TWI401280B - Light semiconductor packaging materials - Google Patents
Light semiconductor packaging materials Download PDFInfo
- Publication number
- TWI401280B TWI401280B TW096114799A TW96114799A TWI401280B TW I401280 B TWI401280 B TW I401280B TW 096114799 A TW096114799 A TW 096114799A TW 96114799 A TW96114799 A TW 96114799A TW I401280 B TWI401280 B TW I401280B
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- TW
- Taiwan
- Prior art keywords
- meth
- acrylate
- group
- component
- ester
- Prior art date
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- 239000004065 semiconductor Substances 0.000 title claims description 61
- 239000005022 packaging material Substances 0.000 title description 3
- -1 acrylate compound Chemical class 0.000 claims description 60
- 239000000463 material Substances 0.000 claims description 37
- 230000003287 optical effect Effects 0.000 claims description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000002723 alicyclic group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000007870 radical polymerization initiator Substances 0.000 claims description 11
- 125000004386 diacrylate group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 description 22
- 239000000126 substance Substances 0.000 description 20
- 239000003963 antioxidant agent Substances 0.000 description 13
- 235000006708 antioxidants Nutrition 0.000 description 13
- 239000008393 encapsulating agent Substances 0.000 description 13
- 230000003078 antioxidant effect Effects 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
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- 229920006362 Teflon® Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
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- 238000006116 polymerization reaction Methods 0.000 description 6
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- 238000004383 yellowing Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- DCTLJGWMHPGCOS-UHFFFAOYSA-N Osajin Chemical compound C1=2C=CC(C)(C)OC=2C(CC=C(C)C)=C(O)C(C2=O)=C1OC=C2C1=CC=C(O)C=C1 DCTLJGWMHPGCOS-UHFFFAOYSA-N 0.000 description 4
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- 229910052799 carbon Inorganic materials 0.000 description 4
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- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910002601 GaN Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 2
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 2
- MZVABYGYVXBZDP-UHFFFAOYSA-N 1-adamantyl 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C(=C)C)C3 MZVABYGYVXBZDP-UHFFFAOYSA-N 0.000 description 2
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical group CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 230000006750 UV protection Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 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 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
