WO2020022188A1 - Agent d'étanchéité bloquant la lumière pour procédés de dépôt de cristaux liquides, et procédé de production d'un panneau d'affichage à cristaux liquides utilisant cet agent - Google Patents

Agent d'étanchéité bloquant la lumière pour procédés de dépôt de cristaux liquides, et procédé de production d'un panneau d'affichage à cristaux liquides utilisant cet agent Download PDF

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Publication number
WO2020022188A1
WO2020022188A1 PCT/JP2019/028313 JP2019028313W WO2020022188A1 WO 2020022188 A1 WO2020022188 A1 WO 2020022188A1 JP 2019028313 W JP2019028313 W JP 2019028313W WO 2020022188 A1 WO2020022188 A1 WO 2020022188A1
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WIPO (PCT)
Prior art keywords
liquid crystal
light
sealant
group
agent
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PCT/JP2019/028313
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English (en)
Japanese (ja)
Inventor
健祐 大塚
Original Assignee
三井化学株式会社
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 三井化学株式会社 filed Critical 三井化学株式会社
Priority to CN201980048301.2A priority Critical patent/CN112424680A/zh
Priority to KR1020207037783A priority patent/KR102509153B1/ko
Priority to JP2020532342A priority patent/JP7181936B2/ja
Publication of WO2020022188A1 publication Critical patent/WO2020022188A1/fr

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Classifications

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

Definitions

  • the present invention relates to a light-shielding sealant for a liquid crystal dropping method and a method for manufacturing a liquid crystal display panel using the same.
  • a liquid crystal display panel has a structure in which a liquid crystal material (hereinafter, also simply referred to as “liquid crystal”) is sandwiched between two transparent substrates provided with electrodes on the surface, and the periphery thereof is sealed with a liquid crystal sealant. It is a panel.
  • liquid crystal a liquid crystal material
  • liquid crystal sealant Although the amount of the liquid crystal sealant used is small, it is in direct contact with the liquid crystal, which greatly affects the reliability of the liquid crystal display panel. Therefore, in order to achieve high image quality of a liquid crystal display panel, liquid crystal sealants are currently required to have high and various characteristics.
  • a liquid crystal dropping method has been widely used as a method of manufacturing a liquid crystal display panel.
  • a liquid crystal sealant is applied on a transparent substrate to form a frame for filling the liquid crystal, and (2) fine liquid crystal is dropped into the frame.
  • a liquid crystal sealant curable by both light and heat may be used.
  • the step (3) after the liquid crystal sealant is temporarily cured by irradiating light such as ultraviolet rays, post-curing by heating can be performed.
  • the liquid crystal sealant is in contact with the liquid crystal for a long time in an uncured state. Therefore, the components of the liquid crystal sealant are more easily dissolved in the liquid crystal than in the conventional liquid crystal injection method. Therefore, it has been proposed to increase the photocurability by adding an organic acid to the liquid crystal sealant to suppress the contamination of the liquid crystal (Patent Document 1).
  • the seal member black for example, a wide wiring or the like can be covered with the seal member, and a color filter can be arranged on the TFT array side. As a result, the degree of freedom in wiring design is widened, and the brightness of the liquid crystal display panel can be increased.
  • the present invention has been made in view of the above problems. That is, a light-shielding sealant for a liquid crystal dropping method, which has good photocurability and can reliably seal between liquid crystal display panel substrates without causing contamination of the liquid crystal, and An object of the present invention is to provide a method for manufacturing a liquid crystal display panel.
  • the present invention provides the following light-shielding sealant for a liquid crystal dropping method.
  • A an organic acid
  • B a photocurable resin having at least one ethylenically unsaturated double bond in one molecule (provided that the (A) organic acid is excluded)
  • C A titanocene-based photopolymerization initiator
  • D a light-shielding agent having a pH of less than 7.0 or more than 8.0
  • E a thermosetting compound having at least one epoxy group in one molecule (provided that ( B) excluding a photocurable resin) and
  • F a thermosetting agent, wherein the (A) organic acid has an oxygen atom equivalent represented by the following formula (1) of 23 g / eq or more and 75 g / eq.
  • Oxygen atom equivalent (g / eq) (molecular weight of organic acid) / (number of oxygen atoms in one molecule of organic acid) (1)
  • R represents an aromatic or aliphatic hydrocarbon or a derivative thereof
  • -P ( O) (OH ) 2 group
  • -SO 3 H group at least one functional group selected from the group consisting of -CONH 2 groups
  • the light-blocking sealant for a liquid crystal dropping method according to any one of [1] to [3].
  • the light-shielding sealant for a liquid crystal dropping method according to any one of [1] to [4], wherein the photocurable resin (B) further has an epoxy group in a molecule.
  • the heat curing agent (F) is selected from the group consisting of a dihydrazide heat latent curing agent, an imidazole heat latent curing agent, an amine adduct heat latent curing agent, and a polyamine heat latent curing agent.
  • the present invention also provides the following method for manufacturing a liquid crystal display panel.
  • the sealant for the liquid crystal dropping method of the present invention has good photocurability despite containing a light-shielding agent. Further, the liquid crystal dropping method sealing agent is unlikely to contaminate the liquid crystal even when it comes into contact with the liquid crystal. Therefore, according to the liquid crystal dropping method sealing agent, a liquid crystal display panel having excellent display reliability can be obtained.
  • Light-shielding sealant for liquid crystal dropping method comprises (A) an organic acid, (B) a photocurable resin, and (C) titanocene.
  • a system photopolymerization initiator comprises (D) a light-shielding agent, (E) a thermosetting compound, and (F) a thermosetting agent.
  • the sealant may contain other components as necessary.
  • the light-shielding agent contained in the sealant of the present invention has a pH of less than 7 (more specifically, less than 7.0) or a pH of more than 8.0, and the dispersibility of the light-shielding agent is much better. It is. Although the reason is not clear, if (D) the pH of the light-shielding agent is less than 7 (more specifically, less than 7.0) or if the pH is more than 8.0, (D) other light- It is considered that components (for example, (A) an organic acid, (B) a photocurable resin, and (E) a thermosetting compound) interact with each other.
