WO2019221027A1 - Agent d'étanchéité pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides - Google Patents

Agent d'étanchéité pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides Download PDF

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Publication number
WO2019221027A1
WO2019221027A1 PCT/JP2019/018764 JP2019018764W WO2019221027A1 WO 2019221027 A1 WO2019221027 A1 WO 2019221027A1 JP 2019018764 W JP2019018764 W JP 2019018764W WO 2019221027 A1 WO2019221027 A1 WO 2019221027A1
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Prior art keywords
liquid crystal
crystal display
display element
sealing agent
compound
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PCT/JP2019/018764
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English (en)
Japanese (ja)
Inventor
慶枝 松井
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積水化学工業株式会社
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Priority to JP2019529280A priority Critical patent/JP6773907B2/ja
Publication of WO2019221027A1 publication Critical patent/WO2019221027A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1339—Gaskets; Spacers; Sealing of cells

Definitions

  • the present invention relates to a sealing agent for a liquid crystal display element, which can suppress liquid crystal contamination due to insertion into a sealing agent by liquid crystal and liquid crystal contamination by the sealing agent, and can obtain a liquid crystal display element having excellent adhesiveness and excellent display performance. Moreover, this invention relates to the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements.
  • a liquid crystal dropping method called a construction method is used.
  • a sealing agent is applied to one of the two transparent substrates with electrodes to form a frame-shaped seal pattern.
  • liquid crystal microdrops are dropped on the entire surface of the seal pattern frame with the sealant uncured, and the other transparent substrate is immediately bonded together, and the seal portion is irradiated with light such as ultraviolet rays or heated.
  • the sealing agent is cured to produce a liquid crystal display element. If the substrates are bonded together under reduced pressure, a liquid crystal display element can be manufactured with extremely high efficiency, and this dripping method is currently the mainstream method for manufacturing liquid crystal display elements.
  • the liquid crystal flows when heated and inserted into the sealant part during curing, resulting in tearing of the seal pattern, etc. Or the liquid crystal is contaminated by a sealant whose viscosity is reduced by heating.
  • the line width of the sealant to be applied has become narrower and the cross-sectional area of the seal after bonding has become smaller as the panel becomes narrower. Therefore, the seal pattern is easily broken.
  • the present invention provides a sealant for a liquid crystal display element that can suppress liquid crystal contamination due to insertion into a sealant with liquid crystal and liquid crystal contamination due to the sealant, and that can provide a liquid crystal display element with excellent adhesiveness and excellent display performance. With the goal.
  • Another object of the present invention is to provide a vertical conduction material and a liquid crystal display element using the sealing agent for a liquid crystal display element.
  • the present invention contains a curable resin, a thermosetting agent, and flexible particles having a maximum particle size of 100% or more of the cell gap of the liquid crystal display element, and the curable resin is 3 or more per molecule. It is the sealing compound for liquid crystal display elements containing the compound which has the epoxy group of. The present invention is described in detail below.
  • PSA Polymer Stained Alignment
  • liquid crystal display elements that can realize high-speed response and high contrast.
  • a liquid crystal composition containing a polymerizable compound is used, and the liquid crystal composition in the liquid crystal composition is irradiated by irradiating light to the liquid crystal composition filled in the cell of the liquid crystal display element.
  • the compound is polymerized to form a concavo-convex shape on the substrate, thereby giving a uniform pretilt angle and controlling the alignment of liquid crystal molecules.
  • a PSA type liquid crystal display element is sealed using a conventional sealant, there is a problem that uneven shapes formed on the substrate vary, and a uniform pretilt angle may not be provided. .
  • the present inventor has found that when a PSA type liquid crystal display element is sealed using a conventional sealant, the unevenness formed on the substrate may cause variations in the sealant as a curable resin. It was considered to be in the (meth) acrylic compound contained. That is, when the polymerizable compound in the liquid crystal is polymerized by elution of the (meth) acrylic compound in the curable resin, the (meth) acrylic compound is also polymerized, and the (meth) acrylic compound is polymerized. It was considered that the uneven shape different from the intended one was formed in the part.
  • the present inventor has studied sealing a PSA type liquid crystal display element using a sealing agent that does not contain a (meth) acrylic compound or has a reduced content of a (meth) acrylic compound.
  • a sealing agent that does not contain a (meth) acrylic compound or has a reduced content of a (meth) acrylic compound.
  • the present inventor has studied to suppress insertion of liquid crystal into the sealing agent and liquid crystal contamination due to the sealing agent by blending flexible particles whose maximum particle diameter is 100% or more of the cell gap of the liquid crystal display element. .
  • flexible particles whose maximum particle diameter is 100% or more of the cell gap of the liquid crystal display element.
  • the resulting sealant is inferior in adhesiveness.
  • the present inventor further examined the use of a compound having three or more epoxy groups in one molecule as the curable resin.
  • a sealant for a liquid crystal display element that can suppress liquid crystal contamination due to insertion into the sealant with liquid crystal and liquid crystal contamination due to the sealant, and can obtain a liquid crystal display element having excellent adhesion and excellent display performance.
  • the present invention has been completed.
