CN113168057B - Sealing agent for display element, vertically conductive material, and display element - Google Patents
Sealing agent for display element, vertically conductive material, and display element Download PDFInfo
- Publication number
- CN113168057B CN113168057B CN202080006255.2A CN202080006255A CN113168057B CN 113168057 B CN113168057 B CN 113168057B CN 202080006255 A CN202080006255 A CN 202080006255A CN 113168057 B CN113168057 B CN 113168057B
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- CN
- China
- Prior art keywords
- display element
- sealant
- curable resin
- polyimide
- cured product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004020 conductor Substances 0.000 title claims abstract description 12
- 238000007789 sealing Methods 0.000 title abstract description 18
- 239000000565 sealant Substances 0.000 claims abstract description 76
- 229920005989 resin Polymers 0.000 claims abstract description 66
- 239000011347 resin Substances 0.000 claims abstract description 66
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 53
- 229920001721 polyimide Polymers 0.000 claims abstract description 52
- 239000004642 Polyimide Substances 0.000 claims abstract description 50
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 22
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 12
- -1 ester compound Chemical class 0.000 claims description 61
- 239000004593 Epoxy Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 31
- 150000002148 esters Chemical group 0.000 claims description 12
- 239000010419 fine particle Substances 0.000 claims description 11
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- 125000000524 functional group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 30
- 239000000758 substrate Substances 0.000 description 30
- 239000003822 epoxy resin Substances 0.000 description 27
- 229920000647 polyepoxide Polymers 0.000 description 27
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- PSIKPHJLTVSQFO-UHFFFAOYSA-N propanedihydrazide Chemical compound NNC(=O)CC(=O)NN PSIKPHJLTVSQFO-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1341—Filling or closing of cells
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
The purpose of the present invention is to provide a sealing agent for display elements, which has excellent adhesion even when exposed to high-temperature and high-humidity environments. The present invention also provides a cured product of the sealant for display element, and a vertically conductive material and a display element using the sealant for display element. The sealant for display element of the present invention comprises a curable resin, and a polymerization initiator and/or a thermosetting agent, wherein the initial adhesion of the cured product to polyimide at 25 ℃ is 2.0kgf/cm 2 or more, and the adhesion of the cured product to polyimide at 25 ℃ is 60% or more of the initial adhesion to polyimide after the cured product is left for 24 hours in an environment of 121 ℃, 100% RH, 2 atm.
Description
Technical Field
The present invention relates to a sealant for display elements having excellent adhesion even when exposed to a high-temperature and high-humidity environment. The present invention also relates to a cured product of the sealant for a display element, and a vertically conductive material and a display element each using the sealant for a display element.
Background
In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having characteristics of thin, light weight, low power consumption, and the like. In these display elements, sealing of liquid crystal, light-emitting layer, and the like is generally performed by using a sealant made of a curable resin composition.
For example, as a liquid crystal display element, a liquid crystal display element using a photo-thermal and curable sealant as disclosed in patent document 1 and patent document 2 is disclosed from the viewpoints of shortening the tact time and optimizing the amount of liquid crystal used.
However, in modern spread of various portable terminals with display panels such as mobile phones and portable game machines, miniaturization of the device is the most required task. With the miniaturization of such devices, the display portion has been narrowed. In particular, in a liquid crystal display element, the distance from the pixel region to the sealant becomes shorter, and the sealant is often disposed on an alignment film such as polyimide. Therefore, it is necessary to make the adhesion of the sealant to the alignment film excellent.
In addition, as a display element, as a high reliability in driving under a high-temperature and high-humidity environment or the like, performance corresponding to a Pressure Cooker Test (PCT) under conditions of 121 ℃, 100% rh, 2atm is also required. In order to obtain a display element having high reliability, it is necessary to provide a sealant with excellent adhesion even when exposed to a high-temperature and high-humidity environment.
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 purpose of the present invention is to provide a sealing agent for display elements, which has excellent adhesion even when exposed to high-temperature and high-humidity environments. The present invention also provides a cured product of the sealant for a display element, and a vertically conductive material and a display element using the sealant for a display element.
Means for solving the problems
The present invention provides a sealant for display elements, which comprises a curable resin, and a polymerization initiator and/or a thermosetting agent, wherein the initial adhesion of a cured product to polyimide at 25 ℃ is 2.0kgf/cm 2 or more, and the adhesion of the cured product to polyimide at 25 ℃ is 60% or more of the initial adhesion to polyimide after the cured product is left for 24 hours in an environment of 121 ℃, 100% RH and 2 atm.
The present invention is described in detail below.
