CN116615489A - Curable resin composition, prepreg, and cured product thereof - Google Patents
Curable resin composition, prepreg, and cured product thereof Download PDFInfo
- Publication number
- CN116615489A CN116615489A CN202280008170.7A CN202280008170A CN116615489A CN 116615489 A CN116615489 A CN 116615489A CN 202280008170 A CN202280008170 A CN 202280008170A CN 116615489 A CN116615489 A CN 116615489A
- Authority
- CN
- China
- Prior art keywords
- resin composition
- curable resin
- compound
- acid
- component
- 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.)
- Pending
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- 239000011342 resin composition Substances 0.000 title claims abstract description 64
- -1 maleimide compound Chemical class 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 14
- 239000011889 copper foil Substances 0.000 abstract description 14
- 229920005989 resin Polymers 0.000 description 76
- 239000011347 resin Substances 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000002904 solvent Substances 0.000 description 39
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 30
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 21
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 238000005227 gel permeation chromatography Methods 0.000 description 15
- 150000004982 aromatic amines Chemical class 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 229920000647 polyepoxide Polymers 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- 239000002966 varnish Substances 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- 239000005011 phenolic resin Substances 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- 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 8
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000004643 cyanate ester Substances 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 239000004848 polyfunctional curative Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920000049 Carbon (fiber) Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000010533 azeotropic distillation Methods 0.000 description 6
- TYMZLIDQEUWXEL-UHFFFAOYSA-N bis(2,3-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC(OP(O)(=O)OC=2C(=C(C)C=CC=2)C)=C1C TYMZLIDQEUWXEL-UHFFFAOYSA-N 0.000 description 6
- 239000004917 carbon fiber Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012948 isocyanate Substances 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
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 239000003566 sealing material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910000064 phosphane Inorganic materials 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 239000009719 polyimide resin Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002759 woven fabric Substances 0.000 description 4
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 3
- SSPMJQOASMQREI-UHFFFAOYSA-N 1-(methoxymethyl)-2-phenylbenzene Chemical group COCC1=CC=CC=C1C1=CC=CC=C1 SSPMJQOASMQREI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000005394 methallyl group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 150000004978 peroxycarbonates Chemical class 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012783 reinforcing fiber Substances 0.000 description 3
- 238000001721 transfer moulding Methods 0.000 description 3
- 239000003799 water insoluble solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-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
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- DAJPMKAQEUGECW-UHFFFAOYSA-N 1,4-bis(methoxymethyl)benzene Chemical compound COCC1=CC=C(COC)C=C1 DAJPMKAQEUGECW-UHFFFAOYSA-N 0.000 description 2
- INZDTEICWPZYJM-UHFFFAOYSA-N 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=C(CCl)C=C1 INZDTEICWPZYJM-UHFFFAOYSA-N 0.000 description 2
- XBPVMINOJXIFKQ-UHFFFAOYSA-N 1-[4-[2-[3-[2-[4-(2,5-dioxopyrrol-1-yl)phenyl]propan-2-yl]phenyl]propan-2-yl]phenyl]pyrrole-2,5-dione Chemical compound C=1C=CC(C(C)(C)C=2C=CC(=CC=2)N2C(C=CC2=O)=O)=CC=1C(C)(C)C(C=C1)=CC=C1N1C(=O)C=CC1=O XBPVMINOJXIFKQ-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-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
- 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 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- GAGWMWLBYJPFDD-UHFFFAOYSA-N 2-methyloctane-1,8-diamine Chemical compound NCC(C)CCCCCCN GAGWMWLBYJPFDD-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
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 description 2
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
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- 239000005770 Eugenol Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000005922 Phosphane Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 108091063785 miR-3000 stem-loop Proteins 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- GYMBMZSWTJBJPE-UHFFFAOYSA-N nonadecane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCCCCC(N)N GYMBMZSWTJBJPE-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- YNVQYOQLKGNUBZ-UHFFFAOYSA-N octadecane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCCCC(N)N YNVQYOQLKGNUBZ-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 101150032584 oxy-4 gene Proteins 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- UMSVUULWTOXCQY-UHFFFAOYSA-N phenanthrene-1,2,7,8-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC=C(C(=O)O)C(C(O)=O)=C3C=CC2=C1C(O)=O UMSVUULWTOXCQY-UHFFFAOYSA-N 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- XGSHEASGZHYHBU-UHFFFAOYSA-N tetradecane-1,1-diamine Chemical compound CCCCCCCCCCCCCC(N)N XGSHEASGZHYHBU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- FRXCPDXZCDMUGX-UHFFFAOYSA-N tridecane-1,1-diamine Chemical compound CCCCCCCCCCCCC(N)N FRXCPDXZCDMUGX-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CAPOZRICGSDRLP-UHFFFAOYSA-N tris(2,3-dimethylphenyl) phosphate Chemical compound CC1=CC=CC(OP(=O)(OC=2C(=C(C)C=CC=2)C)OC=2C(=C(C)C=CC=2)C)=C1C CAPOZRICGSDRLP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- JRHDFVNUWLMGBU-UHFFFAOYSA-L zinc octyl phosphate Chemical compound C(CCCCCCC)OP(=O)([O-])[O-].[Zn+2] JRHDFVNUWLMGBU-UHFFFAOYSA-L 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- IJQXGKBNDNQWAT-UHFFFAOYSA-L zinc;docosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O IJQXGKBNDNQWAT-UHFFFAOYSA-L 0.000 description 1
- PORPEXMDRRVVNF-UHFFFAOYSA-L zinc;octadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCOP([O-])([O-])=O PORPEXMDRRVVNF-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
-
- 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
Abstract
The invention provides a curable resin composition which has excellent heat resistance, copper foil peeling strength, dielectric property and moisture resistance, and a cured product thereof. A curable resin composition comprising a maleimide compound (A) represented by the following formula (1) and a polyphenylene ether compound (B) having an unsaturated double bond, wherein the weight ratio of the component (A) to the component (B) is 50/50 to 5/95. ( In the formula (1), R represents a hydrogen atom or a methyl group. m represents an integer of 0 to 3. n is a repetition number, and the average value of n is more than 1 and less than 5. )
Description
Technical Field
The present invention relates to a curable resin composition, a prepreg, and a cured product thereof, which are preferably used for electrical/electronic parts such as semiconductor sealing materials, printed wiring boards, laminate layers, lightweight high-strength materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics, and three-dimensional (three dimensional, 3D) printing applications.
Background
In recent years, a laminate board on which an electric/electronic component is mounted is required to have wide characteristics and a high level due to expansion of its application field. For example, semiconductor chips have been mainly mounted on metal lead frames, but many semiconductor chips having high processing capability such as a central processing unit (central processing unit, CPU) are mounted on laminated boards made of a polymer material. As the speed of elements such as CPU increases, the clock frequency increases, which causes problems in signal propagation delay and transmission loss, and low dielectric constant and low dielectric loss tangent are required for wiring boards.
In terms of development of communication technology, timing of fifth generation mobile communication (5G) is being developed in recent years, and it is expected that communication devices using not only Sub6 but also quasi-millimeter wave or millimeter wave of 10GHz or more, particularly 28GHz or more will be increased in explosion, and substrate materials corresponding to high frequencies are required in base stations, antennas, and communication devices. Among these substrate materials, materials that can be used stably in these regions are required in order to place high importance on dielectric characteristics (particularly dielectric loss tangent) without lowering the transmission rate.
In addition, in recent years, due to the spread of mobile electronic devices such as mobile phones, precision electronic devices are beginning to be carried to an outdoor environment or used in the very vicinity of the human body, and thus, resistance to an external environment (particularly, a humidity and heat resistant environment) is required. Further, in the automotive field, there is a rapid progress in electronics, and there is a case where precision electronic equipment is disposed in the vicinity of an engine, and there is a demand for higher level of heat resistance and moisture resistance.
A wiring board using a BT resin which is a resin obtained by combining a bisphenol a type cyanate ester compound and a bismaleimide compound as in patent document 1 is widely used as a high-performance wiring board because of excellent heat resistance, chemical resistance, dielectric characteristics, and the like, but in order to cope with the above-described further high performance, improvement is required.
In this case, the maleimide resin available on the market has a significantly improved heat resistance as compared with the epoxy resins and the like conventionally used for the above-mentioned applications, and exhibits excellent dielectric characteristics in a high frequency region, but the maleimide resin having a high heat resistance has the following drawbacks: the moisture resistance is low, and the adhesion to copper foil is also low because of its rigidity and brittleness.
On the other hand, maleimide resins such as patent documents 2 and 3 have been developed, but they have not been sufficiently known.
Further, a composition comprising a maleimide resin and a phenol resin containing an acryl group as in patent document 4 has been proposed, but since a phenolic hydroxyl group which does not participate in the reaction remains during the curing reaction, there is a problem that the water absorption rate is high in addition to the insufficient dielectric characteristics.
