CN114621722A - Liquid crystal sealant for liquid crystal dropping method - Google Patents
Liquid crystal sealant for liquid crystal dropping method Download PDFInfo
- Publication number
- CN114621722A CN114621722A CN202111485713.8A CN202111485713A CN114621722A CN 114621722 A CN114621722 A CN 114621722A CN 202111485713 A CN202111485713 A CN 202111485713A CN 114621722 A CN114621722 A CN 114621722A
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- sealing agent
- meth
- acrylate
- dropping method
- 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 157
- 238000000034 method Methods 0.000 title claims abstract description 39
- 239000000565 sealant Substances 0.000 title claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 88
- 238000007789 sealing Methods 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000000945 filler Substances 0.000 claims abstract description 37
- 239000011164 primary particle Substances 0.000 claims abstract description 8
- 238000013007 heat curing Methods 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 76
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 description 37
- 229920000647 polyepoxide Polymers 0.000 description 37
- -1 2-hydroxypropyl Chemical group 0.000 description 36
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 32
- 239000000758 substrate Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 20
- 239000007870 radical polymerization initiator Substances 0.000 description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 14
- 239000007983 Tris buffer Substances 0.000 description 13
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 239000010419 fine particle Substances 0.000 description 11
- 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 10
- 238000001723 curing Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 229920000058 polyacrylate Polymers 0.000 description 7
- 229930185605 Bisphenol Natural products 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 230000001588 bifunctional effect Effects 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003365 glass fiber Substances 0.000 description 6
- 239000011859 microparticle Substances 0.000 description 6
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- 239000005020 polyethylene terephthalate Substances 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 125000003700 epoxy group Chemical group 0.000 description 5
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- 125000006850 spacer group Chemical group 0.000 description 5
- WTKVMIIQXATOJO-UHFFFAOYSA-N trimethyl-(1,1,2,2-tetraphenyl-2-trimethylsilyloxyethoxy)silane Chemical compound C=1C=CC=CC=1C(C(O[Si](C)(C)C)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O[Si](C)(C)C)C1=CC=CC=C1 WTKVMIIQXATOJO-UHFFFAOYSA-N 0.000 description 5
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 4
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- GJBXIPOYHVMPQJ-UHFFFAOYSA-N hexadecane-1,16-diol Chemical compound OCCCCCCCCCCCCCCCCO GJBXIPOYHVMPQJ-UHFFFAOYSA-N 0.000 description 4
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- LUUFSCNUZAYHAT-UHFFFAOYSA-N octadecane-1,18-diol Chemical compound OCCCCCCCCCCCCCCCCCCO LUUFSCNUZAYHAT-UHFFFAOYSA-N 0.000 description 4
- 235000010292 orthophenyl phenol Nutrition 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FZFFWZJDHRTEMQ-UHFFFAOYSA-N 1,1,2,2-tetraphenyl-2-trimethylsilyloxyethanol Chemical compound OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 FZFFWZJDHRTEMQ-UHFFFAOYSA-N 0.000 description 3
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 3
- QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
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- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 3
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
- G02F1/1341—Filling or closing of cells
- G02F1/13415—Drop filling process
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Inorganic Chemistry (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
Abstract
The present invention relates to a liquid crystal sealing agent for a liquid crystal dropping method. The invention provides a liquid crystal sealant for a liquid crystal dropping method, which has been considered to be difficult to realize in the past and has both transparency and high adhesiveness, and a liquid crystal display unit sealed by a cured product thereof. A liquid crystal sealing agent for a liquid crystal dropping method, comprising a curable compound, a filler and a heat-curing agent, wherein the filler has a primary particle diameter of 0.3 [ mu ] m or less, the filler is contained in an amount of 5 parts by mass or less per 100 parts by mass of the curable compound, and the haze value of a cured product of the liquid crystal sealing agent for a liquid crystal dropping method is 60% or less when the film thickness is 100 [ mu ] m.
Description
Technical Field
The present invention relates to a liquid crystal sealing agent for a liquid crystal dropping method and a liquid crystal display cell encapsulated with a cured product thereof.
Background
In recent years, development of a display having transparency has been carried out, and attempts have been made to provide a display function as a display on a transparent material such as a windshield, a showcase, and a partition of an automobile (patent document 1). Among them, a liquid crystal display has a feature that high transparency can be obtained because it has fewer circuits per unit pixel than an organic Electroluminescence (EL) display and other displays.
However, since the liquid crystal sealing agent generally looks white due to scattering of light by the contained solid filler, there is a problem that the liquid crystal sealing agent deteriorates the appearance of the liquid crystal display.
In order to improve the transparency of the liquid crystal sealing agent, it is necessary to reduce a solid filler which causes scattering, but the conventional liquid crystal sealing agent has a problem that the adhesive force to the substrate is reduced when the filler is reduced, and the liquid crystal sealing agent is peeled off by external stress or impact.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2020-016710
Disclosure of Invention
Problems to be solved by the invention
The purpose of the present invention is to provide a liquid crystal sealant for liquid crystal dropping method which has been considered difficult to achieve in the past and has both transparency and high adhesiveness, and a liquid crystal display cell sealed with a cured product thereof.
Means for solving the problems
The present inventors have conducted extensive studies and, as a result, have found that a specific liquid crystal sealant for liquid crystal dropping method has both transparency and high adhesiveness, and have completed the present invention.
In the present specification, "(meth) acrylate" means "acrylate" and/or "methacrylate".
That is, the present invention relates to the following [1] to [6 ].
[1]
A liquid crystal sealing agent for a liquid crystal dropping method comprising a curable compound, a filler and a heat curing agent, wherein,
the filler has a primary particle diameter of 0.3 μm or less,
the content of the filler is 5 parts by mass or less with respect to 100 parts by mass of the curable compound, and
the cured product of the liquid crystal sealing agent for the liquid crystal dropping method has a haze value of 60% or less when the film thickness is 100 [ mu ] m.
[2]
The liquid crystal sealing agent for liquid crystal dropping method as described in the above item [1], wherein a cured product of the liquid crystal sealing agent for liquid crystal dropping method measured by a universal tester has an elastic modulus at 25 ℃ of 2000MPa or less.
[3]
The liquid crystal sealant for liquid crystal dropping method according to the above item [1] or [2], wherein the liquid crystal sealant for liquid crystal dropping method contains urethane (meth) acrylate as the curable compound.
[4]
The liquid crystal sealant for liquid crystal dropping method as described in the aforementioned item [3], wherein the urethane (meth) acrylate is obtained by reacting (a) a polyol having an aromatic ring, (b) an organic polyisocyanate, and (c) a hydroxyl group-containing (meth) acrylate.