The inventors studied that the initial adhesion of the cured product to polyimide at 25℃was not less than a specific value, and that after leaving the cured product at 121℃under 100% RH and 2atm for 24 hours, the adhesion of the cured product to polyimide at 25℃was not less than a specific ratio to the initial adhesion to polyimide. As a result, it has been found that a sealant for display elements having excellent adhesion even when exposed to a high-temperature and high-humidity environment can be obtained, and the present invention has been completed.
The sealing agent for a display element of the present invention is particularly remarkably exhibited when it is disposed on an alignment film of a liquid crystal display element, in terms of its effect of excellent adhesion even when exposed to a high-temperature and high-humidity environment.
In the sealant for display element of the present invention, the lower limit of the initial adhesion force of the cured product to polyimide at 25 ℃ (hereinafter, also simply referred to as "initial adhesion force to polyimide") is 2.0kgf/cm 2. The preferable lower limit of the initial adhesion to polyimide is
The lower limit of 2.4kgf/cm 2 is more preferably 2.8kgf/cm 2.
The preferable upper limit of the initial adhesion to polyimide is not particularly limited, but the upper limit is substantially 5.0kgf/cm 2.
The initial adhesion to polyimide can be measured by the following method.
Specifically, a sealant was applied to one of 2 substrates (hereinafter, also referred to as "polyimide substrates") obtained by coating a polyimide solution with a film thickness of about 100nm on an ITO substrate having a length of 45mm, a width of 25mm, and a thickness of 0.7mm, and then treating the coated substrate so that the diameter of the substrate when the substrates were bonded became 3 mm. The polyimide substrate on which the sealant is dispensed and the other polyimide substrate are bonded in a cross shape with the sealant interposed therebetween. Then, the sealant was cured by irradiation with light of 100mW/cm 2 for 30 seconds using a metal halide lamp or the like and heated at 120℃for 1 hour, to obtain a test piece. The initial adhesion to polyimide was measured by performing a tensile test under conditions of 5mm/sec using chucks arranged vertically in an environment of 25 ℃.
In the sealant for display element of the present invention, the adhesion of the cured product to polyimide at 25 ℃ after leaving the cured product for 24 hours at 121 ℃, 100% rh, and 2atm (hereinafter, also referred to as "adhesion to polyimide after PCT24 h") is 60% or more of the initial adhesion to polyimide. The adhesion to polyimide after PCT24h is preferably 70% or more, more preferably 80% or more of the initial adhesion to polyimide.
The adhesion to polyimide after PCT24h was measured by the following method.
That is, first, PCT was allowed to stand for 24 hours at 121 ℃, 100% rh and 2atm in an environment, with respect to a test piece obtained in the same manner as the above-described method for measuring the initial adhesion to polyimide. The adhesion to polyimide after PCT24 hours was measured by performing a tensile test on the test piece after PCT24 hours using chucks arranged vertically at 25 ℃.
The initial adhesion to polyimide and the adhesion to polyimide after PCT24 hours can be set as the above by selecting the types and adjusting the content ratio of the curable resin, the polymerization initiator and/or the thermosetting agent to be described later
Range.
The sealant for display element of the present invention contains a curable resin.
The curable resin contains an ester compound, and the weight average value of the concentration of the ester functional group represented by the following formula (I) in the entire curable resin is preferably 20% or less, when the molecular weight of the curable resin component is M and the number of the ester functional group in the molecule of the curable resin component 1 is N, with respect to the curable resin component contained in the curable resin. In the case where the curable resin component has a large number of ester functional groups, hydrolysis is likely to occur under a high-temperature and high-humidity environment, but the hydrolysis can be reduced by setting the weight average value of the concentration of the ester functional groups in the entire curable resin to 20% or less, and the adhesion to polyimide after PCT24 hours can be easily set to the above range.
[ Mathematics 1]
Concentration of ester functional group (%) = (44N +.m) ×100 (I)
The sealant for display element of the present invention contains a thermosetting agent described later, the curable resin contains an epoxy compound, and when the active hydrogen equivalent of the thermosetting agent is represented by X and the content of the thermosetting agent is represented by Y parts by weight relative to 100 parts by weight of the curable resin (the number of active hydrogen of the thermosetting agent contributing to the reaction between the thermosetting agent and the epoxy compound and the number of epoxy compound contributing to the reaction are the same), the apparent epoxy equivalent of the entire curable resin represented by the following formula (II) is preferably 700 or more. By setting the apparent epoxy equivalent of the entire curable resin to 700 or more, the adhesion to polyimide after PCT24 hours can be easily set to the above range.
