JP2013253161A - 光学部品用接着剤組成物 - Google Patents
光学部品用接着剤組成物 Download PDFInfo
- Publication number
- JP2013253161A JP2013253161A JP2012129379A JP2012129379A JP2013253161A JP 2013253161 A JP2013253161 A JP 2013253161A JP 2012129379 A JP2012129379 A JP 2012129379A JP 2012129379 A JP2012129379 A JP 2012129379A JP 2013253161 A JP2013253161 A JP 2013253161A
- Authority
- JP
- Japan
- Prior art keywords
- group
- component
- atom
- meth
- adhesive composition
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000000853 adhesive Substances 0.000 title claims abstract description 46
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 46
- 230000003287 optical effect Effects 0.000 title claims abstract description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 43
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- -1 dinaphthothiophene compound Chemical class 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 5
- XPOTZJLKYZYZQX-UHFFFAOYSA-N C(C(=C)C)(=O)OCC1=CC=2C=CC=CC=2C=2C3=C(SC=21)C=1C=CC=CC=1C=C3 Chemical compound C(C(=C)C)(=O)OCC1=CC=2C=CC=CC=2C=2C3=C(SC=21)C=1C=CC=CC=1C=C3 XPOTZJLKYZYZQX-UHFFFAOYSA-N 0.000 claims description 3
- DMTLQBISMSUAEG-UHFFFAOYSA-N C(C(=C)C)(=O)OCCC1=CC=2C=CC=CC2C=2C3=C(SC21)C=2C=CC=CC2C=C3 Chemical compound C(C(=C)C)(=O)OCCC1=CC=2C=CC=CC2C=2C3=C(SC21)C=2C=CC=CC2C=C3 DMTLQBISMSUAEG-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000003505 polymerization initiator Substances 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- SYXXZXWLYNODHL-UHFFFAOYSA-N dinaphthothiophene Chemical group C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)S3)C3=CC=C21 SYXXZXWLYNODHL-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- LVJFCQSYEZPHJO-UHFFFAOYSA-N 12-thiapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3(8),4,6,9,14,16,18,20-decaen-4-ylmethyl prop-2-enoate Chemical compound C(C=C)(=O)OCC1=CC=CC=2C=CC3=C(C4=C(S3)C=3C=CC=CC3C=C4)C12 LVJFCQSYEZPHJO-UHFFFAOYSA-N 0.000 description 4
- 238000005304 joining Methods 0.000 description 4
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- SQWIEBKHVLRDRG-UHFFFAOYSA-N (2,6-dimethylphenyl)-diphenylphosphorylmethanone Chemical compound CC1=CC=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SQWIEBKHVLRDRG-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- YTWSMYGVWSAPGB-UHFFFAOYSA-N 10-ethenyl-12-thiapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene Chemical compound C(=C)C1=CC=2C=CC=CC=2C=2C3=C(SC=21)C=1C=CC=CC=1C=C3 YTWSMYGVWSAPGB-UHFFFAOYSA-N 0.000 description 2
