TWI391784B - Hardened resin composition and hardened product thereof - Google Patents
Hardened resin composition and hardened product thereof Download PDFInfo
- Publication number
- TWI391784B TWI391784B TW095146460A TW95146460A TWI391784B TW I391784 B TWI391784 B TW I391784B TW 095146460 A TW095146460 A TW 095146460A TW 95146460 A TW95146460 A TW 95146460A TW I391784 B TWI391784 B TW I391784B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin composition
- carboxyl group
- compound
- curable resin
- copolymer resin
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
- 229920006026 co-polymeric resin Polymers 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002245 particle Substances 0.000 claims description 21
- 239000003822 epoxy resin Substances 0.000 claims description 20
- 229920000647 polyepoxide Polymers 0.000 claims description 20
- 239000000919 ceramic Substances 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 9
- 229920001187 thermosetting polymer Polymers 0.000 claims description 9
- 150000008065 acid anhydrides Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000011161 development Methods 0.000 claims description 6
- 239000003505 polymerization initiator Substances 0.000 claims description 6
- 125000000466 oxiranyl group Chemical group 0.000 claims description 5
- 239000007870 radical polymerization initiator Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000013007 heat curing Methods 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- -1 3,4-epoxycyclohexylmethyl Chemical group 0.000 description 20
- 238000000576 coating method Methods 0.000 description 19
