WO2022201620A1 - 樹脂組成物、硬化物、樹脂シート、プリプレグ、金属箔張積層板、多層プリント配線板、封止用材料、繊維強化複合材料、接着剤及び半導体装置 - Google Patents
樹脂組成物、硬化物、樹脂シート、プリプレグ、金属箔張積層板、多層プリント配線板、封止用材料、繊維強化複合材料、接着剤及び半導体装置 Download PDFInfo
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- WO2022201620A1 WO2022201620A1 PCT/JP2021/040619 JP2021040619W WO2022201620A1 WO 2022201620 A1 WO2022201620 A1 WO 2022201620A1 JP 2021040619 W JP2021040619 W JP 2021040619W WO 2022201620 A1 WO2022201620 A1 WO 2022201620A1
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- resin
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- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002866 paraformaldehyde Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- NOHFYJWXIIYRIP-UHFFFAOYSA-N phenyl 4-cyanatobenzoate Chemical compound C=1C=C(OC#N)C=CC=1C(=O)OC1=CC=CC=C1 NOHFYJWXIIYRIP-UHFFFAOYSA-N 0.000 description 1
- CWHFDTWZHFRTAB-UHFFFAOYSA-N phenyl cyanate Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920006290 polyethylene naphthalate film Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-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
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical class NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- ZSOVVFMGSCDMIF-UHFFFAOYSA-N trimethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OC)(OC)OC)=CC=CC2=C1 ZSOVVFMGSCDMIF-UHFFFAOYSA-N 0.000 description 1
- RKLXSINPXIQKIB-UHFFFAOYSA-N trimethoxy(oct-7-enyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCC=C RKLXSINPXIQKIB-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- XQEGZYAXBCFSBS-UHFFFAOYSA-N trimethoxy-(4-methylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=C(C)C=C1 XQEGZYAXBCFSBS-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Substances CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/088—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyamides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
- B32B27/26—Layered products comprising a layer of synthetic resin characterised by the use of special additives using curing agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L79/085—Unsaturated polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/06—Polyhydrazides; Polytriazoles; Polyamino-triazoles; Polyoxadiazoles
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
Definitions
- the present invention relates to a resin composition, a cured product, a resin sheet, a prepreg, a metal foil-clad laminate, a multilayer printed wiring board, a sealing material, a fiber-reinforced composite material, an adhesive, and a semiconductor device.
- the resin composition used as the material of the insulating layer is mainly a thermosetting resin, and holes for obtaining electrical connection between the insulating layers are generally made by laser processing.
- drilling holes by laser processing has the problem that the processing time becomes longer as the number of holes in a high-density substrate increases. Therefore, in recent years, by using a resin composition that allows the exposed area to be cured (exposure process) and the unexposed area to be removed (development process) by irradiation with light, etc., it is possible to perform batch drilling in the exposure and development processes. There is a demand for a resin sheet that makes this possible.
- a method of exposure a method of exposing through a photomask using a mercury lamp as a light source is used, and a material that can be suitably exposed to the light source of this mercury lamp is desired.
- This exposure method using a mercury lamp as a light source uses ghi crosstalk (g-line wavelength 436 nm, h-line wavelength 405 nm, i-line wavelength 365 nm), etc., and a general-purpose photocuring initiator can be selected.
- a direct drawing exposure method has also been introduced in which drawing is performed directly on a photosensitive resin composition layer without using a photomask based on digital data of a pattern.
- This direct writing exposure method has better alignment accuracy than the exposure method that uses a photomask, and can produce highly detailed patterns.
- the light source uses monochromatic light such as a laser.
- a DMD (Digital Micromirror Device) type apparatus capable of forming a high-definition resist pattern uses a light source with a wavelength of 405 nm (h-line).
- a compound having an ethylenically unsaturated group such as (meth)acrylate is used in the photosensitive resin composition used for the laminate or resin sheet in order to enable rapid curing in the exposure process.
- a carboxyl-modified epoxy (meth)acrylate resin obtained by reacting a bisphenol-type epoxy resin and (meth)acrylic acid and then reacting an acid anhydride, a biphenyl-type epoxy resin
- a photosensitive thermosetting resin composition is described that includes a photoinitiator and a diluent.
- Patent Document 2 a photocurable binder polymer, a photopolymerizable compound having an ethylenically unsaturated bond, a photopolymerization (curing) initiator, a sensitizer, and a heat curing agent bisallyl nagic
- a resin composition includes an imide compound and a bismaleimide compound.
- Patent Document 3 describes a resin composition containing a bismaleimide compound (curable resin) and a photoradical polymerization initiator (curing agent) as a photosensitive resin composition used for laminates and resin sheets. ing.
- the cured product obtained from the resin composition described in Patent Document 1 is described as having excellent flexibility and folding resistance as a solder resist, and is also excellent in heat resistance. There is no specific value for , and there is a problem that it is inferior in heat resistance and thermal stability to use as an interlayer insulating layer.
- Patent Document 2 describes the use of a bismaleimide compound, it is described as a thermosetting agent, and (meth)acrylate is used as the photopolymerizable compound. Therefore, there is a problem that it is inferior in heat resistance and thermal stability when used as an interlayer insulating layer.
- Patent Document 3 a bismaleimide compound is used as a curable resin.
- maleimide compounds generally have poor light transmittance, when a maleimide compound is included, sufficient light does not reach the photocuring initiator, resulting in photocuring. The initiator hardly generates radicals and its reactivity is very low. Therefore, in Patent Document 3, the maleimide compound is cured by performing additional heating before development.
- An object of the present invention is to provide a resin composition from which an excellent cured product can be obtained, a resin sheet using the same, a multilayer printed wiring board, and a semiconductor device.
- the present inventors have found that the above problems can be solved by using a resin composition containing a specific bismaleimide compound (A), a specific resin or compound (B), and a photocuring initiator (C). and completed the present invention.
- a bismaleimide compound (A) comprising a structural unit represented by the following formula (1) and maleimide groups at both ends of a molecular chain; At least one resin selected from the group consisting of maleimide compounds other than the bismaleimide compound (A), cyanate ester compounds, benzoxazine compounds, epoxy resins, carbodiimide compounds, and compounds having an ethylenically unsaturated group, or a compound (B); A resin composition comprising a photocuring initiator (C).
- a resin composition comprising a photocuring initiator (C).
- R 1 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- R 2 is It represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms, and each R 3 independently represents a hydrogen atom or 1 to 1 carbon atoms.
- each R4 is independently a hydrogen atom or a straight chain having 1 to 6 carbon atoms; or a branched alkyl group, a halogen atom, a hydroxy group, or a linear or branched alkoxy group having 1 to 6 carbon atoms, each n 1 independently representing an integer of 1 to 4; n2 each independently represents an integer of 1 to 4).
- each R 4 independently represents a substituent represented by the following formula (3) or a phenyl group.
- (A) is represented by the general formula (1)
- a resin sheet comprising a support and a resin layer disposed on one or both sides of the support, wherein the resin layer contains the resin composition according to [1] to [3].
- a prepreg comprising a substrate and the resin composition according to any one of [1] to [4] impregnated or applied to the substrate.
- a sealing material comprising the resin composition according to any one of [1] to [4].
- a fiber-reinforced composite material comprising the resin composition according to any one of [1] to [4] and reinforcing fibers.
- An adhesive comprising the resin composition according to any one of [1] to [4].
- a semiconductor device comprising the resin composition according to any one of [1] to [4].
- the resin composition when used in a multilayer printed wiring board, the resin composition has excellent photocurability and can obtain a cured product having excellent heat resistance, thermal stability and insulation reliability in a well-balanced manner.
- a resin sheet, a multilayer printed wiring board, and a semiconductor device using it can be provided.
- this embodiment the form for carrying out the present invention (hereinafter referred to as "this embodiment") will be described in detail.
- the following embodiments are examples for explaining the present invention, and are not intended to limit the present invention to the following contents.
- the present invention can be appropriately modified and implemented within the scope of the gist thereof.
- (meth)acryloxy means both “acryloxy” and corresponding "methacryloxy
- (meth)acrylate means both “acrylate” and corresponding “methacrylate”.
- (meth)acryl means both “acryl” and the corresponding "methacryl”.
- the resin composition of the present embodiment comprises a specific bismaleimide compound (A) (also referred to as “component (A)”), a maleimide compound other than the bismaleimide compound (A), a cyanate ester compound, a benzoxazine compound, an epoxy At least one resin or compound (B) selected from the group consisting of resins, carbodiimide compounds, and compounds having an ethylenically unsaturated group (also referred to as “component (B)” or “resin or compound (B)” ) and a photo-curing initiator (C) (also referred to as “component (C)”).
- component (A) also referred to as “component (A)”
- component (B) also referred to as “component (B)”
- a photo-curing initiator (C) also referred to as “component (C)
- the resin composition contains a bismaleimide compound (A) (also referred to as component (A)).
- the bismaleimide compound (A) contains a structural unit represented by formula (1) and maleimide groups at both ends of the molecular chain.
- R 1 represents a linear or branched alkylene group having 1 to 16 carbon atoms or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- R 2 represents a linear or branched alkylene group having 1 to 16 carbon atoms or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- Each R 3 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms.
- Each n 1 independently represents an integer of 1 to 4.
- n2 each independently represents an integer of 1 to 4;
- maleimide compounds have poor light transmittance, so when a resin composition contains a maleimide compound, light does not sufficiently reach the photocuring initiator dispersed in the resin composition, causing the photocuring initiator to generate radicals. unlikely to occur. Therefore, the radical photoreaction of the maleimide compound is generally difficult to proceed, and even if the radical polymerization or dimerization reaction of maleimide alone proceeds, the reactivity is very low.
- the bismaleimide compound (A) contains the structural unit represented by the formula (1), it has very excellent light transmittance.
- the light sufficiently reaches the photocuring initiator, the photoradical reaction of the maleimide occurs efficiently, and the bismaleimide compound (A) is mixed with the resin or compound (B) described below and the photocuring initiator (C). , can be photocured using various active energy rays.
- a chloroform solution containing 1% by mass of the bismaleimide compound (A) is prepared, and an active energy ray containing a wavelength of 365 nm (i-line) is used to extract 1% by mass of the bismaleimide compound (A).
- the transmittance of the chloroform solution contained in is measured, the transmittance is 5% or more, indicating very excellent light transmittance.
- the transmittance of a chloroform solution containing 1% by mass of the bismaleimide compound (A) was measured using an active energy ray (light beam) having a wavelength of 405 nm (h-line), the transmittance was 5%. % or more, showing very excellent light transmittance.
- the transmittance at a wavelength of 365 nm (i-line) is preferably 8% or more, more preferably 10% or more, from the viewpoint of exhibiting more excellent light transmittance.
- the transmittance at a wavelength of 405 nm (h-line) is preferably 8% or more, and preferably 10% or more, from the viewpoint of producing a printed wiring board having a higher density and finer wiring formation (pattern). more preferred.
- the upper limits of the transmittance at a wavelength of 365 nm (i-line) and the transmittance at a wavelength of 405 nm (h-line) are, for example, 99.9% or less.
- photocuring initiators tend to have lower absorbance when using long-wavelength light. For example, when an active energy ray containing a wavelength of 405 nm (h-line) is used, since the light of this wavelength is a relatively long wavelength, it is not absorbed by a normal photocuring initiator, and this light is preferably absorbed. Polymerization does not proceed unless a photocuring initiator capable of generating radicals is used.
- the photocuring initiator (C) described later when the absorbance of a chloroform solution containing 0.01% by mass of the photocuring initiator (C) is measured, light with a wavelength of 405 nm (h line)
- a photo-curing initiator exhibiting an extremely excellent absorbency such as an absorbance of 0.1 or more.
- the bismaleimide compound (A) Since the bismaleimide compound (A) has excellent light transmittance as described above, for example, even when an active energy ray containing a wavelength of 365 nm or an active energy ray containing a wavelength of 405 nm is used, light is a photocuring initiator. , a radical reaction using radicals generated from the photocuring initiator proceeds, and photocuring becomes possible even in a composition containing a large amount of the bismaleimide compound (A). Therefore, the resin composition of the present embodiment has excellent photocurability. On the other hand, the bismaleimide compound (A) has a rigid imide ring even after photocuring, and thus has high heat resistance and thermal stability.
- the cured product obtained by homopolymerizing the bismaleimide compound (A) is not suitable for multilayer printed wiring boards.
- the bismaleimide compound (A) together with the resin or compound (B) described below and the photocuring initiator (C) it is possible to achieve higher heat resistance while maintaining excellent photocurability and insulation reliability. and thermally stable. Therefore, the cured product obtained from the resin composition of the present embodiment has excellent heat resistance, thermal stability, and insulation reliability. and an insulating layer can be suitably formed.
- the bismaleimide compound (A) preferably has a weight-average molecular weight of 100 to 6,000, more preferably 300 to 5,500, from the viewpoint that a suitable viscosity can be obtained and an increase in the viscosity of the varnish can be suppressed.
- “mass average molecular weight” means the mass average molecular weight of polystyrene standard conversion by the gel permeation chromatography (GPC) method.
- R 1 is a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. show.
- R 1 is preferably a straight-chain or branched alkylene group, more preferably a straight-chain alkylene group, from the viewpoint that a suitable viscosity can be obtained and the increase in the viscosity of the varnish can be controlled.
- the number of carbon atoms in the alkylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- Linear or branched alkylene groups include, for example, methylene group, ethylene group, propylene group, 2,2-dimethylpropylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group and decylene group.
- the number of carbon atoms in the alkenylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- Linear or branched alkenylene groups include, for example, vinylene group, 1-methylvinylene group, arylene group, propenylene group, isopropenylene group, 1-butenylene group, 2-butenylene group, 1-pentenylene group, 2 -pentenylene group, isopentenylene group, cyclopentenylene group, cyclohexenylene group, dicyclopentadienylene group, and the like.
- R 2 represents a linear or branched alkylene group having 1 to 16 carbon atoms or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- R 2 is preferably a straight-chain or branched alkylene group, more preferably a straight-chain alkylene group, from the viewpoint that a suitable viscosity can be obtained and the increase in the viscosity of the varnish can be controlled.
- the number of carbon atoms in the alkylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- R 1 As a linear or branched alkylene group, reference can be made to R 1 .
- the number of carbon atoms in the alkenylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- R 1 As a linear or branched alkenylene group reference can be made to R 1 .
- R 1 and R 2 may be the same or different, but are preferably the same from the viewpoint of easier synthesis of the bismaleimide compound (A).
- each R 3 is independently a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms. indicates Each R 3 is preferably a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms in order to obtain a suitable viscosity and control the viscosity increase of the varnish.
- R 3 it is more preferable that 1 to 4 groups (R 3 ) are linear or branched alkyl groups having 1 to 16 carbon atoms and the remaining groups (R 3 ) are hydrogen atoms, Among R 3 , it is more preferable that 1 to 3 groups (R 3 ) are C 1-16 linear or branched alkyl groups and the remaining groups (R 3 ) are hydrogen atoms.
- the number of carbon atoms in the alkyl group is preferably from 2 to 14, more preferably from 4 to 12, from the viewpoint that more suitable viscosity can be obtained and the increase in viscosity of the varnish can be more controlled.
- Linear or branched alkyl groups include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, 1-ethylpropyl group, n-butyl group, 2-butyl group, isobutyl group and tert-butyl.
- the number of carbon atoms in the alkenyl group is preferably from 2 to 14, more preferably from 4 to 12, from the viewpoint that a more suitable viscosity can be obtained and the viscosity increase of the varnish can be more controlled.
- Linear or branched alkenyl groups include, for example, vinyl group, allyl group, 4-pentenyl group, isopropenyl group, isopentenyl group, 2-heptenyl group, 2-octenyl group, and 2-nonenyl group. be done.
- each R 4 is independently a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a halogen atom, a hydroxy group, or a linear chain having 1 to 6 carbon atoms. represents a straight or branched alkoxy group. From the viewpoint of dielectric properties, R 4 is preferably a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms.
- the number of carbon atoms in the alkyl group is preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, from the viewpoint of obtaining more suitable viscosity.
- Linear or branched alkyl groups include, for example, methyl, ethyl, n-propyl and isopropyl groups.
- Halogen atoms include, for example, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
- the number of carbon atoms in the alkoxy group is preferably a prime number of 1 to 6, more preferably 1 to 3, from the viewpoint of obtaining a more suitable viscosity.
- Linear or branched alkoxy groups include methoxy, ethoxy, n-propoxy and isopropoxy groups.
- each n 1 independently represents an integer of 1-4.
- n 2 each independently represents an integer of 1 to 4
- the bismaleimide compound (A) has maleimide groups at both ends of the molecular chain.
- both ends mean both ends of the molecular chain of the bismaleimide compound (A).
- the maleimido group is at the chain end of R 1 or at the chain end at the N atom of the maleimide ring or at both ends.
- the bismaleimide compound (A) may have maleimide groups other than both ends of the molecular chain.
- the maleimide group is represented by formula (4) with the N atom attached to the molecular chain of formula (1) above.
- the maleimide groups bonded to the above formula (1) may all be the same or different, but the maleimide groups at both ends of the molecular chain are preferably the same.
- each R 6 independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Both R 6 are preferably hydrogen atoms from the viewpoint of suitable photocuring.
- the number of carbon atoms in the alkyl group is preferably from 1 to 3, more preferably from 1 to 2, from the viewpoint of suitable photocuring.
- Examples of the bismaleimide compound (A) include bismaleimide compounds represented by formula (5). These may be used singly or in admixture of two or more.
- a represents an integer of 1-10. It is preferable that a is an integer of 1 to 6 from the viewpoint that a more suitable viscosity can be obtained and the increase in viscosity of the varnish can be more controlled.
- the content of the bismaleimide compound (A) makes it possible to obtain a cured product containing the bismaleimide compound as a main component, and has well-balanced photocurability, heat resistance, and dielectric properties. From the viewpoint that it can improve the , more preferably 8 to 98 parts by mass, even more preferably 13 to 93 parts by mass.
