CN101056900B - 光半导体密封材料 - Google Patents
光半导体密封材料 Download PDFInfo
- Publication number
- CN101056900B CN101056900B CN2005800382537A CN200580038253A CN101056900B CN 101056900 B CN101056900 B CN 101056900B CN 2005800382537 A CN2005800382537 A CN 2005800382537A CN 200580038253 A CN200580038253 A CN 200580038253A CN 101056900 B CN101056900 B CN 101056900B
- Authority
- CN
- China
- Prior art keywords
- ester
- optical semiconductor
- methacrylic acid
- methyl
- vinylformic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 47
- 230000003287 optical effect Effects 0.000 title claims abstract description 38
- 239000003566 sealing material Substances 0.000 title abstract description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 10
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 10
- -1 hydroxy acryl Chemical group 0.000 claims description 59
- 239000000463 material Substances 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 20
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 14
- 229920005992 thermoplastic resin Polymers 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 238000005476 soldering Methods 0.000 abstract description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 2
- 125000002723 alicyclic group Chemical group 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 abstract 1
- 239000011342 resin composition Substances 0.000 abstract 1
- 238000004383 yellowing Methods 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 26
- 239000000178 monomer Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 125000004185 ester group Chemical group 0.000 description 20
- 230000000704 physical effect Effects 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 18
- 238000011156 evaluation Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000003963 antioxidant agent Substances 0.000 description 14
- 230000003078 antioxidant effect Effects 0.000 description 14
- 235000006708 antioxidants Nutrition 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 9
- 239000007870 radical polymerization initiator Substances 0.000 description 9
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 7
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 7
- 238000005502 peroxidation Methods 0.000 description 7
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 230000000630 rising effect Effects 0.000 description 5
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229910002601 GaN Inorganic materials 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920002050 silicone resin Polymers 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- WKJICCKTDQDONB-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)OCC1OC1 WKJICCKTDQDONB-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- DGZIMLVEXGVYDW-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(=O)C=C DGZIMLVEXGVYDW-UHFFFAOYSA-N 0.000 description 2
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 2
- OXGOEZHUKDEEKS-UHFFFAOYSA-N 3-tert-butylperoxy-1,1,5-trimethylcyclohexane Chemical compound CC1CC(OOC(C)(C)C)CC(C)(C)C1 OXGOEZHUKDEEKS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- 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 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- OMSXMOJHPOJGHP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy heptaneperoxoate Chemical compound CCCCCCC(=O)OOOC(C)(C)C OMSXMOJHPOJGHP-UHFFFAOYSA-N 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-N 0.000 description 1
