KR20240163052A - Sealant for liquid crystal display and liquid crystal display element - Google Patents
Sealant for liquid crystal display and liquid crystal display element Download PDFInfo
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- KR20240163052A KR20240163052A KR1020247019488A KR20247019488A KR20240163052A KR 20240163052 A KR20240163052 A KR 20240163052A KR 1020247019488 A KR1020247019488 A KR 1020247019488A KR 20247019488 A KR20247019488 A KR 20247019488A KR 20240163052 A KR20240163052 A KR 20240163052A
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- KR
- South Korea
- Prior art keywords
- liquid crystal
- crystal display
- sealant
- compound
- meth
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 140
- 239000000565 sealant Substances 0.000 title claims abstract description 102
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 239000004593 Epoxy Substances 0.000 claims abstract description 101
- 239000011347 resin Substances 0.000 claims abstract description 55
- 229920005989 resin Polymers 0.000 claims abstract description 55
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 19
- 239000006185 dispersion Substances 0.000 claims abstract description 14
- 238000005192 partition Methods 0.000 claims abstract description 14
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 12
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 11
- -1 glycidyloxy group Chemical group 0.000 claims description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 23
- 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 claims description 15
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 15
- 239000011256 inorganic filler Substances 0.000 claims description 10
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 10
- 230000001588 bifunctional effect Effects 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims 1
- 230000035699 permeability Effects 0.000 abstract description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 42
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 22
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- 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 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
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- 230000000052 comparative effect Effects 0.000 description 7
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- 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 4
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IPHDZYSMEITSBA-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-4-methylcyclohexyl]phenol Chemical compound C1CC(C)CCC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 IPHDZYSMEITSBA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-N 0.000 description 1
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- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
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- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical class [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-nonanolactone Chemical compound CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 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
- 239000011159 matrix material Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940105570 ornex Drugs 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000077 silane Inorganic materials 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
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
-
- C—CHEMISTRY; METALLURGY
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/064—Polymers containing more than one epoxy group per molecule
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/04—Azo-compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1466—Acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4035—Hydrazines; Hydrazides
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
Abstract
본 발명은, 배향막에 대한 접착성 및 투습 방지성이 뛰어나고, 또한, 신뢰성이 뛰어난 액정 표시 소자를 얻을 수 있는 액정 표시 소자용 씰제를 제공하는 것을 목적으로 한다. 또한, 본 발명은, 상기 액정 표시 소자용 씰제를 이용하여 이루어지는 액정 표시 소자를 제공하는 것을 목적으로 한다.
본 발명은, 경화성 수지와, 중합 개시제 및 열경화제의 적어도 어느 하나를 함유하는 액정 표시 소자용 씰제로서, 상기 경화성 수지는, 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물, 상기 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 화합물, 및, 상기 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 화합물로 이루어지는 군으로부터 선택되는 적어도 1종을 포함하는 액정 표시 소자용 씰제이다.The purpose of the present invention is to provide a sealant for a liquid crystal display element which has excellent adhesion to an alignment film and moisture permeability, and which enables obtaining a liquid crystal display element having excellent reliability. In addition, the purpose of the present invention is to provide a liquid crystal display element formed using the sealant for a liquid crystal display element.
The present invention is a sealant for a liquid crystal display element containing a curable resin and at least one of a polymerization initiator and a thermosetting agent, wherein the curable resin comprises at least one selected from the group consisting of an epoxy compound having a dispersion term of a Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, a compound in which some epoxy groups of the epoxy compound are modified with (meth)acrylic, and a compound in which all epoxy groups of the epoxy compound are modified with (meth)acrylic.
Description
본 발명은, 배향막에 대한 접착성 및 투습 방지성이 뛰어나고, 또한, 신뢰성이 뛰어난 액정 표시 소자를 얻을 수 있는 액정 표시 소자용 씰제에 관한 것이다. 또한, 본 발명은, 상기 액정 표시 소자용 씰제를 이용하여 이루어지는 액정 표시 소자에 관한 것이다.The present invention relates to a sealant for a liquid crystal display element, which has excellent adhesion to an alignment film and moisture permeability, and which enables obtaining a liquid crystal display element having excellent reliability. Furthermore, the present invention relates to a liquid crystal display element formed using the sealant for a liquid crystal display element.
근래, 액정 표시 셀 등의 액정 표시 소자의 제조 방법으로서는, 택트 타임 단축, 사용 액정량의 최적화라고 하는 관점으로부터, 특허문헌 1, 특허문헌 2에 개시되어 있는 바와 같은 씰제를 이용한 적하 공법으로 불리는 액정 적하 방식이 이용되고 있다.Recently, as a method for manufacturing liquid crystal display elements such as liquid crystal display cells, a liquid crystal dropping method called a dropping method using a sealant, as disclosed in Patent Documents 1 and 2, has been used from the viewpoint of shortening the tact time and optimizing the amount of liquid crystal used.
적하 공법에서는, 우선, 2매의 전극 부착 기판의 한쪽에, 디스펜스에 의해 테두리 상(狀)의 씰 패턴을 형성한다. 그 다음에, 씰제가 미경화의 상태로 액정의 미소적(微小滴)을 기판의 씰 테두리 내에 적하하고, 진공 하에서 다른 쪽의 기판을 중첩시키고, 씰제의 경화를 수행하여, 액정 표시 소자를 제작한다. 현재 이 적하 공법이 액정 표시 소자의 제조 방법의 주류가 되고 있다. In the dripping method, first, a border-shaped seal pattern is formed on one side of a two-electrode attachment substrate by dispensing. Then, microdroplets of liquid crystal are dropped into the seal border of the substrate while the sealant is not cured, and the other side of the substrate is superimposed under vacuum, and the sealant is cured to produce a liquid crystal display element. Currently, this dripping method is the mainstream method for manufacturing liquid crystal display elements.
그런데, 휴대 전화, 휴대 게임기 등, 각종 액정 패널 모바일 기기가 보급되어 있는 현대에 있어서, 장치의 소형화는 가장 요구되고 있는 과제이다. 소형화의 수법으로서는, 액정 표시부의 협액자화(狹額緣化)를 들 수 있고, 예를 들면, 씰부의 위치를 블랙 매트릭스 하에 배치하는 것이 수행되고 있다(이하, 「협액자 설계」라고도 한다).However, in modern times when various liquid crystal panel mobile devices such as mobile phones and portable game consoles are widespread, miniaturization of devices is the most demanded task. As a method of miniaturization, a narrow frame design of the liquid crystal display section can be mentioned, and for example, the location of the seal section is arranged under the black matrix (hereinafter also referred to as "narrow frame design").
협액자 설계에 수반하여, 액정 표시 소자에 있어서, 화소 영역으로부터 씰제까지의 거리가 가깝게 되어 있어, 씰제에 의해 액정이 오염되는 것에 의한 표시 얼룩이 생기기 쉬워지고 있는 것에 더하여, 씰제가 배향막 상에 배치되는 경우가 많아지고 있기 때문에, 씰제로는, 저-액정 오염성 및 배향막에 대한 접착성이 뛰어난 것이 요구되고 있다.With the design of narrow-frame structures, the distance from the pixel area to the sealant in the liquid crystal display element has become closer, making it easier for display unevenness to occur due to contamination of the liquid crystal by the sealant. In addition, since the sealant is often arranged on an alignment film, there is a demand for a sealant that has low liquid crystal contamination and excellent adhesion to the alignment film.
또한, 태블릿 단말이나 휴대 단말의 보급에 수반하여, 액정 표시 소자로는 고온 고습 환경 하에서의 구동 등에 있어서의 내습 신뢰성이 더욱 더 요구되고 있고, 씰제로는 외부로부터의 물의 침입을 방지하는 성능이 한층 요구되고 있다. 그 때문에, 씰제의 투습 방지성을 향상시킬 필요가 있지만, 협액자 설계에 수반하여 도포되는 씰제의 선폭이 가늘어지고 있고, 세선화했을 경우에서도 투습 방지성이 뛰어나는 씰제를 얻는 것은 곤란했다.In addition, with the spread of tablet terminals and portable terminals, liquid crystal display elements are increasingly required to have moisture resistance reliability in operation under high temperature and high humidity environments, and sealants are increasingly required to have performance that prevents water from entering from the outside. Therefore, it is necessary to improve the moisture permeability of sealants, but the line width of the sealant applied is becoming thinner due to the design of the narrow frame, and even when the line is made thin, it has been difficult to obtain a sealant with excellent moisture permeability.
본 발명은, 배향막에 대한 접착성 및 투습 방지성이 뛰어나고, 또한, 신뢰성이 뛰어난 액정 표시 소자를 얻을 수 있는 액정 표시 소자용 씰제를 제공하는 것을 목적으로 한다. 또한, 본 발명은, 상기 액정 표시 소자용 씰제를 이용하여 이루어지는 액정 표시 소자를 제공하는 것을 목적으로 한다.The purpose of the present invention is to provide a sealant for a liquid crystal display element which has excellent adhesion to an alignment film and moisture permeability, and which enables obtaining a liquid crystal display element having excellent reliability. In addition, the purpose of the present invention is to provide a liquid crystal display element formed using the sealant for a liquid crystal display element.
본 개시 1은, 경화성 수지와, 중합 개시제 및 열경화제의 적어도 어느 하나를 함유하는 액정 표시 소자용 씰제로서, 상기 경화성 수지는, 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물, 상기 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 화합물, 및, 상기 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 화합물로 이루어지는 군으로부터 선택되는 적어도 1종을 포함하는 액정 표시 소자용 씰제이다. The present disclosure 1 is a sealant for a liquid crystal display element containing a curable resin and at least one of a polymerization initiator and a thermosetting agent, wherein the curable resin comprises at least one selected from the group consisting of an epoxy compound having a dispersion term of a Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, a compound in which some epoxy groups of the epoxy compound are modified with (meth)acrylic, and a compound in which all epoxy groups of the epoxy compound are modified with (meth)acrylic.
본 개시 2는, 상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물은, 하기 식(1-1), (1-2), 또는, (1-3)으로 나타내는 화합물인 본 개시 1의 액정 표시 소자용 씰제이다. The present disclosure 2 is a sealant for a liquid crystal display element of the present disclosure 1, wherein the epoxy compound having a dispersion term of the Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less is a compound represented by the following formula (1-1), (1-2), or (1-3).
본 개시 3은, 상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물은, 하기 식(1-2)로 나타내는 화합물인 본 개시 2의 액정 표시 소자용 씰제이다. The present disclosure 3 is a sealant for a liquid crystal display element of the present disclosure 2, wherein the epoxy compound having a dispersion term of the Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less is a compound represented by the following formula (1-2).
본 개시 4는, 상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물은, 하기 식(1-3)으로 나타내는 화합물인 본 개시 2의 액정 표시 소자용 씰제이다. The present disclosure 4 is a sealant for a liquid crystal display element of the present disclosure 2, wherein the epoxy compound having a dispersion term of the Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less is a compound represented by the following formula (1-3).
본 개시 5는, 상기 경화성 수지 전체 100 중량부 중에 있어서의 상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물, 상기 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 화합물, 및, 상기 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 화합물의 함유량이 10 중량부 이상 90 중량부 이하인 본 개시 1, 2, 3 또는 4의 액정 표시 소자용 씰제이다. The present disclosure 5 is a sealant for a liquid crystal display element according to the present disclosure 1, 2, 3 or 4 , wherein the content of an epoxy compound having a dispersion term of the Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less, and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, a compound in which some epoxy groups of the epoxy compound are modified with (meth)acrylic, and a compound in which all epoxy groups of the epoxy compound are modified with (meth)acrylic, is 10 parts by weight or more and 90 parts by weight or less, with respect to 100 parts by weight of the total curable resin.
본 개시 6은, 상기 경화성 수지는, 추가로, 비스페놀 A형 에폭시 화합물, 비스페놀 F형 에폭시 화합물, 부분 (메타)아크릴 변성 비스페놀 A형 에폭시 화합물, 부분 (메타)아크릴 변성 비스페놀 F형 에폭시 화합물, 비스페놀 A형 에폭시 (메타)아크릴레이트, 및, 비스페놀 F형 에폭시 (메타)아크릴레이트로 이루어지는 군으로부터 선택되는 적어도 1종을 포함하는 본 개시 1, 2, 3, 4 또는 5의 액정 표시 소자용 씰제이다. The present disclosure 6 is a sealant for a liquid crystal display element of the present disclosure 1, 2, 3, 4 or 5, wherein the curable resin further comprises at least one selected from the group consisting of a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a partially (meth)acrylic modified bisphenol A type epoxy compound, a partially (meth)acrylic modified bisphenol F type epoxy compound, a bisphenol A type epoxy (meth)acrylate, and a bisphenol F type epoxy (meth)acrylate.
본 개시 7은, 상기 경화성 수지는, 추가로, 2관능 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 중량 평균 분자량이 850 이상인 화합물, 및, 2관능 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 중량 평균 분자량이 850 이상인 화합물의 적어도 어느 하나를 포함하는 본 개시 1, 2, 3, 4, 5 또는 6의 액정 표시 소자용 씰제이다. The present disclosure 7 is a sealant for a liquid crystal display element according to the present disclosure 1, 2, 3, 4, 5 or 6, wherein the curable resin further comprises at least one of a compound in which some of the epoxy groups of a bifunctional epoxy compound are modified with (meth)acryl and has a weight average molecular weight of 850 or more, and a compound in which all of the epoxy groups of the bifunctional epoxy compound are modified with (meth)acryl and has a weight average molecular weight of 850 or more.
본 개시 8은, 추가로, 무기 충전제를 함유하고, 액정 표시 소자용 씰제 100 중량부 중에 있어서의 상기 무기 충전제의 함유량이 5 중량부 이상 50 중량부 이하인 본 개시 1, 2, 3, 4, 5, 6 또는 7의 액정 표시 소자용 씰제이다. The present disclosure 8 is, additionally, a sealant for a liquid crystal display according to any one of the present disclosures 1, 2, 3, 4, 5, 6 or 7, which contains an inorganic filler and has a content of 5 parts by weight or more and 50 parts by weight or less of the inorganic filler per 100 parts by weight of the sealant for a liquid crystal display.
본 개시 9는, 본 개시 1, 2, 3, 4, 5, 6, 7 또는 8의 액정 표시 소자용 씰제의 경화물을 포함하는 액정 표시 소자이다. The present disclosure 9 is a liquid crystal display device comprising a cured product of the sealant for a liquid crystal display device of the present disclosure 1, 2, 3, 4, 5, 6, 7 or 8.
식(1-1)~(1-3) 중, R1~R6은, 각각 독립적으로, 수소 원자, 수산기, 탄소수 1 이상 4 이하의 알킬기, 탄소수 1 이상 4 이하의 알콕시기, 페닐기, 퓨란일기, 티에닐기, 피로릴기, 피리디닐기, 비페닐기, 또는, 시클로헥실기이며, R7, R8은, 글리시딜옥시기이다. In formulas (1-1) to (1-3), R 1 to R 6 are each independently a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, a furanyl group, a thienyl group, a pyrrolyl group, a pyridinyl group, a biphenyl group, or a cyclohexyl group, and R 7 and R 8 are a glycidyloxy group.
이하에 본 발명을 상술한다. The present invention is described in detail below.
종래, 씰제의 배향막에 대한 접착성을 향상시키기 위해서 씰제의 극성을 조정하는 것이 수행되고 있었지만, 근래의 액정 표시 소자에 이용되는 배향막에서는, 고저항화에 대응하기 위해서 수소 결합 가능 부위가 적은 재료가 이용되고 있어, 극성에 근거하지 않는 분자간 상호 작용에 의해서 씰제의 배향막에 대한 접착성을 향상시킬 필요가 있었다. In the past, adjusting the polarity of the sealant was performed to improve the adhesiveness of the sealant to the alignment film. However, in recent alignment films used in liquid crystal display devices, materials with fewer hydrogen bonding sites are used in order to cope with high resistance, and it was necessary to improve the adhesiveness of the sealant to the alignment film by intermolecular interactions not based on polarity.
본 발명자들은, 경화성 수지로서, 한센 용해도 파라미터의 분산항 및 옥탄올/물 분배 계수가 각각 특정의 범위인 에폭시 화합물이나, 상기 에폭시 화합물의 일부 또는 전부의 에폭시기를 (메타)아크릴 변성한 화합물을 이용하는 것을 검토했다. 그 결과, 배향막에 대한 접착성 및 투습 방지성이 뛰어나고, 또한, 신뢰성이 뛰어난 액정 표시 소자를 얻을 수 있는 액정 표시 소자용 씰제가 얻어지는 것을 찾아내어, 본 발명을 완성시키기에 이르렀다.The present inventors have investigated the use of an epoxy compound, as a curable resin, in which the dispersion term of the Hansen solubility parameter and the octanol/water partition coefficient are each within a specific range, or a compound in which some or all of the epoxy groups of the epoxy compound are modified with (meth)acryl. As a result, the inventors have found that a sealant for a liquid crystal display element can be obtained which has excellent adhesion to an alignment film and moisture permeability prevention properties, and furthermore, enables a liquid crystal display element to be obtained with excellent reliability, thereby completing the present invention.
본 발명의 액정 표시 소자용 씰제는, 경화성 수지를 함유한다. The sealant for a liquid crystal display device of the present invention contains a curable resin.
상기 경화성 수지는, 한센 용해도 파라미터의 분산항(이하, 「dD」라고도 말한다)이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수(이하, 「LogKow」라고도 말한다)가 3.0 이상 9.0 이하인 에폭시 화합물(이하, 「본 발명에 따른 에폭시 화합물」이라고도 말한다), 상기 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 화합물(이하, 「본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물」이라고도 말한다), 및, 상기 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 화합물(이하, 「본 발명에 따른 에폭시 (메타)아크릴레이트」라고도 말한다)로 이루어지는 군으로부터 선택되는 적어도 1종을 포함한다. 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트로 이루어지는 군으로부터 선택되는 적어도 1종을 함유하는 것에 의해, 본 발명의 액정 표시 소자용 씰제는, 배향막에 대한 접착성, 투습 방지성, 및, 저-액정 오염성이 뛰어난 것이 된다. The above-mentioned curable resin contains at least one selected from the group consisting of an epoxy compound (hereinafter also referred to as “the epoxy compound according to the present invention”) having a dispersion term of a Hansen solubility parameter (hereinafter also referred to as “dD”) of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient (hereinafter also referred to as “Log Kow”) of 3.0 or more and 9.0 or less, a compound in which some epoxy groups of the epoxy compound are modified with (meth)acryl (hereinafter also referred to as “the partially (meth)acryl-modified epoxy compound according to the present invention”), and a compound in which all epoxy groups of the epoxy compound are modified with (meth)acryl (hereinafter also referred to as “the epoxy (meth)acrylate according to the present invention”). By containing at least one selected from the group consisting of an epoxy compound according to the present invention, a partially (meth)acrylic modified epoxy compound according to the present invention, and an epoxy (meth)acrylate according to the present invention, the sealant for a liquid crystal display element of the present invention has excellent adhesion to an alignment film, moisture permeability, and low liquid crystal contamination properties.
덧붙여, 본 명세서에 있어서 상기 「(메타)아크릴」은, 아크릴 또는 메타크릴을 의미한다. 또한, 상기 「부분 (메타)아크릴 변성 에폭시 화합물」은, 1 분자 중에 2개 이상의 에폭시기를 가지는 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴산과 반응시켜 얻어지는, 1 분자 중에 에폭시기와 (메타)아크릴로 일기를 각각 1개 이상 가지는 화합물을 의미한다. 또한, 상기 「(메타)아크릴레이트」란, 아크릴레이트 또는 메타크릴레이트를 의미하고, 상기 「에폭시 (메타)아크릴레이트」란, 에폭시 화합물 중의 모든 에폭시기를 (메타)아크릴산과 반응시킨 화합물인 것을 의미한다. In addition, in the present specification, the "(meth)acryl" means acrylic or methacryl. In addition, the "partially (meth)acryl-modified epoxy compound" means a compound having at least one epoxy group and at least one (meth)acryloyl group per molecule, obtained by reacting some epoxy groups of an epoxy compound having at least two epoxy groups per molecule with (meth)acrylic acid. In addition, the "(meth)acrylate" means acrylate or methacrylate, and the "epoxy (meth)acrylate" means a compound which is obtained by reacting all epoxy groups in an epoxy compound with (meth)acrylic acid.
본 발명에 따른 에폭시 화합물은, 상기 dD의 하한이 19.0MPa0.5, 상한이 21.9MPa0.5이다. 상기 dD가 19.0MPa0.5 이상인 것에 의해, 본 발명의 액정 표시 소자용 씰제는, 배향막에 대한 접착성이 뛰어난 것이 된다. 상기 dD가 21.9MPa0.5 이하인 것에 의해, 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트가 기타 경화성 수지와의 상용성이 뛰어난 것이 되기 때문에, 본 발명의 액정 표시 소자용 씰제의 디스펜스 시의 선폭 안정성이 향상함으로써 접착성이나 제작된 액정 표시 소자의 신뢰성이 뛰어난 것이 된다. 본 발명에 따른 에폭시 화합물의 상기 dD의 바람직한 하한은 19. 5MPa0.5, 보다 바람직한 하한은 20.1MPa0.5이며, 바람직한 상한은 21.0MPa0.5, 보다 바람직한 상한은 20.4MPa0.5이다. The epoxy compound according to the present invention has a lower limit of the dD of 19.0 MPa 0.5 and an upper limit of 21.9 MPa 0.5 . When the dD is 19.0 MPa 0.5 or more, the sealant for a liquid crystal display element of the present invention has excellent adhesion to an alignment film. When the dD is 21.9 MPa 0.5 or less, the epoxy compound according to the present invention, the partially (meth)acrylic modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention have excellent compatibility with other curable resins, so that the line width stability at the time of dispensing of the sealant for a liquid crystal display element of the present invention is improved, thereby providing excellent adhesion and the reliability of a manufactured liquid crystal display element. The preferred lower limit of the dD of the epoxy compound according to the present invention is 19.5 MPa 0.5 , a more preferred lower limit is 20.1 MPa 0.5 , a preferred upper limit is 21.0 MPa 0.5 , and a more preferred upper limit is 20.4 MPa 0.5 .
덧붙여, 상기 「한센 용해도 파라미터의 분산항(dD)」은, 구조식으로부터 HSP 소프트를 이용하여 계산하는 것에 의해 도출할 수 있다. 상기 HSP 소프트로서는, Hansen Solubility Parameter in Practice(HSPiP)를 이용할 수 있다. In addition, the above "dispersion term (dD) of the Hansen solubility parameter" can be derived by calculating from the structural formula using HSP software. As the above HSP software, Hansen Solubility Parameter in Practice (HSPiP) can be used.
본 발명에 따른 에폭시 화합물은, 상기 LogKow의 하한이 3.0, 상한이 9.0이다. 상기 LogKow가 3.0 이상인 것에 의해, 본 발명의 액정 표시 소자용 씰제는, 배향막에 대한 접착성 및 투습 방지성이 뛰어난 것이 된다. 상기 LogKow가 9.0 이하인 것에 의해, 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트가 기타 경화성 수지와의 상용성이 뛰어난 것이 되기 때문에, 본 발명의 액정 표시 소자용 씰제가 디스펜스 시의 선폭 안정성이 뛰어난 것이 된다. 본 발명에 따른 에폭시 화합물의 상기 LogKow의 바람직한 하한은 3.2이며, 바람직한 상한은 5.9이다. The epoxy compound according to the present invention has a lower limit of the LogKow of 3.0 and an upper limit of 9.0. When the LogKow is 3.0 or higher, the sealant for a liquid crystal display device of the present invention has excellent adhesion to an alignment film and moisture permeability. When the LogKow is 9.0 or lower, the epoxy compound according to the present invention, the partially (meth)acrylic-modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention have excellent compatibility with other curable resins, so the sealant for a liquid crystal display device of the present invention has excellent line width stability at the time of dispensing. The preferable lower limit of the LogKow of the epoxy compound according to the present invention is 3.2, and the preferable upper limit is 5.9.
덧붙여, 상기 「옥탄올/물 분배 계수(LogKow)」는, 구조식으로부터 HSP 소프트를 이용하여 계산하는 것에 의해 도출할 수 있다. 상기 HSP 소프트로서는, Hansen Solubility Parameter in Practice(HSPiP)를 이용할 수 있다. In addition, the above "octanol/water partition coefficient (LogKow)" can be derived by calculating from the structural formula using HSP software. As the above HSP software, Hansen Solubility Parameter in Practice (HSPiP) can be used.
본 발명에 따른 에폭시 화합물은, 피착체와의 밀착성의 관점으로부터, 상기 식(1-1), (1-2), 또는, (1-3)으로 나타내는 화합물인 것이 바람직하다. 또한, 유연성의 관점에서는, 본 발명에 따른 에폭시 화합물은, 상기 식(1-2)로 나타내는 화합물인 것이 보다 바람직하고, 내열성의 관점에서는, 본 발명에 따른 에폭시 화합물은, 상기 식(1-3)으로 나타내는 화합물인 것이 보다 바람직하다. From the viewpoint of adhesion to an adherend, the epoxy compound according to the present invention is preferably a compound represented by the above formula (1-1), (1-2), or (1-3). Furthermore, from the viewpoint of flexibility, the epoxy compound according to the present invention is more preferably a compound represented by the above formula (1-2), and from the viewpoint of heat resistance, the epoxy compound according to the present invention is more preferably a compound represented by the above formula (1-3).
상기 식(1-1)~(1-3) 중의 R1~R6의 적어도 어느 하나가, 페닐기, 비페닐기, 또는, 시클로헥실기인 경우, 상기 페닐기, 상기 비페닐기, 및, 상기 시클로헥실기는, 수소 원자가 치환되어 있어도 된다. 상기 페닐기, 상기 비페닐기, 및, 상기 시클로헥실기가 치환되어 있는 경우의 치환기로서는, 예를 들면, 탄소수 1 이상 4 이하의 알킬기, 탄소수 1 이상 4 이하의 알콕시기 등을 들 수 있다. When at least one of R 1 to R 6 in the above formulas (1-1) to (1-3) is a phenyl group, a biphenyl group, or a cyclohexyl group, the phenyl group, the biphenyl group, and the cyclohexyl group may be substituted with a hydrogen atom. When the phenyl group, the biphenyl group, and the cyclohexyl group are substituted, examples of the substituent include an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and the like.
본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트로서는, 구체적으로는, 하기 식(2)~(23)으로 나타내는 화합물이 바람직하다. 그 중에서도, 하기 식(3)~(5)로 나타내는 화합물이 보다 바람직하다. As the epoxy compound according to the present invention, the partially (meth)acrylic modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention, compounds represented by the following formulae (2) to (23) are specifically preferable. Among them, compounds represented by the following formulae (3) to (5) are more preferable.
상기 경화성 수지는, 추가로, 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트 이외의 기타 경화성 수지를 포함하고 있어도 된다. The above curable resin may additionally contain an epoxy compound according to the present invention, a partially (meth)acrylic modified epoxy compound according to the present invention, and other curable resins other than the epoxy (meth)acrylate according to the present invention.
상기 기타 경화성 수지를 포함하는 경우, 상기 경화성 수지 100 중량부 중에 있어서의 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트의 함유량의 바람직한 하한은 10 중량부, 바람직한 상한은 90 중량부이다. 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트의 함유량이 10 중량부 이상인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 투습 방지성이 보다 뛰어난 것이 된다. 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트의 함유량이 90 중량부 이하인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 신뢰성이 보다 뛰어난 것이 된다. 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트의 함유량의 보다 바람직한 하한은 20 중량부, 보다 바람직한 상한은 50 중량부이다. When the above-mentioned other curable resin is included, the preferable lower limit of the content of the epoxy compound according to the present invention, the partially (meth)acrylic-modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention in 100 parts by weight of the above-mentioned curable resin is 10 parts by weight, and the preferable upper limit is 90 parts by weight. When the content of the epoxy compound according to the present invention, the partially (meth)acrylic-modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention is 10 parts by weight or more, the resulting liquid crystal display element sealant has more excellent moisture permeability. When the content of the epoxy compound according to the present invention, the partially (meth)acrylic-modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention is 90 parts by weight or less, the resulting liquid crystal display element sealant has more excellent reliability. A more preferable lower limit of the content of the epoxy compound according to the present invention, the partially (meth)acrylic modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention is 20 parts by weight, and a more preferable upper limit is 50 parts by weight.
덧붙여, 상기 「본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트의 함유량」은, 상기 경화성 수지가, 본 발명에 따른 에폭시 화합물, 본 발명에 따른 부분 (메타)아크릴 변성 에폭시 화합물, 및, 본 발명에 따른 에폭시 (메타)아크릴레이트 가운데, 1종의 화합물을 단독으로 함유하는 경우는 그 화합물의 함유량을 의미하고, 2종 이상의 화합물을 조합하여 함유하는 경우는 그 합계의 함유량을 의미한다. In addition, the above-mentioned "content of the epoxy compound according to the present invention, the partially (meth)acrylic modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention" means, when the curable resin contains only one type of compound among the epoxy compound according to the present invention, the partially (meth)acrylic modified epoxy compound according to the present invention, and the epoxy (meth)acrylate according to the present invention, the content of that compound, and when the curable resin contains two or more types of compounds in combination, the content of the sum thereof means.
상기 경화성 수지는, 상기 기타 경화성 수지로서, 비스페놀 A형 에폭시 화합물, 비스페놀 F형 에폭시 화합물, 부분 (메타)아크릴 변성 비스페놀 A형 에폭시 화합물, 부분 (메타)아크릴 변성 비스페놀 F형 에폭시 화합물, 비스페놀 A형 에폭시 (메타)아크릴레이트, 및, 비스페놀 F형 에폭시 (메타)아크릴레이트로 이루어지는 군으로부터 선택되는 적어도 1종(이하, 「기타 경화성 수지 A」라고도 말한다)을 포함하는 것이 바람직하다. 상기 기타 경화성 수지 A를 함유하는 것에 의해, 본 발명의 액정 표시 소자용 씰제는, 경화성이 보다 뛰어난 것이 된다. The above-mentioned curable resin preferably contains at least one selected from the group consisting of a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a partially (meth)acrylic-modified bisphenol A type epoxy compound, a partially (meth)acrylic-modified bisphenol F type epoxy compound, a bisphenol A type epoxy (meth)acrylate, and a bisphenol F type epoxy (meth)acrylate (hereinafter also referred to as “other curable resin A”) as the other curable resin. By containing the above-mentioned other curable resin A, the sealant for a liquid crystal display element of the present invention has more excellent curability.
상기 기타 경화성 수지 A는, 유연 골격을 가지는 것이 바람직하다. It is preferable that the above-mentioned other curable resin A has a flexible skeleton.
상기 유연 골격으로서는, 예를 들면, 락톤의 개환 구조, 폴리알킬렌옥사이드 구조, 공역 디엔에 유래하는 고무 구조, 폴리실록산 구조 등을 들 수 있다. Examples of the flexible skeleton include a ring-opening structure of lactone, a polyalkylene oxide structure, a rubber structure derived from a conjugated diene, a polysiloxane structure, etc.
상기 락톤으로서는, 예를 들면, γ-운데카락톤, ε-카프로락톤, γ-데카락톤, σ-도데카락톤, γ-노나노락톤, γ-헵타노락톤, γ-발레로락톤, σ-발레로락톤, β-부티로락톤, γ-부티로락톤, β-프로피오락톤, σ-헥사노락톤, 7-부틸-2-옥세판온 등을 들 수 있다. Examples of the above lactones include γ-undecalactone, ε-caprolactone, γ-decalactone, σ-dodecalactone, γ-nonanolactone, γ-heptanolactone, γ-valerolactone, σ-valerolactone, β-butyrolactone, γ-butyrolactone, β-propiolactone, σ-hexanolactone, 7-butyl-2-oxephanone, etc.
상기 경화성 수지 100 중량부 중에 있어서의 상기 기타 경화성 수지 A의 함유량의 바람직한 하한은 30 중량부, 바람직한 상한은 70 중량부이다. 상기 기타 경화성 수지 A의 함유량이 30 중량부 이상인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 경화성이 보다 뛰어난 것이 된다. 상기 기타 경화성 수지 A의 함유량이 70 중량부 이하인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 접착성이 보다 뛰어난 것이 된다. The preferred lower limit of the content of the other curable resin A in 100 parts by weight of the above-described curable resin is 30 parts by weight, and the preferred upper limit is 70 parts by weight. When the content of the other curable resin A is 30 parts by weight or more, the resulting liquid crystal display element sealant has better curability. When the content of the other curable resin A is 70 parts by weight or less, the resulting liquid crystal display element sealant has better adhesiveness.
또한, 상기 경화성 수지는, 상기 기타 경화성 수지로서, 2관능 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 중량 평균 분자량이 850 이상인 화합물, 및, 2관능 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 중량 평균 분자량이 850 이상인 화합물로 이루어지는 군으로부터 선택되는 적어도 1종(이하, 「기타 경화성 수지 B」라고도 말한다)을 포함하는 것이 바람직하다. 상기 기타 경화성 수지 B를 함유하는 것에 의해, 본 발명의 액정 표시 소자용 씰제는, 저-액정 오염성이 보다 뛰어난 것이 된다. In addition, it is preferable that the curable resin contains at least one selected from the group consisting of a compound having a weight average molecular weight of 850 or more, in which some of the epoxy groups of a bifunctional epoxy compound are modified with (meth)acryl, and a compound having a weight average molecular weight of 850 or more, in which all of the epoxy groups of a bifunctional epoxy compound are modified with (meth)acryl, as the other curable resin (hereinafter also referred to as “other curable resin B”). By containing the other curable resin B, the sealant for a liquid crystal display element of the present invention has more excellent low-liquid crystal contamination properties.
상기 기타 경화성 수지 B의 중량 평균 분자량의 바람직한 하한은 1000, 보다 바람직한 하한은 1300이다. The preferred lower limit of the weight average molecular weight of the above-mentioned other curable resin B is 1000, and the more preferred lower limit is 1300.
또한, 상기 기타 경화성 수지 B의 중량 평균 분자량의 바람직한 상한은 특별히 없지만 실질적인 상한은 6000이다. In addition, there is no specific preferred upper limit of the weight average molecular weight of the above-mentioned other curable resin B, but the practical upper limit is 6000.
덧붙여, 본 명세서에 있어서 상기 「중량 평균 분자량」은, 겔 퍼미에이션 크로마토그래피(GPC)로 용매로서 테트라히드로퓨란을 이용하여 측정 온도 25℃에서 측정을 수행하고, 폴리스티렌 환산에 의해 구할 수 있는 값이다. GPC에 의해서 폴리스티렌 환산에 의한 중량 평균 분자량을 측정할 때에 이용하는 컬럼으로서는, 예를 들면, Shodex LF-804(쇼와 덴코사 제) 등을 들 수 있다. In addition, the "weight average molecular weight" in this specification is a value that can be obtained by polystyrene conversion by measuring at a measurement temperature of 25°C using tetrahydrofuran as a solvent by gel permeation chromatography (GPC). Examples of the column used when measuring the weight average molecular weight by polystyrene conversion by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.).
또한, 상기 부분 (메타)아크릴 변성 비스페놀 A형 에폭시 화합물, 상기 부분 (메타)아크릴 변성 비스페놀 F형 에폭시 화합물, 상기 비스페놀 A형 에폭시 (메타)아크릴레이트, 또는, 상기 비스페놀 F형 에폭시 (메타)아크릴레이트로서도, 중량 평균 분자량이 850 이상인 화합물은 상기 기타 경화성 수지 B로서 취급한다. In addition, a compound having a weight average molecular weight of 850 or more among the above-mentioned partial (meth)acrylic modified bisphenol A type epoxy compound, the above-mentioned partial (meth)acrylic modified bisphenol F type epoxy compound, the above-mentioned bisphenol A type epoxy (meth)acrylate, or the above-mentioned bisphenol F type epoxy (meth)acrylate is treated as the above-mentioned other curable resin B.
상기 기타 경화성 수지 B로서는, 구체적으로는 예를 들면, EBECRYL 3701, EBECRYL 3703, EBECRYL 3708(모두 다이셀·오르네크스사 제) 등을 들 수 있다. 그 밖에도, 예를 들면, jER1001, jER1002, jER1003, jER1055, jER1004, jER1007, jER1009(모두 미츠비시 케미컬사 제), 데나코르 EX-931, 데나코르 EX-991L(모두 나가세 켐텍스사 제), EPICLON 1050, EPICLON 1055, EPICLON 3050, EPICLON 4050, EPICLON 7050, EPICLON AM-030-P, EPICLON AM-040-P, EPICLON HM-091(모두 DIC사 제) 등의 일부 또는 전부를 (메타)아크릴 변성한 화합물 등을 들 수 있다. As the above other curable resins B, specific examples thereof include EBECRYL 3701, EBECRYL 3703, and EBECRYL 3708 (all manufactured by Daicel Ornex Co., Ltd.). In addition, examples thereof include compounds obtained by modifying part or all of (meth)acrylic compounds, such as jER1001, jER1002, jER1003, jER1055, jER1004, jER1007, jER1009 (all manufactured by Mitsubishi Chemical Corporation), DENACOR EX-931, DENACOR EX-991L (all manufactured by Nagase Chemtex Corporation), EPICLON 1050, EPICLON 1055, EPICLON 3050, EPICLON 4050, EPICLON 7050, EPICLON AM-030-P, EPICLON AM-040-P, EPICLON HM-091 (all manufactured by DIC Corporation).
상기 경화성 수지 100 중량부 중에 있어서의 상기 기타 경화성 수지 B의 함유량의 바람직한 하한은 5 중량부, 바람직한 상한은 20 중량부이다. 상기 기타 경화성 수지 B의 함유량이 5 중량부 이상인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 접착성이 보다 뛰어난 것이 된다. 상기 기타 경화성 수지 B의 함유량이 20 중량부 이하인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 투습 방지성이 보다 뛰어난 것이 된다. 상기 기타 경화성 수지 B의 함유량의 보다 바람직한 하한은 10 중량부, 보다 바람직한 상한은 15 중량부이다. The preferable lower limit of the content of the other curable resin B in 100 parts by weight of the above-mentioned curable resin is 5 parts by weight, and the preferable upper limit is 20 parts by weight. When the content of the other curable resin B is 5 parts by weight or more, the resulting liquid crystal display element sealant has better adhesiveness. When the content of the other curable resin B is 20 parts by weight or less, the resulting liquid crystal display element sealant has better moisture permeability. The more preferable lower limit of the content of the other curable resin B is 10 parts by weight, and the more preferable upper limit is 15 parts by weight.
본 발명의 액정 표시 소자용 씰제는, 중합 개시제 및 열경화제의 적어도 어느 하나를 함유한다. The sealant for a liquid crystal display device of the present invention contains at least one of a polymerization initiator and a thermosetting agent.
상기 중합 개시제로서는, 광 조사에 의해 라디칼을 발생하는 광 라디칼 중합 개시제, 가열에 의해 라디칼을 발생하는 열 라디칼 중합 개시제 등을 들 수 있다. As the polymerization initiator, examples thereof include a photoradical polymerization initiator that generates radicals upon light irradiation, a thermal radical polymerization initiator that generates radicals upon heating, and the like.
상기 광 라디칼 중합 개시제로서는, 예를 들면, 벤조페논계 화합물, 아세토페논계 화합물, 아실 포스핀옥사이드계 화합물, 티타노센계 화합물, 옥심 에스테르계 화합물, 벤조인에테르계 화합물, 티옥산톤계 화합물 등을 들 수 있다. Examples of the photoradical polymerization initiator include benzophenone compounds, acetophenone compounds, acyl phosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, and thioxanthone compounds.
상기 광 라디칼 중합 개시제로서는, 구체적으로는 예를 들면, 1-히드록시시클로헥실 페닐 케톤, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)-1-부탄온, 2-(디메틸아미노)-2-((4-메틸페닐) 메틸)-1-(4-(4-모르폴리닐) 페닐)-1-부탄온, 2,2-디메톡시-1,2-디페닐에탄-1-온, 비스(2,4,6-트리메틸벤조일) 페닐 포스핀 옥사이드, 2-메틸-1-(4-메틸티오페닐)-2-모르폴리노프로판-1-온, 1-(4-(2-히드록시에톡시)-페닐)-2-히드록시-2-메틸-1-프로판-1-온, 1-(4-(페닐티오) 페닐)-1,2-옥탄디온-2-(O-벤조일옥심), 2,4,6-트리메틸벤조일 디페닐 포스핀 옥사이드, 벤조인 메틸 에테르, 벤조인 에틸 에테르, 벤조인 이소프로필 에테르 등을 들 수 있다. As the above-mentioned photo-radical polymerization initiator, specifically, for example, 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-(dimethylamino)-2-((4-methylphenyl) methyl)-1-(4-(4-morpholinyl) phenyl)-1-butanone, 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 1-(4-(2-hydroxyethoxy)-phenyl)-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-(phenylthio) Examples thereof include phenyl)-1,2-octanedione-2-(O-benzoyloxime), 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
상기 광 라디칼 중합 개시제는, 단독으로 이용되어도 되고, 2종 이상이 조합하여 이용되어도 된다. The above photo-radical polymerization initiator may be used alone or in combination of two or more.
상기 열 라디칼 중합 개시제로서는, 예를 들면, 아조 화합물이나 유기 과산화물 등으로 구성되는 것을 들 수 있다. 그 중에서도, 액정 오염을 억제하는 관점으로부터, 아조 화합물로 구성되는 개시제(이하, 「아조 개시제」라고도 말한다)가 바람직하고, 고분자 아조 화합물로 구성되는 개시제(이하, 「고분자 아조 개시제」라고도 말한다)가 보다 바람직하다. As the above-mentioned thermal radical polymerization initiator, for example, those composed of an azo compound or an organic peroxide can be mentioned. Among these, from the viewpoint of suppressing liquid crystal contamination, an initiator composed of an azo compound (hereinafter also referred to as an “azo initiator”) is preferable, and an initiator composed of a polymer azo compound (hereinafter also referred to as a “polymer azo initiator”) is more preferable.
상기 열 라디칼 중합 개시제는, 단독으로 이용되어도 되고, 2종 이상이 조합하여 이용되어도 된다. The above-mentioned thermal radical polymerization initiators may be used alone or in combination of two or more.
덧붙여, 본 명세서에 있어서 상기 「고분자 아조 화합물」이란, 아조기를 갖고, 열에 의해서 (메타)아크릴로일기를 경화시킬 수 있는 라디칼을 생성하는, 수평균 분자량이 300 이상인 화합물을 의미한다. In addition, the “polymer azo compound” in this specification means a compound having an azo group and a number average molecular weight of 300 or more that generates a radical capable of curing a (meth)acryloyl group by heat.
상기 고분자 아조 화합물의 수평균 분자량의 바람직한 하한은 1000, 바람직한 상한은 30만이다. 상기 고분자 아조 화합물의 수평균 분자량이 이 범위인 것에 의해, 액정에의 악영향을 방지하면서, 경화성 수지에 용이하게 혼합할 수 있다. 상기 고분자 아조 화합물의 수평균 분자량의 보다 바람직한 하한은 5000, 보다 바람직한 상한은 10만이며, 더욱 바람직한 하한은 1만, 더욱 바람직한 상한은 9만이다. The preferred lower limit of the number average molecular weight of the above polymer azo compound is 1,000, and the preferred upper limit is 300,000. Since the number average molecular weight of the above polymer azo compound is within this range, it can be easily mixed into a curable resin while preventing adverse effects on liquid crystals. The more preferred lower limit of the number average molecular weight of the above polymer azo compound is 5,000, and the more preferred upper limit is 100,000, and the more preferred lower limit is 10,000, and the more preferred upper limit is 90,000.
덧붙여, 본 명세서에 있어서, 상기 수평균 분자량은, 겔 퍼미에이션 크로마토그래피(GPC)로 용매로서 테트라히드로퓨란을 이용하여 측정 온도 25℃에서 측정을 수행하고, 폴리스티렌 환산에 의해 구할 수 있는 값이다. GPC에 의해서 폴리스티렌 환산에 의한 수평균 분자량을 측정할 때의 컬럼으로서는, 예를 들면, Shodex LF-804(쇼와 덴코사 제) 등을 들 수 있다. In addition, in the present specification, the number average molecular weight is a value that can be obtained by measuring at a measurement temperature of 25°C using tetrahydrofuran as a solvent by gel permeation chromatography (GPC), and by polystyrene conversion. Examples of the column for measuring the number average molecular weight by polystyrene conversion by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.).
상기 고분자 아조 화합물로서는, 예를 들면, 아조기를 통해서 폴리알킬렌옥사이드나 폴리디메틸실록산 등의 유닛이 복수 결합한 구조를 가지는 것을 들 수 있다.As the above polymer azo compound, examples thereof include those having a structure in which multiple units, such as polyalkylene oxide or polydimethylsiloxane, are bonded via an azo group.
상기 아조기를 통해서 폴리알킬렌옥사이드 등의 유닛이 복수 결합한 구조를 가지는 고분자 아조 화합물로서는, 폴리에틸렌옥사이드 구조를 가지는 것이 바람직하다.Among the polymer azo compounds having a structure in which multiple units such as polyalkylene oxide are bonded through the above-mentioned azo group, those having a polyethylene oxide structure are preferable.
상기 고분자 아조 화합물로서는, 구체적으로는 예를 들면, 4,4＇-아조비스(4-시아노펜탄산)과 폴리알킬렌글리콜의 중축합물이나, 4,4＇-아조비스(4-시아노펜탄산)과 말단 아미노기를 가지는 폴리디메틸실록산의 중축합물 등을 들 수 있다.As the above polymeric azo compound, specific examples thereof include a polycondensate of 4,4'-azobis(4-cyanopentanoic acid) and polyalkylene glycol, or a polycondensate of 4,4'-azobis(4-cyanopentanoic acid) and polydimethylsiloxane having a terminal amino group.
상기 고분자 아조 화합물 중 시판되고 있는 것으로서는, 예를 들면, VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001(모두 후지필름 와코준야쿠사 제) 등을 들 수 있다.Among the above polymer azo compounds, commercially available ones include, for example, VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
또한, 고분자가 아닌 아조 개시제로서는, 예를 들면, V-65, V-501(모두 후지필름 와코준야쿠사 제) 등을 들 수 있다.In addition, non-polymer azo initiators include, for example, V-65 and V-501 (both manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
상기 유기 과산화물로서는, 예를 들면, 케톤 퍼옥사이드, 퍼옥시 케탈, 하이드로퍼옥사이드, 디알킬 퍼옥사이드, 퍼옥시 에스테르, 디아실 퍼옥사이드, 퍼옥시 디카보네이트 등을 들 수 있다.Examples of the organic peroxides include ketone peroxide, peroxy ketal, hydroperoxide, dialkyl peroxide, peroxy ester, diacyl peroxide, peroxy dicarbonate, etc.
상기 중합 개시제의 함유량은, 상기 경화성 수지 100 중량부에 대해서, 바람직한 하한이 0.01 중량부, 바람직한 상한이 10 중량부이다. 상기 중합 개시제의 함유량이 이 범위인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 액정 오염을 억제하면서, 보존 안정성이나 경화성이 보다 뛰어난 것이 된다. 상기 중합 개시제의 함유량의 보다 바람직한 하한은 0.1 중량부, 보다 바람직한 상한은 5 중량부이다. The content of the polymerization initiator is preferably a lower limit of 0.01 parts by weight and a higher limit of 10 parts by weight, relative to 100 parts by weight of the curable resin. When the content of the polymerization initiator is within this range, the resulting liquid crystal display element sealant suppresses liquid crystal contamination while having superior preservation stability and curability. The content of the polymerization initiator is more preferably a lower limit of 0.1 parts by weight and a higher limit of 5 parts by weight.
상기 열경화제로서는, 예를 들면, 유기산 히드라지드, 이미다졸 유도체, 아민 화합물, 다가 페놀계 화합물, 산무수물 등을 들 수 있다. 그 중에서도, 유기산 히드라지드가 적합하게 이용된다.Examples of the above thermosetting agent include organic acid hydrazide, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, etc. Among them, organic acid hydrazide is suitably used.
상기 열경화제는, 단독으로 이용되어도 되고, 2종 이상이 조합하여 이용되어도 된다.The above thermosetting agent may be used alone or in combination of two or more.
상기 유기산 히드라지드로서는, 예를 들면, 세바신산 디히드라지드, 이소프탈산 디히드라지드, 아디핀산 디히드라지드, 말론산 디히드라지드 등을 들 수 있다.Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
상기 유기산 히드라지드 중 시판되고 있는 것으로서는, 예를 들면, 오오츠카 카가쿠사 제의 유기산 히드라지드, 아지노모토 파인 테크노사 제의 유기산 히드라지드 등을 들 수 있다.Among the above organic acid hydrazides, those commercially available include, for example, organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd. and organic acid hydrazide manufactured by Ajinomoto Fine Techno Co., Ltd.
상기 오오츠카 카가쿠사 제의 유기산 히드라지드로서는, 예를 들면, SDH, ADH, MDH 등을 들 수 있다.Examples of the organic acid hydrazides manufactured by Otsuka Chemical Co., Ltd. include SDH, ADH, MDH, etc.
상기 아지노모토 파인 테크노사 제의 유기산 히드라지드로서는, 예를 들면, 아미큐아 VDH, 아미큐아 VDH-J, 아미큐아 UDH, 아미큐아 UDH-J 등을 들 수 있다.Examples of the organic acid hydrazides manufactured by Ajinomoto Fine Techno include Amicure VDH, Amicure VDH-J, Amicure UDH, and Amicure UDH-J.
상기 열경화제의 함유량은, 상기 경화성 수지 100 중량부에 대해서, 바람직한 하한이 1 중량부, 바람직한 상한이 50 중량부이다. 상기 열경화제의 함유량이 이 범위인 것에 의해, 얻어지는 액정 표시 소자용 씰제의 도포성이나 보존 안정성 등을 악화시키지 않고, 열강화성이 보다 뛰어난 것으로 할 수 있다. 상기 열경화제의 함유량의 보다 바람직한 상한은 30 중량부이다.The content of the thermosetting agent is preferably a lower limit of 1 part by weight and a higher limit of 50 parts by weight, relative to 100 parts by weight of the curable resin. By having the content of the thermosetting agent within this range, the coating properties or storage stability of the resulting liquid crystal display element sealant are not deteriorated, and the thermosetting properties can be further improved. The upper limit of the content of the thermosetting agent is preferably 30 parts by weight.
본 발명의 액정 표시 소자용 씰제는, 무기 충전제를 함유하는 것이 바람직하다. It is preferable that the sealant for a liquid crystal display device of the present invention contains an inorganic filler.
상기 무기 충전제로서는, 예를 들면, 실리카, 탈크, 글라스 비드, 석면, 석고, 규조토, 스멕타이트, 벤토나이트, 몬모리로나이트, 세리사이트, 활성 백토, 알루미나, 산화 아연, 산화 철, 산화 마그네슘, 산화 주석, 산화 티탄, 탄산 칼슘, 탄산 마그네슘, 수산화 마그네슘, 수산화 알루미늄, 질화 알루미늄, 질화 규소, 황산 바륨, 규산 칼슘 등을 들 수 있다. 그 중에서도, 실리카가 바람직하다.Examples of the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate, and the like. Among them, silica is preferable.
상기 무기 충전제는, 단독으로 이용되어도 되고, 2종 이상이 조합하여 이용되어도 된다. The above-mentioned inorganic fillers may be used alone or in combination of two or more.
본 발명의 액정 표시 소자용 씰제 100 중량부 중에 있어서의 상기 무기 충전제의 함유량의 바람직한 하한은 5 중량부, 바람직한 상한은 50 중량부이다. 상기 무기 충전제의 함유량이 5 중량부 이상인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 투습 방지성이 보다 뛰어난 것이 된다. 상기 무기 충전제의 함유량이 50 중량부 이하인 것에 의해, 얻어지는 액정 표시 소자용 씰제가 도포성이 보다 뛰어난 것이 된다. 상기 무기 충전제의 함유량의 보다 바람직한 하한은 10 중량부, 보다 바람직한 상한은 30 중량부이다. The preferable lower limit of the content of the inorganic filler in 100 parts by weight of the sealant for a liquid crystal display device of the present invention is 5 parts by weight, and the preferable upper limit is 50 parts by weight. When the content of the inorganic filler is 5 parts by weight or more, the resulting sealant for a liquid crystal display device has better moisture permeability. When the content of the inorganic filler is 50 parts by weight or less, the resulting sealant for a liquid crystal display device has better coatability. The more preferable lower limit of the content of the inorganic filler is 10 parts by weight, and the more preferable upper limit is 30 parts by weight.
본 발명의 액정 표시 소자용 씰제는, 유기 충전제를 함유해도 된다. The sealant for a liquid crystal display device of the present invention may contain an organic filler.
상기 유기 충전제로서는, 예를 들면, 폴리에스테르 미립자, 폴리우레탄 미립자, 비닐 중합체 미립자, 아크릴 중합체 미립자 등을 들 수 있다. Examples of the organic filler include polyester microparticles, polyurethane microparticles, vinyl polymer microparticles, and acrylic polymer microparticles.
상기 유기 충전제는, 단독으로 이용되어도 되고, 2종 이상이 조합하여 이용되어도 된다.The above organic fillers may be used alone or in combination of two or more.
본 발명의 액정 표시 소자용 씰제는, 실란 커플링제를 함유해도 된다. 상기 실란 커플링제는, 주로 씰제와 기판 등을 양호하게 접착하기 위한 접착조제로서의 역할을 갖는다.The sealant for a liquid crystal display device of the present invention may contain a silane coupling agent. The silane coupling agent mainly functions as an adhesive agent for satisfactorily bonding the sealant to a substrate, etc.
상기 실란 커플링제로서는, 예를 들면, 3-아미노프로필트리메톡시 실란, 3-머캅토프로필트리메톡시 실란, 3-글리시독시프로필트리메톡시 실란, 3-이소시아네이트프로필트리메톡시 실란 등이 적합하게 이용된다. 이들은, 기판 등과의 접착성을 향상시키는 효과가 뛰어나고, 경화성 수지와 화학 결합하는 것에 의해 액정 중에의 경화성 수지의 유출을 억제할 수 있다.As the above silane coupling agent, for example, 3-aminopropyltrimethoxy silane, 3-mercaptopropyltrimethoxy silane, 3-glycidoxypropyltrimethoxy silane, 3-isocyanatepropyltrimethoxy silane, etc. are suitably used. These have an excellent effect of improving adhesion to a substrate, etc., and can suppress leakage of the curable resin into the liquid crystal by chemically bonding with the curable resin.
상기 실란 커플링제는, 단독으로 이용되어도 되고, 2종 이상이 조합하여 이용되어도 된다.The above silane coupling agent may be used alone or in combination of two or more.
본 발명의 액정 표시 소자용 씰제 100 중량부 중에 있어서의 상기 실란 커플링제의 함유량의 바람직한 하한은 0.1 중량부, 바람직한 상한은 10 중량부이다. 상기 실란 커플링제의 함유량이 이 범위인 것에 의해, 액정 오염의 발생을 억제하면서, 접착성을 향상시키는 효과가 보다 뛰어난 것이 된다. 상기 실란 커플링제의 함유량의 보다 바람직한 하한은 0.3 중량부, 보다 바람직한 상한은 5 중량부이다.The preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the liquid crystal display element sealant of the present invention is 0.1 parts by weight, and the preferable upper limit is 10 parts by weight. When the content of the silane coupling agent is within this range, the effect of improving adhesiveness while suppressing the occurrence of liquid crystal contamination is more excellent. The more preferable lower limit of the content of the silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
본 발명의 액정 표시 소자용 씰제는, 차광제를 함유해도 된다. 상기 차광제를 함유하는 것에 의해, 본 발명의 액정 표시 소자용 씰제는, 차광 씰제로서 적합하게 이용할 수 있다.The sealant for a liquid crystal display device of the present invention may contain a light-blocking agent. By containing the light-blocking agent, the sealant for a liquid crystal display device of the present invention can be suitably used as a light-blocking sealant.
상기 차광제로서는, 예를 들면, 산화철, 티탄 블랙, 아닐린 블랙, 시아닌 블랙, 풀러렌, 카본 블랙, 수지 피복형 카본 블랙 등을 들 수 있다. 그 중에서도, 티탄 블랙이 바람직하다. Examples of the above-mentioned sunblock include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Among them, titanium black is preferable.
상기 티탄 블랙은, 파장 300 nm 이상 800 nm 이하인 광에 대한 평균 투과율과 비교하여, 자외선 영역 부근, 특히 파장 370 nm 이상 450 nm 이하의 광에 대한 투과율이 높아지는 물질이다. 즉, 상기 티탄 블랙은, 가시광 영역의 파장의 광을 충분히 차폐함으로써 본 발명의 액정 표시 소자용 씰제에 차광성을 부여하는 한편, 자외선 영역 부근의 파장의 광은 투과시키는 성질을 가지는 차광제이다. 따라서, 상기 광 라디칼 중합 개시제로서, 상기 티탄 블랙의 투과율이 높아지는 파장(370 nm 이상 450 nm 이하)의 광에 의해서 반응을 개시 가능한 것을 이용함으로써, 본 발명의 액정 표시 소자용 씰제의 광 경화성을 보다 증대시킬 수 있다. 또한 한편으로, 본 발명의 액정 표시 소자용 씰제에 함유되는 차광제로서는, 절연성이 높은 물질이 바람직하고, 절연성이 높은 차광제로서도 티탄 블랙이 적합하다.The above titanium black is a material whose transmittance for light near the ultraviolet range, particularly for light of a wavelength of 370 nm to 450 nm, is increased compared to the average transmittance for light of a wavelength of 300 nm to 800 nm. That is, the titanium black is a light-shielding agent that has the property of sufficiently blocking light of a wavelength in the visible light range, thereby imparting light-shielding properties to the sealant for a liquid crystal display element of the present invention, while transmitting light of a wavelength near the ultraviolet range. Therefore, by utilizing, as the photoradical polymerization initiator, a material capable of initiating a reaction by light of a wavelength (370 nm to 450 nm) at which the transmittance of the titanium black is increased, the photocurability of the sealant for a liquid crystal display element of the present invention can be further increased. In addition, on the other hand, as the light-shielding agent contained in the sealant for a liquid crystal display element of the present invention, a highly insulating material is preferable, and titanium black is also suitable as a light-shielding agent of high insulation.
상기 티탄 블랙은, 1μm당의 광학 농도(OD값)가, 3 이상인 것이 바람직하고, 4 이상인 것이 보다 바람직하다. 상기 티탄 블랙의 차광성은 높으면 높을수록 좋고, 상기 티탄 블랙의 OD값에 바람직한 상한은 특별히 없지만, 통상은 5 이하이면 된다.The above titanium black preferably has an optical density (OD value) per 1 μm of 3 or more, and more preferably 4 or more. The higher the light-blocking property of the titanium black, the better, and there is no particular upper limit to the preferred OD value of the titanium black, but it is usually 5 or less.
상기 티탄 블랙은, 표면 처리되어 있지 않은 것이어도 충분한 효과를 발휘하지만, 표면이 커플링제 등의 유기 성분으로 처리되어 있는 것이나, 산화 규소, 산화 티탄, 산화 게르마늄, 산화 알루미늄, 산화 지르코늄, 산화 마그네슘 등의 무기 성분으로 피복되어 있는 것 등, 표면 처리된 티탄 블랙을 이용할 수도 있다. 그 중에서도, 유기 성분으로 처리되어 있는 것은, 보다 절연성을 향상할 수 있는 점에서 바람직하다.The above titanium black exhibits sufficient effects even when not surface-treated, but surface-treated titanium black may also be used, such as titanium black whose surface is treated with an organic component such as a coupling agent, or titanium black coated with an inorganic component such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, or magnesium oxide. Among these, titanium black treated with an organic component is preferable because it can further improve insulation properties.
또한, 차광제로서 상기 티탄 블랙을 배합한 본 발명의 액정 표시 소자용 씰제를 이용하여 제조한 액정 표시 소자는, 충분한 차광성을 가지기 때문에, 광의 누출이 없고 높은 콘트라스트를 가져, 뛰어난 화상 표시 품질을 가지는 액정 표시 소자를 실현할 수 있다.In addition, a liquid crystal display device manufactured using the liquid crystal display device sealant of the present invention, which contains the titanium black as a light-blocking agent, has sufficient light-blocking properties, and thus a liquid crystal display device having no light leakage, high contrast, and excellent image display quality can be realized.
상기 티탄 블랙 중 시판되고 있는 것으로서는, 예를 들면, 미츠비시 머티리얼사 제의 티탄 블랙, 아코 카세이사 제의 티탄 블랙 등을 들 수 있다. Among the above titanium blacks, those commercially available include, for example, titanium black manufactured by Mitsubishi Materials Co., Ltd. and titanium black manufactured by Ako Kasei Co., Ltd.
상기 미츠비시 머티리얼사 제의 티탄 블랙으로서는, 예를 들면, 12S, 13M, 13M-C, 13R-N, 14M-C 등을 들 수 있다. Examples of the above-mentioned titanium blacks manufactured by Mitsubishi Materials include 12S, 13M, 13M-C, 13R-N, and 14M-C.
상기 아코 카세이사 제의 티탄 블랙으로서는, 예를 들면, 티락크 D 등을 들 수 있다. Examples of the above-mentioned titanium blacks manufactured by Ako Kasei Co., Ltd. include Tilac D, etc.
상기 티탄 블랙의 비표면적의 바람직한 하한은 13 m2/g, 바람직한 상한은 30 m2/g이며, 보다 바람직한 하한은 15 m2/g, 보다 바람직한 상한은 25 m2/g이다.The preferred lower limit of the specific surface area of the above titanium black is 13 m 2 /g, the preferred upper limit is 30 m 2 /g, the more preferred lower limit is 15 m 2 /g, and the more preferred upper limit is 25 m 2 /g.
또한, 상기 티탄 블랙의 체적 저항의 바람직한 하한은 0.5Ω·cm, 바람직한 상한은 3Ω·cm이며, 보다 바람직한 하한은 1Ω·cm, 보다 바람직한 상한은 2.5Ω·cm이다.In addition, the preferable lower limit of the volume resistivity of the titanium black is 0.5Ω·cm, the preferable upper limit is 3Ω·cm, the more preferable lower limit is 1Ω·cm, and the more preferable upper limit is 2.5Ω·cm.
상기 차광제의 1차 입자 지름은, 액정 표시 소자의 기판간의 거리 이하이면 특별히 한정되지 않지만, 바람직한 하한은 1 nm, 바람직한 상한은 5000 nm이다. 상기 차광제의 1차 입자 지름이 이 범위인 것에 의해, 얻어진 액정 표시 소자용 씰제의 도포성 등을 악화시키지 않고 차광성이 보다 뛰어난 것으로 할 수 있다. 상기 차광제의 1차 입자 지름의 보다 바람직한 하한은 5 nm, 보다 바람직한 상한은 200 nm, 더욱 바람직한 하한은 10 nm, 더욱 바람직한 상한은 100 nm이다. The primary particle diameter of the above-described light-shielding agent is not particularly limited as long as it is equal to or smaller than the distance between the substrates of the liquid crystal display element, but the preferred lower limit is 1 nm, and the preferred upper limit is 5000 nm. By having the primary particle diameter of the above-described light-shielding agent within this range, the light-shielding properties of the obtained liquid crystal display element sealant can be made more excellent without deteriorating the coatability thereof, etc. The more preferred lower limit of the primary particle diameter of the above-described light-shielding agent is 5 nm, the more preferred upper limit is 200 nm, the more preferred lower limit is 10 nm, and the more preferred upper limit is 100 nm.
덧붙여, 상기 차광제의 1차 입자 지름은, NICOMP 380 ZLS(PARTICLE SIZING SYSTEMS사 제)를 이용하고, 상기 차광제를 용매(물, 유기 용매 등)에 분산시켜 측정할 수 있다.In addition, the primary particle diameter of the above-mentioned shade agent can be measured by dispersing the shade agent in a solvent (water, organic solvent, etc.) using NICOMP 380 ZLS (manufactured by PARTICLE SIZING SYSTEMS).
본 발명의 액정 표시 소자용 씰제 100 중량부 중에 있어서의 상기 차광제의 함유량의 바람직한 하한은 5 중량부, 바람직한 상한은 80 중량부이다. 상기 차광제의 함유량이 이 범위인 것에 의해, 얻어진 액정 표시 소자용 씰제의 접착성, 경화 후의 강도, 및, 묘화성을 크게 저하시키지 않고, 보다 뛰어난 차광성을 발휘할 수 있다. 상기 차광제의 함유량의 보다 바람직한 하한은 10 중량부, 보다 바람직한 상한은 70 중량부이며, 더욱 바람직한 하한은 30 중량부, 더욱 바람직한 상한은 60 중량부이다.The preferable lower limit of the content of the light-blocking agent in 100 parts by weight of the sealant for a liquid crystal display device of the present invention is 5 parts by weight, and the preferable upper limit is 80 parts by weight. When the content of the light-blocking agent is within this range, the adhesiveness, the strength after curing, and the drawing properties of the obtained sealant for a liquid crystal display device can be exhibited without significantly reducing, and more excellent light-blocking properties can be exhibited. The more preferable lower limit of the content of the light-blocking agent is 10 parts by weight, and the more preferable upper limit is 70 parts by weight, and the more preferable lower limit is 30 parts by weight, and the more preferable upper limit is 60 parts by weight.
본 발명의 액정 표시 소자용 씰제는, 추가로, 필요에 따라서, 응력 완화제, 반응성 희석제, 요변제, 스페이서, 경화촉진제, 소포제, 레벨링제, 중합 금지제 등의 첨가제를 함유해도 된다.The sealant for a liquid crystal display device of the present invention may additionally contain, as necessary, additives such as a stress relaxant, a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor.
본 발명의 액정 표시 소자용 씰제를 제조하는 방법으로서는, 예를 들면, 호모 디스퍼, 호모 믹서, 만능 믹서, 플래니터리 믹서, 니더, 3본롤 등의 혼합기를 이용하여, 경화성 수지와, 중합 개시제 및 열경화제의 적어도 어느 하나와, 필요에 따라서 첨가하는 실란 커플링제 등의 첨가제를 혼합하는 방법 등을 들 수 있다.As a method for manufacturing a sealant for a liquid crystal display device of the present invention, examples thereof include a method of mixing a curable resin, at least one of a polymerization initiator and a thermosetting agent, and an additive such as a silane coupling agent added as needed, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three-roll mixer.
본 발명의 액정 표시 소자용 씰제에 도전성 미립자를 배합하는 것에 의해, 상하 도통 재료를 제조할 수 있다.By blending conductive fine particles into the sealant for a liquid crystal display device of the present invention, a vertically conductive material can be manufactured.
상기 도전성 미립자로서는, 금속 볼, 수지 미립자의 표면에 도전 금속층을 형성한 것 등을 이용할 수 있다. 그 중에서도, 수지 미립자의 표면에 도전 금속층을 형성한 것은, 수지 미립자의 뛰어난 탄성에 의해, 투명 기판 등을 손상하지 않고 도전 접속이 가능한 것으로부터 적합하다.As the conductive fine particles, metal balls, resin fine particles having a conductive metal layer formed on the surface thereof, etc. can be used. Among these, resin fine particles having a conductive metal layer formed on the surface thereof are suitable because conductive connection is possible without damaging a transparent substrate, etc., due to the excellent elasticity of the resin fine particles.
본 발명의 액정 표시 소자용 씰제의 경화물을 포함하는 액정 표시 소자도 또한, 본 발명의 하나이다.A liquid crystal display device comprising a cured product of the sealant for a liquid crystal display device of the present invention is also one of the present inventions.
또한, 본 발명의 액정 표시 소자로서는, 협액자 설계의 액정 표시 소자가 바람직하다. 구체적으로는, 액정 표시부의 주위의 테두리 부분의 폭이 2 mm 이하인 것이 바람직하다.In addition, as the liquid crystal display element of the present invention, a liquid crystal display element having a narrow frame design is preferable. Specifically, it is preferable that the width of the frame portion surrounding the liquid crystal display portion is 2 mm or less.
또한, 본 발명의 액정 표시 소자를 제조할 때의 본 발명의 액정 표시 소자용 씰제의 도포폭은 1 mm 이하인 것이 바람직하다.In addition, when manufacturing the liquid crystal display device of the present invention, it is preferable that the coating width of the sealant for the liquid crystal display device of the present invention be 1 mm or less.
본 발명의 액정 표시 소자용 씰제는, 액정 적하 공법에 의한 액정 표시 소자의 제조에 적합하게 이용할 수 있다.The sealant for a liquid crystal display device of the present invention can be suitably used in the manufacture of a liquid crystal display device by a liquid crystal dropping method.
액정 적하 공법에 따라 본 발명의 액정 표시 소자를 제조하는 방법으로서는, 예를 들면, 이하의 방법 등을 들 수 있다. As a method for manufacturing the liquid crystal display element of the present invention by a liquid crystal dropping method, examples thereof include the following methods.
우선, 기판에, 본 발명의 액정 표시 소자용 씰제를 스크린 인쇄, 디스펜서 도포 등에 의해 도포하여, 테두리 상(狀)의 씰 패턴을 형성하는 공정을 수행한다. 그 다음에, 본 발명의 액정 표시 소자용 씰제 등이 미경화인 상태로 액정의 미소적을 씰 패턴의 테두리 내 전면에 적하 도포하고, 곧바로 다른 기판을 중첩하는 공정을 수행한다. 그 후, 씰 패턴 부분에 자외선 등의 광을 조사하여 씰제를 가경화시키는 공정, 및, 가경화시킨 씰제를 가열하여 본 경화시키는 공정을 수행하는 방법에 의해, 액정 표시 소자를 얻을 수 있다.First, a process is performed in which the liquid crystal display element sealant of the present invention is applied to a substrate by screen printing, dispenser application, or the like, to form a border-shaped seal pattern. Next, a process is performed in which the liquid crystal display element sealant of the present invention, etc., in an uncured state, is applied dropwise in microdroplets over the entire surface within the border of the seal pattern, and then another substrate is immediately superimposed. Thereafter, a process is performed in which the seal pattern portion is irradiated with light such as ultraviolet rays to pre-cure the sealant, and a process is performed in which the pre-cure sealant is heated to fully cure it, thereby obtaining a liquid crystal display element.
본 발명에 의하면, 배향막에 대한 접착성 및 투습 방지성이 뛰어나고, 또한, 신뢰성이 뛰어난 액정 표시 소자를 얻을 수 있는 액정 표시 소자용 씰제를 제공할 수 있다. 또한, 본 발명에 의하면, 상기 액정 표시 소자용 씰제를 이용하여 이루어지는 액정 표시 소자를 제공할 수 있다.According to the present invention, it is possible to provide a sealant for a liquid crystal display element which has excellent adhesion to an alignment film and moisture permeability, and which can obtain a liquid crystal display element having excellent reliability. Furthermore, according to the present invention, it is possible to provide a liquid crystal display element formed using the sealant for a liquid crystal display element.
이하에 실시예를 게재하여 본 발명을 더욱 자세하게 설명하지만, 본 발명은 이들 실시예로만 한정되지 않는다.The present invention is described in more detail below by way of examples, but the present invention is not limited to these examples.
(식(2-1)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (2-1))
온도계, 냉각관, 딘·스타크·트랩, 적하 로트, 및, 교반기를 구비한 200 mL 부피(容)의 3구 둥근 바닥 플라스크를 준비했다. 상기 3구 둥근 바닥 플라스크에, 2,2-비스(2-히드록시-5-비페닐일) 프로판(도쿄 카세이 코교사 제) 38 g, 에피클로로히드린(도쿄 카세이 코교사 제) 174 g, 및, 벤질 트리메틸 암모늄 클로라이드(도쿄 카세이 코교사 제) 3.8 g을 넣었다. 그 다음에, 얻어진 혼합물을, 50 토르(torr)의 감압 하에서 교반하면서 약 50℃로 가열하고, 48% 수산화 나트륨 수용액(칸토 카가쿠사 제) 28.2 g을 3시간 걸쳐서 적하했다. 공비로 유출한 물/에피클로로히드린 혼합물 가운데, 에피클로로히드린을 반응계로 되돌리면서 교반을 계속했다. 첨가 종료 후, 3시간에 걸쳐서 교반을 계속했다. 그 다음에, 반응 혼합물을 실온으로 냉각하고, 톨루엔 90 g 및 메틸 이소부틸 케톤 30 g을 더하고 150 mL의 물로 4회 세정했다. 얻어진 유기상의 용매를 감압 환류에 의해 제거하고, 황색 투명 점조물의 상기 식(2)로 나타내는 화합물 38 g을 얻었다.A 200 mL three-necked round-bottom flask equipped with a thermometer, a condenser, a Dean-Stark trap, a dropping funnel, and a stirrer was prepared. Into the three-necked round-bottom flask were placed 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 174 g of epichlorohydrin (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 3.8 g of benzyl trimethyl ammonium chloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.). Then, the obtained mixture was heated to about 50°C with stirring under a reduced pressure of 50 torr, and 28.2 g of a 48% sodium hydroxide aqueous solution (manufactured by Kanto Chemical Co., Ltd.) was added dropwise over 3 hours. Among the water/epichlorohydrin mixture that had been discharged as azeotrope, the epichlorohydrin was returned to the reaction system and stirred continuously. After the addition was completed, stirring was continued for 3 hours. Then, the reaction mixture was cooled to room temperature, 90 g of toluene and 30 g of methyl isobutyl ketone were added, and the mixture was washed four times with 150 mL of water. The obtained organic solvent was removed by reflux under reduced pressure, and 38 g of a compound represented by the above formula (2) as a yellow, transparent viscous substance was obtained.
얻어진 식(2)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다.The structure of the compound represented by the obtained formula (2) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(3)으로 나타내는 화합물의 제작)(Production of the compound represented by Equation (3))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-디히드록시-p-테르페닐 26 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(3)으로 나타내는 화합물 26 g을 얻었다. Except that 26 g of 4,4'-dihydroxy-p-terphenyl was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 26 g of a compound represented by the above formula (3) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(3)으로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (3) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(4)로 나타내는 화합물의 제작) (Production of the compound represented by Equation (4))
식(3)으로 나타내는 화합물 26 g에 대해서, 트리페닐 포스핀 1.3 g, 히드로퀴논 0.1 g, 및, 아크릴산 18 g을 더하고, 100℃에서 8시간 가열 교반한 후, 100 mL의 물로 3회 세정하여, 황색 투명 점조물의 식(4)로 나타내는 화합물 15 g을 얻었다. To 26 g of the compound represented by formula (3), 1.3 g of triphenyl phosphine, 0.1 g of hydroquinone, and 18 g of acrylic acid were added, and the mixture was heated and stirred at 100°C for 8 hours, then washed three times with 100 mL of water to obtain 15 g of the compound represented by formula (4) as a yellow, transparent viscous substance.
얻어진 식(4)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (4) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(5)로 나타내는 화합물의 제작) (Production of the compound represented by Equation (5))
식(3)으로 나타내는 화합물 26 g에 대해서, 트리페닐 포스핀 1.3 g, 히드로퀴논 0.1 g, 및, 아크릴산 7.2 g을 더하고, 100℃에서 8시간 가열 교반한 후, 100 mL의 물로 3회 세정하여, 황색 투명 점조물의 식(5)로 나타내는 화합물 15 g을 얻었다. To 26 g of the compound represented by formula (3), 1.3 g of triphenyl phosphine, 0.1 g of hydroquinone, and 7.2 g of acrylic acid were added, and the mixture was heated and stirred at 100°C for 8 hours, then washed three times with 100 mL of water to obtain 15 g of the compound represented by formula (5) as a yellow, transparent viscous substance.
얻어진 식(5)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (5) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(6)으로 나타내는 화합물의 제작)(Production of the compound represented by Equation (6))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-디히드록시-m-테르페닐 26 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(6)으로 나타내는 화합물 26 g을 얻었다. Except that 26 g of 4,4'-dihydroxy-m-terphenyl was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 26 g of a compound represented by the above formula (6) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(6)으로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (6) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(7)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (7))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-디히드록시-3-메틸-p-테르페닐 28 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(7)로 나타내는 화합물 28 g을 얻었다. Except that 28 g of 4,4'-dihydroxy-3-methyl-p-terphenyl was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 28 g of a compound represented by the above formula (7) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(7)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (7) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(8)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (8))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-디히드록시-3,5-디메틸-p-테르페닐 29 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(8)로 나타내는 화합물 29 g을 얻었다. Except that 29 g of 4,4'-dihydroxy-3,5-dimethyl-p-terphenyl was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 29 g of a compound represented by the above formula (8) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(8)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (8) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(9)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (9))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(2-퓨릴-메틸렌) 비스(2,6-디메틸페놀) 32 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(9)로 나타내는 화합물 32 g을 얻었다. Except that 32 g of 4,4'-(2-furyl-methylene)bis(2,6-dimethylphenol) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 32 g of a compound represented by the above formula (9) was obtained in the same manner as in “(Preparation of a compound represented by formula (2))” above.
얻어진 식(9)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (9) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(10)으로 나타내는 화합물의 제작)(Production of the compound represented by Equation (10))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(페닐메틸렌) 비스페놀 28 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(10)으로 나타내는 화합물 28 g을 얻었다. Except that 28 g of 4,4'-(phenylmethylene)bisphenol was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 28 g of a compound represented by the above formula (10) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(10)으로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (10) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(11)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (11))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(4-메틸시클로헥실리덴) 비스페놀 28 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(11)로 나타내는 화합물 28 g을 얻었다. Except that 28 g of 4,4'-(4-methylcyclohexylidene)bisphenol was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 28 g of a compound represented by the above formula (11) was obtained in the same manner as in the above “(Preparation of a compound represented by formula (2))”.
얻어진 식(11)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (11) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(12)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (12))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 3,3＇-메틸렌 비스(1,1＇-비페닐-4-올) 35 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(12)로 나타내는 화합물 35 g을 얻었다. Except that 35 g of 3,3'-methylenebis(1,1'-biphenyl-4-ol) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 35 g of a compound represented by the above formula (12) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(12)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (12) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(13)으로 나타내는 화합물의 제작)(Production of the compound represented by Equation (13))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(1-페닐에틸리덴) 비스페놀 29 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(13)으로 나타내는 화합물 29 g을 얻었다. Except that 29 g of 4,4'-(1-phenylethylidene)bisphenol was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 29 g of a compound represented by the above formula (13) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(13)으로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (13) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(14)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (14))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-디히드록시-3-이소프로필-p-테르페닐 30 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(14)로 나타내는 화합물 30 g을 얻었다. Except that 30 g of 4,4'-dihydroxy-3-isopropyl-p-terphenyl was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 30 g of a compound represented by the above formula (14) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(14)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (14) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(15)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (15))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(1-페닐에틸리덴) 비스(2-메틸페놀) 28 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(15)로 나타내는 화합물 32 g을 얻었다. Except that 28 g of 4,4'-(1-phenylethylidene)bis(2-methylphenol) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 32 g of a compound represented by the above formula (15) was obtained in the same manner as in “(Preparation of a compound represented by formula (2))” above.
얻어진 식(15)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (15) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(16)으로 나타내는 화합물의 제작)(Production of the compound represented by Equation (16))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-디히드록시-3-tert-부틸-p-테르페닐 28 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(16)으로 나타내는 화합물 32 g을 얻었다. Except that 28 g of 4,4'-dihydroxy-3-tert-butyl-p-terphenyl was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 32 g of a compound represented by the above formula (16) was obtained in the same manner as in “(Preparation of a compound represented by formula (2))” above.
얻어진 식(16)으로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (16) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(17)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (17))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(3,4-디메톡시페닐메틸렌) 비스(2-시클로헥실-5-메틸페놀) 53 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(17)로 나타내는 화합물 53 g을 얻었다. Except that 53 g of 4,4'-(3,4-dimethoxyphenylmethylene)bis(2-cyclohexyl-5-methylphenol) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 53 g of a compound represented by the above formula (17) was obtained in the same manner as in “(Preparation of a compound represented by formula (2))” above.
얻어진 식(17)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (17) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(18)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (18))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(4-메틸시클로헥실리덴) 비스페놀 28 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(18)로 나타내는 화합물 28 g을 얻었다. Except that 28 g of 4,4'-(4-methylcyclohexylidene)bisphenol was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 28 g of a compound represented by the above formula (18) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(18)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (18) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(19)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (19))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-디히드록시테트라페닐 메탄 35 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(19)로 나타내는 화합물 35 g을 얻었다. Except that 35 g of 4,4'-dihydroxytetraphenyl methane was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 35 g of a compound represented by the above formula (19) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(19)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (19) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(20)으로 나타내는 화합물의 제작)(Production of the compound represented by Equation (20))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 5,5＇-(1-페닐에틸리덴) 비스((1,1＇-비페닐)-2-올) 44 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(20)으로 나타내는 화합물 44 g을 얻었다. A compound represented by the formula (20) was obtained 44 g in the same manner as in “(Preparation of the compound represented by the formula (2))” above, except that 44 g of 5,5'-(1-phenylethylidene)bis((1,1'-biphenyl)-2-ol) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane.
얻어진 식(20)으로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (20) was confirmed by 1 H-NMR, 13 C-NMR, and FT-IR.
(식(21)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (21))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 4,4＇-(4-메톡시페닐메틸렌 비스(2-시클로헥실-5-메틸페놀)) 50 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(21)로 나타내는 화합물 50 g을 얻었다. Except that 50 g of 4,4'-(4-methoxyphenylmethylene bis(2-cyclohexyl-5-methylphenol)) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 50 g of a compound represented by the above formula (21) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(21)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (21) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(22)로 나타내는 화합물의 제작)(Production of the compound represented by Equation (22))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 5,5＇-(4-(1,1＇-비페닐) 메틸렌) 비스((1,1＇-비페닐)-2-올) 50 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(22)로 나타내는 화합물 50 g을 얻었다. Except that 50 g of 5,5'-(4-(1,1'-biphenyl)methylene)bis((1,1'-biphenyl)-2-ol) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane, 50 g of a compound represented by the above formula (22) was obtained in the same manner as in the above “(Production of a compound represented by formula (2))”.
얻어진 식(22)로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (22) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(식(23)으로 나타내는 화합물의 제작)(Production of the compound represented by Equation (23))
2,2-비스(2-히드록시-5-비페닐일) 프로판 38 g에 대신하여 5,5＇-(1,1-시클로헥실리덴) 비스-(1,1＇-(비페닐)-2-올) 42 g을 이용한 것 이외에는, 상기 「(식(2)로 나타내는 화합물의 제작)」과 마찬가지로 하여 상기 식(23)으로 나타내는 화합물 42 g을 얻었다. A compound represented by the formula (23) was obtained 42 g in the same manner as in “(Preparation of the compound represented by the formula (2))” above, except that 42 g of 5,5'-(1,1-cyclohexylidene)bis-(1,1'-(biphenyl)-2-ol) was used instead of 38 g of 2,2-bis(2-hydroxy-5-biphenylyl)propane.
얻어진 식(23)으로 나타내는 화합물의 구조는, 1H-NMR, 13C-NMR, 및, FT-IR에 의해 확인했다. The structure of the compound represented by the obtained formula (23) was confirmed by 1H -NMR, 13C -NMR, and FT-IR.
(실시예 1~28, 비교예 1~3) (Examples 1 to 28, Comparative Examples 1 to 3)
표 1~4에 기재된 배합비에 따라, 각 재료를, 유성식 교반 장치(싱키사 제, 「아와토리렌타로」)에서 교반한 후, 세라믹 3본 롤에서 균일하게 혼합하여 실시예 1~28, 비교예 1~3의 액정 표시 소자용 씰제를 얻었다. 비교예 3에서 이용한 9,9-비스(6-글리시딜옥시-2-나프틸) 플루오렌은 일본 특개 2012-102228호 공보의 합성예 1에 준하여 합성했다.According to the mixing ratios described in Tables 1 to 4, each material was stirred in a planetary stirrer ("Awatorin Taro" manufactured by Shinki Co., Ltd.) and then uniformly mixed in a ceramic three-roller to obtain sealants for liquid crystal display elements of Examples 1 to 28 and Comparative Examples 1 to 3. 9,9-Bis(6-glycidyloxy-2-naphthyl)fluorene used in Comparative Example 3 was synthesized according to Synthesis Example 1 of Japanese Patent Application Laid-Open No. 2012-102228.
<평가><Evaluation>
실시예 및 비교예에서 얻어진 각 액정 표시 소자용 씰제에 대하여 이하의 평가를 수행했다. 결과를 표 1~4에 나타냈다. The following evaluations were performed on each of the sealants for liquid crystal display devices obtained in the examples and comparative examples. The results are shown in Tables 1 to 4.
(배향막에 대한 접착성)(Adhesion to the alignment film)
실시예 및 비교예에서 얻어진 각 액정 표시 소자용 씰제 100 중량부에 스페이서 미립자 1 중량부를 분산시켰다. 스페이서 미립자로서는, 미크로 펄 SI-H050(세키스이 카가쿠코교사 제)를 이용했다. 그 다음에, 스페이서 입자를 분산시킨 액정 표시 소자용 씰제를, 2매의 TN용 배향막 SE7492(닛산 카가쿠사 제) 부착 유리 기판(길이 60 mm, 폭 30 mm) 중 한쪽에 미소 적하했다. 여기에 다른 한쪽의 TN용 배향막 SE7492 부착 유리 기판을 십자상으로 첩합하고, 메탈 할라이드 램프로 3000 mJ/cm2의 자외선을 조사한 후, 120℃에서 60분 가열하는 것에 의해서 접착성 시험편을 얻었다. 제작한 접착 시험편에 있어서의 기판의 단부를 반경 5 mm의 금속 원주를 사용하여 5 mm/min의 속도로 압입했을 때에, 패널 박리가 일어날 때의 강도를 측정했다.1 part by weight of spacer particles was dispersed in 100 parts by weight of each of the liquid crystal display sealants obtained in the examples and comparative examples. As the spacer particles, Micro Pearl SI-H050 (manufactured by Sekisui Chemical Co., Ltd.) was used. Next, the liquid crystal display sealant in which the spacer particles were dispersed was micro-dropped onto one of two glass substrates (60 mm in length, 30 mm in width) with TN alignment film SE7492 (manufactured by Nissan Chemical Co., Ltd.). The other glass substrate with TN alignment film SE7492 attached thereto was cross-laminated, and after irradiating it with 3000 mJ/ cm2 of ultraviolet rays from a metal halide lamp, the adhesive test piece was obtained by heating at 120°C for 60 minutes. When the end of the substrate in the manufactured adhesive test piece was pressed at a speed of 5 mm/min using a metal cylinder with a radius of 5 mm, the strength at which panel peeling occurred was measured.
얻어진 측정치(kgf)를 씰 직경(cm)으로 나눈 값이, 3.0kgf/cm를 초과했을 경우를 「◎」, 2.5kgf/cm를 초과 3.0kgf/cm 이하였을 경우를 「○」, 2.0kgf/cm를 초과 2.5kgf/cm 이하였을 경우를 「△」, 2.0kgf/cm 이하였을 경우를 「Х」로 하여 접착성을 평가했다.The adhesiveness was evaluated by dividing the obtained measurement value (kgf) by the seal diameter (cm) and indicating "◎" when it exceeded 3.0 kgf/cm, "○" when it exceeded 2.5 kgf/cm but was 3.0 kgf/cm or less, "△" when it exceeded 2.0 kgf/cm but was 2.5 kgf/cm or less, and "Х" when it was 2.0 kgf/cm or less.
또한, TN용 배향막 SE7492 부착 유리 기판에 대신하여 VA용 배향막 JALS2021(JSR사 제) 부착 유리 기판을 이용하여 마찬가지로 하여 접착성을 평가했다. In addition, the adhesion was evaluated in the same manner using a glass substrate with VA alignment film JALS2021 (manufactured by JSR) attached instead of a glass substrate with TN alignment film SE7492 attached.
(투습 방지성)(Moisture-proof)
실시예 및 비교예에서 얻어진 각 액정 표시 소자용 씰제를, 평활한 이형 필름 상에 코터를 이용하여 두께 200~300μm가 되도록 도포했다. 그 다음에, 메탈 할라이드 램프를 이용하여 3000 mJ/cm2의 자외선을 조사한 후, 120℃에서 1시간 가열하여 씰제를 경화시켜, 투습도 측정용 필름을 얻었다. JIS Z 0208의 방습 포장 재료의 투습도 시험 방법(컵법)에 준한 방법으로 투습도 시험용 컵을 제작하고, 얻어진 투습도 측정용 필름을 부착하고, 80℃, 90% RH의 항온 항습 오븐에 투입하여 투습도를 측정했다.Each of the sealants for liquid crystal displays obtained in the examples and comparative examples was applied to a smooth release film using a coater to a thickness of 200 to 300 μm. Next, 3000 mJ/cm 2 of ultraviolet rays were irradiated using a metal halide lamp, and the sealant was cured by heating at 120°C for 1 hour, thereby obtaining a film for measuring moisture permeability. A cup for a moisture permeability test was produced by a method according to the moisture permeability test method for moisture-proof packaging materials (cup method) of JIS Z 0208, the obtained film for measuring moisture permeability was attached, and the cup was placed in a constant temperature and humidity oven at 80°C and 90% RH to measure moisture permeability.
얻어진 투습도의 값이, 50 g/m2·24 hr 미만이었을 경우를 「◎」, 50 g/m2·24 hr 이상 75 g/m2·24 hr 미만이었을 경우를 「○」, 75 g/m2·24 hr 이상 100g/m2·24 hr 미만이었을 경우를 「△」, 100 g/m2·24 hr 이상이었을 경우를 「Х」로 하여 투습 방지성을 평가했다.The moisture permeability was evaluated by indicating "◎" when the obtained moisture permeability value was less than 50 g/ m2 ·24 hr, "○" when it was 50 g/ m2 ·24 hr or more but less than 75 g/ m2 ·24 hr, "△" when it was 75 g/ m2 ·24 hr or more but less than 100 g/ m2 ·24 hr, and "Х" when it was 100 g/ m2 ·24 hr or more.
(액정 표시 소자의 신뢰성) (Reliability of liquid crystal display elements)
실시예 및 비교예에서 얻어진 각 액정 표시 소자용 씰제 100 중량부에 스페이서 미립자 1 중량부를 분산시켰다. 스페이서 미립자로서는, 미크로 펄 SI-H050(세키스이 카가쿠코교사 제)를 이용했다. 스페이서 입자를 분산시킨 씰제를 디스펜스용의 실린지에 충전하고, 탈포 처리를 수행하고 나서, 디스펜서에서 2매의 러빙 처리한 TN용 배향막 SE7492 및 ITO 박막 부착의 투명 기판의 한쪽의 배향막 상에 직사각형의 테두리를 그리듯이 도포했다. 실린지로서는 PSY-10E(무사시 엔지니어링사 제)를 이용하고, 디스펜서로서는 SHOTMASTER300(무사시 엔지니어링사 제)를 이용했다. 이어서 액정의 미소적을 테두리 내 전면에 적하 도포하고, 곧바로 또다른 한쪽의 기판을 첩합했다. 액정으로서는, JC-5004 LA(질소사 제)를 이용했다. 이어서, 메탈 할라이드 램프를 이용하여 3000 mJ/cm2의 자외선을 조사한 후, 120℃에서 1시간 가열하여 액정 표시 소자용 씰제를 경화시키는 것에 의해, 액정 표시 소자를 얻었다.In each of the liquid crystal display sealants obtained in the examples and comparative examples, 1 part by weight of spacer particles was dispersed in 100 parts by weight. As the spacer particles, Micro Pearl SI-H050 (manufactured by Sekisui Chemical Industry Co., Ltd.) was used. The sealant in which the spacer particles were dispersed was filled into a dispensing syringe, and after performing a defoaming process, it was applied in a rectangular frame on one side of the alignment film of two rubbed TN alignment films SE7492 and transparent substrates with ITO thin films using a dispenser. PSY-10E (manufactured by Musashi Engineering Co., Ltd.) was used as the syringe, and SHOTMASTER300 (manufactured by Musashi Engineering Co., Ltd.) was used as the dispenser. Next, microdroplets of liquid crystal were applied dropwise over the entire surface within the frame, and immediately the other side of the substrate was bonded. JC-5004 LA (manufactured by Nitrogen Corporation) was used as the liquid crystal. Next, a liquid crystal display element was obtained by irradiating the liquid crystal display element with 3000 mJ/ cm2 of ultraviolet rays using a metal halide lamp and then curing the liquid crystal display element sealant by heating at 120°C for 1 hour.
얻어진 액정 표시 소자에 대해서, 25℃, 50% RH의 환경 하에서 4 V의 전압을 인가하고, 액정 표시 소자의 액정 배향 흐트러짐(표시 얼룩)를 육안으로 확인했다. For the obtained liquid crystal display element, a voltage of 4 V was applied in an environment of 25°C and 50% RH, and the liquid crystal alignment disorder (display unevenness) of the liquid crystal display element was visually confirmed.
전압을 인가하고 나서 500시간 이상 경과해도 표시 얼룩이 확인되지 않았던 경우를 「◎」, 250시간 이상 500시간 미만의 사이에 표시 얼룩이 확인되었을 경우를 「○」, 24시간 이상 250시간 미만의 사이에 표시 얼룩이 확인되었을 경우를 「△」, 24시간 미만에서 표시 얼룩이 확인되었을 경우를 「Х」로 하여 액정 표시 소자의 신뢰성을 평가했다.The reliability of the liquid crystal display element was evaluated by rating it as “◎” when no display unevenness was observed after 500 hours or more since voltage was applied, “○” when display unevenness was observed after 250 hours or more but less than 500 hours, “△” when display unevenness was observed after 24 hours or more but less than 250 hours, and “Х” when display unevenness was observed in less than 24 hours.
본 발명에 의하면, 배향막에 대한 접착성 및 투습 방지성이 뛰어나고, 또한, 신뢰성이 뛰어난 액정 표시 소자를 얻을 수 있는 액정 표시 소자용 씰제를 제공할 수 있다. 또한, 본 발명에 의하면, 상기 액정 표시 소자용 씰제를 이용하여 이루어지는 액정 표시 소자를 제공할 수 있다.According to the present invention, it is possible to provide a sealant for a liquid crystal display element which has excellent adhesion to an alignment film and moisture permeability, and which can obtain a liquid crystal display element having excellent reliability. Furthermore, according to the present invention, it is possible to provide a liquid crystal display element formed using the sealant for a liquid crystal display element.
Claims (9)
상기 경화성 수지는, 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물, 상기 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 화합물, 및, 상기 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 화합물로 이루어지는 군으로부터 선택되는 적어도 1종을 포함하는
것을 특징으로 하는 액정 표시 소자용 씰제. A sealant for a liquid crystal display device containing a curable resin and at least one of a polymerization initiator and a thermosetting agent,
The above-mentioned curable resin comprises at least one selected from the group consisting of an epoxy compound having a dispersion term of a Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, a compound in which some epoxy groups of the above-mentioned epoxy compound are modified with (meth)acrylic, and a compound in which all epoxy groups of the above-mentioned epoxy compound are modified with (meth)acrylic.
A sealant for a liquid crystal display device characterized by:
상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물은, 하기 식(1-1), (1-2), 또는, (1-3)으로 나타내는 화합물인 액정 표시 소자용 씰제.
[화 1]
식(1-1)~(1-3) 중, R1~R6은, 각각 독립적으로, 수소 원자, 수산기, 탄소수 1 이상 4 이하의 알킬기, 탄소수 1 이상 4 이하의 알콕시기, 페닐기, 퓨란일기, 티에닐기, 피로릴기, 피리디닐기, 비페닐기, 또는, 시클로헥실기이며, R7, R8은, 글리시딜옥시기이다.In claim 1,
A sealant for a liquid crystal display element, wherein the epoxy compound has a dispersion term of the above Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, and is a compound represented by the following formula (1-1), (1-2), or (1-3).
[Fire 1]
In formulas (1-1) to (1-3), R 1 to R 6 are each independently a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, a furanyl group, a thienyl group, a pyrrolyl group, a pyridinyl group, a biphenyl group, or a cyclohexyl group, and R 7 and R 8 are a glycidyloxy group.
상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물은, 상기 식(1-2)로 나타내는 화합물인 액정 표시 소자용 씰제. In claim 2,
A sealant for a liquid crystal display element, wherein the epoxy compound has a dispersion term of the above Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, and is a compound represented by the above formula (1-2).
상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물은, 상기 식(1-3)으로 나타내는 화합물인 액정 표시 소자용 씰제. In claim 2,
A sealant for a liquid crystal display device, wherein the epoxy compound has a dispersion term of the above Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, and is a compound represented by the above formula (1-3).
상기 경화성 수지 전체 100 중량부 중에 있어서의 상기 한센 용해도 파라미터의 분산항이 19.0MPa0.5 이상 21.9MPa0.5 이하이며, 또한, 옥탄올/물 분배 계수가 3.0 이상 9.0 이하인 에폭시 화합물, 상기 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 화합물, 및, 상기 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 화합물의 함유량이 10 중량부 이상 90 중량부 이하인 액정 표시 소자용 씰제. In any one of claims 1 to 4,
A sealant for a liquid crystal display element, wherein the content of an epoxy compound having a dispersion term of the Hansen solubility parameter of 19.0 MPa 0.5 or more and 21.9 MPa 0.5 or less, and an octanol/water partition coefficient of 3.0 or more and 9.0 or less, a compound in which some epoxy groups of the epoxy compound are modified with (meth)acrylic, and a compound in which all epoxy groups of the epoxy compound are modified with (meth)acrylic, is 10 parts by weight or more and 90 parts by weight or less, based on 100 parts by weight of the total curable resin,
상기 경화성 수지는, 추가로, 비스페놀 A형 에폭시 화합물, 비스페놀 F형 에폭시 화합물, 부분 (메타)아크릴 변성 비스페놀 A형 에폭시 화합물, 부분 (메타)아크릴 변성 비스페놀 F형 에폭시 화합물, 비스페놀 A형 에폭시 (메타)아크릴레이트, 및, 비스페놀 F형 에폭시 (메타)아크릴레이트로 이루어지는 군으로부터 선택되는 적어도 1종을 포함하는 액정 표시 소자용 씰제. In any one of claims 1 to 5,
A sealant for a liquid crystal display element, wherein the curable resin further comprises at least one selected from the group consisting of a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a partially (meth)acrylic modified bisphenol A type epoxy compound, a partially (meth)acrylic modified bisphenol F type epoxy compound, a bisphenol A type epoxy (meth)acrylate, and a bisphenol F type epoxy (meth)acrylate.
상기 경화성 수지는, 추가로, 2관능 에폭시 화합물의 일부의 에폭시기를 (메타)아크릴 변성한 중량 평균 분자량이 850 이상인 화합물, 및, 2관능 에폭시 화합물의 전부의 에폭시기를 (메타)아크릴 변성한 중량 평균 분자량이 850 이상인 화합물의 적어도 어느 하나를 포함하는 액정 표시 소자용 씰제. In any one of claims 1 to 6,
A sealant for a liquid crystal display element, wherein the curable resin further comprises at least one of a compound in which some of the epoxy groups of a bifunctional epoxy compound are modified with (meth)acryl and has a weight average molecular weight of 850 or more, and a compound in which all of the epoxy groups of a bifunctional epoxy compound are modified with (meth)acryl and has a weight average molecular weight of 850 or more.
추가로, 무기 충전제를 함유하고,
액정 표시 소자용 씰제 100 중량부 중에 있어서의 상기 무기 충전제의 함유량이 5 중량부 이상 50 중량부 이하인 액정 표시 소자용 씰제. In any one of claims 1 to 7,
Additionally, it contains weapon fillers,
A sealant for a liquid crystal display device, wherein the content of the inorganic filler is 5 parts by weight or more and 50 parts by weight or less per 100 parts by weight of the sealant for a liquid crystal display device.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPJP-P-2022-044027 | 2022-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20240163052A true KR20240163052A (en) | 2024-11-18 |
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