JP6155449B2 - High refractive index adhesive composition for optical components - Google Patents
High refractive index adhesive composition for optical components Download PDFInfo
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- JP6155449B2 JP6155449B2 JP2013179273A JP2013179273A JP6155449B2 JP 6155449 B2 JP6155449 B2 JP 6155449B2 JP 2013179273 A JP2013179273 A JP 2013179273A JP 2013179273 A JP2013179273 A JP 2013179273A JP 6155449 B2 JP6155449 B2 JP 6155449B2
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- 239000000203 mixture Substances 0.000 title claims description 49
- 239000000853 adhesive Substances 0.000 title claims description 44
- 230000001070 adhesive effect Effects 0.000 title claims description 44
- 230000003287 optical effect Effects 0.000 title claims description 35
- -1 polyene compound Chemical class 0.000 claims description 50
- SYXXZXWLYNODHL-UHFFFAOYSA-N dinaphthothiophene Chemical compound C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)S3)C3=CC=C21 SYXXZXWLYNODHL-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 12
- 229920006295 polythiol Polymers 0.000 claims description 10
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 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
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 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
- 125000004430 oxygen atom Chemical group O* 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
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 description 9
- 239000011342 resin composition Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000005304 joining Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 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
- 241000511976 Hoya Species 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 229960000834 vinyl ether Drugs 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HAQZWTGSNCDKTK-UHFFFAOYSA-N 2-(3-sulfanylpropanoyloxy)ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOC(=O)CCS HAQZWTGSNCDKTK-UHFFFAOYSA-N 0.000 description 2
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-UHFFFAOYSA-N 0.000 description 2
- XKFYRSQYBLCILF-UHFFFAOYSA-N 4-methyl-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 C1=CC=C2C(SC3=CC=C4C=CC=C(C4=C33)C)=C3C=CC2=C1 XKFYRSQYBLCILF-UHFFFAOYSA-N 0.000 description 2
- 102100027123 55 kDa erythrocyte membrane protein Human genes 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- JHWMAGJBGVHESO-UHFFFAOYSA-N C=CC(=O)OCCOC1=CC=CC2=C1C3=C(C=C2)SC4=C3C=C(C5=CC=CC=C54)OC(=O)C=C Chemical compound C=CC(=O)OCCOC1=CC=CC2=C1C3=C(C=C2)SC4=C3C=C(C5=CC=CC=C54)OC(=O)C=C JHWMAGJBGVHESO-UHFFFAOYSA-N 0.000 description 2
- GLSLQYDMRWNVGD-UHFFFAOYSA-N CC(=C)C(=O)CC1=CC2=C(C=C1)C=CC3=C2C4=C(S3)C5=CC=CC=C5C(=C4)CC(=O)C(=C)C Chemical compound CC(=C)C(=O)CC1=CC2=C(C=C1)C=CC3=C2C4=C(S3)C5=CC=CC=C5C(=C4)CC(=O)C(=C)C GLSLQYDMRWNVGD-UHFFFAOYSA-N 0.000 description 2
- JTBAYBHLXLRNRK-UHFFFAOYSA-N CC(=C)C(=O)OCCOC1=CC=CC2=C1C3=C(C=C2)SC4=C3C=C(C5=CC=CC=C54)OC(=O)C(=C)C Chemical compound CC(=C)C(=O)OCCOC1=CC=CC2=C1C3=C(C=C2)SC4=C3C=C(C5=CC=CC=C54)OC(=O)C(=C)C JTBAYBHLXLRNRK-UHFFFAOYSA-N 0.000 description 2
- UQWWGMATBBQFAD-UHFFFAOYSA-N CC(C(=O)OC1=CC=CC2=C1C3=C(C=C2)SC4=C3C=C(C5=CC=CC=C54)OC(=O)C=C)OC(=O)C=C Chemical compound CC(C(=O)OC1=CC=CC2=C1C3=C(C=C2)SC4=C3C=C(C5=CC=CC=C54)OC(=O)C=C)OC(=O)C=C UQWWGMATBBQFAD-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 101001057956 Homo sapiens 55 kDa erythrocyte membrane protein Proteins 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-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
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000001444 catalytic combustion detection Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 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
- 150000004005 nitrosamines Chemical class 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 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
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-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
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- PAEWNKLGPBBWNM-UHFFFAOYSA-N 1,3,5-tris[2-(3-sulfanylbutoxy)ethyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(S)CCOCCN1C(=O)N(CCOCCC(C)S)C(=O)N(CCOCCC(C)S)C1=O PAEWNKLGPBBWNM-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
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- TWWSEEHCVDRRRI-UHFFFAOYSA-N 2,3-Butanedithiol Chemical compound CC(S)C(C)S TWWSEEHCVDRRRI-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- ZZYASVWWDLJXIM-UHFFFAOYSA-N 2,5-di-tert-Butyl-1,4-benzoquinone Chemical compound CC(C)(C)C1=CC(=O)C(C(C)(C)C)=CC1=O ZZYASVWWDLJXIM-UHFFFAOYSA-N 0.000 description 1
- QYXHDJJYVDLECA-UHFFFAOYSA-N 2,5-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=C(C=2C=CC=CC=2)C(=O)C=C1C1=CC=CC=C1 QYXHDJJYVDLECA-UHFFFAOYSA-N 0.000 description 1
- QSOFJLDXOMMNNK-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O.CC(S)CC(O)=O.CC(S)CC(O)=O.OCC(C)(CO)CO QSOFJLDXOMMNNK-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
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- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 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)
Description
本発明は、レンズ、プリズム、光導波路などの光学素子の接着に用いる光学部品用接着剤組成物に関する。 The present invention relates to an adhesive composition for optical parts used for bonding optical elements such as lenses, prisms and optical waveguides.
従来、カメラや顕微鏡などの光学機器の組立てにおいては、レンズやプリズムなどを接合するため、バルサムやエポキシ樹脂などの透明樹脂が接着剤として用いられていた。また近年、オプトエレクトロニクス産業の発展にともない、光ファイバーやマイクロレンズ等の高度な光学機能を持った光学素子類を接合する用途が増大しており、ビスフェノールＡ型エポキシ（メタ）アクリレートやウレタン（メタ）アクリレート等のラジカル重合性モノマーを配合した接着剤も広く使用されるようになっている。 Conventionally, in assembling optical devices such as cameras and microscopes, transparent resins such as balsams and epoxy resins have been used as adhesives to join lenses and prisms. In recent years, with the development of the optoelectronics industry, applications for joining optical elements with advanced optical functions such as optical fibers and microlenses are increasing, and bisphenol A type epoxy (meth) acrylate and urethane (meth). Adhesives containing radically polymerizable monomers such as acrylates are also widely used.
特に、光導波路素子とマイクロレンズや光ファイバーなどを接合して、光変調器や光スイッチなどの光回路を作製する場合や、薄型レンズの接合等の、高度な光学特性を必要とする光学部品の接合において、高屈折率を有する接着剤が必要とされている。このような接着剤としては、例えば特許文献１〜３には、硫黄含有（メタ）アクリレートを用いた接着剤組成物および光硬化性樹脂組成物が公知である。また例えば特許文献４には、ジフェニルスルフォン構造を有するウレタン（メタ）アクリレートを用いた活性エネルギー線硬化性組成物が開示されており、接着剤として有用であるとされている。 In particular, when optical circuits such as optical modulators and optical switches are manufactured by joining optical waveguide elements and microlenses, optical fibers, etc., and for optical components that require advanced optical properties such as joining thin lenses. In joining, an adhesive having a high refractive index is required. As such an adhesive, for example, Patent Documents 1 to 3 disclose an adhesive composition using a sulfur-containing (meth) acrylate and a photocurable resin composition. Further, for example, Patent Document 4 discloses an active energy ray-curable composition using urethane (meth) acrylate having a diphenylsulfone structure, which is useful as an adhesive.
しかしながら、前記の特許文献に記載の主成分である、硫黄含有（メタ）アクリレートや、ジフェニルスルフォン構造を有するウレタン（メタ）アクリレートでは、４，４'−ジメルカプトジフェニルサルファイドジメタクリレートは、ビスフェノールＡ型エポキシ（メタ）アクリレート等の芳香環を有する化合物よりは高い屈折率を有してはいるものの、光学レンズ等の薄型化に伴う高屈折率の要求を満たすことはできず、また、これら化合物は一般に波長４５０ｎｍ以下の光を吸収するため、黄色く着色し透明性が低下しやすいという課題があった。 However, in the case of sulfur-containing (meth) acrylate and urethane (meth) acrylate having a diphenylsulfone structure, which are the main components described in the above-mentioned patent documents, 4,4′-dimercaptodiphenyl sulfide dimethacrylate is a bisphenol A type. Although it has a higher refractive index than a compound having an aromatic ring, such as epoxy (meth) acrylate, it cannot meet the requirements for a high refractive index associated with the thinning of optical lenses, etc. In general, in order to absorb light having a wavelength of 450 nm or less, there is a problem in that it is colored yellow and transparency tends to be lowered.
