WO2020230678A1 - Agent d'étanchéité à cristaux liquides, écran d'affichage à cristaux liquides l'utilisant et son procédé de production - Google Patents

Agent d'étanchéité à cristaux liquides, écran d'affichage à cristaux liquides l'utilisant et son procédé de production Download PDF

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Publication number
WO2020230678A1
WO2020230678A1 PCT/JP2020/018466 JP2020018466W WO2020230678A1 WO 2020230678 A1 WO2020230678 A1 WO 2020230678A1 JP 2020018466 W JP2020018466 W JP 2020018466W WO 2020230678 A1 WO2020230678 A1 WO 2020230678A1
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Prior art keywords
liquid crystal
resin
crystal sealant
seal pattern
display panel
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PCT/JP2020/018466
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English (en)
Japanese (ja)
Inventor
宙 宮尾
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三井化学株式会社
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Application filed by 三井化学株式会社 filed Critical 三井化学株式会社
Priority to JP2021519386A priority Critical patent/JP7238112B2/ja
Priority to KR1020217035898A priority patent/KR20210148294A/ko
Priority to CN202080027583.0A priority patent/CN113661438A/zh
Publication of WO2020230678A1 publication Critical patent/WO2020230678A1/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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • 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 liquid crystal sealant, a liquid crystal display panel using the liquid crystal sealant, and a method for manufacturing the same.
  • a liquid crystal display panel usually has a pair of substrates, a frame-shaped sealing member arranged between them, and a pair of substrates and a liquid crystal filled in an area surrounded by a sealing agent.
  • a liquid crystal filling method a liquid crystal dropping method is often used.
  • a frame-shaped seal pattern is formed on one of the pair of substrates by using a liquid crystal sealant. Then, the liquid crystal is dropped into the seal pattern without curing the seal pattern. After that, it is common to superimpose the two substrates via the seal pattern and irradiate the seal pattern with light or heat the seal pattern to cure the seal pattern (for example, Patent Document 1 and Patent Document 2).
  • the cured seal pattern (hereinafter also referred to as "seal member") not only prevents leakage of liquid crystal, but also has a function of bonding a pair of substrates.
  • the liquid crystal sealant (seal pattern) applied to the substrate is cured to some extent by photocuring. Then, by further heating this, it is sufficiently cured, and sufficient strength and hardness are developed.
  • the seal pattern is temporarily softened by the heat.
  • the heating of the seal pattern is often performed while moving a plurality of rollers on a transport device arranged in parallel. However, if the seal pattern softens during movement, the substrates may bend between the rollers, or the relative positions of the pair of substrates may shift due to vibration during transportation. Then, by further heating, the seal pattern is hardened, and the substrates remain displaced from each other.
  • the adhesive strength tends to decrease.
  • the substrate and the sealing member may be peeled off, resulting in liquid crystal leakage or the like.
  • the present invention is a liquid crystal sealant that can also be used in the liquid crystal dropping method, and is a liquid crystal seal that is unlikely to cause a relative displacement between a pair of substrates when manufacturing a liquid crystal display panel and has high adhesive strength. Provide the agent.
  • the present invention provides the following liquid crystal sealants.
  • the elasticity of the cured film containing the thermosetting agent (C) containing the thermosetting agent and the photopolymerization initiator (D) and irradiated with light having a wavelength of 365 nm at 3000 mJ / cm 2 at 120 ° C. is 30 MPa.
  • thermosetting agent (C) is selected from the group consisting of a dihydrazide-based thermosetting agent, an imidazole-based thermosetting agent, an amine adduct-based thermosetting agent, and a polyamine-based thermosetting agent.
  • the present invention also provides the following method for manufacturing a liquid crystal display panel.
  • a liquid crystal display having a pair of substrates, a frame-shaped seal member arranged between the pair of substrates, and a liquid crystal filled between the pair of substrates and inside the frame-shaped seal member.
  • the pattern forming step and the region surrounded by the seal pattern on the one substrate, or the region surrounded by the seal pattern on the other substrate and when the other substrate and the one substrate face each other.
  • a liquid crystal display panel including a liquid crystal dropping step of dropping a liquid crystal, a stacking step of superimposing the one substrate and the other substrate via the seal pattern, and a curing step of curing the seal pattern.
  • Manufacturing method [8] The method for manufacturing a liquid crystal display panel according to [7], wherein the seal pattern is irradiated with light in the curing step. [9] The method for manufacturing a liquid crystal display panel according to [8], wherein in the curing step, heating is further performed after irradiation with light.
  • the present invention also provides the following liquid crystal display panels. [10] It has a pair of substrates, a frame-shaped seal member arranged between the pair of substrates, and a liquid crystal filled between the pair of substrates and inside the frame-shaped seal member.
  • liquid crystal sealant of the present invention when a liquid crystal display panel is manufactured by the liquid crystal dropping method, relative misalignment between a pair of substrates is unlikely to occur. In addition, the substrates can be firmly adhered to each other. Therefore, it is possible to manufacture a high-quality liquid crystal display panel.
  • FIG. 1 is a schematic diagram for explaining a method of performing a deviation test in an embodiment.
  • the liquid crystal sealant of the present invention is preferably used as a liquid crystal sealant for the liquid crystal dropping method, which is often used in combination with photocuring and thermosetting, but may be applied to other methods.
  • the liquid crystal sealant of the present invention is a (meth) acrylic resin (A), a resin (B) having an epoxy group and a (meth) acrylic group in one molecule, a thermosetting agent (C), and a photopolymerization initiator (D). )including.
  • the liquid crystal sealant may contain an epoxy resin (E), inorganic particles (F), organic particles (G), various additives and the like, if necessary.
