JP2014189750A - 硬化性組成物、硬化物、及びプリント配線基板 - Google Patents
硬化性組成物、硬化物、及びプリント配線基板 Download PDFInfo
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- JP2014189750A JP2014189750A JP2013069069A JP2013069069A JP2014189750A JP 2014189750 A JP2014189750 A JP 2014189750A JP 2013069069 A JP2013069069 A JP 2013069069A JP 2013069069 A JP2013069069 A JP 2013069069A JP 2014189750 A JP2014189750 A JP 2014189750A
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- Prior art keywords
- resin
- polyphenylene ether
- compound
- curable composition
- ether resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 229920005989 resin Polymers 0.000 claims abstract description 163
- 239000011347 resin Substances 0.000 claims abstract description 163
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 108
- 239000004593 Epoxy Substances 0.000 claims abstract description 89
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 13
- -1 phenol compound Chemical class 0.000 claims description 77
- 238000006243 chemical reaction Methods 0.000 claims description 58
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 239000000539 dimer Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- 239000011889 copper foil Substances 0.000 claims description 7
- 239000002966 varnish Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 230000008859 change Effects 0.000 abstract description 24
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000003822 epoxy resin Substances 0.000 description 110
- 229920000647 polyepoxide Polymers 0.000 description 110
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 58
- 238000000034 method Methods 0.000 description 42
- 239000000047 product Substances 0.000 description 42
- 238000001723 curing Methods 0.000 description 34
- 239000003431 cross linking reagent Substances 0.000 description 32
- 238000005227 gel permeation chromatography Methods 0.000 description 31
- 238000004519 manufacturing process Methods 0.000 description 30
- 239000003063 flame retardant Substances 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000005259 measurement Methods 0.000 description 26
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- JWAZRIHNYRIHIV-UHFFFAOYSA-N beta-hydroxynaphthyl Natural products C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 24
- 229920003986 novolac Polymers 0.000 description 23
- 239000003960 organic solvent Substances 0.000 description 23
- 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 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 235000013824 polyphenols Nutrition 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 239000011342 resin composition Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 16
- 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 16
- 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 16