[ Math figure 2]
Apparent epoxy equivalent = (100×x)/(Y (II))
Among these, the sealant for display element of the present invention preferably contains a thermosetting agent described below, the curable resin contains an ester compound and an epoxy compound, the weight average value of the concentration of the ester functional group represented by the formula (I) in the entire curable resin is 20% or less, and the apparent epoxy equivalent of the entire curable resin represented by the formula (II) is 700 or more. The adhesive strength to polyimide after PCT24 hours can be more easily set to the above range by setting the weight average value of the ester functional group concentration in the curable resin as a whole to 20% or less and the apparent epoxy equivalent of the curable resin as a whole to 700 or more.
The ester compound and the epoxy compound may be the same compound, that is, an epoxy compound having an ester functional group.
The curable resin preferably contains a compound having a polymerizable functional group and a soft skeleton (hereinafter, also referred to as "curable resin having a soft skeleton"). By containing the curable resin having a soft skeleton, the initial adhesion to polyimide can be easily set to the above range.
In the case where the curable resin having a soft skeleton is contained, the obtained sealant for a display element is likely to be a sealant having poor wet heat resistance of a cured product. Accordingly, by setting the weight average value of the concentration of the ester functional group in the curable resin as a whole and the apparent epoxy equivalent of the curable resin as a whole to the above ranges, deterioration in wet heat resistance can be suppressed.
Examples of the polymerizable functional group include a (meth) acryloyl group and an epoxy group. The curable resin having a soft skeleton preferably has 2 or more polymerizable functional groups in 1 molecule.
In the present specification, the "(meth) acryl" means acryl or methacryl.
Examples of the soft skeleton include a rubber structure, a ring-opened structure of a cyclic lactone, and an alkylene oxide (japanese) structure. Among them, a rubber structure is preferable. By using a curable resin having such a soft skeleton, the initial adhesion to polyimide can be set to the above range more easily.
The rubber structure is preferably a structure having an unsaturated bond in the main chain or a structure having a polysiloxane skeleton in the main chain.
Examples of the structure having an unsaturated bond in the main chain include: a structure having a backbone obtained by polymerization of a conjugated diene in the main chain, and the like.
Examples of the skeleton obtained by polymerization of the conjugated diene include an acrylonitrile-butadiene skeleton, a polybutadiene skeleton, a polyisoprene skeleton, a styrene-butadiene skeleton, a polyisobutylene skeleton, a polychloroprene skeleton, and the like.
Among them, the rubber structure is preferably a structure having an acrylonitrile-butadiene skeleton or a polybutadiene skeleton.
Examples of the cyclic lactone include: gamma-undecalactone, epsilon-caprolactone, gamma-decalactone, sigma-dodecalactone, gamma-nonanolactone, gamma-heptanolactone, gamma-valerolactone, sigma-valerolactone, beta-butyrolactone, gamma-butyrolactone, beta-propiolactone, sigma-caprolactone, 7-butyl-2-oxetanone, and the like. Among them, cyclic lactones having 5 to 7 carbon atoms in the straight chain portion of the main skeleton at the time of ring opening are preferable.
Examples of the alkylene oxide structure include an ethylene oxide structure, a propylene oxide structure, and a butylene oxide structure.
The lower limit of the molecular weight of the curable resin having a soft skeleton is preferably 100, and the upper limit is preferably 10 ten thousand. By setting the molecular weight of the curable resin having a soft skeleton to this range, it is easier to set the initial adhesion to polyimide to the above range. The lower limit of the molecular weight of the curable resin having a soft skeleton is more preferably 200, and the upper limit is more preferably 5 ten thousand.
In the present specification, the "molecular weight" is a molecular weight obtained from a structural formula of a compound having a specific molecular structure, but may be expressed by using a weight average molecular weight for a compound having a wide distribution of polymerization degrees and a compound having an unspecified modified site. 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 weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa electric company).
Specific examples of the curable resin having a soft skeleton include NBR-modified epoxy (meth) acrylate, terminal amino group-containing butadiene-Acrylonitrile (ATBN) -modified epoxy (meth) acrylate, terminal carboxyl group-containing butadiene-acrylonitrile (CTBN) -modified epoxy (meth) acrylate, (meth) acrylic acid-modified isoprene rubber, (meth) acrylic acid-modified butadiene rubber, (meth) acrylic acid-modified silicone rubber, caprolactone-modified bisphenol A-type epoxy (meth) acrylate, caprolactone-modified bisphenol F-type epoxy (meth) acrylate, caprolactone-modified bisphenol E-type epoxy (meth) acrylate, ethylene oxide-modified bisphenol A-type epoxy (meth) acrylate, ethylene oxide-modified bisphenol F-type epoxy (meth) acrylate, ethylene oxide-modified bisphenol E-type epoxy (meth) acrylate, propylene oxide-modified bisphenol A-type epoxy (meth) acrylate, propylene oxide-modified bisphenol E-type epoxy (meth) acrylate, polybutadiene-modified urethane (meth) acrylate, modified bisphenol A-type epoxy resin, ATBN-modified epoxy resin, CTBN-modified epoxy rubber, BN-modified epoxy-modified bisphenol A-type epoxy-modified epoxy-lactone-type epoxy-modified epoxy-bisphenol E-type epoxy-modified epoxy-bisphenol-type epoxy-modified epoxy-E-epoxy-acrylate, nitrile-modified epoxy-type epoxy-modified bisphenol-E-type epoxy-modified epoxy-type-bisphenol-E-epoxy-modified epoxy-type-epoxy-type-acrylate, and-modified-E-modified epoxy-bisphenol-type-modified-epoxy-F-epoxy-modified-epoxy-type-epoxy-modified-epoxy-E-epoxy-modified-epoxy-type-resin-modified-epoxy-resin-modified-curable resin Ethylene oxide-modified bisphenol A-type epoxy resin, ethylene oxide-modified bisphenol F-type epoxy resin, ethylene oxide-modified bisphenol E-type epoxy resin, propylene oxide-modified bisphenol A-type epoxy resin, propylene oxide-modified bisphenol F-type epoxy resin, propylene oxide-modified bisphenol E-type epoxy resin, and the like.