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- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
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- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000005476 soldering Methods 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- CJVROGOPKLYNSX-UHFFFAOYSA-N (4-tert-butylcyclohexyl) carboxyoxy carbonate Chemical compound CC(C)(C)C1CCC(OC(=O)OOC(O)=O)CC1 CJVROGOPKLYNSX-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- AEUZJPHUNWZRCJ-UHFFFAOYSA-N 1-butyl-2-propan-2-ylbenzene Chemical group CCCCC1=CC=CC=C1C(C)C AEUZJPHUNWZRCJ-UHFFFAOYSA-N 0.000 description 1
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- YAGPRJYCDKGWJR-UHFFFAOYSA-N 2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxy-n,n-bis[2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxyethyl]ethanamine Chemical compound O1C2=C(C(C)(C)C)C=C(C(C)(C)C)C=C2C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP1OCCN(CCOP1OC2=C(C=C(C=C2C=2C=C(C=C(C=2O1)C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C)CCOP(OC1=C(C=C(C=C11)C(C)(C)C)C(C)(C)C)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C YAGPRJYCDKGWJR-UHFFFAOYSA-N 0.000 description 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
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- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RIQSLGAADRJNSG-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxyperoxy 2-ethylhexyl carbonate Chemical group CCCCC(CC)COC(=O)OOOOC(=O)OCC(CC)CCCC RIQSLGAADRJNSG-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
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- XTDKZSUYCXHXJM-UHFFFAOYSA-N 2-methoxyoxane Chemical compound COC1CCCCO1 XTDKZSUYCXHXJM-UHFFFAOYSA-N 0.000 description 1
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- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CMXLJKWFEJEFJE-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-[(4-methoxyphenyl)methylidene]propanedioate Chemical compound C1=CC(OC)=CC=C1C=C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(=O)OC1CC(C)(C)N(C)C(C)(C)C1 CMXLJKWFEJEFJE-UHFFFAOYSA-N 0.000 description 1
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- OTGOGSVKHCYCCC-UHFFFAOYSA-N carbonic acid;carbonoperoxoic acid Chemical class OC(O)=O.OOC(O)=O OTGOGSVKHCYCCC-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
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- YCWQBZCTYWZZAX-UHFFFAOYSA-N ditert-butyl 7,8-dioxabicyclo[4.2.0]octane-3,6-dicarboxylate Chemical compound C1C(C(=O)OC(C)(C)C)CCC2(C(=O)OC(C)(C)C)OOC21 YCWQBZCTYWZZAX-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 238000004020 luminiscence type Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITUWQZXQRZLLCR-UHFFFAOYSA-N n,n-dioctadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCCC ITUWQZXQRZLLCR-UHFFFAOYSA-N 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- KSSMAVGMASPUIE-UHFFFAOYSA-N pentyl propan-2-yl carbonate Chemical group CCCCCOC(=O)OC(C)C KSSMAVGMASPUIE-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920000193 polymethacrylate Polymers 0.000 description 1