前記の様な課題に対して高い屈折率と高い透明性を有する化合物として特許文献５にジナフトチオフェン骨格を有する化合物および重合体が開示されている。特許文献５の実施例では、エチレン性不飽和二重結合を有するジナフトチオフェンを用いた光重合性組成物を、酢酸エチル等の溶剤を用いて希釈して作成した光硬化膜が開示されている（段落番号［０１４３］）。しかしながら、光学部品の接着に用いる場合は、残存溶剤の影響で強度の低下や、アウトガス発生の要因となり、良好な信頼性を得ることができなかったり、あるいは長時間保存した場合等に結晶性の成分が組成物中に析出しやすく、屈折率が変動したり、塗布できなくなったりするといった欠点があった。また、光成形、ナノインプリントといった微細成形プロセス等においても寸法精度が確保できないため、溶剤を使用できない場合が多く、溶剤で希釈した組成物を使用することは困難であった。 As a compound having a high refractive index and high transparency with respect to the above problems, Patent Document 5 discloses a compound and a polymer having a dinaphthothiophene skeleton. In Examples of Patent Document 5, a photocured film prepared by diluting a photopolymerizable composition using dinaphthothiophene having an ethylenically unsaturated double bond with a solvent such as ethyl acetate is disclosed. (Paragraph number [0143]). However, when used for bonding optical parts, it may cause a decrease in strength or outgassing due to the influence of residual solvent, and it may not be possible to obtain good reliability, or it may be crystalline when stored for a long time. The components are liable to be precipitated in the composition, resulting in a disadvantage that the refractive index varies or cannot be applied. In addition, since a dimensional accuracy cannot be ensured even in a micro-molding process such as photo-molding and nano-imprint, it is often difficult to use a solvent, and it is difficult to use a composition diluted with a solvent.
本発明はこのような事情に鑑みてなされたものであり、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を提供するものである。 This invention is made | formed in view of such a situation, and provides the adhesive composition for optical components which has a high refractive index, high transparency, and does not require the use of a solvent.
本発明によれば、
（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２つ以上有するジナフトチオフェン系ポリエン化合物、
（Ｂ）成分として、ポリチオール化合物、
（Ｃ）成分として、光ラジカル重合開始剤、
（Ｄ）成分として、ジナフトチオフェン系以外であり且つ前記（Ａ）成分よりも炭素数が少ないポリエン化合物、
を含有し、前記（Ａ）成分の含有割合が組成物の総量に対して５〜５０質量部の範囲であり、前記（Ｂ）成分の含有割合が組成物の総量に対して１０〜６０質量部の範囲であり、前記（Ｄ）成分の含有割合が組成物の総量に対して５〜８５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。
According to the present invention,
(1) A dinaphthothiophene-based polyene compound having two or more polymerizable functional groups having an ethylenically unsaturated double bond represented by the following general formula (1) as the component (A):
(B) As a component, a polythiol compound,
(C) As a component, radical photopolymerization initiator,
As the component (D), a polyene compound that is other than dinaphthothiophene and has fewer carbon atoms than the component (A),
The content ratio of the component (A) is in the range of 5 to 50 parts by mass with respect to the total amount of the composition, and the content ratio of the component (B) is 10 to 60 masses with respect to the total amount of the composition. The adhesive composition for optical components is provided, wherein the content ratio of the component (D) is in the range of 5 to 85 parts by mass with respect to the total amount of the composition.
本発明者らは、被覆材用樹脂組成物に適した組成物を得るべく鋭意検討を行なっていたところ、上記一般式（１）に示すようなジナフトチオフェン系ポリエン化合物は、溶媒を用いずに、ポリチオール化合物と混合すると、しばらく静置した後に、容易に溶解しない析出物や分離物が発生し、被覆材用樹脂組成物として利用することが難しいことが分かった。そこで、このような問題を解決すべく、さらに検討を進めたところ、（Ｄ）成分として、ジナフトチオフェン系以外であり且つ（Ａ）成分よりも炭素数が少ないポリエン化合物を添加することによって、ジナフトチオフェン系ポリエン化合物とポリチオール化合物の間の相溶性が向上して、上記（Ａ）〜（Ｄ）成分の混合物を静置させた場合に容易に溶解しない析出物の発生を抑制することができることが見出し、本発明の完成に到った。 The present inventors have intensively studied to obtain a composition suitable for the resin composition for a coating material, and the dinaphthothiophene polyene compound represented by the general formula (1) does not use a solvent. In addition, when mixed with a polythiol compound, it was found that after standing for a while, precipitates and isolates that did not easily dissolve were generated, making it difficult to use as a resin composition for a coating material. Then, when further examination was advanced to solve such a problem, as a component (D), by adding a polyene compound other than dinaphthothiophene and having a smaller number of carbon atoms than the component (A), The compatibility between the dinaphthothiophene-based polyene compound and the polythiol compound is improved, and the generation of precipitates that do not easily dissolve when the mixture of the above components (A) to (D) is allowed to stand is suppressed. As a result, the present invention has been completed.
好ましくは、さらに（Ｅ）成分として、重合禁止剤を含有する。
好ましくは、前記重合性官能基は、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＝０であり、ｃ＝ｄ＝１である。
好ましくは、前記（Ａ）成分は、２，１２−ジアリルエーテルジナフトチオフェンを含む。
好ましくは、前記（Ｄ）成分は、炭素数が６〜２３である。
好ましくは、前記（Ｄ）成分は、（メタ）アクリレート、アリル化合物及びアリルエーテル化合物からなる群のうちの１種以上である。
Preferably, a polymerization inhibitor is further contained as component (E).
Preferably, the polymerizable functional group is an allyl ether group.
Preferably, in the general formula (1), a = b = 0 and c = d = 1.
Preferably, the component (A) includes 2,12-diallyl ether dinaphthothiophene.
Preferably, the component (D) has 6 to 23 carbon atoms.
Preferably, the component (D) is at least one member selected from the group consisting of (meth) acrylates, allyl compounds, and allyl ether compounds.
本発明の接着剤組成物は、２つ以上の重合性官能基を有するジナフトチオフェン系ポリエン化合物、ポリチオール化合物、ラジカル重合開始剤を特定の割合で含有する光学部品用接着剤組成物からなるので、光学部品の接着に求められる高い屈折率と高い透明性を有するという特徴を有している。また、本発明の接着剤組成物は、溶媒を使用する必要がないため、残存溶剤の影響による強度低下や、アウトガス発生の問題を回避することができ、かつ微細成形プロセスにおいても高い寸法精度を確保することができる。 Since the adhesive composition of the present invention comprises an adhesive composition for optical components containing a dinaphthothiophene polyene compound having two or more polymerizable functional groups, a polythiol compound, and a radical polymerization initiator in a specific ratio. And having a high refractive index and high transparency required for adhesion of optical components. In addition, since the adhesive composition of the present invention does not require the use of a solvent, it can avoid the problem of strength reduction and outgas generation due to the influence of the residual solvent, and has high dimensional accuracy even in a fine molding process. Can be secured.
＜用語の説明＞
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。本明細書において、「樹脂組成物の総量」とは、（Ａ）成分、（Ｂ）成分、（Ｄ）成分の合計１００質量部をいう。
<Explanation of terms>
In the present specification, the adhesive composition means an adhesive for bonding parts to each other, particularly an adhesive suitably used for bonding optical parts. In this specification, the “total amount of the resin composition” refers to a total of 100 parts by mass of the component (A), the component (B), and the component (D).
本実施形態に係る接着剤組成物の成分について説明する。 The components of the adhesive composition according to this embodiment will be described.
＜（Ａ）成分：ジナフトチオフェン系ポリエン化合物＞
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２つ以上有するジナフトチオフェン系ポリエン化合物を有する。
The energy ray-curable resin composition according to the present embodiment has, as component (A), dinaphtho having two or more polymerizable functional groups having an ethylenically unsaturated double bond represented by the following general formula (1). It has a thiophene-based polyene compound.