The curable resin having a soft skeleton may be used alone or in combination of 2 or more.
In the present specification, the term "(meth) acrylate" refers to an acrylate or a methacrylate, and the term "epoxy (meth) acrylate" refers to a compound obtained by reacting all epoxy groups in an epoxy compound with (meth) acrylic acid.
The curable resin may contain other curable resins than the curable resin having a soft skeleton.
In the case of containing the other curable resin, the content of the curable resin having a soft skeleton in 100 parts by weight of the curable resin is preferably limited to 5 parts by weight, and the upper limit is preferably limited to 70 parts by weight. By setting the content of the curable resin having a soft skeleton to this range, it is easier to set the initial adhesion to polyimide to the above range. The lower limit of the content of the curable resin having a soft skeleton is more preferably 10 parts by weight, and the upper limit is more preferably 50 parts by weight.
Examples of the other curable resin include other epoxy compounds having no soft skeleton, other (meth) acrylic compounds having no soft skeleton, and the like.
In the present specification, the "(meth) acrylic acid" means acrylic acid or methacrylic acid, and the "(meth) acrylic compound" means a compound having a (meth) acryloyl group.
Examples of the other epoxy compounds include bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2' -diallyl bisphenol a type epoxy resin, hydrogenated bisphenol type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, thioether type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin, o-cresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, biphenyl novolac type epoxy resin, naphthol novolac type epoxy resin, glycidylamine type epoxy resin, and glycidyl ester compound.
The curable resin may contain a compound having an epoxy group and a (meth) acryloyl group in 1 molecule as the other epoxy compound. Examples of such a compound include: and a partially (meth) acrylic acid-modified epoxy resin obtained by reacting a part of epoxy groups of an epoxy compound having 2 or more epoxy groups in 1 molecule with (meth) acrylic acid.
As the other (meth) acrylic compound, a polyfunctional (meth) acrylic compound having 2 or more (meth) acryloyl groups in 1 molecule is preferable.
Further, as the other (meth) acrylic compound, epoxy (meth) acrylate is preferable.
Examples of the epoxy (meth) acrylate include: epoxy (meth) acrylate obtained by reacting an epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method, and the like.
The epoxy compound that is a raw material for synthesizing the epoxy (meth) acrylate is the same as the other epoxy compound.
The curable resin may be used alone or in combination of 2 or more.
In the sealant for display element of the present invention, the content ratio of the (meth) acryloyl group in the total of the (meth) acryloyl groups and the epoxy groups in the curable resin is preferably 50 mol% or more and 95 mol% or less.
The sealant for display elements of the present invention contains a polymerization initiator and/or a thermosetting agent.
Examples of the polymerization initiator include: a photo radical polymerization initiator that generates radicals by irradiation with light, a thermal radical polymerization initiator that generates radicals by heating, and the like.
As the above-mentioned photo radical polymerization initiator, at least any one of an oxime ester compound and a thioxanthone compound is preferably contained from the viewpoint of reactivity.
In the present specification, the "thioxanthone compound" refers to a compound having a thioxanthone group, and the "thioxanthone group" refers to a 9-oxo-9H-thioxanthone group.
Examples of the oxime ester compound include 1- (4- (phenylsulfanyl) phenyl) -1, 2-octanedione 2- (O-benzoyl oxime), O-acetyl-1- (6- (2-methylbenzoyl) -9-ethyl-9H-carbazol-3-yl) ethanone oxime, and a compound represented by the following formula (1).
[ Chemical formula 1]
The thioxanthone compound preferably has a thioxanthone group at the terminal of the main chain.