- 239000000758 substrate Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 230000017525 heat dissipation Effects 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 238000011049 filling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 229910000420 cerium oxide Inorganic materials 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 150000007519 polyprotic acids Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- 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 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001579 optical reflectometry Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 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 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- DYRUVFJAAMUHRF-UHFFFAOYSA-N (2,3-diphenylphenyl)-phenylmethanone Chemical class C=1C=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 DYRUVFJAAMUHRF-UHFFFAOYSA-N 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- HYYJOCXNESGFSB-UHFFFAOYSA-N 1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CNCC1CO1 HYYJOCXNESGFSB-UHFFFAOYSA-N 0.000 description 1
- QZOPRMWFYVGPAI-UHFFFAOYSA-N 1-chloroindole Chemical compound C1=CC=C2N(Cl)C=CC2=C1 QZOPRMWFYVGPAI-UHFFFAOYSA-N 0.000 description 1
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 description 1
- YRTNMMLRBJMGJJ-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;hexanedioic acid Chemical compound OCC(C)(C)CO.OC(=O)CCCCC(O)=O YRTNMMLRBJMGJJ-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
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Landscapes
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- Macromonomer-Based Addition Polymer (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
Description
本發明係有關具有良好的散熱性之硬化性樹脂組成物,及其硬化物,更詳細者係有關一種適用於梱裝基板、表面實裝型發光二極體之樹脂絕緣層等之具有散熱性、保存穩定性良好之硬化性樹脂組成物。
近年來,伴隨電子機器小型化、高性能化,被要求半導體高密度化、高機能化。因應此高密度化,於蕊殼基板上形成樹脂絕緣層,於無電解鍍銅等形成銅箔層,多層化之組裝基板,使形成電路之半導體元件於基板上進行表面實裝之BGA(球.格柵.陣列)、CSP(元件.比例尺.梱裝)等之梱裝基板出現。
用於此組裝基板、梱裝基板之樹脂組成物(如:專利文獻1及專利文獻2)係以低分子量之環氧化合物做為基劑之樹脂組成物,不易進行於低纖維膨脹係數化有用之熔融二氧化矽,提昇散熱性之氧化鋁等無機填充材料之高填充。
