TWI541264B - Epoxy resin, epoxy resin composition, prepreg and the like - Google Patents
Epoxy resin, epoxy resin composition, prepreg and the like Download PDFInfo
- Publication number
- TWI541264B TWI541264B TW101126932A TW101126932A TWI541264B TW I541264 B TWI541264 B TW I541264B TW 101126932 A TW101126932 A TW 101126932A TW 101126932 A TW101126932 A TW 101126932A TW I541264 B TWI541264 B TW I541264B
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- TW
- Taiwan
- Prior art keywords
- group
- epoxy resin
- carbon atoms
- parts
- formula
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims description 178
- 229920000647 polyepoxide Polymers 0.000 title claims description 178
- 239000000203 mixture Substances 0.000 title claims description 71
- -1 phenol compound Chemical class 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 239000011256 inorganic filler Substances 0.000 claims description 21
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 19
- 239000004848 polyfunctional curative Substances 0.000 claims description 13
- 125000005907 alkyl ester group Chemical group 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 239000004065 semiconductor Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- 241000208818 Helianthus Species 0.000 claims description 5
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 150000004060 quinone imines Chemical group 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 63
- 229960003742 phenol Drugs 0.000 description 56
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000002904 solvent Substances 0.000 description 36
- 239000000047 product Substances 0.000 description 35
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000003756 stirring Methods 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 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 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 150000002989 phenols Chemical class 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000001816 cooling Methods 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 238000006735 epoxidation reaction Methods 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
- 238000010438 heat treatment Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 5
- 235000012141 vanillin Nutrition 0.000 description 5
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 5
- 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 4
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 4
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012778 molding material Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 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 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LTMXHUUHBSCKEK-UHFFFAOYSA-N Hexadecan-3-one Chemical compound CCCCCCCCCCCCCC(=O)CC LTMXHUUHBSCKEK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000005575 aldol reaction Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 3
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
- LNOLJFCCYQZFBQ-BUHFOSPRSA-N (ne)-n-[(4-nitrophenyl)-phenylmethylidene]hydroxylamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=N/O)/C1=CC=CC=C1 LNOLJFCCYQZFBQ-BUHFOSPRSA-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
- UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 description 2
- WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 2
- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 2
- YNPDFBFVMJNGKZ-UHFFFAOYSA-N 2'-Hydroxy-5'-methylacetophenone Chemical compound CC(=O)C1=CC(C)=CC=C1O YNPDFBFVMJNGKZ-UHFFFAOYSA-N 0.000 description 2
- FJPGAMCQJNLTJC-UHFFFAOYSA-N 2,3-Heptanedione Chemical compound CCCCC(=O)C(C)=O FJPGAMCQJNLTJC-UHFFFAOYSA-N 0.000 description 2
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 2
- WNCNWLVQSHZVKV-UHFFFAOYSA-N 2,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C=C1O WNCNWLVQSHZVKV-UHFFFAOYSA-N 0.000 description 2
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 description 2
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 2
- LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Chemical compound CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
- CJPNOLIZCWDHJK-UHFFFAOYSA-N 2-Pentadecanone Chemical compound CCCCCCCCCCCCCC(C)=O CJPNOLIZCWDHJK-UHFFFAOYSA-N 0.000 description 2
- POQLVOYRGNFGRM-UHFFFAOYSA-N 2-Tetradecanone Chemical compound CCCCCCCCCCCCC(C)=O POQLVOYRGNFGRM-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- UCQUAMAQHHEXGD-UHFFFAOYSA-N 3',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1 UCQUAMAQHHEXGD-UHFFFAOYSA-N 0.000 description 2
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 description 2
- RGZHEOWNTDJLAQ-UHFFFAOYSA-N 3,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(O)=C1O RGZHEOWNTDJLAQ-UHFFFAOYSA-N 0.000 description 2
- KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical compound CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
- GUARKOVVHJSMRW-UHFFFAOYSA-N 3-ethylpentane-2,4-dione Chemical compound CCC(C(C)=O)C(C)=O GUARKOVVHJSMRW-UHFFFAOYSA-N 0.000 description 2
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- PQCLJXVUAWLNSV-UHFFFAOYSA-N 5-Methyl-2,3-hexanedione Chemical compound CC(C)CC(=O)C(C)=O PQCLJXVUAWLNSV-UHFFFAOYSA-N 0.000 description 2
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
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- C—CHEMISTRY; METALLURGY
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
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Description
本發明係關於一種新型環氧樹脂及環氧樹脂組成物。又,係關於一種利用環氧樹脂組成物形成之預浸物等之硬化物。
環氧樹脂組成物通常成為機械性質、耐水性、耐化學性、耐熱性、電氣性質等優異之硬化物,被利用於接著劑、塗料、積層板、成形材料、注型材料等廣泛領域。近年,對於該等領域所使用之環氧樹脂之硬化物,要求高純度化,難燃性、耐熱性、耐濕性、強韌性、低線膨脹率、低介電常數特性等各特性之進一步提升。
尤其是作為環氧樹脂組成物之代表性用途之電氣、電子產業領域中,以多功能化、高性能化、小型化為目的之半導體之高密度封裝或印刷電路板之高密度佈線化不斷進步,但是伴隨著高密度封裝化或高密度佈線化,會使自半導體元件或印刷電路板之內部所產生之熱增加,成為引起誤動作的原因。因此,就能量效率或機器設計方面而言,如何將所產生之熱高效率地釋放至外部亦成為重要之課題。作為此等熱之對策,研究使用金屬核心基板,在設計之階段組裝易散熱之構造,或對使用之高分子材料(環氧樹脂)細密地充填高導熱填料等各種方法。但是,現狀係由於連接高導熱部位之作為黏合劑之高分子材料的導熱率低,因此高分子材料之導熱速度被限制,而無法有效地散熱。
作為實現環氧樹脂之高導熱化之方法,於專利文獻1報告有將液晶原基(mesogenic group)導入至結構中,於同一文獻作為具有液晶原基之環氧樹脂,記載有具有聯苯骨架之環氧樹脂等。又,作為除聯苯骨架以外之環氧樹脂,記載有苯甲酸苯酯型之環氧樹脂,但是該環氧樹脂必須利用由氧化所引起之環氧化反應來製造,因此安全性或成本存在問題,而不能說其具有實用性。於專利文獻2~4,舉例有使用具有聯苯骨架之環氧樹脂之例,其中於專利文獻3記載有併用具有高導熱率之無機填充材之方法。但是,藉由此等文獻所記載之方法所獲得之硬化物的導熱性並未達到滿足市場需求之水準,業界要求一種使用能夠比較廉價地獲得之環氧樹脂,且提供具有高導熱率之硬化物之環氧樹脂組成物。
又,至此所報告之具有液晶原基之高導熱性環氧樹脂多為熔點非常高且樹脂狀之取出困難,並且溶劑溶解性低劣者。此類環氧樹脂於硬化時由於在完全熔化前開始硬化,因此難以製作均一的硬化物,較為不佳。
專利文獻1:日本特開平11-323162號公報
專利文獻2:日本特開2004-2573號公報
專利文獻3:日本特開2006-63315號公報
專利文獻4:日本特開2003-137971號公報