上記重合性官能基としては、ビニル基、スチリル基、ビニルエーテル基、アリル基、アリルエーテル基、（メタ）アクリロイル基、アクリロニトリル基等が例示できるが、透明性、反応性の点で（メタ）アクリロイル基又はアリルエーテル基が好ましく、アリルエーテル基が特に好ましい。 Examples of the polymerizable functional group include a vinyl group, a styryl group, a vinyl ether group, an allyl group, an allyl ether group, a (meth) acryloyl group, and an acrylonitrile group, but (meth) acryloyl in terms of transparency and reactivity. Group or an allyl ether group is preferable, and an allyl ether group is particularly preferable.
上記ジナフトチオフェン系化合物の具体例としては、２，１２−ジビニルジナフトチオフェン、３，１１−ジビニルジナフトチオフェン、５，９−ジビニルジナフトチオフェン、２，１２−ジアクリロイルメチルジナフトチオフェン、３，１１−ジアクリロイルメチルジナフトチオフェン、２，１２−ジメタクリロイルメチルジナフトチオフェン、３，１１−ジメタクリロイルメチルジナフトチオフェン、２，１２−ジアリルエーテルメチルジナフトチオフェン、３，１１−ジアリルエーテルジナフトチオフェン、２，１２−ジビニルエーテルメチルジナフトチオフェン、３，１１−ジビニルエーテルジナフトチオフェン、２，１２−ジメタクリロイロキシエトキシジナフトチオフェン、２，１２−ジメタクリロイロキシプロピオキシジナフトチオフェン、２，１２−ジアクリロイロキシエトキシジナフトチオフェン、２，１２−ジアクリロイロキシプロピオキシジナフトチオフェン等が挙げられるが、（Ｂ）成分との相溶性の点で、２，１２−置換体である２，１２−ジアクリロイルメチルジナフトチオフェン、２，１２−ジメタクリロイルメ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、２，１２−ジメタクリロイロキシエトキシジナフトチオフェン、２，１２−ジメタクリロイロキシプロピオキシジナフトチオフェン、２，１２−ジアクリロイロキシエトキシジナフトチオフェン、２，１２−ジアクリロイロキシプロピオキシジナフトチオフェンが好ましく、（Ｂ）成分との反応性の点で、２，１２−ジアリルエーテルジナフトチオフェンが特に好ましい。 Specific examples of the dinaphthothiophene compound include 2,12-divinyldinaphthothiophene, 3,11-divinyldinaphthothiophene, 5,9-divinyldinaphthothiophene, 2,12-diacryloylmethyldinaphthothiophene, 3,11-Diacryloylmethyldinaphthothiophene, 2,12-dimethacryloylmethyldinaphthothiophene, 3,11-dimethacryloylmethyldinaphthothiophene, 2,12-diallyl ether methyldinaphthothiophene, 3,11-diallyl ether Dinaphthothiophene, 2,12-divinyl ether methyldinaphthothiophene, 3,11-divinyl ether dinaphthothiophene, 2,12-dimethacryloyloxyethoxydinaphthothiophene, 2,12-dimethacryloyloxypropoxydinaphth Examples include thiophene, 2,12-diacryloyloxyethoxydinaphthothiophene, 2,12-diacryloyloxypropioxydinaphthothiophene, etc., but in terms of compatibility with component (B), 2,12- 2,12-Diacryloylmethyldinaphthothiophene, 2,12-dimethacryloylmethyldinaphthothiophene, 2,12-diallyl ether dinaphthothiophene, 2,12-dimethacryloyloxyethoxydinaphthothiophene, 2 , 12-Dimethacryloyloxypropioxydinaphththiophene, 2,12-diacryloyloxyethoxydinaphthothiophene, 2,12-diacryloyloxypropioxydinaphthothiophene are preferable, and the reactivity with the component (B) 2,12-diallyl ether dinaphthothiophene Preferred.
（Ａ）成分の含有割合は、接着剤組成物の総量に対して５〜５０質量部であることが好ましく、特に高屈折率と（Ｂ）成分との相溶性の点で、１５〜４５質量部がより好ましい。（Ａ）成分の含有割合は、具体的には例えば、５、１０、１５、２０、２５、３０、３５、４０、４５、５０質量部であり、ここで例示した数値の何れか２つの間の範囲内であってもよい。 The content ratio of the component (A) is preferably 5 to 50 parts by mass with respect to the total amount of the adhesive composition, and particularly 15 to 45 masses in terms of compatibility between the high refractive index and the component (B). Part is more preferred. Specifically, the content ratio of the component (A) is, for example, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50 parts by mass, and between any two of the numerical values exemplified here. It may be within the range.
上記ジナフトチオフェン系ポリエン化合物は、特許文献５〜６又は非特許文献１に例示される製造方法をもって製造することができるが、この方法に限らずいかなる製造方法によって製造されたものでも使用できる。 Although the said dinaphtho thiophene type polyene compound can be manufactured with the manufacturing method illustrated by patent documents 5-6 or nonpatent literature 1, what was manufactured by what kind of manufacturing method is not restricted to this method.
＜（Ｂ）成分：ポリチオール化合物＞
本発明の接着剤樹脂組成物は（Ｂ）成分として、ポリチオール化合物を含有する。
<(B) component: polythiol compound>
The adhesive resin composition of the present invention contains a polythiol compound as the component (B).
本発明で使用するポリチオール化合物は、１分子当たり２個以上のチオール基を有する平均分子量が５０〜１５０００の物質である。 The polythiol compound used in the present invention is a substance having an average molecular weight of 50 to 15000 having two or more thiol groups per molecule.
本発明に於いて使用されるポリチオール化合物の具体例としては、ジメルカプトブタンやトリメルカプトヘキサンなどのメルカプト基置換アルキル化合物、ジメルカプトベンゼンなどのメルカプト基置換アリル化合物、トリメチロールプロパン−トリス−（β−チオプロピネート）、トリス−２−ヒドロキシエチル−イソシアヌレート・トリス−β−メルカプトプロピオネート、ペンタエリスリトールテトラキス（β−チオプロピオネート）などのチオグリコール酸やチオプロピオン酸などの多価アルコールエステル、及び１，８−ジメルカプト−３，６−ジオキサオクタン、１，１１−ジメルカプト３，６，９−トリオキサドデカン、ジエチレングリコールビスチオグリコレート、トリエチレングリコールビスチオグリコレート、テトラエチレングリコールビスチオグリコレート、ペンタエチレングリコールビスチオグリコレート、ヘキサエチレングリコールビスチオグリコレート、オクタエチレングリコールビスチオグリコレート、ドデカンエチレングリコールビスチオグリコレート、ジエチレングリコールビス（３−メルカプトプロピオネート）、トリエチレングリコールビス（３−メルカプトプロピオネート）、テトラエチレングリコールビス（３−メルカプトプロピオネート）、ペンタエチレングリコールビス（３−メルカプトプロピオネート）、ヘキサエチレングリコールビス（３−メルカプトプロピオネート）、オクタエチレングリコールビス（３−メルカプトプロピオネート）、ドデカンエチレングリコールビス（３−メルカプトプロピオネート）、ジエチレングリコールビス（３−メルカプトブチレート）、トリエチレングリコールビス（３−メルカプトブチレート）、テトラエチレングリコールビス（３−メルカプトブチレート）、ペンタエチレングリコールビス（３−メルカプトブチレート）、ヘキサエチレングリコールビス（３−メルカプトブチレート）、オクタエチレングリコールビス（３−メルカプトブチレート）、ドデカンエチレングリコールビス（３−メルカプトブチレート）、ポリエチレングリコールビスチオグリコレート、ポリエチレングリコールビス（３−メルカプトプロピオネート）、ポリエチレングリコールビス（３−メルカプトブチレート）、ポリプロピレングリコールビスチオグリコレート、ポリプロピレングリコールビス（３−メルカプトプロピオネート）、ポリプロピレングリコールビス（３−メルカプトブチレート）、１，４−ビス(３−メルカプトブチリルオキシ)ブタン、トリメチロールプロパン−トリス−（３−メルカプトプロピネート）のエチレンオキサイド付加物、トリス−[(３−メルカプトプロピオニルオキシ)−エチル]−イソシアヌレートのエチレンオキサイド付加物、ペンタエリスリトールテトラキス（３−メルカプトプロピオネート）のエチレンオキサイド付加物、ペンタエリスリトールテトラキス(３−メルカプトブチレート) のエチレンオキサイド付加物、トリメチロールエタントリス（３−メルカプトブチレート）のエチレンオキサイド付加物、１，３，５−トリス(３−メルカブトブチルオキシエチル）−１，３，５−トリアジン−２，４，６(１Ｈ，３Ｈ，５Ｈ)−トリオン、ジペンタエリスリトールヘキサキス（３−メルカプトプロピオネート）のエチレンオキサイド付加物等の多価アルコールのアルキレンオキサイド付加物と硫化水素の反応生成物、その他、１，８−ジメルカプト−３，６−ジスルフィドオクタン、トリアジンチオールなどが挙げられる。中でも（Ａ）成分との相溶性の点から、アルキレンオキサイド付加物と硫化水素の反応生成物が好ましく、特に１，８−ジメルカプト−３，６−ジオキサオクタンが好ましい。 