CN117043670A - Sealing agent for liquid crystal display element and liquid crystal display element - Google Patents
Sealing agent for liquid crystal display element and liquid crystal display element Download PDFInfo
- Publication number
- CN117043670A CN117043670A CN202280023421.9A CN202280023421A CN117043670A CN 117043670 A CN117043670 A CN 117043670A CN 202280023421 A CN202280023421 A CN 202280023421A CN 117043670 A CN117043670 A CN 117043670A
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- meth
- acrylate
- crystal display
- display element
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 120
- 239000003795 chemical substances by application Substances 0.000 title abstract description 27
- 238000007789 sealing Methods 0.000 title abstract description 22
- 239000000565 sealant Substances 0.000 claims abstract description 94
- 239000003999 initiator Substances 0.000 claims abstract description 26
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- 238000011109 contamination Methods 0.000 abstract description 20
- 239000011248 coating agent Substances 0.000 abstract description 11
- 238000000576 coating method Methods 0.000 abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 112
- 239000004593 Epoxy Substances 0.000 description 81
- 150000001875 compounds Chemical class 0.000 description 73
- -1 camphorquinone compound Chemical class 0.000 description 58
- 239000000047 product Substances 0.000 description 42
- 239000000499 gel Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- 239000000126 substance Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 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 14
- 238000006243 chemical reaction Methods 0.000 description 14
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000010419 fine particle Substances 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- 229920003986 novolac Polymers 0.000 description 9
- BWOPOAOBPJWDBF-UHFFFAOYSA-N 1,11-bis-epi-artesin Natural products C1CC2(C)C(O)CCC(C)=C2C2C1C(C)C(=O)O2 BWOPOAOBPJWDBF-UHFFFAOYSA-N 0.000 description 8
- BWOPOAOBPJWDBF-UWSPEPLBSA-N Artesin Natural products O[C@@H]([C@]1(C)CC2)CCC(C)=C1[C@@H]1[C@@H]2[C@H](C)C(=O)O1 BWOPOAOBPJWDBF-UWSPEPLBSA-N 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 8
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 description 8
- 229930006711 bornane-2,3-dione Natural products 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 238000012719 thermal polymerization Methods 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920002799 BoPET Polymers 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 239000012346 acetyl chloride Substances 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 206010065042 Immune reconstitution inflammatory syndrome Diseases 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KBKZYWOOZPIUJT-UHFFFAOYSA-N azane;hypochlorous acid Chemical compound N.ClO KBKZYWOOZPIUJT-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000001748 luminescence spectrum Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-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
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- UFUXVJFOILLERS-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCC(C)(C)CO UFUXVJFOILLERS-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- UECGJSXCVLTIMQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)OCCOC(=O)C=C UECGJSXCVLTIMQ-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- RUVNKAUVVBCURD-UHFFFAOYSA-N 2-[[4-[2-[4-(oxiran-2-ylmethoxy)-3-prop-2-enylphenyl]propan-2-yl]-2-prop-2-enylphenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C(CC=C)=CC=1C(C)(C)C(C=C1CC=C)=CC=C1OCC1CO1 RUVNKAUVVBCURD-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
- UZDMJPAQQFSMMV-UHFFFAOYSA-N 4-oxo-4-(2-prop-2-enoyloxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC(=O)C=C UZDMJPAQQFSMMV-UHFFFAOYSA-N 0.000 description 1
- SAXNQWFLHXTRDI-UHFFFAOYSA-N 9-(2-ethylhexyl)carbazole Chemical compound C1=CC=C2N(CC(CC)CCCC)C3=CC=CC=C3C2=C1 SAXNQWFLHXTRDI-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- WUKNPIYSKBLCQI-UHFFFAOYSA-N CC(C=C1)=CC=C1C1=CC=C(C)C=C1.N=C=O.N=C=O Chemical compound CC(C=C1)=CC=C1C1=CC=C(C)C=C1.N=C=O.N=C=O WUKNPIYSKBLCQI-UHFFFAOYSA-N 0.000 description 1
- PNVWNTUCFLZBSE-UHFFFAOYSA-N CC(O)COC(=O)c1ccccc1C(=O)OCCOC(=O)C=C Chemical compound CC(O)COC(=O)c1ccccc1C(=O)OCCOC(=O)C=C PNVWNTUCFLZBSE-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 208000007254 Tetrasomy X Diseases 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
-
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
-
- 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
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
Abstract
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent visible light curability and low liquid crystal contamination properties and can suppress nozzle clogging during coating. The present invention also provides a liquid crystal display element using the sealant for a liquid crystal display element. The sealant for a liquid crystal display element of the present invention comprises a curable resin and a photopolymerization initiator, and is irradiated with an LED lamp having a peak top at a wavelength of 450nm at 100mW/cm 2 The gel fraction at 30 seconds is 70% or more, and the gel fraction at 48 hours when 400 lux of light is irradiated with an LED lamp having a peak at a wavelength of 580nm is less than 10%.
Description
Technical Field
The present invention relates to a sealant for a liquid crystal display element, which has excellent visible light curability and low liquid crystal contamination properties and can suppress nozzle clogging during coating. The present invention also relates to a liquid crystal display element using the sealant for a liquid crystal display element.
Background
In recent years, as a method for manufacturing a liquid crystal display element such as a liquid crystal display cell, a liquid crystal dropping method called a dropping method using a photo-thermal curing type sealant as disclosed in patent document 1 and patent document 2 has been used from the viewpoints of shortening a tact time and optimizing a use amount of liquid crystal.
In the dropping process, first, a frame-like seal pattern is formed on one of 2 transparent substrates having charges by a dispensing method. Next, in a state where the sealing agent is not cured, minute droplets of liquid crystal are dropped onto the entire inner surface of the frame of the transparent substrate, and the other transparent substrate is immediately bonded thereto, and the sealing portion is pre-cured by irradiation with light such as ultraviolet rays. Then, the liquid crystal is heated and cured in a main manner during the liquid crystal annealing, and a liquid crystal display element is manufactured. If the substrates are bonded under reduced pressure, a liquid crystal display device can be manufactured with extremely high efficiency, and the dropping process is currently the mainstream of the manufacturing method of the liquid crystal display device.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2001-133794
Patent document 2: international publication No. 02/092718
Patent document 3: international publication No. 2018/038016
Disclosure of Invention
Problems to be solved by the invention
In modern spread of various mobile devices with liquid crystal panels such as mobile phones and portable game machines, miniaturization of the device is the most required task. As a method of miniaturizing the device, for example, a liquid crystal display portion is narrowed, and a design (hereinafter, also referred to as a narrow frame design) is performed in which a seal portion is arranged under a black matrix.
However, in the narrow frame design, since the sealant is disposed directly under the black matrix, if the dripping process is performed, there is a problem in that: when the sealant is photo-cured, the light irradiated is blocked, and the light cannot reach the inside of the sealant, so that the curing becomes insufficient. If the curing of the sealant becomes insufficient in this way, uncured sealant components dissolve into the liquid crystal, causing a problem of liquid crystal contamination.
