15) (hereinafter, also simply referred to as "central ring"), and the bond on the right side is Q.
  • AL means an alkylene group or an alkaneylene group
  • AR means an arylene group.
  • Q represents a hydrogen atom or a substituent.
  • the plurality of Qs may be the same or different.
  • Examples of the substituent include the groups exemplified in the above-mentioned Substituent Group Y.
  • substituents include a halogen atom, an isocyanate group, a cyano group, the unsaturated polymerizable group, an oxylanyl group, an oxetanyl group, an aziridinyl group, a thiol group, a thioisocyanate group, an aldehyde group, and a sulfo group.
  • three or more Qs in the formulas (D1) to (D15) are independently (meth) acrylic group, (meth) acrylamide group, and oxylanyl because the heat conductivity of the heat conductive sheet is more excellent. It is preferable to represent a specific functional group selected from the group consisting of a group, an oxetanyl group, a hydroxyl group, an amino group, a thiol group, an isocyanate group, a carboxyl group, and an anhydrous carboxylic acid group.
  • a heat conductive sheet formed by using a disk-shaped compound containing three or more of the specific functional groups tends to have a high glass transition temperature and high heat resistance.
  • the disk-shaped compound is less affected by the characteristics of the mesogen moiety even if it contains three or more of the above-mentioned specific functional groups.
  • 8 or less Qs preferably represent the specific functional group, and 6 or less Qs more preferably represent the specific functional group.
  • the carboxylic acid anhydride group means a monovalent substituent obtained by removing an arbitrary hydrogen atom from an acid anhydride such as maleic anhydride, phthalic anhydride, pyromellitic anhydride, and trimellitic anhydride. To do.
  • Q preferably has no fluorine atom.
  • Q preferably represents a substituent having no fluorine atom or a hydrogen atom.
  • the compounds represented by the formulas (D1) to (D15) are more preferably free of fluorine atoms. That is, it is more preferable that L and Q do not have a fluorine atom.
  • Q preferably does not have an alkyl group having 10 or more carbon atoms.
  • Q preferably represents a substituent having no alkyl group having 10 or more carbon atoms or a hydrogen atom.
  • the compounds represented by the formulas (D1) to (D15) are more preferably not having an alkyl group having 10 or more carbon atoms. That is, it is more preferable that L and Q do not have an alkyl group having 10 or more carbon atoms.
  • the compound represented by the formula (D4) is preferable from the viewpoint that the heat conductivity of the heat conductive sheet is more excellent.
  • the compound represented by the formula (D4) the compound represented by the following formula (XI) is preferable because the heat conductivity of the heat conductive sheet is more excellent.
  • R 11, R 12, R 13, R 14, R 15, and R 16 are each independently, * - X 11 -L 11 -P 11, or * -X 12 -L 12 - Represents Y 12.
  • * represents the bonding position with the triphenylene ring.
  • R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 are * -X 11- L 11.
  • -P 11 is more preferable.
  • R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are all the same.
  • L 11 represents a single bond or a divalent linking group.
  • Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, and a heptylene group.
  • Examples of the arylene group include a 1,4-phenylene group, a 1,3-phenylene group, a 1,4-naphthylene group, a 1,5-naphthylene group, and an anthrasenylene group, and a 1,4-phenylene group is preferable.
  • the alkylene group and the arylene group may each have a substituent.
  • the number of substituents contained in the alkylene group or the arylene group is preferably 1 to 3, more preferably 1.
  • the substitution position of the substituent is not particularly limited.
  • As the substituent a halogen atom or an alkyl group having 1 to 3 carbon atoms is preferable, and a methyl group is more preferable.
  • the alkylene group and the arylene group are unsubstituted. Of these, it is more preferable that the alkylene group is unsubstituted.
  • P 11 represents a hydroxyl group, a carboxylic acid group, an anhydrous carboxylic acid group, an amino group, a thiol group, a cyanate ester group, or the unsaturated polymerizable group.
  • P 11 is a hydroxyl group
  • L 11 contains an arylene group, and this arylene group is bonded to P 11.
  • X 12 is synonymous with X 11 and has the same preferred embodiments.
  • L 12 is synonymous with L 11 and has the same preferred embodiments.
  • -X 12 -L 12 - Examples of include examples of the above-mentioned L L101 ⁇ L138.
  • Y 12 is one or one in a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, or a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms.
  • Y 12 is preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, or an alkylene oxide group having 1 to 20 carbon atoms, and is linear or linear or having 1 to 12 carbon atoms.
  • a branched alkyl group, an ethylene oxide group, or a propylene oxide group is more preferable.
  • Specific examples of the compound represented by the formula (XI) include paragraphs 0028 to 0036 of JP-A-7-281028, paragraphs 0016 to 0018 of JP-A-7-306317, and JP-A-2005-156822. Examples thereof include the compounds described in paragraphs 0067 to 0072 of Kai 2006-301614 and pages 330 to 333 of the LCD Handbook (published by Maruzen Co., Ltd., 2000).
  • the compound represented by the formula (XI) conforms to the methods described in JP-A-7-306317, JP-A-7-281028, JP-A-2005-156822, and JP-A-2006-301614. Can be synthesized.
  • R 17X , R 18X , and R 19X each independently represent *-(X 211X- Z 21X ) n21X- L 21X- Q. * Represents the bonding position with the central ring (corresponding to the 6-membered aromatic ring represented by the above formula (D16)).
  • Z 21X represents a 5- or 6-membered aromatic ring group or a 5- or 6-membered non-aromatic ring group.
  • L 21X represents a single bond or a divalent linking group.
  • Q is synonymous with Q in the formulas (D1) to (D15), and the preferred embodiment is also the same.
  • n21X represents an integer of 0 to 3. When n21X is 2 or more, a plurality of them (X 211X- Z 21X ) may be the same or different. As n21X, an integer of 1 to 3 is preferable. Among them, 1 or 2 is more preferable, and 1 is further preferable from the viewpoint that the heat conductivity of the heat conductive sheet is more excellent.
  • Q preferably has no fluorine atom.
  • Q preferably represents a substituent having no fluorine atom or a hydrogen atom.
  • the compound represented by the formula (D16) is more preferably free of fluorine atoms.
  • Q preferably does not have an alkyl group having 10 or more carbon atoms.
  • Q preferably represents a substituent having no alkyl group having 10 or more carbon atoms or a hydrogen atom.
  • the compound represented by the formula (D16) is more preferably not having an alkyl group having 10 or more carbon atoms.
  • the central ring of the disk-shaped compound (corresponding to the 6-membered aromatic ring represented by the above formula (D16)) is preferably a benzene ring or a triazine ring.
  • R 17 , R 18 , and R 19 independently represent *-(X 211- Z 21 ) n21- L 21- P 21 or *-(X 221- Z 22 ) n22- Y 22 .
  • * represents the connection position with the central ring.
  • Two or more of R 17 , R 18 , and R 19 are *-(X 211- Z 21 ) n21- L 21- P 21 .
  • It is preferable that all of R 17 , R 18 , and R 19 are *-(X 211- Z 21 ) n21- L 21- P 21 in that the heat conductivity of the heat conductive sheet is more excellent.
  • R 17 , R 18 , and R 19 are all the same.
  • Z 21 and Z 22 independently represent a 5- or 6-membered aromatic ring group or a 5- or 6-membered non-aromatic ring group, for example, a 1,4-phenylene group, respectively.
  • Examples include 1,3-phenylene group and aromatic heterocyclic group.
  • the aromatic ring group and the non-aromatic ring group may have a substituent.
  • the number of substituents is preferably 1 or 2, more preferably 1.
