TW201900835A - Curable compositions for one drop sealant applications - Google Patents

Abstract

The present invention relates to resins useful in adhesive and sealant compositions and particularly as one drop fill sealants for liquid crystal applications. In particular, the present invention permits assembly of LCD panels without migration of the sealant resin into the liquid crystal or vice versa during LCD assembly and/or curing of the resin.

Description

Curable composition for drip sealant applications

The present invention relates to a resin suitable for use in an adhesive and a sealant composition, and particularly suitable for use in a drip-type injection sealant for liquid crystal applications. In particular, the present invention permits assembly of the LCD panel without moving the encapsulant resin into the liquid crystal during LCD assembly and/or curing of the resin or vice versa.

The Drop Injection ("ODF") method is becoming the mainstream method for assembly of LCD panels in display applications, replacing conventional vacuum injection techniques to meet the demands of faster manufacturing methods. In the ODF method, a sealant is first dispensed onto a substrate of an electrode assembly to form a frame of the display element, and the liquid crystal is dropped into the interior of the frame depicted. In the next step of assembly, the substrate of the other electrode is joined to it under vacuum. Subsequently, the encapsulant is cured by a combination of UV and thermal processes or by a thermal process alone.

Several problems with the ODF process are that the sealant material in an uncured state contacts the liquid crystal ("LC") during the assembly process. Thereby the electro-optical properties of the LC can be reduced by moving the resin or ionic impurities into the LC or vice versa. Therefore, the design of resin systems for sealant materials that exhibit good liquid crystal resistance (less contamination) and good adhesion and moisture barrier properties has been challenging.

In addition, since 5% of the excess LC is typically used as compared to the fill volume requirement, there is a positive pressure of LC on the sealant resin during the vacuum assembly process before the sealant undergoes curing. If the resin is not stable, the LC can penetrate into the sealant during assembly opening. The resin needs to exhibit structural features that are sufficient for LC resistance to minimize LC contamination or penetration. Generally, polar functional groups such as hydroxyl groups, ureas, urethanes, quinones, and aryl groups are required to achieve good LC resistance. Therefore, the design of resin systems for sealant materials that exhibit good liquid crystal resistance (less contamination) and good adhesion and moisture barrier properties has been challenging.

Although some solutions to these problems have been identified in the past (see, for example, International Patent Application Nos. PCT/US2016/04611, PCT/CN2015/083966, and PCT/CN2015/083963), end users need alternative technologies to Provide a broader choice of possible solutions.

The present invention relates to a specific resin and an ODF composition produced therefrom.

In one aspect of the invention, a resin having the following structure I is included: Where Q can be selected from: And an unfunctionalized group, wherein the unfunctionalized group is selected from the group consisting of H, alkyl, alkoxy, aryl, aralkyl, cycloalkyl and heterocycle; and R is selected from the group consisting of a polyvalent hydrocarbon-based linking group: a linear or branched alkyl group, a linear or branched alkyl group, an alkyl group, a cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group, a linear or branched chain. Alkyl, straight or branched chain cycloalkyl, straight or branched chain alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl Aryl, tricycloalkylaryl, bisphenyl, cycloalkyl extended aryl, heterocycloalkyl or heterocyclic aryl; alkyl, cycloalkyl, alkyl, cycloalkyl , alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, tricycloalkyl extended aryl, extended phenyl, cycloalkyl The aryl, heterocycloalkyl and heterocyclic aryl groups may optionally contain O or S or a hydroxyl group; R ₁ is H or methyl; X is selected from CH ₂ , n ₁ and n ₃ are each independently 0-10; n ₂ is 1-10; Y is an aryl group, an alkyl group, an alkenyl group, an aralkyl group, a cycloalkyl group, a dicycloalkyl group or a tricycloalkyl group; and Z is a covalent bond or a hydrocarbyl linkage group linking the aryl group to the carboxylate group.