In general, ultraviolet irradiation is performed as a method of photocuring a sealing agent, but particularly in a liquid crystal dropping process, since the sealing agent is cured after dropping liquid crystal, there is a problem in that the liquid crystal is deteriorated by the irradiation of ultraviolet rays. Accordingly, in order to prevent deterioration of liquid crystal due to ultraviolet rays, a photopolymerization initiator reactive to light in the visible light region is blended into the sealant, and the sealant is cured by irradiation of light through a cutoff filter, and as such a photopolymerization initiator, a camphorquinone compound or the like is disclosed in patent document 3.
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent visible light curability and low liquid crystal contamination properties and can suppress nozzle clogging during coating. The present invention also provides a liquid crystal display element using the sealant for a liquid crystal display element.
Means for solving the problems
The present disclosure 1 is a sealant for a liquid crystal display element, which contains a curable resin and a photopolymerization initiator,
irradiation of 100mW/cm with an LED lamp having a peak at a wavelength of 450nm 2 The gel fraction at 30 seconds of light of (2) is 70% or more, and,
the gel fraction was less than 10% when 400 lux of light was irradiated for 48 hours using an LED lamp having a peak top at a wavelength of 580 nm.
The present disclosure 2 is a liquid crystal display element having a cured product of the sealant for a liquid crystal display element of the present disclosure 1.
The present invention will be described in detail below.
The present inventors studied the following from the viewpoint of reducing energy loss and manufacturing cost: the sealing agent is cured by irradiation with light from an LED lamp having a peak at a long wavelength (for example, a wavelength of 450 nm) without interposing a cut filter therebetween, to manufacture a liquid crystal display element. However, in the case of using a sealant containing camphorquinone-based compound as a photopolymerization initiator and using such an LED lamp to manufacture a liquid crystal display element, it is clear that liquid crystal contamination occurs.
The present inventors consider that: when a liquid crystal display element is produced using a sealant containing a camphorquinone compound as a photopolymerization initiator and using an LED lamp having a peak in a wavelength region on a long wavelength side without a cutoff filter, liquid crystal contamination occurs because the sealant cannot be sufficiently cured due to low reactivity of the camphorquinone compound. Therefore, the present inventors studied to use a photopolymerization initiator such as a titanocene compound having more excellent reactivity to visible light, but in the case of using such a photopolymerization initiator, the sealant may be clogged in a nozzle of a coating apparatus when the sealant is coated. In general, in order to prevent the reaction of a photopolymerization initiator, the application of a sealant using the photopolymerization initiator having excellent reactivity with visible light is performed under a yellow lamp designed so as not to be irradiated with light having a wavelength of 500nm or less, but the present invention considers that the reason for nozzle clogging when the sealant is applied is that the photopolymerization initiator reacts even with the light of the yellow lamp. Accordingly, the present inventors studied: irradiating 100mW/cm with an LED lamp having a peak at 450nm 2 The sealant was prepared such that the gel fraction at 30 seconds was a specific value or more and the gel fraction at 48 hours of irradiation of 400 lux light with an LED lamp having a peak top at a wavelength of 580nm was less than the specific value. As a result, it has been found that a sealant for a liquid crystal display element which is excellent in visible light curability and low in liquid crystal contamination and can suppress nozzle clogging at the time of coating can be obtained, and the present invention has been completed.
The sealant for a liquid crystal display element of the present invention was irradiated with 100mW/cm using an LED lamp having a peak at a wavelength of 450nm (hereinafter also referred to as "450nm LED lamp") 2 The gel fraction at 30 seconds of light of (2) is 70% or more. Irradiating 100mW/cm by using the 450nm LED lamp 2 The gel fraction at 30 seconds of the light of (2) is 70% or more, therebyThe sealant for a liquid crystal display element of the present invention is excellent in visible light curability and low liquid crystal contamination. Irradiation of 100mW/cm with the 450nm LED lamp 2 The lower limit of the gel fraction at 30 seconds of light is preferably 80%, and the lower limit is more preferably 85%.
In the present specification, the term "gel fraction" refers to the degree to which the curable resin contained in the sealant is crosslinked and polymerized. The filler or the like mixed at this time may be regarded as a substance that is gelled at the same time by being incorporated into the polymer.
The gel fraction can be calculated by the following formula.
Gel fraction (wt%) = ((G2-G0)/(G1-G0)) ×100
As a specific operation, the following is given.
The sealant was applied between 2 sheets of polyethylene terephthalate (PET) film so as to have a thickness of 300 μm. Examples of the PET film include PET5011 (manufactured by linde). After light was irradiated from one side of the PET film with a specified LED lamp and a metal halide lamp, 2 PET films were peeled off from each other. When the sealant was not tacky, the cured sealing material was peeled from the PET film and cut into a 1cm×2cm long strip, and the resulting long strip was wrapped with a 200 mesh metal mesh so that the sealant was not released from the area other than the lattice of the mesh. On the other hand, in the case where the sealant has tackiness, the sealant is collected by a plane of a micro spatula and wrapped with a 200 mesh metal mesh so that the sealant is not released from a portion other than the lattice of the mesh. In this case, the weight of the metal net used was measured and denoted as G0, and the total weight of the sealant and the weight of the metal net was measured and denoted as G1. In addition, G0 is 1G or more and less than 3G, and (G1-G0) is 0.2G or more and less than 0.4G. Further, 200 mesh is an index indicating fineness of mesh, and the number of wires between 1 inch is 200. After the metal mesh coated with the sealant was placed in a screw tube No.8 (manufactured by Maruemu Co.), 70g of acetone was added to the screw tube, and the mixture was allowed to stand for 3 hours. The metal mesh coated with the sealant present in the acetone was taken out with forceps, placed in a new screw tube No.8 (manufactured by Maruemu Co.), and then 70g of new acetone was added to the screw tube, followed by further standing for 2 hours. After taking out the metal mesh coated with the sealant with tweezers, the metal mesh was dried in an oven at 80℃under normal pressure for 2 hours. After drying, the weight of the metal mesh coated with the sealant was measured and set to G2. The above-described operation was performed in a darkroom having a volume of 1 lux or less. In addition, a digital illuminometer TM-201L (manufactured by TENMERS Co.) was used for measuring illuminance of the work environment.
Examples of the 450nm LED lamp include UELCL-P-450-X (manufactured by EYE GRAPHICS). The luminescence spectrum of UELCL-P-450-X is shown in FIG. 1.
As for the illuminance of the 450nm LED lamp, an ultraviolet thin illuminometer UIT- θ LED (manufactured by USHIO Motor Co.) was used to set the illuminance at the absolute value correction wavelength of 450nm at mW/cm 2 Is expressed in units of (a).
