CN114621719A - Liquid crystal sealant for liquid crystal dropping method - Google Patents
Liquid crystal sealant for liquid crystal dropping method Download PDFInfo
- Publication number
- CN114621719A CN114621719A CN202111487869.XA CN202111487869A CN114621719A CN 114621719 A CN114621719 A CN 114621719A CN 202111487869 A CN202111487869 A CN 202111487869A CN 114621719 A CN114621719 A CN 114621719A
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- CN
- China
- Prior art keywords
- liquid crystal
- sealing agent
- dropping method
- crystal sealing
- meth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 208
- 238000000034 method Methods 0.000 title claims abstract description 61
- 239000000565 sealant Substances 0.000 title claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 124
- 238000007789 sealing Methods 0.000 claims abstract description 105
- 239000000945 filler Substances 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 79
- 239000007870 radical polymerization initiator Substances 0.000 claims description 29
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 16
- 230000035699 permeability Effects 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
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- 125000003118 aryl group Chemical group 0.000 claims description 7
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- MPQVYFJXQMBTHQ-UHFFFAOYSA-N triethyl-(1,1,2,2-tetraphenyl-2-triethylsilyloxyethoxy)silane Chemical compound C(C)[Si](OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](CC)(CC)CC)(C1=CC=CC=C1)C1=CC=CC=C1)(CC)CC MPQVYFJXQMBTHQ-UHFFFAOYSA-N 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1341—Filling or closing of cells
- G02F1/13415—Drop filling process
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
Abstract
The present invention relates to a liquid crystal sealing agent for a liquid crystal dropping method. The present invention relates to a liquid crystal sealing agent which can be applied to a flexible display and a curved display. More specifically, the present invention provides a liquid crystal sealing agent for a liquid crystal dropping method having excellent crushabilityAnd a liquid crystal display cell sealed with a cured product thereof. A liquid crystal sealing agent for liquid crystal dropping method, which contains a curable compound, a filler and a thermal curing agent, wherein the filler has an average specific surface area of 10.0m2The viscosity of the liquid crystal sealing agent for the liquid crystal dropping method is more than or equal to g, and is less than 500 Pa-s measured by using an E-type viscometer at the conditions of 25 ℃ and 5 rpm.
Description
Technical Field
The present invention relates to a liquid crystal sealing agent for a liquid crystal dropping method and a liquid crystal display cell encapsulated with a cured product thereof.
Background
In recent years, a liquid crystal dropping method having high mass productivity has been widely used as a method for manufacturing a liquid crystal display unit. The liquid crystal dropping method is as follows: liquid crystal is dropped inside a liquid crystal sealing agent formed on one substrate, the other substrate is attached under vacuum, the liquid crystal sealing agent is crushed to a predetermined gap (inter-substrate distance) by atmospheric pressure by opening to the atmosphere, and then the liquid crystal sealing agent is uv-cured and heat-cured to manufacture a liquid crystal display cell.
However, in recent years, due to the effect of increasing the size of the liquid crystal display unit and narrowing the gap, there have been problems such that the liquid crystal sealing agent cannot be crushed to a predetermined gap. Thus, the liquid crystal display cannot exhibit desired display characteristics because the gap is different between the central portion and the peripheral portion.
In addition, recently, a display having a curved shape or a display having high flexibility is developed and manufactured as a product, and a flexible substrate such as a plastic film is used as a substrate used for such a display instead of a conventional rigid substrate such as glass (patent document 1). Such a flexible substrate cannot apply a uniform atmospheric pressure to the entire substrate when forming the gap, and therefore, is one of the main causes of gap defects.
Further, the introduction of a flexible substrate has also gradually required the liquid crystal sealing agent to have a property of following the warpage of the substrate and the like, that is, a property of being flexible even after curing. A liquid crystal sealing agent excellent in flexibility is also advantageous in adhesive strength. For example, peeling and material breakage due to impact can be reduced. From this viewpoint, the demand for imparting flexibility to the liquid crystal sealing agent is also increasing.
On the other hand, in order to improve the flexibility of the cured product, it is an effective means to reduce the crosslinking density of the cured product. However, in general, moisture permeability is deteriorated when the crosslinking density is decreased. This is believed to be due to moisture ingress from loose parts of the network. Therefore, in order to ensure low moisture permeability, it is necessary to achieve contradictory characteristics such as improvement of flexibility without lowering the crosslinking density or no deterioration of moisture permeability even though the crosslinking density is lowered.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2012 and 238005
Disclosure of Invention
Problems to be solved by the invention
The present invention relates to a liquid crystal sealing agent which can be applied to a flexible display and a curved display. More specifically, the present invention aims to provide a liquid crystal sealant for liquid crystal dropping method having excellent crushability (つぶれ property) and a liquid crystal display cell sealed with a cured product thereof.
Means for solving the problems
The present inventors have conducted extensive studies and found that a liquid crystal sealing agent for a specific liquid crystal dropping method is excellent in crushability, and thus have completed the present invention.
In the present specification, "(meth) acrylate" means "acrylate" and/or "methacrylate".
That is, the present invention relates to the following [1] to [11 ].
[1]
A liquid crystal sealing agent for a liquid crystal dropping method comprising a curable compound, a filler and a heat-curing agent, wherein,
the average specific surface area of the filler was 10.0m2A/g or more, and
the viscosity of the liquid crystal sealing agent for liquid crystal dropping method measured by using an E-type viscometer at 25 ℃ and 5rpm is less than 500 pas.
[2]
The liquid crystal sealing agent for liquid crystal dropping method according to the above item [1], wherein a cured product of the liquid crystal sealing agent for liquid crystal dropping method has an elastic modulus at 25 ℃ of 2500MPa or less as measured by a Tensilon universal tester.
[3]
As in the above item [1]Or [ 2]]The liquid crystal sealant for liquid crystal dropping method, wherein the cured product of the liquid crystal sealant for liquid crystal dropping method has a film thickness of 300 μm, and has a moisture permeability of 100g/m measured at 60 ℃ and 90%224h or less.
[4]
The liquid crystal sealing agent for liquid crystal dropping method as described in any one of the above items [1] to [3], wherein the content of the filler is 5 parts by mass or more and less than 50 parts by mass with respect to 100 parts by mass of the curable compound.
[5]
The liquid crystal sealing agent for liquid crystal dropping method according to any one of the above items [1] to [4], wherein the liquid crystal sealing agent for liquid crystal dropping method contains an organic filler and an inorganic filler as the filler, and the inorganic filler is an inorganic filler subjected to hydrophobic surface treatment.
[6]
The liquid crystal sealing agent for liquid crystal dropping method according to any one of the above items [1] to [5], wherein the liquid crystal sealing agent for liquid crystal dropping method contains urethane (meth) acrylate as the curable compound.
[7]
The liquid crystal sealant for liquid crystal dropping method as described in the aforementioned item [6], wherein the urethane (meth) acrylate is obtained by reacting (a) a polyol having an aromatic ring, (b) an organic polyisocyanate, and (c) a hydroxyl group-containing (meth) acrylate.
