WO2018181536A1 - 接着剤組成物及び構造体 - Google Patents
接着剤組成物及び構造体 Download PDFInfo
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- WO2018181536A1 WO2018181536A1 PCT/JP2018/012897 JP2018012897W WO2018181536A1 WO 2018181536 A1 WO2018181536 A1 WO 2018181536A1 JP 2018012897 W JP2018012897 W JP 2018012897W WO 2018181536 A1 WO2018181536 A1 WO 2018181536A1
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- Prior art keywords
- group
- adhesive composition
- silane compound
- circuit
- mass
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 133
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- -1 silane compound Chemical class 0.000 claims abstract description 112
- 229910000077 silane Inorganic materials 0.000 claims abstract description 100
- 239000003822 epoxy resin Substances 0.000 claims abstract description 54
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 54
- 229920005989 resin Polymers 0.000 claims abstract description 38
- 239000011347 resin Substances 0.000 claims abstract description 38
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000000524 functional group Chemical group 0.000 claims abstract description 22
- 239000002245 particle Substances 0.000 claims description 47
- 125000003700 epoxy group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 8
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 125000003566 oxetanyl group Chemical group 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004018 acid anhydride group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 abstract description 22
- 125000002091 cationic group Chemical group 0.000 abstract description 22
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 13
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
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- 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
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
-
- 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
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- 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
- H01L21/18—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 the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/185—Joining of semiconductor bodies for junction formation
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
Definitions
- the present disclosure relates to an adhesive composition and a structure.
- Various adhesives are conventionally used in semiconductor elements and liquid crystal display elements (display display elements) for the purpose of bonding various members in the elements.
- the properties required for adhesives are diverse, including adhesiveness, heat resistance, reliability in high temperature and high humidity conditions, and the like.
- an adherend used for adhesion a printed wiring board, an organic substrate (polyimide substrate, etc.), metal (titanium, copper, aluminum, etc.), ITO (Indium Tin Oxide), IZO (Indium Zinc Oxide)
- Base materials having surface states such as IGZO (Indium Gallium Zinc Oxide), SiN x , and SiO 2 are used, and molecular design of an adhesive suitable for each adherend is necessary.
- thermosetting resins epoxy resins, acrylic resins, etc.
- a latent curing agent that generates an epoxy resin and a cationic species or anionic species having reactivity with the epoxy resin by heat or light
- the latent curing agent is an important factor for determining the curing temperature and the curing rate, and various compounds have been used from the viewpoint of storage stability at normal temperature and curing rate during heating. In the actual process, for example, desired adhesiveness was obtained by curing under a curing condition of a temperature of 170 to 250 ° C. for 10 seconds to 3 hours.
- an epoxy resin cationic curing system using an onium salt as a thermal latent catalyst has attracted attention.
- the cationic curing system is highly reactive with cations, which are reactive species, so that it can be cured for a short time, and the catalyst exists stably below the decomposition temperature of the onium salt. It is a curing system that achieves both curing and storage stability (for example, storage stability near room temperature).
- a cationic curing adhesive for example, a cationic curing adhesive composition containing a silane compound (such as a silane coupling agent) having a functional group capable of cationic polymerization (such as an epoxy group) is known. (For example, refer to Patent Document 1 below).
- an anion-curable adhesive composition containing a silane compound (such as a silane coupling agent) having a functional group capable of anionic polymerization (such as an epoxy group) is known (for example, the following) Patent Document 1).
- the silane compound described above is used to improve the adhesiveness of the adhesive composition.
- a conventional adhesive composition mixture
- a silane compound having a functional group that reacts in a cation or anion curing system as a silane compound is stored, the characteristic deterioration of the silane compound is significant, and the adhesive composition There is a problem that adhesiveness is lowered. Therefore, it is required to improve storage stability with respect to conventional adhesive compositions.
- an object of the present disclosure is to provide an adhesive composition having excellent storage stability and a structure using the same.
- the present inventors presume that the cause of the deterioration of the characteristics of the silane compound in the conventional adhesive composition is as follows. That is, during the storage of the adhesive composition, when another initiator different from the silane compound starts the polymerization reaction, the silane compound is incorporated into the polymerization reaction, so that the constituent material of the adhesive composition (resin etc.) It is taken in inside. Accordingly, the number of molecules of the silane compound that can act on the interface between the adhesive composition and the adherend is reduced, so that the characteristics are estimated to deteriorate.
- the inventors of the present invention improve storage stability (pot life characteristics) in an anionic or cationic polymerization type adhesive composition containing a silane compound (for example, an epoxy resin anion curing system or an epoxy resin cationic curing system).
- a silane compound for example, an epoxy resin anion curing system or an epoxy resin cationic curing system.
- an epoxy resin that is an epoxy group-containing compound or an adhesive composition that contains an oxetane resin that is an oxetane group-containing compound has a functional group that reacts with the epoxy resin or oxetane resin. It has been found that the storage stability of the adhesive composition is remarkably improved when 1 silane compound and the second silane compound that reacts with the first silane compound are used in combination.
- one aspect of the present disclosure is an anion polymerization or a cation polymerization epoxy resin or oxetane resin, a first silane compound having a functional group that reacts with the epoxy resin or oxetane resin, and the first silane compound.
- An adhesive composition containing a reactive second silane compound is provided.
- the adhesive composition according to one aspect of the present disclosure has excellent storage stability as compared with the conventional one.
- Such an adhesive composition can suppress the adhesiveness of the adhesive composition from decreasing over time during storage.
- the present inventors presume that the following factors can provide such an effect. That is, the first silane compound having a functional group that reacts with the epoxy resin or the oxetane resin and the second silane compound that reacts with the first silane compound are present in the adhesive composition, and thus are being stored. Even if the first silane compound is polymerized by an anion or cation curing polymerization reaction and taken into the polymer, the second silane compound and the adherend are the first silane compound in the polymer. It is presumed that the adhesiveness between the adhesive composition or a cured product thereof and the adherend can be maintained.
- the functional group of the first silane compound preferably contains at least one selected from the group consisting of an epoxy group, an oxetane group, an amino group, an acid anhydride group, an isocyanate group, and a mercapto group.
- the second silane compound preferably contains at least one selected from the group consisting of alkyl groups, phenyl groups, alkoxysilyl groups, hydroxyl groups, fluorine-containing groups, (meth) acryloyl groups, and vinyl groups.
- the adhesive composition of the present disclosure may further contain conductive particles.
- the adhesive composition of the present disclosure may be for circuit connection (adhesive composition for circuit connection).
- Another aspect of the present disclosure provides a structure including the adhesive composition according to one aspect of the present disclosure or a cured product thereof.
- Another aspect of the present disclosure includes a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, the first circuit member, and the second circuit member.
- a structure comprising the composition or a cured product thereof is provided.
- the present disclosure it is possible to provide an application of the adhesive composition or the cured product thereof to the structure or the production thereof. According to the present disclosure, it is possible to provide application of an adhesive composition or a cured product thereof to circuit connection. According to the present disclosure, it is possible to provide an application of an adhesive composition or a cured product thereof to a circuit connection structure or a production thereof.