The sealant for a liquid crystal display element of the present invention has a gel fraction of less than 10% when an LED lamp having a peak top at a wavelength of 580nm (hereinafter, also referred to as "580nm LED lamp") is used to irradiate 400 lux for 48 hours. The sealant for a liquid crystal display element according to the present invention can suppress nozzle clogging at the time of coating by making the gel fraction of the sealant less than 10% when the light of 400 lux is irradiated for 48 hours by using the 580nm led lamp. The preferable upper limit of the gel fraction when the light of 400 lux is irradiated for 48 hours using the 580nm led lamp is 7%, and the more preferable upper limit is 3%.
Examples of the 580nm LED lamp include ECOHIUX HES-YF LDG32 T.Y22/22 (IRIS OHYAMA). The emission spectrum of ECOHIUX HES-YF LDG32 T.Y22/22 is shown in FIG. 2.
As for the illuminance of the 580nmLED lamp, the illuminance when using a digital illuminometer TM-201L (manufactured by TENMARS Co.) was expressed in units of lux (lx).
The sealant for a liquid crystal display element of the present invention contains a curable resin.
The curable resin preferably contains a (meth) acrylic compound.
Examples of the (meth) acrylic compound include a (meth) acrylate compound, an epoxy (meth) acrylate, and a urethane (meth) acrylate. Among them, epoxy (meth) acrylate is preferable. From the viewpoint of reactivity, the (meth) acrylic compound preferably has 2 or more (meth) acryloyl groups in 1 molecule.
In the present specification, the "(meth) acrylic acid" means acrylic acid or methacrylic acid, the "(meth) acrylic compound" means a compound having a (meth) acryloyl group, and the "(meth) acryloyl group" means an acryloyl group or a methacryloyl group. The term "(meth) acrylate" refers to an acrylate or a methacrylate. The "epoxy (meth) acrylate" refers to a compound obtained by reacting all epoxy groups in an epoxy compound with (meth) acrylic acid.
Examples of the monofunctional compound among the (meth) acrylate compounds include: methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, dicyclopentenyl (meth) acrylate, and process for the preparation of the same, tetrahydrofurfuryl (meth) acrylate, ethylcarbitol (meth) acrylate, 2-trifluoroethyl (meth) acrylate, 2, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxyethyl 2-hydroxypropyl phthalate, 2- (meth) acryloyloxyethyl phosphate, glycidyl (meth) acrylate, and the like.
Examples of the 2-functional compound in the (meth) acrylate compound include: 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate neopentyl glycol di (meth) acrylate, ethylene oxide addition bisphenol A di (meth) acrylate, propylene oxide addition bisphenol A di (meth) acrylate, ethylene oxide addition bisphenol F di (meth) acrylate, dimethylol dicyclopentadiene di (meth) acrylate, ethylene oxide modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acryloxypropyl (meth) acrylate, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone diol di (meth) acrylate, polybutadiene diol di (meth) acrylate, and the like.
Examples of the compound having 3 or more functions among the (meth) acrylate compounds include: trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tri (meth) acryloxyethyl phosphate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
Examples of the epoxy (meth) acrylate include: epoxy (meth) acrylate obtained by reacting an epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method, and the like.
Examples of the epoxy compound that is a raw material for synthesizing the epoxy (meth) acrylate include: bisphenol A type epoxy compound, bisphenol F type epoxy compound, bisphenol S type epoxy compound, 2' -diallyl bisphenol A type epoxy compound, hydrogenated bisphenol type epoxy compound, propylene oxide addition bisphenol A type epoxy compound, resorcinol type epoxy compound, biphenyl type epoxy compound, thioether type epoxy compound, diphenyl ether type epoxy compound, dicyclopentadiene type epoxy compound, naphthalene type epoxy compound, phenol novolac type epoxy compound, o-cresol novolac type epoxy compound, dicyclopentadiene novolac type epoxy compound, biphenyl novolac type epoxy compound, naphthol novolac type epoxy compound, glycidol amine type epoxy compound, alkyl polyol type epoxy compound, rubber modified type epoxy compound, glycidyl ester compound, and the like.
Examples of commercial products of the bisphenol A type epoxy compound include jER828EL and jER1004 (both manufactured by Mitsubishi chemical corporation), EPICLON EXA-850CRP (manufactured by DIC corporation), and the like.
Examples of commercial products of the bisphenol F type epoxy compound include jER806 and jER4004 (both manufactured by Mitsubishi chemical corporation).
Examples of commercial products of the bisphenol S type epoxy compound include EPICLON EXA1514 (manufactured by DIC Co.).
Examples of the commercial products of the 2,2' -diallylbisphenol A type epoxy compound include RE-810NM (manufactured by Japanese chemical Co., ltd.).
Examples of commercial products of the hydrogenated bisphenol type epoxy compound include EPICLON EXA7015 (manufactured by DIC Co.).
Examples of commercial products obtained by adding propylene oxide to bisphenol A type epoxy compounds include EP-4000S (manufactured by ADEKA).
Examples of commercial products of the resorcinol-type epoxy compound include EX-201 (manufactured by Nagase ChemteX Co., ltd.).
Examples of commercial products of the biphenyl epoxy compounds include jER YX-4000H (manufactured by mitsubishi chemical company).
Examples of commercial products of the above-mentioned thioether-type epoxy compounds include YSLV-50TE (NIPPON STEEL Chemical & Material Co.) and the like.
Examples of commercial products of the diphenyl ether type epoxy compounds include YSLV-80DE (NIPPON STEEL Chemical & Material Co.) and the like.
Examples of commercial products of the dicyclopentadiene type epoxy compound include EP-4088S (manufactured by ADEKA Co., ltd.).
Examples of the commercial products of the naphthalene type epoxy compound include EPICLON HP4032 and EPICLON EXA-4700 (both manufactured by DIC Co.).
Examples of the commercial products of the phenol novolac type epoxy compounds include EPICLON N-770 (manufactured by DIC Co., ltd.).
Examples of the commercial products of the o-cresol novolac type epoxy compounds include EPICLON N-670-EXP-S (manufactured by DIC Co., ltd.).
Examples of commercial products of the dicyclopentadiene phenol type epoxy compound include EPICLON HP7200 (manufactured by DIC Co.).
Examples of commercial products of the biphenyl novolac type epoxy compounds include NC-3000P (manufactured by Japanese chemical Co., ltd.).
Examples of the commercial products of the naphthol novolac type epoxy compounds include ESN-165S (NIPPON STEEL Chemical & Material Co.).
Examples of commercial products of the glycidylamine-type epoxy compounds include jor 630 (manufactured by mitsubishi chemical Co., ltd.), epicalon 430 (manufactured by DIC corporation), tetra-X (manufactured by mitsubishi gas chemical Co., ltd.), and the like.
Examples of commercial products of the alkyl polyol type epoxy compound include ZX-1542 (NIPPON STEEL Chemical & Material Co., ltd.), EPICLON 726 (DIC Co., ltd.), EPOLIGHT 80MFA (Co., ltd.), denacol EX-611 (Nagase ChemteX Co., ltd.), and the like.