In another aspect of the invention, a resin having the following structure II is included: Wherein X ₁ and X ₂ are independently a 3-10 membered cyclic group selected from a functionalized or unfunctionalized alicyclic group optionally having one or more heteroatoms; R is a polyvalent hydrocarbon radical selected from the group consisting of A group: a linear or branched alkyl group, a linear or branched alkyl group, an alkyl group, a cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group, a linear or branched alkyl group, Linear or branched chain alkylene, linear or branched chain alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, three Cycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, heterocycloalkyl or heterocyclic aryl; such alkyl, cycloalkyl, alkyl, cycloalkyl, alkenyl , aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, tricycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, stretch The heterocycloalkyl and heterocyclic aryl group may optionally contain O or S or a hydroxyl group; and R is bonded at any position to a ring structure containing X ₁ and X ₂ ; X ₃ is a (meth) acrylate bond linked to X ₁ of ring bond, or Wherein n is 0-10; and R ₁ is H or methyl; Y is an aryl, alkyl, alkenyl, aralkyl, cycloalkyl, bicycloalkyl or tricycloalkyl The restriction is that the hydroxyl group on the X ₁ ring is adjacent to the X ₃ group containing the (meth) acrylate, and the hydroxyl group on the X ₂ ring is adjacent to the maleimine aryl fluorenyl group or A maleidino aralkyl fluorenyl group; and Z is a covalent bond or a hydrocarbyl bond group linking an aryl group to a carboxylate group.

In still another aspect of the invention, a resin having the following structure III is included: Wherein X ₁ and X ₂ are independently a 3-10 membered cyclic group selected from a functionalized or unfunctionalized alicyclic group optionally having one or more heteroatoms; R is a polyvalent hydrocarbon radical selected from the group consisting of A group: a linear or branched alkyl group, a linear or branched alkyl group, an alkyl group, a cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group, a linear or branched alkyl group, Linear or branched chain alkylene, linear or branched chain alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, three Cycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, heterocycloalkyl or heterocyclic aryl; such alkyl, cycloalkyl, alkyl, cycloalkyl, alkenyl , aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, tricycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, stretch The heterocycloalkyl and heterocyclic aryl groups may optionally contain O or S or a hydroxyl group; and R may be bonded to the ring structures X ₁ and X ₂ at any position, with the proviso that the hydroxyl group on the X ₂ ring is adjacent to the Carboxy horse An imine; and Z is a covalent bond or a hydrocarbyl linkage group linking an aryl group to a carboxylate group.

The resins of the present invention are suitable for a variety of applications including adhesives and sealants. A particularly effective use of the resin of the present invention is as an ODF sealant for assembling an LCD panel.

The present invention provides resins (which also include oligomers and polymers) suitable for use in the preparation of curable compositions useful in ODF sealants.