[5]
The liquid crystal sealant for liquid crystal dropping method according to any one of the above items [1] to [4], wherein the liquid crystal sealant for liquid crystal dropping method is a sealant for transparent liquid crystal display.
[6]
A liquid crystal display unit, wherein the liquid crystal display unit is sealed with a liquid crystal sealing agent by the liquid crystal dropping method according to any one of the preceding items [1] to [4 ].
Effects of the invention
The present invention can provide a liquid crystal sealing agent for a liquid crystal dropping method having both transparency and high adhesiveness, and a liquid crystal display unit encapsulated with a cured product thereof.
Drawings
Fig. 1 is a view of a bonded substrate for adhesion test.
Detailed Description
The liquid crystal sealing agent for the liquid crystal dropping method comprises a curable compound, a filler and a thermal curing agent, wherein the primary particle diameter of the filler is less than 0.3 [ mu ] m, the content of the filler is less than 5 parts by mass relative to 100 parts by mass of the curable compound, and the haze value of a cured product of the liquid crystal sealing agent for the liquid crystal dropping method is less than 60% when the film thickness is 100 [ mu ] m.
The particle diameter of the filler can be measured by a laser diffraction/scattering particle size distribution analyzer (dry type) (LMS-30, manufactured by Kabushiki Kaisha, Ltd.). In addition, if the product is a commercially available product, the method is not limited to the above method, and values explicitly described in the product catalog of each company may be used.
The liquid crystal sealing agent looks white because the filler contained therein scatters light. Therefore, in order to improve the transparency of the liquid crystal sealing agent, it is preferable to reduce the particle size of the filler and also reduce the content of the filler. Specifically, the primary particle diameter of the filler is preferably 0.3 μm or less, more preferably 0.2 μm or less, and particularly preferably 0.1 μm or less. The preferable lower limit is not particularly limited, but when considering the kneading property with the liquid crystal sealing agent, the primary particle diameter of the filler is preferably 0.01 μm or more. The content of the filler is preferably 5 parts by mass or less, and more preferably 2.5 parts by mass or less, per 100 parts by mass of the curable compound. The preferable lower limit value is not particularly limited, but when the adhesiveness is taken into consideration, the content of the filler is preferably 1 part by mass or more. One kind of filler may be used, or a plurality of kinds of fillers may be used in combination.
The liquid crystal sealant of the present invention is preferably transparent. In the present invention, the following transparency evaluation and haze evaluation were performed for the transparency.
The transparency evaluation was performed as follows: a liquid crystal cell was fabricated, and the corner of the liquid crystal cell was observed in the transmission mode of an optical microscope. In this case, the liquid crystal sealing agent is preferably transparent to the extent that the boundary with the liquid crystal is slightly visible, and more preferably substantially integrated without being visible.
Haze evaluation was performed as follows: the resultant was irradiated with a radiation of 3000mJ/cm using a haze meter (manufactured by Tokyo electrochromatography: TC-H3DPK) with the empty state as a zero point2(measurement wavelength: 365nm) and then cured at 120 ℃ for 60 minutes to obtain a cured product having a thickness of 100 μm. The haze value is preferably 60% or less, more preferably 50% or less, and particularly preferably 40% or less.
The liquid crystal sealant of the present invention preferably has high adhesiveness. In the present invention, the following evaluation was made with respect to adhesiveness.
A liquid crystal sealant containing 1 wt% of 4 μm glass fiber was applied to a photo-alignment film substrate so as to transfer a corner having a length of 1cm × 1cm and an R of 0.5mm, the photo-alignment film substrate was bonded to the liquid crystal sealant, and the photo-alignment film substrate was irradiated with UV light at 3000mJ/cm2(measurement wavelength: 365nm) and then heated at 120 ℃ for 60 minutes, thereby making it tacky. The resulting bonded substrate was cut into a shape in which only the lower substrate, which is the terminal portion of the display, was exposed as shown in FIG. 1, and the lower substrate at positions 4mm apart from the diagonal of the corner of the applied liquid crystal sealing agent was pressed by a universal tester (manufactured by Shimadzu corporation: Autograph AG-Xplus500N) having a pin terminal of 3mm phi, and the maximum load at the time of peeling the bonded substrate was measured, thereby obtaining the adhesive strength. The adhesive strength is preferably 1.0kgf or more, more preferably 1.5kgf or more, particularly preferably 2.0kgf or more, and most preferably 2.5kgf or more.
The liquid crystal sealing agent of the present invention preferably has high flexibility. This is because the liquid crystal sealing agent having high flexibility can be used also for a display having a curved shape or a display having high flexibility, and can follow stress applied to the display. Flexibility can be evaluated by the modulus of elasticity.
Measured by irradiating with 3000mJ/cm of light using a universal tester (manufactured by Shimadzu corporation: Autograph AG-Xplus500N)2(measurement wavelength: 365nm) and cured at 120 ℃ for 60 minutes to obtain a cured product having a thickness of 100. mu.mThe modulus of elasticity at room temperature (25 ℃) is preferably 100MPa or more and 3000MPa or less, more preferably 300MPa or more and 2000MPa or less, and particularly preferably 400MPa or more and 1000MPa or less.
[ curable Compound ]
The liquid crystal sealing agent of the present invention contains a curable compound. The curable compound is not particularly limited as long as it is a compound curable by light, heat, or the like, but is preferably a compound having a (meth) acryloyl group or an epoxy group, and particularly preferably an epoxy (meth) acrylate, a urethane (meth) acrylate, or a polybutadiene compound.
[ (meth) acrylic acid ester ]
Specific examples of the (meth) acrylic acid ester include: n-acryloyloxyethylhexahydrophthalimide, acryloylmorpholine, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexane-1, 4-dimethanol mono (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, phenoxyethyl (meth) acrylate, phenylpolyethoxy (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, orthophenylphenol monoethoxy (meth) acrylate, orthophenylphenol polyethoxy (meth) acrylate, p-cumylphenoxyethyl (meth) acrylate, isobornyl (meth) acrylate, tribromophenoxyethyl (meth) acrylate, tetrahydrodicyclopentadiene (meth) acrylate, dihydrodicyclopentadiene (meth) acrylate, phenylmaleimide (meth) acrylate, and the like, Dihydrodicyclopentadiene oxyethyl (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, bisphenol A polyethoxy di (meth) acrylate, bisphenol A polypropoxy di (meth) acrylate, bisphenol F polyethoxy di (meth) acrylate, ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, tris (acryloyloxyethyl) isocyanurate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, tripentaerythritol penta (meth) acrylate, pentaerythritol penta (meth) acrylate, propylene glycol di (meth) acrylate, propylene glycol (meth) acrylate, propylene glycol (acrylate, propylene glycol acrylate, styrene (meth) acrylate, styrene (meth) acrylate, styrene (meth) acrylate, styrene (, Trimethylolpropane tri (meth) acrylate, trimethylolpropane polyethoxy tri (meth) acrylate, trimethylolpropane di (meth) acrylate, diacrylate of an ester of neopentyl glycol and hydroxypivalic acid, or diacrylate of an epsilon-caprolactone adduct of an ester of neopentyl glycol and hydroxypivalic acid. Preferred examples include: o-phenylphenol monoethoxy (meth) acrylate, o-phenylphenol polyethoxy (meth) acrylate.