Prior art literature
Patent literature
Patent document 1: japanese patent publication No. 54-3040
Patent document 2: japanese patent laid-open No. 3-100016
Patent document 3: japanese patent No. 5030297
Patent document 4: japanese patent laid-open No. 04-359911
Patent document 5: japanese patent publication No. 4-75222
Patent document 6: japanese patent publication No. 6-37465
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made in view of such circumstances, and an object thereof is to provide a curable resin composition and a cured product thereof, which exhibit excellent heat resistance, copper foil peel strength, dielectric characteristics, and moisture resistance.
Technical means for solving the problems
The present inventors have made an intensive study to solve the above problems, and as a result, have found that a cured product of a curable resin composition comprising a maleimide compound having a specific structure and a polyphenylene ether compound having an unsaturated double bond is excellent in heat resistance, copper foil peel strength, dielectric characteristics and moisture resistance, and have completed the present invention.
That is, the present invention relates to the following [1] to [7].
[1]
A curable resin composition comprising a maleimide compound (A) represented by the following formula (1) and a polyphenylene ether compound (B) having an unsaturated double bond, wherein the weight ratio of the component (A) to the component (B) is 50/50 to 5/95.
[ chemical 1]
( In the formula (1), R represents a hydrogen atom or a methyl group. m represents an integer of 0 to 3. n is a repetition number, and the average value of n is more than 1 and less than 5. )
[2]
A curable resin composition comprising a maleimide compound (A) represented by the following formula (1) and a polyphenylene ether compound (B) having an unsaturated double bond, wherein the amount of the component (B) is 0.20 to 4.2 equivalents relative to 1 equivalent of the component (A).
[ chemical 2]
( In the formula (1), R represents a hydrogen atom or a methyl group. m represents an integer of 0 to 3. n is a repetition number, and the average value of n is more than 1 and less than 5. )
[3]
The curable resin composition according to the preceding item [1] or [2], wherein the component (B) is a polyphenylene ether compound having a (meth) acrylic group.
[4]
The curable resin composition according to any one of the preceding items [1] to [3], wherein the component (B) is a compound represented by the following formula (2) or a compound represented by the following formula (4).
[ chemical 3]
(in the formula (2), n is a repetition number, and the average value thereof is 1 < n < 10.)
[ chemical 4]
(in the formula (4), n is a repetition number, and the average value thereof is 1 < n < 10.)
[5]
The curable resin composition according to any one of the preceding items [1] to [4], further comprising a hardening accelerator.
[6]
A prepreg comprising a sheet-like fibrous base and the curable resin composition according to any one of the preceding items [1] to [5 ].
[7]
A cured product obtained by curing the curable resin composition according to any one of the preceding items [1] to [5], or the prepreg according to the preceding item [6 ].
ADVANTAGEOUS EFFECTS OF INVENTION
The cured product of the curable resin composition of the present invention has excellent heat resistance, copper foil peel strength, dielectric properties, and moisture resistance.
Drawings
FIG. 1 is a gel permeation chromatography (gel permeation chromatography, GPC) chart of Synthesis example 1.
FIG. 2 is a GPC chart of Synthesis example 2.
Detailed Description
The curable resin composition of the present invention will be described below.
The curable resin composition of the present invention contains a maleimide compound represented by the following formula (1) (hereinafter, also referred to as component (a)), and a polyphenylene ether compound having an unsaturated double bond (hereinafter, also referred to as component (B)).
[ chemical 5]
( In the formula (1), R represents a hydrogen atom or a methyl group. m represents an integer of 0 to 3. n is a repetition number, and the average value of n is more than 1 and less than 5 )
The compound represented by the formula (1) is particularly preferably represented by the following formula (1-a).
[ chemical 6]
In the above formula (1), the value of n can be calculated from the value of the number average molecular weight obtained by measurement of the gel permeation chromatography (GPC, detector: RI (refractive index)) of the maleimide resin or the area ratio of each of the separated peaks.
In the above formula (1), when n=1, the solubility in a solvent is low, and when n is 5 or more, the fluidity at the time of molding is poor, and the characteristics as a cured product cannot be sufficiently exhibited.
The component (a) preferably has a molecular weight distribution, and in the formula (1), the content of n=1 body obtained by GPC analysis (RI) is preferably 98 area% or less, more preferably 20 area% to 90 area%, still more preferably 30 area% to 80 area%, particularly preferably 40 area% to 80 area%. When the content of n=1 bodies is 98 area% or less, heat resistance becomes good. In addition, crystallinity is reduced, and solvent solubility becomes good. On the other hand, when the lower limit of n=1 is 20 area% or more, the viscosity of the resin solution is reduced, and the impregnation property is improved. In addition, since the solvent can be removed at a low temperature when the solvent is taken out as a solid, self-polymerization is less likely to occur, and the operation becomes easy.
The component (a) has excellent solvent solubility by increasing the proportion of the asymmetric structure having different orientations with respect to the maleimide group, and the cured product thereof has improved dielectric characteristics. The orientation ratio in the n=1 body of the formula (1) can be determined by high performance liquid chromatography (high performance liquid chromatography, HPLC) analysis (225 nm), and the ortho-para-body is preferably 30 area% or more and less than 60 area%, more preferably 35 area% or more and less than 55 area%, particularly preferably 40 area% or more and less than 55 area% of the total n=1 body.
The softening point of the component (A) is preferably 50 to 150 ℃, more preferably 80 to 120 ℃, still more preferably 90 to 120 ℃, particularly preferably 95 to 120 ℃. The melt viscosity at 150℃is 0.05 to 100 Pa.s, preferably 0.1 to 40 Pa.s.
The method for producing the component (a) is described below, but is not limited to this method.
[ method for producing aromatic amine resin ]
The component (a) may be an aromatic amine resin represented by the following formula (3) as a precursor.
[ chemical 7]
( In the formula (3), R represents a hydrogen atom or a methyl group. m represents an integer of 0 to 3. n is a repetition number, and the average value of n is more than 1 and less than 5. )
The method for producing the aromatic amine resin represented by the formula (3) is not particularly limited, and for example, in patent document 5, n=1 in the formula (3) is obtained as a main component by reacting aniline with m-diisopropenylbenzene or m-di (α -hydroxyisopropyl) benzene in the presence of an acidic catalyst at 180 to 250 ℃. In the n=1 body, a compound having a symmetrical structure in which the orientation with respect to the aniline 2 molecule is the same as that of 1, 3-bis (p-aminocumyl) benzene or 1, 3-bis (o-aminocumyl) benzene; three isomers of an asymmetric compound having different orientations with respect to the aniline 2 molecule, such as 1- (o-amino cumyl) -3- (p-amino cumyl) benzene. Further, n=2 to 5 is also produced as a subcomponent, but in patent document 5, these were purified by crystallization to obtain 1, 3-bis (p-amino cumyl) benzene with a purity of 98%. In patent document 6, 1, 3-bis (p-amino cumyl) benzene is maleinized to synthesize N, N' - (1, 3-phenylene-bis- (2, 2-propylene) -bis-p-phenylene) bismaleimide, and a product is obtained as a crystal, but heating is required to dissolve the product in a solvent, and if the product is left at room temperature after heating, crystals are precipitated within several hours. Therefore, when the resin composition is adjusted, there is a possibility that crystals will be deposited, and the higher the concentration of N, N' - (1, 3-phenylene-bis- (2, 2-propylene) -bis-p-phenylene) bismaleimide is, the higher the possibility that crystals will be formed. In order to produce a printed wiring board or a composite material, glass cloth or carbon fiber is impregnated in a varnish and a resin is attached, but if crystals are precipitated, the impregnation operation cannot be performed, and if the temperature is increased to maintain a dissolved state, the reaction of the composition is accelerated and the usable time of the varnish is shortened.
Examples of the acidic catalyst used in the synthesis of the aromatic amine resin represented by the above formula (3) include acidic catalysts such as hydrochloric acid, phosphoric acid, sulfuric acid, formic acid, zinc chloride, ferric chloride, aluminum chloride, p-toluenesulfonic acid, methanesulfonic acid and the like. In the present invention, a protonic acid such as hydrochloric acid, p-toluenesulfonic acid, methanesulfonic acid and the like is preferable. These may be used singly or in combination of two or more. The amount of the catalyst to be used is preferably 1 to 12% by weight, more preferably 1 to 10% by weight, particularly preferably 1 to 7% by weight, based on 100% by weight of the aniline to be used, and if more than 12% by weight, the target asymmetric compound is small, and the compound having a symmetrical structure is preferentially formed. On the other hand, if the amount is less than 1%, the reaction proceeds slowly, and the reaction may not be completed, which is not preferable.