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000511976 Hoya Species 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- IEWRMZSVIVEQCP-UHFFFAOYSA-N [methoxy(phenyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(OC)C(=O)C1=C(C)C=C(C)C=C1C IEWRMZSVIVEQCP-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 238000001444 catalytic combustion detection Methods 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000013307 optical fiber 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- KWVVOKMSNYUZCL-UHFFFAOYSA-N (2,4-dimethylbenzoyl)-phenylphosphinic acid Chemical compound CC1=CC(C)=CC=C1C(=O)P(O)(=O)C1=CC=CC=C1 KWVVOKMSNYUZCL-UHFFFAOYSA-N 0.000 description 1
- QAWHMCKOUTZPAL-UHFFFAOYSA-N (2,6-dibromophenyl)-diphenylphosphorylmethanone Chemical compound BrC1=CC=CC(Br)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 QAWHMCKOUTZPAL-UHFFFAOYSA-N 0.000 description 1
- JLLAWIKMLAQZCZ-UHFFFAOYSA-N (2,6-dichlorophenyl)-diphenylphosphorylmethanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 JLLAWIKMLAQZCZ-UHFFFAOYSA-N 0.000 description 1
- PYIMUNFRJFKRDE-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-[methoxy(phenyl)phosphoryl]methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(OC)C1=CC=CC=C1 PYIMUNFRJFKRDE-UHFFFAOYSA-N 0.000 description 1
- ZTESOBUXHNQNGT-UHFFFAOYSA-N (2,6-dimethylphenyl)-diphenylphosphanylmethanone Chemical compound CC1=CC=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C1=CC=CC=C1 ZTESOBUXHNQNGT-UHFFFAOYSA-N 0.000 description 1
- OVDYCAUPPUEIJO-UHFFFAOYSA-N (4-tert-butylphenyl)-diphenylphosphorylmethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 OVDYCAUPPUEIJO-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- QWHUYUGHATYPGB-UHFFFAOYSA-N 1-[methoxy(methyl)phosphoryl]-2-methylpropan-1-one Chemical compound COP(C)(=O)C(=O)C(C)C QWHUYUGHATYPGB-UHFFFAOYSA-N 0.000 description 1
- MFULLOGPOIYABI-UHFFFAOYSA-N 1-[methoxy(phenyl)phosphoryl]-2-methylpropan-1-one Chemical compound CC(C)C(=O)P(=O)(OC)C1=CC=CC=C1 MFULLOGPOIYABI-UHFFFAOYSA-N 0.000 description 1
- VVZUXOSFQDGMIH-UHFFFAOYSA-N 1-[methoxy(phenyl)phosphoryl]prop-2-en-1-one Chemical compound C=CC(=O)P(=O)(OC)C1=CC=CC=C1 VVZUXOSFQDGMIH-UHFFFAOYSA-N 0.000 description 1
- AYKPEZNBCSLOHW-UHFFFAOYSA-N 1-diphenylphosphanylprop-2-en-1-one Chemical compound C=1C=CC=CC=1P(C(=O)C=C)C1=CC=CC=C1 AYKPEZNBCSLOHW-UHFFFAOYSA-N 0.000 description 1
- QTFWVMNQFWUOOH-UHFFFAOYSA-N 1-diphenylphosphoryl-2,2-dimethylheptan-1-one Chemical compound C=1C=CC=CC=1P(=O)(C(=O)C(C)(C)CCCCC)C1=CC=CC=C1 QTFWVMNQFWUOOH-UHFFFAOYSA-N 0.000 description 1
- PIOUPIXFXCOVGD-UHFFFAOYSA-N 1-diphenylphosphoryl-2-ethylhexan-1-one Chemical compound C=1C=CC=CC=1P(=O)(C(=O)C(CC)CCCC)C1=CC=CC=C1 PIOUPIXFXCOVGD-UHFFFAOYSA-N 0.000 description 1
