CN111936924B - Sealing agent for liquid crystal display element, vertically conductive material, and liquid crystal display element - Google Patents
Sealing agent for liquid crystal display element, vertically conductive material, and liquid crystal display element Download PDFInfo
- Publication number
- CN111936924B CN111936924B CN201980021603.0A CN201980021603A CN111936924B CN 111936924 B CN111936924 B CN 111936924B CN 201980021603 A CN201980021603 A CN 201980021603A CN 111936924 B CN111936924 B CN 111936924B
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- Prior art keywords
- meth
- liquid crystal
- crystal display
- display element
- acrylate
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 124
- 239000004020 conductor Substances 0.000 title claims description 9
- 239000003795 chemical substances by application Substances 0.000 title abstract description 35
- 238000007789 sealing Methods 0.000 title abstract description 15
- -1 acrylic compound Chemical class 0.000 claims abstract description 98
- 239000000565 sealant Substances 0.000 claims abstract description 77
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- 229920005992 thermoplastic resin Polymers 0.000 claims abstract description 29
- 150000004292 cyclic ethers Chemical group 0.000 claims abstract description 19
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 10
- 150000002596 lactones Chemical class 0.000 claims description 14
- 239000010419 fine particle Substances 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 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
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical group C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 46
- 230000035699 permeability Effects 0.000 abstract description 20
- 238000011109 contamination Methods 0.000 abstract description 13
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 96
- 150000001875 compounds Chemical class 0.000 description 41
- 239000004593 Epoxy Substances 0.000 description 38
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 23
- 239000010936 titanium Substances 0.000 description 23
- 229910052719 titanium Inorganic materials 0.000 description 23
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- 238000000034 method Methods 0.000 description 15
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 14
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- 239000005020 polyethylene terephthalate Substances 0.000 description 10
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
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- 150000002009 diols Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 4
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- 239000011164 primary particle Substances 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
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- 229920001634 Copolyester Polymers 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 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
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- 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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Abstract
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent adhesion to a flexible substrate, moisture permeability resistance, and low liquid crystal contamination. The present invention also provides a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element. The present invention provides 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 having a 5-membered ring or more, 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 permeability resistance, 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 cell, a liquid crystal dropping method called a dropping method using a photo-thermal curing type sealant as disclosed in patent document 1 and patent document 2 has been used from the viewpoint of shortening a tact time and optimizing a liquid crystal usage amount.
In the dropping process, first, a frame-like seal pattern is formed on one of two transparent substrates with electrodes by dispensing. Next, in a state where the sealing agent is not cured, minute droplets of liquid crystal are dropped onto the entire inner surface of the frame of the transparent substrate, and another transparent substrate is immediately bonded thereto, and the sealing portion is pre-cured by irradiation with light such as ultraviolet rays. Then, heating is performed during the liquid crystal annealing to perform main curing, and a liquid crystal display element is manufactured. If the substrates are bonded under reduced pressure, a liquid crystal display device can be manufactured with extremely high efficiency, and the dropping process is now becoming the mainstream of the manufacturing method of the liquid crystal display device.
Conventionally, glass substrates have been mainly used as substrates for liquid crystal display elements, but in recent years, attention has been paid to flexible substrates using polyethylene terephthalate, polyimide, triacetylcellulose, or the like. However, in the case of using such a flexible substrate, the conventional sealant has a problem that it cannot be sufficiently bonded. In addition, in recent years, a curved display in which a panel is bent has been attracting attention, but conventional sealants have a problem in that the sealant cannot follow the bending of a substrate and display failure is likely to occur.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2001-133794
Patent document 2: japanese patent laid-open 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 permeability resistance, and low liquid crystal contamination. The present invention also provides 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 provides 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 having a 5-membered ring or more, and a polyfunctional (meth) acrylic compound.
The present invention will be described in detail below.
The present inventors have studied to provide a sealant for a liquid crystal display element to a flexible substrate, and have made an investigation on blending a thermoplastic resin into the sealant. However, the obtained sealant exhibits an effect of improving adhesiveness to some extent to a substrate made of polyethylene terephthalate (PET) or the like, but particularly, adhesiveness to a substrate made of Polyimide (PI) or triacetyl cellulose (TAC) is insufficient. Accordingly, 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, it has been found that a sealant for a liquid crystal display element having excellent adhesion to a flexible substrate can be obtained, and the present invention has been completed.
The sealant for a liquid crystal display element of the present invention can be a sealant excellent in moisture permeability and low liquid crystal contamination resistance.
