CN118076668A - Curable resin composition and cured product thereof - Google Patents
Curable resin composition and cured product thereof Download PDFInfo
- Publication number
- CN118076668A CN118076668A CN202280067189.9A CN202280067189A CN118076668A CN 118076668 A CN118076668 A CN 118076668A CN 202280067189 A CN202280067189 A CN 202280067189A CN 118076668 A CN118076668 A CN 118076668A
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- Prior art keywords
- compound
- resin composition
- curable resin
- meth
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- 239000011342 resin composition Substances 0.000 title claims abstract description 106
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- -1 acrylate compound Chemical class 0.000 claims abstract description 78
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 43
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 34
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000853 adhesive Substances 0.000 claims description 12
- 230000001070 adhesive effect Effects 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000000565 sealant Substances 0.000 claims description 11
- 125000005647 linker group Chemical group 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 33
- 230000035699 permeability Effects 0.000 abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 90
- 239000000047 product Substances 0.000 description 64
- 238000002834 transmittance Methods 0.000 description 38
- 150000002430 hydrocarbons Chemical group 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 239000010408 film Substances 0.000 description 9
- 239000012788 optical film Substances 0.000 description 9
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 238000012423 maintenance Methods 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 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 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 229940042596 viscoat Drugs 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 4
- 239000011112 polyethylene naphthalate Substances 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 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 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000003906 humectant Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 2
- RSHKWPIEJYAPCL-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(CC)COC1 RSHKWPIEJYAPCL-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 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
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000006841 cyclic skeleton Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-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
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001333 moisturizer Effects 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 239000003961 penetration enhancing agent Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920006290 polyethylene naphthalate film Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- VCJWMECOBCXFOF-UHFFFAOYSA-N (3-ethyloxetan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)COC1 VCJWMECOBCXFOF-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- 125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 description 1
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- VQYUAFDBUVMFKD-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)octane-1,2-dione Chemical compound C1=CC(C(=O)C(=O)CCCCCC)=CC=C1SC1=CC=CC=C1 VQYUAFDBUVMFKD-UHFFFAOYSA-N 0.000 description 1
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical compound C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 1
- CWRBWLKXTXSMEH-UHFFFAOYSA-N 1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethanone Chemical compound C=1C=C2N(CC)C3=CC=C(C(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C CWRBWLKXTXSMEH-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- WVGXBYVKFQJQGN-UHFFFAOYSA-N 1-tert-butylperoxy-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1OOC(C)(C)C WVGXBYVKFQJQGN-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-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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- 239000003566 sealing material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BGXXXYLRPIRDHJ-UHFFFAOYSA-N tetraethylmethane Chemical compound CCC(CC)(CC)CC BGXXXYLRPIRDHJ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- VNXUJPCYZSNXDG-UHFFFAOYSA-N thiopyran-4-one Chemical compound O=C1C=CSC=C1 VNXUJPCYZSNXDG-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
Abstract
The present invention provides a curable resin composition and a cured product thereof, wherein the cured product has excellent ultraviolet ray permeability, and high light resistance and heat resistance to ultraviolet rays are realized. A curable resin composition comprising the following compound (A), the following compound (B) and a radical polymerization initiator (C). Compound (a): (meth) acrylate having one (meth) acryloyl group and one or more oxetanyl groups in one molecule, compound (B): a (meth) acrylate compound having two or more (meth) acryloyl groups in one molecule.
Description
Technical Field
The present disclosure relates to curable resin compositions and cured products thereof. The present application claims priority from japanese patent application No. 2021-164818, invented in japan, 10/6 of 2021, the contents of which are incorporated herein by reference.
Background
A micro LED display which has been attracting attention as a next-generation display is a display in which fine red, green, and blue light-emitting LED elements are layered on a substrate, and for example, an ultraviolet-curable resin composition is used for sealing the LED elements (for example, patent document 1).
In recent years, as in the case of organic EL displays, a color conversion method (CCM method) has been studied in which a color conversion layer having a function of converting monochromatic light emission (blue light or the like) into green light emission or red light emission is applied to display multiple colors, and recently, in order to realize a light source having higher luminance and replacing light emission of blue light or the like, an ultraviolet LED element has been studied.
The color conversion layer is formed of, for example, a cured product of a curable resin composition containing a pigment or the like that converts the color of ultraviolet light or the like into red, green, and blue light emission, but excellent ultraviolet light transmittance is required in order for the pigment or the like to absorb ultraviolet light or the like effectively. In addition, in order to make the display longer in life, high light resistance to ultraviolet rays is required. Further, since an ultraviolet LED element is used as a light source, high heat resistance is required. Patent document 1 describes that a cured product of a curable resin composition comprising a combination of a difunctional acrylic compound having two (meth) acryloyl groups in one molecule and a polyfunctional acrylic compound having three or four (meth) acryloyl groups in one molecule is excellent in total light transmittance.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2019-210481
Disclosure of Invention
Problems to be solved by the invention
However, the cured product described in patent document 1 does not exhibit sufficient properties with respect to light resistance and heat resistance to ultraviolet rays.
Accordingly, an object of the present disclosure is to provide a curable resin composition and a cured product thereof, which are excellent in ultraviolet light transmittance in the cured product and realize high ultraviolet light resistance and heat resistance.
Solution for solving the problem
As a result of intensive studies to achieve the above object, the inventors of the present disclosure have found that a cured product which realizes high ultraviolet transmittance, high ultraviolet light resistance and heat resistance can be obtained in a curable resin composition containing a specific (meth) acrylate compound.
That is, the present disclosure provides a curable resin composition comprising the following compound (a), the following compound (B), and a radical polymerization initiator (C).
Compound (a): (meth) acrylate compounds having one (meth) acryloyl group and one or more oxetanyl groups in one molecule.
Compound (B): a (meth) acrylate compound having two or more (meth) acryloyl groups in one molecule.
The compound (a) is preferably a compound represented by the following formula (1).
[ Chemical formula 1]
[ In formula (1), R 1 represents a hydrogen atom or a monovalent hydrocarbon group, R 2 represents a single bond or a divalent hydrocarbon group, and R 3 represents a hydrogen atom or a methyl group ]
The compound (B) is preferably a compound represented by the following formula (2).
[ Chemical formula 2]
[ In formula (2), R 4 represents an m-valent hydrocarbon group, a heterocyclic group or a group formed by bonding them via a single bond or a linking group, R 5 represents a hydrogen atom or a methyl group, and m represents an integer of 2 to 5 ]
The present disclosure also provides a sealant comprising the above curable resin composition.
The present disclosure also provides an adhesive comprising the above curable resin composition.
The present disclosure also provides a composition for a color filter, which includes the above curable resin composition.
The color filter composition may be a color filter ink.
The present disclosure also provides a cured product of the curable resin composition.
Further, the present disclosure provides a display member having the above cured product.
Advantageous effects
The curable resin composition of the present disclosure has the above-described constitution, and thus, by curing the resin composition, a cured product can be formed which is excellent in ultraviolet light transmittance, has high ultraviolet light resistance and heat resistance, and particularly can improve high brightness, high definition and reliability of a display member at high temperature and high humidity. Therefore, particularly when the curable resin composition of the present disclosure is used as a composition for a color filter, deterioration in transparency is less likely to occur even under such severe conditions as high temperature (including light), and a display member having high durability and quality can be obtained.
Detailed Description
[ Curable resin composition ]
The curable resin composition of the present disclosure contains the following compound (a), the following compound (B), and a radical polymerization initiator (C).
Compound (a): (meth) acrylate compounds having one (meth) acryloyl group and one or more oxetanyl groups in one molecule.
Compound (B): a (meth) acrylate compound having two or more (meth) acryloyl groups in one molecule.
