CN111936924A - Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element - Google Patents
Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element Download PDFInfo
- Publication number
- CN111936924A CN111936924A CN201980021603.0A CN201980021603A CN111936924A CN 111936924 A CN111936924 A CN 111936924A CN 201980021603 A CN201980021603 A CN 201980021603A CN 111936924 A CN111936924 A CN 111936924A
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- China
- Prior art keywords
- meth
- liquid crystal
- crystal display
- display element
- sealant
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 127
- 239000003795 chemical substances by application Substances 0.000 title claims description 30
- 238000007789 sealing Methods 0.000 title claims description 8
- 239000000463 material Substances 0.000 title abstract description 13
- -1 acrylic compound Chemical class 0.000 claims abstract description 107
- 239000000565 sealant Substances 0.000 claims abstract description 90
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
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- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([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
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
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- 229910001410 inorganic ion Inorganic materials 0.000 description 1
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- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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
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- 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
- 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
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- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
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- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
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- 239000005022 packaging material Substances 0.000 description 1
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- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
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- PSIKPHJLTVSQFO-UHFFFAOYSA-N propanedihydrazide Chemical compound NNC(=O)CC(=O)NN PSIKPHJLTVSQFO-UHFFFAOYSA-N 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 229940007392 tylan Drugs 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
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- 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
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Classifications
-
- 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
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- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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Abstract
The invention aims to provide a sealant for a liquid crystal display element, which has excellent adhesiveness to a flexible substrate, moisture permeability resistance and low liquid crystal contamination. Further, another object of the present invention is to provide a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element. The present invention is a sealant for a liquid crystal display element, which contains a curable resin, a thermoplastic resin, and a polymerization initiator, wherein the curable resin contains a monofunctional (meth) acrylic compound having a cyclic ether skeleton of 5 or more rings, and a polyfunctional (meth) acrylic compound.
Description
Technical Field
The present invention relates to a sealant for a liquid crystal display element, which has excellent adhesion to a flexible substrate, moisture permeation prevention, and low liquid crystal contamination. The present invention also relates to a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element.
Background
In recent years, as a method for manufacturing a liquid crystal display element such as a liquid crystal display unit, a liquid crystal dropping method called a dropping method using a photo-thermal curable sealing agent as disclosed in patent documents 1 and 2 has been used from the viewpoint of shortening the tact time and optimizing the amount of liquid crystal used.
In the one drop fill process, first, a frame-shaped seal pattern is formed on one of two transparent substrates with electrodes by dispensing. Next, in a state where the sealant is not cured, fine droplets of liquid crystal are dropped onto the entire inner surface of the frame of the transparent substrate, another transparent substrate is immediately bonded, and the sealing portion is irradiated with light such as ultraviolet light to perform precuring. Then, the liquid crystal is heated during annealing to perform main curing, thereby producing a liquid crystal display element. The one-drop fill process is currently the mainstream of a method for manufacturing a liquid crystal display element, and can manufacture a liquid crystal display element with extremely high efficiency if bonding of substrates is performed under reduced pressure.
Conventionally, glass substrates have been mainly used as substrates for liquid crystal display elements, but in recent years, flexible substrates using polyethylene terephthalate, polyimide, triacetyl cellulose, and the like have attracted attention. However, the conventional sealing agent has a problem that it cannot be sufficiently bonded when such a flexible substrate is used. In addition, in recent years, a curved display in which a panel is bent has attracted attention, but a conventional sealant has a problem that the sealant cannot follow when a substrate is bent, and a display defect is likely to occur.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2001-133794
Patent document 2: japanese laid-open patent publication No. 5-295087
Disclosure of Invention
Problems to be solved by the invention
The present invention relates to a sealant for a liquid crystal display element, which has excellent adhesion to a flexible substrate, moisture permeation prevention, and low liquid crystal contamination. Further, another object of the present invention is to provide a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element.
Means for solving the problems
The present invention is a sealant for a liquid crystal display element, which contains a curable resin, a thermoplastic resin, and a polymerization initiator, wherein the curable resin contains a monofunctional (meth) acrylic compound having a cyclic ether skeleton with 5 or more ring members, and a polyfunctional (meth) acrylic compound.
The present invention will be described in detail below.
The present inventors have studied to blend a thermoplastic resin in a sealant in order to apply the sealant for a liquid crystal display element to a flexible substrate. However, the obtained sealant exhibits an effect of improving the adhesion to some extent to a substrate made of polyethylene terephthalate (PET) or the like, but the adhesion is not sufficient particularly to a substrate made of Polyimide (PI) or triacetyl cellulose (TAC). Therefore, the present inventors have further studied on the use of a monofunctional (meth) acrylic compound having a specific structure in combination with a polyfunctional (meth) acrylic compound as a curable resin. As a result, they have found that a sealant for a liquid crystal display element having excellent adhesion to a flexible substrate can be obtained, and have completed the present invention.
The sealant for a liquid crystal display element of the present invention can be a sealant having excellent moisture permeation resistance and low liquid crystal contamination.
The sealant for a liquid crystal display element of the present invention contains a curable resin.
The curable resin contains a monofunctional (meth) acrylic compound having a cyclic ether skeleton having 5 or more rings (hereinafter, also referred to as "monofunctional (meth) acrylic compound according to the present invention"). The sealant for a liquid crystal display element of the present invention has excellent adhesion to a flexible substrate and can maintain sufficient adhesion even when the substrate is bent, by containing the monofunctional (meth) acrylic compound of the present invention as the curable resin and a thermoplastic resin described later.
