Classifications

• • 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
  • C08G59/32—Epoxy compounds containing three or more epoxy groups
  • C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
• • 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
  • C08G59/40—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 curing agents used
  • C08G59/62—Alcohols or phenols
• • 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
  • C08K3/013—Fillers, pigments or reinforcing additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

• the present disclosure relates to a liquid resin composition and a cured product of the liquid resin composition, and more particularly, a liquid resin composition containing an epoxy resin, a curing agent, and a ceramic filler, and a cured product of the liquid resin composition. Regarding.
• the encapsulant used for encapsulation in semiconductor packages such as AiP is required to have a small warp after molding in pressure molding of a substrate.
• AiP Antenna in Package
• silicone, acrylic rubber or the like As a method for exhibiting low warpage, it is common to use silicone, acrylic rubber or the like as a low stress agent.
• an epoxy-silicone hybrid resin composition containing an organopolysiloxane and an epoxy resin is known (see Patent Document 1).
• such encapsulants In addition to low warpage, such encapsulants have heat resistance, chemical resistance to alkalis and polar solvents, and wettability of heat-resistant insulating coats such as photosensitive polyimide to the surface after curing and grinding. It is required to be excellent in various characteristics. However, the conventional resin composition cannot satisfy these characteristics.
• An object of the present disclosure is to provide a liquid resin composition having excellent heat resistance, chemical resistance and wettability of a heat-resistant insulating coat while maintaining low warpage, and a cured product of the liquid resin composition.
• the liquid resin composition according to one aspect of the present disclosure contains an epoxy resin, a curing agent, and a ceramic filler.
• the epoxy resin includes a first epoxy resin and a second epoxy resin.
• the first epoxy resin has a polyalkylene glycol skeleton.
• the second epoxy resin has an aromatic ring and has three or more epoxy groups in one molecule.
• the curing agent contains a compound having two or more phenolic hydroxyl groups in one molecule.
• the ratio of the first epoxy resin in the epoxy resin is 10% by mass or more and 25% by mass or less.
• the cured product according to one aspect of the present disclosure is a cured product of the liquid resin composition.
• the liquid resin composition of the present embodiment contains an epoxy resin, a curing agent, and a ceramic filler.
• the epoxy resin includes a first epoxy resin and a second epoxy resin.
• the first epoxy resin has a polyalkylene glycol skeleton.
• the second epoxy resin has an aromatic ring and has three or more epoxy groups in one molecule.
• the curing agent contains a compound having two or more phenolic hydroxyl groups in one molecule.
• the ratio of the first epoxy resin in the epoxy resin is 10% by mass or more and 25% by mass or less.
• the inventors use two specific epoxy resins, a first epoxy resin and a second epoxy resin, and the specific curing agent, and determine the ratio of the first epoxy resin in the epoxy resin. It has been found that the above-mentioned specific range can satisfy all of the low warpage property, heat resistance, chemical resistance and wettability of the heat-resistant insulating coat. As described above, according to the present disclosure, it is possible to provide a liquid resin composition having excellent heat resistance, chemical resistance and wettability of a heat-resistant insulating coat while maintaining low warpage.
• liquid resin composition of the present embodiment has the above-mentioned effect is not necessarily clear, but can be inferred as follows, for example. That is, by using a first epoxy resin having a polyalkylene glycol skeleton and setting the ratio to 10% by mass or more, it is possible to contribute to the reduction of warpage, and by setting it to 25% by mass or less, the wettability is deteriorated. Is considered to be able to be suppressed. Further, by using a second epoxy resin having an aromatic ring and having 3 or more epoxy groups in one molecule, heat resistance is improved due to the presence of the aromatic ring and the formation of a crosslinked structure of the epoxy resin.
• the chemical resistance can be improved by using a curing agent having two or more phenolic hydroxyl groups in one molecule.
• the liquid composition of the present embodiment can be made excellent in all of low warpage, heat resistance, chemical resistance and wettability of the heat-resistant insulating coat.
• Epoxy resin is a compound having two or more epoxy groups in one molecule.
• the epoxy resin includes a first epoxy resin and a second epoxy resin.
• the epoxy resin may contain a third epoxy resin different from the first epoxy resin and the second epoxy resin.
• the epoxy resin is preferably liquid at 25 ° C.
• the first epoxy resin is an epoxy resin having a polyalkylene glycol skeleton.