Examples of the commercial products of the rubber-modified epoxy compound include YR-450, YR-207 (both NIPPON STEEL Chemical and Material Co., ltd.), epolead PB (Daicel Co., ltd.), and the like.
Examples of the commercial products of the above glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Co., ltd.).
Examples of other commercially available products of the epoxy compounds include YDC-1312, YSLV-80XY, YSLV-90CR (both manufactured by NIPPON STEEL Chemical & Material Co., ltd.), XAC4151 (manufactured by Asahi chemical Co., ltd.), jER1031, jER1032 (both manufactured by Mitsubishi chemical Co., ltd.), EXA-7120 (manufactured by DIC Co., ltd.), TEPIC (manufactured by Nissan chemical Co., ltd.), and the like.
Examples of the commercial products of the epoxy (meth) acrylates include epoxy (meth) acrylates manufactured by DAICEL-ALLNEX, epoxy (meth) acrylates manufactured by Xinzhou chemical industry, epoxy (meth) acrylates manufactured by Zosterol chemical industry, and epoxy (meth) acrylates manufactured by Nagase ChemteX.
Examples of the epoxy (meth) acrylate produced by Daicel-ALLNEX include EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3708, EBECRYL3800, EBECRYL6040, and EBECRYL RDX 63182.
Examples of the epoxy (meth) acrylate include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, and EMA-1020.
Examples of the Epoxy (meth) acrylate produced by the company of Cooperation chemical include Epoxy Ester M-600A, epoxy Ester 40EM, epoxy Ester 70PA, epoxy Ester 200PA, epoxy Ester 80MFA, epoxy Ester 3002M, epoxy Ester 3002A, epoxy Ester 1600A, epoxy Ester 3000M, epoxy Ester3000A, epoxy Ester 200EA, epoxy Ester 400EA, and the like.
Examples of the epoxy (meth) acrylate include Denacol Acrylate DA-141, denacol Acrylate DA-314, denacol Acrylate DA-911, and the like, which are manufactured by Nagase ChemteX corporation.
The urethane (meth) acrylate can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with a polyfunctional isocyanate compound in the presence of a catalytic amount of a tin compound.
Examples of the polyfunctional isocyanate compound include: isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, dimethylbiphenyl diisocyanate, xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, 1,6, 11-undecane triisocyanate, etc.
Further, as the above-mentioned polyfunctional isocyanate compound, a chain-extended polyfunctional isocyanate compound obtained by reacting a polyol with an excessive amount of the polyfunctional isocyanate compound may also be used.
Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include hydroxyalkyl mono (meth) acrylate, mono (meth) acrylate of a diol, mono (meth) acrylate or di (meth) acrylate of a triol, and epoxy (meth) acrylate.
Examples of the hydroxyalkyl (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Examples of the dihydric alcohol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol.
Examples of the triol include trimethylolethane, trimethylolpropane, and glycerin.
Examples of the epoxy (meth) acrylate include bisphenol a type epoxy acrylate.
Examples of commercial products of the urethane (meth) acrylate include: urethane (meth) acrylate manufactured by east asia synthesis company, urethane (meth) acrylate manufactured by DAICEL-ALLNEX company, urethane (meth) acrylate manufactured by the company of the industry on the root, urethane (meth) acrylate manufactured by the company of the new yo chemical industry, urethane (meth) acrylate manufactured by the company of the co-Rong chemical industry, and the like.
Examples of the urethane (meth) acrylate produced by the east Asia synthetic company include M-1100, M-1200, M-1210, and M-1600.
Examples of urethane (meth) acrylates manufactured by Daicel-ALLNEX include EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYL4842, EBECRYL4858, EBECRYL5129, EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260, and the like.
Examples of urethane (meth) acrylates produced by the above-mentioned on-the-root industries include Artesin UN-330, artesin SH-500B, artesin UN-1200TPK, artesin UN-1255, artesin UN-3320HB, artesin UN-7100, artesin UN-9000A, and Artesin UN-9000H.
Examples of the urethane (meth) acrylate include U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6HA, U-6LPA, U-10H, U-15HA, U-108A, U-122A, U-122P, U-324A, U-340A, U-340P, U-1084A, U-2061BA, UA-340P, UA-4000, UA-4100, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, and UA-W2A.
As urethane (meth) acrylate produced by the company of Cooperation, AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T and the like are mentioned, for example.
The curable resin may contain an epoxy compound for the purpose of improving the adhesiveness of the obtained sealant for a liquid crystal display element. Examples of the epoxy compound include: an epoxy compound which is a raw material for synthesizing the epoxy (meth) acrylate, a partially (meth) acrylic acid-modified epoxy compound, and the like.
In the present specification, the above-mentioned partial (meth) acrylic-modified epoxy compound means: for example, a compound having 1 or more epoxy groups and 1 or more (meth) acryloyl groups in the molecule, which is obtained by reacting a part of epoxy groups of an epoxy compound having 2 or more epoxy groups in the molecule with (meth) acrylic acid, can be used.
When the curable resin contains the (meth) acrylic compound and the epoxy compound, or when the curable resin contains the partially (meth) acrylic-modified epoxy compound, the ratio of the (meth) acryloyl group in the total of the (meth) acryloyl groups and the epoxy groups in the curable resin is preferably 30 mol% or more and 95 mol% or less. When the ratio of the (meth) acryloyl groups is in this range, the occurrence of liquid crystal contamination is suppressed, and the adhesiveness of the obtained sealant for a liquid crystal display element is further improved.
From the viewpoint of making the low liquid crystal contamination of the obtained sealant for a liquid crystal display element more excellentThe curable resin preferably has an-OH group, -NH-group, -NH 2 Hydrogen-bonding units such as radicals.
The curable resin may be used alone or in combination of 2 or more.
The sealant for a liquid crystal display element of the present invention contains a photopolymerization initiator.
For irradiation of 100mW/cm using the 450nm LED lamp described above 2 The gel fraction at 30 seconds and the gel fraction at 48 hours when 400 lux of light was irradiated with the 580nm led lamp can be adjusted by adjusting the types and the content ratios of the photopolymerization initiator, the combination of the photopolymerization initiator and a sensitizer described later.
As the photopolymerization initiator, the irradiation of the 450nm LED lamp was easily performed at 100mW/cm 2 The compounds represented by the following formulas (1-1) to (1-3) are preferable in terms of adjusting the gel fraction at 30 seconds of light and the gel fraction at 48 hours of light of 400 lux using the 580nm led lamp. When the photopolymerization initiator is contained in combination with a sensitizer described later, camphorquinone is also preferable as the photopolymerization initiator.
