TW201908454A - Sealant for liquid crystal display element, upper and lower conductive materials, and liquid crystal display element - Google Patents
Sealant for liquid crystal display element, upper and lower conductive materials, and liquid crystal display elementInfo
- Publication number
- TW201908454A TW201908454A TW107124131A TW107124131A TW201908454A TW 201908454 A TW201908454 A TW 201908454A TW 107124131 A TW107124131 A TW 107124131A TW 107124131 A TW107124131 A TW 107124131A TW 201908454 A TW201908454 A TW 201908454A
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid crystal
- compound
- meth
- crystal display
- acrylate
- Prior art date
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 93
- 239000004020 conductor Substances 0.000 title claims abstract description 7
- 239000000565 sealant Substances 0.000 title claims description 53
- -1 maleimide compound Chemical class 0.000 claims abstract description 98
- 238000007789 sealing Methods 0.000 claims abstract description 32
- 239000003999 initiator Substances 0.000 claims abstract description 29
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 239000011347 resin Substances 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 125
- 239000004593 Epoxy Substances 0.000 claims description 103
- 239000010419 fine particle Substances 0.000 claims description 11
- 230000008033 biological extinction Effects 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 5
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 31
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 88
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 23
- 239000000758 substrate Substances 0.000 description 21
- 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 16
- 150000002148 esters Chemical class 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 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 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 238000012719 thermal polymerization Methods 0.000 description 6
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- 238000011109 contamination Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000005286 illumination Methods 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
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229910000071 diazene Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 238000003756 stirring Methods 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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 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
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- 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
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 125000000217 alkyl group Chemical group 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
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 150000001451 organic peroxides Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
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- 150000004072 triols Chemical class 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
- BSSNZUFKXJJCBG-UPHRSURJSA-N (z)-but-2-enediamide Chemical group NC(=O)\C=C/C(N)=O BSSNZUFKXJJCBG-UPHRSURJSA-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
- HGCMSCWGVAYWHR-UHFFFAOYSA-N 1,3,5-trimethyl-2-[[phenyl-[(2,4,6-trimethylphenyl)methyl]phosphoryl]methyl]benzene Chemical compound CC1=CC(C)=CC(C)=C1CP(=O)(C=1C=CC=CC=1)CC1=C(C)C=C(C)C=C1C HGCMSCWGVAYWHR-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
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- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-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
- HJEORQYOUWYAMR-UHFFFAOYSA-N 2-[(2-butylphenoxy)methyl]oxirane Chemical group CCCCC1=CC=CC=C1OCC1OC1 HJEORQYOUWYAMR-UHFFFAOYSA-N 0.000 description 1
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 description 1
- WYAFQPYCJBLWAS-UHFFFAOYSA-N 2-[(3-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC(OCC2OC2)=C1 WYAFQPYCJBLWAS-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-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
- RJTQIGKJCAXHLT-UHFFFAOYSA-N 2-formyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC=O RJTQIGKJCAXHLT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 1
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-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
- XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical compound N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-UHFFFAOYSA-N 0.000 description 1
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- FIEKVYPYFQSFTP-UHFFFAOYSA-N 6-methyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C FIEKVYPYFQSFTP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 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
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-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
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
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- FYYIUODUDSPAJQ-XVBQNVSMSA-N [(1S,6R)-7-oxabicyclo[4.1.0]heptan-3-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CC[C@H]2O[C@H]2C1 FYYIUODUDSPAJQ-XVBQNVSMSA-N 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 230000001678 irradiating effect Effects 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
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- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 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
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 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
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
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- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
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- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000003825 pressing Methods 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
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 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
- 239000000600 sorbitol Substances 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
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003568 thioethers Chemical class 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nonlinear Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
- Polymerisation Methods In General (AREA)
- Epoxy Resins (AREA)
Abstract
Description
本發明係關於一種對長波長之光的硬化性優異，且可抑制異物產生之液晶顯示元件用密封劑。又，本發明係關於一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 The present invention relates to a sealant for a liquid crystal display element which is excellent in curability of long-wavelength light and can suppress generation of foreign substances. The present invention also relates to a top-to-bottom conductive material and a liquid crystal display element using the sealant for a liquid crystal display element.
近年來，作為液晶顯示單元等液晶顯示元件之製造方法，就產距時間(tact time)縮短、使用液晶量之最佳化等觀點而言，一直使用如專利文獻1、專利文獻2揭示之使用光熱併用硬化型之密封劑的被稱為滴下法之液晶滴下方式。 In recent years, as a method of manufacturing a liquid crystal display element such as a liquid crystal display unit, from the viewpoint of shortening the tact time and optimizing the amount of liquid crystal used, the use disclosed in Patent Document 1 and Patent Document 2 has been used. The liquid crystal dropping method called the dropping method which uses a combination of light and heat as a hardening type sealant.
於滴下法中，首先，於2片附電極之透明基板中之一者，藉由滴塗(dispense)而形成框狀之密封圖案。繼而，於密封劑未硬化之狀態下將液晶之微滴滴下至透明基板之整個框內，立即貼合另一透明基板，對密封部照射紫外線等光而進行預硬化。然後，於液晶退火時進行加熱而進行正式硬化，從而製作液晶顯示元件。若於減壓下進行基板之貼合，則可以極高之效率製造液晶顯示元件，目前，該滴下法為液晶顯示元件製造方法之主流。 In the dropping method, first, one of the two transparent substrates with electrodes is formed by dispensing to form a frame-shaped sealing pattern. Then, in a state where the sealant is not cured, droplets of liquid crystal are dropped into the entire frame of the transparent substrate, immediately attached to another transparent substrate, and pre-cured by irradiating the sealing portion with light such as ultraviolet rays. Then, when the liquid crystal is annealed, it is heated to formally harden to produce a liquid crystal display element. If the substrates are bonded under reduced pressure, the liquid crystal display element can be manufactured with extremely high efficiency. Currently, the dropping method is the mainstream of the liquid crystal display element manufacturing method.
另外，於行動電話、可攜式遊戲機等各種附液晶面板之移動機器普及之現代，裝置小型化為最迫切之課題。作為裝置小型化之方法，可列舉液晶顯示部之窄邊框化，例如進行將密封部之位置配置於黑矩陣下方之步驟(以下，亦稱為窄邊框設計)。 In addition, as mobile phones, portable game consoles and other modern mobile devices with liquid crystal panels are popular, the miniaturization of devices is the most pressing issue. As a method of miniaturizing the device, a narrow frame of the liquid crystal display portion can be cited, for example, a step of arranging the position of the sealing portion below the black matrix (hereinafter, also referred to as a narrow frame design) is performed.
然而，於窄邊框設計中，由於密封劑被配置於黑矩陣之正下方，故而若進行滴下法，則有使密封劑光硬化時所照射之光被遮蔽，光不會到達至密封劑之內部導致硬化變得不充分之問題。若因此密封劑之硬化不充分，則有未硬化之密封劑成分溶出至液晶中，於液晶中進行由溶出之密封劑成分所引起之硬化反應而產生液晶污染之問題。 However, in the narrow bezel design, since the sealant is disposed directly under the black matrix, if the dripping method is performed, the light irradiated when the sealant is hardened by light is blocked and the light does not reach the inside of the sealant The problem that hardening becomes insufficient. If the hardening of the sealant is insufficient, the uncured sealant component may be eluted into the liquid crystal, and the liquid crystal may be contaminated due to the hardening reaction caused by the eluted sealant component in the liquid crystal.
又，通常作為使密封劑光硬化之方法，係進行紫外線之照射，但於液晶滴下法中，於滴下液晶後使密封劑硬化，故而有因照射紫外線而使得液晶劣化之問題。為了防止由紫外線所引起之液晶之劣化，考慮摻合對長波長之光的反應性優異之光聚合起始劑，藉由經由截止濾光器等之長波長之光進行光硬化。然而，於使用此種光聚合起始劑之情形時，有下述等問題：於光硬化步驟前密封劑因少量之光而局部發生硬化，產生異物。 In addition, as a method of photo-curing the sealant, ultraviolet irradiation is generally used. However, in the liquid crystal dropping method, the sealant is hardened after the liquid crystal is dropped, so that there is a problem that the liquid crystal is deteriorated by ultraviolet irradiation. In order to prevent the deterioration of liquid crystals caused by ultraviolet rays, it is considered to incorporate a photopolymerization initiator excellent in reactivity with long-wavelength light, and photoharden by long-wavelength light passing through a cut-off filter or the like. However, in the case of using such a photopolymerization initiator, there are problems such as: before the photo-curing step, the sealant locally hardens due to a small amount of light to generate foreign matter.
[先前技術文獻] [Prior technical literature]
[專利文獻] [Patent Literature]
專利文獻1：日本專利特開2001-133794號公報 Patent Document 1: Japanese Patent Laid-Open No. 2001-133794
專利文獻2：國際公開第02/092718號 Patent Literature 2: International Publication No. 02/092718
本發明之目的在於提供一種對長波長之光的硬化性優異，且可抑制異物產生之液晶顯示元件用密封劑。又，本發明之目的在於提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 An object of the present invention is to provide a sealant for a liquid crystal display element which is excellent in curability of long-wavelength light and can suppress generation of foreign substances. In addition, an object of the present invention is to provide an upper and lower conduction material and a liquid crystal display element using the sealant for a liquid crystal display element.
本發明係一種液晶顯示元件用密封劑，其含有硬化性樹脂、光聚合起始劑及順丁烯二醯亞胺化合物，上述光聚合起始劑於波長430nm之消光 係數為0.8×102mL/g‧cm以上。 The present invention is a sealant for liquid crystal display elements, which contains a curable resin, a photopolymerization initiator and a maleimide compound, and the extinction coefficient of the photopolymerization initiator at a wavelength of 430 nm is 0.8 × 10 2 mL / g‧cm or more.
以下，詳述本發明。 Hereinafter, the present invention will be described in detail.
本發明人等驚奇地發現，藉由在密封劑中摻合順丁烯二醯亞胺化合物，可獲得即便使用對長波長之光的反應性優異之光聚合起始劑，亦可抑制因光硬化步驟前密封劑局部發生硬化所引起之異物之產生的液晶顯示元件用密封劑，從而完成了本發明。 The present inventors have surprisingly found that by blending a butadiene diimide compound in a sealant, it is possible to obtain a photopolymerization initiator excellent in reactivity with long-wavelength light, and it is also possible to suppress light emission. Before the hardening step, the sealant for the liquid crystal display element was partially generated by hardening of the sealant, and the present invention was completed.
本發明之液晶顯示元件用密封劑含有光聚合起始劑。 The sealing agent for liquid crystal display elements of this invention contains a photopolymerization initiator.
上述光聚合起始劑於波長430nm之消光係數為0.8×102mL/g‧cm以上。以下，亦將波長430nm之消光係數為0.8×102mL/g‧cm以上之光聚合起始劑稱為「本發明之光聚合起始劑」。 The extinction coefficient of the photopolymerization initiator at a wavelength of 430 nm is 0.8 × 10 2 mL / g‧cm or more. Hereinafter, the photopolymerization initiator with an extinction coefficient of 0.8 × 10 2 mL / g‧cm or more at a wavelength of 430 nm is also referred to as “photopolymerization initiator of the present invention”.