本發明係為解決此種問題而進行研究所得者,提供一種其硬化物具有高導熱性之溶劑溶解性優異的環氧樹脂。
本發明人等為解決上述問題而潛心研究,結果完成本發明。
即,本發明係關於
(1)一種環氧樹脂,係藉由將下述式(1)~(5)所示之化合物之一種以上,和下述式(6)所示之化合物反應而得的酚化合物,與該酚化合物和環氧鹵丙烷(epihalohydrin)反應而得的環氧樹脂,在該環氧樹脂量為當量比成為過量之條件下反應所得;
(式(1)中,R1分別獨立地存在,表示氫原子、碳數為1~10之烷基、碳數為6~10之芳香基、羥基、硝基或者碳數為1~10之烷氧基中之任一者。l表示R1之數目,且為1~4之整數),
(式(2)中,R2分別獨立地存在,表示氫原子、碳數為1~20之烷基、碳數為6~10之芳香基、碳數為1~15之烷基羰基、碳數為2~10之烷基酯基、碳數為1~10之烷氧基、啉基羰基(morpholinylcarbonyl)、酞醯亞胺基、
向日葵基(piperonylic)或者羥基中之任一者),
(式(3)中,R3分別獨立地存在,表示氫原子、碳數為0~10之烷基羰基、碳數為1~10之烷基、碳數為6~10之芳香基、碳數為2~10之烷基酯基、碳數為1~10之烷氧基或者羥基中之任一者。n表示碳數,且表示0、1、2中之任一整數。m表示R3之數目,且滿足1≦m≦n+2之關係),
(式(4)中,R12分別獨立地存在,表示氫原子、碳數為1~20之烷基、碳數為6~10之芳香基、碳數為1~10之烷氧基或羥基中之任一者),
(式(5)中,R13分別獨立地存在,表示氫原子、碳數為1~20之烷基、碳數為6~10之芳香基、碳數為1~10之烷氧基、碳數為1~10之烷基酯基或者羥基中之任一者。
又,m為1~10之整數);
(式(6)中,R4分別獨立地存在,表示氫原子、碳數為1~10之烷基、碳數為6~10之芳香基、羥基、硝基、甲醯基、烯丙基或者碳數為1~10之烷氧基中之任一者。k表示R4之數目,且為1~4之整數);(2)一種環氧樹脂組成物,係含有前項(1)之環氧樹脂及硬化劑而成;(3)如前項(2)之環氧樹脂組成物,其含有導熱率20W/m.K以上之無機填充材而成;(4)如前項(3)之環氧樹脂組成物,係用於半導體封裝用途;(5)一種預浸物,係由前項(4)之環氧樹脂組成物及片狀之纖維基材構成;(6)一種硬化物,係由前項(4)之環氧樹脂組成物、或者前項(5)之預浸物硬化而成。
本發明之環氧樹脂由於其硬化物之導熱優異,因此用於以半導體封裝材料、預浸物為代表之各種複合材料、接著劑、塗料等之情形下有用。又,本發明之環氧樹脂由於相較於具有液晶原基之環氧樹脂具有低熔點,進而溶劑溶
解性亦優異,因此可獲得均一之硬化物。
本發明之環氧樹脂係由以莫耳比表示為過量之特定環氧樹脂(A)與下述特定之酚化合物(A)反應而得。
首先,對本發明之酚化合物(A)進行說明。酚化合物(A)係選自由下述式(1)~(5)所示之化合物中之一種以上與下述式(6)所示之化合物反應而得。
(式(1)中,R1分別獨立地存在,表示氫原子、碳數為1~10之烷基、碳數為6~10之芳香基、羥基、硝基或者碳數為1~10之烷氧基中之任一者。l表示R1之數目,且為1~4之整數。)
式(1)中之烷基、芳香基、烷氧基亦可具有取代基,作為取代基可舉出:甲基、乙基、丙基等。
式(1)中,R1分別獨立地存在,較佳為氫原子、碳數為1~10之未經取代之烷基、碳數為6~10之未經取代之芳香基、羥基、硝基或者碳數為1~10之未經取代之烷氧基。
作為式(1)所示之化合物的具體例,可舉出:2-羥基苯乙酮、3-羥基苯乙酮、4-羥基苯乙酮、2',4'-二羥基苯乙酮、2',5'-二羥基苯乙酮、3',4'-二羥基苯乙酮、3',5'
-二羥基苯乙酮、2',3',4'-三羥基苯乙酮、2',4',6'-三羥基苯乙酮-水合物、4'-羥基-3'-甲基苯乙酮、4'-羥基-2'-甲基苯乙酮、2'-羥基-5'-甲基苯乙酮、4'-羥基-3'-甲氧基苯乙酮、2'-羥基-4'-甲氧基苯乙酮、4'-羥基-3'-硝基苯乙酮、4'-羥基-3',5'-二甲氧基苯乙酮、4',6'-二甲氧基-2'-羥基苯乙酮、2'-羥基-3',4'-二甲氧基苯乙酮、2'-羥基-4',5'-二甲氧基苯乙酮、5-乙醯柳酸甲酯(5-acetylsalicylic acid methyl ester)、2’,3’-二羥基-4'-甲氧基苯乙酮水合物。此等之中,就所得之酚化合物進行環氧化時之高溶劑溶解性,且環氧樹脂組成物之硬化物表現出高導熱性而言,較佳為4'-羥基-3'-甲氧基苯乙酮、4'-羥基苯乙酮。
(式(2)中,R2分別獨立地存在,表示氫原子、碳數為1~20之烷基、碳數為6~10之芳香基、碳數為1~15之烷基羰基、碳數為2~10之烷基酯基、碳數為1~10之烷氧基、啉基羰基、酞醯亞胺基、向日葵基或者羥基中之任一者。)
式(2)中之芳香基、烷基羰基、烷基酯基、烷氧基亦可具有取代基,取代基較佳為選自由羰基、酯基、烯基、苯基、烷氧基、醚基、酞醯亞胺基及向日葵基構成之群中
之至少一種。
作為式(2)所示之化合物的具體例,可舉出:丙酮、1,3-二苯基-2-丙酮、2-丁酮、1-苯基-1,3-丁二酮、2-戊酮、3-戊酮、4-甲基-2-戊酮、乙醯丙酮、2-己酮、3-己酮、甲基異戊酮(isoamyl methyl ketone)、乙基異丁基酮、4-甲基-2-己酮、2,5-己二酮、1,6-二苯基-1,6-己二酮、2-庚酮、3-庚酮、4-庚酮、2-甲基-4-庚酮、5-甲基-3-庚酮、6-甲基-2-庚酮、2,6-二甲基-4-庚酮、2-辛酮、3-辛酮、4-辛酮、5-甲基-2-辛酮、2-壬酮、3-壬酮、4-壬酮、5-壬酮、2-癸酮、3-癸酮、4-癸酮、5-癸酮、2-十一酮、3-十一酮、4-十一酮、5-十一酮、6-十一酮、2-甲基-4-十一酮、2-十二酮、3-十二酮、4-十二酮、5-十二酮、6-十二酮、2-十四酮、3-十四酮、8-十五酮、10-十九酮、7-十三酮、2-十五酮、3-十六酮、9-十七酮、11-二十一酮、12-二十三酮、14-二十七酮、16-三十一酮、18-三十五酮、4-乙氧基-2-丁酮、4-(4-甲氧基苯基)-2-丁酮、4-甲氧基-4-甲基-2-戊酮、4-甲氧基苯基丙酮、甲氧基丙酮、苯氧基丙酮、乙醯乙酸甲酯、乙醯乙酸乙酯、乙醯乙酸丙酯、乙醯乙酸丁酯、乙醯乙酸異丁酯、乙醯乙酸第二丁基酯、乙醯乙酸第三丁基酯、乙醯乙酸3-戊基酯、乙醯乙酸戊酯、乙醯乙酸異戊酯、乙醯乙酸己酯、乙醯乙酸庚酯、乙醯乙酸正辛酯、乙醯乙酸苄酯、乙醯基丁二酸二甲酯、丙酮基丙二酸二甲酯、丙酮基丙二
酸二乙酯、乙醯乙酸-2-甲氧基乙酯、乙醯乙酸烯丙酯、4-第二丁氧基-2-丁酮、苄基丁基酮、雙去甲氧基薑黃素、1,1-二甲氧基-3-丁酮、1,3-二乙醯氧基丙酮、4-羥基苯基丙酮、4-(4-羥基苯基)-2-丁酮、異戊基甲基酮、4-羥基-2-丁酮、5-己烯-2-酮、丙酮基丙酮、3,4-二甲氧基苯基丙酮、向日葵基甲基酮、向日葵基丙酮、鄰苯二甲醯亞胺基丙酮、4-異丙氧基-2-丁酮、4-異丁氧基-2-丁酮、乙醯氧基-2-丙酮、N-乙醯乙醯基啉、1-乙醯基-4-哌啶酮等。此等之中,就所得酚化合物進行環氧化時之高溶劑溶解性,且環氧樹脂組成物之硬化物表現出高導熱性而言,較佳為丙酮。
(式(3)中,R3分別獨立地存在,表示氫原子、碳數為0~10之烷基羰基、碳數為1~10之烷基、碳數為6~10之芳香基、碳數為2~10之烷基酯基、碳數為1~10之烷氧基或者羥基中之任一者。n表示碳數,且表示0、1、2中之任一整數。m表示R3之數目,且滿足1≦m≦n+2之關係。)
再者,式(3)中,所謂R3係碳數為0之烷基羰基時,表示包含構成通式(3)之主骨架之環烷的碳原子而成之羰基結構,例如可舉出:1,3-環戊二酮等。
