WO2020217672A1 - 硬化性樹脂組成物 - Google Patents
硬化性樹脂組成物 Download PDFInfo
- Publication number
- WO2020217672A1 WO2020217672A1 PCT/JP2020/006726 JP2020006726W WO2020217672A1 WO 2020217672 A1 WO2020217672 A1 WO 2020217672A1 JP 2020006726 W JP2020006726 W JP 2020006726W WO 2020217672 A1 WO2020217672 A1 WO 2020217672A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- resin composition
- maleimide
- curable resin
- compound
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 92
- -1 amine compound Chemical class 0.000 claims abstract description 151
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims abstract description 99
- 239000003822 epoxy resin Substances 0.000 claims abstract description 75
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 75
- 239000004065 semiconductor Substances 0.000 claims abstract description 29
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 238000001723 curing Methods 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000008393 encapsulating agent Substances 0.000 claims description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 238000010030 laminating Methods 0.000 claims description 11
- 239000011889 copper foil Substances 0.000 claims description 10
- 230000003014 reinforcing effect Effects 0.000 claims description 10
- 238000000465 moulding Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 238000013007 heat curing Methods 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 238000003825 pressing Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000003566 sealing material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- 150000001875 compounds Chemical class 0.000 description 70
- 229920005989 resin Polymers 0.000 description 65
- 239000011347 resin Substances 0.000 description 65
- 239000000047 product Substances 0.000 description 58
- 230000015572 biosynthetic process Effects 0.000 description 47
- 238000005227 gel permeation chromatography Methods 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 44
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 42
- 238000000034 method Methods 0.000 description 34
- 239000002904 solvent Substances 0.000 description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 27
- 229920003986 novolac Polymers 0.000 description 27
- 239000004643 cyanate ester Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 17
- 238000001816 cooling Methods 0.000 description 17
- 239000010410 layer Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- 238000009826 distribution Methods 0.000 description 15
- 239000011572 manganese Substances 0.000 description 15
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000004927 clay Substances 0.000 description 14
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 238000000434 field desorption mass spectrometry Methods 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 12
- 238000006297 dehydration reaction Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 239000004305 biphenyl Substances 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 230000002194 synthesizing effect Effects 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UGPWRRVOLLMHSC-UHFFFAOYSA-N 2-[3-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(C(C)(C)O)=C1 UGPWRRVOLLMHSC-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000013329 compounding Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000005350 fused silica glass Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 3
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 3
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 3
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 0 Cc(c(*)c(*=C)c(O**)c1O*)c1O* Chemical compound Cc(c(*)c(*=C)c(O**)c1O*)c1O* 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 229910002026 crystalline silica Inorganic materials 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 229920001955 polyphenylene ether Polymers 0.000 description 3
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 2
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- 238000009774 resonance method Methods 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Images
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; Imides
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- 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
- C08J5/246—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using polymer based synthetic fibres
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/36—Amides or imides
- C08F22/40—Imides, e.g. cyclic imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- 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
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
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- 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
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
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- 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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- 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
-
- 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
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- 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
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/07—Parts immersed or impregnated in a matrix
- B32B2305/076—Prepregs
-
- 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
- B32B2311/00—Metals, their alloys or their compounds
- B32B2311/12—Copper
-
- 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
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
Definitions
- the present invention relates to a curable resin composition, a cured product obtained from the curable resin composition, a prepreg, a circuit board, a build-up film, a semiconductor encapsulant, and a semiconductor device.
- thermosetting resin such as an epoxy resin or BT (bismaleimide-triazine) resin and heat-dried to obtain a prepreg, which is heat-cured.
- a laminated board, a multilayer board obtained by combining the laminated board and the prepreg and being heat-cured is widely used.
- semiconductor package substrates are becoming thinner, and warpage of the package substrate during mounting becomes a problem.
- a material exhibiting high heat resistance is required.
- thermosetting resin composition that provides a cured product that exhibits a sufficiently low dielectric loss tangent while maintaining a sufficiently low dielectric constant under these environments has been provided. It is desired.
- maleimide resin is attracting attention as a material that has both heat resistance, low dielectric constant, and low dielectric loss tangent.
- the conventional maleimide resin exhibits high heat resistance, its dielectric constant and dielectric loss tangent value do not reach the level required for advanced material applications, and in addition, it is difficult to dissolve in a solvent and is inferior in handleability.
- a cyanate ester-based material having high dielectric properties and heat resistance a phenol novolac type cyanate ester resin, a bisphenol A cyanate ester resin, and a non-halogen epoxy resin are blended.
- a resin composition is known (see Patent Document 1).
- the problem to be solved by the present invention is a curable resin composition having excellent heat resistance and dielectric properties in the cured product and the cured product thereof, and a prepreg, a circuit board, and a build having these performances. It is an object of the present invention to provide an up film, a semiconductor encapsulant, and a semiconductor device.
- the present inventors have made a curable resin composition containing maleimide (A) having an indan skeleton, an amine compound (B), and an epoxy resin (C).
- maleimide (A) having an indan skeleton
- B an amine compound
- C an epoxy resin
- the cured product can have a low dielectric constant and a low dielectric loss tangent while also having excellent heat resistance, and have completed the present invention.
- the present invention relates to a curable resin composition containing maleimide (A) having an indane skeleton, an amine compound (B), and an epoxy resin (C).
- the maleimide (A) is preferably represented by the following general formula (1).
- Ra independently has an alkyl group having 1 to 10 carbon atoms, an alkyloxy group or an alkylthio group, an aryl group having 6 to 10 carbon atoms, an aryloxy group or an arylthio group, and 3 to 3 carbon atoms. It represents a cycloalkyl group of 10, a halogen atom, a nitro group, a hydroxyl group or a mercapto group, where q represents an integer value of 0 to 4. When q is 2 to 4, Ra may be the same in the same ring. Rb may be different, respectively.
- Rb is an alkyl group having 1 to 10 carbon atoms, an alkyloxy group or an alkylthio group, an aryl group having 6 to 10 carbon atoms, an aryloxy group or an arylthio group, and 3 to 10 carbon atoms.
- Rb may be the same or different in the same ring. It may be.
- N is the average number of repeating units and indicates a numerical value of 0.5 to 20.
- the cured product of the present invention is preferably formed by subjecting the curable resin composition to a curing reaction.
- the prepreg of the present invention preferably has a reinforcing base material and a semi-cured product of the curable resin composition impregnated in the reinforcing base material.
- the circuit board of the present invention is preferably obtained by laminating the prepreg and copper foil and heat-pressing molding.
- the build-up film of the present invention preferably contains the curable resin composition.
- the semiconductor encapsulant of the present invention preferably contains the curable resin composition.
- the semiconductor device of the present invention preferably contains a cured product obtained by heat-curing the semiconductor encapsulant.
- the curable resin composition obtained from the curable resin composition has excellent heat resistance and dielectric properties, and has these performances. It is possible to provide a cured product, a prepreg, a circuit board, a build-up film, a semiconductor encapsulant, and a semiconductor device obtained from the curable resin composition, which is useful.
- maleimide (A) having an indane skeleton hereinafter, may be referred to as “component (A)”
- component (B) amine compound
- component (C) amine compound
- the present invention relates to a curable resin composition, which comprises an epoxy resin (C) (hereinafter, may be referred to as “component (C)”).
- component (C) it is preferable that the maleimide (A) is represented by the following general formula (1). Since the maleimide (A) has an indane skeleton, the proportion of polar functional groups in the structure of the maleimide (A) is smaller than that of the conventional maleimide, and thus the dielectric property is excellent, which is preferable.
- a cured product using a conventional maleimide resin tends to be brittle and may be inferior in brittleness.
- the maleimide (A) has an indane skeleton, it has excellent flexibility and brittleness. Improvement is also expected and is preferable.
- Ra independently has an alkyl group having 1 to 10 carbon atoms, an alkyloxy group or an alkylthio group, an aryl group having 6 to 10 carbon atoms, an aryloxy group or an arylthio group, and 3 carbon atoms. It represents a cycloalkyl group of ⁇ 10 (preferably 5-10), a halogen atom, a nitro group, a hydroxyl group or a mercapto group, and q represents an integer value of 0 to 4. When q is 2 to 4, Ra may be the same or different in the same ring.
- Rb is independently an alkyl group having 1 to 10 carbon atoms, an alkyloxy group or an alkylthio group, an aryl group having 6 to 10 carbon atoms, an aryloxy group or an arylthio group, a cycloalkyl group having 3 to 10 carbon atoms, and a halogen atom.
- a hydroxyl group or a mercapto group, and r represents an integer value of 0 to 3. When r is 2 to 3, Rb may be the same or different in the same ring.
- n is the average number of repeating units, and represents a numerical value of 0.5 to 20. When r and q are 0, Ra and Rb each refer to a hydrogen atom.
- the Ra of the general formula (1) is preferably any one of an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and an aryl group having 6 to 10 carbon atoms, and the carbon number 1 is 1.
- an alkyl group of to 4 or the like the solvent solubility is improved due to the decrease in flatness and the decrease in crystallinity in the vicinity of the maleimide group, and a cured product can be obtained without impairing the reactivity of the maleimide group. This is a possible preferred embodiment.
- the q in the general formula (1) is preferably 2 to 3, and more preferably 2.
- q 2 to 3
- the influence of steric hindrance is small, the electron density on the aromatic ring is improved, and this is a preferable embodiment in the production (synthesis) of maleimide.
- r is 0 and Rb is preferably a hydrogen atom, r is 1 to 3, and Rb is an alkyl group having 1 to 4 carbon atoms and 3 carbon atoms. It is preferably at least one selected from the group consisting of a cycloalkyl group of to 6 and an aryl group having 6 to 10 carbon atoms, and in particular, r is 0 and Rb is a hydrogen atom. Therefore, steric hindrance is reduced during the formation of the indan skeleton in maleimide, which is advantageous for the production (synthesis) of maleimide, which is a preferable embodiment.
- the following general formula (2) represents a monovalent functional group in which Rc is independently selected from the group consisting of the following general formulas (3) and (4), and the ortho of at least one of the two Rc is Rc.
- the position is a hydrogen atom, and Rb and r are compounds showing the same as above.
- At least one of the ortho-position and para-position of the amino group is a hydrogen atom
- Ra and q are aniline or a derivative thereof having the same characteristics as described above.
- the following general formula (7) having an indan skeleton is included in the structure, and among the aniline or its derivative represented by the general formula (5), q Is 3 or less, and when at least two of the ortho and para positions of the amino group are hydrogen atoms, the structure is represented by the following general formula (8).
- Ra, Rb, q and r in the following general formula (8) are the same as described above, m is the number of repeating units, and indicates an integer value of 1 to 20.