[ epoxy (meth) acrylate ]
The epoxy (meth) acrylate can be obtained by a reaction of an epoxy resin with (meth) acrylic acid by a known method. The epoxy resin as a raw material is not particularly limited, but is preferably a bifunctional or higher epoxy resin, and examples thereof include: dimer acid-modified epoxy resins, resorcinol diglycidyl ether, bisphenol a-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, phenol novolac-type epoxy resins, cresol novolac-type epoxy resins, bisphenol a novolac-type epoxy resins, bisphenol F novolac-type epoxy resins, alicyclic epoxy resins, aliphatic chain epoxy resins, glycidyl ester-type epoxy resins, glycidyl amine-type epoxy resins, hydantoin-type epoxy resins, isocyanurate-type epoxy resins, phenol novolac-type epoxy resins having a trishydroxyphenylmethane skeleton, diglycidyl etherates of bifunctional phenols such as catechol and resorcinol, diglycidyl etherates of bifunctional alcohols, halides and hydrogenation products thereof. Among them, bisphenol a type epoxy resins and resorcinol diglycidyl ether are preferable from the viewpoint of liquid crystal contamination. The ratio of the epoxy group to the (meth) acryloyl group is not limited, and is appropriately selected from the viewpoint of process suitability.
A partially epoxy (meth) acrylate obtained by acrylating a part of the epoxy group is suitably used. The proportion of acrylation in this case is preferably from about 30% to about 70%.
[ urethane (meth) acrylate ]
Urethane (meth) acrylate has a soft skeleton specific to a urethane structure, and therefore a cured product has characteristics of being soft and low in moisture permeability and also capable of following bending of a flexible display, and therefore urethane (meth) acrylate having a polyester structure is preferably used as a curable compound, and urethane (meth) acrylate having a polyester structure is more preferred.
The urethane (meth) acrylate can be synthesized by a conventional method by reacting (a) a polyol, (b) an organic polyisocyanate, and (c) a hydroxyl group-containing (meth) acrylate, and if necessary, using a catalyst such as a tin compound.
In the synthesis of urethane (meth) acrylate, 1.1 to 2.0 equivalents of isocyanate group in the component (b) are preferably reacted with 1 equivalent of hydroxyl group in the component (a), and particularly 1.3 to 2.0 equivalents of isocyanate group in the component (b) are preferably reacted with each other. The reaction temperature is preferably from room temperature (25 ℃) to 100 ℃.
It is preferable that 0.95 to 1.1 equivalents of the hydroxyl group in the component (c) is reacted with respect to 1 equivalent of the isocyanate group in the reaction product of the component (a) and the component (b). The reaction temperature is preferably from room temperature (25 ℃) to 100 ℃.
Specific examples of the polyol (a) include: tricyclodecanedimethanol, hydrogenated polybutadiene polyol, dimer diol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1, 4-butanediol, neopentyl glycol, 1, 6-hexanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 12-dodecanediol, 1, 14-tetradecanediol, 1, 16-hexadecanediol, 1, 18-octadecanediol, 1, 20-eicosanediol, 1-methyl-1, 8-octanediol, 2-methyl-1, 8-octanediol, 3-methyl-1, 5-pentanediol, 2, 4-diethyl-1, 5-pentanediol, cyclohexane-1, 4-dimethanol, propylene glycol, 1, 4-decanediol, 1, 4-dimethanol, 1, 4-decanediol, 1, 14-tetradecanediol, 1, 16-hexadecanediol, 1, 18-octadecanediol, 1, 20-octanediol, 1, 8-octanediol, 1, 2-methyl-1, 8-octanediol, 2-octanediol, 3-decanediol, 2, 4-dimethanol, 1, 4-diol, 4-dimethyl, and mixtures thereof, And diols (a-1) such as polyethylene glycol, polypropylene glycol, bisphenol A poly (n.apprxeq.2 to 20) ethoxy glycol, bisphenol A poly (n.apprxeq.2 to 20) propoxy glycol, and polyester polyols (a-2) which are reaction products of these diols (a-1) with dibasic acids or anhydrides thereof (for example, succinic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, isophthalic acid, terephthalic acid, phthalic acid, or anhydrides thereof). Polyester polyols and polyols having aromatic rings are preferred, and polyester polyols having aromatic rings are particularly preferred. Examples of the aromatic ring include: aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, phenanthroline ring, etc.; an aromatic heterocyclic ring such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, or a benzothiazole ring, and a benzene ring or a naphthalene ring is preferable.
The component (a) may be used alone or in combination of two or more.
Specific examples of (b) the organic polyisocyanate include: toluene diisocyanate, isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, xylylene diisocyanate, 4 '-diphenylmethane diisocyanate, 4' -dicyclohexylmethane diisocyanate, xylylene diisocyanate, 1, 3-bis (isocyanatomethyl) cyclohexane, trimethylhexamethylene diisocyanate, dimer acid diisocyanate, 1, 5-naphthalene diisocyanate, 3 '-dimethyl-4, 4' -diphenylene diisocyanate, and the like. Preferred examples include: toluene diisocyanate, isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate.
Specific examples of (c) the hydroxyl group-containing (meth) acrylate include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 1, 4-butanediol (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, pentaerythritol tri (meth) acrylate, an epsilon-caprolactone adduct of 2-hydroxyethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, and the like. Preferred examples include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and polyethylene glycol mono (meth) acrylate.
The lower limit of the weight average molecular weight of the urethane (meth) acrylate in terms of polystyrene in GPC is preferably 1000 or more, more preferably 2000 or more, particularly preferably 3000 or more, and most preferably 4000 or more. The upper limit is preferably 10000 or less, more preferably 8000 or less, particularly preferably 7000 or less, and most preferably 6000 or less. When the weight average molecular weight of the urethane (meth) acrylate is in the above range, the viscosity of the liquid crystal sealing agent is in an appropriate range while maintaining good flexibility and moisture permeability.
