WO2014156843A1 - 熱硬化性樹脂組成物 - Google Patents
熱硬化性樹脂組成物 Download PDFInfo
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- WO2014156843A1 WO2014156843A1 PCT/JP2014/057358 JP2014057358W WO2014156843A1 WO 2014156843 A1 WO2014156843 A1 WO 2014156843A1 JP 2014057358 W JP2014057358 W JP 2014057358W WO 2014156843 A1 WO2014156843 A1 WO 2014156843A1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002454 poly(glycidyl methacrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- SQAZDQFHAOTWGX-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](OCC)(OCC)OCC)CCC2OC21 SQAZDQFHAOTWGX-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- LQZHZFUSFHLGHE-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](OC)(OC)OC)CCC2OC21 LQZHZFUSFHLGHE-UHFFFAOYSA-N 0.000 description 1
- LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- 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
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09J161/04, C09J161/18 and C09J161/20
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
- H01L23/3107—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed
- H01L23/3142—Sealing arrangements between parts, e.g. adhesion promotors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
- H01L21/563—Encapsulation of active face of flip-chip device, e.g. underfilling or underencapsulation of flip-chip, encapsulation preform on chip or mounting substrate
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
- H01L2224/29001—Core members of the layer connector
- H01L2224/29099—Material
- H01L2224/2919—Material with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/06—Polymers
- H01L2924/0665—Epoxy resin
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/181—Encapsulation
- H01L2924/186—Material
Definitions
- the present invention provides a thermosetting resin composition containing a novel polymer, a molded product and a cured product obtained from the thermosetting resin composition, and a process for producing a semiconductor device represented by an IC chip.
- the present invention relates to an adhesive composition for bonding between laminates or an underfill composition used for flip chip bonding.
- flip chip bonding is known as a method of mounting an IC chip on a substrate.
- This is a method of providing a plurality of bumps (protruding terminals) on an IC chip and electrically connecting the bumps and electrode terminals of the substrate.
- An underfill agent is used to fill the gap between the substrate and the IC chip and protect the IC chip from moisture and external stress.
- a composition containing an epoxy resin is employed (for example, Patent Document 1 and Patent Document 2).
- an underfill agent is injected after bump connection between a substrate and an IC chip (rear insertion type). Underfill) and thermosetting methods were mainly used.
- thermosetting resin compositions containing a compound having an aromatic benzoxazine ring in the main chain are known (for example, Patent Document 5 and Patent Document 6). It is also known that benzoxazine resins have excellent heat resistance and electrical properties. However, the thermosetting resin composition containing a compound having an aromatic benzoxazine ring in the main chain described in Patent Document 5 and Patent Document 6 has a low crosslinking density and a high coefficient of linear expansion above the glass transition point. In addition, there is a concern about reliability degradation such as cracking or peeling due to thermal history.
- an epoxy resin is mixed with a benzoxazine resin to improve the crosslinking density.
- the above mixed resin has a slow crosslinking reaction, and a sufficient crosslinking density cannot be obtained.
- an epoxy resin curing agent represented by an imidazole compound is added.
- the epoxy resin curing agent has low heat resistance, there is a concern about a decrease in reliability due to generation of voids. Is done.
- the present invention relates to a thermosetting resin composition having high heat resistance, excellent electrical characteristics, and promoting the curing of an epoxy resin, a molded body and a cured product obtained from the thermosetting resin composition, and heat.
- An object is to provide a curable adhesive composition or underfill composition.
- the present invention is a thermosetting resin composition containing a polymer having at least one structural unit represented by the following formula (1).
- R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- X represents a single bond or a divalent organic group
- Y represents the following formula (2): (Wherein Z 1 represents a carbonyl group or a —CONH— group, Z 2 represents an alkylene group having 1 to 5 carbon atoms, or a divalent divalent 5- or 6-membered ring containing at least one nitrogen atom.
- Z 3 represents a 5-membered or 6-membered aromatic ring containing 2 nitrogen atoms, wherein at least one hydrogen atom may be substituted with an alkyl group having 1 to 5 carbon atoms
- Z 2 represents a 5-membered or 6-membered divalent saturated heterocyclic group containing at least one nitrogen atom
- saturated heterocyclic ring examples include a piperazine ring, an imidazolidine ring
- aromatic heterocycle of the 5-membered or 6-membered aromatic heterocyclic group containing two nitrogen atoms represented by Z 3 in the formula (2) include, for example, an imidazole ring, a pyrimidine ring, Examples thereof include a pyrazine ring and a pyrazole ring.
- Z 3 represents, for example, an imidazolyl group
- Z 2 represents, for example, an alkylene group having 1 to 5 carbon atoms
- Z 1 represents, for example, a —CONH— group.
- X is, for example, an alkylene group having 1 to 6 carbon atoms, a cyclic alkylene group or at least one hydrogen atom optionally substituted with a halogen atom, and a halogen atom substituted with a halogen atom.
- a divalent organic group including an arylene group, a sulfonyl group, a carbonyl group, an —O— group or a —COO— group.
- X is, for example, the following formula (3): (Wherein R 3 and R 4 each independently represent a hydrogen atom or a methyl group in which at least one of the hydrogen atoms may be substituted with a halogen atom, and m represents 0 or 1). The divalent organic group represented by these is represented.
- Examples of the divalent organic group represented by the formula (3) include the following formula (3-a) or formula (3-b): It is represented by
- the polymer contained in the thermosetting resin composition of the present invention may further have a structural unit represented by the following formula (4) in addition to the structural unit represented by the formula (1).
