WO2023032723A1 - 硬化性樹脂組成物及び層間絶縁材料 - Google Patents
硬化性樹脂組成物及び層間絶縁材料 Download PDFInfo
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- WO2023032723A1 WO2023032723A1 PCT/JP2022/031479 JP2022031479W WO2023032723A1 WO 2023032723 A1 WO2023032723 A1 WO 2023032723A1 JP 2022031479 W JP2022031479 W JP 2022031479W WO 2023032723 A1 WO2023032723 A1 WO 2023032723A1
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- curable resin
- resin composition
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- 125000004427 diamine group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- ATJCASULPHYKHT-UHFFFAOYSA-N hexadecane-1,16-diamine Chemical compound NCCCCCCCCCCCCCCCCN ATJCASULPHYKHT-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- POIZGMCHYSVWDU-UHFFFAOYSA-N icosane-1,20-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCN POIZGMCHYSVWDU-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- ODZZIKZQNODXFS-UHFFFAOYSA-N n,n'-dimethyl-n'-[2-(methylamino)ethyl]ethane-1,2-diamine Chemical compound CNCCN(C)CCNC ODZZIKZQNODXFS-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- ZCIJAGHWGVCOHJ-UHFFFAOYSA-N naphthalene phenol Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)O ZCIJAGHWGVCOHJ-UHFFFAOYSA-N 0.000 description 1
- AJXNLGUENUIIRW-UHFFFAOYSA-N naphtho[2,3-f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C(C=C3C(=O)OC(=O)C3=C3)C3=CC2=C1 AJXNLGUENUIIRW-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- MFUFBSLEAGDECJ-UHFFFAOYSA-N pyren-2-ylamine Natural products C1=CC=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 MFUFBSLEAGDECJ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000009774 resonance method Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- MSVPBWBOFXVAJF-UHFFFAOYSA-N tetradecane-1,14-diamine Chemical compound NCCCCCCCCCCCCCCN MSVPBWBOFXVAJF-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
Definitions
- the present invention relates to a curable resin composition having excellent dielectric properties and adhesiveness after curing.
- the present invention also relates to an interlayer insulating material using the curable resin composition.
- Curable resins such as epoxy resins, which have low shrinkage and excellent adhesiveness, insulation, and chemical resistance, are used in many industrial products.
- dielectric properties such as a low dielectric constant and a low dielectric loss tangent are required for a curable resin composition used as an interlayer insulating material for printed wiring boards.
- Patent Documents 1 and 2 disclose a curable resin composition containing a curable resin and a compound having a specific structure as a curing agent. ing.
- An object of the present invention is to provide a curable resin composition that exhibits excellent dielectric properties and adhesion after curing. Another object of the present invention is to provide an interlayer insulating material using the curable resin composition.
- the present disclosure 1 contains a curable resin, a curing agent, an inorganic filler, and a dispersant, and has a complex viscosity of 8000 Pa s or less at 90 ° C., 5% strain, and 1 rad / sec. It is a thing.
- the present disclosure 2 is the curable resin composition of the present disclosure 1, wherein the inorganic filler is silica.
- Present Disclosure 3 is the curable resin composition of Present Disclosure 1 or 2, wherein the content of the inorganic filler in 100 parts by weight of the total solid content of the curable resin composition is 65 parts by weight or more.
- the present disclosure 4 is the curable resin composition of the present disclosure 1, 2 or 3, wherein the dispersant is a polyurethane-based dispersant.
- Disclosure 5 is the curable resin composition of Disclosure 1, 2, 3 or 4, further comprising a polymer component.
- the present disclosure 6 is an interlayer insulating material using the curable resin composition of the present disclosure 1, 2, 3, 4 or 5. The present invention will
- the present inventors have found that the cause of peeling on the adherend when a large amount of inorganic filler is blended is that the dispersion state of the inorganic filler in the curable resin composition becomes uneven. It was thought that this was due to the fact that slight unevenness occurred on the surface of the Therefore, the present inventors have studied adjusting the melt viscosity of the curable resin composition, but the peeling of the adherend could not be sufficiently suppressed even if the melt viscosity is lowered. Therefore, the present inventors have investigated to make the complex viscosity of the curable resin composition at 90° C., 5% strain, 1 rad/sec to be a specific value or less. As a result, the inorganic filler in the resulting curable resin composition can be uniformly dispersed, and a cured product having excellent dielectric properties and adhesiveness can be obtained. This led to the completion of the present invention. rice field.
- the curable resin composition of the present invention has an upper limit of complex viscosity of 8000 Pa ⁇ s at 90° C., strain of 5%, and 1 rad/sec.
- the complex viscosity at 90° C., 5% strain, and 1 rad/sec is 8000 Pa s or less
- the curable resin composition of the present invention has a uniform dispersion state of the inorganic filler and adhesion after curing. It will be excellent in quality.
- a preferable upper limit of the complex viscosity at 90° C., 5% strain, and 1 rad/sec is 7500 Pa ⁇ s, and a more preferable upper limit is 7000 Pa ⁇ s.