[ epoxy resin ]
In an embodiment of the present invention, it is also preferable that the curable compound contains an epoxy resin.
The epoxy resin is not particularly limited, but is preferably a bifunctional or higher epoxy resin, and examples thereof include: dimer acid-modified epoxy resins, resorcinol diglycidyl ether, bisphenol a-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, phenol novolac-type epoxy resins, cresol novolac-type epoxy resins, bisphenol a novolac-type epoxy resins, bisphenol F novolac-type epoxy resins, alicyclic epoxy resins, aliphatic chain epoxy resins, glycidyl ester-type epoxy resins, glycidyl amine-type epoxy resins, hydantoin-type epoxy resins, isocyanurate-type epoxy resins, phenol novolac-type epoxy resins having a triphenylolmethane skeleton, and diglycidyl etherates of bifunctional phenols such as catechol and resorcinol, diglycidyl etherates of bifunctional alcohols, halides and hydrogenated products thereof. Among them, bisphenol a type epoxy resins and resorcinol diglycidyl ether are preferable from the viewpoint of liquid crystal staining properties.
[ polybutadiene Compound ]
Further, it is also a preferable embodiment of the present invention to use a polybutadiene compound having an epoxy group or a (meth) acryloyl group as the curable compound. The polybutadiene compound having an epoxy group is commercially available, for example, as JP-100 and JP-200 manufactured by Nippon Kazakh. The polybutadiene compound having a (meth) acryloyl group is commercially available, for example, as TEAI-1000 and TE-2000 manufactured by Nippon Caoda corporation.
From the viewpoint of reducing liquid crystal contamination, the lower limit of the number average molecular weight of these polybutadiene compounds is preferably 500, more preferably 750, and particularly preferably 1000. From the viewpoint of handleability, the upper limit of the number average molecular weight of the polybutadiene compound is preferably 10000, more preferably 8000, and particularly preferably 6000.
The curable compound may be used alone or in combination of two or more. In the case of using a curable compound in the liquid crystal sealing agent of the present invention, the content of the curable compound in the total amount of the liquid crystal sealing agent is preferably 10 to 95% by mass, and more preferably 20 to 90% by mass.
[ Filler ]
The liquid crystal sealing agent of the present invention contains a filler. From the viewpoint of transparency, the primary particle diameter of the filler is preferably 0.3 μm or less, more preferably 0.2 μm or less, and particularly preferably 0.1 μm or less. The preferable lower limit is not particularly limited, but when considering the kneading property with the liquid crystal sealing agent, the primary particle diameter of the filler is preferably 0.01 μm or more. The content of the filler is preferably 5 parts by mass or less, and more preferably 2.5 parts by mass or less, with respect to 100 parts by mass of the curable compound. The preferable lower limit value is not particularly limited, but when the adhesiveness is taken into consideration, the content of the filler is preferably 1 part by mass or more. One kind of filler may be used, or a plurality of kinds of fillers may be used in combination.
The filler contained in the liquid crystal sealing agent of the present invention may contain either an organic filler or an inorganic filler, or both of them.
Examples of the organic filler include: urethane polymer fine particles, acrylic polymer fine particles, styrene-olefin copolymer fine particles, and silicone fine particles. The silicone microparticles are preferably KMP-594, KMP-597, KMP-598 (manufactured by shin-Etsu chemical industries), or TorayfilRTME-5500, 9701, EP-2001 (manufactured by Toray Corning Co., Ltd.), JB-800T, HB-800BK (manufactured by Kokusho Kogyo Co., Ltd.) as the urethane polymer fine particles, and Rabalon as the styrene polymer fine particlesRTMT320C, T331C, SJ4400, SJ5400, SJ6400, SJ4300C, SJ5300C and SJ6300C (manufactured by Mitsubishi chemical), and as the fine particles of the styrene-olefin copolymer, Septon is preferableRTMSEPS2004、SEPS2063。
These organic fillers may be used alone or in combination of two or more. In addition, two or more kinds of core-shell structures can be used. Among them, urethane polymer microparticles, acrylic polymer microparticles, styrene polymer microparticles, and styrene-olefin copolymer microparticles are preferable, and acrylic polymer microparticles are particularly preferable.
When the acrylic polymer fine particles are used, an acrylic rubber having a core-shell structure containing two types of acrylic rubbers is preferable, and an acrylic rubber having a core-shell structure in which a core layer is n-butyl acrylate and a shell layer is methyl methacrylate is particularly preferable. As ZefiacRTMF-351S is sold by Ack industries, Inc.
Further, examples of the silicone fine particles include: organopolysiloxane crosslinked powder, linear dimethylpolysiloxane crosslinked powder, and the like. Further, as the composite silicone rubber, there can be mentioned a composite silicone rubber obtained by coating the surface of the above-mentioned silicone rubber with a silicone resin (for example, a polyorganosilsesquioxane resin). Among these fine particles, silicone rubber as a linear dimethylpolysiloxane crosslinked powder or composite silicone rubber fine particles as a linear dimethylpolysiloxane crosslinked powder coated with a silicone resin are particularly preferable. These organic fillers may be used alone or in combination of two or more.
As the inorganic filler, there may be mentioned: silica, silicon carbide, silicon nitride, boron nitride, calcium carbonate, magnesium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, magnesium oxide, zirconium oxide, aluminum hydroxide, magnesium hydroxide, calcium silicate, aluminum silicate, lithium aluminum silicate, zirconium silicate, barium titanate, glass fiber, carbon fiber, molybdenum disulfide, asbestos, and the like, and preferable examples thereof include: fused silica, crystalline silica, silicon nitride, boron nitride, calcium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, aluminum hydroxide, calcium silicate, aluminum silicate, preferably silica, alumina, talc. These inorganic fillers may be used in combination of two or more.
[ Heat curing agent ]
The liquid crystal sealing agent of the present invention contains a thermosetting agent.