  • components for example, (A) an organic acid, (B) a photocurable resin, and (E) a thermosetting compound
  • (D) the dispersibility of the light-shielding agent is improved. If the dispersibility of (D) the light-shielding agent is low, poor curing is likely to occur in a region where the concentration of the (D) light-shielding agent is high, resulting in uneven curability. On the other hand, when the (D) light-shielding agent is uniformly dispersed in the sealant as in the present invention, the curability of the entire sealant becomes uniform.
  • the sealant of the present invention contains (A) an organic acid, and the (A) organic acid promotes the photocuring reaction of (B) the photocurable resin. Further, at this time, since the oxygen atom equivalent of (A) the organic acid is within a predetermined range, even if the liquid crystal contacts the (A) organic acid, it hardly affects the liquid crystal.
  • the sealant of the present invention contains (C) a titanocene-based photopolymerization initiator having an ability to absorb visible light.
  • Light having a relatively long wavelength for example, visible light
  • the sealant contains (C) a titanocene-based photopolymerization initiator having an ability to absorb visible light.
  • Light having a relatively long wavelength for example, visible light
  • the sealant can be activated by such long-wavelength light. Therefore, by using a titanocene-based photopolymerization initiator that can be activated by such long-wavelength light, the deep curability of the sealant can be enhanced.
  • the sealant of the present invention has good photocurability even though it contains (D) a light-shielding agent so that its blackness is, for example, 2 to 5. Further, according to the sealing agent, it is possible to reliably seal the space between the substrates of the liquid crystal display panel without causing the liquid crystal to be contaminated by the uncured component.
  • the sealing agent contains (A) the organic acid, the photocurability of the sealing agent is enhanced.
  • the organic acid (A) may be a Bronsted acid, and the organic acid (A) includes a compound having an acid anhydride structure.
  • the organic acid has an oxygen atom equivalent represented by the following formula (1) of 23 g / eq to 75 g / eq, preferably 25 to 60 g / eq, more preferably 27 to 55 g. / Eq.
  • Oxygen atom equivalent (g / eq) (molecular weight of organic acid) / (number of oxygen atoms in one molecule of organic acid) (1)
  • the liquid crystal and the organic acid (A) are hardly compatible with each other even when the organic acid (sealant) comes into contact with the liquid crystal during the production of the liquid crystal display panel.
  • the liquid crystal is hardly contaminated.
  • the oxygen atom equivalent is 75 g / eq or less, even if a small amount of the (A) organic acid is eluted into the liquid crystal, the influence is hardly exerted.
  • the organic acid may contain only one kind of these groups, or may contain two or more kinds of these groups.
  • organic acids include acetic acid, butyric acid, oxalic acid, citric acid, lauric acid, stearic acid, malonic acid, adipic acid, tartaric acid, benzoic acid, salicylic acid, phthalic acid, monoethyl phosphate, monophenyl phosphate, Diethyl phosphate, mono-2-ethylhexyl phosphate, di (2-ethylhexyl) phosphate, benzenesulfonic acid, toluenesulfonic acid, sulfobenzoic acid, formic acid, propionic acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargon Acid, capric acid, myristic acid, palmitic acid, margaric acid, succinic acid, glutaric acid, dodecane diacid, sepasic acid, isophthalic acid, terephthalic acid, benzenetricar
  • Examples of the organic acid (A) having no ethylenically unsaturated double bond in one molecule include a compound represented by the following formula.
  • the organic acid (A) may contain an ethylenically unsaturated double bond in the molecule.
  • the (A) organic acid is polymerized with the (B) photocurable resin, and the cured product of the sealant is converted into the (A) organic acid. Is difficult to exude.
  • the number of unsaturated double bonds contained in one molecule of the organic acid may be two or more.
  • Examples of the (A) organic acid having an unsaturated double bond in one molecule include (meth) acrylic acid, itaconic acid, maleic acid, fumaric acid, 2- (meth) acryloyloxyethyl succinic acid, 2- (Meth) acryloyloxyethyl phthalic acid, bisphenol A type epoxy (meth) acrylate acid anhydride modified compound, bisphenol A type epoxy (meth) acrylate phosphoric acid modified compound, bisphenol F type epoxy (meth) acrylate acid anhydride modified Compounds, phosphoric acid-modified compounds of bisphenol F type epoxy acrylate, phosphoric acid (meth) acrylates, and high molecular weights thereof are included.
  • (meth) acryl means either or both of acryl and methacryl.
  • the preferred organic acids (A) include oxalic acid, tartaric acid, trimellitic acid, trimellitic anhydride, isophthalic acid, phenylphosphonic acid, 4'-hydroxy-4-biphenylcarboxylic acid, terephthalic acid, and succinic acid , And glutaric acid.
  • the preferred molecular weight of the organic acid (A) is from 60 to 5,000, more preferably from 60 to 3,000, even more preferably from 100 to 1500.
  • the (A) organic acid easily flows inside the sealant, and photocuring of the sealant is easily promoted.
  • the content of the organic acid (A) is 0.01 to 20 parts by mass, preferably 0.05 to 10 parts by mass, based on 100 parts by mass of the sealant.
  • the photocurable resin is not particularly limited as long as it has at least one ethylenically unsaturated double bond in one molecule. However, in this specification, (B) the photocurable resin does not include the compound corresponding to the (A) organic acid.
  • Examples of the photocurable resin include (B1) a (meth) acrylic resin and (B2) a (meth) acryl-modified epoxy having at least one epoxy group and one (meth) acryl group in one molecule. Resin included.
  • the sealant of the present invention may include both (B1) (meth) acrylic resin and (B2) (meth) acryl-modified epoxy resin.