- R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- X represents a single bond or a divalent organic group
- Q represents the following formula (5) or formula: (6):
- T represents a single bond, a sulfonyl group or —O— group
- R 3 and R 4 each independently represents a hydrogen atom or a methyl group in which at least one of the hydrogen atoms may be substituted with a halogen atom
- R 5 s each independently represent a hydrogen atom, a methyl group, an ethyl group, or a methoxy group
- n represents 0 or 1.
- the divalent organic group represented by the formula (5) or formula (6) is, for example, the following formula (5-a), formula (6-a), formula (6-b) or formula (6-c). : It is represented by
- the weight average molecular weight of the polymer is, for example, 1,000 to 100,000.
- thermosetting resin composition of the present invention can further contain an epoxy resin.
- thermosetting resin composition of the present invention can further contain a silane coupling agent.
- thermosetting resin composition of the present invention can further contain an inorganic filler having a particle size of 1 nm to 700 nm.
- thermosetting resin composition of the present invention can further contain a solvent.
- thermosetting resin composition of the present invention is, for example, an adhesive composition or an underfill composition.
- thermosetting resin composition of the present invention can be cured at a relatively low temperature of 200 ° C. or lower, and can promote the curing reaction of the epoxy resin.
- the film formed from the thermosetting resin composition of the present invention has good adhesion without generating voids, hardly peels after bonding, has excellent heat resistance, and exhibits good electrical characteristics. .
- the crosslinking density improves the thermosetting resin composition of this invention by mixing an epoxy resin. Therefore, the thermosetting resin composition of the present invention is useful as an epoxy curing accelerator, adhesive or underfill agent.
- the thermosetting resin composition of the present invention includes a polymer having at least one structural unit represented by the formula (1) and an epoxy resin
- the epoxy resin includes at least one epoxy in the molecule.
- Compounds having groups can be used. Examples of such epoxy resins include 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol diglycidyl ether, and 2,6-diglycidyl phenyl.
- Glycidyl ether 1,1,3-tris [p- (2,3-epoxypropoxy) phenyl] propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4'-methylenebis (N, N-diglycidylaniline) ), Trimethylolethane triglycidyl ether, triglycidyl-p-aminophenol, tetraglycidylmetaxylenediamine, tetraglycidyldiaminodiphenylmethane, tetraglycidyl-1,3-bisaminomethylcyclohexa Bisphenol-A-diglycidyl ether, bisphenol-S-diglycidyl ether, pentaerythritol tetraglycidyl ether resorcinol diglycidyl ether, phthalic acid diglycidyl ester, neopentyl glycol diglycidyl ether
- the said epoxy resin can use only 1 type, and can also be used in combination of 2 or more type. 1% to 80% by mass, or 5% to 60% by mass, or 10% to 50% by mass of an epoxy resin is used with respect to the polymer contained in the thermosetting resin composition of the present invention. Can do.
- the solvent is not particularly limited as long as it is an organic solvent that can be used in a semiconductor device manufacturing process.
- organic solvents include ketones such as cyclohexanone, cyclopentanone, tetrahydrofuran, methyl isoamyl ketone, 2-butanone, and 2-heptanone; ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol, Propylene glycol monoacetate, dipropylene glycol, dipropylene glycol monoacetate, and polyhydric alcohols such as monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether, monophenyl ether and derivatives thereof; cyclic such as dioxane Ethers; and methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl
- thermosetting resin composition of the present invention may further contain additives such as an inorganic filler, a silane coupling agent, a surfactant, a rheology modifier, and a crosslinking agent as necessary.
- additives such as an inorganic filler, a silane coupling agent, a surfactant, a rheology modifier, and a crosslinking agent as necessary.
- the inorganic filler examples include sols such as silica, aluminum nitride, boron nitride, zirconia, and alumina having a particle diameter of 1 nm to 700 nm.
- the particles contained in the inorganic filler may be surface-treated with a silane coupling agent described later.
- silane coupling agent examples include vinyltrimethoxysilane, vinyltriethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-glycidylpropyltrimethoxysilane, and 3-glycidylpropyl.
- rheology modifier examples include, for example, phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butyl isodecyl phthalate; Acid derivatives, maleic acid derivatives such as di-normal butyl maleate, diethyl maleate, dinonyl maleate, oleic acid derivatives such as methyl oleate, butyl oleate, tetrahydrofurfuryl oleate, and stearic acid derivatives such as normal butyl stearate, glyceryl stearate Can be mentioned.
- phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butyl isodecyl phthalate
- Acid derivatives maleic acid derivatives such as di-normal butyl maleate, diethyl maleate
- surfactant examples include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as ethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as rubitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristea
- thermosetting resin composition of the present invention does not necessarily require the cross-linking agent, but if used, examples of the cross-linking agent include methoxymethyl group, ethoxymethyl group, butoxymethyl group, hexyloxymethyl group, etc. And nitrogen-containing compounds having a nitrogen atom substituted with an alkoxymethyl group or a hydroxymethyl group. Furthermore, a phenol group-containing compound, an allyl group-containing compound, an allyl group-containing polymer, an isocyanate group-containing compound or an isocyanate group-containing polymer can be used as a crosslinking agent.
- nitrogen-containing compound examples include hexamethoxymethyl melamine, tetramethoxymethyl benzoguanamine, 1,3,4,6-tetrakis (butoxymethyl) glycoluril, 1,3,4,6-tetrakis (hydroxymethyl) glycoluril. 1,3-bis (hydroxymethyl) urea, 1,1,3,3-tetrakis (butoxymethyl) urea, 1,1,3,3-tetrakis (methoxymethyl) urea, 1,3-bis (hydroxymethyl) ) -4,5-dihydroxy-2-imidazolinone, 1,3-bis (methoxymethyl) -4,5-dimethoxy-2-imidazolinone and the like nitrogen-containing compounds.