藉由本發明之光聚合起始劑於波長430nm之消光係數為0.8×102mL/g‧cm以上，本發明之液晶顯示元件用密封劑成為對長波長之光的硬化性優異者。本發明之光聚合起始劑於波長430nm之消光係數之較佳下限為1.0×102mL/g‧cm。 When the extinction coefficient of the photopolymerization initiator of the present invention at a wavelength of 430 nm is 0.8 × 10 2 mL / g‧cm or more, the sealant for a liquid crystal display element of the present invention has excellent curability for long-wavelength light. The preferred lower limit of the extinction coefficient of the photopolymerization initiator of the present invention at a wavelength of 430 nm is 1.0 × 10 2 mL / g‧cm.
又，本發明之光聚合起始劑於波長430nm之消光係數之較佳上限為1.0×104mL/g‧cm。 In addition, the preferred upper limit of the extinction coefficient of the photopolymerization initiator of the present invention at a wavelength of 430 nm is 1.0 × 10 4 mL / g‧cm.
再者，上述消光係數可以濃度成為0.1mg/mL之方式將測定對象之化合物溶解於溶劑後，使用分光光度計進行測定。 In addition, the above-mentioned extinction coefficient can be measured using a spectrophotometer after the compound to be measured is dissolved in a solvent so that the concentration becomes 0.1 mg / mL.
上述溶劑若為可溶解測定對象之化合物，且不存在測定之吸收波長下之吸光者則並無特別限定，例如可列舉：乙腈、甲醇等。 The solvent is not particularly limited if it is a compound that can dissolve the measurement object and there is no light absorption at the absorption wavelength of the measurement, and examples include acetonitrile and methanol.
就對長波長之光的反應性優異之方面而言，本發明之光聚合起始劑較佳為具有下述式(1)表示之結構的化合物，更佳為1分子中具有1個該式(1)表示之結構的化合物，進而較佳為下述式(2-1)表示之化合物及/或下述式(2-2)表示之化合物。 In terms of excellent reactivity with long-wavelength light, the photopolymerization initiator of the present invention is preferably a compound having a structure represented by the following formula (1), and more preferably has 1 formula in 1 molecule The compound represented by (1) is more preferably a compound represented by the following formula (2-1) and / or a compound represented by the following formula (2-2).
式(1)中，*為鍵結位置。 In formula (1), * is the bonding position.
式(2-1)、(2-2)中，R係源自單官能環氧化合物之結構。式(2-1)中，m為1~5之整數。 In formulas (2-1) and (2-2), R is derived from the structure of a monofunctional epoxy compound. In formula (2-1), m is an integer of 1 to 5.
作為製造上述(2-1)表示之化合物之方法，例如可列舉於鹼性觸媒之存在下，一面於80℃以上且130℃以下之條件下將2-(羧基甲氧基)-9H-硫-9-酮與單官能環氧化合物攪拌6~72小時一面進行反應之方法等。 As a method for producing the compound represented by the above (2-1), for example, in the presence of an alkaline catalyst, 2- (carboxymethoxy) -9H- sulfur -9-keto and monofunctional epoxy compound are stirred for 6 ~ 72 hours while reacting.
又，作為製造上述(2-2)表示之化合物之方法，例如可列舉於鹼性觸媒之存在下，一面於80℃以上且130℃以下之條件下將2-羥基-9H-硫-9-酮與單官能環氧化合物攪拌6~72小時一面進行反應之方法等。 In addition, as a method for producing the compound represented by (2-2) above, for example, in the presence of an alkaline catalyst, 2-hydroxy-9H-sulfur can be added under the conditions of 80 ° C or more and 130 ° C or less -9-keto and monofunctional epoxy compound are stirred for 6 ~ 72 hours while reacting.
以下，2-(羧基甲氧基)-9H-硫-9-酮及2-羥基-9H-硫 -9-酮亦稱為「原料9-氧硫衍生物」。 Below, 2- (carboxymethoxy) -9H-sulfur -9-keto and 2-hydroxy-9H-sulfur -9-ketone is also known as "raw material 9-oxo derivative".
上述單官能環氧化合物較佳為包含具有至少1個以上之碳數1以上之取代基之芳香族環、或具有至少1個以上之碳數1以上之取代基之脂肪族環。 The monofunctional epoxy compound preferably includes an aromatic ring having at least one or more carbon number 1 or more substituents, or an aliphatic ring having at least one or more carbon number one or more substituents.
作為上述芳香族環或上述脂肪族環，例如可列舉：苯環、萘環、蒽環、環丁烷環、環戊烷環、環己烷環、環辛烷環、降莰烯環、三環癸烷環等芳香族環或脂肪族環中之至少1個以上之氫原子被取代為碳數1以上之取代基者。 Examples of the aromatic ring or the aliphatic ring include a benzene ring, a naphthalene ring, an anthracene ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cyclooctane ring, a norbornene ring, and a tricyclic ring. At least one hydrogen atom in an aromatic ring or an aliphatic ring such as a cyclodecane ring is substituted with a substituent having a carbon number of 1 or more.
上述碳數1以上之取代基可為直鏈狀，亦可為支鏈狀。於上述碳數1以上之取代基為直鏈狀之情形時，較佳為碳數6以上，更佳為碳數10以上。於上述碳數1以上之取代基為支鏈狀之情形時，較佳為碳數4以上。又，上述芳香族環或上述脂肪族環所具有之碳數1以上之取代基之碳數較佳為上述單官能環氧化合物之分子量成為下述300以下的數。 The above-mentioned substituents with a carbon number of 1 or more may be linear or branched. When the above-mentioned carbon number 1 or more substituents are linear, it is preferably carbon number 6 or more, and more preferably carbon number 10 or more. In the case where the above-mentioned carbon number 1 or more substituent is branched, it is preferably carbon number 4 or more. In addition, the carbon number of the substituent having 1 or more carbon atoms of the aromatic ring or the aliphatic ring is preferably such that the molecular weight of the monofunctional epoxy compound becomes the following number of 300 or less.
作為上述芳香族環或上述脂肪族環所具有之碳數1以上之取代基，較佳為烷基。 The substituent having 1 or more carbon atoms in the aromatic ring or the aliphatic ring is preferably an alkyl group.
作為上述單官能環氧化合物，例如可列舉：烷基苯基環氧丙醚、具有環氧丙基之甲苯磺酸酯、2-環氧-4-乙烯基環己烷、甲基丙烯酸3,4-環氧環己基甲酯等。 Examples of the monofunctional epoxy compound include alkylphenyl glycidyl ether, tosylate having glycidyl group, 2-epoxy-4-vinylcyclohexane, and methacrylic acid 3. 4-Epoxycyclohexyl methyl ester, etc.
作為上述烷基苯基環氧丙醚，例如可列舉：鄰甲基苯基環氧丙醚、間甲基苯基環氧丙醚、對甲基苯基環氧丙醚、對三級丁基苯基環氧丙醚等。 Examples of the alkylphenyl glycidyl ether include o-methylphenyl glycidyl ether, m-methylphenyl glycidyl ether, p-methylphenyl glycidyl ether, and p-tertiary butyl group. Phenyl glycidyl ether etc.
作為上述單官能環氧化合物中之市售者，例如可列舉：長瀨化成公司製造之單官能環氧化合物、ADEKA公司製造之單官能環氧化合物、三菱化學公司製造之單官能環氧化合物、東京化成工業公司製造之單官能環氧化合物、大賽璐公司製造之單官能環氧化合物等。 Examples of the commercially available monofunctional epoxy compounds include monofunctional epoxy compounds manufactured by Nagase Chemical Co., Ltd., monofunctional epoxy compounds manufactured by ADEKA, and monofunctional epoxy compounds manufactured by Mitsubishi Chemical Corporation. Monofunctional epoxy compound manufactured by Tokyo Chemical Industry Co., Ltd., monofunctional epoxy compound manufactured by Daicel Corporation, etc.
作為上述長瀨化成公司製造之單官能環氧化合物，例如可列舉Denacol EX -146等。 Examples of the monofunctional epoxy compound manufactured by Nagase Chemicals Co., Ltd. include Denacol EX-146.
作為上述ADEKA公司製造之單官能環氧化合物，例如可列舉：ED-509S、ED-509E、ED-529等。 Examples of the monofunctional epoxy compound manufactured by ADEKA Corporation include ED-509S, ED-509E, and ED-529.
作為上述三菱化學公司製造之單官能環氧化合物，例如可列舉YED-122等。 Examples of the monofunctional epoxy compound manufactured by Mitsubishi Chemical Corporation include YED-122.
作為上述東京化成工業公司製造之單官能環氧化合物，例如可列舉：環氧丙基2-甲氧基苯基醚、1-甲基-1,2-環氧環己烷等。 Examples of the monofunctional epoxy compound manufactured by Tokyo Chemical Industry Co., Ltd. include epoxypropyl 2-methoxyphenyl ether and 1-methyl-1,2-epoxycyclohexane.
作為上述大賽璐公司製造之單官能環氧化合物，例如可列舉：Celloxide 2000、Cyclomer M100等。 Examples of the monofunctional epoxy compound manufactured by Daicel Corporation include Celloxide 2000 and Cyclomer M100.
就本發明之光聚合起始劑與硬化性樹脂之相溶性之觀點而言，上述單官能環氧化合物之分子量較佳為300以下。 From the viewpoint of the compatibility between the photopolymerization initiator of the present invention and the curable resin, the molecular weight of the monofunctional epoxy compound is preferably 300 or less.
作為使上述原料9-氧硫衍生物與上述單官能環氧化合物進行反應時之使用比率，較佳為以莫耳比計，原料9-氧硫衍生物：單官能環氧化合物=1：1~10：1。藉由上述原料9-氧硫衍生物與上述單官能環氧化合物之使用比率為該範圍，可以高產率製造上述式(2-1)表示之化合物或上述式(2-2)表示之化合物。 As the above raw material 9-oxysulfur The use ratio of the derivative when reacting with the above-mentioned monofunctional epoxy compound is preferably based on the molar ratio, and the raw material 9-oxo Derivatives: monofunctional epoxy compound = 1: 1 ~ 10: 1. With the above raw material 9-oxysulfur The use ratio of the derivative to the above-mentioned monofunctional epoxy compound is within this range, and the compound represented by the above formula (2-1) or the compound represented by the above formula (2-2) can be produced with high yield.
作為使上述原料9-氧硫衍生物與上述單官能環氧化合物進行反應時使用之鹼性觸媒，較佳為三價有機磷酸化合物及/或胺化合物。 As the above raw material 9-oxysulfur The basic catalyst used when the derivative reacts with the above-mentioned monofunctional epoxy compound is preferably a trivalent organic phosphoric acid compound and / or an amine compound.