  • the (meth) acrylic resin is a compound containing one or more (meth) acrylic groups in one molecule, and is a compound containing no epoxy group.
  • Examples of the (meth) acrylic resin include diacrylates and / or dimethacrylates such as polyethylene glycol, propylene glycol, and polypropylene glycol; diacrylates and / or dimethacrylates of tris (2-hydroxyethyl) isocyanurate; Diacrylate and / or dimethacrylate of diol obtained by adding 4 moles or more of ethylene oxide or propylene oxide to 1 mole of pentyl glycol; diacrylate of diol obtained by adding 2 moles of ethylene oxide or propylene oxide to 1 mole of bisphenol A; / Or dimethacrylate; diol of triol obtained by adding 3 mol or more of ethylene oxide or propylene oxide to 1 mol of trimethylolpropane.
  • triacrylate and / or di or trimethacrylate diacrylate and / or dimethacrylate of a diol obtained by adding at least 4 moles of ethylene oxide or propylene oxide to 1 mole of bisphenol A; tris (2-hydroxyethyl) isocyanurate triacrylate; Trimethylolpropane triacrylate and / or trimethacrylate, or an oligomer thereof; pentaerythritol triacrylate and / or trimethacrylate, or an oligomer thereof; polyacrylate and / or polymethacrylate of dipentaerythritol; tris (acryloxy) Ethyl) isocyanurate; caprolactone-modified tris (acryloxyethyl) isocyanate Nurate; caprolactone-modified tris (methacryloxyethyl) isocyanurate; alkyl-modified dipentaerythritol polyacrylate and / or polymethacrylate; cap
  • the weight average molecular weight of the (meth) acrylic resin can be, for example, about 310 to 1,000.
  • the weight average molecular weight Mw of the (meth) acrylic resin can be measured by gel permeation chromatography (GPC) using polystyrene as a standard.
  • the amount of the (B1) (meth) acrylic resin in the sealant is 5 to 80 parts by mass with respect to 100 parts by mass of the sealant, depending on the curability required for the sealant and its blackness. And more preferably 10 to 80 parts by mass.
  • the (B2) (meth) acryl-modified epoxy resin is a compound containing at least one each of a (meth) acryl group and an epoxy group.
  • the epoxy resin and the (meth) acrylic acid are tertiary, for example. It is a compound obtained by reacting in the presence of a basic catalyst such as an amine.
  • the (meth) acryl-modified epoxy resin has an epoxy group and a (meth) acryl group in the molecule, it can have both photocurability and thermosetting properties. Further, the (meth) acryl-modified epoxy resin has low solubility in liquid crystal, and hardly affects the liquid crystal.
  • the epoxy resin used as a raw material of the (meth) acryl-modified epoxy resin may be a bifunctional or higher epoxy resin having two or more epoxy groups in a molecule.
  • Examples thereof include bisphenol A type and bisphenol F.
  • a (meth) acryl-modified epoxy resin obtained by modifying a trifunctional or tetrafunctional polyfunctional epoxy resin with a (meth) acrylic resin has a high crosslinking density and a low adhesion strength to a substrate. Therefore, the epoxy resin used as the raw material of the (B2) (meth) acryl-modified epoxy resin is preferably a bifunctional epoxy resin.
  • the bifunctional epoxy resin is preferably a biphenyl type epoxy resin, a naphthalene type epoxy resin, and a bisphenol type epoxy resin.
  • bisphenol type epoxy resins such as bisphenol A type and bisphenol F type are preferably used as a sealing agent. It is preferable from the viewpoint of the applicability and the like.
  • Epoxy resin as a raw material may be only one kind, or two or more kinds may be combined. Further, it is preferable that the epoxy resin as a raw material is highly purified by a molecular distillation method, a washing method, or the like.
  • the (meth) acryl-modified epoxy resin is preferably one in which 10 to 99.5% of the epoxy groups of the epoxy resin as a raw material are modified with (meth) acryl groups, and 30 to 95% % Is more preferably modified with an acrylic group.
  • the epoxy group is modified in the above range with a (meth) acrylic group, the photocurability and the thermosetting property of the sealant are improved, and the moisture resistance of the cured product of the sealant is likely to be lowered.
  • the weight average molecular weight of the (meth) acryl-modified epoxy resin can be, for example, about 310 to 1,000.
  • the weight average molecular weight Mw of the (meth) acryl-modified epoxy resin can be measured, for example, by gel permeation chromatography (GPC) using polystyrene as a standard.
  • the amount of the (B2) (meth) acryl-modified epoxy resin in the sealing agent depends on the degree of curability required, but is preferably 5 to 80 parts by mass, and preferably 10 to 80 parts by mass, per 100 parts by mass of the sealing agent. More preferably, it is 80 parts by mass.
  • the photocurable resin preferably has a hydrogen-bonding functional group such as a hydroxyl group, a urethane bond, an amide group, and a carboxyl group in the molecule.
  • groups may be, for example, hydroxyl groups generated by reacting an epoxy group of an epoxy resin with (meth) acrylic acid, and a compound (B) as a raw material of a photocurable resin (for example, (meth) acrylic acid Or an epoxy resin), or a urethane bond, a carboxyl group, an amide group, or the like contained in a compound as a raw material.
  • the equivalent of the hydrogen bonding functional group contained in the photocurable resin is preferably from 1.0 ⁇ 10 ⁇ 4 to 5 ⁇ 10 ⁇ 3 mol / g, and preferably from 3.5 ⁇ 10 ⁇ 3 to 4. More preferably, it is 5 ⁇ 10 ⁇ 3 mol / g.
  • the hydrogen-bonding functional group equivalent is 1.0 ⁇ 10 ⁇ 4 mol / g or more, the dissolution of the photocurable resin (B) in the liquid crystal is easily suppressed.
  • the hydrogen bonding functional group equivalent is 5 ⁇ 10 ⁇ 3 mol / g or less
  • the cured product of (B) the photocurable resin tends to have sufficient moisture resistance, and the cured product of the sealant has moisture resistance. Is not easily reduced.