- crosslinking agent examples include methoxymethyl type melamine compounds (trade names: CYMEL (registered trademark) 300, 301, 303, 350) manufactured by Nippon Cytec Industries, Ltd., butoxymethyl type melamine compounds (trade name: My Coat (registered trademark) 506, 508), glycoluril compound (trade name: CYMEL (registered trademark) 1170, POWDERLINK (registered trademark) 1174), methylated urea resin (trade name: UFR65), butylated urea resin ( Product names: UFR300, U-VAN10S60, U-VAN10R, U-VAN11HV), urea / formaldehyde resin manufactured by DIC Corporation (high condensation type, product names: Beccamin (registered trademark) J-300S, P-955, N) can be mentioned commercially available compounds
- crosslinking agent only one kind of compound can be used, or two or more kinds of compounds can be used in combination. 1% to 50% by mass, or 8% to 40% by mass, or 15% to 30% by mass of a crosslinking agent is used with respect to the polymer contained in the thermosetting resin composition of the present invention. Can do.
- the thermosetting resin composition of this invention can contain a crosslinking catalyst with the said crosslinking agent.
- a crosslinking catalyst By using a crosslinking catalyst, the reaction of the crosslinking agent is promoted.
- the crosslinking catalyst include p-toluenesulfonic acid, trifluoromethanesulfonic acid, methanesulfonic acid, pyridinium-p-toluenesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, citric acid, benzoic acid, and hydroxybenzoic acid. 4-chlorobenzenesulfonic acid, 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid and 1-naphthalenesulfonic acid.
- the said crosslinking catalyst can use only 1 type, and can also be used in combination of 2 or more type. 0.01 mass% to 10 mass%, or 0.05 mass% to 8 mass%, or 0.1 mass% to 5 mass% with respect to the polymer contained in the thermosetting resin composition of the present invention, or 0.3% to 3% by weight or 0.5% to 1% by weight of a crosslinking catalyst can be used.
- thermosetting resin composition of the present invention can be used as an adhesive composition or an underfill composition.
- a miscible additive such as an adhesive is used as long as the essential characteristics of the present invention are not impaired.
- Conventional additives such as an additional resin, a tackifier, a plasticizer, an adhesion aid, a stabilizer, a colorant, an antifoaming material, and a flux for improving the performance can be added.
- Additional resins (polymers) for improving the performance of the adhesive include addition polymerization polymers such as polyester, polystyrene, polyimide, acrylic polymer, methacrylic polymer, polyvinyl ether, phenol novolac, naphthol novolac, polyether, polyamide, polycarbonate, etc.
- a polycondensation polymer can be used, and a polymer having an aromatic ring such as a benzene ring, a naphthalene ring, an anthracene ring, a triazine ring, a quinoline ring, or a quinoxaline ring is preferably used.
- the polymer having a triazine ring include a polyester having a structural unit represented by the following formula (7). (In the formula, L represents a divalent organic group.)
- the additional resin (polymer) as described above examples include benzyl acrylate, benzyl methacrylate, phenyl acrylate, naphthyl acrylate, anthryl methacrylate, anthryl methyl methacrylate, styrene, hydroxystyrene, benzyl vinyl ether, N-phenylmaleimide, and the like.
- An addition polymerization polymer containing an addition polymerizable monomer as its structural unit, and a polycondensation polymer such as phenol novolak and naphthol novolak can be mentioned.
- a polymer having no aromatic ring can be used as the additional resin (polymer).
- a polymer for example, only an addition polymerizable monomer having no aromatic ring such as alkyl acrylate, alkyl methacrylate, vinyl ether, alkyl vinyl ether, acrylonitrile, maleimide, N-alkylmaleimide, maleic anhydride, etc. Can be mentioned as addition polymerization polymers.
- the polymer may be a homopolymer or a copolymer.
- the weight average molecular weight of the additional resin (polymer) added to the adhesive composition or the underfill composition using the thermosetting resin composition of the present invention is, for example, 1,000 to 1,000,000, or 3,000 to 300,000, or 5,000 to 200,000, or 10,000 to 100,000.
- the content thereof is, for example, 40% by mass or less, or 20% by mass or less, or 1 to 19 in the solid content. % By mass.
- the tackifier is added to control the elastic modulus, viscosity, and surface state.
- the type of the tackifier is preferably determined in consideration of viscosity.
- This tackifier can be contained, for example, in a proportion of 100% by mass or less or 50% by mass or less with respect to the polymer contained in the adhesive composition or the underfill composition of the present invention.
- the GPC (gel permeation chromatography) analysis of the polymers obtained in the synthesis examples described below uses the following apparatus, and the measurement conditions are as follows.
- the obtained polymer is presumed to have a structural unit represented by the following formula (4-b) and a structural unit represented by the following formula (1-a).
- the solution was replaced with nitrogen and reacted at 90 ° C. for 20 hours to obtain a solution containing the polymer. Then, the obtained solution was dripped at methanol and reprecipitated. Thereafter, the mixture was suction filtered with a Buchner funnel, washed twice with methanol, and the resulting powder was dried with a vacuum dryer for 12 hours to obtain a polymer.
- the weight average molecular weight was 9,900 in standard polystyrene conversion.
- the obtained polymer is presumed to have a structural unit represented by the following formula (4-a) and a structural unit represented by the following formula (8).