Specific examples of the polythiol compound used in the present invention include mercapto group-substituted alkyl compounds such as dimercaptobutane and trimercaptohexane, mercapto group-substituted allyl compounds such as dimercaptobenzene, trimethylolpropane-tris- (β -Thiopropionate), tris-2-hydroxyethyl-isocyanurate tris-β-mercaptopropionate, pentaerythritol tetrakis (β-thiopropionate) and other polyhydric alcohols such as thioglycolic acid and thiopropionic acid Esters, and 1,8-dimercapto-3,6-dioxaoctane, 1,11-dimercapto 3,6,9-trioxadodecane, diethylene glycol bisthioglycolate, triethylene glycol bisthioglycolate, tetraethy Glycol bisthioglycolate, pentaethylene glycol bisthioglycolate, hexaethylene glycol bisthioglycolate, octaethylene glycol bisthioglycolate, dodecane ethylene glycol bisthioglycolate, diethylene glycol bis (3-mercaptopropionate), Triethylene glycol bis (3-mercaptopropionate), tetraethylene glycol bis (3-mercaptopropionate), pentaethylene glycol bis (3-mercaptopropionate), hexaethylene glycol bis (3-mercaptopropionate) ), Octaethylene glycol bis (3-mercaptopropionate), dodecane ethylene glycol bis (3-mercaptopropionate), diethylene glycol Bis (3-mercaptobutyrate), triethylene glycol bis (3-mercaptobutyrate), tetraethylene glycol bis (3-mercaptobutyrate), pentaethylene glycol bis (3-mercaptobutyrate), hexaethylene glycol bis ( 3-mercaptobutyrate), octaethylene glycol bis (3-mercaptobutyrate), dodecane ethylene glycol bis (3-mercaptobutyrate), polyethylene glycol bisthioglycolate, polyethylene glycol bis (3-mercaptopropionate), Polyethylene glycol bis (3-mercaptobutyrate), polypropylene glycol bisthioglycolate, polypropylene glycol bis (3-mercaptopropionate), polypropylene Ethylene glycol bis (3-mercaptobutyrate), 1,4-bis (3-mercaptobutyryloxy) butane, trimethylolpropane-tris- (3-mercaptopropinate) ethylene oxide adduct, tris-[(3 -Mercaptopropionyloxy) -ethyl] -isocyanurate ethylene oxide adduct, pentaerythritol tetrakis (3-mercaptopropionate) ethylene oxide adduct, pentaerythritol tetrakis (3-mercaptobutyrate) ethylene oxide adduct, Ethylene oxide adduct of trimethylolethane tris (3-mercaptobutyrate), 1,3,5-tris (3-mercaptobutyloxyethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, dipentae Reaction product of alkylene oxide adduct of polyhydric alcohol such as ethylene oxide adduct of sitolitol hexakis (3-mercaptopropionate) and hydrogen sulfide, 1,8-dimercapto-3,6-disulfide octane, And triazine thiol. Among these, from the point of compatibility with the component (A), a reaction product of an alkylene oxide adduct and hydrogen sulfide is preferable, and 1,8-dimercapto-3,6-dioxaoctane is particularly preferable.
（Ｂ）成分の含有割合は、接着剤組成物の総量に対して１０〜６０質量部であることが好ましく、特に高屈折率、（Ａ）成分との相溶性の点で、２０〜５０質量部がより好ましい。（Ｂ）成分の含有割合は、具体的には例えば、１０、１５、２０、２５、３０、３５、４０、４５、５０、５５、６０質量部であり、ここで例示した数値の何れか２つの間の範囲内であってもよい。 The content ratio of the component (B) is preferably 10 to 60 parts by mass with respect to the total amount of the adhesive composition, particularly 20 to 50 masses in terms of high refractive index and compatibility with the component (A). Part is more preferred. Specifically, the content ratio of the component (B) is, for example, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60 parts by mass, and any of the numerical values exemplified here is 2 It may be within a range between the two.
＜（Ｃ）成分：光ラジカル重合開始剤＞
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。
<(C) component: radical photopolymerization initiator>
The adhesive resin composition of the present embodiment contains (C) a radical photopolymerization initiator. The radical photopolymerization initiator is not particularly limited as long as it is a compound that generates radicals when irradiated with energy rays.
上記光ラジカル重合開始剤としては、ベンジル、ベンゾイン、ベンゾイン安息香酸、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル等のベンゾイン誘導体、ベンゾフェノン、４−フェニルベンゾフェノン等のベンゾフェノン誘導体、２，２−ジエトキシアセトフェノン、ベンジルジメチルケタール等のアルキルアセトフェノン誘導体、１−ヒドロキシシクロヘキシルフェニルケトン、１−（４−イソプロピルフェニル）２−ヒドロキシ−２−メチルプロパン−１−オン、１−（４−（２−ヒドロキシエトキシ）−フェニル）−２−ヒドロキシ−２−メチル−１−プロパン−１−オン、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン等のα−ヒドロキシアセトフェノン誘導体、ビスジエチルアミノベンゾフェノン、２−メチル−１−（４−（メチルチオ）フェニル）−２−モルフォリノプロパン−１−オン、２−ベンジル−２-ジメチルアミノ−1−（４−モルフォリノフェニル）−１−ブタノン−１等のα−アミノアルキルアセトフェノン誘導体、イソブチリル−メチルフォスフィン酸メチルエステル、イソブチリル−フェニルフォスフィン酸メチルエステル、ピバロイル−フェニルフォスフィン酸メチルエステル、２−エチルヘキサノイル−フェニルフォスフィン酸メチルエステル、ピバロイル−フェニルフォスフィン酸イソプロピルエステル、ｐ−トルイル−フェニルフォスフィン酸メチルエステル、ｏ−トルイル−フェニルフォスフィン酸メチルエステル、２，４−ジメチルベンゾイル−フェニルフォスフィン酸メチルエステル、ｐ−３級ブチルベンゾイル−フェニルフォスフィン酸イソプロピルエステル、ビバロイル−（４−メチルフェニル）−フォスフィン酸メチルエステル、ピバロイル−フェニルフォスフィン酸ビニルエステル、アクリロイル−フェニルフォスフィン酸メチルエステル、イソブチリル−ジフェニルフォスフィンオキサイド、ピバロイル−ジフェニルフォスフィンオキサイド、１−メチル−１−シクロヘキサノイル−ジフェニルフォスフィンオキサイド、２−エチルヘキサノイル−ジフェニルフォスフィンオキサイド、ｐ−トルイル−ジフェニルフォスフィンオキサイド、ｏ−トルイル−ジフェニルフォスフィンオキサイド、ｐ−３級ブチルベンゾイル−ジフェニルフォスフィンオキサイド、（メタ）アクリロイルジフェニルフォスフィンオキサイド、ベンゾイル−ジフェニルフォスフィンオキサイド、２，２−ジメチル−ヘプタノイル−ジフェニルフォスフィンオキサイド、テレフタロイル−ビス−ジフェニルフォスフィンオキサイド、アジポイル−ビス−ジフェニルフォスフィンオキサイド、２，６−ジメチルベンゾイル−ジフェニルフォスフィンオキサイド、２，６−ジメトキシベンゾイル−フェニルフォスフィン酸メチルエステル、２，６−ジメチルベンゾイル−ジフェニルフォスフィンオキサイド、２，６−ジメトキシベンゾイル−ジフォスフィンオキサイド、２，４，６−トリメチルベンゾイル−フェニルフォスフィン酸メチルエステル、２，４，６−トリメチルベンゾイル−ジフェニルフォスフィンオキサイド、２，３，６−トリメチルベンゾイル−ジフェニルフォスフィンオキサイド、２，４，６−トリメチルベンゾイル−トリフォスフィン酸メチルエステル、２，４，６−トリメトキシベンゾイル−ジフェニルフォスフィンオキサイド、２，６−ジクロルベンゾイル−フェニルフォスフィン酸エステル、２，６−ジクロルベンゾイル−ジフェニルフォスフィンオキサイド、２，３，４，６−テトラメチルベンゾイル−ジフェニルフォスフィンオキサイド、２，６−ジブロムベンゾイル−ジフェニルフォスフィンオキサイド、２，６−ジメチルベンゾイルジフェニルフォスフィンオキサイド、２，４，６−トリメチルベンゾイルジフェニルフォスフィンオキサイド、２，４，６−トリメチルベンゾイル−フェニルフォスフィン酸メチルエステル、２，６−ジクロルベンゾイル−若しくは２，６−ジメトキシベンゾイル−ジフェニルフォスフィンオキサイド、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、ビス（２，６−ジメトキシベンゾイル）−２，４，４−トリメチル−ペンチルフォスフィンオキサイド等のアシルフォスフィンオキサイド誘導体、１，２−オクタンジオン，１−〔−４−（フェニルチオ）−，２−（Ｏ−ベンゾイルオキシム）〕、エタノン１−［９−エチル−６−（２−メチルベンゾイル）−９Ｈ−カルバゾール−３−イル]−１−(Ｏ−アセチルオキシム)等のオキシムエステル化合物が挙げられる。これらの中では、アルキルアセトフェノン誘導体、α−ヒドロキシアセトフェノン類、ホスフィンオキサイド類からなる１種以上が、反応性、透明性に優れる点で、好ましい。これらは１種又は２種以上組み合わせて用いることができる。 