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- HIAZZWAAYBFEJH-UHFFFAOYSA-N propan-2-yloxy propan-2-ylperoxycarbonyl carbonate Chemical compound CC(C)OOC(=O)OC(=O)OOC(C)C HIAZZWAAYBFEJH-UHFFFAOYSA-N 0.000 description 1
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- RGFNRWTWDWVHDD-UHFFFAOYSA-N sec-butyl ester of butyric acid Natural products CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 description 1
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
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- FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
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- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
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- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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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
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/02—Containers; Seals
- H01L23/10—Containers; Seals characterised by the material or arrangement of seals between parts, e.g. between cap and base of the container or between leads and walls of the container
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
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- Manufacturing & Machinery (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Led Device Packages (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本發明係關於光半導體裝置(半導體發光裝置)中之發光元件或受光元件等的封裝材料,以及光電轉換元件及光電轉換裝置,詳細而言,係關於可製造對紫外光或熱較穩定、難以產生黃變、且黏著性亦優異之硬化物的光半導體用透明封裝材料以及使用其之光電轉換元件及光電轉換裝置。
具有於沈積於結晶基板上之半導體層上形成p-n結,將該接合區域作為發光層之LED(發光二極體)晶片作為發光元件的光半導體裝置(半導體發光裝置)廣泛用於各種顯示裝置、顯示用機器等中。
作為該光半導體裝置之例,例如有:使用有GaN、GaAlN、InGaN及InAlGaN等氮化鎵系化合物半導體的可見光發光裝置或高溫運作電子裝置,最近不斷推進於藍色發光二極體、紫外發光二極體領域之開發。
具有LED晶片作為發光元件的光半導體裝置,於導線架之發光面側裝載LED晶片,藉由線結合使LED晶片與導線架電氣連接,進而利用兼具發光元件之保護及透鏡功能的樹脂加以封裝。
近年來,作為新型光源,白色LED受到關注,今後,以照明用途為中心其市場將會不斷擴大。白色LED有如下兩種類型得以實用化:於GaN之裸晶片上塗佈YAG螢光體,使GaN之藍色發光與螢光體之黃色發光混色而白色發光的類型;將紅.綠.藍之3個晶片封裝一體化而白色發光的類型。又,近年來,為改良色調,亦開發一種將紫外LED晶片作為光源,組合複數種螢光體材料的方法。進而,為於照明用途等中使用LED,業者要求改良其耐久性。
另一方面,作為封裝LED(發光二極體)晶片等發光元件時所使用的封裝材料,較多情況下使用環氧樹脂。由於環氧樹脂透明且加工性良好等原因而利用環氧樹脂。通常LED封裝用環氧樹脂大多為包含雙酚A縮水甘油醚與甲基六氫鄰苯二甲酸酐、胺系或磷系等硬化促進劑者。然而,該等成分會因吸收紫外光而生成羰基,故存在吸收可見光而產生黃變的缺點。為解決該問題,提出有使用經氫化之雙酚A縮水甘油醚的方法(非專利文獻1),但性能並不充分。
為改良因紫外光引起之黃變或亮度之下降,而廣泛使用矽氧樹脂。矽氧樹脂於紫外區域之透明性優異,故由紫外光引起之黃變或透過率之下降非常少。然而,矽氧樹脂存在如下問題:折射率低,故取光效率低,且極性低,故與導線架或反射器之黏著性差。
又,於表面封裝型LED中,以回焊方式進行焊接。於回焊爐內,在260℃之高溫下暴露約10秒,故先前之環氧樹脂或矽氧樹脂有時產生由熱引起之變形、破裂。
再者,於專利文獻1中揭示有,藉由使碳數為10以上之脂環式丙烯酸酯或甲基丙烯酸酯進行均聚合或共聚合,而獲得光學特性、耐熱性及耐水性優異的聚合物。作為該聚合物之用途,揭示有發光二極體之封裝劑,但需要進一步改良黏著性等。