In the present specification, the "(meth) acrylic" refers to an acrylic or methacrylic, the "(meth) acrylic compound" refers to a compound having a (meth) acryloyl group, and the "(meth) acryloyl group" refers to an acryloyl group or a methacryloyl group. The "monofunctional (meth) acrylic compound" is a compound having 1 (meth) acryloyl group in 1 molecule, and the "polyfunctional (meth) acrylic compound" is a compound having 2 or more (meth) acryloyl groups in 1 molecule.
The monofunctional (meth) acrylic compound of the present invention has a cyclic ether skeleton having 5 or more rings (hereinafter, also simply referred to as "cyclic ether skeleton"). The cyclic ether skeleton is preferably a cyclic ether skeleton having 4 or more carbon atoms. The upper limit of the number of carbon atoms in the cyclic ether skeleton is not particularly limited, and the substantial upper limit is 6.
The cyclic ether skeleton is preferably at least 1 selected from a tetrahydrofuran skeleton, a 1, 3-dioxane skeleton, a 1, 4-dioxane skeleton, a 1, 2-oxathiolane skeleton, and a morpholine skeleton.
The monofunctional (meth) acrylic compound of the present invention may have 1 cyclic ether skeleton in 1 molecule or 2 or more, but preferably has 1 cyclic ether skeleton in 1 molecule.
The monofunctional (meth) acrylic compound of the present invention preferably has the above cyclic ether skeleton at the terminal of the molecular chain.
Specific examples of the monofunctional (meth) acrylic compound of the present invention include tetrahydrofurfuryl (meth) acrylate, a compound represented by the following formula (1), and 5-ethyl-5- ((meth) acryloyloxymethyl) -1, 3-dioxane.
In the formula (1), n is an integer of 1 to 6.
The preferable lower limit of the content of the monofunctional (meth) acrylic compound of the present invention in 100 parts by weight of the total of the monofunctional (meth) acrylic compound of the present invention and the polyfunctional (meth) acrylic compound described later is 3 parts by weight, and the preferable upper limit is 95 parts by weight. When the content of the monofunctional (meth) acrylic compound of the present invention is 3 parts by weight or more, the obtained sealant for a liquid crystal display element has more excellent adhesion to a flexible substrate. The content of the monofunctional (meth) acrylic compound of the present invention is 95 parts by weight or less, and thus the obtained sealant for a liquid crystal display element is more excellent in moisture permeation resistance and low liquid crystal contamination. The content of the monofunctional (meth) acrylic compound according to the present invention is more preferably 8 parts by weight at the lower limit, more preferably 80 parts by weight at the upper limit, still more preferably 20 parts by weight at the lower limit, still more preferably 65 parts by weight at the upper limit, and particularly preferably 60 parts by weight at the upper limit.
The curable resin contains a polyfunctional (meth) acrylic compound. The inclusion of the polyfunctional (meth) acrylic compound provides the sealant for liquid crystal display elements of the present invention with excellent moisture permeation resistance and low liquid crystal contamination.
Examples of the polyfunctional (meth) acrylic compound include polyfunctional (meth) acrylate compounds, polyfunctional epoxy (meth) acrylates, polyfunctional urethane (meth) acrylates, and the like. Among them, polyfunctional epoxy (meth) acrylates are preferable.
In the present specification, the "(meth) acrylate" refers to an acrylate or a methacrylate, and the "epoxy (meth) acrylate" refers to a compound obtained by reacting at least 1 epoxy group in an epoxy compound with (meth) acrylic acid.
Examples of the 2-functional (meth) acrylate compound among the above-mentioned polyfunctional (meth) acrylate compounds include 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, and mixtures thereof, Polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide-added bisphenol a di (meth) acrylate, propylene oxide-added bisphenol a di (meth) acrylate, ethylene oxide-added bisphenol F di (meth) acrylate, dimethylol dicyclopentadienyl di (meth) acrylate, ethylene oxide-modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone diol di (meth) acrylate, polybutadiene diol di (meth) acrylate, and the like.
Further, as the (meth) acrylate compound having 3 or more functions among the above polyfunctional (meth) acrylate compounds, examples thereof include trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tri (meth) acryloyloxyethyl phosphate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
Examples of the polyfunctional epoxy (meth) acrylate include polyfunctional epoxy (meth) acrylates obtained by reacting a polyfunctional epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
Examples of the epoxy compound to be used as a raw material for synthesizing the above-mentioned polyfunctional epoxy (meth) acrylate include bisphenol a type epoxy compounds, bisphenol F type epoxy compounds, bisphenol S type epoxy compounds, 2' -diallylbisphenol a type epoxy compounds, hydrogenated bisphenol type epoxy compounds, propylene oxide-added bisphenol a type epoxy compounds, resorcinol type epoxy compounds, biphenyl type epoxy compounds, thioether type epoxy compounds, diphenyl ether type epoxy compounds, dicyclopentadiene type epoxy compounds, naphthalene type epoxy compounds, phenol novolac type epoxy compounds, o-cresol novolac type epoxy compounds, dicyclopentadiene novolac type epoxy compounds, biphenol aldehyde type epoxy compounds, naphthol novolac oxide compounds, glycidyl amine type epoxy compounds, alkyl polyol type epoxy compounds, and the like, Rubber-modified epoxy compounds, glycidyl ester compounds, and the like.
The polyfunctional urethane (meth) acrylate can be obtained, for example, by reacting a polyfunctional isocyanate compound with a (meth) acrylic acid derivative having a hydroxyl group in the presence of a catalytic amount of a tin compound.
Examples of the polyfunctional isocyanate compound include isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, Xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylylene diisocyanate, 1, 6, 11-undecane triisocyanate, and the like.
Further, as the polyfunctional isocyanate compound, a polyfunctional isocyanate compound having an extended chain obtained by a reaction of a polyol and an excessive amount of the polyfunctional isocyanate compound may be used.
Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include hydroxyalkyl mono (meth) acrylates, mono (meth) acrylates of diols, mono (meth) acrylates or di (meth) acrylates of triols, epoxy (meth) acrylates, and the like.
Examples of the hydroxyalkyl mono (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Examples of the dihydric alcohol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol.
Examples of the trihydric alcohol include trimethylolethane, trimethylolpropane, glycerol, and the like.
Examples of the epoxy (meth) acrylate include bisphenol a type epoxy acrylates.
The polyfunctional (meth) acrylic compound preferably has a lactone ring-opening structure. The multifunctional (meth) acrylic compound has a lactone ring-opening structure, and thus the sealant for a liquid crystal display element of the present invention has more excellent adhesion to a flexible substrate.
When the polyfunctional (meth) acrylic compound has a lactone ring-opening structure, examples of the lactone include γ -undecalactone, -caprolactone, γ -decalactone, σ -dodecalactone, γ -nonalactone, γ -nonanoate lactone, γ -valerolactone, σ -valerolactone, β -butyrolactone, γ -butyrolactone, β -propiolactone, σ -caprolactone, and 7-butyl-2-oxatronone. Among them, lactones having 5 to 7 carbon atoms in the linear chain part of the main skeleton at the time of ring opening are preferable, and caprolactone is more preferable. The polyfunctional (meth) acrylic compound may have a ring-opened structure of 1 kind of lactone among these lactones, or may have a ring-opened structure of 2 or more kinds of lactones.
In the case where the polyfunctional (meth) acrylic compound has a lactone ring-opening structure, the lactone ring-opening structure may be only 1 in 1 molecule, or may have a repeating structure. When the ring-opening structure of the lactone has a repeating structure, the preferable upper limit of the number of repetitions is 5.
Among the above polyfunctional (meth) acrylic compounds, as the polyfunctional (meth) acrylic compound having a lactone ring-opening structure, a compound in which a lactone ring-opening structure is introduced into the skeleton of the polyfunctional epoxy (meth) acrylate is preferable, caprolactone-modified epoxy (meth) acrylate is more preferable, and caprolactone-modified bisphenol a-type epoxy (meth) acrylate is even more preferable.
The polyfunctional (meth) acrylic compound may be used alone or in combination of 2 or more.
The preferable lower limit of the weight average molecular weight of the polyfunctional (meth) acrylic compound is 800, and the preferable upper limit is 2000. When the weight average molecular weight of the polyfunctional (meth) acrylic compound is in this range, the obtained sealant for a liquid crystal display element is more excellent in adhesiveness to a flexible substrate, coatability, and moisture permeation prevention.
In the present specification, the weight average molecular weight is a value obtained by measuring by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting into polystyrene. Examples of the column used for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.).
The sealant for a liquid crystal display element of the present invention may further contain another curable resin in addition to the monofunctional (meth) acrylic compound and the polyfunctional (meth) acrylic compound described in the present invention, within a range not to impair the object of the present invention.
Examples of the other curable resins include monofunctional (meth) acrylic compounds other than the monofunctional (meth) acrylic compound described in the present invention, and epoxy compounds.
Examples of the other monofunctional (meth) acrylic compound include a monofunctional (meth) acrylate compound and a monofunctional (meth) acrylamide compound.
Examples of the monofunctional (meth) acrylate compound include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexyl (meth) acrylate, and mixtures thereof, Isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, ethylcarbitol (meth) acrylate, 2, 2, 2-trifluoroethyl (meth) acrylate, 2, 2, 3, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, and mixtures thereof, Imide (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethylsuccinic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxyethyl 2-hydroxypropyl phthalate, 2- (meth) acryloyloxyethyl phosphate, glycidyl (meth) acrylate, and the like.
Examples of the monofunctional (meth) acrylamide compound include diethyl (meth) acrylamide and the like.
Examples of the epoxy compound as the other curable resin include the same epoxy compounds as those used as raw materials for synthesizing the polyfunctional epoxy (meth) acrylate.
The sealant for a liquid crystal display element of the present invention contains a thermoplastic resin.
By using the above thermoplastic resin in combination with the monofunctional (meth) acrylic compound of the present invention as the curable resin, the sealant for a liquid crystal display element of the present invention has excellent adhesion to a flexible substrate and can maintain sufficient adhesion even when the substrate is bent.
The glass transition temperature (hereinafter, also referred to as "Tg") of the thermoplastic resin is preferably 30 ℃ or lower. When the Tg of the thermoplastic resin is 30 ℃ or less, the obtained sealant for a liquid crystal display element has more excellent adhesion to a flexible substrate. The upper limit of the Tg of the thermoplastic resin is more preferably 25 ℃, still more preferably 21 ℃, still more preferably 10 ℃, particularly preferably 7 ℃ and most preferably 4 ℃.
The lower limit of Tg of the thermoplastic resin is preferably-30 ℃.
In the present specification, the glass transition temperature is a value measured by Differential Scanning Calorimetry (DSC) according to JIS K7121, "a method for measuring a transition temperature of a plastic".
The lower limit of the weight average molecular weight of the thermoplastic resin is preferably 5000, and the upper limit is preferably 10 ten thousand. The weight average molecular weight of the thermoplastic resin is 5000 or more, whereby the obtained sealant for a liquid crystal display element is more excellent in moisture permeation resistance. When the weight average molecular weight of the thermoplastic resin is 10 ten thousand or less, the obtained sealant for a liquid crystal display element is more excellent in coatability and adhesiveness to a flexible substrate. The lower limit of the weight average molecular weight of the thermoplastic resin is more preferably 2 ten thousand, and the upper limit is more preferably 8 ten thousand.