作為上述鹼性觸媒，具體而言，例如可列舉：三苯基膦、三乙胺、三丙胺、四甲基乙二胺、二甲基月桂胺、三乙基苄基氯化銨、三甲基鯨蠟基溴化銨、四丁基溴化銨、三甲基丁基溴化鏻、四丁基溴化鏻等。其中，較佳為三苯基膦。 Specific examples of the alkaline catalyst include triphenylphosphine, triethylamine, tripropylamine, tetramethylethylenediamine, dimethyllaurylamine, triethylbenzyl ammonium chloride, and Methyl cetyl ammonium bromide, tetrabutyl ammonium bromide, trimethylbutyl phosphonium bromide, tetrabutyl phosphonium bromide, etc. Among them, triphenylphosphine is preferred.
又，上述鹼性觸媒亦可由聚合物載持，以聚合物載持鹼性觸媒之形式使用。 In addition, the above-mentioned alkaline catalyst may be supported by a polymer, and may be used in the form of a polymer-supported alkaline catalyst.
作為本發明之光聚合起始劑中之具有上述式(1)表示之結構的化合物以外者，例如可列舉雙(2,4,6-三甲基苯甲醯基)苯基氧化膦等。 Examples of the photopolymerization initiator of the present invention other than the compound having the structure represented by the above formula (1) include bis (2,4,6-trimethylbenzyl) phenylphosphine oxide and the like.
本發明之光聚合起始劑之含量相對於硬化性樹脂與順丁烯二醯亞胺化合物之合計100重量份，較佳下限為0.1重量份，較佳上限為20重量份。藉由使本發明之光聚合起始劑之含量為0.1重量份以上，所獲得之液晶顯示元件用密封劑成為對長波長之光的硬化性更優異者。藉由使本發明之光聚合起始劑之含量為20重量份以下，所獲得之液晶顯示元件用密封劑成為抑制異物產生之效果更優異者。本發明之光聚合起始劑之含量之更佳下限為0.2重量份，進而較佳下限為0.3重量份，進而更佳下限為0.5重量份，尤佳下限為1重量份。本發明之光聚合起始劑之含量之更佳上限為10重量份，進而較佳上限為5重量份。 The content of the photopolymerization initiator of the present invention is preferably 100 parts by weight relative to the total of the curable resin and the maleimide compound, and the lower limit is preferably 0.1 part by weight, and the upper limit is preferably 20 parts by weight. When the content of the photopolymerization initiator of the present invention is 0.1 part by weight or more, the obtained sealant for liquid crystal display elements becomes more excellent in curability of long-wavelength light. By setting the content of the photopolymerization initiator of the present invention to 20 parts by weight or less, the obtained sealant for liquid crystal display elements becomes more excellent in suppressing the generation of foreign substances. The lower limit of the content of the photopolymerization initiator of the present invention is more preferably 0.2 parts by weight, further preferably the lower limit is 0.3 parts by weight, further preferably the lower limit is 0.5 parts by weight, and particularly preferably the lower limit is 1 part by weight. The more preferable upper limit of the content of the photopolymerization initiator of the present invention is 10 parts by weight, and the more preferable upper limit is 5 parts by weight.
本發明之液晶顯示元件用密封劑亦可於不阻礙本發明之目的之範圍內含有熱聚合起始劑。 The sealant for liquid crystal display elements of the present invention may contain a thermal polymerization initiator within a range that does not hinder the purpose of the present invention.
作為上述熱聚合起始劑，例如可列舉由偶氮化合物、有機過氧化物等所構成者。其中，較佳為由高分子偶氮化合物所構成之高分子偶氮起始劑。 Examples of the thermal polymerization initiator include those composed of an azo compound, an organic peroxide, and the like. Among them, a polymer azo initiator composed of a polymer azo compound is preferred.
再者，於本說明書中，上述「高分子偶氮化合物」意指具有偶氮基且藉由熱而生成可使(甲基)丙烯醯氧基硬化之自由基的數量平均分子量為300以上之化合物。 In addition, in this specification, the above-mentioned "polymer azo compound" means a radical having an azo group and generated by heat that can harden the (meth) acryloyloxy group with a number average molecular weight of 300 or more Compound.
上述高分子偶氮化合物之數量平均分子量之較佳下限為1000，較佳上限為30萬。藉由使上述高分子偶氮化合物之數量平均分子量為該範圍，可抑制液晶污染，並且與硬化性樹脂容易地混合。上述高分子偶氮化合物之數量平均分子量之更佳下限為5000，更佳上限為10萬，進而較佳下限為1萬，進而較佳上限為9萬。 The preferable lower limit of the number average molecular weight of the above polymer azo compound is 1,000, and the preferable upper limit is 300,000. By setting the number average molecular weight of the above-mentioned polymer azo compound within this range, liquid crystal contamination can be suppressed and it can be easily mixed with the curable resin. The more preferable lower limit of the number average molecular weight of the polymer azo compound is 5000, the more preferable upper limit is 100,000, the more preferable lower limit is 10,000, and the more preferable upper limit is 90,000.
再者，於本說明書中，上述數量平均分子量係利用凝膠滲透層析法(GPC)，使用四氫呋喃作為溶劑進行測定，藉由聚苯乙烯換算所求出之值。 作為利用GPC測定基於聚苯乙烯換算之數量平均分子量時之管柱，例如可列舉Shodex LF-804(昭和電工公司製造)等。 In this specification, the number average molecular weight is measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent, and the value is calculated in terms of polystyrene. Examples of the column when measuring the number average molecular weight based on polystyrene conversion by GPC include Shodex LF-804 (manufactured by Showa Denko).
作為上述高分子偶氮化合物，例如可列舉具有聚環氧烷(polyalkylene oxide)或聚二甲基矽氧烷等單元經由偶氮基鍵結多個而成之結構者。 Examples of the polymer azo compound include those having a structure in which a plurality of units such as polyalkylene oxide or polydimethylsiloxane are bonded via an azo group.
作為上述具有聚環氧烷等單元經由偶氮基鍵結多個而成之結構的高分子偶氮化合物，較佳為具有聚環氧乙烷結構者。 The polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide is bonded via an azo group is preferably a polyethylene oxide structure.
作為上述高分子偶氮化合物，具體而言，例如可列舉：4,4'-偶氮雙(4-氰基戊酸)與聚伸烷基二醇之縮聚物、或4,4'-偶氮雙(4-氰基戊酸)與具有末端胺基之聚二甲基矽氧烷之縮聚物等。 Specific examples of the polymer azo compound include, for example, a polycondensate of 4,4'-azobis (4-cyanovaleric acid) and polyalkylene glycol, or 4,4'-a Polycondensates of bis (4-cyanovaleric acid) and polydimethylsiloxane with terminal amine groups.
作為上述高分子偶氮化合物中之市售者，例如可列舉：VPE-0201、VPE-0401、VPE-0601、VPS-0501、VPS-1001(均為富士軟片和光純藥公司製造)等。 Examples of the commercially available polymer azo compounds include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by Fuji Film and Koko Pure Chemical Industries).
又，作為不為高分子之偶氮化合物，例如可列舉：V-65、V-501(均為富士軟片和光純藥公司製造)等。 In addition, examples of the azo compound that is not a polymer include V-65 and V-501 (both manufactured by Fuji Film and Koko Pure Chemical Industries, Ltd.).
作為上述有機過氧化物，例如可列舉：過氧化酮、過氧化縮酮、過氧化氫、二烷基過氧化物(dialkyl peroxide)、過氧化酯、二醯基過氧化物(diacyl peroxide)、過氧化二碳酸酯等。 Examples of the organic peroxides include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, Peroxydicarbonate, etc.
上述熱聚合起始劑之含量相對於硬化性樹脂與順丁烯二醯亞胺化合物之合計100重量份，較佳下限為0.05重量份，較佳上限為10重量份。藉由使上述熱聚合起始劑之含量為0.05重量份以上，本發明之液晶顯示元件用密封劑成為熱硬化性更優異者。藉由使上述熱聚合起始劑之含量為10重量份以下，本發明之液晶顯示元件用密封劑成為低液晶污染性或保存穩定性更優異者。上述熱聚合起始劑之含量之更佳下限為0.1重量份，更佳上限為5重量份。 The content of the thermal polymerization initiator is preferably 100 parts by weight relative to the total of the curable resin and the maleimide compound, and the lower limit is preferably 0.05 parts by weight, and the upper limit is preferably 10 parts by weight. By setting the content of the thermal polymerization initiator to 0.05 parts by weight or more, the sealing agent for liquid crystal display elements of the present invention becomes more excellent in thermosetting property. By setting the content of the thermal polymerization initiator to 10 parts by weight or less, the sealing agent for liquid crystal display elements of the present invention has low liquid crystal contamination or more excellent storage stability. The more preferable lower limit of the content of the thermal polymerization initiator is 0.1 part by weight, and the more preferable upper limit is 5 parts by weight.
本發明之液晶顯示元件用密封劑含有硬化性樹脂。 The sealing compound for liquid crystal display elements of this invention contains curable resin.
如下所述，於本發明中，順丁烯二醯亞胺化合物不包含於上述硬化性樹脂中。 As described below, in the present invention, the maleimide compound is not included in the curable resin.
上述硬化性樹脂較佳含有(甲基)丙烯酸化合物。 The curable resin preferably contains a (meth) acrylic compound.
作為上述(甲基)丙烯酸化合物，例如可列舉：(甲基)丙烯酸酯化合物、環氧(甲基)丙烯酸酯、(甲基)丙烯酸胺基甲酸酯等。其中，較佳為環氧(甲基)丙烯酸酯。又，就反應性較高之方面而言，上述(甲基)丙烯酸化合物較佳為分子中具有2個以上之(甲基)丙烯醯基者。 Examples of the (meth) acrylic compound include (meth) acrylate compounds, epoxy (meth) acrylates, (meth) acrylate carbamates, and the like. Among them, epoxy (meth) acrylate is preferred. In addition, in terms of high reactivity, the (meth) acrylic compound preferably has two or more (meth) acryl acetyl groups in the molecule.
再者，於本說明書中，上述「(甲基)丙烯酸」意指丙烯酸或甲基丙烯酸，上述「(甲基)丙烯酸化合物」意指具有(甲基)丙烯醯基之化合物，上述「(甲基)丙烯醯基」意指丙烯醯基或甲基丙烯醯基。又，上述「(甲基)丙烯酸酯」意指丙烯酸酯或甲基丙烯酸酯。進而，上述「環氧(甲基)丙烯酸酯」表示使環氧化合物中之所有環氧基與(甲基)丙烯酸進行反應而成之化合物。 Furthermore, in this specification, the above "(meth) acrylic acid" means acrylic acid or methacrylic acid, and the above "(meth) acrylic compound" means a compound having a (meth) acryloyl group, the above "(meth "Acyl) acryl" means acryl or methacryl. In addition, the "(meth) acrylate" means acrylate or methacrylate. Furthermore, the above-mentioned "epoxy (meth) acrylate" means a compound obtained by reacting all epoxy groups in the epoxy compound with (meth) acrylic acid.