  • the seal pattern is temporarily softened by heating after photocuring, and the seal pattern shifts to a relative position of a pair of substrates (hereinafter, "" (Also called “misalignment of the substrate”) was likely to occur.
  • the seal pattern after photo-curing is hardened in order to suppress the deformation of the seal pattern, the adhesive strength may be insufficient and the seal member and the substrate may be peeled off.
  • the heating temperature of the seal pattern is usually 100 to 150 ° C.
  • the thermosetting agent (latent thermosetting agent) contained in the conventional liquid crystal sealant is solid at room temperature and has a melting point of about 100 to 150 ° C.
  • the latent curing agent melts by heating and reacts with a thermosetting resin (for example, an epoxy resin).
  • a thermosetting resin for example, an epoxy resin.
  • the heating temperature of the seal pattern and the melting point of the thermosetting agent are close to each other, not only the thermosetting resin is softened by the heat but also the thermosetting resin reacts with the thermosetting resin during curing. It was clarified that the viscosity of the seal pattern was also lowered by melting the thermosetting agent before the coating. When the viscosity of the seal pattern decreases, the above-mentioned misalignment of the substrate tends to occur.
  • the liquid crystal sealant of the present invention contains, as the thermosetting agent (C), a thermosetting agent having a melting point of 90 ° C. or lower, or a thermosetting agent having a melting point of 170 ° C. or higher.
  • the thermosetting agent (C) dissolves smoothly at a relatively low temperature. Then, since the thermosetting agent (C) cures the thermosetting resin before the thermosetting resin is softened by heat, the above-mentioned displacement of the substrate is unlikely to occur.
  • the thermosetting agent (C) is a thermosetting agent having a melting point of 170 ° C. or higher, the curing agent gradually dissolves, so that the viscosity of the liquid crystal sealant after photocuring is unlikely to decrease excessively, and the position of the substrate. Misalignment is unlikely to occur.
  • the liquid crystal sealant of the present invention will be described in detail, but the elastic modulus of the cured film after photocuring (before heat curing) is within a certain range. If the elastic modulus of the cured film after photocuring is too high, the adhesive strength tends to be low, and if the elastic modulus is too low, the above-mentioned misalignment tends to occur. On the other hand, when the elastic modulus of the cured film is within a certain range, it is possible to achieve both good adhesive strength and prevention of misalignment of the substrate.
  • each component of the liquid crystal sealant of the present invention will be described.
  • the (meth) acrylic resin (A) may be a resin containing one or more (meth) acrylic groups in one molecule.
  • the resin (B) containing a (meth) acrylic group and an epoxy group in one molecule is not included in the (meth) acrylic resin (A).
  • the (meth) acrylic represents methacrylic, acrylic, or both, and the resin includes not only a polymer but also a monomer and an oligomer.
  • examples of the (meth) acrylic resin (A) include di (meth) acrylates such as polyethylene glycol, propylene glycol, and polypropylene glycol; di (meth) acrylates of tris (2-hydroxyethyl) isocyanurate; neopentyl.
  • Acrylate Di or tri (meth) acrylate of triol obtained by adding 3 mol or more of ethylene oxide or propylene oxide to 1 mol of trimethylolpropane; adding 4 mol or more of ethylene oxide or propylene oxide to 1 mol of bisphenol A.
  • a resin having a glass transition temperature of 25 ° C. or higher and lower than 200 ° C. is preferable from the viewpoint that the elastic modulus of the film after photocuring of the liquid crystal sealant easily falls within a desired range.
  • the glass transition temperature is more preferably 40 ° C. to 200 ° C., further preferably 50 to 150 ° C.
  • the glass transition temperature is measured by a viscoelasticity measuring device (DMS).
  • the above-mentioned (meth) acrylic resin (A) preferably contains a hydrogen-bonding functional group such as a hydroxyl group, a urethane bond, an amide group, and a carboxyl group.
  • the hydrogen-bonding functional group also includes a hydroxyl group, a urethane bond, a carboxyl group, an amide group and the like contained in the raw material of the (meth) acrylic resin (A).
  • the compatibility with the liquid crystal which is generally hydrophobic, becomes low.
  • the liquid crystal sealant becomes difficult to dissolve in the liquid crystal, and the liquid crystal sealant suitable for the liquid crystal dropping method is obtained.
  • the hydrogen-bonding functional group equivalent of the (meth) acrylic resin (A) contained in the liquid crystal sealant is preferably 1.0 ⁇ 10 -4 to 5 ⁇ 10 -3 mol / g, preferably 2.0 ⁇ 10 -3 to 4. .5 ⁇ 10 -3 mol / g is more preferable.
  • the hydrogen-bonding functional group equivalent is less than 1.0 ⁇ 10 -4 mol / g, the number of hydrogen-bonding functional groups in one molecule of the (meth) acrylic resin (A) is small, and the effect of suppressing dissolution on the liquid crystal is obtained. Hard to get.
  • the hydrogen-bonding functional group equivalent of the (meth) acrylic resin (A) exceeds 5 ⁇ 10 -3 mol / g, the moisture resistance of the cured product of the liquid crystal sealant tends to decrease.
  • the hydrogen-bonding functional group equivalent (mol / g) of the (meth) acrylic resin (A) is "the number of hydrogen-bonding functional groups contained in one molecule of the (meth) acrylic resin (A)” / "(meth) acrylic resin”. It is determined by "weight average molecular weight (Mw) of (A)".
  • Mw weight average molecular weight
  • the hydrogen-bonding functional group equivalent of the (meth) acrylic resin (A) is adjusted by the number of hydrogen-bonding functional groups contained in the (meth) acrylic resin.