專利文獻1:日本專利特開平2-67248號公報
非專利文獻1:NEDO「高效率光電轉換化合物半導體開發成果報告2001年度21世紀光計劃」
本發明鑒於如上狀況,其目的在於提供一種可製造對紫外線或熱較穩定、難以產生黃變、且黏著性亦優異之硬化物的光半導體用透明封裝材料以及光電轉換元件及光電轉換裝置。
本發明者等人,為達成上述目的而反覆進行努力研究,結果發現包含選自(甲基)丙烯酸酯改質矽酮油、長鏈(甲基)丙烯酸烷基酯、聚(甲基)丙烯酸烷二醇酯[polyalkylene glycol(meth)acrylate]之(甲基)丙烯酸酯化合物,碳數為6以上之脂環式烴基進行酯鍵結而成之(甲基)丙烯酸酯化合物及自由基聚合引發劑的光半導體封裝材料符合上述目的。本發明係基於該知識見解而完成者。
即,本發明提供以下之光半導體封裝材料、光電轉換元件及光電轉換裝置。
1.一種光半導體封裝材料,其特徵在於,包含:(A)選自(甲基)丙烯酸酯改質矽酮油、長鏈(甲基)丙烯酸烷基酯、及數量平均分子量為400以上之(甲基)丙烯酸聚烷二醇酯之一種以上的(甲基)丙烯酸酯化合物,(B)碳數為6以上之脂環式烴基進行酯鍵結而成之(甲基)丙烯酸酯化合物及(C)自由基聚合引發劑。
2.如上述1之光半導體封裝材料,其中(B)成分係選自金剛烷基、降莰基、異莰基及二環戊基(dicyclopentanyl)之一種以上之脂環式烴基進行酯鍵結而成的(甲基)丙烯酸酯化合物。
3.如上述1或2之光半導體封裝材料,其中(A)成分係氫化二丙烯酸聚丁二烯酯及/或數量平均分子量為400以上之二甲基丙烯酸聚乙二醇酯。
4.一種光電轉換元件,其特徵在於,其使用如上述1至3中任一項之光半導體封裝材料。
5.一種光電轉換裝置,其特徵在於,其使用如上述4之光電轉換元件。
本發明之光半導體封裝材料,可製造透明性優異、對紫外線或熱較穩定、不易黃變、黏著性亦優異之硬化物,可較好地用作光半導體裝置(半導體發光裝置)中之發光元件或受光元件等的封裝材料,尤其可較好地用作LED等光半導體用透明封裝材料。
本發明之光半導體封裝材料係包含(A)選自(甲基)丙烯酸酯改質矽酮油(a-1)、長鏈(甲基)丙烯酸烷基酯(a-2)、及數量平均分子量為400以上之(甲基)丙烯酸聚烷二醇酯(a-3)之一種以上的(甲基)丙烯酸酯化合物,(B)碳數為6以上之脂環式烴基進行酯鍵結而成之(甲基)丙烯酸酯化合物及(C)自由基聚合引發劑者。
首先,(A)成分之(甲基)丙烯酸酯改質矽酮油(a-1),係於末端具有丙烯酸基及/或甲基丙烯酸基,於骨架中含有二烷基聚矽氧烷的化合物。該(A)成分之(甲基)丙烯酸酯改質矽酮油(a-1),於多數情況下為二甲基聚矽氧烷之改質物,亦可代替甲基,以苯基或甲基以外之烷基來取代二烷基聚矽氧烷骨架中之烷基之全部或一部分。作為甲基以外之烷基,可列舉乙基、丙基等。作為如上所述者,具體而言可列舉信越化學工業股份有限公司製造之X-24-8201、X-22-174DX、X-22-2426、X-22-2404、X-22-164A、X-22-164C;東麗道康寧(Toray dowcorning)股份有限公司之BY16-152D、BY16-152、BY16-152C等。
又,作為(A)成分之(甲基)丙烯酸酯改質矽酮油(a-1),可使用具有丙烯醯氧基烷基末端或甲基丙烯醯氧基烷基末端之聚二烷基矽氧烷,具體而言,可列舉:甲基丙烯醯氧基丙基末端聚二甲基矽氧烷、(3-丙烯醯氧基-2-羥丙基)末端聚二甲基矽氧烷、丙烯醯氧基末端環氧乙烷二甲基矽氧烷-環氧乙烷ABA嵌段共聚物、甲基丙烯醯氧基丙基末端分支聚二甲基矽氧烷等。
於該等之中,就硬化後之透明性而言,可較好地使用(3-丙烯醯氧基-2-羥丙基)末端聚二甲基矽氧烷及丙烯醯氧基末端環氧乙烷二甲基矽氧烷-環氧乙烷ABA嵌段共聚物。
作為(A)成分之長鏈(甲基)丙烯酸烷基酯(a-2),可列舉:二丙烯酸氫化聚丁二烯酯、二丙烯酸氫化聚異戊二烯酯等具有氫化聚丁二烯、氫化聚異戊二烯骨架的丙烯酸系或甲基丙烯酸系化合物,或甲基丙烯酸硬脂酯等具有碳數為12以上之烷基的(甲基)丙烯酸酯化合物。作為碳數為12以上之烷基,可列舉:十二烷基、十四烷基、十六烷基、十八烷基(包含硬脂基)、二十烷基、三十烷基及四十烷基。藉由使用碳數為12以上之烷基者可獲得優異之黏著性。
於該等之中,就黏著性方面而言,較好的是二丙烯酸氫化聚丁二烯酯或甲基丙烯酸硬脂酯,尤其好的是二丙烯酸氫化聚丁二烯酯。
作為(A)成分之數量平均分子量為400以上之(甲基)丙烯酸聚烷二醇酯(a-3),可列舉:單甲基丙烯酸聚乙二醇酯、單甲基丙烯酸聚丙二醇酯、單甲基丙烯酸聚丁二醇酯、二甲基丙烯酸聚乙二醇酯、二甲基丙烯酸聚丙二醇酯、二甲基丙烯酸聚丁二醇酯等。藉由使用二丙烯酸氫化聚丁二烯酯及/或如數量平均分子量為400以上之二甲基丙烯酸聚乙二醇酯的數量平均分子量為400以上之(甲基)丙烯酸聚烷二醇酯,可獲得優異之韌性或黏著性。尤其可列舉數量平均分子量為400以上之二甲基丙烯酸聚乙二醇酯作為較佳成分。數量平均分子量之最大值並無特別限定,就與(B)成分之相容性之觀點而言,較好的是使用數量平均分子量為10000以下者。
於本發明中,作為(A)成分,可使用選自上述(a-1)成分中之至少一種、選自上述(a-2)成分中之至少一種、或選自上述(a-3)成分中之至少一種,或亦可自上述(a-1)成分、(a-2)成分及(a-3)成分中適當選擇組合。
作為(B)成分之碳數為6以上之脂環式烴基進行酯鍵結而成之(甲基)丙烯酸酯化合物的脂環式烴基,可列舉:環己基、2-十氫萘基、金剛烷基、1-甲基金剛烷基、2-甲基金剛烷基、聯金剛烷基、二甲基金剛烷基、降莰基、1-甲基-降莰基、5,6-二甲基-降莰基、異莰基、四環[4.4.0.12,5
.17,10
]十二烷基、9-甲基-四環[4.4.0.12,5
.17,10
]十二烷基、莰基、二環戊基等,於該等之中較好的是金剛烷基、降莰基、異莰基及二環戊基。其中更好的是金剛烷基,尤其好的是1-金剛烷基。
作為本發明之光半導體封裝材料中所使用的(B)成分之(甲基)丙烯酸酯化合物,可列舉具有上述脂環式烴基之(甲基)丙烯酸酯,例如:丙烯酸環己酯、甲基丙烯酸環己酯、(甲基)丙烯酸1-金剛烷酯、(甲基)丙烯酸降莰酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸二環戊酯等。於本發明中,作為(B)成分,可使用一種上述(甲基)丙烯酸酯,亦可組合兩種以上使用。
於本發明中,藉由使用脂環式烴基之碳數為6以上者,可獲得優異之耐熱性。又,酯取代基為脂環式烴基,不含芳香族等,故難以產生由紫外線引起之劣化。