- (meth) acrylate means at least one of acrylate and methacrylate corresponding thereto.
- the materials exemplified below may be used alone or in combination of two or more unless otherwise specified.
- the content of each component in the composition means the total amount of the plurality of substances present in the composition unless there is a specific notice when there are a plurality of substances corresponding to each component in the composition.
- the numerical range indicated by using “to” indicates a range including the numerical values described before and after “to” as the minimum value and the maximum value, respectively. “A or B” only needs to include either A or B, and may include both.
- Normal temperature means 25 ° C.
- the upper limit value or lower limit value of a numerical range of a certain step may be replaced with the upper limit value or lower limit value of the numerical range of another step. Further, in the numerical ranges described in this specification, the upper limit value or the lower limit value of the numerical range may be replaced with the values shown in the examples.
- the adhesive composition of the present embodiment includes an epoxy resin or oxetane resin (anionic or cationic polymerizable substance) capable of anion polymerization or cationic polymerization, and a first silane compound having a functional group that reacts with the epoxy resin or oxetane resin. And a second silane compound that reacts with the first silane compound.
- the adhesive composition of the present embodiment includes a functional group that reacts with an epoxy resin or an oxetane resin as a silane compound (a functional group that participates in a polymerization reaction of an anionic or cationic curing system.
- the adhesive composition of the present embodiment is an anionic or cationic curing type (anionic polymerization type or cationic polymerization type) adhesive composition.
- the adhesive composition of this embodiment can be suitably used as an adhesive composition for circuit connection.
- the adhesive composition of the present embodiment includes a first silane compound having a functional group that reacts with an epoxy resin or an oxetane resin in an anionic or cationic polymerization system, and a second silane compound that reacts with the first silane compound. Containing.
- the second silane compound is a compound that does not correspond to the first silane compound, and does not have a functional group that reacts with an epoxy resin or an oxetane resin in an anionic or cationic polymerization system.
- the silane compound may be a silane coupling agent.
- the second silane compound can react with the first silane compound by hydrolysis / condensation reaction of an alkoxysilyl group. .
- Examples of functional groups that react with epoxy resins or oxetane resins include epoxy groups, oxetane groups, amino groups, acid anhydride groups, isocyanate groups, and mercapto groups.
- the functional group that reacts with the epoxy resin or the oxetane resin is preferably at least one selected from the group consisting of an epoxy group and an oxetane group, and more preferably an epoxy group, from the viewpoint of obtaining excellent storage stability and adhesiveness.
- the second silane compound may have a functional group that does not participate in the anion or cation polymerization reaction (does not react with the epoxy resin or oxetane resin in the anion or cation polymerization system).
- the functional group not involved in the anionic or cationic polymerization reaction include an alkyl group, a phenyl group, an alkoxysilyl group, a hydroxyl group, a fluorine-containing group, a (meth) acryloyl group, a vinyl group, and a ureido group.
- the second silane compound preferably has at least one selected from the group consisting of an alkyl group, a phenyl group, and an alkoxysilyl group, and has an alkoxysilyl group, from the viewpoint of obtaining excellent storage stability. More preferred.
- silane compound a compound represented by the following general formula (I) can be used.
- the compound represented by the formula (I) can be synthesized by, for example, a method of reacting an organochlorosilane and an alcohol.
- X represents an organic group
- R 1 and R 2 each independently represents an alkyl group
- m represents an integer of 0 to 2
- s represents an integer of 0 or more.
- each R 1 may be the same as or different from each other.
- each R 2 may be the same as or different from each other.
- Each of R 1 , R 2 and C s H 2s may be branched.
- an ethylenically unsaturated bond-containing group (a group containing an ethylenically unsaturated bond), a nitrogen atom-containing group (a group containing a nitrogen atom), a sulfur atom-containing group (a group containing a sulfur atom), an epoxy group , Etc.
- the ethylenically unsaturated bond-containing group include a (meth) acryloyl group, a vinyl group, and a styryl group.
- Examples of the nitrogen atom-containing group include an amino group, a mono-substituted amino group, a di-substituted amino group, an isocyanate group, an imidazole group, a ureido group, and a maleimide group.
- Examples of the mono-substituted amino group include an alkylamino group (such as a methylamino group), a benzylamino group, a phenylamino group, and a cycloalkylamino group (such as a cyclohexylamino group).
- Examples of the disubstituted amino group include an acyclic disubstituted amino group and a cyclic disubstituted amino group.
- Examples of the acyclic disubstituted amino group include a dialkylamino group (such as a dimethylamino group).
- Examples of the cyclic disubstituted amino group include a morpholino group and a piperazino group.
- a mercapto group etc. are mentioned as a sulfur atom containing group.
- the epoxy group may be contained in an epoxy group-containing group (group containing an epoxy group) such as a glycidyl group or a glycidoxy group.
- the (meth) acryloyl group may be contained in the (meth) acryloyloxy group.
- a functional group that reacts with an epoxy resin or an oxetane resin is selected from the above.
- the compound represented by the said general formula (I) as a 2nd silane compound, as an organic group X it does not react with an epoxy resin or an oxetane resin from the above (it does not participate in anion or a cation polymerization reaction) ) Select a functional group.
- the carbon number of the alkyl group of R 1 and R 2 is, for example, 1-20.
- Specific examples of the alkyl group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group.
- each structural isomer of the alkyl group can be used.
- the number of carbon atoms of the alkyl group represented by R 1 is preferably 1 to 10 from the viewpoint of preventing steric hindrance when the alkoxysilyl group portion reacts with the adherend and obtaining further excellent adhesion to the adherend. ⁇ 5 is more preferred.
- the number of carbon atoms of the alkyl group represented by R 2 is preferably 1 to 10 and more preferably 1 to 5 from the viewpoint of obtaining further excellent adhesion to the adherend.
- M is an integer from 0 to 2.
- m is preferably steric hindrance when the alkoxysilyl group moiety reacts with the adherend, and is preferably 0 to 1, more preferably 0 from the viewpoint of obtaining further excellent adhesion to the adherend.
- s is an integer of 0 or more.
- s is preferably an integer of 1 to 20 and more preferably an integer of 1 to 10 from the viewpoint of obtaining further excellent storage stability.
- Examples of the first silane compound include glycidoxyalkyltrialkoxysilane (eg, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 8-glycidoxyoctyltrimethoxysilane, 8- Glycidoxyoctyltriethoxysilane), glycidoxyalkylalkyldialkoxysilane (eg 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 8-glycidoxyoctylmethyldimethoxy) Silane, 8-glycidoxyoctylmethyldiethoxysilane, etc.), N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N -2
- the first silane compound is preferably at least one selected from the group consisting of glycidoxyalkyltrialkoxysilane and glycidoxyalkylalkyldialkoxysilane from the viewpoint of obtaining excellent storage stability and adhesiveness.
- a 1st silane compound may be used individually by 1 type, and may be used in combination of 2 or more type.