• the first epoxy resin preferably has two epoxy groups.
• the first epoxy resin is preferably liquid at 25 ° C.
• the first epoxy resin one kind or two or more kinds can be used.
• the polyalkylene glycol skeleton refers to a skeleton including a structure in which two or more alkylene glycol units are linked, for example, a skeleton represented by (-RO-) n (R is an alkylene group, n is an integer of 2 or more). To say.
• Examples of the first epoxy resin include compounds represented by the following formula (1).
• RA is an alkylene group having 2 to 10 carbon atoms.
• R 1 and R 2 are independently single-bonded or divalent organic groups having 1 to 20 carbon atoms.
• E 1 and E 2 are independently monovalent groups containing an epoxy group.
• n is an integer of 2 or more and 1000 or less.
• Examples of the alkylene group having 2 to 10 carbon atoms represented by R 1 include an ethanediyl group, a propanediyl group, a butanjiyl group, a pentandiyl group, a hexanediyl group, an octanediyl group, a decandyl group and the like.
• Organic group means a group containing at least one carbon atom.
• Examples of the divalent organic group having 1 to 20 carbon atoms represented by R 1 and R 2 include a substituted or unsubstituted divalent hydrocarbon group.
• Examples of the substituent include a hydroxy group, an alkoxy group, a halogen atom and the like.
• Examples of the monovalent group including the epoxy group represented by E 1 and E 2 include a substituted or unsubstituted epoxy group, a substituted or unsubstituted glycidyl group and the like.
• Examples of the substituent include an alkyl group such as a methyl group.
• N is preferably 2 or more and 500 or less, more preferably 5 or more and 300 or less, and further preferably 10 or more and 200 or less.
• Examples of the first epoxy resin include polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytrimethylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, and polyhexamethylene glycol diglycidyl ether.
• the first epoxy resin examples include, for example, SR-4PG and SR-TPG manufactured by Sakamoto Pharmaceutical Co., Ltd., PG-207 and PG-207GS manufactured by Nittetsu Chemical & Materials Co., Ltd., YX7400 manufactured by Mitsubishi Chemical Corporation, and Yokkaichi Chemical Company Limited.
• Epoxy PT made by Epogosei PT and the like can be mentioned.
• the proportion of the first epoxy resin in the entire epoxy resin is 10% by mass or more and 25% by mass or less.
• the ratio of the first epoxy resin in this range, it is possible to achieve both low warpage and wettability of the heat-resistant insulating coat. If the proportion of the first epoxy resin is less than 10% by mass, the warp increases. If this ratio exceeds 25% by mass, the wettability deteriorates.
• the ratio of the first epoxy resin is preferably 13% by mass or more, and more preferably 15% by mass or more.
• the ratio of the first epoxy resin is preferably 22% by mass or less, more preferably 20% by mass or less.
• the ratio of the first epoxy resin to the composition (X) is preferably 1% by mass or more and 10% by mass or less, more preferably 2% by mass or more and 6% by mass or less, and 3% by mass or more and 5% by mass or less. The following is more preferable.
• the second epoxy resin is an epoxy resin having an aromatic ring and having three or more epoxy groups in one molecule.
• the second epoxy resin is preferably liquid at 25 ° C.
• the number of epoxy groups in the second epoxy resin is preferably 3 or more and 10 or less, more preferably 3 or more and 6 or less, and further preferably 3 or 4.
• As the second epoxy resin one kind or two or more kinds can be used.
• aromatic ring examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a tetracene ring, a pentacene ring, an indene ring, a fluorene ring, a perylene ring and the like.
• Examples of the second epoxy resin include compounds represented by the following formula (2).
• Ar 1 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 38 carbon atoms.
• R 3 and R 4 are independently single bonds, oxygen atoms, -NH-, nitrogen atoms or 2- to 5-valent organic groups having 1 to 20 carbon atoms.
• E 3 and E 4 are independently monovalent groups containing an epoxy group. If R 3 is a single bond, an oxygen atom or -NH-, x is 1, if R 3 is a nitrogen atom, x is 2, and if R 3 is a 2-5 valent organic group, x is. It is an integer of 1 to 4.
• R 4 is a single bond, an oxygen atom or -NH-, y is 1, if R 4 is a nitrogen atom, y is 2, and if R 4 is a 2-5 valent organic group, y is. It is an integer of 1 to 4.