- RTPQXHZLCUUIJP-UHFFFAOYSA-N 1,2-dimethyladamantane Chemical compound C1C(C2)CC3CC1C(C)C2(C)C3 RTPQXHZLCUUIJP-UHFFFAOYSA-N 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
- AQPZTEIAYGPWGS-UHFFFAOYSA-N 1,3-dimethyl-5-phenoxybenzene Chemical compound CC1=CC(C)=CC(OC=2C=CC=CC=2)=C1 AQPZTEIAYGPWGS-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- QZYOLNVEVYIPHV-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)peroxybenzene Chemical compound CC1=CC=CC(OOC=2C=C(C)C=CC=2)=C1 QZYOLNVEVYIPHV-UHFFFAOYSA-N 0.000 description 1
- UZUCFTVAWGRMTQ-UHFFFAOYSA-N 1-methyladamantane Chemical compound C1C(C2)CC3CC2CC1(C)C3 UZUCFTVAWGRMTQ-UHFFFAOYSA-N 0.000 description 1
- PITQFWWNUHMYIC-UHFFFAOYSA-N 1-tert-butyl-4-(4-tert-butylcyclohexyl)peroxycyclohexane Chemical compound C1CC(C(C)(C)C)CCC1OOC1CCC(C(C)(C)C)CC1 PITQFWWNUHMYIC-UHFFFAOYSA-N 0.000 description 1
- GOAHRBQLKIZLKG-UHFFFAOYSA-N 1-tert-butylperoxybutane Chemical compound CCCCOOC(C)(C)C GOAHRBQLKIZLKG-UHFFFAOYSA-N 0.000 description 1
- LCALBRTUIUNTQU-UHFFFAOYSA-N 1-tert-butylperoxyhex-1-ene Chemical compound CCCCC=COOC(C)(C)C LCALBRTUIUNTQU-UHFFFAOYSA-N 0.000 description 1
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-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
- 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
- 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
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- GILMNGUTRWPWSY-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(O)COC(=O)C=C GILMNGUTRWPWSY-UHFFFAOYSA-N 0.000 description 1
- VMODAALDMAYACB-UHFFFAOYSA-N 2-methyladamantane Chemical compound C1C(C2)CC3CC1C(C)C2C3 VMODAALDMAYACB-UHFFFAOYSA-N 0.000 description 1
- UPTHZKIDNHJFKQ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane-1,2,3-triol Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(O)CO UPTHZKIDNHJFKQ-UHFFFAOYSA-N 0.000 description 1
- RPBWMJBZQXCSFW-UHFFFAOYSA-N 2-methylpropanoyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(=O)C(C)C RPBWMJBZQXCSFW-UHFFFAOYSA-N 0.000 description 1
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- C08F20/18—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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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Abstract
本发明提供一种包含将含金刚烷基、降冰片烷基、双环戊烷基等碳数7以上的脂环式烃基的甲基丙烯酸酯进行自由基聚合而成的聚合物的光半导体密封材料、及含有将上述含脂环式烃基的甲基丙烯酸酯50~97质量%与含羟基丙烯酸酯3~50质量%进行自由基聚合而成的聚合物的光半导体密封材料。本发明的光半导体密封材料具有如下特性:透明性优良;对紫外线稳定而不发生黄变;耐热性、折射率的平衡优良;而且加工性也优良,在回流焊锡等加热工序中不会发生变形及裂缝,可以优选用作光半导体装置(半导体发光装置)中的发光元件和受光元件等的密封材料。
Description
技术领域
本发明涉及一种光半导体装置(半导体发光装置)中的发光元件或受光元件等的密封材料及光电变换元件与光电变换装置。详细地来讲,提供一种对紫外线稳定而不发生黄变、且耐热性、折射率的平衡优良的固化物,并且还涉及一种加工性也优良的光半导体用透明密封材料及使用有它的光电变换元件与光电变换装置。
背景技术
用结晶基板上成长的半导体层形成p-n偶合,备有以将该接合区域设定为发光层的LED(发光二极管)芯片为发光元件的光半导体装置(半导体发光装置)被广泛用于各种显示装置、显示用设备等中。
作为该光半导体装置的实例,例如举出,使用了GaN、GaAlN、InGaN及InAlGaN等氮化镓系化合物半导体的可见光发光设备、高温动作电子设备,最近,正在蓝色发光二极管、紫外发光二极管领域进行开发。
备有以LED芯片作为发光元件的光半导体装置的组成如下:在引线框架的发光面侧搭载LED芯片,利用引线接合将LED芯片和引线框架电连接,再利用兼具发光元件的保护及透镜功能的树脂进行密封。
近年来,作为新型光源的白色LED倍受瞩目,今后,可以说以照明用途为中心的市场前景巨大。被实用化的白色LED有以下两种类型:在GaN的裸芯片上涂敷YAG荧光体,将GaN的蓝色发光和荧光体的黄色发光进行混色,使其进行白色发光;将红·绿·蓝3个芯片封装为1体,使其进行白色发光。另外,近年来考虑色调的改良还开发了将紫外LED芯片作成光源、将多个荧光体材料组合的方法。而且,为了将LED用于照明用途等,期待改良其耐久性。
另一方面,作为密封LED(发光二极管)芯片等发光元件时使用的密封材料,大多利用环氧树脂。环氧树脂因其透明、加工性良好等因素而被利用。通常情况下,LED密封用环氧树脂几乎都是双酚A缩水甘油醚和甲基六氢邻苯二甲酸酐、胺类或磷类等固化促进剂构成的物质。但是,由于这些成分因吸收紫外线而生成羰基,因此,存在吸收可见光发生黄变的缺点。为了解决该问题,提出了使用氢化过的双酚A缩水甘油醚的方法(非专利文献1),但其性能并不充分。
为了改良由紫外线引起的黄变和亮度降低,可以广泛使用硅树脂。硅树脂在紫外区域中透明性优良,由紫外线引起的黄变和透过率降低非常少。但是,硅树脂存在的问题在于:由于其折射率低,因此光的取出效率低;由于其极性低,因此与引线框架、反射板的密合性差。