- the complex viscosity at 90° C., 5% strain, and 1 rad/sec can be measured using a rotary rheometer at a frequency of 0.01 Hz to 1 Hz and 90° C. for the curable resin composition film. can.
- the curable resin composition film can be obtained by applying the curable resin composition onto a base film and drying the coating.
- the rotational rheometer include HAAKE MARS series (manufactured by Thermo Fisher Scientific), VAR-100 (manufactured by Rheologicala), and ARES (manufactured by TA Instruments).
- the curable resin composition of the present invention contains a curable resin.
- the curable resins include epoxy resins, cyanate resins, phenol resins, imide resins, maleimide resins, silicone resins, acrylic resins, and fluorine resins.
- the curable resin preferably contains at least one selected from the group consisting of epoxy resins, cyanate resins, phenol resins, imide resins, and maleimide resins, and more preferably contains epoxy resins.
- the curable resins may be used alone, or two or more of them may be used in combination.
- the epoxy resin examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2,2'-diallylbisphenol A type epoxy resin, and hydrogenated bisphenol type epoxy resin. , propylene oxide-added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, fluorene type epoxy resin, naphthylene ether type epoxy resin, phenol novolak type epoxy resin, ortho-cresol novolak type epoxy resin, dicyclopentadiene novolak type epoxy resin, biphenyl novolak type epoxy resin, naphthalenephenol novolak type epoxy resin, glycidylamine type epoxy resin, alkyl polyol type epoxy resin, Examples include rubber-modified epoxy resins and glycidyl ester compounds.
- the curable resin composition of the present invention further contains a curing agent.
- the curing agent include an imide skeleton in the main chain and an imide oligomer having a crosslinkable functional group at the end, an acid anhydride-based curing agent, a phenol-based curing agent, a thiol-based curing agent, an amine-based curing agent, and a cyanate-based curing agent. curing agents, active ester curing agents, and the like.
- the curing agent preferably contains the imide oligomer from the viewpoint of the adhesiveness and long-term heat resistance of the cured product of the curable resin composition to be obtained.
- the imide oligomer is represented by the following formula (1-1) or the following formula (1-2), or the following formula (2-1) or the following formula (2-2) as a structure containing the crosslinkable functional group. It is preferred to have a structure that By having a structure represented by the following formula (1-1) or the following formula (1-2), or the following formula (2-1) or the following formula (2-2), the imide oligomer is an epoxy resin It becomes excellent in reactivity and compatibility with curable resins such as.
- A is an acid dianhydride residue
- B is an aliphatic diamine residue or an aromatic diamine residue
- Ar is an optionally substituted divalent aromatic group.
- A is an acid dianhydride residue
- B is an aliphatic triamine residue or an aromatic triamine residue
- Ar is an optionally substituted divalent aromatic group.
- the acid dianhydride residue is preferably a tetravalent group represented by the following formula (3-1) or the following formula (3-2).
- Z is a bond, an oxygen atom, a carbonyl group, a sulfur atom, a sulfonyl group, a direct It is a chain or branched divalent hydrocarbon group or a divalent group having an aromatic ring.
- Z is a hydrocarbon group, it may have an oxygen atom between the hydrocarbon group and each aromatic ring in formula (3-1), Z is a divalent group having an aromatic ring.
- an oxygen atom may be present between the divalent group having the aromatic ring and each aromatic ring in formula (3-1).
- the hydrogen atoms of the aromatic rings in formulas (3-1) and (3-2) may be substituted.
- Z in the above formula (3-1) is a linear or branched divalent hydrocarbon group or a divalent group having an aromatic ring
- these groups are substituted good too.
- substituents in the case where the linear or branched divalent hydrocarbon group or the divalent group having an aromatic ring is substituted include, for example, a halogen atom, a linear or branched chain linear alkyl groups, linear or branched alkenyl groups, alicyclic groups, aryl groups, alkoxy groups, nitro groups, cyano groups and the like.
- Examples of acid dianhydrides from which the acid dianhydride residue is derived include acid dianhydrides represented by formula (9) described later.
- a preferable lower limit of the number of carbon atoms of the aliphatic diamine residue and the aliphatic triamine residue when they are residues is 4. Since the number of carbon atoms in the aliphatic diamine residue and the aliphatic triamine residue is 4 or more, the resulting curable resin composition has flexibility and workability before curing, and dielectric properties after curing. It will be better. A more preferable lower limit for the number of carbon atoms in the aliphatic diamine residue and the aliphatic triamine residue is 5, and a more preferable lower limit is 6. Although there is no particular upper limit for the number of carbon atoms in the aliphatic diamine residue and the aliphatic triamine residue, the practical upper limit is 60.
- Examples of the aliphatic diamine from which the aliphatic diamine residue is derived include aliphatic diamines derived from dimer acid, linear or branched aliphatic diamines, aliphatic ether diamines, and aliphatic lipids. Cyclic diamines and the like can be mentioned. Examples of the aliphatic diamines derived from the above dimer acids include dimer diamines and hydrogenated dimer diamines.