Examples of the thermosetting agent include: a compound having a carboxyl group bonded to an aromatic ring in a molecule, a polyamine, a polyphenol, an organic acid hydrazide, and the like. But are not limited to these. Examples thereof include: aromatic hydrazides include terephthalic acid dihydrazide, isophthalic acid dihydrazide, 2, 6-naphthalenedicarboxylic acid dihydrazide, 2, 6-pyridinedicarboxylic acid dihydrazide, 1,2, 4-benzenetricarboxylic acid trihydrazide, 1,4,5, 8-naphthalenetetracarboxylic acid tetrahydrazide, pyromellitic acid tetrahydrazide, and the like. In addition, in the case of the aliphatic hydrazide, for example, there are mentioned: dihydrazide having a hydantoin skeleton, preferably a valine hydantoin skeleton (skeleton in which a carbon atom of the hydantoin ring is substituted with an isopropyl group), such as formylhydrazine, acetylhydrazine, propionohydrazide, oxalic dihydrazide, malonic dihydrazide, succinic dihydrazide, glutaric dihydrazide, adipic dihydrazide, pimelic dihydrazide, sebacic dihydrazide, 1, 4-cyclohexanedihydrazide, tartaric dihydrazide, malic dihydrazide, iminodiacetic dihydrazide, N' -hexamethylenebissemicarbazide, citric acid trihydrazide, nitrilotriacetic acid trihydrazide, cyclohexanetricarboxylic trihydrazide, 1, 3-bis (hydrazinocarbonylethyl) -5-isopropylhydantoin, etc., dihydrazide having a hydantoin skeleton, preferably a valine hydantoin skeleton (skeleton in which a carbon atom of the hydantoin ring is substituted with an isopropyl group), tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (1-hydrazinocarbonylethyl) isocyanurate, Tris (3-hydrazinocarbonylpropyl) isocyanurate, bis (2-hydrazinocarbonylethyl) isocyanurate, and the like. From the viewpoint of the balance of curing reactivity and latency, isophthalic dihydrazide, malonic dihydrazide, adipic dihydrazide, tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (1-hydrazinocarbonylethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (3-hydrazinocarbonylpropyl) isocyanurate are preferable, and tris (2-hydrazinocarbonylethyl) isocyanurate is particularly preferable.
[ curing accelerators ]
The liquid crystal sealing agent of the present invention can further improve the reactivity by adding a curing accelerator. Examples of the curing accelerator include organic acids and imidazoles.
Examples of the organic acid include organic carboxylic acids and organic phosphoric acids, but organic carboxylic acids are preferable. Specifically, there may be mentioned: aromatic carboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, benzophenone tetracarboxylic acid, and furandicarboxylic acid, succinic acid, adipic acid, dodecanedioic acid, sebacic acid, thiodipropionic acid, cyclohexanedicarboxylic acid, tris (carboxymethyl) isocyanurate, tris (2-carboxyethyl) isocyanurate, tris (2-carboxypropyl) isocyanurate, and bis (2-carboxyethyl) isocyanurate.
Further, as the imidazole compound, there can be mentioned: 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 2, 4-diamino-6- (2 '-methylimidazole (1')) ethyl-s-triazine, 2, 4-diamino-6- (2 '-undecylimidazole (1')) ethyl-s-triazine, 2, 4-diamino-6- (2 '-ethyl-4-methylimidazole (1')) ethyl-s-triazine, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-methyl-2-methyl-imidazole, 2-methyl-s-triazine, 2-methyl-2-methyl-imidazole, 2-methyl-imidazole, 2-methyl imidazole, 2-n-methyl imidazole, 2-methyl imidazole, 2-methyl imidazole, 2-methyl imidazole, 2-methyl imidazole, 2-n, 2, 4-diamino-6- (2 '-methylimidazole (1')) ethyl-s-triazine isocyanuric acid adduct, 2: 3 adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-3, 5-dimethylolimidazole, 2-phenyl-4-hydroxymethyl-5-methylimidazole, 1-cyanoethyl-2-phenyl-3, 5-bis (cyanoethoxymethyl) imidazole and the like.
In the liquid crystal sealing agent of the present invention, when a curing accelerator is used, the content of the curing accelerator is preferably 0.1 to 10% by mass, and more preferably 1 to 5% by mass, in the total amount of the liquid crystal sealing agent.
[ photo radical polymerization initiator ]
The liquid crystal sealing agent of the present invention may contain a photo radical polymerization initiator. The photo radical polymerization initiator is not particularly limited as long as it is a compound that generates a radical or an acid by irradiation of ultraviolet rays or visible light and initiates a chain polymerization reaction, and examples thereof include: benzil dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, diethyl thioxanthone, benzophenone, 2-ethylanthraquinone, 2-hydroxy-2-methylpropiophenone, 2-methyl- [4- (methylthio) phenyl]2-morpholino-1-propanone, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, camphorquinone, 9-fluorenone, diphenyl disulfide, and the like. Specifically, there may be mentioned: IRGACURERTM651、184、2959、127、907、369、379EG、819、784、754、500、OXE01、OXE02、OXE03、OXE04、DAROCURERTM1173、LUCIRINRTMTPO (both manufactured by Pasteur Co., Ltd.), SEIKUOLRTMZ, BZ, BEE, BIP, BBI (all manufactured by Seiko chemical Co., Ltd.), and the like. Among them, IRGACURE as an oxime ester initiator is preferableRTMOXE01、OXE02、OXE03、OXE04。
In addition, from the viewpoint of liquid crystal contamination, it is preferable to use a photo radical polymerization initiator having a (meth) acryloyl group in the molecule, for example, a reaction product of 2-methacryloyloxyethyl isocyanate and 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one. This compound can be obtained by the method described in international publication No. 2006/027982.
In the liquid crystal sealing agent of the present invention, when the photo radical polymerization initiator is used, the content of the photo radical polymerization initiator in the total amount of the liquid crystal sealing agent is preferably 0.001 to 3% by mass, and more preferably 0.002 to 2% by mass.
[ thermal radical polymerization initiator ]
The liquid crystal sealing agent of the present invention can improve curing speed and curability by containing a thermal radical polymerization initiator.
The thermal radical polymerization initiator is not particularly limited as long as it is a compound that generates a radical by heating and initiates a chain polymerization reaction, and examples thereof include an organic peroxide, an azo compound, a benzoin ether compound, an acetophenone compound, and benzopinacol, and it is preferable to use benzopinacol. For example, Kayamek is commercially available as an organic peroxideRTMA、M、R、L、LH、SP-30C；Parkadox CH-50L、BC-FF；Cadox B-40ES；Parkadox14；TrigonoxRTM22-70E、23-C70、121、121-50E、121-LS50E、21-LS50E、42、42LS；KayaesterRTMP-70、TMPO-70、CND-C70、OO-50E、AN；KayabutylRTMB；Parkadox16；KayacarbonRTMBIC-75, AIC-75 (chemical AKZO, manufactured by KOKAI Co., Ltd.); permekRTMN、H、S、F、D、G；PerhexaRTMH、HC、TMH、C、V、22、MC；PercureRTMAH、AL、HB；PerbutylRTMH、C、ND、L；PercumylRTMH、D；PeroylRTMIB、IPP；PeroctaRTMND (manufactured by Nichiki Kaisha) and the like.