- the bismaleimide compound (A) can be used singly or in an appropriate mixture of two or more.
- the bismaleimide compound (A) can be produced by a known method. For example, 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride and a monomer containing a diamine, such as dimer diamine, A maleimide compound such as maleimide anhydride is subjected to a polyaddition reaction at a temperature of usually about 80 to 250° C., preferably about 100 to 200° C., for about 0.5 to 50 hours, preferably about 1 to 20 hours.
- a polyadduct After obtaining a polyadduct, it is usually heated at a temperature of about 60 to 120° C., preferably about 80 to 100° C. for about 0.1 to 2 hours, preferably about 0.1 to 0.5 hours. is subjected to an imidization reaction, ie, a dehydration ring-closing reaction, to obtain a bismaleimide compound (A).
- an imidization reaction ie, a dehydration ring-closing reaction
- Dimer diamine is obtained, for example, by a reductive amination reaction of dimer acid, and the amination reaction is performed by a known method such as a reduction method using ammonia and a catalyst (for example, JP-A-9-12712). method).
- a dimer acid is a dibasic acid obtained by dimerizing an unsaturated fatty acid by an intermolecular polymerization reaction or the like. Although it depends on synthesis conditions and purification conditions, it usually contains a small amount of monomer acid, trimer acid, etc. in addition to dimer acid. A double bond remains in the molecule obtained after the reaction.
- a dimer acid is obtained, for example, by polymerizing an unsaturated fatty acid using a Lewis acid and a Bronsted acid as a catalyst.
- a dimer acid can be produced by a known method (for example, the method described in JP-A-9-12712).
- unsaturated fatty acids include crotonic acid, myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, eicosenoic acid, erucic acid, nervonic acid, linoleic acid, pinolenic acid, eleostearic acid, mead acid, dihomo-gamma-linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, eicosatetraenoic acid, adrenic acid, boseopentaenoic acid, ospondic acid, sardine acid, tetracosapentaenoic acid, docosahexaenoic acid, and herring acid.
- the number of carbon atoms in the unsaturated fatty acid is generally 4-24, preferably 14-20.
- the diamine-containing monomer is previously dissolved or dispersed in an organic solvent in an inert atmosphere such as argon, nitrogen, or the like, to form a diamine-containing monomer solution and preferably.
- an inert atmosphere such as argon, nitrogen, or the like
- 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride is dissolved in an organic solvent or dispersed in slurry form. It is preferably added later, or in a solid state, to the monomer solution containing the diamine.
- solvents can be used in the polyaddition reaction and imidization reaction.
- solvents include amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and isophorone; Esters such as ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -methyl- ⁇ -butyrolactone, ethyl lactate, methyl acetate, ethyl acetate, and butyl acetate; methanol, ethanol , and aliphatic alcohols having 1 to 10 carbon atoms such as propanol; aromatic group-containing phenols such as phenol and cresol; aromatic group-containing alcohols such as benzyl
- a catalyst in the imidization reaction for example, tertiary amines and dehydration catalysts can be used.
- Preferred tertiary amines are heterocyclic tertiary amines such as pyridine, picoline, quinoline, and isoquinoline.
- Dehydration catalysts include, for example, acetic anhydride, propionic anhydride, n-butyric anhydride, benzoic anhydride, and trifluoroacetic anhydride.
- the amount of the catalyst to be added is, for example, about 0.5 to 5.0 times the molar equivalent of the imidizing agent with respect to the amide group, and 0.5 to 10.0 times the molar amount of the dehydration catalyst with respect to the amide group. Equivalent weights are preferred.
- this solution may be used as the bismaleimide compound (A) solution, or a poor solvent may be added to the reaction solvent to turn the bismaleimide compound (A) into a solid.
- poor solvents include water, methyl alcohol, ethyl alcohol, 2-propyl alcohol, ethylene glycol, triethylene glycol, 2-butyl alcohol, 2-pentyl alcohol, 2-hexyl alcohol, cyclopentyl alcohol, cyclohexyl alcohol, phenol, and t-butyl alcohol.
- the resin composition of the present embodiment includes a maleimide compound other than the bismaleimide compound (A), a cyanate ester compound, a benzoxazine compound, an epoxy resin, a carbodiimide compound, and a compound having an ethylenically unsaturated group. containing at least one resin or compound (B) (also referred to as component (B)). These resins or compounds (B) can be used singly or in admixture of two or more depending on the physical properties and intended use of the resulting cured product.
- the bismaleimide compound (A) is extremely excellent in light transmittance, even if the resin or compound (B) is used, the light sufficiently reaches the photocuring initiator, and the photoradical reaction of the maleimide occurs efficiently. It can be photocured using various active energy rays. Therefore, for example, even if an active energy ray containing a wavelength of 365 nm or an active energy ray containing a wavelength of 405 nm is used, the light sufficiently reaches the photocuring initiator, and a radical reaction using radicals generated from the photocuring initiator occurs. Photocuring becomes possible even in a composition containing a resin or a compound (B).
- the resin or compound (B) can be photocured together with the bismaleimide compound (A) and the photocuring initiator (C) using various active energy rays to obtain a cured product.
- the resin or compound (B) each prepares an N-methylpyrrolidone solution containing 1% by mass, and uses an active energy ray containing a wavelength of 365 nm (i-line) to create one carboxy group.
- the transmittance is preferably 5% or more.
- the resin or compound (B) exhibits very good light transmittance.
- the transmittance of an N-methylpyrrolidone solution containing 1% by mass of the resin or compound (B) is measured using an active energy ray having a wavelength of 405 nm (h-line), the transmittance is preferably 5% or more, and even in this case, very excellent light transmittance is exhibited.
- the resin or compound (B) is used, for example, when producing a printed wiring board having a high-density and high-definition wiring formation (pattern) using a direct drawing exposure method, an active material containing a wavelength of 405 nm (h-line) is used. Even when an energy beam is used, the photoradical reaction of maleimide occurs efficiently.
- the transmittance at a wavelength of 365 nm (i-line) is more preferably 8% or more, further preferably 10% or more, because a resin composition having excellent photocurability can be obtained.
- the transmittance at a wavelength of 405 nm (h-line) is more preferably 8% or more, and even more preferably 10% or more, because a resin composition with excellent photocurability can be obtained.
- the upper limit of the transmittance at a wavelength of 365 nm (i-line) and the transmittance at a wavelength of 405 nm (h-line) is, for example, 99.9% or less.
- the resin or compound (B) preferably has a molecular weight of 100 to 5,000 from the viewpoint of suppressing the viscosity increase of the varnish.
- the resin or compound (B) is not particularly limited as long as the effect of the present invention is exhibited, but from the viewpoint of suppressing the viscosity increase of the varnish, it is preferable that the weight average molecular weight is 100 to 50,000.
- “mass average molecular weight” means the mass average molecular weight of polystyrene standard conversion by gel permeation chromatography (GPC) method.
- the total content of the resin or compound (B) is the bismaleimide compound (A ), preferably 0.5 to 85 parts by mass, more preferably 1 to 84 parts by mass with respect to a total of 100 parts by mass of the resin or compound (B) and the photocuring initiator (C) described later. It is preferably 5 to 80 parts by mass, and more preferably 5 to 80 parts by mass.
- a maleimide compound (B1) (also referred to as component (B1)) other than the bismaleimide compound (A) can be used in the resin composition.
- the maleimide compound (B1) is described below.
- the maleimide compound (B-1) is not particularly limited as long as it is a compound other than the maleimide compound (A) and has one or more maleimide groups in the molecule.
- Specific examples include N-phenylmaleimide, N-cyclohexylmaleimide, N-hydroxyphenylmaleimide, N-anilinophenylmaleimide, N-carboxyphenylmaleimide, N-(4-carboxy-3-hydroxyphenyl)maleimide, 6 -maleimidohexanoic acid, 4-maleimidobutyric acid, bis(4-maleimidophenyl)methane, 2,2-bis ⁇ 4-(4-maleimidophenoxy)-phenyl ⁇ propane, 4,4-diphenylmethanebismaleimide, bis(3, 5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, bis(3,
- maleimide compound represented by the following formula (6) a commercially available product can be used, for example, BMI-2300 (trade name) manufactured by Daiwa Kasei Kogyo Co., Ltd. can be mentioned.
- maleimide compound represented by the following formula (7) a commercially available product can be used, for example, MIR-3000 (trade name) manufactured by Nippon Kayaku Co., Ltd. can be mentioned.
- maleimide compound represented by the following formula (8) a commercially available product can be used, for example, MIR-5000 (trade name) manufactured by Nippon Kayaku Co., Ltd. can be mentioned.
- each R 7 independently represents a hydrogen atom or a methyl group.
- n 3 represents an integer of 1 or more, preferably an integer of 1-10, more preferably an integer of 1-5.
- each R 8 independently represents a hydrogen atom or a methyl group.
- n 4 represents an integer of 1 or more, preferably an integer of 1-5.
- each R 9 independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group; each l 2 independently represents an integer of 1 to 3 ; , represents an integer from 1 to 10.
- alkyl groups having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, and neopentyl groups.
- a chloroform solution containing 1% by mass of the maleimide compound (B1) is prepared in order to efficiently cause the photoradical reaction of the bismaleimide compound (A), and includes a wavelength of 365 nm (i line).
- the transmittance of this chloroform solution is measured using an active energy ray, it preferably exhibits a light transmittance of 5% or more. In this case, the transmittance is more preferably 8% or more, more preferably 10% or more.
- a chloroform solution containing 1% by mass of the maleimide compound (B1) was prepared, and an active energy ray containing a wavelength of 405 nm (h-line) was prepared.
- the transmittance of this chloroform solution is measured using , it preferably exhibits a light transmittance of 5% or more.
- the maleimide compound (B1) for example, when producing a printed wiring board having a high-density and high-definition wiring formation (pattern) using a direct drawing exposure method, an activity including a wavelength of 405 nm (h-line) Even when an energy beam is used, the photoradical reaction of maleimide occurs efficiently.
- the light transmittance is more preferably 8% or more, and even more preferably 10% or more, because a resin composition having excellent photocurability can be obtained.
- Examples of the maleimide compound (B-1) include a maleimide compound represented by the following formula (9), a maleimide compound represented by the following formula (10), a maleimide compound represented by the following formula (17), and the like. a maleimide compound represented by the following formula (11), a maleimide compound represented by the following formula (12), a maleimide compound represented by the following formula (13), a maleimide compound represented by the following formula (14), 1, 6-bismaleimide-(2,2,4-trimethyl)hexane (a maleimide compound represented by the following formula (14)), a maleimide compound represented by the following formula (16), and fluorescein-5-maleimide. .
- n 6 (average) is 1 or more, preferably 1 to 21, and more preferably 1 to 16 from the viewpoint of exhibiting excellent photocurability.
- the number of x is 10-35.
- the number of y is 10-35.
- R a represents a linear or branched alkyl group having 1 to 16 carbon atoms or a linear or branched alkenyl group having 2 to 16 carbon atoms.
- R a is preferably a linear or branched alkyl group, and more preferably a linear alkyl group because it exhibits excellent photocurability.
- the number of carbon atoms in the alkyl group is preferably 4 to 12, since excellent photocurability is exhibited.
- the number of carbon atoms in the alkenyl group is preferably 4 to 12, since excellent photocurability is exhibited.
- R 3 in the bismaleimide compound (A) can be referred to.
- an n-heptyl group, an n-octyl group, and an n-nonyl group are preferred, and an n-octyl group is more preferred, since they exhibit excellent photocurability.
- R 3 in the bismaleimide compound (A) can be referred to.
- a 2-heptenyl group, a 2-octenyl group and a 2-nonenyl group are preferred, and a 2-octenyl group is more preferred, since they exhibit excellent photocurability.
- R b represents a linear or branched alkyl group having 1 to 16 carbon atoms or a linear or branched alkenyl group having 2 to 16 carbon atoms.
- R b is preferably a linear or branched alkyl group, more preferably a linear alkyl group because it exhibits excellent photocurability.
- the number of carbon atoms in the alkyl group is preferably 4 to 12, since excellent photocurability is exhibited.
- the number of carbon atoms in the alkenyl group is preferably 4 to 12, since excellent photocurability is exhibited.
- the alkyl group for R a can be referred to.
- an n-heptyl group, an n-octyl group, and an n-nonyl group are preferred, and an n-octyl group is more preferred, since they exhibit excellent photocurability.
- an alkenyl group for R a can be referred to.
- a 2-heptenyl group, a 2-octenyl group and a 2-nonenyl group are preferred, and a 2-octenyl group is more preferred, since they exhibit excellent photocurability.
- the number of n a is 1 or more, preferably 2 to 16, more preferably 3 to 14 from the viewpoint of exhibiting excellent photocurability.
- n b is 1 or more, preferably 2 to 16, more preferably 3 to 14 from the viewpoint of exhibiting excellent photocurability.
- n a and n b may be the same or different.
- n 7 (average) is 0.5 or more, preferably 0.8 to 10, more preferably 1 to 8 from the viewpoint of exhibiting excellent photocurability.
- n 8 represents an integer of 1 or more, preferably an integer of 1-10.
- n 9 represents an integer of 1 or more, preferably an integer of 1-10.
- each R 10 independently represents a hydrogen atom, a methyl group or an ethyl group
- each R 11 independently represents a hydrogen atom or a methyl group.
- a commercially available product can also be used as the maleimide compound (B-1).
- maleimide compound represented by the formula (11) for example, Designer Molecules Inc. BMI-689 (trade name, formula (17) below, functional group equivalent: 346 g/eq.), and the like.
- a commercially available product such as Designer Molecules Inc. can be used.
- (DMI) BMI-1700 trade name
- a commercially available product such as Designer Molecules Inc. can be used.
- DMI BMI-3000 (trade name), Designer Molecules Inc. (DMI) BMI-5000 (trade name), Designer Molecules Inc. (DMI) BMI-9000 (trade name).
- maleimide compound represented by the formula (15) a commercially available product can be used, for example, BMI-TMH (trade name) manufactured by Daiwa Kasei Kogyo Co., Ltd. can be mentioned.
- maleimide compound represented by the formula (16) a commercially available product can be used, for example, BMI-70 (trade name) manufactured by K.I. Kasei Co., Ltd. can be mentioned.
- These maleimide compounds (B1) can be used singly or in admixture of two or more.
- the content of the maleimide compound (B1) is preferably 0.00 parts per 100 parts by mass in total of the bismaleimide compound (A), the maleimide compound (B-1) and the photo-curing initiator (C). It is preferably 5 to 85 parts by mass.
- a cyanate ester compound (B-2) (also referred to as component (B-2)) can be used in the resin composition.
- the cyanate ester compound (B-2) is described below.
- the cyanate ester compound is not particularly limited as long as it is a resin having an aromatic moiety substituted with at least one cyanato group (cyanate ester group) in the molecule.
- Ar 1 represents a benzene ring, a naphthalene ring, or a single bond of two benzene rings. When there are more than one, they may be the same or different. Ar 1 is preferably a naphthalene ring.
- Each Ra is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms.
- Ra is preferably a hydrogen atom.
- the aromatic ring in Ra may have a substituent, and the substituents in Ar 1 and Ra can be selected at arbitrary positions.
- p represents the number of cyanato groups bonded to Ar 1 and each independently represents an integer of 1 to 3, preferably 1;
- q represents the number of Ra atoms bonded to Ar1, and is 4-p when Ar1 is a benzene ring, 6-p when it is a naphthalene ring, and 8-p when two benzene rings are single-bonded.
- t represents the average number of repetitions and is an integer of 0-50, preferably an integer of 1-30, more preferably an integer of 1-10.
- the cyanate ester compound may be a mixture of compounds with different t.
- -NRN- where R represents an organic group
- the alkyl group for Ra in formula (18) may have either a linear or branched chain structure or a cyclic structure (for example, a cycloalkyl group, etc.). Further, the hydrogen atom in the alkyl group in the formula (18) and the aryl group in Ra is substituted with a halogen atom such as a fluorine atom or a chlorine atom, an alkoxyl group such as a methoxy group or a phenoxy group, or a cyano group. good too.
- alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 1-ethylpropyl and 2,2-dimethylpropyl. group, cyclopentyl group, hexyl group, cyclohexyl group, trifluoromethyl group and the like.
- alkenyl groups include vinyl, (meth)allyl, isopropenyl, 1-propenyl, 2-butenyl, 3-butenyl, 1,3-butandienyl, and 2-methyl-2-propenyl. , 2-pentenyl group, and 2-hexenyl group.
- aryl groups include phenyl, xylyl, mesityl, naphthyl, phenoxyphenyl, ethylphenyl, o-, m- or p-fluorophenyl, dichlorophenyl, dicyanophenyl and trifluorophenyl. groups, methoxyphenyl groups, o-, m- or p-tolyl groups, and the like.
- alkoxyl groups include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, and tert-butoxy groups.
- divalent organic group having 1 to 50 carbon atoms for X in formula (18) include a methylene group, an ethylene group, a trimethylene group, a cyclopentylene group, a cyclohexylene group, a trimethylcyclohexylene group, and a biphenylylmethylene group. dimethylmethylene-phenylene-dimethylmethylene group, methylene-phenylene-methylene group, fluorenediyl group, and phthalidodiyl group. Among these, a methylene-phenylene-methylene group is preferred.
- a hydrogen atom in the divalent organic group may be substituted with a halogen atom such as a fluorine atom or a chlorine atom, an alkoxyl group such as a methoxy group or a phenoxy group, a cyano group, or the like.
- a halogen atom such as a fluorine atom or a chlorine atom
- an alkoxyl group such as a methoxy group or a phenoxy group
- a cyano group or the like.
- Examples of the divalent organic group having 1 to 10 nitrogen atoms in X of the formula (18) include an imino group and a polyimide group.
- examples of the organic group of X in the formula (18) include those having a structure represented by the following formula (19) or the following formula (20).
- Ar 2 represents a benzenediyl group, a naphthalenediyl group or a biphenyldiyl group, and when u is an integer of 2 or more, they may be the same or different.
- Rb, Rc, Rf, and Rg are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trifluoromethyl group, or an aryl having at least one phenolic hydroxy group indicates a group.