  • the hydrogen-bonding functional group equivalent (mol / g) of the photocurable resin is represented by "(B) Number of hydrogen-bonding functional groups contained in one molecule of photocurable resin” / "(B) Photocurable Weight average molecular weight (Mw) of the resin ".
  • Mw Photocurable Weight average molecular weight
  • the hydrogen-bonding functional group equivalent is such that the monomer for obtaining the (B1) (meth) acrylic resin is It can be controlled by adjusting the amount of the hydrogen-bonding functional group contained.
  • the (B) photo-curable resin is the above-mentioned (B2) (meth) acryl-modified epoxy resin
  • its hydrogen-bonding functional group equivalent is determined, for example, by reacting (meth) acrylic acid with the epoxy resin as a raw material. Can be controlled by adjusting the number of moles, or by adjusting the amount of hydrogen-bonding functional groups contained in the raw material (meth) acrylic acid or epoxy resin.
  • the total amount of (B) the photocurable resin (for example, the total amount of (B1) (meth) acrylic resin and (B2) (meth) acryl-modified epoxy resin) is 5 to 80 parts by mass with respect to 100 parts by mass of the sealant. And more preferably 10 to 80 parts by mass.
  • the (C) titanocene-based photopolymerization initiator contained in the sealant of the present invention is a compound for curing the (B) photocurable resin described above.
  • the use of the (C) titanocene-based photopolymerization initiator can enhance the deep curability of the sealant. Becomes
  • titanocene-based photopolymerization initiators include bis ( ⁇ 5-2,4-cyclopentadien-1-yl) -bis (2,6-difluoro-3- (1H-pyrrol-1-yl)- Phenyl) titanium, bis (cyclopentadienyl) -dichlorotitanium, bis (cyclopentadienyl) -diphenyltitanium, bis (cyclopentadienyl) -bis (2,3,4,5,6 pentafluorophenyl) titanium , Bis (cyclopentadienyl) -bis (2,6 difluorophenyl) titanium, bis (methylcyclopentadienyl) -bis (2,3,4,5,6 pentafluorophenyl) titanium, bis (methylcyclopenta Dienyl) -bis (2,6-difluorophenyl) titanium, bis (cyclopentadienyl) -bis [2,6-
  • ⁇ ⁇ ⁇ it is preferable to be able to absorb light having a wavelength of 300 to 550 nm, and more preferably to be able to absorb light having a wavelength of 350 to 500 nm.
  • the content of the titanocene photopolymerization initiator (C) is 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, based on 100 parts by mass of the sealant.
  • the sealing agent contains (C) the titanocene-based photopolymerization initiator in the above range, the photocurability of the sealing agent is likely to increase.
  • the light-shielding agent contained in the sealant of the present invention has a pH of less than 7 (specifically, less than 7.0) or a pH of more than 8.0 and a blackness of the sealant of, for example, 2 to 5 There is no particular limitation as long as it is adjustable.
  • the pH of (D) the light-shielding agent is less than 7 (specifically, less than 7.0) or the pH is more than 8.0, the dispersibility of (D) the light-shielding agent in the sealant is excellent as described above. And the curability of the sealant is improved.
  • the pH of the light-shielding agent was determined by diluting and stirring the (D) light-shielding agent 20-fold with pure water, and then measuring the pH of the pure water containing the (D) light-shielding agent with a compact pH meter (B-71X manufactured by HORIBA). It can be obtained by measuring.
  • a compact pH meter B-71X manufactured by HORIBA.
  • the pH of the light-shielding agent is less than 7.0, it is preferably from 1 to 6, more preferably from 1 to 4.
  • the pH of the light-shielding agent (D) exceeds 8.0, the pH is preferably 10.0 or less.
  • Examples of the (D) light-blocking agent satisfying the above-mentioned pH include carbon black, titanium black, vanadium, and inorganic compounds such as iron and copper. Among these, it is preferable to include carbon, and examples thereof include acidic carbon black.
  • the acidic carbon black may be a channel black or an oxidized carbon black.
  • Examples of the method of oxidizing carbon black include air oxidation, nitric acid, mixed gas of nitrogen oxide and air, and oxidation with various oxidizing agents such as ozone.
  • the sealing agent may contain only one type of (D) light-shielding agent, or two or more types. Examples of preferable (D) light-shielding agents also include titanium black.
  • the shape of the light-shielding agent is not particularly limited, and may be a fixed shape such as a sphere, a plate, or a needle, or an irregular shape.
  • the average primary particle diameter of the light-shielding agent (D) is preferably 0.005 to 0.1 ⁇ m, more preferably 0.01 to 0.05 ⁇ m, and more preferably 0.015 to 0.03 ⁇ m. Is more preferable. Average particle diameter It can be measured by a laser diffraction method described in JIS Z8825. The specific surface area can be measured by the BET method described in JIS Z8830.
  • the amount of the (D) light-shielding agent with respect to 100 parts by mass of the sealing agent is not particularly limited as long as the blackness of the sealing agent can be adjusted to, for example, 2 to 5.
  • the amount can be 5 to 46 parts by mass, preferably 7 to 40 parts by mass, and more preferably 10 to 30 parts by mass with respect to the total amount of the sealant.
  • the blackness of the sealing agent tends to fall within a desired range.
  • the amount of the (D) light-shielding agent is excessively large, the (D) light-shielding agent is likely to aggregate, and the photocurability of the sealant is likely to be reduced.
  • the sealant of the present invention contains (E) a thermosetting compound having at least one epoxy group in one molecule.
  • the sealant contains (E) a thermosetting compound, the cured product of the sealant has improved moisture resistance.
  • a resin corresponding to the above-mentioned (B) photocurable resin is not included in (E) the thermosetting compound.
  • the number of epoxy groups contained in the thermosetting compound is preferably two or more, and particularly preferably two.