  • the effect of suppressing the insertion of the liquid crystal into the sealing agent and the liquid crystal contamination by the sealing agent in the sealing agent for a liquid crystal display element of the present invention is particularly remarkable when the sealing agent is cured only by heat.
  • the sealing compound for liquid crystal display elements of this invention is used suitably as a sealing compound for PSA type liquid crystal display elements.
  • the sealing agent for liquid crystal display elements of this invention contains curable resin.
  • the curable resin contains a compound having three or more epoxy groups in one molecule (hereinafter also referred to as “trifunctional or higher functional epoxy compound”).
  • trifunctional or higher functional epoxy compound a compound having three or more epoxy groups in one molecule
  • the trifunctional or higher functional epoxy compound is excellent in reactivity, and the obtained sealing agent for liquid crystal display elements is excellent in the effect of suppressing the liquid crystal contamination due to the insertion into the sealing agent by the liquid crystal and the sealing agent. It preferably has 6 or more epoxy groups.
  • a compound having three or more epoxy groups and an isocyanuric skeleton in one molecule, and / or 1 It is preferably a glycidylamine type epoxy compound having three or more epoxy groups in the molecule. More preferably, it is a compound having three or more epoxy groups and an isocyanuric skeleton in one molecule.
  • the trifunctional or higher functional epoxy compound examples include a compound represented by the following formula (1), a compound represented by the following formula (2), a compound represented by the following formula (3), and the like. Can be mentioned. Especially, the compound represented by the following formula (1) and the compound represented by the following formula (2) are preferable, and the compound represented by the following formula (1) is more preferable.
  • the curable resin may contain another curable resin in addition to the trifunctional or higher functional epoxy compound.
  • the preferable lower limit of the content of the trifunctional or higher functional epoxy compound in 100 parts by weight of the curable resin is 50 parts by weight, and the preferable upper limit is 95 parts by weight.
  • the content of the above-mentioned trifunctional or higher functional epoxy compound is within this range, the resulting liquid crystal display element sealant is excellent in the effect of suppressing elution into the liquid crystal and the insertion of the liquid crystal into the sealant.
  • the more preferable lower limit of the content of the trifunctional or higher epoxy compound is 60 parts by weight, and the more preferable upper limit is 90 parts by weight.
  • a monofunctional epoxy compound or a bifunctional epoxy compound is used suitably.
  • the part which has one or two epoxy groups in 1 molecule formed by making a part of epoxy group of a polyfunctional epoxy compound react with (meth) acrylic acid A (meth) acryl-modified epoxy resin (hereinafter also simply referred to as “partial (meth) acryl-modified epoxy resin”) is preferable.
  • partial (meth) acryl-modified epoxy resin since the fast curing property of the obtained sealant for liquid crystal display elements is improved and the effect of suppressing the insertion of the liquid crystal into the sealant is excellent, the above-mentioned partial (meth) acryl-modified epoxy resin is heat described later. It is preferable to use in combination with a radical polymerization initiator.
  • Examples of other monofunctional epoxy compounds include allyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, and glycidyl (meth) acrylate.
  • the “(meth) acryl” means acryl or methacryl
  • the “(meth) acrylate” means acrylate or methacrylate.
  • bifunctional epoxy compounds examples include bisphenol A type bifunctional epoxy compounds, bisphenol F type bifunctional epoxy compounds, bisphenol S type bifunctional epoxy compounds, and 2,2′-diallyl bisphenol A type bifunctional.
  • the sealing agent for a liquid crystal display element of the present invention may contain a (meth) acrylic compound having no epoxy group as the other curable resin, but by elution into the liquid crystal in the case of a PSA type liquid crystal display element. From the viewpoint of suppressing adverse effects on the uneven shape, it is preferable not to contain a (meth) acrylic compound having no epoxy group.
  • the “(meth) acrylic compound” means a compound having a (meth) acryloyl group
  • the “(meth) acryloyl” means acryloyl or methacryloyl.
  • the sealing agent for liquid crystal display elements of this invention contains a thermosetting agent.
  • the thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, acid anhydrides, and the like. Of these, organic acid hydrazide is preferably used.
  • the said thermosetting agent may be used independently and 2 or more types may be used in combination.
  • Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
  • Examples of commercially available organic acid hydrazides include organic acid hydrazides manufactured by Otsuka Chemical Co., Ltd., organic acid hydrazides manufactured by Ajinomoto Fine Techno Co., and organic acid hydrazides manufactured by Nippon Finechem Co., Ltd., and the like.
  • Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH.
  • Examples of the organic acid hydrazide manufactured by Ajinomoto Fine Techno Co. include Amicure VDH, Amicure VDH-J, Amicure UDH, Amicure UDH-J, and the like.
  • Examples of the organic acid hydrazide manufactured by Nippon Finechem Co., Ltd. include MDH.
  • the content of the thermosetting agent is preferably 1 part by weight with respect to 100 parts by weight of the curable resin, and 50 parts by weight with respect to the preferable upper limit.
  • the upper limit with more preferable content of the said thermosetting agent is 30 weight part.
  • the sealing agent for liquid crystal display elements of this invention contains a polymerization initiator.
  • the polymerization initiator include radical polymerization initiators and cationic polymerization initiators.