- linear or branched aliphatic diamines examples include 1,4-butanediamine, 1,6-hexanediamine, 1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine, 1,14-tetradecanediamine, 1,16-hexadecanediamine, 1,18-octadecanediamine, 1,20-eicosanediamine, 2-methyl-1,8 -octanediamine, 2-methyl-1,9-nonanediamine, 2,7-dimethyl-1,8-octanediamine and the like.
- aliphatic ether diamines examples include 2,2'-oxybis(ethylamine), 3,3'-oxybis(propylamine), 1,2-bis(2-aminoethoxy)ethane and the like.
- aliphatic alicyclic diamines examples include 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, cyclohexanediamine, methylcyclohexanediamine, and isophoronediamine.
- the aliphatic diamine residue is preferably an aliphatic diamine residue derived from the dimer acid.
- aliphatic triamines from which the above-mentioned aliphatic triamine residues are derived include aliphatic triamines derived from trimer acid, linear or branched aliphatic triamines, aliphatic ether triamines, and aliphatic lipids. Cyclic triamines and the like can be mentioned. Examples of aliphatic triamines derived from trimer acids include trimer triamines and hydrogenated trimer triamines.
- linear or branched aliphatic triamines examples include 3,3′-diamino-N-methyldipropylamine, 3,3′-diaminodipropylamine, diethylenetriamine, bis(hexamethylene)triamine, 2 , 2′-bis(methylamino)-N-methyldiethylamine and the like.
- the aliphatic triamine residue is preferably an aliphatic triamine residue derived from the trimer acid.
- a mixture of the dimer diamine and the trimer triamine can also be used as the aliphatic diamine and/or the aliphatic triamine.
- aliphatic diamines and/or aliphatic triamines derived from the dimer acid and/or the trimer acid include, for example, aliphatic diamines and/or triamines manufactured by BASF, and fatty acids manufactured by Croda. triamines and/or aliphatic triamines. Examples of the aliphatic diamines and/or aliphatic triamines manufactured by BASF include Versamin 551 and Versamin 552. Examples of the aliphatic diamines and/or aliphatic triamines manufactured by Croda include Priamine 1071, Priamine 1073, Priamine 1074, and Priamine 1075.
- the aromatic when B in the above formula (1-1), the above formula (1-2), the above formula (2-1), or the above formula (2-2) is the above aromatic diamine residue
- the diamine residue is preferably a divalent group represented by formula (4-1) or formula (4-2) below.
- Y is a bond, an oxygen atom, a carbonyl group, a sulfur atom, a sulfonyl group, a straight It is a chain or branched divalent hydrocarbon group or a divalent group having an aromatic ring.
- Y is a hydrocarbon group, it may have an oxygen atom between the hydrocarbon group and each aromatic ring in formula (4-1), Y is a divalent group having an aromatic ring.
- an oxygen atom may be present between the divalent group having the aromatic ring and each aromatic ring in formula (4-1).
- the hydrogen atoms of the aromatic rings in formulas (4-1) and (4-2) may be substituted.
- Y in the above formula (4-1) is a linear or branched divalent hydrocarbon group or a divalent group having an aromatic ring
- substituents in the case where the linear or branched divalent hydrocarbon group or the divalent group having an aromatic ring is substituted include, for example, a halogen atom, a linear or branched chain linear alkyl groups, linear or branched alkenyl groups, alicyclic groups, aryl groups, alkoxy groups, nitro groups, cyano groups and the like.
- aromatic diamine from which the aromatic diamine residue is derived examples include those in which the diamine represented by formula (10) described below is an aromatic diamine.
- the imide oligomer when it has a siloxane skeleton in its structure, it may lower the glass transition temperature after curing, contaminate the adherend, and cause poor adhesion. , preferably an imide oligomer having no siloxane skeleton in its structure.
- the imide oligomer preferably has a number average molecular weight of 5,000 or less.
- the imide oligomer has a number average molecular weight of 5,000 or less, the resulting cured product of the curable resin composition is excellent in long-term heat resistance.
- a more preferable upper limit of the number average molecular weight of the imide oligomer is 4,000, and a more preferable upper limit is 3,000.
- the number average molecular weight of the imide oligomer is preferably 900 or more and 5000 or less when it has a structure represented by the above formula (1-1) or (2-1), and the above formula (1- 2) When it has a structure represented by the above formula (2-2), it is preferably 550 or more and 4000 or less.
- a more preferable lower limit of the number average molecular weight is 950, and a more preferable lower limit is 1,000 in the case of having a structure represented by the above formula (1-1) or the above formula (2-1).
- a more preferable lower limit of the number average molecular weight is 580, and a more preferable lower limit is 600, in the case of having a structure represented by the formula (1-2) or (2-2).
- the above-mentioned "number average molecular weight" in this specification is a value measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent and calculated by polystyrene conversion. Examples of the column used for measuring the polystyrene-equivalent number-average molecular weight by GPC include JAIGEL-2H-A (manufactured by Japan Analytical Industry Co., Ltd.).