  • the weight average molecular weight of the (meth) acrylic resin (A) is preferably 310 to 1000, more preferably 400 to 900.
  • the weight average molecular weight Mw of the (meth) acrylic resin (A) can be measured (in terms of polystyrene) by, for example, gel permeation chromatography (GPC).
  • the amount of the (meth) acrylic resin (A) contained in the liquid crystal sealant depends on the curability of the desired liquid crystal sealant, but is preferably 1 to 20 parts by mass and 3 to 20 parts by mass with respect to 100 parts by mass of the liquid crystal sealant. 15 parts by mass is more preferable, and 3 to 10 parts by mass is further preferable.
  • the amount of the (meth) acrylic resin (A) is in the above range, the elastic modulus of the liquid crystal sealant after photocuring tends to be good.
  • Resin (B) is a resin having an epoxy group and a (meth) acrylic group in one molecule.
  • an epoxy resin and (meth) acrylic acid are reacted in the presence of a basic catalyst.
  • the resulting (meth) acrylic modified epoxy resin is included.
  • the resin (B) Since the resin (B) has an epoxy group and a (meth) acrylic group in the molecule, it has both photocurability and thermosetting property.
  • the amorphous epoxy resin since the amorphous epoxy resin has high solubility in the liquid crystal, it is generally preferable not to include it in the liquid crystal sealant used in the liquid crystal dropping method.
  • the epoxy resin has a (meth) acrylic group as in the resin (B) of the present invention, the solubility in the liquid crystal is reduced. Therefore, the resin (B) may be a resin in which a (meth) acrylic group is introduced into an amorphous epoxy resin.
  • the epoxy resin used as the raw material of the resin (B) may be a bifunctional or higher functional epoxy resin having two or more epoxy groups in the molecule, and may be bisphenol A type, bisphenol F type, or 2,2'-diallyl bisphenol A type. , Bisphenol AD type, and bisphenol type epoxy resin such as hydrogenated bisphenol type; novolak type epoxy resin such as phenol novolac type, cresol novolac type, biphenyl novolac type, and trisphenol novolac type; biphenyl type epoxy resin; naphthalene type epoxy resin Etc. are included.
  • the (meth) acrylic-modified epoxy resin obtained by (meth) acrylic modification of a trifunctional or tetrafunctional polyfunctional epoxy resin has a high crosslink density, and the adhesive strength between the sealing member and the substrate when used as a liquid crystal display panel. Is easy to decrease. Therefore, a (meth) acrylic-modified epoxy resin obtained by modifying a bifunctional epoxy resin with (meth) acrylic is preferable.
  • the bifunctional epoxy resin is preferably a biphenyl type epoxy resin, a naphthalene type epoxy resin, and a bisphenol type epoxy resin, and a bisphenol type epoxy resin such as bisphenol A type and bisphenol F type is more preferable from the viewpoint of coating efficiency of the liquid crystal sealant. ..
  • the bisphenol type epoxy resin has advantages such as excellent coatability as compared with an epoxy resin such as a biphenyl ether type.
  • the epoxy resin used as the raw material of the resin (B) may be one kind or two or more kinds. Further, the epoxy resin used as a raw material is preferably highly purified by a molecular distillation method, a cleaning method or the like.
  • the resin (B) also contains a hydrogen-bonding functional group such as a hydroxyl group, a urethane bond, an amide group, and a carboxyl group.
  • hydrogen-bonding functional groups also include hydroxyl groups formed by the reaction of the epoxy groups of the epoxy resin with (meth) acrylic acid.
  • examples of the hydrogen-bonding functional group also include a hydroxyl group contained in (meth) acrylic acid or an epoxy resin which is a raw material of the resin (B), a urethane bond, a carboxyl group, an amide group and the like.
  • the compatibility between the resin (B) and the hydrophobic liquid crystal becomes low.
  • the liquid crystal sealant becomes difficult to dissolve in the liquid crystal, and the liquid crystal sealant suitable for the liquid crystal dropping method is obtained.
  • the hydrogen-bonding functional group equivalent of the resin (B) is preferably 1.0 ⁇ 10 -4 to 5 ⁇ 10 -3 mol / g, preferably 2.0 ⁇ 10 -3 to 4.5 ⁇ 10 -3 mol / g. Is more preferable.
  • the hydrogen-bonding functional group equivalent is less than 1.0 ⁇ 10 -4 mol / g, the number of hydrogen-bonding functional groups in the resin (B) is small, and it is difficult to obtain the effect of suppressing dissolution on the liquid crystal.
  • the hydrogen-bonding functional group equivalent of the resin (B) exceeds 5 ⁇ 10 -3 mol / g, the moisture resistance of the cured product of the liquid crystal sealant tends to decrease.
  • the hydrogen-bonding functional group equivalent (mol / g) of the resin (B) is "the number of hydrogen-bonding functional groups contained in one molecule of the resin (B)" / "weight average molecular weight (Mw) of the resin (B)). Is required. For example, when the hydrogen-bonding functional group of the resin (B) is only a hydroxyl group generated by the reaction of (meth) acrylic acid and the epoxy resin, the number of moles of the reacted (meth) acrylic acid is determined by the resin (B). It is obtained by dividing by the weight average molecular weight (Mw) of.
  • the hydrogen-bonding functional group equivalent of the resin (B) is determined by adjusting the number of moles of (meth) acrylic acid to react with the epoxy resin as a raw material, or by having the (meth) acrylic acid or epoxy resin as a raw material. It can be controlled by adjusting the amount of hydrogen-bonding functional groups or the like.