< Compound (A) >
The compound (a) is a (meth) acrylate compound having one (meth) acryloyl group and one or more oxetanyl groups (preferably 1 to 3, more preferably 1) in one molecule, and is a curable compound. The "(meth) acrylate" means "methacrylate" or "acrylate", and the "(meth) acryl" means "acryl" or "methacryl".
The compound (a) is preferably a compound represented by the following formula (1). In the following formula (1), R 1 represents a hydrogen atom or a monovalent hydrocarbon group, R 2 represents a single bond or a divalent hydrocarbon group, and R 3 represents a hydrogen atom or a methyl group.
[ Chemical formula 1]
Examples of the hydrocarbon group of R 1 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. The hydrocarbon group of the above R 1 may optionally have a substituent (e.g., oxetanyl group, etc.).
Examples of the aliphatic hydrocarbon group include: straight-chain or branched alkyl (methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, isopentyl, sec-pentyl, tert-pentyl, hexyl, decyl, dodecyl, etc.) having 1 to 20 carbon atoms (preferably having 2 to 10 carbon atoms, more preferably having 2 to 3 carbon atoms), straight-chain or branched alkenyl (vinyl, allyl, methylpropenyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 5-hexenyl, etc.) having 2 to 20 carbon atoms (preferably having 2 to 10 carbon atoms, more preferably having 2 to 3 carbon atoms), straight-chain or branched alkynyl (ethynyl, propynyl, etc.), and the like.
Examples of the alicyclic hydrocarbon group include: cycloalkyl (cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, etc.) having 3 to 20 carbon atoms (preferably 3 to 15 carbon atoms, more preferably 5 to 8 carbon atoms), cycloalkenyl (cyclopentenyl, cyclohexenyl, etc.) having 3 to 20 carbon atoms (preferably 3 to 15 carbon atoms, more preferably 5 to 8 carbon atoms), bridged cyclic hydrocarbon groups (bicycloheptanoyl, perhydronaphthalen-1-yl, norbornoyl, adamantyl, tetracyclo [4.4.0.1 2,5.17,10 ] dodecane-3-yl, etc.), and the like.
Examples of the aromatic hydrocarbon group include an aromatic hydrocarbon group having 6 to 14 carbon atoms (preferably 6 to 10 carbon atoms) (e.g., phenyl group, naphthyl group, etc.).
Among these hydrocarbon groups represented by R 1, an aliphatic hydrocarbon group is preferable, a linear or branched alkyl group having 1 to 3 carbon atoms is preferable, and a methyl group or an ethyl group is more preferable.
Examples of the divalent hydrocarbon group of R 2 include a group obtained by removing one hydrogen atom from the structural formula of the monovalent hydrocarbon group (aliphatic hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group, etc.) of R 1.
Examples of the divalent aliphatic hydrocarbon group include linear or branched alkylene (methylene, ethylene, methyl methylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene, pentylene, neopentylene, isopentylene, hexylene, decylene, dodecylene, etc.) having 1 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms), linear or branched alkenylene (ethylene, propylene, isopropenyl, butylene, pentylene, hexylene, etc.) having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms), and linear or branched alkylene (ethylene, propylene, etc.) having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms).
Examples of the divalent alicyclic hydrocarbon group include: a group obtained by removing one hydrogen atom from a cyclic alkylene group having 3 to 20 carbon atoms (preferably 3 to 15 carbon atoms, more preferably 5 to 8 carbon atoms) (1, 2-cyclopentylene, 1, 3-cyclopentylene, 1, 2-cyclohexylene, 1, 3-cyclohexylene, 1, 4-cyclohexylene, etc.), a cyclic alkylene group having 3 to 20 carbon atoms (preferably 3 to 15 carbon atoms, more preferably 5 to 8 carbon atoms) (cyclopentyl, cyclohexyl, etc.), a cycloalkenyl group having 3 to 20 carbon atoms (preferably 3 to 15 carbon atoms, more preferably 5 to 8 carbon atoms) (1, 2-cyclopentyl, 1, 2-cyclohexyl, etc.), a bridged cyclic hydrocarbon group (bicycloheptanoyl, perhydronaphthalen-1-yl, norbornoyl, adamantyl, tetracyclo [4.4.0.1 2,5.17,10 ] dodecane-3-yl, etc.), and the like.
Examples of the divalent aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 14 carbon atoms (preferably 6 to 10 carbon atoms) (e.g., 1, 4-phenylene, 1, 3-phenylene, 4 '-biphenylene, 3' -biphenylene, 2, 6-naphthalenediyl, 2, 7-naphthalenediyl, 1, 8-naphthalenediyl, anthracenediyl, etc.).
The hydrocarbon group of R 2 is preferably a divalent aliphatic hydrocarbon group, preferably a linear or branched alkylene group having 1 to 3 carbon atoms, and more preferably a methylene group.
R 3 is preferably methyl.
As a specific example of the compound (A), examples thereof include (meth) acrylic acid (3-ethyl-3-oxetanyl) methyl ester, (meth) acrylic acid 2- (3-ethyl-3-oxetanyl) ethyl ester, (meth) acrylic acid 3- (3-ethyl-3-oxetanyl) propyl ester, (meth) acrylic acid 4- (3-ethyl-3-oxetanyl) butyl ester, (meth) acrylic acid 2- [ (3-ethyl-3-oxetanyl) methoxy ] ethyl ester, (meth) acrylic acid 2- [2- [ (3-ethyl-3-oxetanyl) methoxy ] ethoxy ] ethyl ester, (meth) acrylic acid (3-methyl-3-oxetanyl) methyl ester, (meth) acrylic acid 2- (3-methyl-3-oxetanyl) ethyl ester, 3- (3-methyl-3-oxetanyl) propyl ester, (meth) acrylic acid 4- (3-methyl-3-oxetanyl) butyl ester, (meth) acrylic acid 2- (3-methyl-3-oxetanyl) methoxy ] ethyl ester, 2- [2- [ (3-methyl-3-oxetanyl) methoxy ] ethoxy ] ethyl (meth) acrylate, and the like. Among them, from the viewpoint of excellent effect of improving permeability, (3-ethyl-3-oxetanyl) methyl methacrylate is more preferable. The compound (a) may be used singly or in combination of two or more.
The content of the compound (a) in the curable resin composition of the present disclosure is preferably 5 to 40 parts by weight, more preferably 10 to 30 parts by weight, still more preferably 15 to 25 parts by weight, relative to 100 parts by weight of the total of the compound (a) and the compound (B).
< Compound (B) >
The compound (B) is a (meth) acrylate compound having two or more (meth) acryloyl groups in one molecule, and is a curable compound. The compound (B) is preferably a compound represented by the following formula (2). In the formula (2), R 4 represents an m-valent hydrocarbon group, a heterocyclic group or a group formed by bonding them via a single bond or a linking group, R 5 represents a hydrogen atom or a methyl group, and m represents an integer of 2 to 5.
[ Chemical formula 2]
M is preferably 2 to 3.
Examples of the m-valent hydrocarbon group of R 4 include a group obtained by removing m hydrogen atoms from a structural formula of a hydrocarbon (e.g., an aliphatic hydrocarbon, an alicyclic hydrocarbon, or an aromatic hydrocarbon).
Examples of the aliphatic hydrocarbon include: linear or branched alkanes having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms) (methane, ethane, propane, butane, 2-methylpropane, pentane, 2-methylbutane, 2-dimethylpropane, hexane, decane, dodecane, etc.), linear or branched alkenes having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms) (ethylene, propylene, 2-methylpropene, 1-butene, 2-butene, 1-pentene, 2-pentene, 1-hexene, etc.), linear or branched alkynes having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms) (acetylene, propyne, etc.), and the like.