  • thermosetting compound examples include bisphenol type epoxy resins such as bisphenol A type, bisphenol F type, bisphenol S type, 2,2′-diallylbisphenol A type, bisphenol AD type, and hydrogenated bisphenol type; Diphenyl ether type epoxy resin; phenol novolak type, cresol novolak type, biphenyl novolak type, bisphenol novolak type, naphthol novolak type, trisphenol novolak type, dicyclopentadiene novolak type, etc .; nophenyl type epoxy resin; biphenyl type epoxy resin; naphthyl type epoxy resin Resins; triphenol alkane type epoxy resins such as triphenol methane type, triphenol ethane type, and triphenol propane type; alicyclic epoxy resins.
  • bisphenol type epoxy resins such as bisphenol A type, bisphenol F type, bisphenol S type, 2,2′-diallylbisphenol A type, bisphenol AD type, and hydrogenated bisphenol type
  • Diphenyl ether type epoxy resin phenol
  • bisphenol type epoxy resins such as bisphenol A type and bisphenol F type are preferable.
  • These bisphenol-type epoxy resins have advantages such as lower crystallinity and superior coating stability than diphenyl ether-type epoxy resins and the like.
  • the compound has low solubility and diffusibility in liquid crystal, and not only improves the display characteristics of the obtained liquid crystal display panel, but also increases the moisture resistance of the cured product of the sealant.
  • the thermosetting compound preferably has a weight average molecular weight (Mw) of 300 to 3,000, more preferably 300 to 2,000.
  • Mw weight average molecular weight
  • the weight average molecular weight of the thermosetting compound can be measured, for example, by gel permeation chromatography (GPC) using polystyrene as a standard.
  • the thermosetting compound may be liquid or solid.
  • the softening point is preferably from 40 ° C to 150 ° C.
  • the sealant may contain only one kind of the thermosetting compound (E), or may contain two or more kinds having different kinds and molecular weights.
  • the amount of the thermosetting compound (E) is 5 to 70 parts by mass, preferably 5 to 50 parts by mass, based on 100 parts by mass of the sealant.
  • thermosetting agent The sealant of the present invention contains (F) a thermosetting agent.
  • the (F) thermosetting agent is a compound that contributes to the reaction of the epoxy group contained in the (E) thermosetting compound.
  • the photocurable resin (B) has an epoxy group, it also contributes to the reaction of the epoxy group.
  • thermosetting agents those that do not generate radicals when reacting with an epoxy group are referred to as (F) thermosetting agents.
  • thermosetting agent is not particularly limited, but is preferably a thermal latent curing agent.
  • the thermal latent curing agent is a compound which does not cure the (E) thermosetting compound during storage of the sealant (at room temperature), and contributes to the reaction of the epoxy group of the (E) thermosetting compound by heating, (E) A compound that cures a thermosetting compound.
  • a known compound can be used as the heat latent curing agent, but a heat latent curing agent having a melting point of 50 ° C. or more and 250 ° C. or less is preferable in order to increase the viscosity stability of the sealant. Further, from the viewpoint of curing the resin even at a low thermosetting temperature (about 80 to 100 ° C.), the melting point is more preferably 50 ° C. or more and 200 ° C. or less.
  • Preferred examples of the heat latent curing agent include a dihydrazide heat latent curing agent, an imidazole heat latent curing agent, an amine adduct heat latent curing agent, and a polyamine heat latent curing agent.
  • dihydrazide heat latent curing agents examples include adipic dihydrazide (melting point: 181 ° C.), 1,3-bis (hydrazinocarboethyl) -5-isopropylhydantoin (melting point: 120 ° C.), 7,11-octadecadien Includes -1,18-dicarbohydrazide (melting point 160 ° C.), dodecane diacid dihydrazide (melting point 190 ° C.), sebacic acid dihydrazide (melting point 189 ° C.), and the like.
  • Preferred examples of the imidazole heat latent curing agent include a compound having a structure represented by the following general formula (X).
  • R 1 and R 2 are each independently a hydrogen atom, a lower alkyl group, a lower hydroxyalkyl group, a phenyl group or a benzyl group.
  • R 3 and R 4 are each independently a hydrogen atom, a lower alkyl group or a lower hydroxyalkyl group. At least one of R 1 to R 4 is a lower hydroxyalkyl group. Since the imidazole-based latent heat curing agent having a lower hydroxyalkyl group contains a hydroxyl group, it is difficult to dissolve in a liquid crystal.
  • the lower alkyl group which may be R 1 to R 4 in the above formula (X) is an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, and a propyl group, and is preferably a methyl group or an ethyl group.
  • the lower hydroxyalkyl group is a hydroxyalkyl group having 1 to 4 carbon atoms such as a hydroxymethyl group and a hydroxyethyl group, and is preferably a hydroxymethyl group.
  • the lower hydroxyalkyl group may include a plurality of hydroxyl groups.
  • the number of hydroxyl groups contained in the imidazole-based curing catalyst is not particularly limited, but since the water resistance may decrease when the number of hydroxyl groups is 2 or more, the number of hydroxyl groups is 1 in terms of not reducing water resistance and the like. Preferably, there is.
  • the melting point of the imidazole heat latent curing agent represented by the general formula (X) depends on the heat curing temperature of the sealant, but when the sealant is thermoset at a relatively low temperature (for example, about 80 to 100 ° C.). Is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, still more preferably 60 to 120 ° C., and particularly preferably 80 to 100 ° C. If the melting point of the imidazole heat latent curing agent is too low, the imidazole heat latent curing agent will melt at room temperature. Then, (E) the curing reaction of the thermosetting compound proceeds, and the storage stability of the sealant at room temperature deteriorates.
  • a relatively low temperature for example, about 80 to 100 ° C.
  • the melting point of the imidazole heat latent curing agent can be lowered by, for example, having a structure not containing an aromatic ring.
  • R 2 is preferably a group other than a phenyl group or a benzyl group, that is, a hydrogen atom, a lower alkyl group or a lower hydroxyalkyl group, and a lower hydroxyalkyl group. Is more preferable.