Examples of the thermoplastic resin include polyolefin, polyester, (meth) acrylic resin, polyamide, polyurethane, ABS resin, AES resin, AAS resin, MBS resin, anion/styrene copolymer, styrene/methyl (meth) acrylate copolymer, polystyrene, polycarbonate, polyphenylene ether, and phenoxy resin.
Examples of the polyolefin include polyethylene, polypropylene, ethylene/vinyl acetate copolymers, ethylene/(meth) acrylic acid copolymers, ethylene/(meth) methyl acrylate copolymers, ethylene/(meth) ethyl acrylate copolymers, ethylene/vinyl alcohol copolymers, and ethylene/(meth) ethyl acrylate/maleic anhydride copolymers.
Examples of the (meth) acrylic resin include polymethyl (meth) acrylate.
Among the thermoplastic resins, polyesters and (meth) acrylic resins are preferable, polyesters are more preferable, copolyesters are even more preferable, and saturated polyester resins and saturated copolyester resins are particularly preferable.
These thermoplastic resins may be used alone, or 2 or more of them may be used in combination.
In order to further improve the flexibility and toughness of the cured product of the obtained sealant for liquid crystal display elements, the thermoplastic resin is preferably an amorphous resin, and more preferably an amorphous polyester, from the viewpoint that the adhesiveness of the obtained sealant for liquid crystal display elements to a flexible substrate becomes further excellent.
Examples of commercially available amorphous polyesters among the above amorphous polyesters include VYLON300(Tg7 ℃ C., weight average molecular weight about 55000), VYLON500(Tg4 ℃ C., weight average molecular weight about 55000), VYLON550(Tg-15 ℃ C., weight average molecular weight about 60000), VYLON560(Tg7 ℃ C., weight average molecular weight about 40000), VYLON630(Tg7 ℃ C., weight average molecular weight about 55000), VYLON650(Tg10 ℃ C., weight average molecular weight about 55000), and VYLON670(Tg7 ℃ C., weight average molecular weight about 80000) (all manufactured by Toyo Boseki Kabushiki Kaisha).
In the present specification, the term "amorphous" means that no distinct melting point peak is found by Differential Scanning Calorimetry (DSC) according to JIS K7121, "method for measuring transition temperature of plastics".
The lower limit of the content of the thermoplastic resin in 100 parts by weight of the total of the curable resin and the thermoplastic resin is preferably 10 parts by weight, and the upper limit is preferably 70 parts by weight. When the content of the thermoplastic resin is 10 parts by weight or more, the obtained sealant for a liquid crystal display element has more excellent adhesion to a flexible substrate. When the content of the thermoplastic resin is 70 parts by weight or less, the obtained sealant for a liquid crystal display element is more excellent in coatability and moisture permeation prevention. The lower limit of the content of the thermoplastic resin is more preferably 20 parts by weight, and the upper limit is more preferably 60 parts by weight.
The sealant for a liquid crystal display element of the present invention contains a polymerization initiator.
Examples of the polymerization initiator include a photo radical polymerization initiator which generates radicals by light irradiation, a thermal radical polymerization initiator which generates radicals by heating, and the like.
Examples of the photo radical polymerization initiator include benzophenone-based compounds, acetophenone-based compounds, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, and thioxanthone.
Specific examples of the photo radical polymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, 1, 2- (dimethylamino) -2- ((4-methylphenyl) methyl) -1- (4- (4-morpholinophenyl) -1-butanone, 2-dimethoxy-1, 2-diphenylethan-1-one, bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 1- (4- (2-hydroxyethoxy) -phenyl) -2-hydroxy-2-methyl-propane-1-one 1-propan-1-one, 1- (4- (phenylthio) phenyl) -1, 2-octanedione 2- (O-benzoyloxime), 2, 4, 6-trimethylbenzoyldiphenylphosphine oxide, and the like.
The photo radical polymerization initiator may be used alone, or 2 or more kinds may be used in combination.
Examples of the thermal radical polymerization initiator include thermal radical polymerization initiators composed of azo compounds, organic peroxides, and the like. Among them, from the viewpoint of suppressing liquid crystal contamination, an initiator composed of an azo compound (hereinafter, also referred to as "azo initiator") is preferable, and an initiator composed of a polymer azo compound (hereinafter, also referred to as "polymer azo initiator") is more preferable.
The thermal radical polymerization initiator may be used alone, or 2 or more kinds may be used in combination.
In the present specification, the "macromolecular azo compound" refers to a compound having an azo group, which generates a radical capable of curing a (meth) acryloyl group by heat, and which has a number average molecular weight of 300 or more.
The number average molecular weight of the macromolecular azo compound preferably has a lower limit of 1000 and an upper limit of 30 ten thousand. When the number average molecular weight of the macromolecular azo compound is in this range, the compound can be easily mixed with the curable resin while preventing adverse effects on the liquid crystal. The number average molecular weight of the macromolecular azo compound is preferably 5000 as a lower limit, more preferably 10 ten thousand as an upper limit, still more preferably 1 ten thousand as a lower limit, and yet more preferably 9 ten thousand as an upper limit.
In the present specification, the number average molecular weight is a value obtained by measuring by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting into polystyrene. Examples of the column used for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.).
Examples of the macromolecular azo compound include compounds having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
The polymer azo compound having a structure in which a plurality of polyalkylene oxide units and the like are bonded to each other via an azo group is preferably a compound having a polyethylene oxide structure.
Specific examples of the macromolecular azo compound include a polycondensate of 4, 4 '-azobis (4-cyanovaleric acid) and a polyalkylene glycol, and a polycondensate of 4, 4' -azobis (4-cyanovaleric acid) and a polydimethylsiloxane having a terminal amino group.