- the solution was replaced with nitrogen and reacted at 90 ° C. for 20 hours to obtain a polymer-containing solution. Then, the obtained solution was dripped at methanol and reprecipitated. Thereafter, the mixture was suction filtered with a Buchner funnel, washed twice with methanol, and the resulting powder was dried with a vacuum dryer for 12 hours to obtain a polymer.
- the weight average molecular weight was 7,700 in standard polystyrene conversion.
- the obtained polymer is presumed to have a structural unit represented by the following formula (4-b) and a structural unit represented by the following formula (8).
- the 5 mass% weight loss temperatures of the polymers obtained in Synthesis Example 1 and Synthesis Example 2 are both 380 ° C. or higher, compared with the imidazole-based epoxy resin curing agents prepared in Comparative Examples 1 to 3. It showed high heat resistance.
- thermosetting resin composition ⁇ Example 1> 10 g of the polymer obtained in Synthesis Example 1 was dissolved in 40 g of tetrahydrofuran, and then filtered using a microfilter made of polytetrafluoroethylene (hereinafter abbreviated as PTFE in this specification) having a pore diameter of 0.2 ⁇ m. A composition containing 20% by mass of solid content was prepared.
- PTFE polytetrafluoroethylene
- Example 2 7 g of the polymer obtained in Synthesis Example 1 and 3 g of Epode GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 40 g of tetrahydrofuran, and then filtered using a PTFE microfilter having a pore size of 0.2 ⁇ m to obtain a solid content. A composition containing 20% by mass was prepared.
- Example 3 5 g of the polymer obtained in Synthesis Example 1 and 5 g of Epode GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 40 g of tetrahydrofuran, and then filtered using a PTFE microfilter having a pore size of 0.2 ⁇ m to obtain a solid content. A composition containing 20% by mass was prepared.
- Example 4 10 g of the polymer obtained in Synthesis Example 2 was dissolved in 40 g of tetrahydrofuran, and then filtered using a PTFE microfilter having a pore size of 0.2 ⁇ m to prepare a composition containing 20% by mass of a solid content.
- Example 5 7 g of the polymer obtained in Synthesis Example 2 and 3 g of epoxy resin GT401 (manufactured by Daicel Corporation) were dissolved in 40 g of tetrahydrofuran, and then filtered using a PTFE microfilter having a pore size of 0.2 ⁇ m to obtain a solid content. A composition containing 20% by mass was prepared.
- Example 6 5 g of the polymer obtained in Synthesis Example 2 and 5 g of epoxy resin GT401 (manufactured by Daicel Corporation) are dissolved in 40 g of tetrahydrofuran, and then filtered using a PTFE microfilter having a pore size of 0.2 ⁇ m to obtain a solid content. A composition containing 20% by mass was prepared.
- Example 7 50 g of the polymer obtained in Synthesis Example 1 was dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m to prepare a composition containing 50% by mass of the solid content.
- Example 8 35 g of the polymer obtained in Synthesis Example 1 and 15 g of epoxy resin GT401 (manufactured by Daicel Corporation) were dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- Example 9 25 g of the polymer obtained in Synthesis Example 1 and 25 g of Epode GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- Example 10 50 g of the polymer obtained in Synthesis Example 2 was dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m to prepare a composition containing 50% by mass of the solid content.
- Example 11 35 g of the polymer obtained in Synthesis Example 2 and 15 g of Epode GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- Example 12 25 g of the polymer obtained in Synthesis Example 2 and 25 g of Epode GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- Example 13 5 g of the polymer obtained in Synthesis Example 1, 5 g of Epode GT401 (manufactured by Daicel Corporation) as an epoxy resin, and 2 g of 3-phenylaminopropyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) are dissolved in 65.5 g of tetrahydrofuran. Thereafter, organosilica sol [3-methacryloxypropyltrimethoxysilane-treated silica-methylethylketone dispersion, silica primary particle diameter 40 nm to 50 nm, solid content 30.8% by mass, specific gravity (20 ° C. ) 1.007, viscosity (20 ° C.) 2.5 mPa ⁇ s, moisture 0.08 mass%] 32.5 g was mixed to prepare a composition containing 20 mass% solids.
- Example 14 5 g of the polymer obtained in Synthesis Example 1, 5 g of Epode GT401 (manufactured by Daicel Corporation) as an epoxy resin, and 2 g of 3-phenylaminopropyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) are dissolved in 22 g of cyclopentanone. Thereafter, organosilica sol [3-methacryloxypropyltrimethoxysilane-treated silica-methylethylketone dispersion, silica primary particle diameter 40 nm to 50 nm, solid content 30.8% by mass, specific gravity (20 ° C.
- ⁇ Comparative Example 8 35 g of the polymer obtained in Synthesis Example 3 and 15 g of Epolede GT401 (manufactured by Daicel Corporation) as an epoxy resin are dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- ⁇ Comparative Example 9 25 g of the polymer obtained in Synthesis Example 3 and 25 g of Epode GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- ⁇ Comparative Example 10 35 g of the polymer obtained in Synthesis Example 4 and 15 g of Epolede GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- ⁇ Comparative Example 11 25 g of the polymer obtained in Synthesis Example 4 and 25 g of Epode GT401 (manufactured by Daicel Corporation), which is an epoxy resin, are dissolved in 50 g of cyclopentanone, and then filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m. A composition containing 50% by mass of solid content was prepared.
- ⁇ Comparative Example 13> Dissolve 25 g of the polymer obtained in Synthesis Example 4, 0.5 g of 1-cyanoethyl-2-undecylimidazole of Comparative Example 1 and 25.5 g of epoxy resin Epolide GT401 (manufactured by Daicel Corporation) in 51.0 g of cyclopentanone. Thereafter, the mixture was filtered using a PTFE microfilter having a pore size of 5.0 ⁇ m to prepare a composition containing 50% by mass of a solid content.