另外,在表面安装型的LED中,利用回流焊锡方式来进行焊接。在回流炉内,由于被在260℃的温度暴露约10秒钟,因此,现有的环氧树脂和硅树脂有时会因热而发生变形、裂缝。
非专利文献1:NEDO“高效率电光变换化合物半导体开发成果报告平成13年度21世纪的光计划”
发明内容
根据以上情况,本发明的目的在于,提供一种对紫外线稳定而不发生黄变、且耐热性、折射率的平衡优良的固化物,并且还提供一种粘接性和加工性也优良的光半导体用透明密封材料及光电变换元件与光电变换装置。
本发明者为了实现上述目的而反复进行了潜心研究,结果发现,通过使用将含碳数7以上的脂环式烃基的甲基丙烯酸酯进行自由基聚合而成的聚合物,可以得到折射率和加工性优良的光半导体用密封材料,另外,含有该含脂环式烃基的甲基丙烯酸酯和含羟基丙烯酸酯的热固性树脂组合物,可以提供不仅在粘接性和加工性优良,而且对紫外线稳定而不发生黄变、且耐热性、折射率的平衡优良的固化物,而且可以得到优良的光半导体用密封材料。本发明是基于这样的见解来完成的。
亦即,本发明提供以下的光半导体密封材料、光电变换元件及光电变换装置。
(1)一种光半导体密封材料,其特征在于,包含将含碳数7以上的脂环式烃基的甲基丙烯酸酯进行自由基聚合而成的聚合物。
(2)如(1)所述的光半导体密封材料,其特征在于,其还包含0.5~20质量%的热塑性树脂。
(3)如(1)或(2)任一项所述的光半导体密封材料,其特征在于,碳数7以上的脂环式烃基是包含金刚烷基、降冰片烷基或双环戊烷基的基团。
(4)一种光半导体密封材料,其特征在于,包含将50~97质量%的含碳数7以上的脂环式烃基的甲基丙烯酸酯和3~50质量%的含羟基丙烯酸酯进行自由基聚合而成的聚合物。
(5)如(4)所述的光半导体密封材料,其特征在于,碳数7以上的脂环式烃基是包含金刚烷基、降冰片烷基或双环戊烷基的基团。
(6)一种光电变换元件,其特征在于,使用了如(1)~(5)任一项所述的光半导体密封材料。
(7)一种光电变换装置,其特征在于,使用了如(6)所述的光电变换元件。
附图说明
图1是表示实施例的粘接性实验中测定粘接强度时的试验片的粘接情况的说明图。
图2是表示实施例的粘接性实验中测定与反射板的粘接数时的测定装置的说明图。
具体实施方式
首先,本发明的光半导体密封材料包含将含碳数7以上的脂环式烃基的甲基丙烯酸酯进行自由基聚合而成的聚合物。
作为碳数7以上的脂环式烃基,可以举例为:2-十氢萘基、金刚烷基、1-甲基金刚烷基、2-甲基金刚烷基、联金刚烷基、二甲基金刚烷基、降冰片烷基、1-甲基-降冰片烷基、5,6-二甲基-降冰片烷基、异冰片烷基、四环[4.4.0.12.5.17.10]十二烷基、9-甲基-四环[4.4.0.12.5.17.10]十二烷基、冰片基、双环戊烷基等,优选金刚烷基、降冰片烷基及双环戊烷基。其中,进一步优选金刚烷基,特别优选1-金刚烷基。用于本发明的光半导体密封材料的单体,可以使用具有这些脂环式烃基的甲基丙烯酸酯。当脂环式烃基的碳数低于7时,其耐热性、折射率大多不充分。另外,当该甲基丙烯酸酯的酯取代基含有芳香族等时,容易发生由紫外线引起的老化。
本发明的光半导体密封材料包含的含脂环式烃基的甲基丙烯酸酯的自由基聚合物,可以是上述含碳数7以上的脂环式烃基的甲基丙烯酸酯的均聚物,也可以是将该酯的2种以上组合聚合而成的共聚物。或者,也可以是将1种以上含碳数7以上的脂环式烃基的甲基丙烯酸酯和1种以上作为共聚用单体的其它(甲基)丙烯酸酯聚合而成的共聚物。其它(甲基)丙烯酸酯例如有:丙烯酸甲酯、丙烯酸氟代甲酯、丙烯酸乙酯、丙烯酸丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸2,2,2-三氟乙酯、丙烯酸2-羟乙酯、丙烯酸1,2,2,2-四氯乙酯、丙烯酸丙酯、丙烯酸异丙酯、丙烯酸2-氯-1-(氯二氟甲基)乙酯、丙烯酸1,2,2,2-四氟-1-(三氟甲基)乙酯、丙烯酸2,2,2-三氟-1-(三氟甲基)乙酯、丙烯酸2,2,3,3,3-五氟丙酯、丙烯酸1-甲基乙酯、丙烯酸2-(甲硫基)乙酯、丙烯酸2-甲氧基乙酯、丙烯酸2-羟丙酯、丙烯酸2-丙烯酯、丙烯酸1-乙氧基-2,2,2-三氟乙酯、丙烯酸2-(乙硫基)乙酯、丙烯酸2-乙氧基乙酯、丙烯酸2,2,3,3,4,4,4-七氟丁酯、丙烯酸3-(甲硫基)丙酯、丙烯酸1-甲基丙酯、丙烯酸2,2,3,4,4,4-六氟丁酯、丙烯酸4-氧杂戊酯、丙烯酸2-(三氟乙氧基)乙酯、丙烯酸2-(1,1,2,2-四氟乙氧基)乙酯、丙烯酸3-(乙硫基)丙酯、丙烯酸1-乙基丙酯、丙烯酸2,2,3,3,4,4,5,5-八氟戊酯、丙烯酸2,2-二甲基丙酯、丙烯酸2,2,3,3,4,4,5,5,5-九氟戊酯、丙烯酸4-甲硫基丁酯、丙烯酸2-甲基丁酯、丙烯酸3-甲基丁酯、丙烯酸4-氧杂己酯、丙烯酸3-甲氧基丁酯、丙烯酸己酯、丙烯酸环己酯、丙烯酸2-乙基丁酯、丙烯酸2-甲基戊酯、丙烯酸4-甲基-2-戊酯、丙烯酸苯酯、丙烯酸2-氯苯酯、丙烯酸4-氯苯酯、丙烯酸2,4-二氯苯酯、五氯丙烯酸酯、3,3,4,4,5,5,6,6,6-十一氟丙烯酸酯、五氟丙烯酸酯、丙烯酸庚酯、丙烯酸苯基甲酯、丙烯酸2-甲基苯酯、丙烯酸3-甲基苯酯、丙烯酸4-甲基苯酯、丙烯酸1-甲基己酯、丙烯酸4-甲氧基苯酯、丙烯酸辛酯、丙烯酸2-苯基乙酯、丙烯酸1-甲基庚酯、丙烯酸壬酯、丙烯酸癸酯等丙烯酸酯;甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸2-氯乙酯、甲基丙烯酸2,2,2-三氟乙酯、甲基丙烯酸2-硝基乙酯、甲基丙烯酸2-羟乙酯、甲基丙烯酸丙酯、甲基丙烯酸异丙酯、甲基丙烯酸2-甲氧基乙酯、甲基丙烯酸烯丙酯、甲基丙烯酸缩水甘油酯、甲基丙烯酸2-氯丙酯、甲基丙烯酸三甲基甲硅烷基酯、甲基丙烯酸2,2,2-三氟-1-甲基乙酯、甲基丙烯酸2,2,3,3-四氟丙酯、甲基丙烯酸七氟异丙酯、甲基丙烯酸六氟异丙酯、甲基丙烯酸丁酯、甲基丙烯酸异丁酯、甲基丙烯酸仲丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸2-乙氧基乙酯、二甘醇甲基丙烯酸酯、甲基丙烯酸九氟叔丁酯、甲基丙烯酸2,2,3,3,4,4,4-七氟丁酯、甲基丙烯酸戊酯、甲基丙烯酸环戊酯、甲基丙烯酸2,2-二乙基丙酯、甲基丙烯酸1-甲基丁酯、甲基丙烯酸异戊酯、甲基丙烯酸2,2,3,3,4,4,5,6-八氟戊酯、甲基丙烯酸己酯、甲基丙烯酸环己酯、甲基丙烯酸苯酯、甲基丙烯酸3,3-二甲基丁酯、甲基丙烯酸2-乙基丁酯、甲基丙烯酸1-甲基环己酯、甲基丙烯酸2-甲基环己酯、甲基丙烯酸3-甲基环己酯、甲基丙烯酸4-甲基环己酯、甲基丙烯酸1,1-二乙基丙酯、甲基丙烯酸2-甲基苯酯、甲基丙烯酸3-甲基苯酯、甲基丙烯酸4-甲基苯酯、甲基丙烯酸苄酯、甲基丙烯酸2-甲氧基苯酯、甲基丙烯酸2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚酯、甲基丙烯酸辛酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸2-苯基乙酯、甲基丙烯酸2,4-二甲基苯酯、甲基丙烯酸2,5-二甲基苯酯、甲基丙烯酸2,6-二甲基苯酯、甲基丙烯酸3,5-二甲基苯酯、甲基丙烯酸壬酯、甲基丙烯酸癸酯、甲基丙烯酸异癸酯等甲基丙烯酸酯。
其中,共聚用单体不优选使用含有芳香环的(甲基)丙烯酸酯。另外,聚合物中的共聚用单体单元的含量优选为50摩尔%以下,进一步优选为30摩尔%以下。当其超过50摩尔%时,有时其折射率、耐热性、耐光性的平衡变差。
需要说明的是,上述脂环式烃基含有的三级碳的个数优选为8以下,进一步优选为5以下。当酯部分含有的三级碳的个数超过8以上时,有时容易发生黄变。