- 229930003836 cresol Natural products 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 239000011572 manganese Substances 0.000 description 15
- 238000002156 mixing Methods 0.000 description 14
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 14
- 150000002989 phenols Chemical class 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002313 adhesive film Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 0 CCc(c1ccccc1cc1)c1O* Chemical compound CCc(c1ccccc1cc1)c1O* 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 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 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 9
- 239000005062 Polybutadiene Substances 0.000 description 9
- 239000004793 Polystyrene Substances 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 229920002223 polystyrene Polymers 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 239000011888 foil Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000011810 insulating material Substances 0.000 description 8
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000006462 rearrangement reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
- 230000003014 reinforcing effect Effects 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 5
- 238000010030 laminating Methods 0.000 description 5
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 150000007973 cyanuric acids Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 239000012796 inorganic flame retardant Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 description 3
- 150000004786 2-naphthols Chemical class 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical group C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical group CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides 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
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 3
- 229940007718 zinc hydroxide Drugs 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- YNSSPVZNXLACMW-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3-ethyl-5-methylphenyl]methyl]-2-ethyl-6-methylphenyl]pyrrole-2,5-dione Chemical compound C=1C(C)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(C)=C1N1C(=O)C=CC1=O YNSSPVZNXLACMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 2
- NAILKKRDWBJCNH-UHFFFAOYSA-N 2,6-dipropylphenol Chemical compound CCCC1=CC=CC(CCC)=C1O NAILKKRDWBJCNH-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
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- CIRRFAQIWQFQSS-UHFFFAOYSA-N 6-ethyl-o-cresol Chemical compound CCC1=CC=CC(C)=C1O CIRRFAQIWQFQSS-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
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Abstract
Description
で表される分子構造を有するエポキシ化合物(A1)と、ポリフェニレンエーテル樹脂(B)とを含有することを特徴とする硬化性組成物に関する。
本発明の硬化性組成物において主剤として用いる3官能エポキシ化合物(A1)は、下記構造式(1)