Examples of the alicyclic hydrocarbon include cycloalkanes having 3 to 20 carbon atoms (preferably 3 to 15 carbon atoms, more preferably 5 to 8 carbon atoms) (cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclooctane, etc.), cycloalkenes having 3 to 20 carbon atoms (preferably 3 to 15 carbon atoms, more preferably 5 to 8 carbon atoms) (cyclopentene, cyclohexene, etc.), bridged ring hydrocarbons (bicycloheptane, bicycloheptene, perhydronaphthalene, norbornene, adamantane, tetracyclo [4.4.0.1 2,5.17,10 ] dodecane, etc.), and the like.
Examples of the aromatic hydrocarbon include aromatic hydrocarbons having 6 to 14 carbon atoms (preferably 6 to 10 carbon atoms) (benzene, naphthalene, etc.).
The above hydrocarbon may optionally have various substituents [ e.g., halogen atom, oxy group, hydroxyl group, substituted oxy group (e.g., alkoxy group, aryloxy group, aralkoxy group, acyloxy group, etc.), carboxyl group, substituted oxycarbonyl group (alkoxycarbonyl group, aryloxycarbonyl group, aralkoxycarbonyl group, etc.), substituted or unsubstituted carbamoyl group, cyano group, nitro group, substituted or unsubstituted amino group, sulfo group, heterocyclic group, etc. ]. The hydroxyl group and the carboxyl group may be protected with a protecting group conventionally used in the field of organic synthesis. Further, an aromatic or non-aromatic heterocyclic ring may be condensed on the ring of the alicyclic hydrocarbon or aromatic hydrocarbon.
Examples of the m-valent heterocyclic group include a group obtained by removing m hydrogen atoms from a structural formula of a heterocyclic ring. Examples of the heterocycle include: a heterocyclic ring containing an oxygen atom as a hetero atom (e.g., a four-membered ring (oxetane or the like), a five-membered ring (furan, tetrahydrofuran, oxazole, isoxazole, γ -butyrolactone or the like), a six-membered ring (4-oxo-4H-pyran, tetrahydropyran, morpholine or the like), a condensed ring (benzofuran, isobenzofuran, 4-oxo-4H-benzopyran, chroman, isochroman or the like), a bridged ring (3-oxatricyclo [4.3.1.1 4,8 ] undecan-2-one or the like), a 3-oxatricyclo [4.2.1.0 4,8 ] nonan-2-one or the like), a heterocyclic ring containing a sulfur atom as a hetero atom (e.g., a five-membered ring (thiophene, thiazole, isothiazole, thiadiazole or the like), a six-membered ring (4-oxo-4H-thiopyran or the like), a condensed ring (benzothiophene or the like), a heterocyclic ring containing a nitrogen atom as a hetero atom (e.g., a five-membered ring (pyrrole, pyrrolidine, pyrazole, imidazole, triazole or the like), a six-membered ring (pyridine, pyridazine, pyrimidine, pyrazine, piperidine, piperazine or the like), a condensed ring (indole, indoline, quinoline, a naphthyridine, a cyclic ring, a cyclic alkyl group containing a nitrogen atom, a cyclic group optionally substituted with a nitrogen atom, a cyclic group containing a nitrogen atom, an (e.g., an optionally substituted with a nitrogen atom, an alkyl group, a cyclic group, an aryl group, an optionally substituted with a nitrogen atom, etc.), and the phenyl group, and the like).
Examples of the linking group include: carbonyl (-CO-), ether linkage (-O-), thioether linkage (-S-), ester linkage (-COO-), amide linkage (-CONH-), and carbonate bond (-OCOO-), silyl bond (-Si-), and a group obtained by connecting a plurality of them.
The m-valent hydrocarbon group, heterocyclic group or group bonded thereto via a single bond or a linking group of R 4 may be a residue derived from a hydroxyl group in the corresponding polyol compound. Examples of the polyol compound include: polyalkylene glycols (polyethylene glycol, polypropylene glycol, polytetramethylene glycol, pentaerythritol, etc.), alkylene glycols (ethylene glycol, 1, 4-butanediol, 1, 6-hexanediol, neopentyl glycol, etc.), glycerin, trialkylalkanes (trimethylolpropane, triethylpropane, dimethylolmethanol butane, etc.), pentaerythritol, bisphenol (bisphenol A, etc.) alkylene oxide adducts, isocyanuric acid alkylene oxide adducts, etc.
The hydrocarbon of R 4 is preferably an aliphatic hydrocarbon, more preferably a linear or branched alkane (saturated hydrocarbon) having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms, and still more preferably 1 to 5 carbon atoms). That is, the R 4 is preferably an m-valent hydrocarbon group, more preferably an m-valent aliphatic hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms, still more preferably 1 to 5 carbon atoms), still more preferably an m-valent saturated aliphatic hydrocarbon group having 1 to 5 carbon atoms, and particularly preferably an m-valent linear saturated aliphatic hydrocarbon group having 1 to 5 carbon atoms. The heterocyclic ring of R 4 is preferably a urethane ring.
The R 4 is preferably a residue obtained by removing a hydroxyl group from an alkylene glycol (e.g., 1, 4-butanediol, 1, 6-hexanediol). Among the m-valent heterocyclic groups of R 4, the residue of the alkylene oxide adduct of isocyanuric acid is preferable, and the residue of tris (2-hydroxyethyl) isocyanurate is more preferable.
The compound (B) is, for example, a reaction product in which a part or all of the hydroxyl groups of the above-mentioned polyol compound are bonded to carboxyl groups of (meth) acrylic acid, and has two or more (2 to 5, preferably 2 to 3) (meth) acryloyl groups.
Examples of the compound (B) having two (meth) acryloyl groups include polyalkylene glycol di (meth) acrylate, bisphenol a alkylene oxide modified di (meth) acrylate, alkylene glycol di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, pentaerythritol di (meth) acrylate, and glycerol di (meth) acrylate. They may be used singly or in combination of two or more.
Examples of the polyalkylene glycol di (meth) acrylate include polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and polytetramethylene glycol di (meth) acrylate.
Examples of the bisphenol a alkylene oxide-modified di (meth) acrylate include: bisphenol a ethylene oxide modified di (meth) acrylate, bisphenol a propylene oxide modified di (meth) acrylate, and the like.
The alkylene glycol di (meth) acrylate is preferably an alkylene glycol di (meth) acrylate having an alkylene group having 2 to 10 carbon atoms (more preferably 3 to 6 carbon atoms), and specific examples thereof include ethylene glycol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and the like.
Among them, alkylene glycol di (meth) acrylate is preferable from the viewpoint of improving the permeability of the cured product, and 1, 4-butanediol diacrylate and 1, 6-hexanediol diacrylate are more preferable from the viewpoint of ultraviolet light resistance of the cured product.
Examples of the compound (B) having three (meth) acryloyl groups include: pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, alkylene oxide isocyanurate modified tri (meth) acrylate (tris (2- (meth) acryloxyethyl) isocyanurate, tris (3- (meth) acryloxypropyl) isocyanurate, etc.), epsilon-caprolactone modified tris ((meth) acryloxyalkyl) isocyanurate, etc. Among them, tris (2-acryloyloxyethyl) isocyanurate is preferable from the viewpoint of heat resistance of the cured product. They may be used singly or in combination of two or more.
Examples of the compound (B) having four (meth) acryloyl groups include: di (trimethylolpropane) tetra (meth) acrylate, ethoxylated pentaerythritol tetra (meth) acrylate, and the like. They may be used singly or in combination of two or more.
Examples of the compound (B) having five (meth) acryloyl groups include dipentaerythritol penta (meth) acrylate. They may be used singly or in combination of two or more.
The compounds (B) having different amounts of (meth) acryloyl groups may be used singly or in combination of two or more.
R 5 is preferably a hydrogen atom.
The content of the compound (B) in the curable resin composition of the present disclosure is preferably 60 to 95 parts by weight, more preferably 70 to 90 parts by weight, and even more preferably 75 to 85 parts by weight, relative to 100 parts by weight of the total of the compound (a) and the compound (B).