- CHICHOAVAYZBOD-UHFFFAOYSA-N 1-diphenylphosphoryl-2-methylpropan-1-one Chemical compound C=1C=CC=CC=1P(=O)(C(=O)C(C)C)C1=CC=CC=C1 CHICHOAVAYZBOD-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- MJDOQXICWBBRJC-UHFFFAOYSA-N 2-(12-thiapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3(8),4,6,9,14,16,18,20-decaen-4-yl)ethyl prop-2-enoate Chemical compound C(C=C)(=O)OCCC1=CC=CC=2C=CC3=C(C4=C(S3)C=3C=CC=CC=3C=C4)C1=2 MJDOQXICWBBRJC-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XXHDHAPOSIFMIG-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-phenoxyethanol Chemical compound OCCOCCOCCOCC(O)OC1=CC=CC=C1 XXHDHAPOSIFMIG-UHFFFAOYSA-N 0.000 description 1
- OBFOSROPNNOGQF-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]-1-phenoxyethanol Chemical compound OCCOCCOCCOCCOCCOCC(O)OC1=CC=CC=C1 OBFOSROPNNOGQF-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- PGJKTKAYCLVULZ-UHFFFAOYSA-N 2-methylbut-2-enoic acid prop-2-enoic acid Chemical compound OC(=O)C=C.CC=C(C)C(O)=O PGJKTKAYCLVULZ-UHFFFAOYSA-N 0.000 description 1
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 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
- PMGJMVAMSUFURL-UHFFFAOYSA-N 5,20-bis(ethenyl)-12-thiapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3(8),4,6,9,14,16,18,20-decaene Chemical compound C(=C)C=1C=CC=2C=CC3=C(C4=C(S3)C=3C=CC=CC=3C(=C4)C=C)C=2C=1 PMGJMVAMSUFURL-UHFFFAOYSA-N 0.000 description 1
- VEHGWOMBMHXNOH-UHFFFAOYSA-N 6,18-bis(ethenyl)-12-thiapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3(8),4,6,9,14,16,18,20-decaene Chemical compound C(=C)C1=CC=2C=CC3=C(C4=C(S3)C=3C=CC=C(C=3C=C4)C=C)C=2C=C1 VEHGWOMBMHXNOH-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- SRDIKKIBPZKIOO-UHFFFAOYSA-N C(=C)C1=CC2=C(C3=C(S2)C=2C=C(C=CC=2C=C3)C=C)C=2C=CC=CC1=2 Chemical compound C(=C)C1=CC2=C(C3=C(S2)C=2C=C(C=CC=2C=C3)C=C)C=2C=CC=CC1=2 SRDIKKIBPZKIOO-UHFFFAOYSA-N 0.000 description 1
- VVKBLKAHEULGSW-UHFFFAOYSA-N C(=C)OC1=CC=2C=CC3=C(C4=C(S3)C=3C=CC=C(C=3C=C4)OC=C)C=2C=C1 Chemical compound C(=C)OC1=CC=2C=CC3=C(C4=C(S3)C=3C=CC=C(C=3C=C4)OC=C)C=2C=C1 VVKBLKAHEULGSW-UHFFFAOYSA-N 0.000 description 1
- CTXCVEUSCMKHFW-UHFFFAOYSA-N C(C)(C)OP(=O)C1=CC=C(C=C1)C(C1=CC(=CC=C1)C(C)(C)C)=O Chemical compound C(C)(C)OP(=O)C1=CC=C(C=C1)C(C1=CC(=CC=C1)C(C)(C)C)=O CTXCVEUSCMKHFW-UHFFFAOYSA-N 0.000 description 1
- WJKDFYUHDFJFQZ-UHFFFAOYSA-N C1=CC(P(=O)OC)=CC=C1C1=CC=CC=C1C Chemical compound C1=CC(P(=O)OC)=CC=C1C1=CC=CC=C1C WJKDFYUHDFJFQZ-UHFFFAOYSA-N 0.000 description 1