- Rd and Re are each independently selected from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a hydroxy group.
- . u represents an integer of 0 to 5;
- Ar 3 represents a benzenediyl group, a naphthalenediyl group or a biphenyldiyl group, and when v is an integer of 2 or more, they may be the same or different.
- Ri and Rj are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a benzyl group, an alkoxyl group having 1 to 4 carbon atoms, a hydroxy group, a trifluoromethyl group, or an aryl group substituted with at least one cyanato group.
- v represents an integer of 0 to 5, it may be a mixture of compounds with different v.
- X in the formula (18) includes a divalent group represented by the following formula.
- z represents an integer of 4-7.
- Each Rk independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- Specific examples of Ar 2 in the formula (19) and Ar 3 in the formula (20) include two carbon atoms represented by the formula (19) or two oxygen atoms represented by the formula (20). , benzenediyl groups bonded to the 1,4- or 1,3-positions, two carbon atoms or two oxygen atoms at the 4,4'-, 2,4'-, 2,2'-, 2,3-positions.
- the biphenyldiyl groups attached to the ', 3,3', or 3,4' positions and two carbon atoms or two oxygen atoms are 2,6, 1,5, 1,6 1,8-position, 1,3-position, 1,4-position, or 2,7-position binding naphthalenediyl groups.
- the alkyl group and aryl group for Rb, Rc, Rd, Re, Rf and Rg in formula (19) and Ri and Rj in formula (20) are the same as in formula (18) above.
- cyanato-substituted aromatic compound represented by the formula (18) include cyanatobenzene, 1-cyanato-2-, 1-cyanato-3-, or 1-cyanato-4-methylbenzene, 1- cyanato-2-,1-cyanato-3-, or 1-cyanato-4-methoxybenzene, 1-cyanato-2,3-,1-cyanato-2,4-,1-cyanato-2,5-,1 -cyanato-2,6-,1-cyanato-3,4- or 1-cyanato-3,5-dimethylbenzene, cyanatoethylbenzene, cyanatobutylbenzene, cyanatooctylbenzene, cyanatononylbenzene, 2-( 4-cyanaphenyl)-2-phenylpropane (cyanate of 4- ⁇ -cumylphenol), 1-cyanato-4-cyclohexylbenzene, 1-cyanato-4-vinylbenzen
- cyanate ester compounds can be used singly or in an appropriate mixture of two or more.
- cyanate ester compound represented by the above formula (18) examples include phenol novolac resins and cresol novolac resins (by a known method, phenol, alkyl-substituted phenol or halogen-substituted phenol, formalin, paraformaldehyde, etc.).
- Ar 4 —(CH 2 OR) 2 (R represents an alkyl group) and a phenolic compound reacted in the presence of an acidic catalyst or Ar A bis(hydroxymethyl) compound represented by 4- (CH 2 OH) 2 and a phenol compound are reacted in the presence of an acidic catalyst, or an aromatic aldehyde compound, an aralkyl compound and a phenol compound are polymerized.
- phenol-modified xylene formaldehyde resin by a known method, a xylene formaldehyde resin and a phenolic compound are reacted in the presence of an acidic catalyst
- modified naphthalene formaldehyde resin by a known method, a naphthalene formaldehyde resin and a hydroxy-substituted aromatic compound in the presence of an acidic catalyst
- a phenol-modified dicyclopentadiene resin a phenolic resin having a polynaphthylene ether structure
- a known method a phenolic hydroxy group in one molecule polyhydric hydroxynaphthalene compounds having two or more polyhydric naphthalene compounds, in the presence of a basic catalyst, dehydration-condensed
- These cyanate ester compounds can be used singly or in admixture of
- the method for producing these cyanate ester compounds is not particularly limited, and known methods can be used.
- An example of such a production method includes obtaining or synthesizing a hydroxy group-containing compound having a desired skeleton, and modifying the hydroxy group by a known technique to form a cyanate.
- Methods for cyanating a hydroxy group include, for example, the methods described in Ian Hamerton, Chemistry and Technology of Cyanate Ester Resins, Blackie Academic & Professional.
- Cured products using these cyanate ester compounds have excellent properties such as glass transition temperature, low thermal expansion, and plating adhesion.
- the content of the cyanate ester compound is 0.5 with respect to a total of 100 parts by mass of the bismaleimide compound (A), the cyanate ester compound (B-2) and the photocuring initiator (C). It is preferably to 85 parts by mass.
- a benzoxazine compound (B-3) (also referred to as component (B-3)) can be used in the resin composition.
- the benzoxazine compound (B-3) is described below.
- Benzoxazine compounds also include compounds having a polycyclic oxazine skeleton such as naphthoxazine compounds.
- the compound represented by Formula (21) and the compound represented by Formula (22) are preferable from the viewpoint of obtaining good photocurability.
- each R 12 independently represents a hydrogen atom, an aryl group, an aralkyl group, an alkenyl group, an alkyl group, or a cycloalkyl group.
- Each n 10 independently represents an integer of 1-4.
- Each R 13 independently represents a hydrogen atom, an aryl group, an aralkyl group, an alkenyl group, an alkyl group, or a cycloalkyl group.
- Each n 11 independently represents an integer of 1-4.
- T 1 represents an alkylene group, a group represented by formula (22), a group represented by formula "--SO 2 --", a group represented by "--CO--", an oxygen atom, or a single bond.
- the aryl group for both R 12 and R 13 is preferably an aryl group having 6 to 18 carbon atoms.
- the aryl group include phenyl group, naphthyl group, indenyl group, biphenyl group, and anthryl group. Among them, a phenyl group is more preferable.
- These aryl groups may have one or more, preferably 1 to 3, lower alkyl groups having 1 to 4 carbon atoms. Examples of aryl groups having such lower alkyl groups include tolyl, xylyl, and methylnaphthyl groups.
- the aralkyl groups for both R 12 and R 13 are preferably benzyl and phenethyl groups. These may have one or more, preferably in the range of 1 to 3, lower alkyl groups having 1 to 4 carbon atoms on the phenyl group.
- alkenyl groups for both R 12 and R 13 include vinyl, (meth)allyl, propenyl, butenyl, and hexenyl groups.
- a vinyl group, an allyl group, and a propenyl group are preferable, and an allyl group is more preferable.
- the alkyl group for both R 12 and R 13 is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.
- Alkyl groups having 3 or more carbon atoms may be linear or branched.
- methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, neopentyl group, n-hexyl group, thexyl group examples include n-heptyl, n-octyl, n-ethylhexyl, n-nonyl, and n-decyl groups.
- cycloalkyl groups for both R 12 and R 13 include cyclopentyl, cyclohexyl, and cycloheptyl groups.
- a cyclohexyl group is preferred.
- the alkylene group for T 1 is preferably a linear or branched alkylene group.
- Linear alkylene groups include, for example, methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decanylene, trimethylene, tetramethylene, and pentamethylene. and hexamethylene groups.
- Branched alkylene groups include, for example, -C(CH 3 ) 2 -, -CH(CH 3 )-, -CH(CH 2 CH 3 )-, -C(CH 3 )(CH 2 CH 3 ) alkylmethylene groups of -, -C(CH 3 )(CH 2 CH 2 CH 3 )-, and -C(CH 2 CH 3 ) 2 -; -CH(CH 3 )CH 2 -, -CH(CH 3 ) CH(CH 3 )—, —C(CH 3 ) 2 CH 2 —, —CH(CH 2 CH 3 )CH 2 —, and —C(CH 2 CH 3 ) 2 —CH 2 — alkylethylene groups. be done.
- each R 14 independently represents a hydrogen atom, an aryl group, an aralkyl group, an alkenyl group, an alkyl group, or a cycloalkyl group.
- Each n 12 independently represents an integer of 1 to 3.
- Each R15 independently represents a hydrogen atom, an aryl group, an aralkyl group, an alkenyl group, an alkyl group, or a cycloalkyl group.
- Each n 13 independently represents an integer of 1 to 5.
- T 2 represents an alkylene group, a group represented by formula (22), a group represented by formula "--SO 2 --", a group represented by "--CO--", an oxygen atom, or a single bond.
- the aryl group, aralkyl group, alkenyl group, alkyl group and cycloalkyl group for both R 14 and R 15 are as described above.
- the alkylene group for T 2 is as described above.
- Z is an alkylene group or a hydrocarbon group having 6 or more and 30 or less carbon atoms having an aromatic ring.
- n14 represents an integer of 0 or more and 5 or less.
- n 14 is preferably an integer of 1 or more and 3 or less, more preferably 1 or 2.
- the alkylene group for Z is as described above.
- hydrocarbon groups having 6 to 30 carbon atoms and having an aromatic ring include aromatic compounds such as benzene, biphenyl, naphthalene, anthracene, fluorene, phenanthlene, indacene, terphenyl, acenaphthylene, and phenalene. and a divalent group obtained by removing two hydrogen atoms from the nucleus.
- benzoxazine compound (B-3) a commercially available product may be used. 3,4-dihydro-2H-1,3-benzoxazine), compound represented by formula (20)), Fa-type benzoxazine (manufactured by Shikoku Kasei Kogyo Co., Ltd., 2,2-bis(3,4- Dihydro-2H-3-phenyl-1,3-benzoxazinyl)methane, compound represented by formula (21)), bisphenol A-type benzoxazine BA-BXZ (manufactured by Konishi Chemical Industry Co., Ltd., trade name) Bisphenol F-type benzoxazine BF-BXZ (manufactured by Konishi Chemical Industry Co., Ltd., trade name), bisphenol S-type benzoxazine BS-BXZ (manufactured by Konishi Chemical Industry Co., Ltd., trade name), phenolphthalein-type benzoxazine, etc. is mentioned.
- benzoxazine compounds (B-3) can be used singly or in admixture of two or more.
- the benzoxazine compound is preferably a compound represented by the formula (20) or a compound represented by the formula (21) because it has good heat resistance, and 3,3′-(methylene-1,4 -diphenylene)bis(3,4-dihydro-2H-1,3-benzoxazine is more preferred.
- the content of the benzoxazine compound is 0.5 to 85 with respect to a total of 100 parts by mass of the bismaleimide compound (A), the benzoxazine compound (B-3) and the photocuring initiator (C). Parts by mass are preferred.
- Epoxy resin (B-4) (also referred to as component (B-4)) can be used in the resin composition.
- the epoxy resin (B-4) is described below.
- a commercially available product can also be used as the epoxy resin.
- Commercially available products include, for example, an epoxy resin (NC-3000FH (trade name) manufactured by Nippon Kayaku Co., Ltd.) represented by the following formula (24), in which n 15 is 3 to 5, about 4), and a naphthalene-type epoxy resin represented by the following formula (25) (HP-4710 (trade name) manufactured by DIC Corporation).
- epoxy resins can be used singly or in admixture of two or more.
- the epoxy resin is preferably an epoxy resin represented by the above formula (23) and an epoxy resin represented by the above formula (24), because the cured product has excellent heat resistance. epoxy resins are more preferred.
- the content of the epoxy resin is 0.5 to 85 parts by mass with respect to a total of 100 parts by mass of the bismaleimide compound (A), the epoxy resin (B4) and the photocuring initiator (C). is preferred.
- carbodiimide compound A carbodiimide compound (B-5) (also referred to as component (B-5)) can be used in the resin composition.
- the carbodiimide compound (B-5) is described below.
- carbodiimide compounds (B-5) can be used singly or in admixture of two or more.
- Carbodiimide compounds have good heat resistance and have good adhesion to conductor layers when used in insulating layers of printed wiring boards.
- V05 (trade name, manufactured by Nisshinbo Chemical Co., Ltd.) is preferred, and Carbodilite (registered trademark) B-01 (trade name, manufactured by Nisshinbo Chemical Co., Ltd.) is more preferred.
- the content of the carbodiimide compound in the resin composition is preferably 0.5 to 85 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.
- a compound (B-6) having an ethylenically unsaturated group (also referred to as component (B-6)) can be used in the resin composition.
- the compound (B-6) having an ethylenically unsaturated group is described below.
- As the compound (B-6) having an ethylenically unsaturated group generally known compounds can be used as long as they are compounds having one or more ethylenically unsaturated groups in one molecule. Examples thereof include compounds having (meth)acryloyl groups, vinyl groups, and the like.
- Compounds having a (meth)acryloyl group include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, lauryl (meth)acrylate, polyethylene glycol (meth)acrylate, polyethylene glycol (meth)acrylate monomethyl ether , phenylethyl (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, butanediol di(meth)acrylate, hexanediol di(meth)acrylate, Neopentyl glycol di(meth)acrylate, nonanediol di(meth)acrylate, glycol di(meth)acrylate, diethylene di(meth)acrylate, polyethylene glycol di(meth)acrylate, tris(meth)acrylo
- urethane (meth)acrylates having both a (meth)acryloyl group and a urethane bond in the same molecule
- polyester (meth)acrylates having both a (meth)acryloyl group and an ester bond in the same molecule
- epoxy Epoxy (meth)acrylates derived from resins and having (meth)acryloyl groups and reactive oligomers in which these bonds are used in combination.
- Urethane (meth)acrylates include reaction products of hydroxyl group-containing (meth)acrylates, polyisocyanates, and other alcohols used as necessary.
- hydroxyalkyl (meth)acrylates such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, and hydroxybutyl (meth)acrylate;
- sugar alcohol (meth)acrylates such as pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate; and toluene diisocyanate , hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, xylene diisocyanate, hydrogenated x
- Polyester (meth)acrylates include, for example, caprolactone-modified 2-hydroxyethyl (meth)acrylate, ethylene oxide and/or propylene oxide-modified phthalic acid (meth)acrylate, ethylene oxide-modified succinic acid (meth)acrylate, caprolactone-modified tetrahydro Monofunctional (poly)ester (meth)acrylates such as furfuryl (meth)acrylate; hydroxypivalic acid ester neopentyl glycol di(meth)acrylate, caprolactone-modified hydroxypivalic acid ester neopentyl glycol di(meth)acrylate, epichlorohydrin-modified Di (poly) ester (meth) acrylates such as phthalic acid di (meth) acrylate; 1 mol or more of cyclic lactone compounds such as ⁇ -caprolactone, ⁇ -butyrolactone, and ⁇ -valerolactone per 1 mol of tri
- mono-triol obtained by adding 1 mol or more of a cyclic lactone compound such as ⁇ -caprolactone, ⁇ -butyrolactone, ⁇ -valerolactone to 1 mol of pentaerythritol, dimethylolpropane, trimethylolpropane, or tetramethylolpropane; Di-, tri- or tetra-(meth)acrylates; triols obtained by adding 1 mol or more of a cyclic lactone compound such as ⁇ -caprolactone, ⁇ -butyrolactone, ⁇ -valerolactone to 1 mol of dipentaerythritol, or poly( Examples include mono(meth)acrylates or poly(meth)acrylates of polyhydric alcohols such as triols, tetraols, pentaols or hexaols of meth)acrylates.
- a cyclic lactone compound such as ⁇ -caprolactone, ⁇
- diol components such as (poly)ethylene glycol, (poly)propylene glycol, (poly)tetramethylene glycol, (poly)butylene glycol, 3-methyl-1,5-pentanediol, hexanediol, maleic acid, fumaric Polybasic acids such as acid, succinic acid, adipic acid, phthalic acid, isophthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, dimer acid, sebacic acid, azelaic acid, 5-sodium sulfoisophthalic acid, and anhydrides thereof (meth)acrylate of polyester polyol which is the reaction product of; (meth)acrylate of cyclic lactone-modified polyester diol composed of diol component, polybasic acid and their anhydrides and ⁇ -caprolactone, ⁇ -butyrolactone, ⁇ -valerolactone, etc. and polyfunctional (poly)
- Epoxy (meth)acrylates are carboxylate compounds of a compound having an epoxy group and (meth)acrylic acid.
- phenol novolak type epoxy (meth)acrylate cresol novolak type epoxy (meth)acrylate, trishydroxyphenylmethane type epoxy (meth)acrylate, dicyclopentadiene phenol type epoxy (meth)acrylate, bisphenol A type epoxy (meth)acrylate.
- bisphenol F type epoxy (meth)acrylate bisphenol F type epoxy (meth)acrylate, biphenol type epoxy (meth)acrylate, bisphenol A novolac type epoxy (meth)acrylate, naphthalene skeleton-containing epoxy (meth)acrylate, glyoxal type epoxy (meth)acrylate, heterocyclic epoxy ( meth)acrylates, and acid anhydride-modified epoxy acrylates thereof.
- Examples of compounds having a vinyl group include vinyl ethers such as ethyl vinyl ether, propyl vinyl ether, hydroxyethyl vinyl ether, and ethylene glycol divinyl ether; styrenes such as styrene, methylstyrene, ethylstyrene, and divinylbenzene.
- Other vinyl compounds include triallyl isocyanurate, trimethallyl isocyanurate, bisallyl nadiimide, and the like.
- the compound having an ethylenically unsaturated group commercially available products can be used.
- dicyclopentadiene phenol epoxy acrylate manufactured by Nippon Kayaku Co., Ltd., registered trademark
- ZXA-101H trade name
- an acid-modified dicyclopentadiene phenol-type epoxy acrylate manufactured by Nippon Kayaku Co., Ltd., KAYARAD (registered trademark) ZXA-1807H
- 2-7 is a compound represented by the following formula (27) (trade name), KAYARAD® ZXR-1810H (trade name), KAYARAD® ZXR-1816H (trade name), and KAYARAD® ZXR-1889H (trade name)).
- n 16 represents an integer of 0-10. n 16 is preferably an integer of 0 to 5 from the viewpoint of obtaining more suitable viscosity and being able to control the increase in viscosity of the varnish.
- n 17 represents an integer of 0-10. n 17 is preferably an integer of 0 to 5 from the viewpoint of obtaining a more suitable viscosity and being able to control the increase in the viscosity of the varnish.
- ethylenically unsaturated group-containing compounds (B-6) can be used singly or in admixture of two or more.
- the compound having an ethylenically unsaturated group propylene glycol monomethyl ether acetate, which is a dicyclopentadiene phenol type epoxy acrylate compound, is preferable because it has good thermal stability.