In addition, the thioxanthone compound preferably has 3 or more thioxanthone groups in 1 molecule. By providing the thioxanthone compound having 3 or more thioxanthone groups in 1 molecule, the obtained sealant for display element is more excellent in deep curability with respect to light having a long wavelength.
As the thioxanthone compound, specifically, at least any one of a compound represented by the following formula (2-1) and a compound represented by the following formula (2-2) is preferable.
[ Chemical formula 2]
In the formula (2-2), n is 1 to 10 (average value).
Examples of the photo-radical polymerization initiator other than the oxime ester compound and the thioxanthone compound include a benzophenone compound, an acetophenone compound, an acylphosphine oxide compound, a titanocene compound, and a benzoin ether compound.
Specific examples of the other 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, 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide, benzoin methyl ether, benzoin diethyl ether, benzoin isopropyl ether, 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: a thermal radical polymerization initiator comprising an azo compound, an organic peroxide, or the like. Among them, an initiator containing an azo compound (hereinafter, also referred to as "azo initiator") is preferable from the viewpoint of suppressing liquid crystal contamination, and an initiator containing a polymer azo compound (hereinafter, also referred to as "polymer azo initiator") is more preferable.
In the present specification, the term "polymer azo compound" refers to a compound having an azo group, which generates a radical capable of curing a (meth) acryloyl group by heat, and having a number average molecular weight of 300 or more.
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, adverse effects on the liquid crystal can be prevented and the polymer azo compound can be easily mixed into the curable resin. 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 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).
Examples of the polymer azo compound include: a polymer azo 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 polymer azo compound having a polyethylene oxide structure.
Specific examples of the polymer azo compound include: polycondensates of 4,4 '-azobis (4-cyanovaleric acid) and polyalkylene glycol, polycondensates of 4,4' -azobis (4-cyanovaleric acid) and polydimethylsiloxane having terminal amino groups, and the like.
Examples of the 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-chemical Co., ltd.).
Examples of the organic peroxide include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
The thermal radical polymerization initiator may be used alone or in combination of 2 or more.
The lower limit of the content of the polymerization initiator is preferably 0.01 part by weight, and the upper limit is preferably 10 parts by weight, 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 display elements is more excellent in storage stability and curability. The more preferable lower limit of the content of the above-mentioned polymerization initiator is 0.1 part by weight, and the more preferable upper limit is 5 parts by weight.
Examples of the thermosetting agent include organic acid hydrazides, polyhydric phenol compounds, and acid anhydrides. Among them, organic acid hydrazides are preferably used.
Examples of the organic acid hydrazide include 1, 3-bis (hydrazinocarbonylethyl) -5-isopropyl hydantoin, sebacic dihydrazide, isophthalic dihydrazide, adipic dihydrazide, malonic dihydrazide, and the like.
Examples of the commercial products of the organic acid hydrazide include organic acid hydrazides manufactured by tsukamurella chemical company and organic acid hydrazides manufactured by Ajinomoto Fine-Techno company.
As the organic acid hydrazide manufactured by Katsukamu chemical Co., ltd, SDH, ADH, MDH and the like are mentioned, for example.
Examples of the organic acid hydrazide manufactured by Ajinomoto Fine-Techno include Amicure VDH, amicure VDH-J, and Amicure UDH.
The above-mentioned thermosetting agents may be used alone or in combination of 2 or more.
The content of the thermosetting agent is preferably limited to 1 part by weight, and the content of the thermosetting agent is preferably limited to 4.5 parts by weight, based on 100 parts by weight of the curable resin. By setting the content of the thermosetting agent to this range, thermosetting properties can be further improved without deteriorating coating properties, water absorption properties, and the like of the obtained sealing agent for display elements. The more preferable lower limit of the content of the above-mentioned thermosetting agent is 2 parts by weight, and the more preferable upper limit is 3.5 parts by weight.
The sealant for display element of the present invention preferably contains a filler for the purpose of improving viscosity, further improving adhesiveness due to stress dispersion 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 lower limit of the content of the filler is preferably 10 parts by weight, and the upper limit is preferably 80 parts by weight, based on 100 parts by weight of the curable resin. By setting the content of the filler to this range, the adhesiveness and the like can be further improved without deteriorating the coatability and the like of the obtained sealing agent for display elements. The lower limit of the content of the filler is more preferably 30 parts by weight, and the upper limit is more preferably 60 parts by weight.
The sealing agent for display elements of the present invention preferably contains a silane coupling agent. The silane coupling agent mainly comprises: the adhesive agent functions as an adhesion promoter for well adhering the sealant 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 have excellent effect of improving adhesion to a substrate or the like, and when the obtained sealant for a display element is used as a sealant for a liquid crystal display element, outflow of a curable resin into liquid crystal can be suppressed.