本发明的光半导体密封材料中用于自由基聚合的自由基聚合引发剂,可以举例为:过氧化甲基乙基酮、过氧化甲基异丁基酮、过氧化乙酰丙酮、过氧化环己酮、过氧化甲基环己酮等过氧化酮类;1,1,3,3-四甲基丁基过氧化氢、枯基过氧化氢、叔丁基过氧化氢等过氧化氢类;过氧化二异丁酰、过氧化二-3,5,5-三甲基己醇、过氧化月桂酰、过氧化苯甲酰、过氧化间甲苯酰基苯甲酰等过氧化二酰类;过氧化二异丙苯、2,5-二甲基-2,5-二(叔丁基过氧)己烷、1,3-二(叔丁基过氧异丙基)己烷、过氧化叔丁基枯基、过氧化二叔丁基、2,5-二甲基-2,5-二(叔丁基过氧)己烯等过氧化二烷基类;1,1-二(叔丁基过氧-3,5,5-三甲基)环己烷、1,1-二叔丁基过氧环己烷、2,2-二(叔丁基过氧)丁烷等过氧化缩酮类;1,1,3,3-四甲基丁基过氧新二碳酸酯、α-枯基过氧新二碳酸酯、叔丁基过氧新二碳酸酯、叔己基过氧新戊酸酯、叔丁基过氧新戊酸酯、1,1,3,3-四甲基丁基过氧-2-乙基己酸酯、叔戊基过氧-2-乙基己酸酯、叔丁基过氧-2-乙基己酸酯、叔丁基过氧异丁酸酯、二叔丁基过氧六氢对苯二甲酸酯、1,1,3,3-四甲基丁基过氧-3,5,5-三甲基己酸酯、叔戊基过氧-3,5,5-三甲基己酸酯、叔丁基过氧-3,5,5-三甲基己酸酯、叔丁基过氧乙酸酯、叔丁基过氧苯甲酸酯、二丁基过氧三甲基己二酸酯等过氧化烷基酯类;二-3-甲氧基丁基过氧二碳酸酯、二-2-乙基己基过氧二碳酸酯、二(1,1-丁基环己基氧二碳酸酯)、二异丙基氧基二碳酸酯、叔戊基过氧异丙基碳酸酯、叔丁基过氧异丙基碳酸酯、叔丁基过氧-2-乙基己基碳酸酯、1,6-二(叔丁基过氧羧基)己烷等过氧化碳酸酯类等。
相对上述单体总量100质量份,自由基聚合引发剂的使用量通常为0.01~5质量份,优选为0.05~1.0质量份。上述自由基聚合引发剂可以分别单独使用,也可以多个同时使用。
除了上述自由基聚合引发剂之外,为了得到高强度,也可以使用交联性单体。交联性单体例如有:1,4-丁二醇(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、环氧乙烷改性双酚A二(甲基)丙烯酸酯、环氧丙烷改性双酚A二(甲基)丙烯酸酯、环氧氯丙烷改性双酚A二(甲基)丙烯酸酯、环氧丙烷改性甘油三(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、二三羟甲基丙烷四(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三(丙烯酰氧基乙基)三聚异氰酸酯等。这些交联性单体可以单独使用,也可以两种以上组合使用。交联性单体的含量在所有单体中,优选为0.1~80质量%。进一步优选为1~70质量%,更优选为2~50质量%。当交联性单体的含量低于0.1质量%时,无法得到由交联形成的高强度化的效果。
在本发明的光半导体密封材料中,为了提高耐热性,也可以使其含有热塑性树脂。该热塑性树脂优选透明性高、玻璃化温度为120℃以上的热塑性树脂。当其玻璃化温度低于120℃时,耐热性的改善效果变小。
作为这样的热塑性树脂,可以例举:聚甲基丙烯酸酯、聚苯乙烯、聚碳酸酯、聚芳基酯、聚醚砜、环氧丙烯酸酯、烯烃-马来酰亚胺共聚物、ZEONEX(日本ZEON株式会社制,环烯烃系聚合物)、ZEONOR(日本ZEON株式会社制,环烯烃系聚合物)、ARTON(JSR株式会社制,环烯烃系聚合物)、TOPAS(Ticona社制,环烯烃系聚合物)、透明ABS、透明丙烯、MS(甲基丙烯基苯乙烯)树脂、聚烯丙酯、聚砜、透明尼龙、透明聚对苯二甲酸丁二醇酯、透明氟树脂、聚-4-甲基戊烯-1、透明苯氧树脂等。也可以将这些热塑性树脂的两种以上组合使用。在光半导体密封材料中,热塑性树脂的含量优选为0.5~20质量%。通过将热塑性树脂的含量设定为0.5质量%以上,可以得到耐热性改善效果,通过将热塑性树脂的含量设定为20质量%以下,可以使其流动性优良。
另外,作为本发明的光半导体密封材料,优选使用包含将含碳数7以上的脂环式烃基的甲基丙烯酸酯和含羟基丙烯酸酯进行自由基聚合而成的聚合物的物质。
用于本发明的光半导体密封材料的含羟基丙烯酸酯,可以例举:甲基丙烯酸2-羟乙酯、甲基丙烯酸2-羟丙酯、丙烯酸2-羟乙酯、丙烯酸2-羟丙酯、甲基丙烯酸2-羟丁酯、甘油二甲基丙烯酸酯、甲基丙烯酸2-羟基-3-丙烯酰氧基丙酯、丙烯酸2-羟丁酯、丙烯酸2-羟基-3-苯氧丙酯、丙烯酸2-羟基-3-丙烯酰氧基丙基酯、丙烯酸2-羟基-3-苯氧丙酯、六氢邻苯二甲酸二缩水甘油酯的丙烯酸改性物、乙二醇二缩水甘油醚的甲基丙烯酸改性物、聚乙二醇缩水甘油醚的甲基丙烯酸改性物、二甘醇二缩水甘油醚的甲基丙烯酸改性物、1,4-丁二醇二缩水甘油醚二丙烯酸酯等。在这些物质中,特别优选六氢邻苯二甲酸二缩水甘油酯的丙烯酸改性物、乙二醇二缩水甘油醚的甲基丙烯酸改性物、聚乙二醇缩水甘油醚的甲基丙烯酸改性物、二甘醇二缩水甘油醚的甲基丙烯酸改性物、1,4-丁二醇二缩水甘油醚二丙烯酸酯。
在这样的本发明的光半导体密封材料中的含碳数7以上的脂环式烃基的甲基丙烯酸酯和含羟基丙烯酸酯的组合中,含碳数7以上的脂环式烃基的甲基丙烯酸酯的含量为50~97质量%,优选为60~95质量%;含羟基丙烯酸酯的含量为3~50质量%,优选为5~40质量%。通过将含碳数7以上的脂环式烃基的甲基丙烯酸酯和含羟基丙烯酸酯的含量设定为这样的范围,成为可提供一种对紫外线稳定而不发生黄变、且耐热性、粘接性的平衡优良的固化物的热固性树脂组合物。
上述热固性树脂组合物对塑料成形品显示出足够高的粘接性,也可以优选用作粘接剂,当预先对塑料成形品表面用紫外线照射处理、臭氧处理、等离子处理、电晕放电处理、高压放电处理等方法进行活化处理时,其粘接性进一步提高。
需要说明的是,本发明中所谓的热固性树脂组合物是指仅因热而进行聚合的树脂组合物。聚合后得到的树脂可以不一定具有3维交联结构,也可以是直链状树脂。另外,可以是熔融的,也可以是热塑性的。
紫外线照射处理是在空气中对塑料成形品表面照射紫外线的方法。作为照射紫外线的光源,可以使用低压水银灯、高压水银灯、超高压水银灯、氙灯、金属卤化物灯等。可以认为,通过紫外线照射,塑料内产生自由基,而且,产生来自空气中的氧的活性氧,两者发生反应,在成形品表面引入极性基(-COOH、-COH、-C=O等)。其结果,粘接性提高。对塑料成形品照射的紫外线的能量,因塑料的种类、形状、灯的种类而异,但为了提高与本发明的热固性树脂组合物的粘接性,其优选为10~20000mJ/cm2的范围、进一步优选为100~10000mJ/cm2。当照射能量超过20000mJ/cm2时,有时塑料成形品表面老化。当其低于10mJ/cm2时,有时因能量不充分而无法得到足够的粘接力。通过成形品和灯的距离及照射时间控制照射能量。例如,成形品和灯的距离优选为1~50cm左右,进一步优选为5~30cm的范围。照射时间为5秒钟~10分钟左右,优选10秒钟~5分钟左右。当成形品和灯的距离低于1cm或超过50cm、或者照射时间低于5秒钟或超过10分钟时,有时不能将照射能量控制在10~20000mJ/cm2。
臭氧处理是使塑料成形品表面与臭氧分子接触,以进行以氧化反应为主的改性反应。通过将塑料成形品暴露在臭氧中来进行臭氧处理。暴露方法可以通过在臭氧存在的环境中保持规定时间的方法、在臭氧气流中保持规定时间的方法等适当的方法来进行。臭氧可以通过将空气、氧气或加氧空气等含氧气体供给臭氧发生装置来使其发生。将得到的含臭氧气体引入保持有塑料成形品的容器、槽等中,可以进行臭氧处理。可以推测,通过由臭氧处理而在塑料成形品表面发生的以氧化为主的反应,可以引入过氧化氢基等,其一部分变成羟基、羰基等官能团。
等离子处理是为了将塑料成形品放置在包含氩、氖、氦、氮、二氧化氮、氧或空气等的容器内,暴露在利用辉光放电产生的等离子中,以便在成形品的表面引入包含氧、氮等的官能团。产生等离子的放电方式有:(1)直流放电及低频放电、(2)无线电波放电、(3)微波放电等。
电晕放电处理是如下所述的方法:在设置的金属辊和距其以数mm的间隔放置的刀状电极间,施加数千伏的高电压,使其发生电晕放电,在该放电中的电极-辊间,使塑料成形品通过。
高压放电处理是如下所述的方法:在隧道状处理装置内,设置用于使被处理的塑料成形品移动的传送带,一边使塑料成形品移动,一边在处理装置的内侧壁面安装的多个电极间施加数十万伏的高电压,在空气中使其放电进行处理。通常认为,通过放电,空气中的氧和塑料成形品的表面被活性化,塑料表面吸收氧生成极性基。
另外,在本发明的光半导体密封材料中,还可以使用抗氧化剂及光稳定剂等作为添加剂。抗氧化剂包括:苯酚系抗氧化剂、磷系抗氧化剂、硫系抗氧化剂、维生素系抗氧化剂、内酯系抗氧化剂、胺系抗氧化剂等。