- the content of the compound having an ethylenically unsaturated group is, with respect to a total of 100 parts by mass of the bismaleimide compound (A), the benzoxazine compound (B-3) and the photocuring initiator (C), It is preferably 0.5 to 85 parts by mass.
- the resin composition according to the present embodiment contains a photocuring initiator (C) (also referred to as component (C)).
- a photocuring initiator (C) also referred to as component (C)
- the photocuring initiator (C) those known in the field generally used in photocurable resin compositions can be used.
- the photocuring initiator (C) is used together with the bismaleimide compound (A) and the resin or compound (B) for photocuring using various active energy rays.
- benzoin such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether, benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl Peroxides and organic peroxides exemplified by di-tert-butyl-di-peroxyphthalate; 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethyl phosphine oxides such as benzoyl)-phenylphosphine oxide; acetophenone, 2,2-diethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 2-hydroxy-2 -methyl-phenylpropan-1-one, diethoxyacetophenone, 1-hydroxych
- a commercially available product can also be used as the photo-curing initiator (C).
- Examples of commercially available products include Omnirad (registered trademark) 369 (trade name) manufactured by IGM Resins, Omnirad (registered trademark) 819 (trade name) manufactured by IGM Resins, Omnirad (registered trademark) 819DW (trade name) manufactured by IGM Resins.
- Omnirad (registered trademark) 907 (trade name) manufactured by IGM Resins
- Omnirad (registered trademark) TPO (trade name) manufactured by IGM Resins
- Omnirad (registered trademark) TPO-L (trade name) manufactured by IGM Resins
- IGM Omnirad (registered trademark) 784 (trade name) manufactured by Resins
- Irgacure (registered trademark) OXE01 (trade name) manufactured by BASF Japan K.K.
- Irgacure (trademark) OXE02 (trade name) manufactured by BASF Japan K.K., BASF Japan K.K.
- photo-curing initiators (C) can be used singly or in admixture of two or more.
- the photocuring initiator (C) is prepared by preparing a chloroform solution containing 0.01% by mass, and using an active energy ray containing a wavelength of 365 nm (i-line), the photocuring initiator (C) When measuring the absorbance of a chloroform solution containing 0.01% by mass, the absorbance is preferably 0.1 or more, and this photocuring initiator (C) exhibits very good absorbance. . In addition, when the absorbance of a chloroform solution containing 0.01% by mass of a photocuring initiator (C) is measured using an active energy ray having a wavelength of 405 nm (h-line), the absorbance is 0.1.
- the photocuring initiator (C) when producing a printed wiring board having a high-density and high-definition wiring formation (pattern) using a direct drawing exposure method, Even when active energy rays are used, the photoradical reaction of maleimide occurs efficiently.
- the absorbance at a wavelength of 365 nm (i-line) is more preferably 0.15 or more because a resin composition having excellent photocurability can be obtained.
- the absorbance at a wavelength of 405 nm (h-line) is more preferably 0.15 or more because a resin composition with excellent photocurability can be obtained.
- the upper limit of the absorbance at a wavelength of 365 nm (i-line) and the absorbance at a wavelength of 405 nm (h-line) is, for example, 99.9 or less.
- a compound represented by the following formula (2) is preferable as the photocuring initiator (C).
- each R 4 independently represents a substituent represented by formula (3) below or a phenyl group.
- each R 5 independently represents a hydrogen atom or a methyl group.
- -* represents a bond with the phosphorus atom (P) in formula (2).
- the compound represented by the formula (2) For the compound represented by the formula (2), prepare a chloroform solution containing 0.01% by mass of this compound, and measure the absorbance of this chloroform solution using an active energy ray containing a wavelength of 365 nm (i-line).
- the absorbance is 0.1 or more, showing very excellent absorption of light with a wavelength of 365 nm (i-line). Therefore, this compound suitably generates radicals with respect to light with a wavelength of 365 nm (i-line).
- the absorbance is preferably 0.15 or more.
- the upper limit is, for example, 5.0 or less, and may be 10.0 or less.
- the compound represented by the formula (2) is obtained by preparing a chloroform solution containing 0.01% by mass of this compound, and using an active energy ray containing a wavelength of 405 nm (h-line) to measure the absorbance of this chloroform solution. is measured, the absorbance is 0.1 or more, showing very excellent absorbency for light with a wavelength of 405 nm (h-line). Therefore, this compound suitably generates radicals with respect to light with a wavelength of 405 nm (h-line).
- the absorbance is preferably 0.15 or more.
- the upper limit is, for example, 5.0 or less, and may be 10.0 or less.
- each R 4 independently represents a substituent represented by formula (3) or a phenyl group. At least one of R 4 is preferably a substituent represented by formula (3).
- each R 5 independently represents a hydrogen atom or a methyl group. At least one of R 5 is preferably a methyl group, and more preferably all are methyl groups.
- Examples of the compound represented by the formula (2) include phosphine such as 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide. fin oxides. Among these, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide is preferred because it has excellent light transmittance. These compounds can be used singly or in admixture of two or more.
- Acylphosphine oxides exhibit very excellent absorption of active energy rays including a wavelength of 405 nm (h-line), for example, a bismaleimide compound having a transmittance of 5% or more at a wavelength of 405 nm (h-line).
- (A) can be preferably radically polymerized. Therefore, especially when used for a multilayer printed wiring board, the resin composition, the resin sheet, which has excellent photocurability and can obtain a cured product having a good balance of heat resistance, thermal stability and insulation reliability, It is possible to suitably manufacture a multilayer printed wiring board and a semiconductor device using them.
- the content of the photocuring initiator (C) allows the photocuring of the bismaleimide compound (A) and the resin or compound (B) to proceed sufficiently, resulting in better heat resistance and thermal stability.
- the viewpoint of obtaining the bismaleimide compound (A), the resin or compound (B), and the photocuring initiator (C), with respect to a total of 100 parts by mass it is preferably 0.1 to 10 parts by mass, and 1 to It is more preferably 8 parts by mass, and even more preferably 2 to 7 parts by mass.
- the resin composition of the present embodiment can also contain a filler (D) (also referred to as component (D)) in order to improve various properties such as coating properties and heat resistance.
- a filler (D) also referred to as component (D)
- Examples of the filler (D) include silica (e.g., natural silica, fused silica, amorphous silica, hollow silica, etc.), aluminum compounds (e.g., boehmite, aluminum hydroxide, alumina, aluminum nitride, etc.), and boron compounds.
- silica e.g., natural silica, fused silica, amorphous silica, hollow silica, etc.
- aluminum compounds e.g., boehmite, aluminum hydroxide, alumina, aluminum nitride, etc.
- boron compounds e.g., boron compounds.
- fillers (D) can be used singly or in admixture of two or more.
- magnesium compounds e.g., magnesium oxide, magnesium hydroxide, etc.
- calcium compounds e.g., calcium carbonate, etc.
- molybdenum compounds e.g., molybdenum oxide, zinc molybdate, etc.
- barium compounds e.g., barium sulfate, barium silicate, etc.
- talc e.g., natural talc, calcined talc, etc.
- mica e.g., glass, e.g., short fiber glass, spherical glass, fine powder glass, E glass, T glass, and D glass, etc.
- silicone powder fluororesin fillers, urethane resin fillers, (meth)acrylic resin fillers, polyethylene fillers, styrene-butadiene rubbers, and silicone rubbers.
- These fillers (D) can be used singly or in admixture
- fillers (D) may be surface-treated with a silane coupling agent or the like, which will be described later.
- Silica is preferable, and fused silica is more preferable, from the viewpoint of improving the heat resistance of the cured product and obtaining good coating properties.
- Specific examples of silica include SFP-130MC (trade name) manufactured by Denka Corporation, SC2050-MB (trade name), SC1050-MLE (trade name) and YA010C-MFN (trade name) manufactured by Admatechs Co., Ltd. ), and YA050C-MJA (trade name).
- the particle size of the filler (D) is usually 0.005 to 10 ⁇ m, preferably 0.01 to 1.0 ⁇ m, from the viewpoint of the ultraviolet light transmittance of the resin composition.
- the content of the filler (D) is, from the viewpoint of improving the light transmittance of the resin composition and the heat resistance of the cured product, the bismaleimide compound (A), the resin or It is preferably 300 parts by mass or less, more preferably 200 parts by mass or less, and 100 parts by mass or less with respect to a total of 100 parts by mass of the compound (B) and the photocuring initiator (C). More preferred.
- the upper limit may be 30 parts by mass or less, 20 parts by mass or less, or 10 parts by mass or less.
- the lower limit is the bismaleimide compound (A), the resin or the compound (B) and the It is usually 1 part by mass with respect to a total of 100 parts by mass of the photocuring initiator (C).
- silane coupling agent and wetting and dispersing agent The resin composition of the present embodiment may be used in combination with a silane coupling agent and/or a wetting and dispersing agent in order to improve the dispersibility of the filler and the adhesive strength between the polymer and/or resin and the filler. can.
- silane coupling agents are not limited as long as they are silane coupling agents generally used for surface treatment of inorganic substances.
- Specific examples include 3-aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, 3-aminopropyldimethoxymethylsilane, 3-aminopropyldiethoxymethylsilane, N- ⁇ -(aminoethyl)- ⁇ -amino Propyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropyldimethoxymethylsilane, N-(2-aminoethyl)-3- aminopropyldiethoxymethylsilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, [3-(6-aminohexylamino)propyl]trimethoxysilane, and [3 Ami
- ureidosilanes such as; styrylsilanes such as p-styryltrimethoxysilane; cationic silanes such as N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ -aminopropyltrimethoxysilane hydrochloride; anhydride-based such as trimethoxysilyl)propyl]succinic anhydride; phenylsilane-based such as phenyltrimethoxysilane, phenyltriethoxysilane, dimethoxymethylphenylsilane, diethoxymethylphenylsilane, and p-tolyltrimethoxysilane.
- Arylsilane systems such as trimethoxy(1-naphthyl)silane are included.
- the content of the silane coupling agent is usually based on a total of 100 parts by mass of the bismaleimide compound (A), the resin or compound (B) and the photocuring initiator (C), It is 0.1 to 10 parts by mass.
- the wetting and dispersing agent is not particularly limited as long as it is a dispersion stabilizer used for paints. Specific examples include DISPERBYK (registered trademark)-110 (trade name), 111 (trade name), 118 (trade name), 180 (trade name), 161 (trade name), and BYK manufactured by Big Chemie Japan Co., Ltd.
- wetting and dispersing agents can be used singly or in combination of two or more.
- the content of the wetting and dispersing agent is usually 0 with respect to a total of 100 parts by mass of the bismaleimide compound (A), the resin or compound (B) and the photocuring initiator (C). .1 to 10 parts by mass.
- the resin composition of the present embodiment preferably contains a curing accelerator as necessary in order to appropriately adjust the curing speed.
- a curing accelerator those generally used as curing accelerators such as cyanate ester compounds can be used.
- curing accelerators include organic metal salts such as zinc octoate, zinc naphthenate, cobalt naphthenate, copper naphthenate, iron acetylacetonate, nickel octylate, and manganese octylate; phenol, xylenol, cresol, resorcinol, catechol , octylphenol, and nonylphenol; alcohols such as 1-butanol and 2-ethylhexanol; 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 1-cyanoethyl-2-phenyl Imidazoles such as imidazole, 1-cyanoethyl-2-ethyl
- curing accelerators can be used singly or in admixture of two or more.
- the content of the curing accelerator is usually 0 with respect to a total of 100 parts by mass of the bismaleimide compound (A), the resin or compound (B) and the photocuring initiator (C). .1 to 20 parts by mass.
- the resin composition of the present embodiment may contain an organic solvent, if necessary. By using an organic solvent, it is possible to adjust the viscosity during preparation of the resin composition.
- the type of organic solvent is not particularly limited as long as it can dissolve part or all of the resin in the resin composition.
- organic solvents examples include ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; alicyclic ketones such as cyclopentanone and cyclohexanone; cellosolve solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; Ester solvents such as ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, methyl methoxypropionate, methyl hydroxyisobutyrate, and ⁇ -butyrolactone; Polar solvents such as amides such as dimethylacetamide and dimethylformamide and non-polar solvents such as aromatic hydrocarbons such as toluene, xylene and anisole. These organic solvents can be used singly or in admixture of two or more.
- the resin composition of the present embodiment includes various high-performance resins such as thermosetting resins, thermoplastic resins, oligomers thereof, and elastomers that have not been mentioned so far, as long as the properties of the present embodiment are not impaired.
- Molecular compounds; flame-retardant compounds not mentioned heretofore; additives and the like can also be used in combination. These are not particularly limited as long as they are commonly used.
- flame-retardant compounds include nitrogen-containing compounds such as melamine and benzoguanamine, oxazine ring-containing compounds, phosphate compounds of phosphorus compounds, aromatic condensed phosphates, and halogen-containing condensed phosphates.
- Additives include ultraviolet absorbers, antioxidants, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, lubricants, antifoaming agents, surface modifiers, brighteners, polymerization inhibitors, thermosetting Accelerators and the like. These components can be used singly or in admixture of two or more.
- the content of other components is usually each with respect to a total of 100 parts by mass of the bismaleimide compound (A), the resin or compound (B), and the photocuring initiator (C). It is 0.1 to 10 parts by mass.
- the resin composition of the present embodiment includes a bismaleimide compound (A), a resin or compound (B), a photocuring initiator (C), and optionally a filler (D), other resins, and other compounds. , and additives are appropriately mixed.
- the resin composition can be suitably used as a varnish for producing a resin sheet of this embodiment, which will be described later.
- the organic solvent used for preparing the varnish is not particularly limited, and specific examples thereof are as described above.
- a method for producing the resin composition includes, for example, a method in which each component described above is sequentially blended in a solvent and thoroughly stirred.
- the resin composition is excellent in photocurability, and the cured product obtained from the resin composition is excellent in heat resistance, thermal stability, and insulation reliability.
- the dispersibility of each component in the resin composition can be improved by performing the stirring and dispersing treatment using a stirring tank equipped with a stirrer having an appropriate stirring capacity.
- Stirring, mixing, and kneading are performed by, for example, a stirring device for dispersion such as an ultrasonic homogenizer, a device for mixing such as a triple roll, a ball mill, a bead mill, and a sand mill, and a revolution or rotation type mixing device. It can be appropriately carried out using a known device such as.
- an organic solvent can be used as necessary during the preparation of the resin composition.
- the type of organic solvent is not particularly limited as long as it can dissolve the resin in the resin composition, and specific examples thereof are as described above.
- the resin composition can be suitably used as a varnish when producing the resin sheet of this embodiment, which will be described later.
- a varnish can be obtained by a well-known method.
- the varnish is prepared by adding 10 to 900 parts by mass of an organic solvent to 100 parts by mass of the components excluding the organic solvent in the resin composition of the present embodiment, and performing the known mixing treatment (stirring, kneading treatment, etc.). can be obtained by doing
- the resin composition can be preferably used for applications that require a resin composition with insulation reliability.
- Applications include, for example, photosensitive films, photosensitive films with supports, prepregs, resin sheets, circuit boards (laminated board applications, multilayer printed wiring board applications, etc.), solder resists, underfill materials, die bonding materials, semiconductor encapsulation. It can be used as a sealing material, hole-filling resin, part-embedding resin, and the like.
- the resin composition is excellent in photocurability, heat resistance and thermal stability, and therefore can be suitably used as an insulating layer of a multilayer printed wiring board or as a solder resist.
- a cured product is obtained by curing the resin composition of the present embodiment.
- the cured product can be obtained, for example, by melting or dissolving the resin composition in a solvent, pouring it into a mold, and curing it under normal conditions using light.
- the wavelength region of light is preferably in the range of 100 to 500 nm where curing proceeds efficiently with a photopolymerization initiator or the like.
- the resin sheet of this embodiment is a support-attached resin sheet having a support and a resin layer disposed on one side or both sides of the support, wherein the resin layer contains a resin composition.
- a resin sheet can be produced by coating a resin composition on a support and drying the resin composition.
- the resin layer in the resin sheet has excellent heat resistance, thermal stability and insulation reliability.
- a known support can be used, but a resin film is preferred.
- resin films include polyimide film, polyamide film, polyester film, polyethylene terephthalate (PET) film, polybutylene terephthalate (PBT) film, polypropylene (PP) film, polyethylene (PE) film, polyethylene naphthalate film, and polyvinyl alcohol. film, triacetyl acetate film, and the like. Among them, PET film is preferred.
- a release agent is preferably applied to the surface of the resin film so that it can be easily separated from the resin layer.
- the thickness of the resin film is preferably in the range of 5-100 ⁇ m, more preferably in the range of 10-50 ⁇ m. When the thickness is less than 5 ⁇ m, the support tends to be torn when the support is peeled off before development. be.
- the resin film preferably has excellent transparency in order to reduce scattering of light during exposure.
- the resin layer may be protected with a protective film.
- a protective film By protecting the resin layer side with a protective film, it is possible to prevent dust from adhering to the surface of the resin layer and scratches on the surface of the resin layer.
- the protective film a film made of the same material as the resin film can be used.
- the thickness of the protective film is preferably in the range of 1-50 ⁇ m, more preferably in the range of 5-40 ⁇ m. If the thickness is less than 1 ⁇ m, the protective film tends to be difficult to handle, and if it exceeds 50 ⁇ m, it tends to be inexpensive.
- the protective film preferably has a lower adhesive strength between the resin layer and the protective film than the adhesive strength between the resin layer and the support.
- the method for producing the resin sheet of the present embodiment is, for example, a method of producing a resin sheet by applying the resin composition of the present embodiment to a support such as a PET film and drying it to remove the organic solvent. etc.
- Coating can be performed by a known method using, for example, a roll coater, comma coater, gravure coater, die coater, bar coater, lip coater, knife coater, squeeze coater, and the like. Drying can be carried out, for example, by heating in a dryer at 60 to 200° C. for 1 to 60 minutes.