From the viewpoint of excellent transparency, light resistance, and heat resistance of the cured product, the compound (B) preferably contains at least the compound (B1) having two (meth) acryloyl groups, and more preferably contains the compound (B2) having three compounds (B1) and (meth) acryloyl groups.
When the compound (B) contains the compound (B1) and the compound (B2), the content of the compound (B1) is preferably 55 to 79 parts by weight, more preferably 60 to 77 parts by weight, and even more preferably 65 to 75 parts by weight, relative to 100 parts by weight of the total of the compound (a) and the compound (B). The content of the compound (B2) is preferably 1 to 25 parts by weight, more preferably 3 to 20 parts by weight, and even more preferably 5 to 15 parts by weight, based on 100 parts by weight of the total of the compound (a) and the compound (B).
The content of the compound (b 1) is preferably 60 to 100% by weight, more preferably 75 to 95% by weight, and even more preferably 80 to 90% by weight, in terms of excellent permeability, light resistance, and heat resistance of the cured product, based on 100% by weight of the total amount of the curable compounds having two or more (meth) acryloyl groups.
The content of the compound (b 2) is preferably 0 to 40% by weight, more preferably 5 to 25% by weight, and even more preferably 10 to 20% by weight, based on 100% by weight of the total amount of the curable compound having two or more (meth) acryloyl groups, from the viewpoints of excellent transmittance, light resistance, heat resistance, and color tone of the cured product.
In addition, for R 4, the compound (B) is preferably a compound (B3) containing at least a chain skeleton (aliphatic hydrocarbon group), and more preferably a compound (B4) containing a compound (B3) and a cyclic skeleton (alicyclic hydrocarbon group, aromatic hydrocarbon group, or heterocyclic group).
When the compound (B) contains the compound (B3) and the compound (B4), the content of the compound (B3) is preferably 55 to 79 parts by weight, more preferably 60 to 77 parts by weight, and even more preferably 65 to 75 parts by weight, relative to 100 parts by weight of the total of the compound (a) and the compound (B). The content of the compound (B4) is preferably 1 to 25 parts by weight, more preferably 3 to 20 parts by weight, and even more preferably 5 to 15 parts by weight, based on 100 parts by weight of the total of the compound (a) and the compound (B).
The content of the compound (b 3) is preferably 60 to 100% by weight, more preferably 75 to 95% by weight, and even more preferably 80 to 90% by weight, in terms of excellent permeability, light resistance, and heat resistance of the cured product, based on 100% by weight of the total amount of the curable compounds having two or more (meth) acryloyl groups.
The content of the compound (b 4) is preferably 0 to 40% by weight, more preferably 5 to 25% by weight, and even more preferably 10 to 20% by weight, in terms of excellent permeability, light resistance, and heat resistance of the cured product, based on 100% by weight of the total amount of the curable compounds having two or more (meth) acryloyl groups.
< Radical polymerization initiator (C) >)
The curable resin composition of the present disclosure contains a radical polymerization initiator (C) as a curing catalyst. The radical polymerization initiator (C) is a compound that initiates or accelerates the radical polymerization of the compounds (A) and (B). The radical polymerization initiator (C) is not particularly limited, and examples thereof include a thermal radical polymerization initiator, a photo radical polymerization initiator, and the like. As the radical polymerization initiator (C), either a thermal radical polymerization initiator or a photo radical polymerization initiator may be used, or both a thermal radical polymerization initiator and a photo radical polymerization initiator may be used.
Examples of the thermal radical polymerization initiator include organic peroxides, inorganic peroxides, azo compounds, and the like.
Examples of the organic peroxide include hydrogen peroxide, dialkyl peroxide, peroxy ester, diacyl peroxide, peroxy dicarbonate, peroxy ketal ketone peroxide (benzoyl peroxide, t-butyl peroxy-2-ethylhexanoate, 2, 5-dimethyl-2, 5-di (2-ethylhexanoyl) peroxy hexane, t-butyl peroxybenzoate, t-butyl peroxide, cumene peroxide, dicumyl peroxide, di-t-butyl peroxide, 2, 5-dimethyl-2, 5-dibutyl peroxy hexane, 2, 4-dichlorobenzoyl peroxide, 1, 4-bis (2-t-butylperoxy isopropyl) benzene, 1-bis (t-butylperoxy) -3, 5-trimethylcyclohexane, methyl ethyl ketone peroxide, and 1, 3-tetramethylbutyl peroxy-2-ethylhexanoate. Among them, ketone peroxide is preferable from the viewpoint of storage stability, and tert-butylperoxy-2-ethylhexanoate is more preferable from the viewpoint of permeability of the cured product.
Examples of the inorganic peroxide include hydrogen peroxide, persulfates (potassium persulfate, ammonium persulfate, etc.), and the like.
Examples of the azo compounds include: 2,2' -Azobisisobutyronitrile (AIBN), 2' -azobis (2-methylbutyronitrile), 2' -azobis (4-methoxy-2, 4-dimethylvaleronitrile), 2' -azobis (2-hydroxymethylpropionitrile) 1,1' -azobicyclohexene-1-carbonitrile, 4' -azobis (4-cyanovaleric acid), 2- (carbamoylazo) isobutyronitrile, 2-phenylazo-4-methoxy-2, 4-dimethylvaleronitrile, 2-,2' -azobis (2-methylpropane), 2' -azobis (2, 4-trimethylpentane), dimethyl 2,2' -azobisisobutyrate, and the like.
In the use of the above thermal radical polymerization initiator, naphthenic acid, metal salts of octenoic acid (cobalt naphthenate, manganese naphthenate, zinc naphthenate, nickel naphthenate, vanadium naphthenate, cobalt octenoate, manganese octenoate, nickel octenoate, copper octenoate, etc.) may be used in combination. In addition, tertiary amine (dimethylaniline, etc.) may be used in combination.
Examples of the photo-radical polymerization initiator include an alkyl benzophenone-based photo-radical polymerization initiator, an acyl phosphine oxide-based photo-radical polymerization initiator, an oxime ester-based photo-radical polymerization initiator, and an α -hydroxy ketone-based photo-radical polymerization initiator. Among them, alkylbenzene-based photo radical polymerization initiators are preferable.
Examples of the alkylbenzene-based photo radical polymerization initiator include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -1-butanone, 2- (dimethylamino) -2- [ (4-methylphenyl) ] methyl ] - [4- (4-morpholinyl) phenyl ] -1-butanone, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropane-1-one, benzophenone, methylbenzophenone, o-benzoylbenzoic acid, benzoyldiethyl ether, 2-diethoxyacetophenone, 2, 4-diethylthioxanthone, diphenyl- (2, 4, 6-trimethylbenzoyl) phosphine oxide, ethyl- (2, 4, 6-trimethylbenzoyl) phenylphosphonate, 4' -bis (diethylamino) benzophenone, 1-hydroxycyclohexylphenyl ketone, 2-dimethoxy-1, 2-diphenylethane-1-one, 1- [4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-isopropenyl) -1-one, and the like. Among them, 1-hydroxycyclohexyl phenyl ketone is preferable from the viewpoint of storage stability.
Examples of the acyl phosphine oxide-based photo-radical polymerization initiator include 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide and bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide.
Examples of the oxime ester-based photo-radical polymerization initiator include 1- [4- (phenylthio) phenyl ] -1, 2-octanedione 2- (O-benzoyloxy) and 1- [6- (2-methylbenzoyl) -9-ethyl-9H-carbazol-3-yl ] ethanone O-acetoxime.
Examples of the α -hydroxyketone photo-radical polymerization initiator include: benzoin, benzoin methyl ether, benzoin butyl ether, 1-hydroxycyclohexyl phenyl ketone, 1-phenyl-2-hydroxy-2-methylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, and the like.
The radical polymerization initiator (C) may be used singly or in combination of two or more.