苯酚系抗氧化剂可以例举:Irganox1010(Ciba Specialty Chemicals社,商标)、Irganox1076(Ciba Specialty Chemicals社,商标)、Irganox1330(Ciba Specialty Chemicals社,商标)、Irganox3114(Ciba SpecialtyChemicals社,商标)、Irganox3125(Ciba Specialty Chemicals社,商标)、Irganox3790(Ciba Specialty Chemicals社,商标)BHT、Cyanox1790(Cyanamid社,商标)、SumilizerGA-80(住友化学社,商标)等市售品。
磷系抗氧化剂可以例举:Irgafos168(Ciba Specialty Chemicals社,商标)、Irgafos 12(Ciba Specialty Chemicals社,商标)、Irgafos38(Ciba SpecialtyChemicals社,商标)、ADKSTAB329K(旭电化社,商标)、ADKSTABPEP36(旭电化社,商标)、ADKSTAB PEP-8(旭电化社,商标)、SardstabP-EPQ(Clariant社,商标)、Weston 618(GE社,商标)、Weston 619G(GE社,商标)、Weston-624(GE社,商标)等市售品。
硫系抗氧化剂可以例举例如:DSTP(吉富)(吉富社,商标)、DLTP(吉富)(吉富社,商标)、DLTOIB(吉富)(吉富社,商标)、DMTP(吉富)(吉富社,商标)、Seenox412S(SHIPRO化成社,商标)、Cyanox1212(Cyanamid社,商标)等市售品。
维生素系抗氧化剂有:维生素E、IrganoxE201(Ciba Specialty Chemicals社,商标,化合物名:2,5,7,8-四甲基-2(4’,8’,12’-三甲基十三烷基)苯并呋喃-6-醇)等市售品。
内酯系抗氧化剂可以使用特开平7-233160号公报、特开平7-247278号公报所述的物质。还有HP-136(Ciba Specialty Chemicals社,商标,化合物名:5,7-二叔丁基-3-(3,4-二甲基苯基)-3H-苯并呋喃-2-酮)等。
胺系抗氧化剂可以例举:Irgastab FS042(Ciba Specialty Chemicals社,商标)、GENOX EP(クロンプトン社,商标,化合物名:二烷基-N-甲胺氧化物)等市售品。
相对树脂成分总量100质量份,这些添加剂的使用量通常为0.005~5质量份,优选为0.02~2质量份。这些添加剂也可以两种以上组合使用。
而且,在本发明的光半导体密封材料中,可以添加光稳定剂。光稳定剂可以使用通常已知的物质,但优选受阻胺类光稳定剂。具体来讲,作为商品名可以例举:旭电化社制的ADK STAB LA-52、LA-57、LA-62、LA-63、LA-67、LA-68、LA-77、LA-82、LA-87、LA-94、CSC社制的Tinuvin123、144、440、662、Chimassorb2020、119、944、Hoechst社制的Hostavin N30、Cytec社制的Cyasorb UV-3346、UV-3526、GLC社制的Uval 299、Clariant社制的SanduvorPR-31等。
相对树脂成分总量100质量份,光稳定剂的添加量通常为0.005~5重量份,优选为0.002~2重量份。这些光稳定剂也可以两种以上组合使用。另外,还可以添加各种荧光体。
利用本发明的光半导体密封材料密封的元件没有特别限制,可以例举例如:发光二极管(LED)芯片、半导体激光、光电二极管、光电断流器、光电耦合器、光敏晶体管、场致发光元件、CCD、太阳能电池等。本发明的光电变换元件,可以例举利用本发明的光半导体密封材料密封的LED等,本发明的光电变换装置,可以例举使用了该LED的照明装置和信号机等各种半导体装置。
实施例
下面,利用实施例对本发明进行详细说明,但本发明不限定于这些实例。
需要说明的是,在各实施例及比较例中得到的光半导体密封材料(固化物)的物性评价方法如下所述。
(1)玻璃化温度
使用差示扫描量热仪(Perkin Elmer社制,DSC-7),将试样10mg在氮气气氛下50℃保持5分钟后,使其以20℃/分钟的速度升温,将由此得到的热流量曲线中可以观测到的不连续点设定为玻璃化温度Tg。
(2)全光线穿透率
使用作为试样的厚3mm的试验片,以JIS K7105为基准进行测定(单位:%)。测定装置使用HGM-2DP(Suga试验机株式会社)。
另外,在140℃的恒温槽中,将样品放置100小时,将其前后的全光线穿透率的差值(%)设定为Δ全光线穿透率。
(3)400nm中的穿透率
用UV可见分光计(岛津制作所制UV-2400PC),在200nm~700nm的波长范围测定透过率。
(4)耐候性试验(ΔYI的测定)
对黄变度(YI)的测定而言,使用作为试样的厚3mm的试验片,以JISK7105为基准进行测定。测定装置使用SZ-optical SENSOR(日本电色工业株式会社制),进行如下耐候性试验。
ΔYI1:使用耐候性试验机(JASCO International制solarbox1500e),以500W/m2的功率对试样照射紫外线100小时,测定紫外线照射前后的YI,将其差值设定为ΔYI1。
ΔYI2:在140℃的恒温槽中,将样品放置100小时,将其前后的YI的差值设定为ΔYI2。
(5)弯曲弹性模数:以JIS K7203为基准进行测定。
(6)软化点
使用长10mm、一边长3mm的圆柱型,使用热物性测定仪(TMA/SS6100,Seiko Instruments株式会社),在升温速度为5℃/mm、载荷为49mN的条件下进行测定。
(7)折射率
使用Elmer社制的折射率计,在25℃进行测定。
(8)粘接性试验
粘接强度:在64mm×13mm×3mm的聚酰胺复合材料试验片a)的从一端到20mm的区域(面积=20mm×13mm),涂敷热固性树脂组合物(液状),在其上重叠相同尺寸的试验片,在规定条件下进行热固化,使两试验片粘接(参照图1)。然后,以拉伸速度20mm/分钟进行拉伸试验。将试验时的最大点载荷(N)作为粘接强度的指标。
和反射板粘接的数:将聚酰胺复合材料b)和引线框架进行一体成形,作成如图2所示的部件,准备10个这样的部件。在部件的凹部填充热固性树脂组合物(液状),在规定条件下进行热固化。观察每一个部件,观察固化物和反射板之间的粘接状态。根据10个部件内有几个没有剥离的部件,来评价其粘接性。
(备注)
a):将b)的聚酰胺复合材料颗粒在70℃干燥一昼夜后,在滚筒温度280℃、模具温度120℃进行注塑而成的试验片。
b)将半芳香族聚酰胺(AMODEL A4000、Solvay Advanced聚合物)/氧化钛(PF-726,石原产业)/玻璃纤维(JAFT164G旭FIBER GLASS)以70/10/20(质量比)的比例混合,在进行干混后,投入内径30mm的双螺杆挤出机的料斗中,在滚筒温度285℃进行熔融混练,成形为颗粒。
c)上述粘接性试验是在对聚酰胺复合材料试验片或引线框架状态部件照射紫外线和没有照射紫外线这两种情况下进行的。紫外线照射装置使用高压水银灯(3kW Eyegrantage ECS-301G1,EYE GRAPHICS株式会社制,120W,照射距离15cm),照射紫外线,以使其照射能量为1000mJ/cm2。
实施例1
在甲基丙烯酸1-金刚烷基酯(出光兴产株式会社制)单体21g中,加入作为自由基聚合引发剂的1,1-二(叔丁基过氧)-3,3,5-三甲基环己烷(日本油脂株式会社制PERHEXA 3M-95)0.021g,作成固化性组合物。使该组合物流入2片玻璃板夹持作为3mm厚的特氟隆制的隔板制作的单元中,用烘箱以100℃/1小时、110℃/1小时、120℃/1小时、130℃/30分钟进行加热后,慢慢冷却至室温,由此得到无色透明的板状固化物。得到的固化物的物性评价结果如表1所示。
实施例2
在实施例1中,将单体变更为甲基丙烯酸双环戊烷基酯(日立化成工业株式会社制FANCRYL FM-513)单体,将自由基聚合引发剂变更为偶氮二异丁腈(东京化成工业株式会社制),除此以外,用和实施例6同样的方法得到固化物。得到的固化物的物性评价结果如表1所示。