- the imide oligomer is represented by the following formula (5-1), the following formula (5-2), the following formula (5-3), the following formula (5-4), or the following formula (5-5 ), or the following formula (6-1), the following formula (6-2), the following formula (6-3), the following formula (6-4), or the following formula (6-5 ) is preferably an imide oligomer represented by
- A is the acid dianhydride residue
- B is the aliphatic diamine residue or the aromatic diamine residue, or the aliphatic triamine residue or the aromatic triamine residue
- X is a hydrogen atom, a halogen atom, or an optionally substituted monovalent hydrocarbon group
- W is a hydrogen atom, a halogen atom , or an optionally substituted monovalent hydrocarbon group.
- n is the number of repetitions.
- A is the acid dianhydride residue, and in formulas (6-1) to (6-5), A is the same. may be different.
- R is a hydrogen atom, a halogen atom, or an optionally substituted monovalent hydrocarbon group, formula (6-1), formula (6 -3) and in formula (6-5), R may be the same or different.
- W is a hydrogen atom, a halogen atom, or an optionally substituted monovalent hydrocarbon group.
- B is the aliphatic diamine residue or the aromatic diamine residue, or the aliphatic triamine residue or the aromatic triamine residue, In (6-3) and formula (6-4), B may be the same or different.
- a in the above formulas (5-1) to (5-5) and the above formulas (6-1) to (6-5) is the following formula (7-1) or the following formula (7-2) It is preferably a tetravalent group represented.
- Z is a bond, an oxygen atom, a carbonyl group, a sulfur atom, a sulfonyl group, a direct It is a chain or branched divalent hydrocarbon group or a divalent group having an aromatic ring.
- Z is a hydrocarbon group, it may have an oxygen atom between the hydrocarbon group and each aromatic ring in formula (7-1), Z is a divalent group having an aromatic ring.
- an oxygen atom may be present between the divalent group having an aromatic ring and each aromatic ring in formula (7-1).
- the hydrogen atoms of the aromatic rings in formulas (7-1) and (7-2) may be substituted.
- Y is a bond, an oxygen atom, a carbonyl group, a sulfur atom, a sulfonyl group, a straight It is a chain or branched divalent hydrocarbon group or a divalent group having an aromatic ring.
- Y is a hydrocarbon group, it may have an oxygen atom between the hydrocarbon group and each aromatic ring in formula (8-1), Y is a divalent group having an aromatic ring.
- an oxygen atom may be present between the divalent group having an aromatic ring and each aromatic ring in formula (8-1).
- the hydrogen atoms of the aromatic rings in formulas (8-1) and (8-2) may be substituted.
- an imide oligomer having a structure represented by the above formula (1-1) for example, an acid dianhydride represented by the following formula (9) and a diamine represented by the following formula (10) and the like. Also, by using an aliphatic triamine or an aromatic triamine instead of the diamine represented by the following formula (10), an imide oligomer having a structure represented by the above formula (2-1) can be produced.
- A is the same tetravalent group as A in formula (1-1) above.
- B is the same divalent group as B in formula (1-1) above, and R 1 to R 4 are each independently a hydrogen atom or a monovalent hydrocarbon group. .
- a specific example of the method for reacting the acid dianhydride represented by the above formula (9) with the diamine represented by the above formula (10) is shown below.
- the diamine represented by the above formula (10) is dissolved in advance in a solvent (for example, N-methylpyrrolidone, etc.) in which the amic acid oligomer obtained by the reaction is soluble, and the resulting solution is added with the above formula (9).
- An acid dianhydride represented by is added and reacted to obtain an amic acid oligomer solution.
- the solvent is removed by heating, pressure reduction, or the like, and the mixture is heated at about 200° C. or higher for 1 hour or longer to react the amic acid oligomer.
- the acid dianhydride represented by the above formula (9) and the acid anhydride represented by the following formula (11) may be added simultaneously or separately. Furthermore, by replacing part of the diamine represented by the above formula (10) with a monoamine represented by the following formula (12), it has a desired number average molecular weight, and one end has the above formula (1-1) ) and having at the other end a structure derived from a monoamine represented by the following formula (12). In this case, the diamine represented by the above formula (10) and the monoamine represented by the following formula (12) may be added simultaneously or separately.
- Ar is an optionally substituted divalent aromatic group.
- Ar is an optionally substituted monovalent aromatic group
- R 5 and R 6 are each independently a hydrogen atom or a monovalent hydrocarbon group.
- an imide oligomer having a structure represented by the above formula (1-2) for example, an acid dianhydride represented by the above formula (9) and a diamine represented by the above formula (10) Examples thereof include a method of reacting with a phenolic hydroxyl group-containing monoamine represented by the following formula (13). Further, by using an aliphatic triamine or an aromatic triamine instead of the diamine represented by the above formula (10), an imide oligomer having a structure represented by the above formula (2-2) can be produced.
- Ar is an optionally substituted divalent aromatic group
- R 7 and R 8 are each independently a hydrogen atom or a monovalent hydrocarbon group.
- the solvent is removed by heating, pressure reduction, or the like, and the mixture is heated at about 200° C. or higher for 1 hour or longer to react the amic acid oligomer.