- thermosetting resin composition of the present invention promotes the epoxy curing reaction.
- thermosetting resin film The compositions prepared in Examples 7 to 12 and 14 and the compositions prepared in Comparative Examples 12 to 13 were baked on a 4-inch silicon wafer so that the thickness after baking was 15 ⁇ m to 25 ⁇ m. After spin coating and baking at 100 ° C. for 5 minutes, the solvent was evaporated by baking at 150 ° C. for 5 minutes to form a thermosetting resin film. Thereafter, using a bonding apparatus (Ayumi Kogyo Co., Ltd., VJ-300), the silicon wafer on which the resin film was formed was subjected to other conditions under the conditions of a vacuum of 10 Pa or less, a temperature of 140 ° C., and an applied load of 300 kg.
- a bonding apparatus Alumi Kogyo Co., Ltd., VJ-300
- the resin was cured by bonding to a 4-inch glass wafer and then heating at 180 ° C. for 60 minutes.
- attach favorably without a void was evaluated as (circle) and the case where a void existed and the adhesion defect was seen was evaluated as x.
- the results are shown in Table 3 below.
- compositions prepared in Examples 7 to 12 and Example 14 had good adhesion and heat resistance after adhesion.
- compositions prepared in Comparative Example 12 and Comparative Example 13 using 1-cyanoethyl-2-undecylimidazole, which is an existing epoxy resin curing agent had low heat resistance, and voids thought to be caused by sublimation occurred. .
- Tg linear expansion coefficient (CTE) of Tg pre-Tg temperature and post-Tg temperature was 5 ° C./minute from room temperature to 200 ° C. with TMA (manufactured by NETZSCH). Evaluation was made by measuring the elongation of the cured film when the temperature was raised. Tg is judged as ⁇ at 140 ° C. or more and less than 140 ° C., CTE at temperature before Tg is judged as ⁇ when less than 70 ppm / ° C., and CTE at 70 ppm / ° C. or more is judged as ⁇ Was judged as ⁇ and 1000 ppm / ° C. or more was judged as ⁇ . Tg here is the temperature at which the amount of elongation of the cured film changes. The measurement results are shown in Table 4 below.
- compositions prepared in Examples 7 to 12 were diluted by adding cyclopentanone, coated on a silicon wafer using a spin coater, baked on a hot plate at 100 ° C. for 2 minutes, and then at 130 ° C. Baking was performed for 2 minutes, and further, baking was performed at 180 ° C. for 60 minutes in an oven purged with nitrogen to form a cured film having a thickness of 500 nm.
- the leakage current value and dielectric constant when an electric field of 1 MV / cm was applied to the prepared sample with Cvmap 92B (manufactured by Four Dimensions) were measured. The results are shown in Table 5 below.
- the cured films obtained from the compositions prepared in Examples 7 to 12 were found to have good electrical properties for adhesive or underfill applications.
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Abstract
Description
{式中、R1及びR2はそれぞれ独立に水素原子又は炭素原子数1乃至4のアルキル基を表し、Xは単結合又は2価の有機基を表し、Yは下記式(2):
(式中、Z1はカルボニル基又は-CONH-基を表し、Z2は炭素原子数1乃至5のアルキレン基、又は窒素原子を少なくとも1つ含有する5員環又は6員環の2価の飽和複素環基を表し、Z3は水素原子の少なくとも1つが炭素原子数1乃至5のアルキル基で置換されていてもよい、窒素原子を2つ含有する5員環又は6員環の芳香族複素環基を表す。)
で表されるアリーレン基を表す。}
(式中、R3及びR4はそれぞれ独立に、水素原子、又は水素原子の少なくとも1つがハロゲン原子で置換されていてもよいメチル基を表し、mは0又は1を表す。)
で表される2価の有機基を表す。
{式中、R1及びR2はそれぞれ独立に水素原子又は炭素原子数1乃至4のアルキル基を表し、Xは単結合又は2価の有機基を表し、Qは下記式(5)又は式(6):
