JP7041855B2 - 硬化性組成物及びその硬化物 - Google Patents
硬化性組成物及びその硬化物 Download PDFInfo
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- JP7041855B2 JP7041855B2 JP2020509888A JP2020509888A JP7041855B2 JP 7041855 B2 JP7041855 B2 JP 7041855B2 JP 2020509888 A JP2020509888 A JP 2020509888A JP 2020509888 A JP2020509888 A JP 2020509888A JP 7041855 B2 JP7041855 B2 JP 7041855B2
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- aromatic compound
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- 239000000203 mixture Substances 0.000 title claims description 46
- -1 maleimide compound Chemical class 0.000 claims description 120
- 150000001491 aromatic compounds Chemical class 0.000 claims description 119
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 229920005989 resin Polymers 0.000 claims description 53
- 239000011347 resin Substances 0.000 claims description 53
- 239000000047 product Substances 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 239000000126 substance Substances 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 14
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 7
- 239000004065 semiconductor Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
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- 238000001723 curing Methods 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 17
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 10
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- 125000003545 alkoxy group Chemical group 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
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- 125000002950 monocyclic group Chemical group 0.000 description 9
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- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 239000002245 particle Substances 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
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- 238000005227 gel permeation chromatography Methods 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- 125000006017 1-propenyl group Chemical group 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
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- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 4
- JNTJHNYWRVBIOU-UHFFFAOYSA-N 1-prop-2-enylnaphthalen-2-ol Chemical compound C1=CC=CC2=C(CC=C)C(O)=CC=C21 JNTJHNYWRVBIOU-UHFFFAOYSA-N 0.000 description 4
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 4
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- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 3
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- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 3
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- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 3
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- 150000007513 acids Chemical class 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 3
- 229910002113 barium titanate Inorganic materials 0.000 description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 125000001153 fluoro group Chemical group F* 0.000 description 3
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
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- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 3