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 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 resulting sealant for a display element is used as a sealant for a liquid crystal display element, and the effect of suppressing the occurrence of liquid crystal contamination and improving the adhesion becomes more excellent. The more preferable lower limit of the content of the above silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
The sealant for display element of the present invention may contain an opacifying agent. By containing the light-shielding agent, the sealing agent for a display element of the present invention can be suitably used 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. Among them, titanium black is preferable.
The titanium black is a substance having a higher transmittance for light in the vicinity of the ultraviolet region, particularly in the range of from 370nm to 450nm, than for light having a wavelength of from 300nm to 800 nm. That is, the titanium black is an opacifier having the following properties: the sealant for a display element of the present invention is provided with light shielding properties by sufficiently shielding light having a wavelength in the visible light range, and is transmitted by light having a wavelength in the vicinity of the ultraviolet range. Therefore, the photocurability of the sealant for a display element of the present invention can be further increased by using, as the polymerization initiator, a polymerization initiator capable of initiating a reaction by light having a wavelength (370 nm to 450 nm) at which the transmittance of the titanium black is high. The light-shielding agent contained in the sealant for 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 OD value of the titanium black is not particularly limited, but is usually 5 or less.
The titanium black exhibits sufficient effects even without surface treatment, but may be used: titanium black surface-treated with an organic component such as a coupling agent, or titanium black surface-treated with an inorganic component such as silica, titania, germania, alumina, zirconia, magnesia, or the like. Among them, titanium black treated with an organic component is preferable in that the insulation property can be further improved.
In addition, since the liquid crystal display element manufactured using the sealant for a display element of the present invention containing the titanium black as the light shielding agent has sufficient light shielding properties, a liquid crystal display element having no light leakage, high contrast, and excellent image display quality can be realized.
Examples of the commercial products of the above titanium black include titanium black manufactured by Mitsubishi Materials, titanium black manufactured by red ear formation, and the like.
Examples of the titanium black manufactured by Mitsubishi Materials include 12S, 13M-C, 13R-N, and 14M-C.
Examples of the titanium black produced 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 titanium black preferably has a lower limit of 0.5 Ω·cm, an upper limit of 3 Ω·cm, a lower limit of 1 Ω·cm, and an upper limit of 2.5 Ω·cm.
The primary particle diameter of the light-shielding agent is not particularly limited as long as it is not more than the distance between 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 display elements. The primary particle diameter of the light-shielding agent is more preferably 5nm in lower limit, more preferably 200nm in upper limit, still more preferably 10nm in lower limit, and still more preferably 100nm in upper limit.
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 content of the light-shielding agent in 100 parts by weight of the sealant for display element of the present invention is preferably 5 parts by weight, and the upper limit is preferably 80 parts by weight. By setting the content of the light-shielding agent to this range, the adhesiveness, strength after curing, and drawing properties of the obtained sealant for display elements are not reduced, and the effect of improving light-shielding properties can be further exhibited. 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 display element of the present invention may further contain additives such as a stress-relaxing 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 display elements of the present invention include a method in which a curable resin, a polymerization initiator and/or a thermosetting agent, and optionally an additive such as a silane coupling agent are mixed using a mixer. Examples of the mixer include a homogenizing and dispersing machine, a homogenizing and mixing machine, a universal mixer, a planetary mixer, a kneader, and a three-roll machine.
By incorporating conductive fine particles into the sealing agent for display elements of the present invention, a vertically conductive material can be produced. Such a vertically conductive material containing the sealing agent for a 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 preferable because the fine resin particles have excellent elasticity and can be electrically connected without damaging the transparent substrate or the like.
The cured product of the sealant for display element of the present invention is also one of the present invention.
A display element having the cured product of the sealant for a display element of the present invention or the cured product of the vertically conductive material of the present invention is also one of the present invention.
The sealant for a display element of the present invention is suitably used as a sealant for a liquid crystal display element.
In particular, the sealant for a display element of the present invention can be suitably used for manufacturing a liquid crystal display element by a liquid crystal dropping process. As a method for manufacturing a liquid crystal display element by a liquid crystal dropping method, for example, the following method is given as examples of the display element of the present invention.
First, a process of forming a frame-shaped seal pattern by applying the seal agent for a display element of the present invention on a substrate by screen printing, dispenser application, or the like is performed. Next, the following steps were performed: in the uncured state such as the sealing agent for display element of the present invention, minute droplets of liquid crystal are applied dropwise to the entire inner frame surface of the seal pattern, and the other substrate is immediately superimposed. Then, a liquid crystal display element can be obtained by performing a step of temporarily curing the sealing agent by irradiating the sealing pattern portion with light such as ultraviolet light and a step of final curing the temporarily cured sealing agent by heating.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a sealant for a display element having excellent adhesion even when exposed to a high-temperature and high-humidity environment can be provided. Further, according to the present invention, a cured product of the sealant for a display element, and a vertically conductive material and a display element using the sealant for a display element can be provided.