The glycidyl ether/ester compound suitable for the synthesis of the mixed resin of the present invention described herein is not particularly limited, and examples of the epoxy compound available in the market include: bisphenol A type epoxy resin such as Epikote 828EL and Epikote 1004 (all manufactured by Japan Epoxy Resin Co., Ltd.); bisphenol F type epoxy resin such as Epikote 806 and Epikote 4004 (all manufactured by Japan Epoxy Resin Co., Ltd.); bisphenol S type epoxy resin Such as Epiclon EXA1514 (manufactured by Dainippon Ink and Chemicals Inc.) and SE 650 manufactured by Shin A T&C; 2,2'-diallyl bisphenol A type epoxy resin such as RE-81 ONM (by Nippon Kayaku Co., Ltd. manufactured; hydrogenated bisphenol type epoxy resin such as Epiclon EXA7015 (manufactured by Dainippon Ink and Chemicals Inc.); propylene oxide addition bisphenol A type epoxy resin such as EP-4000S ( Manufactured by ADEKA Corporation; resorcinol type epoxy resin such as EX-201 (manufactured by Nagase ChemteX Corporation); biphenyl type epoxy resin such as Epikote YX-4000H (manufactured by Japan Epoxy Resin Co., Ltd.) Sulfide type epoxy tree Fat, such as YSLV 50TE (manufactured by Tohto Kasei Co., Ltd.); ether type epoxy resin such as YSLV 80DE (manufactured by Tohto Kasei Co., Ltd.); dicyclopentadiene type epoxy resin such as EP -4088S and EP4088L (manufactured by ADEKA Corporation); naphthalene type epoxy resin such as SE-80, SE-90, manufactured by Shin A T&C; glycidylamine type epoxy resin such as Epikote 630 (by Japan Epoxy Resin) Co., Ltd., Epiclon 430 (manufactured by Dainippon Ink and Chemicals Inc.) and TETRAD-X (manufactured by Mitsubishi Gas Chemical Company Inc.); alkyl polyol type epoxy resin such as ZX-1542 (by Tohto Kasei Co., Ltd.), Epiclon 726 (manufactured by Dainippon Ink and Chemicals Inc.), Epolight 8OMFA (manufactured by Kyoeisha Chemical Co., Ltd.), and Denacol EX-611 (manufactured by Nagase ChemteX Corporation); rubber A modified type epoxy resin such as YR-450, YR-207 (all manufactured by Tohto Kasei Co., Ltd.) and Epolead PB (manufactured by Daicel Chemical Industries, Ltd.); a glycidyl ester compound such as Denacol EX- 147 (manufactured by Nagase ChemteX Corporation) Bisphenol A type epoxy sulfide resin such as Epikote YL-7000 (manufactured by Japan Epoxy Resin Co., Ltd.); and other compounds such as YDC-1312, YSLV-BOXY, YSLV-90CR (both by Tohto Kasei Co) , manufactured by Asahi Kasei Corporation, Epikote 1031, Epikote 1032 (all manufactured by Japan Epoxy Resin Co., Ltd.), EXA-7120 (manufactured by Dainippon Ink and Chemicals Inc.), TEPIC (manufactured by Nissan Chemical Industries, Ltd.). Examples of commercially available phenol varnish type phenol resin type epoxy compounds include Epiclon N-740, N-770, N-775 (all manufactured by Dainippon Ink and Chemicals Inc.), Epikote 152, and Epikote 154 (both by Japan Epoxy Resin Co) ., manufactured by Ltd.) and its analogues. Examples of commercially available cresol varnish type phenolic resin type epoxy compounds include Epiclon N-660, N-665, N-670, N-673, N-680, N-695, N-665-EXP, and N-672- EXP (all manufactured by Dainippon Ink and Chemicals Inc.); an example of a commercially available biphenyl varnish type phenol resin type epoxy compound is NC-3000P (manufactured by Nippon Kayaku Co., Ltd.); commercially available trisphenol varnish type phenol no. Examples of the resin type epoxy compound include EP1032S50 and EP1032H60 (both manufactured by Japan Epoxy Resin Co., Ltd.); examples of commercially available dicyclopentadiene varnish type phenol resin type epoxy compounds include XD-1000-L (by Nippon Kayaku Co., Ltd.) and HP-7200 (manufactured by Dainippon Ink and Chemicals Inc.); examples of commercially available bisphenol A type epoxy compounds include Epikote 828, Epikote 834, Epikote 1001, and Epikote 1004 (both by Japan Epoxy Resin Co., Ltd.), Epiclon 850, Epiclon 860 and Epiclon 4055 (all manufactured by Dainippon Ink and Chemicals Inc.); examples of commercially available bisphenol F type epoxy compounds include Epikote 807 (by Japan Epoxy Resin) Co., Ltd.) and Epiclon 830 (by Dainippon Ink and Chem Manufactured by icals Inc.; an example of a commercially available 2,2'-diallyl bisphenol A type epoxy compound is RE-81ONM (manufactured by Nippon Kayaku Co., Ltd.); a commercially available hydrogenated bisphenol type ring An example of the oxygen compound is ST-5080 (manufactured by Tohto Kasei Co., Ltd.); examples of commercially available polyoxypropylene bisphenol A type epoxy compounds include EP-4000 and EP-4005 (all manufactured by ADEKA Corporation); And its analogues. HP4032 and Epiclon EXA-4700 (all manufactured by Dainippon Ink and Chemicals Inc.); phenol varnish type phenol resin type epoxy resin such as Epiclon N-770 (manufactured by Dainippon Ink and Chemicals Inc.); o-cresol varnish type phenolic Resin type epoxy resin, such as Epiclon N-670-EXP-S (manufactured by Dainippon Ink and Chemicals Inc.); dicyclopentadiene varnish type phenolic resin type epoxy resin, such as Epiclon HP7200 (by Dainippon Ink and Chemicals Inc . Manufactured); a biphenyl varnish type phenol resin type epoxy resin such as NC-3000P (manufactured by Nippon Kayaku Co., Ltd.); and a naphthol varnish type phenol resin type epoxy resin such as ESN-165S (by Tohto Made by Kasei Co., Ltd.).