The content of the radical polymerization initiator (C) in the curable resin composition of the present disclosure is preferably 0.01 to 3.0 parts by weight, more preferably 0.05 to 2.0 parts by weight, and even more preferably 0.10 to 1.0 parts by weight, relative to 100 parts by weight of the total of the compound (a) and the compound (B). If the content is less than 0.1 parts by weight, the curing reaction is easy to proceed, and if it is less than 3.0 parts by weight, sufficient ultraviolet light resistance is easy to be obtained.
The curable resin composition of the present disclosure may contain a cationic polymerization initiator, a volatile organic solvent, a monofunctional (meth) acrylate as a reactive diluent, a curable compound other than the compound (a) and the compound (B), and other components, as long as the effects of the present disclosure are not impaired.
The amount of the volatile organic solvent to be blended is, for example, preferably 100 parts by weight or less, more preferably 50 parts by weight or less, based on 100 parts by weight of the total of the compound (a) and the compound (B).
The amount of the monofunctional (meth) acrylate to be blended is, for example, preferably 0 to 100 parts by weight, more preferably 0 to 20 parts by weight, based on 100 parts by weight of the total of the compound (a) and the compound (B). The amount of the above compound is preferably 5 parts by weight or less, more preferably 1 part by weight or less, based on 100 parts by weight of the total of the compound (a) and the compound (B).
The content of the curable compound other than the compound (a) and the compound (B) is preferably 100 parts by weight or less, more preferably 50 parts by weight or less, and still more preferably 10 parts by weight or less, based on 100 parts by weight of the total of the compound (a) and the compound (B).
Examples of the other components include: sensitizer, light stabilizer, inorganic or organic filler, reinforcing material such as carbon fiber and glass fiber, lubricant, antistatic agent, silane coupling agent, defoamer, leveling agent, surfactant, flame retardant, colorant, antioxidant, ultraviolet absorber, ion adsorbent, phosphor, mold release agent, etc. The amount of the compound (a) and the compound (B) is preferably 5 parts by weight or less based on 100 parts by weight of the total of these components.
The curable resin composition of the present disclosure can be prepared by stirring/mixing the compound (a), the compound (B), and the radical polymerization initiator (C) while eliminating bubbles under vacuum as needed. The temperature during stirring/mixing is, for example, about 20 to 50 ℃. Well-known devices (e.g., autorotation mixers, single or multiple screw extruders, planetary mixers, kneaders, dissolvers (dissolver), etc.) may be used in the stirring/mixing.
The curable resin composition of the present disclosure contains the compound (a), the compound (B), and the radical polymerization initiator (C), and thus is excellent in curability.
In the case where the radical polymerization initiator (C) is a thermal radical polymerization initiator, the curable resin composition of the present disclosure can form a cured product by performing a heat treatment.
The heating temperature for obtaining the cured product is, for example, 80 to 180 ℃. The heating time is, for example, 30 to 600 minutes. The heating temperature can be appropriately adjusted by shortening the heating time and by extending the heating time when the heating temperature is lowered.
In the case where the radical polymerization initiator (C) is a photo radical polymerization initiator, the curable resin composition of the present disclosure can form a cured product by performing a light irradiation treatment.
In order to obtain light irradiation of the cured product, ultraviolet rays are preferably used. The wavelength of the ultraviolet light used is preferably 200 to 400nm. The preferable irradiation conditions are illuminance of 5 to 300mW/cm 2 and irradiation amount of 50 to 18000mJ/cm 2.
The method of applying/printing the curable resin composition of the present disclosure is not particularly limited depending on the application, and examples thereof include screen printing, mask printing, offset printing, inkjet printing, flexography, gravure printing, squeegee printing, screen printing, die, dispensing, spraying, brush coating, comma coating, gravure coating, die coating, and the like.
The curable resin composition of the present disclosure includes, for example, sealants, adhesives, color filter compositions, coating agents, electrically insulating materials, laminated plates, sealants, resists, composite materials, transparent substrates, transparent sheets, transparent films, optical elements, optical lenses, light molding, electronic papers, touch panels, solar cell substrates, optical waveguides, various applications useful for light guide plates, holographic memories, light detection sensors, and the like.
[ Sealant ]
The curable resin composition of the present disclosure forms a cured product having excellent ultraviolet light transmittance and high light resistance and heat resistance to ultraviolet light, and therefore can be preferably used as a sealant or the like for sealing a light emitting element (an ultraviolet light emitting element or the like) in a display member or the like. When the curable resin composition of the present disclosure is used as the sealant, a light-emitting element (such as an ultraviolet light-emitting element) can be sealed with a cured product (=sealing material) having excellent ultraviolet light transmittance, light resistance to ultraviolet light, and heat resistance.
When the curable resin composition of the present disclosure is used as a sealant, at least the curable resin composition of the present disclosure is contained. The sealant of the present disclosure may contain components other than the curable resin composition (penetration enhancer, humectant (moisturizer), fixer, mildewproof agent, preservative, antioxidant, ultraviolet absorber, chelating agent, tackifier, etc.), and the content thereof may be 10 wt% or less (preferably 5 wt% or less) with respect to 100 wt% of the entire sealant.
[ Adhesive ]
The curable resin composition of the present disclosure forms a cured product having excellent ultraviolet light transmittance and high light resistance and heat resistance to ultraviolet light, and therefore, for example, an adhesive for fixing optical films (a polarizing plate, a polarizing plate protective film, a phase difference film, and the like) to an image member or for bonding optical films to other films in a display member, and an adhesive for bonding/fixing members and the like to an adherend in a film contact paste for bonding an optical semiconductor element to a metal electrode in an optical semiconductor device can be preferably used for various applications requiring light transmittance, light resistance, and heat resistance, such as an adhesive for bonding lenses to each other or the like to an adherend.
The curable resin composition of the present disclosure is particularly preferably used as an adhesive for an optical film. By using the adhesive of the present disclosure as an adhesive for an optical film, a display member in which an image member and an optical film are bonded to each other by a cured product having excellent ultraviolet light transmittance, light resistance to ultraviolet light, and heat resistance can be obtained.
When the curable resin composition of the present disclosure is used as an adhesive for an optical film, at least the curable resin composition of the present disclosure is contained. The pressure-sensitive adhesive of the present disclosure may contain components other than the curable resin composition (penetration enhancer, humectant (moisturizer), fixer, mildewproof agent, preservative, antioxidant, ultraviolet absorber, chelating agent, tackifier, etc.), and the content thereof is preferably 10% by weight or less (preferably 5% by weight or less) relative to 100% by weight of the entire pressure-sensitive adhesive for an optical film.
[ Composition for color Filter ]
The curable resin composition of the present disclosure forms a cured product that is excellent in ultraviolet light transmittance and high in light resistance and heat resistance to ultraviolet light, and thus can be preferably used as a color filter composition for forming a color filter. The color filter may be a layer for improving the color purity by transmitting light in a specific wavelength region of visible light to a desired color tone by containing a known pigment or dye, or may be a color conversion layer having a function of converting ultraviolet light or the like into visible light of a specific wavelength by containing a known pigment or dye, or may be a color conversion layer having a desired color tone. By using the curable resin composition of the present disclosure as the composition for a color filter, a display member having a color filter formed of a cured product having excellent ultraviolet light transmittance and excellent light resistance and heat resistance to ultraviolet light can be obtained.
The color filter composition of the present disclosure can be preferably used as a color filter ink capable of forming color conversion layers of different hues with very high accuracy by an inkjet printing method or the like, for example.
When the curable resin composition of the present disclosure is used as a composition for a color filter, it contains at least the curable resin composition of the present disclosure, a pigment, and a dye. The composition for color filters of the present disclosure may contain a curable resin composition and components other than pigments and dyes (permeation enhancers, humectants, fixing agents, mold inhibitors, preservatives, antioxidants, ultraviolet absorbers, chelating agents, tackifiers, and the like), and the content thereof may be 100% by weight, preferably 10% by weight or less (preferably 5% by weight or less) relative to the entire composition for color filters.