[8]
The liquid crystal sealing agent for liquid crystal dropping method according to any one of the above items [1] to [7], wherein the liquid crystal sealing agent for liquid crystal dropping method further contains a thermal radical polymerization initiator.
[9]
The liquid crystal sealant for liquid crystal dropping method as described in the aforementioned item [8], wherein the thermal radical polymerization initiator is a thermal radical polymerization initiator which does not contain an oxygen-oxygen bond (-O-O-) and a nitrogen-nitrogen bond (-N ═ N-) in a molecule.
[10]
The liquid crystal sealing agent for liquid crystal dropping method according to any one of the above items [1] to [9], wherein the liquid crystal sealing agent for liquid crystal dropping method further contains a photo radical polymerization initiator.
[11]
A liquid crystal display unit, wherein the liquid crystal display unit is sealed with a liquid crystal sealant by the liquid crystal dropping method according to any one of the preceding items [1] to [10 ].
Effects of the invention
The present invention can provide a liquid crystal sealing agent having excellent crushability in a liquid crystal dropping method and a liquid crystal display cell sealed with a cured product thereof.
Drawings
Fig. 1 is a graph showing the relationship between the dark line of the interference fringe and the average specific surface area of the liquid crystal sealing agent of the example and the comparative example.
Detailed Description
The liquid crystal sealing agent for the liquid crystal dropping method comprises a curable compound, a filler and a thermal curing agent, wherein the average specific surface area of the filler is 10.0m2The viscosity of the liquid crystal sealing agent for the liquid crystal dropping method is more than or equal to g, and is less than 500 Pa-s measured by using an E-type viscometer at the conditions of 25 ℃ and 5 rpm.
The average specific surface area of the filler can be measured by a BET method or the like by mixing all the fillers contained in the liquid crystal sealing agent, or can be calculated from the specific surface area of each filler contained in the liquid crystal sealing agent. In examples of the present invention described later, the average specific surface area of the filler is calculated based on the following formula (1).
Average specific surface area (m)2(ii) per gram [ (specific surface area (m) of each filler)2(g)) × (content of each filler)]Sum of (1)/(total filler)Content) … … formula (1)
The method for measuring the specific surface area of the filler is not particularly limited, and the specific surface area can be measured by a BET method in general. In addition, if the product is a commercially available product, the method is not limited to the above method, and values explicitly described in the product catalog of each company may be used.
Specifically, the above formula (1) is described, for example, with 100 parts by mass of the curable compound and the filler A (specific surface area: 7.0 m)2(g) 5 parts by mass, filler B (specific surface area: 2.0m2(g) 10 parts by mass of a liquid crystal sealing agent having an average specific surface area of [ (7.0X 5) + (2.0X 10)]/15＝3.0(m2/g)。
The liquid crystal sealing agent of the present invention has excellent crushability. That is, the liquid crystal sealing agent of the present invention is easily crushed to a desired gap when the upper and lower substrates are bonded under vacuum and opened to the atmosphere.
The present inventors have conducted a bonding test on various liquid crystal sealing agents and found that there is a certain relationship between the crushability of the liquid crystal sealing agent and the average specific surface area of the filler. This is because a filler having a small specific surface area tends to have a large particle diameter and is difficult to crush into a predetermined gap. Therefore, the average specific surface area of the filler is preferably 10.0m2A value of at least g, more preferably 14.0m2A specific ratio of 17.0m to g2More than g. The preferable upper limit is not particularly limited, but the average specific surface area of the filler is preferably 200.0m in consideration of kneading with a liquid crystal sealing agent2A value of 100.0m or less per gram2The ratio of the carbon atoms to the carbon atoms is less than g.
The inventors of the present invention have found that the crushing property is also affected by the viscosity of the liquid crystal sealing agent. This is considered to be because the liquid crystal sealing agent having a high viscosity becomes strong against the atmospheric pressure when the gap is formed. The viscosity of the liquid crystal sealing agent measured with an E-type viscometer at 25 ℃ and 5rpm is preferably less than 500 pas, more preferably less than 450 pas, and particularly preferably less than 400 pas. The preferable lower limit is not particularly limited, but is preferably 100Pa · s or more, and more preferably 200Pa · s or more in consideration of liquid crystal insertion resistance.
The viscosity measurement in the present invention is performed under the following conditions.
A liquid crystal sealing agent (0.15 mL) was added to a measuring cup of an E-type viscometer (RE 105, manufactured by Toyobo industries Co., Ltd.). The sample was preheated at 25 ℃ for 120 seconds under a cone angle of 3 ℃ X R7.7, and then the value after rotating at 5rpm for 180 seconds was measured.
The viscosity at 0.5rpm was measured for a sample exceeding the measurement limit of 5rpm (600Pa · s). The results are shown in tables 1 and 2.
The gap after bonding the substrates can be measured by an optical device, a height difference meter, or the like, but in the present invention, the dark lines of interference fringes after bonding the substrates are observed as follows. The obtained liquid crystal sealing agent was applied in a quadrangular shape on a glass substrate with an alignment film, and liquid crystal was dropped to the inside thereof. On the other glass substrate with an alignment film, 5 μm in-plane spacers were scattered and thermally fixed, and both substrates were bonded in vacuum using a bonding apparatus. The liquid crystal sealing agent was opened to the atmosphere for 3 minutes and then cured by ultraviolet rays or heat to prepare a liquid crystal cell for evaluation. Next, the evaluation liquid crystal cell was observed with an interference fringe inspection lamp, and the number of interference fringe dark lines outside the liquid crystal sealant was measured. In this case, the number of interference fringe dark lines is preferably 2 or less. Since the liquid crystal sealing agent having excellent crushability is crushed to the height of the in-plane spacer by atmospheric pressure, the glass substrate is flat, and the number of interference fringe dark lines is 2 or less. However, since a liquid crystal sealing agent having poor crushability cannot be crushed to the height of the in-plane spacer, a large number of interference fringes and dark lines are observed in the liquid crystal sealing agent, unlike the gap around the liquid crystal sealing agent.
The liquid crystal sealing agent of the present invention preferably has high flexibility and low moisture permeability. Flexibility can be evaluated by the modulus of elasticity. The measured specimen was irradiated at 3000mJ/cm in accordance with the irradiation of a universal tester (manufactured by Shimadzu corporation: Autograph AG-Xplus500N)2The elastic modulus of a cured product having a thickness of 100 μm obtained by curing ultraviolet light (measurement wavelength: 365nm) at 120 ℃ for 60 minutes at room temperature (25 ℃) is preferably 100MPa or more and 3000MPa or less, more preferably 300MPa or more and 2500MPa or moreParticularly, it is preferably 400MPa or more and 2000MPa or less. A liquid crystal sealing agent having an elastic modulus within the above range can follow the stress applied to the display, and is therefore preferable.