  • the hydroxyl value equivalent of the resin (B) is particularly preferably 2.0 ⁇ 10 -3 to 5 ⁇ 10 -3 mol / g.
  • the weight average molecular weight of the resin (B) is preferably, for example, 310 to 1000, more preferably 350 to 900.
  • the weight average molecular weight Mw of the resin (B) can be measured (in terms of polystyrene) by, for example, gel permeation chromatography (GPC).
  • the amount of the resin (B) contained in the liquid crystal sealant is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass, and even more preferably 40 to 70 parts by mass with respect to 100 parts by mass of the liquid crystal sealant. When the amount of the resin (B) is within the above range, the thermosetting property of the liquid crystal sealant tends to be good.
  • thermosetting agent (C) contains one or both of a thermosetting agent having a melting point of 90 ° C. or lower and a thermosetting agent having a melting point of 170 ° C. or higher. It is more preferable that the thermosetting agent (C) contains at least a thermosetting agent having a melting point of 90 ° C. or lower.
  • the melting point of the thermosetting agent having a melting point of 90 ° C. or lower is preferably 60 to 90 ° C., more preferably 70 to 90 ° C.
  • the melting point of the thermosetting agent is 90 ° C. or lower, as described above, the displacement of the substrate is unlikely to occur when the liquid crystal display panel is manufactured.
  • the melting point of the thermosetting agent is 60 ° C. or higher, the storage stability of the liquid crystal sealant tends to be good.
  • the melting point of the thermosetting agent having a melting point of 170 ° C. or higher is preferably 170 to 300 ° C., more preferably 170 to 230 ° C.
  • the melting point of the thermosetting agent is 170 ° C. or higher, as described above, when the liquid crystal display panel is manufactured, the seal pattern is less likely to be softened excessively and the substrate is less likely to be misaligned.
  • the melting point of the thermosetting agent is 230 ° C. or lower, it is not necessary to raise the temperature excessively when the liquid crystal sealant is cured, and it is easy to sufficiently heat-cure.
  • thermosetting agent (C) is not particularly limited as long as it has the above melting point and can cure the above-mentioned resin (B) by heating, but a dihydrazide-based thermosetting curing agent, an imidazole-based thermosetting curing agent, and the like. It is preferably at least one thermosetting agent selected from the group consisting of amine adduct-based thermosetting agents and polyamine-based thermosetting agents.
  • the thermosetting agent (C) may contain only one kind of these, or may contain two or more kinds of them.
  • dihydrazide-based thermal latent curing agent examples include adipic acid dihydrazide (melting point 181 ° C.), dodecanedioic acid dihydrazide (melting point 190 ° C.), sebacic acid dihydrazide (melting point 189 ° C.), and the like.
  • imidazole-based thermal latent curing agents examples include 2,4-diamino-6- [2'-ethylimidazolyl- (1')]-ethyltriazine (melting point 215 to 225 ° C.).
  • the amine adduct-based thermal latent curing agent is a thermal latent curing agent composed of an additional compound obtained by reacting an amine-based compound having catalytic activity with an arbitrary compound.
  • the polyamine-based thermal latent curing agent is a thermal latent curing agent having a polymer structure obtained by reacting an amine with an epoxy, and an example thereof is ADEKA Hardener EH4357S (softening point 73 to 83 ° C.) manufactured by ADEKA Corporation. , ADEKA Hardener EH5057P (melting point 75 to 85 ° C.) and the like.
  • the amount of the thermosetting agent (C) is preferably 1 to 20 parts by mass, more preferably 3 to 15 parts by mass, and even more preferably 5 to 13 parts by mass with respect to 100 parts by mass of the liquid crystal sealant. When the amount of the thermosetting agent (C) is in the above range, the liquid crystal sealant can be sufficiently cured by heating.
  • Photopolymerization initiator (D) The photopolymerization initiator (D) may be a compound capable of generating an active species by irradiation with light, may be a self-cleaving type photopolymerization initiator, or is a hydrogen abstraction type photopolymerization initiator. You may.
  • the liquid crystal sealant may contain only one type of photopolymerization initiator (D), or may contain two or more types.
  • self-cleaving photopolymerization initiators include benzyl dimethyl ketals such as alkylphenone compounds (eg 2,2-dimethoxy-1,2-diphenylethane-1-one (BASF IRGACURE 651)), 2- ⁇ -Aminoalkylphenone such as methyl-2-morpholino (4-thiomethylphenyl) propan-1-one (IRGACURE 907 manufactured by BASF), 1-hydroxy-cyclohexyl-phenyl-ketone (IRGACURE 184 manufactured by BASF), etc.
  • alkylphenone compounds eg 2,2-dimethoxy-1,2-diphenylethane-1-one (BASF IRGACURE 651)
  • 2- ⁇ -Aminoalkylphenone such as methyl-2-morpholino (4-thiomethylphenyl) propan-1-one
  • IRGACURE 907 manufactured by BASF
  • 1-hydroxy-cyclohexyl-phenyl-ketone IRGACURE 184 manufactured by BA
  • acylphosphine oxide compounds eg 2,4,6-trimethylbenzoindiphenylphosphenyl oxide, etc.
  • titanosen compounds eg bis ( ⁇ 5-2,4-cyclopentadiene-1-yl)- Bis (2,6-difluoro-3- (1H-pyrrole-1-yl) -phenyl) titanium, etc.