  • the substitution position of the substituent is not particularly limited.
  • As the substituent a halogen atom or a methyl group is preferable. It is also preferable that the aromatic ring group and the non-aromatic ring group are unsubstituted.
  • aromatic heterocyclic group examples include the following aromatic heterocyclic groups.
  • a 41 and A 42 each independently represent a methine group or a nitrogen atom.
  • X 4 represents an oxygen atom, a sulfur atom, a methylene group, or an imino group. At least one of A 41 and A 42 is preferably a nitrogen atom, and more preferably both are nitrogen atoms. Further, X 4 is preferably an oxygen atom.
  • n21 and n22 which will be described later, are two or more, a plurality of (X 211- Z 21 ) and (X 221- Z 22 ) may be the same or different, respectively.
  • L 21 represents a single bond or a divalent linking group and is synonymous with L 11 in the above formula (XI).
  • an arylene group the number of carbon atoms is preferably 6 to 20, more preferably 6 to 14, and even more preferably 6 to 10, or a group composed of a combination thereof is preferable.
  • n22 is 1 or more, -L 21 - Examples of are examples of L in the above formula (D1) ⁇ (D15) L101 ⁇ L138 and the like as well.
  • P 21 represents a hydroxyl group, a carboxylic acid group, an anhydrous carboxylic acid group, an amino group, a thiol group, a cyanate ester group, or the unsaturated polymerizable group.
  • the preferred embodiment of Y 22 is the same as the preferred embodiment of Y 12 in the formula (XI).
  • N21 and n22 independently represent an integer of 0 to 3, and an integer of 1 to 3 is preferable. Among them, 1 or 2 is more preferable, and 1 is further preferable from the viewpoint that the heat conductivity of the heat conductive sheet is more excellent.
  • Preferred examples of the compound represented by the formula (XII) include the following compounds.
  • R represents ⁇ L 21 ⁇ P 21.
  • the compound represented by the formula (XII) can be synthesized according to the methods described in JP-A-2010-244038, JP-A-2006-07692, and JP-A-2007-002220.
  • the compounds represented by the above formulas (D1) to (D16) are used.
  • the length of the divalent linking group connecting the central ring and the specific functional group represented by Q is short. More specifically, in the divalent linking group (L or L 21X ) connecting the central ring and the specific functional group, the atom bonded to the central ring and the atom bonded to the specific functional group are connected by the shortest distance.
  • the number of atoms on the bond (hereinafter, also referred to as "the number of atoms between both ends of the divalent linking group”) is preferably 11 or less, and preferably 7 or less.
  • both the atom bonded to the ring as the starting point and the atom bonded to the specific functional group as the ending point shall be counted.
  • the lower limit of the number of atoms between both ends of the divalent linking group is not particularly limited and may be 0. That is, in the compounds represented by the above formulas (D1) to (D16), the central ring and the specific functional group represented by Q may be directly bonded.
  • the composition when the heat conductive sheet formed by using the composition containing the disk-shaped compound contains a cured product obtained by curing the composition containing the disk-shaped compound, the composition is a disk.
  • the state compound may be contained as a main agent or as a curing agent. Further, the above composition may contain a disk-shaped compound as both a main agent and a curing agent.
  • the composition preferably contains at least a disk-shaped compound as a main agent.
  • the "main agent” is selected from the group consisting of unsaturated polymerizable groups ((meth) acrylic group, (meth) acrylamide group, etc.), oxylanyl group, oxetanyl group, and aziridinyl group. It means a compound having a functional group.
  • the "hardener” is selected from the group consisting of a hydroxyl group, an amino group, a thiol group, an isocyanate group, a thioisocyanate group, an aldehyde group, a carboxyl group, an anhydrous carboxylic acid group, and a sulfo group. It means a compound having a functional group.
  • the composition When the composition is cured to form a heat conductive sheet, the composition may or may not contain a curing agent as a disc-shaped compound or a curable compound described later.
  • one or more Qs are from the group consisting of a (meth) acrylic group, a (meth) acrylamide group, an oxylanyl group, and an oxetanyl group. It is preferably the reactive group of choice. Among them, it is more preferable that two or more Qs are the above-mentioned reactive groups, and it is further preferable that three or more Qs are the above-mentioned reactive groups, in that the heat conductivity of the heat conductive sheet is more excellent.
  • the upper limit of the number of Qs, which are the reactive groups is not particularly limited, but is preferably 8 or less, and more preferably 6 or less.
  • an oxylanyl group or an oxetanyl group is more preferable, and an oxylanyl group is further preferable.
  • the disk-shaped compounds represented by the formulas (D1) to (D16) are curing agents, a group in which one or more Qs are composed of a hydroxyl group, an amino group, a thiol group, an isocyanate group, a carboxyl group and an anhydrous carboxylic acid group. It is preferably an active hydrogen-containing functional group that is more selected. Among them, in terms of the heat conductivity of the heat conductive sheet being more excellent, it is more preferable that two or more Qs are the active hydrogen-containing functional groups, and three or more Qs are the active hydrogen-containing functional groups. Is more preferable.
  • the upper limit of the number of Qs, which are the active hydrogen-containing functional groups is not particularly limited, but is preferably 8 or less, and more preferably 6 or less.
  • As the active hydrogen-containing functional group a hydroxyl group, an amino group, a thiol group or an carboxylic acid anhydride group is more preferable, and a hydroxyl group or an amino group is further preferable.
  • the disk-shaped compound may be used alone or in combination of two or more.
  • the content of the disk-shaped compound in the composition is preferably 1 to 50% by mass, more preferably 3 to 40% by mass, still more preferably 5 to 30% by mass, based on the total mass of the solid content of the composition.
  • the solid content means a component of the composition that forms a heat conductive sheet, and the solvent is removed. The solid content is calculated as the solid content even if the property is liquid.
  • the composition of the present invention contains at least one polymer compound (specific polymer) selected from the group consisting of thermoplastic resins and rubbers.
  • specific polymer selected from the group consisting of thermoplastic resins and rubbers.
  • thermoplastic resin is not particularly limited as long as it is a resin that is plasticized by heating to a glass transition temperature (Tg) or a melting point or higher.
  • Tg glass transition temperature
  • the thermoplastic resin includes a thermoplastic elastomer.
  • the rubber may be natural rubber or synthetic rubber, but synthetic rubber is preferable.
  • thermoplastic resins examples of the thermoplastic resin having a cyclic structure such as an aromatic ring in the main chain include polyamide (PA), polycarbonate (PC), modified polyphenylene ether (m-PPE), and polyethylene terephthalate (PET). , Polybutylene terephthalate (PBT), cyclic polyolefin (COP), polyphenylene sulfide (PPS), polytetrafluoroethylene (PTFE), polysulfone (PSF), polyethersulfone (PES), amorphous polyallylate (PAR), Examples thereof include polyetheretherketone (PEEK), thermoplastic polyimide (PI), polyetherimide (PEI), and polyamideimide (PAI).
  • PA polyamide
  • PC polycarbonate
  • m-PPE modified polyphenylene ether
  • PET polyethylene terephthalate
  • PBT Polybutylene terephthalate
  • COP cyclic polyolefin
  • PPS polyphenylene sul
  • thermoplastic resins examples of the thermoplastic resin having no cyclic structure in the main chain include polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC), polyvinylidene chloride, polystyrene (PS), and poly.
  • PE polyethylene
  • PP polypropylene
  • PVC polyvinyl chloride
  • PS polystyrene
  • examples thereof include vinyl chloride (PVAC), polytetrafluoroethylene (PTFE), ABS resin (acrylonitrile butadiene resin), AS resin (acrylic nitrile styrene resin), acrylic resin (PMMA), and polyacetal (POM).