  • Examples of the imidazole heat latent curing agent represented by the general formula (X) include 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-hydroxy Methyl imidazole, 1-benzyl-5-hydroxymethyl imidazole, 1,2-dihydroxyethyl imidazole and the like are included.
  • examples of the imidazole-based heat latent curing agent having a melting point of 150 ° C. or lower include 2-hydroxymethylimidazole.
  • the amine adduct thermal latent curing agent is an additional compound obtained by reacting an amine compound having catalytic activity with an arbitrary compound.
  • the amine is dissociated by heat and activated.
  • Examples of the amine-based compound include compounds having 1, 2, and tertiary amino groups, such as Amicure PN-40 (melting point 110 ° C.), Amicure PN-23 (melting point 100 ° C.), and Amicure PN-31 ( Melting point 115 ° C.), AMICURE PN-24 (melting point 115 ° C.), AMICURE MY-24 (melting point 120 ° C.), AMICURE MY-H (melting point 130 ° C.) (all manufactured by Ajinomoto Fine Techno Co., Ltd.) and the like.
  • Amicure PN-40 melting point 110 ° C.
  • Amicure PN-23 melting point 100 ° C.
  • Amicure PN-31 Melting point 115 ° C.
  • AMICURE PN-24 melting point 115 ° C.
  • AMICURE MY-24 melting point 120 ° C.
  • AMICURE MY-H melting point 130 ° C.
  • the polyamine-based heat latent curing agent is a heat latent curing agent having a polymer structure obtained by reacting an amine with an epoxy, and specific examples thereof include Adeka Hardener EH4339S (softening point of 120 to 130) manufactured by ADEKA Corporation. ° C) and Adeka Hardener EH4357S (softening point 73-83 ° C) manufactured by ADEKA Corporation.
  • thermosetting agent (F) is preferably 5 to 100 parts by mass, more preferably 10 to 100 parts by mass, based on 100 parts by mass of the total of (B) the photocurable resin and (E) the thermosetting compound. It is 50 parts by mass or less. (F) When a thermosetting agent is contained, the thermosetting reaction of the sealing agent easily proceeds sufficiently.
  • the sealant of the present invention may contain components other than those described above. Examples of other components include inorganic fillers and organic fillers, various additives, and the like.
  • the viscosity of the sealant can be adjusted to a desired range, and the strength and linear expansion of a cured product of the sealant can be controlled.
  • the inorganic filler include calcium carbonate, magnesium carbonate, barium sulfate, magnesium sulfate, aluminum silicate, zirconium silicate, iron oxide, titanium oxide, aluminum oxide (alumina), zinc oxide, silicon dioxide, potassium titanate, kaolin, and talc.
  • the sealant may include only one of these, or may include two or more thereof.
  • the shape of the inorganic filler is not particularly limited, and may be any of a fixed shape such as a sphere, a plate, and a needle, or an irregular shape.
  • the inorganic filler preferably has an average primary particle diameter of 1.5 ⁇ m or less, and preferably has a specific surface area of 1 m 2 / g to 500 m 2 / g.
  • the average primary particle diameter of the inorganic filler can be measured by a laser diffraction method described in JIS Z8825.
  • the specific surface area can be measured by the BET method described in JIS Z8830.
  • the amount of the inorganic filler is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, based on 100 parts by mass of the sealant.
  • the sealant contains an organic filler
  • the impact resistance and the like of the sealant are improved.
  • the type of the organic filler is not particularly limited, but the melting point of the sealant is preferably higher than the thermosetting temperature.
  • the softening point of the organic filler is preferably 30 to 120 ° C.
  • organic filler examples include fine particles selected from the group consisting of silicone fine particles, acrylic fine particles, styrene fine particles such as styrene-divinylbenzene copolymer, and polyolefin fine particles.
  • the sealant may contain only one type of organic filler, or may contain two or more types of organic filler.
  • the shape of the organic filler is not particularly limited, and may be, for example, spherical.
  • the average particle size of the organic filler is preferably 0.05 to 5 ⁇ m, more preferably 0.07 to 3 ⁇ m, since the gap of the liquid crystal cell is usually 5 ⁇ m or less.
  • the average particle size of the organic filler can be measured, for example, by a laser diffraction method described in JIS Z8825.
  • the amount of the organic filler is preferably 30 parts by mass or less, more preferably 15 parts by mass or less, based on 100 parts by mass of the sealant.
  • additives examples include a thermal radical polymerization initiator, a coupling agent such as a silane coupling agent, an ion trapping agent, an ion exchange agent, a leveling agent, a pigment, a dye, a plasticizer, a defoaming agent, and the like. Further, a spacer or the like may be blended for adjusting the gap of the liquid crystal display panel. These contents are not particularly limited as long as the objects and effects of the present invention are not impaired.
  • the above-mentioned sealant preferably has a blackness of 2 to 5, more preferably 3 to 4.
  • the blackness of the sealant can be measured as follows.
  • a sealing agent is collected with a spatula, and dropped on a 25 mm ⁇ 45 mm ⁇ 5 mm thick non-alkali glass to form a circle having a diameter of 5 mm. Then, a pair of non-alkali glass is attached so as to overlap with each other and fixed with a jig.
  • the test piece fixed with the jig is irradiated with an ultraviolet ray of 500 mW / cm 2 from an ultraviolet ray irradiation device (manufactured by Ushio Inc.) to cure the sealant. At this time, the illuminance energy of the ultraviolet light is 3.0 J / cm 2 .
  • the viscosity of the sealant at 25 ° C. and 2.5 rpm using an E-type viscometer is preferably 30 to 350 Pa ⁇ s.
  • a liquid crystal sealant having a viscosity in the above range has excellent coating stability.
  • the method for producing the above-mentioned sealant is not particularly limited, and all the components may be mixed, or the components may be mixed twice or more.