[ Cured product ]
The cured product of the present disclosure is obtained by curing the curable resin composition of the present disclosure.
The cured product of the present disclosure has excellent ultraviolet transmittance. The transmittance of ultraviolet rays (wavelength 385 nm) of the cured product (thickness 100 μm) of the present disclosure is preferably 89.5% or more, more preferably 90.0% or more, still more preferably 90.5% or more, and the upper limit is preferably 100%.
The transmittance of light (wavelength 450 nm) of the cured product (thickness 100 μm) of the present disclosure is preferably 90.5% or more, more preferably 91.0% or more, still more preferably 91.5% or more, and the upper limit is preferably 100%.
The transmittance of ultraviolet light (wavelength 385 nm) and light (wavelength 450 nm) can be measured in accordance with JIS K7361-1.
Further, the cured product of the present disclosure is excellent in light resistance to ultraviolet rays. The cured product (thickness 100 μm) of the present disclosure preferably has a transmittance maintenance rate of 91.5% or more, more preferably 92.0% or more, still more preferably 92.5% or more, and the upper limit preferably 100% after exposure to ultraviolet rays having an intensity of 10mW/cm 2 for 200 hours while heating at 120 ℃.
The cured product of the present disclosure is also excellent in heat resistance. The cured product (thickness 100 μm) of the present disclosure preferably has a transmittance maintenance rate of 91.0% or more, more preferably 91.5% or more, still more preferably 92.0% or more, and an upper limit of 100% after heating at 120℃for 100 hours.
[ Display Member ]
The display member of the present disclosure is characterized by comprising a cured product of the curable resin composition of the present disclosure. Examples of the display member include a display member including a light emitting element (such as an ultraviolet light emitting element) sealed with a cured product of the curable resin composition of the present disclosure, and a micro LED display member including an image member bonded to an optical film by a cured product of the curable resin composition of the present disclosure, wherein the display member includes an ultraviolet LED element as a light source and a color conversion layer for converting the color of the ultraviolet LED element into blue, green, and red.
The display member of the present disclosure has a light emitting element sealed with a cured product of the curable resin composition of the present disclosure, an image member bonded with an optical film with a cured product of the curable resin composition of the present disclosure, or a color filter formed of the curable resin composition of the present disclosure is excellent in structural light extraction efficiency, light resistance, and heat resistance.
As described above, each configuration and the combination of each configuration of the present disclosure are examples, and the addition, omission, substitution, and modification of the configuration may be appropriately performed within the scope not departing from the gist of the present disclosure. Further, the present disclosure is not limited by the embodiments, but is limited only by the descriptions of the patent claims.
Examples
Hereinafter, the present disclosure will be described in more detail based on examples, but the present disclosure is not limited to any of these examples.
The compound (a), the compound (B), the radical polymerization initiator (C) and the (meth) acrylate compound having one (meth) acryloyl group but no oxetanyl group in one molecule used in examples and comparative examples are as follows.
(Compound (A)
OXMA: (3-ethyl-3-oxetanyl) methyl methacrylate, trade name "ETERNACOLL OXMA", manufactured by Yu Xingjinggao Co., ltd.
(Compound (B))
Viscoat #230:1, 6-hexanediol diacrylate, trade name "Viscoat #230", manufactured by osaka organic chemical industry, inc.
Viscoat #195:1, 4-butanediol diacrylate, trade name "Viscoat #195", manufactured by Osaka organic chemical industries, ltd.
A-9300: tris- (2-acryloyloxyethyl) isocyanurate, trade name "NK EsterA-9300", manufactured by new Zhongcun chemical industry Co., ltd.
(Compound (C))
Omnirad184: 1-hydroxycyclohexyl phenyl ketone, trade name "Omnirad184", IGM RESINS B.V. company.
PERBUTYLO: tert-butyl peroxy-2-ethylhexanoate, trade name "PERBUTYLO", manufactured by japan oil and fat (ltd).
(A (meth) acrylate compound having one (meth) acryloyl group in one molecule and no oxetanyl group)
Viscoat #190: ethoxyethoxyethyl acrylate, trade name "Viscoat #190", manufactured by osaka organic chemical industry, inc.
< Examples 1 to 5, comparative examples 1 to 3>
The components were added to a flask in accordance with the compounding compositions shown in table 1, and stirred and mixed at room temperature, thereby obtaining a uniform curable resin composition.
In the cases of examples 1, 3, 5 and comparative examples 1 and 3, the obtained curable resin composition was cast and coated on a PEN (polyethylene naphthalate) film (trade name "TEONEX", manufactured by DuPont Teijin Films, inc. and having a thickness of 50 μm) using a bar coater so that the thickness after curing was 100 μm, and then irradiated with ultraviolet light for 10 seconds (ultraviolet light wavelength 365nm, ultraviolet light irradiation amount 3000mJ/cm 2), and the PEN film was peeled off to give a cured product having a thickness of 100 μm.
In the cases of examples 2,4 and comparative example 2, the obtained curable resin composition was cast and coated on a PEN (polyethylene naphthalate) film (trade name "TEONEX", manufactured by DuPont Teijin Films, product of Kagaku Kogyo Co., ltd., thickness: 50 μm) using a bar coater so that the thickness after curing was 100 μm, and then heated in an oven at 90℃for 30 minutes, and then heated at 120℃for 60 minutes, and then the PEN film was peeled off to give a cured product having a thickness of 100. Mu.m.
The obtained cured product (thickness: 100 μm) was evaluated for permeability, light resistance and heat resistance as follows.
(Permeability)
The transmittance (%) was measured by using a spectrophotometer (product name "UV-2450", manufactured by Shimadzu corporation) with respect to ultraviolet rays (wavelength 385 nm) or light rays (wavelength 450 nm). The larger the value of the transmittance, the more excellent the transmittance of the cured product.
(Light resistance)
The obtained cured product (thickness: 100 μm) was heated at 120℃and exposed to ultraviolet light having an intensity of 10mW/cm 2 for 200 hours, and then the transmittance (%) of ultraviolet light (wavelength: 385 nm) was measured using a spectrophotometer (product name: UV-2450; manufactured by Shimadzu corporation). The value of the light transmittance after exposure relative to the light transmittance before exposure (the maintenance rate of the light transmittance of the cured product) was evaluated as the transmittance maintenance rate (light resistance) (%). The larger the value of the transmittance maintenance ratio, the more excellent the light resistance of the cured product to ultraviolet rays.
(Heat resistance)
After the obtained cured product (thickness 100 μm) was heated at 120℃for 100 hours, the transmittance (%) of ultraviolet light (wavelength 385 nm) was measured using a spectrophotometer (product name "UV-2450", manufactured by Shimadzu corporation). The value of the light transmittance after exposure relative to the light transmittance before exposure (the maintenance rate of the light transmittance of the cured product) was evaluated as the transmittance maintenance rate (heat resistance) (%). The larger the value of the permeability maintenance ratio, the more excellent the heat resistance of the cured product.
TABLE 1
TABLE 1
The following describes modifications of the disclosed invention.
[ Additional note 1] A curable resin composition comprising the following compound (A), the following compound (B), and a radical polymerization initiator (C).
Compound (a): (meth) acrylate compounds having one (meth) acryloyl group and one or more oxetanyl groups in one molecule.
Compound (B): a (meth) acrylate compound having two or more (meth) acryloyl groups in one molecule.
[ Additional note 2] the curable resin composition according to additional note 1, wherein the compound (a) is a compound represented by the following formula (1).