  • acetophenone compounds eg diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1- On, benzyl dimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1, -Hydroxycyclohexyl-phenylketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-
  • hydrogen abstraction initiators examples include benzophenone compounds (eg, benzophenone, o-benzoylmethylbenzoate methyl-4-phenylbenzophenone, 4,4'-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'- Methyl-diphenylsulfide, acrylicized benzophenone, 3,3', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, etc.), thioxone compounds (eg, thioxanthone, etc.) 2-Chlorothioxanthone (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 1-chloro-4-propoxythioxanthone, 1-chloro-4-ethoxythioxanthone (Rambson Limited manufactured by Speedcure CPTX), 2-isopropylxantone (manufactured by Ram
  • thioxanthone-based compounds, anthraquinone-based compounds, and oxime ester-based compounds are preferable, and thioxanthone-based compounds and oxime ester-based compounds are particularly preferable.
  • the molecular weight of the photopolymerization initiator (D) is preferably 200 or more and 5000 or less. When the molecular weight is 200 or more, it is difficult to elute into the liquid crystal. When the molecular weight is 5000 or less, the compatibility with the (meth) acrylic resin (A) is enhanced, and sufficient curability can be easily obtained.
  • the molecular weight of the photopolymerization initiator (D) is more preferably 230 or more and 3000 or less, and further preferably 230 or more and 1500 or less.
  • the content of the photopolymerization initiator (D) is preferably 0.1 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, and 0.5 to 3 parts by mass with respect to 100 parts by mass of the liquid crystal sealant. Is even more preferable.
  • the amount of the photopolymerization initiator (D) is within the above range, the above-mentioned (meth) acrylic resin (A) and resin (B) can be sufficiently photocured.
  • Epoxy resin (E) The liquid crystal sealant may further contain an epoxy resin (E) that is liquid at room temperature.
  • the liquid crystal sealant contains the epoxy resin (E)
  • the display characteristics of the obtained liquid crystal panel are improved, and the moisture resistance of the cured product of the liquid crystal sealant is further improved.
  • Examples of such an epoxy resin (E) include an epoxy resin having a weight average molecular weight of 500 to 10000, and an aromatic epoxy resin having a weight average molecular weight of 1000 to 5000 is more preferable.
  • the weight average molecular weight of the epoxy resin can be measured (in terms of polystyrene) by, for example, gel permeation chromatography (GPC).
  • aromatic epoxy resins examples include aromatic diols typified by bisphenol A, bisphenol S, bisphenol F, bisphenol AD, etc., and diols obtained by modifying these with ethylene glycol, propylene glycol, and alkylene glycol.
  • Aromatic polyvalent glycidyl ether compound obtained by reaction with epichlorohydrin; novolak resin derived from phenol or cresol and formaldehyde, polyphenols represented by polyalkenylphenol and its copolymers, etc., by reaction with epichlorohydrin
  • the obtained novolak-type polyvalent glycidyl ether compound; glycidyl ether compounds of xylylene phenol resin and the like are included.
  • cresol novolac type epoxy resin cresol novolac type epoxy resin, phenol novolac type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, triphenol methane type epoxy resin, triphenol ethane type epoxy resin, trisphenol type epoxy Resins, dicyclopentadiene type epoxy resins, diphenyl ether type epoxy resins, and biphenyl type epoxy resins are preferable.
  • the liquid crystal sealant may contain only one kind of these, or may contain two or more kinds of these.
  • the content of the liquid epoxy resin (E) is preferably 0.5 to 20 parts by mass, more preferably 1 to 15 parts by mass, and even more preferably 1 to 10 parts by mass with respect to 100 parts by mass of the liquid crystal sealant.
  • the amount of the liquid epoxy resin (E) is within this range, the moisture resistance of the cured product of the liquid crystal sealant tends to increase.
  • the liquid crystal sealant may further contain inorganic particles (F) and organic particles (G), if necessary.
  • the liquid crystal sealant may contain either one of the inorganic particles (F) and the organic particles (G), or may contain both.
  • inorganic particles (F) include calcium carbonate, magnesium carbonate, barium sulfate, magnesium sulfate, aluminum silicate, zirconium silicate, iron oxide, titanium oxide, aluminum oxide (alumina), zinc oxide, silicon dioxide (silica), and titanium.
  • Inorganic fillers such as potassium acid, kaolin, talc, glass beads, sericite active white clay, bentonite, aluminum oxide, silicon nitride and the like are included, and silicon dioxide and talc are preferably included. Of these, silicon dioxide (silica) or talc is preferred.
  • the liquid crystal sealant may contain only one type of inorganic particles (F), or may contain two or more types of inorganic particles (F).
  • the shape of the inorganic particles (F) is not particularly limited, and may be a fixed shape such as a spherical shape, a plate shape, a needle shape, or a non-fixed shape.
  • the average primary particle diameter of the inorganic particles (F) is preferably 1.5 ⁇ m or less, and the specific surface area thereof is preferably 0.5 m 2 / g to 20 m 2 / g.
  • the average primary particle diameter of the inorganic particles (F) can be measured by the laser diffraction method described in JIS Z8825-1.
  • the specific surface area can be measured by the BET method described in JIS Z8830.
  • the content of the inorganic particles (F) is preferably 1 to 30 parts by mass, more preferably 3 to 25 parts by mass, and even more preferably 5 to 20 parts by mass with respect to 100 parts by mass of the liquid crystal sealant.
  • the amount of the inorganic particles (F) is in the above range, the viscosity of the liquid crystal sealant or the like tends to fall within the desired range.
  • examples of the organic particles (G) include silicone particles, acrylic particles, styrene particles such as a styrene / divinylbenzene copolymer, and polyolefin particles.
  • the liquid crystal sealant may contain only one type of organic particles (G), or may contain two or more types of organic particles (G).