- the structure represented by the following general formula (8) may also be included in the structure of the above general formula (6).
- the average number of repeating units n is a low melting point (low softening point), a low melt viscosity, and handleability.
- the average number of repeating units n (average value) is 0.5 to 20, preferably 0.7 to 10.0, and more preferably 0.95 to 10.0 in order to make the value excellent. , More preferably 0.98 to 9.0, still more preferably 0.99 to 8.0, still more preferably 1.0 to 7.0, still more preferably 1.0 to 6.0. Is.
- the solvent solubility is excellent as compared with the maleimides used so far, which is a preferable embodiment. If n is less than 0.5, the content ratio of the refractory substance in the structure of maleimide (A) becomes high, the solvent solubility is inferior, and the high molecular weight component contributing to brittleness. Since the ratio is low, the brittleness of the obtained cured product is lowered, and the flexibility and flexibility may be lowered, which is not preferable.
- n exceeds 20
- the heat resistance will be inferior
- the amount of high molecular weight components will be too large, the fluidity will be lowered when molding the cured product, and the handleability will be inferior. It is not preferable.
- the value of n is preferably 0.5 to 10.0, more preferably 0.95 to 10.0, from the viewpoint of high thermal deformation temperature, high glass transition temperature, and the like.
- compound (a) is not particularly limited, but is typically p- and m-diisopropenylbenzene, p- and. m-bis ( ⁇ -hydroxyisopropyl) benzene, 1- ( ⁇ -hydroxyisopropyl) -3-isopropenylbenzene, 1- ( ⁇ -hydroxyisopropyl) -4-isopropenylbenzene or a mixture thereof is used.
- nuclear alkyl group substituents of these compounds such as diisopropenyltoluene and bis ( ⁇ -hydroxyisopropyl) toluene can also be used, and further nuclear halogen substituents such as chlorodiisopropenylbenzene and chlorobis ( ⁇ ). -Hydroxyisopropyl) benzene and the like can also be used.
- examples of the compound (a) include 2-chloro-1,4-diisopropenylbenzene, 2-chloro-1,4-bis ( ⁇ -hydroxyisopropyl) benzene, and 2-bromo-1,4-di.
- the substituent contained in the compound (a) is not particularly limited, and the above-exemplified compound can be used. However, in the case of a substituent having a large steric hindrance, it is compared with a substituent having a small steric hindrance. Stacking of the obtained maleimides is less likely to occur, and crystallization of the maleimides is less likely to occur, that is, the solvent solubility of the maleimides is improved, which is a preferable embodiment.
- compound (b) in addition to aniline, for example, dimethylaniline, diethylaniline, diisopropylaniline, ethylmethylaniline, chloro Aniline, dichloroaniline, toluidine, xylidine, phenylaniline, nitroaniline, aminophenol, cyclohexylaniline and the like can be used.
- methoxyaniline, ethoxyaniline, phenoxyaniline, naphthoxyaniline, aminothiol, methylthioaniline, ethylthioaniline and phenylthioaniline can be exemplified.
- the compound (b) is not particularly limited, and the above-exemplified compound can be used, and methyl as a substituent, for example, 2,6-dimethylaniline.
- the benzene ring and the 5-membered ring of maleimide take a twisted conformation due to the steric hindrance of the methyl group, which makes stacking difficult, so that the crystallinity is lowered, the solvent solubility is improved, and this is a preferable embodiment. ..
- the steric hindrance is too large, there is a concern that the reactivity of maleimide during synthesis may be hindered. Therefore, for example, it is preferable to use the compound (b) having an alkyl group having 2 to 4 carbon atoms.
- the compound (a) and the compound (b) are converted into moles of the compound (b) with respect to the compound (a).
- the compound (compound (b) / compound (a)) is subjected to a charging reaction (first step) at a ratio of preferably 0.1 to 2.0, more preferably 0.2 to 1.0
- the compound (1st step) is further subjected to b) is further added in an amount of preferably 0.5 to 20.0, more preferably 0.7 to 5.0 in terms of molar ratio to the compound (a) previously added, and reacted (second step).
- a maleimide (A) having an indan skeleton can be obtained.
- the compound (b) is preferably added as a molar ratio (compound (b) / compound (a)) to the compound (a) added earlier, preferably 0.10 to 0.49. , More preferably 0.15 to 0.40, and even more preferably 0.20 to 0.39, so that the content ratio of the low molecular weight high melting point compound having a wide molecular weight distribution is low and high. Since the proportion of the molecular weight component is high, it is preferable to obtain an intermediate amine compound and maleimide which are excellent in solvent solubility and can contribute to flexibility and brittleness resistance.
- Examples of the acid catalyst used in the reaction include inorganic acids such as phosphoric acid, hydrochloric acid and sulfuric acid, oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, fluoromethanesulfonic acid and other organic acids, and active white clay.
- Acidic white clay, silica alumina, zeolite, solid acids such as strongly acidic ion exchange resins, heteropolyhydrochloride, etc. can be mentioned, but solid acids that can be easily removed by filtration after the reaction are from the viewpoint of hand linkability. When other acids are used, it is preferable to neutralize with a base and wash with water after the reaction.
- the blending amount of the acid catalyst is such that the acid catalyst is blended in the range of 5 to 40 parts by mass with respect to 100 parts by mass of the compound (a) and the compound (b), which are the raw materials to be charged first. From the viewpoint of handleability and economy, 5 to 30 parts by mass is preferable.
- the reaction temperature may usually be in the range of 100 to 300 ° C., but is preferably 150 to 230 ° C. in order to suppress the formation of isomer structures and avoid side reactions such as thermal decomposition.
- the reaction time the reaction does not proceed completely in a short time, and side reactions such as a thermal decomposition reaction of the product occur in a long time. Therefore, under the reaction temperature conditions, usually, the total reaction time is increased. It is in the range of 2 to 48 hours, preferably in the range of 2 to 24 hours in total, more preferably in the range of 4 to 24 hours in total, and further preferably in the range of 4 to 12 hours in total. A total of 8 to 12 hours is more preferable for reducing the low molecular weight component and increasing the high molecular weight component.
- aniline or a derivative thereof also serves as a solvent
- a solvent capable of azeotropic dehydration such as toluene, xylene, or chlorobenzene is used.
- the solvent may be distilled off, and then the reaction may be carried out within the above reaction temperature range.
- the maleimide (A) used in the present invention is prepared by charging an intermediate amine compound represented by the above general formula (6) obtained by the above method into a reactor, dissolving it in an appropriate solvent, and then using maleic anhydride and a catalyst. It can be obtained by reacting in the presence of, and after the reaction, removing unreacted maleic anhydride and other impurities by washing with water or the like, and removing the solvent by reducing the pressure. Moreover, you may use a dehydrating agent at the time of a reaction.
- the maleimide (A) used in the present invention has the skeleton of the general formula (1) and includes a structure represented by the general formula (7) having an indane skeleton, but has a q of 3 or less and an amino group.
- the structure corresponding to the above general formula (8) that is, the structure represented by the following general formula (9) is also represented by the above general formula (1). Included as a structure to be.
- Ra, Rb, q, r and m in the general formula (9) are the same as those described above.
- Examples of the organic solvent used in the maleimization reaction for synthesizing maleimide (A) include ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, cyclohexanone, and acetophenone, N, N-dimethylformamide, N, Aprotonic solvents such as N-dimethylacetamide, dimethylsulfoxide, N-methyl-2-pyrrolidone, acetonitrile and sulfolane, cyclic ethers such as dioxane and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, benzene, toluene and xylene. Examples thereof include aromatic solvents such as, and these may be used alone or in combination.
- ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, cyclohexanone, and
- the intermediate amine compound and maleic anhydride are preferably blended in the range of 1 to 1.5, more preferably the equivalent ratio of maleic anhydride to the amino equivalent of the intermediate amine compound.
- Examples of the catalyst used in the maleimization reaction include acetates such as nickel, cobalt, sodium, calcium, iron, lithium and manganese, inorganic salts such as chlorides, bromides, sulfates and nitrates, phosphoric acid, hydrochloric acid and sulfuric acid.
- Inorganic acids such as oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, organic acids such as fluoromethanesulfonic acid, active clay, acidic clay, silica alumina, zeolite, solids such as strongly acidic ion exchange resin. Acids, heteropolyhydrochloric acid and the like can be mentioned, but toluenesulfonic acid is particularly preferable.
- Examples of the dehydrating agent used in the maleimidization reaction include lower aliphatic carboxylic acid anhydrides such as acetic anhydride, propionic anhydride and butyric anhydride, oxides such as phosphorus pentoxide, calcium oxide and barium oxide, and inorganic acids such as sulfuric acid. , Porous ceramics such as molecular sieves, etc., but acetic anhydride can be preferably used.
- the amount of the catalyst and dehydrating agent used in the maleimidization reaction is not particularly limited, but usually 0.0001 to 1.0 mol, preferably 0, of the catalyst is based on 1 equivalent of the amino group of the intermediate amine compound. It can be used in an amount of 0.01 to 0.5 mol, more preferably 0.01 to 0.3 mol, and a dehydrating agent of 1 to 3 mol, preferably 1 to 1.5 mol.
- the reaction conditions for maleimide formation the intermediate amine compound and maleic anhydride are charged, and the temperature range is 10 to 100 ° C., preferably 30 to 50 ° C. for 0.5 to 12 hours, preferably 1 to 8 hours.
- the catalyst can be added and the reaction can be carried out in a temperature range of 90 to 130 ° C., preferably 105 to 120 ° C. for 2 to 24 hours, preferably 4 to 10 hours to reduce low molecular weight components. 6-10 hours are more preferred for increasing the high molecular weight components.
- unreacted maleic anhydride and other impurities are removed by washing with water or the like, and heat aging also reduces the low molecular weight component and increases the high molecular weight component.
- the maleimide (A) has a molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) calculated from gel permeation chromatography (GPC) measurement because it is excellent in low dielectric constant and low dielectric loss tangent. It is preferably in the range of 1.0 to 10.0, more preferably 1.1 to 9.0, still more preferably 1.1 to 8.0, and even more preferably 1.2 to 5.0. It is more preferably 1.2 to 4.0, further preferably 1.3 to 3.8, particularly preferably 1.3 to 3.6, and most preferably 1.3 to 3.6. It is 3.4.
- the curable resin composition of the present invention is characterized by containing an amine compound (B) (hereinafter, may be referred to as "component (B)"). Since the amine compound (B) can contribute to low-temperature curing and exhibits excellent molding processability, it can be used as a molding material for structural materials and is useful. Further, by reacting with the maleimide (A) having the indane skeleton, it acts as a curing agent, can form a three-dimensional crosslink, and can obtain a cured product having excellent heat resistance, which is a preferable embodiment. Further, in relation to the epoxy resin (C) described in detail below, it also acts as a curing agent and improves the adhesion to copper, which is useful in, for example, manufacturing a circuit board using a copper foil.