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- NHEVNUARLCWEED-UHFFFAOYSA-N 1,4,5-Naphthalenetriol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1O NHEVNUARLCWEED-UHFFFAOYSA-N 0.000 description 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 2
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- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 2
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
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- 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 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
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- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- ZJTLZYDQJHKRMQ-UHFFFAOYSA-N menadiol Chemical compound C1=CC=CC2=C(O)C(C)=CC(O)=C21 ZJTLZYDQJHKRMQ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical class C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- VOTYOVOSRFKUSM-UHFFFAOYSA-N pyridine-2,3,4-tricarboxylic acid Chemical class OC(=O)C1=CC=NC(C(O)=O)=C1C(O)=O VOTYOVOSRFKUSM-UHFFFAOYSA-N 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- IFLXVSWHQQZRQI-UHFFFAOYSA-N pyridine-2,4,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=N1 IFLXVSWHQQZRQI-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- AQLYZDRHNHZHIS-UHFFFAOYSA-N quinoline-2,6-diol Chemical compound N1C(=O)C=CC2=CC(O)=CC=C21 AQLYZDRHNHZHIS-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000009774 resonance method Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 125000005717 substituted cycloalkylene group Chemical group 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GHPYAGKTTCKKDF-UHFFFAOYSA-M tetraphenylphosphanium;thiocyanate Chemical compound [S-]C#N.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GHPYAGKTTCKKDF-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- UCAJPHQTEWYXEA-UHFFFAOYSA-N triazine-4-carboxylic acid Chemical class OC(=O)C1=CC=NN=N1 UCAJPHQTEWYXEA-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QLAGHGSFXJZWKY-UHFFFAOYSA-N triphenylborane;triphenylphosphane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QLAGHGSFXJZWKY-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
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
Classifications
-
- 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
- C08F222/00—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
- C08F222/10—Esters
-
- 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
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/47—Polyesters chemically modified by esterification by unsaturated monocarboxylic acids or unsaturated monohydric alcohols or reactive derivatives thereof
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/547—Hydroxy compounds containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—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
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- 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
- H05K1/032—Organic insulating material consisting of one material
- H05K1/034—Organic insulating material consisting of one material containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Computer Hardware Design (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Description