又,先行技術之液狀光焊料光阻組成物(如:專利文獻3)中,其無機填充材料之含有率為50質量%以下,如:硫酸鋇、二氧化矽、滑石、黏土等無機填充材料,特別以硫酸鋇使用頻率極高。此系中,塗膜之吸水率為1.2~1.5 wt%,經由吸水之爆米花現象,經由塗膜中之水份導致電蝕性之問題。更於高溫時由樹脂被分解釋出多鹼酸酐、光聚合引發劑氣化後引起電子機器作動不良之問題產生。
[專利文獻1]特開平9-148748號公報(特許請求之範圍)
[專利文獻2]特開平11-288091號公報(特許請求之範圍)
[專利文獻3]特開昭61-243869號公報(特許請求之範圍)
本發明鑑於上述問題點進而開發,其目的係為提供一種適用於梱裝基板、表面實裝型發光二極體之樹脂絕緣層等之具有散熱性、保存穩定性良好之硬化性樹脂組成物。
更提供一種使上述硬化性樹脂組成物經活性能量線照射及/或熱硬化後取得散熱性良好之硬化物。
本發明者針對上述目的之實現而進行精密研討後結果發現,由含有(A)含有羧基之共聚樹脂、(B)具有2個經由活性能量線進行硬化之反應基之化合物、(C)共聚合引發劑、及(D)發射遠紅外線之陶瓷粒子所成,且該發射遠紅外線之陶瓷粒子(D)之含有率於固形成份中為60容量%以上者為其特徵之硬化性樹脂組成物,具有良好的散熱性,且可輕易呈高導熱率化等,可藉由稀鹼水溶液進行顯像,進而完成本發明。
更理想之形態者,其上述含有羧基之共聚樹脂(A)係含有以下述一般式(I)或(II)所示之化合物為構成成份之羧基之共聚樹脂(A-1)。
又,由光硬化性面視之,該具有2個以上經由活性能量線進行硬化之反應基之化合物(B)為具有2個以上乙烯性不飽和鍵之化合物(B-1),且該該光聚合引發劑(C)為光自由基聚合引發劑(C-1)者宜。
另外,做為本發明硬化性樹脂組成物之第2形態者,係提供一種於上述組成物中更含有熱硬化性成份(E)之光硬化性、熱硬化性組成物。此理想形態中該熱硬化性份(E)為1分子中具有2個以上之環氧乙烷環之多官能環氧樹脂(E-1)。
用於本發明硬化性樹脂組成物之含羧基共聚樹脂(A)係為共聚樹脂,因此,可提供一種即使以有機溶劑等進行稀釋,仍可維持適度之黏性,藉由此,可使發射遠紅外線之陶瓷粒子進行高填充,具良好的散熱性,且可輕易呈高導熱率化等,可經由稀鹼水溶液顯像之樹脂組成物。
此具有良好的散熱性,且可輕易呈高導熱率化等之硬化性樹脂組成物可適用於易產生翹曲問題之薄板組裝基板,搭載發熱量多之半導體元件之梱裝基板之焊料光阻。又,使用可視光反射性高之無機填充材料,具遮光性之有機填充材料後,可於焊料光阻附與光反射性、光擴散性或遮光性,適用於要求加入絕緣性之光學機能之LED裝置等光學裝置。
本發明硬化性樹脂組成物之基本形態其特徵係由含有(A)含有羧基之共聚樹脂、(B)具有2個以上經由活性能量線進行硬化之反應基之化合物、(C)光聚合引發劑、及(D)發射遠紅外線之陶瓷粒子所成,且該發射遠紅外線之陶瓷粒子(D)之含有率於固形份中為60容量%以上。為進一步提昇耐熱性,亦可含有(E)熱硬化性成份。
以下針對本發明硬化性樹脂組成物之各構成成份進行詳細之說明。
首先,含有羧基之共聚樹脂(A)可使用分子中具有羧基之公知慣用之共聚樹脂。更由光硬化性、耐顯像性面視之,可使用分子中兼具有乙烯性不飽和鍵之感光性含羧基之共聚樹脂為更佳。
具體而言,如下述列舉之含羧基之共聚樹脂例。
(1)藉由共聚(甲基)丙烯酸等不飽和羧酸與具有其以外之不飽和雙鍵化合物之1種以上所得之含有羧基之共聚樹脂、(2)於(甲基)丙烯酸等不飽和羧酸與具有其以外之不飽和鍵化合物之1種以上之相互共聚物中,藉由縮水甘油基(甲基)丙烯酸酯、3,4-環氧基環己基甲基(甲基)丙烯酸酯等之環氧基與具有不飽和雙鍵之化合物、(甲基)丙烯酸氯化物等,以乙烯性不飽和基做為側基加成後取得感光性之含羧基共聚樹脂、(3)於縮水甘油基(甲基)丙烯酸酯、3,4-環氧基環己基甲基(甲基)丙烯酸酯等環氧基與具不飽和雙鍵之化合物以及具其以外之不飽和雙鍵之化合物之共聚物中,使(甲基)丙烯酸等不飽和羧酸進行反應,於所生成之二級羥基中使多鹼基酸酐經反應後取得感光性之含羧基共聚樹脂、(4)於具有馬來酸酐等不飽和雙鍵之酸酐與有其以外不飽和雙鍵化合物之共聚物中,使2-羥基乙基(甲基)丙烯酸酯等羥基與具有不飽和雙鍵化合物進行反應後取得感光性之含羧基共聚樹脂、(5)於聚乙烯酸衍生物等之含羥基之共聚聚合物中,使多鹼基酸酐進行反應後取得含羧基之樹脂、(6)更於含上述羧基之樹脂中使縮水甘油基(甲基)丙烯酸酯、3,4-環氧基環己基甲基(甲基)丙烯酸酯等環氧基與具有不飽和雙鍵化合物進行反應後取得感光性之含羧基共聚樹脂等例。