Detailed Description
The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
Examples 1 to 8 and comparative examples 1 to 5
The display element sealants of examples 1 to 8 and comparative examples 1 to 5 were prepared by mixing the respective materials using a planetary mixer according to the mixing ratios shown in tables 1 and 2, and then further mixing the materials using a three-roll mixer. As the planetary mixer, a deaeration milan (manufactured by the company thin) was used.
A sealant for display elements was obtained by applying a polyimide solution to 1 substrate out of 2 substrates (polyimide substrates) obtained by processing an ITO substrate having a length of 45mm, a width of 25mm, and a thickness of 0.7mm with a film thickness of about 100nm, and dispensing the resultant film so that the diameter of the substrate when the substrates were bonded became 3 mm. The polyimide substrate on which the sealant is dispensed and the other polyimide substrate are bonded in a cross shape with the sealant interposed therebetween. Then, after irradiation of ultraviolet rays of 3000mJ/cm 2 with a metal halide lamp, the resultant was heated at 120℃for 60 minutes, thereby obtaining an adhesion test piece. The initial adhesion to polyimide was measured by performing a tensile test on the obtained adhesion test piece under conditions of 5mm/sec using chucks arranged vertically in an environment of 25 ℃. The measurement results of the initial adhesion to polyimide are shown in tables 1 and 2.
Further, a PCT was allowed to stand for 24 hours at 121 ℃, 100% rh and 2atm in an environment, with respect to a test piece obtained by the same procedure as the method for measuring the initial adhesion to polyimide. PCT used was an autoclave (manufactured by Yamato Scientific Co., ltd., "SP 510F"). For the test piece after PCT, the adhesion to polyimide after PCT24 hours was measured by performing a tensile test with chucks arranged vertically under conditions of 5mm/sec at 25 ℃. The ratio of the adhesion to polyimide after PCT24h to the initial adhesion to polyimide is shown in tables 1 and 2.
< Evaluation >
The sealants for display elements obtained in examples and comparative examples were evaluated as follows. The results are shown in tables 1 and 2.
(Moist heat resistance)
Polyimide resin was applied to a glass substrate with an ITO thin film by spin coating, prebaked at 80 ℃ and then fired at 230 ℃ to thereby produce a substrate with an alignment film. As the polyimide resin, SE7492 (manufactured by daily chemical company) was used.
For 100 parts by weight of each of the display element sealants obtained in examples and comparative examples, 1 part by weight of the silica spacer was added, uniformly dispersed by a planetary stirring device, subjected to a defoaming treatment, and after removing bubbles in the display element sealant, the mixture was filled into a dispensing syringe, and subjected to a defoaming treatment again. As the silica spacer, SI-H055 (manufactured by water chemical industry Co., ltd.) was used, and as the syringe for dispensing, PSY-10E (manufactured by Musashi Engineering Co., ltd.) was used. Next, a sealant for display elements is applied to the alignment film of the substrate with the alignment film in a frame-drawing manner using a dispenser. SHOTMASTER300 (manufactured by Musashi Engineering) was used as the dispenser. Next, a liquid crystal dropping device was used to drop-apply minute droplets of the TN liquid crystal into the frame of the sealant for display elements. The other substrate with alignment film was laminated on the substrate with alignment film coated with TN liquid crystal by dropping via the sealant for display element, and 2 substrates were bonded under reduced pressure of 5Pa by a vacuum bonding apparatus to obtain a cell. JC-5001LA (manufactured by CHISSO Co.) was used as the TN liquid crystal. The obtained cell was irradiated with ultraviolet light of 3000mJ/cm 2 using a metal halide lamp, and then heated at 120℃for 60 minutes, whereby a sealant for a display element was cured, thereby producing a liquid crystal display element.
The obtained liquid crystal display element was exposed to PCT conditions (121 ℃, 100% RH, 2 atm) for 24 hours. The liquid crystal display element after exposure to PCT conditions was observed under a microscope, and the case where peeling of the substrate was not confirmed was marked "o", and the case where peeling of the substrate was confirmed was marked "x", and the wet heat resistance was evaluated.
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Industrial applicability
According to the present invention, a sealant for a display element having excellent adhesion even when exposed to a high-temperature and high-humidity environment can be provided. Further, according to the present invention, a cured product of the sealant for a display element, and a vertically conductive material and a display element using the sealant for a display element can be provided.