- the amine compound (B) is not particularly limited, and for example, diaminodiphenylmethane, diaminodiphenylethane, diaminodiphenyl ether, diaminodiphenylsulfone, orthophenylenediamine, metaphenylenediamine, paraphenylenediamine, metaxylenediamine, paraxylenediamine, and the like.
- Examples thereof include diethyltoluenediamine, diethylenetriamine, triethylenetetramine, isophoronediamine, imidazole, BF3-amine complex, guanidine derivative, guanamine derivative and the like.
- the curable resin composition of the present invention is characterized by containing an epoxy resin (C) (hereinafter, may be referred to as "component (C)").
- the epoxy resin (C) is useful because it can prepare a curable resin composition which has good fluidity at the time of preparation of the curable resin composition and can obtain a cured product having excellent adhesion. .. Further, when the amine compound (B) and the epoxy resin (C) are used, the adhesion to copper is improved, which is useful in, for example, manufacturing a circuit board using a copper foil.
- the epoxy resin (C) is not particularly limited, and for example, phenol novolac type epoxy resin, cresol novolac type epoxy resin, ⁇ -naphthol novolac type epoxy resin, ⁇ -naphthol novolac type epoxy resin, bisphenol A novolac type epoxy resin.
- Novolak type epoxy resin such as biphenyl novolac type epoxy resin
- aralkyl type epoxy resin such as phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, phenol biphenyl aralkyl type epoxy resin
- bisphenol A type epoxy resin bisphenol AP type epoxy resin, Bisphenol AF type epoxy resin, bisphenol B type epoxy resin, bisphenol BP type epoxy resin, bisphenol C type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, tetrabromo bisphenol A type epoxy resin, etc.
- Biphenyl type epoxy resin biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, biphenyl type epoxy resin such as epoxy resin having biphenyl skeleton and diglycidyloxybenzene skeleton; naphthalene type epoxy resin; binaphthol type epoxy resin; binaphthyl type epoxy Resin: Dicyclopentadiene type epoxy resin such as dicyclopentadienephenol type epoxy resin; glycidylamine such as tetraglycidyldiaminodiphenylmethane type epoxy resin, triglycidyl-p-aminophenol type epoxy resin, glycidylamine type epoxy resin of diaminodiphenylsulfone Type epoxy resin; diglycidyl ester type epoxy resin such as 2,6-naphthalenedicarboxylic acid diglycidyl ester type epoxy resin, glycidyl ester type epoxy resin of hexahydrophthalic anhydr
- a curing agent other than the amine compound (B) can be added to the curable resin composition of the present invention as long as the curing of the present invention is not impaired.
- the amine compound (B) is preferably 50% by mass or more, more preferably 60% by mass or more, further preferably 70% by mass or more, and particularly preferably 80% by mass or more, based on 100% by mass of the total amount of the curing agent. , 90% by mass or more is most preferable.
- Examples of the curing agent other than the amine compound (B) include an amide compound, an acid anhydride compound, a phenol compound, a polyphenylene ether compound, a cyanate ester compound, and a compound having an unsaturated double bond-containing substituent. , Diene-based polymers and the like. These curing agents may be used alone or in combination of two or more.
- amide compound examples include a polyamide resin synthesized from a dimer of dicyandiamide and linolenic acid and ethylenediamine.
- Examples of the acid anhydride-based compound include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, and hexahydrophthalic anhydride. Examples thereof include methylhexahydrophthalic anhydride.
- phenolic compound examples include phenol novolac resin, cresol novolac resin, aromatic hydrocarbon formaldehyde resin modified phenol resin, dicyclopentadienephenol-added resin, phenol aralkyl resin (Zyroc resin), and resorcin novolac resin.
- the polyphenylene ether-based compound has, for example, a structure represented by the following general formula (10) or (11).
- Rd in the general formulas (10) and (11) are independently hydrogen atoms, alkyl groups having 1 to 5 carbon atoms, alkoxy groups having 1 to 5 carbon atoms, and cycloalkyl groups having 3 to 5 carbon atoms. , Alkoxy group with 1 to 5 carbon atoms, thioether group with 1 to 5 carbon atoms, alkylcarbonyl group with 2 to 5 carbon atoms, alkyloxycarbonyl group with 2 to 5 carbon atoms, alkylcarbonyloxy group with 2 to 5 carbon atoms , Alkoxysulfonyl groups having 1 to 5 carbon atoms and the like.
- Examples of the terminal structure of the structures of the general formulas (10) and (11) include those having a hydroxyl group or a reactive double bond-containing group. Further, s is an integer value of 1 to 30, and t and u are also integer values of 1 to 30.
- the alkyl group having 1 to 5 carbon atoms is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and a propyl group. Be done.
- the alkenyl group having 1 to 5 carbon atoms is not particularly limited, and examples thereof include a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentenyl group, and an isopropenyl group.
- the cycloalkyl group having 3 to 5 carbon atoms is not particularly limited, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a methylcyclobutyl group.
- the alkoxy group having 1 to 5 carbon atoms is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and a pentyloxy group.
- the thioether group having 1 to 5 carbon atoms is not particularly limited, and examples thereof include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, and a pentylthio group.
- the alkylcarbonyl group having 2 to 5 carbon atoms is not particularly limited, and examples thereof include a methylcarbonyl group, an ethylcarbonyl group, a propylcarbonyl group, an isopropylcarbonyl group, and a butylcarbonyl group.
- the alkyloxycarbonyl group having 2 to 5 carbon atoms is not particularly limited, and examples thereof include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, and a butyloxycarbonyl group.
- the alkylcarbonyloxy group having 2 to 5 carbon atoms is not particularly limited, and examples thereof include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, an isopropylcarbonyloxy group, and a butylcarbonyloxy group.
- the alkylsulfonyl group having 1 to 5 carbon atoms is not particularly limited, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, and a pentylsulfonyl group.
- the Rd is preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and a cycloalkyl group having 3 to 5 carbon atoms, and preferably a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. It is more preferably a hydrogen atom, a methyl group, or an ethyl group, and particularly preferably a hydrogen atom or a methyl group.
- Y in (11) above includes a divalent aromatic group derived from an aromatic compound having two phenolic hydroxyl groups.
- the aromatic compound having two phenolic hydroxyl groups is not particularly limited, but is not particularly limited, but is catechol, resorcinol, hydroquinone, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-.
- examples thereof include dihydroxynaphthalene, 4,4'-biphenol, bisphenol A, bisphenol B, bisphenol BP, bisphenol C, bisphenol F, tetramethylbisphenol A and the like.
- hydroquinone, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 4,4'-biphenol, bisphenol A, bisphenol E, and bisphenol F are preferable, and 4,4'-biphenol and bisphenol A are preferable.
- Tetramethylbisphenol A is more preferable.
- Y is an aromatic having two phenolic hydroxyl groups. It is a divalent aromatic group derived from a group compound.
- cyanate ester compound examples include bisphenol A type cyanate ester resin, bisphenol F type cyanate ester resin, bisphenol E type cyanate ester resin, bisphenol S type cyanate ester resin, bisphenol sulfide type cyanate ester resin, and phenylene ether type cyanate ester resin. , Naftyrene ether type cyanate ester resin, biphenyl type cyanate ester resin, tetramethylbiphenyl type cyanate ester resin, polyhydroxynaphthalene type cyanate ester resin, phenol novolac type cyanate ester resin, cresol novolac type cyanate ester resin, triphenylmethane type cyanate.
- Ester resin tetraphenylethane type cyanate ester resin, dicyclopentadiene-phenol addition reaction type cyanate ester resin, phenol aralkyl type cyanate ester resin, naphthol novolac type cyanate ester resin, naphthol aralkyl type cyanate ester resin, naphthol-phenol co-condensed novolak
- examples thereof include type cyanate ester resin, naphthol-cresol co-condensed novolak type cyanate ester resin, aromatic hydrocarbon formaldehyde resin modified phenol resin type cyanate ester resin, biphenyl modified novolac type cyanate ester resin, and anthracene type cyanate ester resin.
- the compound having an unsaturated double bond-containing substituent is not particularly limited as long as it is a compound having two or more unsaturated bond-containing substituents in the molecule, but the unsaturated bond-containing substituent may be used.
- Examples thereof include compounds having an allyl group, an isopropenyl group, a 1-propenyl group, an acryloyl group, a methacryloyl group, a styryl group, a styrylmethyl group and the like.
- the diene-based polymer examples include non-modified diene-based polymers that have not been modified by polar groups.
- the polar group is a functional group that affects the dielectric property, and examples thereof include a phenol group, an amino group, and an epoxy group.
- the diene polymer is not particularly limited, and for example, 1,2-polybutadiene, 1,4-polybutadiene and the like can be used.
- the diene polymer a homopolymer of butadiene in which 50% or more of the butadiene units in the polymer chain are 1,2-bonds and a derivative thereof can also be used.
- a curing accelerator can be appropriately used in combination with the curable resin composition of the present invention, if necessary.
- Various curing accelerators can be used, and examples thereof include phosphorus compounds, tertiary amines, imidazoles, organic acid metal salts, Lewis acids, and amine complex salts.
- phosphorus compounds tertiary amines, imidazoles, organic acid metal salts, Lewis acids, and amine complex salts.
- phosphorus compounds tertiary amines, imidazoles, organic acid metal salts, Lewis acids, and amine complex salts.
- -[5.4.0]-Undesen (DBU) is preferred.
- the curable resin composition of the present invention is characterized by containing maleimide (A) having an indane skeleton, an amine compound (B), and an epoxy resin (C). Since the maleimide (A) has an indan skeleton, the maleimide (A) has excellent solvent solubility, easy preparation of a curable resin composition, and excellent handleability as compared with the conventional maleimide. Since the proportion of polar functional groups in the structure is small, a cured product having excellent dielectric properties can be obtained. Further, the amine compound (B) acting as a curing agent can contribute to low-temperature curing, and the epoxy resin (C) has good fluidity during preparation of the curable resin composition and is excellent in adhesion.
- a cured product can be obtained. Further, when the amine compound (B) acting as a curing agent reacts with the maleimide (A) and the epoxy resin (C), three-dimensional cross-linking can be generated and curing with excellent heat resistance is possible. A product can be obtained, which is a preferable embodiment. Further, the reaction between the amine compound (B) and the epoxy resin (C) improves the adhesion to copper, which is useful in, for example, manufacturing a circuit board using a copper foil.