2以上のフェノール性水酸基を有する第1の芳香族化合物と、フェノール性水酸基を有する第2の芳香族化合物と、2以上のカルボキシ基を有する第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物との反応生成物であり、前記第1の芳香族化合物、前記第2の芳香族化合物、並びに前記第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物の少なくとも1つが重合性不飽和結合含有置換基を有するものである。
第1の芳香族化合物は、2以上のフェノール性水酸基を有する。2以上のフェノール性水酸基を有することにより、後述する第3の芳香族化合物等と反応することで芳香族エステル樹脂(A)中において、ポリエステル構造を形成しうる。
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 G4000HXL」
+東ソー株式会社製「TSK-GEL G3000HXL」
+東ソー株式会社製「TSK-GEL G2000HXL」
+東ソー株式会社製「TSK-GEL G2000HXL」
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」
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-8320 GPC」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: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)。
第2の芳香族化合物は、フェノール性水酸基を有する。第2の芳香族化合物はフェノール性水酸基を1つ有することから、上述の第1の芳香族化合物および後述の第3の芳香族化合物等のポリエステル化の反応を停止させる機能を有する。
第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物は、2以上のカルボキシ基を有するカルボン酸、またはその誘導体、具体的には酸ハロゲン化物、エステル化物である(本明細書において、第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物を併せて「第3の芳香族化合物等」と称することがある)。第3の芳香族化合物等は、2以上のカルボキシ基等を有することにより、上述の第1の芳香族化合物と反応することで芳香族エステル樹脂(A)において、ポリエステル構造を形成しうる。なお、上述の第2の芳香族化合物と反応することで、ポリエステル化反応は停止する。
上述の第1の芳香族化合物、第2の芳香族化合物、並びに第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物(第3の芳香族化合物等)の少なくとも1つは重合性不飽和結合含有置換基を有する。すなわち、第1の芳香族化合物、第2の芳香族化合物、第3の芳香族化合物等すべてが重合性不飽和結合含有置換基を有していてもよいし、第1の芳香族化合物および第2の芳香族化合物が重合性不飽和結合含有置換基を有していてもよいし、第2の芳香族化合物のみが重合性不飽和結合含有置換基を有していてもよい。また、2種以上の第1の芳香族化合物、第2の芳香族化合物、第3の芳香族化合物等を用いる場合には、その一部のみが重合性不飽和結合含有置換基を有していてもよい。
芳香族エステル樹脂(A))の製造方法は特に制限されず、適宜公知の方法により製造することができる。
第1の芳香族化合物、第2の芳香族化合物、および第3の芳香族化合物等としては、上述したものが用いられる。
[他の樹脂成分]
他の樹脂成分の具体例としては、特に制限されないが、前記芳香族エステル化合物(A)以外のポリエステル樹脂、前記マレイミド化合物(B)以外のイミド樹脂、エポキシ樹脂、フェノール樹脂、アミン化合物、イミダゾール化合物、酸無水物、シアネートエステル樹脂、ベンゾオキサジン樹脂、トリアジン含有クレゾールノボラック樹脂、シアン酸エステル樹脂、スチレン-無水マレイン酸樹脂、ジアリルビスフェノールやトリアリルイソシアヌレート等のアリル基含有樹脂、ポリリン酸エステル、リン酸エステル-カーボネート共重合体、ポリフェニレンエーテル樹脂、ポリブタジエン樹脂等が挙げられる。これらの他の樹脂は単独で用いても、2種以上を組み合わせて用いてもよい。
一実施形態において、組成物は溶媒を含んでいてもよい。前記溶媒は、組成物の粘度を調整する機能等を有する。
一実施形態において、組成物は添加剤を含んでいてもよい。当該添加剤としては、硬化促進剤、難燃剤、充填剤等が挙げられる。
硬化促進剤としては、特に制限されないが、リン系硬化促進剤、アミン系硬化促進剤、イミダゾール系硬化促進剤、グアニジン系硬化促進剤、尿素系硬化促進剤、過酸化物、アゾ化合物等が挙げられる。
難燃剤としては、特に制限されないが、無機リン系難燃剤、有機リン系難燃剤、ハロゲン系難燃剤等が挙げられる。
充填剤としては、有機充填剤、無機充填剤が挙げられる。充填剤は、伸びを向上させる機能、機械的強度を向上させる機能等を有する。
本発明の一実施形態によれば、上述の芳香族エステル化合物(A)とマレイミド化合物(B)とを含有する硬化性組成物を硬化してなる硬化物が提供される。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、ジシクロペンタジエンとフェノールとの重付加反応樹脂(水酸基当量165g/当量、軟化点85℃)165g、オルソアリルフェノール134g、及びトルエン1200gを仕込み、系内を減圧窒素置換しながら内容物を溶解させた。次いで、イソフタル酸クロライド203gを仕込み、系内を減圧窒素置換しながら溶解させた。テトラブチルアンモニウムブロマイド0.6gを加えて溶解させ、窒素ガスパージを施しながら、系内を60℃以下に制御して、20%水酸化ナトリウム水溶液412gを3時間かけて滴下した。滴下終了後、同温度条件下で1時間撹拌を続けた。反応混合物を静置して分液させ、水層を取り除いた。得られた有機相に水を加えて約15分間撹拌し、静置して分液させ、水層を取り除いた。水層のpHが7になるまでこの水洗操作を繰り返した。水洗後の有機相を加熱減圧条件下乾燥させ、芳香族エステル化合物(A-1)385gを得た。芳香族エステル化合物(A-1)の理論構造を下記に示す。芳香族エステル化合物(A-1)のエステル基当量は214g/当量、アリル基当量は428g/当量、軟化点は82℃であった。
製造例1のジシクロペンタジエンとフェノールとの重付加反応樹脂165gをジアリルビスフェノールA160gに変更した以外は、製造例1と同様にして芳香族エステル化合物(A-2)402gを得た。芳香族エステル化合物(A-2)の理論構造を下記に示す。芳香族エステル化合物(A-2)のエステル基当量は212g/当量、アリル基当量は212g/当量、軟化点は51℃であった。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコにジシクロペンタジエンとフェノールの重付付加反応樹脂(水酸基当量:165g/eq、軟化点85℃)165gとα-ナフトール72g(0.5モル)とトルエン630gを仕込み、系内を減圧窒素置換し溶解させた。次いで、イソフタル酸クロライド152g(0.75モル)を仕込み、系内を減圧窒素置換し溶解させた。その後、テトラブチルアンモニウムブロマイド 0.6gを溶解させ、窒素ガスパージを施しながら、系内を60℃以下に制御して、20%水酸化ナトリウム水溶液315gを3時間かけて滴下した。次いでこの条件下で1.0時間撹拌を続けた。反応終了後、静置分液し、水層を取り除いた。更に反応物が溶解しているトルエン層に水を投入して約15分間撹拌混合し、静置分液して水層を取り除いた。水層のpHが7になるまでこの操作を繰り返した。その後、熱減圧下乾燥して活性エステル樹脂(A’)を合成した。この活性エステル樹脂(A’)のエステル基当量は223g/eq、軟化点は150℃であった。