Examples of the photo radical polymerization initiator include benzyl derivatives such as benzyl, benzoin, benzoin benzoic acid, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether, benzophenone derivatives such as benzophenone and 4-phenylbenzophenone, and 2,2-diethoxy. Alkylacetophenone derivatives such as acetophenone and benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, 1- (4-isopropylphenyl) 2-hydroxy-2-methylpropan-1-one, 1- (4- (2-hydroxyethoxy) -Phenyl) -2-hydroxy-2-methyl-1-propan-1-one, α-hydroxyacetophenone derivatives such as 2-hydroxy-2-methyl-1-phenylpropan-1-one, Sudiethylaminobenzophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1- Α-Aminoalkylacetophenone derivatives such as butanone-1, isobutyryl-methylphosphinic acid methyl ester, isobutyryl-phenylphosphinic acid methyl ester, pivaloyl-phenylphosphinic acid methyl ester, 2-ethylhexanoyl-phenylphosphinic acid methyl ester Ester, pivaloyl-phenylphosphinic acid isopropyl ester, p-toluyl-phenylphosphinic acid methyl ester, o-toluyl-phenylphosphinic acid methyl ester, 2,4-dimethylbenzoyl-phenylphosphinic acid Tilester, p-3 tertiary butylbenzoyl-phenylphosphinic acid isopropyl ester, bivaloyl- (4-methylphenyl) -phosphinic acid methyl ester, pivaloyl-phenylphosphinic acid vinyl ester, acryloyl-phenylphosphinic acid methyl ester, isobutyryl- Diphenylphosphine oxide, pivaloyl-diphenylphosphine oxide, 1-methyl-1-cyclohexanoyl-diphenylphosphine oxide, 2-ethylhexanoyl-diphenylphosphine oxide, p-toluyl-diphenylphosphine oxide, o-toluyl -Diphenylphosphine oxide, p-tert-butylbenzoyl-diphenylphosphine oxide, (meth) acryloyldiphenylphosphine Finoxide, benzoyl-diphenylphosphine oxide, 2,2-dimethyl-heptanoyl-diphenylphosphine oxide, terephthaloyl-bis-diphenylphosphine oxide, adipoyl-bis-diphenylphosphine oxide, 2,6-dimethylbenzoyl-diphenylphosphine Fin oxide, 2,6-dimethoxybenzoyl-phenylphosphinic acid methyl ester, 2,6-dimethylbenzoyl-diphenylphosphine oxide, 2,6-dimethoxybenzoyl-diphosphine oxide, 2,4,6-trimethylbenzoyl- Phenylphosphinic acid methyl ester, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, 2,3,6-trimethylbenzoyl-diphe Ruphosphine oxide, 2,4,6-trimethylbenzoyl-triphosphinic acid methyl ester, 2,4,6-trimethoxybenzoyl-diphenylphosphine oxide, 2,6-dichlorobenzoyl-phenylphosphinic acid ester, 2, 6-dichlorobenzoyl-diphenylphosphine oxide, 2,3,4,6-tetramethylbenzoyl-diphenylphosphine oxide, 2,6-dibromobenzoyl-diphenylphosphine oxide, 2,6-dimethylbenzoyldiphenylphosphine Oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyl-phenylphosphinic acid methyl ester, 2,6-dichlorobenzoyl- or 2,6- Acyl such as methoxybenzoyl-diphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl-pentylphosphine oxide Phosphine oxide derivative, 1,2-octanedione, 1-[-4- (phenylthio)-, 2- (O-benzoyloxime)], ethanone 1- [9-ethyl-6- (2-methylbenzoyl)- And oxime ester compounds such as 9H-carbazol-3-yl] -1- (O-acetyloxime). In these, 1 or more types which consist of an alkyl acetophenone derivative, (alpha) -hydroxy acetophenone, and phosphine oxides are preferable at the point which is excellent in reactivity and transparency. These can be used alone or in combination of two or more.
（Ｃ）成分の含有割合は、接着剤組成物の総量に対して、０．１〜１０質量部の割合で含有させることが好ましく、特に０．５〜５質量部がより好ましい。０．１〜１０質量部の範囲にあれば硬化性が悪くなることもないし、透明性も低下させることもない。（Ｃ）成分の含有割合は、具体的には例えば、０．１、０．５、１、２、３、４、５、６、７、８、９、１０質量部であり、ここで例示した数値の何れか２つの間の範囲内であってもよい。 (C) It is preferable to make the content rate of a component contain in the ratio of 0.1-10 mass parts with respect to the total amount of an adhesive composition, and 0.5-5 mass parts is especially more preferable. If it exists in the range of 0.1-10 mass parts, sclerosis | hardenability will not worsen and transparency will not fall. Specifically, the content ratio of the component (C) is, for example, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 parts by mass, and is exemplified here. It may be within a range between any two of the numerical values.
＜（Ｄ）成分：ジナフトチオフェン系以外のポリエン化合物＞
本発明の樹脂組成物は、（Ｄ）成分として、ジナフトチオフェン系以外のポリエン化合物を含有する。
<(D) component: polyene compound other than dinaphthothiophene type>
The resin composition of the present invention contains a polyene compound other than dinaphthothiophene as component (D).
上記（Ｄ）成分として、ジナフトチオフェン系以外のポリエン化合物の具体例としては、分子当たり２個以上の炭素−炭素不飽和結合を有するアルケン類であれば限定されないが、ジビニルベンゼン、ジビニルトルエン等のビニル化合物、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、トリメチロールプロパンジ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、テトラエチレングリコールジ（メタ）アクリレート等の（メタ）アクリレート、ジアリルフタレート、ジアリルマレエート、トリアリルシアヌレート、トリアリルイソシアヌレート、トリアリルトリメリテート、テトラアリロキシエタン等のアリル化合物、ポリオキシプロピレンジアリルエーテル等のアリルエーテル化合物等が挙げられる。これらの中では、（Ａ）成分および（Ｂ）成分との相溶性、反応性が優れる点で、（メタ）アクリレート、アリル化合物、及びアリルエーテル化合物からなる群のうちの１種以上が好ましく、アリル化合物とアリルエーテル化合物からなる群のうちの１種以上がより好ましい。 Specific examples of polyene compounds other than dinaphthothiophene as the component (D) are not limited as long as they are alkenes having two or more carbon-carbon unsaturated bonds per molecule, but include divinylbenzene, divinyltoluene, and the like. Vinyl compounds, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri ( (Meth) acrylates, pentaerythritol tetra (meth) acrylate, (meth) acrylates such as tetraethylene glycol di (meth) acrylate, diallyl phthalate, diallyl maleate, triallyl cyanurate , Triallyl isocyanurate, triallyl trimellitate, allyl compounds such as tetraallyloxyethane, allyl ethers such as polyoxypropylene diallyl ether compounds, and the like. Among these, one or more members selected from the group consisting of (meth) acrylates, allyl compounds, and allyl ether compounds are preferable in terms of excellent compatibility and reactivity with the components (A) and (B). One or more members selected from the group consisting of allyl compounds and allyl ether compounds are more preferred.