- the component (A): (component (B) + component (C)) is 90 :. It is preferably 10 to 10:90, more preferably 80:20 to 20:80, further preferably 70:30 to 30:70, and particularly preferably 60:40 to 40:60. Is. By adjusting the compounding ratio within the above range, heat resistance, low dielectric constant, and low dielectric loss tangent can be obtained, which is preferable.
- the compounding ratio (parts by mass) of the amine compound (B) and the epoxy resin (C) in the curable resin composition of the present invention is not particularly limited, but the obtained cured product characteristics are good.
- the (C) component is preferably 90:10 to 10:90, more preferably 80:20 to 20:80, and even more preferably 65:35 to 35:65. Is. By adjusting the compounding ratio within the above range, heat resistance, low dielectric constant, and low dielectric loss tangent can be obtained, which is preferable.
- the curable resin composition of the present invention contains an alkenyl group-containing compound, for example, a bismaleimide other than the maleimide (A), an allyl ether compound, a triallyl cyanurate, and an alkenyl phenol compound, as long as the object is not impaired.
- an alkenyl group-containing compound for example, a bismaleimide other than the maleimide (A), an allyl ether compound, a triallyl cyanurate, and an alkenyl phenol compound, as long as the object is not impaired.
- Vinyl group-containing polyolefin compound and the like can also be added.
- other thermosetting resins such as a thermosetting polyimide resin, a polyphenylene ether, a phenol resin, an active ester resin, a benzoxazine resin, and a cyanate resin can also be appropriately blended depending on the intended purpose.
- a non-halogen flame retardant that does not substantially contain a halogen atom can be blended in order to exhibit flame retardancy within a range that does not impair the purpose.
- the non-halogen flame retardant include phosphorus flame retardants, nitrogen flame retardants, silicone flame retardants, inorganic flame retardants, organic metal salt flame retardants, and the like, and these are used alone or in combination. be able to.
- An inorganic filler can be added to the curable resin composition of the present invention, if necessary.
- the inorganic filler include fused silica, crystalline silica, alumina, silicon nitride, aluminum hydroxide and the like.
- fused silica When the blending amount of the inorganic filler is particularly large, it is preferable to use fused silica.
- the molten silica can be used in either a crushed form or a spherical shape, but in order to increase the blending amount of the molten silica and suppress an increase in the melt viscosity of the molding material, it is preferable to mainly use a spherical one.
- the filling rate is preferably high in consideration of flame retardancy, and is particularly preferably 20% by mass or more with respect to the total amount of the curable resin composition.
- a conductive filler such as silver powder or copper powder can be used.
- the curable resin composition of the present invention can be added with various compounding agents such as a silane coupling agent, a mold release agent, a pigment, and an emulsifier, if necessary.
- the cured product of the present invention is preferably formed by subjecting the curable resin composition to a curing reaction.
- the curable resin composition is obtained by uniformly mixing each of the above-mentioned components, and can be easily made into a cured product by the same method as a conventionally known method.
- Examples of the cured product include molded products such as laminates, cast products, adhesive layers, coating films, and films.
- the curing (heat curing) reaction is easily carried out without a catalyst, but if a faster reaction is desired, a polymerization initiator such as an organic peroxide or an azo compound, a phosphine compound, or a tertiary compound is used.
- a polymerization initiator such as an organic peroxide or an azo compound, a phosphine compound, or a tertiary compound is used.
- a basic catalyst such as amine is effective.
- there are benzoyl peroxide, dicumyl peroxide, azobisisobutyronitrile, triphenylphosphine, triethylamine, imidazoles, etc. and the blending amount is 0.05 to 5% by mass of the entire curable resin composition. preferable.
- the prepreg of the present invention preferably has a reinforcing base material and a semi-cured product of the curable resin composition impregnated in the reinforcing base material.
- a method for producing the prepreg a known method can be used, but a reinforcing group in which the reinforcing base material is impregnated with a resin varnish obtained by dissolving (diluting) the curable resin composition in an organic solvent and impregnated with the resin varnish.
- a prepreg can be obtained by semi-curing (or uncuring) the curable resin composition by heat-treating the material.
- organic solvent examples include toluene, xylene, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, methyl ethyl ketone (MEK), methyl isobutyl ketone, dioxane, tetrahydrofuran and the like. , Alone, or as a mixed solvent of two or more kinds.
- the reinforcing base material impregnated with the resin varnish is woven fabric or non-woven fabric made of glass fiber, polyester fiber, polyamide fiber or other inorganic fiber, organic fiber, matte, paper or the like, and these may be used alone or in combination. Can be used.
- the mass ratio of the curable resin composition and the reinforcing base material in the prepreg is not particularly limited, but usually, the curable resin composition (resin content in the prepreg) is 20 to 60% by mass. It is preferable to prepare.
- the conditions for the heat treatment of the prepreg are appropriately selected depending on the type and amount of the organic solvent, catalyst, and various additives used, but are usually 3 to 30 minutes at a temperature of 80 to 220 ° C. It is done under such conditions.
- the cured product obtained by the curable resin composition of the present invention is excellent in heat resistance and dielectric properties, it can be suitably used for heat-resistant members and electronic members.
- it can be suitably used for circuit boards, semiconductor encapsulants, semiconductor devices, build-up films, build-up boards, adhesives, resist materials, and the like.
- it can be suitably used for a matrix resin of a fiber reinforced resin, and is particularly suitable as a prepreg having high heat resistance.
- the maleimide (A) having the indane skeleton contained in the curable resin composition can be made into a paint because it exhibits excellent solubility in various solvents.
- the heat-resistant members and electronic members thus obtained can be suitably used for various purposes.
- the circuit board is preferably obtained by laminating the prepreg and the copper foil and heat-pressing molding.
- the above prepregs are laminated by a conventional method, copper foils are appropriately laminated, and the temperature is 170 to 300 ° C. under a pressure of 1 to 10 MPa.
- a method of heat-pressing molding for 10 minutes to 3 hours can be mentioned.
- the semiconductor encapsulant preferably contains the curable resin composition.
- the curable resin composition is further mixed with a curing accelerator as an optional component and a compounding agent such as an inorganic filler. If necessary, a method of sufficiently melting and mixing the mixture with an extruder, a feeder, a roll, or the like until the mixture becomes uniform can be mentioned.
- fused silica is usually used as the inorganic filler, but when used as a high thermal conductivity semiconductor encapsulant for power transistors and power ICs, crystalline silica, alumina, and silicon nitride having higher thermal conductivity than fused silica It is preferable to use high-filling silicon or the like, or use fused silica, crystalline silica, alumina, silicon nitride, or the like.
- an inorganic filler in the range of 30 to 95 parts by mass per 100 parts by mass of the curable resin composition, and among them, flame retardancy, moisture resistance, solder crack resistance improvement, and linear expansion
- 70 parts by mass or more is more preferable, and 80 parts by mass or more is further preferable.
- the semiconductor device preferably includes a cured product obtained by heat-curing the semiconductor encapsulant.
- the semiconductor encapsulant is cast, or molded using a transfer molding machine, an injection molding machine, or the like, and further. Examples thereof include a method of heat curing at 50 to 250 ° C. for 2 to 10 hours.
- step 1 the curable resin composition in which rubber, a filler and the like are appropriately mixed is applied to a circuit board on which a circuit is formed by a spray coating method, a curtain coating method or the like, and then cured.
- step 2 if necessary, a circuit board coated with the curable resin composition is drilled with a predetermined through-hole portion or the like, treated with a roughening agent, and the surface thereof is washed with hot water. Unevenness is formed on the substrate, and a metal such as copper is plated.
- step 3 the operations of steps 1 and 2 are sequentially repeated as desired, and the resin insulating layer and the conductor layer having a predetermined circuit pattern are alternately built up to form a build-up substrate.
- the through-hole portion may be drilled after the resin insulating layer of the outermost layer is formed.
- the build-up substrate in the present invention is roughened by heat-pressing a resin-containing copper foil obtained by semi-curing the resin composition on a copper foil onto a wiring board on which a circuit is formed at 170 to 300 ° C. It is also possible to produce a build-up substrate by omitting the steps of forming a surface and plating.
- the build-up film of the present invention preferably contains the curable resin composition.
- a curable resin composition is applied on a support film and then dried to form a resin composition layer on the support film. The method can be mentioned.
- the curable resin composition of the present invention is used as a build-up film, the film is softened under the temperature conditions of lamination (usually 70 ° C. to 140 ° C.) in the vacuum laminating method, and is applied to the circuit board at the same time as laminating the circuit board.
- the diameter of the through hole of the circuit board is usually 0.1 to 0.5 mm, and the depth is usually 0.1 to 1.2 mm, and it is usually preferable to enable resin filling in this range.
- a varnished resin composition is prepared by blending an organic solvent, and then the varnished resin composition is applied to the surface of the support film (Y). Then, the organic solvent is further dried by heating, hot air blowing, or the like to form the resin composition layer (X).
- organic solvent used here examples include ketones such as acetone, methyl ethyl ketone and cyclohexanone, acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate, cellosolve and butyl carbitol.
- ketones such as acetone, methyl ethyl ketone and cyclohexanone
- acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate, cellosolve and butyl carbitol.
- Carbitols, aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like are preferably used, and the non-volatile
- the thickness of the resin composition layer (X) to be formed usually needs to be equal to or greater than the thickness of the conductor layer. Since the thickness of the conductor layer included in the circuit board is usually in the range of 5 to 70 ⁇ m, the thickness of the resin composition layer (X) is preferably 10 to 100 ⁇ m.
- the resin composition layer (X) in the present invention may be protected by a protective film described later. By protecting with a protective film, it is possible to prevent dust and the like from adhering to the surface of the resin composition layer and scratches.
- the support film and protective film described above include polyolefins such as polyethylene, polypropylene and polyvinyl chloride, polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate, polycarbonates and polyimides, and metals such as release paper, copper foil and aluminum foil. Foil and the like can be mentioned.
- the support film and the protective film may be subjected to a mold release treatment in addition to the mud treatment and the corona treatment.
- the thickness of the support film is not particularly limited, but is usually 10 to 150 ⁇ m, and is preferably used in the range of 25 to 50 ⁇ m.
- the thickness of the protective film is preferably 1 to 40 ⁇ m.
- the support film (Y) is peeled off after being laminated on a circuit board or after forming an insulating layer by heat curing. If the support film (Y) is peeled off after the resin composition layer constituting the build-up film is heat-cured, it is possible to prevent the adhesion of dust and the like in the curing step. When peeling after curing, the support film is usually subjected to a mold release treatment in advance.