Examples of the alicyclic epoxy compound suitable for the synthesis of the resin of the present invention include a polyglycidyl ether of a polyol having at least one alicyclic ring and a phenol obtained by epoxidation of a cyclohexene ring-containing or cyclopentene ring compound. Epoxycyclohexane or epoxycyclopentene compound. Specific examples include hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, cyclohexyl-3,4-epoxy-l-methyl ring 3,4-Epoxy-1-methyl hexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxy-cyclohexanecarboxylic acid Ester, 3,4-epoxy-3-methylcyclohexanecarboxylic acid 3,4-epoxy-3-methylcyclohexylmethyl, 3,4-epoxy-5-methylcyclohexyl 3-,4-epoxy-5-methylcyclohexanecarboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane -m-dioxane, bis(3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexanate, methylene bis (3,4- Epoxycyclohexane), dicyclopentadiene diepoxide, ethyl bis(3,4-epoxycyclohexanecarboxylate), dioctyl epoxy hexahydrophthalate Acid ester and di-2-ethylhexyl hexahydrophthalate.

Some of these cycloaliphatic epoxy resins are available under the trade names UVR-6100, UVR-6105, UVR-6110, UVR-6128 and UVR-6200 (products of Union Carbide Corporation); CELLOXIDE 2021, CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE 2085, CELLOXIDE 2000, CELLOXIDE 3000, CYCLMER A200, CYCLMER M100, CYCLMER M101, EPOLEAD GT-301, EPOLEAD GT-302, EPOLEAD 401, EPOLEAD 403, ETHB and EPOLEADHD 300 (from Daicel Chemical Industries, Ltd .); KRM-2110 and KRM-2199 (from ADEKA Corporation).

In addition to the curable polymer of the present invention, the ODF sealant composition can also include a free radical initiator (which can be triggered by exposure to high temperature conditions or electromagnetic spectrum radiation) and a curing agent. In embodiments in which an epoxide ring is present, a latent epoxy curing agent can also be employed.

Suitable thermal free radical initiators include organic peroxides and azo compounds, examples of which include: azo radical initiators such as AIBN (azobisisobutyronitrile), 2,2'-azobis (4- Methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-propionic acid) Methyl ester), 2,2'-azobis(2-methylbutyronitrile), 1,1,1-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis [ N-(2-propenyl)-2-methylpropionamine]; a dialkyl peroxide free radical initiator such as 1,1-di(butylperoxy-3,3,5-trimethyl) Base cyclohexane); peracid alkyl ester free radical initiator, such as TBPEH (tert-butyl per-2-ethylhexanoate); dimercapto peroxide free radical initiator, such as benzamidine peroxide Peroxydicarbonate free radical initiator, such as ethylhexyl percarbonate; ketone peroxide initiator, such as methyl ethyl ketone peroxide, bis (tert-butyl peroxide) diisopropyl benzene , tert-butyl perbenzoate, t-butyl peroxy neodecanoate, and combinations thereof.