  • the spring back by the soft particles described later is affected not only by the maximum particle size of the soft particles but also by the curing rate of the sealant. Since the radical polymerization initiator can significantly increase the curing rate compared to the thermosetting agent, by using in combination with the flexible particles, it suppresses the occurrence of springback that is likely to occur due to the flexible particles, The obtained liquid crystal display element becomes more excellent in gap retention.
  • the radical polymerization initiator examples include a thermal radical polymerization initiator that generates radicals by heating, a photo radical polymerization initiator that generates radicals by light irradiation, and the like.
  • a thermal radical polymerization initiator is preferable.
  • the partial (meth) acryl-modified epoxy is used. More preferably, the resin is used in combination with the thermal radical polymerization initiator.
  • thermal radical polymerization initiator what is comprised with an azo compound, an organic peroxide, etc. is mentioned, for example.
  • an initiator composed of an azo compound hereinafter also referred to as “azo initiator”
  • an initiator composed of a polymer azo compound hereinafter referred to as “polymer azo”.
  • azo initiator an initiator composed of an azo compound
  • polymer azo an initiator composed of a polymer azo compound
  • Also referred to as “initiator” is more preferred.
  • the said thermal radical polymerization initiator may be used independently, and 2 or more types may be used in combination.
  • the “polymer azo compound” means a compound having an azo group and generating a radical capable of reacting with a (meth) acryloyl group by heat and having a number average molecular weight of 300 or more. To do.
  • the preferable lower limit of the number average molecular weight of the polymer azo compound is 1000, and the preferable upper limit is 300,000.
  • the more preferable lower limit of the number average molecular weight of the polymer azo compound is 5000, the more preferable upper limit is 100,000, the still more preferable lower limit is 10,000, and the still more preferable upper limit is 90,000.
  • the said number average molecular weight is a value calculated
  • Examples of the polymer azo compound include those 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 units such as polyalkylene oxide are bonded via the azo group those having a polyethylene oxide structure are preferable.
  • Specific examples of the polymer azo compound include polycondensates of 4,4′-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4′-azobis (4-cyanopentanoic acid). And a polycondensate of polydimethylsiloxane having a terminal amino group.
  • Examples of commercially available polymer azo initiators include VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001 (all manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.). Can be mentioned.
  • Examples of the azo initiator that is not a polymer include V-65 and V-501 (both manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.).
  • organic peroxide examples include ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
  • the said thermal radical polymerization initiator may be used independently, and 2 or more types may be used in combination.
  • photo radical polymerization initiator examples include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, and thioxanthone compounds.
  • Specific examples of the photo radical polymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, and 2- (dimethylamino).
  • a photocationic polymerization initiator is preferably used as the cationic polymerization initiator.
  • the cationic photopolymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and may be of an ionic photoacid generation type or a nonionic photoacid generation type. It may be.
  • Examples of the photocationic polymerization initiator include onium salts such as aromatic diazonium salts, aromatic halonium salts, and aromatic sulfonium salts, organometallic complexes such as iron-allene complexes, titanocene complexes, and arylsilanol-aluminum complexes. Is mentioned.
  • photocationic polymerization initiators examples include Adekaoptomer SP-150 and Adekaoptomer SP-170 (both manufactured by ADEKA).
  • the said cationic photopolymerization initiator may be used independently and 2 or more types may be used in combination.
  • the content of the polymerization initiator is preferably 0.01 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the polymerization initiator is within this range, the obtained sealing agent for liquid crystal display elements is excellent in storage stability and curability while suppressing liquid crystal contamination.
  • the minimum with more preferable content of the said polymerization initiator is 0.1 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for liquid crystal display elements of this invention is used suitably for sealing of the liquid crystal between the board
  • the sealing agent for liquid crystal display elements of the present invention contains flexible particles (hereinafter also simply referred to as “soft particles”) having a maximum particle size of 100% or more of the cell gap of the liquid crystal display element.
  • the flexible particles serve as a barrier between the other sealing agent component and the liquid crystal, preventing the liquid crystal from being inserted into the sealing agent and the sealing agent from being eluted into the liquid crystal. Have a role to play. Further, by blending the flexible particles, it is possible to prevent the substrate from being displaced until the sealing agent is cured after the substrates are bonded together.
  • the cell gap of the liquid crystal display element is not limited because it varies depending on the display element, but the cell gap of a general liquid crystal display element is 2 ⁇ m or more and 10 ⁇ m or less.
  • the maximum particle diameter of the flexible particles is 100% or more of the cell gap of the liquid crystal display element.
  • the maximum particle diameter of the flexible particles is preferably more than 100% of the cell gap of the liquid crystal display element.
  • the maximum particle size of the flexible particles is preferably 5 ⁇ m or more.
  • the preferable upper limit of the maximum particle size of the flexible particles is 20 ⁇ m. When the maximum particle size of the flexible particles is 20 ⁇ m or less, the spring back is suppressed, and the obtained liquid crystal display element is more excellent in gap retention.
  • a more preferable upper limit of the maximum particle size of the flexible particles is 15 ⁇ m. Furthermore, the maximum particle size of the flexible particles is preferably 260% or less of the cell gap. When the maximum particle size of the flexible particles is 260% or less of the cell gap, the spring back is suppressed, and the obtained liquid crystal display device is more excellent in gap retention. A more preferred upper limit of the maximum particle size of the flexible particles is 220% of the cell gap, and a more preferred upper limit is 170% of the cell gap.