  • the mixing method is not particularly limited, but is preferably a method capable of sufficiently dispersing the (D) light-shielding agent, such as a three-roll mill.
  • the liquid crystal display panel is usually a display substrate, a counter substrate to be paired with the display substrate, a frame-shaped sealing member interposed between the display substrate and the counter substrate, a display substrate and the counter substrate. And a liquid crystal layer filled in a space surrounded by the seal member.
  • a cured product of the above-described sealant can be used as a seal member.
  • Both the display substrate and the counter substrate are transparent substrates.
  • the material of the transparent substrate can be glass or plastic such as polycarbonate, polyethylene terephthalate, polyethersulfone, and PMMA.
  • a matrix-like TFT, color filter, black matrix, and the like are arranged on the surface of the display substrate or the counter substrate.
  • An alignment film is further formed on the surface of the display substrate or the counter substrate.
  • the alignment film contains a known organic or inorganic alignment agent.
  • a black matrix and a color filter may be arranged on a display substrate side, a black matrix may be arranged on a display substrate side, and a color filter may be arranged on a counter substrate side.
  • a black matrix and a color filter may be arranged on the substrate side.
  • Such a liquid crystal display panel can be manufactured by the following method. Specifically, 1) a first step of applying the above-mentioned sealant to one substrate to form a liquid crystal seal pattern, and 2) the liquid crystal in a state where the liquid crystal seal pattern made of the sealant is uncured. A second step of dropping liquid crystal on a region surrounded by a seal pattern or a region of the other substrate facing the region surrounded by the liquid crystal seal pattern; 3) forming one substrate and the other substrate , A third step of superimposing via a liquid crystal seal pattern, and 4) a fourth step of curing the sealant.
  • the above-mentioned sealant is applied in a desired pattern.
  • the method for applying the sealant is not particularly limited as long as the sealant can be applied to a desired region, and may be, for example, an application using a dispenser.
  • the liquid crystal seal pattern to be manufactured is appropriately selected according to the type of the liquid crystal display panel and the like, and can be usually formed in a rectangular frame shape or the like.
  • the line width of the sealant in the liquid crystal seal pattern is preferably 300 to 2000 ⁇ m, more preferably 500 to 1500 ⁇ m.
  • Sectional area of the sealing agent is preferably 1000 ⁇ 10000 2, more preferably 1500 ⁇ 5000 ⁇ m 2.
  • liquid crystal is applied in a state where the liquid crystal seal pattern produced in the first step is in an uncured state.
  • the method of dropping the liquid crystal is not particularly limited, and may be a known method.
  • the “state in which the liquid crystal seal pattern is not cured” means a state in which the curing reaction of the sealant has not progressed to the gel point. Therefore, in the second step, the liquid crystal seal pattern may be semi-cured by irradiating or heating the liquid crystal in order to suppress the dissolution of the sealant into the liquid crystal.
  • one substrate and the other substrate are overlapped via a liquid crystal seal pattern.
  • the superposition can be performed by a known method, and is usually performed under a high vacuum.
  • the sealant is cured. It is preferable that the sealing agent is cured by heating (main curing) after being subjected to light curing (temporary curing). By instantly curing the sealant by temporary curing by light irradiation, dissolution in liquid crystal can be suppressed.
  • the sealant of the present invention contains (C) a titanocene-based photopolymerization initiator. Therefore, the irradiation light preferably includes not only ultraviolet light but also light in the visible light region. In this specification, the visible light region refers to a wavelength range from 360 nm to 800 nm.
  • the light source is not particularly limited, but is preferably an LED, a metal halide lamp, a high-pressure mercury lamp, or a low-pressure mercury lamp, and more preferably an LED or a metal halide lamp. From the viewpoint of sufficiently activating the (C) titanocene-based photopolymerization initiator, the wavelength preferably ranges from 360 to 550 nm, and more preferably ranges from 360 to 450 nm.
  • the heating temperature at the time of heating after light irradiation depends on the composition of the sealing agent, but is preferably as low as possible, for example, about 120 ° C., from the viewpoint of reducing deterioration of the liquid crystal.
  • the temperature is more preferably 80 to 120 ° C.
  • the heat curing time is about 1 to 2 hours.
  • the obtained compound was washed 20 times with ultrapure water, and a methacrylic acid-modified bisphenol F-type epoxy resin (95% partially methacrylated) (weight average molecular weight (Mw) 485, hydrogen bonding functional group equivalent 4.0 ⁇ ). 10 ⁇ 3 mol / g).
  • Example 1 As a photocurable resin, 330 parts by mass of a methacrylic acid-modified bisphenol F type epoxy resin obtained in a synthesis example and polyethylene glycol diacrylate (manufactured by Kyoeisha Chemical Co., Ltd .: light acrylate 14EG-A, weight average molecular weight 722, hydrogen bonding) 172 parts by mass of a functional group equivalent (0.9 ⁇ 10 ⁇ 3 mol / g), 6 parts by mass of (A) trimellitic acid (manufactured by Tokyo Chemical Industry Co., Ltd., oxygen atom equivalent 35 g / eq) as an organic acid, and (C) ) 12 parts by mass of a titanocene-based photopolymerization initiator (manufactured by Insight High Technology: IHT-PI 784) and (E) an epoxy resin as a thermosetting compound (manufactured by Mitsubishi Chemical Corporation: jER1004, softening point 97 ° C, weight average
  • Example 2 A sealant was obtained in the same manner as in Example 1 except that the content was changed to the content shown in Table 1.
  • Example 3 A sealant was used in the same manner as in Example 1 except that carbon (Mitsubishi Chemical Corporation: # 2600, pH 6.5, particle size: 13 nm) was used instead of carbon (MA-100R) as a light-shielding agent. I got
  • Example 4 Sealing agent in the same manner as in Example 1, except that titanium black (13M, pH 8.8, particle diameter 97 nm, manufactured by Mitsubishi Materials Corporation) was used instead of carbon (MA-100R) as a light-shielding agent. I got
  • Example 5 A sealant was obtained in the same manner as in Example 1, except that phenylphosphonic acid (oxygen atom equivalent: 53 g / eq) was used as the organic acid instead of trimellitic acid.