  • the average primary particle size of the organic particles (G) is preferably 0.05 to 13 ⁇ m, more preferably 0.1 to 10 ⁇ m, and even more preferably 0.1 to 8 ⁇ m.
  • the shape of the organic particles (G) is not particularly limited, but is preferably spherical, and more preferably true spherical.
  • the average primary particle size of the organic particles (G) can be measured by a microscope method, specifically, an image analysis of an electron microscope.
  • the surface of the organic particles (G) is preferably smooth. When the surface is smooth, the specific surface area decreases and the amount of organic particles (G) that can be added to the liquid crystal sealant increases.
  • the content of the organic particles (G) is preferably 0.1 to 30 parts by mass, more preferably 0.3 to 20 parts by mass, and further preferably 0.3 to 15 parts by mass with respect to 100 parts by mass of the liquid crystal sealant. preferable.
  • the amount of the organic particles (G) is in the above range, the elastic modulus of the liquid crystal sealant after photocuring tends to be within a desired range.
  • Liquid crystal sealants include coupling agents such as silane coupling agents, ion trapping agents, ion exchangers, leveling agents, pigments, dyes, plasticizers, and defoamers, if necessary. It may further contain a foaming agent or the like. Further, a spacer or the like may be further included to adjust the gap of the liquid crystal display panel.
  • the viscosity of the E-type viscometer of the liquid crystal sealant at 25 ° C. and 2.5 rpm is preferably 200 to 450 Pa ⁇ s, more preferably 300 to 400 Pa ⁇ s.
  • the liquid crystal sealant is likely to be deformed so as to fill these gaps when the pair of substrates are superposed on each other via the liquid crystal sealant (seal pattern). Therefore, the gap width between the pair of substrates of the liquid crystal display panel can be appropriately controlled.
  • the thixotropy index (TI value) of the liquid crystal sealant of the present invention is preferably 1.0 to 1.5, more preferably 1.1 to 1.3, from the viewpoint of coatability of the liquid crystal sealant.
  • TI value the viscosity ⁇ 1 of the liquid crystal sealant at room temperature (25 ° C.) and 0.5 rpm was measured using an E-type viscometer, and the viscosity ⁇ 2 of the liquid crystal sealant at 5 rpm was measured. ) Is the value obtained.
  • TI value (viscosity ⁇ 1 (25 ° C) at 0.5 rpm) / (viscosity ⁇ 2 (25 ° C) at 5 rpm) ... (1)
  • the elastic modulus of the cured film obtained by irradiating the liquid crystal sealant with light having a wavelength of 365 nm 2 at 3000 mJ / cm 2 at 120 ° C. is 30 MPa or more and 100 MPa or less, more preferably 32 to 90 MPa, still more preferably 34 to 88 MPa.
  • the elastic modulus of the film cured under the above conditions substantially corresponds to the elastic modulus after photocuring and before heat curing of the liquid crystal sealant.
  • the elastic modulus is 30 MPa or more, the seal pattern is not excessively deformed when the liquid crystal display panel is manufactured, and the position of the substrate is less likely to shift.
  • the elastic modulus when the elastic modulus is 100 MPa or less, the adhesive strength between the seal member and the substrate is sufficiently increased when the liquid crystal display panel is used.
  • the elastic modulus can be adjusted by the structure of the (meth) acrylic resin (A), the structure of the resin (B) having an epoxy group and a (meth) acrylic group in one molecule, the equivalent of reactive functional groups, and the like.
  • the elastic modulus is a storage elastic modulus measured as follows. First, a liquid crystal sealant is applied using an applicator or the like to a thickness of 100 ⁇ m, and light having a wavelength of 365 nm is irradiated at 3000 mJ / cm 2 in a nitrogen atmosphere to be photocured. The obtained cured film is cut into strips and heated from room temperature to 180 ° C. at 5 ° C./min using a viscoelasticity measuring device DMS to specify the storage elastic modulus at 120 ° C.
  • the glass transition temperature when the liquid crystal sealant is irradiated with light having a wavelength of 365 nm at 3000 mJ / cm 2 and then cured at 120 ° C. for 1 hour is preferably 120 ° C. or lower, more preferably 80 to 120 ° C., and 80 to 110 ° C. °C is more preferable.
  • the glass transition temperature of the cured product under the above conditions substantially corresponds to the glass transition temperature after photocuring and heat curing of the liquid crystal sealant.
  • the adhesive strength between the sealing member and the substrate tends to increase.
  • the glass transition temperature can be adjusted by the glass transition temperature of the (meth) acrylic resin (A) and the like.
  • the glass transition temperature of the cured product of the liquid crystal sealant can be measured as follows.
  • the liquid crystal sealant is applied using an applicator so as to have a thickness of 100 ⁇ m, and is irradiated with light having a wavelength of 365 nm at 3000 mJ / cm 2 in a nitrogen atmosphere to be photocured. Then, it is heat-cured in an oven at 120 ° C. for 1 hour to obtain a cured film having a thickness of 100 ⁇ m. Then, the obtained cured film was cut into strips and heated from room temperature to 180 ° C. at 5 ° C./min using a viscoelasticity measuring device DMS, and the obtained storage elastic modulus (E') and loss elastic modulus were obtained. The point at which the ratio with (E'') is maximized is defined as the glass transition temperature.
  • the liquid crystal display panel of the present invention includes a pair of substrates, a frame-shaped seal member arranged between the substrates, and a liquid crystal filled between the pair of substrates and inside the frame-shaped seal member.
  • the sealing member is a cured product of the above-mentioned liquid crystal sealing agent.
  • the pair of substrates are both transparent substrates.
  • transparent substrate materials include glass or polycarbonate, polyethylene terephthalate, polyether sulfone, PMMA and the like.