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 sealing agent for a liquid crystal display element of the present invention is excellent in adhesion to a flexible substrate, and can maintain a sufficient adhesion force even when the substrate is bent, by containing the monofunctional (meth) acrylic compound of the present invention as the curable resin and containing a thermoplastic resin described later.
In the present specification, the "(meth) acrylic" means acrylic or methacrylic, the "(meth) acrylic compound" means a compound having a (meth) acryloyl group, and the "(meth) acryloyl group" means an acryloyl group or a methacryloyl group. The "monofunctional (meth) acrylic compound" refers to a compound having 1 (meth) acryloyl group in 1 molecule, and the "polyfunctional (meth) acrylic compound" refers to 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-membered rings or more (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 carbon number of the cyclic ether skeleton is not particularly limited, but the upper limit is substantially 6.
The cyclic ether skeleton is preferably at least 1 selected from the group consisting of 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 in1 molecule, or may have 2 or more cyclic ether skeletons, but preferably has 1 cyclic ether skeleton in1 molecule.
The monofunctional (meth) acrylic compound of the present invention preferably has the above-described 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), 5-ethyl-5- ((meth) acryloyloxymethyl) -1, 3-dioxane, and the like.
In the formula (1), n is an integer of 1 to 6.
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 and the polyfunctional (meth) acrylic compound described later is preferably 3 parts by weight, and the upper limit is preferably 95 parts by weight. The monofunctional (meth) acrylic compound of the present invention is contained in an amount of 3 parts by weight or more, whereby the resulting sealant for a liquid crystal display element has more excellent adhesion to a flexible substrate. The monofunctional (meth) acrylic compound of the present invention is contained in an amount of 95 parts by weight or less, whereby the resulting sealant for a liquid crystal display element is more excellent in moisture permeability resistance and low liquid crystal contamination resistance. The content of the monofunctional (meth) acrylic compound of the present invention is more preferably 8 parts by weight, still more preferably 80 parts by weight, still more preferably 20 parts by weight, still more preferably 65 parts by weight, and particularly preferably 60 parts by weight.
The curable resin contains a polyfunctional (meth) acrylic compound. The sealing agent for a liquid crystal display element of the present invention is excellent in moisture permeability resistance and low liquid crystal contamination resistance by containing the polyfunctional (meth) acrylic compound.
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, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide addition bisphenol A di (meth) acrylate, ethylene oxide addition bisphenol F di (meth) acrylate, dimethylol di (meth) acrylate, ethylene oxide modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acrylate, propylene carbonate, polyether glycol di (meth) acrylate, polyester glycol di (meth) acrylate, polycaprolactone glycol di (meth) acrylate, polybutadiene glycol di (meth) acrylate, and the like.
Examples of the (meth) acrylate compound having 3 or more functions among the above-mentioned polyfunctional (meth) acrylate compounds 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 a polyfunctional epoxy (meth) acrylate obtained by reacting a polyfunctional epoxy compound with a (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
Examples of the epoxy compound serving as a raw material for synthesizing the multifunctional epoxy (meth) acrylate include bisphenol a type epoxy compound, bisphenol F type epoxy compound, bisphenol S type epoxy compound, 2' -diallyl bisphenol a type epoxy compound, hydrogenated bisphenol type epoxy compound, propylene oxide addition bisphenol a type epoxy compound, resorcinol type epoxy compound, biphenyl type epoxy compound, thioether type epoxy compound, diphenyl ether type epoxy compound, dicyclopentadiene type epoxy compound, naphthalene type epoxy compound, phenol novolac type epoxy compound, o-cresol novolac type epoxy compound, dicyclopentadiene novolac type epoxy compound, biphenyl novolac type epoxy compound, naphthol novolac type epoxy compound, glycidol type epoxy compound, alkyl polyol type epoxy compound, rubber modified type epoxy compound, and glycidyl ester compound.
The polyfunctional urethane (meth) acrylate can be obtained, for example, by reacting a polyfunctional isocyanate compound with a (meth) acrylic 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, and 1,6, 11-undecane triisocyanate.
Further, as the above-mentioned polyfunctional isocyanate compound, a chain-extended polyfunctional isocyanate compound obtained by reacting a polyol with an excessive amount of the polyfunctional isocyanate compound may also 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) acrylate, mono (meth) acrylate of a diol, mono (meth) acrylate or di (meth) acrylate of a triol, and epoxy (meth) acrylate.