(式中、Tは単結合、スルホニル基又は-O-基を表し、R3及びR4はそれぞれ独立に、水素原子、又は水素原子の少なくとも1つがハロゲン原子で置換されていてもよいメチル基を表し、4つのR5はそれぞれ独立に水素原子、メチル基、エチル基又はメトキシ基を表し、nは0又は1を表す。)
で表される2価の有機基を表す。}
(式中、Lは二価の有機基を表す。)
装置:一体型高速GPCシステム HLC-8220GPC 東ソー(株)製
カラム:KF-G,KF-804L
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
流量:1.0mL/分
標準試料:ポリスチレン
ディテクター:RI
3-イミダゾリルプロピル-1,5-ジアミノベンズアミド(別名:1-イミダゾリルプロピル-3,5-ジアミノベンズアミド)4.68g、4,4’-ジアミノ-3,3’-ジエチルジフェニルメタン(日本化薬(株)製、KAYAHARD A-A)41.21g、ビスフェノールM(三井化学ファイン(株)製)69.29g、パラホルムアルデヒド(東京化成工業(株)製)25.34g及びトリエチルアミン4.06gをN-メチル-2-ピロリドン327.49gに溶解させた後、窒素置換し90℃で20時間反応させポリマーを含む溶液を得た。その後、得られた溶液をメタノールに滴下し、再沈殿させた。その後、ブフナーロートで吸引ろ過し、メタノールにて2回洗浄し、得られた粉体を減圧乾燥機で12時間乾燥させ重合体を得た。得られた重合体のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は3,800であった。なお、得られた重合体は、下記式(4-a)で表される構造単位及び下記式(1-a)で表される構造単位を有すると推定される。
3-イミダゾリルプロピル-1,5-ジアミノベンズアミド(別名:1-イミダゾリルプロピル-3,5-ジアミノベンズアミド)4.68g、4,4’-ジアミノ-3,3’,5,5’-テトラメチルジフェニルメタン(日本化薬(株)製、KAYABOND 200S)41.21g、ビスフェノールM(三井化学ファイン(株)製)69.29g、パラホルムアルデヒド(東京化成工業(株)製)25.34g及びトリエチルアミン4.05gをN-メチル-2-ピロリドン327.49gに溶解させた後、窒素置換し90℃で20時間反応させポリマーを含む溶液を得た。その後、得られた溶液をメタノールに滴下し、再沈殿させた。その後、ブフナーロートで吸引ろ過し、メタノールにて2回洗浄し、得られた粉体を減圧乾燥機で12時間乾燥させ重合体を得た。得られた重合体のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は5,000であった。なお、得られた重合体は、下記式(4-b)で表される構造単位及び下記式(1-a)で表される構造単位を有すると推定される。
1,3-フェニレンジアミン(東京化成工業(株)製)1.95g、4,4’-ジアミノ-3,3’-ジエチルジフェニルメタン(日本化薬(株)製、KAYAHARD A-A)41.20g、ビスフェノールM(三井化学ファイン(株)製)69.30g、パラホルムアルデヒド(東京化成工業(株)製)22.87g及びトリエチルアミン4.05gをN-メチル-2-ピロリドン320.48gに溶解させた後、窒素置換し90℃で20時間反応させポリマーを含む溶液を得た。その後、得られた溶液をメタノールに滴下し、再沈殿させた。その後、ブフナーロートで吸引ろ過し、メタノールにて2回洗浄し、得られた粉体を減圧乾燥機で12時間乾燥させ重合体を得た。得られた重合体のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は9,900であった。なお、得られた重合体は、下記式(4-a)で表される構造単位及び下記式(8)で表される構造単位を有すると推定される。
1,3-フェニレンジアミン(東京化成工業(株)製)1.95g、4,4’-ジアミノ-3,3’,5,5’-テトラメチルジフェニルメタン(日本化薬(株)製、KAYABOND 200S)41.20g、ビスフェノールM(三井化学ファイン(株)製)69.34g、パラホルムアルデヒド(東京化成工業(株)製)22.82g及びトリエチルアミン4.09gをN-メチル-2-ピロリドン320.75gに溶解させた後、窒素置換し90℃で20時間反応させポリマーを含む溶液を得た。その後、得られた溶液をメタノールに滴下し、再沈殿させた。その後、ブフナーロートで吸引ろ過し、メタノールにて2回洗浄し、得られた粉体を減圧乾燥機で12時間乾燥させ重合体を得た。得られた重合体のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は7,700であった。なお、得られた重合体は、下記式(4-b)で表される構造単位及び下記式(8)で表される構造単位を有すると推定される。
エポキシ樹脂硬化剤である1-シアノエチル-2-ウンデシルイミダゾール(東京化成工業(株)製)を用意した。
エポキシ樹脂硬化剤である2-エチル-4-メチルイミダゾール(東京化成工業(株)製)を用意した。
エポキシ樹脂硬化剤である4-メチル-2-フェニルイミダゾール(東京化成工業(株)製)を用意した。
合成例1及び合成例2で得られた重合体、並びに比較例1乃至比較例3で用意されたイミダゾール系のエポキシ樹脂硬化剤の耐熱性について、TG-DTA(NETZSCH社製、TG/DTA2010SR)にて、試料を10℃/分で昇温し5質量%の重量減少を生ずる温度(以下、本明細書では5質量%重量減温度と略称する。)を測定した結果から評価した。5質量%重量減温度の測定結果を下記表1に示す。
<実施例1>
合成例1で得られた重合体10gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのポリテトラフルオロエチレン(以下、本明細書ではPTFEと略称する。)製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例1で得られた重合体7gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)3gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例1で得られた重合体5gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例2で得られた重合体10gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例2で得られた重合体7gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)3gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例2で得られた重合体5gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例1で得られた重合体50gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例1で得られた重合体35gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)15gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例1で得られた重合体25gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例2で得られた重合体50gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例2で得られた重合体35gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)15gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例2で得られた重合体25gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例1で得られた重合体5g、エポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5g及び3-フェニルアミノプロピルトリメトキシシラン(東京化成工業株式会社製)2gをテトラヒドロフラン65.5gに溶解させ、その後、無機フィラーであるオルガノシリカゾル[3-メタクリロキシプロピルトリメトキシシランで表面処理したシリカのメチルエチルケトン分散液、前記シリカの一次粒子径40nm乃至50nm、固形分30.8質量%、比重(20℃)1.007、粘度(20℃)2.5mPa・s、水分0.08質量%]32.5gを混和させ、固形分を20質量%含有する組成物を調製した。
