TWI300073B - Resin composition for sealing a photo semiconductor - Google Patents
Resin composition for sealing a photo semiconductor Download PDFInfo
- Publication number
- TWI300073B TWI300073B TW091120834A TW91120834A TWI300073B TW I300073 B TWI300073 B TW I300073B TW 091120834 A TW091120834 A TW 091120834A TW 91120834 A TW91120834 A TW 91120834A TW I300073 B TWI300073 B TW I300073B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin composition
- cured product
- group
- anhydride
- acid
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims description 49
- 239000004065 semiconductor Substances 0.000 title claims description 18
- 238000007789 sealing Methods 0.000 title claims 2
- -1 alicyclic carboxylic anhydride Chemical class 0.000 claims description 36
- 238000002834 transmittance Methods 0.000 claims description 23
- 125000003700 epoxy group Chemical group 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 20
- 230000003647 oxidation Effects 0.000 claims description 20
- 238000007254 oxidation reaction Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 230000003287 optical effect Effects 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229920000058 polyacrylate Polymers 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000005538 encapsulation Methods 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 230000009477 glass transition Effects 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 3
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims description 3
- 230000003064 anti-oxidating effect Effects 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
- 206010003497 Asphyxia Diseases 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 41
- 239000002253 acid Substances 0.000 description 17
- 239000003822 epoxy resin Substances 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 150000008065 acid anhydrides Chemical class 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 7
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 229940116229 borneol Drugs 0.000 description 7
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 7
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 7
- 229960000834 vinyl ether Drugs 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000004848 polyfunctional curative Substances 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 230000006750 UV protection Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910021653 sulphate ion Inorganic materials 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000101 thioether group Chemical group 0.000 description 3