  • thermoplastic elastomer examples include polyolefin-based thermoplastic elastomers, polyester-based thermoplastic elastomers, polyurethane-based thermoplastic elastomers, PVC (polyvinyl chloride), and nitrile rubber.
  • Examples of the rubber include styrene-butadiene copolymer, polybutadiene, polyisoprene, butadiene-isoprene copolymer, butadiene-styrene-isoprene copolymer, acrylonitrile-butadiene copolymer, chloroprene rubber, butyl rubber, and butyl halide rubber.
  • examples thereof include urethane rubber, silicone rubber, fluororubber, chlorinated polyethylene rubber, and acrylic rubber.
  • thermoplastic resin having a cyclic structure in the main chain is preferable, and a thermoplastic resin having an aromatic ring in the main chain is more preferable, because the heat conductive sheet is excellent in thermal conductivity.
  • the cyclic structure (preferably aromatic ring) of these resins is a disk such as an aromatic ring of a disk-shaped compound. It is presumed that the thermal conductivity is improved by the ⁇ - ⁇ interaction between the molecules with the state structure.
  • PC polycarbonate
  • m-PPE modified polyphenylene ether
  • PSF polysulfone
  • PES polyethersulfone
  • PEEK polyetheretherketone
  • PI polyetherimide
  • amorphous polyallylate Liquid crystal polymers, polyimides, or polyphenylene sulfides are more preferred, with polysulfone, polyethersulfone, or polyetherimide being particularly preferred.
  • the weight average molecular weight of the specific polymer is not particularly limited, but is preferably 10,000 to 300,000, more preferably 20,000 to 100,000.
  • the specific polymer may be used alone or in combination of two or more.
  • the content of the specific polymer is preferably 0.1 to 30% by mass, more preferably 1 to 15% by mass, still more preferably 3 to 10% by mass, based on the total mass of the solid content of the composition.
  • the composition of the present invention contains inorganic particles.
  • a heat conductive sheet having better heat conductivity can be formed.
  • any inorganic particles conventionally used as an inorganic filler for a heat conductive material may be used.
  • the inorganic particles include inorganic oxides, inorganic nitrides and inorganic nitrides, and particles of inorganic oxides or inorganic nitrides are preferable.
  • the shape of the inorganic particles is not particularly limited, and may be in the form of particles, a film, or a flat plate. Examples of the particle-like shape include rice granules, spherical shape, cube shape, spindle shape, scaly shape, agglutinating shape, and indefinite shape.
  • inorganic oxide examples include zirconium oxide (ZrO 2 ), titanium oxide (TiO 2 ), silicon oxide (SiO 2 ), aluminum oxide (Al 2 O 3 ), iron oxide (Fe 2 O 3 , FeO, Fe 3).
  • the inorganic oxide is preferably titanium oxide, aluminum oxide, or zinc oxide.
  • the inorganic oxide may be an oxide produced by oxidizing a metal prepared as a non-oxide in an environment.
  • inorganic nitride examples include boron nitride (BN), carbon nitride (C 3 N 4 ), silicon nitride (Si 3 N 4 ), gallium nitride (GaN), indium nitride (InN), and aluminum nitride (AlN).
  • BN boron nitride
  • C 3 N 4 carbon nitride
  • Si 3 N 4 silicon nitride
  • GaN gallium nitride
  • InN indium nitride
  • AlN aluminum nitride
  • the inorganic nitride preferably contains an aluminum atom, a boron atom, or a silicon atom, more preferably aluminum nitride, boron nitride, or silicon nitride, and even more preferably aluminum nitride or boron nitride.
  • Boron nitride is particularly preferable.
  • the inorganic particles contain an inorganic nitride in that the heat conductive sheet is more excellent in heat conductivity.
  • the content of the inorganic nitride in the composition is preferably 40% by mass or more, more preferably 60% by mass or more, and more preferably 80% by mass, based on the total mass of the inorganic particles, in that the heat conductivity of the heat conductive sheet is more excellent. % Or more is more preferable.
  • the size of the inorganic particles is not particularly limited, but the average particle size of the inorganic particles is preferably 500 ⁇ m or less, more preferably 300 ⁇ m or less, still more preferably 200 ⁇ m or less, in that the dispersibility of the inorganic particles is more excellent.
  • the lower limit is not particularly limited, but from the viewpoint of handleability, 10 nm or more is preferable, and 100 nm or more is more preferable.
  • the average particle size of the inorganic particles is determined by randomly selecting 100 inorganic particles using an electron microscope, measuring the particle size (major axis) of each inorganic particle, and arithmetically averaging them. Be done. When a commercially available product of inorganic particles is used, the catalog value may be used.
  • Inorganic particles may be used alone or in combination of two or more. Among them, it is preferable to use two or more kinds of inorganic particles having different average particle diameters, and it is more preferable to use three or more kinds of inorganic particles having different average particle diameters.
  • the content of the inorganic particles in the composition is preferably 30% by mass or more, more preferably 40% by mass or more, and the heat conductivity of the heat conductive sheet is more excellent with respect to the total mass of the solid content of the composition. , 55% by mass or more is more preferable.
  • the upper limit is not particularly limited, but is preferably 95% by mass or less, more preferably 90% by mass or less, based on the total mass of the solid content of the composition.
  • the content of the inorganic particles in the heat conductive sheet is preferably 1 to 95% by mass, more preferably 5 to 95% by mass, further preferably 30 to 90% by mass, and 40 to 40 to the total mass of the heat conductive sheet. 90% by mass is particularly preferable.
  • the ratio of the content of the specific polymer to the content of the inorganic particles is a mass in that the peel strength and the thermal conductivity of the heat conductive sheet are well-balanced.
  • the ratio is preferably 0.01 to 0.2, more preferably 0.02 to 0.12, and even more preferably 0.04 to 0.08.
  • the composition may contain any component other than the above-mentioned disk-shaped compound, specific polymer and inorganic particles.
  • Optional components include, for example, solvents, other curing agents and main agents that do not correspond to disc-shaped compounds (hereinafter, also referred to as "curable compounds" in the present specification), curing accelerators, dispersants, and surfaces of inorganic particles. Examples thereof include a modifier and a polymerization initiator.
  • the curable compound, the curing accelerator, and the polymerization initiator are components that the composition may contain as optional components when the composition is cured to form a heat conductive sheet. Further, the heat conductive sheet may contain an uncured disk-shaped compound.
  • optional components that may be contained in the composition will be described in detail.
  • the composition may further contain a solvent.
  • the type of solvent is not particularly limited, but an organic solvent is preferable.
  • the organic solvent include ethyl acetate, methyl ethyl ketone (MEK), dichloromethane, tetrahydrofuran (THF), hexane, cyclopentanone, and cyclohexanone.
  • the solvent may be used alone or in combination of two or more.
  • the content of the solvent in the composition is preferably such that the total mass (solid content concentration) of the solid content in the composition is 1 to 90% by mass with respect to the total mass of the composition, and is 5 to 85% by mass.
  • the amount is more preferable, and the amount is more preferably 10 to 80% by mass.
  • the composition may further contain a curing agent that does not correspond to the above-mentioned disc-shaped compound or a curing compound that is a main agent.
  • the curing agent corresponding to the curable compound has a functional group selected from a hydroxyl group, an amino group, a thiol group, an isocyanate group, a thioisocyanate group, an aldehyde group, a carboxyl group, an anhydrous carboxylic acid group, and a sulfo group.
  • a curing agent suitable for the disk-shaped compound used as a main agent in the composition is preferable.