（Ｄ）成分の炭素数は、（Ａ）成分および（Ｂ）成分との相溶性の観点から、（Ａ）成分よりも少なく、例えば６〜２３であり、６〜１８が好ましい。（Ｄ）成分の炭素数は、具体的には例えば、６、７、８、９、１０、１１、１２、１３、１４、１５、１６、１７、１８、１９、２０、２１、２２、２３であり、ここで例示した数値の何れか２つの間の範囲内であってもよい。（Ｄ）成分の炭素数が２３を超えても、（Ｄ）成分の炭素数が、本実施形態で使用する（Ａ）成分の炭素数より少なければ、使用することができる。
（Ｄ）成分の分子量は、特に限定されないが、例えば１００〜７００であり、具体的には例えば、１００、１５０、２００、２５０、３００、３５０、４００、４５０、５００、５５０、６００、６５０、７００であり、ここで例示した数値の何れか２つの間の範囲内であってもよい。
The number of carbon atoms of the component (D) is less than that of the component (A) from the viewpoint of compatibility with the components (A) and (B), and is, for example, 6 to 23, preferably 6 to 18. Specifically, the carbon number of the component (D) is, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23. It may be within the range between any two of the numerical values exemplified here. Even if the number of carbon atoms of the component (D) exceeds 23, the component (D) can be used if the number of carbon atoms of the component (D) is less than the number of carbon atoms of the component (A) used in this embodiment.
Although the molecular weight of (D) component is not specifically limited, For example, it is 100-700, for example, 100, 150, 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, and may be within a range between any two of the numerical values exemplified here.
（Ｄ）成分の含有割合は、接着剤組成物の総量に対して５〜８５質量部であることが好ましく、特に高屈折率、透明性、（Ａ）成分および（Ｂ）成分との相溶性の点で、１５〜６５質量部がより好ましい。（Ｄ）成分の含有割合は、具体的には例えば、５、１０、１５、２０、２５、３０、３５、４０、４５、５０、５５、６０、６５、７０、７５、８０、８５質量部であり、ここで例示した数値の何れか２つの間の範囲内であってもよい。 It is preferable that the content rate of (D) component is 5-85 mass parts with respect to the total amount of adhesive composition, and especially high refractive index, transparency, and compatibility with (A) component and (B) component. In this respect, 15 to 65 parts by mass are more preferable. Specifically, the content ratio of the component (D) is, for example, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85 parts by mass. It may be within the range between any two of the numerical values exemplified here.
さらに本発明の接着剤組成物には、発明の効果を損なわない範囲で、単官能の（メタ）アクリレート化合物、単官能のビニル化合物、単官能のビニルエーテル化合物、単官能のアリルエーテル化合物、単官能のチオール化合物を含有しても良い。 Furthermore, the adhesive composition of the present invention includes a monofunctional (meth) acrylate compound, a monofunctional vinyl compound, a monofunctional vinyl ether compound, a monofunctional allyl ether compound, a monofunctional compound, as long as the effects of the invention are not impaired. The thiol compound may be contained.
＜（Ｅ）成分：重合禁止剤＞
本発明の樹脂組成物は、発明の効果を損なわない範囲で、貯蔵安定性付与を目的として、（Ｅ）重合禁止剤を含有しても良い。（Ｅ）重合禁止剤としては、キノン系化合物とニトロソアミン系化合物からなる群のうちの1種以上が挙げられる。キノン系化合物としては、β−ナフトキノン、２−メトキシ−１，４−ナフトキノン、４−メトキシ−１−ナフトール、メチルハイドロキノン、ハイドロキノン、ハイドロキノンモノメチルエーテル、モノ−ｔｅｒｔ−ブチルハイドロキノン、２，５−ジ−ｔｅｒｔ−ブチルハイドロキノン、ｐ−ベンゾキノン、２，５−ジフェニル−ｐ−ベンゾキノン、２，５−ジ−ｔｅｒｔ−ブチル−ｐ−ベンゾキノン等が挙げられる。ニトロソアミン系化合物としては、Ｎ−ニトロソフェニルヒドロキシルアミンアンモニウム塩（クペロン）、Ｎ−ニトロソフェニルヒドロキシルアミンアルミニウム塩等が挙げられる。キノン系化合物の中では、ハイドロキノン、ハイドロキノンモノメチルエーテルからなる群のうちの１種以上が好ましい。ニトロソアミン系化合物の中では、クペロン、Ｎ−ニトロソフェニルヒドロキシルアミンアルミニウム塩からなる群のうちの１種以上が好ましい。
<(E) component: Polymerization inhibitor>
The resin composition of the present invention may contain (E) a polymerization inhibitor for the purpose of imparting storage stability as long as the effects of the invention are not impaired. (E) As a polymerization inhibitor, 1 or more types in the group which consists of a quinone type compound and a nitrosamine type compound are mentioned. As quinone compounds, β-naphthoquinone, 2-methoxy-1,4-naphthoquinone, 4-methoxy-1-naphthol, methylhydroquinone, hydroquinone, hydroquinone monomethyl ether, mono-tert-butylhydroquinone, 2,5-di- Examples include tert-butyl hydroquinone, p-benzoquinone, 2,5-diphenyl-p-benzoquinone, 2,5-di-tert-butyl-p-benzoquinone, and the like. Examples of the nitrosamine compound include N-nitrosophenylhydroxylamine ammonium salt (cuperon), N-nitrosophenylhydroxylamine aluminum salt, and the like. Among the quinone compounds, one or more members selected from the group consisting of hydroquinone and hydroquinone monomethyl ether are preferable. Among the nitrosamine compounds, one or more members selected from the group consisting of cuperone and N-nitrosophenylhydroxylamine aluminum salt are preferable.
（Ｅ）重合禁止剤の含有量は、接着剤組成物の総量に対して０．００００１〜１．０質量部が好ましく、０．０００５〜０．１質量部がより好ましく、０．００１〜０．０１質量部が最も好ましい。（Ｅ）重合禁止剤の含有量は、具体的には例えば、０．００００１、０．０００１、０．０００５、０．００１、０．００２、０．００３、０．００４、０．００５、０．０１、０．１、１質量部であり、ここで例示した数値の何れか２つの間の範囲内であってもよい。 (E) 0.00001-1.0 mass part is preferable with respect to the total amount of an adhesive composition, as for content of a polymerization inhibitor, 0.0005-0.1 mass part is more preferable, 0.001-0 0.01 parts by weight is most preferred. (E) Specifically, the content of the polymerization inhibitor is, for example, 0.00001, 0.0001, 0.0005, 0.001, 0.002, 0.003, 0.004, 0.005, 0. .01, 0.1, and 1 part by mass, and may be within a range between any two of the numerical values exemplified here.
＜その他の添加剤＞
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、ジエン系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。
<Other additives>
As long as the purpose of the present embodiment is not impaired, various elastomers such as antioxidants, silane coupling agents, acrylic rubbers, urethane rubbers, diene rubbers, photosensitizers, light stabilizers, solvents, extenders, fillers Further, additives such as reinforcing materials, plasticizers, thickeners, dyes, pigments, flame retardants and surfactants may be contained.
上記構成からなる接着剤組成物は、エネルギー線の照射により硬化体とすることができる。 The adhesive composition having the above configuration can be made into a cured body by irradiation with energy rays.
また、上記構成からなる接着剤組成物は、エネルギー線の照射により部品同士を接着することができるため、高透明性、高屈折率など光学特性に優れた貼り合わせレンズ、プリズム、積層ガラス、積層フィルム等の光学部品の接合体を提供することができる。 In addition, since the adhesive composition having the above-described configuration can adhere parts to each other by irradiation with energy rays, it has excellent optical properties such as high transparency and high refractive index. A joined body of an optical component such as a film can be provided.
さらに、上記構成からなる接着剤組成物は、高透明性、高屈折率など光学特性に優れるため、高度な光学部品の接着が必要な液晶パネル、有機エレクトロルミネッセンスパネル、タッチパネル、プロジェクター、スマートフォン、携帯電話、デジタルカメラ、デジタルムービーの表示装置や、光ピックアップ、ＬＥＤ、プリンター、コピー機、光照射機等の光源装置や、太陽電池、リチウムイオン電池等エネルギー部材や、ＣＣＤ、ＣＭＯＳ等の各種センサー部品、フラッシュメモリー、ＤＲＡＭ、半導体レーザー等の半導体素子を提供することができる。 Furthermore, the adhesive composition having the above structure is excellent in optical properties such as high transparency and a high refractive index, so that a liquid crystal panel, an organic electroluminescence panel, a touch panel, a projector, a smartphone, a mobile phone and the like that require bonding of advanced optical components are required. Telephones, digital cameras, digital movie display devices, light pickup devices such as optical pickups, LEDs, printers, copiers, and light irradiators, energy members such as solar cells and lithium ion batteries, and various sensor components such as CCDs and CMOSs Semiconductor devices such as flash memory, DRAM, and semiconductor laser can be provided.