  • the maximum particle diameter of the flexible particles and the average particle diameter described later are values obtained by measuring the particles before blending with the sealant using a laser diffraction particle size distribution measuring device. Means.
  • the laser diffraction particle size distribution measuring device Mastersizer 2000 (manufactured by Malvern) or the like can be used.
  • the maximum value and the average value of the particle diameter of ten particles observed by the magnification of 10,000 times using the scanning electron microscope are meant.
  • the scanning electron microscope a field emission scanning electron microscope S-4800 (manufactured by Hitachi High-Technologies Corporation) or the like can be used.
  • the maximum particle size of the flexible particles Is 100% or more of the cell gap of the liquid crystal display element.
  • the content ratio of particles having a particle diameter of 5 ⁇ m or more in the particle size distribution of the flexible particles measured by the laser diffraction type distribution measuring device is preferably 60% or more by volume frequency.
  • the content ratio of the particles having a particle diameter of 5 ⁇ m or more is 60% or more by volume frequency, the effect of suppressing insertion of liquid crystal into the sealing agent and liquid crystal contamination by the sealing agent is excellent.
  • the content ratio of particles having a particle diameter of 5 ⁇ m or more is more preferably 80% or more.
  • the content ratio of particles of 100% or more of the cell gap of the liquid crystal display element is 70% or more by volume frequency.
  • the liquid crystal display element is more excellent in the effect of suppressing insertion into the sealing agent by liquid crystal and liquid crystal contamination by the sealing agent.
  • the flexible particles are composed of particles having a volume content of 100% or more of the cell gap of the liquid crystal display element by volume frequency, ie, 100% or more of the cell gap of the liquid crystal display element.
  • the preferable lower limit of the average particle diameter of the flexible particles is 2 ⁇ m, and the preferable upper limit is 15 ⁇ m.
  • the average particle diameter of the flexible particles is 2 ⁇ m or more, the effect of suppressing the liquid crystal contamination due to the insertion of the liquid crystal into the sealing agent and the sealing agent becomes excellent.
  • the average particle diameter of the flexible particles is 15 ⁇ m or less, the obtained liquid crystal display element is more excellent in gap retention.
  • the more preferable lower limit of the average particle diameter of the flexible particles is 4 ⁇ m, and the more preferable upper limit is 12 ⁇ m.
  • two or more kinds of flexible particles having different maximum particle diameters may be mixed and used as long as the overall maximum particle diameter is in the above-described range. That is, a soft particle having a maximum particle diameter of less than 100% of the cell gap of the liquid crystal display element and a soft particle having a maximum particle diameter of 100% or more of the cell gap of the liquid crystal display element may be mixed and used.
  • the coefficient of variation (hereinafter also referred to as “CV value”) of the flexible particles is preferably 30% or less.
  • the CV value of the particle diameter of the flexible particles is more preferably 28% or less, and further preferably 15% or less.
  • the flexible particles are classified so that the maximum particle diameter, average particle diameter, and CV value are within the above-described ranges. Can do.
  • flexible particles with a particle size of less than 100% of the cell gap of the liquid crystal display element do not contribute to the suppression of liquid crystal contamination due to the insertion of the liquid crystal into the sealing agent or the sealing agent. Therefore, it is preferable to remove by classification.
  • the method for classifying the flexible particles include wet classification and dry classification. Of these, wet classification is preferable, and wet sieving classification is more preferable.
  • the soft particles are unloaded from the reversal load value to the origin load value when releasing the load, with the compression displacement from the origin load value when applying the load to the predetermined reversal load value being L1.
  • the displacement is L2
  • the recovery rate expressed as a percentage of L2 / L1 is 80% or less.
  • the recovery rate of the flexible particles is 80% or less, the effect of suppressing insertion of liquid crystal into the sealant and liquid crystal contamination due to the sealant is excellent.
  • a more preferable upper limit of the recovery rate of the flexible particles is 70%, and a more preferable upper limit is 60%. Further, the recovery rate of the flexible particles is substantially 5% or more.
  • grain can be derived
  • the flexible particles preferably have a 1 g strain expressed as a percentage of L3 / Dn as a percentage of 30% or more when the compression displacement when a load of 1 g is applied is L3 and the particle diameter is Dn.
  • a 1 g strain of the flexible particles is 30% or more, the effect of suppressing insertion of liquid crystal into the sealing agent and liquid crystal contamination due to the sealing agent is improved.
  • a more preferable lower limit of 1 g strain of the flexible particles is 40%.
  • the 1 g strain of the flexible particles can be derived by applying a load of 1 g to each particle using a micro compression tester and measuring the amount of displacement at that time.
  • the flexible particles preferably have a fracture strain expressed as a percentage of L4 / Dn of 50% or more, where L4 is the compression displacement when the particles are broken and Dn is the particle diameter.
  • L4 is the compression displacement when the particles are broken
  • Dn is the particle diameter.
  • the fracture strain of the flexible particles can be derived by applying a load to one particle using a micro compression tester and measuring the displacement at which the particle breaks.