  • the composition contains a disk-shaped compound having an oxylanyl group as a main agent
  • a curing agent having a functional group selected from the group consisting of a hydroxyl group, an amino group and an carboxylic acid anhydride group is used as the curable compound.
  • the number of the functional groups contained in the curing agent is not particularly limited, but is preferably 4 or less, and more preferably 3 or less, in terms of the peel strength of the heat conductive sheet being more excellent.
  • the lower limit is not particularly limited, but two or more are preferable.
  • Examples of the curing agent that is not a disk-shaped compound include the epoxy resin curing agent described in paragraph 0028 of Japanese Patent No. 4118691, the amine-based curing agent described in paragraphs 0016 to 0018 of Japanese Patent Application Laid-Open No. 2008-013759, and phenol. Examples thereof include system-based curing agents and acid anhydride-based curing agents, and amine-based curing agents and phenol-based curing agents described in paragraphs 0101 to 0150 of JP2013-227451A.
  • the main agent corresponding to the curable compound has a functional group selected from the group consisting of a (meth) acrylic group, a (meth) acrylamide group, an oxylanyl group, an oxetanyl group, and an aziridinyl group, and has a disk-like structure.
  • the compound is not particularly limited as long as it is not present, but a main agent suitable for the disk-shaped compound used as a curing agent in the composition is preferable.
  • the composition contains a disk-shaped compound having a hydroxyl group, an amino group, or an carboxylic acid anhydride group as a functional group as a curing agent, it is preferable to use a main agent having an oxylanyl group as the curing compound.
  • the number of the functional groups contained in the main agent is not particularly limited, but is preferably 4 or less, and more preferably 3 or less, in that the peel strength of the heat conductive sheet is more excellent.
  • the lower limit is not particularly limited, but two or more are preferable.
  • the number of the functional groups contained in the main agent is not particularly limited, but is preferably two or more.
  • the main agent that is not a disk-shaped compound may be a known epoxy resin monomer or acrylic resin monomer.
  • the main agent that is not a disk-shaped compound include the epoxy resin monomer and acrylic resin monomer described in paragraph 0028 of Japanese Patent No. 4118691, the epoxy compounds described in paragraphs 0006 to 0011 of JP-A-2008-013759, and Examples thereof include the epoxy resin mixture described in paragraphs 0032 to 0100 of JP2013-227451.
  • the curable compound may be used alone or in combination of two or more.
  • the content of the curing agent is preferably 1 to 50% by mass, more preferably 2 to 20% by mass, based on the total mass of the solid content of the composition.
  • the content of the main agent is preferably 1 to 50% by mass, more preferably 3 to 30% by mass, based on the total mass of the solid content of the composition.
  • the composition may further contain a curing accelerator.
  • the curing accelerator include triphenylphosphine, 2-ethyl-4-methylimidazole, boron trifluoride amine complex, 1-benzyl-2-methylimidazole, and paragraph 0052 of JP2012-06722.
  • Examples include curing accelerators.
  • 2-methylimidazole (trade name; 2MZ), 2-undecylimidazole (trade name: C11-Z), 2-heptadecylimidazole (trade name: C17Z), 1,2-dimethylimidazole (trade name).
  • the curing accelerator may be used alone or in combination of two or more.
  • the content of the curing accelerator is preferably 0.01 to 30% by mass, more preferably 0.01 to 20% by mass, based on the total mass of the solid content of the composition. It is preferable, and 0.01 to 10% by mass is more preferable.
  • the composition may further contain a dispersant.
  • the composition preferably contains a dispersant in that the dispersibility of the inorganic particles in the composition is improved and the heat conductivity and adhesiveness of the heat conductive sheet are more excellent.
  • the dispersant can be appropriately selected from the dispersants conventionally used for the heat conductive material. Examples of the dispersant include DISPERBYK-106 (manufactured by BYK-Chemie GmbH), DISPERBYK-111 (manufactured by BYK-Chemie GmbH), ED-113 (manufactured by Kusumoto Kasei Co., Ltd.), and Ajinomoto Fine-Techno Co., Ltd.
  • the dispersant may be used alone or in combination of two or more.
  • the content of the dispersant is preferably 0.01 to 20% by mass, more preferably 0.01 to 10% by mass, based on the total mass of the solid content of the composition.
  • the ratio of the content of the dispersant to the content of the inorganic particles is 0.0001 to 10 in terms of mass ratio. It is preferable, 0.001 to 5 is more preferable.
  • the composition may further contain a surface modifier, which is a component that surface-modifies inorganic particles (for example, inorganic nitrides and inorganic oxides).
  • a surface modifier which is a component that surface-modifies inorganic particles (for example, inorganic nitrides and inorganic oxides).
  • surface modification means a state in which an organic substance is adsorbed on at least a part of the surface of the inorganic particles.
  • the form of adsorption is not particularly limited as long as it is in a bonded state. That is, the surface modification also includes a state in which an organic group obtained by desorbing a part of an organic substance is bonded to the surface of an inorganic particle.
  • the bond may be any bond such as a covalent bond, a coordination bond, an ionic bond, a hydrogen bond, a van der Waals bond, and a metal bond.
  • the surface modification may be made to form a monolayer on at least a part of the surface.
  • the monolayer is a monolayer formed by the chemical adsorption of organic molecules and is known as Self-Assembled MonoLayer (SAM).
  • SAM Self-Assembled MonoLayer
  • only a part of the surface of the inorganic particles may be surface-modified, or the entire surface of the inorganic particles may be surface-modified.
  • the inorganic particles may constitute surface-modified inorganic particles together with the surface modifier.
  • the method for producing the surface-modified inorganic particles is not particularly limited, and examples thereof include a method having a step of bringing the inorganic particles into contact with the surface modifier.
  • the contact between the inorganic particles and the surface modifier is carried out, for example, by stirring in a mixture of the inorganic particles, the surface modifier and the organic solvent.
  • the surface-modified inorganic particles may be separately prepared and then mixed with some or all of the other components in the composition.
  • the composition preferably contains an organic silane molecule (preferably a compound having an alkoxysilyl group) as a surface modifier (preferably a surface modifier for inorganic oxides, more preferably a surface modifier for aluminum oxide).
  • organic silane molecule include 3-aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, and 3- (2-aminoethyl) aminopropyltrimethoxy.
  • Examples thereof include silane, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptotriethoxysilane, and 3-ureidopropyltriethoxysilane.
  • the surface modifier may be used alone or in combination of two or more.
  • the surface modifier preferably an organic silane molecule
  • the content of the inorganic particles preferably an inorganic oxide such as aluminum oxide
  • the mass ratio of the contents is preferably 0.00001 to 0.1, and more preferably 0.00005 to 0.05.
  • the composition may further contain a polymerization initiator.
  • the polymerization initiator include the polymerization initiators described in paragraph 0062 of JP-A-2010-125782 and paragraph 0054 of JP-A-2015-052710.
  • the composition contains a disk-shaped compound having a (meth) acrylic group or a (meth) acrylamide group, or other main agent, it is preferable that the composition contains the above-mentioned polymerization initiator.
  • the polymerization initiator may be used alone or in combination of two or more.
  • the content of the polymerization initiator in the composition is preferably 0.01 to 30% by mass, preferably 0.01 to 20% by mass, based on the total mass of the solid content of the composition.
  • the mass% is more preferable, and 0.01 to 10% by mass is further preferable.
  • the method for producing the composition is not particularly limited, and a known method can be adopted.
  • it can be produced by mixing each of the above-mentioned components (disk-shaped compound, specific polymer, inorganic particles, solvent and optional component) by a known method.