- Examples of the second silane compound include alkyltrialkoxysilane, dialkyldialkoxysilane, phenyltrialkoxysilane, fluoroalkyltrialkoxysilane, fluoroalkylalkyldialkoxysilane, (meth) acryloxyalkyltrialkoxysilane, (meth) acrylic.
- Roxyalkylalkyldialkoxysilane (meth) acryloxytrialkylalkoxysilane, alkenyltrialkoxysilane, alkenylalkyldialkoxysilane, styryltrialkoxysilane, styrylalkyltrialkoxysilane, 3-ureidopropyltriethoxysilane, 8-ureido Examples include octyltriethoxysilane.
- Alkyltrialkoxysilanes include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, butyltriethoxysilane, and pentyltrimethoxy.
- Silane pentyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, heptyltrimethoxysilane, heptyltriethoxysilane, octyltrimethoxysilane, octyltriethoxysilane, nonyltrimethoxysilane, nonyltriethoxysilane, decyltrimethoxy Examples include silane and decyltriethoxysilane.
- Dialkyl dialkoxysilanes include dimethyldimethoxysilane, dimethyldiethoxysilane, ethylmethyldimethoxysilane, ethylmethyldiethoxysilane, propylmethyldimethoxysilane, propylmethyldiethoxysilane, butylmethyldimethoxysilane, butylmethyldiethoxysilane, and pentyl.
- Methyldimethoxysilane pentylmethyldiethoxysilane, hexylmethyldimethoxysilane, hexylmethyldiethoxysilane, heptylmethyldimethoxysilane, heptylmethyldiethoxysilane, octylmethyldimethoxysilane, octylmethyldiethoxysilane, nonylmethyldimethoxysilane, nonylmethyl Examples include diethoxysilane, decylmethyldimethoxysilane, and decylmethyldiethoxysilane.
- phenyltrialkoxysilane examples include phenyltrimethoxysilane and phenyltriethoxysilane.
- fluoroalkyltrialkoxysilane examples include trifluoropropyltrimethoxysilane and trifluoropropyltriethoxysilane.
- fluoroalkylalkyldialkoxysilane examples include trifluoropropylmethyldimethoxysilane and trifluoropropylmethyldiethoxysilane.
- Examples of (meth) acryloxyalkyltrialkoxysilane include 3- (meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, 8- (meth) acryloxyoctyltrimethoxysilane, 8- (Meth) acryloxyoctyltriethoxysilane and the like.
- Examples of (meth) acryloxyalkylalkyldialkoxysilane include 3- (meth) acryloxypropylmethyldimethoxysilane, 3- (meth) acryloxypropylmethyldiethoxysilane, 8- (meth) acryloxyoctylmethyldimethoxysilane, Examples include 8- (meth) acryloxyoctylmethyldiethoxysilane.
- alkenyl trialkoxysilane examples include vinyl trialkoxysilane and octenyl trialkoxysilane.
- vinyltrialkoxysilane examples include vinyltrimethoxysilane and vinyltriethoxysilane.
- octenyltrialkoxysilane examples include 7-octenyltrimethoxysilane and 7-octenyltriethoxysilane.
- alkenyl alkyl dialkoxy silane examples include vinyl alkyl dialkoxy silane and octenyl alkyl dialkoxy silane.
- vinyl alkyl dialkoxy silane examples include vinyl methyl dimethoxy silane and vinyl methyl diethoxy silane.
- octenylalkyl dialkoxysilane examples include 7-octenylmethyldimethoxysilane, 7-octenylmethyldiethoxysilane and the like.
- styryltrialkoxysilane examples include p-styryltrimethoxysilane.
- styrylalkyltrialkoxysilane examples include p-styryloctyltrimethoxysilane.
- the second silane compound is preferably at least one selected from the group consisting of alkyltrialkoxysilane, phenyltrialkoxysilane, and (meth) acryloxyalkyltrialkoxysilane, from the viewpoint of obtaining further excellent storage stability. More preferred is at least one selected from the group consisting of methyltrimethoxysilane and 3- (meth) acryloxypropyltrimethoxysilane.
- a 2nd silane compound may be used individually by 1 type, and may be used in combination of 2 or more type.
- Examples of the second silane compound other than the compound represented by the formula (I) include tetraalkoxysilane, alkyltrialkoxysilane, and dialkyl dialkoxysilane.
- Examples of the second silane compound include methyltrimethoxysilane, methyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, dimethyldimethoxysilane, tetramethoxysilane, tetraethoxysilane, and phenyltrimethoxy. Examples thereof include silane and phenyltriethoxysilane.
- the second silane compound other than the compound represented by the formula (I) at least one selected from the group consisting of alkyltrialkoxysilane and tetraalkoxysilane is preferable from the viewpoint of obtaining further excellent storage stability. More preferred is at least one selected from the group consisting of methyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane and tetraethoxysilane.
- the second silane compound other than the compound represented by the formula (I) may be used alone or in combination of two or more.
- a silane compound (a 1st silane compound, a 2nd silane compound, and another silane compound are included) is not specifically limited, A to-be-adhered body (circuit member etc.), an adhesive composition, or its hardened
- the following ranges are preferable based on the total mass of the adhesive component (solid content other than conductive particles in the adhesive composition; the same applies hereinafter).
- the content of the silane compound is preferably 0.1% by mass or more, more preferably 0.25% by mass or more, further preferably 0.5% by mass or more, and 1% by mass or more. It is particularly preferable that it is 2% by mass or more, very preferably 3% by mass or more.
- the content of the silane compound is preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less, and particularly preferably 5% by mass or less. From these viewpoints, the content of the silane compound is preferably 0.1 to 20% by mass, more preferably 0.25 to 15% by mass, and 0.5 to 10% by mass. More preferably, it is 1 to 5% by mass, particularly preferably 2 to 5% by mass, and most preferably 3 to 5% by mass.
- the content of the first silane compound is the adhesive from the viewpoint of easily suppressing the generation of exfoliated bubbles at the interface between the adherend (circuit member or the like) and the adhesive composition or the cured product thereof (circuit connection member or the like).
- the following ranges are preferred based on the total mass of the adhesive component of the composition.
- the content of the first silane compound is preferably 0.1% by mass or more, more preferably 0.25% by mass or more, further preferably 0.5% by mass or more, and 1% by mass. % Or more is particularly preferable, and 1.5% by mass or more is extremely preferable.
- the content of the first silane compound is preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less, and further preferably 5% by mass or less. Particularly preferred is 3% by mass or less. From these viewpoints, the content of the first silane compound is preferably 0.1 to 20% by mass, more preferably 0.25 to 15% by mass, and 0.5 to 10% by mass. More preferably, it is 1 to 5% by mass, particularly preferably 1.5 to 3% by mass.
- the content of the second silane compound is the adhesive from the viewpoint of easily suppressing the generation of exfoliated bubbles at the interface between the adherend (circuit member or the like) and the adhesive composition or its cured product (circuit connection member or the like).
- the following ranges are preferred based on the total mass of the adhesive component of the composition.