实施例3
在实施例6中,将单体变更为甲基丙烯酸异冰片酯单体(和光纯药工业株式会社制),除此以外,用和实施例6同样的方法得到固化物。得到的固化物的物性评价结果如表1所示。
实施例4
在实施例1中,将单体变更为甲基丙烯酸降冰片酯(和光纯药工业株式会社制),除此以外,用和实施例1同样的方法得到固化物。得到的固化物的物性评价结果如表1所示。
实施例5
在实施例1中,再加入作为交联性单体的乙二醇二甲基丙烯酸酯(和光纯药工业株式会社制)0.42g,除此以外,用和实施例6同样的方法得到固化物。得到的固化物的物性评价结果如表1所示。
实施例6
在实施例5中,再将作为热塑性树脂的TOPAS 8007(Ticona社制)2.1g在室温下边搅拌边均匀溶解,除此以外,用和实施例5同样的方法得到固化物。得到的固化物的物性评价结果如表1所示。
实施例7
在甲基丙烯酸1-金刚烷基酯(出光兴产株式会社制)单体21g中,加入作为自由基聚合引发剂的1,1-二(叔丁基过氧)-3,3,5-三甲基环己烷(日本油脂株式会社制PERHEXA 3M-95)0.021g及二异丙基苯过氧化氢(日本油脂株式会社制PERCUMYL P)0.021g,作成固化性组合物。使该组合物流入2片玻璃板夹持作为3mm厚的特氟隆制的隔板作成的单元中,用烘箱以100℃/1小时、110℃/1小时、120℃/1小时、130℃/30分钟进行加热后,以2℃/分钟的速度升温至200℃热处理1小时,慢慢冷却至室温,由此得到无色透明的板状固化物。得到的固化物的物性评价结果如表1所示。
实施例8
在甲基丙烯酸1-金刚烷基酯(出光兴产株式会社制)单体22g中,加入甲基丙烯酸甲酯单体(Sigma Aldrich Japan株式会社制)2.5g,加入作为自由基聚合引发剂的过氧化二(4-叔丁基环己基)二碳酸酯(PERROYL TCP,日本油脂株式会社制)0.068g,作成固化性组合物。使该组合物流入2片玻璃板夹持作为3mm厚的特氟隆制的隔板作成的单元中,用烘箱以60℃/3小时、200℃/30分钟进行加热后,慢慢冷却至室温,由此得到无色透明的板状固化物。得到的固化物的物性评价结果如表2所示。
实施例9
在甲基丙烯酸1-金刚烷基酯(出光兴产株式会社制)单体21g中,加入作为交联性单体的聚乙二醇二甲基丙烯酸酯(新中村化学工业株式会社制NK ESTER 9G)7g,加入作为自由基聚合引发剂的二(4-叔丁基环己基)过氧二碳酸酯(PERROYL TCP,日本油脂株式会社制)0.12g,作成固化性组合物。使该组合物流入2片玻璃板夹持作为3mm厚的特氟隆制的隔板作成的单元中,用烘箱以70℃/3小时、160℃/1小时进行加热后,慢慢冷却至室温,由此得到无色透明的板状固化物。得到的固化物的物性评价结果如表1所示。
比较例1
在双酚A型液状环氧树脂(Japan Epoxy Resins株式会社制EPIKOTE 828)单体14g中,加入甲基六氢邻苯二甲酸酐(和光纯药工业株式会社制)14g,混合1,8-重氮二环[5,4,0]十一烷基-7-烯(Sigma Aldrich Japan株式会社制)0.028g,将进行均匀混合而成的混合物流入密闭好的特氟隆制的隔板中,用烘箱以3小时慢慢升温至130℃后,慢慢冷却至室温,由此得到板状试样。得到的固化物的物性评价结果如表1及表2所示。
实施例10
在甲基丙烯酸1-金刚烷基酯(出光兴产株式会社制)单体18.9g、1,4-丁二醇缩水甘油醚二丙烯酸酯(新中村化学工业株式会社制)2.1g中,加入作为聚合引发剂的PERHEXA 3M-95(日本油脂株式会社制)0.021g,作成固化性组合物。使该组合物流入2片玻璃板夹持3mm厚的特氟隆制的隔板作成的单元中,用烘箱以100℃/1小时、110℃/1小时、120℃/1小时、130℃/30分钟进行加热后,慢慢冷却至室温,由此得到无色透明的板状固化物。得到的固化物(树脂)的物性评价结果如表2所示。
实施例11
在实施例1中,取代甲基丙烯酸1-金刚烷基酯,变更为甲基丙烯酸双环戊二烯酯(日立化成工业株式会社制FANCRYL FM-513),除此以外,用和实施例10同样的方法得到固化物。得到的固化物的物性评价结果如表2所示。
实施例12
在实施例10中,取代甲基丙烯酸1-金刚烷基酯,变更为甲基丙烯酸降冰片酯(和光纯药工业株式会社制),除此以外,用和实施例10同样的方法得到固化物。得到的固化物的物性评价结果如表2所示。
实施例13
在实施例10中,将甲基丙烯酸1-金刚烷基酯设定为14g、1,4-丁二醇缩水甘油醚二丙烯酸酯设定为7g,除此以外,用和实施例1同样的方法得到固化物。得到的固化物的物性评价结果如表2所示。
实施例14
在实施例1中,将甲基丙烯酸1-金刚烷基酯的混合量设定为15.8g,再加入作为交联性单体的乙二醇二甲基丙烯酸酯(和光纯药工业株式会社制)3.1g,除此以外,用和实施例10同样的方法得到固化物。得到的固化物的物性评价结果如表2所示。
比较例2
在实施例10中,将甲基丙烯酸1-金刚烷基酯设定为21g、1,4-丁二醇缩水甘油醚二丙烯酸酯设定为0g,除此以外,用和实施例10同样的方法得到固化物。得到的固化物的物性评价结果如表2所示。
比较例3
在实施例14中,将1,4-丁二醇缩水甘油醚二丙烯酸酯设定为0g、乙二醇二甲基丙烯酸酯设定为5.2g,除此以外,用和实施例14同样的方法得到固化物。得到的固化物的物性评价结果如表2所示。
工业应用的可能性
本发明的光半导体密封材料具有如下特性:透明性优良;对紫外线稳定而不发生黄变;耐热性、折射率的平衡优良;而且,在回流焊锡等加热工序中不发生变形及裂缝的加工性也优良;可以优选用作光半导体装置(半导体发光装置)中的发光元件和受光元件等的密封材料。
Claims (5)
1.一种光半导体密封材料,其特征在于,包含将具有金刚烷基的甲基丙烯酸酯进行自由基聚合而成的聚合物。
2.如权利要求1所述的光半导体密封材料,其特征在于,其还包含基于所述光半导体密封材料的0.5~20质量%的热塑性树脂。
3.一种光半导体密封材料,其特征在于,包含基于具有金刚烷基的甲基丙烯酸酯和含羟基丙烯酸酯的组合,将50~97质量%的具有金刚烷基的甲基丙烯酸酯和3~50质量%的含羟基丙烯酸酯进行自由基聚合而成的聚合物。
4.一种光电变换元件,其特征在于,使用了权利要求1~3中任一项所述的光半导体密封材料。
5.一种光电变换装置,其特征在于,使用了权利要求4所述的光电变换元件。
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Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5192143B2 (ja) * | 2006-11-22 | 2013-05-08 | 出光興産株式会社 | シラップ用(メタ)アクリレート共重合体およびその樹脂組成物 |
JP5080114B2 (ja) * | 2007-03-20 | 2012-11-21 | 出光興産株式会社 | 光半導体用反射材 |
JP4967761B2 (ja) * | 2007-03-30 | 2012-07-04 | 住友ベークライト株式会社 | 樹脂組成物および樹脂組成物を使用して作製した半導体装置 |
KR20090055272A (ko) * | 2007-11-28 | 2009-06-02 | 삼성전자주식회사 | Led패키지, 이의 제조 방법 및 이를 포함하는 백라이트어셈블리 |
KR20110020862A (ko) * | 2008-06-02 | 2011-03-03 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 접착성 캡슐화 조성물 및 그것을 사용하여 제조한 전자 소자 |
EP2463316B1 (en) * | 2009-08-04 | 2016-06-08 | Idemitsu Kosan Co., Ltd. | Acrylate composition |