- the molar ratio of the acid dianhydride represented by the above formula (9), the diamine represented by the above formula (10) and the phenolic hydroxyl group-containing monoamine represented by the above formula (13), and the imidization conditions By adjusting, it is possible to obtain an imide oligomer having a desired number average molecular weight and a structure represented by the above formula (1-2) at both ends.
- the phenolic hydroxyl group-containing monoamine represented by the above formula (13) by replacing part of the phenolic hydroxyl group-containing monoamine represented by the above formula (13) with the monoamine represented by the above formula (12), it has a desired number average molecular weight, and one end has the above formula An imide oligomer having a structure represented by (1-2) and having a structure derived from a monoamine represented by the above formula (12) at the other end can be obtained.
- the phenolic hydroxyl group-containing monoamine represented by the above formula (13) and the monoamine represented by the above formula (12) may be added simultaneously or separately.
- Examples of the acid dianhydride represented by the above formula (9) include pyromellitic anhydride, 3,3'-oxydiphthalic anhydride, 3,4'-oxydiphthalic anhydride, 4,4'-oxydiphthalic anhydride.
- acid anhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 4,4'-bis(2,3-dicarboxylphenoxy)diphenyl ether dianhydride, p-phenylene Bis(trimellitate anhydride), 2,3,3',4'-biphenyltetracarboxylic acid dianhydride and the like can be mentioned.
- aromatic acid dianhydrides having a melting point of 240° C. or less are preferable as the acid dianhydrides used as raw materials for the imide oligomers, since they are excellent in solubility and heat resistance, and have a melting point of 220° C.
- the following aromatic acid dianhydrides are more preferred, and aromatic acid dianhydrides having a melting point of 200°C or less are more preferred, and 3,4'-oxydiphthalic dianhydride (melting point 180°C), 4,4'-(4,4'-Isopropylidenediphenoxy)diphthalic anhydride (melting point 190°C) is particularly preferred.
- the "melting point” means a value measured as an endothermic peak temperature when the temperature is raised at 10°C/min using a differential scanning calorimeter.
- Examples of the differential scanning calorimeter include EXTEAR DSC6100 (manufactured by SII Nano Technology Co., Ltd.).
- aromatic diamines include, for example, 3,3′-diaminodiphenylmethane, 3,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, 3,3′- Diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 3,3'-diaminodiphenylsulfone, 4,4'-diaminodiphenyl Sulfone, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, bis(4-(4-aminophenoxy ) phenyl)
- Examples of acid anhydrides represented by the above formula (11) include phthalic anhydride, 3-methylphthalic anhydride, 4-methylphthalic anhydride, 1,2-naphthalic anhydride, and 2,3-naphthalic anhydride.
- Monoamines represented by the above formula (12) include, for example, aniline, o-toluidine, m-toluidine, p-toluidine, 2,4-dimethylaniline, 3,4-dimethylaniline, 3,5-dimethylaniline, 2-tert-butylaniline, 3-tert-butylaniline, 4-tert-butylaniline, 1-naphthylamine, 2-naphthylamine, 1-aminoanthracene, 2-aminoanthracene, 9-aminoanthracene, 1-aminopyrene, 3- Chloroaniline, o-anisidine, m-anisidine, p-anisidine, 1-amino-2-methylnaphthalene, 2,3-dimethylaniline, 2,4-dimethylaniline, 2,5-dimethylaniline, 3,4-dimethyl aniline, 4-ethylaniline, 4-ethynylaniline, 4-is
- Examples of the phenolic hydroxyl group-containing monoamine represented by the above formula (13) include 3-aminophenol, 4-aminophenol, 4-amino-o-cresol, 5-amino-o-cresol, 4-amino-2 ,3-xylenol, 4-amino-2,5-xylenol, 4-amino-2,6-xylenol, 4-amino-1-naphthol, 5-amino-2-naphthol, 6-amino-1-naphthol, 4 -amino-2,6-diphenylphenol and the like.
- 4-amino-o-cresol and 5-amino-o-cresol are preferred because they are excellent in availability and storage stability and provide a high glass transition temperature after curing.
- the imide oligomer is a plurality of imide oligomers having a structure represented by the above formula (1-1) or a structure represented by the above formula (1-2). and a mixture of each raw material (imide oligomer composition).
- the imide oligomer is a plurality of imide oligomers having a structure represented by the formula (2-1).
- it can be obtained as one contained in a mixture (imide oligomer composition) of a plurality of kinds of imide oligomers having a structure represented by the above formula (2-2) and each raw material.
- the imide oligomer composition When the imide oligomer composition has an imidization rate of 70% or more, it can provide a cured product having excellent mechanical strength at high temperatures and long-term heat resistance when used as a curing agent.
- a preferred lower limit for the imidization rate of the imide oligomer composition is 75%, and a more preferred lower limit is 80%. Although there is no particular upper limit for the imidization rate of the imide oligomer composition, the practical upper limit is 98%.
- the above-mentioned "imidation rate” is measured by a total reflection measurement method (ATR method) using a Fourier transform infrared spectrophotometer (FT-IR), and is derived from the carbonyl group of amic acid at 1660 cm -1 It can be derived from the peak absorbance area in the vicinity by the following formula.