[ Chemical formula 1]
[ In formula (1), R 1 represents a hydrogen atom or a monovalent hydrocarbon group, R 2 represents a single bond or a divalent hydrocarbon group, and R 3 represents a hydrogen atom or a methyl group ]
[ Additional note 3] the curable resin composition according to additional note 2, wherein the monovalent hydrocarbon group is an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, or an aromatic hydrocarbon group, which may be substituted.
[ Additional note 4] the curable resin composition according to additional note 3, wherein the substituent is an oxetanyl group.
The curable resin composition according to any one of the additional notes 3 or 4, wherein the aliphatic hydrocarbon group is a linear or branched alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms), a linear or branched alkenyl group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms), or a linear or branched alkynyl group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms).
[ Appendix 6] the curable resin composition according to appendix 2, wherein R 1 is methyl or ethyl.
The curable resin composition according to any one of supplementary notes 7, wherein R 2 is a linear or branched alkylene group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms), a linear or branched alkenylene group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms), or a linear or branched alkynyl group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms).
[ Additional note 8] the curable resin composition according to any one of additional notes 2 to 6, wherein R 2 is methylene.
[ Additional note 9] the curable resin composition according to additional note 1, wherein the compound (A) is (3-ethyl-3-oxetanyl) methacrylate.
[ Additional note 10] the curable resin composition according to any one of additional notes 1 to 9, wherein the content of the compound (a) is 5 to 40 parts by weight (preferably 10 to 30 parts by weight, more preferably 15 to 25 parts by weight) relative to 100 parts by weight of the total of the compound (a) and the compound (B).
[ Additional note 11] the curable resin composition according to any one of additional notes 1 to 10, wherein the compound (B) is a compound represented by the following formula (2).
[ Chemical formula 2]
[ In formula (2), R 4 represents an m-valent hydrocarbon group, a heterocyclic group or a group formed by bonding them via a single bond or a linking group, R 5 represents a hydrogen atom or a methyl group, and m represents an integer of 2 to 5 ]
[ Additional note 12] the curable resin composition according to additional note 11, wherein m is 2 to 3.
The curable resin composition according to any one of appendixes 11 or 12, wherein the hydrocarbon group is a group obtained by removing m hydrogen atoms from a structural formula of an aliphatic hydrocarbon, alicyclic hydrocarbon or aromatic hydrocarbon.
The curable resin composition according to item 13, wherein the aliphatic hydrocarbon is a linear or branched alkane having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms), a linear or branched alkene having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms), or a linear or branched alkyne having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms, more preferably 2 to 3 carbon atoms).
[ Additional note 15] the curable resin composition according to additional note 11, wherein the heterocyclic group is a group obtained by removing m hydrogen atoms from the structural formula of a heterocyclic ring.
[ Additional note 16] the curable resin composition according to additional note 11, wherein the heterocyclic group is a residue obtained by removing a hydroxyl group from tris- (2-hydroxyethyl) isocyanurate.
[ Additional note 17] the curable resin composition according to any one of additional notes 11 to 16, wherein R 5 is a hydrogen atom.
[ Additional note 18] the curable resin composition according to any one of additional notes 1 to 10, wherein the compound (B) is 1, 4-butanediol diacrylate or 1, 6-hexanediol diacrylate.
[ Additional note 19] the curable resin composition according to any one of additional notes 1 to 10, wherein the compound (B) is tris (2-acryloyloxyethyl) isocyanurate.
[ Additional note 20] the curable resin composition according to any one of additional notes 1 to 19, wherein the content of the compound (B) is 60 to 95 parts by weight (preferably 70 to 90 parts by weight, more preferably 75 to 85 parts by weight) based on 100 parts by weight of the total of the compound (a) and the compound (B).
[ Appendix 21] the curable resin composition according to any one of appendixes 1 to 20, wherein compound (B) comprises at least compound (B1) having two (meth) acryloyl groups (preferably comprises compound (B1) and compound (B2) having three (meth) acryloyl groups).
The curable resin composition according to appendix 22, wherein the content of compound (B1) is 55 to 79 parts by weight (preferably 60 to 77 parts by weight, more preferably 65 to 75 parts by weight) based on 100 parts by weight of the total of compound (a) and compound (B).
The curable resin composition according to any one of supplementary notes 21 to 22, wherein the content of the compound (B2) is 1 to 25 parts by weight (preferably 3 to 20 parts by weight, more preferably 5 to 15 parts by weight) based on 100 parts by weight of the total of the compound (a) and the compound (B).
[ Additional note 24] the curable resin composition according to any one of additional notes 21 to 23, wherein the content of the compound (b 1) is 60 to 100 wt% (preferably 75 to 95 wt%, more preferably 80 to 90 wt%) with respect to 100 wt% of the total amount of the curable compounds having two or more (meth) acryloyl groups.
[ Additional note 25] the curable resin composition according to any one of additional notes 21 to 24, wherein the content of the compound (b 2) is 0 to 40% by weight (preferably 5 to 25% by weight, more preferably 10 to 20% by weight) relative to 100% by weight of the total amount of the curable compounds having two or more (meth) acryloyl groups.
[ Appendix 26] the curable resin composition according to any one of appendixes 1 to 25, wherein the compound (B) comprises at least a compound (B3) having a chain skeleton (preferably comprises a compound (B3) and a compound (B4) having a cyclic skeleton) for R 4.
The curable resin composition according to any one of supplementary notes 27, 26, wherein the content of the compound (B3) is 55 to 79 parts by weight (preferably 60 to 77 parts by weight, more preferably 65 to 75 parts by weight) based on 100 parts by weight of the total of the compound (a) and the compound (B).
The curable resin composition according to any one of supplementary notes 28 to 26 or 27, wherein the content of the compound (B4) is 1 to 25 parts by weight (preferably 3 to 20 parts by weight, more preferably 5 to 15 parts by weight) based on 100 parts by weight of the total of the compound (a) and the compound (B).
[ Additional note 29] the curable resin composition according to any one of additional notes 26 to 28, wherein the content of the compound (b 3) is 60 to 100 wt% (preferably 75 to 95 wt%, more preferably 80 to 90 wt%) with respect to 100 wt% of the total amount of the curable compounds having two or more (meth) acryloyl groups.
The curable resin composition according to any one of supplementary notes 26 to 29, wherein the content of the compound (b 4) is 0 to 40% by weight (preferably 5 to 25% by weight, more preferably 10 to 20% by weight) based on 100% by weight of the total amount of the curable compounds having two or more (meth) acryloyl groups.
The curable resin composition according to any one of supplementary notes 31 to 30, wherein the compound (C) is a thermal radical polymerization initiator and/or a photopolymerization initiator.
[ Additional note 32] the curable resin composition according to additional note 31, wherein the thermal radical polymerization initiator is an organic peroxide (preferably a ketone peroxide, more preferably t-butylperoxy-2-ethylhexanoate).
[ Appendix 33] the curable resin composition according to appendix 31 or 32, wherein the photo radical polymerization initiator is an alkyl-benzophenone-based photo radical polymerization initiator (preferably 1-hydroxycyclohexyl phenyl ketone).
The curable resin composition according to any one of supplementary notes 1 to 33, wherein the content of the radical polymerization initiator (C) is 0.01 to 3.0 parts by weight, preferably 0.05 to 2.0 parts by weight, more preferably 0.10 to 1.0 part by weight, based on 100 parts by weight of the total of the compound (A) and the compound (B).
The curable resin composition according to any one of supplementary notes 1 to 34, wherein the amount of the volatile organic solvent is 100 parts by weight or less (preferably 50 parts by weight or less) based on 100 parts by weight of the total of the compound (A) and the compound (B).
The curable resin composition according to any one of supplementary notes 36, wherein the amount of the monofunctional (meth) acrylate to be blended is 5 parts by weight or less (preferably 1 part by weight or less) relative to 100 parts by weight of the total of the compound (a) and the compound (B).