於式(3)中,上述取代基較佳為醚基或者羰基。
式(3)中之烷基羰基、烷基、芳香基、烷基酯基、烷氧基亦可具有取代基,作為取代基可舉出:甲基、乙基、丙基等。
作為式(3)所示之化合物的具體例,可舉出:環戊酮、3-苯基環戊酮、2-乙醯基環戊酮、1,3-環戊二酮、2-甲基-1,3-環戊二酮、2-乙基-1,3-環戊二酮、環己酮、3-甲基環己酮、4-甲基環己酮、4-乙基環己酮、4-第三丁基環己酮、4-戊基環己酮、3-苯基環己酮、4-苯基環己酮、3,3-二甲基環己酮、3,4-二甲基環己酮、3,5-二甲基環己酮、4,4-二甲基環己酮、3,3,5-三甲基環己酮、2-乙醯基環己酮、4-環己酮甲酸乙酯、1,4-環己二酮單乙烯縮酮(1,4-cyclohexanedione monoethylene ketal)、二環己烷-4,4'-二酮單乙烯縮酮、1,4-環己二酮單-2,2-二甲基伸丙烯縮酮、2-乙醯基-5,5-二甲基-1,3-環己二酮、1,2-環己二酮、1,3-環己二酮、1,4-環己二酮、2-甲基-1,3-環己二酮、5-甲基-1.3-環己二酮、達米酮(dimedone)、1,4-環己二酮-2,5-二羧酸二甲酯、4,4'-二環己酮、2,2-二(4-氧代環己基)丙酮(2,2-Bis(4-oxocyclohexyl)propane)、環庚酮等。此等之中,就所得酚化合物進行環氧化時之高溶劑溶解性,且環氧樹脂組成物之硬化物表現出高導熱性而言,較佳為環戊酮、環己酮、環庚酮、4-甲基環己酮。
(式(4)中,R12分別獨立地存在,表示氫原子、碳數為1~20之烷基、碳數為6~10之芳香基、碳數為1~10之烷氧基或者羥基中之任一者。)
於式(4)中,R12分別獨立地存在,較佳為氫原子、碳數為1~20之未經取代之烷基、碳數為6~10之未經取代之芳香基、碳數為1~10之之未經取代之烷氧基或者羥基。
式(4)中之烷基、芳香基、烷氧基亦可具有取代基,作為取代基可舉出:甲基、乙基、丙基等。
作為式(4)所示之化合物的具體例,可舉出:2,3-丁二酮、2,3-戊二酮、3,4-己二酮、5-甲基-2,3-己二酮、2,3-庚二酮等。此等之中,就所得酚化合物進行環氧化時之高溶劑溶解性,且環氧樹脂組成物之硬化物表現出高導熱性而言,較佳為2,3-丁二酮。
(式(5)中,R13分別獨立地存在,表示氫原子、碳數為1~20之烷基、碳數為6~10之芳香基、碳數為1~10
之烷氧基、碳數為1~10之烷基酯基或者羥基中之任一者。又,m為1~10之整數。)
式(5)中之烷基、芳香基、烷氧基亦可具有取代基,作為取代基可舉出:甲基、乙基、丙基等。
式(5)中,R13分別獨立地存在,較佳為氫原子、碳數為1~20之未經取代之烷基、碳數為6~10之未經取代之芳香基、碳數為1~10之未經取代之烷氧基、碳數為1~10之未經取代之烷基酯基或者羥基。
作為式(5)所示的化合物之具體例,可舉出:二乙醯乙酸乙酯、2,5-己二酮、3-甲基-2,4-戊二酮、3-乙基-2,4-戊二酮、3-丁基-2,4-戊二酮、3-苯基-2,4-戊二酮、4-乙醯基-5-氧代己酸乙酯等。此等之中,就所得酚化合物進行環氧化時之高溶劑溶解性,且環氧樹脂組成物之硬化物表現出高導熱性而言,較佳為3-甲基-2,4-戊二酮、3-乙基-2,4-戊二酮。
(式(6)中,R4分別獨立地存在,表示氫原子、碳數為1~10之烷基、碳數為6~10之芳香基、羥基、硝基、甲醯基、烯丙基或者碳數為1~10之烷氧基中之任一者。k表示R4之數目,且為1~4之整數。)
式(6)中之烷基、芳香基、烷氧基亦可具有取代基,作為取代基可舉出:甲基、乙基、丙基等。
作為式(6)所示的化合物之具體例,可舉出:2-羥基苯甲醛、3-羥基苯甲醛、4-羥基苯甲醛、2,3-二羥基苯甲醛、2,4-二羥基苯甲醛、2,5-二羥基苯甲醛、3,4-二羥基苯甲醛、丁香醛、3,5-二-三級-丁基-4-羥基苯甲醛、異香草醛(isovanillin)、4-羥基-3-硝基苯甲醛、5-羥基-2-硝基苯甲醛、3,4-二羥基-5-硝基苯甲醛、香草醛、鄰-香草醛、2-羥基-1-萘醛、2-羥基-5-硝基-間大茴香醛(2-hydroxy-5-nitro-m-anisaldehyde)、2-羥基-5-甲基異酞醛、2-羥基-4-甲氧基苯甲醛、1-羥基-2-萘醛、2-羥基-5-甲氧基苯甲醛、5-硝基香草醛、5-烯丙基-3-甲氧基柳醛(5-allyl-3-methoxysalicylaldehyde)、3,5-二-三級-丁基柳醛(3,5-Di-tert-butylsalicylaldehyde)、3-乙氧基柳醛(ethoxysalicylaldehyde)、4-羥基異丁醛、4-羥基-3,5-二甲基苯甲醛、2,4,6-三羥基苯甲醛、2,4,5-三羥基苯甲醛、2,3,4-三羥基苯甲醛、3,4,5-三羥基苯甲醛、3-乙氧基-4-羥基苯甲醛等。此等可僅使用一種,亦可併用兩種以上。此等之中,就所得酚化合物進行環氧化時之高溶劑溶解性,且環氧樹脂組成物之硬化物表現出高導熱性而言,較佳為單獨使用香草醛。
酚化合物(A)係酸性條件下或鹼性條件下,藉由式(1)~(5)所示之化合物之一種以上與式(6)所示之化合物
之醛醇縮合反應而得。
式(6)所示之化合物相對於式(1)所示之化合物1莫耳,較佳為使用1.0~1.05莫耳,相對於式(2)、式(3)、式(4)及式(5)所示之化合物1莫耳,較佳為使用2.0~3.15莫耳。
於酸性條件下進行醛醇縮合反應時,作為可使用之酸性觸媒,可舉出:鹽酸、硫酸、硝酸之類的無機酸,甲苯磺酸、二甲苯磺酸、草酸等有機酸。此等可單獨使用,亦可併用多種。酸性觸媒之使用量相對於式(6)所示之化合物1莫耳較佳為0.01~1.0莫耳,更佳為0.2~0.5莫耳。
另一方面,於鹼性條件下進行醛醇縮合反應時,作為可使用之鹼性觸媒,可舉出:氫氧化鈉及氫氧化鉀等金屬氫氧化物,碳酸鉀及碳酸鈉等碳酸鹼金屬鹽,二乙基胺、三乙基胺、三丁基胺、二異丁基胺、吡啶及哌啶等胺衍生物,以及二甲基胺基乙醇及二乙基胺基乙醇等胺基醇衍生物。於鹼性條件下,可單獨使用上述所舉出之鹼性觸媒,亦可併用多種。鹼性觸媒之使用量相對於式(6)所示之化合物1莫耳較佳為0.1~2.5莫耳,更佳為0.2~2.0莫耳。
於獲得酚化合物(A)之反應中,視需要亦可使用溶劑。作為可使用之溶劑,若為如酮類般具有與式(6)所示之化合物之反應性者,則並無特別限制,但就容易使原料之式(6)所示之化合物溶解之方面而言,較佳為使用醇類。
反應溫度通常為10~90℃,較佳為35~70℃。反應時間通常為0.5~10小時,但根據原料化合物之種類會使反應
性存在差異,因此並不限定於此。反應結束後,於取出作為樹脂時,對反應物進行水洗後或不進行水洗,於加熱減壓下自反應液中去除未反應物或溶劑等。於以結晶之形式取出時,藉由將反應液滴加至大量之水中而使結晶析出。於鹼性條件下進行反應時,由於所生成之酚化合物(A)亦有可能溶入水中,較佳為添加鹽酸等形成中性~酸性條件,使其以結晶析出。
接著,對環氧樹脂(A)進行說明。
環氧樹脂(A)係藉由使利用上述方法所獲得之酚化合物(A)與環氧鹵丙烷反應,並進行環氧化而得。再者,於環氧化時,可僅使用一種酚化合物(A),亦可併用兩種以上。又,於酚化合物(A)中亦可併用酚化合物(A)以外之酚化合物。
上述可併用之酚化合物(A)以外之酚化合物,若作為環氧樹脂之原料而通常使用之酚化合物,則可無特別限制地使用,但因有損及硬化物具有高導熱率之本發明的效果之虞,故較佳為與其他酚化合物之併用量極少,特佳為僅使用酚化合物(A)。
作為環氧樹脂(A),就可獲得表現特別優異之溶劑溶解性,且具有高導熱率之硬化物而言,較佳為藉由式(6)所示化合物與式(3)所示化合物之反應所得的酚化合物(A)的環氧化物。於以下,就作為酚化合物時,指出可單獨使用酚化合物(A),或視需要與此併用之其他酚化合物的混合物兩者。