The water vapor permeability is determined by irradiating 3000mJ/cm2(measurement wavelength: 365nm) ultraviolet ray, 120 degrees C, 60 minutes under conditions of curing and 300 u m thickness of the cured material of moisture permeability at 60 degrees C, 90% conditions are preferably 100g/m224h or less, more preferably 80g/m224h or less, particularly preferably 70g/m224h or less.
[ curable Compound ]
The liquid crystal sealing agent of the present invention contains a curable compound. The curable compound is not particularly limited as long as it is a compound curable by light, heat, or the like, but is preferably a compound having a (meth) acryloyl group or an epoxy group, and particularly preferably an epoxy (meth) acrylate, a urethane (meth) acrylate, or a polybutadiene compound.
[ (meth) acrylic acid ester ]
Specific examples of the (meth) acrylic acid ester include: n-acryloyloxyethylhexahydrophthalimide, acryloylmorpholine, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexane-1, 4-dimethanol mono (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, phenoxyethyl (meth) acrylate, phenylpolyethoxy (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, orthophenylphenol monoethoxy (meth) acrylate, orthophenylphenol polyethoxy (meth) acrylate, p-cumylphenoxyethyl (meth) acrylate, isobornyl (meth) acrylate, tribromophenoxyethyl (meth) acrylate, tetrahydrodicyclopentadiene (meth) acrylate, dihydrodicyclopentadiene (meth) acrylate, phenyldicyclopentadiene (meth) acrylate, and the like, Dihydrodicyclopentadiene oxyethyl (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, bisphenol A polyethoxy di (meth) acrylate, bisphenol A polypropoxy (meth) acrylate, bisphenol F polyethoxy di (meth) acrylate, ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, tris (acryloyloxyethyl) isocyanurate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, tripentaerythritol penta (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, bisphenol A polypropylenoxide (meth) acrylate, bisphenol F polyethoxy di (meth) acrylate, ethylene glycol tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol hexa (meth) acrylate, and mixtures thereof, Trimethylolpropane tri (meth) acrylate, trimethylolpropane polyethoxy tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, diacrylate of an ester of neopentyl glycol and hydroxypivalic acid or diacrylate of an epsilon-caprolactone adduct of an ester of neopentyl glycol and hydroxypivalic acid. Preferred examples include: o-phenylphenol monoethoxy (meth) acrylate, o-phenylphenol polyethoxy (meth) acrylate.
[ epoxy (meth) acrylate ]
The epoxy (meth) acrylate can be obtained by a reaction of an epoxy resin with (meth) acrylic acid by a known method. The epoxy resin as a raw material is not particularly limited, but is preferably a bifunctional or higher epoxy resin, and examples thereof include: dimer acid-modified epoxy resins, resorcinol diglycidyl ether, bisphenol a-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, phenol novolac-type epoxy resins, cresol novolac-type epoxy resins, bisphenol a novolac-type epoxy resins, bisphenol F novolac-type epoxy resins, alicyclic epoxy resins, aliphatic chain epoxy resins, glycidyl ester-type epoxy resins, glycidyl amine-type epoxy resins, hydantoin-type epoxy resins, isocyanurate-type epoxy resins, phenol novolac-type epoxy resins having a triphenylolmethane skeleton, and diglycidyl etherates of bifunctional phenols such as catechol and resorcinol, diglycidyl etherates of bifunctional alcohols, halides and hydrogenation products thereof. Among them, bisphenol a type epoxy resins and resorcinol diglycidyl ether are preferable from the viewpoint of liquid crystal contamination. The ratio of the epoxy group to the (meth) acryloyl group is not limited, and is appropriately selected from the viewpoint of process suitability.
A partially epoxy (meth) acrylate obtained by acrylating a part of the epoxy group can be suitably used. The proportion of acrylation in this case is preferably from about 30% to about 70%.
[ urethane (meth) acrylate ]
The urethane (meth) acrylate has a soft skeleton specific to a urethane structure, and thus a cured product has characteristics of being soft and low in moisture permeability and also can follow bending of a flexible display, and therefore, is preferably used as a curable compound, and a urethane (meth) acrylate having a polyester structure is more preferred.
The urethane (meth) acrylate can be synthesized by a conventional method by reacting (a) a polyol, (b) an organic polyisocyanate, and (c) a hydroxyl group-containing (meth) acrylate, and if necessary, using a catalyst such as a tin compound.
In the synthesis of urethane (meth) acrylate, 1.1 to 2.0 equivalents of isocyanate group in the component (b) are preferably reacted with 1 equivalent of hydroxyl group in the component (a), and particularly 1.3 to 2.0 equivalents of isocyanate group in the component (b) are preferably reacted with each other. The reaction temperature is preferably from room temperature (25 ℃) to 100 ℃.
It is preferable that 0.95 to 1.1 equivalents of the hydroxyl group in the component (c) is reacted with respect to 1 equivalent of the isocyanate group in the reaction product of the component (a) and the component (b). The reaction temperature is preferably from room temperature (25 ℃) to 100 ℃.
Specific examples of the polyol (a) include: tricyclodecanedimethanol, hydrogenated polybutadiene polyol, dimer diol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1, 4-butanediol, neopentyl glycol, 1, 6-hexanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 12-dodecanediol, 1, 14-tetradecanediol, 1, 16-hexadecanediol, 1, 18-octadecanediol, 1, 20-eicosanediol, 1-methyl-1, 8-octanediol, 2-methyl-1, 8-octanediol, 3-methyl-1, 5-pentanediol, 2, 4-diethyl-1, 5-pentanediol, cyclohexane-1, 4-dimethanol, propylene glycol, 1, 4-decanediol, 1, 4-dimethanol, 1, 4-decanediol, 1, 14-tetradecanediol, 1, 16-hexadecanediol, 1, 18-octadecanediol, 1, 20-octanediol, 1, 8-octanediol, 1, 2-methyl-1, 8-octanediol, 2-octanediol, 3-decanediol, 2, 4-dimethanol, 1, 4-diol, 4-dimethyl, and mixtures thereof, And diols (a-1) such as polyethylene glycol, polypropylene glycol, bisphenol A poly (n.apprxeq.2 to 20) ethoxy glycol, bisphenol A poly (n.apprxeq.2 to 20) propoxy glycol, and polyester polyols (a-2) which are reaction products of these diols (a-1) with dibasic acids or anhydrides thereof (for example, succinic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, isophthalic acid, terephthalic acid, phthalic acid, or anhydrides thereof). Polyester polyols and polyols having aromatic rings are preferred, and polyester polyols having aromatic rings are particularly preferred. Examples of the aromatic ring include: aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, phenanthroline ring, etc.; an aromatic heterocyclic ring such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, or a benzothiazole ring, and a benzene ring or a naphthalene ring is preferable.
The component (a) may be used alone or in combination of two or more.