與僅由單鍵形成之脂肪族烴進行酯鍵結而成之(甲基)丙烯酸酯化合物相比較,芳香族基或脂環式烴基進行酯鍵結而成之(甲基)丙烯酸酯化合物於耐熱性方面更優異。於本發明之光半導體封裝材料中所使用之(B)成分為脂環式結構,故較之具有芳香族結構之類似化合物,於紫外區域之光線吸收較少。因此,難以產生由紫外線引起之劣化。又,由於無雙鍵部位,因此難以受到氧化劣化,該方面亦有利於耐紫外線性。
此處,如金剛烷基、降莰基、異莰基、二環戊基之由兩個以上脂環式烴基組合而成之多環式基,更難以受到氧化劣化或由熱引起之劣化,故更好。
且,金剛烷基為三個穩定結構之6員環組合而成之多環式基,故於耐熱性或耐紫外線性方面尤其好。
本發明之光半導體封裝材料中之(A)成分與(B)成分之比例,相對於(A)成分與(B)成分之總量,較好的是將(A)成分設為10~80質量%,更好的是設為15~70質量%。藉由將(A)成分設為10質量%以上可獲得優異之黏著性或韌性,藉由設為80質量%以下可獲得優異之剛性或耐熱性。
作為(C)成分之自由基聚合引發劑,可列舉:甲基乙基酮過氧化物、甲基異丁基酮過氧化物、乙醯丙酮過氧化物、環己酮過氧化物、甲基環己酮過氧化物等酮過氧化物類;1,1,3,3-四甲基丁基氫過氧化物、異丙苯氫過氧化物、三級丁基氫過氧化物等氫過氧化物類;二異丁醯基過氧化物、雙-3,5,5-三甲基己醇過氧化物、月桂醯基過氧化物、苯甲醯基過氧化物、間甲苯甲醯基苯甲醯基過氧化物等二醯基過氧化物類;過氧二異丙苯、2,5-二甲基-2,5-二(三級丁過氧)己烷、1,3-雙(三級丁過氧異丙基)己烷、三級丁基異丙苯過氧化物、二(三級丁基)過氧化物、2,5-二甲基-2,5-二(三級丁過氧)己烯等二烷基過氧化物類;1,1-二(三級丁過氧-3,5,5-三甲基)環己烷、1,1-二(三級丁過氧)環己烷、2,2-二(三級丁過氧)丁烷等過氧化縮酮類;過氧新二碳酸-1,1,3,3-四甲基丁酯、過氧新二碳酸-α-異丙苯酯、過氧新二碳酸三級丁酯、過氧三甲基乙酸三級己酯、過氧三甲基乙酸三級丁酯、過氧-2-乙基己酸-1,1,3,3-四甲基酯、過氧-2-乙基己酸三級戊酯、過氧-2-乙基己酸三級丁酯、過氧異丁酸三級丁酯、過氧六氫對苯二甲酸二-三級丁酯、過氧-3,5,5-三甲基己酸-1,1,3,3-四甲基丁酯、過氧-3,5,5-三甲基己酸三級戊酯、過氧-3,5,5-三甲基己酸三級丁酯、過氧乙酸三級丁酯、過氧苯甲酸三級丁酯、過氧三甲基己二酸二丁酯等烷基過氧化酯類;過氧二碳酸二(3-甲氧基丁基)酯、過氧二碳酸二(2-乙基己基)酯、雙(二碳酸-1,1-丁基環己氧基酯)、二碳酸二異丙氧酯、過氧異丙基碳酸三級戊酯、過氧異丙基碳酸三級丁酯、過氧-2-乙基己基碳酸三級丁酯、1,6-雙(過氧羧基三級丁)己烷等過氧化碳酸酯類;2,2'-偶氮二異丁腈等偶氮化合物,進而,可列舉實施例中所使用之1,1-雙(三級己過氧)環己烷或過氧二碳酸(4-三級丁基環己基)酯等。
(C)成分之自由基聚合引發劑之使用量,相對於單體成分之總量100質量份,通常為0.01~5質量份,較好的是0.05~2質量份。上述自由基聚合引發劑可分別單獨使用,又,亦可併用複數種自由基聚合引發劑。
再者,於本發明中,單體成分之總量為(A)成分、(B)成分及後述之(D)成分[其他(甲基)丙烯酸酯化合物]的總量。
於本發明之光半導體封裝材料中,除上述自由基聚合引發劑外,亦可進而使用周知之抗氧化劑及光穩定劑等。作為抗氧化劑,有:酚系抗氧化劑、磷系抗氧化劑、硫系抗氧化劑、維生素系抗氧化劑、內酯系抗氧化劑、胺系抗氧化劑等。
作為酚系抗氧化劑,可列舉Irganox 1010(汽巴精化(Ciba specialty chemicals)公司,商標)、Irganox 1076(汽巴精化公司,商標)、Irganox 1330(汽巴精化公司,商標)、Irganox 3114(汽巴精化公司,商標)、Irganox 3125(汽巴精化公司,商標)、Irganox 3790(汽巴精化公司,商標)BHT、Cyanox 1790(美國氰胺(Cyanamide)公司,商標)、Sumilizer GA-80(住友化學公司,商標)等市售品。作為磷系抗氧化劑,可列舉Irgafos 168(汽巴精化公司,商標)、Irgafos 12(汽巴精化公司,商標)、Irgafos 38(汽巴精化公司,商標)、ADKSTAB 329K(旭電化公司,商標)、ADKSTAB PEP36(旭電化公司,商標)、ADKSTAB PEP-8(旭電化公司,商標)、Sardstab P-EPQ(Clariant公司,商標)、Weston 618(GE公司,商標)、Weston 619G(GE公司,商標)、Weston-624(GE公司,商標)等市售品。作為硫系抗氧化劑,例如可列舉:DSTP(YOSHITOMI)(吉富公司,商標)、DLTP(YOSHITOMI)(吉富公司,商標)、DLTOIB(吉富公司,商標)、DMTP(YOSHITOMI)(吉富公司,商標)、Seenox 412S(SHIPRO KASEI公司,商標)、Cyanox 1212(美國氰胺公司,商標)等市售品。
作為維生素系抗氧化劑,有:維生素E、Irganox E201(汽巴精化公司,商標,化合物名:2,5,7,8-四甲基-2(4',8',12'-三甲基十三烷基)苯幷呋喃-6-醇)等市售品。
作為內酯系抗氧化劑,可使用日本專利特開平7-233160號公報、日本專利特開平7-247278號公報中揭示者。又,有HP-136(汽巴精化公司,商標,化合物名:5,7-二三級丁基-3-(3,4-二甲基苯基)-3H-苯幷呋喃-2-酮)等。
作為胺系抗氧化劑,可列舉:Irgastab FS042(汽巴精化公司,商標)、GENOX EP(Crompton公司,商標,化合物名:二烷基-N-甲基胺氧化物)等市售品。
於使用該等添加劑之情形時,其使用量,相對於單體成分之總量100質量份,通常為0.005~5質量份,較好的是0.02~2質量份。該等添加劑亦可組合兩種以上使用。
進而,於本發明之光半導體封裝材料中,可添加光穩定劑。作為光穩定劑,可使用通常眾所周知者,較好的是受阻胺系光穩定劑。具體而言,作為商品名,可列舉:旭電化公司製造之ADK STAB LA-52、LA-57、LA-62、LA-63、LA-67、LA-68、LA-77、LA-82、LA-87、LA-94;CSC公司製造之Tinuvin 123、144、440、662、Chimassorb 2020、119、944;Hoechst公司製造之Hostavin N30;Cytec公司製造之Cyasorb UV-3346、UV-3526;GLC公司製造之Uval 299;Clariant公司製造之Sanduvor PR-31等。
於使用光穩定劑之情形時,其添加量,相對於單體成分之總量100質量份,通常為0.005~5質量份,較好的是0.002~2質量份,該等光穩定劑亦可組合兩種以上。又,亦可添加各種螢光體。