The reaction may be carried out using an organic solvent such as toluene or xylene, if necessary, or may be carried out in the absence of a solvent. For example, when the catalyst contains water after adding an acidic catalyst to a mixed solution of aniline and a solvent, it is preferable to remove water from the system by azeotropic distillation. Then diisopropenylbenzene or di (alpha-hydroxyisopropyl) benzene is added, and then the temperature is raised while removing the solvent from the system, and the reaction is carried out at 140 to 190 ℃, preferably 160 to 190 ℃ for 5 to 50 hours, preferably 5 to 30 hours. When the reaction temperature is too high, the asymmetric structure is formed and then the rebinding is performed, and the symmetric structure is preferentially formed, so that the aimed solvent solubility and electrical characteristics cannot be exhibited. When bis (. Alpha. -hydroxyisopropyl) benzene is used, water is by-produced and is therefore removed from the system at a temperature rise while being azeotroped with a solvent. After the reaction, neutralizing the acid catalyst with an aqueous alkali solution, adding a water-insoluble organic solvent to the oil layer, repeatedly washing with water until the wastewater becomes neutral, and then removing the solvent and the excess aniline derivative under reduced pressure and heating. When activated clay or ion exchange resin is used, the reaction mixture is filtered after the completion of the reaction to remove the catalyst.
Further, diphenylamine is formed as a by-product depending on the reaction temperature and the kind of the catalyst, and is preferably removed as needed. The diphenyl amine derivative is removed to 1 wt% or less, preferably 0.5 wt% or less, more preferably 0.2 wt% or less at high temperature/high vacuum, or by steam distillation or the like.
[ method for producing maleimide resin ]
Component (a) can be obtained by: the aromatic amine resin represented by the formula (3) obtained in the above step is subjected to an addition or dehydration condensation reaction with maleic acid or maleic anhydride (hereinafter also referred to as "maleic anhydride") in the presence of a solvent and a catalyst.
The solvent used in the reaction is preferably a water-insoluble solvent because water produced in the reaction needs to be removed from the system. Examples include: aromatic solvents such as toluene and xylene; aliphatic solvents such as cyclohexane and n-hexane; ethers such as diethyl ether and diisopropyl ether; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as methyl isobutyl ketone and cyclopentanone, etc., but the present invention is not limited thereto, and two or more kinds may be used in combination.
In addition, an aprotic polar solvent may be used in addition to the water-insoluble solvent. Examples thereof include dimethylsulfone, dimethylsulfoxide, dimethylformamide, dimethylacetamide, 1, 3-dimethyl-2-imidazolidinone, and N-methyl-2-pyrrolidone, and two or more of them may be used in combination. When an aprotic polar solvent is used, it is preferable to use an aprotic polar solvent having a boiling point higher than that of the water-insoluble solvent used in combination.
The catalyst used in the reaction is an acidic catalyst, and examples thereof include, but are not particularly limited to, p-toluenesulfonic acid, hydroxy-p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, phosphoric acid, and the like. The amount of the acid catalyst used is usually 0.1 to 10% by weight, preferably 1 to 5% by weight, relative to the aromatic amine resin.
For example, an aromatic amine resin represented by the formula (3) is dissolved in toluene and N-methyl-2-pyrrolidone, maleic anhydride is added thereto to produce amic acid, and then p-toluenesulfonic acid is added thereto, and the reaction is carried out while removing water produced under reflux conditions from the system.
Alternatively, maleic anhydride is dissolved in toluene, and the N-methyl-2-pyrrolidone solution of the aromatic amine resin represented by the above formula (3) is added with stirring to produce amic acid, and then p-toluenesulfonic acid is added thereto, and the reaction is carried out while removing water produced under reflux conditions from the system.
Alternatively, maleic anhydride is dissolved in toluene, p-toluenesulfonic acid is added, and the reaction is carried out while removing water generated during azeotropy from the middle of the system while dropping the N-methyl-2-pyrrolidone solution of the aromatic amine resin represented by the above formula (3) in a stirred/refluxed state, and toluene is returned to the system (the first-stage reaction above).
In either method, the maleic anhydride is usually used in an amount of 1.0 to 3.0 equivalents, preferably 1.2 to 2.0 equivalents, relative to the amino group of the aromatic amine resin represented by the formula (3).
In order to reduce the non-ring-closed amic acid, water is added to the reaction solution after the maleinization reaction listed above to separate the reaction solution into a resin solution layer and an aqueous layer, and the excess maleic acid or maleic anhydride, aprotic polar solvent, catalyst, etc. are dissolved in the aqueous layer side, so that the solution is separated and removed, and the same operation is repeated to completely remove the excess maleic acid or maleic anhydride, aprotic polar solvent, catalyst, etc. The catalyst is added again to the maleimide resin solution from which the excess maleic acid or maleic anhydride, aprotic polar solvent, and organic layer of the catalyst have been removed, and the dehydration ring-closure reaction of the residual amic acid under the condition of heating reflux is carried out again, whereby a maleimide resin solution having a low acid value (the above is the second-stage reaction) is obtained.
The period of the re-dehydration ring-closure reaction is usually 1 to 5 hours, preferably 1 to 3 hours, and the aprotic polar solvent may be added as needed. After the reaction was completed, the reaction mixture was cooled, and the washing was repeated until the washing water became neutral. After the water is removed by azeotropic dehydration under reduced pressure by heating, the solvent may be distilled off, or a resin solution prepared by adding another solvent to a desired concentration may be removed as a solid resin by completely distilling off the solvent.
Next, the component (B) will be described.
The component (B) is not particularly limited as long as it has an unsaturated double bond and a polyphenylene ether structure. The unsaturated double bond in the component (B) may be: (meth) acrylic groups, styryl groups, allyl groups, vinyl groups, methallyl groups (methallyl groups), preferably (meth) acrylic groups. As commercial products, SA-9000-111 (polyphenylene ether compound having a methacrylic group, manufactured by Sabio corporation (Saudi Basic Industries Corporation) of the Sand foundation Co., ltd.) represented by the following formula (2) or OPE-2St 1200 (polyphenylene ether compound having a styryl group, manufactured by Mitsubishi gas chemical corporation) represented by the following formula (4) can be mentioned. In particular, from the viewpoint of dielectric characteristics, a compound represented by the following formula (2) is preferable.
[ chemical 8]
(in the formula (2), n is a repetition number, and the average value is 1 < n < 10)
[ chemical 9]
(in the formula (4), n is a repetition number, and the average value is 1 < n < 10)
The weight average molecular weight (Mw) of the component (B) is preferably 500 to 5000, more preferably 2000 to 5000, and further preferably 2000 to 4000. When the molecular weight is 500 or more, the heat resistance of the cured product is improved. When the molecular weight is 5000 or less, the melt viscosity is reduced, sufficient fluidity can be obtained, and the moldability is good. In addition, since the reactivity is improved, the curing time can be shortened, and the heat resistance of the cured product is also improved. Specifically, the weight average molecular weight can be measured by gel permeation chromatography or the like.
The component (B) can be imparted with radical polymerizability by reacting a polyphenylene ether compound with a compound having an unsaturated double bond such as methacryloyl chloride, acryloyl chloride, chloromethylstyrene, or the like.
The polyphenylene ether compound can be obtained by polymerization reaction, or by redistribution reaction of a high molecular weight polyphenylene ether compound having a weight average molecular weight of 10000 to 30000. For example, the redistribution reaction is carried out by heating a high molecular weight polyphenylene ether compound in a solvent such as toluene in the presence of a phenol compound and a radical initiator. The polyphenylene ether compound obtained by the redistribution reaction in this way has hydroxyl groups derived from the phenolic compound which contribute to hardening at both ends of the molecular chain, and thus can maintain higher heat resistance, which is preferable in this respect. In addition, polyphenylene ether compounds obtained by polymerization are preferable in terms of exhibiting excellent fluidity.
In the case of the polyphenylene ether compound obtained by the polymerization reaction, the adjustment of the molecular weight of the polyphenylene ether compound can be performed by adjusting the polymerization conditions or the like. In the case of the polyphenylene ether compound obtained by the redistribution reaction, the molecular weight can be adjusted by adjusting the conditions of the redistribution reaction, and the like. More specifically, it is conceivable to adjust the amount of the phenolic compound to be used in the redistribution reaction. That is, the larger the blending amount of the phenol compound, the lower the molecular weight of the obtained component polyphenylene ether compound.
Specific examples of the polyphenylene ether compound include poly (2, 6-dimethyl-1, 4-phenylene ether). That is, in the case of the component (B) obtained by the redistribution reaction, examples of the high molecular weight polyphenylene ether compound include polyphenylene ether compounds obtained by using poly (2, 6-dimethyl-1, 4-phenylene ether) and the like. The phenol compound used in the redistribution reaction is not particularly limited, and for example, a polyfunctional phenol compound having two or more phenolic hydroxyl groups in the molecule such as bisphenol a, phenol novolac, cresol novolac, or the like can be preferably used. These may be used alone or in combination of two or more.