- 239000012780 transparent material Substances 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000004844 aliphatic epoxy resin Substances 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 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
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical class CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical group COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical group CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- OIXUMCLBEXJAQZ-UHFFFAOYSA-N 1-methyl-4-oxatricyclo[5.2.1.02,6]dec-2(6)-ene-3,5-dione Chemical compound O=C1OC(=O)C2=C1C1(C)CC2CC1 OIXUMCLBEXJAQZ-UHFFFAOYSA-N 0.000 description 1
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-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
- AQKDMKKMCVJJTC-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)oxirane Chemical compound CC(C)COCC1CO1 AQKDMKKMCVJJTC-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 2-dodecanoyloxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCC ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 0.000 description 1
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 1
- XCYWUZHUTJDTGS-UHFFFAOYSA-N 2-methoxy-3,4-dihydro-2h-pyran Chemical compound COC1CCC=CO1 XCYWUZHUTJDTGS-UHFFFAOYSA-N 0.000 description 1
- ZQTHQBSAGHGWSL-UHFFFAOYSA-N 2-methyl-3-(oxiran-2-yl)propanoic acid Chemical compound OC(=O)C(C)CC1CO1 ZQTHQBSAGHGWSL-UHFFFAOYSA-N 0.000 description 1
- MBEQREFLONMSSX-UHFFFAOYSA-N 2-methylprop-2-enoyl cyanide Chemical compound CC(=C)C(=O)C#N MBEQREFLONMSSX-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- UMNVUZRZKPVECS-UHFFFAOYSA-N 2-propanoyloxyethyl propanoate Chemical compound CCC(=O)OCCOC(=O)CC UMNVUZRZKPVECS-UHFFFAOYSA-N 0.000 description 1
- GYIUDLLQLVWKPP-UHFFFAOYSA-N 2-propylpentanoyl 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OC(=O)C(CCC)CCC GYIUDLLQLVWKPP-UHFFFAOYSA-N 0.000 description 1
- WMNWJTDAUWBXFJ-UHFFFAOYSA-N 3,3,4-trimethylheptane-2,2-diamine Chemical compound CCCC(C)C(C)(C)C(C)(N)N WMNWJTDAUWBXFJ-UHFFFAOYSA-N 0.000 description 1
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical group CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
- GFUSSNHNFRXUHB-UHFFFAOYSA-N 3-methylbut-2-en-2-yl acetate Chemical compound CC(C)=C(C)OC(C)=O GFUSSNHNFRXUHB-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
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- C—CHEMISTRY; METALLURGY
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- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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Description