為獲得高強度,亦可於本發明之光半導體封裝材料中添加一種以上之其他(甲基)丙烯酸酯化合物[(A)成分及(B)成分以外之(甲基)丙烯酸酯化合物]作為(D)成分。作為(D)成分之(甲基)丙烯酸酯化合物,可列舉:二(甲基)丙烯酸乙二醇酯、二(甲基)丙烯酸丙二醇酯、(甲基)丙烯酸-1,4-丁二醇酯、二(甲基)丙烯酸-1,6-己二醇酯、二(甲基)丙烯酸-1,9-壬二醇酯、二(甲基)丙烯酸新戊二醇酯、數量平均分子量小於400之二(甲基)丙烯酸聚乙二醇酯或二(甲基)丙烯酸聚丙二醇酯、甲基丙烯酸甲氧基聚乙烯酯等(甲基)丙烯酸烷氧基聚烷二醇酯;二(甲基)丙烯酸環氧乙烷改質雙酚A酯、二(甲基)丙烯酸環氧氯丙烷改質雙酚A酯、二(甲基)丙烯酸環氧氯丙烷改質雙酚A酯、三(甲基)丙烯酸環氧丙烷改質甘油酯、三(甲基)丙烯酸三羥甲基丙烷酯、四(甲基)丙烯酸二(三羥甲基丙烷)酯、六(甲基)丙烯酸二季戊四醇酯、異三聚氰酸三(丙烯醯氧基乙基)酯、(甲基)丙烯酸甲氧基聚乙二醇酯等。
(D)成分之(甲基)丙烯酸酯化合物之含量,相對於(A)成分及(B)成分之總量,為50質量%以下。
於本發明中,對於(B)成分,可預先實施預聚合,進行黏度之調整,其後添加(A)成分等,製成光半導體封裝材料。可於上述(B)成分之(甲基)丙烯酸酯化合物中添加上述(C)成分之自由基聚合引發劑而進行預聚合。藉由添加經黏度調整之(B)成分作為本發明之光半導體封裝材料之成分,可調整光半導體封裝材料整體之黏度,使其後之硬化步驟變得簡單。
作為自由基聚合引發劑之添加量,並無特別限制,通常相對於(B)成分為10~20000 ppm,較好的是50~10000 ppm。藉由設為10 ppm以上,可確實地進行預聚合,藉由設為20000 ppm以下,可容易地控制反應。又,為精密控制反應,可於預聚合反應時使惰性溶劑存在。
又,進行預聚合時,可僅使用一種以上之(B)成分,亦可組合(B)成分以外之自由基聚合性化合物進行使用。較好的是,使具有碳數為6以上之脂環式烴基之(甲基)丙烯酸系化合物成為10質量%以上。藉由成為10質量%以上可避免剛性或耐熱性之降低。
作為預聚合溶劑,可使用通常之自由基聚合中所使用者。具體而言,可列舉:四氫呋喃等醚類,甲基乙基酮等酮類,甲苯等芳香族烴,己烷、環己烷等飽和烴,乙酸乙酯等酯類,三氯甲烷等鹵化烴。其中,較好的是可溶解於預聚合中生成之聚合物的溶劑。作為如此之溶劑,具體而言可列舉:四氫呋喃、甲苯、三氯甲烷等。
於預聚合中使用溶劑之情形時,較好的是於預聚合後進行蒸餾或減壓,餾去溶劑。此時,較好的是殘留之溶劑量為5質量%以下,更好的是1質量%以下。藉由使殘留溶劑量為5質量%以下,可於硬化封裝材料時避免發泡等之產生。
預聚合時之溫度依據自由基聚合引發劑之種類,通常為0~150℃,較好的是20~100℃。又,藉由預聚合而生成之聚合物與單體之混合物的黏度通常為100~10000 mPa.s,較好的是200~5000 mPa.s。
作為停止預聚合之方法,可採用如下方法:降低聚合反應系之溫度、於聚合反應系內導入空氣或氧氣、或添加對苯二酚單甲醚等聚合抑制劑等。
本發明之光半導體封裝材料,藉由以來自(C)成分之自由基所產生之溫度以上的溫度進行加熱處理,而可製造硬化物。硬化條件可考慮上述情況適當採用。藉此封裝之元件並無特別限制,例如可列舉:發光二極體(LED)晶片、半導體雷射、光二極體、光斷續器、光耦合器、光電晶體、電致發光元件、CCD、太陽電池等。作為本發明之光電轉換元件,可列舉以本發明之光半導體封裝材料封裝的LED等,作為本發明之光電轉換裝置,可列舉使用有該LED之照明裝置或信號器等各種半導體裝置。
其次,根據實施例,進一步詳細說明本發明,但本發明並不受該等例之任何限定。
再者,於各實施例及比較例中所得之光半導體封裝材料及硬化物的物性評價方法如下所述。數量平均分子量藉由NMR測定。
使用厚3 mm之試驗片作為樣品,依據JIS K7105進行測定(單位%)。測定裝置使用HGM-2DP(SUGA TEST INSTRUMENTS股份有限公司)。
又,於140℃之恆溫槽中將樣品放置100小時,將其前後之全光線透過率的差(%)作為△全光線透過率。
使用厚3 mm之試驗片作為樣品,依據JIS K7105測定黃變度(YI)。測定裝置使用SZ-optical SENSOR(日本電色工業(股)製造),進行以下耐候性試驗。
△YI1
:使用耐候性試驗機(Jasco international製造之solarbox 1500e),以500 W/m2
之功率對樣品照射100小時紫外光,測定紫外光照射前後之YI,將其差作為△YI1
。
△YI2
:於140℃之恆溫槽中將樣品放置100小時,將其前後之YI的差作為△YI2
。
初始霧值(%):使用SUGA TEST INSTRUMENTS製造,全自動直讀Haze Computer HGM-2DP(C光源),依據JIS K7105進行測定。
又,於140℃之恆溫槽中將樣品放置100小時,將其前後之霧值差(%)作為△霧值。
準備10個將聚醯胺複合材料與導線架一體成形,製成如圖1所示之零件者。於零件之凹部填充硬化性光半導體封裝材料(液態),以特定條件進行熱硬化。觀察每一個零件,觀察硬化物與反射器間的黏著狀態。藉由判斷10個零件中,有幾個未剝離之零件,來評價黏著性。
再者,作為聚醯胺複合材料,使用如下製造者:以半芳香族聚醯胺(AMODEL A4000,Solvay Advanced Polymer)/氧化鈦(PF-726,石原產業)/玻璃纖維(JAFT164G,Asahi Fiber Glass)=70/10/20(質量比)的比例進行調配,乾摻合後,投入內徑30 mm之雙軸擠出機之漏斗中,於機筒溫度285℃下進行熔融混練,成形為顆粒。
於25 g作為(B)成分之甲基丙烯酸1-金剛烷酯[大阪有機化學工業(股)製造]及25 g作為(A)成分之二丙烯酸氫化聚丁二烯酯(a-2)[信越化學工業(股)製造,商品名:SPBDA S30]中,添加0.2 g作為(C)成分之1,1-雙(三級己過氧)環己烷[日本油脂(股)製造,商品名:Perhexa HC]及0.2 g之過氧化二碳酸雙(4-三級丁基環己基)酯[日本油脂(股)製造,商品名:Peroyl TCP]進行混合,製成硬化性光半導體封裝材料。將該硬化性光半導體封裝材料灌入於2片玻璃板中夾入3 mm厚之鐵氟龍(註冊商標)製隔片而製成的單元、或圖1所示之零件的凹部中,於烘箱中於70℃下加熱3小時,繼而於160℃下加熱1小時後,冷卻至室溫,藉此獲得無色透明之板狀硬化物。將所得半導體封裝材料及硬化物之物
性評價結果示於第1表中。