做為此等含羧基共聚樹脂(A)之構成成份者,如含有下述一般式(I)或(II)所示之化合物。
另外,本明細書中,(甲基)丙烯酸酯係指丙烯酸酯、甲基丙烯酸酯、及此等混合物之總稱用語,對於其他類似之表示亦相同。
該含有羧基共聚樹脂(A)之固形成份酸價為40~200 mgKOH/g之範圍,更佳者為80~120 mgKOH/g之範圍。當含有羧基之共聚樹脂酸價未達40 mgKOH/g時,則不易進行鹼顯像,反之,超出200 mgKOH/g則將促使經由顯像液之曝光部之溶解,因此,導致線細至必要以上,不同情況下出現未區分曝光部與未曝光部於顯像液之溶解剝離,導致正常光阻圖型之描繪困難,而不理想。
又,含此羧基之共聚樹脂(A)之重量平均分子量以2,000~50,000者宜,更佳者為5,000~20,000。當重量平均分子量未達2,000時,將降低塗膜之指觸乾燥性,不易取得硬化物之耐撞擊性而不理想。反之,重量平均分子量超出50,000時,則降低顯像性而不理想。
做為該具有2個以上經由活性能量線進行硬化之反應基化合物(B)者如:具有2個以上乙烯性不飽和鍵之化合物、環氧乙烷環、氧雜環丁烷環等陽離子聚合性之環狀醚化合物、芳基丙烯醯芳烴、桂皮酸酯等經光二量化之化合物等例。此等中,由光硬化性、保存穩定性面視之,又以具有2個以上乙烯性不飽和鍵之化合物(B-1)為較佳者。
該具有2個以上乙烯性不飽和鍵之化合物(B-1)係進行光硬化後,為使該含羧基之共聚樹脂(A)對於烯鹼水溶液時為不溶化而使用。其代表例如:2-羥基乙基(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、聚乙烯二醇二(甲基)丙烯酸酯、新戊二醇己二酸酯二(甲基)丙烯酸酯、羥基三甲基乙酸新戊二醇二(甲基)丙烯酸酯、二環戊烯二(甲基)丙烯酸酯、己內酯改性二環戊烯基二(甲基)丙烯酸酯、EO改性磷酸二(甲基)丙烯酸酯、烯丙基化環己基二(甲基)丙烯酸酯、三聚異氰酸酯二(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、二季戊四醇三(甲基)丙烯酸酯、丙酸改性二季戊四醇三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、PO改性三羥甲基丙烷三(甲基)丙烯酸酯、三(丙烯醯氧基乙基)三聚異氰酸酯、丙烯改性二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、己內酯改性二季戊四醇六(甲基)丙烯酸酯等例。
此等中,特別由耐顯像性面視之,又以二官能以上,更佳者為三官能以上之(甲基)丙烯酸酯為最佳。
做為此等具2個以上乙烯性不飽和鍵之化合物(B-1)之配合量者,對於100質量份之該含有羧基之共聚樹脂(A)而言,以5~100質量份者宜,特別以10~50質量份為最佳。當(B-1)成份未達5質量份時,則無法取得充足的硬化性,未能取得如所設計之形狀。反之,超出100質量份則指觸乾燥性變差而不理想。
做為用於本發明之該光聚合引發劑(C)者,係藉由照射活性能量線產生活性基之化合物,如:光自由基聚合引發劑、光陽離子聚合引發劑、光陰離子聚合引發劑等例。此等中由其光硬化性、保存穩定性、硬化物之電氣特性等面視之,又以光自由基聚合引發劑(C-1)為較佳。
做為該自由基聚合引發劑(C-1)者,可使用公知者如:苯偶因、苯偶因甲基醚、苯偶因乙基醚、苯偶因丙基醚等之苯偶因與苯偶因烷基醚類;苯乙酮、2,2-二甲氧基-2-苯基苯乙酮、2,2-二乙氧基-2-苯基苯乙酮、2,2-二乙氧基-2-苯基苯乙酮、1,1-二氯苯乙酮等之苯乙酮類;2-甲基-1-[4-(甲基硫代)苯基]-2-嗎啉丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉苯基)-丁酮-1等之胺基苯乙酮類;2-甲基蒽醌、2-乙基蒽醌、2-第三-丁基蒽醌、1-氯蒽醌等蒽醌類;2,4-二甲基噻噸酮、2,4-二乙基噻噸酮、2-氯噻噸酮、2,4-二異丙基噻噸酮等噻噸酮類;苯乙酮二甲基縮酮、苄基二甲基縮酮等縮酮類;二苯甲酮等之二苯甲酮類;或咕噸酮類;(2,6-二甲氧基苯甲醯基)-2,4,4-戊基膦氧化物、雙(2,4,6-三甲基苯甲醯基)-苯基膦氧化物、2,4,6-三甲基苯甲醯基二苯基膦氧化物、乙基-2,4,6-三甲基苯甲醯基苯基磷酸酯等之三膦氧化物類等例,此等公知慣用之光自由基聚合引發劑(C-1)可單獨或組合2種以上均可。