Other examples of organic peroxide free radical initiators include: barium peroxide, 2,2-bis(4,4-di(t-butylperoxy)cyclohexyl)propane, and di(t-butyl) Peroxyisopropyl)benzene, bis(4-tert-butylcyclohexyl peroxydicarbonate), dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate, 2,3-dimethyl Base-2,3-diphenylbutane, dicumyl peroxide, benzamidine peroxide, diisopropyl peroxydicarbonate, tert-butyl monoperoxy maleate, 2, 5-Dimethyl-2,5-di(t-butylperoxy)hexane, tert-butylperoxy 2-ethylhexyl carbonate, peroxy-2-ethylhexanoate Ester, third amyl peroxypivalate, third amyl peroxy 2-ethylhexyl carbonate, 2,5-dimethyl-2,5-di(2-ethylhexylperoxy) Hexane 2,5-dimethyl-2,5-di(t-butylperoxy)hex-3, bis(3-methoxybutyl)peroxydicarbonate, diisobutylphosphonium peroxide , tert-butyl peroxy-2-ethylhexanoate (Trigonox 21 S), 1,1-di(t-butylperoxy)cyclohexane, tert-butyl peroxy neodecanoate, Third butyl pivorate, third butyl peroxy neoheptanoate , tert-butyl peroxydiethylacetate, 1,1-di(t-butylperoxy)-3,3,5-trimethylcyclohexane, 3,6,9-triethyl -3,6,9-trimethyl-1,4,7-triperoxydecane, bis(3,5,5-trimethylhexanyl peroxide), tert-butylperoxy hexanoate- 3,5,5-trimethyl ester, peroxy-2-ethylhexanoic acid 1,1,3,3-tetramethylbutyl ester, peroxy neodecanoic acid 1,1,3,3-tetramethyl Butyl ester, butyl butylperoxy-3,5,5-trimethyl hexanoate, cumene peroxy neodecanoate, di-tert-butyl peroxide, tert-butylperoxy carbonate Isopropyl ester, tert-butyl peroxybenzoate, di(2-ethylhexyl)peroxydicarbonate, tert-butyl peroxyacetate, isopropyl cumene hydroperoxide, peroxidation third Butyl cumene and mixtures thereof.

A thermal radical initiator having a higher decomposition rate is generally required because it is easier to generate radicals at a common curing temperature (such as in the range of 80 to 130 ° C) and a faster curing speed, which lowers the liquid state. The contact time between the resin and the liquid crystal, and reduces liquid crystal contamination. On the other hand, if the decomposition rate of the initiator is too high, the viscosity stability at room temperature will be affected, and thus the service life of the sealant will be shortened.

A suitable way of exhibiting the rate of decomposition of the initiator at a given temperature is with respect to its half-life, i.e., the time required to decompose half of the initially present peroxide. To compare the reactivity of the different initiators, the temperature at which each initiator has a 10-hour half-life (" _T1⁄2 ") is used. Most reactive (fastest) initiator should initiator having the lowest temperature T _1/2 of 10 hours.

In the present invention, a thermal radical initiator having a T _2⁄2 temperature of 30 to 80 ° C for 10 hours is preferred, and a thermal radical initiator having a T _1⁄2 temperature of 40 to 70 ° C for 10 hours is more preferable.

In order to balance the reactivity and viscosity stability of the composition, the thermal radical initiator for the resin composition is usually from 0.01 to 3 parts by weight, based on 100 parts by weight of the resin of the invention in the curable composition of the invention, and is preferably An amount of 0.5 to 2 parts by weight.

Suitable UV free radical initiators include Norrish Type I split photoinitiators available from CIBA and BASF. These photoinitiators are used in the formulation in an amount of from 0.1 to 5% by weight, more preferably from about 0.2 to 3% by weight.