- the content of the second silane compound is preferably 0.1% by mass or more, more preferably 0.25% by mass or more, further preferably 0.5% by mass or more, and 1% by mass. % Or more is particularly preferable, and 1.5% by mass or more is extremely preferable.
- the content of the second silane compound is preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less, and further preferably 5% by mass or less.
- the content of the second silane compound is preferably 0.1 to 20% by mass, more preferably 0.25 to 15% by mass, and 0.5 to 10% by mass. More preferably, it is 1 to 5% by mass, particularly preferably 1.5 to 3% by mass.
- the ratio of the content of the first silane compound to the content of the second silane compound is a viewpoint of obtaining further excellent storage stability and adhesiveness. Therefore, 0.01 or more is preferable, 0.1 or more is more preferable, 0.2 or more is further preferable, 0.5 or more is particularly preferable, and 1 or more is extremely preferable.
- the ratio is preferably 100 or less, more preferably 10 or less, still more preferably 5 or less, particularly preferably 3 or less, and extremely preferably 2 or less from the viewpoint of obtaining further excellent storage stability and adhesiveness.
- anion or cation polymerizable component epoxy resin or oxetane resin capable of anion polymerization or cation polymerization
- anion- or cation-polymerizable epoxy resin that can be anionic or cationically polymerizable include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin, cresol Novolac epoxy resin, bisphenol A novolac epoxy resin, bisphenol F novolac epoxy resin, alicyclic epoxy resin, glycidyl ester epoxy resin, glycidyl amine epoxy resin, hydantoin epoxy resin, isocyanurate epoxy resin, aliphatic Examples thereof include chain epoxy resins.
- the anionic or cationic polymerizable component may be halogenated or hydrogenated.
- An anion or a cation polymerizable component may be used individually by 1 type, and may be used in combination of 2 or more type.
- the content of the anionic or cationic polymerizable component is preferably in the following range based on the total mass of the adhesive component of the adhesive composition from the viewpoint of further improving the adhesion with the adherend.
- the content of the anionic or cationic polymerizable component is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 15% by mass or more.
- the content of the anionic or cationic polymerizable component is preferably 90% by mass or less, more preferably 80% by mass or less, and still more preferably 70% by mass or less. From these viewpoints, the content of the anionic or cationic polymerizable component is preferably 5 to 90% by mass, more preferably 10 to 80% by mass, and further preferably 15 to 70% by mass.
- the adhesive composition of this embodiment may further contain a curing agent.
- the curing agent is not particularly limited as long as it can cure an anionic or cationic polymerizable epoxy resin or oxetane resin. Curing agents that can generate anionic species by heat or light (such as anion-polymerizable catalytic curing agent), and curing agents that can generate cationic species by heat or light (cationic polymerizable) Catalyst-type curing agents, etc.) and polyaddition-type curing agents. A hardening
- curing agent may be used individually by 1 type, and may be used in combination of 2 or more type.
- the curing agent is preferably a curing agent capable of generating anionic species or cationic species by heat or light from the viewpoint of being excellent in rapid curability and not requiring consideration in terms of chemical equivalents.
- the catalyst type curing agent is more preferable.
- anionic polymerizable catalyst-type curing agents examples include imidazole-based curing agents, hydrazide-based curing agents, boron trifluoride-amine complexes, amine imides, tertiary amines, diaminomaleonitrile, melamine and derivatives thereof, polyamine salts, Examples thereof include dicyandiamide, and these modified products can also be used.
- examples of the cationic polymerizable catalyst-type curing agent include diazonium salts and sulfonium salts, and these modified products can also be used.
- Examples of the polyaddition type curing agent include polyamines, polymercaptans, polyphenols, and acid anhydrides.
- the epoxy resin or oxetane resin is cured by heating at a medium temperature of about 160 to 200 ° C. for several tens of seconds to several hours. be able to. Therefore, the pot life (pot life) can be made relatively long.
- a photosensitive onium salt aromatic diazonium salt, aromatic sulfonium salt, etc.
- aliphatic sulfonium salt etc. are mentioned as what activates by heat other than energy ray irradiation, and hardens an epoxy resin or an oxetane resin.
- a curing agent is preferable because it has fast curability.
- Curing agents coated with polymer materials polyurethanes, polyesters, etc.
- metal nickel, copper, etc.
- inorganic substances calcium silicate, etc.
- the content of the curing agent is preferably in the following range with respect to 100 parts by mass of the anionic or cationic polymerizable component from the viewpoint of further improving the adhesion with the adherend. 10 mass parts or more are preferable, as for content of a hardening
- the adhesive composition of the present embodiment may contain a film forming material as necessary.
- Film-forming material improves the handling of the film under normal conditions (normal temperature and normal pressure) when the liquid adhesive composition is solidified into a film, and is difficult to tear, hard to break, and sticky Can be imparted to the film.
- the film forming material include phenoxy resin, polyvinyl formal, polystyrene, polyvinyl butyral, polyester, polyamide, xylene resin, and polyurethane.
- a phenoxy resin is preferable from the viewpoint of excellent adhesiveness, compatibility, heat resistance, and mechanical strength.
- a film forming material may be used individually by 1 type, and may be used in combination of 2 or more type.
- the phenoxy resin examples include a resin obtained by polyaddition of a bifunctional epoxy resin and a bifunctional phenol, and a resin obtained by reacting the bifunctional phenol and epihalohydrin until they are polymerized.
- the phenoxy resin contains 1 mol of a bifunctional phenol and 0.985 to 1.015 mol of epihalohydrin in the presence of a catalyst such as an alkali metal hydroxide at a temperature of 40 to 120 ° C. in a non-reactive solvent. It can be obtained by reacting.
- An organic solvent amide type, ether type, ketone type, lactone type, alcohol type
- a catalyst such as an alkali metal compound, an organic phosphorus type compound, a cyclic amine type compound, etc. Etc.
- a phenoxy resin may be used individually by 1 type, and may be used in combination of 2 or more type.
- bifunctional epoxy resin examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD type epoxy resin, bisphenol S type epoxy resin, biphenyl diglycidyl ether, methyl substituted biphenyl diglycidyl ether, and the like.
- Bifunctional phenols are compounds having two phenolic hydroxyl groups. Examples of the bifunctional phenols include hydroquinones, bisphenol A, bisphenol F, bisphenol AD, bisphenol S, bisphenol fluorene, methyl substituted bisphenol fluorene, dihydroxy biphenyl, and methyl substituted dihydroxy biphenyl.
- the phenoxy resin may be modified (for example, epoxy-modified) with a radical polymerizable functional group or other reactive compound.
- the content of the film forming material is preferably 10 to 90% by mass, more preferably 20 to 60% by mass, and more preferably 30 to 50% by mass based on the total amount of the adhesive component of the adhesive composition. More preferably it is.
- the adhesive composition of this embodiment may further contain conductive particles.
- conductive particles examples include gold (Au), silver (Ag), nickel (Ni), copper (Cu), metals such as solder, carbon, and the like.