Examples of commercially available products of the above-mentioned polymeric azo initiators include VPE-0201, VPE-0401, VPE-0601, VPS-0501 and VPS-1001 (all manufactured by Fuji film and Wako pure chemical industries, Ltd.).
Examples of azo initiators which are not polymers include V-65 and V-501 (both manufactured by Fuji film and Wako pure chemical industries, Ltd.).
Examples of the organic peroxide include ketone peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, peroxyesters, diacylperoxides, and peroxydicarbonates.
The lower limit of the content of the polymerization initiator is preferably 0.01 part by weight and the upper limit is preferably 10 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the polymerization initiator is in this range, the obtained sealant for a liquid crystal display element is more excellent in storage stability and curability while suppressing contamination of liquid crystal. The lower limit of the content of the polymerization initiator is more preferably 0.1 part by weight, and the upper limit is more preferably 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a thermosetting agent.
Examples of the heat-curing agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyphenol compounds, and acid anhydrides. Among them, organic acid hydrazide is suitably used.
The thermosetting agent may be used alone, or 2 or more of them may be used in combination.
Examples of the organic acid hydrazide include sebacic dihydrazide, isophthalic dihydrazide, adipic dihydrazide, malonic dihydrazide, and the like.
Examples of commercially available organic acid hydrazides include organic acid hydrazides manufactured by Otsuka chemical corporation, and organic acid hydrazides manufactured by Ajinomoto Fine-Techno Co., Inc.
Examples of the organic acid hydrazide available from Otsuka chemical company include SDH and ADH.
Examples of the organic acid hydrazide manufactured by Inc. of the Ajinomoto Fine-technique Co., include Amicure VDH, Amicure VDH-J, Amicure UDH and Amicure UDH-J.
The lower limit of the content of the thermosetting agent is preferably 1 part by weight and the upper limit is preferably 50 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the thermosetting agent is in this range, the thermosetting property can be further improved without deteriorating the coating property and the like of the obtained sealant for a liquid crystal display element. A more preferable upper limit of the content of the thermosetting agent is 30 parts by weight.
The sealant for a liquid crystal display element of the present invention preferably contains a filler for the purpose of improving viscosity, further improving adhesiveness by a stress dispersion effect, improving a linear expansion coefficient, improving moisture resistance of a cured product, and the like.
As the filler, an inorganic filler or an organic filler can be used.
Examples of the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate, and the like.
Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The fillers may be used alone, or 2 or more of them may be used in combination.
The lower limit of the content of the filler in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is preferably 10 parts by weight, and the upper limit is preferably 70 parts by weight. When the content of the filler is in this range, the effect of improving the adhesiveness and the like can be further improved without deteriorating the coating property and the like. The lower limit of the content of the filler is more preferably 20 parts by weight, and the upper limit is more preferably 60 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a silane coupling agent. The silane coupling agent mainly functions as an adhesion aid for satisfactorily adhering the sealant to a substrate or the like.
As the silane coupling agent, for example, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are suitably used. These silane coupling agents have an excellent effect of improving adhesion to a substrate or the like, and can inhibit the outflow of a curable resin into a liquid crystal by chemically bonding with the curable resin.
The silane coupling agents may be used alone, or 2 or more of them may be used in combination.
The content of the silane coupling agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention preferably has a lower limit of 0.1 part by weight and an upper limit of 10 parts by weight. When the content of the silane coupling agent is within this range, the effect of suppressing the occurrence of liquid crystal contamination and improving the adhesiveness is further excellent. The lower limit of the content of the silane coupling agent is more preferably 0.3 part by weight, and the upper limit is more preferably 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a light-shading agent. By containing the light-shading agent, the sealant for a liquid crystal display element of the present invention can be suitably used as a light-shielding sealant.
Examples of the light-shading agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Among them, titanium black is preferable.
The titanium black has a higher transmittance for light in the vicinity of the ultraviolet region, particularly at a wavelength of 370nm to 450nm, than the average transmittance for light at a wavelength of 300nm to 800 nm. That is, the titanium black is a light-shading agent having the following properties: the sealant for a liquid crystal display element of the present invention is provided with light-shielding properties by sufficiently shielding light having a wavelength in the visible light region, while transmitting light having a wavelength in the vicinity of the ultraviolet region. Therefore, the photo-curing property of the sealant for a liquid crystal display element of the present invention can be further increased by using, as the photo-radical polymerization initiator or the photo-cation polymerization initiator, an initiator capable of initiating a reaction by light having a wavelength (370nm or more and 450nm or less) at which the transmittance of the titanium black becomes high. On the other hand, the light-shading agent contained in the sealant for a liquid crystal display element of the present invention is preferably a high-insulating material, and titanium black is also suitable as a high-insulating light-shading agent.
The optical density (OD value) of the titanium black per 1 μm is preferably 3 or more, and more preferably 4 or more. The higher the light-shielding property of the titanium black, the better, and the preferable upper limit of the OD value of the titanium black is not particularly limited, but is usually 5 or less.
The titanium black exhibits a sufficient effect without being surface-treated, but a titanium black having a surface treated with an organic component such as a coupling agent, or a surface-treated titanium black such as a titanium black covered with an inorganic component such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, or magnesium oxide may be used. Among them, titanium black treated with an organic component is preferable from the viewpoint of further improving the insulation properties.
Further, since a liquid crystal display element produced using the sealant for a liquid crystal display element of the present invention containing the titanium black as a light-shielding agent has sufficient light-shielding properties, it is possible to realize: a liquid crystal display element having high contrast without light leakage and excellent image display quality.
Examples of commercially available products among the above titanium blacks include titanium black manufactured by mitsubishi integrated materials corporation, and titanium black manufactured by gibberella chemical corporation.