Examples of suitable epoxy-based curing agents include, but are not limited to, Ajicure series hardeners available from Ajinomoto Fine-Techno Co., Inc.; Amicure series curing agents available from Air Products and JERCURETM products available from Mitsubushi Chemical. These curing agents or hardeners or accelerators are used in an amount of from about 1% to about 50% by weight of the total composition, more preferably from about 5% to about 20% by weight of the total composition. .

The curable composition may optionally contain another component capable of photopolymerization, such as a vinyl ether compound, as needed. In addition, the curable composition may further comprise an additive, a resin component, and the like to improve or modify after curing such as the following characteristics: fluidity, distribution or printing characteristics, storage characteristics, curing characteristics, and physical properties.

The composition may contain various additives as needed, such as organic or inorganic fillers, shakers, decane coupling agents, diluents, modifiers, colorants (such as pigments and dyes), surfactants, preservatives, stabilizers, Plasticizers, lubricants, defoamers, leveling agents, and the like; however, are not limited to such additives. In particular, the composition preferably comprises an additive selected from the group consisting of organic or inorganic fillers, shakers and decane coupling agents. Such additives may be present in an amount of from about 0.1% to about 50% by weight of the total composition, more preferably from about 2% to about 10% by weight of the total composition.

The filler may include an inorganic filler such as cerium oxide, diatomaceous earth, aluminum oxide, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, magnesium hydroxide, aluminum hydroxide, magnesium carbonate, barium sulfate, gypsum. , calcium citrate, talc, glass beads, sericite-activated clay, bentonite, aluminum nitride, tantalum nitride and the like; and organic fillers such as poly(methyl)methacrylate, poly(B) Methyl acrylate, poly(propyl) methacrylate, poly(butyl) methacrylate, butyl acrylate-methacrylic acid-(meth) methacrylate copolymer, polyacrylonitrile Polystyrene, polybutadiene, polypentadiene, polyisoprene, polyisopropene and the like. These materials can be used singly or in combination. These fillers may be present in an amount from about 1% to about 80%, more preferably from about 5% to about 30% by weight of the total composition.

The rocking agent may include, but is not limited to, talc, aerosolized cerium oxide, finely processed surface treated calcium carbonate, finely divided alumina, platy alumina; layered compounds such as montmorillonite, acicular compounds such as aluminum borate Whiskers, and the like. Among them, talc, aerosolized cerium oxide and finely divided alumina are preferred. These agents may be present in an amount from about 1% to about 50%, more preferably from about 1% to about 30%, by weight of the total composition.

The decane coupling agent may include, but is not limited to, γ-aminopropyltriethoxydecane, γ-mercaptopropyltrimethoxydecane, γ-methacryloxypropyltrimethoxydecane, γ-glycidyloxygen Propyltrimethoxydecane and its analogs.

The curable composition according to the present invention can be obtained by mixing the aforementioned components by means of, for example, a mixer such as a stirrer having a stirring blade and a three-roll mill. The composition was a liquid at a viscosity of 200-400 Pa.s (at 25 ° C) at a shear rate of 1.5 s-1.

The present invention also relates to a method for manufacturing a liquid crystal display having a liquid crystal layer between a first substrate and a second substrate by means of a liquid crystal dropping type implantation method. The method comprises the steps of: (a) applying a curable composition according to the invention to a sealing region at the outer periphery of the surface of the first substrate; (b) dropping the liquid crystal onto the first substrate (c) covering the second substrate with the second substrate; (d) partially curing by the UV radiation of the curable composition, and (e) heating by the curing The curable composition is subjected to final curing.

The first substrate and the second substrate used in the present invention are generally transparent glass substrates. Generally, a transparent electrode, an active matrix element such as a TFT, an alignment film, a color filter, and the like are formed on at least one of opposite faces of the two substrates. These configurations can be modified depending on the type of LCD. The manufacturing method according to the present invention can be considered to be applicable to any type of LCD.