作為上述(甲基)丙烯酸酯化合物中之單官能者，例如可列舉：(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸三級丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸異癸酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸異肉豆蔻酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸2-丁氧基乙酯、(甲基)丙烯酸2-苯氧基乙酯、甲氧基乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯、苯氧基二乙二醇(甲基)丙烯酸酯、苯氧基聚乙二醇(甲基)丙烯酸酯、 (甲基)丙烯酸四氫糠酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸2,2,2-三氟乙酯、(甲基)丙烯酸2,2,3,3-四氟丙酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、醯亞胺(甲基)丙烯酸酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸二乙基胺基乙酯、丁二酸2-(甲基)丙烯醯氧基乙酯、六氫鄰苯二甲酸2-(甲基)丙烯醯氧基乙酯、鄰苯二甲酸2-(甲基)丙烯醯氧基乙酯2-羥基丙酯、磷酸2-(甲基)丙烯醯氧基乙酯、(甲基)丙烯酸環氧丙酯等。 Examples of the monofunctional in the (meth) acrylate compound include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, and n-butyl (meth) acrylate. Ester, isobutyl (meth) acrylate, tertiary 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, (meth) 2-hydroxyethyl 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-ethoxy (meth) acrylate Ethyl acetate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxypolyethylene glycol ( Meth) acrylate, phenoxy diethylene glycol (Meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, ethyl carbitol (meth) acrylate, (meth) acrylic acid 2, 2,2-Trifluoroethyl ester, (meth) acrylic acid 2,2,3,3-tetrafluoropropyl ester, (meth) acrylic acid 1H, 1H, 5H-octafluoropentyl ester, amide imine (methyl) Acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinate, hexahydrophthalic acid 2- (meth) acryloxyethyl formate, 2- (meth) acryloxyethyl 2-hydroxypropyl phthalate, 2- (meth) acryloxyethyl phosphate, (Meth) glycidyl acrylate, etc.
又，作為上述(甲基)丙烯酸酯化合物中之2官能者，例如可列舉：1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、2-正丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、環氧乙烷加成雙酚A二(甲基)丙烯酸酯、環氧丙烷加成雙酚A二(甲基)丙烯酸酯、環氧乙烷加成雙酚F二(甲基)丙烯酸酯、二羥甲基二環戊二烯二(甲基)丙烯酸酯、環氧乙烷改質異三聚氰酸二(甲基)丙烯酸酯、(甲基)丙烯酸2-羥基-3-(甲基)丙烯醯氧基丙酯、碳酸酯二醇二(甲基)丙烯酸酯、聚醚二醇二(甲基)丙烯酸酯、聚酯二醇二(甲基)丙烯酸酯、聚己內酯二醇二(甲基)丙烯酸酯、聚丁二烯二醇二(甲基)丙烯酸酯等。 In addition, examples of the two functions of the (meth) acrylate compound include 1,3-butanediol di (meth) acrylate and 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, neopentyl glycol Alcohol 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 isocyanurate di (meth) acrylate, (meth) acrylic acid 2-Hydroxy-3- (meth) acrylic acid propyl propyl ester, carbonate diol bis (meth) propylene Ester, polyetherdiol di (meth) acrylate, polyesterdiol di (meth) acrylate, polycaprolactonediol di (meth) acrylate, polybutadienediol di (meth) acrylate ) Acrylic esters, etc.
又，作為上述(甲基)丙烯酸酯化合物中之3官能以上者，例如可列舉：三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、環氧丙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、己內酯改質三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成異三聚氰酸三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、環氧丙烷加成甘油三(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯 酸酯、磷酸三[(甲基)丙烯醯氧基乙基]酯、二(三羥甲基丙烷)四(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯等。 In addition, examples of the trifunctional or higher among the (meth) acrylate compounds include trimethylolpropane tri (meth) acrylate and ethylene oxide addition trimethylolpropane tri (methyl ) Acrylate, propylene oxide addition trimethylolpropane tri (meth) acrylate, caprolactone modified trimethylolpropane tri (meth) acrylate, ethylene oxide addition isocyanurate Acid tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide addition glycerol tri (meth) acrylate, neopentaerythritol tri (meth) acrylate, triphosphate ((methyl ) Propylene oxyethyl] ester, di (trimethylolpropane) tetra (meth) acrylate, neopentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate , Dipentaerythritol hexa (meth) acrylate, etc.
作為上述環氧(甲基)丙烯酸酯，例如可列舉藉由按照常規方法於鹼性觸媒之存在下使環氧化合物與(甲基)丙烯酸進行反應所獲得者等。 Examples of the epoxy (meth) acrylates include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of an alkaline catalyst according to a conventional method.
作為成為用以合成上述環氧(甲基)丙烯酸酯之原料之環氧化合物，例如可列舉：雙酚A型環氧化合物、雙酚F型環氧化合物、雙酚S型環氧化合物、2,2'-二烯丙基雙酚A型環氧化合物、氫化雙酚型環氧化合物、環氧丙烷加成雙酚A型環氧化合物、間苯二酚型環氧化合物、聯苯型環氧化合物、硫醚(sulfide)型環氧化合物、二苯醚型環氧化合物、二環戊二烯型環氧化合物、萘型環氧化合物、苯酚酚醛清漆型環氧化合物、鄰甲酚酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物、聯苯酚醛清漆型環氧化合物、萘酚酚醛清漆型環氧化合物、環氧丙胺型環氧化合物、烷基多元醇型環氧化合物、橡膠改質型環氧化合物、環氧丙酯化合物等。 Examples of the epoxy compound used as a raw material for synthesizing the epoxy (meth) acrylate include bisphenol A-type epoxy compounds, bisphenol F-type epoxy compounds, and bisphenol S-type epoxy compounds. 2 , 2'-diallyl bisphenol A epoxy compound, hydrogenated bisphenol epoxy compound, propylene oxide addition bisphenol A epoxy compound, resorcinol epoxy compound, biphenyl ring Oxygen compounds, sulfide epoxy compounds, diphenyl ether epoxy compounds, dicyclopentadiene epoxy compounds, naphthalene epoxy compounds, phenol novolac epoxy compounds, o-cresol novolac Type epoxy compound, dicyclopentadiene novolac type epoxy compound, biphenol novolac type epoxy compound, naphthol novolac type epoxy compound, propylene oxide type epoxy compound, alkyl polyol type epoxy compound Compounds, rubber-modified epoxy compounds, glycidyl ester compounds, etc.
作為上述雙酚A型環氧化合物中之市售者，例如可列舉：jER 828EL、jER 1004(均為三菱化學公司製造)；Epiclon 850CRP(DIC公司製造)等。 Examples of commercially available bisphenol A-type epoxy compounds include jER 828EL and jER 1004 (all manufactured by Mitsubishi Chemical Corporation); Epiclon 850CRP (manufactured by DIC Corporation) and the like.
作為上述雙酚F型環氧化合物中之市售者，例如可列舉：jER 806、jER 4004(均為三菱化學公司製造)等。 Examples of commercially available bisphenol F-type epoxy compounds include jER 806 and jER 4004 (all manufactured by Mitsubishi Chemical Corporation).
作為上述雙酚S型環氧化合物中之市售者，例如可列舉Epiclon EXA1514(DIC公司製造)等。 Examples of the commercially available bisphenol S-type epoxy compound include Epiclon EXA1514 (manufactured by DIC).
作為上述2,2'-二烯丙基雙酚A型環氧化合物中之市售者，例如可列舉RE-810NM(日本化藥公司製造)等。 As a commercial item among the said 2,2'- diallyl bisphenol A type epoxy compounds, RE-810NM (made by Nippon Kayaku Co., Ltd.) etc. are mentioned, for example.
作為上述氫化雙酚型環氧化合物中之市售者，例如可列舉Epiclon EXA7015(DIC公司製造)等。 Examples of the commercially available hydrogenated bisphenol-type epoxy compounds include Epiclon EXA7015 (manufactured by DIC).
作為上述環氧丙烷加成雙酚A型環氧化合物中之市售者，例如可列舉EP-4000S(ADEKA公司製造)等。 Examples of commercially available propylene oxide-added bisphenol A-type epoxy compounds include EP-4000S (manufactured by ADEKA).
作為上述間苯二酚型環氧化合物中之市售者，例如可列舉EX-201(長瀨化成公司製造)等。 As a marketer among the resorcinol type epoxy compounds, for example, EX-201 (manufactured by Nagase Kasei Corporation) and the like can be cited.
作為上述聯苯型環氧化合物中之市售者，例如可列舉jER YX-4000H(三菱化學公司製造)等。 Examples of the commercially available ones of the biphenyl-type epoxy compounds include jER YX-4000H (manufactured by Mitsubishi Chemical Corporation) and the like.
作為上述硫醚型環氧化合物中之市售者，例如可列舉YSLV-50TE(新日鐵住金化學公司製造)等。 Examples of commercially available thioether epoxy compounds include YSLV-50TE (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.) and the like.
作為上述二苯醚型環氧化合物中之市售者，例如可列舉YSLV-80DE(新日鐵住金化學公司製造)等。 Examples of the commercially available diphenyl ether-type epoxy compounds include YSLV-80DE (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.) and the like.
作為上述二環戊二烯型環氧化合物中之市售者，例如可列舉EP-4088S(ADEKA公司製造)等。 Examples of the commercially available dicyclopentadiene-type epoxy compounds include EP-4088S (manufactured by ADEKA).
作為上述萘型環氧化合物中之市售者，例如可列舉：Epiclon HP4032、Epiclon EXA-4700(均為DIC公司製造)等。 Examples of commercially available naphthalene-type epoxy compounds include Epiclon HP4032 and Epiclon EXA-4700 (all manufactured by DIC Corporation).
作為上述苯酚酚醛清漆型環氧化合物中之市售者，例如可列舉Epiclon N-770(DIC公司製造)等。 Examples of the commercially available phenol novolac-type epoxy compounds include Epiclon N-770 (manufactured by DIC Corporation) and the like.
作為上述鄰甲酚酚醛清漆型環氧化合物中之市售者，例如可列舉Epiclon N-670-EXP-S(DIC公司製造)等。 As a commercially available one among the above-mentioned o-cresol novolac-type epoxy compounds, for example, Epiclon N-670-EXP-S (manufactured by DIC Corporation) and the like can be cited.
作為上述二環戊二烯酚醛清漆型環氧化合物中之市售者，例如可列舉Epiclon HP7200(DIC公司製造)等。 Examples of the commercially available dicyclopentadiene novolac-type epoxy compounds include Epiclon HP7200 (manufactured by DIC).
作為上述聯苯酚醛清漆型環氧化合物中之市售者，例如可列舉NC-3000P(日本化藥公司製造)等。 Examples of the commercially available ones of the biphenol novolac-type epoxy compounds include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.) and the like.
作為上述萘酚酚醛清漆型環氧化合物中之市售者，例如可列舉ESN-165S (新日鐵住金化學公司製造)等。 Examples of the commercially available naphthol novolak-type epoxy compounds include ESN-165S (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.).
作為上述環氧丙胺型環氧化合物中之市售者，例如可列舉：jER 630(三菱化學公司製造)、Epiclon 430(DIC公司製造)、TETRAD-X(三菱瓦斯化學公司製造)等。 Examples of commercially available glycidylamine-type epoxy compounds include jER 630 (manufactured by Mitsubishi Chemical Corporation), Epiclon 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Corporation), and the like.