獲得環氧樹脂(A)之反應中,作為環氧鹵丙烷,可使用:表氯醇(epichlorohydrin)、α-甲基表氯醇、β-甲基表氯醇、表溴醇等,較佳為工業上容易獲得之表氯醇。環氧鹵丙烷之使用量相對於酚化合物(A)之羥基1莫耳通常為2~20莫耳,較佳為2~15莫耳,特佳為2~6莫耳。環氧樹脂(A)係於鹼金屬氧化物之存在下,,藉由如下之反應而得:將酚化合物與環氧鹵丙烷加成,接著使生成之1,2-鹵丙烷醚基閉環進行環氧化之反應。此時,如上述之方式以較通常更為少量地使用環氧鹵丙烷,藉此可使環氧樹脂之分子量增大並且分子量分布廣泛。結果所得之環氧樹脂,以具有較低軟化點之樹脂狀物由系統中取出,且表現出優異之溶劑溶解性。
作為可用於環氧化反應之鹼金屬氫氧化物,可舉出:氫氧化鈉、氫氧化鉀等,此等可直接使用固形物,或者亦可使用此等之水溶液。於使用水溶液之情形時,亦可為如下方法:將該鹼金屬氫氧化物之水溶液連續地添加至反應系統內,並且自於減壓下或常壓下連續地餾出之水與環氧鹵丙烷之混合液中分液以去除水,而僅使環氧鹵丙烷連續地返回至反應系統內。鹼金屬氫氧化物之使用量相對於酚化合物之羥基1莫耳通常為0.9~3.0莫耳,較佳為1.0~2.5莫耳,更佳為1.0~2.0莫耳,特佳為1.0~1.3莫耳。
又,本發明人等發現,於環氧化反應,尤其是藉由使用片狀之氫氧化鈉,較使用水溶液之氫氧化鈉更可顯著地降低獲得之環氧樹脂所含之鹵素量。此鹵素為來自環氧鹵
丙烷,且環氧樹脂中混入越多越會引起硬化物之導熱性下降。進而此片狀之氫氧化鈉,較佳為分次添加於反應系統內。藉由進行分次添加,可防止反應溫度之急驟下降,且藉此可防止雜質之1,3-鹵丙烷體或鹵亞甲基體(halomethylene)之生成,可形成導熱率更高之硬化物。
為促進環氧化反應,較佳為添加四甲基氯化銨、四甲基溴化銨、三甲基苄基氯化銨等四級銨鹽作為觸媒。四級銨鹽之使用量,相對於酚化合物之羥基1莫耳通常為0.1~15 g,較佳為0.2~10 g。
又,於環氧化時,就反應進行方面而言,較佳為添加甲醇、乙醇、異丙醇等醇類,二甲碸、二甲亞碸、四氫呋喃、二烷等非質子性極性溶劑(aprotic polar solvent)等來進行反應。此等之中,較佳為醇類或者二甲亞碸。於使用醇類之情形時,可以高效率獲得環氧樹脂。另一方面,於使用二甲亞碸之情形時,可進一步降低環氧樹脂中之鹵素量。
於使用上述醇類之情形時,其使用量相對於環氧鹵丙烷之使用量通常為2~50質量%,較佳為4~35質量%。又,於使用非質子性極性溶劑之情形時,相對於環氧鹵丙烷之使用量通常為5~100質量%,較佳為10~80質量%。
反應溫度通常為30~90℃,較佳為35~80℃。反應時間通常為0.5~10小時,較佳為1~8小時。
反應結束後,對反應物進行水洗後或不進行水洗,於加熱減壓下自反應液中去除環氧鹵丙烷或溶劑等。又,為
進一步減少環氧樹脂中所含之鹵素量,亦可將所回收之環氧樹脂溶解於甲苯、甲基異丁基酮等溶劑,且添加氫氧化鈉、氫氧化鉀等鹼金屬氫氧化物之水溶液而進行反應,可確實地進行閉環。於此情形時,鹼金屬氫氧化物之使用量,相對於酚化合物之羥基1莫耳通常為0.01~0.3莫耳,較佳為0.05~0.2莫耳。反應溫度通常為50~120℃,反應時間通常為0.5~2小時。
反應結束後,藉由過濾、水洗等去除所生成之鹽,進而於加熱減壓下餾去溶劑,藉此獲得環氧樹脂(A)。又,於環氧樹脂(A)作為結晶析出時,亦可於將所生成之鹽溶解於大量之水,之後過濾取出環氧樹脂(A)之結晶。
接著,對藉由上述方法所得之環氧樹脂(A)與酚化合物(A)反應而獲得本發明之環氧樹脂之方法進行說明。
酚化合物(A)之使用量,係以相對於環氧樹脂(A)之環氧基1莫耳酚化合物(A)之羥基量通常為0.1~0.8莫耳,較佳為0.1~0.7莫耳,更佳為0.2~0.6莫耳之方式來使用。若酚化合物(A)之量少,則無法維持優異之溶劑溶解性,反之若過多,則進行高分子量化而軟化點會提高,且熔融黏度亦提高,造成作業性之劣化。
於獲得本發明之環氧樹脂之反應中,可使用硬化促進劑。硬化促進劑可舉出三苯膦作為具體例,但不限定於此。硬化促進劑之使用量相對於環氧樹脂(A)100質量份通常使用0.01~0.2質量份,較佳為0.02~0.15質量份。
於獲得本發明之環氧樹脂之反應中,亦可視需要使用
溶劑。使用之溶劑並無特別限制,但就易使環氧樹脂(A)、酚化合物(A)之兩者溶解之溶劑而言,較佳為使用甲基乙基酮或甲基異丁基酮等之酮類或者環己酮或環戊酮之環酮(anone)類之溶劑作為溶劑。
反應溫度通常為30~120℃,較佳為35~110℃。反應時間通常為0.5~15小時,較佳為1~10小時。反應結束後,對反應物進行水洗後或不進行水洗,於加熱減壓下自反應液中去除溶劑等獲得本發明之環氧樹脂。
以下,對本發明之環氧樹脂組成物加以記載。本發明之環氧樹脂組成物係含有本發明之環氧樹脂作為必須成分。
於本發明之環氧樹脂組成物中,本發明之環氧樹脂可單獨使用或者可併用其他之環氧樹脂。
作為其他環氧樹脂之具體例,可舉出:雙酚類(雙酚A、雙酚F、雙酚S、聯苯酚、雙酚AD及雙酚I等)或酚類(苯酚、經烷基取代之苯酚、經芳香族取代之苯酚、萘酚、經烷基取代之萘酚、二羥基苯、經烷基取代之二羥基苯及二羥基萘等)與各種醛(甲醛、乙醛、烷基醛、苯甲醛、經烷基取代之苯甲醛、羥基苯甲醛、萘甲醛、戊二醛、苯二甲醛、巴豆醛及桂皮醛等)之縮聚物、二甲苯等芳香族化合物、甲醛之縮聚物與酚類的縮聚物、酚類與各種二烯化合物(二環戊二烯、萜烯類、乙烯基環己烯、降冰片二烯(norbornadiene)、乙烯基降莰烯(vinyl norbornene)、四氫茚、二乙烯基苯、二乙烯基聯苯、二異丙烯基聯苯、丁二
烯及異戊二烯等)之縮聚物、酚類與酮類(丙酮、甲基乙基酮、甲基異丁基酮、苯乙酮及二苯甲酮等)之縮聚物、酚類與芳香族二甲醇類(苯二甲醇及聯苯二甲醇等)之縮聚物、酚類與芳香族二氯甲基類(α,α'-二氯二甲苯及二氯甲基聯苯等)之縮聚物、酚類與芳香族雙烷氧基甲基類(雙甲氧基甲基苯、雙甲氧基甲基聯苯及雙苯氧基甲基聯苯等)之縮聚物、雙酚類與各種醛之縮聚物、以及將醇類等環氧丙基化而成之環氧丙基醚系環氧樹脂、脂環式環氧樹脂、環氧丙基胺系環氧樹脂、環氧丙基酯系環氧樹脂等,只要為通常所使用之環氧樹脂,則並不限定於此等。此等既可僅使用一種,亦可併用兩種以上。
於併用其他之環氧樹脂時,本發明之環氧樹脂於本發明之環氧樹脂組成物中之所有環氧樹脂成分中所佔的比例較佳為30質量%以上,更佳為40質量%以上,進而更佳為70質量%以上,特佳為100質量%(不併用其他之環氧樹脂之情形)。其中,於使用本發明之環氧樹脂作為環氧樹脂組成物之改質劑使用時,以於所有環氧樹脂中成為1~30%之比例添加。本發明之環氧樹脂組成物,最佳為使用本發明之環氧樹脂100質量%作為環氧樹脂。
本發明之環氧樹脂組成物係含有硬化劑。作為硬化劑,例如可舉出:胺系化合物、酸酐系化合物、醯胺系化合物及酚系化合物等。此等硬化劑之具體例示於下述(a)~(e)。
(a)胺系化合物:二胺基二苯基甲烷、二乙三胺、三乙四胺、二胺基二苯基碸、異佛酮二胺(isophorone diamine)
及萘二胺等
(b)酸酐系化合物:鄰苯二甲酸酐、偏苯三甲酸酐、均苯四甲酸酐(pyromellitic anhydride)、順丁烯二酸酐、四氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、甲基耐地酸酐(methylnadic anhydride)、六氫鄰苯二甲酸酐及甲基六氫鄰苯二甲酸酐等