In the step (a), the curable composition is applied to the outer periphery of the surface of the first substrate so as to surround the periphery of the substrate in a frame shape. The portion of the curable composition that is coated in the shape of a frame is referred to as a sealed region. The curable composition can utilize known methods such as screen printing and dispensing coating.

In the step (b), the liquid crystal is then dropped onto the central region surrounded by the sealing region in the shape of a frame on the surface of the first substrate. This step is preferably carried out under reduced pressure.

In step (c), the second substrate is then placed over the first substrate and UV radiation is performed in step (d). By UV irradiation, the curable composition is partially cured and exhibits a level of resistance that does not occur at the level of displacement, thereby temporarily fixing the two substrates. Generally, the irradiation time is preferably shorter, for example, no longer than 5 minutes, preferably no longer than 3 minutes, and more preferably no longer than 1 minute.

In step (e), the curable composition is heated to achieve a final cure strength whereby the two substrates eventually bond together. The heat curing in the step (e) is generally carried out at a temperature of 80 to 130 ° C and preferably 100 to 120 ° C for a heating time of 30 minutes to 3 hours, usually 1 hour.

By the aforementioned method, the main parts of the LCD panel are completed.

Example Example 1 : Example 2

Add N , N -diglycidyl-4-glycidyloxyaniline (24.18 g, 87 mmol), 6-maleimidohexanoic acid to a 500 mL 3-neck flask equipped with a magnetic stir bar (18.42 g, 87 mmol), Hycat 2000S (340 mg, 0.8% by weight) and methyl hydroquinone (42 mg, 1000 ppm) in ethyl acetate (42 mL). The mixture was stirred at 65 ° C for 4 h. After cooling, 300 mL of ethyl acetate was added, and the organic layer was washed once with NaHCO ₃ aqueous solution, once with 5% NaOH aqueous solution, and washed three times with deionized water. After drying over anhydrous Na ₂ SO ₄ , the solution was stirred with 5 g (10% by weight) of cerium oxide and 5 g of sillitin (sillitin) for 1 h. The solution was filtered off and washed with 100 mL ethyl acetate. 70 mg of methyl hydroquinone (2000 ppm total) was added and the solvent was evaporated to give a liquid (35 g, 83%). ¹ H NMR indicated the presence of a mixture of N-glycidyl and O-glycidyl adducts of maleimide hexanoic acid.

Claims (10)