於25 g作為(B)成分之甲基丙烯酸1-金剛烷酯[大阪有機化學工業(股)製造]及25 g作為(A)成分之(3-丙烯醯氧基-2-羥丙基)末端聚二甲基矽氧烷(a-1)[Azmax(股)製造,商品名:DMS-U22]中,添加0.2 g作為(C)成分之1,1-雙(過氧化第三己基)環己烷[日本油脂(股)製造,商品名:Perhexa HC]及0.2 g之過氧化二碳酸雙(4-三級丁基環己基)酯[日本油脂(股)製造,商品名:Peroyl TCP]進行混合,製成硬化性光半導體封裝材料。將該硬化性光半導體封裝材料灌入於2片玻璃板中夾入3 mm厚之鐵氟龍(註冊商標)製隔片而製成的單元、或圖1所示之零件的凹部中,於烘箱中於70℃下加熱3小時,繼而於160℃下加熱1小時後,冷卻至室溫,藉此獲得無色透明之板狀硬化物。將所得半導體封裝材料及硬化物之物性評價結果示於第1表中。
於25 g之作為(B)成分之甲基丙烯酸1-金剛烷酯[大阪有機化學工業(股)製造]及25 g之作為(A)成分之# 400二甲基丙烯酸聚乙二醇酯(a-3)[新中村化學工業(股)製造,商品名:NK ester 9G,數量平均分子量540]中,添加0.2 g作為(C)成分之1,1-雙(三級己過氧)環己烷[日本油脂(股)製造,商品名:Perhexa HC]及0.2 g之過氧化二碳酸雙(4-三級丁基環己基)酯[日本油脂(股)製造,商品名:Peroyl TCP]進行混合,製成硬化性光半導體封裝材料。將該硬化性光半
導體封裝材料灌入於2片玻璃板中夾入3 mm厚之鐵氟龍(註冊商標)製隔片而製成的單元、或圖1所示之零件的凹部中,於烘箱中於70℃下加熱3小時,繼而於160℃下加熱1小時後,冷卻至室溫,藉此獲得無色透明之板狀硬化物。將所得半導體封裝材料及硬化物之物性評價結果示於第1表中。
於25 g作為(B)成分之甲基丙烯酸1-金剛烷酯[大阪有機化學工業(股)製造]及5 g作為(A)成分之# 400二甲基丙烯酸聚乙二醇酯(a-3)[新中村化學工業(股)製造,商品名:NK ester 9G,數量平均分子量540]及20 g之甲基丙烯酸硬脂酯(a-2)[Mitsubishi Rayon(股)製造]中,添加0.2 g作為(C)成分之1,1-雙(三級己過氧)環己烷[日本油脂(股)製造,商品名:Perhexa HC]及0.2 g之過氧化二碳酸雙(4-三級丁基環己基)酯[日本油脂(股)製造,商品名:Peroyl TCP]進行混合,製成硬化性光半導體封裝材料。將該硬化性光半導體封裝材料灌入於2片玻璃板中夾入3 mm厚之鐵氟龍(註冊商標)製隔片而製成的單元、或圖1所示之零件的凹部中,於烘箱中於70℃下加熱3小時,繼而於160℃下加熱1小時後,冷卻至室溫,藉此獲得無色透明之板狀硬化物。將所得半導體封裝材料及硬化物之物性評價結果示於第1表中。
對50 g作為(B)成分之甲基丙烯酸1-金剛烷酯[大阪有機
化學工業(股)製造]及50 g作為(D)成分之# 400甲基丙烯酸甲氧基聚乙二醇酯[新中村化學工業(股)製造,商品名:NK ester M-90G,數量平均分子量470],添加100 ppm作為(C)成分之過氧化二碳酸(4-三級丁基環己基)酯(日本油脂(股)製造,商品名:Peroyl TCP),於氮環境下,以60℃進行2小時反應。所得預聚合漿料之黏度為600 mPa.s。
於25 g之該漿料中添加12.5 g作為(B)成分之甲基丙烯酸1-金剛烷酯[大阪有機化學工業(股)製造]及12.5 g作為(A)成分之# 400二甲基丙烯酸聚乙二醇酯(a-3)[新中村化學工業(股)製造,商品名:NK ester 9G,數量平均分子量540]、0.2 g作為(C)成分之1,1-雙(三級己過氧)環己烷[日本油脂(股)製造,商品名:Perhexa HC]及0.2 g之過氧化二碳酸(4-三級丁基環己基)酯[日本油脂(股)製造,商品名:Peroyl TCP]進行混合,製成硬化性光半導體封裝材料。將該硬化性光半導體封裝材料灌入於2片玻璃板中夾入3 mm厚之鐵氟龍(註冊商標)製隔片而製成的單元、或圖1所示之零件的凹部中,於烘箱中於70℃下加熱3小時,繼而於160℃下加熱1小時後,冷卻至室溫,藉此獲得無色透明之板狀硬化物。將所得半導體封裝材料及硬化物之物性評價結果示於第1表中。
再者,本實施例係使用使(D)成分及(B)成分之一部分進行預聚合而得者的情形,於第1表中*表示預聚合中所使用之分量。
於14 g之雙酚A型液態環氧樹脂單體[日本環氧樹脂(股)製造之Epikote 828]中添加14 g之甲基六氫鄰苯二甲酸酐[和光純藥工業(股)製造),調配0.028 g之1,8-二氮雜雙環[5,4,0]-7-十一烯(Sigma-Aldrich Japan(股)製造],均勻混合後,灌入密封的鐵氟龍(註冊商標)製隔片中,於烘箱中於130℃下以3小時緩慢升溫後,逐漸冷卻至室溫,藉此獲得板狀樣品。將所得半導體封裝材料及硬化物之物性評價結果示於第1表中。
本發明之光半導體封裝材料,可製造具有透明性優異、對紫外線或熱較穩定、難以產生黃變、且黏著性亦優異之特性的硬化物,可較好地用作光半導體裝置(半導體發光裝置)中之發光元件或受光元件等的封裝材料,尤其可較好地用作LED等光半導體用透明封裝材料。
圖1係實施例之黏著性試驗中測定與反射器之黏著數時之測定裝置的說明圖。
Claims (5)
- 一種光半導體封裝材料,其特徵在於,包含:(A)選自(甲基)丙烯酸酯改質矽酮油、具有氫化聚丁二烯或氫化聚異戊二烯骨架的(甲基)丙烯酸酯或長鏈(甲基)丙烯酸烷基酯之一種以上的(甲基)丙烯酸酯化合物,(B)碳數為6以上之脂環式烴基進行酯鍵結而成之(甲基)丙烯酸酯化合物及(C)自由基聚合引發劑。
- 如請求項1之光半導體封裝材料,其中(B)成分係選自金剛烷基、降莰基、異莰基及二環戊基(dicyclopentanyl)之一種以上之脂環式烴基進行酯鍵結而成的(甲基)丙烯酸酯化合物。
- 如請求項1或2之光半導體封裝材料,其中(A)成分係二丙烯酸氫化聚丁二烯酯。
- 一種光電轉換元件,其特徵在於,其使用如請求項1至3中任一項之光半導體封裝材料。
- 一種光電轉換裝置,其特徵在於,其使用如請求項4之光電轉換元件。
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JP2006127631 | 2006-05-01 |
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TW200804468A TW200804468A (en) | 2008-01-16 |
TWI401280B true TWI401280B (zh) | 2013-07-11 |