- the amount of the organic solvent remaining in the resin layer is preferably 5% by mass or less with respect to the total mass of the resin layer from the viewpoint of preventing diffusion of the organic solvent in subsequent steps.
- the thickness of the resin layer is preferably 1 to 50 ⁇ m from the viewpoint of improving handleability.
- the resin sheet can be preferably used for manufacturing insulating layers of multilayer printed wiring boards.
- the multilayer printed wiring board of this embodiment has an insulating layer and a conductor layer formed on one side or both sides of the insulating layer, and the insulating layer contains a resin composition.
- the insulating layer can also be obtained, for example, by stacking one or more resin sheets and curing them.
- the number of laminations of each of the insulating layer and the conductor layer is not particularly limited, and the number of laminations can be appropriately set according to the intended use. Also, the order of the insulating layer and the conductor layer is not particularly limited.
- the conductor layer may be a metal foil used for various printed wiring board materials, and examples thereof include metal foils of copper, aluminum, and the like. Copper metal foils include copper foils such as rolled copper foils and electrolytic copper foils.
- the thickness of the conductor layer is usually 1-100 ⁇ m. Specifically, it can be produced by the following method.
- the resin layer side of the resin sheet is laminated on one side or both sides of the circuit board using a vacuum laminator.
- circuit substrates include glass epoxy substrates, metal substrates, ceramic substrates, silicon substrates, semiconductor sealing resin substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates.
- the circuit board refers to a board having a patterned conductor layer (circuit) formed on one side or both sides of the board.
- a board in which one or both sides of the outermost layer of the multilayer printed wiring board is a patterned conductor layer (circuit) is also a circuit board.
- the insulating layer laminated on the multilayer printed wiring board may be an insulating layer obtained by stacking one or more resin sheets of the present embodiment and curing the resin sheet of the present embodiment,
- the insulating layer may be obtained by stacking one or more known resin sheets different from the resin sheet of the present embodiment.
- the method of stacking the resin sheet of the present embodiment and a known resin sheet different from the resin sheet of the present embodiment is not particularly limited.
- the surface of the conductor layer may be roughened in advance by blackening and/or copper etching.
- the resin sheet and the circuit board are preheated as necessary to pressurize and heat the resin layer of the resin sheet. while crimping it onto the circuit board.
- a method of laminating a resin layer of a resin sheet on a circuit board under reduced pressure by a vacuum lamination method is preferably used.
- the conditions of the lamination process are, for example, a pressure bonding temperature (laminating temperature) of 50 to 140° C., a pressure of 1 to 15 kgf/cm 2 , a pressure bonding time of 5 to 300 seconds, and an air pressure of 20 mmHg or less under reduced pressure. Lamination is preferred. Moreover, the lamination process may be of a batch type or a continuous type using rolls. A vacuum lamination method can be performed using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include 2-stage build-up laminator (trade name) manufactured by Nikko Materials Co., Ltd., and the like.
- a predetermined portion of the resin layer is irradiated with active energy rays as a light source to cure the resin layer in the irradiated portion.
- the irradiation may be performed through a mask pattern, or a direct writing method for direct irradiation may be used.
- Active energy rays include, for example, ultraviolet rays, visible rays, electron beams, and X-rays.
- the wavelength of the active energy ray is, for example, in the range of 200-600 nm. When ultraviolet rays are used, the irradiation dose is about 10 to 1000 mJ/cm 2 .
- an active energy ray for example, an active energy ray containing a wavelength of 365 nm (i-line) is used. is preferred.
- an active energy ray containing a wavelength of 365 nm (i-line) is used, the dose is approximately 10 to 10,000 mJ/cm 2 .
- an active energy ray containing, for example, a wavelength of 405 nm (h-line) is used as the active energy ray. is preferred.
- the method of exposure through a mask pattern includes a contact exposure method in which the mask pattern is brought into close contact with the multilayer printed wiring board, and a non-contact exposure method in which parallel light beams are used for exposure without close contact. I don't mind. Further, when a support exists on the resin layer, exposure may be performed from above the support, or exposure may be performed after peeling off the support.
- a development step may be included as necessary. That is, when there is no support on the resin layer, after the exposure step, the pattern of the insulating layer is formed by removing the portion not photocured (unexposed portion) by wet development and developing. can be formed. In addition, when a support exists on the resin layer, after removing the support after the exposure step, the portion not photocured (unexposed portion) is removed by wet development, followed by development. Thereby, the pattern of the insulating layer can be formed.
- the developer is not particularly limited as long as it selectively dissolves the unexposed portions.
- organic solvents such as cyclohexanone, cyclopentanone, and ⁇ -butyrolactone
- alkaline developers such as tetramethylammonium hydroxide aqueous solution, sodium carbonate aqueous solution, potassium carbonate aqueous solution, sodium hydroxide aqueous solution, and potassium hydroxide aqueous solution are used. .
- These developers can be used singly or in admixture of two or more.
- the developing method for example, known methods such as dipping, paddle, spraying, rocking immersion, brushing, and scraping can be used. In pattern formation, these developing methods may be used in combination, if necessary.
- a developing method it is preferable to use a high-pressure spray because the resolution is further improved. A spray pressure of 0.02 to 0.5 MPa is preferable when a spray method is employed.
- Post-baking process After the exposure process is completed or the development process is completed, a post-baking process is performed to form an insulating layer (cured product).
- the post-baking process include an ultraviolet irradiation process using a high-pressure mercury lamp, a heating process using a clean oven, and the like, and these processes can be used in combination.
- the irradiation dose can be adjusted as necessary, and for example, irradiation can be carried out at a dose of approximately 50 to 10,000 mJ/cm 2 .
- the heating conditions can be appropriately selected as necessary, preferably in the range of 150 to 220° C. for 20 to 180 minutes, more preferably in the range of 160 to 200° C. and 30 to 150 minutes.
- Conductor layer forming step After forming the insulating layer (hardened material), a conductor layer is formed on the surface of the insulating layer by dry plating.
- dry plating known methods such as vapor deposition, sputtering, and ion plating can be used.
- a vapor deposition method vacuum vapor deposition method
- a vapor deposition method can form a metal film on an insulating layer, for example, by placing a multilayer printed wiring board in a vacuum vessel and heating and evaporating metal.
- a multilayer printed wiring board is placed in a vacuum chamber, an inert gas such as argon is introduced, a direct current voltage is applied, and the ionized inert gas collides with the target metal, and is ejected.
- a metal film can be formed on the insulating layer from a metal.
- a conductor layer is formed by electroless plating, electrolytic plating, or the like.
- a method for subsequent pattern formation for example, a subtractive method, a semi-additive method, or the like can be used.
- the encapsulating material of the present embodiment contains the resin composition of the present embodiment.
- a method for producing the sealing material generally known methods can be appropriately applied, and there is no particular limitation.
- a sealing material can be produced by mixing the resin composition of the present embodiment with various known additives or solvents generally used for sealing material applications using a known mixer. can.
- the method of adding the maleimide compound, various additives, and the solvent of the present embodiment during mixing is not particularly limited, and generally known methods can be appropriately applied.
- the fiber-reinforced composite material of this embodiment includes the resin composition of this embodiment and reinforcing fibers.
- the reinforcing fiber generally known ones can be used, and there is no particular limitation.
- glass fibers such as E glass, D glass, L glass, S glass, T glass, Q glass, UN glass, NE glass, spherical glass; carbon fiber; aramid fiber; boron fiber; PBO fiber; alumina fiber; silicon carbide fiber;
- the form and arrangement of the reinforcing fibers are not particularly limited, and can be appropriately selected from woven fabrics, non-woven fabrics, mats, knits, braids, unidirectional strands, rovings, chopped and the like.
- preforms laminated fabric base fabrics made of reinforcing fibers, or those integrated by stitching with stitch threads, or fiber structures such as three-dimensional fabrics and braids
- stitch threads or fiber structures such as three-dimensional fabrics and braids
- the resin transfer molding method which is one of the liquid composite molding methods, allows materials other than preforms, such as metal plates, foam cores, and honeycomb cores, to be set in advance in the mold. Since it can be applied to various applications, it is preferably used when mass-producing composite materials with relatively complicated shapes in a short time.
- the adhesive of this embodiment contains the resin composition of this embodiment.
- the method for producing the adhesive generally known methods can be appropriately applied, and there is no particular limitation.
- an adhesive can be produced by mixing the resin composition of the present embodiment with various known additives or solvents generally used for adhesives using a known mixer.
- the method of adding the maleimide compound, various additives, and the solvent of the present embodiment during mixing is not particularly limited, and generally known methods can be appropriately applied.
- the semiconductor device of this embodiment contains a resin composition. Specifically, it can be produced by the following method.
- a semiconductor device can be manufactured by mounting a semiconductor chip on a conductive portion of a multilayer printed wiring board.
- the conductive portion means a portion of the multilayer printed wiring board that transmits an electric signal, and the portion may be a surface or an embedded portion.
- the semiconductor chip is not particularly limited as long as it is an electric circuit element made of a semiconductor.
- the method of mounting a semiconductor chip when manufacturing a semiconductor device is not particularly limited as long as the semiconductor chip functions effectively. Specifically, a wire bonding mounting method, a flip chip mounting method, a mounting method using a bumpless build-up layer (BBUL), a mounting method using an anisotropic conductive film (ACF), and a mounting method using a non-conductive film (NCF). etc.
- a semiconductor device can also be manufactured by forming an insulating layer containing a resin composition on a semiconductor chip or a substrate on which a semiconductor chip is mounted.
- the shape of the substrate on which the semiconductor chips are mounted may be wafer-like or panel-like. After formation, it can be manufactured using the same method as the multilayer printed wiring board.
- THPA 1,2,3,6-tetrahydrophthalic anhydride
- THPA 1,2,3,6-tetrahydrophthalic anhydride
- propylene glycol monomethyl ether monoacetate was added as a solvent so that the solid content was 65%, reacted at 100 ° C. for 6 hours, and the compound (B-6) having an ethylenically unsaturated group was obtained. Obtained.
- the obtained compound (B-6) having an ethylenically unsaturated group had a solid content acid value (AV: mgKOH/g) of 110.
- A-1 Bismaleimide resin containing a structural unit represented by the general formula (1) and a maleimide group at both ends of the molecular chain Bismaleimide resin A-1 of Synthesis Example 1 (represented by the following formula (3) compound, highly viscous liquid at 25°C)
- a represents an integer of 1-10. It is preferable that a is an integer of 1 to 6 from the viewpoint that a more suitable viscosity can be obtained and the increase in viscosity of the varnish can be more controlled.
- n 19 represents an integer of 1 or more, preferably an integer of 1-10, more preferably an integer of 1-5.
- n 9 represents an integer of 1 or more, preferably an integer of 1-10.
- n 20 represents an integer of 1 or more, preferably an integer of 1-6.
- n 21 represents an integer of 1-10.
- Sensitivity was evaluated according to the following criteria, and the evaluation results are shown in Table 1.
- Evaluation criteria ⁇ : 7 stages remaining at an exposure amount of less than 500 mJcm 2 ⁇ : 7 stages remaining at an exposure amount of 500 mJ/cm 2 or more and less than 1000 mJ/cm 2 ⁇ : 7 stages remaining at an exposure amount of 1000 mJ/cm 2 or more and less than 3000 mJ/cm 2 ⁇ : Exposure No hardening even at 3000 mJ/cm 2 or more
- the photosensitive resin composition obtained in each example and comparative example was applied onto an ultra-low roughness electrolytic copper foil (CF-T4X-SV (trade name), manufactured by Fukuda Metal Foil & Powder Co., Ltd.) having a thickness of 12 ⁇ m. After application using an applicator, it was dried at a temperature of 80° C. for 30 minutes to form a film-like photosensitive resin composition on the copper foil. The coating thickness of the photosensitive resin composition was adjusted so that the film thickness of the film-like photosensitive resin composition after drying was 20 ⁇ m.
- CF-T4X-SV ultra-low roughness electrolytic copper foil
- This film-shaped photosensitive resin composition is exposed using a light source capable of irradiating an active energy ray containing a wavelength of 405 nm (h-line) (super-high pressure mercury lamp 500 W multilight (trade name) manufactured by USHIO Co., Ltd.).
- a cured film was obtained by performing exposure at an amount of 3000 mJ/cm 2 , then curing by heating at a temperature of 180° C. for 60 minutes, and then removing the copper foil by etching.
- the obtained cured film was cut into a 6 cm ⁇ 5 mm test piece, and a tensile tester (trade name "RTG-1201" manufactured by A&D Co., Ltd.) was used at 25 ° C. at a speed of 5 mm / min.
- the tensile modulus (MPa) and elongation at break (%) were measured using
- test piece 10 cm ⁇ 5 cm.
- the dielectric constant and dielectric loss tangent at 10 GHz of the obtained test piece were measured with a cavity resonator method dielectric constant measuring device (manufactured by AET Co., Ltd.). After the measurement, the test piece was immersed in water for 24 hours to absorb water, then removed from the water, wiped off the moisture, left to stand in an environment of 25°C and 30% for one day, and then the dielectric constant and dielectric loss tangent at 10 GHz were measured again. .
- the copper foil on both sides of the copper foil laminate was removed by etching, dried at 130° C. for 30 minutes, and then the cured resin film was cut to prepare a test piece of 10 cm ⁇ 5 cm.
- the obtained test piece was immersed in water for 24 hours to absorb water, then removed from the water and wiped off, and the weight increase rate of the test piece was taken as the water absorption rate.
- the resin compositions of Examples 1 to 8 have low dielectric properties, little change in dielectric properties after water absorption, low elasticity, high elongation, high heat resistance, and low water absorption. It was confirmed that the insulation reliability was excellent.
- the resin composition of the present embodiment is excellent in photocurability and alkali developability, it is industrially useful. Applications, multilayer printed wiring board applications, etc.), solder resists, underfill materials, die bonding materials, semiconductor sealing materials, hole-filling resins, part-embedding resins, fiber-reinforced composite materials, etc.