  • each component may be mixed all at once or sequentially.
  • the heat conductive sheet of the present invention is formed using the composition of the present invention.
  • the method for producing the heat conductive sheet is not particularly limited, but for example, it is preferable to cure the composition of the present invention to obtain a heat conductive sheet containing the cured product.
  • a method for curing the composition a method suitable for the type of the disk-shaped compound and other components contained in the composition may be appropriately selected, but a thermosetting reaction is preferable.
  • the heating temperature during the thermosetting reaction is not particularly limited.
  • the thermosetting reaction may be carried out in the range of 50 to 250 ° C.
  • heat treatments having different temperatures may be carried out a plurality of times.
  • the curing treatment is preferably performed on a film-like, sheet-like or plate-like composition. Specifically, for example, the composition may be applied and formed, and the obtained coating film may be cured. At that time, press working may be performed.
  • the curing treatment may be completed when the composition is in a semi-cured state.
  • main curing such as heating may be performed to further cure the heat conductive sheet. It is also preferable to bond the device and the heat conductive sheet by the above-mentioned main curing carried out by heating or the like.
  • main curing carried out by heating or the like.
  • the shape of the heat conductive sheet is not particularly limited, and examples thereof include a shape having a planar spread, and a shape called a film shape, a sheet shape, a plate shape, or the like.
  • the heat conductive sheet has excellent heat conductivity, and can improve the efficiency of heat transfer between objects in contact with both main surfaces of the heat conductive sheet.
  • the thermal conductivity in the film thickness direction (direction perpendicular to the main surface) of the heat conductive sheet is not particularly limited, but is preferably 3 W / mK or more, more preferably 5 W / mK or more, and 8 W / mK. The above is more preferable.
  • the upper limit is not particularly limited, but it is often 30 W / mK or less.
  • the thermal conductivity in the film thickness direction of the heat conductive sheet can be calculated by measuring the thermal diffusivity, specific gravity and specific heat in the film thickness direction of the heat conductive sheet using a known measuring device and multiplying them.
  • the film thickness of the heat conductive sheet is not particularly limited, but is preferably 60 ⁇ m or more, more preferably 100 ⁇ m or more, and further preferably 150 ⁇ m or more in that the insulating property in the film thickness direction is more excellent.
  • the upper limit of the film thickness of the heat conductive sheet is not particularly limited, but is preferably 5000 ⁇ m or less, and more preferably 3000 ⁇ m or less.
  • the film thickness of the heat conductive sheet is the average film thickness.
  • the method for measuring the film thickness of the heat conductive sheet is not particularly limited, and a method of measuring the film thickness of any number of points of the heat conductive sheet using a known film thickness measuring device and calculating the average value thereof can be mentioned. ..
  • the heat conductive sheet is more excellent in peel strength, and the toughness parameter obtained by the following test method 1 is preferably 15 MPa ⁇ % or more, more preferably 30 MPa ⁇ % or more, and 45 MPa ⁇ % or more. Is even more preferable.
  • the upper limit of the toughness parameter is not particularly limited, but is preferably 100 MPa ⁇ % or less.
  • Test method 1 The heat conductive sheet is subjected to a tensile test at a tensile speed of 1 mm / min using a tensile tester in a temperature environment of 25 ° C., and the stress and strain of the heat conductive sheet are measured.
  • a stress-strain curve is created with stress on the vertical axis and strain on the horizontal axis.
  • the stress-strain curve in the section from the origin to the breaking point, the perpendicular line drawn from the breaking point to the horizontal axis, and the area of the figure surrounded by the horizontal axis are integrated and calculated.
  • the integrated value (unit: MPa ⁇ %) is used as the toughness parameter of the heat conductive sheet.
  • the tensile tester include a Tensilon universal material tester (product name "RTC-1225A", manufactured by A & D Co., Ltd.). Further, in the tensile test, a heat conductive sheet cut into a strip of 10 mm ⁇ 45 mm is used as a test sample.
  • the heat conductive sheet can be used as a heat radiating material such as a heat radiating sheet, and can be used for heat radiating applications of various devices. More specifically, by arranging the heat conductive sheet on the device to produce the device with the heat conductive sheet, the heat generated from the device can be efficiently dissipated through the heat conductive sheet. Since the heat conductive sheet has sufficient heat conductivity and high heat resistance, it is used for heat dissipation of power semiconductor devices used in various electric devices such as personal computers, general home appliances, and automobiles. Are suitable.
  • the heat conductive sheet has sufficient heat conductivity even in a semi-cured state, heat dissipation is arranged in a part where it is difficult for light for photocuring to reach, such as a gap between members of various devices. It can also be used as a material. It can also be used as an adhesive layer having thermal conductivity.
  • the heat conductive sheet may be used in combination with other members other than the members formed from the composition.
  • the heat conductive sheet may be combined with a sheet-like support other than the heat conductive sheet.
  • the sheet-shaped support include a plastic film, a metal film, and a glass plate.
  • the material of the plastic film include polyester such as polyethylene terephthalate (PET), polycarbonate, acrylic resin, epoxy resin, polyurethane, polyamide, polyolefin, cellulose derivative, and silicone.
  • PET polyethylene terephthalate
  • acrylic resin epoxy resin
  • polyurethane polyamide
  • polyolefin polyamide
  • cellulose derivative polyolefin
  • silicone silicone
  • the metal film include a copper film.
  • An adhesive layer and / or an adhesive layer may be combined with the heat conductive sheet.
  • a heat conductive sheet and a heat conductive sheet in which an adhesive layer or an adhesive layer is provided on one side or both sides of the heat conductive sheet may be produced.
  • the heat conductive multilayer sheet can be combined with the heat conductive sheet by joining the heat conductive material to an object such as a device to transfer heat through such an adhesive layer and / or an adhesive layer. A stronger bond with the object can be realized.
  • Only one of the adhesive layer and the pressure-sensitive adhesive layer may be provided on one side or both sides of the heat conductive sheet, or both the adhesive layer and the pressure-sensitive adhesive layer may be provided.
  • An adhesive layer may be provided on one surface of the heat conductive sheet, and an adhesive layer may be provided on the other surface. Further, the adhesive layer and / or the adhesive layer may be partially provided on one side or both sides of the heat conductive sheet, or may be provided on the entire surface.
  • the heat conductive sheet may be in a semi-cured state (semi-cured film), and the heat conductive sheet in the heat conductive multilayer sheet may be in a semi-cured state.
  • the adhesive layer in the heat conductive multilayer sheet may be in a cured state, a semi-cured state, or an uncured state.
  • Adhesive layer examples include a layer containing at least one of an adhesive compound (resin and / or low molecular weight compound, etc.).
  • the adhesive layer may further contain other components such as fillers, if desired.
  • the compound having adhesiveness a compound having insulating property, adhesiveness and / or flexibility at the time of adhesion to an object is preferable.
  • the epoxy compound may be an epoxy resin containing an acrylic modified rubber.
  • polyimide resin and the modified polyimide resin examples include Iupicort FS-100L (manufactured by Ube Industries, Ltd.), Semicofine SP-300, SP-400, SP-800 (manufactured by Toray Industries, Inc.), and Uimide series (Unitika Ltd.). Products such as (manufactured by Co., Ltd.) can be mentioned.
  • examples of the polyamide-imide resin and the modified polyamide-imide resin include the KS series (manufactured by Hitachi Kasei Kogyo Co., Ltd.), the Vilomax series (manufactured by Toyo Spinning Co., Ltd.), and Toron (manufactured by Solvay Advanced Polymers Co., Ltd.). Among them, from the viewpoint of high heat resistance and high adhesiveness, it is preferable to use a modified polyamide-imide resin represented by the KS series (manufactured by Hitachi Kasei Kogyo Co., Ltd.).