- Examples of the Fourier transform infrared spectrophotometer include UMA600 (manufactured by Agilent Technologies).
- the imide oligomer composition dissolve in 10 g of tetrahydrofuran at 25°C.
- the preferable lower limit of the content of the curing agent in the total 100 parts by weight of the curable resin and the curing agent (further curing accelerator when containing the curing accelerator described later) is 20 parts by weight, and the preferable upper limit is 80 parts. weight part.
- the content of the curing agent is within this range, the resulting curable resin composition is more excellent in curability and storage stability.
- a more preferable lower limit to the content of the curing agent is 25 parts by weight, and a more preferable upper limit is 75 parts by weight.
- the curable resin composition of the present invention contains an inorganic filler. By containing the inorganic filler, the curable resin composition of the present invention provides a cured product with excellent dielectric properties.
- examples of the inorganic filler include silica, alumina, boron nitride, magnesium oxide, and boehmite. Among them, silica is preferable.
- a preferable lower limit of the average particle size of the inorganic filler is 0.2 ⁇ m, and a preferable upper limit thereof is 5 ⁇ m.
- the average particle size of the inorganic filler is within this range, it becomes more excellent in dispersibility in the curable resin composition without deteriorating the coatability, etc., and the dielectric properties and adhesiveness of the cured product are improved. It becomes excellent by the effect of compatibility.
- a more preferable lower limit of the average particle size of the inorganic filler is 0.5 ⁇ m, and a more preferable upper limit thereof is 2 ⁇ m.
- the average particle size of the inorganic filler can be measured by dispersing the inorganic filler in a solvent (water, organic solvent, etc.) using a particle size distribution analyzer. Examples of the particle size distribution analyzer include NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
- a preferable lower limit of the content of the inorganic filler in 100 parts by weight of the solid content of the curable resin composition is 65 parts by weight.
- the content of the inorganic filler is 65 parts by weight or more, the resulting curable resin composition is more excellent in dielectric properties after curing.
- a more preferable lower limit for the content of the inorganic filler is 70 parts by weight.
- the upper limit of the content of the inorganic filler in 100 parts by weight of the total solid content of the curable resin composition is preferably 73 parts by weight, and a more preferred upper limit is 71 parts by weight. be.
- the above-mentioned "entire solid content of the curable resin composition” means the entire components other than the solvent when the curable resin composition contains a solvent described later.
- the curable resin composition of the present invention contains a dispersant. By containing the dispersant, the curable resin composition of the present invention can uniformly disperse the inorganic filler, and the cured product has excellent adhesiveness.
- dispersant examples include polyurethane-based dispersants, fatty acid-based dispersants, polyamino-based dispersants, and polyacrylate-based dispersants.
- polyurethane-based dispersants are preferred because they make it particularly easy to set the complex viscosity at 90° C., 5% strain, and 1 rad/sec within the above range.
- a preferable lower limit of the content of the dispersing agent in 100 parts by weight of the total solid content of the curable resin composition is 0.05 parts by weight, and a preferable upper limit thereof is 1.0 parts by weight.
- the content of the dispersant is within this range, the resulting curable resin composition is more excellent in the effect of achieving both dielectric properties and adhesiveness after curing.
- a more preferred lower limit to the content of the dispersant is 0.1 parts by weight, and a more preferred upper limit is 0.7 parts by weight.
- the curable resin composition of the present invention preferably contains a curing accelerator.
- a curing accelerator By containing the curing accelerator, the curing time can be shortened and the productivity can be improved.
- the curing accelerator examples include imidazole-based curing accelerators, tertiary amine-based curing accelerators, phosphine-based curing accelerators, phosphorus-based curing accelerators, photobase generators, sulfonium salt-based curing accelerators, and the like. . Of these, imidazole-based curing accelerators are preferred because of their excellent storage stability. The curing accelerators may be used alone, or two or more of them may be used in combination.
- the content of the curing accelerator has a preferable lower limit of 0.01 parts by weight and a preferable upper limit of 10 parts by weight based on a total of 100 parts by weight of the curable resin, the curing agent and the curing accelerator.
- a more preferred lower limit to the content of the curing accelerator is 0.05 parts by weight, and a more preferred upper limit is 5 parts by weight.
- the curable resin composition of the present invention may contain an organic filler for the purpose of relaxing stress, imparting toughness, and the like.
- organic filler include silicone rubber particles, acrylic rubber particles, urethane rubber particles, polyamide particles, polyamideimide particles, polyimide particles, benzoguanamine particles, and core-shell particles thereof. Among them, polyamide particles, polyamideimide particles, and polyimide particles are preferred.
- the preferred upper limit of the content of the organic filler is 300 parts by weight with respect to a total of 100 parts by weight of the curable resin and the curing agent (and the curing accelerator when the curing accelerator is contained). be.
- the content of the organic filler is within this range, the obtained cured product is superior in toughness and the like while maintaining excellent adhesiveness and the like.
- a more preferable upper limit of the content of the organic filler is 200 parts by weight.
- the curable resin composition of the present invention may contain a polymer component as long as the object of the present invention is not impaired.
