JP2007277467A - 硬化性樹脂組成物 - Google Patents
硬化性樹脂組成物 Download PDFInfo
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- JP2007277467A JP2007277467A JP2006108111A JP2006108111A JP2007277467A JP 2007277467 A JP2007277467 A JP 2007277467A JP 2006108111 A JP2006108111 A JP 2006108111A JP 2006108111 A JP2006108111 A JP 2006108111A JP 2007277467 A JP2007277467 A JP 2007277467A
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- refractive index
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- carbazole
- curable resin
- polymerizable
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- 239000011342 resin composition Substances 0.000 title claims abstract description 65
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 122
- 239000000178 monomer Substances 0.000 claims abstract description 52
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 34
- 238000007789 sealing Methods 0.000 claims abstract description 26
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 5
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 5
- 239000004305 biphenyl Substances 0.000 claims abstract description 5
- 125000005577 anthracene group Chemical group 0.000 claims abstract description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- -1 N-substituted carbazole Chemical class 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000011882 ultra-fine particle Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 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 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005641 methacryl group Chemical group 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 13
- 229920000647 polyepoxide Polymers 0.000 abstract description 13
- 239000000047 product Substances 0.000 description 48
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- 238000002156 mixing Methods 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 229920002050 silicone resin Polymers 0.000 description 11
- 238000001723 curing Methods 0.000 description 9
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 6
- 229910052594 sapphire Inorganic materials 0.000 description 6
- 239000010980 sapphire Substances 0.000 description 6
- VAZQKPWSBFZARZ-UHFFFAOYSA-N 2-(2-phenylphenoxy)ethyl prop-2-enoate Chemical group C=CC(=O)OCCOC1=CC=CC=C1C1=CC=CC=C1 VAZQKPWSBFZARZ-UHFFFAOYSA-N 0.000 description 5
- KOHMQTTZAWPDNE-UHFFFAOYSA-N 2-carbazol-9-ylethyl prop-2-enoate Chemical compound C1=CC=C2N(CCOC(=O)C=C)C3=CC=CC=C3C2=C1 KOHMQTTZAWPDNE-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000008646 thermal stress Effects 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- GHBQLFWTMLRYKN-UHFFFAOYSA-N 9-prop-2-enylcarbazole Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3C2=C1 GHBQLFWTMLRYKN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 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
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- XFQDAAPROSJLSX-UHFFFAOYSA-N 2-[4-(9h-fluoren-1-yl)phenoxy]ethyl prop-2-enoate Chemical compound C1=CC(OCCOC(=O)C=C)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C21 XFQDAAPROSJLSX-UHFFFAOYSA-N 0.000 description 1
- VIYWVRIBDZTTMH-UHFFFAOYSA-N 2-[4-[2-[4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCOC(=O)C(C)=C)C=C1 VIYWVRIBDZTTMH-UHFFFAOYSA-N 0.000 description 1
- YCPMSWJCWKUXRH-UHFFFAOYSA-N 2-[4-[9-[4-(2-prop-2-enoyloxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethyl prop-2-enoate Chemical compound C1=CC(OCCOC(=O)C=C)=CC=C1C1(C=2C=CC(OCCOC(=O)C=C)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YCPMSWJCWKUXRH-UHFFFAOYSA-N 0.000 description 1
- PCRXBGQWYLIHKQ-UHFFFAOYSA-N 2-carbazol-9-ylethyl 2-methylprop-2-enoate Chemical compound C1=CC=C2N(CCOC(=O)C(=C)C)C3=CC=CC=C3C2=C1 PCRXBGQWYLIHKQ-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- OPZLDVPRAIERSE-UHFFFAOYSA-N 3-[4-[2-[4-[3-(2-methylprop-2-enoyloxy)propoxy]phenyl]propan-2-yl]phenoxy]propyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCCOC(=O)C(C)=C)C=C1 OPZLDVPRAIERSE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NHIZBKTYLXRSOL-UHFFFAOYSA-N 9-[(4-ethenylphenyl)methyl]carbazole Chemical compound C1=CC(C=C)=CC=C1CN1C2=CC=CC=C2C2=CC=CC=C21 NHIZBKTYLXRSOL-UHFFFAOYSA-N 0.000 description 1
- XWUNIDGEMNBBAQ-UHFFFAOYSA-N Bisphenol A ethoxylate diacrylate Chemical compound C=1C=C(OCCOC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCCOC(=O)C=C)C=C1 XWUNIDGEMNBBAQ-UHFFFAOYSA-N 0.000 description 1
- RJLBFJJPDLNYHE-UHFFFAOYSA-N C=CC(CC(COCCOC(C=C1)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C21)O)=O Chemical compound C=CC(CC(COCCOC(C=C1)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C21)O)=O RJLBFJJPDLNYHE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Led Device Packages (AREA)
Abstract
【解決手段】 硬化性樹脂組成物が、屈折率1.52以上の高屈折率アクリル系モノマーと非重合性カルバゾールを含有し、さらに必要に応じて重合性カルバゾールを含有する。高屈折率アクリル系モノマーとしては、フルオレン骨格、ビスフェノールA骨格、ビフェニル骨格、ナフタリン骨格又はアントラセン骨格を有するアクリレート又はメタクリレートを使用する。
【選択図】なし
Description
(式中、A:アクリル又はメタクリル
R0:-(CH2CH2O)n- 又は-(CH2CH2O)n-CH2CH(OH)CH2O- 、
n=1〜5)
R1:水素又はメチル)
をあげることができる。
(式中、A:アクリル又はメタクリル
X:フェニル、クミルフェニル、ビフェニル、テルフェニル又は
多環式芳香族炭化水素基
Y:-(CH2CH2O)n- もしくは-(CH2CH2CH2O)n- 、n=1〜5、又は
-(CH2CH2O)n1-(CH2CH2CH2O)n2- 、n1+n2=2〜5)
本発明において、式(2)の単官能(メタ)アクリレートは、その単独種を使用してもよく、複数種を適宜組合せて使用してもよい。
(式中、R:水素、メチル、エチル、フェニル
X1 、X2:それぞれ水素、メチル、メトキシ又は水酸基)
(1)硬化性樹脂組成物の調製
2-(2-アクリロキシエトキシ)ビフェニル(東亞合成社、TO1463)(屈折率1.5785、粘度125mPa)に、N-ビニルカルバゾール硬化物粉末(東京化成工業社)(屈折率1.68)を表1に示す割合で溶解し、さらに光開始剤(チバスペシャリティーケミカルズ社、D1173)1重量部を配合し、遊星式混合機を用いて均一に分散し、硬化性樹脂組成物を得た。
(1)の硬化性樹脂組成物を2枚のPETからなる離型フィルムに挟み込み、水銀ランプで紫外線を照射し(1J)、厚さ0.5mmの硬化物シートを得た。
上述の硬化性樹脂組成物及び硬化物シートに対し、以下の評価を行った。結果を表1に示す。
硬化性樹脂組成物の粘度をE型粘度計(25℃)で測定した。
硬化性樹脂組成物及び硬化物シートの屈折率を、それぞれアッベの屈折率計(ナトリウムD線(589nm)、25℃)を用いて測定した。この場合、硬化物シートには、マッチングオイルを用いて測定した。
硬化性樹脂組成物の透過スペクトルを測定し、カットオフ波長を求めた。なお、カットオフ波長は、青色LEDの発光波長である440±20nmよりも十分低いことが実用上必要とされる。
硬化物シートを試料片とし、JIS A 1415に基づき、紫外線カーボンアークランプによる96時間の耐光試験を行った。
硬化物シートを試料片とし、150℃の空気雰囲気下で96時間おく耐熱性試験を行い、その前後の透明性の変化の有無を目視で調べた。
ASTM D2240に基づき、タイプAデュロメータを用いて硬化物シートのショアA硬度(室温)を測定した。
組成を表1のように変更する以外は実施例1と同様にして硬化性樹脂組成物及び硬化物シートを作製した。ここで、硬化剤として日本油脂社パーヘキサOを使用した場合には、組成物を80℃で1時間熱処理することにより硬化させた。
Claims (11)
- 屈折率1.52以上の高屈折率アクリル系モノマーと非重合性カルバゾールを含有してなる硬化性樹脂組成物。
- さらに重合性カルバゾールを含有する請求項1記載の硬化性樹脂組成物。
- 高屈折率アクリル系モノマーとカルバゾールの合計含量が50重量%以上である請求項1又は2記載の硬化性樹脂組成物。
- 硬化物の屈折率が1.55以上である請求項1〜3のいずれかに記載の硬化性樹脂組成物。
- 高屈折率アクリル系モノマーが、フルオレン骨格、ビスフェノールA骨格、ビフェニル骨格、ナフタリン骨格又はアントラセン骨格を有するアクリレート又はメタクリレートである請求項1〜4のいずれかに記載の硬化性樹脂組成物。
- 高屈折率アクリル系モノマーが、次式(1)で表されるフルオレン基含有アクリレート又はメタクリレート、及び次式(2)で表される単官能アクリレート又はメタクリレートから選ばれる1種又は2種以上である請求項1〜4のいずれかに記載の硬化性樹脂組成物。
(式中、A:アクリル又はメタクリル
R0:-(CH2CH2O)n- 又は-(CH2CH2O)n-CH2CH(OH)CH2O- 、
n=1〜5
R1:水素又はメチル
X:フェニル、クミルフェニル、ビフェニル、テルフェニル又は
多環式芳香族炭化水素基
Y:-(CH2CH2O)n- もしくは-(CH2CH2CH2O)n- 、n=1〜5、又は
-(CH2CH2O)n1-(CH2CH2CH2O)n2- 、n1+n2=2〜5) - 非重合性カルバゾールが次式(3)で表されるN置換カルバゾールである請求項1〜6のいずれかに記載の硬化性樹脂組成物。
(式中、R:水素、メチル、エチル、フェニル
X1 、X2:それぞれ水素、メチル、メトキシ又は水酸基) - 高屈折率アクリル系モノマーと非重合性カルバゾールとの混合物よりも屈折率の高い超微粒子が分散されている請求項1〜7のいずれかに記載の硬化性樹脂組成物。
- 請求項1〜8のいずれかに記載の硬化性樹脂組成物からなる光学封止用硬化性樹脂組成物。
- 請求項1〜8のいずれかに記載の硬化性樹脂組成物を硬化させてなる硬化物。
- 請求項9記載の硬化性樹脂組成物を用いて封止されてなる発光素子。
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US12/084,707 US7868109B2 (en) | 2006-04-10 | 2007-03-14 | Curable resin composition |
PCT/JP2007/055063 WO2007116625A1 (ja) | 2006-04-10 | 2007-03-14 | 硬化性樹脂組成物 |
CN2007800121216A CN101415736B (zh) | 2006-04-10 | 2007-03-14 | 硬化性树脂组合物 |
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WO2007116625A1 (ja) | 2007-10-18 |
US20090143505A1 (en) | 2009-06-04 |
HK1128483A1 (en) | 2009-10-30 |
CN101415736B (zh) | 2012-01-04 |
US7868109B2 (en) | 2011-01-11 |
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