- coated conductive particles in which a non-conductive resin, glass, ceramic, plastic, or the like is used as a core, and the metal (metal particles or the like) or carbon is coated on the core may be used. Since the coated conductive particles or the hot-melt metal particles are deformable by heating and pressing, the variation in the height of the circuit electrode is eliminated at the time of connection, and the contact area with the electrode is increased at the time of connection, thereby improving the reliability. Therefore, it is preferable.
- the average particle diameter of the conductive particles is preferably 1 to 50 ⁇ m, more preferably 2 to 30 ⁇ m, and further preferably 3 to 20 ⁇ m from the viewpoint of excellent dispersibility and conductivity.
- the average particle diameter of the conductive particles can be measured using instrumental analysis such as laser diffraction.
- the content of the conductive particles is preferably 0.1 part by volume or more, and more preferably 1 part by volume or more with respect to 100 parts by volume of the total volume of the adhesive component of the adhesive composition.
- the content of the conductive particles is preferably 50 parts by volume or less, more preferably 20 parts by volume or less, based on the total volume of the adhesive component of the adhesive composition, from the viewpoint of easily suppressing short-circuiting of electrodes (circuit electrodes, etc.).
- 10 parts by volume or less is more preferable, 5 parts by volume or less is particularly preferable, and 3 parts by volume or less is extremely preferable.
- the content of the conductive particles is preferably 0.1 to 50 parts by volume, more preferably 0.1 to 20 parts by volume, still more preferably 1 to 20 parts by volume, and particularly preferably 1 to 10 parts by volume. 1 to 5 parts by volume is very preferable, and 1 to 3 parts by volume is very preferable.
- the “volume part” is determined based on the volume of each component before curing at 23 ° C., and the volume of each component can be converted from mass to volume using specific gravity.
- the volume of the target component is increased by adding the target component to a container in which a suitable solvent (water, alcohol, etc.) that does not dissolve or swell the target component and wets the target component well is placed in a graduated cylinder. Can also be sought.
- the adhesive composition of this embodiment is a homopolymer or copolymer obtained by polymerizing at least one monomer component selected from the group consisting of (meth) acrylic acid, (meth) acrylic acid ester and acrylonitrile. Furthermore, you may contain.
- the adhesive composition of the present embodiment preferably contains acrylic rubber or the like, which is a copolymer obtained by polymerizing glycidyl (meth) acrylate having a glycidyl ether group, from the viewpoint of excellent stress relaxation.
- the weight average molecular weight of the acrylic rubber is preferably 200,000 or more from the viewpoint of increasing the cohesive strength of the adhesive composition.
- the content of the acrylic rubber is preferably 1 to 60% by mass, more preferably 10 to 50% by mass, and more preferably 20 to 40% by mass based on the total amount of the adhesive component of the adhesive composition. More preferably.
- the adhesive composition of the present embodiment may contain coated fine particles obtained by coating the surfaces of the conductive particles with a polymer resin or the like.
- coated fine particles obtained by coating the surfaces of the conductive particles with a polymer resin or the like.
- the coated fine particles may be used alone without using conductive particles, or the coated fine particles and conductive particles may be used in combination.
- the “adhesive component of the adhesive composition” in the present specification means a solid content other than the conductive particles and the coated fine particles in the adhesive composition.
- the adhesive composition of the present embodiment can also contain rubber fine particles, fillers (silica particles, etc.), softeners, accelerators, anti-aging agents, colorants, flame retardants, thixotropic agents, and the like.
- the adhesive composition of this embodiment may contain additives, such as a thickener, a leveling agent, and a weather resistance improver, as appropriate.
- the rubber fine particles have an average particle size not more than twice the average particle size of the conductive particles, and the storage elastic modulus at normal temperature is 1/2 of the storage elastic modulus at normal temperature of the conductive particles and the adhesive composition.
- the following particles are preferred.
- the rubber fine particles are made of silicone, acrylic emulsion, SBR (Styrene-Butadiene Rubber), NBR (Nitril-Butadiene Rubber) or polybutadiene rubber
- the rubber fine particles may be used alone or in combination of two or more. Is preferred.
- the three-dimensionally cross-linked rubber fine particles have excellent solvent resistance and are easily dispersed in the adhesive composition.
- the filler can improve the electrical characteristics (connection reliability, etc.) between the circuit electrodes.
- the filler for example, particles having an average particle size of 1/2 or less of the average particle size of the conductive particles can be suitably used.
- particles having no conductivity are used in combination with a filler, particles having an average particle size not more than the particles having no conductivity can be used as the filler.
- the content of the filler is preferably 0.1 to 60% by mass based on the total amount of the adhesive component of the adhesive composition. When the content is 60% by mass or less, the effect of improving connection reliability tends to be obtained more sufficiently. When the content is 0.1% by mass or more, the effect of adding the filler tends to be sufficiently obtained.
- the adhesive composition of this embodiment can be used in the form of a paste when it is liquid at room temperature.
- the adhesive composition When the adhesive composition is solid at room temperature, it may be heated and used, or may be made into a paste using a solvent.
- the solvent that can be used is not particularly limited as long as it is not reactive with the components in the adhesive composition and exhibits sufficient solubility.
- the solvent is preferably a solvent having a boiling point of 50 to 150 ° C. at normal pressure. When the boiling point is 50 ° C. or higher, the solvent is poorly volatile at room temperature, and can be used even in an open system. When the boiling point is 150 ° C. or lower, it is easy to volatilize the solvent, and thus good reliability can be obtained after bonding.
- the adhesive composition of the present embodiment may be in the form of a film. If necessary, an adhesive composition containing a solvent or the like is applied onto a fluororesin film, a polyethylene terephthalate film, a peelable substrate (release paper, etc.), and then the solvent is removed to remove the solvent. A composition can be obtained. Moreover, after impregnating base materials, such as a nonwoven fabric, with the said solution and mounting on a peelable base material, a film-form adhesive composition can be obtained by removing a solvent etc. When the adhesive composition is used in the form of a film, the handleability is excellent.
- the adhesive composition of this embodiment can be adhered by applying pressure together with heating or light irradiation. By using heating and light irradiation in combination, it can be bonded at a lower temperature in a shorter time.
- the light irradiation is preferably performed in the wavelength region of 150 to 750 nm.
- As the light source a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp (extra-high-pressure mercury lamp, etc.), a xenon lamp, a metal halide lamp, or the like can be used.
- the irradiation dose may be 0.1-10 J / cm 2 .
- the heating temperature is not particularly limited, but a temperature of 50 to 170 ° C. is preferable.
- the pressure is not particularly limited as long as it does not damage the adherend, but is preferably 0.1 to 10 MPa. Heating and pressurization are preferably performed in the range of 0.5 seconds to 3 hours.
- the adhesive composition of the present embodiment may be used as an adhesive for the same type of adherend, or as an adhesive for different types of adherends having different thermal expansion coefficients.
- circuit connection materials typified by anisotropic conductive adhesive, silver paste, silver film, etc .; CSP (Chip Size Package) elastomer, CSP underfill material, LOC (Lead on Chip) tape, etc. It can be used as a semiconductor element adhesive material.
- the structure of this embodiment includes the adhesive composition of this embodiment or a cured product thereof.