合成例1で得られた重合体5g、エポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5g及び3-フェニルアミノプロピルトリメトキシシラン(東京化成工業株式会社製)2gをシクロペンタノン22gに溶解させ、その後、無機フィラーであるオルガノシリカゾル[3-メタクリロキシプロピルトリメトキシシランで表面処理したシリカのメチルエチルケトン分散液、前記シリカの一次粒子径40nm乃至50nm、固形分30.8質量%、比重(20℃)1.007、粘度(20℃)2.5mPa・s、水分0.08質量%]32.5gを混和させた。その後エバポレーターを用いて濃縮を行い、固形分を50質量%含有する組成物を調製した。
合成例3で得られた重合体7gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)3gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例3で得られた重合体5gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例4で得られた重合体7gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)3gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例4で得られた重合体5gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例3で得られた重合体35gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)15gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例3で得られた重合体25gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例4で得られた重合体35gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)15gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例4で得られた重合体25gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例3で得られた重合体25g、比較例1の1-シアノエチル-2-ウンデシルイミダゾール0.5g及びエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25.5gをシクロペンタノン51.0gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例4で得られた重合体25g、比較例1の1-シアノエチル-2-ウンデシルイミダゾール0.5g及びエポキシ樹脂エポリードGT401(株式会社ダイセル製)25.5gをシクロペンタノン51.0gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
実施例1乃至実施例6及び実施例13で調製した組成物1g並びに比較例4乃至比較例7で調製した組成物1gを直径40mmの金属製カップにいれ、50℃で60分間ベーク後、65℃で60分間ベークし、更に80℃で30分間ベークして溶媒を蒸発させ、熱硬化性の樹脂膜を形成した。その後、前記樹脂膜の硬化温度を、レオメーター(アントンパール社製、MCR102)を用いて5℃/分で昇温して評価し、硬化温度が190℃未満なら○、190℃以上なら×と判断した。なお、ここで示す硬化温度とは、樹脂膜の硬化反応によって複素粘度が10,000Pa・sとなる温度である。その硬化温度の結果を下記表2に示す。
実施例7乃至実施例12及び実施例14で調製した組成物並びに比較例12乃至比較例13で調製した組成物を、4インチのシリコンウェハー上に、ベーク後の厚みが15μm乃至25μmとなるようスピンコートし、100℃で5分間ベーク後、150℃で5分間ベークして溶媒を蒸発させ、熱硬化性の樹脂膜を形成した。その後、貼り合せ装置(アユミ工業(株)製、VJ-300)を使用して、真空度10Pa以下、温度140℃、印加荷重300kgの条件下で、前記樹脂膜を形成したシリコンウェハーを他の4インチガラスウェハーと接着させ、その後、180℃で60分間加熱して樹脂を硬化させた。ボイド無く良好に接着できた場合を○、ボイドが存在し接着不良が見られた場合を×と評価した。その結果を下記表3に示す。
上記接着性の評価で良好に接着できたサンプルについて、200℃で5分間の加熱後、250℃のホットプレートに載せ、剥離発生の有無を確認した。前記ホットプレートにそのサンプルを載せてから1時間以上経過しても剥離が発生しない場合を○、1時間未満にて剥離が発生する場合を×と評価した。その結果を下記表3に示す。
実施例8、実施例9、実施例11、実施例12及び実施例14で調製した組成物並びに比較例8乃至比較例13で調製した組成物を、アルミ箔をラミネートしたシリコンウェハー上に、ベーク後の厚みが15μm乃至25μmとなるようスピンコートし、100℃で5分間ベーク後、150℃で5分間ベークして溶媒を蒸発させ、アルミ箔に積層された熱硬化性の樹脂膜を得た。その後、窒素雰囲気中でさらに180℃で60分間ベークして樹脂膜を硬化させた後、6mol/Lの塩酸水溶液に投入してアルミ箔を溶解させ、硬化膜を得た。得られた硬化膜を幅5mmにカットし、Tgと、Tg前温度及びTg後温度の線膨張係数(CTE)を、TMA(NETZSCH社製、TMA4000SA)で5℃/分で室温から200℃まで昇温したときの硬化膜の伸びを測定することにより評価した。Tgは140℃以上を○、140℃未満を×と判断し、Tg前温度のCTEは70ppm/℃未満を○、70ppm/℃以上を×と判断し、Tg後温度のCTEは1000ppm/℃未満を○、1000ppm/℃以上を×と判断した。ここでいうTgは、硬化膜の伸び量の変曲する温度である。測定結果を下記表4に示す。
実施例7乃至実施例12で調製した組成物に、シクロペンタノンを加えて希釈し、シリコンウェハー上にスピンコーターを用いて塗布し、ホットプレート上において100℃で2分間ベーク後、130℃で2分間ベークを行い、さらに、窒素置換されたオーブン中で、180℃で60分間ベークを行い、膜厚500nmの硬化膜を形成した。作製したサンプルに対し、Cvmap 92B (Four Dimensions社製)にて1MV/cmの電界を印加したときのリーク電流値、及び誘電率を測定した。その結果を下記表5に示す。
Claims (15)
- 前記式(2)においてZ3はイミダゾリル基を表す、請求項1に記載の熱硬化性樹脂組成物。