(c)醯胺系化合物:由二氰二胺或次亞麻油酸之二聚物與乙二胺所合成之聚醯胺樹脂等
(d)酚系化合物多元酚類(雙酚A、雙酚F、雙酚S、茀雙酚、萜二酚(terpene diphenol)、4,4'-二羥基聯苯、2,2'-二羥基聯苯、3,3',5,5'-四甲基-(1,1'-聯苯基)-4.4'-二醇、對苯二酚、間苯二酚、萘二醇、三-(4-羥基苯基)甲烷(tris(4-hydroxyphenyl)methane)及1,1,2,2-四(4-羥基苯基)乙烷(1,1,2,2-tetrakis(4-hydroxyphenyl)ethane)等);藉由酚類(例如苯酚、經烷基取代之苯酚、萘酚、經烷基取代之萘酚、二羥基苯及二羥基萘等)與醛類(甲醛、乙醛、苯甲醛、對羥基苯甲醛、鄰羥基苯甲醛及糠醛等)、酮類(對羥基苯乙酮及鄰羥基苯乙酮等)或二烯類(二環戊二烯及三環戊二烯等)之縮合所獲得之酚樹脂;藉由上述酚類與經取代之聯苯類(4,4'-雙(氯甲基)-1,1'-聯苯及4,4'-雙(甲氧基甲基)-1,1'-聯苯等)、或經取代之苯基類(1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯及1,4-雙(羥基甲基)苯等)等之縮聚所獲得之酚樹脂;上述酚類及/或上述酚樹脂之改質物;四溴雙酚A及溴化酚樹脂(brominated
phenolresin)等鹵化酚類
(e)其他咪唑類、BF3-胺錯合物、胍衍生物
於此等其他硬化劑之中,較佳為以對環氧樹脂排列有益之二胺基二苯基甲烷,二胺基二苯基碸及萘二胺等胺系化合物,以及鄰苯二酚與醛類、酮類、二烯類、經取代之聯苯類或經取代之苯基類之縮合物等具有活性氫基彼此鄰接結構的硬化劑。
硬化劑可單獨使用,亦可併用多種。所有硬化劑之使用量相對於所有環氧樹脂之環氧基1當量,較佳為0.5~2.0當量,特佳為0.6~1.5當量。
本發明之環氧樹脂組成物可視需要使其含有導熱優異之無機填充材,藉此賦予其硬化物更優異之高導熱性。
本發明之環氧樹脂組成物含有之無機填充材係以對環氧樹脂組成物之硬化物賦予更高之導熱率為目的而添加者,當無機填充材本身之導熱率過低時,會有藉由環氧樹脂與硬化劑之組合而獲得之高導熱率受損之虞。因此,作為本發明之環氧樹脂組成物所含有之無機填充材,導熱率越高者越佳,只要係具有通常為20 W/m.K以上、較佳為30 W/m.K以上、更佳為50 W/m.K以上之導熱率者,則並無任何限制。
再者,此處所述之導熱率係指以根據ASTM E1530之方法測定之值。作為具有此種特性之無機填充材之具體例,可舉出:氮化硼、氮化鋁、氮化矽、碳化矽、氮化鈦、氧化鋅、碳化鎢、氧化鋁、氧化鎂等無機粉末填充材,合成
纖維、陶瓷纖維等纖維質填充材,著色劑等。此等無填充材之形狀可為粉末(塊狀、球狀)、單絲、長絲等中之任一者,尤其是若為平板狀者,則藉由無機填充材本身之積層效果而使得硬化物之導熱性變得更高,且硬化物之散熱性進一步提昇,故較佳。
本發明之環氧樹脂組成物中之無機填充材的使用量相對於環氧樹脂組成物中之樹脂成分100質量份通常為2~1000質量份,但為了儘可能地提高導熱率,較佳為於不對本發明之環氧樹脂組成物在具體用途中之使用等造成障礙的範圍內,儘可能地增加無機填充材之使用量。此等無機填充材既可僅使用一種,亦可併用兩種以上。
又,若可將作為填充材整體之導熱率維持於20 W/m.K以上之範圍,則亦可於導熱率為20 W/m.K以上之無機填充材中併用導熱率為未達20 W/m.K之填充材,但就儘可能獲得導熱率較高之硬化物之本發明之目的而言,導熱率未達20 W/m.K之填充材之使用應限於最小限度。可併用之填充材之種類或形狀並無特別限制。
本發明之環氧樹脂組成物用於半導體封裝用途之情形時,就硬化物之耐熱性、耐濕性、力學性質等方面而言,較佳為以於環氧樹脂組成物中佔75~93質量%之比例使用導熱率為20 W/m.K以上之無機填充材。於此情形時,殘餘為環氧樹脂成分、硬化劑成分及其他視需要而添加之添加劑,可併用之添加劑為其他無機填充材或後述之硬化促進劑等。
本發明之環氧樹脂組成物亦可含有硬化促進劑。作為可使用之硬化促進劑,例如可舉出:2-甲基咪唑、2-乙基咪唑、2-苯基咪唑及2-乙基-4-甲基咪唑等咪唑類,2-(二甲基胺基甲基)苯酚、三乙二胺、三乙醇胺及1,8-二氮雜雙環(5,4,0)十一烯-7(1,8-diazabicyclo(5.4.0)-undecene-7)等三級胺類,三苯膦、二苯膦及三丁基膦等有機膦類,辛酸錫等金屬化合物,四苯鏻-四苯基硼酸鹽及四苯鏻-乙基三苯基硼酸鹽等四取代鏻-四取代硼酸鹽,2-乙基-4-甲基咪唑-四苯基硼酸鹽及N-甲基啉-四苯基硼酸鹽等四苯基硼鹽等。硬化促進劑相對於環氧樹脂100質量份,視需要使用0.01~15質量份。
本發明之環氧樹脂組成物組成物中,視需要可添加矽烷偶合劑、脫模劑及顏料等各種調配劑,各種熱硬化性樹脂以及各種熱塑性樹脂等。作為熱硬化性樹脂及熱塑性樹脂之具體例,可舉出:乙烯酯樹脂、不飽和聚酯樹脂、馬來醯亞胺樹脂(maleimide resin)、氰酸酯樹脂、異氰酸酯化合物、苯并化合物、乙烯基苄基醚化合物、聚丁二烯及其改質物、丙烯腈共聚物之改質物、茚樹脂、氟樹脂、矽樹脂、聚醚醯亞胺、聚醚碸、聚苯醚、聚縮醛、聚苯乙烯、聚乙烯、二環戊二烯樹脂等。熱硬化性樹脂或熱塑性樹脂係以於本發明之環氧樹脂組成物中佔60質量%以下之量使用。
本發明之環氧樹脂組成物可藉由將上述各成分均勻地混合而獲得,作為其較佳用途,可舉出半導體封裝材料或
印刷電路板等。
本發明之環氧樹脂組成物可藉由與先前眾所周知之方法相同之方法而容易地製成其硬化物。例如:視需要使用擠出機、捏合機或輥等將本發明之環氧樹脂之必要成分之環氧樹脂、硬化劑及導熱率為20 W/m.K以上之無機填充材、以及視需要之硬化促進劑、調配劑、各種熱硬化性樹脂或各種熱塑性樹脂等充分地混合直至達到均勻為止而獲得本發明之環氧樹脂組成物,然後利用熔融澆鑄法、轉注成型法、射出成型法或壓縮成型法等使其成型,進而藉由於其熔點以上加熱2~10小時而獲得本發明之環氧樹脂組成物之硬化物。由於以上述方法藉由將搭載於導線架等之半導體元件密封,故本發明之環氧樹脂組成物可用於半導體封裝用途。
又,本發明之環氧樹脂組成物亦可形成為包含溶劑之清漆。該清漆例如可藉由將環氧樹脂、硬化劑中包含至少一種本發明之環氧樹脂、或本發明之酚樹脂之至少一種,及視需要包含導熱率為20 W/m.K以上之無機填充材等之其他成分的混合物與如下有機溶劑混合而獲得:甲苯,二甲苯,丙酮,甲基乙基酮,甲基異丁基酮,環己酮,環戊酮,N,N'-二甲基甲醯胺,N,N'-二甲基乙醯胺,二甲亞碸,N-甲基吡咯啶酮,乙二醇二甲醚、乙二醇二乙醚、二丙二醇二甲醚、二丙二醇二乙醚、三乙二醇二甲醚、三乙二醇二乙醚等二醇醚(glycol ether)類,乙酸乙酯、乙酸丁酯、甲基溶纖劑乙酸酯(methyl cellosolve acetate)、乙基溶纖劑
乙酸酯(ethyl cellosolve acetate)、丁基溶纖劑乙酸酯(butyl cellosolve acetate)、卡必醇乙酸酯(carbitol acetate)、丙二醇單甲醚乙酸酯、戊二酸二烷基酯、丁二酸二烷基酯、己二酸二烷基酯等酯類,γ-丁內酯(γ-butylolactone)等環狀酯類,石油醚、石油腦、氫化石油腦及溶劑石油腦(solvent naphtha)等石油系溶劑等。溶劑之量相對於清漆整體通常為10~95質量%,較佳為15~85質量%。