Examples of the titanium black manufactured by Mitsubishi Integrated materials include 12S, 13M-C, 13R-N and 14M-C.
Examples of the titanium black manufactured by red spike formation company include Tilack D.
The lower limit of the specific surface area of the titanium black is preferably 13m2A preferred upper limit of 30 m/g2A more preferred lower limit is 15m2A more preferred upper limit is 25 m/g2/g。
The volume resistance of the titanium black is preferably 0.5 Ω · cm at the lower limit, 3 Ω · cm at the upper limit, 1 Ω · cm at the lower limit, and 2.5 Ω · cm at the upper limit.
The primary particle size of the light-shading agent is not particularly limited as long as it is not more than the distance between the substrates of the liquid crystal display element, and the lower limit is preferably 1nm, and the upper limit is preferably 5000 nm. By setting the primary particle size of the light-shielding agent in this range, the light-shielding property can be further improved without deteriorating the coatability and the like of the obtained sealant for a liquid crystal display element. The lower limit of the primary particle diameter of the light-shading agent is more preferably 5nm, the upper limit is more preferably 200nm, the lower limit is more preferably 10nm, and the upper limit is more preferably 100 nm.
The primary PARTICLE size of the light-shading agent can be measured by dispersing the light-shading agent in a solvent (water, organic solvent, etc.) using NICOMP380ZLS (manufactured by part SIZING SYSTEMS).
The content of the light-shading agent in 100 parts by weight of the sealant for liquid crystal display elements of the present invention preferably has a lower limit of 5 parts by weight and an upper limit of 80 parts by weight. When the content of the light-shielding agent is within this range, the obtained sealant for a liquid crystal display element can exhibit more excellent light-shielding properties without significantly reducing the adhesiveness, strength after curing, and drawing properties of the sealant. The content of the light-shading agent is more preferably 10 parts by weight at the lower limit, more preferably 70 parts by weight at the upper limit, still more preferably 30 parts by weight at the lower limit, and still more preferably 60 parts by weight at the upper limit.
The sealant for a liquid crystal display element of the present invention may further contain additives such as a stress relaxation agent, a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor, as required.
Examples of the method for producing the sealant for a liquid crystal display element of the present invention include a method in which a curable resin, a thermoplastic resin, a polymerization initiator, and an additive such as a silane coupling agent used as needed are mixed by using a mixer. Examples of the mixer include a homomixer, a universal mixer, a planetary mixer, a kneader, and a three-roll mixer.
By adding conductive fine particles to the sealant for a liquid crystal display element of the present invention, a vertical conduction material can be produced. The vertical conduction material comprising the sealant for liquid crystal display element of the present invention and conductive fine particles is also one aspect of the present invention.
As the conductive fine particles, metal balls, fine particles in which a conductive metal layer is formed on the surface of resin fine particles, or the like can be used. Among these, the fine particles having the conductive metal layer formed on the surface of the resin fine particles are preferable because the fine particles can be electrically connected without damaging the transparent substrate or the like due to the excellent elasticity of the resin fine particles.
Further, a liquid crystal display element using the sealant for a liquid crystal display element of the present invention or the vertical conduction material of the present invention is also one aspect of the present invention.
The sealant for a liquid crystal display element of the present invention can be suitably used for manufacturing a liquid crystal display element by a one drop fill process. Examples of a method for manufacturing the liquid crystal display element of the present invention by a liquid crystal dropping method include the following methods.
First, a step of applying the sealant for a liquid crystal display element of the present invention on a substrate by screen printing, dispenser application, or the like to form a frame-shaped seal pattern; next, a step of applying fine droplets of liquid crystal dropwise to the entire inner surface of the frame of the seal pattern in an uncured state of the sealant for a liquid crystal display element of the present invention and immediately superposing the other substrate; then, by performing a step of irradiating the seal pattern portion with light such as ultraviolet rays to photocure the sealant, a liquid crystal display element can be obtained by performing the above-described method. In addition to the step of photocuring the sealant, the step of heating and curing the sealant may be performed.
The substrate is preferably a flexible substrate.
Examples of the flexible substrate include substrates made of polyethylene terephthalate (PET), Polyimide (PI), triacetyl cellulose (TAC), polyester, poly (meth) acrylate, polycarbonate, polyether sulfone, and the like. The sealant for a liquid crystal display element of the present invention has excellent adhesion to a flexible substrate made of Polyimide (PI) or triacetyl cellulose (TAC), in particular.
The sealant for a liquid crystal display element of the present invention can also be used for bonding a general glass substrate.
The substrate is usually formed with a transparent electrode made of indium oxide or the like, an alignment film made of polyimide or the like, an inorganic ion shielding film, and the like.
Effects of the invention
According to the present invention, a sealant for a liquid crystal display element excellent in adhesion to a flexible substrate, moisture permeation prevention, and low liquid crystal contamination can be provided. Further, according to the present invention, a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element can be provided.
Detailed Description
The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.
Examples 1 to 13 and comparative examples 1 to 4
The liquid crystal display element sealants of examples 1 to 13 and comparative examples 1 to 4 were prepared by mixing the respective materials at the mixing ratios described in tables 1 and 2 using a planetary mixer (manufactured by THINKY, "あわとり tylan") and then further mixing the mixture using a three-roll mill.
< evaluation >
The following evaluations were made with respect to the sealants for liquid crystal display elements obtained in examples and comparative examples. The results are shown in tables 1 and 2.
(adhesion to PET substrate)
The sealant for liquid crystal display elements obtained in examples and comparative examples was applied to a 25mm × 60mm polyethylene terephthalate (PET) film (manufactured by Lintec Corporation, PET 5011) to a width of 25mm and a thickness of 40 μm, to produce test pieces. The 180-degree peel strength of the obtained test piece was measured using a tensile tester (EZ Graph, manufactured by Shimadzu corporation) at 25 ℃ and at a peel speed of 300 mm/min.
