CN106397697A - Liquid crystal sealant and liquid crystal display cell using same - Google Patents
Liquid crystal sealant and liquid crystal display cell using same Download PDFInfo
- Publication number
- CN106397697A CN106397697A CN201610060537.6A CN201610060537A CN106397697A CN 106397697 A CN106397697 A CN 106397697A CN 201610060537 A CN201610060537 A CN 201610060537A CN 106397697 A CN106397697 A CN 106397697A
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- sealing agent
- drop method
- crystal sealing
- described composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 217
- 239000000565 sealant Substances 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 85
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 21
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 15
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 132
- 238000007789 sealing Methods 0.000 claims description 103
- -1 (methyl) acryloyl group Chemical group 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 17
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000007711 solidification Methods 0.000 claims description 13
- 230000008023 solidification Effects 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910000077 silane Inorganic materials 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
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- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 claims description 4
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- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 7
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- 239000003054 catalyst Substances 0.000 description 5
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- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
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- 238000001879 gelation Methods 0.000 description 4
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
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- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910002026 crystalline silica Inorganic materials 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 2
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LMVLVUPTDRWATB-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-ol Chemical compound CO[Si](C)(OC)CCCO LMVLVUPTDRWATB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
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- 101800000021 N-terminal protease Proteins 0.000 description 1
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- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
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- 230000008901 benefit Effects 0.000 description 1
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- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
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- 239000004917 carbon fiber Substances 0.000 description 1
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- 238000010030 laminating Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 125000005641 methacryl group Chemical group 0.000 description 1
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- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- IFZUFHWISBKFJP-UHFFFAOYSA-N n'-[4-[dimethoxy(methyl)silyl]oxybutyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)OCCCCNCCN IFZUFHWISBKFJP-UHFFFAOYSA-N 0.000 description 1
- HNPPKZRZKDKXDO-UHFFFAOYSA-N n,n-dimethylformamide;propan-2-one Chemical compound CC(C)=O.CN(C)C=O HNPPKZRZKDKXDO-UHFFFAOYSA-N 0.000 description 1
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- 239000012860 organic pigment Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-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
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
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- 239000005011 phenolic resin Substances 0.000 description 1
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- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical class CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000001869 rapid Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229910010271 silicon carbide 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
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Provided is a liquid crystal sealant for a liquid crystal dropping process, having excellent handling properties and storage stability, as well as extremely low staining with respect to liquid crystal in process, due to having fast response to heat. This liquid crystal sealant for a liquid crystal dropping process contains (a) a thermal radical polymerization initiator not having an oxygen-oxygen bond (-O-O-) and a nitrogen-nitrogen bond (-N=N-) in the molecule thereof, (b) a radical polymerization inhibitor, and (c) a curable resin having a (meth)acryloyl group.
Description
The application be the applying date is on July 12nd, 2012, Application No. 201280034501.0, send out
The division Shen of the patent application of bright entitled " liquid crystal sealing agent and use its liquid crystal display "
Please, entire contents are hereby expressly incorporated by reference.
Technical field
The present invention relates to the liquid crystal drop method liquid crystal sealing agent that a kind of heat can solidify.More specifically
, it is related to a kind of there is good heat curable and operability, storage stability, bonding strength etc.
Solidfied material characteristic also good liquid crystal drop method liquid crystal sealing agent and its manufacture method and its solidification
Thing.
Background technology
With the maximization of liquid crystal display in recent years, as a kind of manufacture of liquid crystal display
Method is it is proposed that have the so-called liquid crystal drop method (patent documentation 1,2) of producing property of higher amount.Specifically
For, the manufacture method of this liquid crystal display is, in the liquid crystal sealing agent being formed at side substrate
After the inner side dropping liquid crystal of weir dike, by fitting, opposite side substrate makes sealing liquid crystal.
But, liquid crystal drop method is due to being that the liquid crystal sealing agent of its uncured state contacts liquid crystal, now liquid
The composition of brilliant sealant is dissolved in liquid crystal (dissolution) makes the resistance value of liquid crystal reduce, and produces sealant attached
The bad problem of near display.
For solving this problem, in present practical application, it is the sealing liquid crystal by a kind of photo-thermal and with type
Agent is used as the liquid crystal sealing agent (patent documentation 3,4) of liquid crystal drop method.Using this sealing liquid crystal
The liquid crystal drop method of agent is characterised by, carries out once to the liquid crystal sealing agent irradiation light by substrate clamping
After solidification, carry out heating and carry out secondary solidification again.According to this method, uncured liquid crystal can be made
Sealant solidified rapidly by light it is suppressed that dissolving (dissolution) from liquid crystal sealing agent composition to liquid crystal.
And, if only using photocuring, because cure shrinkage during photocuring etc. also can produce bonding strength not
The problem of foot, but if using photo-thermal and using type, have and secondary solidification can be carried out by heating
Advantage, thus this problem is addressed.
But, in recent years, with the miniaturization of liquid crystal display cells, due to the battle array of liquid crystal display cells
The black matrix" part of the metal wiring section of row substrate or colored filter substrate, creating light cannot
Expose to the light shielding part of liquid crystal sealing agent so that the bad problem of the display near sealant is than in the past more
Seriously.That is, the one-step solidification being carried out by above-mentioned light due to the presence of light shielding part is insufficient,
Uncured composition in a large number is remained in liquid crystal sealing agent.When secondary curing process is carried out with the heating of this state,
Result promotes the dissolving to liquid crystal for this uncured composition due to heat, causes the display near sealant
Bad.
For solving this problem it is proposed that by using hot radical propellant, to improve heat solidification speed
Degree, reduces the scheme of composition dissolution, only realizes liquid crystal drippage by heat in addition with applying this technology
The motion (patent documentation 5,6) of method.But, use organic peroxide or azo-compound at present
As hot radical propellant, when these pass through heating generation free radical, nitrogen or oxygen etc. can be produced,
Produce bubble in solidfied material, thus there is decline of bonding strength etc. and reduce asking of solidfied material characteristic
Topic.
Additionally, said method is from the point of view of its response speed, its operability is relatively low also to become a problem.
Operability refers to the easy degree of the use of liquid crystal sealing agent.For example, in the deaeration work of liquid crystal sealing agent
Sequence or sept (spacer) mixed processes etc. need in the operation place under vacuo or need heating,
Have the phenomenon of liquid crystal sealing agent solidification or gelation, the easy-suffering level of this phenomenon is defined as operating
Property.Therefore, using be not susceptible to gelation as good operability liquid crystal sealing agent, be susceptible to coagulate
Gel then as the liquid crystal sealing agent that operability is bad.
Additionally, in addition to aforesaid operations, storage stability is also the key property of liquid crystal sealing agent.This
Refer to make sealing apply the property becoming difficult by viscosity increase at room temperature, sent out using hot radical
This storage stability of liquid crystal sealing agent of raw agent is also bad.This problem of solution is proposed in patent documentation 7
Method, but as solving above-mentioned method of all the problems, or insufficient.
Although as described above, people have carried out positive opening to the liquid crystal sealing agent for liquid crystal drop method
While sending out, but not yet realize there is good heat reactivity or light shielding part curable, also have good
Operability, storage stability, and the also excellent liquid crystal sealing agent of solidfied material characteristic.