- a multilayer printed circuit board can be manufactured from the build-up film obtained as described above.
- the resin composition layer (X) is protected by a protective film, the resin composition layer (X) is peeled off, and then the resin composition layer (X) is directly contacted with the circuit board on one or both sides of the circuit board.
- laminating is performed by a vacuum laminating method.
- the laminating method may be a batch method or a continuous method using a roll. If necessary, the build-up film and the circuit board may be preheated if necessary before laminating.
- the crimping temperature (lamination temperature) is preferably 70 to 140 ° C., and the crimping pressure is 1 to 11 kgf / cm 2 (9.8 ⁇ 10 4 to 107.9 ⁇ 10 4 N / m 2 ). It is preferable to laminate under a reduced air pressure of 20 mmHg (26.7 hPa) or less.
- Examples of the method for obtaining the conductive paste from the curable resin composition of the present invention include a method for dispersing the conductive particles in the composition.
- the conductive paste can be used as a paste resin composition for circuit connection or an anisotropic conductive adhesive depending on the type of conductive particles used.
- Softening point measurement method The softening point (° C.) of the intermediate amine compound obtained in the synthetic example shown below was measured in accordance with JIS K7234 (ring ball method).
- the amine equivalent of the intermediate amine compound was measured by the following measuring method. Approximately 2.5 g of the sample intermediate amine compound, 7.5 g of pyridine, 2.5 g of anhydrous acetic acid, and 7.5 g of triphenylphosphine were precisely weighed in a 500 mL Erlenmeyer flask with a stopper, and then a cooling tube was attached to the flask at 120 ° C. The mixture was heated under reflux for 150 minutes in the oil bath set in.
- GPC measurement Measurement was performed using the following measuring devices and measurement conditions, and GPC charts (FIGS. 1 to 9) of maleimide obtained in the synthetic examples shown below were obtained. From the results of the GPC chart, the molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) and the average number of repeating units "n" that contribute to the indan skeleton in maleimide are changed to the number average molecular weight (Mn). Based on this, it was measured and calculated.
- Mw weight average molecular weight
- Mn number average molecular weight
- Measuring device "HLC-8320 GPC” manufactured by Tosoh Corporation Column: Guard column “HXL-L” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G3000HXL” manufactured by Tosoh Corporation + Tosoh Corporation Made by “TSK-GEL G4000HXL” Detector: RI (Differential Refractometer) Data processing: "GPC Workstation EcoSEC-WorkStation” manufactured by Tosoh Corporation Measurement conditions: Column temperature 40 ° C Developing solvent Tetrahydrofuran Flow velocity 1.0 ml / min Standard: The following monodisperse polystyrene with a known molecular weight was used in accordance with the measurement manual of the above-mentioned "GPC workstation EcoSEC-WorkStation".
- the mixture was cooled to 140 ° C., 145.4 g (1.2 mol) of 2,6-dimethylaniline was charged, the temperature was raised to 220 ° C., and the reaction was carried out for 3 hours.
- the mixture is air-cooled to 100 ° C., diluted with 300 g of toluene, activated clay is removed by filtration, and low molecular weight substances such as a solvent and an unreacted compound are distilled off under reduced pressure to obtain the following general formula (A-2). ) Was obtained, and 278.4 g of the intermediate amine compound represented by) was obtained.
- the amine equivalent was 294 and the softening point was 65 ° C.
- toluene was used so that the non-volatile content was 10, 20, 30, 40, 50, 60, and 70% by mass using each maleimide obtained in the above synthesis example and comparative example.
- a solution and a methyl ethyl ketone (MEK) solution were prepared.
- the vials containing the maleimides obtained in the above synthesis examples and comparative examples were left at room temperature (25 ° C.) for 60 days and uniformly dissolved in each solution in each non-volatile composition (insoluble). (No substance) was evaluated as ⁇ , and when it was not dissolved (with insoluble substance), it was evaluated as ⁇ (visually).
- the non-volatile content is 20% by mass or more, it is practically preferable if it can be dissolved in a solvent.
- cured product (molded product) was prepared by subjecting the curable resin composition to the following conditions. Curing conditions: After heating at 200 ° C. for 2 hours, the mixture was further heat-cured at 250 ° C. for 2 hours. Plate thickness of cured product (molded product) after molding: 2.4 mm Various physical properties and properties of the obtained cured product were evaluated by the following methods. The evaluation results are shown in Table 3.
- ⁇ Glass transition temperature (Tg)> A cured product having a thickness of 2.4 mm was cut into a size of 5 mm in width and 54 mm in length, and this was used as a test piece. This test piece is used as a viscoelasticity measuring device (DMA: solid viscoelasticity measuring device "DMS6100” manufactured by Hitachi High-Tech Science Co., Ltd., deformation mode: double-sided bending, measurement mode: sinusoidal vibration, frequency 1 Hz, heating rate 3 ° C./min) The temperature at which the change in viscoelasticity was maximized (the rate of change in tan ⁇ was the largest) was evaluated as the glass transition temperature Tg (° C.). From the viewpoint of heat resistance, the glass transition temperature Tg is preferably 255 ° C. or higher, more preferably 260 ° C. or higher, and even more preferably 260 ° C. or higher.
- thermogravimetric decomposition property A cured product with a thickness of 2.4 mm is cut into small pieces and measured in a nitrogen atmosphere at a temperature rise rate of 5 ° C./min using a thermogravimetric analyzer (thermogravimetric analyzer "TGA / DSC1" manufactured by METTTLER TOREDO). The temperature at which the weight was reduced by 5% was evaluated as the thermogravimetric decomposition temperature (Td5) (° C.).