- QLWYIKMDORWIQA-UHFFFAOYSA-N CC(=C)C(=O)CC1=CC2=CC=CC=C2C3=C1SC4=C3C=CC5=CC=CC=C54 Chemical compound CC(=C)C(=O)CC1=CC2=CC=CC=C2C3=C1SC4=C3C=CC5=CC=CC=C54 QLWYIKMDORWIQA-UHFFFAOYSA-N 0.000 description 1
- SOKKXNAGNBNDND-UHFFFAOYSA-N CC(=C)C(=O)CCC1=CC2=CC=CC=C2C3=C1SC4=C3C=CC5=CC=CC=C54 Chemical compound CC(=C)C(=O)CCC1=CC2=CC=CC=C2C3=C1SC4=C3C=CC5=CC=CC=C54 SOKKXNAGNBNDND-UHFFFAOYSA-N 0.000 description 1
- PAJBVENNGOIVIA-UHFFFAOYSA-N COC1=C(C=CC=C1)P(C1=CC=CC=C1)(C(C1=CC=CC=C1)=O)=O Chemical compound COC1=C(C=CC=C1)P(C1=CC=CC=C1)(C(C1=CC=CC=C1)=O)=O PAJBVENNGOIVIA-UHFFFAOYSA-N 0.000 description 1
- POATXWYDVORIMN-UHFFFAOYSA-N COP(=O)C1=CC=CC=C1C1=CC=CC=C1C Chemical compound COP(=O)C1=CC=CC=C1C1=CC=CC=C1C POATXWYDVORIMN-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- FPRGRFCEZKNBKD-UHFFFAOYSA-N [PH3]=O.COC1=C(C(=O)P(CC(CC(C)(C)C)C)(C(C2=C(C=CC=C2OC)OC)=O)=O)C(=CC=C1)OC Chemical class [PH3]=O.COC1=C(C(=O)P(CC(CC(C)(C)C)C)(C(C2=C(C=CC=C2OC)OC)=O)=O)C(=CC=C1)OC FPRGRFCEZKNBKD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CSNNWDJQKGMZPO-UHFFFAOYSA-N benzoic acid;2-hydroxy-1,2-diphenylethanone Chemical compound OC(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 CSNNWDJQKGMZPO-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- XVKKIGYVKWTOKG-UHFFFAOYSA-N diphenylphosphoryl(phenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 XVKKIGYVKWTOKG-UHFFFAOYSA-N 0.000 description 1
- STSOCJAMYLSXKR-UHFFFAOYSA-N diphenylphosphoryl-(2,3,4,6-tetramethylphenyl)methanone Chemical compound CC1=C(C)C(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 STSOCJAMYLSXKR-UHFFFAOYSA-N 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000001053 micromoulding Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
【解決手段】(A)成分が一般式(1)で表されるジナフトチオフェン化合物、(B)成分が1つ以上の芳香環を含有する単官能(メタ)アクリレート、(C)成分が光ラジカル重合開始剤、を含有し、前記(A)成分の含有割合が15〜50質量部であり、(B)成分の含有割合が50〜85質量部である光学部品用接着剤組成物。
【選択図】なし
Description
(1)(A)成分として、下記一般式(1)で表されるエチレン性不飽和二重結合を有する重合性官能基を1つ以上有するジナフトチオフェン系化合物、
(B)成分として、1つ以上の芳香環を含有する単官能(メタ)アクリレート、
(C)成分として、光ラジカル重合開始剤、
を含有し、前記(A)成分の含有割合は15〜50質量部の範囲であり、前記(B)成分の含有割合は50〜85質量部の範囲であることを特徴とする光学部品用接着剤組成物が提供される。
以上より、重合性官能基を有するジナフトチオフェン系化合物と、芳香環を含有する単官能(メタ)アクリレートと、光ラジカル重合開始剤との組み合わせによる相乗効果によって、高い屈折率と高い透明性を有し且つ溶剤の使用が不要である光学部品用接着剤組成物が得られることが分かった。
好ましくは、前記(B)成分が、ベンジル(メタ)アクリレート及びフェノキシエチル(メタ)アクリレートから選ばれる1つ以上を含む。
好ましくは、前記重合性官能基は、(メタ)アクリロイル基又はアリルエーテル基である。
好ましくは、前記一般式(1)において、a=b=c=0であり、d=1である。
好ましくは、前記(A)成分は、6−メタクリロイルメチルジナフトチオフェン、6−メタクリロイルエチルジナフトチオフェン、2,12−ジアリルエーテルジナフトチオフェン、及び3,11−ジアリルエーテルジナフトチオフェンから選ばれる1つ以上を含む。
好ましくは、前記(C)成分の含有割合は、組成物の総量に対して、0.2〜10質量部である。
本明細書において、接着剤組成物とは、部品と部品等を貼り合わせるための接着剤、特に光学部品の接着に好適に用いられる接着剤を意味する。