- the polymer component serves as a film-forming component.
- a preferable lower limit of the number average molecular weight of the polymer component is 3,000, and a preferable upper limit thereof is 100,000. When the number average molecular weight of the polymer component is within this range, the resulting curable resin composition will be superior in flexibility and workability before curing and in heat resistance after curing.
- a more preferable lower limit of the number average molecular weight of the polymer component is 5,000, and a more preferable upper limit thereof is 80,000.
- polymer component examples include polyimide, phenoxy resin, polyamide, polyamideimide, polymaleimide, cyanate resin, benzoxazine resin, acrylic resin, urethane resin, and polyester.
- polyimide, polyamide, polyamideimide, and polymaleimide are preferable, and polyimide is more preferable.
- the preferable lower limit of the content of the polymer component is 0.5 parts by weight with respect to a total of 100 parts by weight of the curable resin and the curing agent (and the curing accelerator when the curing accelerator is contained).
- the preferred upper limit is 20 parts by weight.
- a more preferable lower limit of the content of the polymer component is 1 part by weight, and a more preferable upper limit is 10 parts by weight.
- the curable resin composition of the present invention may contain a flame retardant as long as the object of the present invention is not impaired.
- the flame retardant include boehmite-type aluminum hydroxide, aluminum hydroxide, metal hydrates such as magnesium hydroxide, halogen-based compounds, phosphorus-based compounds, and nitrogen compounds. Among them, boehmite-type aluminum hydroxide is preferable.
- the content of the flame retardant is preferably 200 parts by weight with respect to a total of 100 parts by weight of the curable resin and the curing agent (and the curing accelerator when the curing accelerator is contained). .
- the content of the flame retardant is within this range, the resulting curable resin composition has excellent flame retardancy while maintaining excellent adhesion and the like.
- a more preferable upper limit of the content of the flame retardant is 150 parts by weight.
- the curable resin composition may contain a solvent from the viewpoint of coatability and the like.
- a solvent having a boiling point of less than 200° C. is preferable from the viewpoint of coatability, storage stability, and the like.
- the solvent having a boiling point of less than 200° C. include alcohol-based solvents, ketone-based solvents, ester-based solvents, hydrocarbon-based solvents, halogen-based solvents, ether-based solvents, and nitrogen-containing solvents.
- the alcohol solvent include methanol, ethanol, isopropyl alcohol, normal propyl alcohol, isobutyl alcohol, normal butyl alcohol, tertiary butyl alcohol, and 2-ethylhexanol.
- Examples of the ketone solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl propyl ketone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, and diacetone alcohol.
- Examples of the ester solvent include methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, methoxybutyl acetate, amyl acetate, normal propyl acetate, isopropyl acetate, methyl lactate, ethyl lactate, butyl lactate and the like.
- hydrocarbon solvent examples include benzene, toluene, xylene, normal hexane, isohexane, cyclohexane, methylcyclohexane, ethylcyclohexane, isooctane, normal decane, normal heptane, and the like.
- halogen-based solvent examples include dichloromethane, chloroform, and trichlorethylene.
- ether solvent examples include diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,3-dioxolane, diisopropyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether acetate. , propylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, ethylene glycol monotertiary butyl ether, propylene glycol monomethyl ether propionate, 3-methoxybutanol, diethylene glycol dimethyl ether, anisole, 4-methylanisole and the like. be done.
- nitrogen-containing solvent examples include acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide and the like.
- ketone solvents with a boiling point of 60 ° C. or higher and lower than 200 ° C. from the viewpoint of handleability and solubility of imide oligomers, ketone solvents with a boiling point of 60 ° C. or higher and lower than 200 ° C., ester solvents with a boiling point of 60 ° C. or higher and lower than 200 ° C., and boiling points of 60 ° C. or higher and 200 ° C.
- At least one selected from the group consisting of ether-based solvents having a temperature of less than °C is preferred.
- solvents examples include methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, isobutyl acetate, 1,4-dioxane, 1,3-dioxolane, tetrahydrofuran, cyclohexanone, methylcyclohexanone, diethylene glycol dimethyl ether, and anisole.
- the "boiling point” means a value measured under conditions of 101 kPa, or a value converted to 101 kPa using a boiling point conversion chart or the like.
- a preferable lower limit of the content of the solvent in 100 parts by weight of the curable resin composition containing the solvent is 20 parts by weight, and a preferable upper limit thereof is 90 parts by weight.
- the content of the solvent is within this range, the resulting curable resin composition is more excellent in coatability and the like.
- a more preferable lower limit for the content of the solvent is 30 parts by weight, and a more preferable upper limit is 80 parts by weight.
- the curable resin composition of the present invention may contain a reactive diluent as long as the object of the present invention is not impaired.
- the reactive diluent is preferably a reactive diluent having two or more reactive functional groups in one molecule.
- the curable resin composition of the present invention may further contain additives such as coupling agents, storage stabilizers, anti-bleeding agents, fluxing agents and leveling agents.
- the method for producing the curable resin composition of the present invention includes, for example, a method of mixing a curable resin, a curing agent, an inorganic filler, a dispersant, a polymer component, etc. using a mixer. is mentioned.