Further, VA-044, 086, V-070, VPE-0201, VSP-1001 (manufactured by Wako pure chemical industries, Ltd.) and the like are commercially available as azo compounds.
The thermal radical polymerization initiator is preferably a thermal radical polymerization initiator having no oxygen-oxygen bond (-O — O-) or nitrogen-nitrogen bond (-N ═ N-) in the molecule. A thermal radical polymerization initiator having an oxygen-oxygen bond (-O-) or a nitrogen-nitrogen bond (-N ═ N-) in a molecule generates a large amount of oxygen or nitrogen gas when generating radicals, and therefore, the thermal radical polymerization initiator is cured in a state where bubbles remain in the liquid crystal sealing agent, and there is a possibility that the adhesive strength is lowered, the moisture permeability is lowered, the characteristics under a moist heat environment are lowered, and the like. Particularly preferred is a thermal radical polymerization initiator of the benzopinacol type (including a product obtained by chemically modifying benzopinacol). Specifically, there may be mentioned: benzopinacol, 1, 2-dimethoxy-1, 1,2, 2-tetraphenylethane, 1, 2-diethoxy-1, 1,2, 2-tetraphenylethane, 1, 2-diphenoxy-1, 1,2, 2-tetraphenylethane, 1, 2-dimethoxy-1, 1,2, 2-tetrakis (4-methylphenyl) ethane, 1, 2-diphenoxy-1, 1,2, 2-tetrakis (4-methoxyphenyl) ethane, 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane, 1, 2-bis (triethylsiloxy) -1,1,2, 2-tetraphenylethane, 1, 2-bis (tert-butyldimethylsiloxy) -1,1,2, 2-tetraphenylethane, 1-hydroxy-2-trimethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-triethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-tert-butyldimethylsilyloxy-1, 1,2, 2-tetraphenylethane and the like, preferably 1-hydroxy-2-trimethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-triethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-tert-butyldimethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane, more preferably 1-hydroxy-2-trimethylsiloxy-1, 1,2, 2-tetraphenylethane, 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane, particularly preferably 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane.
The benzopinacol is sold by Tokyo Kasei Kogyo, Wako pure chemical industries, Ltd. In addition, the etherification of the hydroxyl group of benzopinacol can be easily performed by a known method. The silylizing of the hydroxyl group of benzopinacol can be obtained by a method of heating the corresponding benzopinacol and various silylating agents in the presence of a basic catalyst such as pyridine. Examples of the silylating agent include Trimethylchlorosilane (TMCS), Hexamethyldisilazane (HMDS), N, O-bis (trimethylsilyl) trifluoroacetamide (BSTFA), Triethylchlorosilane (TECS) as a triethylsilylating agent, and tert-butylmethylsilane (TBMS) as a tert-butyldimethylsilylating agent, which are generally known as trimethylsilylating agents. These reagents are readily available from silicon derivative manufacturers and the like. The reaction amount of the silylation agent is preferably 1.0 to 5.0 times by mole based on 1 mole of the hydroxyl group in the target compound. More preferably 1.5 to 3.0 times by mole. When the amount is less than 1.0 time by mol, the reaction efficiency is poor and the reaction time is prolonged, so that thermal decomposition is promoted. When it is more than 5.0 times mole, separation upon recovery becomes poor or purification becomes difficult.
The content of the thermal radical polymerization initiator in the total amount of the liquid crystal sealing agent of the present invention is preferably 0.0001 to 10% by mass, more preferably 0.0005 to 5% by mass, and particularly preferably 0.001 to 3% by mass.
The liquid crystal sealing agent of the present invention may further contain additives such as a silane coupling agent, a radical polymerization inhibitor, a pigment, a leveling agent, an antifoaming agent, and a solvent, as required.
[ silane coupling agent ]
Examples of the silane coupling agent include: 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, N-phenyl-gamma-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl) -3-aminopropyltrimethoxysilane hydrochloride, 3-methacryloxypropyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane and the like. These silane coupling agents are commercially available as KBM series, KBE series and the like, and are sold by shin-Etsu chemical industries, Ltd. When a silane coupling agent is used in the liquid crystal sealing agent of the present invention, the content of the silane coupling agent in the total amount of the liquid crystal sealing agent is preferably 0.05 to 3% by mass.
[ radical polymerization inhibitor ]
The radical polymerization inhibitor is not particularly limited as long as it is a compound that inhibits polymerization by reacting with a radical generated by a photoradical polymerization initiator, a thermal radical polymerization initiator, or the like, and quinones, piperidines, hindered phenols, nitroses, or the like can be used. Specifically, there may be mentioned: naphthoquinone, 2-hydroxynaphthoquinone, 2-menadione, 2-methoxynaphthoquinone, 2,6, 6-tetramethylpiperidin-1-oxyl, 2,6, 6-tetramethyl-4-hydroxypiperidin-1-oxyl, 2,6, 6-tetramethyl-4-methoxypiperidin-1-oxyl, 2,6, 6-tetramethyl-4-phenoxypiperidin-1-oxyl, hydroquinone, 2-methylhydroquinone, 2-methoxyhydroquinone, p-benzoquinone, butylated hydroxyanisole, 2, 6-di-tert-butyl-4-ethylphenol, 2, 6-di-tert-butylcresol, beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid stearyl ester, stearyl ester, 2,2 ' -methylenebis (4-ethyl-6-tert-butylphenol), 4 ' -thiobis (3-methyl-6-tert-butylphenol), 4 ' -butylidenebis (3-methyl-6-tert-butylphenol), 3, 9-bis [1, 1-dimethyl-2- [ beta- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy ] ethyl ] -2,4,8, 10-tetraoxaspiro [5.5] undecane, tetrakis [ methylene-3- (3 ', 5 ' -di-tert-butyl-4 ' -hydroxyphenylpropionate) methane ], 1,3, 5-tris (3 ', 5 ' -di-tert-butyl-4 ' -hydroxybenzyl) -s-triazine-2, 4,6- (1H,3H,5H) trione, p-methoxyphenol, 4-methoxy-1-naphthol, thiodiphenylamine, aluminum salt of N-nitrosophenylhydroxylamine, trade name ADK STAB LA-81, trade name ADK STAB LA-82 (manufactured by Ediko Co., Ltd.), and the like, but is not limited thereto. Among them, naphthoquinones, hydroquinones, nitros, and piperazines are preferable, naphthoquinones, 2-hydroxynaphthoquinones, hydroquinones, 2, 6-di-tert-butyl-P-cresol, POLYSTOP 7300P (manufactured by boston corporation) is more preferable, and POLYSTOP 7300P (manufactured by boston corporation) is most preferable.