  • the polyimide resin, the polyamide-imide resin, and the modified polyamide-imide resin used for the adhesive layer may be used alone or in combination of two or more. Further, these resins are often in a varnish state in which the resin is dissolved in a solvent, and can be used as an adhesive layer by directly applying the resin to a support such as a PET film and drying the solvent to form a film.
  • an epoxy compound as a compound having adhesiveness.
  • an epoxy composition containing an epoxy compound, a curing agent thereof, and a curing agent accelerator may be used as an adhesive layer. It is preferable to add glycidyl acrylate to the epoxy composition.
  • the descriptions of JP-A-2002-134531, JP-A-2002-226996, and JP-A-2003-221573 can also be referred to.
  • the epoxy compound used for the adhesive layer is not particularly limited as long as it cures and exhibits an adhesive action.
  • a bisphenol A type or bisphenol F type liquid epoxy compound having a molecular weight of 500 or less can be mentioned. These epoxy compounds are preferable because they can improve the fluidity during lamination.
  • a polyfunctional epoxy compound may be added to the adhesive layer for the purpose of increasing the Tg (glass transition temperature). Examples of the polyfunctional epoxy compound include a phenol novolac type epoxy compound and a cresol novolac type epoxy compound.
  • the epoxy compound used for the adhesive layer the above-mentioned disk-shaped compound or an epoxy compound that can be used as a curable compound may be used.
  • the curing agent for the epoxy compound examples include polyamide, polyamine, acid anhydride, polysulfide, boron trifluoride, and phenol compound (phenol novolac resin, bisphenol, which is a compound having two or more phenolic hydroxyl groups in one molecule. A, bisphenol F, bisphenol S, etc.). Phenolic novolak resin, bisphenol novolak resin, or cresol novolak resin, which are phenol compounds, are preferable because they are excellent in electrolytic corrosion resistance during moisture absorption. Further, as the curing agent, a phenol compound that can be used as the above-mentioned disc-shaped compound or curable compound may be used.
  • a curing accelerator When a curing agent is used, it is preferable to use a curing accelerator together with the curing agent.
  • an imidazole compound is preferable.
  • the imidazole compound include 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, and 1-cyanoethyl-2-phenylimidazolium trimerite.
  • the imidazole compound is commercially available from Shikoku Kasei Kogyo Co., Ltd. under the trade names of 2E4MZ, 2PZ-CN, and 2PZ-CNS.
  • a compound (triphenylphosphine or the like) described as the curing accelerator that may be contained in the above composition may be used.
  • the epoxy compound used for the adhesive layer is also preferably used in combination with a high molecular weight resin compatible with the epoxy compound.
  • the high molecular weight resin compatible with the epoxy compound include a high molecular weight epoxy compound, a functional group-containing rubber having a large polarity, and a functional group-containing reactive rubber having a large polarity.
  • the above-mentioned highly polar functional group-containing reactive rubber include acrylic modified rubber in which a highly polar functional group such as a carboxyl group is added to acrylic rubber.
  • compatible with an epoxy compound means a property of forming a homogeneous admixture without separating from the epoxy compound and separating into two or more phases after curing.
  • the weight average molecular weight of the above high molecular weight resin is not particularly limited. A high molecular weight resin having a weight average molecular weight of 30,000 or more is preferable in terms of reducing the tackiness of the adhesive in the B stage and improving the flexibility at the time of curing.
  • the high molecular weight epoxy compounds include high molecular weight epoxy compounds having a molecular weight of 30,000 to 80,000 and ultrahigh molecular weight epoxy compounds having a molecular weight of more than 80,000 (Special Fair 7-059617, Special Fair 7-059618, Special Fair 7). There are -059619, Tokuho 7-059620, Tokuho 7-064911, and Tokuho 7-068327), all of which are manufactured by Hitachi Kasei Kogyo Co., Ltd.
  • the highly polar functional group-containing reactive rubbers as the carboxyl group-containing acrylic rubber, for example, HTR-860P (trade name) is sold by Nagase ChemteX Corporation.
  • the amount added is 10 parts by mass or more when the resin constituting the adhesive layer is 100 parts by mass. It is preferable to have.
  • the upper limit is not particularly limited, but is preferably 40 parts by mass or less.
  • the high molecular weight resin is 10 parts by mass or more, it is easy to improve the flexibility, tackiness, and / or crack suppression of the phase containing the epoxy compound as the main component (hereinafter referred to as the epoxy compound phase). Insulation does not easily deteriorate.
  • the high molecular weight resin is 40 parts by mass or less, the Tg of the epoxy compound phase can be improved.
  • the weight average molecular weight of the high molecular weight epoxy compound is preferably 20,000 to 500,000. In this range, the strength and / or flexibility in the sheet state and / or the film state is improved, and the tackiness is easily suppressed.
  • silane coupling agent- A silane coupling agent may be added to the adhesive layer in order to improve the interfacial bond between different materials.
  • the silane coupling agent include ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -ureidopropyltriethoxysilane, and N- ⁇ -. Aminoethyl- ⁇ -aminopropyltrimethoxysilane can be mentioned.
  • ⁇ -mercaptopropyltrimethoxysilane or ⁇ -aminopropyltriethoxysilane is preferable in terms of adhesive strength.
  • the adhesive layer contains a silane coupling agent, the blending amount thereof is 0.1 to 10 parts by mass with respect to 100 parts by mass of the adhesive compound in terms of the effect of the addition and / or the influence on heat resistance. Is preferable.
  • the adhesive layer may contain a filler (preferably an inorganic filler).
  • a filler preferably an inorganic filler.
  • the handleability and thermal conductivity of the adhesive layer are improved.
  • flame retardancy is imparted to the adhesive layer, melt viscosity of the adhesive layer is adjusted, thixotropic property is imparted to the adhesive layer, and / or surface hardness. Can be improved.
  • the content thereof is not particularly limited, but 20 parts by volume or more is preferable with respect to 100 parts by volume of the above-mentioned adhesive compound contained in the adhesive layer, and the effect of blending is important. Therefore, 30 parts by volume or more is more preferable.
  • the upper limit is not particularly limited, the above is included in the adhesive layer from the viewpoint of optimizing the storage elastic modulus of the adhesive layer, improving the adhesiveness, and / or suppressing the void and suppressing the decrease in the insulating property. It is preferably 50 parts by volume or less with respect to 100 parts by volume of the compound having the adhesiveness of.
  • the inorganic filler examples include aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, alumina (aluminum oxide), aluminum nitride, aluminum borate whisker, and boron nitride. , Crystalline silica, amorphous silica, silicon nitride, talc, mica, and barium sulfate. Among them, alumina, boron nitride, or aluminum nitride is preferable because it has high thermal conductivity, good heat dissipation, easy control of impurities, and / or good heat resistance and insulation.
  • the average particle size of the filler contained in the adhesive layer is not particularly limited. For example, from the viewpoint of thermal conductivity, 0.1 to 10 ⁇ m is preferable, and 0.2 to 5 ⁇ m is more preferable.
  • the content of the filler in the adhesive layer is 50% by volume or less (for example, 20% by volume or more and 50% by volume or less) with respect to the total volume of the adhesive layer from the viewpoint of balancing adhesiveness and thermal conductivity. It is also preferable.
  • the adhesive layer contains at least one selected from the group consisting of an epoxy compound and a modified polyamideimide resin as a compound having adhesiveness, and at least one selected from the group consisting of alumina and silicon oxide as a filler.