で表される2量体エポキシ化合物(A2)を含有していても良く、硬化物における熱履歴後の耐熱性変化がより小さくなることから、前記2量体エポキシ化合物(A2)を含有することが好ましい。
で表される4官能エポキシ化合物(A3)を含有しても良い。該4官能エポキシ化合物(A3)は特に官能基濃度が高く、その反応性も非常に高いことから、これを含有することにより硬化物がより高密に架橋されたものとなり、熱履歴による耐熱性変化を抑制する効果がより一層顕著なものとなることから好ましい。
においてnが3以上であるその他の多官能エポキシ化合物(A4)を含有していても良い。
で表される3官能エポキシ化合物(A1−1)となる。本発明で用いるエポキシ樹脂は前記3官能エポキシ化合物(A1)以外のエポキシ化合物を含有していても良く、前記3官能エポキシ化合物(A1−1)を必須の成分とする場合には、熱膨張率及び熱履歴後の耐熱性変化がより小さく、かつ、誘電率及び誘電正接の低い硬化物が得られることから、エポキシ樹脂中における前記3官能エポキシ化合物(A1−1)の含有率が、GPC測定における面積比率で55%以上であることが好ましく、70〜98%の範囲であることがより好ましく、80〜95%の範囲であることが特に好ましい。
<GPC測定条件>
測定装置 :東ソー株式会社製「HLC−8220 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−8020モデルIIバージョン4.10」
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−8020モデルIIバージョン4.10」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)。
で表される3官能エポキシ化合物(A1−2)となる。本発明で用いるエポキシ樹脂は前記3官能エポキシ化合物(A1)以外のエポキシ化合物を含有していても良く、前記3官能エポキシ化合物(A1−2)を必須の成分とする場合には、熱膨張率及び熱履歴後の耐熱性変化がより小さく、かつ、誘電率及び誘電正接の低い硬化物が得られることから、エポキシ樹脂中における前記3官能エポキシ化合物(A1−2)の含有率が、GPC測定における面積比率で25%以上であることが好ましく、25〜70%の範囲であることがより好ましく、30〜60%の範囲であることが特に好ましい。
で表される4官能エポキシ化合物(A3−2)を含有することが好ましく、エポキシ樹脂中の含有率は、熱履歴後の耐熱性変化も小さい硬化物が得られることから、GPC測定における面積比率で10〜40%の範囲であることが好ましく、10〜30%の範囲であることがより好ましい。
で表されるその他の多官能エポキシ化合物(A4−2)を含有していても良く、その場合、硬化物における膨張率及び熱履歴後の耐熱性変化をより低減できるという本願発明の硬化が十分に発揮されることから、エポキシ樹脂中の前記3官能エポキシ化合物(A1−2)、前記2量体化合物(A2)、及び前記4官能化合物(A3−2)の合計の含有率がGPC測定における面積比率で65%以上であり、かつ、前記3官能エポキシ化合物(A1−2)、前記2量体化合物(A2)、前記4官能化合物(A3−2)及び前記多官能化合物(A4−2)においてnが3〜5の何れかである化合物の合計の含有率が85%以上であることが好ましい。
方法1:有機溶剤及びアルカリ触媒の存在下、β−ナフトール化合物とホルムアルデヒドとを反応させ、次いで、ホルムアルデヒドの存在下、クレゾールを加え反応させて、クレゾール−ナフトール樹脂を得(工程1)、次いで、得られたクレゾール−ナフトール樹脂にエピハロヒドリンを反応させて(工程2)、目的とするエポキシ樹脂を得る方法。
方法2:有機溶剤及びアルカリ触媒の存在下、クレゾール、β−ナフトール化合物、及びホルムアルデヒドを反応させて、クレゾール−ナフトール樹脂を得(工程1)、次いで、得られたクレゾール−ナフトール樹脂にエピハロヒドリンを反応させて(工程2)、目的とするエポキシ樹脂を得る方法。
(1)フェノール性水酸基を有する化合物を単独で用いる単独重縮合や、該化合物を2種以上用いる共重合により得られる化合物(以下「ポリフェニレンエーテル樹脂(B1)」とする。)
(2)ポリスチレンなどとアロイ化されたポリフェニレンエーテル樹脂(以下「ポリフェニレンエーテル樹脂(B2)」とする。)
(3)ポリフェニレンエーテル樹脂とフェノール性化合物とを反応開始剤の存在下で分解再配列反応させて得られる化合物(以下「ポリフェニレンエーテル樹脂(B3)」とする。)
(4)ポリブタジエンポリマーで変性されたポリフェニレンエーテル樹脂(以下「ポリフェニレンエーテル樹脂(B4)」とする。)
(3−2)数平均分子量が10,000〜30,000のポリフェニレンエーテル樹脂とフェノール性水酸基を二つ以上有するフェノール系化合物とを反応開始剤の存在下で分解再配列反応させて得られる数平均分子量5,000以下の化合物(以下「ポリフェニレンエーテル樹脂(B3−2)」とする。)
」は特に断わりのない限り質量基準である。尚、軟化点、13C−NMR、GPC及びMSは以下の条件にて測定した。
装置:日本電子(株)製 AL−400
測定モード:SGNNE(NOE消去の1H完全デカップリング法)
溶媒 :ジメチルスルホキシド
パルス角度:45℃パルス
試料濃度 :30wt%
積算回数 :10000回
測定装置 :東ソー株式会社製「HLC−8220 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−8020モデルIIバージョン4.10」
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−8020モデルIIバージョン4.10」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。
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)。
H)