The weight ratio of the component (A) to the component (B) in the curable resin composition of the present invention is preferably 50/50 to 5/95, more preferably 30/70 to 5/95, still more preferably 25/75 to 5/95, and particularly preferably 25/75 to 10/90. The functional group equivalent ratio of the component (a) to the component (B) is preferably 0.2 to 4.2 equivalents, more preferably 0.5 to 4.2 equivalents, still more preferably 0.7 to 4.2 equivalents, and particularly preferably 0.7 to 2.0 equivalents, relative to 1 equivalent of the component (a). When the component (B) is less than 0.2 equivalent, the water absorption property is deteriorated due to an increase in maleimide groups, and the hardened product becomes brittle, so that the copper foil peel strength is lowered. On the other hand, when the component (B) is more than 4.2 equivalents, the crosslinking density is lowered and the heat resistance is deteriorated.
In the curable resin composition of the present invention, any known resin material may be used in addition to the component (a) and the component (B). Specifically, there may be mentioned: phenol resins, epoxy resins, amine resins, resins containing active olefins, isocyanate resins, polyamide resins, polyimide resins, cyanate resins, acryl resins, methallyl resins, active ester resins, and the like may be used singly or in combination. In addition, maleimide compounds other than component (A) may be used in combination.
As the phenol resin, the epoxy resin, the amine resin, the resin containing an active olefin, the isocyanate resin, the polyamide resin, the polyimide resin, the cyanate resin, and the active ester resin, the resins exemplified below can be used, respectively, but are not limited thereto.
Phenol resin: polycondensates of phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, hydroquinone, resorcinol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) with various aldehydes (formaldehyde, acetaldehyde, alkyl aldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthalene aldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde (cinnamaldehyde), furfural, etc.); polymers of phenols with various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc.); polycondensates of phenols with ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.); phenol resins obtained by polycondensation of phenols with substituted biphenyls (4, 4 '-bis (chloromethyl) -1,1' -biphenyl, 4 '-bis (methoxymethyl) -1,1' -biphenyl, etc.), or substituted phenyls (1, 4-bis (chloromethyl) benzene, 1, 4-bis (methoxymethyl) benzene, 1, 4-bis (hydroxymethyl) benzene, etc.), etc.; polycondensates of bisphenols with various aldehydes; polyphenylene ether.
Epoxy resin: the phenol resin; glycidyl ether-based epoxy resins obtained by glycidylating alcohols and the like; alicyclic epoxy resins represented by 4-vinyl-1-cyclohexene diepoxide or 3, 4-epoxycyclohexylmethyl-3, 4' -epoxycyclohexane carboxylate; glycidyl amine-based epoxy resins represented by tetraglycidyl diaminodiphenylmethane (tetraglycidyl diamino diphenylmethane, TGDDM) or triglycidyl-p-aminophenol; glycidyl ester-based epoxy resins.
Amine resin: diaminodiphenyl methane; diamino diphenyl sulfone; isophorone diamine; naphthalene diamine; aniline novolac; o-ethylaniline novolac; an aniline resin obtained by reacting aniline with dichloroxylene (xylylene chloride); amine resins obtained by reacting aniline described in japanese patent No. 6429862 with substituted biphenyls (4, 4 '-bis (chloromethyl) -1,1' -biphenyl, 4 '-bis (methoxymethyl) -1,1' -biphenyl, etc.), or substituted phenyls (1, 4-bis (chloromethyl) benzene, 1, 4-bis (methoxymethyl) benzene, 1, 4-bis (hydroxymethyl) benzene, etc.).
Resins containing active olefins: polycondensates of the above phenol resins with halogen compounds containing active olefins (chloromethylstyrene, allyl chloride, methallyl chloride, acryloyl chloride, etc.); polycondensates of phenols containing an active olefin (e.g., 2-allylphenol, 2-propenylphenol, 4-allylphenol, 4-propenylphenol, eugenol (eugenol), isoeugenol (isoeugenol), etc.) with a halogen compound (e.g., 4' -bis (methoxymethyl) -1,1' -biphenyl, 1, 4-bis (chloromethyl) benzene, 4' -difluorobenzophenone, 4' -dichlorobenzophenone, 4' -dibromobenzophenone, cyanuric chloride (cyanuric chloride); polycondensates of epoxy resins or alcohols with substituted or unsubstituted acrylic esters (acrylic esters, methacrylic esters, etc.); maleimide resins (4, 4' -diphenylmethane bismaleimide, polyphenylmethane maleimide, m-phenylene bismaleimide, 2' -bis [ 4- (4-maleimidophenoxy) phenyl ] propane, 3' -dimethyl-5, 5' -diethyl-4, 4' -diphenylmethane bismaleimide, 4-methyl-1, 3-phenylene bismaleimide, 4' -diphenyl ether bismaleimide, 4' -diphenyl sulfone bismaleimide, 1, 3-bis (3-maleimidophenoxy) benzene, 1, 3-bis (4-maleimidophenoxy) benzene).
Isocyanate resin: aromatic diisocyanates such as p-phenylene diisocyanate, m-phenylene diisocyanate, p-xylene diisocyanate, m-xylene diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, 4' -diphenylmethane diisocyanate, and naphthalene diisocyanate; aliphatic or alicyclic diisocyanates such as isophorone diisocyanate, hexamethylene diisocyanate, 4' -dicyclohexylmethane diisocyanate, hydrogenated xylene diisocyanate, norbornene diisocyanate, and lysine diisocyanate; polyisocyanates such as one or more biurets of an isocyanate monomer or an isocyanate obtained by trimerizing the above-mentioned diisocyanate compound; a polyisocyanate obtained by a urethanization reaction of the isocyanate compound with a polyol compound.
Polyamide resin: with aliphatic diamines such as amino acids (6-aminocaproic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, and p-aminomethylbenzoic acid), lactams (ε -caprolactam, ω -undecanoic lactam, ω -laurolactam), alicyclic diamines such as diamine (ethylenediamine, trimethylene diamine, tetramethylenediamine, pentamethylene diamine, hexamethylene diamine, heptamethylene diamine, octamethylene diamine, nonamethylene diamine, decamethylene diamine, undecanediamine, dodecandiamine, tridecanediamine, tetradecanediamine, pentadecamethylene diamine, hexadecanediamine, heptadecanediamine, octadecanediamine, nonadecanediamine, eicosanediamine, 2-methyl-1, 5-diaminopentane, 2-methyl-1, 8-diaminooctane), alicyclic diamines such as cyclohexanediamine, bis- (4-aminocyclohexyl) methane, and aromatic diamines such as xylenediamine, with dicarboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, undecanediamine, dodecanediamine, 5-diaminopentane, 2-methyl-1, 8-diaminooctane, and 5-terephthalic acid, and 5-isophthalic acid, and terephthalic acid such as aliphatic terephthalic acid, and isophthalic acid, terephthalic acid and isophthalic acid, aromatic dicarboxylic acids such as hexahydroisophthalic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; dialkyl esters of these dicarboxylic acids and dichloride), and one or more of these dicarboxylic acids as a main raw material.