13〇0〇73 〔發明說^ χ明所屬之技術領域] 硬化體封裝用樹脂組成物,該組成物 ”光體封裝用硬化以及封裝在該硬化物 先前技術] 由脂,ί光半導體封裝用樹脂組成物者,P ^女 物长式環氧樹脂及酸酐硬化劑 知有例如使用 邀2開平6一 3 1 6 6 2 6號公報),成之^明性樹脂組成 鱗=導體之密著性,具體揭示有關 2之光半導體封裴用樹脂組成物。有甲基丙烯酸系 势从、年又有一種光半導體正被實用彳μ 〆 ☆等短波長光之發光二極管=此=出青色光或 二鸯光體而成U色發光二才 U專發光二極管上 時二:係要求自青色光到紫色光之透光二極管之封 發巧發熱而降低透過率(以下稱:;=;以= :先、紫色光等高能量短波長光中透=。亦即要求在青 也不會著色之特性(以了,稱為耐势:使經長時間照射, 因此,曾有提議以非芳香族環^ I光性)。 Ϊ鳴組合物做為封裝發光二極管:J ” :為有效成分之 ^ ΐ Γ 〇!〇~ 19615m ^ , 3, ^ Λ 甲基〜3, 4一環氧基環已烷羧 衣乳基% 酐做為有效成分之發光二極管封·田曰/、匕土六氫苯二酸 本案發明人針對由脂環式環‘二月曰組合物。 乳树知與脂環式羰酸酐做
314017.ptd 1300073 五、發明說明(2) "" 成之透明性樹脂組成物,例如,被用來封裝發光二極管之 樹脂組成物之以3, 4—環氧基環已基甲基—3, 4_環氧基環 已烷羧酸酯與甲基六氫苯二酸酐做為有效成分之環氧樹脂 組成物的硬化物加以檢討時,發現該組成物之硬化物在硬 化之後已纟至使透明物著色,在高溫(1 5 )保管時,更 會再著色之問題產生。 “本發明之目的,係提供硬化後之光透過性優異,經青 色光、紮外光長時間照射,或在高溫長時間使用也有優異 之f透過性’亦即提供初期透過性、耐紫外光性以及财熱
I4生等任一種特性皆優之硬化物的光半導體封裝用樹脂組合 物 、、σ [發明之概要] 發明係提供以含有下述(A)及(Β )成分為特徵之光丰 體封裝用樹脂組合物。 千 (A) ·含環氧基之(曱基)丙烯酸系聚合物 (β ) ·選自由下述(b 1)至(b 4 )所組成族群中至少一種之 化劑 ^又 (b 1)多價羧酸 (b 2)多價魏酸酐
(b s)多價羧酸與下述一般式(B—丨)所示化合物 生成物 7 <反應 (b J多價羧酸酐與下述一般式(B— 2 )所示化合物 應生成物 反
314017.ptd 第9頁 1300073 五、發明說明(3) R1、 B2
(式中,R 1至R嚷示分別獨立之氫原子或碳原子數1至8之烷 基;R 3及R %可以是與R輿R結合之碳原子數1至8之烯基; R 7表示烯基;在R1至R所示烷基及烯基中所含甲烯基也可以 是有醚基及/或羰基所取代者;Y 1及Y浪示分別獨立之氧原 子、硫原子。) 本發明又提供上述樹脂組成物硬化而成之硬化物,以 及選自發光二極管元件及光二極管元件所組成族群之光半 導體而以由上述硬化物所封裝為特徵之光二極管。 [發明之實施形態] 本發明之(A)成分係含有環氧基之(曱基)丙烯酸系聚 合物,具體而言,可列舉選自丙稀酸烧酯、甲基丙烯酸烧 酯、丙烯氰及甲基丙烯氰中至少1種之單體,與下述一般 式(A— 1)所示單體聚合而成含有環氧基之(曱基)丙烯酸 系聚合物等。 R- X- CH2- E (A- 1) (式中,R表示碳原子數為2至1 2之脂稀基,X表示羰氧基或
314017.ptd 第10頁 1300073 五、發明說明(4) 亞曱氧基,E表示選自下述
Η 之環氧基。) 具體之一般式(A— 1)所示單體,可列舉烯丙基縮水 甘油基醚、2—甲基稀丙基縮水甘油基醚等不飽和縮水甘 油基醚;縮水甘油基丙浠酸S旨、縮水甘油基甲基丙烯酸 酉旨、依康酸縮水甘油基醚等不飽和縮水甘油基醚;3,4— 環氧基環己基甲基丙烯酸酯、3,4一環氧環己基甲基甲基 丙烯酸酯等飽和環狀脂肪族環氧基(曱基)丙烯酸酯等。 做為一般式(A— 1 )所示之單體者,也可使用2種以上 之一般式(A— 1 )所示單體。 做為一般式(A— 1 )所示單體者,其中,以不飽和縮水 甘油基醚及飽和環狀脂肪族環氧基(甲基)丙烯酸酯為佳, 尤其,以3,4—環氧基環己基甲基丙烯酸酯及縮水甘油基 曱基丙烯酸酯為宜。 又,做為製造(Α)成分所使用之(甲基)丙烯酸系單體 者,例如可列舉丙烯酸曱酯、曱基丙烯酸曱酯、丙烯酸乙 酯、甲基丙烯酸乙酯等具有碳原子數1至2 0左右之直鏈烷 基之(曱基)丙烯酸烷酯;丙烯酸第3丁酯、甲基丙烯酸第3 丁酯等具有碳原子數3至2 0左右之分枝狀烷基之(甲基)丙 烯酸烷酯;丙烯酸環己酯、甲基丙烯酸環己酯等具有碳原
314017.ptd 第11頁 1300073 五、發明說明(5) 子數5至2 0左右之飽和環狀脂肪族烷基之(甲基)丙烯酸烷 酯;丙烯氰、甲基丙烯氰等(甲基)丙烯氰等。 / 做為(曱基)丙浠酸系單體者,也可使用2種以上之(甲 基)丙烯酸系單體。 做為(曱基)丙烯酸系單體者,其中,以(甲基)丙烯酸 烷酯為宜,尤其以具有直鏈或分枝狀之碳原子數1至4之烷 基的(甲基)丙烯酸烷酯,或具有飽和環狀脂肪族烷基之 (甲基)丙烯酸院醋為佳。 在(A)成分中由(甲基)丙烯酸系單體構成之構造單位 之含量,通常為0至9 5莫爾%程度,較佳為1 0至8 0莫爾%。 在製造(A)成分時,也可以使用與(甲基)丙烯酸系單 體不同之單體,例如使與(甲基)丙烯酸系單體共聚合製得 之在分子内含有1個乙烯性雙鍵之脂肪族單體聚合亦可。 具體而言,可列舉丁酸乙烯、丙酸乙烯、三甲基乙酸乙 烯、月桂酸乙烯、異壬酸乙浠、華沙地酸乙烯(versatic acid vinyl)巴他等烧基酸乙稀酯;氯乙稀、溴乙烯等鹵 化乙烯;偏氯乙烯等偏i化乙烯類。 在(A )成分中該脂肪族單體使用量,相對於以構成含 有環氧基之(曱基)丙烯酸系聚合物之全部單體為100重量 部而言,通常在1 0重量份以下,實質上以不使用較佳。 (A)成分之製造方法者,例如,在甲醇、異丙醇等醇 類;丙酮、甲乙酮、甲異丁酮等酮類;醋酸乙酯、醋酸丁 酯等酯類;甲苯、二甲苯等芳香族碳化氫等有機溶劑中, 將使用之單體及自由基產生劑混合,再視需要混入連鎖移