- ⁇ Thermal expansion property> A cured product having a thickness of 2.4 mm was cut into a size having a width of 5 mm and a length of 5 mm, and this was used as a test piece. This test piece was measured for a coefficient of thermal expansion CTE (ppm) in the range of 40 to 60 ° C. using a thermal analyzer (“TMA / SS6100” manufactured by SII Nanotechnology Inc., heating rate of 3 ° C./min). From the viewpoint of heat resistance and prevention of warpage, the coefficient of thermal expansion is preferably 60 ppm or less, more preferably 50 ppm or less.
- the dielectric constant and the dielectric loss tangent were measured at.
- the dielectric constant and the dielectric loss tangent the dielectric constant is preferably 2.80 or less, and more preferably 2.75 or less, from the viewpoint of reducing transmission loss as an electronic material.
- the dielectric loss tangent is preferably 0.0080 or less, more preferably 0.0070 or less.
- Comparative Example 3 had a lower glass transition temperature and was inferior in heat resistance as compared with Examples because no epoxy resin or the like was used.
- the curable resin composition of the present invention can be suitably used for heat-resistant members and electronic members because the cured product is excellent in heat resistance and dielectric properties, and in particular, a semiconductor encapsulant, a circuit board, and a build. It can be suitably used for up films, build-up substrates, etc., adhesives and resist materials. Further, it can be suitably used for a matrix resin of a fiber reinforced resin, and is suitable as a prepreg having high heat resistance.
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Abstract
Description
前記マレイミド(A)の製造方法について、以下に説明する。
以下の条件により、ゲルパーミエーションクロマトグラフィー(GPC)に基づき、マレイミド(A)の分子量分布(Mw/Mn)を測定した。
測定装置 :東ソー株式会社製「HLC-8320 GPC」
カラム:東ソー株式会社製ガードカラム「HXL-L」+東ソー株式会社製「TSK-GEL G2000HXL」+東ソー株式会社製「TSK-GEL G2000HXL」+東ソー株式会社製「TSK-GEL G3000HXL」+東ソー株式会社製「TSK-GEL G4000HXL」
検出器:RI(示差屈折計)
データ処理:東ソー株式会社製「GPCワークステーション EcoSEC-WorkStation」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準:前記「GPCワークステーション EcoSEC-WorkStation」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A-500」
東ソー株式会社製「A-1000」
東ソー株式会社製「A-2500」
東ソー株式会社製「A-5000」
東ソー株式会社製「F-1」
東ソー株式会社製「F-2」
東ソー株式会社製「F-4」
東ソー株式会社製「F-10」
東ソー株式会社製「F-20」
東ソー株式会社製「F-40」
東ソー株式会社製「F-80」
東ソー株式会社製「F-128」
試料:合成例で得られたマレイミドの樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)。
本発明の硬化性樹脂組成物は、アミン化合物(B)(以下、「(B)成分」という場合がある。)を含有することを特徴とする。前記アミン化合物(B)は、低温硬化に寄与することができ、優れた成形加工性を発現することから、構造材料用の成形材料として用いることができ、有用である。また、前記インダン骨格を有するマレイミド(A)との反応により、硬化剤として作用し、三次元架橋を生じることができ、耐熱性にも優れた硬化物を得ることができ、好ましい態様となる。更に、下記に詳述するエポキシ樹脂(C)との関係においても、硬化剤として作用し、銅への密着性が向上し、例えば、銅箔を使用する回路基板など製造において、有用となる。
本発明の硬化性樹脂組成物は、エポキシ樹脂(C)(以下、「(C)成分」という場合がある。)を含有することを特徴とする。前記エポキシ樹脂(C)は、硬化性樹脂組成物の調製時の流動性が良好となり、密着性に優れた硬化物を得ることができる硬化性樹脂組成物を調製することができ、有用である。また、前記アミン化合物(B)と前記エポキシ樹脂(C)を使用した際には、銅への密着性が向上し、例えば、銅箔を使用する回路基板など製造において、有用となる。
本発明の硬化性樹脂組成物は、インダン骨格を有するマレイミド(A)、アミン化合物(B)、及び、エポキシ樹脂(C)を含有することを特徴とする。前記マレイミド(A)がインダン骨格を有することにより、これまでのマレイミドと比較して、溶剤溶解性に優れ、硬化性樹脂組成物の調製が容易で、ハンドリング性に優れ、前記マレイミド(A)の構造中に極性官能基の割合が少ないため、誘電特性に優れた硬化物を得ることができる。また、硬化剤として作用する前記アミン化合物(B)は、低温硬化に寄与でき、更に前記エポキシ樹脂(C)は、硬化性樹脂組成物の調製時の流動性が良好となり、密着性に優れた硬化物を得ることができる。また、前記マレイミド(A)と前記エポキシ樹脂(C)に対して、硬化剤として作用する前記アミン化合物(B)が反応することにより、三次元架橋を生じることができ、耐熱性に優れた硬化物を得ることができ、好ましい態様となる。また、前記アミン化合物(B)と前記エポキシ樹脂(C)との反応により、銅への密着性が向上し、例えば、銅箔を使用する回路基板など製造において、有用となる。
本発明の硬化物は、前記硬化性樹脂組成物を硬化反応させてなることが好ましい。前記硬化性樹脂組成物は、上述した各成分を均一に混合することにより得られ、従来知られている方法と同様の方法で容易に硬化物とすることができる。前記硬化物としては、積層物、注型物、接着層、塗膜、フィルム等の成形硬化物が挙げられる。
本発明のプリプレグは、補強基材、及び、前記補強基材に含浸した前記硬化性樹脂組成物の半硬化物を有することが好ましい。前記プリプレグの作製方法としては、公知の方法を使用できるが、前記硬化性樹脂組成物を、有機溶剤に溶解(希釈)した樹脂ワニスを補強基材に含浸させ、樹脂ワニスを含浸させた補強基材を熱処理することにより、前記硬化性樹脂組成物を半硬化(あるいは未硬化)させることで、プリプレグとすることができる。
本発明の硬化性樹脂組成物により得られる硬化物が、耐熱性、及び、誘電特性に優れることから、耐熱部材や電子部材に好適に使用可能である。特に、回路基板、半導体封止材、半導体装置、ビルドアップフィルム、ビルドアップ基板、接着剤やレジスト材料などに好適に使用できる。また、繊維強化樹脂のマトリクス樹脂にも好適に使用でき、高耐熱性のプリプレグとして特に適している。また、前記硬化性樹脂組成物に含まれる前記インダン骨格を有するマレイミド(A)は、各種溶剤への優れた溶解性を示すことから塗料化が可能である。こうして得られる耐熱部材や電子部材は、各種用途に好適に使用可能であり、例えば、産業用機械部品、一般機械部品、自動車・鉄道・車両等部品、宇宙・航空関連部品、電子・電気部品、建築材料、容器・包装部材、生活用品、スポーツ・レジャー用品、風力発電用筐体部材等が挙げられるが、これらに限定される物ではない。
本発明において、回路基板としては、前記プリプレグ、及び、銅箔を積層し、加熱圧着成型して得られることが好ましい。具体的には、本発明の硬化性樹脂組成物から回路基板を得る方法としては、上記プリプレグを、常法により積層し、適宜銅箔を重ねて、1~10MPaの加圧下に170~300℃で10分~3時間、加熱圧着成型させる方法が挙げられる。
本発明において、半導体封止材としては、前記硬化性樹脂組成物を含有することが好ましい。具体的には、本発明の硬化性樹脂組成物から半導体封止材を得る方法としては、前記硬化性樹脂組成物に、更に任意成分である硬化促進剤、および無機充填剤等の配合剤とを必要に応じて押出機、ニ-ダ、ロ-ル等を用いて均一になるまで充分に溶融混合する方法が挙げられる。その際、無機充填剤としては、通常、溶融シリカが用いられるが、パワートランジスタ、パワーIC用高熱伝導半導体封止材として用いる場合は、溶融シリカよりも熱伝導率の高い結晶シリカ,アルミナ,窒化ケイ素などの高充填化、または溶融シリカ、結晶性シリカ、アルミナ、窒化ケイ素などを用いるとよい。その充填率は、硬化性樹脂組成物100質量部当たり、無機充填剤を30~95質量部の範囲で用いることが好ましく、中でも、難燃性や耐湿性や耐ハンダクラック性の向上、線膨張係数の低下を図るためには、70質量部以上がより好ましく、80質量部以上であることがさらに好ましい。
本発明において、半導体装置としては、前記半導体封止材を加熱硬化した硬化物を含むことが好ましい。具体的には、本発明の硬化性樹脂組成物から半導体装置を得る半導体パッケージ成形としては、上記半導体封止材を注型、または、トランスファー成形機、射出成形機などを用いて成形し、さらに50~250℃で、2~10時間の間、加熱硬化する方法が挙げられる。
本発明の硬化性樹脂組成物からビルドアップ基板を得る方法としては、工程1~3を経由する方法が挙げられる。工程1では、まず、ゴム、フィラーなどを適宜配合した前記硬化性樹脂組成物を、回路を形成した回路基板にスプレーコーティング法、カーテンコーティング法等を用いて塗布した後、硬化させる。工程2では、必要に応じて、硬化性樹脂組成物が塗布された回路基板に所定のスルーホール部等の穴あけを行った後、粗化剤により処理し、その表面を湯洗することによって、前記基板に凹凸を形成させ、銅などの金属をめっき処理する。工程3では、工程1~2の操作を所望に応じて順次繰り返し、樹脂絶縁層及び所定の回路パターンの導体層を交互にビルドアップしてビルドアップ基板を成形する。なお、前記工程において、スルーホール部の穴あけは、最外層の樹脂絶縁層の形成後に行うとよい。また、本発明におけるビルドアップ基板は、銅箔上で当該樹脂組成物を半硬化させた樹脂付き銅箔を、回路を形成した配線基板上に、170~300℃で加熱圧着することで、粗化面を形成、メッキ処理の工程を省き、ビルドアップ基板を作製することも可能である。
本発明のビルドアップフィルムは、前記硬化性樹脂組成物を含有することが好ましい。本発明の硬化性樹脂組成物からビルドアップフィルムを得る方法としては、例えば、支持フィルム上に硬化性樹脂組成物を塗布したのち、乾燥させて、支持フィルムの上に樹脂組成物層を形成する方法が挙げられる。本発明の硬化性樹脂組成物をビルドアップフィルムに用いる場合、該フィルムは、真空ラミネート法におけるラミネートの温度条件(通常70℃~140℃)で軟化し、回路基板のラミネートと同時に、回路基板に存在するビアホール或いはスルーホール内の樹脂充填が可能な流動性(樹脂流れ)を示すことが肝要であり、このような特性を発現するよう前記各成分を配合することが好ましい。なお、得られるビルドアップフィルムや回路基板(銅張積層板等)においては、相分離などに起因する、局所的に異なる特性値を示すといった現象を生じさせず、任意の部位において、一定の性能を発現させるため、外観均一性が要求される。
本発明の硬化性樹脂組成物から導電ペーストを得る方法としては、例えば、導電性粒子を該組成物中に分散させる方法が挙げられる。上記導電ペーストは、用いる導電性粒子の種類によって、回路接続用ペースト樹脂組成物や異方性導電接着剤とすることができる。
測定法:JIS K7234(環球法)に準拠して、以下に示す合成例で得られた中間アミン化合物の軟化点(℃)を測定した。
以下の測定法により、中間体アミン化合物のアミン当量を測定した。
500mL共栓付き三角フラスコに、試料である中間体アミン化合物を約2.5g、ピリジン7.5g、無水酢酸2.5g、トリフェニルホスフィン7.5gを精秤後、冷却管を装着し120℃に設定したオイルバスにて150分加熱還流した。