此等光自由基聚合引發劑(C-1)之配合量對於100質量份之該含有羧基之共聚樹脂(A)而言,以含有0.1~30質量份,較佳者為2~20質量份之比例者宜。當光自由基聚合引發劑(C-1)之配合量對於100質量份之該含羧基之共聚樹脂(A)而言,未達0.1質量份時,將降低光硬化性,作業性而不理想。反之,超出30質量份則將降低塗膜特性,亦不理想。
可用於本發明硬化性樹脂組成物所使用發射遠紅外線之陶瓷粒子(D)之材料有公知慣用之遠紅外線陶瓷,如:氧化鋁(Al2
O3
)、二氧化矽(SiO2
)、氧化鋯(ZrO2
)、氧化鈦(TiO2
)、氧化鎂(MgO)、模來石(3Al2
O3
.2SiO2
)、鋯石特別是(ZrO2
.SiO2
)、謹青石(2MgO.2Al2
O3
.5SiO2
)、氮化矽(Si3
N4
)、碳化矽(SiC)、氧化錳(MnO2
)、氧化鐵(Fe2
O3
)、氧化鈷(CoO)等。其中又以氧化鋁其化學性亦穩定、絕緣性良好,特別是使用球狀之氧化鋁更可緩和高填充時之黏度上昇。此氧化鋁之粒子平均粒徑為0.01μm~30μm,更佳者為0.01μm~20μm。當小於0.01μm則組成物之黏度太高,分散不易亦不易塗佈於被塗佈物。反之,超出30μm則產生突出塗膜,沈澱速度變快,保存穩定性變差。另外,藉由配合具有最密填充粒度分佈之2種以上平均粒徑後,可進一步進行高填充,由保存穩定性、導熱率之兩側面為宜。
該陶瓷粒子(D)之折射率更接近樹脂組成物之折射率,為1.4~2.0,更佳者為1.5~1.8之折射率者不會阻礙光透過性,因此為理想者。具體例如:二氧化矽、氧化鋁之例。
此發射遠紅外線之陶瓷粒子(D)之配合量係於固形物(硬化物)中為60容量%以上。該發射遠紅外線之陶瓷
粒子(D)之配合量若未達60容量%時,將因不易藉由高填充本發明目的之發射遠紅外線之陶瓷粒子後取得良好散熱性,且難以高導熱率化等,而不理想。
本發明硬化性樹脂組成物為提昇硬化物之耐熱性,亦可配合(E)熱硬化性成份。做為該熱硬化性成份者如:分子中具有2個以上環氧乙烷環之多官能環氧樹脂、分子中具有2個以上氧雜環丁烷環之多官能氧雜環丁烷環之化合物、熱硬化性聚醯亞胺樹脂、蜜胺樹脂等例。
此等中由其硬化性、保存穩定性,硬化塗膜特性面視之,又以多官能環氧樹脂(E-1)為較佳使用者。
做為該多官能環氧樹脂(E-1)可使用公知慣用之環氧化合物,如:雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚S型環氧樹脂、溴化雙酚A型環氧樹脂、氫化雙酚A型環氧樹脂、聯苯酚型環氧樹脂、聯二甲苯酚型環氧樹脂、苯酚漆用酚醛型環氧樹脂、甲酚漆用酚醛型環氧樹脂、溴化苯酚漆用酚醛型環氧樹脂、雙酚A之漆用酚醛型環氧樹脂等之縮水甘油醚化合物;對苯二甲酸二縮水甘油酯、六氫酞酸二縮水甘油酯、二聚物酸二縮水甘油酯等之縮水甘油酯化合物;三縮水甘油基三聚異氰酸酯、N,N,N’,N’-四縮水甘油基間二甲苯二胺、N,N,N’,N’-四縮水甘油基雙胺基甲基環己烷、N,N-二縮水甘油基苯胺等之縮水甘油胺化合物;聚丁二烯等之具不飽和鍵樹脂經氧化取得之環氧化聚丁二烯等例。更可使用縮水甘油基(甲基)丙烯酸酯之共聚樹脂等。
此等多官能環氧樹脂(E-1)可單獨或組合2種以上使用之。對於1當量該含羧基共聚樹脂(A)之羧基而言,其配合量以0.6~2.0當量,較佳者為0.8~1.5當量之範圍。當多官能環氧樹脂之配合量少於上述範圍時,則殘留羧基,降低耐熱性、耐鹼性、電氣絕緣性等,而不理想。反之,超出上述範圍時,則經由殘留低分子量之多官能環氧樹脂後,降低塗膜之強度等而不理想。
本發明硬化性樹脂組成物為使高填充化更易進行,以添加(F)濕潤.分散劑者宜。做為此濕潤.分散劑(F)者,可使用具有與羧基、羥基、酸酯等遠紅外線陶瓷粒子(D)具親和性之極性基化合物、高分子化合物,如:磷酸酯類等含酸之化合物、含酸基之共聚物、含羥基之聚羧酸酯、聚矽氧烷、長鏈聚胺基醯胺與酸酯之鹽等。於市售之濕潤.分散劑(F)特別適用者如:Disperbyk(註冊商標)-101、-103、-110、-111、-160、-171、-174、-190、-300、Bykumen(註冊商標)、BYK-P150、-P104、-P104S、-240(均為big.chemi公司製)、EFKA-聚合物150、EFKA-44、-63、-64、-65、-66、-71、-764、-766、N(均為efka)公司製)之例。