  • the compression displacement L4 is calculated as the time when the particle breaks when the amount of displacement increases discontinuously with respect to the applied load. If the deformation does not break even if the load is increased, the fracture strain is considered to be 100% or more.
  • the flexible particles have a preferable lower limit of the glass transition temperature of ⁇ 200 ° C. and a preferable upper limit of 40 ° C.
  • the lower the glass transition temperature of the flexible particles the better the tendency from the viewpoint of preventing the liquid crystal from being inserted into the sealant and the liquid crystal contamination by the sealant. It will be better.
  • the glass transition temperature of the flexible particles is 40 ° C. or less, the obtained liquid crystal display element is more excellent in gap retention.
  • a more preferable lower limit of the glass transition temperature of the flexible particles is ⁇ 150 ° C., and a more preferable upper limit is 35 ° C.
  • the glass transition temperature of the said flexible particle shows the value measured by the differential scanning calorimetry (DSC) based on "The plastics transition temperature measuring method" of JISK7121.
  • the flexible particles include silicone particles, vinyl particles, urethane particles, fluorine particles, and nitrile particles. Of these, silicone particles and vinyl particles are preferable.
  • grain a silicone rubber particle is preferable from a dispersible viewpoint to resin.
  • examples of commercially available silicone particles include KMP-594, KMP-597, KMP-598, KMP-600, KMP-601, KMP-602 (all manufactured by Shin-Etsu Chemical Co., Ltd.), Trefil E-506S, EP-9215 (both manufactured by Toray Dow Corning Co., Ltd.) and the like can be mentioned, and these can be classified and used.
  • grains may be used independently and 2 or more types may be used together.
  • (Meth) acrylic particles are preferably used as the vinyl particles.
  • the (meth) acrylic particles can be obtained by polymerizing monomers as raw materials by a known method. Specifically, for example, a method in which a monomer is suspension-polymerized in the presence of a radical polymerization initiator, and a seed particle is swollen by absorbing the monomer into a non-crosslinked seed particle in the presence of a radical polymerization initiator. And a seed polymerization method.
  • the “(meth) acryl” means acryl or methacryl.
  • a monofunctional monomer can be used as a monomer as a raw material for forming the (meth) acrylic particles.
  • the monofunctional monomer include alkyl mono (meth) acrylates, oxygen atom-containing mono (meth) acrylates, nitrile-containing mono (meth) acrylic monomers, and fluorine atom-containing mono (meth) acrylates.
  • alkyl mono (meth) acrylate examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, 2- Examples include ethylhexyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, and isobornyl (meth) acrylate.
  • Examples of the oxygen atom-containing mono (meth) acrylate include 2-hydroxyethyl (meth) acrylate, glycerol (meth) acrylate, polyoxyethylene (meth) acrylate, and glycidyl (meth) acrylate.
  • Examples of the nitrile-containing mono (meth) acrylic monomer include (meth) acrylonitrile.
  • Examples of the fluorine atom-containing mono (meth) acrylate include trifluoromethyl (meth) acrylate and pentafluoroethyl (meth) acrylate.
  • alkyl mono (meth) acrylate is preferable.
  • the “(meth) acrylate” means acrylate or methacrylate.
  • a polyfunctional monomer may be used as the monomer in order to give a crosslinked structure.
  • the polyfunctional monomer include tetramethylolmethane tetra (meth) acrylate, tetramethylolmethane tri (meth) acrylate, tetramethylolmethane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, and dipentaerythritol.
  • a preferable lower limit of the amount of the polyfunctional monomer used in the whole monomer is 1% by weight, and a preferable upper limit is 90% by weight.
  • the amount of the polyfunctional monomer used is 1% by weight or more, the solvent resistance of the flexible particles is improved, and when mixed with other sealing agent components, problems such as swelling do not occur, and it is uniform. Easy to disperse.
  • the amount of the polyfunctional monomer used is 90% by weight or less, the recovery rate of the flexible particles can be lowered, and problems such as springback are less likely to occur.
  • a more preferable lower limit of the amount of the polyfunctional monomer used is 3% by weight, and a more preferable upper limit is 80% by weight.
  • styrene monomers for example, styrene monomers, vinyl ethers, vinyl esters, unsaturated hydrocarbons, halogen atom-containing monomers And monomers such as triallyl (iso) cyanurate, triallyl trimellitate, divinylbenzene, diallyl phthalate, diallylacrylamide, diallyl ether, 3- (meth) acryloxypropyltrimethoxysilane, vinyltrimethoxysilane May be.
  • the styrene monomer include styrene, ⁇ -methylstyrene, trimethoxysilylstyrene, and the like.
  • Examples of the vinyl ethers include methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, and the like.
  • Examples of the vinyl esters include vinyl acetate, vinyl butyrate, vinyl laurate, and vinyl stearate.
  • Examples of the unsaturated hydrocarbon include ethylene, propylene, isoprene, butadiene and the like.
  • Examples of the halogen atom-containing monomer include vinyl chloride, vinyl fluoride, chlorostyrene, and the like.
  • vinyl particles for example, polydivinylbenzene particles, polychloroprene particles, butadiene rubber particles and the like may be used.
  • urethane-based particles examples include Art Pearl (manufactured by Negami Kogyo Co., Ltd.), Dimic Beads (manufactured by Dainichi Seika Kogyo Co., Ltd.), and the like, which can be classified and used. .