[ chemical formula 1]
The content of the photopolymerization initiator is preferably limited to 0.3 parts by weight and the content of the photopolymerization initiator is preferably limited to 10 parts by weight based on 100 parts by weight of the curable resin. When the content of the photopolymerization initiator is 0.3 parts by weight or more, the obtained sealant for a liquid crystal display element is more excellent in the visible light curability and the low liquid crystal contamination property. When the content of the photopolymerization initiator is 10 parts by weight or less, the resulting sealant for a liquid crystal display element is more excellent in low liquid crystal contamination. The more preferable lower limit of the content of the photopolymerization initiator is 0.5 parts by weight, and the more preferable upper limit is 4 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a sensitizer.
In the case of using the camphorquinone as the photopolymerization initiator, irradiation of 100mW/cm with the 450nm LED lamp can be easily adjusted by using the sensitizer in combination with the camphorquinone 2 Gel fraction at 30 seconds, and gel fraction at 48 hours when 400 lux of light was irradiated using the 580nm led lamp.
As the sensitizer, the use of the combination with camphorquinone makes it easy to irradiate the 450nm LED lamp with 100mW/cm 2 The compound represented by the following formula (2-1) and the compound represented by the following formula (2-2) are preferable in terms of adjusting the gel fraction at 30 seconds and the gel fraction at 48 hours when 400 lux of light is irradiated with the 580nm led lamp.
[ chemical formula 2]
The lower limit of the content of the sensitizer is preferably 0.001 parts by weight and the upper limit is preferably 0.5 parts by weight relative to 100 parts by weight of the curable resin. When the content of the sensitizer is in this range, the obtained sealant for a liquid crystal display element is more excellent in the visible light curability and the low liquid crystal contamination property, and the effect of suppressing nozzle clogging at the time of coating is more excellent. The lower limit of the content of the sensitizer is more preferably 0.005 parts by weight, and the upper limit is more preferably 0.1 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a thermal polymerization initiator within a range that does not hinder the object of the present invention.
Examples of the thermal polymerization initiator include thermal polymerization initiators composed of azo compounds, organic peroxides, and the like. Among them, a polymeric azo initiator composed of a polymeric azo compound is preferable.
The thermal polymerization initiator may be used alone or in combination of 2 or more.
In the present specification, the "polymer azo compound" refers to a compound having an azo group and having a number average molecular weight of 300 or more, which generates radicals capable of curing (meth) acryloyloxy groups by heat.
The number average molecular weight of the polymer azo compound is preferably 1000 at the lower limit and 30 tens of thousands at the upper limit. When the number average molecular weight of the polymer azo compound is in this range, contamination of the liquid crystal can be suppressed and the polymer azo compound can be easily mixed with the curable resin. The number average molecular weight of the polymer azo compound is more preferably limited to 5000, more preferably to 10 ten thousand, still more preferably to 1 ten thousand, and still more preferably to 9 ten thousand.
Examples of the polymer azo compound include: a polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via azo groups.
The polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via an azo group is preferably a polymer azo compound having a polyethylene oxide structure.
Specific examples of the polymer azo compound include: polycondensates of 4,4 '-azobis (4-cyanovaleric acid) and polyalkylene glycol, polycondensates of 4,4' -azobis (4-cyanovaleric acid) and polydimethylsiloxane having terminal amino groups, and the like.
Examples of commercial products of the polymer azo compound include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (both manufactured by Fuji photo-pure chemical Co., ltd.).
Examples of azo compounds other than the polymer include V-65 and V-501 (both manufactured by Fuji photo-pure chemical Co., ltd.).
Examples of the organic peroxide include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
The preferable lower limit of the content of the thermal polymerization initiator is 0.05 parts by weight and the preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the thermal polymerization initiator is 0.05 parts by weight or more, the sealant for a liquid crystal display element of the present invention is more excellent in thermosetting property. When the content of the thermal polymerization initiator is 10 parts by weight or less, the sealant for a liquid crystal display element of the present invention is further excellent in low liquid crystal contamination and storage stability. The lower limit of the content of the thermal polymerization initiator is more preferably 0.1 part by weight, and the upper limit is more preferably 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a thermosetting agent.
Examples of the thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, and acid anhydrides. Among them, organic acid hydrazides are suitably used.
The above-mentioned thermosetting agents may be used alone or in combination of 2 or more.
Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
Examples of the commercial products of the organic acid hydrazide include organic acid hydrazides manufactured by Otsuka chemical company, and organic acid hydrazides manufactured by Ajinomoto Fine-Techno company.
Examples of the organic acid hydrazide manufactured by Otsuka chemical Co., ltd include SDH and ADH.
Examples of the organic acid hydrazide manufactured by Ajinomoto Fine-Techno include Ajicure VDH, ajicure VDH-J, ajicure UDH, and Ajicure UDH-J.
The content of the thermosetting agent is preferably 1 part by weight at a lower limit and 50 parts by weight at an upper limit, based on 100 parts by weight of the curable resin. By setting the content of the thermosetting agent to this range, thermosetting properties can be further improved without deteriorating the coatability and the like of the obtained sealing agent for a liquid crystal display element. The more preferable upper limit of the content of the above-mentioned thermosetting agent is 30 parts by weight.
The sealing agent for a liquid crystal display element of the present invention preferably contains a filler for the purpose of increasing viscosity, improving adhesiveness due to stress dispersion effect, improving linear expansion coefficient, and the like.
As the filler, an inorganic filler and an organic filler can be used.
Examples of the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate.
Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The filler also has a power of 100mW/cm when irradiated with 450nm LED lamp 2 For 30 seconds, the effect of promoting scattering of light and increasing gel fraction is preferable. In particular, an organic filler is more preferable than an inorganic filler in view of ensuring light transmittance at the same time.
The above fillers may be used alone or in combination of 2 or more.
The preferable lower limit of the content of the filler is 10 parts by weight and the preferable upper limit is 60 parts by weight relative to 100 parts by weight of the curable resin. When the content of the filler is within this range, the effect of improving the adhesion and the like is further improved without deteriorating the coating property and the like. The lower limit of the content of the filler is more preferably 20 parts by weight, and the upper limit is more preferably 50 parts by weight.
The sealing agent for a liquid crystal display element of the present invention preferably contains a silane coupling agent. The silane coupling agent mainly has a role as an adhesion promoter for favorably adhering the sealing agent to a substrate or the like.
Examples of suitable silane coupling agents include 3-aminopropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, and 3-isocyanatopropyl trimethoxysilane. These are excellent in the effect of improving the adhesion to a substrate or the like, and can suppress the outflow of the curable resin into the liquid crystal by chemical bonding with the curable resin.
The silane coupling agent may be used alone or in combination of 2 or more.
The preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is 0.1 part by weight, and the preferable upper limit is 10 parts by weight. When the content of the silane coupling agent is within this range, the effect of suppressing the occurrence of liquid crystal contamination and improving the adhesion becomes more excellent. The more preferable lower limit of the content of the above silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may further contain additives such as a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor, as necessary.