此濕潤.分散劑(F)之配合量為每100質量份該遠紅外線陶瓷粒子(D)以0.01~5質量份為適當者。當濕潤.分散劑(F)之配合量低於上述範圍則將無法取得濕潤.分散劑添加之效果,不易組成物高填充化之進行。反之,超出上述範圍則增加無光硬化成份之比例,而降低塗膜強度,導致組成物搖變性增大之主因,而不理想。
本發明硬化性樹脂組成物於必要時亦可添加為調整黏度之有機溶劑。該有機溶劑可使用如:丁酮、環己酮等酮類;甲苯、二甲苯、四甲基苯等之芳香族烴類;溶纖劑、甲基溶纖劑、丁基溶纖劑、卡必醇、甲基卡必醇、丁基卡必醇、丙二醇單甲基醚、二丙二醇單甲基醚、二丙二醇二乙基醚、三丙二醇單甲基醚等之二醇醚類;乙酸乙酯、乙酸丁酯、乳酸丁酯、溶纖劑乙酸酯、丁基溶纖劑乙酸酯、卡必醇乙酸酯、丁基卡必醇乙酸酯、丙二醇單甲基醚乙酸酯、二丙二醇單甲基醚乙酸酯、碳酸丙烯酯等酯類;辛烷、癸烷等之脂肪族烴類;石油醚、石蠟油、溶劑油等石油系溶劑等有機溶劑。此等有機溶劑可單獨或組合2種以上使用之。
此等有機溶劑之配合量並未特別限定,依其塗佈方法進行適當調整即可,一般於組成物中配合50質量%以下者宜,較佳者為30質量%以下。有機溶劑之含量太多時,將提昇遠紅外線陶瓷粒子(D)之沈澱速度,降低保存穩定性,而不理想。
本發明硬化性樹脂組成物更於必要時可配合酞菁、藍、酞菁、綠、碘.綠、二重氮黃、結晶紫、氧化鈦、碳黑、萘黑等之公知慣用著色劑、氫輥、氫輥單甲基醚、第3-丁基與茶酚、焦棓酚、吩噻嗪等公知慣用之熱聚合禁止劑、微粉二氧化矽、有機膨潤土、蒙脫石等公知慣用之增黏劑、聚矽氧系、高分子系等消泡劑及/或矯正劑、咪唑系、噻唑系、三唑系等矽烷偶合劑等公知慣用添加劑類。
本發明硬化性樹脂組成物於該有機溶劑以塗佈方法調整適當黏度後,於基材上藉由浸漬塗層法、流動塗層法、輥筒塗層法、棒塗層法、網版塗層法、簾塗層法等方法進行塗佈,於約60~100℃之溫度下揮發含於組成物之有機溶劑乾燥(暫時乾燥)後,可形成無黏著之塗膜。又,將該組成物塗佈於塑膠薄膜後,乾燥後薄膜卷取者貼合於基材後,可形成樹脂絕緣層。之後,藉由接觸式(或非接觸方式),通過形成圖型之光罩後經由活性光線選擇性曝光,使未曝光部藉由稀鹼水溶液(如0.3~3%碳酸鈉鹼水溶液)顯像後形成光阻圖型。更加熱至約140~180℃之溫度後,藉由熱硬化,使該含有羧基之共聚樹脂(A)之羧基與分子中具有2個以上之環氧乙烷環之多官能環氧樹脂(E-1)環氧基進行反應後,可形成耐熱性等各特性良好之硬化塗膜。
其中,做為為使塗膜光硬化之照射光源者如:低壓水銀燈、中壓水銀燈、高壓水銀燈、超高壓水銀燈、氙燈或金屬鹵素燈為適當者。此外,雷射光線等亦可利用於曝光用活性光源,直接進行描繪。
另外,做為上述顯像所使用之稀鹼水溶液者,可使用氫氧化鉀、氫氧化鈉、碳酸鈉、碳酸鉀、矽酸鈉、氨、胺類等鹼水溶液,特別以碳酸鈉為較佳。
又,重覆進行2次上之塗佈.揮發乾燥後,層合塗膜後亦可形成立體的絕緣構造。更於顯像後之塗膜上加入Tg以上之熱能,藉由熱流動使圖型側壁呈斜錐形進行熱變形亦無妨。此曝光及顯像亦可適度進行塗佈.揮發乾燥,亦可一併進行。
以下顯示本發明之實施例及比較例,針對本發明進行具體說明,惟本發明並未受限於以下實施例。又,以下「份」及「%」在未特別限定下,均代表「質量份」及「質量%」。
<合成例1>(含有羧基之共聚樹脂A之合成)於具備攪拌機、溫度計、迴流冷卻管、滴入漏斗及氮導入管之21容可分離燒瓶中置入900g之二乙二醇二甲基醚、及21.4g之第三-丁基過氧化2-乙基己酸酯[日本油脂(股份)製過丁基O],昇溫至90℃後,使309.9g之甲基丙烯酸、116.4g甲基丙烯酸甲酯、及109.8g之一般式(I)所示之內酯改性2-羥基乙基甲基丙烯酸酯[dicell化學工業(股份)製praccell FM1]以3個小時的時間與21.4g之雙(4-第三-丁基環己基)過氧化二碳酸酯[日本油脂(股份)製peroil TCP]同時滴入二乙二醇二甲基醚中,更進行熟化6小時後,取得含有羧酸之共聚樹脂溶液。反應係於氮氛圍下進行。