Examples of the hydroxyalkyl (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 triol include trimethylolethane, trimethylolpropane, and glycerin.
Examples of the epoxy (meth) acrylate include bisphenol a type epoxy acrylate.
The polyfunctional (meth) acrylic compound preferably has a ring-opened lactone structure. The polyfunctional (meth) acrylic compound has a lactone ring-opened structure, so that the sealing agent for a liquid crystal display element of the present invention is more excellent in adhesion to a flexible substrate.
In the case where the polyfunctional (meth) acrylic compound has a lactone ring-opening structure, examples of the lactone include gamma-undecalactone, epsilon-caprolactone, gamma-decalactone, sigma-dodecalactone, gamma-nonanolactone, gamma-valerolactone, sigma-valerolactone, beta-butyrolactone, gamma-butyrolactone, beta-propiolactone, sigma-caprolactone, 7-butyl-2-oxazepinone, and the like. Among them, lactones having 5 to 7 carbon atoms in the linear part of the main skeleton at the time of ring opening are preferable, and epsilon-caprolactone is more preferable. The polyfunctional (meth) acrylic compound may have a ring-opened structure of 1 lactone or may have a ring-opened structure of 2 or more lactones among these lactones.
In the case where the polyfunctional (meth) acrylic compound has a ring-opened structure of a lactone, the ring-opened structure of the lactone may be 1 in 1 molecule or may be a repeating structure. When the ring-opened structure of the lactone is a repeating structure, the preferable upper limit of the number of repeating is 5.
Among the above-mentioned polyfunctional (meth) acrylic compounds, a polyfunctional (meth) acrylic compound having a lactone ring-opened structure is preferable, a compound having a lactone ring-opened structure is introduced into the skeleton of the above-mentioned polyfunctional epoxy (meth) acrylate, more preferable is caprolactone-modified epoxy (meth) acrylate, and still more preferable is caprolactone-modified bisphenol a-type epoxy (meth) acrylate.
The polyfunctional (meth) acrylic compound may be used alone or in combination of 2 or more.
The weight average molecular weight of the polyfunctional (meth) acrylic compound is preferably limited to 800 at a lower limit and 2000 at an upper limit. When the weight average molecular weight of the polyfunctional (meth) acrylic compound falls within this range, the resulting sealant for a liquid crystal display element is more excellent in adhesiveness to a flexible substrate, coatability, and moisture permeability resistance.
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 the obtained product 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 electric company).
The sealant for a liquid crystal display element of the present invention may further contain other curable resins in addition to the monofunctional (meth) acrylic compound of the present invention and the polyfunctional (meth) acrylic compound described above, within a range that does not hinder the object of the present invention.
Examples of the other curable resin include monofunctional (meth) acrylic compounds other than the monofunctional (meth) acrylic compounds 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, 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, diethylene glycol (meth) acrylate, and (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, ethylcarbitol (meth) acrylate, 2-trifluoroethyl (meth) acrylate, 2, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, imide (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl hexahydrophthalic 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.
The epoxy compound as the other curable resin may be the same as the epoxy compound as a raw material for synthesizing the polyfunctional epoxy (meth) acrylate.
The sealant for a liquid crystal display element of the present invention contains a thermoplastic resin.
The use of the monofunctional (meth) acrylic compound of the present invention as the curable resin and the use of the thermoplastic resin makes the sealing agent for a liquid crystal display element of the present invention excellent in adhesion to a flexible substrate and can maintain a 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. The thermoplastic resin has a Tg of 30 ℃ or lower, so that the resulting sealant for a liquid crystal display element has more excellent adhesion to a flexible substrate. The upper limit of 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 refers to a value measured by Differential Scanning Calorimetry (DSC) based on "a plastic transition temperature measurement method" of JIS K7121.
The weight average molecular weight of the thermoplastic resin is preferably limited to 5000 as a lower limit and 10 ten thousand as an upper limit. The weight average molecular weight of the thermoplastic resin is 5000 or more, and thus the resulting sealant for a liquid crystal display element is further excellent in moisture permeability resistance. The thermoplastic resin has a weight average molecular weight of 10 ten thousand or less, and thus the resulting sealant for a liquid crystal display element is more excellent in coating property and adhesion to a flexible substrate. 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/(meth) acrylic acid methyl ester copolymer, polystyrene, polycarbonate, polyphenylene ether, and phenoxy resin.