Specific examples of (b) the organic polyisocyanate include: toluene diisocyanate, isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, xylylene diisocyanate, 4 '-diphenylmethane diisocyanate, 4' -dicyclohexylmethane diisocyanate, xylylene diisocyanate, 1, 3-bis (isocyanatomethyl) cyclohexane, trimethylhexamethylene diisocyanate, dimer acid diisocyanate, 1, 5-naphthalene diisocyanate, 3 '-dimethyl-4, 4' -diphenylene diisocyanate, and the like. Preferred examples include: toluene diisocyanate, isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate.
Specific examples of (c) the hydroxyl group-containing (meth) acrylate include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 1, 4-butanediol (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, pentaerythritol tri (meth) acrylate, an epsilon-caprolactone adduct of 2-hydroxyethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, and the like. Preferred examples include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and polyethylene glycol mono (meth) acrylate.
The lower limit of the weight average molecular weight of the urethane (meth) acrylate in terms of polystyrene in GPC is preferably 1000 or more, more preferably 2000 or more, particularly preferably 3000 or more, and most preferably 4000 or more. The upper limit is preferably 10000 or less, more preferably 8000 or less, particularly preferably 7000 or less, and most preferably 6000 or less. When the weight average molecular weight of the urethane (meth) acrylate is in the above range, the viscosity of the liquid crystal sealing agent is in an appropriate range while maintaining good flexibility and moisture permeability.
[ epoxy resin ]
In an embodiment of the present invention, it is also preferable that the curable compound contains an epoxy resin.
The epoxy resin is not particularly limited, but is preferably a bifunctional or higher epoxy resin, and examples thereof include: dimer acid-modified epoxy resins, resorcinol diglycidyl ether, bisphenol a-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, phenol novolac-type epoxy resins, cresol novolac-type epoxy resins, bisphenol a novolac-type epoxy resins, bisphenol F novolac-type epoxy resins, alicyclic epoxy resins, aliphatic chain epoxy resins, glycidyl ester-type epoxy resins, glycidyl amine-type epoxy resins, hydantoin-type epoxy resins, isocyanurate-type epoxy resins, phenol novolac-type epoxy resins having a triphenylolmethane skeleton, and diglycidyl etherates of bifunctional phenols such as catechol and resorcinol, diglycidyl etherates of bifunctional alcohols, halides and hydrogenated products thereof. Among them, bisphenol a type epoxy resins and resorcinol diglycidyl ether are preferable from the viewpoint of liquid crystal contamination.
[ polybutadiene Compound ]
Further, it is also a preferable embodiment of the present invention to use a polybutadiene compound having an epoxy group or a (meth) acryloyl group as the curable compound. The polybutadiene compound having an epoxy group is commercially available as JP-100 and JP-200, manufactured by Nippon Kabushiki Kaisha, for example. The polybutadiene compound having a (meth) acryloyl group is commercially available, for example, as TEAI-1000 and TE-2000 manufactured by Nippon Caoda corporation.
From the viewpoint of reducing liquid crystal contamination, the lower limit of the number average molecular weight of these polybutadiene compounds is preferably 500, more preferably 750, and particularly preferably 1000. From the viewpoint of handleability, the upper limit of the number average molecular weight of the polybutadiene compound is preferably 10000, more preferably 8000, and particularly preferably 6000.
The curable compound may be used alone or in combination of two or more. In the liquid crystal sealing agent of the present invention, when a curable compound is used, the content of the curable compound in the total amount of the liquid crystal sealing agent is preferably 10 to 95% by mass, and more preferably 20 to 90% by mass.
[ Filler ]
The liquid crystal sealing agent of the present invention contains a filler. The specific surface area of the filler is preferably 10.0m from the viewpoint of the crushability of the liquid crystal sealing agent2A value of at least 15.0 m/g, more preferably2A specific ratio of 18.0m or more per gram2More than g. The shape of the filler is preferably spherical. Since the filler is spherical, the fluidity of the liquid crystal sealing agent is improved, and the crushing property is improved. In addition, the surface of the filler is preferably subjected to hydrophobic surface treatment. By performing the hydrophobic surface treatment, the filler is easily compatible with the curable compound, and the fluidity of the liquid crystal sealing agent is improved, so that the crushing property is improved. Examples of the hydrophobic surface treatment include methylation treatment and various coupling treatments.
The particle size of the filler is preferably 0.01 to 1.0. mu.m, more preferably 0.05 to 0.7. mu.m, and particularly preferably 0.05 to 0.3. mu.m. The filler content is preferably not less than 1 part by mass and less than 60 parts by mass, more preferably not less than 5 parts by mass and less than 50 parts by mass, particularly preferably not less than 10 parts by mass and less than 30 parts by mass, and most preferably not less than 10 parts by mass and less than 20 parts by mass, relative to 100 parts by mass of the curable compound. The amount of the filler having a particle diameter of 0.5 μm or more is preferably less than 20 parts by mass, and more preferably less than 10 parts by mass, based on 100 parts by mass of the curable compound.
The filler contained in the liquid crystal sealing agent of the present invention may contain either an organic filler or an inorganic filler, or both of them.
Examples of the organic filler include: urethane polymer fine particles, acrylic polymer fine particles, styrene-olefin copolymer fine particles, and silicone fine particles. The silicone microparticles are preferably KMP-594, KMP-597, KMP-598 (manufactured by shin-Etsu chemical industries), or TorayfilRTME-5500, 9701, EP-2001 (manufactured by Toray Corning Co., Ltd.), JB-800T, HB-800BK (manufactured by Kokusho Kogyo Co., Ltd.) as the urethane polymer fine particles, and Rabalon as the styrene polymer fine particlesRTMT320C, T331C, SJ4400, SJ5400, SJ6400, SJ4300C, SJ5300C and SJ6300C (manufactured by Mitsubishi chemical), and as the fine particles of the styrene-olefin copolymer, Septon is preferableRTMSEPS2004、SEPS2063。
These organic fillers may be used alone or in combination of two or more. In addition, two or more kinds of core-shell structures can be used. Among them, urethane polymer microparticles, acrylic polymer microparticles, styrene polymer microparticles, and styrene-olefin copolymer microparticles are preferable, and acrylic polymer microparticles are particularly preferable.
When the acrylic polymer fine particles are used, an acrylic rubber having a core-shell structure containing two types of acrylic rubbers is preferable, and an acrylic rubber having a core-shell structure containing n-butyl acrylate as a core layer and methyl methacrylate as a shell layer is particularly preferable. As ZefiacRTMF-351S is sold by Ack industries, Inc.
Further, examples of the silicone fine particles include: organopolysiloxane crosslinked powder, linear dimethylpolysiloxane crosslinked powder, and the like. Further, as the composite silicone rubber, there can be mentioned a composite silicone rubber obtained by coating the surface of the above-mentioned silicone rubber with a silicone resin (for example, a polyorganosilsesquioxane resin). Among these fine particles, silicone rubber as a linear dimethylpolysiloxane crosslinked powder or composite silicone rubber fine particles of a linear dimethylpolysiloxane crosslinked powder coated with a silicone resin are particularly preferable. These organic fillers may be used alone or in combination of two or more.