  • the preferable lower limit of the hardness of the flexible particles is 3, and the preferable upper limit is 50.
  • the more preferable lower limit of the hardness of the flexible particle is 10, the more preferable upper limit is 40, and the more preferable lower limit is 20.
  • the above-mentioned “hardness of flexible particles” means durometer A hardness measured by a method based on JIS K 6253.
  • the minimum with preferable content of the said flexible particle in the sealing compound for liquid crystal display elements of this invention is 5 weight%, and a preferable upper limit is 60 weight%.
  • a preferable upper limit is 60 weight%.
  • the content of the flexible particles is 5% by weight or more, the effect of suppressing insertion of liquid crystal into the sealing agent and liquid crystal contamination due to the sealing agent is improved.
  • the content of the flexible particles is 60% by weight or less, the obtained sealing agent for liquid crystal display elements is more excellent in adhesiveness.
  • the more preferable lower limit of the content of the flexible particles is 10% by weight, the more preferable upper limit is 50% by weight, the still more preferable lower limit is 20% by weight, and the still more preferable upper limit is 40% by weight.
  • the sealing agent for liquid crystal display elements of the present invention preferably contains a filler for the purpose of improving the viscosity, improving the adhesiveness due to the stress dispersion effect, improving the linear expansion coefficient, and the like.
  • an inorganic filler or an organic filler can be used as the filler.
  • 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, and titanium oxide.
  • the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles. The said filler may be used independently and 2 or more types may be used in combination.
  • the preferable lower limit of the content of the filler in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight.
  • the minimum with more preferable content of the said filler is 20 weight part, and a more preferable upper limit is 60 weight part.
  • the sealing agent for liquid crystal display elements of the present invention may contain a silane coupling agent.
  • the silane coupling agent mainly has a role as an adhesion assistant for favorably bonding the sealing agent and the substrate.
  • silane coupling agent for example, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are preferably used. These are excellent in the effect of improving the adhesion to a substrate or the like, and can suppress the outflow of the curable resin into the liquid crystal by chemically bonding with the curable resin.
  • the said silane coupling agent may be used independently and 2 or more types may be used in combination.
  • the minimum with preferable content of the said silane coupling agent in 100 weight part of sealing compounds for liquid crystal display elements of this invention is 0.1 weight part, and a preferable upper limit is 10 weight part.
  • a preferable upper limit is 10 weight part.
  • the minimum with more preferable content of the said silane coupling agent is 0.3 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for liquid crystal display elements of the present invention may contain a light shielding agent.
  • the sealing compound for liquid crystal display elements of this invention can be used suitably as a light shielding sealing agent.
  • Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Of these, titanium black is preferable.
  • Titanium black is a substance having higher transmittance for light in the vicinity of the ultraviolet region, particularly for light with a wavelength of 370 nm to 450 nm, compared to the average transmittance for light with a wavelength of 300 nm to 800 nm. That is, the above-described titanium black sufficiently shields light having a wavelength in the visible light region, thereby providing a light shielding property to the sealing agent for liquid crystal display elements of the present invention, while transmitting light having a wavelength in the vicinity of the ultraviolet region.
  • a shading agent is a substance having higher transmittance for light in the vicinity of the ultraviolet region, particularly for light with a wavelength of 370 nm to 450 nm, compared to the average transmittance for light with a wavelength of 300 nm to 800 nm. That is, the above-described titanium black sufficiently shields light having a wavelength in the visible light region, thereby providing a light shielding property to the sealing agent for liquid crystal display elements of the present invention, while transmitting light having a wavelength
  • the photo radical polymerization initiator or the photo cationic polymerization initiator that can start the reaction with light having a wavelength (370 nm or more and 450 nm or less) that increases the transmittance of the titanium black.
  • the light shielding agent contained in the liquid crystal display element sealant of the present invention is preferably a highly insulating material, and titanium black is also preferred as the highly insulating light shielding agent.
  • the titanium black preferably has an optical density (OD value) per ⁇ m of 3 or more, more preferably 4 or more. The higher the light-shielding property of the titanium black, the better.
  • the OD value of the titanium black is not particularly limited, but is usually 5 or less.
  • the above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
  • the liquid crystal display element produced using the sealing agent for liquid crystal display elements of the present invention containing the above-described titanium black as a light-shielding agent has sufficient light-shielding properties, and therefore has high contrast without light leakage. A liquid crystal display element having excellent image display quality can be realized.
  • Examples of commercially available titanium black include titanium black manufactured by Mitsubishi Materials Corporation and titanium black manufactured by Ako Kasei Co., Ltd. Examples of the titanium black manufactured by Mitsubishi Materials include 12S, 13M, 13M-C, 13R-N, and 14M-C. Examples of the titanium black manufactured by Ako Kasei Co., Ltd. include Tilac D.
  • the preferable lower limit of the specific surface area of the titanium black is 13 m 2 / g, the preferable upper limit is 30 m 2 / g, the more preferable lower limit is 15 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
  • the preferred lower limit of the volume resistance of the titanium black is 0.5 ⁇ ⁇ cm, the preferred upper limit is 3 ⁇ ⁇ cm, the more preferred lower limit is 1 ⁇ ⁇ cm, and the more preferred upper limit is 2.5 ⁇ ⁇ cm.