The content of the radical polymerization inhibitor in the total amount of the liquid crystal sealing agent of the present invention is preferably 0.0001 to 1% by mass, more preferably 0.001 to 0.5% by mass, and particularly preferably 0.01 to 0.2% by mass.
As an example of a method for obtaining the liquid crystal sealing agent of the present invention, the following method can be mentioned. First, the curable compound, and if necessary, the photo radical polymerization initiator, the thermal radical polymerization initiator, and the radical polymerization inhibitor are dissolved by heating. Next, the liquid crystal sealing agent of the present invention can be produced by cooling to room temperature, adding a thermosetting agent, a curing accelerator, a filler, a silane coupling agent, an antifoaming agent, a leveling agent, a solvent, and the like as needed, uniformly mixing them by a known mixing device such as a three-roll mill, a sand mill, a ball mill, and the like, and filtering them with a metal mesh.
As for the liquid crystal display unit of the present invention, an example is shown below.
The liquid crystal display unit of the present invention is obtained by: a pair of substrates having a predetermined electrode formed on the substrate are arranged to face each other at a predetermined interval, the periphery is sealed with the liquid crystal sealing agent of the present invention, and a liquid crystal is sealed in the gap. The type of the liquid crystal to be sealed is not particularly limited. The substrate comprises glass and stoneQuartz, plastic, silicon, and the like, and at least one of them has light transmission properties. As a method for producing the same, a spacer (gap control material) such as glass fiber is added to the liquid crystal sealing agent of the present invention, and then the liquid crystal sealing agent is applied to one of the pair of substrates by using a dispenser, a screen printing apparatus, or the like, and then precured at 80 to 120 ℃ as necessary. Then, liquid crystal is dropped inside the bank of the liquid crystal sealing agent, and the other glass substrate is stacked in vacuum to form a gap. After the gap is formed, the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 ℃ for 30 minutes to 2 hours. When the liquid crystal sealing material is used in a photothermal type, the liquid crystal sealing material is irradiated with ultraviolet rays by an ultraviolet ray irradiation machine to be photocured. The ultraviolet irradiation dose is preferably 500mJ/cm2～6000mJ/cm2More preferably 1000mJ/cm2～4000mJ/cm2(measurement wavelength: 365 nm). Then, the cured product is cured at 90 to 130 ℃ for 30 minutes to 2 hours as required, whereby the liquid crystal display cell of the present invention can be obtained. The liquid crystal display unit of the present invention obtained in this way is free from display defects caused by liquid crystal contamination and is excellent in adhesiveness and moisture resistance reliability. Examples of the spacer include: glass fibers, silica beads, polymer beads, and the like. The diameter thereof varies depending on the purpose, and is preferably 2 to 8 μm, and more preferably 4 to 7 μm. The amount of the spacer to be used is preferably 0.1 to 4 parts by mass, more preferably about 0.5 to about 2 parts by mass, and particularly preferably about 0.9 to about 1.5 parts by mass, based on 100 parts by mass of the liquid crystal sealing agent of the present invention.
[ examples ]
The present invention will be described in more detail with reference to examples, but the present invention is not limited to the examples. It is to be noted that, unless otherwise specified, "parts" and "%" are based on mass in the present document.
[ Synthesis example 1]
A flask equipped with a thermometer, a condenser and a stirrer was charged with 776.99g of a polyester polyol comprising methylpentanediol, adipic acid and isophthalic acidAlcohol (P-2012, hydroxyl value 54.6mgKOH/g, manufactured by Coli corporation) and 131.68g of toluene diisocyanate (Coronate T-100, molecular weight 174.2, manufactured by Tosoh corporation), and reacted at 80 ℃. The isocyanate content at this time was determined by adding an excess of amine and back-titrating with hydrochloric acid, and it was confirmed that the value was within plus or minus 2% of the residual amount of isocyanate determined from the calculated value. Subsequently, 0.6g of p-methoxyphenol (polymerization inhibitor), 90.43g of 2-hydroxyethyl acrylate (molecular weight: 116.1), and 0.3g of dibutyltin dilaurate (catalyst) were added thereto, and the mixture was stirred at 80 ℃ to carry out a reaction until the absorption spectrum of the isocyanate group in the infrared absorption spectrum (2280 cm)-1) Disappeared to thereby obtain a urethane acrylate oligomer having a weight average molecular weight of 6300.
[ Synthesis example 2]
100 parts (0.28 mol) of commercially available benzopinacol (manufactured by tokyo chemical synthesis) was dissolved in 350 parts of dimethylformamide. To this, 32 parts (0.4 mol) of pyridine as a basic catalyst and 150 parts (0.58 mol) of BSTFA (manufactured by shin Etsu chemical Co., Ltd.) as a silylating agent were added, and the mixture was heated to 70 ℃ and stirred for 2 hours. The resultant reaction liquid was cooled, and 200 parts of water was added while stirring to precipitate the product while inactivating the unreacted silylating agent. The precipitated product was separated by filtration and then sufficiently washed with water. Next, the obtained product was dissolved in acetone, and water was added to the solution to conduct recrystallization and purification. 105.6 parts (yield 88.3%) of 1, 2-bis (trimethylsilyloxy) -1,1,2, 2-tetraphenylethane as a target product were obtained.
Examples 1 to 17 and comparative examples 1 to 9
A curable compound, a photo radical polymerization initiator, and a radical polymerization inhibitor were heated and dissolved at 90 ℃ in the proportions shown in tables 1 to 3 below, and then cooled to room temperature, and a thermal radical polymerization initiator, a thermal curing agent, a curing accelerator, an organic filler, an inorganic filler, and a silane coupling agent were added and stirred, and then dispersed by a three-roll mill, and filtered by a metal mesh (635 mesh), thereby preparing a liquid crystal sealing agent. The particle size of the filler is a value clearly described in each company catalog.
[ evaluation ]
[ haze ]
The liquid crystal sealing agents produced in examples and comparative examples were sandwiched between polyethylene terephthalate (PET) films to prepare films having a thickness of 100 μm, and the films were irradiated with 3000mJ/cm by a UV irradiator2(measurement wavelength: 365nm), and then placed in an oven to be thermally cured at 120 ℃ for 60 minutes. The obtained cured film was cut into a square of 3cm × 3cm, and the polyethylene terephthalate film was peeled off, and the haze value was measured with a haze meter (manufactured by tokyo electrochromism: TC-H3DPK) with the empty state as a zero point. The results are shown in tables 1 to 3.