Polyimide resin: the diamine is mixed with tetracarboxylic dianhydride (4, 4'- (hexafluoroisopropylidene) diphthalic anhydride, 5- (2, 5-dioxotetrahydro-3-furyl) -3-methyl-cyclohexene-1, 2-dicarboxylic anhydride, pyromellitic dianhydride, 1,2,3, 4-benzene tetracarboxylic dianhydride, 3',4,4 '-benzophenone tetracarboxylic dianhydride, 2',3 '-benzophenone tetracarboxylic dianhydride, 3',4,4 '-biphenyltetracarboxylic dianhydride, 3',4 '-diphenylsulfone tetracarboxylic dianhydride, 2',3,3 '-biphenyltetracarboxylic dianhydride, methylene-4, 4' -diphthalic dianhydride, 1-ethylene-4, 4 '-diphthalic dianhydride, 2' -propylene-4, 4 '-diphthalic dianhydride, 1, 2-ethylene-4, 4' -diphthalic dianhydride, 1, 3-trimethylene-4, 4 '-diphthalic dianhydride, 1, 4-tetramethylene-4, 4' -diphthalic dianhydride, 1, 5-pentamethylene-4, 4 '-diphthalic dianhydride, 4' -oxydiphthalic dianhydride, thio-4, 4 '-diphthalic dianhydride, sulfonyl-4, 4' -diphthalic dianhydride, 1, 3-bis (3, 4-dicarboxyphenyl) phthalic dianhydride, 1, 3-bis (3, 4-dicarboxyphenoxy) phthalic dianhydride, 1, 4-bis (3, 4-dicarboxyphenoxy) phthalic dianhydride, 1, 3-bis [2- (3, 4-dicarboxyphenyl) -2-propyl ] benzene dianhydride, 1, 4-bis [2- (3, 4-dicarboxyphenyl) -2-propyl ] benzene dianhydride, bis [3- (3, 4-dicarboxyphenoxy) phenyl ] methane dianhydride, bis [4- (3, 4-dicarboxyphenoxy) phenyl ] methane dianhydride, 2-bis [3- (3, 4-dicarboxyphenoxy) phenyl ] propane dianhydride, 2-bis [4- (3, 4-dicarboxyphenoxy) phenyl ] propane dianhydride, bis (3, 4-dicarboxyphenoxy) dimethylsilane dianhydride 1, 3-bis (3, 4-dicarboxyphenyl) -1, 3-tetramethyldisiloxane dianhydride, 2,3,6, 7-naphthalene tetracarboxylic dianhydride, 1,4,5, 8-naphthalene tetracarboxylic dianhydride, 1,2,5, 6-naphthalene tetracarboxylic dianhydride, 3,4,9, 10-perylene tetracarboxylic dianhydride, 2,3,6, 7-anthracene tetracarboxylic dianhydride, 1,2,7, 8-phenanthrene tetracarboxylic dianhydride, ethylene tetracarboxylic dianhydride, 1,2,3, 4-butane tetracarboxylic dianhydride, 1,2,3, 4-cyclobutane tetracarboxylic dianhydride, cyclopentane tetracarboxylic dianhydride, cyclohexane-1, 2,3, 4-tetracarboxylic dianhydride, cyclohexane-1, 2,4, 5-tetracarboxylic dianhydride, 3 '; 4,4' -dicyclohexyltetracarboxylic dianhydride, carbonyl-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, methylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, 1, 2-ethylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, 1, 1-ethylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, 2-propylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, oxy-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, thio-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, sulfonyl-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, bicyclo [2, 2] oct-7-ene-2, 3,5, 6-tetracarboxylic acid dianhydride, rel- [1S,5R,6R ] -3-oxabicyclo [3,2,1] octane-2, 4-dione-6-spiro-3 ' - (tetrahydrofuran-2 ',5' -dione), 4- (2, 5-dioxotetrahydrofuran-3-yl) -1,2,3, 4-tetrahydronaphthalene-1, 2-dicarboxylic anhydride, ethylene glycol-3- (4, 4-diphenyl) dicarboxylic acid anhydride, 4' -bis (diphenyl) dicarboxylic acid) dianhydride, and bis (diphenyl ether).
Cyanate resin: specific examples of the cyanate ester compound obtained by reacting a phenol resin with a cyanogen halide include: dicyanoxybenzene (dicyanoxybenzene), tricyanatobenzene, dicyanoxynaphthalene, dicyanoxybiphenyl, 2 '-bis (4-cyanoxyphenyl) propane, bis (4-cyanoxyphenyl) methane, bis (3, 5-dimethyl-4-cyanoxyphenyl) methane, 2' -bis (3, 5-dimethyl-4-cyanoxyphenyl) propane, 2 '-bis (4-cyanoxyphenyl) ethane, 2' -bis (4-cyanoxyphenyl) hexafluoropropane, bis (4-cyanoxyphenyl) sulfone, bis (4-cyanoxyphenyl) sulfide, phenol novolac cyanate, a cyanate group conversion of the hydroxyl group of the phenol-dicyclopentadiene cocondensate, and the like, but are not limited thereto.
Further, JP-A2005-264154 describes that a cyanate ester compound obtained by a synthesis method is particularly preferable as a cyanate ester compound because of low hygroscopicity, flame retardancy and excellent dielectric properties.
The cyanate ester resin may contain a catalyst such as zinc naphthenate, cobalt naphthenate, copper naphthenate, lead naphthenate, zinc octoate, tin octoate, lead acetylacetonate, and dibutyltin maleate, in order to trimerize the cyanate ester group to form a sym-triazine (sym-triazine) ring, if necessary. The catalyst is usually used in an amount of 0.0001 to 0.10 parts by mass, preferably 0.00015 to 0.0015 parts by mass, based on 100 parts by mass of the total mass of the curable resin composition.
Active ester resin: if necessary, a compound having one or more active ester groups in one molecule may be used as a hardener for curable resins such as epoxy resins. The active ester-based hardener is preferably a compound having two or more ester groups having high reactivity in one molecule, such as phenol esters, thiophenol esters, N-hydroxylamine esters, and esters of heterocyclic hydroxyl compounds. The active ester-based hardener is preferably obtained by condensation reaction of at least one compound selected from a carboxylic acid compound and a thiocarboxylic acid compound with at least one compound selected from a hydroxyl compound and a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester-based hardener obtained from a carboxylic acid compound and a hydroxyl compound is preferable, and an active ester-based hardener obtained from a carboxylic acid compound and at least one compound selected from a phenol compound and a naphthol compound is preferable.
Examples of the carboxylic acid compound include: benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and the like.
Examples of the phenol compound or the naphthol compound include: hydroquinone, resorcinol, bisphenol a, bisphenol F, bisphenol S, acid phenolphthalein, methylated bisphenol a, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α -naphthol, β -naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, dicyclopentadiene type diphenol compounds, phenol novolac, and the like. The "dicyclopentadiene type diphenol compound" herein means a diphenol compound obtained by condensing phenol having two molecules in one molecule of dicyclopentadiene.
Preferable specific examples of the active ester-based hardener include an active ester compound containing a dicyclopentadiene type diphenol structure, an active ester compound containing a naphthalene structure, an active ester compound containing an acetyl compound of phenol novolac, and an active ester compound containing a benzoyl compound of phenol novolac. Among them, an active ester compound containing a naphthalene structure and an active ester compound containing a dicyclopentadiene type diphenol structure are more preferable. The "dicyclopentadiene type diphenol structure" means a divalent structural unit containing phenylene-dicyclopentylene-phenylene.
Examples of commercial products of the active ester-based hardening agent include: "EXB9451", "EXB9460S", "HPC-8000-65T", "HPC-8000H-65TM", "EXB-8000L-65TM", "EXB-8150-65T" (manufactured by Dielsen (DIC)) as an active ester compound comprising a dicyclopentadiene type diphenol structure; "EXB9416-70BK" (manufactured by Dielsen (DIC)) as an active ester compound containing a naphthalene structure; "DC808" as an active ester compound comprising an acetyl compound of a phenol novolac (manufactured by Mitsubishi chemical corporation); "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi chemical corporation) as active ester compounds comprising benzoyl of phenol novolac; "DC808" as an active ester-based hardener which is an acetyl compound of phenol novolac (Mitsubishi chemical corporation); "EXB-9050L-62M" manufactured by Dielsen (DIC) Co., ltd.
The curable resin composition of the present invention may further be used in combination with a curing accelerator (curing catalyst) to improve the curability. Specific examples of the curing accelerator that can be used include radical polymerization initiators for the purpose of promoting the self-polymerization of a radically polymerizable curable resin such as an olefin resin or a maleimide resin or the radical polymerization of other components. Examples of the radical polymerization initiator include: ketone peroxides such as methyl ethyl ketone peroxide and acetylacetone peroxide; diacyl peroxides such as benzoyl peroxide; dialkyl peroxides such as dicumyl peroxide and 1, 3-bis (t-butylperoxyisopropyl) benzene; peroxy ketals such as t-butyl peroxybenzoate and 1, 1-di-t-butylperoxycyclohexane; alkyl peroxyacid esters such as α -cumyl peroxyneodecanoate, t-butyl peroxytrimethylacetate, 1, 3-tetramethylbutyl peroxy-2-ethylhexanoate, t-amyl peroxy-2-ethylhexanoate, t-butyl peroxy-2-ethylhexanoate, t-amyl peroxy-3, 5-trimethylhexanoate, t-butyl peroxy-3, 5-trimethylhexanoate, t-amyl peroxybenzoate; peroxycarbonates such as di-2-ethylhexyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butylperoxyisopropyl carbonate, and 1, 6-bis (t-butylperoxycarbonyloxy) hexane; known curing accelerators for azo compounds such as t-butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxyoctanoate, organic peroxides such as lauroyl peroxide, azobisisobutyronitrile, 4 '-azobis (4-cyanovaleric acid) and 2,2' -azobis (2, 4-dimethylvaleronitrile), but are not particularly limited thereto. Ketone peroxides, diacyl peroxides, hydroperoxides, dialkyl peroxides, peroxyketals, alkyl peroxyacid esters, peroxycarbonates (peroxycarbonates), and the like are preferable, and dialkyl peroxides are more preferable. The amount of the radical polymerization initiator to be added is preferably 0.01 to 5 parts by mass, particularly preferably 0.01 to 3 parts by mass, based on 100 parts by mass of the curable resin composition. If the amount of the radical polymerization initiator used is large, the dielectric characteristics of the cured product are deteriorated.