  • Example 1 A sealant was obtained in the same manner as in Example 1, except that trimellitic acid was not added, and t-butyl peroxypivalate (manufactured by Mitsubishi Chemical: Luperox 11) was added as a thermal radical generator.
  • the test piece cured by light was heated in an oven at 120 ° C. for 60 minutes to obtain a sample for measuring blackness.
  • the seal pattern was a circle having a diameter of 5 mm.
  • a pair of non-alkali glass was stuck together so as to overlap, and fixed with a jig.
  • the test piece fixed with the jig was irradiated with ultraviolet light (wavelength 365 nm) of 500 mW / cm 2 from an ultraviolet irradiation device (manufactured by Ushio Inc.) to cure the sealant.
  • the illuminance energy of the ultraviolet light was 3.0 J / cm 2 .
  • the test piece cured by light was heated in an oven at 120 ° C. for 60 minutes to obtain a sample for dispersibility evaluation. This sample was observed with a microscope, and the number of foreign substances (aggregates of light-shielding agents) present in a visual field of 2 mm ⁇ 2 mm was counted.
  • ⁇ No foreign matter
  • ⁇ Less than 10 foreign matters
  • ⁇ 10 or more foreign matters
  • a liquid crystal material manufactured by MLC-7021-00 Merck Co., Ltd.
  • a dispenser After bonding the glass substrates to be paired under reduced pressure, they were opened to the atmosphere and bonded. Thereafter, light of 1000 mJ / cm 2 (light calibrated by a sensor having a wavelength of 365 nm) is irradiated in a state where the black matrix is covered with a substrate formed with a line / space of 300 ⁇ m / 100 ⁇ m so as to cover the lower half of the main seal. And further heated at 120 ° C. for 1 hour.
  • the liquid crystal display panel after the hardening treatment of the light shielding sealant was evaluated as follows. :: No liquid crystal leakage occurred ⁇ : No liquid crystal leakage occurred, but liquid crystal was inserted into sealant ⁇ : Liquid crystal leakage occurred
  • the 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 having a diameter of 1 mm. Then, they were mounted on a pair of non-alkali glass in a seal pattern and fixed with a jig.
  • the test piece fixed by the jig was irradiated with an ultraviolet ray (wavelength: 365 nm) of 500 mW / cm 2 by an ultraviolet ray irradiation device (manufactured by Ushio Inc.) to cure the light-shielding sealant.
  • the illuminance energy of the ultraviolet rays was 3.0 J / cm 2 .
  • the test piece obtained by curing the light-shielding sealant with light was heated at 120 ° C. for 60 minutes using an oven to obtain a sample for measuring the adhesive strength.
  • the tensile speed was set to 2 mm / min, and the cured light-shielding sealant was peeled off in a direction parallel to the glass bottom surface to measure the tensile strength in a plane.
  • the adhesive strength was evaluated in the following four stages according to the magnitude of the plane tensile strength.
  • ⁇ Tensile strength of 15 MPa or more
  • ⁇ Tensile strength of 10 MPa or more and less than 15 MPa
  • the stability was evaluated as follows. ((Excellent): The ratio of the viscosity after one week to the initial viscosity (increase rate) was 1.2 times or less. ⁇ (somewhat excellent): The ratio of the viscosity after one week to the initial viscosity (increase rate) was 1 X: less than 1.5 times ⁇ (poor): The ratio of the viscosity after one week to the initial viscosity (increase rate) exceeded 1.5 times
  • the sealant of the present invention has high photocurability and can reliably seal between substrates of a liquid crystal display panel without causing contamination of liquid crystal. Therefore, a highly reliable display panel can be manufactured, which is suitable for manufacturing various liquid crystal display panels.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

La présente invention concerne un agent d'étanchéité bloquant la lumière pour des procédés de dépôt de cristaux liquides, qui présente une bonne aptitude au photodurcissement et est capable d'étanchéfier de manière fiable l'espace entre des substrats d'un panneau d'affichage à cristaux liquides sans engendrer de contamination des cristaux liquides ; et un procédé de production d'un panneau d'affichage à cristaux liquides qui utilise cet agent d'étanchéité bloquant la lumière pour des procédés de dépôt de cristaux liquides. L'agent d'étanchéité bloquant la lumière pour des procédés de dépôt de cristaux liquides selon la présente invention, contient : (A) un acide organique, (B) une résine photodurcissable qui comporte au moins une liaison double éthyléniquement insaturée dans chaque molécule, (C) un initiateur de photopolymérisation à base de titanocène, (D) un agent bloquant la lumière dont le pH est inférieur à 7,0 ou supérieur à 8,0, (E) un composé thermodurcissable qui comporte au moins un groupe époxy dans chaque molécule (à l'exclusion de la résine photodurcissable (B)), et (F) un agent de durcissement thermique. Par rapport à cet agent d'étanchéité bloquant la lumière destiné à des procédés de dépôt de cristaux liquides, l'équivalent d'atomes d'oxygène de l'acide organique (A) est compris entre 23 g/Eq et 75 g/Eq (inclus).
PCT/JP2019/028313 2018-07-24 2019-07-18 Agent d'étanchéité bloquant la lumière pour procédés de dépôt de cristaux liquides, et procédé de production d'un panneau d'affichage à cristaux liquides utilisant cet agent WO2020022188A1 (fr)

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KR1020207037783A KR102509153B1 (ko) 2018-07-24 2019-07-18 액정 적하 공법용 차광 실링제, 및 이것을 이용한 액정 표시 패널의 제조 방법
JP2020532342A JP7181936B2 (ja) 2018-07-24 2019-07-18 液晶滴下工法用遮光シール剤、およびこれを用いた液晶表示パネルの製造方法

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