下記表1~3に示す割合で各成分を配合し、硬化性組成物を得た。得られた硬化性組成物について、下記要領で硬化物の耐熱性評価と誘電正接値の測定を行った。結果を表1~3に示す。
・エポキシ樹脂(1):ジシクロペンタジエンフェノール型エポキシ樹脂(DIC株式会社製「HP-7200H」、エポキシ当量:277g/eq)
・エポキシ樹脂(2):ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON850S」エポキシ当量188g/当量)
・DABPA:ジアリルビスフェノールA(大和化成株式会社製、アリル基当量:154g/eq)
・DMAP:ジメチルアミノピリジン
硬化性組成物を11cm×9cm×2.4mmの型枠に流し込み、プレス機を用いて150℃で60分間、次いで175℃で90分間、更に200℃で90分間成形した。型枠から成形物を取り出し、230℃で4時間更に硬化させて硬化物を得た。
先で得た厚さ2.4mmの硬化物から幅5mm、長さ54mmの試験片を切り出した。レオメトリック社製「固体粘弾性測定装置RSAII」を用い、レクタンギュラーテンション法によるDMA(動的粘弾性)測定により、試験片の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として測定した。測定条件は周波数1Hz、昇温速度が3℃/分とした。
先で得た硬化物を105℃で2時間加熱真空乾燥させた後、温度23℃、湿度50%の室内に24時間保管したものを試験片とした。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、空洞共振法により試験片の1GHzでの誘電正接を測定した。
Claims (9)
- 2以上のフェノール性水酸基を有する第1の芳香族化合物と、
1つのフェノール性水酸基を有する第2の芳香族化合物と、
2以上のカルボキシ基を有する第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物と、
の反応生成物である、活性エステル樹脂であって、
前記第1の芳香族化合物、前記第2の芳香族化合物、並びに前記第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物の少なくとも1つが重合性不飽和結合含有置換基を有する、芳香族エステル樹脂(A)と、マレイミド化合物(B)とを含有する硬化性組成物。 - 前記第1の芳香族化合物が、下記化学式(1):
Ar1が、それぞれ独立して、置換または非置換の炭素原子数3~30の第1の芳香族環基であり、
Ar2が、それぞれ独立して、置換または非置換の炭素原子数3~30の第2の芳香族環基であり、
Xが、それぞれ独立して、酸素原子、硫黄原子、置換または非置換の炭素原子数1~20のアルキレン、置換または非置換の炭素原子数3~20のシクロアルキレン、炭素原子数8~20のアラルキレンであり、
nが、0~10であり、
この際、前記Ar1および前記Ar2を構成する水素原子の少なくとも2つが、ヒドロキシ基に置換されてなる。)
で表される、請求項1に記載の硬化性組成物。 - 前記Xが、置換または非置換の炭素原子数3~20のシクロアルキレン、炭素原子数8~20のアラルキレンである、請求項2に記載の硬化性組成物。
- 前記第2の芳香族化合物が、縮環芳香族化合物である、請求項1~3のいずれか1項に記載の硬化性組成物。
- 前記マレイミド化合物(B)が、1分子中にマレイミド基を2個以上有する化合物である請求項1~4の何れか1項記載の硬化性組成物。
- 請求項1~5の何れか1項記載の硬化性組成物の硬化物。
- 請求項1~5の何れか1項記載の硬化性組成物を用いてなるプリント配線基板。
- 請求項1~5の何れか1項記載の硬化性組成物を用いてなる半導体封止材料。
- 請求項1~5の何れか1項記載の硬化性組成物を用いてなるビルドアップフィルム。
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Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000212270A (ja) | 1999-01-20 | 2000-08-02 | Mitsubishi Chemicals Corp | 芳香族ポリカ―ボネ―トの製造方法 |
JP2001226478A (ja) | 2000-02-15 | 2001-08-21 | Mitsubishi Chemicals Corp | 芳香族ポリカーボネートの製造方法 |
JP2010235941A (ja) | 2009-03-11 | 2010-10-21 | Toyobo Co Ltd | 芳香族ポリエステル及びそれからなるポリエステル成形体 |
JP2010235940A (ja) | 2009-03-11 | 2010-10-21 | Toyobo Co Ltd | 芳香族ポリエステル成形体 |
WO2013100072A1 (ja) | 2011-12-28 | 2013-07-04 | 三菱瓦斯化学株式会社 | 高分子量ポリカーボネート樹脂の連続製造方法 |
WO2013172317A1 (ja) | 2012-05-18 | 2013-11-21 | 三菱瓦斯化学株式会社 | 高分子量ポリカーボネート樹脂の連続製造方法 |
WO2014077350A1 (ja) | 2012-11-17 | 2014-05-22 | 三菱瓦斯化学株式会社 | 高分子量化された芳香族ポリカーボネート樹脂の製造方法 |
WO2014077342A1 (ja) | 2012-11-17 | 2014-05-22 | 三菱瓦斯化学株式会社 | 高分子量化された芳香族ポリカーボネート樹脂の製造方法 |
WO2015072473A1 (ja) | 2013-11-15 | 2015-05-21 | 三菱瓦斯化学株式会社 | 高分子量芳香族ポリカーボネート樹脂の製造方法 |
JP2015189905A (ja) | 2014-03-28 | 2015-11-02 | 三菱瓦斯化学株式会社 | 芳香族ポリカーボネート樹脂組成物 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5359020A (en) * | 1990-05-22 | 1994-10-25 | Ciba-Geigy Corporation | Hardenable compositions comprising bismaleimides, alkenylphenols and phenol diallyl ethers |
EP0489691A3 (en) * | 1990-12-05 | 1992-11-04 | Ciba-Geigy Ag | Tetraallylesters as coreactants for bismaleimides |