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Abstract
Description
例えば、特許文献1には、ビスフェノール型エポキシ樹脂と(メタ)アクリル酸とを反応させた後、酸無水物を反応させて得られるカルボキシル変性エポキシ(メタ)アクリレート樹脂と、ビフェニル型エポキシ樹脂と、光硬化開始剤と、希釈剤とを含む感光性熱硬化型樹脂組成物が記載されている。
[1]下記式(1)で表される構成単位と、分子鎖の両末端にマレイミド基と、を含む、ビスマレイミド化合物(A)と、
前記ビスマレイミド化合物(A)以外のマレイミド化合物、シアン酸エステル化合物、ベンゾオキサジン化合物、エポキシ樹脂、カルボジイミド化合物、及びエチレン性不飽和基を有する化合物からなる群より選択される少なくとも1種以上の樹脂又は化合物(B)と、
光硬化開始剤(C)と、を含む、樹脂組成物。
[4]充填材を更に含む、[1]~[3]のいずれか一項に記載の樹脂組成物。
[5][1]~[3]のいずれか一項に記載の樹脂組成物を含む、硬化物。
[6]支持体と、前記支持体の片面又は両面に配された樹脂層と、を有し、前記樹脂層が、[1]~[3]に記載の樹脂組成物を含む、樹脂シート。
[7]前記樹脂層の厚さが1~50μmである、[6]に記載の樹脂シート。
[8]基材と、前記基材に含浸又は塗布された、[1]~[4]のいずれか一項に記載の樹脂組成物と、を含む、プリプレグ。
[9][7]に記載の樹脂シート、及び[8]に記載のプリプレグからなる群より選ばれる少なくとも1 種を含む層と、前記層の片面又は両面に配された金属箔と、を有し、前記層が、前記樹脂組成物の硬化物を含む、金属箔張積層板。
[10]絶縁層と、前記絶縁層の片面又は両面に形成された導体層と、
を有し、前記絶縁層が、[1]~[4]のいずれか一項に記載の樹脂組成物を含む、多層プリント配線板。
[11][1]~[4]のいずれか一項に記載の樹脂組成物を含む、封止用材料。
[12][1]~ [4]のいずれか一項に記載の樹脂組成物と、強化繊維と、を含む、繊維強化複合材料。
[13][1]~[4]のいずれか一項に記載の樹脂組成物を含む、接着剤。
[14][1]~[4]のいずれか一項に記載の樹脂組成物を有する、半導体装置。
本実施形態の樹脂組成物は、特定のビスマレイミド化合物(A)(「成分(A)」とも称す)と、ビスマレイミド化合物(A)以外のマレイミド化合物、シアン酸エステル化合物、ベンゾオキサジン化合物、エポキシ樹脂、カルボジイミド化合物、及びエチレン性不飽和基を有する化合物からなる群より選択される少なくとも1種以上の樹脂又は化合物(B)(「成分(B)」、又は「樹脂又は化合物(B)」とも称す)と、光硬化開始剤(C)(「成分(C)」とも称す)と、を含む。以下、各成分について説明する。
樹脂組成物は、ビスマレイミド化合物(A)(成分(A)とも称す)を含む。ビスマレイミド化合物(A)は、式(1)で表される構成単位と、分子鎖の両末端にマレイミド基と、を含む。
一方、ビスマレイミド化合物(A)は、光硬化しても剛直なイミド環を有することから、高い耐熱性及び熱安定性を有するが、ビスマレイミド化合物を光硬化した硬化物を、露光工程終了後、又は現像工程終了後に行うポストベーク工程などにおいて加熱により更に硬化する際にシワが生じる。そのため、ビスマレイミド化合物(A)を単独重合して得られる硬化物は、多層プリント配線板の用途には不適である。しかし、ビスマレイミド化合物(A)を、後述の樹脂又は化合物(B)と光硬化開始剤(C)と共に配合することで、優れた光硬化性及び絶縁信頼性を有しながら、より高い耐熱性及び熱安定性を有する。それゆえ、本実施形態の樹脂組成物から得られる硬化物は、耐熱性、熱安定性、及び絶縁信頼性に優れ、本実施形態によれば、多層プリント配線板及び半導体装置における、保護膜、及び絶縁層を好適に形成することができる。
ビスマレイミド化合物(A)の式(1)中、R1は、炭素数1~16の直鎖状若しくは分岐状のアルキレン基、又は炭素数2~16の直鎖状若しくは分岐状のアルケニレン基を示す。R1としては、好適な粘度が得られ、ワニスの粘度上昇が制御できる点から、直鎖状若しくは分岐状のアルキレン基であることが好ましく、直鎖状のアルキレン基であることがより好ましい。
アルキレン基の炭素数としては、より好適な粘度が得られ、ワニスの粘度上昇をより制御できる点から、2~14であることが好ましく、4~12であることがより好ましい。
直鎖状若しくは分岐状のアルキレン基としては、例えば、メチレン基、エチレン基、プロピレン基、2,2-ジメチルプロピレン基、ブチレン基、ペンチレン基、ヘキシレン基、ヘプチレン基、オクチレン基、ノニレン基、デシレン基、ドデシレン基、ウンデシレン基、トリデシレン基、テトラデシレン基、ペンタデシレン基、ヘキサデシレン基、ネオペンチレン基、ジメチルブチレン基、メチルヘキシレン基、エチルヘキシレン基、ジメチルヘキシレン基、トリメチルヘキシレン基、メチルヘプチレン基、ジメチルヘプチレン基、トリメチルヘプチレン基、テトラメチルヘプチレン基、エチルヘプチレン基、メチルオクチレン基、メチルノニレン基、メチルデシレン基、メチルドデシレン基、メチルウンデシレン基、メチルトリデシレン基、メチルテトラデシレン基、及びメチルペンタデシレン基、が挙げられる。
アルケニレン基の炭素数としては、より好適な粘度が得られ、ワニスの粘度上昇をより制御できる点から、2~14であることが好ましく、4~12であることがより好ましい。
直鎖状若しくは分岐状のアルケニレン基としては、例えば、ビニレン基、1-メチルビニレン基、アリレン基、プロペニレン基、イソプロペニレン基、1-ブテニレン基、2-ブテニレン基、1-ペンテニレン基、2-ペンテニレン基、イソペンテニレン基、シクロペンテニレン基、シクロヘキセニレン基、及びジシクロペンタジエニレン基等が挙げられる。
直鎖状若しくは分岐状のアルキレン基としては、R1が参照できる。
直鎖状若しくは分岐状のアルケニレン基としては、R1が参照できる。
アルキル基の炭素数としては、より好適な粘度が得られ、ワニスの粘度上昇がより制御できる点から、2~14であることが好ましく、4~12であることがより好ましい。
直鎖状若しくは分岐状のアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、1-エチルプロピル基、n-ブチル基、2-ブチル基、イソブチル基、tert-ブチル基、n-ペンチル基、2-ペンチル基、tert-ペンチル基、2-メチルブチル基、3-メチルブチル基、2,2-ジメチルプロピル基、n-ヘキシル基、2-ヘキシル基、3-ヘキシル基、n-へプチル基、n-オクチル基、2-メチルペンチル基、3-メチルペンチル基、4-メチルペンチル基、2-メチルペンタン-3-イル基、及びn-ノニル基が挙げられる。
アルケニル基の炭素数としては、より好適な粘度が得られ、ワニスの粘度上昇がより制御できる点から、2~14であることが好ましく、4~12であることがより好ましい。
直鎖状若しくは分岐状のアルケニル基としては、例えば、ビニル基、アリル基、4-ペンテニル基、イソプロペニル基、イソペンテニル基、2-ヘプテニル基、2-オクテニル基、及び2-ノネニル基が挙げられる。
直鎖状若しくは分枝状のアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基が挙げられる。
直鎖状若しくは分枝状のアルコキシ基としては、メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基が挙げられる。
本実施形態において、マレイミド基は、式(4)で表され、N原子が前記式(1)の分子鎖に結合している。また、前記式(1)に結合されるマレイミド基は、全て同一であっても異なっていてもよいが、分子鎖の両末端のマレイミド基は同一であることが好ましい。
アルキル基の炭素数としては、好適に光硬化する点から、1~3であることが好ましく、1~2であることがより好ましい。
直鎖状若しくは分岐状のアルキル基としては、R3が参照できる。
前記ビスマレイミド化合物(A)は、公知の方法により製造することができる。例えば、4-(2,5-ジオキソテトラヒドロフラン-3-イル)-1,2,3,4-テトラヒドロナフタレン-1,2-ジカルボン酸無水物と、ダイマージアミン等を含むジアミンを含むモノマーと、無水マレイミド酸等のマレイミド化合物とを、通常80~250℃程度、好ましくは100~200℃程度の温度において、通常0.5~50時間程度、好ましくは1~20時間程度、重付加反応させて重付加物を得る、その後、通常60~120℃程度、好ましくは80~100℃程度の温度において、通常0.1~2時間程度、好ましくは0.1~0.5時間程度、重付加物をイミド化反応、すなわち、脱水閉環反応させることで、ビスマレイミド化合物(A)を得ることができる。
4-(2,5-ジオキソテトラヒドロフラン-3-イル)-1,2,3,4-テトラヒドロナフタレン-1,2-ジカルボン酸無水物のモル数と、ジアミンを含むモノマー及びマレイミド化合物との全量のモル数とを調整することで、任意のビスマレイミド化合物(A)を得ることができる。
触媒の添加量は、例えば、イミド化剤を、アミド基に対して、0.5~5.0倍モル当量程度、脱水触媒を、アミド基に対して、0.5~10.0倍モル当量とすることが好ましい。
本実施形態の樹脂組成物には、ビスマレイミド化合物(A)以外のマレイミド化合物、シアン酸エステル化合物、ベンゾオキサジン化合物、エポキシ樹脂、カルボジイミド化合物、及びエチレン性不飽和基を有する化合物からなる群より選択される少なくとも1種以上の樹脂又は化合物(B)(成分(B)とも称す)を含む。これらの樹脂又は化合物(B)は、得られる硬化物の物性及び用途に応じて、1種単独又は2種以上を適宜混合して使用することも可能である。
本実施形態において、ビスマレイミド化合物(A)及び後述の光硬化開始剤と共に、樹脂又は化合物(B)を用いると、光硬化性、耐熱性及び熱安定性に優れる。この理由は定かではないが、本発明者らは、ビスマレイミド化合物(A)が有する光硬化性及び絶縁信頼性と、樹脂又は化合物(B)が有する耐熱性及び熱安定性とを両立することが可能であるためと推定している。また、得られる硬化物には、ビスマレイミド化合物(A)と、樹脂又は化合物(B)とが有する種々の物性を付与することも可能となる。ビスマレイミド化合物(A)は、光透過性に非常に優れるため、樹脂又は化合物(B)を用いても、光硬化開始剤まで十分に光が届き、マレイミドの光ラジカル反応が効率的に起き、種々の活性エネルギー線を用いて光硬化させることができる。そのため、例えば、波長365nmを含む活性エネルギー線、又は波長405nmを含む活性エネルギー線を用いても、光が光硬化開始剤まで十分に届き、光硬化開始剤から発生したラジカルを用いたラジカル反応が進行し、樹脂又は化合物(B)が配合されている組成物においても光硬化が可能となる。
本実施形態において、樹脂又は化合物(B)は、それぞれ、1質量%で含まれるN-メチルピロリドン溶液を調製し、波長365nm(i線)を含む活性エネルギー線を用いて、カルボキシ基を1つ以上含む化合物(B)が1質量%で含まれるN-メチルピロリドン溶液の透過率を測定した場合においては、その透過率は5%以上であることが好ましい。該樹脂又は化合物(B)は、非常に優れた光透過性を示す。また、波長405nm(h線)を含む活性エネルギー線を用いて、それぞれ、樹脂又は化合物(B)が1質量%で含まれるN-メチルピロリドン溶液の透過率を測定した場合においては、その透過率が5%以上であることが好ましく、この場合においても非常に優れた光透過性を示す。該樹脂又は化合物(B)を用いると、例えば、直接描画露光法を用いて高密度で高精細な配線形成(パターン)を有するプリント配線板を製造するに際し、波長405nm(h線)を含む活性エネルギー線を用いた場合でも、マレイミドの光ラジカル反応が効率的に起こる。なお、波長365nm(i線)における透過率は、光硬化性により優れる樹脂組成物を得ることができることから、8%以上であることがより好ましく、10%以上であることが更に好ましい。波長405nm(h線)における透過率は、光硬化性により優れる樹脂組成物を得ることができることから、8%以上であることがより好ましく、10%以上であることが更に好ましい。なお、波長365nm(i線)における透過率、及び波長405nm(h線)における透過率において、それぞれの上限は、例えば、99.9%以下である。
樹脂組成物には、ビスマレイミド化合物(A)以外のマレイミド化合物(B1)(成分(B1)とも称す)を用いることができる。以下にマレイミド化合物(B1)について述べる。
炭素数1~5のアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、t-ブチル基、n-ペンチル基、及びネオペンチル基が挙げられる。
また、ビスマレイミド化合物(A)の光ラジカル反応を効率的に起こさせるために、マレイミド化合物(B1)が1質量%で含まれるクロロホルム溶液を調製し、波長405nm(h線)を含む活性エネルギー線を用いてこのクロロホルム溶液の透過率を測定した場合に、透過率が5%以上の光透過性を示すことが好ましい。該マレイミド化合物(B1)を用いることで、例えば、直接描画露光法を用いて高密度で高精細な配線形成(パターン)を有するプリント配線板を製造するに際し、波長405nm(h線)を含む活性エネルギー線を用いた場合でも、マレイミドの光ラジカル反応が効率的に起こる。光透過率は、光硬化性により優れる樹脂組成物を得ることができることから、8%以上であることがより好ましく、10%以上であることが更に好ましい。
前記式(10)中、yの数は、10~35である。
アルキル基の炭素数としては、優れた光硬化性を示すことから、4~12が好ましい。
アルケニル基の炭素数としては、優れた光硬化性を示すことから、4~12が好ましい。
直鎖状若しくは分岐状のアルケニル基としては、ビスマレイミド化合物(A)におけるR3が参照できる。これらの中でも、優れた光硬化性を示すことから、2-ヘプテニル基、2-オクテニル基、2-ノネニル基が好ましく、2-オクテニル基がより好ましい。
アルキル基の炭素数としては、優れた光硬化性を示すことから、4~12が好ましい。
アルケニル基の炭素数としては、優れた光硬化性を示すことから、4~12が好ましい。
アルケニル基の具体例としては、Raにおけるアルケニル基を参照できる。この中でも、優れた光硬化性を示すことから、2-ヘプテニル基、2-オクテニル基、2-ノネニル基が好ましく、2-オクテニル基がより好ましい。
式(9)で表されるマレイミド化合物としては、例えば、ケイ・アイ化成(株)製BMI-1000P(商品名、前記式(9)中のn6=13.6(平均))、ケイ・アイ化成(株)社製BMI-650P(商品名、前記式(9)中のn6=8.8(平均))、ケイ・アイ化成(株)社製BMI-250P(商品名、前記式(9)中のn6=3~8(平均))、ケイ・アイ化成(株)社製CUA-4(商品名、前記式(9)中のn6=1)等が挙げられる。
前記式(10)で表されるマレイミド化合物としては、例えば、Designer Molecules Inc.製BMI-6100(商品名、前記式(10)中のx=18、y=18)等が挙げられる。
前記式(11)で表されるマレイミド化合物としては、例えば、Designer Molecules Inc.製BMI-689(商品名、下記式(17)、官能基当量:346g/eq.)等が挙げられる。
前記式(13)で表されるマレイミド化合物としては、市販品を利用することもでき、例えば、Designer Molecules Inc.(DMI)製BMI-1700(商品名)が挙げられる。
前記式(14)で表されるマレイミド化合物としては、市販品を利用することもでき、例えば、Designer Molecules Inc.(DMI)製BMI-3000(商品名)、Designer Molecules Inc.(DMI)製BMI-5000(商品名)、Designer Molecules Inc.(DMI)製BMI-9000(商品名)が挙げられる。
前記式(15)で表されるマレイミド化合物としては、市販品を利用することもでき、例えば、大和化成工業株式会社製BMI-TMH(商品名)が挙げられる。
前記式(16)で表されるマレイミド化合物としては、市販品を利用することもでき、例えば、ケイ・アイ化成(株)製BMI-70(商品名)が挙げられる。
これらのマレイミド化合物(B1)は、1種単独又は2種以上を適宜混合して使用することも可能である。
樹脂組成物には、シアン酸エステル化合物(B―2)(成分(B―2)とも称す)を用いることができる。以下にシアン酸エステル化合物(B―2)について述べる。
シアン酸エステル化合物としては、シアナト基(シアン酸エステル基)が少なくとも1個置換された芳香族部分を分子内に有する樹脂であれば特に限定されない。
また、前記式(18)におけるアルキル基及びRaにおけるアリール基中の水素原子は、フッ素原子、塩素原子等のハロゲン原子、メトキシ基、フェノキシ基等のアルコキシル基、又はシアノ基等で置換されていてもよい。
アルケニル基の具体例としては、ビニル基、(メタ)アリル基、イソプロペニル基、1-プロペニル基、2-ブテニル基、3-ブテニル基、1,3-ブタンジエニル基、2-メチル-2-プロペニル、2-ペンテニル基、及び2-ヘキセニル基等が挙げられる。
アリール基の具体例としては、フェニル基、キシリル基、メシチル基、ナフチル基、フェノキシフェニル基、エチルフェニル基、o-,m-又はp-フルオロフェニル基、ジクロロフェニル基、ジシアノフェニル基、トリフルオロフェニル基、メトキシフェニル基、及びo-,m-又はp-トリル基等が挙げられる。更にアルコキシル基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、n-ブトキシ基、イソブトキシ基、及びtert-ブトキシ基等が挙げられる。
前記式(18)のXにおける窒素数1~10の2価の有機基としては、イミノ基、ポリイミド基等が挙げられる。
前記式(19)のAr2及び前記式(20)のAr3の具体例としては、前記式(19)に示す2個の炭素原子、又は前記式(20)に示す2個の酸素原子が、1,4位又は1,3位に結合するベンゼンジイル基、2個の炭素原子又は2個の酸素原子が4,4’位、2,4’位、2,2’位、2,3’位、3,3’位、又は3,4’位に結合するビフェニルジイル基、及び、2個の炭素原子又は2個の酸素原子が、2,6位、1,5位、1,6位、1,8位、1,3位、1,4位、又は2,7位に結合するナフタレンジイル基が挙げられる。
前記式(19)のRb、Rc、Rd、Re、Rf及びRg、並びに前記式(20)のRi、Rjにおけるアルキル基及びアリール基は、前記式(18)におけるものと同義である。
樹脂組成物には、ベンゾオキサジン化合物(B―3)(成分(B―3)とも称す)を用いることができる。以下にベンゾオキサジン化合物(B―3)について述べる。
ベンゾオキサジン化合物(B―3)としては、基本骨格としてオキサジン環を有していれば、一般に公知のものを用いることができる。ベンゾオキサジン化合物には、ナフトオキサジン化合物などの多環オキサジン骨格を有する化合物も含まれる。