Claims (6)
1. A sealant for display elements, characterized by comprising a curable resin and a polymerization initiator and/or a thermosetting agent,
The curable resin contains an ester compound,
When the molecular weight of the curable resin component is M and the number of ester functional groups in the molecule of the curable resin component 1 is N, the weight average value of the concentration of the ester functional groups represented by the following formula (I) in the whole curable resin is 20% or less,
The curable resin contains a compound having a polymerizable functional group and a soft skeleton,
The initial adhesion of the cured product to polyimide at 25 ℃ is 2.0kgf/cm 2 or more, and after the cured product is left to stand for 24 hours in an environment of 121 ℃, 100% RH and 2atm, the adhesion of the cured product to polyimide at 25 ℃ is 60% or more of the initial adhesion to polyimide,
Ester functional group concentration (%) = (44N +.m) ×100 (I).
2. The sealant for display element according to claim 1, wherein the sealant for display element contains a thermosetting agent,
The curable resin contains an epoxy compound,
When the active hydrogen equivalent of the thermosetting agent is X and the content of the thermosetting agent relative to 100 parts by weight of the curable resin is Y parts by weight, the apparent epoxy equivalent of the entire curable resin represented by the following formula (II) is 700 or more,
Apparent epoxy equivalent= (100×x)/(Y (II)).
3. The sealant for a display element according to claim 1 or 2, wherein the soft skeleton is a rubber structure.
4. A cured product obtained by curing the sealant for display elements according to claim 1, 2 or 3.
5. A vertically conductive material comprising the sealant for a display element according to claim 1,2 or 3 and conductive fine particles.
6. A display element having the cured product of the sealant for a display element according to claim 1,2 or 3 or the cured product of the vertically conductive material according to claim 5.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| JP2019031870 | 2019-02-25 | ||
| JP2019-031870 | 2019-02-25 | ||
| PCT/JP2020/007375 WO2020175443A1 (en) | 2019-02-25 | 2020-02-25 | Display element sealing agent, vertically conducting material, and display element |
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| Publication Number | Publication Date |
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| CN113168057A CN113168057A (en) | 2021-07-23 |
| CN113168057B true CN113168057B (en) | 2024-06-18 |
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| JP (2) | JP6783972B1 (en) |
| KR (1) | KR20210129029A (en) |
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| WO (1) | WO2020175443A1 (en) |
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| JP6783972B1 (en) * | 2019-02-25 | 2020-11-11 | 積水化学工業株式会社 | Sealing agent for display elements, vertical conductive materials, and display elements |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013218168A (en) * | 2012-04-10 | 2013-10-24 | Sekisui Chem Co Ltd | Sealant for liquid crystal drop method, vertical conduction material, and liquid crystal display element |
| WO2018207730A1 (en) * | 2017-05-08 | 2018-11-15 | 積水化学工業株式会社 | Sealant for liquid crystal display element, top-bottom conductive material, and liquid crystal display element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH021820A (en) * | 1988-06-09 | 1990-01-08 | Ube Ind Ltd | Composition for sealing liquid crystal display element |
| 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 |
| JP2009275166A (en) * | 2008-05-16 | 2009-11-26 | Jsr Corp | Sealing agent for liquid crystal display and liquid crystal display |
| KR102224443B1 (en) * | 2014-12-10 | 2021-03-09 | 엘지디스플레이 주식회사 | Liquid Crystal Display Device |
| JP6037070B1 (en) * | 2016-02-22 | 2016-11-30 | 大日本印刷株式会社 | Dimming cell |
| JP6783972B1 (en) * | 2019-02-25 | 2020-11-11 | 積水化学工業株式会社 | Sealing agent for display elements, vertical conductive materials, and display elements |
-
2020
- 2020-02-25 JP JP2020514639A patent/JP6783972B1/en active Active
- 2020-02-25 KR KR1020217009900A patent/KR20210129029A/en not_active Application Discontinuation
- 2020-02-25 WO PCT/JP2020/007375 patent/WO2020175443A1/en active Application Filing
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013218168A (en) * | 2012-04-10 | 2013-10-24 | Sekisui Chem Co Ltd | Sealant for liquid crystal drop method, vertical conduction material, and liquid crystal display element |
| WO2018207730A1 (en) * | 2017-05-08 | 2018-11-15 | 積水化学工業株式会社 | Sealant for liquid crystal display element, top-bottom conductive material, and liquid crystal display element |
Also Published As
| Publication number | Publication date |
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| CN113168057A (en) | 2021-07-23 |
| WO2020175443A1 (en) | 2020-09-03 |
| KR20210129029A (en) | 2021-10-27 |
| JP2021015286A (en) | 2021-02-12 |
| JPWO2020175443A1 (en) | 2021-03-11 |
| TW202041647A (en) | 2020-11-16 |
| JP6783972B1 (en) | 2020-11-11 |
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