- the structure of this embodiment is a semiconductor device such as a circuit connection structure.
- the circuit connection structure includes a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, and a first circuit member. And a circuit connecting member disposed between the second circuit members.
- the first circuit member includes, for example, a first substrate and a first circuit electrode disposed on the first substrate.
- the second circuit member includes, for example, a second substrate and a second circuit electrode disposed on the second substrate. The first circuit electrode and the second circuit electrode face each other and are electrically connected.
- the circuit connection member includes the adhesive composition of the present embodiment or a cured product thereof.
- the structure which concerns on this embodiment should just be equipped with the adhesive composition which concerns on this embodiment, or its hardened
- the structure manufacturing method of the present embodiment includes a step of curing the adhesive composition of the present embodiment.
- the circuit connection structure manufacturing method includes a first circuit member having a first circuit electrode, and a second circuit member having a second circuit electrode. Between the step of arranging the adhesive composition of the present embodiment, and pressurizing the first circuit member and the second circuit member to electrically connect the first circuit electrode and the second circuit electrode. And a heating and pressing step of heating and curing the adhesive composition. In the arranging step, the first circuit electrode and the second circuit electrode can be arranged to face each other. In the heating and pressurizing step, the first circuit member and the second circuit member can be pressurized in the opposite directions.
- FIG. 1 is a schematic cross-sectional view showing an embodiment of a structure.
- a circuit connection structure 100 a shown in FIG. 1 includes a circuit member (first circuit member) 20 and a circuit member (second circuit member) 30 that are opposed to each other, and between the circuit member 20 and the circuit member 30.
- the circuit connection member 10 which connects these is arrange
- the circuit connection member 10 includes a cured product of the adhesive composition of the present embodiment.
- the circuit member 20 includes a substrate (first substrate) 21 and a circuit electrode (first circuit electrode) 22 disposed on the main surface 21 a of the substrate 21.
- An insulating layer (not shown) may be disposed on the main surface 21a of the substrate 21 as the case may be.
- the circuit member 30 includes a substrate (second substrate) 31 and a circuit electrode (second circuit electrode) 32 disposed on the main surface 31 a of the substrate 31.
- An insulating layer (not shown) may be disposed on the main surface 31a of the substrate 31 in some cases.
- the circuit connecting member 10 contains an insulating substance (cured product of components excluding conductive particles) 10a and conductive particles 10b.
- the conductive particles 10b are disposed at least between the circuit electrode 22 and the circuit electrode 32 facing each other. In the circuit connection structure 100a, the circuit electrode 22 and the circuit electrode 32 are electrically connected via the conductive particles 10b.
- the circuit members 20 and 30 have one or a plurality of circuit electrodes (connection terminals).
- a chip component such as a semiconductor chip (IC chip), a resistor chip, or a capacitor chip; a substrate such as a printed board or a semiconductor mounting board can be used.
- Examples of the combination of the circuit members 20 and 30 include a semiconductor chip and a semiconductor mounting substrate.
- the material of the substrate include inorganic substances such as semiconductor, glass, and ceramic; organic substances such as polyimide, polyethylene terephthalate, polycarbonate, (meth) acrylic resin, and cyclic olefin resin; and composites of glass and epoxy.
- the substrate may be a plastic substrate.
- FIG. 2 is a schematic cross-sectional view showing another embodiment of the structure.
- the circuit connection structure 100b shown in FIG. 2 has the same configuration as the circuit connection structure 100a except that the circuit connection member 10 does not contain the conductive particles 10b.
- the circuit electrode 22 and the circuit electrode 32 are in direct contact and are electrically connected without interposing conductive particles.
- the circuit connection structures 100a and 100b can be manufactured, for example, by the following method. First, when the adhesive composition is in a paste form, the resin layer containing the adhesive composition is disposed on the circuit member 20 by applying and drying the adhesive composition. When the adhesive composition is in the form of a film, the resin layer containing the adhesive composition is disposed on the circuit member 20 by sticking the film-like adhesive composition to the circuit member 20. Subsequently, the circuit member 30 is placed on the resin layer disposed on the circuit member 20 so that the circuit electrode 22 and the circuit electrode 32 are opposed to each other. And a heat treatment or light irradiation is performed to the resin layer containing an adhesive composition, an adhesive composition hardens
- Examples 1 to 14 and Comparative Examples 1 to 11 (Preparation of conductive particles) A nickel layer having a thickness of 0.2 ⁇ m was formed on the surface of the polystyrene particles. Further, a gold layer having a thickness of 0.04 ⁇ m was formed outside the nickel layer. Thereby, conductive particles having an average particle diameter of 4 ⁇ m were produced.
- Phenoxy resin PKHC (Union Carbide Co., Ltd., trade name, weight average molecular weight 45,000) was used in the form of a solution having a solid content of 40% by mass prepared by dissolving 60 g of methyl ethyl ketone.
- Acrylic rubber An acrylic rubber (a copolymer of 40 parts by weight of butyl acrylate, 30 parts by weight of ethyl acrylate, 30 parts by weight of acrylonitrile, 3 parts by weight of glycidyl methacrylate, and a weight average molecular weight of 800,000) is prepared as a rubber component.
- Curing agent-containing epoxy resin A microcapsule-type latent curing agent (a microencapsulated amine-based curing agent), a bisphenol F-type epoxy resin, and a naphthalene-type epoxy resin are contained at a mass ratio of 34:49:17.
- a liquid curing agent-containing epoxy resin (epoxy equivalent: 202) was used.
- Silane compound A1 3-glycidoxypropylmethyldimethoxysilane (trade name: KBM-402, manufactured by Shin-Etsu Chemical Co., Ltd.) was used.
- Silane compound A2 3-glycidoxypropyltrimethoxysilane (trade name: KBM-403, manufactured by Shin-Etsu Chemical Co., Ltd.) was used.
- Silane compound A3 3-glycidoxypropylmethyldiethoxysilane (trade name: KBE-402, manufactured by Shin-Etsu Chemical Co., Ltd.) was used.
- Silane compound A4 3-glycidoxypropyltriethoxysilane (trade name: KBE-403, manufactured by Shin-Etsu Chemical Co., Ltd.) was used.
- Silane compound B1 Methyltrimethoxysilane (trade name: KBM-13, manufactured by Shin-Etsu Chemical Co., Ltd.) was used.
- Silane compound B2 3-methacryloxypropyltrimethoxysilane (trade name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.) was used.
- Silane compound B3 Tetraethoxysilane (trade name: KBE-04, manufactured by Shin-Etsu Chemical Co., Ltd.) was used.
- the substrate and a SiN x substrate (thickness 0.7 mm) having a thin layer of 0.2 ⁇ m thick silicon nitride (SiN x ) formed on the glass substrate were connected.
- the connection was performed by heating and pressurizing at 200 ° C. and 5 MPa for 15 seconds using a thermocompression bonding apparatus (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.).
- connection body in which the FPC and the SiN x substrate were connected by the cured product of the film adhesive over a width of 1.5 mm was produced.