Examples of the polyolefin include polyethylene, polypropylene, ethylene/vinyl acetate copolymer, ethylene/(meth) acrylic acid methyl ester copolymer, ethylene/(meth) acrylic acid ethyl ester copolymer, ethylene/vinyl alcohol copolymer, and ethylene/(meth) acrylic acid ethyl ester/maleic anhydride copolymer.
Examples of the (meth) acrylic resin include polymethyl (meth) acrylate.
Among the thermoplastic resins, polyester, (meth) acrylic resins are preferable, polyester is more preferable, copolyester is further preferable, and saturated polyester resins and saturated copolyester resins are particularly preferable.
These thermoplastic resins may be used alone or in combination of 2 or more.
In order to make the cured product of the obtained sealant for a liquid crystal display element more excellent in flexibility and toughness, the thermoplastic resin is preferably an amorphous resin, and more preferably an amorphous polyester in view of the fact that the obtained sealant for a liquid crystal display element is more excellent in adhesion to a flexible substrate.
Examples of the amorphous polyesters commercially available include VYLON300 (Tg 7 ℃, weight average molecular weight of about 55000), VYLON500 (Tg 4 ℃, weight average molecular weight of about 55000), VYLON550 (Tg-15 ℃, weight average molecular weight of about 60000), VYLON560 (Tg 7 ℃, weight average molecular weight of about 40000), VYLON630 (Tg 7 ℃, weight average molecular weight of about 55000), VYLON650 (Tg 10 ℃, weight average molecular weight of about 55000), VYLON670 (Tg 7 ℃, weight average molecular weight of about 80000) (all manufactured by eastern textile corporation), and the like.
In the present specification, the term "amorphous" refers to a case where no clear melting point peak is found by Differential Scanning Calorimetry (DSC) based on "plastic transition temperature measurement method" of JIS K7121.
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 resulting 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 resulting sealant for a liquid crystal display element is more excellent in coating property and moisture permeability resistance. The content of the thermoplastic resin is more preferably limited to 20 parts by weight, and still more preferably limited to 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 that generates radicals by irradiation with light, and a thermal radical polymerization initiator that generates radicals by heating.
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 thioxanthones.
Specific examples of the photo radical polymerization initiator include 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, 1,2- (dimethylamino) -2- ((4-methylphenyl) methyl) -1- (4- (4-morpholinyl) phenyl) -1-butanone, 2-dimethoxy-1, 2-diphenylethane-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-1-propan-1-one, 1- (4- (phenylthio) phenyl) -1, 2-octanedione 2- (O-benzoyloxime), 2,4, 6-trimethylbenzoyl diphenylphosphine oxide, and the like.
The photo radical polymerization initiator may be used alone or in combination of 2 or more.
Examples of the thermal radical polymerization initiator include thermal radical polymerization initiators composed of azo compounds, organic peroxides, and the like. Among them, an initiator composed of an azo compound (hereinafter, also referred to as "azo initiator") is preferable from the viewpoint of suppressing liquid crystal contamination, 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 in combination of 2 or more.
In the present specification, the "polymer azo compound" refers to a compound having an azo group and having a number average molecular weight of 300 or more, which generates radicals capable of curing a (meth) acryloyl group by heat.
The number average molecular weight of the polymer azo compound is preferably 1000 at the lower limit and 30 ten thousand at the upper limit. When the number average molecular weight of the polymer azo compound is in this range, the polymer azo compound can be easily mixed with the curable resin while preventing adverse effects on the liquid crystal. The number average molecular weight of the polymer azo compound is more preferably limited to 5000, more preferably to 10 ten thousand, still more preferably to 1 ten thousand, and still more preferably to 9 ten thousand.
In the present specification, the number average molecular weight is a value obtained by measuring the number average molecular weight by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting the number average molecular weight 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 electric company).
Examples of the polymer azo compound include a compound having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via azo groups.
The polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via azo groups is preferably a compound having a polyethylene oxide structure.
Specific examples of the polymer azo compound include a polycondensate of 4,4 '-azobis (4-cyanovaleric acid) and polyalkylene glycol, and a polycondensate of 4,4' -azobis (4-cyanovaleric acid) and polydimethylsiloxane having a terminal amino group.
Examples of commercially available products of the polymeric azo initiator include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (both manufactured by Fuji film and Wako pure chemical industries, ltd.).
Examples of azo initiators other than polymers include V-65 and V-501 (both of Fuji photo-pure chemical Co., ltd.).