• x is 2 or more, the plurality of E3s may be the same or different from each other, and when y is 2 or more, the plurality of E4s may be the same or different from each other.
• x + y is 3 or more.
• Examples of the divalent aromatic hydrocarbon group represented by Ar 1 include a benzenediyl group, a toluenediyl group, a xylendyl group, a naphthalenediyl group, an anthracendyl group, a phenanthrendiyl group, a pyrenidyl group, a tetrasendyl group and a pentacene.
• Examples thereof include a diyl group, an indendiyl group, a fluorinatedyl group, a perylenediyl group, a biphenyldiyl group, a terphenyldiyl group and the like.
• Examples of the substituent of the aromatic hydrocarbon group include a hydroxy group, a halogen atom, and a monovalent group containing an epoxy group.
• Examples of the second epoxy resin include N, N, N', N'-tetraglycidyl-4,4'-methylenebisbenzeneamine, p-aminophenol-diglycidyl ether and the like.
• Examples of commercially available second epoxy resins include Araldite MY510, MY600, MY720, MY721, MY725 manufactured by HUNTSMAN, 630 manufactured by Mitsubishi Chemical Corporation, and EP3900 manufactured by ADEKA.
• the ratio of the second epoxy resin in the entire epoxy resin is preferably 5% by mass or more and 80% by mass or less.
• the heat resistance of the composition (X) can be further improved. This ratio is more preferably 10% by mass or more and 70% by mass or less, and further preferably 20% by mass or more and 60% by mass or less.
• the ratio of the second epoxy resin to the composition (X) is preferably 2% by mass or more and 30% by mass or less, more preferably 3% by mass or more and 20% by mass or less, and 5% by mass or more and 10% by mass or less. The following is more preferable.
• the third epoxy resin other than the first epoxy resin and the second epoxy resin is preferably liquid at 25 ° C.
• the third epoxy resin include bisphenol F type epoxy resin, bisphenol A type epoxy resin, hydrogenated bisphenol type epoxy resin, biphenyl type epoxy resin, naphthalene ring-containing epoxy resin, alicyclic epoxy resin, and dicyclopentadiene type epoxy resin. , Phenol novolak type epoxy resin, cresol novolak type epoxy resin, triphenylmethane type epoxy resin, aliphatic epoxy resin, glycidyl group-containing silicone resin, glycidylamine type epoxy resin, etc., which have two epoxy groups. And so on.
• the third epoxy resin preferably contains a bisphenol F type epoxy resin (one having two epoxy groups) from the viewpoint of further improving heat resistance.
• the proportion of the third epoxy resin in the entire epoxy resin is preferably 10% by mass or more and 80% by mass or less.
• the heat resistance of the composition (X) can be further improved.
• This ratio is more preferably 15% by mass or more and 70% by mass or less, and further preferably 20% by mass or more and 60% by mass or less.
• the ratio of the third epoxy resin to the composition (X) is preferably 1% by mass or more and 20% by mass or less, more preferably 2% by mass or more and 15% by mass or less, and 3% by mass or more and 10% by mass or less. The following is more preferable.
• the curing agent contains a compound having two or more phenolic hydroxyl groups in one molecule (hereinafter, also referred to as curing agent A).
• the curing agent A is preferably liquid at 25 ° C.
• the curing agent may contain a curing agent other than the curing agent A.
• the curing agent one kind or two or more kinds can be used.
• Examples of the curing agent A include novolak-type resins such as phenol novolac resin, cresol novolak resin, and naphthol novolak resin; and aralkyl-type resins such as phenol aralkyl resin having a phenylene skeleton or biphenylene skeleton, and naphthol aralkyl resin having a phenylene skeleton or biphenylene skeleton.
• Polyfunctional phenol resin such as triphenol methane type resin; Dicyclopentadiene type phenol resin such as dicyclopentadiene type phenol novolac resin, dicyclopentadiene type naphthol novolac resin; Terpen modified phenol resin; Bisphenol A, bisphenol F, etc.
• Bisphenol type resin; Triazine-modified novolak resin and the like can be mentioned.
• the ratio of the curing agent A to the entire curing agent is preferably 50% by mass or more.
• the chemical resistance of the composition (X) can be further improved.
• This ratio is more preferably 80% by mass or more, and further preferably 95% by mass or more.