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TW096114799A TWI401280B (zh) | 2006-05-01 | 2007-04-26 | Light semiconductor packaging materials |
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US (1) | US20100234527A1 (zh) |
JP (1) | JP5580985B2 (zh) |
KR (1) | KR101365834B1 (zh) |
CN (1) | CN101432357B (zh) |
DE (1) | DE112007001060T5 (zh) |
TW (1) | TWI401280B (zh) |
WO (1) | WO2007129536A1 (zh) |
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TWI389925B (zh) | 2004-11-09 | 2013-03-21 | Idemitsu Kosan Co | Optoelectronic semiconductors |
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EP2463316B1 (en) * | 2009-08-04 | 2016-06-08 | Idemitsu Kosan Co., Ltd. | Acrylate composition |
JP5621236B2 (ja) * | 2009-10-05 | 2014-11-12 | 日立化成株式会社 | ウレタン樹脂組成物、硬化体及び硬化体を用いた光半導体装置 |
JP2011129901A (ja) * | 2009-11-19 | 2011-06-30 | Mitsubishi Chemicals Corp | 半導体発光装置の製造方法 |
US20110242818A1 (en) * | 2010-03-30 | 2011-10-06 | Panasonic Corporation | Highly reflective white material and led package |
JP5775525B2 (ja) | 2010-10-25 | 2015-09-09 | 出光興産株式会社 | (メタ)アクリレート系組成物 |
KR101771175B1 (ko) | 2011-06-10 | 2017-09-06 | 삼성전자주식회사 | 광전자 소자 및 적층 구조 |
JP6020895B2 (ja) * | 2011-08-22 | 2016-11-02 | 三菱レイヨン株式会社 | 硬化性樹脂組成物、硬化物及び光学部材 |
US8778704B1 (en) * | 2013-02-13 | 2014-07-15 | Freescale Semiconductor, Inc. | Solar powered IC chip |
US8809078B1 (en) | 2013-02-13 | 2014-08-19 | Freescale Semiconductor, Inc. | Solar powered IC chip |
JP2018168219A (ja) * | 2017-03-29 | 2018-11-01 | 日立化成株式会社 | 樹脂組成物及び樹脂硬化物 |
WO2021002375A1 (ja) * | 2019-07-04 | 2021-01-07 | 積水化学工業株式会社 | 有機el表示素子用封止剤 |
CN110387210B (zh) * | 2019-07-31 | 2021-10-19 | 中广核达胜加速器技术有限公司 | 一种基于eb固化的胶黏剂及具有其的云母带的制备方法 |
AR126394A1 (es) * | 2021-07-07 | 2023-10-11 | Ypf Tecnologia Sa | Surfactantes poliméricos que tienen tolerancia aumentada a la sal y método de preparación de los mismos |
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- 2007-04-19 DE DE112007001060T patent/DE112007001060T5/de not_active Withdrawn
- 2007-04-19 CN CN2007800157186A patent/CN101432357B/zh active Active
- 2007-04-19 WO PCT/JP2007/058515 patent/WO2007129536A1/ja active Application Filing
- 2007-04-19 KR KR1020087026599A patent/KR101365834B1/ko active IP Right Grant
- 2007-04-19 JP JP2008514419A patent/JP5580985B2/ja active Active
- 2007-04-26 TW TW096114799A patent/TWI401280B/zh active
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Publication number | Publication date |
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CN101432357A (zh) | 2009-05-13 |
KR20090009841A (ko) | 2009-01-23 |
TW200804468A (en) | 2008-01-16 |
JP5580985B2 (ja) | 2014-08-27 |
CN101432357B (zh) | 2012-06-27 |
DE112007001060T5 (de) | 2009-03-12 |
US20100234527A1 (en) | 2010-09-16 |
KR101365834B1 (ko) | 2014-02-21 |
JPWO2007129536A1 (ja) | 2009-09-17 |
WO2007129536A1 (ja) | 2007-11-15 |
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