Examples of the organic peroxide include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
The content of the polymerization initiator is preferably 0.01 part by weight at a lower limit, and 10 parts by weight at an upper limit, based on 100 parts by weight of the curable resin. When the content of the polymerization initiator is within this range, the resulting sealant for a liquid crystal display element is more excellent in storage stability and curability while suppressing contamination of the 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 thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, and acid anhydrides. Among them, organic acid hydrazides are suitably used.
The above-mentioned thermosetting agents may be used alone or in combination of 2 or more.
Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
Examples of the commercial products of the organic acid hydrazide include organic acid hydrazides manufactured by tsukamurelchemical corporation, and organic acid hydrazides manufactured by Ajinomoto Fine-Techno co.
Examples of the organic acid hydrazide manufactured by tsukamurelchemical corporation include SDH and ADH.
Examples of the organic acid hydrazide produced by Ajinomoto Fine-Techno co., inc. Include Amicure VDH, amicure VDH-J, amicure UDH, and Amicure UDH-J.
The content of the thermosetting agent is preferably 1 part by weight at a lower limit, and 50 parts by weight at an upper limit, based on 100 parts by weight of the curable resin. When the content of the thermosetting agent is within this range, thermosetting properties can be further improved without deteriorating the coatability and the like of the obtained sealing agent for a liquid crystal display element. The more preferable upper limit of the content of the above-mentioned 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 due to a stress dispersing effect, improving linear expansion coefficient, improving moisture resistance of a cured product, and the like.
As the filler, an inorganic filler and 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, and calcium silicate.
Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The above fillers may be used alone or in combination of 2 or more.
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 within this range, the effect of improving the adhesion and the like is 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 has a role as an adhesion promoter for favorably adhering the sealing agent to a substrate or the like.
As the silane coupling agent, for example, 3-aminopropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-isocyanatopropyl trimethoxysilane and the like are suitably used. These silane coupling agents have excellent effect of improving adhesion to a substrate or the like, and can inhibit the outflow of the curable resin into the liquid crystal by chemically bonding the curable resin.
The silane coupling agent may be used alone or in combination of 2 or more.
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 is preferably limited to 0.1 part by weight, and more preferably limited to 10 parts by weight. When the content of the silane coupling agent is within this range, the occurrence of liquid crystal contamination is suppressed, and the effect of improving the adhesion is further improved. The lower limit of the content of the silane coupling agent is more preferably 0.3 parts 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 shielding agent. The sealant for a liquid crystal display element of the present invention can be suitably used as a light-shielding sealant by containing the above-mentioned light-shielding agent.
Examples of the light-shielding 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 is a material having a higher transmittance for light in the vicinity of the ultraviolet region, particularly at a wavelength of 370nm to 450nm, than an average transmittance for light at a wavelength of 300nm to 800 nm. That is, the titanium black is an opacifier 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 range, while transmitting light having a wavelength in the vicinity of the ultraviolet range. Therefore, as the photo-radical polymerization initiator or the photo-cation polymerization initiator, the photo-curability of the sealant for a liquid crystal display element of the present invention can be further increased by using an initiator capable of initiating a reaction by using light having a wavelength (370 nm or more and 450nm or less) at which the transmittance of the titanium black is high. On the other hand, the light-shielding agent contained in the sealant for a liquid crystal display element of the present invention is preferably a material having high insulation properties, and titanium black is also suitable as the light-shielding agent having high insulation properties.
The optical density (OD value) of the titanium black per 1 μm is preferably 3 or more, more preferably 4 or more. The higher the light-shielding property of the titanium black, the better, and the upper limit of the OD value of the titanium black is preferably not particularly limited, but is usually 5 or less.
The titanium black exhibits a sufficient effect even without surface treatment, but may be surface-treated titanium black such as titanium black having a surface treated with an organic component such as a coupling agent or titanium black covered with an inorganic component such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, magnesium oxide, or the like. Among them, titanium black treated with an organic component is preferable from the viewpoint of further improving the insulation property.
Further, since a liquid crystal display element produced using the sealant for a liquid crystal display element of the present invention in which the titanium black is blended as a light shielding agent has a sufficient light shielding property, it is possible to realize: a liquid crystal display device having high contrast without light leakage and excellent image display quality.
Examples of the commercially available titanium black include titanium black manufactured by Mitsubishi composite materials, titanium black manufactured by Santa Clara, and titanium black manufactured by Santa Clara.
Examples of the titanium black manufactured by Mitsubishi composite Co., ltd include 12S, 13M-C, 13R-N, and 14M-C.