US20130237660A1 (en) * | 2010-10-25 | 2013-09-12 | Idemitsu Kosan Co. Ltd | (meth)acrylate composition |
KR102050029B1 (ko) * | 2011-08-26 | 2019-11-29 | 삼성디스플레이 주식회사 | 도너 기판, 도너 기판의 제조 방법, 유기 발광 표시 장치 및 유기 발광 표시 장치의 제조 방법 |
TWI580701B (zh) * | 2011-10-27 | 2017-05-01 | 三菱麗陽股份有限公司 | 乙烯基聚合物粉末、硬化性樹脂組成物及硬化物 |
JP5810012B2 (ja) * | 2012-03-07 | 2015-11-11 | 富士フイルム株式会社 | 硬化性組成物、これを用いた半導体発光装置用封止材及び半導体発光装置 |
KR101473308B1 (ko) | 2012-11-23 | 2014-12-16 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
DE202013009203U1 (de) | 2013-10-18 | 2013-11-26 | Schiffer+Farber Dekorationsbau GmbH | Warmlichtfilter für Leuchtdioden Lichtquellen |
JPWO2016088646A1 (ja) * | 2014-12-04 | 2017-09-14 | 昭和電工株式会社 | 半導体ナノ粒子含有硬化性組成物、硬化物、光学材料および電子材料 |
JP6590269B1 (ja) * | 2018-09-27 | 2019-10-16 | パナソニックIpマネジメント株式会社 | 有機el素子封止用紫外線硬化性樹脂組成物、有機el発光装置の製造方法、有機el発光装置、及びタッチパネル |
WO2021085241A1 (ja) * | 2019-10-29 | 2021-05-06 | 積水化学工業株式会社 | 電子デバイス用光硬化性樹脂組成物 |
Family Cites Families (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2659133C2 (de) * | 1976-12-28 | 1978-09-21 | Roehm Gmbh, 6100 Darmstadt | Verfahren zur Herstellung von blockfesten Überzügen |
JPS58142931A (ja) | 1982-02-19 | 1983-08-25 | Konishiroku Photo Ind Co Ltd | 光学用樹脂組成物および光学用素子 |
US4563438A (en) * | 1983-05-06 | 1986-01-07 | Ciba Geigy Corporation | Liquid mixture of photoinitiators |
US4591626A (en) * | 1983-10-24 | 1986-05-27 | Hitachi Chemical Company, Ltd. | Polymers of tricyclo[5.2.1.02,6 ]deca-8-yl (meth)acrylate |
JPS60124608A (ja) * | 1983-12-09 | 1985-07-03 | Japan Synthetic Rubber Co Ltd | アダマンタン誘導体からなる重合体の製造方法 |
JPS62201913A (ja) | 1986-02-28 | 1987-09-05 | Hitachi Chem Co Ltd | 光学用樹脂材料 |
JPS63243113A (ja) | 1987-03-30 | 1988-10-11 | Idemitsu Kosan Co Ltd | アクリル酸とアダマンチル基を含有するアクリル酸エステルとの共重合体及びその製造方法 |
US4868261A (en) * | 1987-06-18 | 1989-09-19 | Hitachi Chemical Company, Ltd. | Optical resin material |
USH1482H (en) * | 1987-12-04 | 1995-09-05 | Shell Oil Company | Coatings for metals based on functionalized block copolymers |
JPH01234406A (ja) * | 1988-03-14 | 1989-09-19 | Nippon Kayaku Co Ltd | ジ(メタ)アクリル酸エステル、これを用いた樹脂組成物及びコーテイング剤 |
JPH0229408A (ja) | 1988-07-20 | 1990-01-31 | Hitachi Ltd | 低吸水性透明プラスチツク |
JPH0267248A (ja) * | 1988-08-31 | 1990-03-07 | Mitsubishi Petrochem Co Ltd | 新規な(メタ)アクリル酸エステル |
JP2515010B2 (ja) * | 1989-01-26 | 1996-07-10 | 株式会社メニコン | 眼用レンズ材料 |
JPH0339304A (ja) | 1989-07-05 | 1991-02-20 | Hakusui Chem Ind Ltd | アダマンチルモノクロトネート系重合体 |
AU634338B2 (en) * | 1990-02-08 | 1993-02-18 | Mitsubishi Rayon Company Limited | Composition for plastic lenses |
EP0443864A1 (en) * | 1990-02-23 | 1991-08-28 | Mitsubishi Petrochemical Company Limited | Thermoplastic elastomer and a process for its production |
EP0590573B1 (en) * | 1992-10-01 | 1998-01-07 | Hitachi Chemical Company, Ltd. | Resin for plastic lens |
JPH06340849A (ja) * | 1993-04-28 | 1994-12-13 | Nippon Zeon Co Ltd | 紫外線硬化性組成物、それを用いた接着法、及び接着物 |
US5883147A (en) * | 1994-01-04 | 1999-03-16 | Japan Institute Of Advanced Dentistry | Photopolymerizable adhesive composition |
US5412049A (en) * | 1994-03-31 | 1995-05-02 | Union Carbide Chemicals & Plastics Technology Corporation | Polymer compositions containing hydroxyl functional (meth)acrylates and hydroxyalkyl carbamate (meth)acrylates and mixtures thereof |
JP3497258B2 (ja) * | 1994-11-18 | 2004-02-16 | Jsr株式会社 | 放射線硬化性組成物 |
US6025449A (en) * | 1997-03-05 | 2000-02-15 | Kansai Paint Co., Ltd. | Water-soluble acrylic resin, resin composition containing the same for use in water-based coating composition, water-based coating composition and coating method by use of the same |
JP3546128B2 (ja) * | 1997-11-05 | 2004-07-21 | 昭和高分子株式会社 | 透明封止用樹脂組成物 |
JP2000082848A (ja) * | 1998-09-04 | 2000-03-21 | Showa Highpolymer Co Ltd | オプトデバイスの封止成形方法 |
JP2000294836A (ja) * | 1999-04-02 | 2000-10-20 | Sharp Corp | 発光ダイオードの樹脂封止方法 |
JP2000336232A (ja) | 1999-05-26 | 2000-12-05 | Daicel Chem Ind Ltd | 水性樹脂組成物 |
JP2000345111A (ja) * | 1999-06-07 | 2000-12-12 | Three M Innovative Properties Co | 接着剤組成物及びそれを用いた光ディスク |
JP4585636B2 (ja) | 1999-09-30 | 2010-11-24 | ダイセル化学工業株式会社 | アクリル系単量体の重合方法 |
KR100557543B1 (ko) * | 2000-06-30 | 2006-03-03 | 주식회사 하이닉스반도체 | 신규한 포토레지스트 단량체, 그의 중합체 및 이를함유하는 포토레지스트 조성물 |
JP2002206010A (ja) | 2000-11-09 | 2002-07-26 | Dainippon Ink & Chem Inc | 硬化性組成物 |
EP1209528B1 (en) * | 2000-11-28 | 2015-07-22 | Eternal Technology Corporation | Photoresist composition |
JP2003221406A (ja) * | 2002-01-31 | 2003-08-05 | Asahi Glass Co Ltd | 水性分散液 |
JP2003268188A (ja) * | 2002-03-19 | 2003-09-25 | Jsr Corp | 半導体装置およびその製造方法 |
JP4010841B2 (ja) * | 2002-03-26 | 2007-11-21 | 松下電工株式会社 | 光半導体素子封止用エポキシ樹脂組成物及び光半導体装置 |
JP2004128468A (ja) * | 2002-07-29 | 2004-04-22 | Mitsui Chemicals Inc | 発光素子封止材料用組成物とその使用方法 |
US6806320B2 (en) * | 2002-11-15 | 2004-10-19 | 3M Innovative Properties Company | Block copolymer melt-processable compositions, methods of their preparation, and articles therefrom |
JP2004175866A (ja) * | 2002-11-26 | 2004-06-24 | Nippon Kayaku Co Ltd | 光ディスク用接着剤組成物、硬化物および物品 |
JP2006188544A (ja) * | 2003-02-03 | 2006-07-20 | Daikin Ind Ltd | 耐熱性光学材料およびそれを用いた光伝送用媒体 |
JP2004346155A (ja) * | 2003-05-21 | 2004-12-09 | Nippon Petrochemicals Co Ltd | 光学材料用樹脂組成物 |
JP2005258000A (ja) | 2004-03-11 | 2005-09-22 | Jsr Corp | 光導波路形成用感光性組成物および光導波路 |
JP2005272697A (ja) * | 2004-03-25 | 2005-10-06 | Shin Etsu Chem Co Ltd | 硬化性シリコーン樹脂組成物、光半導体用封止材および光半導体装置 |
JP2005281363A (ja) | 2004-03-29 | 2005-10-13 | Mitsui Chemicals Inc | メタクリル樹脂組成物および透明部材 |
US20100234527A1 (en) | 2006-05-01 | 2010-09-16 | Idemitsu Kosan Co., Ltd. | Optical semiconductor encapsulating material |
EP2463316B1 (en) | 2009-08-04 | 2016-06-08 | Idemitsu Kosan Co., Ltd. | Acrylate composition |
-
2005
- 2005-11-09 CN CN2005800382537A patent/CN101056900B/zh not_active Expired - Fee Related
- 2005-11-09 TW TW094139299A patent/TWI389925B/zh not_active IP Right Cessation
- 2005-11-09 KR KR1020077010025A patent/KR101270821B1/ko not_active IP Right Cessation
- 2005-11-09 US US11/718,855 patent/US20080097072A1/en not_active Abandoned
- 2005-11-09 JP JP2006544907A patent/JP5022709B2/ja active Active
- 2005-11-09 WO PCT/JP2005/020509 patent/WO2006051803A1/ja active Application Filing
- 2005-11-09 DE DE112005002739T patent/DE112005002739T5/de not_active Withdrawn
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2012
- 2012-02-06 JP JP2012023495A patent/JP2012117079A/ja active Pending
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JP平2-67248 1990.03.07 |
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TW200621818A (en) | 2006-07-01 |
US20120305982A1 (en) | 2012-12-06 |
KR101270821B1 (ko) | 2013-06-05 |
JP5022709B2 (ja) | 2012-09-12 |
US8648160B2 (en) | 2014-02-11 |
US20080097072A1 (en) | 2008-04-24 |
JP2012117079A (ja) | 2012-06-21 |
TWI389925B (zh) | 2013-03-21 |
CN101056900A (zh) | 2007-10-17 |
DE112005002739T5 (de) | 2007-09-27 |
KR20070083920A (ko) | 2007-08-24 |
JPWO2006051803A1 (ja) | 2008-05-29 |
WO2006051803A1 (ja) | 2006-05-18 |
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