• the ratio of the curing agent A may be 100% by mass.
• the ratio of the curing agent A to 100 parts by mass of the epoxy resin is preferably 30 parts by mass or more and 100 parts by mass or less.
• the chemical resistance of the composition (X) can be further improved. This ratio is more preferably 40 parts by mass or more and 80 parts by mass or less, and further preferably 50 parts by mass or more and 70 parts by mass or less.
• the ratio of the curing agent A to the composition (X) is preferably 2% by mass or more and 30% by mass or less, more preferably 4% by mass or more and 20% by mass or less, and 8% by mass or more and 15% by mass or less. Is more preferable.
• curing agents examples include acid anhydride-based curing agents, aromatic amine-based curing agents, imidazole-based curing agents, hydrazide-based curing agents, polypeptide-based curing agents, Lewis acid-amine complex-based curing agents, and the like. ..
• the equivalent of the curing agent to 1 equivalent of the epoxy resin is, for example, 0.6 or more and 1.4 or less.
• the ratio of the curing agent to 100 parts by mass of the epoxy resin is preferably 30 parts by mass or more and 100 parts by mass or less, more preferably 40 parts by mass or more and 80 parts by mass or less, and 50 parts by mass or more and 70 parts by mass or less. It is more preferable to have.
• the ratio of the curing agent to the composition (X) is preferably 2% by mass or more and 30% by mass or less, more preferably 4% by mass or more and 20% by mass or less, and 8% by mass or more and 15% by mass or less. It is more preferable to have.
• composition (X) can contain a curing accelerator.
• curing accelerator examples include imidazoles such as 2-methylimidazole, 2-ethyl imidazole, 2-phenyl imidazole, and 2-ethyl-4-methyl imidazole; 1,8-diazabicyclo [5.4.0] undecene-7.
• the ratio of the curing accelerator to 100 parts by mass of the epoxy resin is preferably 0.1 part by mass or more and 10 parts by mass or less, and more preferably 1 part by mass or more and 5 parts by mass or less.
• the ratio of the curing accelerator to the composition (X) is, for example, 0.05% by mass or more and 1% by mass or less.
• Ceramic filler examples include silica, alumina, aluminum nitride, silicon nitride and the like. Examples of silica include crystalline silica, non-crystalline silica, amorphous silica, fused silica, and crushed silica. The ceramic filler may be used by blending two or more of these.
• Examples of the shape of the particles of the ceramic filler include spherical shape, chain shape, cocoon shape, irregular shape, and irregular shape.
• the average particle size of the ceramic filler is preferably 0.5 ⁇ m or more and 10 ⁇ m or less, and more preferably 0.5 ⁇ m or more and 5 ⁇ m or less.
• the ceramic filler one kind of filler may be used, or two or more kinds of fillers having different average particle sizes may be used.
• the ceramic filler preferably contains two types of fillers having different average particle sizes.
• the average particle size of the ceramic filler is the median diameter (D50) obtained from the particle size distribution obtained from the measurement results by the laser diffraction / scattering method.
• the ceramic filler When the ceramic filler contains two types of filler, the ceramic filler has an average particle size of 1 ⁇ m or more and 50 ⁇ m or less (hereinafter, also referred to as filler 1) and an average particle size of 0.1 ⁇ m or more and 1 ⁇ m. It is preferable to include a filler (hereinafter, also referred to as filler 2) which is less than or equal to. In this case, the content of the ceramic filler can be further increased.
• the average particle size of the filler 1 is preferably 0.5 ⁇ m or more and 10 ⁇ m or less, and more preferably 0.5 ⁇ m or more and 5 ⁇ m or less.
• the ratio of the filler 1 in the entire ceramic filler is preferably 50% by mass or more and 99% by mass or less, more preferably 60% by mass or more and 90% by mass or less, and 70% by mass or more and 85% by mass or less. It is more preferable to have.
• the average particle size of the filler 2 is preferably 0.2 ⁇ m or more and 0.9 ⁇ m or less, and more preferably 0.5 ⁇ m or more and 0.7 ⁇ m or less.
• the ratio of the filler 2 in the entire ceramic filler is preferably 1% by mass or more and 50% by mass or less, more preferably 10% by mass or more and 40% by mass or less, and 15% by mass or more and 30% by mass or less. It is more preferable to have.