本実施形態に係るエネルギー線硬化性樹脂組成物は、(A)成分として、下記一般式(1)で表されるエチレン性不飽和二重結合を有する重合性官能基を1つ以上有するジナフトチオフェン系化合物を有する。
本発明の接着剤樹脂組成物は(B)成分として、1つ以上の芳香環を有する単官能(メタ)アクリレートを含有する。芳香環の数は、例えば、1,2,3であり、好ましくは、1つである。
本実施の接着剤樹脂組成物は、(C)光ラジカル重合開始剤を含有する。光ラジカル重合開始剤は、エネルギー線を照射することによりラジカルが発生する化合物であれば、特に制限されない。
本実施形態の目的を損なわない範囲で、酸化防止剤、シランカップリング剤、アクリルゴム、ウレタンゴム等の各種エラストマー、光増感剤、光安定剤、溶剤、増量材、充填剤、補強材、可塑剤、増粘剤、染料、顔料、難燃剤及び界面活性剤等の添加剤が含有しても良い。
ジナフトチオフェン化合物は、特開2011−178985(上記特許文献5)に記載の合成方法([実施例][0106]〜[0121])にて製造したものを用いた。
(A−1)6−メタクリロイルオキシメチルジナフトチオフェン(略号:DNTMA)
(A−2)6−ビニルジナフトチオフェン(略号:VDNT)
(A−3)6−メタクリロイルオキシエチルジナフトチオフェン(略号:EDNTMA)
(A−4)2,12−ジアリルオキシジナフトチオフェン(略号:DAODNT)
(A−5)3,11−ジアリルオキシジナフトチオフェン(略号:i−DAODNT)
(A−6)ジナフトチオフェン(略号:DNT)
(B−1)ベンジルメタクリレート(共栄社化学社製「ライトエステルBZ」)
(B−2)ベンジルアクリレート(大阪有機化学工業社製「ビスコート#160」)
(B−3)フェノキシエチルメタクリレート(共栄社化学社製「ライトエステルPO」)
(B−4)フェノキシエチルアクリレート(共栄社化学社製「ライトアクリレートPO−A」)
(B−5)2−(o−フェニルフェノキシ)エチルアクリレート(新中村化学工業社製「NKエステルA−LEN−10」)
(C−1)ベンジルジメチルケタール(BASF社製「イルガキュアー651」)
(C−2)1−ヒドロキシ−シクロヘキシルフェニルケトン(BASF社製「イルガキュアー184」)
(C−3)ビス(2,4,6−トリメチルベンゾイル)−フェニルフォスフィンオキサイド(BASF社製「イルガキュアー819」)
(D−1)ビスフェノールA型エポキシアクリレート(共栄社化学社製「エポキシエステル3002M」
(D−2)スチレン(和光純薬工業社製「スチレン」)
(D−3)メチルメタクリレート(三菱ガス化学社製「MMA」)
表1〜表2に示す種類の原材料を、表1〜表2に示す組成割合(単位は質量部)で混合し、接着剤組成物を調製し、後述の評価を実施した。溶媒は用いなかった。各種評価結果を表1〜表2に示す。特記しない限り、23℃、湿度50%の環境下で実施した。
30mlのバイアル瓶に接着剤組成物10mlを入れ密封したサンプルを準備し、サンプルを温度23℃の雰囲気中に24時間静置し、24時間後の液の状態を目視で確認し、以下の基準で評価した。
○:静置前と変化がなかった
△:析出物や分離物がみられるが50℃加温により再溶解した
×:析出物や分離物がみられ50℃加温でも再溶解しなかった
(1)液屈折率
液屈折率の評価は、多波長アッベ屈折率計(アタゴ社製「DR−M2」)を用いて、温度25℃、波長589nmにおける屈折率を測定した。
(2)硬化物屈折率
接着剤組成物を容積15mm×15mm×1.0mmのシリコーンゴム製の型枠に流し込み、超高圧水銀ランプ搭載装置(HOYA社製「UL−750」)にて、365nmの波長の照射強度30mW/cm2、積算光量30,000mJ/cm2の条件にて硬化した硬化物試験片を作成し、屈折率を評価した。屈折率の評価は、分光プリズムカプラ屈折率測定装置(メトリコン社製「MODEL 2010 PRISM COUPLER」)を用いて、波長633nmにおける屈折率を測定した。
接着剤組成物を耐熱ガラス(商品名「耐熱パイレックス(登録商標)ガラス」、25mm×25mm×2.0mm)上に膜厚30μmで塗布した後に、超高圧水銀ランプ搭載装置(HOYA社製「UL−750」)にて、365nmの波長の照射強度50mW/cm2、積算光量30,000mJ/cm2の条件にて硬化した試験片を作成し、紫外−可視分光光度計(島津製作所社製「UV−2550」)、リファレンスを耐熱ガラスとして、450nmの透過率を測定した。
実施例1〜10では、何れも液安定性・屈折率・分光透過率の点で優れた結果が得られた。但し、実施例1では、ジナフトチオフェン系化合物の配合割合が少ないため、屈折率が若干低かった。実施例6では、ジナフトチオフェン系化合物の配合割合が多いため、液安定性が若干悪化した。また、ビニル基を有するジナフトチオフェン系化合物を用いた実施例10では、(メタ)アクリロイル基又はアリルエーテル基を有するジナフトチオフェン系化合物を用いた実施例1〜9、実施例11〜14に比べて、液安定性及び分光透過率が好ましくなかった。この結果は、(メタ)アクリロイル基又はアリルエーテル基を有するジナフトチオフェン系化合物を用いることの優位性を示している。さらに、実施例3と実施例11〜13を比較すると、実施例3のようにDNTMAを用いた場合、屈折率及び分光透過率が特に高くなることが分かった。さらに、実施例14のように、(B)成分として芳香環を2つ有するアクリレートを用いたところ、液安定性及び分光透過率が悪化した。
Claims (7)
- (A)成分として、下記一般式(1)で表されるエチレン性不飽和二重結合を有する重合性官能基を1つ以上有するジナフトチオフェン系化合物、
(B)成分として、1つ以上の芳香環を含有する単官能(メタ)アクリレート、
(C)成分として、光ラジカル重合開始剤、