使如上所述而獲得之清漆含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維及紙等纖維基材後,藉由加熱以去除溶劑,並且使本發明之環氧樹脂組成物成為半硬化狀態,藉此可獲得本發明之預浸物。再者,此處所謂之「半硬化狀態」係指反應性官能基之環氧基的一部分未反應而殘留之狀態。可將該預浸物熱壓成型而獲得硬化物。
以下,以實施例更詳細地說明本發明,但本發明並不限定於此等實施例。於合成例、實施例、比較例中,份係指質量份。
再者,環氧當量、熔點、軟化點、總氯量、導熱率係由以下之條件進行測定。
.環氧當量
利用JIS K-7236記載之方法進行測定,單位為g/eq.。
.熔點
Seiko Instruments Inc.製造之EXSTAR6000
測定試樣2mg~5mg升溫速度10℃/min
.軟化點
根據JIS K-7234之方法進行測定,單位為℃。
.導熱率
根據ASTM E1530之方法進行測定,單位為W/m.K。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中裝入136份4'-羥基苯乙酮、152份香草醛及200份乙醇,並且加以溶解。向其添加20份97質量%硫酸後升溫至60℃為止,於此溫度反應10小時後,將反應液注入至1200份水,使其結晶。過濾結晶後,以600份水進行2次水洗,其後進行真空乾燥,獲得256份黃色結晶之酚化合物1。所得之結晶藉由DSC測定之吸熱尖峰溫度為233℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中裝入166份4'-羥基-3'-甲氧基苯乙酮、122份4-羥基苯甲醛及200份乙醇,並且加以溶解。向其添加20份97%質量硫酸後升溫至50℃,並於此溫度反應10小時後,將反應液注入至1200份水,使其結晶。過濾結晶後,以600份水進行2次水洗,其後進行真空乾燥,獲得285份茶褐色結晶之酚化合物2。所得之結晶藉由DSC測定之吸熱尖峰溫度為193℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中裝入
56份4-甲基環己酮、152份香草醛及150份乙醇,並且加以溶解。向其添加10份97質量%硫酸後升溫至50℃,並於此溫度反應10小時後,加入25份三聚磷酸鈉且攪拌30分鐘。其後添加500份甲基異丁基酮後,以200份水進行2次水洗,之後以蒸發器餾去溶劑,獲得304份半固形之酚化合物3。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中裝入29份丙酮、152份香草醛及300份乙醇,並且加以溶解。向其添加80份50%氫氧化鈉水溶液後升溫至45℃,並於此溫度反應120小時後,將反應液注入至800mL1.5N鹽酸,使其結晶。過濾結晶後,以600份水進行2次水洗,其後進行真空乾燥,獲得165份黃色結晶之酚化合物4。所獲得之結晶之熔點藉由DSC測定為201℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加135份於合成例1所獲得之酚化合物1、370份表氯醇、93份二甲亞碸(以下稱為DMSO),於攪拌下升溫至70℃並進行溶解,於90分鐘間分次添加41份片狀之氫氧化鈉後,維持70℃進行2.5小時反應。反應結束後,使用旋轉蒸發器於135℃減壓下,餾去過量之表氯醇等溶劑。將殘留物溶解於440份甲基異丁基酮(以下稱為MIBK)後水洗去除鹽。水洗後,將MIBK溶液升溫至70℃,並且於攪拌下添加11份30%氫氧化鈉水溶液,進行反應1
小時後,進行水洗至清洗水變為中性為止,並且將所獲得之溶液使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得200份環氧樹脂1。所獲得之環氧樹脂之環氧當量為240g/eq.,軟化點為56℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加135份於合成例2所獲得之酚化合物2、370份表氯醇、93份二甲亞碸(以下稱為DMSO),於攪拌下升溫至70℃並進行溶解,於90分鐘間分次添加41份片狀之氫氧化鈉後,維持70℃進行2.5小時反應。反應結束後,使用旋轉蒸發器於135℃減壓下,餾去過量之表氯醇等溶劑。將殘留物溶解於440份MIBK後水洗去除鹽。水洗後,將MIBK溶液升溫至70℃,並且於攪拌下添加11份30%氫氧化鈉水溶液,進行反應1小時後,進行水洗至清洗水變為中性為止,並且將所獲得之溶液使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得201份環氧樹脂2。所獲得之環氧樹脂之環氧當量為243g/eq.,軟化點為60℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加190份於合成例3所獲得之酚化合物3、370份表氯醇、93份二甲亞碸(以下稱為DMSO),於攪拌下升溫至70℃並進行溶解,於90分鐘間分次添加41份片狀之氫氧化鈉後,維持70℃進行2.5小時反應。反應
結束後,使用旋轉蒸發器於135℃減壓下,餾去過量之表氯醇等溶劑。將殘留物溶解於492份MIBK後水洗去除鹽。水洗後,將MIBK溶液升溫至70℃,並且於攪拌下添加11份30%氫氧化鈉水溶液,進行反應1小時後,進行水洗至清洗水變為中性為止,並且將所獲得之溶液使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得224份環氧樹脂3。所獲得之環氧樹脂之環氧當量為270g/eq.,軟化點為62℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加163份於合成例4所獲得之酚化合物4、370份表氯醇、93份二甲亞碸(以下稱為DMSO),於攪拌下升溫至70℃並進行溶解,於90分鐘間分次添加41份片狀之氫氧化鈉後,維持70℃進行2.5小時反應。反應結束後,使用旋轉蒸發器於135℃減壓下,餾去過量之表氯醇等溶劑。將殘留物溶解於438份MIBK後水洗去除鹽。水洗後,將MIBK溶液升溫至70℃,並且於攪拌下添加11份30%氫氧化鈉水溶液,進行反應1小時後,進行水洗至清洗水為中性為止,並且將所獲得之溶液使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得200份環氧樹脂4。所獲得之環氧樹脂之環氧當量為240g/eq.,軟化點為52℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實
施氮氣沖洗,一面添加200份於合成例5所獲得之環氧樹脂1、68份於合成例1所獲得之酚化合物1、200份MIBK,於攪拌下升溫至80℃並進行溶解,添加0.2份三苯膦後升溫至100℃,維持100℃進行8小時反應。反應後,使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得268份環氧樹脂5。所獲得之環氧樹脂之環氧當量為540g/eq.,軟化點為87℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加201份於合成例6所獲得之環氧樹脂2、68份於合成例2所獲得之酚化合物2、200份MIBK,於攪拌下升溫至80℃並進行溶解,添加0.2份三苯膦後升溫至100℃,維持100℃進行6小時反應。反應後,使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得269份環氧樹脂6。所獲得之環氧樹脂之環氧當量為542g/eq.,軟化點為89℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加235份於合成例7所獲得之環氧樹脂3、93份於合成例3所獲得之酚化合物3、235份MIBK,於攪拌下升溫至80℃並進行溶解,添加0.2份三苯膦後升溫至100℃,維持100℃進行6小時反應。反應後,使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得328份環氧樹脂7。所獲得之環氧樹脂之環氧當量為667g/eq.,軟