As the inorganic filler, there may be mentioned: silica, silicon carbide, silicon nitride, boron nitride, calcium carbonate, magnesium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, magnesium oxide, zirconium oxide, aluminum hydroxide, magnesium hydroxide, calcium silicate, aluminum silicate, lithium aluminum silicate, zirconium silicate, barium titanate, glass fiber, carbon fiber, molybdenum disulfide, asbestos, and the like, and preferable examples thereof include: fused silica, crystalline silica, silicon nitride, boron nitride, calcium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, aluminum hydroxide, calcium silicate, aluminum silicate, preferably silica, alumina, talc. These inorganic fillers may be used in combination of two or more.
[ Heat curing agent ]
The liquid crystal sealing agent of the present invention contains a thermosetting agent.
Examples of the thermosetting agent include: a compound having a carboxyl group bonded to an aromatic ring in the molecule, a polyamine, a polyphenol, an organic acid hydrazide, and the like. But are not limited to these. Examples thereof include: aromatic hydrazides include terephthalic acid dihydrazide, isophthalic acid dihydrazide, 2, 6-naphthalenedicarboxylic acid dihydrazide, 2, 6-pyridinedicarboxylic acid dihydrazide, 1,2, 4-benzenetricarboxylic acid trihydrazide, 1,4,5, 8-naphthalenetetracarboxylic acid tetrahydrazide, pyromellitic acid tetrahydrazide, and the like. In addition, in the case of the aliphatic hydrazide, for example, there are mentioned: formyl hydrazine, acetyl hydrazine, propionyl hydrazide, oxalic dihydrazide, malonic dihydrazide, succinic dihydrazide, glutaric dihydrazide, adipic dihydrazide, pimelic dihydrazide, sebacic dihydrazide, 1, 4-cyclohexanedihydrazide, tartaric dihydrazide, malic dihydrazide, iminodiacetic dihydrazide, N' -hexamethylenebis semicarbazide, citric trihydrazide, nitrilotriacetic acid trihydrazide, cyclohexanetricarboxylic trihydrazide, 1, 3-bis (hydrazinocarbonylethyl) -5-isopropylhydantoin and the like dihydrazide having a hydantoin skeleton, preferably a valine hydantoin skeleton (a skeleton in which a carbon atom of the hydantoin ring is replaced with an isopropyl group), tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (1-hydrazinocarbonylethyl) isocyanurate, Tris (3-hydrazinocarbonylpropyl) isocyanurate, bis (2-hydrazinocarbonylethyl) isocyanurate, and the like. From the viewpoint of the balance of curing reactivity and latency, isophthalic dihydrazide, malonic dihydrazide, adipic dihydrazide, tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (1-hydrazinocarbonylethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (3-hydrazinocarbonylpropyl) isocyanurate are preferable, and tris (2-hydrazinocarbonylethyl) isocyanurate is particularly preferable.
[ curing accelerators ]
The liquid crystal sealing agent of the present invention can further improve the reactivity by adding a curing accelerator. Examples of the curing accelerator include organic acids and imidazoles.
Examples of the organic acid include organic carboxylic acids and organic phosphoric acids, but organic carboxylic acids are preferable. Specifically, there may be mentioned: aromatic carboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, benzophenone tetracarboxylic acid, and furandicarboxylic acid, succinic acid, adipic acid, dodecanedioic acid, sebacic acid, thiodipropionic acid, cyclohexanedicarboxylic acid, tris (carboxymethyl) isocyanurate, tris (2-carboxyethyl) isocyanurate, tris (2-carboxypropyl) isocyanurate, and bis (2-carboxyethyl) isocyanurate.
Further, as the imidazole compound, there can be mentioned: 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 2, 4-diamino-6- (2 '-methylimidazole (1')) ethyl-s-triazine, 2, 4-diamino-6- (2 '-undecylimidazole (1')) ethyl-s-triazine, 2, 4-diamino-6- (2 '-ethyl-4-methylimidazole (1')) ethyl-s-triazine, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-methyl-2-methyl-imidazole, 2-methyl-s-triazine, 2-methyl-2-methyl-imidazole, 2-methyl-imidazole, 2-methyl imidazole, 2-n-methyl imidazole, 2-methyl imidazole, 2-methyl imidazole, 2-methyl imidazole, 2-methyl imidazole, 2-n, 2, 4-diamino-6- (2 '-methylimidazole (1')) ethyl-s-triazine isocyanuric acid adduct, 2: 3 adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-3, 5-dimethylolimidazole, 2-phenyl-4-hydroxymethyl-5-methylimidazole, 1-cyanoethyl-2-phenyl-3, 5-bis (cyanoethoxymethyl) imidazole and the like.
In the liquid crystal sealing agent of the present invention, when a curing accelerator is used, the content of the curing accelerator is preferably 0.1 to 10% by mass, and more preferably 1 to 5% by mass, in the total amount of the liquid crystal sealing agent.
[ photo radical polymerization initiator ]
The liquid crystal sealing agent of the present invention may contain a photo radical polymerization initiator. The photo radical polymerization initiator is not particularly limited as long as it is a compound that generates a radical or an acid by irradiation of ultraviolet rays or visible light and initiates a chain polymerization reaction, and examples thereof include: benzil dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, diethyl thioxanthone, benzophenone, 2-ethylanthraquinone, 2-hydroxy-2-methyl propiophenone, 2-methyl- [4- (methylthio) phenyl ] propanone]2-morpholino-1-propanone, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, camphorquinone, 9-fluorenone, diphenyl disulfide, and the like. Specifically, there may be mentioned: IRGACURERTM651、184、2959、127、907、369、379EG、819、784、754、500、OXE01、OXE02、OXE03、OXE04、DAROCURERTM1173、LUCIRINRTMTPO (both manufactured by Pasteur Co., Ltd.), SEIKUOLRTMZ, BZ, BEE, BIP, BBI (all manufactured by Seiko chemical Co., Ltd.), and the like. Among them, IRGACURE as an oxime ester initiator is preferableRTMOXE01、OXE02、OXE03、OXE04。
In addition, from the viewpoint of liquid crystal contamination, it is preferable to use a photo radical polymerization initiator having a (meth) acryloyl group in the molecule, for example, a reaction product of 2-methacryloyloxyethyl isocyanate and 1- [4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propan-1-one. This compound can be obtained by the method described in international publication No. 2006/027982.
In the liquid crystal sealing agent of the present invention, when the photo radical polymerization initiator is used, the content of the photo radical polymerization initiator in the total amount of the liquid crystal sealing agent is preferably 0.001 to 3% by mass, and more preferably 0.002 to 2% by mass.
[ thermal radical polymerization initiator ]
The liquid crystal sealing agent of the present invention can improve curing speed and curability by containing a thermal radical polymerization initiator.