314017.ptd 第12頁 1300073 五、發明說明(6) 動劑,於60至1 2 0°C左右共聚合之方法;例如特開平丨〇— 1 9 5 1 1 1連續在聚合器中供應預期使用之單體,在該聚合器 内於聚合起始劑存在下或不存在下,將上述混合物在1 8 〇 至3 0 〇°C中加熱5至6 0分鐘,連續將所得反應生成物自該器 中取出之方法等。 做為(A )成分者也可以使用2種以上含有環氧基之(甲 基)丙烯酸系聚合物。 旦又,含有環氧基之(甲基)丙烯酸系聚合物的環氧當 里,以1 28g/當量以上為宜,較佳為i 5〇至45〇〇g/當量。 含有環氧基之(甲基)丙烯酸系聚合物,例如,也可以 =用Premer — CP— 5 0M (縮水甘油甲基丙稀酸酯·丙烯酸 甲酯共聚合物,曰本油脂(株)製)等市隹σ 。 只要不使本^明之硬化物著色、,做分者,也 了以混合斑含有環乳基之(甲其、τ < 2二t ^ 基M浠酸系聚合物不同,實 貝上在分子内不含有雙鍵之環氧樹脂。 做為如此實質上分子内不人士 ^ m . .. ^ 3有雙鍵之環氧樹脂者’具 脂肪族環氧樹月“由脂肪j型芳香族環氧樹脂、 油喊)、叛酸之縮水甘油環氳㈣炫所得之縮水甘 所得之縮水甘油醋或脂環式脂肪族緩酸與環氫鹵丙烧 甘油醋等)、飽和環狀脂心》與環氫•丙烧所得之縮水 等。 4私每氧樹脂、含螺環環氧樹脂 在此,做為含雜環環轰钟 型環氧樹脂、三縮水甘油ί树脂者,例如可列舉乙内醯脲 異氰酸酯等。
1300073 五、發明說明(7) 做為加氫型芳香族環氧樹脂者,例如可列舉加氨雙紛 A型環氧樹脂、加氫雙S分F型環氧樹脂、加氫紛酸清漆型環 氧樹脂、加氫甲酚醛清漆型環氧樹脂、加氫聯苯型環氧樹 脂等。 做為脂肪族環氧樹脂者,例如可列舉丁基縮水甘油 醚、1,6—己烷二醇二縮水甘油醚、新戊基乙二醇二縮水 甘油醚、環己烧二甲醇二縮水甘油、聚丙二醇二縮水甘 油醚、三羥甲基丙烷三縮水甘油醚等。 做為羧酸之縮水甘油酯者,例如可列舉新癸酸縮水甘 油S旨、六氫苯二酸二縮水甘油S旨等。 飽和環狀脂肪族環氧樹脂者,有在分子内不含有二價 結合之脂環式環氧樹脂,例如下述式(A— 2 )
所示3,4一環氧基環己基甲基一 3,4一環氧基環己烷羧酸 酯、ε —己内酯改質3,4—環氧基環己基甲基一 3,4一環氧 基環己烷羧酸酯、雙(3,4—環氧環己基)己二酸酯, 1,2, 8, 9一二環氧檸檬烯等。 在(A)成分中,分子内不含碳一碳雙鍵之環氧樹脂的 含量,通常是與含環氧基之(甲基)丙烯酸系聚合物相同重 量程度以下。 做為本發明之(B )成分者,為選自由下述(b 〇至(b 4)所
314017.ptd 第14頁 1300073 五、發明說明(8) 組成族群中至少一種之硬化劑。 (b 〇多價羧酸 (b2)多價羧酸酐 (b 3)多價羧酸與下述一般式(B · 1 )所示化合物之反應 生成物 (b4)多價羧酸酐與下述一般式(B· 2)所示化合物之反 應生成物
-C R3 (B-1) V—R4 R5 V=CH HC:=Cv (Β·2) \2 Υ2 R6 (式中,R 1至R嚷示分別獨立之氫原子或碳原子數1至8之烷 基;R 3及R隻也可以與R輿R結合之碳原子數1至8之烯基; R 7表示烯基R1至R所示烷基及烯基中所含甲烯基也可以是有 醚基及/或羰基所取代者;Υ 1及Υ涑示分別獨立之氧原子、 硫原子。) 做為(b 〇者,通常是分子内含有2個以上游離羧基之碳 原子數2至2 2之化合物,具體而言,例如,丁二酸、己二
314017.ptd 第15頁 1300073 五、發明說明(9) 酸、壬二酸、癸二酸、癸二魏酸、十二碳稀玻ίό酸、乙基 十八基二酸等脂肪族多價羧酸;鄰苯二甲酸、間苯二甲 酸、對苯二甲酸、偏苯三酸、均苯四甲酸、4,4’一二四苯 四羧酸、3,3’,4,4’一羥基二苯二甲酸、3,3’,4,4’一雙苯 基四羧酸、苯基十八基二酸等之芳香族多價羧酸;六氫化 苯二甲酸、甲基四氫化苯二甲酸、甲基六氫化苯二甲酸、 5 —原冰片烧一 2,3—二魏酸、5—原冰片稀一2,3—二魏 酸、甲基原冰片烷一 2,3—二羧酸、甲基原冰片烯一 2,3— 二魏酸、1,4,5,6,7,7—六氯一5—原冰片稀一2,3—二羧 酸、5—( 2,5—二氧代四氫一3—咲喃甲醯基[註: furanyl])— 3—甲基一3—環己稀一1,2—二魏酸、5— (2, 5—二氧代四氫一3—咲喃甲酿基)原冰片烧一 2,3—二魏 酸等脂環式多價羧酸:聚合(甲基)丙烯酸所得丙烯酸樹 脂;馬林化聚丁二烯樹脂等。 做為(b 2)者,係上述(b D之分子内酸酐及/或是分子間 酸酐,具體而言,可列舉苯二甲酸酐、四溴合苯二曱酸 酐、四氫苯二甲酸gf、均苯四甲酸酐、4,4’一二苯甲酮四 羧酸酐、3, 3’,4,4’一羥基二苯二酸酐、3, 3’,4, 4’一聯 苯四羧酸二酐、乙二醇雙偏苯三酸酯(新日本理化(株)
製,商品名TMEG)、甘油三偏苯三酸酯(新曰本理化(株) 製,商品名TMT A)等芳香族多價羧酸酐;六氫化苯二甲酸 酐、甲基四氫化苯二甲酸酐、甲基六氫化苯二甲酸酐、5 —原冰片烧一 2,3—二魏酸酐、5—原冰片稀一2,3—二魏 酸酐、甲基原冰片烷一2,3—二羧酸酐、馬來酸酐與C
314017.ptd 第16頁 1300073 五、發明說明(ίο) 烯之Diels— Alder反應物(日本環氧樹脂(株)公司製 YH 一 3 0 6等)、1,4, 5, 6, 7, 7—六氯一 5—原冰片烯一2, 3—二 魏酸酐、5— (2,5—二氧代四氫一 3—咲喃曱酷基)一3—甲 基一 3—環己烯一1,2—二魏酸酐、5— (2,5—二氧代四氫 一 3—呋喃曱醯基甲基)原冰片烯一2,3—二羧酸酐等脂環 式多價魏酸酐;十二碳琥拍酸酐、聚己二酸酐、聚壬二酸 酐、聚癸二酸酐、聚(乙基十八基二酸)酐,聚(苯基十 八基二酸)酐等之脂肪族多價羧酸酐等。 做為(b 2)者,其中也以分子内酸酐為宜,尤其,脂環 式多價羧酸之分子内酸酐為佳,其中尤其,六氫化苯二甲 酸酐、甲基六氫化苯二甲酸酐、原冰片烯一2,3—二羧酸 酐、甲基原冰片烯一 2,3—二羧酸酐、5— (2,4—二氧代四 氮一 3—咲喃甲酸基甲基)原冰片稀一2,3—二魏酸野等’ 實質上以在分子内不含有二價結合之脂環式羧酸酐為佳。 做為(b 3)者,係上述多價羧酸(b )與一般式(B— 1 ) 所示化合物之反應生成物,(b 〇之游離魏氧基係以一般 式(B— 1 )所保護者。在此,做為一般式(B— 1 )所示化合物 者,可列舉如曱基乙烯醚、乙基乙烯醚、異丙基乙烯醚、 正一丙基乙烯醚、正一丁基乙烯醚、異丁基乙烯醚、2— 乙基己基乙烯醚、環己基乙烯醚等之脂肪族乙烯醚化合物 及此等之醚基係硫醚基中所取代之脂肪族乙烯硫醚化合 物,再者2,3—二氫咲喃、2 . 5—二氫咲喃、3,4—二氫一 2H—吡喃、3, 4—二氫一2—甲氧基一2H—吡喃、3, 4—二 氮—6—甲基一2 Η—吼喃一2—酉同、5,6 —二氯一4 一曱氧基