  • a matrix-like TFT, a color filter, a black matrix, etc. are arranged on the surface of the display board or the facing board.
  • An alignment film is further formed on the surface of the display substrate or the facing substrate.
  • the alignment film includes known organic alignment agents, inorganic alignment agents, and the like. Further, a known liquid crystal can be used as the liquid crystal.
  • the liquid crystal display panel manufacturing method generally includes a liquid crystal dropping method and a liquid crystal injection method, but the liquid crystal display panel manufacturing method of the present invention is preferably the liquid crystal dropping method.
  • the method for manufacturing a liquid crystal display panel by the liquid crystal dropping method is as follows: 1) a seal pattern forming step of applying the above-mentioned liquid crystal sealant to one substrate to form a frame-shaped seal pattern, and 2) the seal pattern is uncured. Liquid crystal that drops liquid crystal on one substrate and in the area surrounded by the seal pattern, or on the other substrate and in the area surrounded by the seal pattern when the other substrate and one substrate face each other. It includes a dropping step, a superposition step of 3) superimposing one substrate and the other substrate via a seal pattern, and 4) a curing step of curing the seal pattern.
  • the above-mentioned liquid crystal sealant is applied to one of the substrates.
  • the method of applying the liquid crystal sealant is not particularly limited as long as it is a method capable of forming a seal pattern with a desired thickness and width, such as screen printing or coating with a dispenser. It is the same as the coating method.
  • the shape of the seal pattern to be formed may be appropriately selected according to the application of the liquid crystal display panel and the like so that the liquid crystal does not leak.
  • it may have a rectangular frame shape, but is not limited to the shape.
  • the line width of the seal pattern is preferably 0.2 to 1.0 mm, more preferably 0.2 to 0.7 mm.
  • the pair of substrates are opposed to each other with the seal pattern uncured.
  • the state in which the seal pattern is uncured means a state in which the curing reaction of the liquid crystal sealant has not progressed to the gel point.
  • the seal pattern may be semi-cured by irradiating or heating the seal pattern in order to suppress the dissolution of the liquid crystal sealant in the liquid crystal.
  • the liquid crystal dropping method is the same as the known liquid crystal dropping method, and the liquid crystal may be dropped on the substrate on which the seal pattern is formed, and the liquid crystal may be dropped on the substrate on which the seal pattern is not formed (the other substrate). May be dropped.
  • one substrate and the other substrate are laminated so as to face each other via a seal pattern. At this time, the gap between the substrates is controlled to be within a desired range.
  • the seal pattern is cured.
  • the method for curing the seal pattern is not particularly limited, but it is preferable that the seal pattern is temporarily cured by irradiation with light having a predetermined wavelength and then finally cured by heating. By light irradiation, the seal pattern can be instantly cured, and the components in the liquid crystal sealant can be suppressed from being dissolved in the liquid crystal.
  • the wavelength of the light to be irradiated is appropriately selected according to the type of the photopolymerization initiator, and ultraviolet light is preferable.
  • the light irradiation time is, for example, about 10 minutes, although it depends on the composition of the liquid crystal sealant.
  • the amount of energy to be irradiated at this time may be an amount of energy that can cure the (meth) acrylic resin (A), the resin (B), and the like.
  • the heating temperature is, for example, 100 to 150 ° C., although it depends on the composition of the liquid crystal sealant, and the heating time is preferably about 2 hours.
  • E > -Epoxy resin (E-1): Epicoat 1004AF (manufactured by Mitsubishi Chemical Corporation, epoxy resin, softening point 97 ° C.) -Epoxy resin (E-2): YL983U (manufactured by Mitsubishi Chemical Corporation, epoxy resin, screw F type, liquid at room temperature)
  • Resin (B-1) methacrylic acid-modified bisphenol F type epoxy resin
  • JER 828 manufactured by Mitsubishi Chemical Co., Ltd., epoxy equivalent 190 g / eq
  • polymerization inhibitor p-methoxyphenol
  • catalytic triethanolamine 0.2 g
  • acrylic acid 54 0.0 g was charged in a flask, dry air was sent in, and the reaction was carried out for 5 hours while refluxing and stirring at
  • the liquid crystal sealant was printed approximately in the center on non-alkali glass having a width of 25 mm, a length of 45 mm, and a thickness of 5 mm.
  • the seal pattern was a circle with a diameter of 1 mm.
  • the paired non-alkali glass was placed on the seal pattern with a slight vertical shift, and fixed with a jig.
  • the test piece fixed with the jig was irradiated with light having a wavelength of 365 nm at an intensity of 500 mW / cm 2 with an ultraviolet irradiation device (manufactured by Ushio, Inc.) to cure the liquid crystal sealant.
  • the illuminance energy of ultraviolet rays was set to 3000 mJ / cm 2 .
  • the end of one glass 10a of this test piece was grasped by the jig 20 and hung vertically.
  • a weight 21 of 500 g was hung from the lower end of the other glass 10b.
  • the cured product 11 of the liquid crystal sealant is arranged between the pair of glasses 10a and 10b.
  • the test piece with the weight 21 suspended was placed in an oven at 120 ° C., and the time until the other substrate 10b fell was measured and evaluated as follows. ⁇ : Did not fall for 10 minutes or more ⁇ : Falled in less than 10 minutes
  • the liquid crystal sealant was printed on a 25 mm ⁇ 45 mm ⁇ 5 mm thick non-alkali glass using a screen plate.
  • the seal pattern was a circle with a diameter of 1 mm.
  • a pair of non-alkali glass was placed on the seal pattern and fixed with a jig.