Examples of the titanium black manufactured by the above-mentioned red spike chemical company include Tilack D.
The specific surface area of the titanium black is preferably limited to 13m 2/g, more preferably to 30m 2/g, still more preferably to 15m 2/g, and still more preferably to 25m 2/g.
The volume resistance of the titanium black is preferably limited to 0.5 Ω·cm at a lower limit, preferably to 3 Ω·cm at a lower limit, more preferably to 1 Ω·cm at a lower limit, and even more preferably to 2.5 Ω·cm at a higher limit.
The primary particle diameter of the light-shielding agent is not particularly limited as long as it is not more than the distance between substrates of the liquid crystal display element, and is preferably limited to 1nm at a lower limit and 5000nm at an upper limit. By setting the primary particle diameter of the light-shielding agent to this range, the light-shielding property can be further improved without deteriorating the coating property and the like of the obtained sealing agent for a liquid crystal display element. The primary particle diameter of the light-shielding agent is more preferably limited to 5nm, still more preferably limited to 200nm, still more preferably limited to 10nm, and still more preferably limited to 100nm.
The primary particle diameter of the light-shielding agent may be measured by dispersing the light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP380ZLS (PARTICLE SIZING SYSTEMS).
The lower limit of the content of the light shielding agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is preferably 5 parts by weight, and the upper limit is preferably 80 parts by weight. When the content of the light blocking agent is in this range, more excellent light blocking properties can be exhibited without significantly reducing the adhesiveness, the strength after curing, and the paintability of the obtained sealant for a liquid crystal display element. The content of the light-shielding agent is more preferably 10 parts by weight, still more preferably 70 parts by weight, still more preferably 30 parts by weight, and still more preferably 60 parts by weight.
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 necessary.
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 optionally an additive such as a silane coupling agent are mixed by using a mixer. Examples of the mixer include a homomixer, a general-purpose mixer, a planetary mixer, a kneader, and a three-roll mixer.
By incorporating conductive fine particles into the sealing agent for a liquid crystal display element of the present invention, a vertically conductive material can be produced. The vertical conductive material containing the sealing agent for a liquid crystal display element and conductive fine particles of the present invention is also one of the present invention.
As the conductive fine particles, metal balls, fine particles having a conductive metal layer formed on the surface of the resin fine particles, and the like can be used. Among them, the fine particles having the conductive metal layer formed on the surface of the fine resin particles are suitable because the fine resin particles have excellent elasticity and can be electrically connected without damaging the transparent substrate or the like.
The liquid crystal display element using the sealant for a liquid crystal display element of the present invention or the vertically conductive material of the present invention is also one 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 liquid crystal dropping process. Examples of the method for manufacturing the liquid crystal display element of the present invention by the liquid crystal dropping method include the following methods.
First, a step of forming a frame-like seal pattern by applying the sealant for a liquid crystal display element of the present invention on a substrate by screen printing, dispenser application, or the like; next, a step of applying a fine droplet of liquid crystal to the entire inner surface of the frame of the seal pattern in an uncured state such as a sealant for a liquid crystal display element of the present invention, and immediately superposing the other substrate is performed; then, a step of irradiating the seal pattern portion with light such as ultraviolet light to photocure the sealant is performed, whereby a liquid crystal display element can be obtained by a method in which the above step is performed. In addition to the step of photocuring the sealant, the sealant may be heated to be cured.
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, polyethersulfone, and the like. The sealant for a liquid crystal display element of the present invention has excellent adhesion particularly to a flexible substrate composed of Polyimide (PI) and triacetyl cellulose (TAC).
The sealant for a liquid crystal display element of the present invention can be used for bonding a normal 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, or 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 permeability resistance, and low liquid crystal contamination can be provided. Further, according to the present invention, it is possible to provide a vertically conductive material and a liquid crystal display element using the sealant for a liquid crystal display element.
Detailed Description
Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.
Examples 1 to 13 and comparative examples 1 to 4
The respective materials were mixed using a planetary mixer (prepared by using a method of THINKY) according to the mixing ratio described in tables 1 and 2, and then mixed using a three-roll machine, thereby preparing the sealing agents for liquid crystal display elements of examples 1 to 13 and comparative examples 1 to 4.
< Evaluation >
The following evaluations were performed on 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 sealants for liquid crystal display elements obtained in examples and comparative examples were applied to a polyethylene terephthalate (PET) film (Lintec Corporation, made of "PET 5011") having a width of 25mm and a thickness of 40. Mu.m, to prepare test pieces. The 180-degree peel strength of the obtained test piece was measured using a tensile tester (manufactured by Shimadzu corporation, "EZ Graph") at 25℃and a peel speed of 300 mm/min.