を含有し、組成物の総量に対して、前記(A)成分の含有割合は15〜50質量部の範囲であり、前記(B)成分の含有割合は50〜85質量部の範囲であることを特徴とする光学部品用接着剤組成物。 - 前記(B)成分は、1つの芳香環を含有する単官能(メタ)アクリレートである請求項1に記載の光学部品用接着剤組成物。
- 前記(B)成分は、ベンジル(メタ)アクリレート及びフェノキシエチル(メタ)アクリレートから選ばれる1つ以上を含むことを特徴とする請求項1又は2に記載の光学部品用接着剤組成物。
- 前記重合性官能基は、(メタ)アクリロイル基又はアリルエーテル基であることを特徴とする請求項1〜3の何れか1項に記載の光学部品用接着剤組成物。
- 前記一般式(1)において、a=b=c=0であり、d=1である請求項1〜4のいずれか1項に記載の光学部品用接着剤組成物。
- 前記(A)成分は、6−メタクリロイルオキシメチルジナフトチオフェン、6−メタクリロイルオキシエチルジナフトチオフェン、2,12−ジアリルオキシジナフトチオフェン、及び3,11−ジアリルオキシジナフトチオフェンから選ばれる1つ以上を含む請求項1〜5のいずれか1項に記載の光学部品用接着剤組成物。
- 前記(C)成分の含有割合は、組成物の総量に対して、0.2〜10質量部である請求項1〜6のいずれか1項に記載の光学部品用接着剤組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012129379A JP5878830B2 (ja) | 2012-06-06 | 2012-06-06 | 光学部品用接着剤組成物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012129379A JP5878830B2 (ja) | 2012-06-06 | 2012-06-06 | 光学部品用接着剤組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013253161A true JP2013253161A (ja) | 2013-12-19 |
JP5878830B2 JP5878830B2 (ja) | 2016-03-08 |
Family
ID=49950967
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012129379A Active JP5878830B2 (ja) | 2012-06-06 | 2012-06-06 | 光学部品用接着剤組成物 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5878830B2 (ja) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016104214A1 (ja) * | 2014-12-25 | 2016-06-30 | 三菱瓦斯化学株式会社 | 化合物、樹脂、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜、パターン形成方法及び精製方法 |
US10377734B2 (en) | 2013-02-08 | 2019-08-13 | Mitsubishi Gas Chemical Company, Inc. | Resist composition, method for forming resist pattern, polyphenol derivative for use in the composition |
US11137686B2 (en) | 2015-08-31 | 2021-10-05 | Mitsubishi Gas Chemical Company, Inc. | Material for forming underlayer film for lithography, composition for forming underlayer film for lithography, underlayer film for lithography and production method thereof, and resist pattern forming method |
US11143962B2 (en) | 2015-08-31 | 2021-10-12 | Mitsubishi Gas Chemical Company, Inc. | Material for forming underlayer film for lithography, composition for forming underlayer film for lithography, underlayer film for lithography and production method thereof, pattern forming method, resin, and purification method |
US11243467B2 (en) | 2015-09-10 | 2022-02-08 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, resist composition or radiation-sensitive composition, resist pattern formation method, method for producing amorphous film, underlayer film forming material for lithography, composition for underlayer film formation for lithography, method for forming circuit pattern, and purification method |