- 前記式(2)においてZ2は炭素原子数1乃至5のアルキレン基を表す、請求項1又は請求項2に記載の熱硬化性樹脂組成物。
- 前記式(2)においてZ1は-CONH-基を表す、請求項1乃至請求項3のいずれか一項に記載の熱硬化性樹脂組成物。
- 前記式(1)においてXは、水素原子の少なくとも1つがハロゲン原子で置換されていてもよい炭素原子数1乃至6のアルキレン基、環状アルキレン基、水素原子の少なくとも1つがハロゲン原子で置換されていてもよいアリーレン基、スルホニル基、カルボニル基、-O-基又は-COO-基を含む2価の有機基を表す、請求項1乃至請求項4のいずれか一項に記載の熱硬化性樹脂組成物。
- 前記重合体の重量平均分子量は1,000乃至100,000である請求項1乃至請求項9のいずれか一項に記載の熱硬化性樹脂組成物。
- エポキシ樹脂をさらに含む請求項1乃至請求項10のいずれか一項に記載の熱硬化性樹脂組成物。
- 溶剤をさらに含む請求項1乃至請求項11のいずれか一項に記載の熱硬化性樹脂組成物。
- 接着剤組成物又はアンダーフィル組成物である請求項1乃至請求項12のいずれか一項に記載の熱硬化性樹脂組成物。
- シランカップリング剤をさらに含む請求項1乃至請求項13のいずれか一項に記載の熱硬化性樹脂組成物。
- 粒子径が1nm以上700nm以下の無機フィラーをさらに含む請求項1乃至請求項14のいずれか一項に記載の熱硬化性樹脂組成物。
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007129640A1 (ja) * | 2006-05-01 | 2007-11-15 | Sekisui Chemical Co., Ltd. | 樹脂焼成物及びこれを搭載した電子機器 |
JP2008291070A (ja) * | 2007-05-22 | 2008-12-04 | Sekisui Chem Co Ltd | 熱硬化性樹脂の製造方法、及び熱硬化性樹脂 |
WO2009008468A1 (ja) * | 2007-07-10 | 2009-01-15 | Sekisui Chemical Co., Ltd. | ベンゾキサジン構造を有する熱硬化性樹脂及びその製造方法 |
JP2009242669A (ja) * | 2008-03-31 | 2009-10-22 | Sekisui Chem Co Ltd | 熱硬化性樹脂組成物の製造方法、熱硬化性樹脂組成物、成形体、硬化体及び電子部品 |
JP2009256650A (ja) * | 2008-03-26 | 2009-11-05 | Sekisui Chem Co Ltd | 熱硬化性樹脂及びその製造方法、熱硬化性樹脂を含む熱硬化性組成物及びその成形体、硬化体、硬化成形体、並びにそれらを含む電子機器 |
WO2011040459A1 (ja) * | 2009-09-30 | 2011-04-07 | 積水化学工業株式会社 | ベンゾオキサジン環を有する熱硬化性樹脂及びその製造方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1419619A (en) | 1972-01-25 | 1975-12-31 | Redifon Ltd | Scanning devices |
JPS4931079A (ja) | 1972-07-21 | 1974-03-20 | ||
JP4887850B2 (ja) | 2006-03-16 | 2012-02-29 | 住友ベークライト株式会社 | アンダーフィル用液状樹脂組成物、並びにそれを用いた半導体装置の製造方法及び半導体装置 |
JP5019363B2 (ja) | 2007-02-22 | 2012-09-05 | 信越化学工業株式会社 | エポキシ樹脂接着剤組成物 |
JP5132220B2 (ja) * | 2007-08-09 | 2013-01-30 | 電気化学工業株式会社 | スチレン系樹脂組成物 |
JP4931079B2 (ja) | 2007-12-21 | 2012-05-16 | パナソニック株式会社 | アンダーフィル用液状熱硬化性樹脂組成物とそれを用いた半導体装置 |
KR101615990B1 (ko) | 2008-09-18 | 2016-04-28 | 고쿠리츠다이가쿠호우진 도쿄다이가쿠 | 반도체장치의 제조방법 |
DE102009003033B4 (de) * | 2009-05-12 | 2013-02-21 | Henkel Ag & Co. Kgaa | Polymerisierbare Benzoxazin-Verbindungen mit grenzflächenaktiven bzw. oberflächenaktiven Eigenschaften |
-
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007129640A1 (ja) * | 2006-05-01 | 2007-11-15 | Sekisui Chemical Co., Ltd. | 樹脂焼成物及びこれを搭載した電子機器 |
JP2008291070A (ja) * | 2007-05-22 | 2008-12-04 | Sekisui Chem Co Ltd | 熱硬化性樹脂の製造方法、及び熱硬化性樹脂 |
WO2009008468A1 (ja) * | 2007-07-10 | 2009-01-15 | Sekisui Chemical Co., Ltd. | ベンゾキサジン構造を有する熱硬化性樹脂及びその製造方法 |
JP2009256650A (ja) * | 2008-03-26 | 2009-11-05 | Sekisui Chem Co Ltd | 熱硬化性樹脂及びその製造方法、熱硬化性樹脂を含む熱硬化性組成物及びその成形体、硬化体、硬化成形体、並びにそれらを含む電子機器 |
JP2009242669A (ja) * | 2008-03-31 | 2009-10-22 | Sekisui Chem Co Ltd | 熱硬化性樹脂組成物の製造方法、熱硬化性樹脂組成物、成形体、硬化体及び電子部品 |
WO2011040459A1 (ja) * | 2009-09-30 | 2011-04-07 | 積水化学工業株式会社 | ベンゾオキサジン環を有する熱硬化性樹脂及びその製造方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020116313A1 (ja) * | 2018-12-03 | 2020-06-11 | パナソニックIpマネジメント株式会社 | 補強用樹脂組成物、電子部品、電子部品の製造方法、実装構造体及び実装構造体の製造方法 |
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JPWO2014156843A1 (ja) | 2017-02-16 |
SG11201507940TA (en) | 2015-10-29 |
CN105051105A (zh) | 2015-11-11 |
KR101967369B1 (ko) | 2019-04-09 |
TWI620767B (zh) | 2018-04-11 |
JP6288074B2 (ja) | 2018-03-07 |
US20160272764A1 (en) | 2016-09-22 |
CN105051105B (zh) | 2017-04-26 |
KR20150137052A (ko) | 2015-12-08 |
TW201502167A (zh) | 2015-01-16 |
US9567435B2 (en) | 2017-02-14 |
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