314017.ptd 第17頁 1300073 五、發明說明(11) —2 Η— D比喃、3,4 —二氮一2—乙氧基一2 Η—吼σ南等環狀乙 烯醚化合物及在此等以硫醚基取代醚基之環狀乙烯硫醚化 合物等。 做為(b 4)者,係上述多價羧酸酐(b Ο與一般式(Β— 2 )所示化合物之反應生成物,(b Ο之酸酐基開環後,以 一般式(B— 2 )所保護者,在此,做為一般式(B— 2 )所示化 合物者,可列舉如三甲基二醇二乙烯醚、乙二醇二乙烯 醚、聚乙二醇二乙烯醚、丁基二醇二乙烯醚、戊基二醇二 乙烯醚、己基二醇二乙烯醚、1,4—環己烷二甲醇乙烯 醚、氫醒之乙稀醚化合物、雙紛A之乙稀醚化合物、雙齡F 之乙烯醚化合物、及此等之醚基由硫醚基所取代之二乙硫 醚類等。 本發明之光半導體封裝用樹脂組成物可用之(B)成 分,其中以(b2)為佳。 在樹脂組合物中(B)成分之含量係依(b 〇至(b 4)之種 類不同而異,(b !)之場合,相對於(A )成分中所含有之環氧 基合計1莫爾,(b 〇之遊離羧基為1. 0至3 . 0莫爾左右,但較 佳是1 · 6至2 · 4莫爾程度;(b 2)之場合,相對於(A)成分中所 含有之環氧基合計1莫爾,(b2)之酸酐基(-CO-0-C0-)通 常是0 . 5至1. 5莫爾左右,但較佳是0 . 8至1. 2莫爾程度;(b 3)之場合,相對於(A)成分中所含有之環氧基合計1莫爾, 與(Β- 1)反應所得之酯基為1. 0至3. 0莫爾左右,但較佳是 1 _ 6至2 _ 4莫爾程度;(b 4)之場合,相對於(A )成分中所含有 之環氧基合計1莫爾,與(B-2)反應所得之酯基為1. 0至3. 0
314017.ptd 第18頁 1300073 五、發明說明(12) 莫爾左右,但較佳是1. 6至2. 4莫爾程度。 (B )成分中,因應需求,也可含有硬化促進劑。做為 硬化促進劑者,例如可列舉三級胺、三級胺鹽、第四級銨 鹽、味嗤化合物、二氮雜雙環烯化合物及其鹽、膦化合 物、第四級鱗鹽、侧化合物、醇類、金屬鹽、有機金屬錯 鹽等。 在此,做為三級胺者,可列舉如三乙醇胺、四甲基己 烷二胺、三乙二胺、二甲基苯胺、二甲基胺基乙醇、二乙 基胺基乙醇、2, 4, 6—三(二甲基胺基甲基)酚、Ν,Ν’一二 甲基哌嗪、吡啶、甲基吡啶、苄基二甲基胺及2—(二甲基 胺基)甲基酚等,做為三級胺者,可列舉如三級胺之2—乙 基己酸鹽、辛酸鹽等。 做為四級銨鹽者,例如,十二基三甲基銨氯化物、十 六基三甲基銨氯化物、苄基二甲基四癸基銨氯化物及十八 基三甲基銨氯化物、上述氯化物以溴化物、碘化物取代 做為咪唑化合物者,可列舉如1—苄基一2—苯基咪 σ坐、2—甲基。米σ坐、2—十二基口米唾、2—乙基坐、1 一卞 基一2—甲基咪唑、1一氰乙基一2—十二基咪唑等。 做為二氮雜雙環稀化合物及其鹽者,例如,1,8—二 氮雜雙環(5,4,0 )十二一7—烯、1,5—二氮雜雙環(4,3,0 ) 壬一 5—烯、及此等之酚鹽、辛酸鹽、對位甲苯磺酸鹽、 犧酸鹽、鄰位苯二酸鹽、四苯基棚酸鹽、8—卞基一 1 一氮 雜一8—偶氮二氮雜雙環(5 . 4. 0 )十二一7_烯四苯基硼酸
314017.ptd 第19頁 1300073 五、發明說明(13) 鹽等。 做為膦化合物者,可列舉如三苯基膦、三一正一丁基 膦、三一正一辛基膦、三甲苯基膦、三環己基膦、三一對 位一甲氧基苯基鱗、三一(2,6—二曱氧基苯基)鱗等。 做為第四級鱗鹽者,可列舉如四一正一丁基鎸溴化合 物、四一正一 丁基鱗苯并偶氮鹽、四一正一 丁基鱗四敗石朋 酸鹽、四一正一丁基鱗四苯基硼酸鹽、四苯鱗溴化物、曱 基三苯基鱗溴化物、乙基三苯鱗溴化物、乙基三苯基鱗碘 化合物、乙基三苯鱗醋酸鹽、正一丁基三苯鱗溴化物、苄 基三苯鱗溴化物、四苯鱗四苯硼酸鹽等。 做為硼化合物者可列舉如三乙胺四苯基硼酸鹽、N— 甲基嗎啉四苯基硼酸鹽等之四苯基硼鹽類等。 做為醇類者,可列舉如乙二醇、甘油類等。 做為硬化促進劑者,也可使用2種以上之硬化促進 劑。 做為硬化促進劑者,其中以第四級鱗鹽、咪唑化合 物、二氮雜雙環烯化合物及其鹽為佳。 本發明之光半導體封裝用樹脂組合物為了更提高所賦 與之硬化物耐熱性能,鼓勵在該組合物中含有作為氧化防 止劑之添加劑。 做為氧化防止劑者,可列舉如(C )酚系氧化防止劑、 (D )硫系氧化防止劑、磷系氧化防止劑等。 本發明所使用之(C )酚系氧化防止劑,可列舉如下述 一般式(C-l)
314017.ptd 第20頁 1300073 五、發明說明(14)
(式中’ η表示1至2 2之整數) 所示之酚系氧化防止劑,尤其以碳原子數11為8至丨8程度之 盼系氧化防止劑為適當。 本發明樹脂組合物中(C )成分之含量,相對於(Α )及 (Β)成分合計為1 〇 〇重量份,以〇 · 〇 3至3重量份左右為宜, 更佳為0 · 1至1重量份左右。 做為本發明所用之(D)硫系氧化防止劑者,可列舉如 下述一般式(D- 1) 牛
- CmH2m+1 (D - (式中’ in表示1 〇至2 2之整數) 所示之化合物等’其中以1„為12至19之硫系氧化防止劑為 適當。 本發明樹脂組合物中(D )成分之含量,相 (B )成分合計為1 〇 〇重量份,以〇 · 〇 3至3重量a + ; 击乂土达λ , r 里伤左右為宜, 更仏為0· 1至1重量份左右。 做為氧化防止劑者,以(c)酚系氧化防止添 硫系氧化防止劑為宜,尤其以併用(C )與(D )為d ’及(D ) 本發明之光半導體封裝用樹脂組合物中y,° 。 害所得硬化物之光透過性、耐熱性、耐紫只要在不損 J系外線之範圍内,
314017.ptd