- the pressure of the pressurization was calculated with the crimping area as 0.495 cm 2 .
- connection evaluation After the connection body was left in a constant temperature and humidity chamber at 85 ° C. and 85% RH for 250 hours (after the high temperature and high humidity test), the connection appearance was observed using an optical microscope. The area (peeling area) where peeling occurred at the interface between the SiN x substrate and the cured product in the space was measured, and the presence or absence of peeling was evaluated. The case where the ratio of the peeled area occupying the entire space exceeded 30% was evaluated as “B” (with peeling), and the case where the peeled area ratio was 30% or less was evaluated as “A” (without peeling). This evaluation result is shown in Table 1 and Table 2 as the peel evaluation result of the untreated film.
- the film-like adhesives of the examples are connected to the film-like adhesives after being treated in a constant temperature bath at 40 ° C. for 3 days as compared with the film-like adhesives of the comparative examples. It was confirmed that the adhesiveness to the surface of the substrate (inorganic substrate) can be kept good even when the substrate is processed at high temperature and high humidity, and that the storage stability is excellent.
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Abstract
Description
本実施形態の接着剤組成物は、アニオン重合又はカチオン重合可能なエポキシ樹脂又はオキセタン樹脂(アニオン又はカチオン重合性物質)と、上記エポキシ樹脂又はオキセタン樹脂と反応する官能基を有する第1のシラン化合物と、上記第1のシラン化合物と反応する第2のシラン化合物と、を含有する。本実施形態の接着剤組成物は、シラン化合物として、エポキシ樹脂又はオキセタン樹脂と反応する官能基(アニオン又はカチオン硬化系の重合反応に関与する官能基。アニオン又はカチオン重合系においてエポキシ樹脂又はオキセタン樹脂と反応し得る官能基)を有する第1のシラン化合物と、上記第1のシラン化合物と反応する第2のシラン化合物(上記第1のシラン化合物に該当する化合物を除く)とを含有する。本実施形態の接着剤組成物は、アニオン又はカチオン硬化系(アニオン重合系又はカチオン重合系)の接着剤組成物である。本実施形態の接着剤組成物は、回路接続用接着剤組成物として好適に用いることができる。以下、各成分について説明する。
本実施形態の接着剤組成物は、アニオン又はカチオン重合系においてエポキシ樹脂又はオキセタン樹脂と反応する官能基を有する第1のシラン化合物と、上記第1のシラン化合物と反応する第2のシラン化合物とを含有する。第2のシラン化合物は、第1のシラン化合物に該当しない化合物であり、アニオン又はカチオン重合系においてエポキシ樹脂又はオキセタン樹脂と反応する官能基を有していない。シラン化合物は、シランカップリング剤であってもよい。例えば、第1及び第2のシラン化合物の両方がシランカップリング剤である場合、第2のシラン化合物は、アルコキシシリル基の加水分解・縮合反応により、第1のシラン化合物と反応することができる。
アニオン又はカチオン重合性成分であるアニオン重合又はカチオン重合可能なエポキシ樹脂としては、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、ナフタレン型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビスフェノールAノボラック型エポキシ樹脂、ビスフェノールFノボラック型エポキシ樹脂、脂環式エポキシ樹脂、グリシジルエステル型エポキシ樹脂、グリシジルアミン型エポキシ樹脂、ヒダントイン型エポキシ樹脂、イソシアヌレート型エポキシ樹脂、脂肪族鎖状エポキシ樹脂等が挙げられる。また、アニオン又はカチオン重合性成分であるアニオン重合又はカチオン重合可能なオキセタン樹脂としては、3-エチル-3-ヒドロキシメチルオキセタン、2-エチルヘキシルオキセタン、キシリレンビスオキセタン、3-エチル-3{[(3-エチルオキセタン-3-イル)メトキシ]メチル}オキセタン、3-エチルオキセタン-3-イル)メチルアクリレート、(3-エチルオキセタン-3-イル)メチルメタクリレート等が挙げられる。アニオン又はカチオン重合性成分は、ハロゲン化されていてもよく、水素添加されていてもよい。アニオン又はカチオン重合性成分は、1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本実施形態の接着剤組成物は、硬化剤を更に含んでいてもよい。硬化剤としては、アニオン重合又はカチオン重合可能なエポキシ樹脂又はオキセタン樹脂を硬化させることができるものであれば特に限定されない。硬化剤としては、熱又は光によりアニオン種を発生することができる硬化剤(アニオン重合性の触媒型硬化剤等)、熱又は光によりカチオン種を発生することができる硬化剤(カチオン重合性の触媒型硬化剤等)、重付加型の硬化剤などが挙げられる。硬化剤は、1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。硬化剤は、速硬化性に優れ、且つ、化学当量的な考慮が不要である観点から、熱又は光によりアニオン種又はカチオン種を発生することができる硬化剤が好ましく、アニオン重合性又はカチオン重合性の触媒型硬化剤がより好ましい。
本実施形態の接着剤組成物は、必要に応じて、フィルム形成材を含有してもよい。フィルム形成材は、液状の接着剤組成物をフィルム状に固形化した場合に、通常の状態(常温常圧)でのフィルムの取扱い性を向上させ、裂け難い、割れ難い、べたつき難い等の特性をフィルムに付与することができる。フィルム形成材としては、フェノキシ樹脂、ポリビニルホルマール、ポリスチレン、ポリビニルブチラール、ポリエステル、ポリアミド、キシレン樹脂、ポリウレタン等が挙げられる。これらの中でも、接着性、相溶性、耐熱性及び機械的強度に優れる観点から、フェノキシ樹脂が好ましい。フィルム形成材は、1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本実施形態の接着剤組成物は、導電粒子を更に含有していてもよい。導電粒子の構成材料としては、金(Au)、銀(Ag)、ニッケル(Ni)、銅(Cu)、はんだ等の金属、カーボンなどが挙げられる。また、非導電性の樹脂、ガラス、セラミック、プラスチック等を核とし、この核に上記金属(金属粒子等)又はカーボンを被覆した被覆導電粒子でもよい。被覆導電粒子又は熱溶融金属粒子は、加熱加圧により変形性を有するため、接続時に回路電極の高さのばらつきを解消し、接続時に電極との接触面積が増加することから信頼性が向上するため好ましい。