The adhesiveness to the PET substrate was evaluated by "X" when the 180-degree peel strength was 10N/cm or more, "O" when the 180-degree peel strength was 5N/cm or more and less than 10N/cm, "Delta" when the 180-degree peel strength was 2N/cm or more and less than 5N/cm, and "X" when the 180-degree peel strength was less than 2N/cm.
(adhesion to TAC substrate)
The sealant for liquid crystal display elements obtained in examples and comparative examples was applied to a 25mm × 60mm triacetyl cellulose (TAC) film (manufactured by Fuji photo film Co., Ltd. "TD 80 UL") to a thickness of 40 μm in a width of 25mm, thereby producing test pieces. The 180-degree peel strength of the obtained test piece was measured using a tensile tester (EZ Graph, manufactured by Shimadzu corporation) at 25 ℃ and at a peel speed of 300 mm/min.
The adhesiveness to the TAC substrate was evaluated by "X" when the 180-degree peel strength was 10N/cm or more, "O" when the 180-degree peel strength was 5N/cm or more and less than 10N/cm, "Delta" when the 180-degree peel strength was 2N/cm or more and less than 5N/cm, and "X" when the 180-degree peel strength was less than 2N/cm.
(moisture permeability prevention)
The sealants for liquid crystal display elements obtained in examples and comparative examples were applied to a smooth release film using a coater so that the thickness thereof was 200 to 300 μm. Next, the resultant was irradiated with a metal halide lamp at 100mW/cm2For 30 seconds, thereby obtaining a film for moisture permeability measurement. A cup for moisture permeability test was prepared by the moisture permeability test method (cup method) of the moisture-proof packaging material according to JIS Z0208, and the obtained film for moisture permeability measurement was attached and put into a constant temperature and humidity oven at 60 ℃ and 90% RH to measure the moisture permeability. The value of the obtained moisture permeability is lower than 500g/m2The time period of 24 hours was "O", and it was 500g/m224 hours or more and less than 800g/m2The delta was set in the case of 24 hours, and it was 800g/m224 hours toThe above case was "x", and the moisture permeation preventive property was evaluated.
(Low liquid Crystal contamination)
1 part by weight of spacer particles (Micropearl SI-H050, manufactured by waterlogging chemical industries, Ltd.) was dispersed in 100 parts by weight of each of the liquid crystal display element sealants obtained in examples and comparative examples. Next, the sealant in which the spacer particles were dispersed was filled in a dispensing syringe (manufactured by Musashi engineering co., LTD, "PSY-10E"), and subjected to defoaming treatment. The defoamed sealant was applied to one of 2 TAC films (manufactured by fuji film corporation, "TD 80 UL") having a ground alignment film and a transparent electrode so that the line width of the sealant became 1mm by a dispenser (manufactured by LTD, "SHOTMASTER 300").
Then, minute droplets of liquid crystal (JC-5004 LA, manufactured by Chisso Corporation) were applied dropwise to the entire surface of the sealing agent frame of the TAC film, and another TAC film was immediately bonded thereto. Then, the sealant portion was irradiated with 100mW/cm using a metal halide lamp2Ultraviolet rays of (2) for 30 seconds, thereby obtaining a liquid crystal display element.
The obtained liquid crystal display element was visually observed to have liquid crystal alignment disorder (display unevenness) in the vicinity of the sealant after a voltage was applied for 24 hours in an environment of 60 ℃ and 90% RH.
The low liquid crystal contamination was evaluated by assuming that the display unevenness was not seen at all in the liquid crystal display element as "o", assuming that the display unevenness was seen near the sealant (peripheral portion) of the liquid crystal display element as "Δ", and assuming that the display unevenness spread not only in the peripheral portion but also in the central portion as "x".
Note that the liquid crystal display element evaluated as "o" is a level at which there is no problem at all in actual use, the liquid crystal display element of "Δ" is a level at which there is a possibility of a problem depending on display design, and the liquid crystal display element of "x" is a level at which it cannot withstand actual use.
[ Table 1]
[ Table 2]
Industrial applicability
According to the present invention, a sealant for a liquid crystal display element excellent in adhesion to a flexible substrate, moisture permeation prevention, and low liquid crystal contamination can be provided. Further, according to the present invention, a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element can be provided.
Claims (9)
1. A sealant for a liquid crystal display element, comprising a curable resin, a thermoplastic resin and a polymerization initiator,
the curable resin contains a monofunctional (meth) acrylic compound having a cyclic ether skeleton of 5 or more rings and a polyfunctional (meth) acrylic compound.
2. The sealing agent for a liquid crystal display element according to claim 1, wherein the cyclic ether skeleton having 5 or more membered rings is at least 1 selected from a tetrahydrofuran skeleton, a 1, 3-dioxane skeleton, a 1, 4-dioxane skeleton, a 1, 2-oxathiolane skeleton, and a morpholine skeleton.
3. The sealing agent for a liquid crystal display element according to claim 1 or 2, wherein the cyclic ether skeleton having 5 or more rings is a cyclic ether skeleton having 4 or more carbon atoms.
4. The sealant for a liquid crystal display element according to claim 1, 2 or 3, wherein a content of the monofunctional (meth) acrylic compound having a cyclic ether skeleton of 5 or more rings is 3 parts by weight or more and 95 parts by weight or less in 100 parts by weight in total of the monofunctional (meth) acrylic compound having a cyclic ether skeleton of 5 or more rings and the polyfunctional (meth) acrylic compound.
5. The sealant for a liquid crystal display element according to claim 1, 2, 3, or 4, wherein the polyfunctional (meth) acrylic compound has a ring-opening structure of a lactone.
6. The sealant for a liquid crystal display element according to claim 1, 2, 3, 4, or 5, wherein the thermoplastic resin is an amorphous polyester.
7. The sealant for a liquid crystal display element according to claim 1, 2, 3, 4, 5, or 6, wherein a content of the thermoplastic resin is 10 parts by weight or more and 70 parts by weight or less in 100 parts by weight in total of the curable resin and the thermoplastic resin.
8. A vertically conducting material comprising the sealant for liquid crystal display element according to claim 1, 2, 3, 4, 5, 6 or 7 and conductive fine particles.
9. A liquid crystal display element, which is obtained by using the sealant for a liquid crystal display element according to claim 1, 2, 3, 4, 5, 6 or 7 or the vertically conducting material according to claim 8.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018-100693 | 2018-05-25 | ||
| JP2018100693 | 2018-05-25 | ||
| PCT/JP2019/019515 WO2019225473A1 (en) | 2018-05-25 | 2019-05-16 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
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| Publication Number | Publication Date |
|---|---|
| CN111936924A true CN111936924A (en) | 2020-11-13 |
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| CN201980021603.0A Pending CN111936924A (en) | 2018-05-25 | 2019-05-16 | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Country Status (5)
| Country | Link |
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| JP (2) | JP6625790B1 (en) |
| KR (1) | KR20210014093A (en) |
| CN (1) | CN111936924A (en) |
| TW (1) | TWI813690B (en) |
| WO (1) | WO2019225473A1 (en) |
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| WO2021241704A1 (en) * | 2020-05-28 | 2021-12-02 | 積水化学工業株式会社 | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element |
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| JP2002069160A (en) * | 1999-12-14 | 2002-03-08 | Mitsui Chemicals Inc | Sealing agent for liquid crystal display cell, composition for sealing agent for liquid crystal display cell and liquid crystal display element |
| CN1346375A (en) * | 1999-12-14 | 2002-04-24 | 三井化学株式会社 | Sealing agent for liquid-crystal display, cell, composition for sealing agent for liquid-crystal display cell, and liquid-crystal display element |
| JP2006178053A (en) * | 2004-12-21 | 2006-07-06 | Dainippon Ink & Chem Inc | Photocurable composition for sealing liquid crystal panel, and liquid crystal panel |
| JP2010254891A (en) * | 2009-04-28 | 2010-11-11 | Hitachi Chem Co Ltd | Photocurable resin composition, photocurable moisture-proof insulation coating, electronic part, and flat panel display, using the same |
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| WO2017082000A1 (en) * | 2015-11-09 | 2017-05-18 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
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| JP3162179B2 (en) | 1992-04-17 | 2001-04-25 | 協立化学産業株式会社 | Liquid crystal display frame sealant composition |
| JP3583326B2 (en) | 1999-11-01 | 2004-11-04 | 協立化学産業株式会社 | Sealant for dripping method of LCD panel |
| JP2003105207A (en) * | 2001-09-28 | 2003-04-09 | Chisso Corp | Resin composition and display device using the same |
| WO2013065828A1 (en) * | 2011-11-04 | 2013-05-10 | 積水化学工業株式会社 | Sealing agent for liquid crystal display element, vertically conducting material, and liquid crystal display element |
| JP6901292B2 (en) * | 2017-03-15 | 2021-07-14 | 株式会社Adeka | A water-soluble composition, a method for producing a cured product thereof, a cured product thereof, and an acylphosphinate. |
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2019
- 2019-05-16 CN CN201980021603.0A patent/CN111936924A/en active Pending
- 2019-05-16 WO PCT/JP2019/019515 patent/WO2019225473A1/en active Application Filing
- 2019-05-16 KR KR1020207022027A patent/KR20210014093A/en not_active Application Discontinuation
- 2019-05-16 JP JP2019532815A patent/JP6625790B1/en active Active
- 2019-05-21 TW TW108117483A patent/TWI813690B/en active
- 2019-10-16 JP JP2019189415A patent/JP6667042B2/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002069160A (en) * | 1999-12-14 | 2002-03-08 | Mitsui Chemicals Inc | Sealing agent for liquid crystal display cell, composition for sealing agent for liquid crystal display cell and liquid crystal display element |
| CN1346375A (en) * | 1999-12-14 | 2002-04-24 | 三井化学株式会社 | Sealing agent for liquid-crystal display, cell, composition for sealing agent for liquid-crystal display cell, and liquid-crystal display element |
| JP2006178053A (en) * | 2004-12-21 | 2006-07-06 | Dainippon Ink & Chem Inc | Photocurable composition for sealing liquid crystal panel, and liquid crystal panel |
| JP2010254891A (en) * | 2009-04-28 | 2010-11-11 | Hitachi Chem Co Ltd | Photocurable resin composition, photocurable moisture-proof insulation coating, electronic part, and flat panel display, using the same |
| TW201510044A (en) * | 2013-05-23 | 2015-03-16 | Nippon Kayaku Kk | Resin composition for sealing organic el element, and cured product thereof |
| WO2017082000A1 (en) * | 2015-11-09 | 2017-05-18 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2019225473A1 (en) | 2020-05-28 |
| KR20210014093A (en) | 2021-02-08 |
| TWI813690B (en) | 2023-09-01 |
| JP6667042B2 (en) | 2020-03-18 |
| JP6625790B1 (en) | 2019-12-25 |
| WO2019225473A1 (en) | 2019-11-28 |
| JP2020013165A (en) | 2020-01-23 |
| TW202003775A (en) | 2020-01-16 |
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