[ modulus of elasticity ]
The liquid crystal sealants manufactured in examples and comparative examples were sandwiched between polyethylene terephthalate (PET) films to prepare films having a thickness of 100 μm, and the films were irradiated with 3000mJ/cm using a UV irradiator2(measurement wavelength: 365nm), and then placed in an oven to be thermally cured at 120 ℃ for 60 minutes. The obtained cured film was cut into a dumbbell-shaped test piece having an overall length of 75mm, an overall width of 10mm and a thickness of 100 μm (length of narrow parallel portion 30 mm. times. width 5mm) according to JIS7113-1(1/2), and the polyethylene terephthalate film was peeled off and subjected to tensile measurement by a universal tester (manufactured by Shimadzu corporation: Autograph AG-Xplus500N) at a temperature of 25 ℃, a nip length of 50mm and a test speed of 5 mm/min, and the elastic modulus was calculated from the results of tensile stress and strain within the proportional limits. The results are shown in tables 1 to 3.
[ production of substrate with photo-alignment oriented film ]
A photo-alignment film liquid (NRB-U738, manufactured by Nissan chemical Co., Ltd.) was spin-coated on a glass substrate, prebaked on a hot plate at 80 ℃ for 3 minutes, and baked in an oven at 230 ℃ for 30 minutes. Then, 500mJ/cm was irradiated with a UV irradiator having a polarizing filter2(measurement wavelength: 254nm) ultraviolet ray, thereby carrying out alignment treatment, and further baking in an oven at 230 deg.CThe substrate was baked for 30 minutes, thereby obtaining a photo alignment film substrate.
[ evaluation of transparency ]
To the liquid crystal sealing materials prepared in examples and comparative examples, 1 wt% of 4 μm glass fiber as a spacer was added, and the mixture was stirred by a planetary stirring apparatus (manufactured by EME: VMX-360). The prepared liquid crystal sealing agent was coated on the prepared photo-alignment film substrate in a square of 1cm × 1cm, a predetermined amount of liquid crystal (MLC-3007 manufactured by Merck) was dropped on the center thereof, the opposite photo-alignment film substrates were attached under vacuum, and then irradiated with UV irradiation at 3000mJ/cm2(measurement wavelength: 365nm) and then heated at 120 ℃ for 60 minutes, thereby producing a liquid crystal cell. The obtained corner of the liquid crystal cell was observed in the transmission mode of an optical microscope, and the state where the liquid crystal sealant was transparent and substantially integrated with the liquid crystal without being seen at the boundary was evaluated as "o", the state where the boundary was slightly seen as "Δ", and the state where the transparency was impaired by scattering of the filler in the liquid crystal sealant and the boundary with the liquid crystal was clearly seen as "x". The results are shown in tables 1 to 3.
[ adhesive Strength ]
To the liquid crystal sealing materials prepared in examples and comparative examples, 1 wt% of 4 μm glass fiber as a spacer was added, and the mixture was mixed and stirred by a planetary stirring apparatus (manufactured by EME, Inc.: VMX-360). The prepared liquid crystal sealing agent was applied to the prepared photo alignment film substrate in a manner of duplicating a corner having a length of 1cm × 1cm and an R of 0.5mm, the opposite photo alignment film substrate was attached, and 3000mJ/cm was irradiated by a UV irradiator2(measurement wavelength: 365nm) and then heated at 120 ℃ for 60 minutes, thereby adhering it. The obtained bonded substrate was cut into a shape in which only the lower substrate, which is the terminal portion of the display, was exposed as shown in fig. 1, and the lower substrate at positions 4mm apart from the diagonal of the corner of the applied liquid crystal sealing agent was pressed by a universal tester (manufactured by shimadzu corporation: Autograph AG-Xplus500N) having a pin terminal of 3mm phi, and the maximum load at the time of peeling the bonded substrate was measured, thereby obtaining the adhesive strength. AboutAs a result, a state where the adhesive strength was sufficiently strong, that is, a state where the maximum load was 2.0kgf or more was evaluated as ∘, a state where the adhesive strength was slightly poor, that is, a state where the maximum load was 1.0kgf or more and less than 2.0kgf was evaluated as Δ, and a state where the maximum load was less than 1.0kgf and the adhesive strength was significantly insufficient was evaluated as x. The results are shown in tables 1 to 3.
TABLE 1
TABLE 2
TABLE 3
TABLE 4
From the results of tables 1 to 4, it was confirmed that the liquid crystal sealing agent of the present invention has both transparency and high adhesiveness. In addition, it was confirmed that the liquid crystal sealing agent of the present invention also has high flexibility.
Industrial applicability
The liquid crystal sealing agent of the present invention has both transparency and high adhesiveness, and therefore, is particularly useful as a liquid crystal sealing agent for a transparent liquid crystal display.
Claims (6)
1. A liquid crystal sealing agent for a liquid crystal dropping method comprising a curable compound, a filler and a heat-curing agent, wherein,
the filler has a primary particle diameter of 0.3 μm or less,
the content of the filler is 5 parts by mass or less with respect to 100 parts by mass of the curable compound, and
the cured product of the liquid crystal sealing agent for the liquid crystal dropping method has a haze value of 60% or less when the film thickness is 100 [ mu ] m.
2. The liquid crystal sealing agent for liquid crystal dropping method according to claim 1, wherein a cured product of the liquid crystal sealing agent for liquid crystal dropping method measured by a universal tester has an elastic modulus at 25 ℃ of 2000MPa or less.
3. The liquid crystal sealing agent for liquid crystal dropping method according to claim 1 or 2, wherein the liquid crystal sealing agent for liquid crystal dropping method contains urethane (meth) acrylate as the curable compound.
4. The liquid crystal sealing agent for liquid crystal dropping method according to claim 3, wherein the urethane (meth) acrylate is obtained by reacting (a) a polyol having an aromatic ring, (b) an organic polyisocyanate, and (c) a hydroxyl group-containing (meth) acrylate.
5. The liquid crystal sealant according to any one of claims 1 to 4, wherein the liquid crystal sealant for liquid crystal dropping is a sealant for a transparent liquid crystal display.
6. A liquid crystal display unit, wherein the liquid crystal display unit is encapsulated with a liquid crystal sealing agent by the liquid crystal dropping method according to any one of claims 1 to 5.
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