冷却後、蒸留水5.0mL、プロピレングリコールモノメチルエーテル100mL、テトラヒドロフラン75mLを加え、0.5mol/L水酸化カリウム-エタノール溶液で電位差滴定法により滴定した。同様の方法で空試験を行なって補正した。
アミン当量(g/eq.)=(S×2,000)/(Blank-A)
S:試料の量(g)
A:0.5mol/L水酸化カリウム-エタノール溶液の消費量(mL)
Blank:空試験における0.5mol/L水酸化カリウム-エタノール溶液の消費量(mL)
以下の測定装置、測定条件を用いて測定し、以下に示す合成例で得られたマレイミドのGPCチャート(図1~図9)を得た。前記GPCチャートの結果より、分子量分布(重量平均分子量(Mw)/数平均分子量(Mn))、及び、マレイミド中のインダン骨格に寄与する平均繰り返し単位数「n」を数平均分子量(Mn)に基づき、測定・算出した。具体的にはn=0~4の化合物について、理論分子量とGPCにおけるそれぞれの実測値分子量とで散布図上にプロット、近似直線を引き、直線上の実測値Mn(1)が示す点より数平均分子量(Mn)を求め、nを算出した。
測定装置 :東ソー株式会社製「HLC-8320 GPC」
カラム:東ソー株式会社製ガードカラム「HXL-L」+東ソー株式会社製「TSK-GEL G2000HXL」+東ソー株式会社製「TSK-GEL G2000HXL」+東ソー株式会社製「TSK-GEL G3000HXL」+東ソー株式会社製「TSK-GEL G4000HXL」
検出器:RI(示差屈折計)
データ処理:東ソー株式会社製「GPCワークステーション EcoSEC-WorkStation」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準:前記「GPCワークステーション EcoSEC-WorkStation」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A-500」
東ソー株式会社製「A-1000」
東ソー株式会社製「A-2500」
東ソー株式会社製「A-5000」
東ソー株式会社製「F-1」
東ソー株式会社製「F-2」
東ソー株式会社製「F-4」
東ソー株式会社製「F-10」
東ソー株式会社製「F-20」
東ソー株式会社製「F-40」
東ソー株式会社製「F-80」
東ソー株式会社製「F-128」
試料:合成例で得られたマレイミドの樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)。
FD-MSスペクトルは、以下の測定装置、測定条件を用いて測定した。
測定装置:JMS-T100GC AccuTOF
測定条件
測定範囲:m/z=4.00~2000.00
変化率:51.2mA/min
最終電流値:45mA
カソード電圧:-10kV
記録間隔:0.07sec
(1)中間体アミン化合物の合成
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた1Lフラスコに2,6-ジメチルアニリン48.5g(0.4mol)、α,α’-ジヒドロキシ-1,3-ジイソプロピルベンゼン272.0g(1.4mol)、キシレン280gおよび活性白土70gを仕込み、攪拌しながら120℃まで加熱した。さらに留出水をディーンスターク管で取り除きながら210℃になるまで昇温し、3時間反応させた。その後140℃まで冷却し、2,6-ジメチルアニリン145.4g(1.2mol)を仕込んだ後、220℃まで昇温し、3時間反応させた。反応後、100℃まで空冷し、トルエン300gで希釈して、ろ過により活性白土を除き、減圧下で溶剤及び未反応物等の低分子量物を留去することにより、下記一般式(A-1)で表される中間体アミン化合物364.1gを得た。アミン当量は298であり、軟化点は70℃であった。
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた2Lフラスコに無水マレイン酸131.8g(1.3mol)、トルエン700gを仕込み室温で攪拌した。次に反応物(A-1)を364.1gとDMF175gの混合溶液を1時間かけて滴下した。
滴下終了後、室温でさらに2時間反応させた。p-トルエンスルホン酸一水和物37.1gを加え、反応液を加熱し還流下で共沸してくる水とトルエンを冷却・分離した後、トルエンだけを系内に戻して脱水反応を8時間行った。室温まで空冷後、減圧濃縮し褐色溶液を酢酸エチル600gに溶解させイオン交換水150gで3回、2%炭酸水素ナトリウム水溶液150gで3回洗浄し、硫酸ナトリウムを加え乾燥後、減圧濃縮し得られた反応物を80℃で4時間真空乾燥を行い、マレイミド化合物A-1を含有する生成物を413.0g得た。このマレイミド化合物A-1のFD-MSスペクトルにて、M+=560、718、876のピークが確認され、それぞれのピークは、nが0、1、2の場合に相当する。なお、前記マレイミドA-1中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図1であり、n=1.47であり、分子量分布(Mw/Mn)=1.81であった。
(1)中間体アミン化合物の合成
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた1Lフラスコに2,6-ジメチルアニリン48.5g(0.4mol)、α,α’-ジヒドロキシ-1,3-ジイソプロピルベンゼン233.2g(1.2mol)、キシレン230gおよび活性白土66gを仕込み、攪拌しながら120℃まで加熱した。さらに留出水をディーンスターク管で取り除きながら210℃になるまで昇温し、3時間反応させた。その後140℃まで冷却し、2,6-ジメチルアニリン145.4g(1.2mol)を仕込んだ後、220℃まで昇温し、3時間反応させた。反応後、100℃まで空冷し、トルエン300gで希釈して、ろ過により活性白土を除き、減圧下で溶剤及び未反応物等の低分子量物を留去することにより、下記一般式(A-2)で表される中間体アミン化合物278.4gを得た。アミン当量は294であり、軟化点は65℃であった。
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた2Lフラスコに無水マレイン酸107.9g(1.1mol)、トルエン600gを仕込み室温で攪拌した。次に反応物(A-2)を278.4gとDMF150gの混合溶液を1時間かけて滴下した。
滴下終了後、室温でさらに2時間反応させた。p-トルエンスルホン酸一水和物27.0gを加え、反応液を加熱し還流下で共沸してくる水とトルエンを冷却・分離した後、トルエンだけを系内に戻して脱水反応を8時間行った。室温まで空冷後、減圧濃縮し褐色溶液を酢酸エチル500gに溶解させイオン交換水120gで3回、2%炭酸水素ナトリウム水溶液120gで3回洗浄し、硫酸ナトリウムを加え乾燥後、減圧濃縮し得られた反応物を80℃で4時間真空乾燥を行い、マレイミド化合物A-2を含有する生成物を336.8g得た。このマレイミド化合物A-2のFD-MSスペクトルにて、M+=560、718、876のピークが確認され、それぞれ、nが0、1、2の場合に相当する。なお、前記マレイミドA-2中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図2であり、n=1.25であり、分子量分布(Mw/Mn)=3.29であった。
(1)中間体アミン化合物の合成
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた2Lフラスコに2,6-ジメチルアニリン48.5g(0.4mol)、α,α’-ジヒドロキシ-1,3-ジイソプロピルベンゼン388.6g(2.0mol)、キシレン350gおよび活性白土123gを仕込み、攪拌しながら120℃まで加熱した。さらに留出水をディーンスターク管で取り除きながら210℃になるまで昇温し、3時間反応させた。その後140℃まで冷却し、2,6-ジメチルアニリン145.4g(1.2mol)を仕込んだ後、220℃まで昇温し、3時間反応させた。反応後、100℃まで空冷し、トルエン500gで希釈して、ろ過により活性白土を除き、減圧下で溶剤及び未反応物等の低分子量物を留去することにより、下記一般式(A-3)で表される中間体アミン化合物402.1gを得た。アミン当量は306であり、軟化点は65℃であった。
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた2Lフラスコに無水マレイン酸152.1g(1.5mol)、トルエン700gを仕込み室温で攪拌した。次に反応物(A-3)を402.1gとDMF200gの混合溶液を1時間かけて滴下した。
滴下終了後、室温でさらに2時間反応させた。p-トルエンスルホン酸一水和物37.5gを加え、反応液を加熱し還流下で共沸してくる水とトルエンを冷却・分離した後、トルエンだけを系内に戻して脱水反応を8時間行った。室温まで空冷後、減圧濃縮し褐色溶液を酢酸エチル800gに溶解させイオン交換水200gで3回、2%炭酸水素ナトリウム水溶液200gで3回洗浄し、硫酸ナトリウムを加え乾燥後、減圧濃縮し得られた反応物を80℃で4時間真空乾燥を行い、マレイミド化合物A-3を含有する生成物を486.9g得た。このマレイミド化合物A-3のFD-MSスペクトルにて、M+=560、718、876のピークが確認され、それぞれ、nが0、1、2の場合に相当する。なお、前記マレイミドA-3中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図3であり、n=1.96であり、分子量分布(Mw/Mn)=1.52であった。
(1)中間体アミン化合物の合成
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた2Lフラスコに2,6-ジエチルアニリン59.7g(0.4mol)、α,α’-ジヒドロキシ-1,3-ジイソプロピルベンゼン272.0g(1.4mol)、キシレン350gおよび活性白土94gを仕込み、攪拌しながら120℃まで加熱した。さらに留出水をディーンスターク管で取り除きながら210℃になるまで昇温し、3時間反応させた。その後140℃まで冷却し、2,6-ジエチルアニリン179.1g(1.2mol)を仕込んだ後、220℃まで昇温し、3時間反応させた。反応後、100℃まで空冷し、トルエン500gで希釈して、ろ過により活性白土を除き、減圧下で溶剤及び未反応物等の低分子量物を留去することにより、下記一般式(A-4)で表される中間体アミン化合物342.1gを得た。アミン当量は364であり、軟化点は47℃であった。
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた2Lフラスコに無水マレイン酸107.9g(1.1mol)、トルエン600gを仕込み室温で攪拌した。次に反応物(A-4)を342.1gとDMF180gの混合溶液を1時間かけて滴下した。
滴下終了後、室温でさらに2時間反応させた。p-トルエンスルホン酸一水和物26.8gを加え、反応液を加熱し還流下で共沸してくる水とトルエンを冷却・分離した後、トルエンだけを系内に戻して脱水反応を8時間行った。室温まで空冷後、減圧濃縮し褐色溶液を酢酸エチル500gに溶解させイオン交換水200gで3回、2%炭酸水素ナトリウム水溶液200gで3回洗浄し、硫酸ナトリウムを加え乾燥後、減圧濃縮し得られた反応物を80℃で4時間真空乾燥を行い、マレイミド化合物A-4を含有する生成物を388.1g得た。このマレイミド化合物A-4のFD-MSスペクトルにて、M+=616、774、932のピークが確認され、それぞれ、nが0、1、2の場合に相当する。なお、前記マレイミドA-4中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図4であり、n=1.64であり、分子量分布(Mw/Mn)=1.40であった。
(1)中間体アミン化合物の合成
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた1Lフラスコに2,6-ジイソプロピルアニリン70.9g(0.4mol)、α,α’-ジヒドロキシ-1,3-ジイソプロピルベンゼン272.0g(1.4mol)、キシレン350gおよび活性白土97gを仕込み、攪拌しながら120℃まで加熱した。さらに留出水をディーンスターク管で取り除きながら210℃になるまで昇温し、3時間反応させた。その後140℃まで冷却し、2,6-ジイソプロピルアニリン212.7g(1.2mol)を仕込んだ後、220℃まで昇温し、3時間反応させた。反応後、100℃まで空冷し、トルエン500gで希釈して、ろ過により活性白土を除き、減圧下で溶剤及び未反応物等の低分子量物を留去することにより、下記一般式(A-5)で表される中間体アミン化合物317.5gを得た。アミン当量は366であり、軟化点は55℃であった。
温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた2Lフラスコに無水マレイン酸107.9g(1.1mol)、トルエン600gを仕込み室温で攪拌した。次に反応物(A-5)を317.5gとDMF175gの混合溶液を1時間かけて滴下した。
滴下終了後、室温でさらに2時間反応させた。p-トルエンスルホン酸一水和物24.8gを加え、反応液を加熱し還流下で共沸してくる水とトルエンを冷却・分離した後、トルエンだけを系内に戻して脱水反応を8時間行った。室温まで空冷後、減圧濃縮し褐色溶液を酢酸エチル600gに溶解させイオン交換水200gで3回、2%炭酸水素ナトリウム水溶液200gで3回洗浄し、硫酸ナトリウムを加え乾燥後、減圧濃縮し得られた反応物を80℃で4時間真空乾燥を行い、マレイミド化合物A-5を含有する生成物を355.9g得た。このマレイミド化合物A-5のFD-MSスペクトルにて、M+=672、830、988のピークが確認され、それぞれ、nが0、1、2の場合に相当する。なお、前記マレイミドA-5中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図5であり、n=1.56であり、分子量分布(Mw/Mn)=1.24であった。
(1)中間体アミン化合物の合成