本実施形態に係る接着剤組成物の製造方法については、上記の材料を十分に混合できれば特に制限はない。材料の混合方法としては、特に限定されないが、プロペラの回転に伴う撹拌力を利用する撹拌法、自転公転による遊星式撹拌機等の通常の分散機を利用する方法等が挙げられる。これらの混合方法は、低コストで、安定した混合を行えるので好ましい。 About the manufacturing method of the adhesive composition which concerns on this embodiment, if said material can fully be mixed, there will be no restriction | limiting in particular. The mixing method of the material is not particularly limited, and examples thereof include a stirring method using a stirring force accompanying rotation of a propeller, a method using a normal disperser such as a planetary stirrer by rotation and revolution, and the like. These mixing methods are preferable because stable mixing can be performed at low cost.
上記の混合を行った後、下記の光源を用いたエネルギー線の照射により、接着剤組成物の硬化を行うことができる。 After performing the above mixing, the adhesive composition can be cured by irradiation with energy rays using the following light source.
本実施形態において、接着剤組成物の硬化、接着に用いられる光源としては、特に限定されないが、ハロゲンランプ、メタルハライドランプ、ハイパワーメタルハライドランプ（インジウム等を含有する）、低圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、キセノンランプ、キセノンエキシマランプ、キセノンフラッシュランプ、ライトエミッティングダイオード（以下、ＬＥＤという）等が挙げられる。これらの光源は、それぞれの光ラジカル重合開始剤の反応波長に対応したエネルギー線の照射を効率よく行える点で、好ましい。 In the present embodiment, the light source used for curing and adhering the adhesive composition is not particularly limited. However, a halogen lamp, a metal halide lamp, a high power metal halide lamp (containing indium, etc.), a low pressure mercury lamp, and a high pressure mercury lamp. , Ultra high pressure mercury lamp, xenon lamp, xenon excimer lamp, xenon flash lamp, light emitting diode (hereinafter referred to as LED), and the like. These light sources are preferable in that they can efficiently irradiate energy rays corresponding to the reaction wavelengths of the respective radical photopolymerization initiators.
上記光源は、各々放射波長、エネルギー分布が異なる。そのため、上記光源は光重合開始剤の反応波長等により適宜選択される。又、自然光（太陽光）も反応開始光源になり得る。 Each of the light sources has a different emission wavelength and energy distribution. Therefore, the light source is appropriately selected depending on the reaction wavelength of the photopolymerization initiator. Natural light (sunlight) can also be a reaction initiation light source.
上記光源は、直接照射、反射鏡等による集光照射、ファイバー等による集光照射を行ってもよい。低波長カットフィルター、熱線カットフィルター、コールドミラー等も用いることもできる。 The light source may perform direct irradiation, condensing irradiation using a reflecting mirror, or condensing irradiation using a fiber or the like. A low wavelength cut filter, a heat ray cut filter, a cold mirror, or the like can also be used.
上記構成からなる接着剤組成物は、高い屈折率と高い透明性を兼ね備えることから光学部品を接着するのに好適な接着剤を提供できる。 Since the adhesive composition having the above configuration has both a high refractive index and high transparency, an adhesive suitable for bonding optical components can be provided.
以下に、実施例及び比較例を挙げて、本発明を更に詳細に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto.
実施例では、以下の化合物を使用した。 In the examples, the following compounds were used.
（Ａ）ジナフトチオフェン系ポリエン化合物
ジナフトチオフェン系ポリエン化合物は、非特許文献１に記載の合成方法にて製造したものを用いた。
（Ａ−１）２，１２−ジアリルエーテルジナフトチオフェン（炭素数２６、略号：ＤＡＯＤＮＴ）
(A) Dinaphthothiophene-based polyene compound As the dinaphthothiophene-based polyene compound, one produced by the synthesis method described in Non-Patent Document 1 was used.
(A-1) 2,12-diallyl ether dinaphthothiophene (26 carbon atoms, abbreviation: DAODNT)
（Ｂ）ポリチオール化合物
（Ｂ−１）１，８−ジメルカプト−３，６−ジオキサオクタン（丸善石油化学社製「ＤＭＤＯ」、略号：ＤＭＤＯ）
（Ｂ−２）トリメチロールプロパン−トリス−（β−チオプロピネート）（ＳＣ有機社製「ＴＭＭＰ−２０Ｐ」、略号：ＴＭＭＰ）
（Ｂ−３）ペンタエリスリトール テトラキス（３−メルカプトプロピオネート）（ＳＣ有機社製「ＰＥＭＰ」、略号：ＰＥＭＰ）
（Ｂ−４）トリス-[(3-メルカプトプロピオニルオキシ)-エチル]-イソシアヌレート（ＳＣ有機社製「ＴＥＭＰＩＣ」、略号：ＴＥＭＰＩＣ）
(B) Polythiol compound (B-1) 1,8-dimercapto-3,6-dioxaoctane ("DMDO" manufactured by Maruzen Petrochemical Co., Ltd., abbreviation: DMDO)
(B-2) Trimethylolpropane-tris- (β-thiopropinate) (“TMMP-20P”, abbreviation: TMMP, manufactured by SC Organic Chemical Co., Ltd.)
(B-3) Pentaerythritol tetrakis (3-mercaptopropionate) ("PEMP" manufactured by SC Organic Chemicals, abbreviation: PEMP)
(B-4) Tris-[(3-mercaptopropionyloxy) -ethyl] -isocyanurate (“TEMPIC”, abbreviated as TEMPIC, manufactured by SC Organic Chemical Co., Ltd.)
（Ｃ）光ラジカル重合開始剤
（Ｃ−１）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」、略号：ＢＡＰＯ）
(C) Photoradical polymerization initiator (C-1) Bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (“Irgacure 819” manufactured by BASF, abbreviation: BAPO)
（Ｄ）ジナフトチオフェン系以外のポリエン化合物
（Ｄ−１）トリアリルイソシアヌレート（炭素数１２、日本化成社製「ＴＡＩＣ」、略号：ＴＡＩＣ）
（Ｄ−２）イソシアヌル酸エチレンオキシド変性トリアクリレート（炭素数１８、東亜合成社製「アロニックスＭ−３１５」、略号：ＴＡＥＯＩＣ）
（Ｄ−３）ジビニルベンゼン（炭素数８、東京化成工業社製「ジビニルベンゼン」、略号：ＤＶＢ）
（Ｄ−４）ジペンタエリスリトールヘキサアクリレート（炭素数２８、共栄社化学社製「ライトアクリレートＤＰＥ−６Ａ」、略号：ＤＰＨＡ）、（Ｄ−４）は炭素数が多いため、比較例として使用
(D) Polyene compounds other than dinaphthothiophene series (D-1) triallyl isocyanurate (carbon number 12, “TAIC” manufactured by Nippon Kasei Co., Ltd., abbreviation: TAIC)
(D-2) Isocyanuric acid ethylene oxide-modified triacrylate (18 carbon atoms, “Aronix M-315” manufactured by Toa Gosei Co., Ltd., abbreviation: TAEOC)
(D-3) Divinylbenzene (8 carbon atoms, “Divinylbenzene” manufactured by Tokyo Chemical Industry Co., Ltd., abbreviation: DVB)
(D-4) Dipentaerythritol hexaacrylate (carbon number 28, “Light acrylate DPE-6A” manufactured by Kyoeisha Chemical Co., abbreviation: DPHA), (D-4) is used as a comparative example because it has a large number of carbon atoms.
（Ｅ）重合禁止剤
（Ｅ−１）Ｎ−ニトロソフェニルヒドロキシルアミンアルミニウム塩（和光純薬工業社製「Ｑ−１３０１」、略号：ＮＰＨＡＡ）
(E) Polymerization inhibitor (E-1) N-nitrosophenylhydroxylamine aluminum salt (“Q-1301”, abbreviation: NPHAA, manufactured by Wako Pure Chemical Industries, Ltd.)
（実施例１〜１３、比較例１〜４）
表１に示す種類の原材料を、表１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に示す。特記しない限り、２３℃、湿度５０％の環境下で実施した。
(Examples 1-13, Comparative Examples 1-4)
The raw materials of the type shown in Table 1 were mixed at the composition ratio (unit: parts by mass) shown in Table 1, to prepare an adhesive composition, and the evaluation described below was performed. No solvent was used. Various evaluation results are shown in Table 1. Unless otherwise specified, the test was carried out in an environment of 23 ° C. and 50% humidity.