The thermal radical polymerization initiator is not particularly limited as long as it is a compound that generates a radical by heating and initiates a chain polymerization reaction, and examples thereof include an organic peroxide, an azo compound, a benzoin ether compound, an acetophenone compound, and benzopinacol, and it is preferable to use benzopinacol. For example, Kayamek is commercially available as an organic peroxideRTMA、M、R、L、LH、SP-30C；Parkadox CH-50L、BC-FF；Cadox B-40ES；Parkadox14、TrigonoxRTM22-70E、23-C70、121、121-50E、121-LS50E、21-LS50E、42、42LS；KayaesterRTMP-70、TMPO-70、CND-C70、OO-50E、AN；KayabutylRTMB；Parkadox16；KayacarbonRTMBIC-75, AIC-75 (chemical AKZO corporation); permekRTMN、H、S、F、D、G；PerhexaRTMH、HC、TMH、C、V、22、MC；PercureRTMAH、AL、HB；PerbutylRTMH、C、ND、L、；PercumylRTMH、D；PeroylRTMIB、IPP；PeroctaRTMND (manufactured by Nichiki Kaisha) and the like.
The thermal radical polymerization initiator is preferably a thermal radical polymerization initiator having no oxygen-oxygen bond (-O — O-) or nitrogen-nitrogen bond (-N ═ N-) in the molecule. A thermal radical polymerization initiator having an oxygen-oxygen bond (-O-) or a nitrogen-nitrogen bond (-N ═ N-) in a molecule generates a large amount of oxygen or nitrogen gas when generating radicals, and therefore, the thermal radical polymerization initiator is cured in a state where bubbles remain in the liquid crystal sealing agent, and there is a possibility that the adhesive strength is lowered, the moisture permeability is lowered, the characteristics under a moist heat environment are lowered, and the like. Particularly preferred is a thermal radical polymerization initiator of the benzopinacol type (including a product obtained by chemically modifying benzopinacol). Specifically, there may be mentioned: benzopinacol, 1, 2-dimethoxy-1, 1,2, 2-tetraphenylethane, 1, 2-diethoxy-1, 1,2, 2-tetraphenylethane, 1, 2-diphenoxy-1, 1,2, 2-tetraphenylethane, 1, 2-dimethoxy-1, 1,2, 2-tetrakis (4-methylphenyl) ethane, 1, 2-diphenoxy-1, 1,2, 2-tetrakis (4-methoxyphenyl) ethane, 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane, 1, 2-bis (triethylsiloxy) -1,1,2, 2-tetraphenylethane, 1, 2-bis (tert-butyldimethylsiloxy) -1,1,2, 2-tetraphenylethane, 1-hydroxy-2-trimethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-triethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-tert-butyldimethylsilyloxy-1, 1,2, 2-tetraphenylethane and the like, preferably 1-hydroxy-2-trimethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-triethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1-hydroxy-2-tert-butyldimethylsilyloxy-1, 1,2, 2-tetraphenylethane, 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane, more preferably 1-hydroxy-2-trimethylsiloxy-1, 1,2, 2-tetraphenylethane, 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane, particularly preferably 1, 2-bis (trimethylsiloxy) -1,1,2, 2-tetraphenylethane.
The benzopinacol is sold by Tokyo Kasei Kogyo, Wako pure chemical industries, Ltd. In addition, the etherification of the hydroxyl group of benzopinacol can be easily performed by a known method. The silylizing of the hydroxyl group of benzopinacol can be obtained by a method of heating the corresponding benzopinacol and various silylating agents in the presence of a basic catalyst such as pyridine. Examples of the silylating agent include Trimethylchlorosilane (TMCS), Hexamethyldisilazane (HMDS), N, O-bis (trimethylsilyl) trifluoroacetamide (BSTFA), Triethylchlorosilane (TECS) as a triethylsilylating agent, and tert-butylmethylsilane (TBMS) as a tert-butyldimethylsilylating agent, which are generally known as trimethylsilylating agents. These reagents are readily available from silicon derivative manufacturers and the like. The reaction amount of the silylation agent is preferably 1.0 to 5.0 times by mole based on 1 mole of the hydroxyl group in the target compound. More preferably 1.5 to 3.0 times by mole. When the amount is less than 1.0 time by mol, the reaction efficiency is poor and the reaction time is prolonged, so that thermal decomposition is promoted. When it is more than 5.0 times mole, separation upon recovery becomes poor or purification becomes difficult.
Further, VA-044, 086, V-070, VPE-0201, VSP-1001 (manufactured by Wako pure chemical industries, Ltd.) and the like are commercially available as azo compounds.
The content of the thermal radical polymerization initiator in the total amount of the liquid crystal sealing agent of the present invention is preferably 0.0001 to 10% by mass, more preferably 0.0005 to 5% by mass, and particularly preferably 0.001 to 3% by mass.
The liquid crystal sealing agent of the present invention may further contain additives such as a silane coupling agent, a radical polymerization inhibitor, a pigment, a leveling agent, an antifoaming agent, and a solvent, as required.
[ silane coupling agent ]
Examples of the silane coupling agent include: 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, N-phenyl-gamma-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl) -3-aminopropyltrimethoxysilane hydrochloride, 3-methacryloxypropyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane and the like. These silane coupling agents are commercially available as KBM series, KBE series and the like, and are sold by shin-Etsu chemical industries, Ltd. When a silane coupling agent is used in the liquid crystal sealing agent of the present invention, the content of the silane coupling agent in the total amount of the liquid crystal sealing agent is preferably 0.05 to 3% by mass.
[ radical polymerization inhibitor ]
The radical polymerization inhibitor is not particularly limited as long as it is a compound that inhibits polymerization by reacting with a radical generated by a photo radical polymerization initiator, a thermal radical polymerization initiator, or the like, and quinones, piperidines, hindered phenols, nitroso groups, or the like can be used. Specifically, there may be mentioned: naphthoquinone, 2-hydroxynaphthoquinone, 2-menadione, 2-methoxynaphthoquinone, 2,6, 6-tetramethylpiperidin-1-oxyl, 2,6, 6-tetramethyl-4-hydroxypiperidin-1-oxyl, 2,6, 6-tetramethyl-4-methoxypiperidin-1-oxyl, 2,6, 6-tetramethyl-4-phenoxypiperidin-1-oxyl, hydroquinone, 2-methylhydroquinone, 2-methoxyhydroquinone, p-benzoquinone, butylated hydroxyanisole, 2, 6-di-tert-butyl-4-ethylphenol, 2, 6-di-tert-butylcresol, beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid stearyl ester, stearyl ester, 2,2 ' -methylenebis (4-ethyl-6-tert-butylphenol), 4 ' -thiobis (3-methyl-6-tert-butylphenol), 4 ' -butylidenebis (3-methyl-6-tert-butylphenol), 3, 9-bis [1, 1-dimethyl-2- [ beta- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy ] ethyl ] -2,4,8, 10-tetraoxaspiro [5.5] undecane, tetrakis [ methylene-3- (3 ', 5 ' -di-tert-butyl-4 ' -hydroxyphenylpropionate) methane ], 1,3, 5-tris (3 ', 5 ' -di-tert-butyl-4 ' -hydroxybenzyl) -s-triazine-2, 4,6- (1H,3H,5H) trione, p-methoxyphenol, 4-methoxy-1-naphthol, thiodiphenylamine, aluminum salt of N-nitrosophenylhydroxylamine, trade name ADK STAB LA-81, trade name ADK STAB LA-82 (manufactured by Ediko Co., Ltd.), and the like, but is not limited thereto. Among them, naphthoquinones, hydroquinones, nitros, and piperazines are preferable, naphthoquinones, 2-hydroxynaphthoquinones, hydroquinones, 2, 6-di-tert-butyl-P-cresol, POLYSTOP 7300P (manufactured by boston corporation) is more preferable, and POLYSTOP 7300P (manufactured by boston corporation) is most preferable.