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、β−ナフトール216質量部(1.5モル)、イソプロピルアルコール250質量部、37%ホルマリン水溶液122質量部(1.50モル)、49%水酸化ナトリウム31質量部(0.38モル)を仕込み、室温から75℃まで攪拌しながら昇温し、75℃で1時間撹拌した。続いて、パラクレゾール81質量部(0.75モル)を仕込み、さらに75℃で8時間攪拌した。反応終了後、第1リン酸ソーダ45質量部を添加して中和した後、メチルイソブチルケトン630質量部加え、水158量部で3回洗浄を繰り返した後に、加熱減圧下乾燥してクレゾール−ナフトール樹脂(a−1)290質量部得た。得られたクレゾール−ナフトール樹脂(a−1)のGPCチャートを図1に示す。クレゾール−ナフトール樹脂(a−1)の水酸基当量は140グラム/当量であり、GPCチャートから算出される下記構造式(a)で表される3官能化合物の含有率は83.5%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、β−ナフトール216質量部(1.5モル)、イソプロピルアルコール250質量部、37%ホルマリン水溶液122質量部(1.50モル)、49%水酸化ナトリウム31質量部(0.38モル)を仕込み、室温から75℃まで攪拌しながら昇温し、75℃で1時間撹拌した。続いて、オルソクレゾール81質量部(0.75モル)を仕込み、さらに75℃で8時間攪拌した。反応終了後、第1リン酸ソーダ45質量部を添加して中和した後、メチルイソブチルケトン630質量部加え、水158質量部で3回洗浄を繰り返した後に、加熱減圧下乾燥してクレゾール−ナフトール樹脂(a−2)290質量部得た。得られたクレゾール−ナフトール樹脂(a−2)のGPCチャートを図5に示す。クレゾール−ナフトール樹脂(a−2)の水酸基当量は140グラム/当量であり、GPCチャートから算出される下記構造式(a)で表される3官能化合物の含有率は51.5%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、トルエン250質量部を入れ、内温を90℃に制御しながらポリフェニレンエーテル樹脂[SABIC社製「ノリル640−111」数平均分子量(Mn)25,000]90質量部、ビスフェノールA 7質量部、過酸化ベンゾイル7質量部を入れ、2時間撹拌を続けて反応させることにより、数平均分子量(Mn)2,500のポリフェニレンエーテル樹脂(B−2)を得た。
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、α−ナフトール505質量部(3.50モル)、水158質量部、蓚酸5質量部を仕込み、室温から100℃まで45分で昇温しながら撹拌した。続いて、42質量%ホルマリン水溶液177質量部(2.45モル)を1時間要して滴下した。滴下終了後、さらに100℃で1時間攪拌し、その後180℃まで3時間で昇温した。反応終了後、反応系内に残った水分を加熱減圧下に除去しナフトール樹脂(a’−1)498質量部を得た。得られたナフトール樹脂(a’−1)の水酸基当量は154グラム/当量であった。
下記要領で硬化性組成物を調整し、誘電特性、熱履歴による耐熱性変化、及び熱膨張率の評価を行った。結果を表1に示す。
主剤であるエポキシ成分として、(A−1)、(A−2)、又は(A’−1)を、硬化剤としてポリフェニレンエーテル樹脂(B−1)(SABIC社製「SA90−100」)又は前記(B−2)を、硬化促進剤として2−エチル−4−メチルイミダゾール(2E4MZ)を用いて表1に示した組成で配合し、更にメチルエチルケトンを加えて不揮発分が58質量%となるように調整し、硬化性組成物を得た。
先で得た硬化性組成物をプレスで150℃の温度で10分間成形した後、175℃で5時間硬化させて評価サンプルを作成した。これについてJIS−C−6481に準拠し、アジレント・テクノロジー株式会社製インピーダンス・マテリアル・アナライザ「HP4291B」を用いて、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。
下記条件で積層板を作成した。
基材:日東紡績株式会社製 ガラスクロス「#2116」(210×280mm)
プライ数:6 プリプレグ化条件:160℃
硬化条件:200℃、40kg/cm2で1.5時間、成型後板厚:0.8mm
先で得た積層板について、粘弾性測定装置(DMA:レオメトリック社製固体粘弾性測定装置「RSAII」、レクタンギュラーテンション法;周波数1Hz、昇温速度3℃/min)を用いて、以下の温度条件で2回、弾性率変化が最大となる(tanδ変化率が最も大きい)温度(Tg)を測定した。
温度条件
第1回測定:35℃から275℃まで3℃/minで昇温
第2回測定:35℃から330℃まで3℃/minで昇温
それぞれ得られた温度差をΔTgとして評価した。
先で得た積層板を5mm×5mm×0.8mmのサイズに切り出し、これを試験片として熱機械分析装置(TMA:セイコーインスツルメント社製SS−6100)を用いて、圧縮モードで熱機械分析を行った。
測定条件
測定架重:88.8mN
昇温速度:10℃/分で2回
測定温度範囲:−50℃から300℃
上記条件での測定を同一サンプルにつき2回実施し、2回目の測定における、40℃から60℃の温度範囲における平均線膨張率を熱膨張係数として評価した。
Claims (7)
- 前記ポリフェニレンエーテル樹脂(B)が、重量平均分子量(Mw)を1,000〜5,000の範囲に有するものである請求項1又は2記載の硬化性組成物。
- 前記ポリフェニレンエーテル樹脂(B)が、数平均分子量が10,000〜30,000のポリフェニレンエーテル樹脂とフェノール性水酸基を2つ以上有するフェノール系化合物とを、反応開始剤の存在下で分解再配列反応させて得られるものである請求項1〜3の何れか一つに記載の硬化性組成物。
- 前記ポリフェニレンエーテル樹脂(B)が、一つのフェニレン骨格につき、該フェニレン骨格の炭素原子に結合したメチル基を1〜4つ有する樹脂である請求項1〜4の何れか一つに記載の硬化性組成物。
- 請求項1〜5の何れか一つに記載の硬化性組成物を硬化させてなる硬化物。
- 請求項1〜5の何れか一つに記載の硬化性組成物に、更に有機溶剤を配合したワニス組成物を、補強基材に含浸し銅箔を重ねて加熱圧着させることにより得られるプリント配線基板。
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KR20190081995A (ko) * | 2017-12-29 | 2019-07-09 | 삼성에스디아이 주식회사 | 반도체 소자 밀봉용 에폭시 수지 조성물 및 이를 이용하여 밀봉된 반도체 소자 |
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