ベンゾオキサジン化合物は、良好な耐熱性を有するとの理由から、式(20)で表される化合物、及び式(21)で表される化合物が好ましく、3,3’-(メチレン-1,4-ジフェニレン)ビス(3,4-ジヒドロ-2H-1,3-ベンゾオキサジンがより好ましい。
樹脂組成物には、エポキシ樹脂(B―4)(成分(B―4)とも称す)を用いることができる。以下にエポキシ樹脂(B―4)について述べる。
エポキシ樹脂(B―4)としては、一般に公知のものを使用できる。例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールE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、ビスフェノールAノボラック型エポキシ樹脂、ビフェニル型エポキシ樹脂、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、キシレンノボラック型エポキシ樹脂、多官能フェノール型エポキシ樹脂、ナフタレン型エポキシ樹脂、ナフタレン骨格変性ノボラック型エポキシ樹脂、ナフチレンエーテル型エポキシ樹脂、フェノールアラルキル型エポキシ樹脂、アントラセン型エポキシ樹脂、3官能フェノール型エポキシ樹脂、4官能フェノール型エポキシ樹脂、トリグリシジルイソシアヌレート、グリシジルエステル型エポキシ樹脂、脂環式エポキシ樹脂、ジシクロペンタジエンノボラック型エポキシ樹脂、ビフェニルノボラック型エポキシ樹脂、フェノールアラルキルノボラック型エポキシ樹脂、ナフトールアラルキルノボラック型エポキシ樹脂、アラルキルノボラック型エポキシ樹脂、ナフトールアラルキル型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、ポリオール型エポキシ樹脂、リン含有エポキシ樹脂、グリシジルアミン、ブタジエン等の二重結合をエポキシ化した化合物、水酸基含有シリコーン樹脂類とエピクロルヒドリンとの反応により得られる化合物、及びこれらのハロゲン化物が挙げられる。これらのエポキシ樹脂は、1種単独又は2種以上を適宜混合して使用することも可能である。
エポキシ樹脂は、硬化物の耐熱性に優れるとの理由から、前記式(23)で表されるエポキシ樹脂、及び前記式(24)で表されるエポキシ樹脂が好ましく、前記式(23)で表されるエポキシ樹脂がより好ましい。
樹脂組成物には、カルボジイミド化合物(B―5)(成分(B―5)とも称す)を用いることができる。以下にカルボジイミド化合物(B―5)について述べる。
カルボジイミド化合物(B―5)としては、少なくとも分子中に1個以上のカルボジイミド基を有していれば、一般に公知のものを使用できる。例えば、N,N’-ジシクロヘキシルカルボジイミド、ジシクロヘキシルカルボジイミド、ジイソプロピルカルボジイミド、ジメチルカルボジイミド、ジイソブチルカルボジイミド、ジオクチルカルボジイミド、t-ブチルイソプロピルカルボジイミド、ジフェニルカルボジイミド、ジ-t-ブチルカルボジイミド、ジ-β-ナフチルカルボジイミド、N,N’-ジ-2,6-ジイソプロピルフェニルカルボジイミド、2,6,2’,6’-テトライソプロピルジフェニルカルボジイミド、環状カルボジイミド、カルボジライト(登録商標)B-01(日清紡ケミカル(株)製)、及びスタバクゾール(登録商標:Rhein Chemie社製)等のポリカルボジイミド等が挙げられる。
カルボジイミド化合物は、良好な耐熱性を有し、プリント配線板の絶縁層に用いた場合に導体層と良好な密着性を有するとの理由から、カルボジライト(登録商標)B-01、V-03、V05(以上、商品名、日清紡ケミカル(株)製)が好ましく、カルボジライト(登録商標)B-01(商品名、日清紡ケミカル(株)製)がより好ましい。
樹脂組成物には、エチレン性不飽和基を有する化合物(B―6)(成分(B―6)とも称す)を用いることができる。以下にエチレン性不飽和基を有する化合物(B―6)について述べる。
エチレン性不飽和基を有する化合物(B―6)としては、1分子中に1個以上のエチレン性不飽和基を有する化合物であれば、一般に公知のものを使用できる。例えば、(メタ)アクリロイル基、及びビニル基等を有する化合物が挙げられる。
エチレン性不飽和基を有する化合物としては、良好な熱安定性を有するとの理由から、ジシクロペンタジエンフェノール型エポキシアクリレート化合物のプロピレングリコールモノメチルエーテルアセテートが好ましい。
本実施形態に係る樹脂組成物には、光硬化開始剤(C)(成分(C)とも称す)を含む。光硬化開始剤(C)は、一般に光硬化性樹脂組成物で用いられる分野で公知のものを使用することができる。光硬化開始剤(C)は、ビスマレイミド化合物(A)、及び樹脂又は化合物(B)と共に、種々の活性エネルギー線を用いて光硬化させるために用いられる。
p-メトキシフェニルジアゾニウムフロロホスホネート、及びN,N-ジエチルアミノフェニルジアゾニウムヘキサフロロホスホネート等のルイス酸のジアゾニウム塩;ジフェニルヨードニウムヘキサフロロホスホネート、及びジフェニルヨードニウムヘキサフロロアンチモネート等のルイス酸のヨードニウム塩;トリフェニルスルホニウムヘキサフロロホスホネート、及びトリフェニルスルホニウムヘキサフロロアンチモネート等のルイス酸のスルホニウム塩;トリフェニルホスホニウムヘキサフロロアンチモネート等のルイス酸のホスホニウム塩;その他のハロゲン化物;トリアジン系開始剤;ボーレート系開始剤;その他の光酸発生剤等のカチオン系光硬化開始剤が挙げられる。
これらの光硬化開始剤(C)は、1種単独又は2種以上を適宜混合して使用することも可能である。
式(3)中、R5は、各々独立に水素原子又はメチル基を表す。R5のうち、1つ以上がメチル基であることが好ましく、全てメチル基であることがより好ましい。
本実施形態の樹脂組成物には、塗膜性や耐熱性等の諸特性を向上させるために、充填材(D)(成分(D)とも称す)を含むこともできる。充填材(D)としては、絶縁性を有し、光硬化に用いる種々の活性エネルギー線に対する透過性を阻害しないものであることが好ましく、波長365nm(i線)、及び/又は波長405nm(h線)を含む活性エネルギー線に対する透過性を阻害しないものであることがより好ましい。
これらの充填材(D)は、後述のシランカップリング剤等で表面処理されていてもよい。
本実施形態の樹脂組成物には、充填材の分散性、ポリマー及び/又は樹脂と、充填材との接着強度を向上させるために、シランカップリング剤及び/又は湿潤分散剤を併用することができる。
これらのシランカップリング剤としては、一般に無機物の表面処理に使用されているシランカップリング剤であれば、限定されない。具体例としては、3-アミノプロピルトリメトキシシラン、γ-アミノプロピルトリエトキシシラン、3-アミノプロピルジメトキシメチルシラン、3-アミノプロピルジエトキシメチルシラン、N-β-(アミノエチル)-γ-アミノプロピルトリメトキシシラン、N-(2-アミノエチル)-3-アミノプロピルトリエトキシシラン、N-(2-アミノエチル)-3-アミノプロピルジメトキシメチルシラン、N-(2-アミノエチル)-3-アミノプロピルジエトキシメチルシラン、 N-フェニル-3-アミノプロピルトリメトキシシラン、N-フェニル-3-アミノプロピルトリエトキシシラン、[3-(6-アミノヘキシルアミノ)プロピル]トリメトキシシラン、及び[3-(N,N-ジメチルアミノ)-プロピル]トリメトキシシラン等のアミノシラン系;γ-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルトリエトキシシラン、3-グリシドキシプロピルジメトキシメチルシラン、3-グリシドキシプロピルジエトキシメチルシラン、2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、及び[8-(グリシジルオキシ)-n-オクチル]トリメトキシシラン等のエポキシシラン系;ビニルトリス(2-メトキシエトキシ)シラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ジメトキシメチルビニルシラン、ジエトキシメチルビニルシラン、トリメトキシ(7-オクテン-1-イル)シラン、及びトリメトキシ(4-ビニルフェニル)シランなどのビニルシラン系;3-メタクリロキシプロピルトリメトキシシラン、3-メタクリロキシプロピルトリエトキシシラン、3-メタクリロキシプロピルジメトキシメチルシラン、3-メタクリロキシプロピルジエトキシメチルシランなどのメタクリルシラン系、γ-アクリロキシプロピルトリメトキシシラン、及び3-アクリロキシプロピルトリエトキシシラン等の(メタ)アクリルシラン系;3-イソシアネートプロピルトリメトキシシラン、及び3-イソシアネートプロピルトリエトキシシランなどのイソシアネートシラン系;トリス-(トリメトキシシリルプロピル)イソシアヌレートなどのイソシアヌレートシラン系;3-メルカプトプロピルトリメトキシシラン、及び3-メルカプトプロピルジメトキシメチルシランなどのメルカプトシラン系;3-ウレイドプロピルトリエトキシシランなどのウレイドシラン系;p-スチリルトリメトキシシランなどのスチリルシラン系;N-β-(N-ビニルベンジルアミノエチル)-γ-アミノプロピルトリメトキシシラン塩酸塩等のカチオニックシラン系;[3-(トリメトキシシリル)プロピル]コハク酸無水物などの酸無水物系;フェニルトリメトキシシラン、フェニルトリエトキシシラン、ジメトキシメチルフェニルシラン、ジエトキシメチルフェニルシラン、及びp-トリルトリメトキシシラン等のフェニルシラン系トリメトキシ(1-ナフチル)シランなどのアリールシラン系が挙げられる。これらのシランカップリング剤は、1種単独又は2種以上を適宜混合して使用することも可能である。
湿潤分散剤としては、塗料用に使用されている分散安定剤であれば、特に限定されない。具体例としては、ビッグケミー・ジャパン(株)製のDISPERBYK(登録商標)-110(商品名)、111(商品名)、118(商品名)、180(商品名)、161(商品名)、BYK(登録商標)-W996(商品名)、W9010(商品名)、W903(商品名)等の湿潤分散剤が挙げられる。これらの湿潤分散剤は、1種単独又は2種以上を適宜混合して使用することも可能である。
本実施形態の樹脂組成物において、湿潤分散剤の含有量は、通常、ビスマレイミド化合物(A)、樹脂又は化合物(B)及び光硬化開始剤(C)の合計100質量部に対して、0.1~10質量部である。
本実施形態の樹脂組成物には、必要に応じて、硬化速度を適宜調節するために、硬化促進剤を含むことが好ましい。硬化促進剤としては、シアン酸エステル化合物等の硬化促進剤として一般に使用されているものを用いることができる。硬化促進剤としては、例えば、オクチル酸亜鉛、ナフテン酸亜鉛、ナフテン酸コバルト、ナフテン酸銅、アセチルアセトン鉄、オクチル酸ニッケル、及びオクチル酸マンガン等の有機金属塩類;フェノール、キシレノール、クレゾール、レゾルシン、カテコール、オクチルフェノール、及びノニルフェノール等のフェノール化合物;1-ブタノール、及び2-エチルヘキサノール等のアルコール類;2-メチルイミダゾール、2-エチル-4-メチルイミダゾール、2-フェニルイミダゾール、1-シアノエチル-2-フェニルイミダゾール、1-シアノエチル-2-エチル-4-メチルイミダゾール、2-フェニル-4,5-ジヒドロキシメチルイミダゾール、及び2-フェニル-4-メチル-5-ヒドロキシメチルイミダゾール等のイミダゾール類及びこれらのイミダゾール類のカルボン酸もしくはその酸無水類の付加体等の誘導体;ジシアンジアミド、ベンジルジメチルアミン、及び4-メチル-N,N-ジメチルベンジルアミン等のアミン類;ホスフィン系化合物、ホスフィンオキサイド系化合物、ホスホニウム塩系化合物、及びダイホスフィン系化合物等のリン化合物;エポキシ-イミダゾールアダクト系化合物;ベンゾイルパーオキサイド、p-クロロベンゾイルパーオキサイド、ジ-t-ブチルパーオキサイド、ジイソプロピルパーオキシカーボネート、及びジ-2-エチルヘキシルパーオキシカーボネート等の過酸化物;2,2’-アゾビスイソブチロニトリル(以下、「AIBN」とも称す)等のアゾ化合物が挙げられる。これらの硬化促進剤は、1種単独又は2種以上を適宜混合して使用することも可能である。
本実施形態の樹脂組成物において、硬化促進剤の含有量は、通常、ビスマレイミド化合物(A)、樹脂又は化合物(B)及び光硬化開始剤(C)の合計100質量部に対して、0.1~20質量部である。
本実施形態の樹脂組成物には、必要に応じて、有機溶剤を含んでもよい。有機溶剤を用いると、樹脂組成物の調製時における粘度を調整することができる。有機溶剤の種類は、樹脂組成物中の樹脂の一部又は全部を溶解可能なものであれば、特に限定されない。有機溶剤としては、例えば、アセトン、メチルエチルケトン、及びメチルイソブチルケトン等のケトン類;シクロペンタノン、及びシクロヘキサノン等の脂環式ケトン類;プロピレングリコールモノメチルエーテル、及びプロピレングリコールモノメチルエーテルアセテート等のセロソルブ系溶媒;乳酸エチル、酢酸メチル、酢酸エチル、酢酸ブチル、酢酸イソアミル、メトキシプロピオン酸メチル、ヒドロキシイソ酪酸メチル、及びγ―ブチロラクトン等のエステル系溶媒;ジメチルアセトアミド、及びジメチルホルムアミド等のアミド類などの極性溶剤類;トルエン、キシレン及びアニソール等の芳香族炭化水素等の無極性溶剤が挙げられる。
これらの有機溶剤は、1種単独又は2種以上を適宜混合して使用することも可能である。
本実施形態の樹脂組成物には、本実施形態の特性が損なわれない範囲において、これまでに挙げられていない熱硬化性樹脂、熱可塑性樹脂、及びそのオリゴマー、並びにエラストマー類等の種々の高分子化合物;これまでに挙げられていない難燃性の化合物;添加剤等の併用も可能である。これらは一般に使用されているものであれば、特に限定されない。例えば、難燃性の化合物では、メラミンやベンゾグアナミン等の窒素含有化合物、オキサジン環含有化合物、及びリン系化合物のホスフェート化合物、芳香族縮合リン酸エステル、含ハロゲン縮合リン酸エステル等が挙げられる。添加剤としては、紫外線吸収剤、酸化防止剤、蛍光増白剤、光増感剤、染料、顔料、増粘剤、滑剤、消泡剤、表面調整剤、光沢剤、重合禁止剤、熱硬化促進剤等が挙げられる。これらの成分は、1種単独又は2種以上を適宜混合して使用することも可能である。
本実施形態の樹脂組成物において、その他の成分の含有量は、通常、ビスマレイミド化合物(A)、樹脂又は化合物(B)及び光硬化開始剤(C)の合計100質量部に対して、それぞれ0.1~10質量部である。
本実施形態の樹脂組成物は、ビスマレイミド化合物(A)、樹脂又は化合物(B)、光硬化開始剤(C)と、必要に応じて、充填材(D)、その他の樹脂、その他の化合物、及び添加剤等を適宜混合することにより調製される。樹脂組成物は、後述する本実施形態の樹脂シートを作製する際のワニスとして、好適に使用することができる。なお、ワニスの調製に使用する有機溶媒は、特に限定されず、その具体例は、前記したとおりである。
樹脂組成物は、絶縁信頼性の樹脂組成物が必要とされる用途に好ましく使用することができる。用途としては、例えば、感光性フィルム、支持体付き感光性フィルム、プリプレグ、樹脂シート、回路基板(積層板用途、多層プリント配線板用途等)、ソルダーレジスト、アンダーフィル材、ダイボンディング材、半導体封止材、穴埋め樹脂、及び部品埋め込み樹脂等に使用することができる。それらの中でも、樹脂組成物は、光硬化性、耐熱性及び熱安定性に優れるため、多層プリント配線板の絶縁層用として、又はソルダーレジスト用として好適に使用することができる。
硬化物は、本実施形態の樹脂組成物を硬化させてなる。硬化物は、例えば、樹脂組成物を溶融又は溶媒に溶解させた後、型内に流し込み、光を用いて通常の条件で硬化させることにより得ることができる。光の波長領域は、光重合開始剤等により効率的に硬化が進む100~500nmの範囲で硬化させることが好ましい。
本実施形態の樹脂シートは、支持体と、支持体の片面又は両面に配された樹脂層と、を有し、樹脂層が、樹脂組成物を含む、支持体付き樹脂シートである。樹脂シートは、樹脂組成物を支持体上に塗布、及び乾燥して製造することができる。樹脂シートにおける樹脂層は、優れた耐熱性、熱安定性及び絶縁信頼性を有する。
樹脂層側を保護フィルムで保護することにより、樹脂層表面へのゴミ等の付着やキズを防止することができる。保護フィルムとしては、樹脂フィルムと同様の材料により構成されたフィルムを用いることができる。保護フィルムの厚さは、1~50μmの範囲であることが好ましく、5~40μmの範囲であることがより好ましい。厚さが1μm未満では、保護フィルムの取り扱い性が低下する傾向にあり、50μmを超えると廉価性に劣る傾向にある。なお、保護フィルムは、樹脂層と支持体との接着力に対して、樹脂層と保護フィルムとの接着力の方が小さいものが好ましい。
塗布方法は、例えば、ロールコーター、コンマコーター、グラビアコーター、ダイコーター、バーコーター、リップコーター、ナイフコーター、及びスクイズコーター等を用いた公知の方法で行うことができる。乾燥は、例えば、60~200℃の乾燥機中で、1~60分加熱させる方法等により行うことができる。
本実施形態の多層プリント配線板は、絶縁層と、絶縁層の片面又は両面に形成された導体層とを有し、絶縁層が、樹脂組成物を含む。絶縁層は、例えば、樹脂シートを1枚以上重ねて硬化して得ることもできる。絶縁層と導体層のそれぞれの積層数は、特に限定されず、目的とする用途に応じて適宜積層数を設定することができる。また、絶縁層と導体層の順番も特に限定されない。導体層としては、各種プリント配線板材料に用いられる金属箔であってもよく、例えば、銅、及びアルミニウム等の金属箔が挙げられる。銅の金属箔としては、圧延銅箔、及び電解銅箔等の銅箔が挙げられる。導体層の厚みは、通常、1~100μmである。具体的には、以下の方法により製造することができる。
ラミネート工程では、樹脂シートの樹脂層側を、真空ラミネーターを用いて回路基板の片面又は両面にラミネートする。回路基板としては、例えば、ガラスエポキシ基板、金属基板、セラミック基板、シリコン基板、半導体封止樹脂基板、ポリエステル基板、ポリイミド基板、BTレジン基板、及び熱硬化型ポリフェニレンエーテル基板等が挙げられる。なお、回路基板とは、基板の片面又は両面にパターン加工された導体層(回路)が形成された基板をいう。また、導体層と絶縁層とを交互に積層してなる多層プリント配線板において、多層プリント配線板の最外層の片面又は両面がパターン加工された導体層(回路)となっている基板も回路基板に含まれる。なお、この多層プリント配線板に積層されている絶縁層は、本実施形態の樹脂シートを1枚以上重ねて硬化して得られた絶縁層であってもよく、本実施形態の樹脂シートと、本実施形態の樹脂シートと異なる公知の樹脂シートとをそれぞれ1枚以上重ねて得られた絶縁層であってもよい。なお、本実施形態の樹脂シートと、本実施形態の樹脂シートと異なる公知の樹脂シートとの重ね方は、特に限定されない。導体層表面には、黒化処理、及び/又は銅エッチング等により予め粗化処理が施されていてもよい。ラミネート工程において、樹脂シートが保護フィルムを有している場合には、保護フィルムを剥離除去した後、必要に応じて樹脂シート及び回路基板をプレヒートし、樹脂シートの樹脂層を加圧及び加熱しながら回路基板に圧着する。本実施形態においては、真空ラミネート法により減圧下で回路基板に樹脂シートの樹脂層をラミネートする方法が好適に用いられる。