a resin comprising the following structure, Where Q can be selected from: An unfunctionalized group, wherein the unfunctionalized group is selected from the group consisting of H, alkyl, alkoxy, aryl, aralkyl, cycloalkyl, and heterocycle; and R is selected from the group consisting of a polyvalent hydrocarbon-based linking group: a linear or branched alkyl group, a linear or branched alkyl group, an alkyl group, a cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group, a linear or branched chain. Alkyl, straight or branched chain cycloalkyl, straight or branched chain alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl Aryl, tricycloalkylaryl, bisphenyl, cycloalkyl extended aryl, heterocycloalkyl or heterocyclic aryl; alkyl, cycloalkyl, alkyl, cycloalkyl , alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, tricycloalkyl extended aryl, extended phenyl, cycloalkyl The aryl, heterocycloalkyl and heterocyclic aryl groups may optionally contain O or S or a hydroxyl group; R ₁ is H or methyl; X is selected from CH ₂ , n ₁ and n ₃ are each independently 0-10; n ₂ is 1-10; Y is an aryl group, an alkyl group, an alkenyl group, an aralkyl group, a cycloalkyl group, a dicycloalkyl group or a tricycloalkyl group; and Z is a covalent bond or a hydrocarbyl linkage group linking the aryl group to the carboxylate group. A resin comprising the following structure: Wherein X ₁ and X ₂ are independently a 3-10 membered cyclic group selected from a functionalized or unfunctionalized alicyclic group optionally having one or more heteroatoms; R is a polyvalent hydrocarbon radical selected from the group consisting of A group: a linear or branched alkyl group, a linear or branched alkyl group, an alkyl group, a cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group, a linear or branched alkyl group, Linear or branched chain alkylene, linear or branched chain alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, three Cycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, heterocycloalkyl or heterocyclic aryl; such alkyl, cycloalkyl, alkyl, cycloalkyl, alkenyl , aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, tricycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, stretch The heterocycloalkyl and heterocyclic aryl group may optionally contain O or S or a hydroxyl group; and R is bonded at any position to a ring structure containing X ₁ and X ₂ ; X ₃ is a (meth) acrylate bond bond linked to X ₁ of the ring, Is Wherein n is 0-10; and R ₁ is H or methyl; Y is an aryl, alkyl, alkenyl, aralkyl, cycloalkyl, bicycloalkyl or tricycloalkyl The restriction is that the hydroxyl group on the X ₁ ring is adjacent to the X ₃ group containing the (meth) acrylate, and the hydroxyl group on the X ₂ ring is adjacent to the maleimine group, respectively. A mercapto or maleinimidoarylalkyl group; and Z is a covalent bond or a hydrocarbyl linkage group linking the aryl group to a carboxylate group. A resin comprising the following structure: Wherein X ₁ and X ₂ are independently a 3-10 membered cyclic group selected from a functionalized or unfunctionalized alicyclic group optionally having one or more heteroatoms; R is a polyvalent hydrocarbon radical selected from the group consisting of A group: a linear or branched alkyl group, a linear or branched alkyl group, an alkyl group, a cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group, a linear or branched alkyl group, Linear or branched chain alkylene, linear or branched chain alkenyl, aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, three Cycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, heterocycloalkyl or heterocyclic aryl; such alkyl, cycloalkyl, alkyl, cycloalkyl, alkenyl , aryl, aralkyl, arylbicycloalkyl, aryltricycloalkyl, bicycloalkyl extended aryl, tricycloalkyl extended aryl, extended bisphenyl, cycloalkyl extended aryl, stretch The heterocycloalkyl and heterocyclic aryl groups may optionally contain O or S or a hydroxyl group; R may be bonded to the ring structures X ₁ and X ₂ at any position, with the proviso that the hydroxyl group on the X ₂ ring is adjacent to Carboxyl group To (PEI); and Z is an aryl group is attached to the covalent bond of an ester group or a carboxylic acid stretch hydrocarbon linking group. An ODF sealant composition comprising the resin of claim 1 and a material selected from the group consisting of a photoinitiator, a free radical initiator, a curing agent, a filler, and combinations thereof. The ODF sealant composition of claim 4, further comprising a material selected from the group consisting of photopolymerizable compounds, thermosetting resins, shakers, decane coupling agents, diluents, modifiers, colorants, interfacial activity Agents, preservatives, stabilizers, plasticizers, lubricants, defoamers, leveling agents, and combinations thereof. An ODF sealant composition comprising the resin of claim 2 and a material selected from the group consisting of photoinitiators, free radical initiators, curing agents, fillers, and combinations thereof. The ODF sealant composition of claim 6, further comprising a material selected from the group consisting of a photopolymerizable compound, a thermosetting resin, a shaker, a decane coupling agent, a diluent, a modifier, a colorant, an interface Active agents, preservatives, stabilizers, plasticizers, lubricants, defoamers, leveling agents, and combinations thereof. An ODF sealant composition comprising the resin of claim 3 and a material selected from the group consisting of photoinitiators, free radical initiators, curing agents, fillers, and combinations thereof. The ODF sealant composition of claim 8, which further comprises a material selected from the group consisting of photopolymerizable compounds, thermosetting resins, shakers, decane coupling agents, diluents, modifiers, colorants, interfaces Active agents, preservatives, stabilizers, plasticizers, lubricants, defoamers, leveling agents, and combinations thereof. An example of a compound selected from the following 2 .