作為上述烷基多元醇型環氧化合物中之市售者，例如可列舉：ZX-1542(新日鐵住金化學公司製造)、Epiclon 726(DIC公司製造)、Epolight 80MFA(共榮社化學公司製造)、Denacol EX-611(長瀨化成公司製造)等。 Examples of the commercially available among the alkyl polyol-type epoxy compounds include ZX-1542 (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.), Epiclon 726 (manufactured by DIC), and Epolight 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.) ), Denacol EX-611 (made by Nagase Chemical Co., Ltd.), etc.
作為上述橡膠改質型環氧化合物中之市售者，例如可列舉：YR-450、YR-207(均為新日鐵住金化學公司製造)；Epolead PB(大賽璐公司製造)等。 Examples of commercially available rubber-modified epoxy compounds include YR-450 and YR-207 (all manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.); Epolead PB (manufactured by Daicel Corporation) and the like.
作為上述環氧丙酯化合物中之市售者，例如可列舉Denacol EX-147(長瀨化成公司製造)等。 Examples of the commercially available glycidyl compounds include Denacol EX-147 (manufactured by Nagase Chemical Co., Ltd.) and the like.
作為上述環氧化合物中之其他市售者，例如可列舉：YDC-1312、YSLV-80XY、YSLV-90CR(均為新日鐵住金化學公司製造)；XAC4151(旭化成公司製造)；jER 1031、jER 1032(均為三菱化學公司製造)；EXA-7120(DIC公司製造)；TEPIC(日產化學公司製造)等。 As other commercially available ones among the above epoxy compounds, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.); XAC4151 (manufactured by Asahi Kasei Corporation); jER 1031, jER 1032 (all made by Mitsubishi Chemical Corporation); EXA-7120 (made by DIC Corporation); TEPIC (made by Nissan Chemical Corporation), etc.
作為上述環氧(甲基)丙烯酸酯中之市售者，例如可列舉：大賽璐湛新公司製造之環氧(甲基)丙烯酸酯、新中村化學工業公司製造之環氧(甲基)丙烯酸酯、共榮社化學公司製造之環氧(甲基)丙烯酸酯、長瀨化成公司製造之環氧(甲基)丙烯酸酯等。 Examples of the commercially available epoxy (meth) acrylates include epoxy (meth) acrylate made by Daicel Zhanxin Co., Ltd., and epoxy (meth) acrylic made by Shin Nakamura Chemical Industry Co., Ltd. Ester, epoxy (meth) acrylate made by Kyoeisha Chemical Co., Ltd., epoxy (meth) acrylate made by Nagase Chemical Co., Ltd., etc.
作為上述大賽璐湛新公司製造之環氧(甲基)丙烯酸酯，例如可列舉：EBECRYL 860、EBECRYL 3200、EBECRYL 3201、EBECRYL 3412、EBECRYL 3600、EBECRYL 3700、EBECRYL 3701、EBECRYL 3702、EBECRYL 3703、EBECRYL 3800、EBECRYL 6040、EBECRYL RDX63182等。 Examples of the epoxy (meth) acrylate produced by the above-mentioned Daicel Zhanxin include: EBECRYL 860, EBECRYL 3200, EBECRYL 3201, EBECRYL 3412, EBECRYL 3600, EBECRYL 3700, EBECRYL 3701, EBECRYL 3702, EBECRYL 3703, EBECRYL 3800, EBECRYL 6040, EBECRYL RDX63182, etc.
作為上述新中村化學工業公司製造之環氧(甲基)丙烯酸酯，例如可列舉：EA-1010、EA-1020、EA-5323、EA-5520、EA-CHD、EMA-1020等。 Examples of the epoxy (meth) acrylates manufactured by Shin Nakamura Chemical Industry Co., Ltd. include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020, and the like.
作為上述共榮社化學公司製造之環氧(甲基)丙烯酸酯，例如可列舉：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 Ester 3000A、Epoxy Ester 200EA、Epoxy Ester 400EA等。 Examples of the epoxy (meth) acrylates manufactured by Kyoeisha Chemical Company 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 Ester 3000A, Epoxy Ester 200EA, Epoxy Ester 400EA, etc.
作為上述長瀨化成公司製造之環氧(甲基)丙烯酸酯，例如可列舉：Denacol Acrylate DA-141、Denacol Acrylate DA-314、Denacol Acrylate DA-911等。 Examples of the epoxy (meth) acrylate produced by the Nagase Chemical Company include Denacol Acrylate DA-141, Denacol Acrylate DA-314, Denacol Acrylate DA-911, and the like.
上述(甲基)丙烯酸胺基甲酸酯例如可藉由在觸媒量之錫系化合物存在下使具有羥基之(甲基)丙烯酸衍生物2當量與具有2個異氰酸基之異氰酸酯化合物1當量進行反應而獲得。 The (meth) acrylic acid carbamate can be obtained by, for example, using an equivalent of a (meth) acrylic acid derivative having a hydroxyl group in the presence of a catalyst amount of a tin compound and an isocyanate compound 1 having two isocyanate groups 1 Equivalent reaction to obtain.
作為上述異氰酸酯化合物，例如可列舉：異佛酮二異氰酸酯、2,4-甲伸苯基二異氰酸酯、2,6-甲伸苯基二異氰酸酯、六亞甲基二異氰酸酯、三甲基六亞甲基二異氰酸酯、二苯基甲烷-4,4'-二異氰酸酯(MDI)、氫化MDI、聚合MDI、1,5-萘二異氰酸酯、降莰烷二異氰酸酯、聯甲苯胺二異氰酸酯、伸茬基二異氰酸酯(XDI)、氫化XDI、離胺酸二異氰酸酯、三苯基甲烷三異氰酸酯、硫代磷酸三(異氰酸基苯基)酯、四甲基伸茬基二異氰酸酯、1,6,11-十一烷三異氰酸酯等。 Examples of the isocyanate compound include isophorone diisocyanate, 2,4-tolyl diisocyanate, 2,6-tolyl diisocyanate, hexamethylene diisocyanate, and trimethyl hexamethylene Diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, succinyl diisocyanate Isocyanate (XDI), hydrogenated XDI, urethane diisocyanate, triphenylmethane triisocyanate, thiophosphoric acid tri (isocyanatophenyl), tetramethyl stubble diisocyanate, 1,6,11- Undecane triisocyanate, etc.
又，作為上述異氰酸酯化合物，亦可使用藉由多元醇與過量之異氰酸酯化合物之反應所獲得之經鏈延長之異氰酸酯化合物。 In addition, as the above-mentioned isocyanate compound, a chain-extended isocyanate compound obtained by the reaction of a polyol and an excess of isocyanate compound can also be used.
作為上述多元醇，例如可列舉：乙二醇、丙二醇、甘油、山梨醇、三羥甲基丙烷、碳酸酯二醇、聚醚二醇、聚酯二醇、聚己內酯二醇等。 Examples of the above-mentioned polyols include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
作為上述具有羥基之(甲基)丙烯酸衍生物，例如可列舉：單(甲 基)丙烯酸羥基烷基酯、二元醇之單(甲基)丙烯酸酯、三元醇之單(甲基)丙烯酸酯或二(甲基)丙烯酸酯、環氧(甲基)丙烯酸酯等。 Examples of the (meth) acrylic acid derivatives having hydroxyl groups include hydroxyalkyl mono (meth) acrylates, mono (meth) acrylates of glycols, and mono (meth) acrylic acid of triols. Ester or di (meth) acrylate, epoxy (meth) acrylate, etc.
作為上述單(甲基)丙烯酸羥基烷基酯，例如可列舉：(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸4-羥基丁酯等。 Examples of the hydroxyalkyl mono (meth) acrylate include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-Hydroxybutyl (meth) acrylate and the like.
作為上述二元醇，例如可列舉：乙二醇、丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、聚乙二醇等。 Examples of the diols include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and polyethylene glycol.
作為上述三元醇，例如可列舉：三羥甲基乙烷、三羥甲基丙烷、甘油等。 Examples of the triols include trimethylolethane, trimethylolpropane, and glycerin.
作為上述環氧(甲基)丙烯酸酯，例如可列舉雙酚A型環氧丙烯酸酯等。 Examples of the epoxy (meth) acrylate include bisphenol A epoxy acrylate.
作為上述(甲基)丙烯酸胺基甲酸酯中之市售者，例如可列舉：東亞合成公司製造之(甲基)丙烯酸胺基甲酸酯、大賽璐湛新公司製造之(甲基)丙烯酸胺基甲酸酯、根上工業公司製造之(甲基)丙烯酸胺基甲酸酯、新中村化學工業公司製造之(甲基)丙烯酸胺基甲酸酯、共榮社化學公司製造之(甲基)丙烯酸胺基甲酸酯等。 Examples of the commercially available among the (meth) acrylic acid urethanes include (meth) acrylic acid urethanes manufactured by Toya Synthetic Corporation and (meth) acrylic acid manufactured by Daicel Zhanxin Carbamate, (meth) acrylic acid carbamate manufactured by Negami Industrial Co., Ltd., (meth) acrylic acid carbamate manufactured by Shin Nakamura Chemical Industry Co., Ltd. ) Acrylic urethane, etc.
作為上述東亞合成公司製造之(甲基)丙烯酸胺基甲酸酯，例如可列舉：M-1100、M-1200、M-1210、M-1600等。 Examples of the (meth) acrylic acid urethanes manufactured by the above-mentioned East Asia Synthesizer include M-1100, M-1200, M-1210, and M-1600.
作為上述大賽璐湛新公司製造之(甲基)丙烯酸胺基甲酸酯，例如可列舉：EBECRYL 210、EBECRYL 220、EBECRYL 230、EBECRYL 270、EBECRYL 1290、EBECRYL 2220、EBECRYL 4827、EBECRYL 4842、EBECRYL 4858、EBECRYL 5129、EBECRYL 6700、EBECRYL 8402、EBECRYL 8803、EBECRYL 8804、EBECRYL 8807、EBECRYL 9260等。 Examples of the (meth) acrylic urethanes manufactured by the above-mentioned Daicel Zhanxin Company include: EBECRYL 210, EBECRYL 220, EBECRYL 230, EBECRYL 270, EBECRYL 1290, EBECRYL 2220, EBECRYL 4827, EBECRYL 4842, EBECRYL 4858 , EBECRYL 5129, EBECRYL 6700, EBECRYL 8402, EBECRYL 8803, EBECRYL 8804, EBECRYL 8807, EBECRYL 9260, etc.
作為上述根上工業公司製造之(甲基)丙烯酸胺基甲酸酯，例如可列舉：Artresin UN-330、Artresin SH-500B、Artresin UN-1200TPK、Artresin UN-1255、Artresin UN-3320HB、Artresin UN-7100、Artresin UN-9000A、 Artresin UN-9000H等。 Examples of the (meth) acrylic acid carbamates produced by the above-mentioned Kinshang Industrial Company include Artresin UN-330, Artresin SH-500B, Artresin UN-1200TPK, Artresin UN-1255, Artresin UN-3320HB, Artresin UN- 7100, Artresin UN-9000A, Artresin UN-9000H, etc.