露光工程では、ラミネート工程により、回路基板上に樹脂層が設けられた後、樹脂層の所定部分に光源として、活性エネルギー線を照射し、照射部の樹脂層を硬化させる。
照射は、マスクパターンを通してもよいし、直接照射する直接描画法を用いてもよい。活性エネルギー線としては、例えば、紫外線、可視光線、電子線、及びX線等が挙げられる。活性エネルギー線の波長としては、例えば、200~600nmの範囲である。紫外線を用いる場合、その照射量はおおむね10~1000mJ/cm2である。また、ステッパー露光法を用いて高密度で高精細な配線形成(パターン)を有するプリント配線板を製造するに際しては、活性エネルギー線として、例えば、波長365nm(i線)を含む活性エネルギー線を用いることが好ましい。波長365nm(i線)を含む活性エネルギー線を用いた場合、その照射量は、おおむね10~10,000mJ/cm2である。直接描画露光法を用いて高密度で高精細な配線形成(パターン)を有するプリント配線板を製造するに際しては、活性エネルギー線として、例えば、波長405nm(h線)を含む活性エネルギー線を用いることが好ましい。波長405nm(h線)を含む活性エネルギー線を用いた場合、その照射量は、おおむね10~10,000mJ/cm2である。
マスクパターンを通す露光方法には、マスクパターンを多層プリント配線板に密着させて行う接触露光法と、密着させずに平行光線を使用して露光する非接触露光法とがあるが、どちらを用いてもかまわない。また、樹脂層上に支持体が存在している場合は、支持体上から露光してもよいし、支持体を剥離後に露光してもよい。
本実施形態では、必要に応じて、現像工程を含んでもよい。
すなわち、樹脂層上に支持体が存在していない場合には、露光工程後、ウエット現像にて光硬化されていない部分(未露光部)を除去し、現像することにより、絶縁層のパターンを形成することができる。また、樹脂層上に支持体が存在している場合には、露光工程後、その支持体を除去した後に、ウエット現像にて光硬化されていない部分(未露光部)を除去し、現像することにより、絶縁層のパターンを形成することができる。
露光工程終了後、又は現像工程終了後、ポストベーク工程を行い、絶縁層(硬化物)を形成する。ポストベーク工程としては、高圧水銀ランプによる紫外線照射工程やクリーンオーブンを用いた加熱工程等が挙げられ、これらを併用することも可能である。紫外線を照射する場合は、必要に応じてその照射量を調整することができ、例えば、50~10,000mJ/cm2程度の照射量で照射を行うことができる。また加熱の条件は、必要に応じて適宜選択できるが、好ましくは150~220℃で20~180分間の範囲、より好ましくは160~200℃で30~150分間の範囲で選択される。
絶縁層(硬化物)を形成後、乾式めっきにより絶縁層表面に導体層を形成する。乾式めっきとしては、蒸着法、スパッタリング法、及びイオンプレーティング法等の公知の方法を使用することができる。蒸着法(真空蒸着法)は、例えば、多層プリント配線板を真空容器内に入れ、金属を加熱蒸発させることにより、絶縁層上に金属膜を形成することができる。スパッタリング法も、例えば、多層プリント配線板を真空容器内に入れ、アルゴン等の不活性ガスを導入し、直流電圧を印加して、イオン化した不活性ガスをターゲット金属に衝突させ、叩き出された金属により絶縁層上に金属膜を形成することができる。
本実施形態の封止用材料は、本実施形態の樹脂組成物を含む。封止用材料の製造方法としては、一般に公知の方法を適宜適用でき、特に限定されない。例えば、本実施形態の樹脂組成物と、封止材料用途で一般的に用いられる各種公知の添加剤あるいは溶媒等を、公知のミキサーを用いて混合することで封止用材料を製造することができる。なお、混合の際の、本実施形態のマレイミド化合物、各種添加剤、溶媒の添加方法は、一般に公知の方法を適宜適用でき、特に限定されない。
本実施形態の繊維強化複合材料は、本実施形態の樹脂組成物と、強化繊維とを含む。強化繊維としては、一般的に公知のものを用いることができ、特に限定されない。例えば、Eガラス、Dガラス、Lガラス、Sガラス、Tガラス、Qガラス、UNガラス、NEガラス、球状ガラス等のガラス繊維;炭素繊維;アラミド繊維;ボロン繊維;PBO繊維;高強力ポリエチレン繊維;アルミナ繊維;炭化ケイ素繊維が挙げられる。強化繊維の形態や配列については、特に限定されず、織物、不織布、マット、ニット、組み紐、一方向ストランド、ロービング、及びチョップド等から適宜選択できる。また、強化繊維の形態としてプリフォーム(強化繊維からなる織物基布を積層したもの、又はこれをステッチ糸により縫合一体化したもの、あるいは立体織物や編組物などの繊維構造物)を適用することもできる。
本実施形態の接着剤は、本実施形態の樹脂組成物を含む。接着剤の製造方法としては、一般に公知の方法を適宜適用でき、特に限定されない。例えば、本実施形態の樹脂組成物と、接着剤用途で一般的に用いられる各種公知の添加剤あるいは溶媒等を、公知のミキサーを用いて混合することで接着剤を製造することができる。なお、混合の際の、本実施形態のマレイミド化合物、各種添加剤、溶媒の添加方法は、一般に公知の方法を適宜適用でき、特に限定されない。
本実施形態の半導体装置は、樹脂組成物を含む。具体的には、以下の方法により製造することができる。多層プリント配線板の導通箇所に、半導体チップを実装することにより半導体装置を製造することができる。ここで、導通箇所とは、多層プリント配線板における電気信号を伝える箇所のことであって、その場所は表面であっても、埋め込まれた箇所であってもよい。また、半導体チップは、半導体を材料とする電気回路素子であれば特に限定されない。
分子量の測定条件は以下の通りである。
機種:GPC TOSOH HLC-8220GPC
カラム:Super HZM-N
溶離液:THF(テトラヒドロフラン);0.35ml/分、40℃
検出器:RI(示差屈折計)
分子量標準:ポリスチレン
[合成例1]
フッ素樹脂コーティングされた撹拌バーを装備した500mlの丸底フラスコに、100gのトルエンと33gのN-メチルピロリドンを投入した。次にPRIAMINE 1075(クローダジャパン株式会社製)80.2g(0.16mol)を加え、ついで無水メタンスルホン酸14.4g(0.16mol)をゆっくりと加え、塩を形成した。ほぼ10分間撹拌して混合し、ついで4-(2,5--ジオキソテトラヒドロフラン-3-イル)-1,2,3,4-テトラヒドロナフタレン-1,2ジカルボン酸無水物(22.5g、0.08mol)を、撹拌された混合物にゆっくり加えた。ディーンスタークトラップとコンデンサーをフラスコに取り付けた。混合物を6時間熱して還流し、アミン末端のジイミドを形成した。この縮合からの生成水の理論量は、この時までに得られた。反応混合物は、室温以下に冷却され、無水マレイン酸の17.6g(0.19mol)がフラスコに加えられた。混合物は、さらに8時間還流され、期待された量の生成水を得た。室温に冷却された後、さらにトルエン200mlがフラスコに加えられた。次に、希釈された有機層を水(100ml×3回)で洗浄し、塩や未反応の原料を除去した。その後、溶剤を真空下で除去し、暗琥珀色液状のビスマレイミド化合物104g(収率93%、Mw=3,700)を得た(A-1)。
フッ素樹脂コーティングされた撹拌バーを装備した500mlの丸底フラスコに、110gのトルエンと36gのN-メチルピロリドンを投入した。次にPRIAMINE 1075(クローダジャパン株式会社製)90.5g(0.17mol)を加え、ついで無水メタンスルホン酸16.3g(0.17mol)をゆっくりと加え、塩を形成した。ほぼ10分間撹拌して混合し、ついで1,2,4,5-シクロヘキサンテトラカルボン酸二無水物(18.9g、0.08mol)を、撹拌された混合物にゆっくり加えた。ディーンスタークトラップとコンデンサーをフラスコに取り付けた。混合物を6時間熱して還流し、アミン末端のジイミドを形成した。この縮合からの生成水の理論量は、この時までに得られた。反応混合物は、室温以下に冷却され、無水マレイン酸19.9g(0.20mol)がフラスコに加えられた。混合物は、さらに8時間還流され、期待された量の生成水を得た。室温に冷却された後、さらにトルエン200mlがフラスコに加えられた。次に、希釈された有機層を水(100ml×3回)で洗浄し、塩や未反応の原料を除去した。その後、溶剤を真空下で除去し、琥珀色ワックス状のビスマレイミド化合物110g(収率92%、Mw=3,000)を得た(A‘-3)。
[合成例2]
α-ナフトールアラルキル型フェノール樹脂(新日鐵化学(株)製SN495V(商品名)、OH基当量:236g/eq.、ナフトールアラルキルの繰り返し単位数nは1~5のものが含まれる)0.47mol(OH基換算)を、クロロホルム500mLに溶解させ、この溶液にトリエチルアミン0.7molを添加した(溶液1)。
温度を-10℃に保ちながら、0.93molの塩化シアンのクロロホルム溶液300gに対して、溶液1を1.5時間かけて滴下し、滴下終了後、30分撹拌した。
その後さらに、0.1molのトリエチルアミンとクロロホルム30gの混合溶液を反応器内に滴下し、30分撹拌して反応を完結させた。副生したトリエチルアミンの塩酸塩を反応液から濾別した後、得られた濾液を0.1N塩酸500mLで洗浄した後、水500mLでの洗浄を4回繰り返した。これを硫酸ナトリウムにより乾燥した後、75℃でエバポレートし、さらに90℃で減圧脱気することにより、褐色固形のα-ナフトールアラルキル型シアン酸エステル樹脂(SNCN、式(28)、n18は1~4のものが含まれる)を得た(B-2)。得られたα-ナフトールアラルキル型シアン酸エステル樹脂を赤外吸収スペクトルにより分析したところ、2264cm-1付近のシアン酸エステル基の吸収が確認された。
[合成例3]
温度計、冷却管、撹拌機を取り付けたフラスコにXD-1000(日本化薬(株)製、軟化点74.8℃、エポキシ当量255g/eq.)を225g、アクリル酸を72.1g、触媒としてトリフェニルホスフィン3g、溶剤としてプロピレングリコールモノメチルエーテルモノアセテートを固形分含有量80%となるように加え、100℃で24時間反応させ、反応中間体であるエポキシカルボキシレート化合物溶液を得た。
続いて、得られた反応性エポキシカルボキシレート化合物溶液に、多塩基酸無水物として1,2,3,6-テトラヒドロフタル酸無水物(THPA)(商品名:リカシッドTH、新日本理化(株)製)を140g入れ、溶剤として固形分含有量が65%となるようにプロピレングリコールモノメチルエーテルモノアセテートを加え、100℃で6時間反応させ、エチレン性不飽和基を有する化合物(B-6)を得た。得られたエチレン性不飽和基を有する化合物(B-6)の固形分酸価(AV:mgKOH/g)は110であった。
(A-1)一般式(1)で表される構成単位と、分子鎖の両末端にマレイミド基を含む、ビスマレイミド樹脂
合成例1のビスマレイミド樹脂A-1(下記式(3)で表される化合物、25℃で高粘度液体)
(A’-1)BMI-2300(ポリフェニルメタンマレイミド、下記式(29)で表される化合物、大和化成(株)製、25℃で固形)
(A’-2)BMI-3000(下記式(14)で表される化合物、DESIGNER MOLECURES Inc.製、25℃で固形)
(A’-3)比較合成例1(下記式(30)で表される化合物、25℃で液状)
(B-1)ビスマレイミド樹脂であるMIR-5000(下記式(31)で表される化合物、日本化薬(株)製、25℃で固形)
(B-2)合成例2で得られたα-ナフトールアラルキル型シアン酸エステル樹脂(SNCN、シアン酸エステル樹脂)
(B-3)P-d型ベンゾオキサジン化合物(四国化成工業(株)製、3,3’-(メチレン-1,4-ジフェニレン)ビス(3,4-ジヒドロ-2H-1,3-ベンゾオキサジン)、ベンゾオキサジン化合物)
(B-4)ビフェニルアラルキル型エポキシ樹脂(日本化薬(株)製NC-3000H(商品名)、エポキシ樹脂)
(B-5)カルボジイミド化合物(日清紡ケミカル(株)製カルボジライトB-01(商品名))
(B-6)合成例3で得られた酸変性ジシクロペンタジエンフェノール型エポキシアクリレート化合物(日本化薬(株)製KAYARAD(登録商標)ZXR-1889H(商品名)、エチレン性不飽和基を有する化合物)
(C-1)ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins社製Omnirad(登録商標)819(商品名))
(C-2)2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1(IGM Resins社製Omnirad(登録商標)369(商品名))
(C-3)2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン(IGM Resins社製Omnirad(登録商標)907(商品名))
実施例1~8及び比較例1~3の樹脂組成物について、以下に示す評価を行った。その結果を表1にまとめて示した。
実施例1~8及び比較例1~3で得られた感光性樹脂組成物を銅貼積層板(住友ベークライト(株)ELC4762)上にアプリケーターで塗布して、温度80℃において30分間加熱し、膜厚20μmの塗膜を形成した。次いで、波長405nm(h線)を含む活性エネルギー線を照射可能な光源(USHIO(株)製超高圧水銀灯 USH-500BY1(商品名))を用いて、21段ステップタブレットを用いて、現像後の残存段数が7段となる露光量にて投影露光機で露光した。
以下の基準にて感度を評価し、評価結果を表1に示した。
[評価基準]
◎:露光量500mJcm2未満で7段残存
○:露光量500mJ/cm2以上1000mJ/cm2未満で7段残存
△:露光量1000mJ/cm2以上3000mJ/cm2未満で7段残存
×:露光量3000mJ/cm2以上でも硬化せず
先ず、厚み12μmの超低粗度電解銅箔(CF-T4X-SV(商品名)、福田金属箔粉工業株式会社製)上に各実施例及び比較例で得られた感光性樹脂組成物をアプリケーターを用いて塗布後、温度80℃において30分間乾燥させ、銅箔上にフィルム状感光性樹脂組成物を形成させた。乾燥後のフィルム状感光性樹脂組成物の膜厚は20μmとなるように感光性樹脂組成物の塗布厚みを調整した。このフィルム状感光性樹脂組成物に対して、波長405nm(h線)を含む活性エネルギー線を照射可能な光源(USHIO(株)製超高圧水銀灯 500Wマルチライト(商品名))を用いて、露光量3000mJ/cm2にて露光を行い、次いで、温度180℃において60分間加熱して硬化させた後、銅箔をエッチングによって除去することにより、硬化膜を得た。
銅箔積層体の銅箔をエッチングにより除去し、130℃で30分乾燥させた後、樹脂フィルムの硬化物を切断して10cm×5cmの試験片を作製した。得られた試験片について、空洞共振器法誘電率測定装置(株式会社エーイーティー製)にて、10GHzでの比誘電率及び誘電正接を測定した。測定後、試験片を24時間水に浸漬して吸水後、水から取り出して水分を拭き取り、25℃30%の環境に一日放置したのち、再び10GHzでの比誘電率及び誘電正接を測定した。
銅箔積層体の両面の銅箔をエッチングにより除去し、130℃で30分乾燥させた後、樹脂フィルムの硬化物を切断して5cm×5mmの試験片を作製した。得られた試験片について、動的粘弾性試験機(DMA:商品名「RSA-G2」、TAInstruments製)により測定し、tanδが最大値のときの温度をガラス転移温度として求めた。
銅箔積層体の両面の銅箔をエッチングにより除去し、130℃で30分乾燥させた後、樹脂フィルムの硬化物を切断して10cm×5cmの試験片を作製した。得られた試験片を24時間水に浸漬して吸水後、水から取り出して水分を拭き取った後、試験片の重量増加率を吸水率とした。
各組成物を、スクリーン印刷法により25μmの厚さになるようにL/S=100μm/100μmのくし型パターンが形成されたエスパネックスMシリーズ(新日鐵化学製:ベースイミド厚25μm Cu厚18μm)上に塗布し、塗膜を80℃の熱風乾燥器で60分乾燥させた。次いで、アフレックス(Grade:25N NT)(AGC株式会社製)を樹脂面に被せ、220℃で2時間加熱することによって、HAST評価用の試験基板を得た。得られた基板の電極部分をはんだによる配線接続を行い、130℃、85%RHの環境下に置き、100Vの電圧をかけ、抵抗値が1×108Ω以下となるまでの時間を測定した。
○‥300時間以上
△‥30~300時間
×‥30時間以下
また、実施例1~8の樹脂組成物は、その硬化物の特性として、低誘電特性かつ吸水後の誘電特性に変化が小さく、低弾性でかつ高伸度、高耐熱でかつ低吸水率であり、優れた絶縁信頼性有していることが確認できた。
Claims (14)
- 下記式(1)で表される構成単位と、分子鎖の両末端にマレイミド基と、を含む、ビスマレイミド化合物(A)と、
前記ビスマレイミド化合物(A)以外のマレイミド化合物、シアン酸エステル化合物、ベンゾオキサジン化合物、エポキシ樹脂、カルボジイミド化合物、及びエチレン性不飽和基を有する化合物からなる群より選択される少なくとも1種以上の樹脂又は化合物(B)と、
光硬化開始剤(C)と、を含む、樹脂組成物。
- 前記ビスマレイミド化合物(A)と前記樹脂又は化合物(B)と前記光硬化開始剤(C)の総量を100質量部とした場合、前記式(1)で表されるビスマレイミド樹脂の含有量が5~99.4質量部である、請求項1または2に記載の樹脂組成物。
- 充填材を更に含む、請求項1~3のいずれか一項に記載の樹脂組成物。
- 請求項1~4のいずれか一項に記載の樹脂組成物を含む、硬化物。
- 支持体と、
前記支持体の片面又は両面に配された樹脂層と、を有し、
前記樹脂層が、請求項1又は2に記載の樹脂組成物を含む、
樹脂シート。 - 前記樹脂層の厚さが1~50μmである、請求項6に記載の樹脂シート。
- 基材と、
前記基材に含浸又は塗布された、請求項1~4 のいずれか一項に記載の樹脂組成物と、を含む、プリプレグ。 - 請求項7に記載の樹脂シート、及び請求項8に記載のプリプレグからなる群より選ばれる少なくとも1 種を含む層と、
前記層の片面又は両面に配された金属箔と、を有し、前記層が、前記樹脂組成物の硬化物を含む、金属箔張積層板。 - 絶縁層と、
前記絶縁層の片面又は両面に形成された導体層と、
を有し、前記絶縁層が、請求項1~4のいずれか一項に記載の樹脂組成物を含む、多層プリント配線板。 - 請求項1~4のいずれか一項に記載の樹脂組成物を含む、封止用材料。
- 請求項1~ 4のいずれか一項に記載の樹脂組成物と、強化繊維と、を含む、繊維強化複合材料。
- 請求項1~4のいずれか一項に記載の樹脂組成物を含む、接着剤。
- 請求項1~4のいずれか一項に記載の樹脂組成物を有する、半導体装置。
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