The content of the radical polymerization inhibitor in the total amount of the liquid crystal sealing agent of the present invention is preferably 0.0001 to 1% by mass, more preferably 0.001 to 0.5% by mass, and particularly preferably 0.01 to 0.2% by mass.
As an example of a method for obtaining the liquid crystal sealing agent of the present invention, the following method can be mentioned. First, the curable compound, and if necessary, the photo radical polymerization initiator, the thermal radical polymerization initiator, and the radical polymerization inhibitor are dissolved by heating. Next, the liquid crystal sealing agent of the present invention can be produced by cooling to room temperature, adding a thermosetting agent, a curing accelerator, a filler, a silane coupling agent, an antifoaming agent, a leveling agent, a solvent, and the like as needed, uniformly mixing them by a known mixing device such as a three-roll mill, a sand mill, a ball mill, and the like, and filtering them with a metal mesh.
As for the liquid crystal display unit of the present invention, an example is shown below.
The liquid crystal display unit of the present invention is obtained by: a pair of substrates having a predetermined electrode formed on the substrate are arranged to face each other at a predetermined interval, the periphery is sealed with the liquid crystal sealing agent of the present invention, and a liquid crystal is sealed in the gap. The type of the liquid crystal to be sealed is not particularly limited. Here, the substrate is composed of a composite substrate including glass, quartz, plastic, silicon, and the like, at least one of which has light transmittance. As a method for producing the same, a spacer (gap control material) such as glass fiber is added to the liquid crystal sealing agent of the present invention, and then the liquid crystal sealing agent is applied to one of the pair of substrates by using a dispenser, a screen printing apparatus, or the like, and then precured at 80 to 120 ℃ as necessary. Then, liquid crystal is dropped inside the bank of the liquid crystal sealing agent, and another glass substrate is stacked in vacuum to form a gap. After the gap is formed, the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 ℃ for 30 minutes to 2 hours. When the liquid crystal sealing material is used in a photothermal type, the liquid crystal sealing material is irradiated with ultraviolet rays by an ultraviolet ray irradiation machine to be photocured. The ultraviolet irradiation dose is preferably 500mJ/cm2～6000mJ/cm2More preferably 1000mJ/cm2～4000mJ/cm2(measurement wavelength: 365 nm). Then, the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 ℃ for 30 minutes to 2 hours, if necessary. In such a way as to obtainThe liquid crystal display unit of the present invention has no display defects caused by liquid crystal contamination, and is excellent in adhesiveness and moisture resistance reliability. Examples of the spacer include: glass fibers, silica beads, polymer beads, and the like. The diameter thereof varies depending on the purpose, but is preferably 2 to 8 μm, and more preferably 4 to 7 μm. The amount of the spacer to be used is preferably 0.1 to 4 parts by mass, more preferably about 0.5 to about 2 parts by mass, and particularly preferably about 0.9 to about 1.5 parts by mass, based on 100 parts by mass of the liquid crystal sealing agent of the present invention.
[ examples ]
The present invention will be described in more detail with reference to examples, but the present invention is not limited to the examples. It is to be noted that "part" and "%" herein are on a mass basis unless otherwise specified.
[ Synthesis example 1]
A flask equipped with a thermometer, condenser and stirrer was charged with 776.99g of a polyester polyol (P-2012, hydroxyl value: 54.6mgKOH/g) comprising methylpentanediol, adipic acid and isophthalic acid and 131.68g of toluene diisocyanate (Coronate T-100, molecular weight: 174.2, manufactured by Tosoh corporation) and reacted at 80 ℃. The isocyanate content at this time was determined by adding an excess of amine and back-titrating with hydrochloric acid, and it was confirmed that the value was within plus or minus 2% of the residual amount of isocyanate determined from the calculated value. Subsequently, 0.6g of methoxyphenol (polymerization inhibitor), 90.43g of 2-hydroxyethyl acrylate (molecular weight: 116.1), and 0.3g of dibutyltin dilaurate (catalyst) were added thereto, and the mixture was stirred at 80 ℃ to effect a reaction until the absorption spectrum of the isocyanate group in the infrared absorption spectrum (2280 cm)-1) Disappeared to thereby obtain a urethane acrylate oligomer having a weight average molecular weight of 6300.
[ Synthesis example 2]
100 parts (0.28 mol) of commercially available benzopinacol (manufactured by tokyo chemical synthesis) was dissolved in 350 parts of dimethylformamide. To this, 32 parts (0.4 mol) of pyridine as a basic catalyst and 150 parts (0.58 mol) of BSTFA (manufactured by shin Etsu chemical Co., Ltd.) as a silylating agent were added, and the mixture was heated to 70 ℃ and stirred for 2 hours. The resultant reaction liquid was cooled, and 200 parts of water was added while stirring to precipitate the product while inactivating the unreacted silylating agent. The precipitated product was separated by filtration and then sufficiently washed with water. Next, the obtained product was dissolved in acetone, and water was added to conduct recrystallization and purification. 105.6 parts (yield 88.3%) of 1, 2-bis (trimethylsilyloxy) -1,1,2, 2-tetraphenylethane as a target product were obtained.
Examples 1 to 16 and comparative examples 1 to 10
A curable compound, a photo radical polymerization initiator, and a radical polymerization inhibitor were heated and dissolved at 90 ℃ in the proportions shown in tables 1 to 3 below, and then cooled to room temperature, and a thermal radical polymerization initiator, a thermal curing agent, a curing accelerator, an organic filler, an inorganic filler, and a silane coupling agent were added and stirred, and then dispersed by a three-roll mill, and filtered by a metal mesh (635 mesh), thereby preparing a liquid crystal sealing agent. The specific surface area of the filler is a value which is clearly described in each company catalog, and the value measured by the BET method is used for F-351S.
[ evaluation ]
[ viscosity ]
The viscosity measurement in the present invention is performed under the following conditions.