DE69701869T2 (de) * | 1997-07-10 | 2000-11-02 | Dainippon Ink And Chemicals, Inc. | Bei hoher Temperatur vernetzbare flüssigkristalline Polyestermischungen |
US7297370B2 (en) * | 2004-12-22 | 2007-11-20 | General Electric Company | Curable encapsulant composition, device including same, and associated method |
JP6042054B2 (ja) * | 2011-05-26 | 2016-12-14 | Dic株式会社 | 熱硬化性樹脂組成物、その硬化物、半導体封止材料、プリプレグ、回路基板、及びビルドアップフィルム |
TW201817807A (zh) * | 2012-05-31 | 2018-05-16 | 日商味之素股份有限公司 | 樹脂組成物 |
JP6412329B2 (ja) * | 2014-04-02 | 2018-10-24 | 株式会社ダイセル | 熱硬化性芳香族エステルの製造方法 |
TWI685540B (zh) * | 2014-12-15 | 2020-02-21 | 日商迪愛生股份有限公司 | 熱硬化性樹脂組成物、其硬化物、及用於其之活性酯樹脂 |
JP6025952B1 (ja) * | 2015-11-11 | 2016-11-16 | エア・ウォーター株式会社 | ビニルベンジル化フェノール化合物、当該ビニルベンジル化フェノール化合物の製造方法、活性エステル樹脂、当該活性エステル樹脂の製造方法、熱硬化性樹脂組成物、当該熱硬化性樹脂組成物の硬化物、層間絶縁材料、プリプレグ、およびプリプレグの製造方法 |
US10252965B2 (en) * | 2015-11-11 | 2019-04-09 | Air Water Inc. | Vinylbenzylated phenol compound, method of manufacturing vinylbenzylated phenol compound, activated ester resin, method of manufacturing activated ester resin, thermoset resin composition, hardened material of thermoset resin composition, interlayer insulating material, prepreg, and method of manufacturing prepreg |
KR102276114B1 (ko) * | 2016-07-06 | 2021-07-13 | 디아이씨 가부시끼가이샤 | 활성 에스테르 수지 조성물과 그 경화물 |
KR102278300B1 (ko) * | 2016-07-06 | 2021-07-19 | 디아이씨 가부시끼가이샤 | 활성 에스테르 수지와 그 경화물 |
CN106977717B (zh) * | 2017-04-26 | 2019-03-26 | 黑龙江省科学院石油化学研究院 | 一种含烯基酯基化合物及其制备方法和利用其改性的双马来酰亚胺树脂 |
WO2018235425A1 (ja) * | 2017-06-21 | 2018-12-27 | Dic株式会社 | 活性エステル樹脂並びにこれを用いた組成物および硬化物 |
-
2019
- 2019-03-14 WO PCT/JP2019/010502 patent/WO2019188330A1/ja active Application Filing
- 2019-03-14 JP JP2020509888A patent/JP7041855B2/ja active Active
- 2019-03-14 US US17/041,674 patent/US11901249B2/en active Active
- 2019-03-14 CN CN201980023019.9A patent/CN111918891B/zh active Active
- 2019-03-14 KR KR1020207028458A patent/KR102453731B1/ko active IP Right Grant
- 2019-03-22 TW TW108109964A patent/TWI781305B/zh active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000212270A (ja) | 1999-01-20 | 2000-08-02 | Mitsubishi Chemicals Corp | 芳香族ポリカ―ボネ―トの製造方法 |
JP2001226478A (ja) | 2000-02-15 | 2001-08-21 | Mitsubishi Chemicals Corp | 芳香族ポリカーボネートの製造方法 |
JP2010235941A (ja) | 2009-03-11 | 2010-10-21 | Toyobo Co Ltd | 芳香族ポリエステル及びそれからなるポリエステル成形体 |
JP2010235940A (ja) | 2009-03-11 | 2010-10-21 | Toyobo Co Ltd | 芳香族ポリエステル成形体 |
WO2013100072A1 (ja) | 2011-12-28 | 2013-07-04 | 三菱瓦斯化学株式会社 | 高分子量ポリカーボネート樹脂の連続製造方法 |
WO2013172317A1 (ja) | 2012-05-18 | 2013-11-21 | 三菱瓦斯化学株式会社 | 高分子量ポリカーボネート樹脂の連続製造方法 |
WO2014077350A1 (ja) | 2012-11-17 | 2014-05-22 | 三菱瓦斯化学株式会社 | 高分子量化された芳香族ポリカーボネート樹脂の製造方法 |
WO2014077342A1 (ja) | 2012-11-17 | 2014-05-22 | 三菱瓦斯化学株式会社 | 高分子量化された芳香族ポリカーボネート樹脂の製造方法 |
WO2015072473A1 (ja) | 2013-11-15 | 2015-05-21 | 三菱瓦斯化学株式会社 | 高分子量芳香族ポリカーボネート樹脂の製造方法 |
JP2015189905A (ja) | 2014-03-28 | 2015-11-02 | 三菱瓦斯化学株式会社 | 芳香族ポリカーボネート樹脂組成物 |
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US11901249B2 (en) | 2024-02-13 |
CN111918891A (zh) | 2020-11-10 |
TW201942165A (zh) | 2019-11-01 |
KR102453731B1 (ko) | 2022-10-14 |
US20210009804A1 (en) | 2021-01-14 |
KR20200130364A (ko) | 2020-11-18 |
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