第21頁 1300073 五、發明說明(15) — 也可含有離型劑、石々校偶人添丨 塑南j、、$、々$丨 夕凡 Ό ^、低應力化劑、充填劑、可 -二=加:與觸變㈣、染料、光散亂劑、紫外線 如,匕導八體封裝用樹脂組合物之製造方法,可以列舉 (Α)忠八 =(B)成分及添加劑等主要為固體時,在粉碎 機將(1)成八1成二及f加劑之後加以混合之方法;以混練 劑中、、々統(β)成分及添加劑等熔融混練之方法;在溶 除去& 、、刀、(β)成分及添加劑等,均勻攪拌混合後 能日/合蜊之方法;(Α)成分、(Β)成分及添加劑等主要為液 ;;日^將此等搜拌混合之方4;在溶劑中,轉(Α)成 法。)成7刀及添加劑等均勾攪拌混合後除去溶劑之方 /武、/斤侍樹脂組合物在常溫為固體時,也可以經再粉碎及 4進行打錠。 \ 1 0 (TC本發明之樹脂組合物,通常在8 〇°C至2 0 0°C,較佳為 加熱Λ180°〇 ’更佳在120°c至170°c程度之溫度中’藉由 同砍至2 4小時左右使其硬化。硬化時,以2階段以上不 ’、牛組合進行步進處理較佳。 物。本發明之硬化物是攪拌後所得之樹脂組合物的硬化 使用ΐ化物之初期透過率,通常在7〇%以上,但(Β)成分若 裎片=質上在分子内不含雙鍵之脂環式綾酸酐,可得75 〇/ 又u上之更佳硬化物。 在此,初期透過率係指樹脂組合物於硬化後,冷卻到
第22頁 1300073 五、發明說明(16) 至溫為止’將厚度調整到2mm之硬化物,在冷卻後2天之 内,於波長370nm中測定厚方向之透過率。 本發明之硬化物之耐紫外線及耐熱性優異。 本發明之硬化物,通常在耐紫外線試驗中透過率在 40%以上在此,耐紫外線試驗係將調整到2jnm之硬化物,在 4〇°C、50%相對濕度之條件下,於波長34〇nm中以光量為〇· 55W/m之光照射3 0 0小時之後,在波長3 70nm中測定厚方向 之透過率的試驗。 本發明之硬化物,通常在耐熱性試驗中透過率在4 〇 % 以上。在此,耐熱性試驗係將調整到2 mm之硬化物在1 5 0°C 之條件下保管72小時後,在波長370nm中測定厚方向之透 過率的試驗。 耐紫外線試驗、耐熱性試驗後之該透過率在4 〇 %以上 者’表示可防止由紫外線或熱造成之著色,該透過率在 5 0 %以上的硬化物尤佳。做為(B)成分者,使用實質上在分 子内不含雙鍵之脂環式羧酸酐,併用第四級鱗鹽、味唾化 合物、二氮雜雙環烯化合物及其鹽做成之硬化促進劑,再 藉由添加(C)成分及/或(D )成分之氧化防止劑,可得5 〇 %以 上之硬化物。 本發明硬化物之玻璃轉移溫度,通常在1 3 0^以上, 玻璃轉移溫度在1 3(TC以上時,因有耐熱性優異之傾向所 以較佳。 做為本發明之光二極管者,例如,將發光二極管元 件光一極管元件等光半導體以本發明之硬化物加以封裝
導線等之電極,接;::發:如在光半導體上視需要安裝 f、注型等之模組方法進樹脂組成物藉由轉移成 板上實裝光半導體, =^袁、硬化之方法進行,·在基 裴、硬化之方法。 本發明之樹脂組合物進行封 半導ί不ii::二,極管+,也可以裝著與螢光體等光 化物使ΐϊ:之it導體封裝用樹脂組成物硬化而成之硬 青色光、紫外光ί 1 ΐ ί之光透過性優異,即使長期照射 優。再者’,、 ,二犯里紐波長光也很少著色,光透過性 又士义使在鬲溫中長時間使用,光透過性仍優異。 化物,所樹脂組成物因可提供如此優異特性之硬 封裝材、透明淨料發ΐ二極管等透明之電1、電子零件用 ^ 透^塗枓、透明接著劑、玻璃代用材料等。 χ下以貫施例詳細說明本發明,但並不限定本發明之 乾㈤,例中之份及%若無特別指定,則表示重量基準。 〈硬化物之物性測定方法> (1) 初期透過率 使樹脂組成物硬化,冷卻到室溫時甚至在冷卻後2天 之内,以曰本分光(株)製V— 5 6 0分光光度計測定厚2mm之 硬化物的透過光譜,計算波長3 70nm中之透過率。 (2) 高溫保存後之透過率 將硬化物在1 50°C之送風乾燥爐中保存72小時後,以
314017.ptd 第24頁 1300073 五、發明說明(18) 與上述(1 )相同方法在波長3 7 0 nm中測定透過率。 (3 )紫外線照射後之透過率 硬化物使用ATLAS Ci 40 0 0 kISENON天氣器,在40 °C、5 0%R騰件下,在340 nm中以光量為〇· 55W/m2之光照 射3 0 0小時後,用與上述(1 )相同方法在波長3 7 〇 nm中測定 透過率。 (4 )玻璃轉移溫度 使用SI I製TMA— 1 0 0熱分析裝置,昇溫速度丨0。(3 /分、 荷重1 0g之條件下測定,計算TMA曲線之變彎點,以此做為 玻璃轉移溫度(Tg)。 (實施例1) 在10 0份(B)成分ΗN— 5500(甲基六氫苯二甲酸酐、曰 立化成(株)製)中、添加1份硬化劑U— CAT 5 0 0 3 (第4級鱗 溴化物、SUNAPPR0(株)製)製成硬化劑。 將5 5份上述硬化劑成分,與做為(a )成分之1 〇 〇份 PREMER— CP— 5 0M (縮水甘油甲基丙烯酸酯—丙烯酸甲酯 共聚合物、MW= 10,000、環氧基當量=320g/當量、Tg= 7 0 C ’曰本油脂(株)製)溶解到1 〇 〇份丙酮中,均勻混合 後,以真空乾燥機蒸餾除去丙酮,在室溫可得固狀之光半 導體封裝用樹脂組成物。此時,環氧基與酸酐之莫爾比為 等量。 將該樹脂組成物盛放在經1 〇 o°c預熱之玻璃板上,介 入2mm厚之間隔基後再以另一片經1 〇 〇°c預熱之玻璃板挾 住,用挾子固定時,該樹脂組合物熔融後成型為2mm厚板
314017.ptd 第25頁 1300073 五、發明說明(19) 狀。就以挾子固定形態在1 〇 〇°c放置2小時’接著持續在 1 2 0°C放置2小時使硬化而得厚度2mm之硬化物。 硬化物之物性測定結果在表1中表示。 (實施例2 ) 除了將硬化促進劑改為四一正一 丁基鱗溴化物(北興 化學工業(株)製、TBP- BB)之外,其餘與實施例!相同得 到樹脂組成物。 將該樹脂組成物,在1 0 0°C熱壓機加壓2小時使硬化 後,在1 2 0°C之硬化爐中硬化2小時,製得厚度2mm之硬化 物,硬化物之物性測定結果在表1中記述。 (實施例3) 除了相對於實施例2樹脂組成物1 0 0份添加〇 · 5份下述 式(C— 2)所示之紛系氧化防止劑之外,其餘與實施例2 相同製得樹脂組成物及硬化物,硬化物之物性測定纟士果如 表1所示。
(實施例4) 除了相對於實施例2之樹脂組合物1 〇 〇份添加〇 2 5份式 (C— 2)所示之酚系氧化防止劑及〇· 25份式(d — 2)所示> 之硫系氧化防止劑之外,其餘與實施例2相同製得樹脂組 成物及硬化物,硬化物之物性測定結果如表1所示。