Examples of the method for producing the sealant for a liquid crystal display element of the present invention include: a method of mixing the curable resin, the photopolymerization initiator, the sensitizer, and the silane coupling agent, if necessary, using a mixer such as a homodisperser, homomixer, universal mixer, planetary mixer, kneader, or three-roll mixer.
By incorporating conductive fine particles into the sealing agent for a liquid crystal display element of the present invention, a vertically conductive material can be produced.
As the conductive fine particles, metal balls, conductive fine particles having a conductive metal layer formed on the surface of the resin fine particles, and the like can be used. Among them, conductive fine particles having a conductive metal layer formed on the surface of the resin fine particles are preferable because conductive connection can be performed without damaging the transparent substrate or the like due to excellent elasticity of the resin fine particles.
The liquid crystal display element having the cured product of the sealant for a liquid crystal display element of the present invention is also one of the present invention.
As the liquid crystal display element of the present invention, a liquid crystal display element of a narrow frame design is preferable. Specifically, the width of the frame portion around the liquid crystal display portion is preferably 2mm or less.
The width of the sealant for a liquid crystal display element of the present invention applied in the production of the liquid crystal display element of the present invention is preferably 1mm or less.
As a method for manufacturing the liquid crystal display element of the present invention, a liquid crystal dropping method is suitably used, and specifically, for example, a method having the following steps is exemplified.
First, a step of forming a frame-like seal pattern by applying the sealant for a liquid crystal display element of the present invention to one of 2 transparent substrates having an electrode such as an ITO thin film and an alignment film by screen printing, dispenser coating, or the like is performed. Next, the following steps are performed: in the state where the sealing agent for a liquid crystal display element of the present invention is not cured, minute droplets of liquid crystal are applied dropwise to the inside of the frame of the sealing pattern of the substrate, and another transparent substrate is superimposed under vacuum. Then, a liquid crystal display element can be obtained by performing the steps of: and a step of irradiating the seal pattern portion of the sealing agent for a liquid crystal display element of the present invention with light through a cut filter or the like to thereby photocure the sealing agent. In addition to the step of photocuring the sealant, a step of heating the sealant to thermally cure the sealant may be performed.
Effects of the invention
According to the present invention, a sealant for a liquid crystal display element which is excellent in visible light curability and low in liquid crystal contamination and can suppress nozzle clogging at the time of coating can be provided. Further, according to the present invention, a liquid crystal display element using the sealant for a liquid crystal display element can be provided.
Drawings
FIG. 1 is an emission spectrum of UELCL-P-450-X.
FIG. 2 is a luminescence spectrum of ECOHIMUX HES-YF LDG32 T.Y22/22.
Detailed Description
Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
(Synthesis of Compound represented by the formula (1-1))
5 parts by weight of N-ethylcarbazole, 2.81 parts by weight of 2, 5-thiophenedicarboxychloride and 3.76 parts by weight of aluminum chloride were added to 40mL of methylene chloride, and the mixture was stirred at room temperature overnight. To the obtained reaction solution, 2.21 parts by weight of acetyl chloride and 3.76 parts by weight of aluminum chloride were added, and the mixture was further stirred at room temperature for 4 hours. After the obtained reaction solution was poured into ice water, the organic layer was extracted with ethyl acetate. The extracted solution was washed with a saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated to give a product (A1).
3 parts by weight of the obtained product (A1), 0.76 part by weight of ammonium hydroxychloride and 0.86 part by weight of pyridine were added to 30mL of ethanol, and the mixture was stirred under reflux for 10 hours. The obtained reaction solution was poured into ice water, followed by filtration. The filtrate was washed with water, dissolved in ethyl acetate, dried over anhydrous magnesium sulfate and concentrated to give a product (B1).
After 1.5 parts by weight of the obtained product (B1) was dissolved in 25 parts by weight of N, N-dimethylformamide, 0.59 part by weight of acetyl chloride was added. While cooling the obtained solution to 10℃or lower, 0.78 parts by weight of triethylamine was added dropwise thereto, and the mixture was stirred at room temperature for 4 hours. The obtained reaction solution was poured into water and then filtered. The filtrate was purified by silica gel column chromatography using a mixed solvent of dichloromethane and hexane (dichloromethane: hexane=2:1), whereby the compound represented by the above formula (1-1) was obtained.
The structure of the obtained compound represented by the above formula (1-1) is represented by 1 H-NMR、 13 C-NMR and FT-IR were confirmed.
(Synthesis of Compound represented by the formula (1-2))
5 parts by weight of N- (2-ethylhexyl) carbazole, 2.81 parts by weight of 2, 5-thiophenedicarboxychloride and 3.76 parts by weight of aluminum chloride were added to 40mL of methylene chloride, and the mixture was stirred at room temperature overnight. To the obtained reaction solution, 2.21 parts by weight of acetyl chloride and 3.76 parts by weight of aluminum chloride were added, and the mixture was further stirred at room temperature for 4 hours. After the obtained reaction solution was poured into ice water, the organic layer was extracted with ethyl acetate. The extracted solution was washed with a saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated to give a product (A2).
3 parts by weight of the obtained product (A2), 0.76 part by weight of ammonium hydroxychloride and 0.86 part by weight of pyridine were added to 30mL of ethanol, and stirred under reflux for 10 hours. The obtained reaction solution was poured into ice water, followed by filtration. The filtrate was washed with water, dissolved in ethyl acetate, dried over anhydrous magnesium sulfate and concentrated to give the product (B2).
After 1.5 parts by weight of the obtained product (B2) was dissolved in 25 parts by weight of N, N-dimethylformamide, 0.59 part by weight of acetyl chloride was added. While cooling the obtained solution to 10℃or lower, 0.78 parts by weight of triethylamine was added dropwise thereto, and the mixture was stirred at room temperature for 4 hours. The obtained reaction solution was poured into water and then filtered. The filtrate was purified by silica gel column chromatography using a mixed solvent of dichloromethane and hexane (dichloromethane: hexane=2:1), whereby the compound represented by the above formula (1-2) was obtained.
The structure of the obtained compound represented by the above formula (1-2) is represented by 1 H-NMR、 13 C-NMR and FT-IR were confirmed.
(Synthesis of Compound represented by the formula (1-3))
5 parts by weight of ethyl 3- (9H-carbazol-9-yl) propionate, 2.64 parts by weight of hexanoyl chloride and 2.62 parts by weight of aluminum chloride were added to 80mL of methylene chloride, and stirred at room temperature overnight. To the obtained reaction solution, 1.84 parts by weight of 2, 5-thiophenedicarboxychloride and 5.24 parts by weight of aluminum chloride were added, and the mixture was further stirred at room temperature for 4 hours. After the obtained reaction solution was poured into ice water, the organic layer was extracted with ethyl acetate. The extracted solution was washed with a saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated to give a product (A3).