化點為97℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加220份於合成例8所獲得之環氧樹脂4、82份於合成例4所獲得之酚化合物4、220份MIBK,於攪拌下升溫至80℃並進行溶解,添加0.2份三苯膦後升溫至100℃,維持100℃進行6小時反應。反應後,使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得302份環氧樹脂8。所獲得之環氧樹脂之環氧當量為610g/eq.,軟化點為88℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加200份於合成例5所獲得之環氧樹脂1、68份於合成例2所獲得之酚化合物2、200份MIBK,於攪拌下升溫至80℃並進行溶解,添加0.2份三苯膦後升溫至100℃,維持100℃進行8小時反應。反應後,使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得268份環氧樹脂9。所獲得之環氧樹脂之環氧當量為542g/eq.,軟化點為82℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加200份於合成例5所獲得之環氧樹脂1、92份於合成例3所獲得之酚化合物3、200份MIBK,於攪拌下升溫至80℃並進行溶解,添加0.2份三苯膦後升
溫至100℃,維持100℃進行8小時反應。反應後,使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得292份環氧樹脂10。所獲得之環氧樹脂之環氧當量為600g/eq.,軟化點為93℃。
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中一面實施氮氣沖洗,一面添加200份於合成例5所獲得之環氧樹脂1、82份於合成例4所獲得之酚化合物4、200份MIBK,於攪拌下升溫至80℃並進行溶解,添加0.2份三苯膦後升溫至100℃,維持100℃進行8小時反應。反應後,使用旋轉蒸發器於180℃減壓下餾去MIBK等,藉此獲得282份環氧樹脂11。所獲得之環氧樹脂之環氧當量為570g/eq.,軟化點為52℃。
相對於60℃、100℃之MIBK,含有藉由此等操作所得之環氧樹脂5~11之各種環氧樹脂,其於樹脂濃度30%之溶解性示於表1。
○:於60℃溶解
×:於100℃不完全溶解(有溶解殘留)
環氧樹脂12:下述式(7)所示之環氧樹脂(商品名:NC-3000日本化藥製造 環氧當量276g/eq.)
環氧樹脂13:含有等莫耳下述式(8)及(9)所示之環氧樹脂之雙酚型環氧樹脂(商品名:YL-6121H Japan Epoxy Resins製造 環氧當量175g/eq.)
以表2之比例(份)調配各種成分,利用混合輥之捏合、錠劑化後,藉由轉注成形來製備樹脂成型體,且於160℃加熱2小時,進而於180℃加熱8小時,獲得本發明之環氧樹脂組成物及比較用環氧樹脂組成物之硬化物。將測定此等硬化物之導熱率之結果示於表2。
硬化劑1:下述式(10)所示之酚醛清漆(phenol novolac)(商品名:H-1,明和化成製造,羥基當量105g/eq.)
硬化促進劑:三苯膦(北興化學工業製造)
以表3之比例(份)調配各種成分,利用混合輥之捏合、錠劑化後,藉由轉注成形來製備樹脂成型體,且於160℃加熱2小時,進而於180℃加熱8小時,獲得本發明之環氧樹脂組成物及比較用樹脂組成物之硬化物。將測定此等硬化物之導熱率之結果示於表3。
無機填充材1:球狀氧化鋁(商品名:DAW-100電氣化學工業製造 導熱率38 W/m.K)
無機填充材2:氮化硼(商品名:SGP電氣化學工業製造 導熱率60 W/m.K)
於70℃使100份於實施例1所獲得之環氧樹脂5溶解於1000份二甲基甲醯胺後,恢復至室溫。於70℃使7份硬化劑之1,5-萘二胺(東京化成製造,胺當量40g/eq.)溶解於48份二甲基甲醯胺後,恢復至室溫。利用攪拌翼型之均質攪拌機混合、攪拌上述環氧樹脂溶液與硬化劑溶液而製成均勻之清漆,進而添加204份(相對於樹脂固體成分100體積份為50體積份)之無機填充材(商品名:SGP電氣化學工業製造,導熱率為60 W/m.K)、及100份二甲基甲醯胺進行混合、攪拌,從而製備本發明之環氧樹脂組成物。
使該環氧樹脂組成物之清漆含浸於厚度為0.2mm之玻璃纖維織布(商品名:7628/AS890AW Asahi-Schwebel製造),進行加熱乾燥而獲得預浸物。將4片該預浸物與配置於其兩側之銅箔重疊後,於溫度為175℃、壓力為4 MPa之條件下加熱加壓成型90分鐘而一體化,從而獲得厚度為0.8mm之積層板。測定該積層板之導熱率,結果為4.3 W/m.K。
分別將實施例22中之環氧樹脂5變更為100份環氧樹脂7,1,5-萘二胺之量變更為6份,無機填充材之量變更
為201份之外,與實施例22相同之操作順序而獲得積層板。測定該積層板之導熱率,結果為4.5 W/m.K。
分別將實施例22中之環氧樹脂5變更為100份環氧樹脂13(YL-6121H),1,5-萘二胺之量變更為23份,無機填充材之量變更為234份之外,與實施例22相同之操作順序而獲得積層板。測定該積層板之導熱率,結果為3.6 W/m.K。
藉由以上結果可確認,本發明之環氧樹脂係溶劑溶解性優異,再者含有本發明環氧樹脂之環氧樹脂組成物之硬化物具有優異之導熱性。因此,本發明之環氧樹脂在用於電氣、電子零件用絕緣材料及積層板(印刷電路板等)等之用途極其有用。
參照特定之態樣詳細地說明了本發明,但對於本領域業者而言,可在不脫離本發明之精神與範圍的情況下進行各種變更及修改。
再者,本申請案係基於20011年7月26日所申請之日本專利申請(日本特願2011-163006),藉由引用而援引其全部內容。又,此處所引用之所有參照係作為整體而編入。
本發明之環氧樹脂組成物之硬化物,與先前之環氧樹脂之硬化物相比具有優異之導熱性,並且溶劑溶解性亦優異。因此,作為密封材料、預浸物等於電氣、電子材料、成型材料、注型材料、積層材料、塗料、接著劑、光阻劑、光學材料等廣範之用途極其有用。
Claims (6)
- 一種環氧樹脂,係藉由將下述式(1)~(5)所示之化合物之一種以上,和下述式(6)所示之化合物反應而得的酚化合物、與該酚化合物和環氧鹵丙烷反應而得的環氧樹脂,在該環氧樹脂量為當量比成為過量之條件下反應所得,並且環氧當量為540g/eq.以上;
- 一種環氧樹脂組成物,係含有申請專利範圍第1項之環氧樹脂及硬化劑而成。
- 如申請專利範圍第2項之環氧樹脂組成物,其含有導熱率20W/m‧K以上之無機填充材而成。
- 如申請專利範圍第3項之環氧樹脂組成物,係用於半導體封裝用途。
- 一種預浸物,係由申請專利範圍第4項之環氧樹脂組成物及片狀之纖維基材構成。
- 一種硬化物,係由申請專利範圍第4項之環氧樹脂組成物、或者申請專利範圍第5項之預浸物硬化而成。
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