〔液安定性評価〕
３０ｍｌのバイアル瓶に樹脂組成物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
尚、混合後の液の状態を目視で確認し、析出物や分離物がみられた試料については続く評価は実施しなかった。
(Liquid stability evaluation)
Prepare a sealed sample by placing 10 ml of the resin composition in a 30 ml vial, leave the sample in an atmosphere at a temperature of 23 ° C. for 24 hours, visually check the liquid state after 24 hours, and use the following criteria: evaluated.
◯: No change from before standing Δ: Precipitates and isolates were seen but redissolved by heating at 50 ° C. x: Precipitates and isolates were seen and did not dissolve again even at 50 ° C. The state of the liquid after mixing was visually confirmed, and subsequent evaluation was not carried out for the sample in which precipitates and separated matters were observed.
〔屈折率の評価〕
（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。
(Evaluation of refractive index)
(1) Liquid Refractive Index The liquid refractive index was evaluated by measuring the refractive index at a temperature of 25 ° C. and a wavelength of 589 nm using a multiwavelength Abbe refractometer (“DR-M2” manufactured by Atago Co., Ltd.).
(2) Refractive index of cured product The adhesive composition was poured into a silicone rubber mold having a volume of 15 mm × 15 mm × 1.0 mm, and 365 nm with an ultra-high pressure mercury lamp mounting device (“UL-750” manufactured by HOYA). A cured product test piece cured under the conditions of an irradiation intensity of 30 mW / cm 2 and an integrated light quantity of 30,000 mJ / cm 2 was prepared, and the refractive index was evaluated. The refractive index was evaluated by measuring the refractive index at a wavelength of 633 nm using a spectroscopic prism coupler refractive index measuring device ("MODEL 2010 PRISM COUPLER" manufactured by Metricon).
〔分光透過率測定〕
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。
(Spectral transmittance measurement)
After applying the adhesive composition on heat-resistant glass (trade name “heat-resistant Pyrex (registered trademark) glass”, 25 mm × 25 mm × 2.0 mm) with a film thickness of 30 μm, an ultra-high pressure mercury lamp mounting device (“UL” manufactured by HOYA -750 "), a test piece cured under conditions of irradiation intensity of a wavelength of 365 nm of 50 mW / cm 2 and integrated light quantity of 30,000 mJ / cm 2 was prepared, and an ultraviolet-visible spectrophotometer (manufactured by Shimadzu Corporation) UV-2550 "), the transmittance was measured at 450 nm using a heat resistant glass as a reference.
〔引張剪断接着強さ測定〕
ＪＩＳ Ｋ ６８５０に従い測定した。具体的には被着材とした（商標）テンパックスガラス（２５ｍｍ×２５ｍｍ×２．０ｍｍ）を用いて、接着部位を直径８ｍｍとして、作製した樹脂組成物にて、２枚のテンパックスガラスを貼り合わせ、前記の厚さ８０μｍで接着剤を塗布した後に、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の条件にて硬化させ、引張剪断接着強さ試験片を作製した。作製した試験片は、引張試験機を使用して、温度２３℃、湿度５０％の環境下、引張速度１０ｍｍ／分で引張剪断断接着強さを測定した。
[Measurement of tensile shear bond strength]
It measured according to JIS K 6850. Specifically, (Tempax glass) (trademark) (25 mm × 25 mm × 2.0 mm) as an adherend was used, and the bonded portion was 8 mm in diameter. After bonding and applying an adhesive with the thickness of 80 μm, the irradiation intensity of 365 nm wavelength is 50 mW / cm 2 , the integrated light amount is 30, using an ultra-high pressure mercury lamp mounting device (“UL-750” manufactured by HOYA). Curing was performed under the condition of 000 mJ / cm 2 to prepare a tensile shear bond strength test piece. The produced test piece was measured for tensile shear bond strength at a tensile speed of 10 mm / min in an environment of a temperature of 23 ° C. and a humidity of 50% using a tensile tester.
＜考察＞
実施例１〜１３では、何れも液安定性・屈折率・分光透過率・引張剪断接着強さの点で優れた結果が得られた。但し、実施例１〜２では、（Ｄ）成分の配合量が少ないため、液安定性が若干劣っていた。実施例８では、ジナフトチオフェン系ポリエン化合物が少ないために、実施例１３では、（Ｄ）成分としてビニル化合物を用いたために、接着強さが若干劣っていた。
また、比較例１では、ジナフトチオフェン系ポリエン化合物を用いなかったため、屈折率が十分でなかった。比較例２では、ジナフトチオフェン系ポリエン化合物の配合量が多すぎたため、比較例３では、ジナフトチオフェン系以外のポリエン化合物を配合しなかったために、液安定性が悪くて容易に再溶解しない析出物が発生したため、評価のための試験片を作成することができなかった。比較例４では、ジナフトチオフェン系以外のポリエン化合物を配合したが、このポリエン化合物の炭素数が多すぎるために、液安定性が悪くて容易に再溶解しない析出物が発生したため、評価のための試験片を作成することができなかった。
<Discussion>
In each of Examples 1 to 13, excellent results were obtained in terms of liquid stability, refractive index, spectral transmittance, and tensile shear bond strength. However, in Examples 1-2, since there were few compounding quantities of (D) component, liquid stability was a little inferior. In Example 8, since there was little dinaphtho thiophene type polyene compound, in Example 13, since the vinyl compound was used as (D) component, adhesive strength was a little inferior.
In Comparative Example 1, since the dinaphthothiophene polyene compound was not used, the refractive index was not sufficient. In Comparative Example 2, since the blending amount of the dinaphthothiophene polyene compound was too large, in Comparative Example 3, since the polyene compound other than the dinaphthothiophene compound was not blended, the liquid stability was poor and it was not easily redissolved. Since precipitates were generated, a test piece for evaluation could not be prepared. In Comparative Example 4, a polyene compound other than the dinaphthothiophene compound was blended. However, because the polyene compound has too many carbon atoms, a precipitate that does not easily re-dissolve due to poor liquid stability was generated. The test piece could not be made.
本発明の接着剤組成物は、高い屈折率と高い透明性を有するため、液晶パネル、有機エレクトロルミネッセンスパネル、タッチパネル、プロジェクター、スマートフォン、携帯電話、デジタルカメラ、デジタルムービー、光ピックアップ、ＬＥＤ、太陽電池、リチウムイオン電池等に用いられるレンズ、プリズム、ガラス部材、フィルム等の光学部品の接着および各種部品の組み立て、さらにはＣＣＤ、ＣＭＯＳ等の各種センサー、フラッシュメモリー、ＤＲＡＭ、半導体レーザー等の半導体素子のパッケージ等に用いられるガラス部材、フィルム等の接着に好適に用いることができ、産業上非常に有用である。
Since the adhesive composition of the present invention has a high refractive index and high transparency, a liquid crystal panel, an organic electroluminescence panel, a touch panel, a projector, a smartphone, a mobile phone, a digital camera, a digital movie, an optical pickup, an LED, and a solar cell Adhesion of optical parts such as lenses, prisms, glass members, and films used in lithium ion batteries, and assembly of various parts, as well as various sensors such as CCD and CMOS, flash memory, DRAM, semiconductor elements such as semiconductor lasers It can be suitably used for bonding glass members and films used for packages and the like, and is very useful in industry.
Claims (7)
（Ｂ）成分として、ポリチオール化合物、
（Ｃ）成分として、光ラジカル重合開始剤、
（Ｄ）成分として、ジナフトチオフェン系以外であり且つ前記（Ａ）成分よりも炭素数が少ないポリエン化合物、
を含有し、前記（Ａ）成分の含有割合が組成物の総量に対して５〜５０質量部の範囲であり、前記（Ｂ）成分の含有割合が組成物の総量に対して１０〜６０質量部の範囲であり、前記（Ｄ）成分の含有割合が組成物の総量に対して５〜８５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。 As the component (A), a dinaphthothiophene-based polyene compound having two or more polymerizable functional groups having an ethylenically unsaturated double bond represented by the following general formula (1):
(B) As a component, a polythiol compound,
(C) As a component, radical photopolymerization initiator,
As the component (D), a polyene compound that is other than dinaphthothiophene and has fewer carbon atoms than the component (A),
The content ratio of the component (A) is in the range of 5 to 50 parts by mass with respect to the total amount of the composition, and the content ratio of the component (B) is 10 to 60 masses with respect to the total amount of the composition. The adhesive composition for optical parts, wherein the content ratio of the component (D) is in the range of 5 to 85 parts by mass with respect to the total amount of the composition.
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