The adhesiveness to PET substrates was evaluated by setting "verygood" when the 180 degree peel strength was 10N/cm or more, setting "good" when the 180 degree peel strength was 5N/cm or more and less than 10N/cm, setting "good" when the 180 degree peel strength was 2N/cm or more and less than 5N/cm, setting "DELTA" when the 180 degree peel strength was less than 2N/cm, and setting "×" when the 180 degree peel strength was less than 2N/cm.
(Adhesion to TAC substrate)
The sealants for liquid crystal display elements obtained in examples and comparative examples were applied to a triacetyl cellulose (TAC) film (manufactured by Fuji film Co., ltd., "TD80 UL") having a width of 25mm and a thickness of 40. Mu.m, to prepare test pieces. The 180-degree peel strength of the obtained test piece was measured using a tensile tester (manufactured by Shimadzu corporation, "EZ Graph") at 25℃and a peel speed of 300 mm/min.
The adhesion to the TAC substrate was evaluated by setting "verygood" when the 180 degree peel strength was 10N/cm or more, setting "good" when the 180 degree peel strength was 5N/cm or more and less than 10N/cm, setting "good" when the 180 degree peel strength was 2N/cm or more and less than 5N/cm, setting "DELTA" when the 180 degree peel strength was less than 2N/cm, and setting "×" 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 coated on a smooth release film using a coater so that the thickness reached 200 to 300. Mu.m. Next, a film for measuring the moisture permeability was obtained by irradiating ultraviolet rays of 100mW/cm 2 with a metal halide lamp for 30 seconds. A cup for moisture permeability test was prepared by a method of moisture permeability test method (cup method) for moisture permeability packaging material according to JIS Z0208, and the obtained film for moisture permeability measurement was attached, and the film was put into a constant temperature and humidity oven at 60℃and 90% RH to measure moisture permeability. The moisture permeability was evaluated by setting the value of the obtained moisture permeability to be "O" when the value was less than 500g/m 2.24 hours, setting the value to be "delta" when the value was 500g/m 2.24 hours or more and less than 800g/m 2.24 hours, and setting the value to be "X" when the value was 800g/m 2.24 hours or more.
(Low liquid Crystal contamination)
1 Part by weight of spacer particles (Micropearl SI-H050, manufactured by water chemical industry Co., ltd.) was dispersed in 100 parts by weight of each of the sealants for liquid crystal display elements obtained in examples and comparative examples. Next, the dispensing syringe (Musashi engineering co., LTD, "PSY-10E") was filled with the sealant in which the spacer particles were dispersed, and the defoaming treatment was performed. The sealant after the defoaming treatment was applied to one of 2 TAC films (manufactured by fuji film corporation, "TD80 UL") having a polished alignment film and a transparent electrode so that the line width became 1mm by using a dispenser (Musashi engineering co., LTD., "SHOTMASTER").
Next, a minute drop of liquid crystal (Chisso Corporation, "JC-5004 LA") was applied dropwise to the entire inner surface of the frame of the sealant of the TAC film, and another TAC film was immediately attached. Then, the sealant portion was irradiated with ultraviolet rays of 100mW/cm 2 for 30 seconds using a metal halide lamp, thereby obtaining a liquid crystal display element.
The obtained liquid crystal display element was visually checked for disturbance (display unevenness) of the alignment of the liquid crystal in the vicinity of the sealant after 24 hours of voltage application in an environment of 60 ℃ and 90% rh.
The low liquid crystal contamination property was evaluated by setting "o" when no display unevenness was observed in the liquid crystal display element, setting "Δ" when display unevenness was observed in the vicinity of the sealant (peripheral portion) of the liquid crystal display element, and setting "x" when display unevenness was spread not only in the peripheral portion but also in the central portion.
The liquid crystal display element evaluated as "o" is a level that is completely free from problems in actual use, the liquid crystal display element of "Δ" is a level that may cause problems depending on display design, and the liquid crystal display element of "x" is a level that 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 permeability resistance, and low liquid crystal contamination can be provided. Further, according to the present invention, it is possible to provide a vertically conductive material and a liquid crystal display element using the sealant for a liquid crystal display element.
Claims (5)
1. A sealant for a liquid crystal display element, characterized by comprising a curable resin, a thermoplastic resin and a polymerization initiator,
The curable resin comprises a monofunctional (meth) acrylic compound having a cyclic ether skeleton having 5 or more rings, and a polyfunctional (meth) acrylic compound,
The cyclic ether skeleton with more than 5-membered ring is at least 1 selected from tetrahydrofuran skeleton, 1, 3-dioxane skeleton, 1, 4-dioxane skeleton, 1, 2-oxathiolane skeleton and morpholine skeleton,
The monofunctional (meth) acrylic compound having a cyclic ether skeleton of 5-membered ring or more contains 3 to 95 parts by weight of the monofunctional (meth) acrylic compound having a cyclic ether skeleton of 5-membered ring or more,
The thermoplastic resin is a non-crystalline polyester,
The weight average molecular weight of the thermoplastic resin is 5000 or more and 10 ten thousand or less,
The content of the thermoplastic resin is 10 to 70 parts by weight in 100 parts by weight of the total of the curable resin and the thermoplastic resin.
2. The sealant for a liquid crystal display element according to claim 1, wherein the cyclic ether skeleton having at least 5 rings is a cyclic ether skeleton having at least 4 carbon atoms.
3. The sealant for a liquid crystal display element according to claim 1 or 2, wherein the polyfunctional (meth) acrylic compound has a ring-opened structure of lactone.
4. A vertically conductive material comprising the sealant for a liquid crystal display element according to claim 1, 2 or 3, and conductive fine particles.
5. A liquid crystal display element comprising the sealant for a liquid crystal display element according to claim 1,2 or 3 or the vertically conductive material according to claim 4.
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 |
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| CN111936924A CN111936924A (en) | 2020-11-13 |
| CN111936924B true CN111936924B (en) | 2024-07-26 |
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| CN201980021603.0A Active CN111936924B (en) | 2018-05-25 | 2019-05-16 | Sealing agent for liquid crystal display element, vertically conductive material, and liquid crystal display element |
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| Country | Link |
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| JP (2) | JP6625790B1 (en) |
| KR (1) | KR20210014093A (en) |
| CN (1) | CN111936924B (en) |
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| JP6989732B1 (en) * | 2020-05-28 | 2022-01-05 | 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201510044A (en) * | 2013-05-23 | 2015-03-16 | Nippon Kayaku Kk | Resin composition for sealing organic el element, and cured product thereof |
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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 |
| 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 |
| WO2001044342A1 (en) * | 1999-12-14 | 2001-06-21 | Mitsui Chemicals, Inc. | Sealing agent for liquid-crystal display cell, composition for sealing agent for liquid-crystal display cell, and liquid-crystal display element |
| JP2003105207A (en) * | 2001-09-28 | 2003-04-09 | Chisso Corp | Resin composition and display device using the same |
| JP4702594B2 (en) * | 2004-12-21 | 2011-06-15 | Ｄｉｃ株式会社 | Photocurable composition for liquid crystal panel seal and liquid crystal panel |
| JP5561511B2 (en) * | 2009-04-28 | 2014-07-30 | 日立化成株式会社 | Photo-curable resin composition, photo-curable moisture-proof insulating paint, electronic component using the same, and flat panel display |
| KR101475190B1 (en) * | 2011-11-04 | 2014-12-19 | 세키스이가가쿠 고교가부시키가이샤 | Sealing agent for liquid crystal display element, vertically conducting material, and liquid crystal display element |
| CN110041887B (en) * | 2015-11-09 | 2021-03-16 | 积水化学工业株式会社 | Sealing agent for liquid crystal display element, vertical conduction 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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- 2019-05-16 WO PCT/JP2019/019515 patent/WO2019225473A1/en active Application Filing
- 2019-05-16 KR KR1020207022027A patent/KR20210014093A/en not_active Application Discontinuation
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW201510044A (en) * | 2013-05-23 | 2015-03-16 | Nippon Kayaku Kk | Resin composition for sealing organic el element, and cured product thereof |
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| WO2019225473A1 (en) | 2019-11-28 |
| JP6667042B2 (en) | 2020-03-18 |
| KR20210014093A (en) | 2021-02-08 |
| JPWO2019225473A1 (en) | 2020-05-28 |
| JP2020013165A (en) | 2020-01-23 |
| TW202003775A (en) | 2020-01-16 |
| CN111936924A (en) | 2020-11-13 |
| TWI813690B (en) | 2023-09-01 |
| JP6625790B1 (en) | 2019-12-25 |
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