接著於上述含有羧基之共聚樹脂溶液中加入363.9g之3,4-環氧基環己基甲基丙烯酸酯[Dicell化學(股份)製Cyclomer A200]、3.6g之二甲基苄胺、1.80g之氫輥單甲基醚後,昇溫至100℃,攪拌後進行環氧基之開環加成反應。16小時後,取得含有53.8 wt%(不揮發份)之固形成份酸價=108.9 mgKOH/g、重量平均分子量=25,000(苯乙烯換算)之含有羧基之共聚樹脂溶液。以下此反應溶液稱A-1清漆。
<比較合成例1>(含有羧基樹脂之合成)於備有溫度計、攪拌器、滴入漏斗、及迴流冷卻器之燒瓶中,置入210g之甲酚漆用酚醛型環氧樹脂(epicron N-680、大日本油墨化學工業公司製、環氧當量=210)與96.4g之卡必醇乙酸酯進行加熱溶解。再加入0.1g聚合禁止劑之氫輥、與2.0g之反應觸媒之三苯基膦。將此混合物加熱至95~105℃後,緩緩滴入72g之丙烯酸,至酸價呈3.0 mgKOH/g以下為止,反應約進行16小時。此反應生成物冷卻至80~90℃後,加入76.1g之四氫酞酸酐,藉由紅外吸光分析後,約反應6小時至未出現酸酐之吸收波峰(1780 cm-1
)為止。此反應液中加入96.4g之出光石油化學公司製之芳香族系溶劑IPZOL #150,稀釋後取出。如此取得含有羧基之感光性聚合物溶液為不揮發份=65 wt%、固形物之酸價78 mgKOH/g。以下此反應溶液稱為R-1清漆。
以3根輥筒研磨機進行混煉利用上述合成例取得之A-1清漆及R-1清漆示於表1之配合成份後,取得硬化性樹脂組成物。各硬化性組成物之特性評定結果示於表2。
另外,上述表2中性能試驗方法如以下。
(1)耐溶劑性使上述各實施例及比較例之組成物以網版印刷全面塗佈於於試驗基板上呈約為40 μm之乾燥塗膜,於80℃下進行乾燥20分鐘。冷卻至室溫後,於橡樹製作所製之曝光裝置(金屬鹵素燈7KW)減壓下,kodack製層錠No.2約呈6層之曝光量下進行全面曝光後,使30℃之1 wt% Na2
CO3
水溶液於噴霧壓0.2MPa之條件下,進行顯像60秒,於150℃下進行60分鐘熱硬化。將取得基板浸漬於丙二醇單甲基醚乙酸脂30分鐘後,乾燥之後,藉由透明膠帶進行剝離試驗,針對塗膜之剝離、變色進行評定。
○:未出現剝離、變色者×:出現剝離、變色者
(2)耐熱性於使用上述各實施例及比較例之組成物與耐溶劑性同法取得之基板上塗佈松脂系碎片於260℃之焊料槽流動10秒後,以丙二醇單甲基醚乙酸酯進行洗淨,乾燥後,藉由透明膠帶進行剝離試驗,針對塗膜之剝離進行評定。
○:未剝離者×:剝離者
(3)鉛筆硬度於使用上述各實施例及比較例之組成物與耐溶劑性同法取得之基板上將鉛筆由B削成9H之頂端呈平的筆心,以約45°角進行下壓記錄塗膜未剝離之鉛筆硬度。
(4)電氣絕緣性以使用上述各實施例及比較例之組成物與耐溶劑性同法利用IPC B-25試驗圖型之梳型電路B試樣,以上述條件製作基板,於此梳型電極外加DC 500V之偏壓,測定絕緣電阻值。
(5)散熱試驗於使用上述各實施例及比較例之組成物與耐溶劑性同法取得之基板的一角上壓入60W加熱做為熱源,進行加熱10分鐘,將此時之基板溫度以由加熱距離3mm處貼上K型熱電偶進行測定。
由表2所示結果證明,本發明硬化性組成物係提供一種可取得散熱性良好,且做為印刷配線板用之耐絕緣材料具十足特性之硬化物,可藉由稀鹼水溶液顯像之硬化性樹脂組成物。
Claims (5)
- 一種可鹼顯像之硬化性樹脂組成物,其特徵為由含有(A)含有羧基之共聚樹脂、(B)具有2個以上經由活性能量線進行硬化之反應基之化合物、(C)光聚合引發劑、及(D)發射遠紅外線之陶瓷粒子所成,且該發射遠紅外線之陶瓷粒子(D)之含有率於固形成份中為60容積%以上,其中該含有羧基之共聚樹脂(A)係含有以下述一般式(I)或(II)所示化合物為構成成份之含有羧基之共聚樹脂(A-1)
- 如申請專利範圍第1項之硬化性樹脂組成物,其中該發射遠紅外線之陶瓷粒子(D)為氧化鋁。
- 如申請專利範圍第1或2項之硬化性樹脂組成物,其中更含有(E)熱硬化性成份。
- 如申請專利範圍第3項之硬化性樹脂組成物,其中該熱硬化性成份(E)為1分子中具有2個以上之環氧乙烷環之多官能環氧樹脂(E-1)。
- 一種硬化物,其特徵係使該申請專利範圍第1項至第4項中任一項之硬化性樹脂組成物進行活性能量線照射及/或熱硬化後取得。
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