作為上述新中村化學工業公司製造之(甲基)丙烯酸胺基甲酸酯，例如可列舉：U-2HA、U-2PHA、U-3HA、U-4HA、U-6H、U-6HA、U-6LPA、U-10H、U-15HA、U-108、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、UA-W2A等。 Examples of the (meth) acrylic acid carbamates manufactured by Shin Nakamura Chemical Industry Co., Ltd. include U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6HA, and U- 6LPA, U-10H, U-15HA, U-108, 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, UA-W2A, etc.
作為上述共榮社化學公司製造之(甲基)丙烯酸胺基甲酸酯，例如可列舉：AH-600、AI-600、AT-600、UA-101I、UA-101T、UA-306H、UA-306I、UA-306T等。 Examples of the (meth) acrylic acid urethanes manufactured by the Kyoeisha Chemical Company include: AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA- 306I, UA-306T, etc.
上述硬化性樹脂較佳為以提昇所獲得之液晶顯示元件用密封劑之接著性為目的，進而含有環氧化合物。作為上述環氧化合物，例如可列舉：成為用以合成上述環氧(甲基)丙烯酸酯之原料之環氧化合物、或部分(甲基)丙烯酸改質環氧化合物等。 The curable resin preferably contains an epoxy compound for the purpose of improving the adhesiveness of the obtained sealing compound for liquid crystal display elements. Examples of the epoxy compound include an epoxy compound used as a raw material for synthesizing the epoxy (meth) acrylate, or a partially (meth) acrylic modified epoxy compound.
再者，於本說明書中，上述部分(甲基)丙烯酸改質環氧化合物意指1分子中分別具有1個以上之環氧基及(甲基)丙烯醯基之化合物，例如可藉由使1分子中具有2個以上環氧基之環氧化合物之一部分環氧基與(甲基)丙烯酸進行反應而獲得。 In addition, in this specification, the above-mentioned (meth) acrylic modified epoxy compound means a compound having one or more epoxy groups and (meth) acryloyl groups in one molecule, for example, by using It is obtained by reacting a part of epoxy groups with (meth) acrylic acid in an epoxy compound having two or more epoxy groups in one molecule.
於本發明之液晶顯示元件用密封劑含有上述環氧化合物之情形時，較佳使上述硬化性樹脂中之(甲基)丙烯醯基與環氧基之合計中之(甲基)丙烯醯基的比率成為30莫耳%以上且95莫耳%以下。藉由使上述(甲基)丙烯醯基之比率為30莫耳%以上，所獲得之液晶顯示元件用密封劑成為低液晶污染性更優異者。藉由使上述(甲基)丙烯醯基之比率為95莫耳%以下，所獲得之液晶顯示元件用密封劑成為接著性更優異者。 When the sealing compound for liquid crystal display elements of the present invention contains the epoxy compound, it is preferable to make the (meth) acryloyl group in the total of the (meth) acryloyl group and the epoxy group in the curable resin The ratio becomes 30 mol% or more and 95 mol% or less. When the ratio of the (meth) acryl acetyl group is 30 mol% or more, the obtained sealing compound for liquid crystal display elements becomes more excellent in low liquid crystal contamination. When the ratio of the (meth) acryloyl group is 95 mol% or less, the obtained sealing compound for liquid crystal display elements becomes more excellent in adhesiveness.
就進一步抑制液晶污染之觀點而言，上述硬化性樹脂較佳為具有-OH基、-NH-基、-NH2基等氫鍵結性之單元者。 From the viewpoint of further suppressing liquid crystal contamination, the curable resin is preferably a unit having hydrogen bonding properties such as -OH group, -NH- group, and -NH 2 group.
本發明之液晶顯示元件用密封劑含有順丁烯二醯亞胺化合物。 The sealing compound for liquid crystal display elements of this invention contains a maleimide compound.
藉由使用上述順丁烯二醯亞胺化合物，本發明之液晶顯示元件用密封劑即便使用本發明之光聚合起始劑，亦可抑制異物產生。 By using the above-mentioned maleimide compound, the sealing agent for liquid crystal display elements of the present invention can suppress the generation of foreign matter even if the photopolymerization initiator of the present invention is used.
再者，於本發明中，上述順丁烯二醯亞胺化合物不包含於硬化性樹脂中。 Furthermore, in the present invention, the maleimide compound is not included in the curable resin.
上述順丁烯二醯亞胺化合物之分子量之較佳下限為400。藉由使上述順丁烯二醯亞胺化合物之分子量為400以上，所獲得之液晶顯示元件用密封劑成為同時實現對長波長之光的硬化性之提昇、及異物產生之抑制的效果更優異者。上述順丁烯二醯亞胺化合物之分子量之更佳下限為500。 The preferable lower limit of the molecular weight of the maleimide diimide compound is 400. By setting the molecular weight of the maleimide diimide compound to 400 or more, the obtained sealant for a liquid crystal display element achieves both the effect of improving the curability of long-wavelength light and the suppression of the generation of foreign substances. By. The lower limit of the molecular weight of the maleimide diimide compound is more preferably 500.
又，就反應性之觀點而言，上述順丁烯二醯亞胺化合物之分子量之較佳上限為1500，更佳上限為1000。 Moreover, from the viewpoint of reactivity, the preferable upper limit of the molecular weight of the maleimide compound is 1500, and the more preferable upper limit is 1,000.
就反應性之觀點而言，上述順丁烯二醯亞胺化合物較佳為1分子中具有2個以上順丁烯二醯亞胺基之多官能順丁烯二醯亞胺化合物。 From the viewpoint of reactivity, the maleic diimide compound is preferably a polyfunctional maleic diimide compound having two or more maleic diimide groups in one molecule.
作為上述多官能順丁烯二醯亞胺化合物，可較佳地使用下述式(3)表示之化合物或下述式(4)表示之化合物。 As the above-mentioned polyfunctional maleimide compound, compounds represented by the following formula (3) or compounds represented by the following formula (4) can be preferably used.
式(3)中，R1表示碳數2~3之伸烷基，n為2~40之整數。 In formula (3), R 1 represents an alkylene group having 2 to 3 carbon atoms, and n is an integer of 2 to 40.
式(4)中，R2表示碳數1~40之二價脂肪族基。 In formula (4), R 2 represents a divalent aliphatic group having 1 to 40 carbon atoms.
上述式(4)中，R2之碳數較佳為12~36。又，R2較佳為具有脂肪族環。 In the above formula (4), the carbon number of R 2 is preferably 12 to 36. In addition, R 2 preferably has an aliphatic ring.
作為上述式(4)表示之化合物，具體而言，例如可列舉：1,4-雙(順丁烯二醯亞胺)丁烷、1,20-雙順丁烯二醯亞胺-10,11-二辛基二十烷(下述式(5-1)表示之化合物)、1-伸庚基順丁烯二醯亞胺-2-伸辛基順丁烯二醯亞胺-4-辛基-5-庚基環己烷(下述式(5-2)表示之化合物)、1,2-二伸辛基順丁烯二醯亞胺-3-辛基-4-己基環己烷(下述式(5-3)表示之化合物)等。 As the compound represented by the above formula (4), specifically, for example, 1,4-bis (cis-butadiene diimide) butane, 1,20-bis-cis-butadiene diimide-10, 11-dioctyl eicosane (compound represented by the following formula (5-1)), 1-heptylheptyl maleimide bisimide-2- octyl maleimide bisimide-4-octyl -5-heptylcyclohexane (compound represented by the following formula (5-2)), 1,2-bis-octyl-cis-butenediimide-3-octyl-4-hexylcyclohexane (described below Compound represented by formula (5-3)), etc.
上述式(4)表示之化合物例如可藉由美國專利第5973166號說明書中所記載之方法等進行合成。 The compound represented by the above formula (4) can be synthesized by, for example, the method described in US Patent No. 5,973,166.
作為上述順丁烯二醯亞胺化合物中之1分子中具有1個順丁烯二醯亞胺基之單官能順丁烯二醯亞胺化合物，例如可列舉N-生物素基(biotinyl)-N'-(3-順丁烯二醯亞胺丙醯基)-3,6-二氧辛烷-1,8-二胺等。 As a monofunctional maleimide compound having one maleimide group in one molecule of the maleimide compound, for example, N-biotinyl (biotinyl)- N '-(3-cis-butenediimidepropionyl) -3,6-dioxoctane-1,8-diamine, etc.
上述硬化性樹脂與上述順丁烯二醯亞胺化合物之合計100重量份 中之上述順丁烯二醯亞胺化合物之含量的較佳下限為2重量份，較佳上限為50重量份。藉由使上述順丁烯二醯亞胺化合物之含量為2重量份以上，所獲得之液晶顯示元件用密封劑成為抑制異物產生之效果更優異者。藉由使上述順丁烯二醯亞胺化合物之含量為50重量份以下，所獲得之液晶顯示元件用密封劑成為光硬化性更優異者。上述順丁烯二醯亞胺化合物之含量之更佳下限為3重量份，進而較佳下限為5重量份，尤佳下限為10重量份。上述順丁烯二醯亞胺化合物之含量之更佳上限為45重量份，進而較佳上限為40重量份，進而更佳上限為35重量份，尤佳上限為30重量份，最佳上限為25重量份。 The preferable lower limit of the content of the maleic diimide compound in 100 parts by weight of the total of the curable resin and the maleic diimide compound is 2 parts by weight, and the preferred upper limit is 50 parts by weight. By setting the content of the maleimide diimide compound to 2 parts by weight or more, the obtained sealing compound for liquid crystal display elements becomes more excellent in the effect of suppressing the generation of foreign substances. When the content of the maleimide diimide compound is 50 parts by weight or less, the obtained sealant for liquid crystal display elements becomes more excellent in photocurability. The more preferable lower limit of the content of the maleimide diimide compound is 3 parts by weight, the more preferable lower limit is 5 parts by weight, and the more preferable lower limit is 10 parts by weight. The more preferable upper limit of the content of the maleimide compound is 45 parts by weight, the more preferable upper limit is 40 parts by weight, the more preferable upper limit is 35 parts by weight, the more preferable upper limit is 30 parts by weight, and the most preferable upper limit is 25 parts by weight.
本發明之液晶顯示元件用密封劑亦可含有熱硬化劑。 The sealing compound for liquid crystal display elements of this invention may contain a thermosetting agent.
作為上述熱硬化劑，例如可列舉：有機酸醯肼、咪唑衍生物、胺化合物、多酚系化合物、酸酐等。其中，可較佳地使用有機酸醯肼。 Examples of the thermosetting agent include organic acid hydrazine, imidazole derivatives, amine compounds, polyphenol compounds, and acid anhydrides. Among them, the organic acid hydrazine can be preferably used.
作為上述有機酸醯肼，例如可列舉：癸二酸醯肼、間苯二甲酸二醯肼、己二酸醯肼、丙二酸醯肼等。 Examples of the above-mentioned organic acid hydrazine include, for example, hydrazide sebacate, hydrazide isophthalate, hydrazide adipate, and hydrazide malonate.
作為上述有機酸醯肼中之市售者，例如可列舉：大塚化學公司製造之有機酸醯肼、Ajinomoto Fine-Techno公司製造之有機酸醯肼等。 Examples of the commercially available organic acid hydrazide include organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd., and organic acid hydrazide manufactured by Ajinomoto Fine-Techno.
作為上述大塚化學公司製造之有機酸醯肼，例如可列舉：SDH、ADH等。 Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH.
作為上述Ajinomoto Fine-Techno公司製造之有機酸醯肼，例如可列舉：Amicure VDH、Amicure VDH-J、Amicure UDH、Amicure UDH-J等。 Examples of the organic acid hydrazide manufactured by Ajinomoto Fine-Techno include Amicure VDH, Amicure VDH-J, Amicure UDH, and Amicure UDH-J.
上述熱硬化劑之含量相對於硬化性樹脂與順丁烯二醯亞胺化合物之合計100重量份，較佳下限為1重量份，較佳上限為50重量份。藉由使上述熱硬化劑之含量為該範圍，可於不使所獲得之液晶顯示元件用密封劑之塗佈性等惡化之情況下使熱硬化性更優異。上述熱硬化劑之含量之更佳上限為30重量份。 The content of the thermosetting agent is preferably 100 parts by weight relative to the total of the curable resin and the maleimide compound, and the lower limit is preferably 1 part by weight, and the upper limit is preferably 50 parts by weight. By setting the content of the above-mentioned thermosetting agent to this range, the thermosetting property can be made more excellent without deteriorating the coating properties and the like of the obtained sealing compound for liquid crystal display elements. The more preferable upper limit of the content of the above-mentioned thermosetting agent is 30 parts by weight.
本發明之液晶顯示元件用密封劑較佳為以黏度之提昇、由應力 分散效果所帶來之接著性之改善、線膨脹率之改善等為目的而含有填充劑。 The sealant for a liquid crystal display element of the present invention preferably contains a filler for the purpose of improving viscosity, improving adhesion due to the effect of stress dispersion, improving linear expansion rate, and the like.
作為上述填充劑，可使用無機填充劑或有機填充劑。 As the filler, an inorganic filler or an organic filler can be used.
作為上述無機填充劑，例如可列舉：二氧化矽、滑石、玻璃珠、石棉、石膏、矽藻土、膨潤石、膨潤土、蒙脫石、絹雲母、活性白土、氧化鋁、氧化鋅、氧化鐵、氧化鎂、氧化錫、氧化鈦、碳酸鈣、碳酸鎂、氫氧化鎂、氫氧化鋁、氮化鋁、氮化矽、硫酸鋇、矽酸鈣等。 Examples of the inorganic fillers include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, bentonite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, and iron oxide. , Magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate, etc.
作為上述有機填充劑，例如可列舉：聚酯微粒子、聚胺基甲酸酯微粒子、乙烯基聚合物微粒子、丙烯酸聚合物微粒子等。 Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, acrylic polymer fine particles, and the like.
上述填充劑可單獨使用，亦可組合2種以上而使用。 These fillers may be used alone or in combination of two or more.
本發明之液晶顯示元件用密封劑100重量份中之上述填充劑之含量的較佳下限為10重量份，較佳上限為70重量份。藉由使上述填充劑之含量為該範圍，於不使塗佈性等惡化之情況下，接著性之改善等效果更優異。上述填充劑之含量之更佳下限為20重量份，更佳上限為60重量份。 The preferable lower limit of the content of the filler in 100 parts by weight of the sealing compound for liquid crystal display elements of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight. When the content of the filler is within this range, the effect of improving the adhesiveness and the like is more excellent without deteriorating the coatability and the like. The more preferable lower limit of the content of the filler is 20 parts by weight, and the more preferable upper limit is 60 parts by weight.
本發明之液晶顯示元件用密封劑較佳為含有矽烷偶合劑。上述矽烷偶合劑主要具有作為用以將密封劑與基板等良好地接著之接著助劑之作用。 The sealing agent for liquid crystal display elements of the present invention preferably contains a silane coupling agent. The above-mentioned silane coupling agent mainly has a role as an adhesion aid for good adhesion of the sealant and the substrate.
作為上述矽烷偶合劑，例如可較佳地使用3-胺基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-異氰酸基丙基三甲氧基矽烷等。該等係提昇與基板等之接著性之效果優異，藉由與硬化性樹脂進行化學鍵結，可抑制硬化性樹脂流出至液晶中。 As the silane coupling agent, for example, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-iso Cyanopropyl trimethoxysilane etc. These are excellent in improving the adhesion with the substrate, etc. By chemical bonding with the curable resin, the curable resin can be prevented from flowing out into the liquid crystal.
本發明之液晶顯示元件用密封劑100重量份中之上述矽烷偶合劑之含量的較佳下限為0.1重量份，較佳上限為10重量份。藉由使上述矽烷偶合劑之含量為該範圍，抑制液晶污染之產生，並且提昇接著性之效果更優異。上述矽烷偶合劑之含量之更佳下限為0.3重量份，更佳上限為5重量份。 The preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the sealing compound for liquid crystal display elements of the present invention is 0.1 part by weight, and the preferable upper limit is 10 parts by weight. By setting the content of the above-mentioned silane coupling agent to this range, the generation of liquid crystal contamination is suppressed, and the effect of improving adhesion is more excellent. The more preferable lower limit of the content of the above-mentioned silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
本發明之液晶顯示元件用密封劑亦可進而視需要含有反應性稀釋劑、搖變劑、間隔劑、硬化促進劑、消泡劑、調平劑、聚合抑制劑等添加劑。 The sealing agent for liquid crystal display elements of this invention may further contain additives, such as a reactive diluent, a shaker, a spacer, a hardening accelerator, a defoamer, a leveling agent, a polymerization inhibitor, etc., as needed.
作為製造本發明之液晶顯示元件用密封劑之方法，例如可列舉如下方法等：使用勻相分散機、均質混合器、萬能混合器、行星式混合器、捏合機、三輥研磨機等混合機，將硬化性樹脂、本發明之光聚合起始劑、順丁烯二醯亞胺化合物及視需要添加之矽烷偶合劑等進行混合。 As a method of manufacturing the sealing compound for liquid crystal display elements of the present invention, for example, the following methods may be mentioned: a mixer such as a homogenizer, a homomixer, a universal mixer, a planetary mixer, a kneader, a three-roll mill, etc. , The curable resin, the photopolymerization initiator of the present invention, the maleimide compound, and the silane coupling agent added as needed are mixed.
藉由在本發明之液晶顯示元件用密封劑中摻合導電性微粒子，可製造上下導通材料。又，含有此種本發明之液晶顯示元件用密封劑及導電性微粒子之上下導通材料亦為本發明之一。 By blending conductive fine particles in the sealant for liquid crystal display elements of the present invention, a vertical conduction material can be manufactured. In addition, the upper and lower conducting materials containing such a sealant for liquid crystal display elements of the present invention and conductive fine particles are also one of the present invention.
作為上述導電性微粒子，可使用金屬球、於樹脂微粒子之表面形成有導電金屬層者等。其中，於樹脂微粒子之表面形成有導電金屬層者由於藉由樹脂微粒子之優異彈性，可不損傷透明基板等而實現導電連接，故而較佳。 As the conductive fine particles, metal balls, those having a conductive metal layer formed on the surface of the resin fine particles, and the like can be used. Among them, those having a conductive metal layer formed on the surface of the resin microparticles are preferred because of the excellent elasticity of the resin microparticles, which can achieve conductive connection without damaging the transparent substrate or the like.
又，使用本發明之液晶顯示元件用密封劑或本發明之上下導通材料而成之液晶顯示元件亦為本發明之一。 Moreover, the liquid crystal display element using the sealing compound for liquid crystal display elements of this invention or the upper-lower conduction material of this invention is also one of this invention.
作為製造本發明之液晶顯示元件之方法，可較佳地使用液晶滴下法，具體而言，例如可列舉具有以下之各步驟之方法等。 As a method of manufacturing the liquid crystal display element of the present invention, a liquid crystal dropping method can be preferably used. Specifically, for example, a method having the following steps can be cited.
首先，進行如下步驟：於附ITO薄膜等電極之玻璃基板或聚對酞酸乙二酯基板等2片基板中之一者，藉由網版印刷、點膠機塗佈等塗佈本發明之液晶顯示元件用密封劑並形成為框狀之密封圖案。繼而，進行如下步驟：於本發明之液晶顯示元件用密封劑未硬化之狀態下，將液晶之微滴滴下塗佈於基板之密封圖案之框內，於真空下重疊另一基板。然後，藉由進行如下步驟之方法，可獲得液晶顯示元件：藉由經由420nm截止濾光器等對本發明之液晶顯示元件用密 封劑之密封圖案部分照光，而利用長波長之光使密封劑光硬化。又，除上述使密封劑光硬化之步驟以外，亦可進行對密封劑進行加熱而使之熱硬化之步驟。 First, perform the following steps: apply one of the two substrates, such as a glass substrate with electrodes such as an ITO film or a polyethylene terephthalate substrate, by screen printing, dispenser coating, etc. The sealing compound for liquid crystal display elements is formed into a frame-shaped sealing pattern. Then, the following steps are performed: in a state where the sealant for a liquid crystal display element of the present invention is not cured, droplets of liquid crystal are dropped onto a frame of a sealing pattern applied to a substrate, and another substrate is overlapped under vacuum. Then, a liquid crystal display element can be obtained by performing the following steps: by illuminating the sealing pattern portion of the sealant for liquid crystal display elements of the present invention through a 420nm cut filter, etc., and using long wavelength light to make the sealant light hardening. In addition to the above-mentioned step of photo-curing the sealant, a step of heating the sealant to thermally cure it may also be performed.
根據本發明，可提供一種對長波長之光的硬化性優異，且可抑制異物產生之液晶顯示元件用密封劑。又，根據本發明，可提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 According to the present invention, it is possible to provide a sealant for a liquid crystal display element which is excellent in curability of long-wavelength light and can suppress generation of foreign substances. Furthermore, according to the present invention, it is possible to provide a top-to-bottom conductive material and a liquid crystal display element using the sealant for a liquid crystal display element.
以下，揭示實施例更詳細地說明本發明，但本發明並不僅限定於該等實施例。 The following examples are disclosed to explain the present invention in more detail, but the present invention is not limited to these examples.
(式(2-1)表示之化合物之製作) (Preparation of compound represented by formula (2-1))
於鹼性觸媒之存在下，一面於110℃將2-(羧基甲氧基)-9H-硫-9-酮87重量份、及作為單官能環氧化合物之對三級丁基苯基環氧丙醚(ADEKA公司製造，「ED-509S」)62重量份攪拌48小時一面進行反應，藉此獲得上述式(2-1)表示之化合物(m=1)。作為鹼性觸媒，使用PS-PPh3(Biotage Japan公司製造，於聚苯乙烯(PS)載持三苯基膦而成之鹼性觸媒)5.2重量份。 In the presence of an alkaline catalyst, at a temperature of 110 ℃, 2- (carboxymethoxy) -9H-sulfur 87 parts by weight of -9-one and 62 parts by weight of p-tertiary butylphenyl glycidyl ether (manufactured by ADEKA, "ED-509S") as a monofunctional epoxy compound were reacted while stirring for 48 hours, whereby The compound represented by the above formula (2-1) (m = 1) is obtained. As an alkaline catalyst, 5.2 parts by weight of PS-PPh 3 (produced by Biotage Japan Co., Ltd., triphenylphosphine supported on polystyrene (PS)) was used.