314017.ptd 第26頁 1300073 五、發明說明(20) 0 0 〇12H25\〇Av-/^s/^A〇.Ci2H25 ( D - 2 ) (比較例1) 在1 0 0份(A )成分之EPOTED YD— 1 2 8Μ (雙紛A二縮水甘 油醚、環氧當量=1 8 5、東都化成(株)製)中,添加9 2人 份在實施例1製得之硬化劑成分,經攪拌、混合得到在室 溫中呈溶液狀之樹脂組成物。此時,環氧基與酸酐之莫爾 比為等量。將2片玻璃板挾入2mm之間隔基固定後做為模 具,在1 0 0°C預熱模具。在模具中注入樹脂組合物成型 後,在1 0 0°C加熱2小時,接著在1 2 0°C加熱2小時使硬化, 得厚度2mm之硬化物。 硬化物之物性測定結果在表1表示。 (比較例2) 做為(八)成分者為使用75份£?0丁£0丫1)—12 811«與2 5份 SELOXIDE 2021P( 3,4—環氧基環己基甲基3,4—環氧基 環己烧竣酸酯,環氧當量=134、DI C E L化學(株)製)之混 合物,該混合物((A )成分)之環氧當量為1 6 9。 該(A )成分1 0 0份與實施1所得之硬化劑成分1 〇 〇份,經 攪拌、混合,得到在室溫中呈溶液狀之樹脂組成物。此 時,環氧基與酸酐之物質量比(當量)為等量。接著,與 比較例1相同成型,使硬化,得到2mra#之硬化物。 硬化物.之物性測定結果如表1所示。 (比較例3 ) 在做為(A)成分之1〇〇份SELOXIDE 2 0 2 1 P中,添加實施
314017.ptd 第 27 頁 1300073 五、發明說明(21) 1所得之硬化劑成分1 2 7份,經攪拌、混合得到在室溫中呈 溶液狀之樹脂組成物。此時,環氧基與酸酐之物質量比 (當量)為等量。接著,與比較例1相同成型,使硬化, 得到2mm厚之硬化物。 硬化物之物性測定結果如表1所示 (比較例4) 在做為(A)成分之1 0 0份HBPADGE (嚴化雙紛A二縮水甘 油醚,環氧當量=2 1 0、丸善石油化學(株)製)中,添加 實施1所得之硬化劑成分8 1份,經攪拌、混合得到在室溫 中呈溶液狀之樹脂組成物。此時,環氧基與酸酐之莫爾比 為等量。接著,與比較例1相同成型,使硬化,得到2mm厚 之硬化物。 硬化物之物性測定結果如表1所示。 表1 實施例 比較例 1 2 3 4 1 2 3 4 透 (1) 76 78 80 79 71 67 67 73 過 〇 〇 〇 〇 〇 X X 〇 率 (2) 51 50 62 69 50 41 39 39 (%) 〇 〇 〇 〇 〇 〇 X X (3) 52 46 50 51 27 37 60 60 〇 〇 〇 〇 X X 〇 〇 Tg(°C) ⑷ 145 138 138 138 131 133 159 114 (1 )初期透過率
314017.ptd 第28頁 1300073 五、發明說明(22) 7 0 %以上以〇表示,未滿7 0 %以X表示 (2 )高溫(1 5 0°C X 7 2小時)保存後之透過率 4 0 %以上以〇表示,未滿4 0 %以X表示。 (3 )紫外光照射後之透過率 (在34 0nm波長以光量為0. 55W/m^:光照射3 0 0小時) 4 0 %以上以〇表示,未滿4 0 %以X表示。
314017.ptd 第29頁 1300073 圖式簡單說明 本案無圖式說明。
IlKIi 314017.ptd 第30頁
Claims (1)
- 威)〇_則 ;…,—’ ————— 案號f 91120834 奶年|0月qr]泊修正_ 六、申請專利範圍 一——~ ·— 1. 一種光半導體封裝用樹脂組成物,其係含有下述 (A)及(B)成分者: (A):含環氧基之(甲基)丙烯酸系聚合物, (B ):脂環式羧酸酐。 2 .如申請專利範圍第1項之樹脂組成物,其中,(A)成分 係選自丙烯酸烷酯、甲基丙烯酸烷酯、丙烯氰及甲基 丙烯氰所成組群中至少1種之單體與下述一般式(A— 1 )所示單體聚合而得之含環氧基之(甲基)丙烯酸系聚 合物者: R- X- CH2- E (A- 1) (式中,R表示碳原子數為2至1 2之脂烯基,X表示 羰氧基或亞甲氧基,E表示選自下述Η 之環氧基)。 3. 如申請專利範圍第1或2項之樹脂組成物,其中,(Α)成 分之環氧基當量係128g/當量以上,且該組成物之硬化 物具有1 3 0°C以上之玻璃轉移溫度者。 4. 如申請專利範圍第1或2項之樹脂組成物,其中,(B)成 分係六氫化苯二甲酸酐或甲基六氫化苯二甲酸酐。 5. 如申請專利範圍第1或2項之樹脂組成物,其中,以光314017 修正本.ptc 第31頁 1300073 -—-SS_ill20834_63年穸_月 q g_修正 六、申請專利範圍 " " ^S 半導體封袭用樹脂組成物含有氧化防止劑。 6 ·如申請專利範圍第5項之樹脂組成物,其中,氧化防止 齊Μ系含有盼系氧化防止劑(C)及/或硫系氧化防止 (D)。 ^ 7 ·如申請專利範圍第6項之樹脂組成物,其中,(c)成分 係下述一般式(C— 1 )所示之紛系氧化防止劑:(C-D (式中’喊示以^之整數)。 (D)成分 如申清專利範圍第6項之樹脂纟且成物,其中 係下述一般式(D-丨)所示之硫系氧化防止劑 〇 〇 0mH㈣、〇人,A〇^〇mH2m+i (D - ” (式中’ m表示1〇至22之整數)。 9 · 一種光半導體封裝硬化物,係由如申請專利範圍第 8項中任一項之光半導體用樹脂組合物硬化而成者。至 1 0·如申請專利範圍第9項之光半導體封裝硬化物,係調 整此硬化物厚度為2mm、於波長3 70nm中之厚度方向之 初期透過率在7 0 %以上;調整為2 m m之該硬化物在4 0 °C、50% RH之條件下,用340nm波長、光量〇.55W/m乏 光進行3 0 0小時照射試驗後,該硬化物厚度方向之透過 率在4 0 %以上;該硬化物之玻璃轉移溫度在1 3 0°C以上314017 修正本.ptc 第32頁 1300073 _案號91120834_年7月Π日 修正_ 六、申請專利範圍 者。 11. 一種光二極管,係將選自發光二極管元件及光二極管 元件所成組群之光半導體,以如申請專利範圍第9或 1 0項之硬化物加以封裝者。314017 修正本.ptc 第33頁
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JP2001323135A (ja) | 2000-03-06 | 2001-11-20 | Sumitomo Bakelite Co Ltd | 光半導体封止用エポキシ樹脂組成物および光半導体装置 |