前記中間体アミン化合物A-1の合成法において、210℃の反応時間を6時間、220℃の反応時間を3時間に変えて同様の操作を行い、下記一般式(A-9)で表される中間体アミン化合物345.2gを得た。アミン当量は348であり、軟化点は71℃であった。
前記マレイミド化合物A-1の合成法から中間体をA-9に代えて同様に操作を行い、マレイミド化合物A-9を含有する生成物を407.6g得た。このマレイミド化合物A-9のFD-MSスペクトルにて、M+=560、718、876のピークが確認され、それぞれのピークは、nが0、1、2の場合に相当する。なお、前記マレイミドA-9中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図6であり、n=2.59であり、分子量分布(Mw/Mn)=1.49であった。
前記中間体アミン化合物A-1の合成法において、210℃の反応時間を6時間、220℃の反応時間を3時間に変えて同様の操作を行い、合成した中間体アミン化合物(アミン当量は347、軟化点は71℃)に対し、マレイミド化反応における還流下の脱水反応を10時間とする以外は、前記マレイミド化合物A-1の合成法と同様の条件に付すことで、マレイミド化合物A-10を含有する生成物を415.6g得た。このマレイミド化合物A-10のFD-MSスペクトルにて、M+=560、718、876のピークが確認され、それぞれのピークは、nが0、1、2の場合に相当する。なお、前記マレイミドA-10中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図7であり、n=2.91であり、分子量分布(Mw/Mn)=1.64であった。
前記中間体アミン化合物A-1の合成法において、210℃の反応時間を9時間、220℃の反応時間を3時間に変えて同様の操作を行い、合成した中間体アミン化合物(アミン当量は342、軟化点は69℃)に対し、マレイミド化反応における還流下の脱水反応を10時間とする以外は、前記マレイミド化合物A-1の合成法と同様の条件に付すことで、マレイミド化合物A-11を含有する生成物を398.7g得た。このマレイミド化合物A-11のFD-MSスペクトルにて、M+=560、718、876のピークが確認され、それぞれのピークは、nが0、1、2の場合に相当する。なお、前記マレイミドA-11中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図8であり、n=3.68であり、分子量分布(Mw/Mn)=2.09であった。
前記中間体アミン化合物A-1の合成法において、210℃の反応時間を9時間、220℃の反応時間を3時間に変えて同様の操作を行い、合成した中間体アミン化合物(アミン当量は347、軟化点は70℃)に対し、マレイミド化反応における還流下の脱水反応を12時間とする以外は、前記マレイミド化合物A-1の合成法と同様の条件に付すことで、マレイミド化合物A-12を含有する生成物を422.7g得た。このマレイミド化合物A-12のFD-MSスペクトルにて、M+=560、718、876のピークが確認され、それぞれのピークは、nが0、1、2の場合に相当する。なお、前記マレイミドA-12中のインダン骨格部分における繰り返し単位数nの値(数平均分子量に基づく)をGPCで求めたところ、そのGPCチャートが図9であり、n=4.29であり、分子量分布(Mw/Mn)=3.02であった。
<マレイミドの溶剤溶解性>
合成例1~9で得られたマレイミド(A-1)~(A-5)、(A-9)~(A-12)、及び、比較用の市販のマレイミド(A-6)(4,4'-ジフェニルメタンビスマレイミド、「BMI-1000」大和化成工業株式会社製)のトルエン、メチルエチルケトン(MEK)に対する溶解性の評価を行い、評価結果を表1に示した。
溶剤溶解性の評価方法としては、上記合成例及び比較例で得られた各マレイミドを用いて、不揮発分が10、20、30、40、50、60、及び、70質量%になるようにトルエン溶液、及び、メチルエチルケトン(MEK)溶液を調製した。
具体的には、上記合成例及び比較例で得られた各マレイミドを入れたバイアルを室温(25℃)で60日間放置し、各不揮発分組成における各溶液中において、均一に溶解した場合(不溶物なし)を〇、溶解しなかった場合(不溶物あり)を×と評価(目視)した。なお、不揮発分が20質量%以上の場合に、溶剤に溶解することができれば、実用上、好ましい。
<硬化性樹脂組成物の調製>
合成例1~9で得られたマレイミド(A-1)~(A-5)、(A-9)~(A-12)、比較用マレイミド(A-6)(4,4'-ジフェニルメタンビスマレイミド、「BMI-1000」、大和化成工業株式会社製)、アミン化合物(B-1)(4,4‘-ジアミノジフェニルメタン、東京化成工業株式会社製)、エポキシ樹脂(C-1)(BPA型エポキシ樹脂「850-S」、当量:188g/eq、DIC株式会社製)、及び、硬化促進剤(D-1)(トリフェニルホスフィン(東京化成工業株式会社製))を表2に示す割合で配合し、硬化性樹脂組成物を調製した。なお、比較例3については、前記エポキシ樹脂(C-1)及び硬化促進剤(D-1)を配合していない。
上記硬化性樹脂組成物を以下の条件に付すことで硬化物(成型物)を作製した。
硬化条件:200℃で2時間加熱後、更に、250℃で2時間加熱硬化させた。
成型後の硬化物(成型物)の板厚:2.4mm
得られた硬化物について、下記の方法で種々の物性・特性の評価を行った。評価結果を表3に示した。
<硬化性樹脂組成物の調製>
合成例1、合成例6~9で得られたマレイミド(A-1)、(A-9)~(A12)、比較用マレイミド(A-6)(4,4'-ジフェニルメタンビスマレイミド、「BMI-1000」、大和化成工業株式会社製)、比較用マレイミド(A-7)(ビスフェノールAジフェニルエーテルビスマレイミド、「BMI-4000」大和化成工業株式会社製)、比較用マレイミド(A-8)(3,3'-ジメチル-5,5'-ジエチル-4,4'-ジフェニルメタンビスマレイミド、「BMI-5100」大和化成工業株式会社製)、アミン化合物(B-1)(4,4’-ジアミノジフェニルメタン、東京化成工業株式会社製)、アミン化合物(B-2)(ビスアニリンM、三井化学ファイン株式会社製)、アミン化合物(B-3)(2,2’-ビス[4-(4-アミノフェノキシ)フェニル]プロパン、東京化成工業株式会社製)、アミン化合物(B-4)(上記一般式(A-1)で表される中間体アミン化合物)、エポキシ樹脂(C-1)(BPA型エポキシ樹脂「850-S」、当量:188g/eq、DIC株式会社製)、硬化促進剤(D-1)(トリフェニルホスフィン(東京化成工業株式会社製))、及び、メチルエチルケトン(MEK)を表4に示す割合で配合し、硬化性樹脂組成物を調製した。
実施例19~26、及び、比較例4~18において、表4に示す割合で、それぞれメチルエチルケトン(MEK)を混合・溶解し硬化性樹脂組成物を得た。各硬化性樹脂組成物5gを離型PETフィルム状に塗布(乾燥後の厚み:295μm)し、80℃で1時間乾燥(加熱)後、更に、120℃で1時間乾燥(加熱)することにより、フィルム成形物を作製し、得られたフィルム成形物の外観を目視にて、確認した。フィルム外観が均一の場合を〇、フィルム外観が不均一な場合を×(例えば、濁りや不溶物などが確認できる場合)と評価した。評価結果を表4に示した。
厚さ2.4mmの硬化物を幅5mm、長さ54mmのサイズに切り出し、これを試験片とした。この試験片を粘弾性測定装置(DMA:日立ハイテクサイエンス社製固体粘弾性測定装置「DMS6100」、変形モード:両持ち曲げ、測定モード:正弦波振動、周波数1Hz、昇温速度3℃/分)を用いて、弾性率変化が最大となる(tanδ変化率が最も大きい)温度をガラス転移温度Tg(℃)として評価した。なお、耐熱性の観点から、ガラス転移温度Tgとしては、255℃以上が好ましく、260℃以上がより好ましく、265℃以上が更に好ましい。
厚さ2.4mmの硬化物を細かく裁断し、熱重量分析装置(METTLER TOREDO社製熱重量測定装置「TGA/DSC1」)を用いて、昇温速度を5℃/分として窒素雰囲気下で測定を行い、5%重量減少する温度を耐熱分解温度(Td5)(℃) として評価した。
厚さ2.4mmの硬化物を幅5mm、長さ5mmのサイズに切り出し、これを試験片とした。この試験片を熱分析装置(SIIナノテクノロジー社製「TMA/SS6100」、昇温速度3℃/分)を用いて40~60℃の範囲の熱膨張係数CTE(ppm)を測定した。なお、耐熱性や反りの防止等の観点から、熱膨張係数としては、60ppm以下が好ましく、より好ましくは、50ppm以下である。
JIS-C-6481に準拠し、アジレント・テクノロジー株式会社製ネットワークアナライザ「E8362C」を用い空洞共振法にて、絶乾後23℃、湿度50%の室内に24時間保管した後の試験片の1GHzでの誘電率及び誘電正接を測定した。なお、誘電率及び誘電正接としては、電子材料としての伝送損失低減の観点から、誘電率は、2.80以下が好ましく、2.75以下がより好ましい。また、誘電正接は、0.0080以下が好ましく、0.0070以下がより好ましい。
Claims (8)
- インダン骨格を有するマレイミド(A)、アミン化合物(B)、及び、エポキシ樹脂(C)を含有することを特徴とする硬化性樹脂組成物。
- 前記マレイミド(A)が、下記一般式(1)で示されることを特徴とする請求項1に記載の硬化性樹脂組成物。
- 請求項1又は2に記載の硬化性樹脂組成物を硬化反応させてなることを特徴とする硬化物。
- 補強基材、及び、前記補強基材に含浸した請求項1又は2に記載の硬化性樹脂組成物の半硬化物を有することを特徴とするプリプレグ。
- 請求項4に記載のプリプレグ、及び、銅箔を積層し、加熱圧着成型して得られることを特徴とする回路基板。
- 請求項1~3のいずれかに記載の硬化性樹脂組成物を含有することを特徴とするビルドアップフィルム。
- 請求項1~3のいずれかに記載の硬化性樹脂組成物を含有することを特徴とする半導体封止材。
- 請求項7に記載の半導体封止材を加熱硬化した硬化物を含むことを特徴とする半導体装置。
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CN202080031440.7A CN113728019B (zh) | 2019-04-26 | 2020-02-20 | 固化性树脂组合物 |
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WO2022145377A1 (ja) * | 2020-12-28 | 2022-07-07 | 昭和電工マテリアルズ株式会社 | 樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ |
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JPH0347814A (ja) * | 1989-04-20 | 1991-02-28 | Kawasaki Steel Corp | イミド化共重合体およびそれを用いた樹脂改質剤、樹脂相溶化剤 |
WO1993012933A1 (en) * | 1991-12-27 | 1993-07-08 | Sumitomo Chemical Company, Limited | Polyamino-oligomer and polymaleimide compound |
JP2009084391A (ja) * | 2007-09-28 | 2009-04-23 | Sekisui Chem Co Ltd | ジヒドロベンゾキサジン環構造を有する熱硬化性樹脂の製造方法 |
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US5218069A (en) * | 1989-04-20 | 1993-06-08 | Kawasaki Steel Corporation | Imidated copolymers and uses thereof |
JP2004182850A (ja) | 2002-12-03 | 2004-07-02 | Mitsubishi Gas Chem Co Inc | 特性バランスに優れるプリプレグ及び積層板 |
JP6452335B2 (ja) * | 2013-08-09 | 2019-01-16 | 日鉄ケミカル&マテリアル株式会社 | エポキシ樹脂組成物及びその硬化物 |
JP6278239B2 (ja) * | 2014-03-18 | 2018-02-14 | Dic株式会社 | 活性エステル樹脂、エポキシ樹脂組成物、その硬化物、プリプレグ、回路基板、及びビルドアップフィルム |
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JPH0347814A (ja) * | 1989-04-20 | 1991-02-28 | Kawasaki Steel Corp | イミド化共重合体およびそれを用いた樹脂改質剤、樹脂相溶化剤 |
WO1993012933A1 (en) * | 1991-12-27 | 1993-07-08 | Sumitomo Chemical Company, Limited | Polyamino-oligomer and polymaleimide compound |
JP2009084391A (ja) * | 2007-09-28 | 2009-04-23 | Sekisui Chem Co Ltd | ジヒドロベンゾキサジン環構造を有する熱硬化性樹脂の製造方法 |
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WO2022145377A1 (ja) * | 2020-12-28 | 2022-07-07 | 昭和電工マテリアルズ株式会社 | 樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ |
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