  • the content of the filler is 20 parts by volume or more and 50 parts by volume or less with respect to 100 parts by volume of the adhesive having adhesiveness, and the average particle size of the filler is 0.2 to 5 ⁇ m. It is preferable from the viewpoint of.
  • the film thickness of the adhesive layer is preferably 1 to 16 ⁇ m, more preferably 2 to 15 ⁇ m, further preferably 3 to 14 ⁇ m, and particularly preferably 4 to 12 ⁇ m from the viewpoint of thermal conductivity and adhesiveness.
  • the film thickness of the adhesive layer can be measured using a micrometer, a stylus type film thickness meter, and a needle type film thickness meter.
  • any material having the required heat resistance and heat conduction performance such as various pressure-sensitive adhesives and / or thermosetting materials, can be used without particular limitation.
  • a pressure-sensitive adhesive may be used in which various heat-conductive fillers are mixed in the pressure-sensitive adhesive layer to improve the heat-conductivity.
  • Examples of the pressure-sensitive adhesive forming the pressure-sensitive adhesive layer include an acrylic pressure-sensitive adhesive, an olefin-based pressure-sensitive adhesive, a silicone-based pressure-sensitive adhesive, a natural rubber-based pressure-sensitive adhesive, and a synthetic rubber-based pressure-sensitive adhesive.
  • an acrylic pressure-sensitive adhesive or an olefin-based pressure-sensitive adhesive is preferable because outgas is less likely to be generated.
  • a silicone-based adhesive containing a silicone resin as a main raw material is preferable.
  • the "adhesive containing a silicone resin as a main raw material” is a pressure-sensitive adhesive containing 60% by mass or more (preferably 80% by mass or more) of a silicone resin.
  • the pressure-sensitive adhesive using a silicone resin as a main raw material include peroxide-crosslinked (cured) type silicone-based pressure-sensitive adhesives and addition-reaction type silicone-based pressure-sensitive adhesives.
  • an addition reaction type silicone-based pressure-sensitive adhesive is preferable because it has high thickness accuracy when it is made into a thin layer and it is easy to form a pressure-sensitive adhesive layer by a transfer method.
  • addition reaction type silicone adhesive examples include silicone rubber and silicone resin, and if necessary, a cross-linking agent, a filler, a plasticizing agent, an antiaging agent, an antioxidant, and / or a coloring agent.
  • adhesives containing additives such as (pigment or dye).
  • the silicone rubber is not particularly limited as long as it is a silicone-based rubber component, but is a silicone rubber containing an organopolysiloxane having a phenyl group (particularly, an organopolysiloxane having methylphenylsiloxane as a main constituent unit). Is preferable. Various functional groups such as vinyl groups may be introduced into the organopolysiloxane in such silicone rubber, if necessary.
  • the silicone resin is not particularly limited as long as it is a silicone-based resin used in a silicone-based pressure-sensitive adhesive, and is, for example, from a unit consisting of the constituent unit "R 3 SiO 1/2 " and the constituent unit "SiO 2 ". comprising units, units consisting of constituent units "RSiO 3/2", and consists of at least one kind of unit selected from the group consisting of units consisting of constituent units "R 2 SiO" (co) polymer Examples include silicone resins containing organopolysiloxane.
  • R in the said structural unit represents a hydrocarbon group or a hydroxyl group.
  • acrylic pressure-sensitive adhesive examples include homopolymers and copolymers of (meth) acrylic acid and / or (meth) acrylic acid ester.
  • the acrylic pressure-sensitive adhesive is a monomer such as butyl acrylate or 2-ethylhexyl acrylate because it is excellent in flexibility, chemical stability, processability, and / or controllability of adhesiveness.
  • a poly (meth) acrylic acid ester-based polymer compound as a main raw material component is preferable.
  • the above-mentioned polymer compound is obtained by copolymerizing one or more monomers selected from butyl acrylate, ethyl acrylate, and diethylhexyl acrylate with acrylate, acrylonitrile, and / or hydroxyethyl acrylate.
  • the obtained copolymer having a structure in which polar groups such as -COOH group, -CN group, and -OH group are introduced is preferable.
  • a crosslinked structure may be introduced into the acrylic pressure-sensitive adhesive as long as the flexibility is not impaired.
  • a crosslinked structure it is easy to improve long-term adhesion retention and film strength.
  • a crosslinked structure can be introduced by reacting a polymer having a polar group such as an ⁇ OH group with a compound having a functional group that binds to a plurality of polar groups such as an isocyanate group and an epoxy group.
  • the disk-shaped compounds A-1 to A-5 and B-1 to B-3 are all compounds represented by the above formula (D4) or the above formula (D16), and are divalent linking groups thereof.
  • the number of atoms between both ends of the above is 19, 4, 5, 6, 5, 14, 14, 6 and 7, respectively.
  • Compounds C-1 to C-6 are curing agents that are not disc-shaped compounds, and compounds D-1 to D-4 are main agents that are not disc-shaped compounds.
  • Compound C-6 is "MEH-7500” manufactured by Meiwakasei Workers Co., Ltd.
  • Compound D-1 is "YX-4000” manufactured by Mitsubishi Chemical Co., Ltd.
  • Compound D-2 is a mixture of two types of epoxy compounds (trade name "Epototo ZX-1059", manufactured by Toto Kasei Co., Ltd.).
  • Compound D-3 is "Denacol EX-201” manufactured by Nagase ChemteX Corporation
  • Compound D-4 is "EPPN-501HY” manufactured by Nippon Kayaku Co., Ltd.
  • E-2 "Sumika Excel 5003 PS” manufactured by Sumitomo Chemical Co., Ltd.
  • E-4" Made by Aldrich (melt index 18g / 10min)
  • the structural formulas of the compounds E-1 to E-8 are shown below.
  • Inorganic particles The inorganic particles used in the examples are shown below.
  • “HP-40 MF100” Aggregated boron nitride (average particle size: 40 ⁇ m, manufactured by Mizushima Ferroalloy Co., Ltd.)
  • AA-3 Aluminum oxide (average particle size: 3 ⁇ m, manufactured by Sumitomo Chemical Co., Ltd.)
  • AA-04 Aluminum oxide (average particle size: 0.4 ⁇ m, manufactured by Sumitomo Chemical Co., Ltd.)
  • SP-3 Scaly boron nitride (average particle size: 4 ⁇ m, manufactured by Denka Co., Ltd.)
  • Triphenylphosphine (PPh 3 ) was used as a curing accelerator.
  • Dispersant DISPERBYK-106 (a polymer salt having an acidic group) was used as a dispersant.
  • Examples 1 to 53, Comparative Examples 1 to 4 [Preparation of composition] A cured liquid was prepared by blending the disc-shaped compound shown in the table below and an arbitrary curable compound in the addition amounts shown in the table below. The total amount of the obtained curing liquid, the solvent, the dispersant, any surface modifier for aluminum oxide, and the curing accelerator were mixed in this order, and then inorganic particles were added. The obtained mixture was treated with a rotation revolution mixer (manufactured by THINKY, Awatori Rentaro ARE-310) for 5 minutes to obtain a composition (composition for forming a heat conductive sheet) of each Example or Comparative Example.
  • a rotation revolution mixer manufactured by THINKY, Awatori Rentaro ARE-310
  • the amount of the solvent added was set so that the solid content concentration of the composition was 50 to 80% by mass.
  • the solid content concentration of the composition was adjusted for each composition within the above range so that the viscosities of the compositions were about the same.
  • Dispersants, inorganic particles and curing accelerators were added in the amounts shown in the table below.