  • the test piece fixed with the jig was irradiated with light having a wavelength of 365 nm at 500 mW / cm 2 with an ultraviolet irradiation device (manufactured by Ushio, Inc.) to cure the liquid crystal sealant.
  • the illuminance energy of ultraviolet rays was set to 3000 mJ / cm 2 .
  • a test piece obtained by photo-curing a liquid crystal sealant with ultraviolet rays was heat-treated at 120 ° C. for 60 minutes using an oven to prepare a sample for measuring adhesive strength.
  • the tensile speed was set to 2 mm / min, and the cured liquid crystal sealant was peeled off in a direction parallel to the glass surface to measure the tensile strength of the flat surface.
  • the adhesive strength was evaluated as follows according to the magnitude of the planar tensile strength.
  • thermosetting agent (C) is in the range of more than 90 ° C. and less than 170 ° C. The result of the deviation test was low (Comparative Example 4). Since the melting point of the thermal polymerization initiator is relatively high, it is presumed that the liquid crystal sealant after photocuring was temporarily softened before heat curing, causing a shift.
  • the liquid crystal dropping method can firmly bond the substrates to each other without causing a displacement of the substrates. Therefore, it is very useful for manufacturing a high quality liquid crystal display panel.

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  • Organic Chemistry (AREA)
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  • Crystallography & Structural Chemistry (AREA)
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Abstract

La présente invention aborde le problème de la fourniture d'un agent d'étanchéité à cristaux liquides qui peut également être utilisé dans une technique d'égouttement de cristaux liquides, le rend moins susceptible de provoquer un désalignement relatif d'une paire de substrats lors de la production d'un écran d'affichage à cristaux liquides, et a une force adhésive élevée. Cet agent d'étanchéité à cristaux liquides en tant que solution au problème contient une résine (méth)acrylique (A), une résine (B) ayant un groupe époxy et un groupe (méth)acrylique par molécule, un agent thermodurcissable (C) comprenant un agent thermodurcissable ayant un point de fusion de 90 °C ou moins et/ou un agent thermodurcissable ayant un point de fusion de 170 °C ou plus, et un initiateur de photopolymérisation (D). Un film durci obtenu par irradiation de l'agent d'étanchéité à cristaux liquides avec 3000 mJ/cm2 de lumière ayant une longueur d'onde de 365 nm a un module d'élasticité de 30 à 100 MPa à 120 °C.
PCT/JP2020/018466 2019-05-10 2020-05-01 Agent d'étanchéité à cristaux liquides, écran d'affichage à cristaux liquides l'utilisant et son procédé de production WO2020230678A1 (fr)

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JP2021519386A JP7238112B2 (ja) 2019-05-10 2020-05-01 液晶シール剤、これを用いた液晶表示パネル、およびその製造方法
KR1020217035898A KR20210148294A (ko) 2019-05-10 2020-05-01 액정 실링제, 이것을 이용한 액정 표시 패널, 및 그의 제조 방법
CN202080027583.0A CN113661438A (zh) 2019-05-10 2020-05-01 液晶密封剂、使用其的液晶显示面板、及其制造方法

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Citations (4)

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WO2008102550A1 (fr) * 2007-02-20 2008-08-28 Mitsui Chemicals, Inc. Composition de résine durcissable pour sceller un cristal liquide, et procédé de fabrication d'un panneau d'affichage à cristaux liquides utilisant cette composition
JP2011232631A (ja) * 2010-04-28 2011-11-17 Mitsui Chemicals Inc 液晶表示パネルの製造方法および液晶表示パネル
WO2012020754A1 (fr) * 2010-08-10 2012-02-16 積水化学工業株式会社 Agent d'étanchéité pour procédé de déposition par gouttelettes de cristaux liquides
WO2017082000A1 (fr) * 2015-11-09 2017-05-18 積水化学工業株式会社 Produit d'étanchéité pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides

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JP2009013282A (ja) * 2007-07-04 2009-01-22 Nippon Kayaku Co Ltd 液晶シール剤およびそれを用いた液晶表示セル
JP5508001B2 (ja) 2008-03-26 2014-05-28 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
CN103238106B (zh) * 2011-08-17 2016-03-23 积水化学工业株式会社 液晶显示元件用密封剂以及液晶显示元件
CN104620166B (zh) * 2013-11-13 2016-01-13 Dic株式会社 液晶显示装置
JP6046868B1 (ja) * 2015-05-20 2016-12-21 積水化学工業株式会社 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP6097454B1 (ja) 2015-09-02 2017-03-15 積水化学工業株式会社 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子
JP6643944B2 (ja) * 2016-04-25 2020-02-12 日本化薬株式会社 液晶光学素子用シール剤及びそれを用いた液晶光学素子

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WO2008102550A1 (fr) * 2007-02-20 2008-08-28 Mitsui Chemicals, Inc. Composition de résine durcissable pour sceller un cristal liquide, et procédé de fabrication d'un panneau d'affichage à cristaux liquides utilisant cette composition
JP2011232631A (ja) * 2010-04-28 2011-11-17 Mitsui Chemicals Inc 液晶表示パネルの製造方法および液晶表示パネル
WO2012020754A1 (fr) * 2010-08-10 2012-02-16 積水化学工業株式会社 Agent d'étanchéité pour procédé de déposition par gouttelettes de cristaux liquides
WO2017082000A1 (fr) * 2015-11-09 2017-05-18 積水化学工業株式会社 Produit d'étanchéité pour élément d'affichage à cristaux liquides, matériau à conduction verticale, et élément d'affichage à cristaux liquides

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JP7238112B2 (ja) 2023-03-13

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