JP2001272775A (ja) | 2000-03-24 | 2001-10-05 | Nippon Paint Co Ltd | 水性フォトソルダーレジスト組成物 |
US7034075B1 (en) * | 2000-11-28 | 2006-04-25 | H. B. Fuller Licensing & Financing Inc. | Low gloss powder coating compositions |
US20030059618A1 (en) * | 2001-03-23 | 2003-03-27 | Hideyuke Takai | Method of producing epoxy compound, epoxy resin composition and its applications, ultraviolet rays-curable can-coating composition and method of producing coated metal can |
CN1247651C (zh) * | 2001-09-14 | 2006-03-29 | 住友化学工业株式会社 | 光电半导体密封用树脂组合物 |
JP2003255120A (ja) | 2002-02-28 | 2003-09-10 | Showa Denko Kk | カラーフィルタ用樹脂組成物 |
US7291684B2 (en) * | 2003-03-11 | 2007-11-06 | Sumitomo Bakelite Co., Ltd. | Resin composition for encapsulating semiconductor chip and semiconductor device therewith |
SG109590A1 (en) * | 2003-08-29 | 2005-03-30 | Sumitomo Bakelite Co | Latent catalyst for epoxy resin, epoxy resin composition, and semiconductor device |
JP2006131867A (ja) * | 2004-10-08 | 2006-05-25 | Hitachi Chem Co Ltd | 樹脂組成物、及びそれを用いた光学部材とその製造方法 |
-
2002
- 2002-09-12 CN CNB028093712A patent/CN1247651C/zh not_active Expired - Fee Related
- 2002-09-12 US US10/472,091 patent/US7423083B2/en not_active Expired - Fee Related
- 2002-09-12 KR KR1020037015033A patent/KR100946609B1/ko not_active IP Right Cessation
- 2002-09-12 SG SG200302845A patent/SG97310A1/en unknown
- 2002-09-12 CA CA002442314A patent/CA2442314A1/en not_active Abandoned
- 2002-09-12 EP EP02798825A patent/EP1426394A4/en not_active Withdrawn
- 2002-09-12 TW TW091120834A patent/TWI300073B/zh not_active IP Right Cessation
- 2002-09-12 KR KR1020097001239A patent/KR100946607B1/ko not_active IP Right Cessation
- 2002-09-12 WO PCT/JP2002/009310 patent/WO2003025043A1/ja active Application Filing
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2008
- 2008-05-09 US US12/149,916 patent/US7919550B2/en not_active Expired - Fee Related
- 2008-09-19 JP JP2008240759A patent/JP2009041028A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
EP1426394A4 (en) | 2010-11-03 |
KR100946607B1 (ko) | 2010-03-09 |
US7423083B2 (en) | 2008-09-09 |
US20080249220A1 (en) | 2008-10-09 |
WO2003025043A1 (en) | 2003-03-27 |
CN1507462A (zh) | 2004-06-23 |
SG97310A1 (en) | 2006-09-29 |
US20040092668A1 (en) | 2004-05-13 |
CN1247651C (zh) | 2006-03-29 |
KR100946609B1 (ko) | 2010-03-09 |
KR20090027737A (ko) | 2009-03-17 |
JP2009041028A (ja) | 2009-02-26 |
EP1426394A1 (en) | 2004-06-09 |
KR20040032099A (ko) | 2004-04-14 |
CA2442314A1 (en) | 2003-03-27 |
US7919550B2 (en) | 2011-04-05 |
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