  • the amount of the surface modifier for aluminum oxide added is 0.2% by mass based on the content of the surface modifier for aluminum oxide in the composition with respect to the content of aluminum oxide (total content of AA-3 and AA04). The amount was set to When the composition did not contain aluminum oxide as inorganic particles, no surface modifier for aluminum oxide was used.
  • an adhesive layer film 1 which is a polyester film with a coating film of the coating liquid 1 was obtained.
  • the coating amount of the coating liquid 1 was adjusted so that the film thickness of the adhesive layer 1 formed by curing the coating film of the coating liquid 1 was 5 ⁇ m.
  • adhesive layer film 2 epoxy adhesive layer with filler 21.6 parts by mass of the disk-shaped compound B-3, 13.3 parts by mass of the disk-shaped compound A-1 as a curing agent, 0.21 parts by mass of triphenylphosphine (PPh 3) as a curing accelerator, and the above. 35 parts by mass of "AA-04" (aluminum oxide) and 100 parts by mass of cyclopentanone were mixed to obtain a coating liquid 2.
  • An adhesive layer film 2 which is a polyester film with a coating film of the coating liquid 2 was obtained according to the method for producing the adhesive layer film 1 except that the coating liquid 2 was used instead of the coating liquid 1.
  • An adhesive layer film 3 which is a polyester film with a coating film of the coating liquid 3 was obtained according to the method for producing the adhesive layer film 1 except that the coating liquid 3 was used instead of the coating liquid 1.
  • the layer formed of the acrylic acid ester copolymer resin is an adhesive layer, but in the examples of the present specification, it is referred to as an adhesive layer for convenience.
  • Polyester film / semi-cured adhesive layer 2/half according to the above method for producing the semi-cured multilayer sheet 1 except that two adhesive layer films 2 are used instead of the two adhesive layer films 1.
  • a semi-cured multilayer sheet 2 having a cured sheet / semi-cured adhesive layer 2 / polyester film layer structure was obtained.
  • the polyester film / semi-cured adhesive layer 3 is according to the above-mentioned method for producing the semi-curable multilayer sheet 1.
  • a semi-cured multilayer sheet 3 having a layer structure of / semi-cured sheet / semi-cured adhesive layer 3 / polyester film was obtained.
  • a semi-cured sheet or a semi-cured multilayer sheet was prepared according to the above-mentioned production method, and the obtained semi-cured sheet or semi-cured sheet or A heat conductive sheet was prepared by the following method using a semi-cured multilayer sheet, and each evaluation test of toughness, peel strength and heat conductivity was performed on the obtained heat conductive sheet.
  • a method for producing the heat conductive sheet and each test method for toughness, peel strength and heat conductivity of the obtained heat conductive sheet will be described.
  • the semi-cured sheet produced by the above method is treated with a hot press under air (heat plate temperature 180 ° C., pressure 20 MPa for 5 minutes, then hot plate temperature 180 ° C., 90 minutes without pressurization).
  • the sheet was cured by this to prepare a resin sheet sandwiched between two polyester films.
  • the polyester films on both sides of the resin sheet were peeled off to obtain a heat conductive sheet having an average film thickness of 200 ⁇ m.
  • the obtained heat conductive sheet was cut into strips of 10 mm ⁇ 45 mm to prepare a sample for a tensile test.
  • the obtained sample was subjected to a tensile test under the following measurement conditions using a Tencilon universal material tester (product name "RTC-1225A", manufactured by A & D Co., Ltd.), and strain (break elongation) ( %) And stress (MPa) were measured until the sample broke. From the measurement results, a stress-strain curve was created with stress on the vertical axis and strain on the horizontal axis. Of the obtained stress-strain curves, the stress-strain curve in the section from the origin to the breaking point, the perpendicular line drawn from the breaking point to the horizontal axis, and the area of the figure surrounded by the horizontal axis were integrated. The calculated integral value (unit: MPa ⁇ %) was used as the toughness parameter of the measured sample.
  • Toughness evaluation criteria "A +": Toughness parameter is 60 MPa ⁇ % or more "A”: Toughness parameter is 45 MPa ⁇ % or more and less than 60 MPa ⁇ % "B”: Toughness parameter is 30 MPa ⁇ % or more and less than 45 MPa ⁇ % "C”: Toughness parameter is 15 MPa ⁇ % % Or more and less than 30 MPa ⁇ % "D”: Toughness parameter is less than 15 MPa ⁇ %
  • the polyester film is peeled off from the semi-cured sheet with a polyester film produced by the above method, and the obtained semi-cured sheet is cut into strips of 20 mm ⁇ 60 mm, and the electrolytic copper foil (20 mm ⁇ 100 mm, thickness: 20 mm ⁇ 100 mm) as an adherend. It was sandwiched between an aluminum plate (30 mm ⁇ 60 mm, thickness: 1 mm) (35 ⁇ m).
  • the obtained laminate was heat-pressed under air (hot plate temperature 180 ° C., pressure 20 MPa for 5 minutes, then hot plate temperature 180 ° C., normal pressure for 90 minutes) to form a heat conductive sheet.
  • An aluminum base substrate with a copper foil integrated with the adherend was obtained.
  • the copper foil peel strength of the obtained sample was measured by JIS C 6481. It was measured according to the method for measuring the peeling strength under normal conditions described in 1. The peeling of the copper foil in the peel strength test was carried out at an angle of 90 ° with respect to the aluminum base substrate with the copper foil at a peeling speed of 50 mm / min.
  • the peel strength of the heat conductive sheet was evaluated based on the following criteria. The higher the measured value, the better the peel strength of the heat conductive sheet.
  • the semi-cured sheet produced by the above method is treated with a hot press under air (treated at a hot plate temperature of 180 ° C. and a pressure of 20 MPa for 5 minutes, and then treated at a hot plate temperature of 180 ° C. and a normal pressure for 90 minutes).
  • the sheet was cured by the above method to prepare a resin sheet sandwiched between two polyester films.
  • the polyester films on both sides of the resin sheet were peeled off to obtain a heat conductive sheet having an average film thickness of 200 ⁇ m.
  • the thermal conductivity of the obtained heat conductive sheet was measured by the following method. From the measured thermal conductivity, the thermal conductivity of the heat conductive sheets of each Example and each Comparative Example was evaluated according to the following evaluation criteria.
  • Tables 1 and 2 show the evaluation results of the toughness, peel strength and thermal conductivity of the heat conductive sheets of each example and each comparative example.
  • the “amount (%)" of each component of the composition means the content (mass%) of each component with respect to the total mass of the solid content of the composition.
  • the “ratio” column of the “composition” represents the ratio (mass ratio) of the content of the specific polymer (thermoplastic resin or rubber) to the content of the inorganic particles.
  • the notation “none” indicates that each evaluation was performed on the heat conductive sheet having no adhesive layer
  • "1", “2” and " The notation of "3” indicates that each evaluation was performed on the heat conductive sheets having the adhesive layers 1 to 3 on both sides.
  • thermoplastic resin having an aromatic ring in the main chain the thermal conductivity of the heat conductive sheet is more excellent (comparison of Examples 1 to 8).
  • the ratio of the content of the specific polymer to the content of the inorganic particles (content of the specific polymer / content of the inorganic particles) in the composition is 0.04 or more by mass ratio, the peel strength of the heat conductive sheet becomes higher. It was confirmed to be excellent (comparison between Example 2 and Example 9).
  • the ratio of the content of the specific polymer to the content of the inorganic particles (content of the specific polymer / content of the inorganic particles) in the composition is 0.12 or less by mass ratio, the thermal conductivity of the heat conductive sheet is high.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesive Tapes (AREA)
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CN114846086A (zh) 2022-08-02
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