A liquid crystal sealing agent (0.15 mL) was added to a measuring cup of an E-type viscometer (RE 105, manufactured by Toyobo industries Co., Ltd.). The sample was left as a preheat at a temperature of 25 ℃ for 120 seconds with a cone of 3 ℃ for R7.7, and then the value after rotating at 5rpm for 180 seconds was measured.
The viscosity at 0.5rpm was measured for a sample exceeding the measurement limit of 5rpm (600Pa · s). The results are shown in tables 1 to 3.
[ production of substrate with photo-alignment-treated alignment film ]
An alignment film solution (NRB-U738, manufactured by Nissan chemical Co., Ltd.) was spin-coated on a glass substrate, prebaked on a hot plate at 80 ℃ for 3 minutes, and baked in an oven at 230 ℃ for 30 minutes. Then, the substrate with the alignment film was irradiated with UV lightPlate irradiation 500mJ/cm2(measurement wavelength: 254nm) and further baked in an oven at 230 ℃ for 30 minutes.
[ production of liquid Crystal cell for evaluation ]
On the substrate with the photo-alignment type alignment film, a main seal and a dummy seal (ダミーシール) were dispensed so as to form a square having a line width of 0.6mm, a longitudinal direction of 10mm, and a transverse direction of 10mm after the liquid crystal sealant was attached, and then, fine droplets of a liquid crystal (JC-5015 LA; manufactured by JNC corporation) were dropped into a frame of a seal pattern. Then, an in-plane Spacer (Natoco Spacer KSEB-525F; manufactured by Natoco corporation; gap width 5 μm after bonding) was spread on another photo-alignment-treated substrate, heat-fixed, and bonded to the substrate on which the liquid crystal was previously dropped in a vacuum using a bonding apparatus. After opening to the atmosphere for 3 minutes, only the inside of the frame of the seal pattern was masked, and irradiated with UV light at 3000mJ/cm2Then, the resultant was put into an oven and thermally cured at 120 ℃ for 60 minutes to prepare a liquid crystal cell for evaluation.
[ Observation of interference fringes ]
The liquid crystal cell for evaluation was observed with an interference fringe inspection lamp (FNA-35; Funatech corporation), and the number of interference fringe dark lines outside the liquid crystal sealant was measured. The results are shown in tables 1 to 3. Fig. 1 shows the relationship between the average specific surface area and the number of interference fringe dark lines.
[ moisture permeability ]
The liquid crystal sealants manufactured in examples and comparative examples were sandwiched between polyethylene terephthalate (PET) films to prepare films having a thickness of 300. mu.m, and the films were irradiated with 3000mJ/cm by a UV irradiator2(measurement wavelength: 365nm), then placed in an oven, thermally cured at 120 ℃ for 60 minutes, and after curing, the PET film was peeled off to prepare a sample. The moisture permeability of the sample at 60 ℃ and 90% was measured by a moisture permeability measuring apparatus (L80-5000, manufactured by Lyssy Co.). The results are shown in tables 1 to 3.
[ modulus of elasticity ]
Will be described in the examples and comparative examplesThe liquid crystal sealant produced in example was sandwiched between polyethylene terephthalate (PET) films to prepare a film having a thickness of 100 μm, and the film was irradiated with 3000mJ/cm by a UV irradiation machine2(measurement wavelength: 365nm), then placed in an oven, thermally cured at 120 ℃ for 60 minutes, and after curing, the PET film was peeled off to prepare a sample. A Tensilon Universal testing machine (A corporation) was used&Manufactured by D, RTG-1210) was measured by subjecting a sample to a tensile test at a test speed of 5 mm/min at room temperature (25 ℃). The results are shown in tables 1 to 3.
TABLE 1
TABLE 2
TABLE 3
TABLE 4
The results of tables 1 to 4 and fig. 1 confirm that the liquid crystal sealing agent of the present invention is excellent in the crushability. In addition, it was confirmed that the liquid crystal sealing agent of the present invention has both flexibility and low moisture permeability.
Industrial applicability
The liquid crystal sealing agent of the present invention has excellent crushing properties, and combines flexibility and low moisture permeability, and therefore, is particularly useful as a liquid crystal sealing agent for a thin liquid crystal display or a liquid crystal display having a curved shape.
Claims (11)
1. A liquid crystal sealing agent for a liquid crystal dropping method comprising a curable compound, a filler and a heat-curing agent, wherein,
the average specific surface area of the filler was 10.0m2A/g or more, and
the viscosity of the liquid crystal sealing agent for liquid crystal dropping method measured by using an E-type viscometer at the conditions of 25 ℃ and 5rpm is less than 500Pa s.
2. The liquid crystal sealing agent for liquid crystal dropping method according to claim 1, wherein a cured product of the liquid crystal sealing agent for liquid crystal dropping method has an elastic modulus at 25 ℃ of 2500MPa or less as measured by a Tensilon universal tester.
3. The liquid crystal sealing agent for liquid crystal dropping method according to claim 1 or 2, wherein a moisture permeability measured at 60 ℃ and 90% when a film thickness of a cured product of the liquid crystal sealing agent for liquid crystal dropping method is 300 μm is 100g/m224h or less.
4. The liquid crystal sealing agent for liquid crystal dropping method according to any one of claims 1 to 3, wherein the content of the filler is 5 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the curable compound.
5. The liquid crystal sealing agent for liquid crystal dropping method according to any one of claims 1 to 4, wherein the liquid crystal sealing agent for liquid crystal dropping method contains an organic filler and an inorganic filler as the filler, and the inorganic filler is an inorganic filler subjected to hydrophobic surface treatment.
6. The liquid crystal sealing agent for liquid crystal dropping method according to any one of claims 1 to 5, wherein the liquid crystal sealing agent for liquid crystal dropping method contains urethane (meth) acrylate as the curable compound.
7. The liquid crystal sealing agent for liquid crystal dropping method according to claim 6, wherein the urethane (meth) acrylate is obtained by reacting (a) a polyol having an aromatic ring, (b) an organic polyisocyanate, and (c) a hydroxyl group-containing (meth) acrylate.
8. The liquid crystal sealing agent for liquid crystal dropping method according to any one of claims 1 to 7, wherein the liquid crystal sealing agent for liquid crystal dropping method further contains a thermal radical polymerization initiator.
9. A liquid crystal sealing agent for liquid crystal dropping method according to claim 8, wherein said thermal radical polymerization initiator is a thermal radical polymerization initiator not containing oxygen-oxygen bond (-O-) and nitrogen-nitrogen bond (-N ═ N-) in a molecule.
10. The liquid crystal sealing agent for liquid crystal dropping method according to any one of claims 1 to 9, wherein the liquid crystal sealing agent for liquid crystal dropping method further contains a photo radical polymerization initiator.
11. A liquid crystal display unit, wherein the liquid crystal display unit is encapsulated with a liquid crystal sealant by a liquid crystal dropping method according to any one of claims 1 to 10.
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