再者，所獲得之上述式(2-1)表示之化合物之結構係藉由1H-NMR、13C-NMR及FT-IR進行確認。 The structure of the obtained compound represented by the above formula (2-1) was confirmed by 1 H-NMR, 13 C-NMR and FT-IR.
又，2-(羧基甲氧基)-9H-硫-9-酮與對三級丁基苯基環氧丙醚之摻合比率係以莫耳比計，為2-(羧基甲氧基)-9H-硫-9-酮：對三級丁 基苯基環氧丙醚=1：1。 Also, 2- (carboxymethoxy) -9H-sulfur The blending ratio of -9-one to p-tertiary butyl phenyl glycidyl ether is calculated as the molar ratio, which is 2- (carboxymethoxy) -9H-sulfur -9-one: p-tertiary butyl phenyl glycidyl ether = 1: 1.
(式(2-2)表示之化合物之製作) (Preparation of compound represented by formula (2-2))
於鹼性觸媒之存在下，一面於110℃將2-羥基-9H-硫-9-酮69重量份、及作為單官能環氧化合物之對三級丁基苯基環氧丙醚(ADEKA公司製造，「ED-509S」)62重量份攪拌48小時一面進行反應，藉此獲得上述式(2-2)表示之化合物。作為鹼性觸媒，使用PS-PPh3(Biotage Japan公司製造，於聚苯乙烯(PS)載持三苯基膦而成之鹼性觸媒)5.2重量份。 In the presence of an alkaline catalyst, at a temperature of 110 ℃ 2-hydroxy-9H-sulfur 69 parts by weight of -9-ketone and 62 parts by weight of tertiary butyl phenyl glycidyl ether (made by ADEKA Corporation) as a monofunctional epoxy compound were reacted while stirring for 48 hours, whereby The compound represented by the above formula (2-2) is obtained. As an alkaline catalyst, 5.2 parts by weight of PS-PPh 3 (produced by Biotage Japan Co., Ltd., triphenylphosphine supported on polystyrene (PS)) was used.
再者，所獲得之上述式(2-2)表示之化合物之結構係藉由1H-NMR、13C-NMR及FT-IR進行確認。 The structure of the obtained compound represented by the above formula (2-2) was confirmed by 1 H-NMR, 13 C-NMR and FT-IR.
又，2-羥基-9H-硫-9-酮與對三級丁基苯基環氧丙醚之摻合比率係以莫耳比計，為2-羥基-9H-硫-9-酮：對三級丁基苯基環氧丙醚=1：1。 Also, 2-hydroxy-9H-sulfur The blending ratio of -9-ketone and p-tertiary butyl phenyl glycidyl ether is calculated as the molar ratio, which is 2-hydroxy-9H-sulfur -9-one: p-tertiary butyl phenyl glycidyl ether = 1: 1.
(實施例1~9及比較例1~3) (Examples 1 to 9 and Comparative Examples 1 to 3)
按照表1、2中所記載之摻合比，使用行星式攪拌機(Thinky公司製造，「去泡攪拌太郎」)混合各材料後，進而使用三輥研磨機進行混合，藉此製備實施例1~9及比較例1~3之液晶顯示元件用密封劑。 According to the blending ratio described in Tables 1 and 2, the materials were mixed using a planetary mixer (Thinky Corporation, "defoaming and stirring Taro"), and then further mixed using a three-roll mill to prepare Examples 1 ~ 9 and the sealants for liquid crystal display elements of Comparative Examples 1 to 3.
再者，針對實施例及比較例中所使用之光聚合起始劑，以濃度成為0.1mg/mL之方式溶解於丙烯腈中後，使用分光光度計(日立高新技術科學公司製造，「U-3900」)測定波長430nm之消光係數。將結果示於表1、2。 Furthermore, the photopolymerization initiator used in the examples and comparative examples was dissolved in acrylonitrile at a concentration of 0.1 mg / mL, and then a spectrophotometer (manufactured by Hitachi High-Technology Corporation, "U- 3900 ") Determine the extinction coefficient at a wavelength of 430 nm. The results are shown in Tables 1 and 2.
又，於表中記載為順丁烯二醯亞胺化合物之聚四亞甲基醚二醇之二順丁烯二醯亞胺乙酸酯(DIC公司製造，「LUMICURE MIA200」)係上述式(3)表示之化合物。 In addition, the polytetramethylene ether glycol dicis-butadiene diimide acetate (manufactured by DIC Corporation, "LUMICURE MIA200") described in the table as polytetramethylene ether glycol of the maleimide diimide compound is the above formula ( 3) The compound represented.
<評價> <Evaluation>
對實施例及比較例中所獲得之各液晶顯示元件用密封劑進行以下之評價。 將結果示於表1、2。 The following evaluation was performed about each sealing compound for liquid crystal display elements obtained in the Example and the comparative example. The results are shown in Tables 1 and 2.
(光硬化性) (Photohardenability)
使間隔劑微粒子(積水化學工業公司製造，「Micropearl SI-H050」)1重量份分散於實施例及比較例中所獲得之各液晶顯示元件用密封劑100重量份中。繼而，將密封劑填充至點膠用注射器(武藏高科技公司製造，「PSY-10E」)中，進行脫泡處理後，藉由點膠機(武藏高科技公司製造，「SHOTMASTER 300」)塗佈於玻璃基板上。藉由真空貼合裝置於5Pa之減壓下將相同尺寸之玻璃基板貼合於該基板。使用金屬鹵化物燈對貼合之玻璃基板之密封劑部分照射100mW/cm2之光10秒。照光係進行無420nm截止濾光器之情形、及有420nm截止濾光器之情形2個模式。 1 part by weight of spacer fine particles (manufactured by Sekisui Chemical Industry Co., Ltd., "Micropearl SI-H050") was dispersed in 100 parts by weight of each sealant for liquid crystal display elements obtained in Examples and Comparative Examples. Then, the sealant was filled into a syringe for dispensing (Musashi Hi-Tech Co., Ltd., "PSY-10E"), defoamed, and applied by a dispenser (Musashi Hi-Tech Co., Ltd., "SHOTMASTER 300") Cloth on glass substrate. The glass substrate of the same size was bonded to the substrate with a vacuum bonding device under a reduced pressure of 5 Pa. Using a metal halide lamp, 100 mW / cm 2 of light was irradiated to the sealant portion of the bonded glass substrate for 10 seconds. Illumination is performed in two modes: no 420nm cut-off filter and 420nm cut-off filter.
使用紅外分光裝置(BIORAD公司製造，「FTS3000」)進行密封劑之FT-IR測定，測定來自(甲基)丙烯醯基之波峰於照光前後之變化量，藉此進行硬化性之評價。將於照光後來自(甲基)丙烯醯基之波峰減少80%以上之情形設為「◎」，將減少70%以上且未達80%之情形設為「○」，將減少50%以上且未達70%之情形設為「△」，將照光後之來自(甲基)丙烯醯基之波峰之減少未達50%的情形設為「×」而評價光硬化性。 Using an infrared spectrometer (manufactured by Biorad, "FTS3000"), the FT-IR measurement of the sealant was performed, and the amount of change of the peak from (meth) acryloyl group before and after illumination was measured, thereby evaluating the hardenability. The case where the peak from (meth) acryloyl group is reduced by more than 80% after illumination is set to "◎", and the case where it is reduced by more than 70% and less than 80% is set to "○", which is reduced by more than 50% and When it is less than 70%, it is set to "△", and when the reduction of the peak from the (meth) acryloyl group after illumination is less than 50%, it is set to "×" and the photocurability is evaluated.
(異物防止性) (Foreign matter prevention)
使間隔劑微粒子(積水化學工業公司製造，「Micropearl SI-H050」)1重量份分散於實施例及比較例中所獲得之各液晶顯示元件用密封劑100重量份中，於螢光燈正下方放置3小時。繼而，將密封劑填充至點膠用注射器(武藏高科技公司製造，「PSY-10E」)中，進行脫泡處理後，藉由點膠機(武藏高科技公司製造，「SHOTMASTER 300」)塗佈於玻璃基板上。藉由真空貼合裝置於5Pa之減壓下將相同尺寸之玻璃基板貼合於該基板。此時，若於放置於上述螢光燈正下方時於密封劑中產生異物，則該異物咬入至基板間，而產生間 隙不良。 1 part by weight of spacer fine particles (manufactured by Sekisui Chemical Industry Co., Ltd., "Micropearl SI-H050") was dispersed in 100 parts by weight of each sealant for liquid crystal display elements obtained in Examples and Comparative Examples, directly under the fluorescent lamp Leave for 3 hours. Then, the sealant was filled into a syringe for dispensing (Musashi Hi-Tech Co., Ltd., "PSY-10E"), defoamed, and applied by a dispenser (Musashi Hi-Tech Co., Ltd., "SHOTMASTER 300") Cloth on glass substrate. The glass substrate of the same size was bonded to the substrate with a vacuum bonding device under a reduced pressure of 5 Pa. At this time, if a foreign object is generated in the sealant when placed under the fluorescent lamp, the foreign object bites between the substrates, resulting in a poor gap.
確認所貼合之基板，將完全未產生間隙不良之情形設為「○」，將稍微產生間隙不良之情形設為「△」，將明顯產生間隙不良之情形設為「×」而評價異物防止性。 Confirm the attached substrate, set the case where no gap defect occurs at all as "○", set the gap defect slightly as "△", and set the gap defect significantly as "×" to evaluate the prevention of foreign matter Sex.
[產業上之可利用性] [Industrial availability]
根據本發明，可提供一種對長波長之光的硬化性優異，且可抑制異物產生之液晶顯示元件用密封劑。又，根據本發明，可提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 According to the present invention, it is possible to provide a sealant for a liquid crystal display element which is excellent in curability of long-wavelength light and can suppress generation of foreign substances. Furthermore, according to the present invention, it is possible to provide a top-to-bottom conductive material and a liquid crystal display element using the sealant for a liquid crystal display element.
Claims (8)
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| 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 |
| JP3795459B2 (en) | 2001-05-16 | 2006-07-12 | 積水化学工業株式会社 | Curable resin composition, display element sealing agent and display element sealing agent |
| CN1798786B (en) * | 2003-06-04 | 2013-05-15 | 积水化学工业株式会社 | Curing resin composition, sealing material for liquid crystal display device and liquid crystal display device |
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| JP6197020B2 (en) * | 2015-12-17 | 2017-09-13 | 三井化学株式会社 | Photocurable resin composition, display element sealant, liquid crystal sealant, liquid crystal display panel, and method for producing the same |
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