US11256170B2 (en) | 2015-03-31 | 2022-02-22 | Mitsubishi Gas Chemical Company, Inc. | Compound, resist composition, and method for forming resist pattern using it |
US11480877B2 (en) | 2015-03-31 | 2022-10-25 | Mitsubishi Gas Chemical Company, Inc. | Resist composition, method for forming resist pattern, and polyphenol compound used therein |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6710125B2 (ja) * | 2016-08-04 | 2020-06-17 | 日本化薬株式会社 | 液晶シール剤及びそれを用いた液晶表示セル |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011178985A (ja) * | 2010-02-04 | 2011-09-15 | Kanagawa Univ | 屈折率向上剤、並びにそれを含む樹脂組成物、重合若しくは硬化性組成物及び光学材料 |
JP2012136576A (ja) * | 2010-12-24 | 2012-07-19 | Kanagawa Univ | 耐硬化収縮性の硬化性組成物、及び当該硬化性組成物を硬化させた硬化物 |
-
2012
- 2012-06-06 JP JP2012129379A patent/JP5878830B2/ja active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011178985A (ja) * | 2010-02-04 | 2011-09-15 | Kanagawa Univ | 屈折率向上剤、並びにそれを含む樹脂組成物、重合若しくは硬化性組成物及び光学材料 |
JP2012136576A (ja) * | 2010-12-24 | 2012-07-19 | Kanagawa Univ | 耐硬化収縮性の硬化性組成物、及び当該硬化性組成物を硬化させた硬化物 |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10377734B2 (en) | 2013-02-08 | 2019-08-13 | Mitsubishi Gas Chemical Company, Inc. | Resist composition, method for forming resist pattern, polyphenol derivative for use in the composition |
WO2016104214A1 (ja) * | 2014-12-25 | 2016-06-30 | 三菱瓦斯化学株式会社 | 化合物、樹脂、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜、パターン形成方法及び精製方法 |
JPWO2016104214A1 (ja) * | 2014-12-25 | 2017-10-05 | 三菱瓦斯化学株式会社 | 化合物、樹脂、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜、パターン形成方法及び精製方法 |
US20170349564A1 (en) | 2014-12-25 | 2017-12-07 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and purification method |
US10745372B2 (en) | 2014-12-25 | 2020-08-18 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and purification method |
JP7026439B2 (ja) | 2014-12-25 | 2022-02-28 | 三菱瓦斯化学株式会社 | 化合物、樹脂、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜、パターン形成方法及び精製方法 |
US11256170B2 (en) | 2015-03-31 | 2022-02-22 | Mitsubishi Gas Chemical Company, Inc. | Compound, resist composition, and method for forming resist pattern using it |
US11480877B2 (en) | 2015-03-31 | 2022-10-25 | Mitsubishi Gas Chemical Company, Inc. | Resist composition, method for forming resist pattern, and polyphenol compound used therein |
US11137686B2 (en) | 2015-08-31 | 2021-10-05 | Mitsubishi Gas Chemical Company, Inc. | Material for forming underlayer film for lithography, composition for forming underlayer film for lithography, underlayer film for lithography and production method thereof, and resist pattern forming method |