• the mass ratio of the filler 2 to the filler 1 is preferably 0.1 or more and 1 or less, and preferably 0.2 or more and 0.5 or less.
• the proportion of the ceramic filler in the composition (X) is preferably 50% by mass or more, more preferably 60% by mass or more, and further preferably 70% by mass or more. This ratio is preferably 90% by mass or less, more preferably 80% by mass or less, and further preferably 75% by mass or less.
• the ceramic filler is preferably surface-treated with, for example, a coupling agent. Since the ceramic filler is surface-treated, the affinity with the epoxy resin can be improved.
• a coupling agent include a silane coupling agent, a titanate coupling agent, an aluminum coupling agent, an aluminum / zirconium coupling agent, and the like.
• the silane coupling include glycidoxysilanes such as ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, and ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane; N.
• Aminosilanes such as - ⁇ (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane; alkylsilanes; ureidosilanes; vinylsilanes and the like can be mentioned.
• the ratio of the coupling agent to the total amount of the ceramic filler and the coupling agent is, for example, 0.01% by mass or more and 1% by mass or less.
• composition (X) may contain additives other than the above-mentioned components as long as the effects of the present embodiment are not impaired.
• the additive include a flame retardant, a flame retardant aid, an ion trapping agent, a colorant, a low stress agent, a tackifier, a silicone flexible agent and the like.
• Examples of the flame retardant include magnesium hydroxide, aluminum hydroxide, red phosphorus and the like.
• colorant examples include carbon black, red iron oxide, titanium oxide, phthalocyanine, perylene black and the like.
• Examples of the low stress agent include silicone elastomers, silicone resins, silicone oils, and butadiene rubbers.
• examples of the butadiene rubber include methyl acrylate-butadiene-styrene copolymer, methyl methacrylate-butadiene-styrene copolymer and the like.
• composition (X) is excellent in low warpage, heat resistance, chemical resistance and wettability of the heat-resistant insulating coat, it can be suitably used for encapsulation in a semiconductor package such as AiP.
• the cured product of this embodiment is a cured product of the composition (X).
• the cured product of the present embodiment can be obtained by heat-molding the composition (X) on a ceramic substrate such as, for example, alumina ceramics by a vacuum press molding machine or the like.
• the temperature of the heat molding is, for example, 100 ° C. or higher and 180 ° C. or lower, and preferably 120 ° C. or higher and 150 ° C. or lower.
• the heat molding time is, for example, 10 seconds or more and 1 hour or less, preferably 1 minute or more and 20 minutes or less.
• ⁇ Preparation of liquid resin composition The raw materials shown in Table 1 were blended and uniformly mixed and dispersed with a mixer to obtain a liquid resin composition.
• the details of the raw materials are as follows.
• -Second epoxy resin "Araldite MY720" manufactured by HUNTSMAN. N, N, N'N'-tetraglycidyl-4,4'-methylenebisbenzeneamine.
• -Third epoxy resin Bisphenol F type epoxy resin. "806” manufactured by Mitsubishi Chemical Corporation.
• -Curing agent / phenolic curing agent "MEH8000H” manufactured by Meiwa Kasei Co., Ltd.
• -Acid anhydride-based curing agent "Ricacid MH-700” manufactured by Shin Nihon Rika Co., Ltd.
• -Aromatic amine-based curing agent "Kayahard AA” manufactured by Nippon Kayaku Co., Ltd. 4,4'-Diamino-3,3'-diethyldiphenylmethane.
• -Curing accelerator / imidazole-based curing accelerator “2E4MZ” manufactured by Shikoku Chemicals Corporation
• -Ceramic filler / filler 1 "FB-3SDX” manufactured by Denka. Fused silica.
• Tg glass transition temperature
• DMA dynamic viscoelasticity measuring device
• A No coating film defects or wavy patterns of 1.0 mm 2 or more were observed.
• B No film defect of 1.0 mm 2 or more was observed, but a wavy pattern was observed.
• C A coating film defect of 1.0 mm 2 or more was observed.

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• Paints Or Removers (AREA)
• Epoxy Resins (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 2021
  • 2021-10-12 JP JP2022557018A patent/JPWO2022085522A1/ja active Pending
  • 2021-10-12 CN CN202180070761.2A patent/CN116390967A/zh active Pending
  • 2021-10-12 WO PCT/JP2021/037787 patent/WO2022085522A1/ja not_active Ceased
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