  • the primary particle diameter of the said light-shielding agent will not be specifically limited if it is below the distance between the board
  • the more preferable lower limit of the primary particle diameter of the light shielding agent is 5 nm
  • the more preferable upper limit is 200 nm
  • the still more preferable lower limit is 10 nm
  • the still more preferable upper limit is 100 nm.
  • the primary particle size of the light shielding agent can be measured by using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS) and dispersing the light shielding agent in a solvent (water, organic solvent, etc.).
  • the preferable lower limit of the content of the light-shielding agent in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 5 parts by weight, and the preferable upper limit is 80 parts by weight.
  • the more preferable lower limit of the content of the light shielding agent is 10 parts by weight, the more preferable upper limit is 70 parts by weight, the still more preferable lower limit is 30 parts by weight, and the still more preferable upper limit is 60 parts by weight.
  • the sealant for a liquid crystal display element of the present invention may further include a stress relaxation agent, a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, a polymerization inhibitor, etc., if necessary.
  • the additive may be contained.
  • the method for producing the sealing agent for liquid crystal display elements of the present invention is not particularly limited. For example, using a mixer, a curable resin, a thermosetting agent, flexible particles, and a silane coupling added as necessary.
  • the method of mixing additives, such as an agent, is mentioned.
  • the mixer include a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll.
  • a vertical conduction material can be produced by blending conductive fine particles with the sealing agent for liquid crystal display elements of the present invention.
  • the vertical conduction material containing the sealing agent for liquid crystal display elements of the present invention and conductive fine particles is also one aspect of the present invention.
  • the conductive fine particles a metal ball, a resin fine particle formed with a conductive metal layer on the surface, or the like can be used.
  • the one in which the conductive metal layer is formed on the surface of the resin fine particles is preferable because the conductive connection is possible without damaging the transparent substrate due to the excellent elasticity of the resin fine particles.
  • the liquid crystal display element using the sealing agent for liquid crystal display elements of this invention or the vertical conduction material of this invention is also one of this invention.
  • a liquid crystal display element having a narrow frame design is preferable.
  • the width of the frame portion around the liquid crystal display unit is preferably 2 mm or less.
  • variety of the sealing compound for liquid crystal display elements of this invention at the time of manufacturing the liquid crystal display element of this invention is 1 mm or less.
  • a liquid crystal dropping method is preferably used as a method for producing the liquid crystal display element of the present invention.
  • a method for producing the liquid crystal display element of the present invention includes a method having the following steps. First, a process for forming a frame-shaped seal pattern by applying the liquid crystal display element sealant of the present invention to one of two transparent substrates having an electrode such as an ITO thin film and an alignment film by screen printing, dispenser application, etc. I do. Next, the liquid crystal composition-containing liquid crystal composition-containing liquid crystal composition-containing liquid crystal composition containing the polymerizable compound in an uncured sealant is dropped into the seal pattern frame of the substrate, and the other transparent substrate is applied under vacuum. The process of superimposing is performed. Then, the process of hardening the sealing compound for liquid crystal display elements of this invention by heating is performed.
  • a PSA type liquid crystal display element can be obtained by a method in which a polymerizable compound in a liquid crystal composition is polymerized by light irradiation or the like in a voltage applied state to form a concavo-convex shape on a substrate.
  • a step of temporarily curing the sealing agent by light irradiation may be performed, but in the sealing agent for liquid crystal display elements of the present invention, The effect of suppressing the insertion of the liquid crystal into the sealant and the liquid crystal contamination due to the sealant is particularly remarkable when the sealant is cured only by heat.
  • the sealing agent for liquid crystal display elements which can suppress the liquid crystal contamination by the insertion to the sealing agent with a liquid crystal and liquid crystal contamination by a sealing agent, and is excellent in adhesiveness and display performance is provided. can do.
  • the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements can be provided.
  • Resorcinol type epoxy resin (manufactured by Nagase ChemteX Corporation, “Denacol EX-201”) 1000 parts by weight, p-methoxyphenol 2 parts by weight as a polymerization inhibitor, triethylamine 2 parts by weight, and 649 parts by weight of acrylic acid Then, the reaction was carried out by stirring at 90 ° C. for 5 hours while feeding air.
  • Silicone rubber particles (manufactured by Shin-Etsu Chemical Co., Ltd., “KMP-601”) are dispersed in methanol so that the particle diameter is in the range of 5 to 8 ⁇ m with an 8 ⁇ m aperture sieve and a 5 ⁇ m aperture sieve. Wet sieve classification. The classified particles were collected and dried to obtain a silicone rubber particle classified product. As the sieve, a polyimide film having a hole with extremely high accuracy obtained by applying ultrahigh precision fine processing with a laser was used. The obtained silicone rubber particle classification product had a maximum particle size of 8 ⁇ m as measured using a laser diffraction particle size distribution analyzer (manufactured by Malvern, “Mastersizer 2000”).