US11143962B2 (en) | 2015-08-31 | 2021-10-12 | Mitsubishi Gas Chemical Company, Inc. | Material for forming underlayer film for lithography, composition for forming underlayer film for lithography, underlayer film for lithography and production method thereof, pattern forming method, resin, and purification method |
US11243467B2 (en) | 2015-09-10 | 2022-02-08 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, resist composition or radiation-sensitive composition, resist pattern formation method, method for producing amorphous film, underlayer film forming material for lithography, composition for underlayer film formation for lithography, method for forming circuit pattern, and purification method |
US11572430B2 (en) | 2015-09-10 | 2023-02-07 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, resist composition or radiation-sensitive composition, resist pattern formation method, method for producing amorphous film, underlayer film forming material for lithography, composition for underlayer film formation for lithography, method for forming circuit pattern, and purification method |
Also Published As
Publication number | Publication date |
---|---|
JP5878830B2 (ja) | 2016-03-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5878830B2 (ja) | 光学部品用接着剤組成物 | |
JP6155449B2 (ja) | 光学部品用高屈折率接着剤組成物 | |
JP6105574B2 (ja) | 被覆材用樹脂組成物 | |
CN106414525B (zh) | 光固化性树脂组合物 | |
JP6063228B2 (ja) | 光硬化性樹脂組成物 | |
JP2020090671A (ja) | 被覆材用樹脂組成物 | |
JP5810611B2 (ja) | 硬化性組成物および光学接着剤 | |
JP6174942B2 (ja) | 光学部品用光硬化性樹脂組成物及び光学部品の製造方法 | |
JP4589211B2 (ja) | 光学用紫外線硬化型液状樹脂組成物 | |
JP7035728B2 (ja) | 液晶パネル封止材樹脂組成物、および該液晶パネル封止材樹脂組成物で端部を封止したフィルム液晶パネル | |
JP7002237B2 (ja) | 光硬化性高屈折率樹脂組成物 | |
JP2003238904A (ja) | 光硬化型光学用接着剤組成物 | |
JPWO2004011511A1 (ja) | 光重合性組成物およびその用途 | |
WO2023188968A1 (ja) | 多官能(メタ)アクリル酸チオエステル組成物、硬化性組成物、硬化物、成形体、光学材料及び多官能(メタ)アクリル酸チオエステル組成物の製造方法 | |
JP2006008740A (ja) | 紫外線硬化型樹脂組成物 | |
JP5849432B2 (ja) | 硬化性組成物および光学接着剤 | |
JPH115952A (ja) | 光学用接着剤組成物 | |
JP6507683B2 (ja) | 樹脂組成物及び光学部材 | |
JP4331644B2 (ja) | 紫外線硬化型樹脂組成物 | |
WO2022196516A1 (ja) | 硬化性組成物、及び当該組成物から得られる光学材料 | |
JP2013053199A (ja) | 光硬化性組成物 | |
JP2021055051A (ja) | 紫外線硬化性樹脂組成物、発光装置、及び発光装置の製造方法 | |
JP2010222435A (ja) | 硬化性樹脂組成物、硬化樹脂、および硬化樹脂の製造方法 | |
JP2008216792A (ja) | 光学素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150416 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20151224 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160112 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160129 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5878830 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |