WO2017130786A1 - 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 - Google Patents
液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 Download PDFInfo
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- WO2017130786A1 WO2017130786A1 PCT/JP2017/001347 JP2017001347W WO2017130786A1 WO 2017130786 A1 WO2017130786 A1 WO 2017130786A1 JP 2017001347 W JP2017001347 W JP 2017001347W WO 2017130786 A1 WO2017130786 A1 WO 2017130786A1
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- Prior art keywords
- liquid crystal
- crystal display
- compound
- meth
- acrylate
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 117
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 59
- 238000007789 sealing Methods 0.000 title claims abstract description 52
- 239000004020 conductor Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 28
- 239000011347 resin Substances 0.000 claims abstract description 28
- 239000003999 initiator Substances 0.000 claims abstract description 23
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- 239000000463 material Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000011109 contamination Methods 0.000 abstract description 21
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 72
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- 238000000034 method Methods 0.000 description 13
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
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- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
- KSMGAOMUPSQGTB-UHFFFAOYSA-N 9,10-dibutoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=C(OCCCC)C2=C1 KSMGAOMUPSQGTB-UHFFFAOYSA-N 0.000 description 1
- GJNKQJAJXSUJBO-UHFFFAOYSA-N 9,10-diethoxyanthracene Chemical compound C1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 GJNKQJAJXSUJBO-UHFFFAOYSA-N 0.000 description 1
- LBQJFQVDEJMUTF-UHFFFAOYSA-N 9,10-dipropoxyanthracene Chemical compound C1=CC=C2C(OCCC)=C(C=CC=C3)C3=C(OCCC)C2=C1 LBQJFQVDEJMUTF-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
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- 239000004386 Erythritol Substances 0.000 description 1
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
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- 239000000440 bentonite Substances 0.000 description 1
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- 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
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- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
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- 239000012933 diacyl peroxide Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000005259 measurement Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZCIJAGHWGVCOHJ-UHFFFAOYSA-N naphthalene phenol Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)O ZCIJAGHWGVCOHJ-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 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
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 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
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
-
- 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
Definitions
- the present invention relates to a sealant for a liquid crystal display element that is excellent in light-shielding part curability and can suppress liquid crystal contamination. Moreover, this invention relates to the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements.
- a liquid crystal dropping method called a dropping method using a photothermal combined curing type sealing agent containing a polymerization initiator and a thermosetting agent is used.
- a rectangular seal pattern is formed on one of two transparent substrates with electrodes by dispensing.
- a liquid crystal micro-droplet is dropped on the entire surface of the transparent substrate frame in a state where the sealant is uncured, and the other transparent substrate is immediately overlaid, and the seal portion is irradiated with light such as ultraviolet rays for temporary curing. . Thereafter, heating is performed at the time of liquid crystal annealing to perform main curing, and a liquid crystal display element is manufactured. If the substrates are bonded together under reduced pressure, a liquid crystal display element can be manufactured with extremely high efficiency, and this dripping method is currently the mainstream method for manufacturing liquid crystal display elements.
- the position of the seal portion is arranged under the black matrix (hereinafter also referred to as a narrow frame design).
- Patent Document 3 discloses that a highly sensitive photopolymerization initiator is blended with a sealant. However, liquid crystal contamination could not be sufficiently suppressed in the light-shielding part only by blending a highly sensitive photopolymerization initiator.
- An object of this invention is to provide the sealing compound for liquid crystal display elements which is excellent in sclerosis
- hardenability of light-shielding part, and can suppress liquid-crystal contamination. Another object of the present invention is to provide a vertical conduction material and a liquid crystal display element using the sealing agent for a liquid crystal display element.
- the present invention relates to a sealing agent for a liquid crystal display element comprising a curable resin and a radical photopolymerization initiator, the curable resin comprising a compound having a molecular weight of 100 or more and less than 500, and a compound having a molecular weight of 500 to 3000
- the radical photopolymerization initiator is a sealing agent for liquid crystal display elements, which is a compound having a carbazole skeleton.
- the present inventor has examined the use of a compound having a carbazole skeleton as a particularly sensitive photoradical polymerization initiator.
- a radical photopolymerization initiator even when such a radical photopolymerization initiator is used, there is a problem that the light-shielding part is not sufficiently cured and liquid crystal contamination is likely to occur.
- the present inventor believes that although the compound having a carbazole skeleton used as the radical photopolymerization initiator is highly sensitive, the light-curing part curability could not be sufficiently improved due to low solubility in the curable resin. It was.
- the present inventor not only uses a compound having a carbazole skeleton as a radical photopolymerization initiator, but also has excellent light-shielding part curability by using a combination of a compound having a specific molecular weight as a curable resin, and The present inventors have found that a sealing agent for liquid crystal display elements that can suppress liquid crystal contamination can be obtained, and have completed the present invention.
- the sealing agent for liquid crystal display elements of this invention contains curable resin.
- the curable resin contains a compound having a molecular weight of 100 or more and less than 500 and a compound having a molecular weight of 500 to 3000.
- the compound having a carbazole skeleton as a radical photopolymerization initiator can be sufficiently dissolved.
- the sealing agent for liquid crystal display elements of the present invention is excellent in light-shielding part curability and can suppress liquid crystal contamination.
- the “molecular weight” is a molecular weight obtained from the structural formula for a compound whose molecular structure is specified, but for a compound having a wide distribution of polymerization degree and a compound whose modification site is unspecified. , Sometimes expressed using weight average molecular weight.
- the above “weight average molecular weight” is a value determined by polystyrene conversion after measurement by gel permeation chromatography (GPC). Examples of the column used when measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko).
- the curable resin contains a compound having a molecular weight of 100 or more and less than 500.
- the compound having a molecular weight of 100 or more and less than 500 preferably has a molecular weight of 300 or more and less than 500 from the viewpoint of the solubility of the compound having a carbazole skeleton.
- the curable resin preferably contains a (meth) acrylic compound as the compound having a molecular weight of 100 or more and less than 500.
- a (meth) acrylic compound for example, (meth) acrylic acid ester compound obtained by reacting (meth) acrylic acid with a compound having a hydroxyl group, (meth) acrylic acid and epoxy compound are reacted.
- examples include epoxy (meth) acrylates obtained, urethane (meth) acrylates obtained by reacting an isocyanate compound with a (meth) acrylic acid derivative having a hydroxyl group. Of these, epoxy (meth) acrylate is preferable.
- the (meth) acrylic compound preferably has two or more (meth) acryloyl groups in one molecule because of its high reactivity.
- the “(meth) acryl” means acryl or methacryl
- the “(meth) acryl compound” means an acryloyl group or a methacryloyl group (hereinafter referred to as “(meth) acryloyl group”). Also referred to as).
- the “(meth) acrylate” means acrylate or methacrylate.
- the “epoxy (meth) acrylate” represents a compound obtained by reacting all epoxy groups in the epoxy compound with (meth) acrylic acid.
- Examples of the monofunctional compounds among the (meth) acrylic acid ester compounds include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, and isobutyl (meth) acrylate.
- Examples of the bifunctional compound among the (meth) acrylic acid ester compounds include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexane.
- those having three or more functions include, for example, trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, glycerin tri (meth) acrylate, penta Examples include erythritol tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, pentaerythritol tetra (meth) acrylate, and the like.
- Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
- Examples of the epoxy compound used as a raw material for synthesizing the epoxy (meth) acrylate include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol E diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, and hydrogenated bisphenol.
- diglycidyl ether hydrogenated bisphenol E diglycidyl ether, resorcinol diglycidyl ether, biphenyl-4,4′-diylbis (glycidyl ether), 1,6-naphthalenediylbis (glycidyl ether), ethylene glycol diglycidyl ether, 1 1,3-propanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, and the like.
- Examples of the urethane (meth) acrylate obtained by reacting a hydroxyl group-containing (meth) acrylic acid derivative with the isocyanate compound include, for example, (meth) acrylic having a hydroxyl group with respect to 1 equivalent of an isocyanate compound having two isocyanate groups. Two equivalents of the acid derivative can be obtained by reacting in the presence of a catalytic amount of a tin-based compound.
- isocyanate compound used as the raw material for the urethane (meth) acrylate examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4.
- Examples include '-diisocyanate (MDI), hydrogenated MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, and tetramethylxylylene diisocyanate.
- MDI '-diisocyanate
- XDI xylylene diisocyanate
- XDI hydrogenated XDI
- lysine diisocyanate lysine diisocyanate
- tetramethylxylylene diisocyanate examples include tetramethylxylylene diisocyanate.
- Examples of the (meth) acrylic acid derivative having a hydroxyl group as a raw material for the urethane (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-hydroxybutyl (meth). Divalents such as hydroxyalkyl (meth) acrylates such as acrylate and 4-hydroxybutyl (meth) acrylate, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, etc. And mono (meth) acrylates of alcohols.
- the curable resin preferably contains an epoxy compound as a compound having a molecular weight of 100 or more and less than 500 from the viewpoint of adhesion and solubility of the compound having a carbazole skeleton.
- an epoxy compound the epoxy compound used as a raw material for synthesize
- the partial (meth) acryl-modified epoxy resin means a compound having one or more epoxy groups and (meth) acryloyl groups in one molecule, for example, two or more epoxy compounds. Can be obtained by reacting a part of the epoxy group with (meth) acrylic acid.
- the curable resin contains a compound having a molecular weight of 500 to 3000.
- the preferable lower limit of the molecular weight of the compound having a molecular weight of 500 to 3000 is 600, and the preferable upper limit is 2500.
- the molecular weight of the compound having a molecular weight of 500 to 3000 is 600 or more, the solubility of the compound having a carbazole skeleton is improved.
- the molecular weight of the compound having a molecular weight of 500 to 3000 is 2500 or less, the obtained sealing agent for liquid crystal display elements is more excellent in low liquid crystal contamination.
- the more preferable lower limit of the molecular weight of the compound having a molecular weight of 500 to 3000 is 1000, and the more preferable upper limit is 2000.
- the compound having a molecular weight of 500 to 3000 is preferably an oligomer compound, and more preferably an oligomer compound having a polymerization degree of 3 to 6.
- the compound having a molecular weight of 500 to 3000 is preferably a polyfunctional compound having two or more epoxy groups and / or (meth) acryloyl groups in one molecule, which increases the crosslinking density and further suppresses elution. Since it can do, it is more preferable that it is a polyfunctional compound which has a comb-shaped structure like a novolak-type structure.
- the compound having a molecular weight of 500 to 3000 include, for example, phenol novolac type epoxy resins, orthocresol novolac type epoxy resins, dicyclopentadiene novolac type epoxy resins, biphenyl novolac type epoxy resins, and naphthalene phenol novolac type epoxy resins.
- Bisphenol A type epoxy resin bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2,2'-diallyl bisphenol A type epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide added bisphenol A type Epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadi Reaction of oligomeric epoxy resins such as ene-type epoxy resins, naphthalene-type epoxy resins, glycidylamine-type epoxy resins, alkyl polyol-type epoxy resins, rubber-modified epoxy resins, and these oligomer-type epoxy resins with (meth) acrylic acid Examples thereof include oligomer-type epoxy (meth) acrylates and oligomer-type partial (meth) acryl-modified epoxy resins. Among these, oligomer type epoxy (meth) acrylate is preferable.
- the preferable lower limit of the content of the compound having the molecular weight of 500 to 3000 in the total of 100 parts by weight of the compound having the molecular weight of 100 or more and less than 500 and the compound having the molecular weight of 500 to 3000 is 10 parts by weight, and the preferable upper limit is 30 parts by weight. Part.
- the content of the compound having a molecular weight of 500 to 3000 is within this range, the obtained sealing agent for liquid crystal display elements is more excellent in the light-shielding part curability and the effect of suppressing liquid crystal contamination.
- a more preferable lower limit of the content of the compound having a molecular weight of 500 to 3000 is 12 parts by weight, and a more preferable upper limit is 20 parts by weight.
- the sealing agent for liquid crystal display elements of this invention contains radical photopolymerization initiator.
- the photo radical polymerization initiator is a compound having a carbazole skeleton.
- the sealing agent for liquid crystal display elements of the present invention is excellent in light-shielding part curability.
- the minimum with a preferable molecular weight of the compound which has the said carbazole skeleton is 300, and a preferable upper limit is 1000.
- a preferable molecular weight of the compound having the carbazole skeleton is within this range, the solubility in the curable resin is improved.
- the more preferable lower limit of the molecular weight of the compound having a carbazole skeleton is 400, and the more preferable upper limit is 700.
- the compound having a carbazole skeleton preferably has an aromatic ring other than the aromatic ring contained in the carbazole skeleton from the viewpoint of solubility in the curable resin. Moreover, since the compound having the carbazole skeleton is more excellent in light-shielding part curability, it preferably has a nitrogen atom other than the nitrogen atom contained in the carbazole skeleton, and more preferably has an oxime ester bond.
- the compound having the carbazole skeleton preferably has an absorption coefficient of 50 mL / g ⁇ cm or more at a wavelength of 365 nm measured in acetonitrile mixed with the compound having the carbazole skeleton so that the concentration becomes 0.1 mg / mL.
- the compound having the carbazole skeleton has an extinction coefficient of 50 mL / g ⁇ cm or more, the obtained sealing agent for liquid crystal display elements is more excellent in light-shielding part curability.
- the light absorption coefficient of the compound having a carbazole skeleton is more preferably 100 mL / g ⁇ cm or more. Further, there is no particular upper limit of the light absorption coefficient of the compound having a carbazole skeleton, but the substantial upper limit is 1000 mL / g ⁇ cm.
- the compound having the carbazole skeleton include, for example, O-acetyl-1- (6- (2-methylbenzoyl) -9-ethyl-9H-carbazol-3-yl) ethanone oxime, 3,6 -Bis- (2methyl-2morpholino-propionyl) -9-N-octylcarbazole, 3,6-bis (2-methyl-2-morpholinopropionyl) -9-benzoylcarbazole, 3,6-bis (2-methyl) -2-morpholinopropionyl) -9-n-butylcarbazole, 3,6-bis (2-methyl-2-morpholinopropionyl) -9-n-dodecylcarbazole, 2- (Nn-butyl-3′-carbazolyl) ) -4,6-bis (trichloromethyl) -s-triazine and the like.
- Examples of commercially available compounds having the carbazole skeleton include IRGACURE OXE02 (manufactured by BASF).
- the content of the compound having a carbazole skeleton is preferably 0.5 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the curable resin.
- the content of the compound having the carbazole skeleton is within this range, the obtained sealing agent for liquid crystal display elements is excellent in light-shielding part curability, weather resistance, storage stability, and the effect of suppressing liquid crystal contamination.
- the more preferable lower limit of the content of the compound having a carbazole skeleton is 1 part by weight, and the more preferable upper limit is 3 parts by weight.
- the sealing agent for liquid crystal display elements of the present invention may contain other photoradical polymerization initiator as the photoradical polymerization initiator in addition to the compound having the carbazole skeleton, but the light-shielding part curability and the liquid crystal From the viewpoint of achieving both the effect of suppressing contamination, it is preferable that no other radical photopolymerization initiator is contained.
- the sealing agent for liquid crystal display elements of the present invention may contain a sensitizer.
- the sealing agent for liquid crystal display elements of this invention can obtain the sealing agent for liquid crystal display elements which is more sensitive and is excellent in light-shielding part curability by containing the said sensitizer.
- the sensitizer preferably has a sufficient light absorption band in the ultraviolet / visible region, a compound having a benzophenone skeleton, a compound having an anthracene skeleton, a compound having an anthraquinone skeleton, a compound having a coumarin skeleton, a thioxanthone skeleton And at least one compound selected from the group consisting of compounds having a phthalocyanine skeleton, and a group consisting of a compound having an anthracene skeleton, a compound having an anthraquinone skeleton, and a compound having a thioxanthone skeleton More preferably, it is at least one compound selected.
- Examples of the compound having a benzophenone skeleton include benzophenone, 2,4-dichlorobenzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, and the like.
- Examples of the compound having an anthracene skeleton include 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, and 9,10-dibutoxyanthracene.
- Examples of the compound having an anthraquinone skeleton include 1-methylanthraquinone, 2-ethylanthraquinone, 1,4-dihydroxyanthraquinone, 2- (2-hydroxyethoxy) anthraquinone and the like.
- Examples of the compound having a coumarin skeleton include 7-diethylamino-4-methylcoumarin.
- Examples of the compound having a thioxanthone skeleton include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propylthioxanthone, and the like.
- Examples of the compound having a phthalocyanine skeleton include phthalocyanine.
- phthalocyanine examples include phthalocyanine.
- 4,4′-bis (dimethylamino) benzophenone and 4,4′-bis ( At least one of diethylamino) benzophenone is preferred.
- the content of the sensitizer is such that a preferred lower limit is 2 parts by weight and a preferred upper limit is 50 parts by weight with respect to 100 parts by weight of the radical photopolymerization initiator.
- a preferred lower limit is 2 parts by weight
- a preferred upper limit is 50 parts by weight with respect to 100 parts by weight of the radical photopolymerization initiator.
- the content of the sensitizer is within this range, the obtained sealing agent for a liquid crystal display element is more excellent in light-shielding part curability while suppressing liquid crystal contamination.
- the minimum with more preferable content of the said sensitizer is 5 weight part, and a more preferable upper limit is 40 weight part.
- the sealing agent for liquid crystal display elements of the present invention may contain a thermal radical polymerization initiator.
- a thermal radical polymerization initiator what consists of an azo compound, an organic peroxide, etc. is mentioned, for example.
- an initiator made of a polymer azo compound (hereinafter also referred to as “polymer azo initiator”) is preferable.
- the polymer azo compound means a compound having an azo group and generating a radical by heat and having a number average molecular weight of 300 or more.
- the preferable lower limit of the number average molecular weight of the polymeric azo initiator is 1000, and the preferable upper limit is 300,000.
- the more preferable lower limit of the number average molecular weight of the polymeric azo initiator is 5000, the more preferable upper limit is 100,000, the still more preferable lower limit is 10,000, and the still more preferable upper limit is 90,000.
- the said number average molecular weight is a value calculated
- polymer azo initiator examples include those having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
- polymer azo initiator having a structure in which a plurality of units such as polyalkylene oxide are bonded via the azo group those having a polyethylene oxide structure are preferable.
- Examples of such a polymer azo initiator include polycondensates of 4,4′-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4′-azobis (4-cyanopentanoic acid) Examples thereof include polycondensates of polydimethylsiloxane having a terminal amino group, such as VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (all of which are Wako Pure Chemical Industries, Ltd.) Manufactured) and the like.
- Examples of azo compounds that are not a polymer include V-65 and V-501 (both manufactured by Wako Pure Chemical Industries, Ltd.).
- organic peroxide examples include ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
- the content of the thermal radical polymerization initiator is preferably 0.05 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the curable resin.
- the thermal radical polymerization initiator is within this range, the obtained sealing agent for liquid crystal display elements is excellent in storage stability and curability while suppressing liquid crystal contamination.
- the minimum with more preferable content of the said thermal radical polymerization initiator is 0.1 weight part, and a more preferable upper limit is 5 weight part.
- the sealing agent for liquid crystal display elements of the present invention may contain a thermosetting agent.
- thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, and the like. Of these, organic acid hydrazide is preferably used.
- organic acid hydrazide examples include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
- organic acid hydrazides examples include, for example, SDH, ADH (all manufactured by Otsuka Chemical Co., Ltd.), Amicure VDH, Amicure VDH-J, Amicure UDH, Amicure UDH-J (all Ajinomoto Fine Techno Co., Ltd.) Manufactured) and the like.
- the content of the thermosetting agent is preferably 1 part by weight with respect to 100 parts by weight of the curable resin, and 50 parts by weight with respect to the preferable upper limit.
- the upper limit with more preferable content of the said thermosetting agent is 30 weight part.
- the sealing agent for liquid crystal display elements of the present invention may contain a filler for the purpose of improving the viscosity, improving the adhesion due to the stress dispersion effect, improving the linear expansion coefficient, and further improving the moisture resistance of the cured product. preferable.
- the filler examples 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,
- Organic fillers such as calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate, and organic materials such as polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles A filler is mentioned.
- the preferable lower limit of the content of the filler in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight.
- the minimum with more preferable content of the said filler is 20 weight part, and a more preferable upper limit is 60 weight part.
- the sealing compound for liquid crystal display elements of this invention contains a silane coupling agent.
- the silane coupling agent mainly has a role as an adhesion assistant for favorably bonding the sealing agent and the substrate.
- silane coupling agent since it is excellent in the effect which improves adhesiveness with a board
- -Aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are preferably used.
- These silane coupling agents may be used alone or in combination of two or more.
- the minimum with preferable content of the said silane coupling agent in 100 weight part of sealing compounds for liquid crystal display elements of this invention is 0.1 weight part, and a preferable upper limit is 10 weight part.
- a preferable upper limit is 10 weight part.
- the minimum with more preferable content of the said silane coupling agent is 0.3 weight part, and a more preferable upper limit is 5 weight part.
- the sealing agent for liquid crystal display elements of the present invention may contain a light shielding agent.
- the sealing compound for liquid crystal display elements of this invention can be used suitably as a light shielding sealing agent.
- the light-shielding agent examples include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Of these, titanium black is preferred because of its high insulating properties.
- the above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
- the liquid crystal display element produced using the sealing agent for liquid crystal display elements of the present invention containing the above-described titanium black as a light-shielding agent has sufficient light-shielding properties, and therefore has high contrast without light leakage A liquid crystal display element having excellent image display quality can be realized.
- titanium black examples include 12S, 13M, 13M-C, 13R-N, 14M-C (all manufactured by Mitsubishi Materials Corporation), Tilak D (manufactured by Ako Kasei Co., Ltd.), and the like. Can be mentioned.
- the preferable lower limit of the specific surface area of the titanium black is 13 m 2 / g, the preferable upper limit is 30 m 2 / g, the more preferable lower limit is 15 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
- the preferred lower limit of the volume resistance of the titanium black is 0.5 ⁇ ⁇ cm, the preferred upper limit is 3 ⁇ ⁇ cm, the more preferred lower limit is 1 ⁇ ⁇ cm, and the more preferred upper limit is 2.5 ⁇ ⁇ cm.
- the primary particle diameter of the light-shielding agent is not particularly limited as long as it is not more 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 5 ⁇ m. When the primary particle diameter of the light-shielding agent is within this range, the light-shielding property can be improved without deteriorating the applicability of the obtained sealing agent for liquid crystal display elements.
- the more preferable lower limit of the primary particle diameter of the light shielding agent is 5 nm
- the more preferable upper limit is 200 nm
- the still more preferable lower limit is 10 nm
- the still more preferable upper limit is 100 nm.
- the primary particle size of the light shielding agent can be measured by using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS) and dispersing the light shielding agent in a solvent (water, organic solvent, etc.).
- the preferable lower limit of the content of the light-shielding agent in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 5 parts by weight, and the preferable upper limit is 80 parts by weight.
- the content of the light-shielding agent is within this range, the liquid crystal display element sealant can exhibit better light-shielding properties without reducing the adhesion to the substrate, the strength after curing, and the drawability. it can.
- the more preferable lower limit of the content of the light shielding agent is 10 parts by weight, the more preferable upper limit is 70 parts by weight, the still more preferable lower limit is 30 parts by weight, and the still more preferable upper limit is 60 parts by weight.
- a method for producing the sealing agent for liquid crystal display elements of the present invention for example, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin, a light
- a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin, a light
- a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin, a light
- a method for producing the sealing agent for liquid crystal display elements of the present invention for example, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll, a curable resin,
- a vertical conducting material can be produced by blending conductive fine particles with the liquid crystal display element sealant of the present invention.
- Such a vertical conduction material containing the sealing agent for liquid crystal display elements of the present invention and conductive fine particles is also one aspect of the present invention.
- the conductive fine particles a metal ball, a resin fine particle formed with a conductive metal layer on the surface, or the like can be used.
- the one in which the conductive metal layer is formed on the surface of the resin fine particles is preferable because the conductive connection is possible without damaging the transparent substrate due to the excellent elasticity of the resin fine particles.
- the liquid crystal display element using the sealing agent for liquid crystal display elements of this invention or the vertical conduction material of this invention is also one of this invention.
- a liquid crystal dropping method is preferably used.
- the liquid crystal display element sealant of the present invention is applied to one of two substrates such as a glass substrate with electrodes such as an ITO thin film or a polyethylene terephthalate substrate by screen printing, dispenser application, or the like.
- Examples of the method include a step of combining, and a step of irradiating light such as ultraviolet rays to the seal pattern portion of the sealant for liquid crystal display element of the present invention to photocur the sealant.
- a step of heating and thermosetting the sealant may be performed.
- the sealing compound for liquid crystal display elements which is excellent in light-shielding part curability and can suppress liquid-crystal contamination can be provided.
- the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements can be provided.
- Examples 1 to 9, Comparative Examples 1 to 5 According to the blending ratios described in Tables 1 and 2, each material was mixed using a planetary stirrer ("Shinky”, “Awatori Nertaro”), and then mixed by using three rolls. Sealants for liquid crystal display elements of Examples 1 to 9 and Comparative Examples 1 to 5 were prepared.
- the obtained sealant is applied to the central part of the substrate A (boundary between the chromium vapor deposition part and the non-deposition part), and after the substrate B is bonded, the sealant is sufficiently applied.
- 100 mW / cm 2 ultraviolet rays were irradiated from the substrate A side using a metal halide lamp for 30 seconds.
- the substrates A and B are peeled off using a cutter, and the spectrum is measured by a microscopic IR method for the sealant on a point 50 ⁇ m away from the direct ultraviolet irradiation part (the part shielded from light by chromium vapor deposition).
- the conversion rate of the inside (meth) acryloyl group was calculated
- the conversion rate was 90% or more, “ ⁇ ”, 70% or more, but less than 90%, “ ⁇ ”, 50% or more, less than 70%, “ ⁇ ”, less than 50%.
- the curability of the light-shielding part was evaluated with “ ⁇ ” as the sample.
- TN liquid crystal manufactured by Chisso Corporation, “JC-5001LA”
- JC-5001LA fine droplets of TN liquid crystal
- the other transparent electrode substrate is 5 Pa with a vacuum bonding device. Bonding was performed under vacuum to obtain a cell.
- the obtained cell was irradiated with 100 mW / cm 2 of ultraviolet rays for 30 seconds using a metal halide lamp, and then heated at 120 ° C. for 1 hour to cure the sealant to obtain a liquid crystal display element.
- the display unevenness generated in the liquid crystal (especially the corner portion) around the seal portion was visually observed, and when the display unevenness was not confirmed, “ ⁇ ”, slight display unevenness was confirmed.
- the display performance (low liquid crystal contamination) of the liquid crystal display element was evaluated with “ ⁇ ” as the case, “ ⁇ ” when the display unevenness was clearly confirmed, and “X” when the severe display unevenness was confirmed. Note that the liquid crystal display elements evaluated as “ ⁇ ” and “ ⁇ ” are at a level that causes no problem in practical use.
- the sealing compound for liquid crystal display elements which is excellent in light-shielding part curability and can suppress liquid-crystal contamination can be provided.
- the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements can be provided.
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Abstract
Description
滴下工法では、まず、2枚の電極付き透明基板の一方に、ディスペンスにより長方形状のシールパターンを形成する。次いで、シール剤が未硬化の状態で液晶の微小滴を透明基板の枠内全面に滴下し、すぐに他方の透明基板を重ね合わせ、シール部に紫外線等の光を照射して仮硬化を行う。その後、液晶アニール時に加熱して本硬化を行い、液晶表示素子を作製する。基板の貼り合わせを減圧下で行うようにすれば、極めて高い効率で液晶表示素子を製造することができ、現在この滴下工法が液晶表示素子の製造方法の主流となっている。
液晶汚染を抑制する方法として、特許文献3には、シール剤に高感度の光重合開始剤を配合することが開示されている。しかしながら、高感度の光重合開始剤を配合しただけでは、遮光部において充分に液晶汚染を抑制することができなかった。
以下に本発明を詳述する。
本発明者は、光ラジカル重合開始剤として用いたカルバゾール骨格を有する化合物は高感度であるものの、硬化性樹脂に対する溶解性が低かったために遮光部硬化性を充分に向上させることができなかったと考えた。そこで本発明者は、光ラジカル重合開始剤としてカルバゾール骨格を有する化合物を用いるだけでなく、更に、硬化性樹脂として特定の分子量の化合物を組み合わせて用いることにより、遮光部硬化性に優れ、かつ、液晶汚染を抑制することができる液晶表示素子用シール剤を得ることができることを見出し、本発明を完成させるに至った。
上記硬化性樹脂は、分子量が100以上500未満の化合物と、分子量が500~3000の化合物とを含有する。上記分子量が100以上500未満の化合物と、上記分子量が500~3000の化合物とを組み合わせて用いることにより、光ラジカル重合開始剤であるカルバゾール骨格を有する化合物を充分に溶解させることができ、その結果、本発明の液晶表示素子用シール剤が遮光部硬化性に優れ、かつ、液晶汚染を抑制することができるものとなる。
なお、本明細書において、上記「分子量」は、分子構造が特定される化合物については、構造式から求められる分子量であるが、重合度の分布が広い化合物及び変性部位が不特定な化合物については、重量平均分子量を用いて表す場合がある。本明細書において、上記「重量平均分子量」は、ゲルパーミエーションクロマトグラフィー(GPC)で測定を行い、ポリスチレン換算により求められる値である。GPCによってポリスチレン換算による重量平均分子量を測定する際に用いるカラムとしては、例えば、Shodex LF-804(昭和電工社製)等が挙げられる。
上記分子量が100以上500未満の化合物は、カルバゾール骨格を有する化合物の溶解性の観点から、分子量が300以上500未満であることが好ましい。
上記(メタ)アクリル化合物としては、例えば、(メタ)アクリル酸に水酸基を有する化合物を反応させることにより得られる(メタ)アクリル酸エステル化合物、(メタ)アクリル酸とエポキシ化合物とを反応させることにより得られるエポキシ(メタ)アクリレート、イソシアネート化合物に水酸基を有する(メタ)アクリル酸誘導体を反応させることにより得られるウレタン(メタ)アクリレート等が挙げられる。なかでも、エポキシ(メタ)アクリレートが好ましい。また、上記(メタ)アクリル化合物は、反応性の高さから1分子中に(メタ)アクリロイル基を2個以上有するものが好ましい。
なお、本明細書において、上記「(メタ)アクリル」とは、アクリル又はメタクリルを意味し、上記「(メタ)アクリル化合物」とは、アクリロイル基又はメタクリロイル基(以下、「(メタ)アクリロイル基」ともいう)を有する化合物を意味する。また、上記「(メタ)アクリレート」とは、アクリレート又はメタクリレートを意味する。更に、上記「エポキシ(メタ)アクリレート」とは、エポキシ化合物中の全てのエポキシ基を(メタ)アクリル酸と反応させた化合物のことを表す。
上記エポキシ化合物としては、例えば、上記エポキシ(メタ)アクリレートを合成するための原料となるエポキシ化合物や、部分(メタ)アクリル変性エポキシ樹脂等が挙げられる。
なお、本明細書において上記部分(メタ)アクリル変性エポキシ樹脂とは、1分子中にエポキシ基と(メタ)アクリロイル基とをそれぞれ1つ以上有する化合物を意味し、例えば、2つ以上のエポキシ化合物の一部分のエポキシ基を(メタ)アクリル酸と反応させることによって得ることができる。
上記分子量が500~3000の化合物の分子量の好ましい下限は600、好ましい上限は2500である。上記分子量が500~3000の化合物の分子量が600以上であることにより、カルバゾール骨格を有する化合物の溶解性により優れるものとなる。上記分子量が500~3000の化合物の分子量が2500以下であることにより、得られる液晶表示素子用シール剤が低液晶汚染性により優れるものとなる。上記分子量が500~3000の化合物の分子量のより好ましい下限は1000、より好ましい上限は2000である。
また、上記分子量が500~3000の化合物は、エポキシ基及び/又は(メタ)アクリロイル基を1分子中に合計2個以上有する多官能化合物であることが好ましく、架橋密度が高まり、溶出をより抑制できることから、ノボラック型構造のような櫛形構造を有する多官能化合物であることがより好ましい。
上記光ラジカル重合開始剤は、カルバゾール骨格を有する化合物である。上記光ラジカル重合開始剤として上記カルバゾール骨格を有する化合物を用いることにより、本発明の液晶表示素子用シール剤は遮光部硬化性に優れるものとなる。
また、上記カルバゾール骨格を有する化合物は、遮光部硬化性により優れることから、カルバゾール骨格に含まれる窒素原子以外の窒素原子を有することが好ましく、オキシムエステル結合を有することがより好ましい。
また、上記カルバゾール骨格を有する化合物の吸光係数の好ましい上限は特にないが、実質的な上限は1000mL/g・cmである。
本発明の液晶表示素子用シール剤は、上記増感剤を含有することにより、より高感度で遮光部硬化性に優れる液晶表示素子用シール剤を得ることができる。
上記アントラセン骨格を有する化合物としては、例えば、9,10-ジエトキシアントラセン、9,10-ジプロポキシアントラセン、9,10-ジブトキシアントラセン等が挙げられる。
上記アントラキノン骨格を有する化合物としては、例えば、1-メチルアントラキノン、2-エチルアントラキノン、1,4-ジヒドロキシアントラキノン、2-(2-ヒドロキシエトキシ)アントラキノン等が挙げられる。
上記クマリン骨格を有する化合物としては、例えば、7-ジエチルアミノ-4-メチルクマリン等が挙げられる。
上記チオキサントン骨格を有する化合物としては、例えば、2,4-ジエチルチオキサントン、2-クロロチオキサントン、4-イソプロピルチオキサントン、1-クロロ-4-プロピルチオキサントン等が挙げられる。
上記フタロシアニン骨格を有する化合物としては、例えば、フタロシアニン等が挙げられる。
これらの増感剤のなかでも、得られる液晶表示素子用シール剤が遮光部硬化性に特に優れるものとなることから、4,4’-ビス(ジメチルアミノ)ベンゾフェノン及び4,4’-ビス(ジエチルアミノ)ベンゾフェノンの少なくともいずれかが好ましい。
上記熱ラジカル重合開始剤としては、例えば、アゾ化合物、有機過酸化物等からなるものが挙げられる。なかでも、高分子アゾ化合物からなる開始剤(以下、「高分子アゾ開始剤」ともいう)が好ましい。
なお、本明細書において高分子アゾ化合物とは、アゾ基を有し、熱によってラジカルを生成する、数平均分子量が300以上の化合物を意味する。
なお、本明細書において、上記数平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)で測定を行い、ポリスチレン換算により求められる値である。GPCによってポリスチレン換算による数平均分子量を測定する際のカラムとしては、例えば、Shodex LF-804(昭和電工社製)等が挙げられる。
上記アゾ基を介してポリアルキレンオキサイド等のユニットが複数結合した構造を有する高分子アゾ開始剤としては、ポリエチレンオキサイド構造を有するものが好ましい。このような高分子アゾ開始剤としては、例えば、4,4’-アゾビス(4-シアノペンタン酸)とポリアルキレングリコールの重縮合物や、4,4’-アゾビス(4-シアノペンタン酸)と末端アミノ基を有するポリジメチルシロキサンの重縮合物等が挙げられ、具体的には例えば、VPE-0201、VPE-0401、VPE-0601、VPS-0501、VPS-1001(いずれも和光純薬工業社製)等が挙げられる。
また、高分子ではないアゾ化合物の例としてはV-65、V-501(いずれも和光純薬工業社製)等が挙げられる。
上記熱硬化剤としては、例えば、有機酸ヒドラジド、イミダゾール誘導体、アミン化合物、多価フェノール系化合物、酸無水物等が挙げられる。なかでも、有機酸ヒドラジドが好適に用いられる。
上記有機酸ヒドラジドのうち市販されているものとしては、例えば、SDH、ADH(いずれも大塚化学社製)、アミキュアVDH、アミキュアVDH-J、アミキュアUDH、アミキュアUDH-J(いずれも味の素ファインテクノ社製)等が挙げられる。
また、遮光剤として上記チタンブラックを含有する本発明の液晶表示素子用シール剤を用いて製造した液晶表示素子は、充分な遮光性を有するため、光の漏れ出しがなく高いコントラストを有し、優れた画像表示品質を有する液晶表示素子を実現することができる。
また、上記チタンブラックの体積抵抗の好ましい下限は0.5Ω・cm、好ましい上限は3Ω・cmであり、より好ましい下限は1Ω・cm、より好ましい上限は2.5Ω・cmである。
なお、上記遮光剤の一次粒子径は、NICOMP 380ZLS(PARTICLE SIZING SYSTEMS社製)を用いて、上記遮光剤を溶媒(水、有機溶媒等)に分散させて測定することができる。
ビスフェノールAジグリシジルエーテル(DIC社製、「EPICLON EXA-850CRP」)340gをトルエン500mLに溶解させた後、トリフェニルホスフィン0.1gを加え、均一な溶液とした。得られた溶液にアクリル酸144gを還流撹拌下にて2時間かけて滴下した後、更に、還流撹拌を8時間行った。次に、トルエンを除去することによって、ビスフェノールA型エポキシアクリレートAを得た。
1H-NMR、13C-NMR、LC-TOF/MS、及び、IRにより、得られたビスフェノールA型エポキシアクリレートAは、ビスフェノールAジグリシジルエーテルジアクリレート(分子量484)であることを確認した。
ビスフェノールA型エポキシ樹脂(三菱化学社製、「jER834」)500gをトルエン500mLに溶解させた後、トリフェニルホスフィン0.1gを加え、均一な溶液とした。得られた溶液にアクリル酸144gを還流撹拌下にて2時間かけて滴下した後、更に、還流撹拌を8時間行った。次に、トルエンを除去することによって、ビスフェノールA型エポキシアクリレートBを得た。
1H-NMR、13C-NMR、LC-TOF/MS、及び、IRにより、得られたビスフェノールA型エポキシアクリレートBは、分子量が644のオリゴマー型エポキシアクリレートであることを確認した。
表1、2に記載された配合比に従い、各材料を遊星式撹拌機(シンキー社製、「あわとり練太郎」)を用いて混合した後、更に3本ロールを用いて混合することにより実施例1~9、比較例1~5の液晶表示素子用シール剤を調製した。
実施例及び比較例で得られた各液晶表示素子用シール剤について以下の評価を行った。結果を表1、2に示した。
まず、厚さ0.7mmのコーニングガラスの半面をクロム蒸着した基板Aと、前面をクロム蒸着した基板Bとを準備した。次に、実施例及び比較例で得られた各液晶表示素子用シール剤100重量部に対して平均粒子径5μmのスペーサー微粒子(積水化学工業社製、「ミクロパールSI-H050」)1重量部を遊星式撹拌装置によって均一に分散させ、得られたシール剤を基板Aの中央部(クロム蒸着部と非蒸着部との境界)に塗布し、基板Bを貼り合わせてからシール剤を充分に押し潰し、基板A側からメタルハライドランプを用いて100mW/cm2の紫外線を30秒照射した。
その後、カッターを用いて基板A及びBを剥がし、紫外線直接照射部の際から50μm離れた点(クロム蒸着により遮光されていた部分)上のシール剤について顕微IR法によってスペクトルを測定し、シール剤中の(メタ)アクリロイル基の転化率を以下の方法により求めた。即ち、815~800cm-1のピーク面積を(メタ)アクリロイル基のピーク面積とし、845~820cm-1のピーク面積をリファレンスピーク面積として、下記式により(メタ)アクリロイル基の転化率を算出し、転化率が90%以上であったものを「◎」、70%以上90%未満であったものを「○」、50%以上70%未満であったものを「△」、50%未満であったものを「×」として遮光部硬化性を評価した。
(メタ)アクリロイル基の転化率=(1-(紫外線照射後の(メタ)アクリロイル基のピーク面積/紫外線照射後のリファレンスピーク面積)/(紫外線照射前の(メタ)アクリロイル基のピーク面積/紫外線照射前のリファレンスピーク面積))×100
実施例及び比較例で得られた各液晶表示素子用シール剤100重量部に対して平均粒子径5μmのスペーサー粒子(積水化学工業社製、「ミクロパールSI-H050」)1重量部を遊星式撹拌装置によって均一に分散させ、得られたシール剤をディスペンス用のシリンジ(武蔵エンジニアリング社製、「PSY-10E」)に充填し、脱泡処理を行ってから、ディスペンサー(武蔵エンジニアリング社製、「SHOTMASTER300」)にて、2枚のITO薄膜付きの透明電極基板の一方にシール剤を枠状に塗布した。続いて、TN液晶(チッソ社製、「JC-5001LA」)の微小滴を液晶滴下装置にてシール剤の枠内に滴下塗布し、他方の透明電極基板を、真空貼り合わせ装置にて5Paの真空下にて貼り合わせ、セルを得た。得られたセルに、メタルハライドランプを用いて100mW/cm2の紫外線を30秒照射した後、120℃で1時間加熱してシール剤を硬化させ、液晶表示素子を得た。
得られた液晶表示素子について、シール部周辺の液晶(特にコーナー部)に生じる表示むらを目視にて観察し、表示むらが確認されなかった場合を「◎」、わずかな表示むらが確認された場合を「○」、はっきりと表示むらが確認された場合を「△」、酷い表示むらが確認された場合を「×」として液晶表示素子の表示性能(低液晶汚染性)を評価した。
なお、評価が「◎」、「○」の液晶表示素子は、実用に全く問題のないレベルである。
Claims (5)
- 硬化性樹脂と光ラジカル重合開始剤とを含有する液晶表示素子用シール剤であって、
前記硬化性樹脂は、分子量が100以上500未満の化合物と、分子量が500~3000の化合物とを含有し、
前記光ラジカル重合開始剤は、カルバゾール骨格を有する化合物である
ことを特徴とする液晶表示素子用シール剤。 - カルバゾール骨格を有する化合物は、カルバゾール骨格に含まれる芳香環以外の芳香環を有することを特徴とする請求項1記載の液晶表示素子用シール剤。
- 遮光剤を含有することを特徴とする請求項1又は2記載の液晶表示素子用シール剤。
- 請求項1、2又は3記載の液晶表示素子用シール剤と導電性微粒子とを含有することを特徴とする上下導通材料。
- 請求項1、2若しくは3記載の液晶表示素子用シール剤又は請求項4記載の上下導通材料を用いてなることを特徴とする液晶表示素子。
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- 2017-01-17 CN CN201780001988.5A patent/CN107710060B/zh active Active
- 2017-01-17 WO PCT/JP2017/001347 patent/WO2017130786A1/ja active Application Filing
- 2017-01-17 KR KR1020177033055A patent/KR20180101166A/ko not_active Application Discontinuation
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WO2015152030A1 (ja) * | 2014-03-31 | 2015-10-08 | 積水化学工業株式会社 | 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子 |
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WO2021177316A1 (ja) * | 2020-03-03 | 2021-09-10 | 積水化学工業株式会社 | 硬化性樹脂組成物、表示素子用シール剤、液晶表示素子用シール剤、上下導通材料、表示素子、電子部品用接着剤、及び、電子部品 |
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JPWO2017130786A1 (ja) | 2018-11-15 |
CN107710060B (zh) | 2021-11-12 |
TWI714709B (zh) | 2021-01-01 |
CN107710060A (zh) | 2018-02-16 |
JP7048314B2 (ja) | 2022-04-05 |
TW201739831A (zh) | 2017-11-16 |
KR20180101166A (ko) | 2018-09-12 |
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