  • a silicone rubber particle classified product (maximum particle size) was obtained in the same manner except that wet sieve classification was performed so that the particle diameter would be in the range of 3 to 6 ⁇ m with a 6 ⁇ m aperture sieve and a 3 ⁇ m aperture sieve. 6 ⁇ m in diameter) was obtained. Further, a silicone rubber particle classified product (maximum particle diameter 3 ⁇ m) was obtained in the same manner except that the wet sieve classification was performed so that the particle diameter was 3 ⁇ m or less with a sieve having an opening of 3 ⁇ m.
  • Examples 1 to 10 Comparative Examples 1 to 3
  • each material was mixed using a planetary stirrer (“Shinky Co., Ltd.,“ Awatori Nertaro ”), and then mixed using three rolls.
  • the sealants for liquid crystal display elements 1 to 10 and Comparative Examples 1 to 3 were prepared.
  • One part by weight of spacer particles (Sekisui Chemical Co., Ltd., “Micropearl SP-2050”) having an average particle diameter of 5 ⁇ m is used for 100 parts by weight of each sealing agent for liquid crystal display elements obtained in Examples and Comparative Examples. It was uniformly dispersed by a stirrer. A very small amount of the sealant in which the spacer particles are dispersed was taken in the center of a glass substrate (20 mm ⁇ 50 mm ⁇ thickness 0.7 mm), and the same type of glass substrate was overlaid thereon. The sealing agent for liquid crystal display elements was spread and heated at 120 ° C. for 1 hour to cure the sealing agent to obtain an adhesion test piece.
  • the adhesive strength was measured using the tension gauge.
  • the case where the adhesive strength was 200 N / cm 2 or more was “ ⁇ ”
  • the case where the adhesive strength was 150 N / cm 2 or more and less than 200 N / cm 2 was “ ⁇ ”
  • the case was evaluated as “x” and the adhesion was evaluated.
  • One part by weight of spacer particles (Sekisui Chemical Co., Ltd., “Micropearl SP-2050”) having an average particle diameter of 5 ⁇ m is used for 100 parts by weight of each sealing agent for liquid crystal display elements obtained in Examples and Comparative Examples. It was uniformly dispersed by a stirrer. The sealing agent in which the spacer particles were dispersed was filled in a dispensing syringe (“PSY-10E” manufactured by Musashi Engineering Co., Ltd.), and defoamed.
  • PSY-10E dispensing syringe
  • the sealing agent subjected to defoaming treatment was applied with a dispenser (manufactured by Musashi Engineering Co., Ltd., “SHOTMASTER 300”) on a glass substrate having an ITO thin film and an alignment film so as to draw a rectangular frame. Subsequently, fine droplets of a liquid crystal composition containing a polymerizable compound (1% by weight of biphenyl 4,4′-diylbis (2-methylacrylate) added to MLC-6833 (Merck)) were dropped into a liquid crystal dropping device. And was applied dropwise.
  • a dispenser manufactured by Musashi Engineering Co., Ltd., “SHOTMASTER 300
  • fine droplets of a liquid crystal composition containing a polymerizable compound 1% by weight of biphenyl 4,4′-diylbis (2-methylacrylate) added to MLC-6833 (Merck)
  • the pressure is reduced to 5 Pa with a vacuum bonding apparatus.
  • a cell The obtained cell was heated at 120 ° C. for 1 hour to cure the sealant.
  • a mercury lamp is used to irradiate 100 mW / cm 2 of ultraviolet rays (wavelength 313 nm) for 50 seconds to polymerize the polymerizable compound in the liquid crystal composition, thereby forming a concavo-convex shape.
  • An element (cell gap 5 ⁇ m) was obtained.
  • a liquid crystal display element with an evaluation of “ ⁇ ” is a level at which there is no problem in practical use, and a liquid crystal display element with a “ ⁇ ” level is a level that may cause a problem depending on the display design.
  • a display element is a level which cannot endure practical use.
  • the sealing agent for liquid crystal display elements which can suppress the liquid crystal contamination by the insertion to the sealing agent with a liquid crystal and liquid crystal contamination by a sealing agent, and is excellent in adhesiveness and display performance is provided. can do.
  • the vertical conduction material and liquid crystal display element which use this sealing compound for liquid crystal display elements can be provided.

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Abstract

Un objectif de l'invention est de fournir un agent d'étanchéité pour élément d'affichage à cristaux liquides permettant que la pénétration de l'agent d'étanchéité par un cristal liquide et la pollution du cristal liquide par l'agent d'étanchéité puissent être supprimées, que l'agent d'étanchéité présente une excellente adhésivité et qu'un élément d'affichage à cristaux liquides ayant d'excellentes performances d'affichage puisse être obtenu. Un autre objectif de l'invention est de fournir un matériau à conduction verticale ainsi qu'un élément d'affichage à cristaux liquides formé au moyen de l'agent d'étanchéité pour élément d'affichage à cristaux liquides. L'invention concerne un agent d'étanchéité pour élément d'affichage à cristaux liquides contenant une résine durcissable, un agent de durcissement thermique, ainsi que des particules molles ayant un diamètre de particule maximal inférieur ou égal à 100 % des espaces cellulaires dans l'élément d'affichage à cristaux liquides, la résine durcissable étant un composé avec au moins trois groupes époxy dans une molécule.
PCT/JP2019/018764 2018-05-17 2019-05-10 Agent d'étanchéité pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides WO2019221027A1 (fr)

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