Citation
Patent documentation
Patent documentation 1：JP 63-179323 publication
Patent documentation 2：Unexamined Patent 10-239694 publication
Patent documentation 3：Specially permit No. 3583326 publication
Patent Document 4：JP 2004-61925 publication
Patent documentation 5：JP 2004-126211 publication
Patent documentation 6：JP 2009-8754 publication
Patent documentation 7：JP 2009-42409 publication
Content of the invention
Invention problem to be solved
Liquid crystal sealing agent proposed by the present invention is a kind of liquid crystal sealing agent for liquid crystal drop method, described
Liquid crystal drop method is used for the inner side drippage liquid of the weir dike of liquid crystal sealing agent on being formed at side substrate
After crystalline substance, opposite side substrate of fitting, it is used in combination by only heating to liquid crystal sealing agent portion or being passed through photo-thermal
It is made to solidify, thus manufacturing the liquid crystal drop method of liquid crystal display, because heat reaction is very fast,
In whole process, extremely low to the contaminative of liquid crystal, and the operability such as deaeration is good, this is export-oriented
The screening characteristics of substrate, stickiness, bonding strength etc. are excellent, are therefore applicable to the liquid crystal of any design
Panel.
Means to solve the problem
The inventors of the present invention pass through to study with keen determination, it is found that simultaneously using certain hot radical
The liquid crystal sealing agent of polymerization initiator and radical polymerization preventing agent can have above-mentioned thermal response simultaneously
Property and operability, its result can suppress liquid crystal pollution, the solidfied material characteristic of bonding strength etc. in addition
Also very outstanding, it has been finally completed the present invention.
That is, the present invention is the technical scheme being related to following (1)～(12).Additionally, this
In description, " (methyl) acrylic acid ((metha) acryl) " refers to " acrylic acid " and " methyl
The one or both of which of acrylic acid ".Equally, in this specification, " (methyl) acryloyl " is
Refer to the one or both of which of " acryloyl " and " methacryl ".
(1) a kind of liquid crystal drop method liquid crystal sealing agent is it is characterised in that contain：(a) molecule
Inside there is no o-o bond (- O-O-) and the hot radical of nitrogen-nitrogen key (- N=N-) gathers
Close initiator, (b) radical polymerization preventing agent and (c) and there is (methyl) acryloyl group
Curable resin.
(2) the liquid crystal drop method liquid crystal sealing agent described in above-mentioned (1), wherein, mentioned component (a)
It is the compound being represented by following formula (1)：
[chemical formula 1]
In formula (1), Y1、Y2Represent hydrogen atom, phenyl or silicon atom, R independently of one another1~
R6Represent the straight or branched alkyl of hydrogen atom or carbon number 1～4, X independently of one another1～X4Respectively
From independently representing hydrogen atom, methyl, ethyl, methoxyl group, ethyoxyl, phenoxy group or halogen atom,
Wherein, work as Y1Or Y2When being hydrogen atom, it is joined respectively to Y1Or Y2R1～R3Or R4～R6
It is non-existent.
(3) the drop method liquid crystal sealing agent described in above-mentioned (1) or (2), wherein, above-mentioned one-tenth
(b) is divided to be to prevent selected from one of following formula (2) to (4) or two or more radical polymerization
Agent：
[chemical formula 2]
In formula (2), R7Represent hydrogen atom, hydroxyl, the straight or branched alkane of carbon number 1～4
Epoxide or the straight or branched alkyl of carbon number 1～4,
[chemical formula 3]
In formula (3), R8Represent hydrogen atom, hydroxyl, the straight or branched alkane of carbon number 1～4
Epoxide, phenoxy group, acetamido, amino, carboxyl, cyano group, benzoyloxy, isothiocyanate
Base or epoxide, R9～R12Represent the straight or branched alkyl of carbon number 1～4 independently of one another,
[chemical formula 4]
In formula (4), R13Represent the straight or branched alkyl of hydrogen atom or carbon number 1～4.
(4) above-mentioned (1) liquid crystal drop method liquid crystal sealing agent any one of to (3),
Also contain curable resin and (e) thermal curing agents that (d) has epoxy radicals.
(5) the liquid crystal drop method liquid crystal sealing agent according to above-mentioned (4), wherein, above-mentioned one-tenth
(e) is divided to be organic hydrazides.
(6) above-mentioned (1) liquid crystal drop method liquid crystal sealing agent any one of to (5),
Wherein, also contain (f) silane coupler.
(7) above-mentioned (1) liquid crystal drop method liquid crystal sealing agent any one of to (6),
Wherein, also contain (g) inorganic filler.
(8) above-mentioned (1) liquid crystal drop method liquid crystal sealing agent any one of to (7),
Wherein, also contain (h) Photoepolymerizationinitiater initiater.
(9) the liquid crystal drop method liquid crystal sealing agent described in above-mentioned (4) or (5), wherein, on
The total amount stating composition (c) and mentioned component (d) is with 100 mass parts timing, mentioned component (b)
Content be 0.0001 mass parts to 1 mass parts.
(10) above-mentioned (1) liquid crystal drop method liquid crystal sealing agent any one of to (9)
Manufacture method, wherein, including operation mentioned component (b) being dissolved in mentioned component (c).
(11) manufacture method of the liquid crystal drop method liquid crystal sealing agent described in above-mentioned (4) or (5),
Wherein, including operation mentioned component (b) being dissolved in mentioned component (d).
(12) liquid crystal display, wherein, above-mentioned liquid crystal display is by by above-mentioned (1)
Liquid crystal drop method any one of to (9) with liquid crystal sealing agent or by above-mentioned (10) or
(11) the liquid crystal drop method liquid crystal sealing agent that the manufacture method described in obtains solidifies and obtains ground solidfied material
Hermetically sealed liquid crystal display.
Invention effect
The liquid crystal sealing agent of the present invention is fast due to curing rate during heat cure, thus can be used for only leading to
Cross the liquid crystal drop method that heating is solidified to liquid crystal sealing agent.Additionally, in photo-thermal and using type liquid crystal drop
Fall in method, even light is difficult to also there is sufficient curable under the distribution reaching, therefore, it is possible to guarantee
The degree of freedom of the distribution design of panel, so that the manufacture of the display panels of high reliability is more
Easily.
Specific embodiment
Used in the present invention, (a) intramolecular does not contain o-o bond (- O-O-) and nitrogen-nitrogen key
The hot radical polymerization initiator of (- N=N-), as long as free radical can be produced by heating,
Start chain polymerization reaction compound be not particularly limited, can for Benzoinum class (benzoin),
Benzoinum ethers, acetophenones, benzpinacone (benzopinacol) class.Wherein from reactivity
Consider with the dissolubility to liquid crystal, the compound that particularly preferably above-mentioned formula (1) represents.
In above-mentioned formula (1), Y1And Y2Represent hydrogen atom, phenyl or silicon atom independently of one another,
Preferably at least one of them is silicon atom.In formula (1), R1～R6In as carbon number 1～
4 straight or branched alkyl (below only claim C1～C4 alkyl), for example can for methyl, ethyl,
N-pro-pyl, isopropyl, tert-butyl group etc..Additionally, X1～X4Middle halogen can for fluorine atom, chlorine atom,
Bromine atoms etc..
The Y of formula (1)1Or Y2For when beyond hydrogen atom, R1R2R3Y1- or R4R5R6Y2-
It is preferably phenyl, the phenyl with C1～C4 alkyl displacement of 1～3, two C1～C4 alkyl first silicon
Alkyl or three C1～C4 aIkylsilyl groups, more preferably two C1～C4 aIkylsilyl groups
Or three C1～C4 aIkylsilyl groups, more preferably three C1～C4 aIkylsilyl groups.
The R of formula (1)1R2R3Y1-, R4R5R6Y2- in, two or three C1～C4 straight chain or
In branched alkyl silicyl, C1～C4 alkyl of 2 or 3 can be the same or different.
This silicyl (silyl) can be dimetylsilyl, diethylsilane base, Methylethyl
Two C1 of silicyl etc.～C4 aIkylsilyl groups；Trimethyl silyl, triethyl-silicane
Three C1 of base, dimethylethylsilyl, t-butyldimethylsilyl etc.～C4 alkyl first
Silylation.Among these, most preferably three C1～C4 aIkylsilyl groups, more preferably trimethyl
Silicyl.
The X of formula (1)1～X4Represent hydrogen atom, methyl, ethyl, methoxyl group, second independently of one another
Epoxide, phenoxy group or halogen atom, preferably X1～X4It is hydrogen atom.
As the compound represented by formula (1), specific for, can for benzpinacone, 1,2-
Dimethoxy -1,1,2,2- tetraphenyl ethane, 1,2- diethoxy -1,1,2,2- tetraphenyl ethane, 1,2- bis-
Phenoxy group -1,1,2,2- tetraphenyl ethane, 1,2- dimethoxy -1,1,2,2- four (4- aminomethyl phenyl) ethane, 1,2-
Hexichol Oxy-1, double (the trimethylsiloxy group) -1,1,2,2- four of 1,2,2- tetra- (4- methoxyphenyl) ethane, 1,2-
Diphenylphosphino ethane (1,2-bis (trimethylsiloxy) -1,1,2,2-tetraphenylethane), 1,2- double (triethyl groups
Siloxy) -1,1,2,2- tetraphenyl ethane, double (tertiary butyl dimethyl Si the base) -1,1,2,2- tetraphenyl of 1,2-
Ethane, 1- hydroxyl -2- trimethylsiloxy group -1,1,2,2- tetraphenyl ethane, 1- hydroxyl -2- triethyl group silica
Base -1,1,2,2- tetraphenyl ethane, 1- hydroxyl -2- tertiary butyl dimethyl Si base -1,1,22- tetraphenyl ethane
Deng, preferably 1- hydroxyl -2 trimethylsiloxy group -1,1,2,2- tetraphenyl ethane, 1- hydroxyl -2- triethyl group
Siloxy -1,1,2,2- tetraphenyl ethane, 1- hydroxyl -2- tertiary butyl dimethyl Si base -1,1,2,2- tetraphenyl
Double (trimethylsiloxy group) -1 of ethane, 1,2-, 1,2,2- tetraphenyl ethane, more preferably 1- hydroxyl -2 front three
Double (the trimethylsiloxy group) -1,1,2,2- tetraphenyl ethane of base siloxy -1,1,2,2- tetraphenyl ethane, 1,2-.
But, as long as there is the structure of formula (1) it is not limited to these compounds.Additionally, also may be used
Used with two or more simultaneously.
In above-mentioned hot radical polymerization initiator, benzpinacone by Tokyo chemical conversion industry (strain) and
Wako Pure Chemical Industries (strain) etc. are sold in market.Additionally, the hydroxy ether compound of benzpinacone can be used
Known method is readily synthesized.Additionally, the hydroxyl monosilane etherate of benzpinacone, permissible
By heating corresponding benzpinacone and various monosilane agent under the base catalyst of pyridine etc.
Method synthesis obtain.
As silylating agent, can for people commonly known as trimethylsilylation agent
Trim,ethylchlorosilane (TMCS), hexamethyldisiloxane (HMDS), N, the double (trimethyl of O-
Monosilane) trifluoroacetamide (BSTFA) and the triethyl group chlorine as triethylsilyl agent
Silane (TECS), the tertbutyl methyl monosilane (TBMS) as t-butyldimethylsilyl
Deng.These chemical reagent silicon derivative maker from the market etc. can have been bought.As silicyl
The response magnitude of agent, preferably with respect to 1.0～5.0 times moles of 1 mole of hydroxyl of subject compound.
It is more preferably 1.5～3.0 times moles.If less than 1.0 times moles then reaction efficiency poor, the time is long,
Thus promote thermal decomposition.And if greater than 5. times moles, then separation when reclaiming is deteriorated, or carry
Pure become difficult.
Can be pyridine, triethylamine etc. as base catalyst.Produce during base catalyst capture reaction
Raw hydrogen chloride, has an effect that reaction system is maintained at alkalescence, and extracts the hydrogen of hydroxyl, enters one
Step promotes the effect of reaction.As long as content is more than 0.5 times mole with respect to the hydroxyl of object,
Can also use as solvent.
As solvent, the non-polar organic solvent of hexane, ether, toluene etc. due to being not involved in reaction thus
More suitable.Additionally, also, it is preferred that pyridine, dimethylformamide (dimethylformaldehyde)
(DMF), the polar solvent of dimethyl sulfoxide (DMSO), oxolane (THF), acetonitrile etc..
Content is preferably the mass concentration of solute about 5～40 mass parts.It is more preferably 10～30 matter
Amount part.If the content of solvent is very few, reaction can be slack-off, promotes heat and decomposes, and so that yield is reduced.
If contrary excessive, by-product also can become many so that yield declines.
(a) hot radical polymerization initiator that the present invention uses is preferably nominal particle size, and uniformly divides
Dissipate.If its mean diameter is excessive, when manufacturing the liquid crystal display of narrow gap, can become upper and lower
Can not form the undesirable element in gap etc. during glass substrate laminating well, therefore preferably 5 μm with
Under, more preferably less than 3 μm.In addition it is also possible to make it infinitely tiny, but usual lower limit is
0.1 μm about.Particle diameter passes through laser diffraction and scattering formula particle size distribution measurement device (dry type) (strain formula meeting
SEISHIN enterprise of society manufactures, LMS-30) measure.
When with the total amount of the curable resin of the liquid crystal sealing agent of the present invention for 100 mass parts timing, should
The content of hot radical polymerization initiator is 1 mass 0.0001～10 mass parts, more preferably
0.0005～5 mass parts, particularly preferably 0.001～3 mass parts.Additionally, curable resin refers to
(c) composition and (d) composition in the case of containing as needed.Following all same in this application.
As long as additionally, used in the present invention composition (b) radical polymerization preventing agent can with from
In radical polymerization initiator, above-mentioned curable resin monomer produce radical reaction and be prevented from
The compound of polymerization, is not particularly limited, it is possible to use quinones, piperidines base class, Hinered phenols, Asia
Nitro (nitroso) class etc..For specific, can be naphthoquinone, 2 hydroxy naphthalene quinone, 2- methyl naphthalene
Quinone, 2- methoxynaphthoquinone, 2,2,6,6,-tetramethyl-piperidyl -1- epoxide, 2,2,6,6,-tetramethyl -4- hydroxyl
Piperidyl -1- epoxide, 2,2,6,6,-tetramethyl -4- methoxypiperidinyl -1- epoxide, 2,2,6,6,-tetramethyl -4-
Phenoxypiperidines base -1- epoxide, hydroquinone, 2- methyl hydroquinone, 2- methoxyl group hydroquinone,
1,4-benzoquinone, butylated hydroxyanisol, 2,6- di-t-butyl -4- ethyl -phenol, 2,6- di-t-butyl first
Phenol, stearyl β-(3,5- di-tert-butyl-hydroxy phenyl) propanoic acid, 2,2 '-di-2-ethylhexylphosphine oxide (4- ethyl
- 6- tert-butyl phenol), 4,4 '-thio two -3 methy 6 tert butyl phenol), the double (3- of 4,4 '-butylidene
Methyl-6-tert-butylphenol), double [1,1- dimethyl -2- [β-(the 3- tertiary butyl-4-hydroxy -5- aminomethyl phenyl) of 3,9-
Propionyloxy] ethyl], 2,4,8,10- tetra- oxaspiro [5,5] hendecane, four-[methyl -3- (3 ', 5 '-two-tertiary fourth
Base -4 '-hydroxy-phenylpropionic acid ester) methane, 1,3,5- tri- (3 ', 5 '-di-t-butyl -, 4 '-hydroxybenzyl)-sec-
Triazine -2,4,6- (1H, 3H, 5H) triketone, p methoxy phenol, 4- methoxyl group -1- naphthols, thio hexichol
Amine, the aluminium salt of N- nitroso-group phenylhydroxylamine, trade name ADEKA ' s Tab LA-81, commodity
Title ADEKA ' s Tab LA-82 (ADEKA Corp.'s production) etc., but be not limited thereto.
Wherein, with above-mentioned hot radical polymerization initiator and with and play remarkable result, be above-mentioned formula
(2) the radical polymerization preventing agent described in～(4).These radical polymerization preventing agents can be independent
Using it is also possible to two or more is used in combination.
Additionally, R8 represents hydrogen atom, hydroxyl, the straight chain of carbon number 1～4 in above-mentioned formula (3)
Or branched alkoxy, phenoxy group, acetamido (- NHCOCH3), amino (- NH2), carboxylic
Base (- COOH), cyano group (CN), benzoyloxy (benzoyloxy) (- OCOC6H5),
Isothiocyanate group (- NCS) or oxo base (=O), preferably hydrogen atom, hydroxyl, carbon is former
The straight or branched alkoxyl of subnumber 1～4, phenoxy group, amino, carboxyl, more preferably hydrogen are former
Son, hydroxyl, amino, carboxyl, particularly preferably hydrogen atom, hydroxyl.
Composition (b) radical polymerization preventing agent, can have (methyl) third with synthetic ingredient (c)
The method added during the curable resin of enoyl- is it is also possible to have (methyl) third to composition (c)
The curable resin of enoyl- and composition (d) have the one of of the curable resin of epoxy radicals or
Two are added and make the method that it dissolves, in order to obtain more effect, preferably to composition (c)
There is the curable resin of (methyl) acryloyl group and composition (d) has the curable tree of epoxy radicals
The method that it dissolves is added and made to wherein one or two of fat.
B () is when the total amount of the curable resin in the liquid crystal sealing agent with the present invention is for 100 mass parts
Timing, the content of radical polymerization preventing agent is preferably 1 mass 0.0001～1 mass parts, more excellent
Elect 0.001～0.5 mass parts, particularly preferably 0.01～0.2 mass parts as.Radical polymerization prevents
If agent is very few, sufficient operability can not be obtained, if crossing at most prolonging due to thermal response in addition
There is liquid crystal pollution late.
The liquid crystal sealing agent of the present invention has the curable tree of (methyl) acryloyl group for composition (c)
Fat.As this curable resin, for example can for (methyl) acrylate ((metha) acryl ester),
Epoxy (methyl) acrylate (epoxy (metha) acrylate) etc..As (methyl) acrylic acid
Ester, can be benzyl methacrylate, cyclohexyl methacrylate, two (methyl) acrylic acid third
Three alcohol esters, glycerol triacrylate, EO modification glycerol triacrylate, tetramethylolmethane propylene
Acid esters, trimethylolpropane trimethacrylate, three (acrylyl oxy-ethyl) isocyanuric acid ester, double season
Penta tetrol six acrylate, phloroglucinol triacrylate etc..Epoxy (methyl) acrylate is permissible
Obtained with known method by epoxy resin and (methyl) acrylic acid reaction.As raw material epoxy
Resin is not particularly limited, epoxy resin more than preferably 2 senses, for example, can be bisphenol A-type
Epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, phenol novolak-type epoxy
Resin, cresol novolak type epoxy resin, phenol novolak type epoxy resin, bisphenol A novolac type epoxy resin, Bisphenol F
Phenolic resin varnish type epoxy resin, alicyclic epoxy resin, aliphatic chain epoxy resin, (+)-2,3-Epoxy-1-propanol
Ester type epoxy resin, glycidyl amine type epoxy resin, hydantoin type epoxy resin, isocyanuric acid
Ester type epoxy resin, there is the phenol novolak type epoxy resin of tris-phenol skeleton, additionally,
Can also be catechol, resorcinol etc. two trifunctional phenol class 2-glycidyl etherate, two functional alcohol
Class 2-glycidyl etherate and their halogenide, hydrogen addition product etc..Wherein from liquid crystal pollution
From the viewpoint of, more preferred resorcinolformaldehyde resin.Additionally, epoxy radicals and (methyl)
The ratio of acryloyl group is not particularly limited it is contemplated that operation adaptability and liquid crystal pollution suitably select
Select.
Additionally, when setting the total amount of liquid crystal sealing agent as 100 mass parts, (c) has (methyl) propylene
Containing ratio in liquid crystal drop method liquid crystal sealing agent for the curable resin of acyl group is preferably 30～90
In the range of mass parts, more preferably 50～90 mass parts.
Also by using composition (d), there is epoxy in the liquid crystal drop method liquid crystal sealing agent of the present invention
The curable resin of base, and bonding strength can be improved.As being used the curable with epoxy radicals
Resin, is not particularly limited, epoxy resin more than preferably 2 senses, such as bisphenol type epoxy
Resin, bisphenol F epoxy resin, bisphenol-s epoxy resin, phenol novolak type epoxy resin,
Cresol novolak type epoxy resin, phenol novolak type epoxy resin, bisphenol A novolac type epoxy resin, bisphenol F phenolic varnish
Type epoxy resin, alicyclic epoxy resin, aliphatic chain epoxy resin, glycidyl ester type epoxy
Resin, glycidyl amine type epoxy resin, hydantoin type epoxy resin, isocyanurate type epoxy
Resin, there is the phenol novolak type epoxy resin of tris-phenol skeleton, further, it is also possible to be
The 2-glycidyl etherate of two trifunctional phenol classes, the 2-glycidyl etherate of two sense alcohols, and
Their halogenide, hydrogen addition product etc..When setting the total amount of liquid crystal sealing agent as 100 mass parts, become
Point (d) have epoxy radicals the content shared in liquid crystal sealing agent of curable resin be preferably 1～
30 mass parts.
In the liquid crystal drop method liquid crystal sealing agent of the present invention, and the composition that composition (d) is used in conjunction with
E () thermal curing agents are not particularly limited, can be polyamines class, polyhydric phenols, hydrazide compound etc.,
Particularly preferably use organic hydrazides of solid-state.For example, it is possible to be the salicylic acid acyl as aromatic hydrazide
Hydrazine, benzoic acid hydrazide, 1- naphthoic acid hydrazides, terephthaldehyde's acid dihydrazide, isophthalic dihydrazide,
2,6- naphthoic acid two hydrazides, 2,6- pyridine two hydrazides, 1,2,4 benzene three hydrazides, 1,4,5,8- naphthoic acid four acyl
Hydrazine, Pyromellitic Acid four hydrazides etc..Additionally, if aliphatic hydrazide compound, such as can be
Formylhydrazine, acethydrazide, propanoic acid hydrazides, careless acid dihydrazide, acid dihydrazide, succinum acid dihydrazide,
Glutaric, adipic dihydrazide, 1,5-pentanedicarboxylic acid. two hydrazides, sebacic dihydrazide, 1,4- hexamethylene
Alkane two hydrazides, winestone acid dihydrazide, Fructus Mali pumilae acid dihydrazide, iminodiacetic acid two hydrazides, N, N '-
Hexamethylene bis semicarbazides, citric acid three hydrazides, nitriloacetic acids three hydrazides, cyclohexanetricarboxylic acid three
The hydantoin skeleton of double (diazanyl ethyl) -5- isopropyl hydantoin of hydrazides, 1,3- etc., preferably tool
Have the two of L-Valine hydantoin skeleton (skeleton that the carbon atom of hydantoin ring is replaced by isopropyl)
Hydrazide compound, three (1- Hydrazinocarbonyl methyl) isocyanuric acid ester, three (2- Hydrazinocarbonyl ethyl) isocyanide urea
Acid esters, three (2- Hydrazinocarbonyl ethyl) isocyanuric acid ester, three (3- Hydrazinocarbonyl propyl group) isocyanuric acid ester,
Double (2- Hydrazinocarbonyl ethyl) isocyanuric acid ester etc..This thermal curing agents can be used alone it is also possible to 2
Plant use mixed above.In terms of the balance of solidification reactivity and potentiality, preferably M-phthalic acid
Two hydrazides, acid dihydrazide, adipic dihydrazide, sebacic dihydrazide, three (1- Hydrazinocarbonyl first
Base) isocyanuric acid ester, three (2- Hydrazinocarbonyl ethyl) isocyanuric acid ester, three (2- Hydrazinocarbonyl ethyls) are different
Cyanurate, three (3- Hydrazinocarbonyl propyl group) isocyanuric acid ester, particularly preferably acid dihydrazide,
Sebacic dihydrazide.With regard to using usage amount during related (e) thermal curing agents, being set as point (d) tool
Have the curable resin of epoxy radicals epoxy radicals epoxide equivalent be 1 when, be 0.5～2.0 equivalent, excellent
Elect 0.8～1.2 equivalent as.
In the liquid crystal drop method liquid crystal sealing agent of the present invention, using composition (f) silane coupler,
Bonding strength and moisture-proof reliability can be improved.As silane coupler, can be 3- (2,3- epoxy the third oxygen)
Propyl trimethoxy silicane (3-glycidoxypropyltrimethoxysilane), 3- (2,3- epoxy third oxygen)
Hydroxypropyl methyl dimethoxysilane, 3- (2,3- epoxy the third oxygen) hydroxypropyl methyl dimethoxysilane, 2- (3,
4- epoxycyclohexyl) ethyl trimethoxy silane, N- phenyl-gamma-amino propyl trimethoxy silicane, N- (2-
Amino-ethyl) 3- amino propyl methyl dimethoxysilane, N- (2- amino-ethyl) 3- amino propyl methyl
Trimethoxy silane, 3- TSL 8330,3- mercaptopropyl trimethoxysilane, ethylene
Base trimethoxy silane, N- (2- (vinyl benzyl amino) ethyl) 3- TSL 8330 hydrochloric acid
Salt, 3- methacryloxypropyl trimethoxy silane, 3- chloropropylmethyldimethoxysilane,
3- r-chloropropyl trimethoxyl silane etc..(f) silane coupler shared content in liquid crystal sealing agent be by
When the total amount of the liquid crystal sealing agent of the present invention is calculated as 100 mass parts, preferably 0.05～3 mass parts.
In the liquid crystal drop method liquid crystal sealing agent of the present invention, use (g) inorganic filler, permissible
Improve bonding strength and moisture-proof reliability.As this composition (g) inorganic filler, can be for dissolving
Silicon dioxide, crystalline silica, carborundum, silicon nitride, boron nitride, Calcium Carbonate, magnesium carbonate,
Barium sulfate, calcium sulfate, Muscovitum, Talcum, clay, aluminium oxide, magnesium oxide, zirconium oxide, hydroxide
Aluminum, magnesium hydroxide, calcium silicates, aluminium silicate, lithium aluminium silicate, Zirconium orthosilicate., Barium metatitanate., glass fibre,
Carbon fiber, molybdenum bisuphide, asbestos etc., preferably dissolve silicon dioxide, crystalline silica, nitridation
Silicon, boron nitride, Calcium Carbonate, barium sulfate, calcium sulfate, Muscovitum, Talcum, clay, aluminium oxide, hydrogen
Aluminium oxide, calcium silicates, aluminium silicate, more preferably dissolve silicon dioxide, crystalline silica, oxygen
Change aluminum, Talcum.These inorganic fillers can also be mixed two or more use.Its mean diameter,
If mean diameter is excessive, when manufacturing the liquid crystal cells of narrow gap, become upper lower glass substrate patch
The main cause in gap can not be formed well, therefore less than 3 μm is suitable during conjunction, preferably 2 μm
Below.Particle diameter passes through laser diffraction and scattering formula particle size distribution measurement device (dry type) (Co., Ltd.
SEISHIN enterprise manufactures, LMS-30) measure.
Can be used for the inorganic filler (g) of liquid crystal sealing agent of the present invention content in liquid crystal sealing agent
It is usually 1～60 mass parts with 100 mass parts timing by the total amount of the liquid crystal sealing agent of the present invention,
It is preferably 1～40 mass parts.If the content of inorganic filler is very few, the bonding to glass substrate is strong
Degree can decline, and moisture-proof reliability is also bad, and after moisture absorption, bonding strength can be greatly reduced.And inorganic fill out
Fill agent content excessive when, then be unlikely to deform it is impossible to form the gap of liquid crystal cells.
The liquid crystal sealing agent of the present invention, due to the liquid crystal sealing agent for photo-thermal and with curing type, can also contain
There is composition (h) Photoepolymerizationinitiater initiater.As long as Photoepolymerizationinitiater initiater can be by UV or visible ray
Irradiation produce free radical and cause chain polymerization reaction compound, be not particularly limited, for example
Can for benzyl dimethyl ketal, 1- hydroxyl cyclohexyl-phenyl ketone, diethyl thioxanthone, benzophenone,
2-ethyl-anthraquinone, 2- hydroxy-2-methyl propiophenone, 2- methyl-(4- (first sulfur) phenyl) -2- morpholino -1-
Propane, 2,4,6- trimethyl benzoyl diphenyl base phosphine oxide etc..Additionally, the angle from liquid crystal pollution
Degree sets out, and preferably uses intramolecular and has the material of (methyl) acryloyl group, for example, preferably use 2-
Methacryloxyethyl isocyanates and 1- [4- (2- hydroxyl-oxethyl)-phenyl] -2- hydroxyl -2-
The reaction product of methyl isophthalic acid-propane -1- ketone.This compound can be according to International Publication No.
Method manufacture described in No. 2006/027982.Photoepolymerizationinitiater initiater is shared in liquid crystal sealing agent
When content is to set the total amount of liquid crystal sealing agent as 100 mass parts, preferably 1～10 mass parts.
In the liquid crystal sealing agent of the present invention, as needed, the solidification such as organic acid and imidazoles can also be combined
The additive such as accelerator, organic filler and pigment, levelling agent, defoamer, solvent.
Obtain an example of the method for liquid crystal sealing agent as the present invention, can be side shown below
Method.First, in (c) composition as needed, dissolving mixing (d) composition.Then by (b)
Composition is dissolved in this mixture, as needed, dissolves (h) composition.Next, add (a) becoming
Point, (f) composition, (e) composition, (g) composition, and be added as needed on organic filler, froth breaking
Agent, levelling agent, solvent etc., using known mixing arrangement, such as three rollers, sand mill, ball grind
The mix homogeneously such as machine, are filtered with metallic screen, thus to manufacture the liquid crystal sealing agent of the present invention.
The liquid crystal display of the present invention is arranged to be formed with a pair of base of regulation electrode on substrate
Plate keeps at a certain distance away relative configuration, around uses the liquid crystal sealing agent sealing of the present invention, its gap is enclosed
Liquid crystal.The species of the liquid crystal being enclosed is not particularly limited.Here, substrate refer to by glass, quartz,
At least side of the compositions such as plastics, silicon has the substrate of the combination of light transmission.Its preparation method can be at this
After the pad (gap control material) of glass fibre etc. is added on the liquid crystal sealing agent of invention, this one
After one of them upper this liquid crystal sealing agent of coating using point gum machine or silk-screen printing device etc. of substrate,
After carrying out precuring at 80 DEG C～120 DEG C as needed, liquid crystal is dropped in this liquid crystal sealing agent
Weir dike inside, and overlapping opposite side glass substrate in a vacuum, and reserve gap.After gap is formed,
At 90 DEG C～130 DEG C, solidification just can obtain the liquid crystal display of the present invention for 1～2 hour.Additionally,
Using photo-thermal and when using type, with ultraviolet irradiation machine to liquid crystal sealing agent portion irradiation ultraviolet radiation, carry out light
Solidification.Ultraviolet irradiation amount is preferably 500mJ/cm2～6000mJ/cm2, more preferably 1000
mJ/cm2～4000mJ/cm2.Afterwards as needed, solidify 1～2 hour at 90 DEG C～130 DEG C,
Thus obtaining the liquid crystal display of the present invention.The liquid crystal display of the present invention being achieved in that does not have
Because the display that liquid crystal pollution causes is bad, there is good cohesive, moisture-proof reliability.As pad,
Can be glass fibre, silicon grain, polymer strain etc..Its diameter can be different according to purpose, usually
2～8 μm, preferably 4～7 μm.Its usage amount is with respect to liquid crystal sealing agent 100 mass of the present invention
Part, usually 0.1～4 mass parts, preferably 0.5～2 mass parts, more preferably 0.9～1.5
About mass parts.
The liquid crystal display of the present invention is arranged to be formed with a pair of base of regulation electrode on substrate
Plate keeps at a certain distance away relative configuration, around uses the liquid crystal sealing agent sealing of the present invention, its gap is enclosed
Liquid crystal.The species of the liquid crystal being enclosed is not particularly limited.Here, substrate refer to by glass, quartz,
At least side of the compositions such as plastics, silicon has the substrate of the combination of light transmission.Its preparation method can be at this
After the pad (gap control material) of glass fibre etc. is added on the liquid crystal sealing agent of invention, this one
After one of them upper this liquid crystal sealing agent of coating using point gum machine or silk-screen printing device etc. of substrate,
After carrying out precuring at 80～120 DEG C as needed, liquid crystal is dropped in this liquid crystal sealing agent
Inside the dike of weir, and overlapping opposite side glass substrate in a vacuum, and reserve gap.After gap is formed,
At 90～130 DEG C, solidification just can obtain the liquid crystal display of the present invention for 1～2 hour.Additionally, making
With photo-thermal and when using type, with ultraviolet irradiation machine to liquid crystal sealing agent portion irradiation ultraviolet radiation, carry out light solid
Change.Ultraviolet irradiation amount is preferably 500mJ/cm2～6000mJ/cm2, more preferably
1000mJ/cm2～4000mJ/cm2.Afterwards as needed, solidify 1～2 at 90 DEG C～130 DEG C
Hour, thus obtaining the liquid crystal display of the present invention.The liquid crystal display list of the present invention being achieved in that
The display that unit does not cause because of liquid crystal pollution is bad, has good cohesive, moisture-proof reliability.Make
For pad, can be glass fibre, silicon grain, polymer strain etc..Its diameter can be different according to purpose,
It is usually 2 μm～8 μm, preferably 4 μm～7 μm.Its usage amount is close with respect to the liquid crystal of the present invention
Envelope agent 100 mass parts, usually 0.1～4 mass parts, preferably 0.5～2 mass parts are more preferred
About 0.9～1.5 mass parts.
The Thermocurable of the liquid crystal sealing agent of the present invention is very good, in the heating process of liquid crystal drop method
Can solidify rapidly.Therefore, constituent is also few to the dissolution of liquid crystal, can reduce liquid crystal display
The display of unit is bad.Further, since operability and storage stability are also very well it is adaptable to liquid crystal
Show the manufacture of unit.Further, since its solidfied material also has good bonding strength, thermostability, resistance to
The various solidfied material characteristic such as moist, thus using the present invention liquid crystal sealing agent, can make have excellent
The liquid crystal display of different reliability.Additionally, the liquid crystal being made using the liquid crystal sealing agent of the present invention
Show that unit also has as liquid crystal display needed voltage retention height, the low spy of ion concentration
Property.
Embodiment
Hereinafter, the present invention is explained in more detail by synthesis example, embodiment, but the present invention is not
Embodiment is limited.Additionally, in the case of there is no specified otherwise, " part " and " % " herein
For quality standard.
[synthesis example 1]
(synthesis of 1- hydroxyl -2- trimethylsiloxy group -1,1,2,2- tetraphenyl ethane)
Marketed 100 parts (0.28 mole) benzpinacones (Tokyo chemical conversion system) are dissolved in
In 350 parts of dimethylformamides (dimethylformaldehyde), and it is added thereto to 32 part (0.4
Mole) pyridine as base catalyst, 150 parts of (0.58 mole) BSTFA (SHIN-ETSU HANTOTAI's chemical industry
System) as silylating agent, it is warmed up to 70 DEG C, stir 2 hours.By the reactant liquor obtaining cooling,
200 parts of water being stirred while pouring into, so that product is precipitated, inactivation separates unreacted monosilane
Base agent.Fully wash after filtration separation, so that it is recrystallized with acetone, after purification, obtain 1- hydroxyl
105.6 parts of trimethylsiloxy group -1,1,2,2- tetraphenyl ethane of -2- (yield 88.3%).Through with HPLC
Analysis, is 99.0% (area percentage).Additionally, in HPLC-MASS obtain 438 point
Daughter ion peak value.Also from being dissolved in DMSO-d6NMR (proton) spectrum in identified purpose
Thing.The chemical displacement value of NMR spectra, hydroxyl proton is 5.8ppm (1H), siloxy onychostroma
Son is 0.0ppm (9H), and phenyl protons are 7.1ppm (16H), 7.4ppm (4H).
[with reference to synthesis example 1]
(synthesis of the epoxy acrylate of bisphenol A type epoxy resin)
By 282.5g bisphenol A type epoxy resin (name of product：YD-8125, Nippon Steel's chemistry strain
Formula commercial firm system) it is dissolved in 266.8g toluene, and it is added thereto to 0.8g dibenzylatiooluene work
Forbid agent for polymerization, be warmed up to 60.Afterwards, add the acrylic acid 117.5g of epoxy radicals 100% equivalent,
It is warmed up to 80 DEG C again, is added to catalysts alkyl trimethyl ammonium chloride 0.6g, at 98 DEG C
Lower stir about 30 hours, obtains reactant liquor.Wash this reactant liquor, by distilling out toluene, obtain
Epoxy acrylate 395g (the KAYARAD of target bisphenol A-typeRTMR-93100).
[embodiment 1～5, comparative example 1～3]
(modulation of liquid crystal drop method liquid crystal sealing agent)
After each resinous principle of ratio mix and blend shown in table 1 below (composition (c), composition (d)),
Heating for dissolving radical polymerization preventing agent (composition (b)), Photoepolymerizationinitiater initiater (ingredient h)).Cooling
To after room temperature, be properly added silane coupler (composition (f)), inorganic filler (composition (g)),
Thermal free radical initiator (composition (a)), thermal curing agents (composition (e)) etc., in three rollers after stirring
So that it is disperseed in grinder, and filtered with metallic screen (635 mesh), to modulate the liquid of embodiment 1～5
Brilliant drop method liquid crystal sealing agent.In addition similarly, using each composition comparison example shown in table 1
1～3 liquid crystal drop method liquid crystal sealing agent.
It is below the assessment item content of each liquid crystal drop method liquid crystal sealing agent and its result of modulation.
(Thermocurable test)
The each liquid crystal drop method liquid crystal sealing agent casting mold making is 3cm × 3cm × 1mm,
Solidify under 120 DEG C × 1hr.By measuring the Shaw A hardness of solidfied material, evaluate curable.Result
As shown in table 1.
(operability test)
To each liquid crystal drop method making with adding 5 μm of pad in liquid crystal sealing agent 15g
(PF-50S：Nippon Electric Glass Co., Ltd.'s system) after 0.15g, with rotation 500rpm, revolution
1500rpm carries out vacuum stirring deaeration in 5 minutes.Using vacuum stirring deaeration blender
(VMXC-360k：EME Corp.'s system) as vacuum stirring defoaming device.Place it in
In the environment of 23 DEG C, the time of measurement gelation, and evaluated according to following benchmark.Result such as table
Shown in 1.
○：There is not gelation more than or equal to 168 hours
△：It was less than more than or equal to 96 hours 168 hours and gel occurs
×：To less than 96 hours generation gels after deaeration
(liquid crystal pollution test)
By irradiated 3000mJ/cm2Ultraviolet each liquid crystal drop method liquid crystal sealing agent 100mg
Left and right is coated in the bottom of 10ml sample bottle, is subsequently adding the liquid crystal (MLC-6866-100 of 10 times amount：
Merck Co. Ltd. system).After heating 1 hour at 120 DEG C, cool down 30 minutes.Use decantation respectively
Separate supernatant, with the super megger (R8340 of numeral：Advantest Corp's system) measurement resistance
Resistivity in the case of rate, with no sealant is compared.Judged according to following.
○：Resistivity is more than or equal to 1.0E+11
△：Resistivity is more than or equal to 1.0E+11, less than 1.0E+11
×：Resistivity is less than 1.0E+10
Additionally, " 1.0E+11 " expression " 1.0 × 10 of resistivity11", other descriptions are also identical.
[table 1]
1. synthesis example 1 synthesizes
2. KayaesterO (chemical medicine Akzo Co. Ltd. system)
3. Port リ ス ト ッ プ 7300P (Hakuto KK's system)
4. NQI (Kawasaki chemical conversion Co. Ltd. system)
5. LSN (Kawasaki chemical conversion Co. Ltd. system)
6. HQ (Kawaguchi's chemical industry Co. Ltd. system)
7. BHT (Tokyo HuaCheng Industry Co., Ltd's system)
8. synthesized by with reference to synthesis example 1
9. double (Oxiranylmethoxy) benzene (1,3-bis (oxiranylmethoxy) benzene) of 1,3-
(rapids this Co., Ltd. safe of length sells)
10. SDH (big KCC system)
※ is ground into after the microgranule of 1.5 μm of mean diameter by SDH jet mill and uses
Sila-Ace S-510 (Chisso Co. Ltd. system)
D-600 (Japanese Talcum Co. Ltd. system)
Method synthesis with No. WO2006/027982 record of International Publication
According to the result of table 1, confirm and comprised (a) intramolecular without o-o bond (- O-O
-) and the hot radical polymerization initiator of nitrogen-nitrogen key (- N=N-), (b) radical polymerization
Preventing agent and (c) have the liquid crystal drop method liquid of the curable resin of (methyl) acryloyl group
The Thermocurable of brilliant sealant (embodiment 1～5), operability, liquid crystal pollution are all very outstanding.
Wherein, as (b) radical polymerization preventing agent, the liquid crystal drop method containing predetermined substances such as naphthoquinone
Particularly outstanding with liquid crystal sealing agent (embodiment 1～4).
[Industrial Availability]
The liquid crystal drop method liquid crystal sealing agent of the present invention, has good heat curable, and operates
The solidfied material characteristic of property and storage stability, bonding strength etc. is also very outstanding.Thus it is ensured that liquid
Degree of freedom in the design of brilliant display unit, also has contributed much to productivity ratio and long-term reliability.
Claims (11)
1. a kind of liquid crystal drop method liquid crystal sealing agent is it is characterised in that contain：A () intramolecular does not have the hot radical polymerization initiator of o-o bond (- O-O-) and nitrogen-nitrogen key (- N=N-), (b) radical polymerization preventing agent and (c) have the curable resin of (methyl) acryloyl group
Described composition (b) is the radical polymerization preventing agent of following formula (4)：
In formula (4), R13Represent the straight or branched alkyl of hydrogen atom or carbon number 1～4.
2. liquid crystal drop method liquid crystal sealing agent according to claim 1, wherein, described composition (a) is the compound being represented by following formula (1)：
In formula (1), Y1、Y2Represent hydrogen atom, phenyl or silicon atom, R independently of one another1～R6Represent the straight or branched alkyl of hydrogen atom or carbon number 1～4, X independently of one another1～X4Represent hydrogen atom, methyl, ethyl, methoxyl group, ethyoxyl, phenoxy group or halogen atom independently of one another, wherein, work as Y1Or Y2When being hydrogen atom, it is joined respectively to Y1Or Y2R1～R3Or R4～R6It is non-existent.
3. liquid crystal drop method liquid crystal sealing agent according to claim 1, also contains curable resin and (e) thermal curing agents that (d) has epoxy radicals.
4. liquid crystal drop method liquid crystal sealing agent according to claim 3, wherein, described composition (e) is organic hydrazides.
5. liquid crystal drop method liquid crystal sealing agent according to claim 1, wherein, also contains (f) silane coupler.
6. liquid crystal drop method liquid crystal sealing agent according to claim 1, wherein, also contains (g) inorganic filler.
7. liquid crystal drop method liquid crystal sealing agent according to claim 1, wherein, also contains (h) Photoepolymerizationinitiater initiater.
8. liquid crystal drop method liquid crystal sealing agent according to claim 3, wherein, with 100 mass parts timing, the content of described composition (b) is 0.0001 mass parts to 1 mass parts to the total amount of described composition (c) and described composition (d).
9. the manufacture method of the liquid crystal drop method liquid crystal sealing agent any one of a kind of claim 1 to 8, wherein, described manufacture method includes described composition (b) being dissolved in the operation of described composition (c).
10. the manufacture method of the liquid crystal drop method liquid crystal sealing agent described in a kind of claim 3 or 4, wherein, described manufacture method includes described composition (b) being dissolved in the operation of described composition (d).
A kind of 11. liquid crystal displays, wherein, described liquid crystal display is by by the hermetically sealed liquid crystal display of solidfied material obtained by the solidification of liquid crystal drop method liquid crystal sealing agent any one of claim 1 to 8.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011154581 | 2011-07-13 | ||
| JP2011-154581 | 2011-07-13 | ||
| CN201280034501.0A CN103649825B (en) | 2011-07-13 | 2012-07-12 | Liquid crystal sealing agent and use its liquid crystal display |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280034501.0A Division CN103649825B (en) | 2011-07-13 | 2012-07-12 | Liquid crystal sealing agent and use its liquid crystal display |
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| CN201610060537.6A Pending CN106397697A (en) | 2011-07-13 | 2012-07-12 | Liquid crystal sealant and liquid crystal display cell using same |
| CN201280034501.0A Active CN103649825B (en) | 2011-07-13 | 2012-07-12 | Liquid crystal sealing agent and use its liquid crystal display |
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| JP (2) | JP6092103B2 (en) |
| KR (1) | KR101885944B1 (en) |
| CN (2) | CN106397697A (en) |
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| JP6212055B2 (en) * | 2013-01-11 | 2017-10-11 | 日本化薬株式会社 | Liquid crystal sealant and liquid crystal display cell using the same |
| JP6445780B2 (en) * | 2013-05-09 | 2018-12-26 | 積水化学工業株式会社 | Liquid crystal dropping method sealing agent, vertical conduction material, and liquid crystal display element |
| WO2014189110A1 (en) * | 2013-05-24 | 2014-11-27 | 積水化学工業株式会社 | Sealing agent for liquid crystal dropping methods, vertically conducting material, and liquid crystal display element |
| CN106462014A (en) * | 2014-10-08 | 2017-02-22 | 积水化学工业株式会社 | Sealing agent for liquid crystal dropping methods, vertically conducting material and liquid crystal display element |
| JP6426050B2 (en) * | 2015-04-24 | 2018-11-21 | 日本化薬株式会社 | Liquid crystal sealing agent and liquid crystal display cell using the same |
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|---|---|---|---|---|
| CN1711300A (en) * | 2002-11-06 | 2005-12-21 | 日本化药株式会社 | Sealing material for liquid crystal and liquid crystal display cell using same |
| JP2006010870A (en) * | 2004-06-23 | 2006-01-12 | Sekisui Chem Co Ltd | Sealing material for liquid crystal display element, vertically conducting material, and the liquid crystal display element |
| JP2007316624A (en) * | 2006-04-25 | 2007-12-06 | Sekisui Chem Co Ltd | Sealing material for liquid crystal dispensing method, vertically conducting material, and liquid crystal display device |
| CN101210169A (en) * | 2006-12-30 | 2008-07-02 | 比亚迪股份有限公司 | Liquid crystal sealing agent composition and preparing method thereof |
| CN101861545A (en) * | 2007-11-16 | 2010-10-13 | 日本化药株式会社 | Liquid crystal sealing agent and liquid crystal display cell using the same |
| WO2011061910A1 (en) * | 2009-11-17 | 2011-05-26 | 日本化薬株式会社 | Novel thermal radical generator, method for producing the same, liquid crystal sealing agent, and liquid crystal display cell |
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| US3583326A (en) | 1969-01-27 | 1971-06-08 | Raoul Poissant | Turntable |
| JPH0820627B2 (en) | 1987-01-20 | 1996-03-04 | 松下電器産業株式会社 | Liquid crystal display element manufacturing method |
| JPH10239694A (en) | 1997-02-24 | 1998-09-11 | Hitachi Ltd | Manufacturing method of liquid crystal display device |
| JP2004061925A (en) | 2002-07-30 | 2004-02-26 | Nippon Kayaku Co Ltd | Liquid crystal sealing agent and liquid crystal display cell using the same |
| JP2004126211A (en) | 2002-10-02 | 2004-04-22 | Mitsui Chemicals Inc | Resin composition for sealing liquid crystal, and method of manufacturing liquid crystal display panel |
| JP5139735B2 (en) | 2007-06-26 | 2013-02-06 | 積水化学工業株式会社 | Sealant for liquid crystal dropping method, vertical conduction material, and liquid crystal display element |
| JP4948317B2 (en) | 2007-08-08 | 2012-06-06 | 三井化学株式会社 | Liquid crystal sealant, liquid crystal display panel manufacturing method using the same, and liquid crystal display panel |
| JP4528358B2 (en) * | 2008-11-21 | 2010-08-18 | 積水化学工業株式会社 | Sealant for liquid crystal dropping method and liquid crystal display element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1711300A (en) * | 2002-11-06 | 2005-12-21 | 日本化药株式会社 | Sealing material for liquid crystal and liquid crystal display cell using same |
| JP2006010870A (en) * | 2004-06-23 | 2006-01-12 | Sekisui Chem Co Ltd | Sealing material for liquid crystal display element, vertically conducting material, and the liquid crystal display element |
| JP2007316624A (en) * | 2006-04-25 | 2007-12-06 | Sekisui Chem Co Ltd | Sealing material for liquid crystal dispensing method, vertically conducting material, and liquid crystal display device |
| CN101210169A (en) * | 2006-12-30 | 2008-07-02 | 比亚迪股份有限公司 | Liquid crystal sealing agent composition and preparing method thereof |
| CN101861545A (en) * | 2007-11-16 | 2010-10-13 | 日本化药株式会社 | Liquid crystal sealing agent and liquid crystal display cell using the same |
| WO2011061910A1 (en) * | 2009-11-17 | 2011-05-26 | 日本化薬株式会社 | Novel thermal radical generator, method for producing the same, liquid crystal sealing agent, and liquid crystal display cell |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103649825A (en) | 2014-03-19 |
| JP6092103B2 (en) | 2017-03-08 |
| JP6231230B2 (en) | 2017-11-15 |
| CN103649825B (en) | 2016-05-18 |
| TW201319092A (en) | 2013-05-16 |
| KR101885944B1 (en) | 2018-08-06 |
| TWI543992B (en) | 2016-08-01 |
| KR20140047081A (en) | 2014-04-21 |
| JP2017083899A (en) | 2017-05-18 |
| JPWO2013008884A1 (en) | 2015-02-23 |
| WO2013008884A1 (en) | 2013-01-17 |
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