To 4.0 parts by weight of the product (A3) in 20mL of ethanol was added 2.77 parts by weight of a 20% aqueous sodium hydroxide solution, and the mixture was refluxed for 3 hours. After the completion of the reaction, 50mL of water was added, the mixture was acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was then washed with water and brine, was dried over anhydrous sodium sulfate and concentrated to give the product (B3).
3 parts by weight of the obtained product (B3), 0.58 part by weight of ammonium hydroxychloride and 0.65 part by weight of pyridine were added to 30mL of ethanol, and the mixture was stirred under reflux for 10 hours. The obtained reaction solution was poured into ice water, followed by filtration. The filtrate was washed with water, dissolved in ethyl acetate, dried over anhydrous sodium sulfate and concentrated to give a product (C3).
After 1.5 parts by weight of the obtained product (C3) was dissolved in 20 parts by weight of N, N-dimethylformamide, 0.45 parts by weight of acetyl chloride was added. While cooling the obtained solution to 10℃or lower, 0.59 parts by weight of triethylamine was added dropwise thereto, and the mixture was stirred at room temperature for 4 hours. The obtained reaction solution was poured into water and then filtered. The compound was separated by silica gel column chromatography, whereby the compound represented by the above formula (1-3) was obtained.
The structure of the obtained compound represented by the above formula (1-3) is represented by 1 H-NMR、 13 C-NMR and FT-IR were confirmed.
Examples 1 to 10 and comparative examples 1 to 6
The respective materials were mixed by a planetary mixer in accordance with the mixing ratios shown in tables 1 and 2, and then mixed by a 3-roll machine, whereby the sealants for liquid crystal display elements of examples 1 to 10 and comparative examples 1 to 6 were prepared. As the planetary mixer, a deaeration milan (manufactured by the company thin) was used. The obtained sealant for liquid crystal display element was subjected to defoaming treatment with ARV-310LED (manufactured by THINKY Co.) as a pretreatment.
The obtained sealant for liquid crystal display elements was spread between 2 sheets of polyethylene terephthalate (PET) film (manufactured by linde corporation, "PET 5011") so as to have a thickness of 300 μm. Irradiation of 100mW/cm from one side of the PET film using a 450nm LED lamp 2 After 30 seconds, 2 PET films were peeled off from each other. When the sealant is not tacky, the cured sealing material is peeled from the PET film and cut into a 1cm x 2cm long strip,the resulting long test piece was wrapped with a 200 mesh metal mesh so that the sealant was not released from the site other than the lattice of the mesh. On the other hand, in the case where the sealant has tackiness, the sealant is collected by a plane of a micro spatula and wrapped with a 200 mesh metal mesh so that the sealant is not released from a portion other than the lattice of the mesh. In this case, the weight of the metal net used was measured and denoted as G0, and the total weight of the sealant and the weight of the metal net was measured and denoted as G1. In addition, G0 is 1G or more and less than 3G, and (G1-G0) is 0.2G or more and less than 0.4G. After the metal mesh coated with the sealant was placed in a screw tube No.8 (manufactured by Maruemu Co.), 70g of acetone was added to the screw tube, and the mixture was allowed to stand for 3 hours. The metal mesh coated with the sealant present in the acetone was taken out with forceps, placed in a new screw tube No.8 (manufactured by Maruemu Co.), and then 70g of new acetone was added to the screw tube, followed by further standing for 2 hours. After taking out the metal mesh coated with the sealant with tweezers, the metal mesh was dried in an oven at 80℃under normal pressure for 2 hours. After drying, the weight of the metal mesh coated with the sealant was measured and set to G2. The above-described operation was performed in a darkroom having a volume of 1 lux or less. In addition, a digital illuminometer TM-201L (manufactured by TENMARS Co.) manufactured by TENMARS was used for measuring illuminance of the work environment. The gel fraction was measured by substituting the obtained values of G0 to G2 into the above formula.
As a 450nm LED lamp, UELCL-P-450-X (manufactured by EYE GRAPHICS Co.) was used.
In addition, a 580nm led lamp was used instead of the 450nm led lamp, and the sealant after irradiation with light was irradiated with 400 lux for 48 hours to measure the gel fraction similarly. As a 580nm LED lamp, ECOHIUX HES-YF LDG32 T.Y22/22 (manufactured by IRIS OHYAMA Co.).
Further, instead of the 450nm LED lamp, a metal halide lamp was used, and 100mW/cm was irradiated via a cut-off filter (340 nm cut-off filter) for cutting off light of 340nm or less 2 The gel fraction was measured in the same manner as in the case of the sealant after irradiation with light for 30 seconds. The sealants for liquid crystal display elements obtained in examples 7, 9 and 10 were not measured for each sealant with a 340nm cut filter interposed therebetweenSheet irradiation 100mW/cm 2 Gel fraction at 30 seconds of light.
The gel fractions obtained are shown in tables 1 and 2.
< evaluation >
The sealants for liquid crystal display elements obtained in examples and comparative examples were evaluated as follows. The results are shown in tables 1 and 2.
(nozzle blockage)
The liquid crystal display elements obtained in examples and comparative examples were filled with the sealant into a dispensing syringe, and after deaeration treatment, a nozzle was provided in the syringe. Next, a syringe provided with a nozzle is set in the dispenser. In order to fill the tip of the nozzle with the sealing agent, compressed air is applied to the syringe to discharge the sealing agent from the tip of the nozzle. Then, the compressed air was stopped and the front end of the nozzle was wiped with becot.
The inside of the syringe was depressurized with a pressure that the sealing agent did not drop from the tip of the nozzle and the sealing agent did not lose from the tip of the nozzle, and left to stand for 48 hours in a state where the back suction was performed. Then, a pressure of 100kPa was applied to the inside of the syringe, the case where the sealant was discharged from the tip of the nozzle was marked "o", the case where the sealant was not discharged was marked "x", and the nozzle clogging was evaluated.
As a syringe for dispensing, PSY-10EU-OR (manufactured by Musashi Engineering Co.) was used, HN-0.3N (manufactured by Musashi Engineering Co.) was used as a nozzle provided in the syringe, and SHOTMASTER300 (manufactured by Musashi Engineering Co.) was used as a dispenser. The evaluation was performed under an environment where 400 lux of light was irradiated with a 580nm led lamp. As a 580nm LED lamp, ECOHIUX HES-YF LDG32 T.Y22/22 (IRIS OHYAMA Co., ltd.) was used, and illuminance was measured using TM-201L (TENMARS Co.).