The curable resin composition of the present invention may optionally contain a curing accelerator other than a radical polymerization initiator. Specific examples of the hardening accelerator that can be used include: tertiary amines such as 2- (dimethylaminomethyl) phenol or 1, 8-diaza-bicyclo (5, 4, 0) undecene-7; phosphines such as triphenylphosphine; quaternary ammonium salts such as tetrabutylammonium salt, triisopropylmethyl ammonium salt, trimethyldecyl ammonium salt, cetyltrimethylammonium salt, and cetyltrimethylammonium hydroxide; quaternary phosphonium salts such as triphenylbenzyl phosphonium salt, triphenylethyl phosphonium salt and tetrabutylphosphonium salt (the counter ion of the quaternary phosphonium salt is halogen, organic acid ion, hydroxide ion, etc., and is not particularly limited, and particularly preferably a transition metal compound (transition metal salt) such as zinc compound such as organic acid ion, hydroxide ion, etc.), tin octoate, zinc carboxylate (zinc 2-ethylhexanoate, zinc stearate, zinc behenate, zinc myristate, etc.), zinc phosphate (zinc octylphosphate, zinc stearyl phosphate, etc.), etc., and the like. The amount of the hardening accelerator to be blended may be 0.01 to 5.0 parts by weight based on 100 parts by weight of the curable resin composition, if necessary.
Further, the curable resin composition of the present invention may contain a phosphorus-containing compound as a flame retardancy-imparting material. The phosphorus-containing compound may be a reactive phosphorus-containing compound or an additive phosphorus-containing compound. Specific examples of the phosphorus-containing compound include: phosphates such as trimethyl phosphate, triethyl phosphate, trimethyl phenyl phosphate, tri (xylyl) phosphate, tolyl diphenyl phosphate, tolyl-2, 6-di (xylyl) phosphate, 1, 3-phenylenedi (di (xylyl) phosphate), 1, 4-phenylenedi (di (xylyl) phosphate), and 4,4' -biphenyl (di (xylyl) phosphate; phosphanes (phosphanes) such as 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and 10- (2, 5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide; the phosphorus-containing epoxy compound, red phosphorus, etc. obtained by reacting the epoxy resin with active hydrogen of the phosphane is preferably a phosphate, a phosphane or a phosphorus-containing epoxy compound, and particularly preferably 1, 3-phenylenedi (di (xylyl) phosphate), 1, 4-phenylenedi (di (xylyl) phosphate), 4' -biphenyl (di (xylyl) phosphate) or a phosphorus-containing epoxy compound. The content of the phosphorus-containing compound is preferably in the range of 0.1 to 0.6 (weight ratio) per resin component in the curable resin composition. If the flame retardance is 0.1 or less, the hygroscopicity of the cured product may be adversely affected, and if the flame retardance is 0.6 or more.
Further, a light stabilizer may be added to the curable resin composition of the present invention as needed. The light stabilizer is preferably a hindered amine light stabilizer, and particularly preferably a hindered amine light stabilizer (Hindered Amine Light Stabilizer, HALS) or the like. The HALS is not particularly limited, and typical HALS include: dibutylamine-1, 3, 5-triazine-N, polycondensates of N' -bis (2, 6-tetramethyl-4-piperidinyl) -1, 6-hexamethylenediamine and N- (2, 6-tetramethyl-4-piperidinyl) butylamine, polycondensates of dimethyl-1- (2-hydroxyethyl) -4-hydroxy-2, 6-tetramethylpiperidine succinate poly- [ 6- (1, 3-tetramethylbutyl) amino-1, 3, 5-triazin-2, 4-diyl } { (2, 6-tetramethyl-4-piperidinyl) imino } hexamethylene{ (2, 6-tetramethyl-4-piperidinyl) imino } ], poly { (2, 6-tetramethyl } { (1, 3-tetramethylbutyl) amino-1, 3, 5-triazine-2, 4-diyl) -4-piperidinyl) imino } hexamethylene{ (2, 6-tetramethyl-4-piperidinyl) imino } ]. The HALS may be used alone or in combination of two or more.
Further, in the curable resin composition of the present invention, a binder resin may be formulated as needed. Examples of the binder resin include, but are not limited to, butyral resins, acetal resins, acrylic resins, epoxy-nylon resins, nitrile butadiene rubber (nitrile butadiene rubber, NBR) -phenol resins, epoxy-NBR resins, polyamide resins, polyimide resins, silicone resins, and the like. The amount of the binder resin to be blended is preferably in a range not impairing the flame retardancy and heat resistance of the cured product, and is preferably 0.05 to 50 parts by mass, more preferably 0.05 to 20 parts by mass, per 100 parts by mass of the resin component.
Further, if necessary, powder such as fused silica, crystalline silica, porous silica, alumina, zircon, calcium silicate, calcium carbonate, quartz powder, silicon carbide, silicon nitride, boron nitride, zirconia, aluminum nitride, graphite, forsterite (forsterite), steatite (spinel), mullite (mullite), titanium dioxide, talc (tac), clay, iron oxide, asbestos (ascestos), glass powder, or an inorganic filler in a spherical or crushed form may be added to the curable resin composition of the present invention. In particular, in the case of obtaining a curable resin composition for semiconductor packaging, the amount of the inorganic filler used in the curable resin composition is usually in the range of 80 to 92 mass%, preferably 83 to 90 mass%.
Further, in the curable resin composition of the present invention, a known additive may be formulated as needed. Specific examples of the additive that can be used include polybutadiene and its modified products, modified products of acrylonitrile copolymers, polyphenylene ether, polystyrene, polyethylene, polyimide, fluororesin, silicone gel, silicone oil, a filler such as a silane coupling agent, a release agent, carbon black, phthalocyanine blue, phthalocyanine green, and other colorants. The blending amount of these additives is preferably 1,000 parts by mass or less, more preferably 700 parts by mass or less, per 100 parts by mass of the resin component.
The curable resin composition of the present invention can be obtained by uniformly mixing the above-mentioned components in a predetermined ratio, and is usually pre-cured at 130 to 180℃for 30 to 500 seconds, and further post-cured at 150 to 200℃for 2 to 15 hours, whereby a sufficient curing reaction is performed to obtain the cured product of the present invention. In addition, the components of the curable resin composition may be uniformly dispersed or dissolved in a solvent or the like, and the solvent may be removed and cured.
The curable resin composition of the present invention obtained in the above manner has moisture resistance, heat resistance, high adhesion, low dielectric constant, and low dielectric loss tangent. Therefore, the curable resin composition of the present invention can be used in a wide range of fields where moisture resistance, heat resistance, high adhesion, low dielectric constant, and low dielectric loss tangent are required. Specifically, the material is useful as a material for all electric/electronic parts such as an insulating material, a laminate (printed wiring board, ball Grid Array (BGA) substrate, build-up substrate, etc.), a sealing material, and a resist. In addition, the present invention can be used in fields such as coating materials, adhesives, and 3D printing, in addition to molding materials and composite materials. Particularly in semiconductor encapsulation, solder reflow resistance is beneficial.
The semiconductor device has a semiconductor device sealed with the curable resin composition of the present invention. Examples of the semiconductor device include: dual in-line package (DIP), quad flat package (quad flat package, QFP), ball Grid Array (BGA), chip scale package (chip size package, CSP), small outline package (small outline package, SOP), thin small outline package (thin small outline package, TSOP), thin quad flat package (thin quad flat package, TQFP), and the like.
The method for producing the curable resin composition of the present invention is not particularly limited, and the curable resin composition may be produced by dispersing or dissolving the components in a solvent or the like as described above, uniformly mixing the components, and optionally distilling off the solvent, or may be prepared as a prepolymer. For example, the prepolymer is formed by heating the component (a) and the component (B) in the presence or absence of a catalyst and in the presence or absence of a solvent. Similarly, in addition to the component (a) and the component (B), a curing agent such as an epoxy resin, an amine compound, a maleimide compound, a cyanate ester compound, a phenol resin, and an acid anhydride compound, and other additives may be added to carry out the prepolymer. For mixing or prepolymer formation of each component, for example, an extruder, kneader, roll or the like is used in the absence of a solvent, and a reaction vessel or the like with a stirring device is used in the presence of a solvent.
As a method of uniformly mixing without using a solvent or the like, a uniform curable resin composition is prepared by mixing at a temperature in the range of 50 to 100 ℃ with a kneading machine, a roll, a planetary mixer or the like. The obtained curable resin composition may be molded into a cylindrical ingot shape by a molding machine such as a tablet machine (tablet machine), or into a granular powder or a powdery molded body, or the composition may be melted on a surface support and molded into a sheet shape having a thickness of 0.05 to 10mm, to obtain a molded article of the curable resin composition. The obtained molded article is a molded article which is tack-free at 0 to 20 ℃, and has little deterioration in fluidity and hardenability even when stored at-25 to 0 ℃ for 1 week or more.
The molded article obtained can be molded into a cured product by a transfer molding machine or a compression molding machine.
The curable resin composition of the present invention may be prepared by adding an organic solvent to a varnish-like composition (hereinafter, also simply referred to as varnish). The curable resin composition of the present invention can be prepared by dissolving the curable resin composition of the present invention in a solvent such as toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethylformamide, dimethylacetamide, or N-methylpyrrolidone to prepare a varnish, impregnating the varnish with a base material such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, or paper, heating and drying the resultant prepreg, and hot-press-molding the resultant prepreg. The solvent used in this case is usually used in an amount of 10 to 70% by weight, preferably 15 to 70% by weight, based on the mixture of the curable resin composition of the present invention and the solvent. If the amount of the solvent is less than the above range, the varnish viscosity becomes high, and workability becomes poor, and if the amount of the solvent is large, voids are generated in the cured product. In addition, in the case of a liquid composition, a cured resin containing carbon fibers may be obtained directly by, for example, resin transfer molding (resin transfer molding, RTM).
The curable composition of the present invention can also be used as a modifier for film compositions. Specifically, the method can be used for improving the flexibility of the B-stage. The film-type resin composition is obtained by preparing the curable resin composition of the present invention into the curable resin composition varnish, applying the curable resin composition varnish onto a release film, removing the solvent under heating, and then performing B-staging. The sheet-like adhesive can be used as an interlayer insulating layer of a multilayer substrate or the like.
The curable resin composition of the present invention can be heat-melted and reduced in viscosity to impregnate reinforcing fibers such as glass fibers, carbon fibers, polyester fibers, polyamide fibers, and alumina fibers, thereby obtaining a prepreg. Specific examples thereof include glass fibers such as E glass cloth, D glass cloth, S glass cloth, Q glass cloth, spherical glass cloth, NE glass cloth, and T glass cloth, and further include fibers of inorganic substances other than glass, poly (paraphenylene terephthalamide) (polyparaphenylene terephthalamide) (kevlar) (registered trademark), manufactured by Dupont (Dupont), wholly aromatic polyamide, and polyester; and organic fibers such as polyparaphenylene benzoxazole (polyparaphenylene benzoxazole), polyimide, and carbon fibers, but are not particularly limited thereto. The shape of the base material is not particularly limited, and examples thereof include woven fabric, nonwoven fabric, roving (winding), and chopped strand mat (chopped strand mat). As a weaving method of the woven fabric, a plain weave, a basket weave (basket weave), a twill weave (twill weave), or the like is known, and may be used as appropriate according to the intended use or performance from among these known weaving methods. In addition, a woven fabric having a fabric subjected to a fiber opening treatment or a glass woven fabric having a surface treated with a silane coupling agent or the like is preferably used. The thickness of the base material is not particularly limited, but is preferably about 0.01mm to 0.4 mm. The prepreg may be obtained by impregnating the reinforcing fiber with the varnish and drying the impregnated reinforcing fiber by heating.
The laminated board of the present embodiment includes one or more prepregs. The laminate is not particularly limited as long as it is a laminate including one or more prepregs, and may have any other layers. As a method for producing the laminated board, a generally known method can be suitably applied, and is not particularly limited. For example, in the case of molding a laminate sheet on which a metal foil is attached, a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, or the like may be used, and the laminate sheet may be obtained by laminating the prepregs to each other and performing heat and pressure molding. In this case, the heating temperature is not particularly limited, but is preferably 65℃to 300℃and more preferably 120℃to 270 ℃. The pressure of the pressurization is not particularly limited, but if the pressurization is too large, the solid content of the resin of the laminate is difficult to adjust, and the quality is unstable, and if the pressure is too small, the adhesiveness between the bubbles and the laminate is deteriorated, so that it is preferably 2.0MPa to 5.0MPa, more preferably 2.5MPa to 4.0MPa. The laminated sheet of the present embodiment can be preferably used as a laminated sheet with a metal foil, which will be described later, by including a layer with a metal foil.
The prepreg is cut into a desired shape, and if necessary, laminated with copper foil or the like, and then the curable resin composition is cured by heating while applying pressure to the laminate by press molding, autoclave molding, sheet winding molding, or the like, whereby a laminate for electric and electronic use (printed wiring board) or a carbon fiber reinforcement can be obtained.
The cured product of the present invention can be used for various applications such as molding materials, adhesives, composite materials, and paints. The cured product of the curable resin composition of the present invention exhibits excellent heat resistance and dielectric characteristics, and is therefore preferably used in a sealing material for semiconductor elements, a sealing material for liquid crystal display elements, a sealing material for organic Electroluminescence (EL) elements, an electrical/electronic component such as a printed wiring board or a laminate, or a composite material for lightweight high-strength structural materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics.
Examples
Hereinafter, the present invention will be specifically described with reference to examples and comparative examples. Herein, "parts" and "%" respectively represent "parts by weight" and "% by weight". The softening point and the melt viscosity were measured by the following methods.
Softening point: by a method according to Japanese Industrial Standard (Japanese Industrial Standards, JIS) K-7234
Melt viscosity: measured by ICI melt viscosity (150 ℃ C.) cone-plate method, the unit is Pa.s.
Gel Permeation Chromatography (GPC) analysis
The manufacturer: volter world (Waters)
And (3) pipe column: sodekes (SHODEX) GPC KF-601 (two), KF-602, KF-602.5, KF-603
Flow rate: 0.5ml/min.
Column temperature: 40 DEG C
Solvent was used: tetrahydrofuran (THF)
A detector: RI (differential refraction detector)
High Performance Liquid Chromatography (HPLC) analysis
And (3) pipe column: xionsil ODS-2
Flow rate: 1.0ml/min.
Column temperature: 40 DEG C
Solvent was used: acetonitrile/water
A detector: LED array (225 nm)
Differential scanning calorimetry (differential scanning calorimetry, DSC) analysis
The manufacturer: TA instruments (TA instruments)
The device comprises: DSC2500
Heating rate: 10 ℃/min
Measuring temperature range: 30-350 DEG C
Dynamic mechanical analysis (dynamic mechanical analysis, DMA)
The manufacturer: TA instruments (TA instruments)
The device comprises: DMAQ800
Measurement mode: stretching
Heating rate: 2 ℃/min.
Measuring temperature range: 25-350 DEG C
Measuring frequency: 10Hz
The temperature at which the value of tan delta was maximum was set as Tg.
Td5 analysis
The manufacturer: fine instruments (Seiko Instruments) Co., ltd
The device comprises: thermogravimetric-differential thermal analysis (TG/DTA) 6200
Measuring temperature range: 30-580 DEG C
Heating rate: 10 ℃/min
Thermo-mechanical analysis (thermomechanical analysis, TMA)
The manufacturer: TA instruments (TA instruments)
The device comprises: TMAQ400
Measurement mode: stretching
Heating rate: 2 ℃/min.
Measuring temperature range: 25-330 DEG C
Mechanical strength
The manufacturer: shijin production station
The device comprises: ottogulaft (Autograph) AGS-X
Stretching speed: 0.5mm/min
The specimen was held so that the length of the specimen became 5cm, and the tensile measurement was performed at the test speed in the 180 ° direction.
Peel strength test
The manufacturer: shijin production station
The device comprises: ottogulaft (Autograph) AGS-X
Peel test tensile speed: 50mm/min
A test piece was produced by sandwiching the curable resin composition between the roughened surface of an electrolytic copper foil (CF-T4X-SV-18; manufactured by Fufield Metal foil powder Co., ltd.) having a thickness of 18 μm and the roughened surface of an electrolytic copper foil (CF-T9B-HTE; manufactured by Fufield Metal foil powder Co., ltd.) having a thickness of 35 μm, and curing the composition at 220℃for 2 hours under a pressure of 1 MPa. After the obtained test piece was cut to a width of 2cm, an electrolytic copper foil having a thickness of 18 μm was cut and removed so as to leave a residual width of 1 cm. The electrolytic copper foil having a width of 1cm and a thickness of 18 μm was stretched in the direction of 90℃at the test speed, and the peel strength was measured.
Water absorption test
Immersed in water for 24 hours, taken out, left at 25℃for 24 hours under 30% conditions, and then measured for weight.
Dielectric constant test, dielectric loss tangent test
The manufacturer: AET shares Limited
The device comprises: 10GHz cavity resonator
The test piece having a width of 2.5mm and a length of 5cm was dried at 120℃for 2 hours by a dryer, and then measured. Further, the test piece was immersed in water for 24 hours, taken out, left at 25℃for 24 hours in a 30% environment, and then measured again.