- the mixer include a homodisper, a universal mixer, a Banbury mixer, a kneader, and the like.
- a curable resin composition film comprising the curable resin composition of the present invention can be obtained by applying the curable resin composition of the present invention onto a substrate film and drying the curable resin composition.
- a cured product can be obtained by curing the product film.
- the preferable upper limit of dielectric loss tangent at 23° C. of the cured product is 0.0045. Since the cured product has a dielectric loss tangent within this range at 23° C., the curable resin composition of the present invention can be suitably used as an interlayer insulating material for multilayer printed wiring boards and the like. A more preferable upper limit of the dielectric loss tangent at 23° C. of the cured product is 0.0040, and a more preferable upper limit is 0.0035.
- the above-mentioned "dielectric loss tangent” is a value measured under conditions of 1.0 GHz using a dielectric constant measuring device and a network analyzer.
- the cured product for measuring the “dielectric loss tangent” can be obtained by heating the curable resin composition film having a thickness of 40 to 200 ⁇ m at 190° C. for 90 minutes.
- the curable resin composition of the present invention can be used in a wide variety of applications.
- adhesives for printed wiring boards, adhesives for coverlays of flexible printed circuit boards, copper-clad laminates, adhesives for bonding semiconductors, interlayer insulating materials, prepregs, sealants for LEDs, adhesives for structural materials, etc. can be used.
- the curable resin composition of the present invention can be suitably used as an interlayer insulating material such as a multilayer printed wiring board because the cured product thereof has a low dielectric constant and a low dielectric loss tangent and is excellent in dielectric properties.
- An interlayer insulating material using the curable resin composition of the present invention is also one aspect of the present invention.
- the curable resin composition which is excellent in the dielectric property and adhesiveness after hardening can be provided. Further, according to the present invention, it is possible to provide an interlayer insulating material using the curable resin composition.
- the obtained imide oligomer composition was confirmed by 1 H-NMR, GPC, and FT-IR analysis as an aliphatic diamine residue having a structure represented by the above formula (5-1) or (5-3). It was confirmed that a group-containing imide oligomer (A is a 4,4′-(4,4′-isopropylidenediphenoxy)diphthalic anhydride residue, B is a dimer diamine residue). Moreover, the weight average molecular weight of the imide oligomer composition was 2,200.
- Examples 1 to 7, Comparative Examples 1 to 4 According to the compounding ratio shown in Table 1, each material was stirred and mixed to prepare curable resin compositions of Examples 1 to 7 and Comparative Examples 1 to 4. Each obtained curable resin composition was coated on a substrate PET film so as to have a thickness of about 20 ⁇ m, and dried to prepare a curable resin composition film on the substrate PET film. The PET film was peeled off from the obtained curable resin composition film, and laminated with a laminator to a thickness of 500 ⁇ m to obtain a laminate. Using a rotary rheometer, the obtained laminate was heated to 90° C.
- the laminate obtained in the same manner was heated from 40° C. to 120° C. at a frequency of 1.0 Hz, a strain of 21%, and the melt viscosity at 90° C. was measured using a rotary rheometer.
- ARES manufactured by TA Instruments
- Table 1 shows the measurement results of the complex viscosity and the melt viscosity.
- Each curable resin composition obtained in Examples and Comparative Examples was coated on a base PET film and dried to form a base PET film and a cured film having a thickness of 40 ⁇ m on the base PET film.
- An uncured laminated film having a flexible resin composition layer was obtained.
- the obtained uncured laminated film was cut into a size of 2 mm in width and 80 mm in length.
- the substrate PET film was peeled off from the curable resin composition layer of the cut uncured laminated film, and five curable resin composition layers were laminated using a laminator to obtain a laminate having a thickness of about 200 ⁇ m.
- the resulting laminate was heated at 190° C. for 90 minutes to obtain a cured product.
- a cavity resonance perturbation method permittivity measuring device CP521 manufactured by Kanto Denshi Applied Development Co., Ltd.
- a network analyzer N5224A PNA manufactured by Keysight Technologies
- the resulting laminate was cut to a width of 1 cm, and a 35 ⁇ m thick copper foil (manufactured by Fukuda Metal Foil and Powder Co., Ltd., a glossy surface of electrolytic copper foil, “CF-T8G-UN-35 ”) was laminated and heat-pressed under the conditions of 190° C., 3 MPa, and 1 hour to cure the curable resin composition layer and obtain a test piece.
- a test piece within 24 hours after preparation was subjected to a 90° peel test at a peel rate of 50 mm/min at 25° C. using a tensile tester ("UCT-500" manufactured by ORIENTEC) to measure the peel strength.
- the curable resin composition which is excellent in the dielectric property and adhesiveness after hardening can be provided. Further, according to the present invention, it is possible to provide an interlayer insulating material using the curable resin composition.
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JP2020522593A (ja) * | 2017-12-11 | 2020-07-30 | エルジー・ケム・リミテッド | 金属薄膜コーティング用熱硬化性樹脂組成物およびこれを用いた金属積層体 |
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