The curable resin composition according to any one of supplementary notes 37, wherein the content of the curable compound other than the compound (a) and the compound (B) is 100 parts by weight or less (preferably 50 parts by weight or less, more preferably 10 parts by weight or less) per 100 parts by weight of the total of the compound (a) and the compound (B).
[ Additional note 38] a sealant comprising the curable resin composition according to any one of additional notes 1 to 37.
[ Appendix 39] an adhesive comprising the curable resin composition according to any one of appendix 1 to 37.
[ Appendix 40] A composition for a color filter comprising the curable resin composition according to any one of appendix 1 to 37.
The composition for a color filter according to appendix 41, which is an ink for a color filter.
[ Appendix 42] is a cured product of the curable resin composition according to any one of appendix 1 to 37.
The composition for a color filter according to appendix 43, wherein the transmittance of ultraviolet light having a wavelength of 385nm with respect to a thickness of 100 μm is 89.5% or more (preferably 90.0% or more, more preferably 90.5% or more).
[ Additional note 44] the cured product according to additional note 42 or 43, wherein the transmittance of light having a wavelength of 450nm with respect to a thickness of 100 μm is 90.5% or more (preferably 91.0% or more, more preferably 91.5% or more).
[ Additional note 45] the cured product according to any one of additional notes 42 to 44, wherein the transmittance of ultraviolet light having a wavelength of 385nm after exposure to ultraviolet light having an intensity of 10mW/cm 2 for 200 hours while heating at 120℃with respect to a thickness of 100 μm is maintained at 91.5% or more (preferably 92.0% or more, more preferably 92.5% or more).
The cured product according to any one of supplementary notes 46 to 42 to 45, wherein the transmittance of ultraviolet light having a wavelength of 385nm after heating at 120℃for 100 hours with respect to a thickness of 100. Mu.m, is maintained at 91.0% or more (preferably 91.5% or more, more preferably 92.0% or more).
[ Additional note 47] a display member comprising the cured product according to any one of additional notes 42 to 46.
[ Additional note 48] the use of the curable resin composition according to any one of additional notes 1 to 37 as a composition for a color filter.
[ Additional note 49] A method for producing a composition for color filters, comprising mixing a compound (A), a compound (B), a radical polymerization initiator (C), and at least one selected from pigments and dyes.
Industrial applicability
When the curable resin composition of the present disclosure is used, it is excellent in ultraviolet light transmittance, has high ultraviolet light resistance and heat resistance, and particularly, can form a cured product having high brightness, high definition and reliability at high temperature and high humidity of a display member, and therefore, when it is used as a composition for a color filter, deterioration in transparency is less likely to occur even under severe conditions such as the following, and a display member having high durability and quality can be obtained. Accordingly, the present disclosure has industrial applicability.
Claims (9)
1. A curable resin composition comprising the following compound (A), the following compound (B) and a radical polymerization initiator (C),
Compound (a): a (meth) acrylate compound having one (meth) acryloyl group and one or more oxetanyl groups in one molecule,
Compound (B): a (meth) acrylate compound having two or more (meth) acryloyl groups in one molecule.
2. The curable resin composition according to claim 1, wherein,
The compound (A) is a compound represented by the following formula (1),
[ Chemical formula 1]
In the formula (1), R 1 represents a hydrogen atom or a monovalent hydrocarbon group, R 2 represents a single bond or a divalent hydrocarbon group, and R 3 represents a hydrogen atom or a methyl group.
3. The curable resin composition according to claim 1 or 2, wherein,
The compound (B) is a compound represented by the following formula (2),
[ Chemical formula 2]
In the formula (2), R 4 represents an m-valent hydrocarbon group, a heterocyclic group or a group formed by bonding them via a single bond or a linking group, R 5 represents a hydrogen atom or a methyl group, and m represents an integer of 2 to 5.
4. A sealant comprising the curable resin composition according to any one of claims 1 to 3.
5. An adhesive comprising the curable resin composition according to any one of claims 1 to 3.
6. A composition for color filters comprising the curable resin composition according to any one of claims 1 to 3.
7. The composition for color filters according to claim 6, which is an ink for color filters.
8. A cured product of the curable resin composition according to any one of claims 1 to 3.
9. A display member comprising the cured product according to claim 8.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021164818A JP2023055434A (en) | 2021-10-06 | 2021-10-06 | Curable resin composition and cured product thereof |
| JP2021-164818 | 2021-10-06 | ||
| PCT/JP2022/036993 WO2023058604A1 (en) | 2021-10-06 | 2022-10-03 | Curable resin composition and cured object obtained therefrom |
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| CN118076668A true CN118076668A (en) | 2024-05-24 |
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| CN202280067189.9A Pending CN118076668A (en) | 2021-10-06 | 2022-10-03 | Curable resin composition and cured product thereof |
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| KR (1) | KR20240070670A (en) |
| CN (1) | CN118076668A (en) |
| TW (1) | TW202330636A (en) |
| WO (1) | WO2023058604A1 (en) |
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| JP4736387B2 (en) * | 2004-09-28 | 2011-07-27 | 住友化学株式会社 | Laminated body having scratch resistance and antireflection properties |
| JP5452860B2 (en) * | 2007-11-21 | 2014-03-26 | フクビ化学工業株式会社 | Curable resin composition for forming protective film on transparent resin substrate |
| WO2013146651A1 (en) * | 2012-03-27 | 2013-10-03 | 興人ホールディングス株式会社 | (meth)acrylate containing cyclic ether group |
| JP5925021B2 (en) * | 2012-04-05 | 2016-05-25 | Ｋｊケミカルズ株式会社 | Method for producing cyclic ether group-containing (meth) acrylate |
| JP2015021045A (en) * | 2013-07-18 | 2015-02-02 | Ｋｊケミカルズ株式会社 | Optical three-dimensional contouring resin composition consisting of cyclic ether group-containing (meth)acrylate |
| JP6492799B2 (en) * | 2015-03-10 | 2019-04-03 | 大日本印刷株式会社 | Photocurable resin composition for forming protective layer, cured product thereof, and optical film |
| JP6511917B2 (en) * | 2015-03-30 | 2019-05-15 | 大日本印刷株式会社 | PHOTO-CURABLE RESIN COMPOSITION, CURED PRODUCT THEREOF, AND OPTICAL FILM |
| JP7051336B2 (en) * | 2016-09-20 | 2022-04-11 | ナガセケムテックス株式会社 | Patterning material for 3D stereolithography and casting method using it |
| WO2019065075A1 (en) * | 2017-09-28 | 2019-04-04 | 富士フイルム株式会社 | Photopolymerizable composition, hard coat film, method for manufacturing hard coat film, and article provided with hard coat film |
| US11597874B2 (en) * | 2018-03-23 | 2023-03-07 | Tokuyama Corporation | Photochromic curable composition |
| JP6573089B1 (en) | 2018-05-31 | 2019-09-11 | パナソニックＩｐマネジメント株式会社 | Ultraviolet curable resin composition, method for manufacturing light emitting device, and light emitting device |
| JP7262038B2 (en) * | 2018-08-03 | 2023-04-21 | パナソニックＩｐマネジメント株式会社 | Ultraviolet curable resin composition for encapsulating organic EL element, method for manufacturing organic EL light emitting device, and organic EL light emitting device |
| CN112739726B (en) * | 2018-09-26 | 2023-09-19 | 富士胶片株式会社 | Coloring composition, method for forming cured film, method for manufacturing color filter, and method for manufacturing display device |
| JP7263813B2 (en) * | 2019-02-08 | 2023-04-25 | 王子ホールディングス株式会社 | Adhesive sheet and laminate |
| CN113265219B (en) * | 2021-06-16 | 2023-03-14 | 深圳市撒比斯科技有限公司 | UV adhesive for PDLC electrochromic film and preparation method thereof |
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| JP2023055434A (en) | 2023-04-18 |
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