Synthesis example 1
Synthesis of aromatic amine resin (A-1)
A flask equipped with a thermometer, a cooling tube, a Dean-Stark (Dean-Stark) azeotropic distillation trap and a stirrer was charged with 192 parts of aniline and 112 parts of toluene and 100 parts of 1, 3-bis (2-hydroxy-2-propyl) benzene, and 21.5 parts of 35% hydrochloric acid was added dropwise over a period of 10 minutes. The temperature in the system was raised to 160℃and the reaction was carried out at that temperature for 17 hours while removing water and toluene by distillation. After cooling to 80 ℃, 124 parts of toluene was added, and 30 parts of 30% aqueous sodium hydroxide solution was added dropwise over 10 minutes. Thereafter, the mixture was stirred at the above temperature for 2 hours and allowed to stand for 30 minutes. The separated lower aqueous layer was removed, and the reaction mixture was repeatedly washed with water until the washing liquid became neutral. Then, 158 parts of the aromatic amine resin (A-1) represented by the formula (2) was obtained by distilling off excess aniline and toluene from the oil layer under reduced pressure and heating by a rotary evaporator. The amine equivalent of the aromatic amine resin (A-1) was 186.1g/eq and the softening point was 58.8 ℃. According to GPC analysis (RI), the n=1 bodies were 62.5 area%. GPC chart is shown in FIG. 1.
Synthesis example 2
Synthesis of Maleimide resin (M-1)
A flask equipped with a thermometer, a cooling tube, a dean-Stark azeotropic distillation trap and a stirrer was charged with 73.5 parts of maleic anhydride, 126 parts of toluene, 1.86 parts of methanesulfonic acid and 12.6 parts of N-methyl-2-pyrrolidone, and the mixture was heated to reflux. Then, a resin solution obtained by dissolving 93 parts of the aromatic amine resin (A-1) in 55.8 parts of toluene was added dropwise over 4 hours while maintaining the reflux state. During this time, the condensed water and toluene which are azeotroped under reflux conditions were cooled/separated in a dean-stark azeotropic distillation trap, and then toluene was returned to the system as an organic layer, and the water was discharged outside the system. After the completion of the addition of the resin solution, the reaction was carried out for 10 hours while maintaining the reflux state and carrying out the dehydration operation.
After the completion of the reaction, water was repeatedly washed 4 times to remove methanesulfonic acid and excess maleic anhydride, and water was removed from the system by azeotropic distillation of toluene and water under a reduced pressure of 70 ℃. Then, 2 parts of methanesulfonic acid was added thereto, and the reaction was carried out under reflux for 4 hours. After the completion of the reaction, the reaction was repeatedly washed with water 3 times until the water washing became neutral, after which water was removed from the system by azeotropic distillation of toluene and water under a heating pressure reduction at 70 ℃ or lower, the solvent was distilled off under a heating pressure reduction until the toluene became a resin concentration of about 70% to 80%, and toluene was added to adjust the resin concentration to 60%. Thus, a maleimide solution (V-1) containing the maleimide (M-1) of the present invention was obtained. According to GPC analysis (RI), the obtained maleimide resin (M-1) had 57.4 area% of n=1 bodies, 21.3 area% of n=2 bodies, and 21.3 area% or more of n=3 bodies. According to HPLC analysis (225 nm), the orientation ratio (ortho-ortho/para-para/ortho-para) in n=1 bodies was 32.0%/25.4%/42.6%. The softening point was 115.5℃and the viscosity was 6.0 Pa.s. GPC chart is shown in FIG. 2.
Examples 1 to 5 and comparative examples 1 to 6
The maleimide compound and the polyphenylene ether compound having an unsaturated double bond were weighed in the proportions shown in Table 1, toluene was added so that the resin solid content became 50%, and then heated and mixed at 70℃for 1 hour, thereby producing a varnish. The solubility and compatibility of the resin at this time were visually confirmed, and the evaluation was performed under the conditions described below. The results are shown in Table 1.
Dicumyl peroxide (DCP (dicumyl peroxide), manufactured by Nouryon) as a hardening accelerator was further dissolved in the varnish. The varnish in which the hardening accelerator was dissolved was heated at 80℃for 30 minutes and at 120℃for 1 hour by a vacuum dryer, whereby a curable resin composition was prepared. The obtained curable resin composition was sandwiched between copper foils, and cured at 220℃for 2 hours under a pressure of 1MPa applied under vacuum. The hardenability was confirmed at this time, and the evaluation was performed under the conditions described below. The results of various measurements on the cured products obtained are shown in Table 1.
Solubility determination conditions: no precipitate in … solution
The X … solution had precipitate
Compatibility determination conditions: is compatible with …
X … incompatibility (phase separation)
220 ℃ hardenability determination conditions: can obtain a hardened product from (…)
X … the cured product was not obtained (the cured product was brittle and could not be taken out)
M-1 (obtained by distilling off the solvent obtained in Synthesis example 2 under reduced pressure and heating)
MIR-3000 (MIR-3000-70 MT (manufactured by Nippon chemical Co., ltd.) by distillation under reduced pressure and heating)
BMI-70 (manufactured by KI chemical Co., ltd.)
BMI-2300 (manufactured by Dahe Chemicals Co., ltd.)
SA-9000-111 (manufactured by Saint Foundation industries Co., ltd. (Saudi Basic Industries Corporation, sabic)) Mw:3653, mn:2648
OPE-2st1200 (Mitsubishi gas chemical Co., ltd.) Mn:1200
TABLE 1
In examples 1 to 5, it was confirmed that the solvent solubility and compatibility were good, and the hardening reaction was well performed at 220℃for 2 hours, and the heat resistance, copper foil peel strength, moisture resistance, and dielectric characteristics were excellent. In comparative example 1, since maleimide compound (M-1) was used in a large amount, it was confirmed that the water absorption and dielectric characteristics were high (poor). When the maleimide compound (M-1) was used alone as in comparative example 2, it was confirmed that the heat resistance and the dielectric loss tangent were good, but the dielectric loss tangent after water absorption was also deteriorated because the copper foil had low peel strength and further had high water absorption. When the polyphenylene ether compound having an unsaturated double bond was used alone as in comparative example 3, it was not cured under curing conditions of 220℃for 2 hours. When other maleimide resins are used as in comparative examples 4 to 6, the solvent solubility and compatibility are poor, and the dielectric characteristics and dielectric characteristics after water absorption are high (poor) as a result.
Claims (7)
1. A curable resin composition comprising a maleimide compound (A) represented by the following formula (1) and a polyphenylene ether compound (B) having an unsaturated double bond, wherein the weight ratio of the component (A) to the component (B) is 50/50 to 5/95,
[ chemical 1]
(in the formula (1), R represents a hydrogen atom or a methyl group; m represents an integer of 0 to 3; n is a repetition number, and the average value of n is 1 < n < 5).
2. A curable resin composition comprising a maleimide compound (A) represented by the following formula (1) and a polyphenylene ether compound (B) having an unsaturated double bond, wherein the amount of the component (B) is 0.20 to 4.2 equivalents relative to 1 equivalent of the component (A),
[ chemical 2]
(in the formula (1), R represents a hydrogen atom or a methyl group; m represents an integer of 0 to 3; n is a repetition number, and the average value of n is 1 < n < 5).
3. The curable resin composition according to claim 1 or 2, wherein the component (B) is a polyphenylene ether compound having a (meth) acrylic group.
4. The curable resin composition according to any one of claims 1 to 3, wherein the component (B) is a compound represented by the following formula (2) or a compound represented by the following formula (4),
[ chemical 3]
(in the formula (2), n is a repetition number, and the average value is 1 < n < 10)
[ chemical 4]
In the formula (4), n is a repetition number, and the average value is 1 < n < 10).
5. The curable resin composition according to any one of claims 1 to 4, further comprising a hardening accelerator.
6. A prepreg comprising a sheet-like fibrous base material and the curable resin composition according to any one of claims 1 to 5.
7. A cured product obtained by curing the curable resin composition according to any one of claims 1 to 5 or the prepreg according to claim 6.
Applications Claiming Priority (3)
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KR (1) | KR20230150253A (en) |
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JPS5030297B1 (en) | 1969-09-30 | 1975-09-30 | ||
JPS5430440A (en) | 1977-08-10 | 1979-03-06 | Japan Storage Battery Co Ltd | Inverter |
JPH03100016A (en) | 1989-09-14 | 1991-04-25 | Mitsui Toatsu Chem Inc | Preparation of polymaleimide compound |
JP2855138B2 (en) | 1990-07-17 | 1999-02-10 | 財団法人東北電気保安協会 | How to replace the operation cord of a pole switch etc. |
JP2570923B2 (en) | 1991-06-07 | 1997-01-16 | 信越化学工業株式会社 | Thermosetting resin composition |
JPH0637465A (en) | 1992-07-17 | 1994-02-10 | Mitsubishi Electric Corp | Fitting device for cover |
US7329708B2 (en) * | 2004-08-18 | 2008-02-12 | General Electric Company | Functionalized poly(arylene ether) composition and method |
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TW201938658A (en) * | 2018-03-06 | 2019-10-01 | 日商日立化成股份有限公司 | Prepreg, layered plate, multilayer printed wiring board, semiconductor package, and resin composition, and method of manufacturing prepreg, layered plate, and multilayer printed wiring board |
JP7081950B2 (en) * | 2018-03-27 | 2022-06-07 | 旭化成株式会社 | Resin composition, prepreg, metal-clad laminate, and printed wiring board |
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