本実施形態の接着剤組成物は、(メタ)アクリル酸、(メタ)アクリル酸エステル及びアクリロニトリルからなる群より選ばれる少なくとも1種のモノマー成分を重合させて得られる単独重合体又は共重合体を更に含有していてもよい。本実施形態の接着剤組成物は、応力緩和に優れる観点から、グリシジルエーテル基を有するグリシジル(メタ)アクリレートを重合させて得られる共重合体であるアクリルゴム等を含有することが好ましい。上記アクリルゴムの重量平均分子量は、接着剤組成物の凝集力を高める観点から、20万以上が好ましい。アクリルゴムの含有量は、接着剤組成物の接着剤成分全量を基準として、1~60質量%であることが好ましく、10~50質量%であることがより好ましく、20~40質量%であることが更に好ましい。
本実施形態の構造体は、本実施形態の接着剤組成物又はその硬化物を備える。本実施形態の構造体は、例えば、回路接続構造体等の半導体装置である。本実施形態の構造体の一態様として、回路接続構造体は、第一の回路電極を有する第一の回路部材と、第二の回路電極を有する第二の回路部材と、第一の回路部材及び第二の回路部材の間に配置された回路接続部材と、を備える。第一の回路部材は、例えば、第一の基板と、当該第一の基板上に配置された第一の回路電極と、を有する。第二の回路部材は、例えば、第二の基板と、当該第二の基板上に配置された第二の回路電極と、を有する。第一の回路電極及び第二の回路電極は、相対向すると共に電気的に接続されている。回路接続部材は、本実施形態の接着剤組成物又はその硬化物を含んでいる。本実施形態に係る構造体は、本実施形態に係る接着剤組成物又はその硬化物を備えていればよく、上記回路接続構造体の回路部材に代えて、回路電極を有していない部材(基板等)を用いてもよい。
(導電粒子の作製)
ポリスチレン粒子の表面に厚さ0.2μmのニッケル層を形成した。更に、このニッケル層の外側に厚さ0.04μmの金層を形成させた。これにより、平均粒径4μmの導電粒子を作製した。
表1及び表2に示す成分を、表1及び表2に示す質量比(固形分)で混合して混合物を得た。この混合物に上記導電粒子を1.5体積部の割合(基準:接着剤組成物の接着剤成分の全体積100体積部に対する割合)で分散させて、フィルム状接着剤を形成するための塗工液を得た。この塗工液を厚さ50μmのポリエチレンテレフタレート(PET)フィルムに、塗工装置を用いて塗布した。塗膜を70℃で10分熱風乾燥して、厚さ18μmの実施例1~14及び比較例1~11のフィルム状接着剤を形成させた。
フェノキシ樹脂:PKHC(ユニオンカーバイド株式会社製、商品名、重量平均分子量45000)40gをメチルエチルケトン60gに溶解して調製した固形分40質量%の溶液の形態で用いた。
アクリルゴム:ゴム成分としてアクリルゴム(ブチルアクリレート40質量部-エチルアクリレート30質量部-アクリロニトリル30質量部-グリシジルメタクリレート3質量部の共重合体、重量平均分子量80万)を用意し、このアクリルゴムをトルエン/酢酸エチル=50/50(質量比)の混合溶剤に溶解して調製した固形分15質量%の溶液の形態で用いた。
硬化剤含有エポキシ樹脂:マイクロカプセル型潜在性硬化剤(マイクロカプセル化されたアミン系硬化剤)と、ビスフェノールF型エポキシ樹脂と、ナフタレン型エポキシ樹脂とを、質量比34:49:17で含有する液状の硬化剤含有エポキシ樹脂(エポキシ当量:202)を用いた。
シラン化合物A1:3-グリシドキシプロピルメチルジメトキシシラン(商品名:KBM-402、信越化学工業株式会社製)を用いた。
シラン化合物A2:3-グリシドキシプロピルトリメトキシシラン(商品名:KBM-403、信越化学工業株式会社製)を用いた。
シラン化合物A3:3-グリシドキシプロピルメチルジエトキシシラン(商品名:KBE-402、信越化学工業株式会社製)を用いた。
シラン化合物A4:3-グリシドキシプロピルトリエトキシシラン(商品名:KBE-403、信越化学工業株式会社製)を用いた。
シラン化合物B1:メチルトリメトキシシラン(商品名:KBM-13、信越化学工業株式会社製)を用いた。
シラン化合物B2:3-メタクリロキシプロピルトリメトキシシラン(商品名:KBM-503、信越化学工業株式会社製)を用いた。
シラン化合物B3:テトラエトキシシラン(商品名:KBE-04、信越化学工業株式会社製)を用いた。
実施例1~14及び比較例1~11のフィルム状接着剤を用いて、ライン幅75μm、ピッチ150μm(スペース75μm)及び厚さ18μmの銅回路を2200本有するフレキシブル回路基板(FPC)と、ガラス基板、及び、ガラス基板上に形成された厚さ0.2μmの窒化珪素(SiNx)の薄層を有するSiNx基板(厚さ0.7mm)とを接続した。接続は、熱圧着装置(加熱方式:コンスタントヒート型、東レエンジニアリング株式会社製)を用い、200℃、5MPaで15秒間の加熱及び加圧により行った。これにより、幅1.5mmにわたりFPCとSiNx基板とがフィルム状接着剤の硬化物により接続された接続体を作製した。加圧の圧力は、圧着面積を0.495cm2として計算した。
上記接続体を85℃、85%RHの恒温恒湿槽中に250時間放置した後(高温高湿試験後)の接続外観を、光学顕微鏡を用いて観察した。スペース部分におけるSiNx基板と硬化物との界面において剥離が発生している面積(剥離面積)を測定し、剥離の有無を評価した。スペース全体に占める剥離面積の割合が30%を超える場合を「B」(剥離有り)と評価し、剥離面積の割合が30%以下の場合を「A」(剥離なし)と評価した。この評価結果を、未処理フィルムの剥離評価結果として表1及び表2に示す。
上記フィルム状接着剤を40℃の恒温槽にて3日処理した。このフィルム状接着剤を用いて、上記と同様の方法で接続体を作製した後、上記と同様の方法で高温高湿試験を行い、剥離評価を行った。この評価結果を、40℃3日処理フィルムの剥離評価結果として表1及び表2に示す。
Claims (7)
- アニオン重合又はカチオン重合可能なエポキシ樹脂又はオキセタン樹脂と、
前記エポキシ樹脂又はオキセタン樹脂と反応する官能基を有する第1のシラン化合物と、
前記第1のシラン化合物と反応する第2のシラン化合物と、
を含有する、接着剤組成物。 - 前記第1のシラン化合物の前記官能基が、エポキシ基、オキセタン基、アミノ基、酸無水物基、イソシアネート基、及びメルカプト基からなる群より選ばれる少なくとも1種を含む、請求項1に記載の接着剤組成物。
- 前記第2のシラン化合物が、アルキル基、フェニル基、アルコキシシリル基、水酸基、フッ素含有基、(メタ)アクリロイル基及びビニル基からなる群より選ばれる少なくとも1種を含む、請求項1又は2に記載の接着剤組成物。
- 導電粒子を更に含有する、請求項1~3のいずれか一項に記載の接着剤組成物。
- 回路接続用である、請求項1~4のいずれか一項に記載の接着剤組成物。
- 請求項1~5のいずれか一項に記載の接着剤組成物又はその硬化物を備える、構造体。
- 第一の回路電極を有する第一の回路部材と、
第二の回路電極を有する第二の回路部材と、
前記第一の回路部材及び前記第二の回路部材の間に配置された回路接続部材と、を備え、
前記第一の回路電極及び前記第二の回路電極が電気的に接続されており、
前記回路接続部材が、請求項1~5のいずれか一項に記載の接着剤組成物又はその硬化物を含む、構造体。
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