(Low liquid Crystal contamination)
To the sample bottle, 0.5g of negative liquid crystal (manufactured by JNC Petroleum chemical Co., ltd., "JC-7129 XX") was added, and after adding 0.1g of each of the sealants for liquid crystal display elements obtained in examples and comparative examples and shaking, the mixture was heated at 120℃for 1 hour and then returned to room temperature (25 ℃). Having transparent electrodes and having been performed The sealants for liquid crystal display elements obtained in examples and comparative examples were applied to the alignment film of the glass substrate of the alignment film (RB-089 manufactured by japanese chemical Co., ltd.) by a dispenser so as to draw a square frame. The sealant was applied under an environment where light of 1 lux or less was irradiated with a 580nm led lamp. As a 580nm LED lamp, ECOHIUX HES-YF LDG32 T.Y22/22 (manufactured by IRIS OHYAMA Co.). Next, minute droplets of the liquid crystal taken out from the sample bottle were applied dropwise to the entire inner surface of the frame on the substrate, and another glass substrate was superimposed in vacuum. Vacuum was released and 100mW/cm was irradiated with a 450nm LED lamp 2 For 30 seconds. As a 450nm LED lamp, UELCL-P-450-X (manufactured by EYE GRAPHICS Co.) was used. Then, the sealant was thermally cured by heating at 120 ℃ for 1 hour, thereby obtaining a liquid crystal display element.
The voltage holding ratio of the liquid crystal was calculated by applying an alternating voltage of 5V and 1Hz at 25℃using a liquid crystal physical property evaluation system (model 6254, manufactured by TOYO Corporation) to the obtained liquid crystal display element, and measuring the holding voltage after 1 second. The voltage holding ratio of 95% or more was "very good", the voltage holding ratio of 80% or more and less than 95% was "good", the voltage holding ratio of less than 80% was "poor", and the liquid crystal contamination was evaluated.
/>
Industrial applicability
According to the present invention, a sealant for a liquid crystal display element which is excellent in visible light curability and low in liquid crystal contamination and can suppress nozzle clogging at the time of coating can be provided. Further, according to the present invention, a liquid crystal display element using the sealant for a liquid crystal display element can be provided.
Claims (2)
1. A sealant for a liquid crystal display element, characterized by comprising a curable resin and a photopolymerization initiator,
irradiation of 100mW/cm with an LED lamp having a peak at a wavelength of 450nm 2 The gel fraction at 30 seconds of light of (2) is 70% or more, and,
the gel fraction was less than 10% when 400 lux of light was irradiated for 48 hours using an LED lamp having a peak top at a wavelength of 580 nm.
2. A liquid crystal display element comprising the cured product of the sealant for a liquid crystal display element according to claim 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021094542 | 2021-06-04 | ||
| JP2021-094542 | 2021-06-04 | ||
| PCT/JP2022/022496 WO2022255452A1 (en) | 2021-06-04 | 2022-06-02 | Sealing agent for liquid crystal display elements and liquid crystal display element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117043670A true CN117043670A (en) | 2023-11-10 |
Family
ID=84324263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280023421.9A Pending CN117043670A (en) | 2021-06-04 | 2022-06-02 | Sealing agent for liquid crystal display element and liquid crystal display element |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP7201881B1 (en) |
| KR (1) | KR20240017908A (en) |
| CN (1) | CN117043670A (en) |
| TW (1) | TW202313921A (en) |
| WO (1) | WO2022255452A1 (en) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3583326B2 (en) | 1999-11-01 | 2004-11-04 | 協立化学産業株式会社 | Sealant for dripping method of LCD panel |
| KR100906926B1 (en) | 2001-05-16 | 2009-07-10 | 세키스이가가쿠 고교가부시키가이샤 | Curing Resin Composition and Sealants and End-Sealing Materials for Displays |
| JP2003313216A (en) * | 2002-04-18 | 2003-11-06 | Henkel Loctite Corp | Visual light curable resin composition |
| JP4344400B1 (en) * | 2009-02-16 | 2009-10-14 | 株式会社日本化学工業所 | Oxime ester compounds and photosensitive resin compositions using them |
| WO2018038016A1 (en) | 2016-08-26 | 2018-03-01 | シャープ株式会社 | Seal material composition, liquid crystal cell, and method for producing liquid crystal cell |
| CN106405946A (en) * | 2016-11-29 | 2017-02-15 | 深圳市华星光电技术有限公司 | Sealant curing method and liquid crystal panel manufacturing method |
| JP7297499B2 (en) * | 2019-04-04 | 2023-06-26 | 東京応化工業株式会社 | Photosensitive resin composition, method for producing patterned cured film, and patterned cured film |
| KR20220149651A (en) * | 2020-03-03 | 2022-11-08 | 세키스이가가쿠 고교가부시키가이샤 | Curable resin composition, sealing compound for display elements, sealing compound for liquid crystal display elements, vertical conduction material, display element, adhesive for electronic components, and electronic component |
-
2022
- 2022-06-02 CN CN202280023421.9A patent/CN117043670A/en active Pending
- 2022-06-02 TW TW111120745A patent/TW202313921A/en unknown
- 2022-06-02 JP JP2022537078A patent/JP7201881B1/en active Active
- 2022-06-02 KR KR1020247000209A patent/KR20240017908A/en unknown
- 2022-06-02 WO PCT/JP2022/022496 patent/WO2022255452A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| JP7201881B1 (en) | 2023-01-10 |
| KR20240017908A (en) | 2024-02-08 |
| JPWO2022255452A1 (en) | 2022-12-08 |
| WO2022255452A1 (en) | 2022-12-08 |
| TW202313921A (en) | 2023-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI801554B (en) | Photopolymerization initiator, sealant for display elements, upper and lower conduction materials, display elements and compounds | |
| JP5337293B1 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN114667302B (en) | Curable resin composition, sealant for display element, sealant for liquid crystal display element, vertically conductive material, display element, adhesive for electronic component, and electronic component | |
| JP6703650B1 (en) | Liquid crystal element sealant, vertical conduction material, and liquid crystal element | |
| WO2015178357A1 (en) | Sealant for one-drop filling process, vertically conductive material, and liquid crystal display element | |
| JP5340502B2 (en) | Liquid crystal dropping method sealing agent, vertical conduction material, and liquid crystal display element | |
| JP6216260B2 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP7084560B1 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP6725771B1 (en) | Sealant for liquid crystal display device, vertical conduction material, and liquid crystal display device | |
| CN117043670A (en) | Sealing agent for liquid crystal display element and liquid crystal display element | |
| JP7253117B1 (en) | Sealant for liquid crystal display element and liquid crystal display element | |
| JP7053262B2 (en) | Manufacturing method of sealant for liquid crystal display element | |
| JP5918606B2 (en) | Sealant for liquid crystal dropping method, vertical conduction material, and liquid crystal display element | |
| CN111164178B (en) | Composition for electronic material, sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| WO2023032543A1 (en) | Liquid crystal display element sealant and liquid crystal display element | |
| TW202208587A (en) | Sealing agent for liquid crystal display elements, vertical conduction material, and liquid crystal display element | |
| WO2021177314A1 (en) | Curable resin composition, display element sealant, liquid crystal display element sealant, vertical conductive material, display element, electronic component adhesive, and electronic component | |
| CN115996959A (en) | Thioxanthone compound, photopolymerization initiator, curable resin composition, composition for display element, sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| TW202003776A (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |