Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
  • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
  • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
  • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
  • C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms

Definitions

• the present invention relates to provision of an acrylic or methacrylic compound having a hydroxyl group, which is expected to be used as an additive for imparting a function to a resin composition, and a method for producing these.
• the photoreactive group has an acrylic group or a methacryl group, and has a plurality of hydroxy groups that are crosslinkable groups. Certain compounds are also known (Patent Document 2).
• a technique for enhancing the function by forming a strong network by introducing a crosslinking agent and a low-molecular compound that reacts with the crosslinking agent into the resin composition is often used.
• satisfactory characteristics cannot be obtained after the light irradiation step, and there are problems that peeling due to the film strength is observed and the deterioration rate is high.
• a compound having an aromatic ring generally has an ability to absorb ultraviolet light, it absorbs light energy, impairs photopatterning, and transparency may be impaired by coloring by an oxidation reaction, which is not preferable.
• the present inventors have produced a compound having an acrylic group or a methacrylic group that is a photoreactive group and a plurality of hydroxy groups that are crosslinkable groups. A method was found and the present invention was completed. That is, the present invention 1.
• R 1 is a hydrogen atom or a methyl group
• R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a hydroxyl alkyl group having 1 to 20 carbon atoms
• R 4 is a hydroxyl group or a hydroxylalkyl group having 1 to 20 carbon atoms.
• R 1 is a hydrogen atom or a methyl group
• glycidyl acrylate or glycidyl methacrylate represented by the following formula (B)
• R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a hydroxyl alkyl group having 1 to 20 carbon atoms, and R 4 is a hydroxyl group or having 1 to 20 carbon atoms.
• R 1 is a hydrogen atom or a methyl group
• R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a hydroxyl alkyl group having 1 to 20 carbon atoms
• R 4 is a hydroxyl group or a hydroxyl alkyl group having 1 to 20 carbon atoms.
• R 2 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and R 3 and R 4 are both hydroxymethyl groups. 7).
• R 5 is a hydrogen atom or a methyl group
• R 6 is a hydroxyl group or a hydroxylalkyl group having 1 to 20 carbon atoms
• R 7 and R 8 are a hydroxylalkyl group having 1 to 20 carbon atoms
• L is alkylene having 2 to 20 carbon atoms).
• R 6 is a hydroxyl group or a hydroxylalkyl group having 1 to 20 carbon atoms
• R 7 and R 8 are hydroxylalkyl groups having 1 to 20 carbon atoms.
• R 5 is a hydrogen atom or a methyl group
• R 6 is a hydroxyl group or a hydroxylalkyl group having 1 to 20 carbon atoms
• R 7 and R 8 are a hydroxylalkyl group having 1 to 20 carbon atoms
• L is alkylene having 2 to 20 carbon atoms.
• the function of the resin composition can be improved by the crosslinking effect, and further improvement of the function can be expected by the crosslinking effect after the light irradiation step. Moreover, since it is a compound which does not contain an aromatic ring, there is no fear of coloring, it is excellent in transparency, and the resin composition excellent in durability, such as heat resistance and water resistance, can be obtained.
• a method for producing an acrylic or methacrylic compound having a hydroxyl group represented by the above formula [1] (hereinafter abbreviated as compound 1) is represented by the following reaction scheme. That is, the target compound 1 is produced by reacting glycidyl acrylate (GA) or glycidyl methacrylate (GMA) represented by the following formula (A) with a carboxylic acid compound represented by the following formula (B).
• G glycidyl acrylate
• GMA glycidyl methacrylate
• B carboxylic acid compound represented by the following formula (B).
• R 1 is a hydrogen atom or a methyl group
• R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a hydroxylalkyl group having 1 to 20 carbon atoms
• 4 is a hydroxyl group or a hydroxylalkyl group having 1 to 20 carbon atoms.
• the alkyl group having 1 to 20 carbon atoms may be linear or branched. Specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, 1-methyl-n-butyl, 2-methyl- n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, n-hexyl, 1-methyl-n-pentyl, 2-methyl-n-pentyl, 1,1-dimethyl-n- Butyl, 1-ethyl-n-butyl, 1,1,2-trimethyl-n-propyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, Examples include
• the hydroxyalkyl group having 1 to 20 carbon atoms is preferably a hydroxy group substituted at the terminal of the alkyl group, such as hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl, 6 -Hydroxyhexyl, 7-hydroxyheptyl, 8-hydroxyoctyl, 9-hydroxynonyl, 10-hydroxydecyl, 11-hydroxyundecyl, 12-hydroxydodecyl, 13-hydroxytridecyl, 14-hydroxytetradecyl, 15-hydroxy Examples include pentadecyl, 16-hydroxyhexadecyl, 17-hydroxyheptadecyl, 18-hydroxyoctadecyl, 19-hydroxynonadecyl and 20-hydroxyeicosyl.
• the amount of the carboxylic acid compound used with respect to GA or GMA is not particularly limited, but a method of removing excess carboxylic acid compound by washing with water after GA or GMA is eliminated is efficient. That is, the amount of the carboxylic acid compound is preferably 1.0 to 3.0 equivalents relative to GA or GMA. More preferably, it is 1.0 equivalent to 1.2 equivalent.
• the reaction solvent is not particularly limited as long as it is inert to the reaction.
• hydrocarbons such as hexane, cyclohexane, benzene and toluene; halogens such as carbon tetrachloride, chloroform and 1,2-dichloroethane Hydrocarbons; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; nitriles such as acetonitrile and propionitrile; ethyl acetate and ethyl propionate N-containing aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone; Dimethyl sul
• Sulfur aprotic polar solvent pyridine, pyridines picoline and the like. These solvents may be used alone, or two or more of these may be mixed and used. Preferred are DMF, ethyl acetate, acetonitrile, and 1,4-dioxane, and more preferred are DMF and ethyl acetate.
• the amount of the solvent used is not particularly limited, but the reaction may be carried out without using a solvent.
• the solvent is 0.1 to 100 times the mass of GA or GMA. May be used.
• the amount is preferably 1 to 10 times by mass, more preferably 2 to 5 times by mass.
• the reaction temperature is not particularly limited, but is, for example, ⁇ 90 to 200 ° C., preferably 0 to 150 ° C., and more preferably 50 ° C. to 120 ° C.
• the reaction time is usually 0.05 to 200 hours, preferably 0.5 to 100 hours.
• a polymerization inhibitor may be added.
• BHT 2,6-di-tert-butyl-para-cresol
• hydroquinone para-methoxyphenol, etc.
• para-methoxyphenol para-methoxyphenol
• the addition amount in the case of adding a polymerization inhibitor is not particularly limited, but is preferably 0.00001 mol to 0.1 mol with respect to the number of moles of the acrylic ester compound (GA) or methacrylic ester compound (GMA). Is 0.001 to 0.01 mol.
• Catalysts may be added to shorten the reaction time, examples of which include benzyltrimethylammonium chloride (BTMAC), benzyltriethylammonium chloride (BTEAC), benzyltrimethylammonium bromide (BTMAB), benzyltriethylammonium bromide (BTEAB). ), Quaternary ammonium salts such as tetrabutylammonium chloride (TBAC) and tetrabutylammonium bromide (TBAB), and quaternary phosphonium salts such as tetraphenylphosphonium bromide (TPPB).
• BTMAC benzyltrimethylammonium chloride
• BTEAC benzyltriethylammonium chloride
• BTMAB benzyltrimethylammonium bromide
• BTEAB benzyltriethylammonium bromide
• Quaternary ammonium salts such as
• a base catalyst may be added, and examples thereof include triethylamine, trimethylamine, tripropylamine, tributylamine, diisopropylethylamine, pyridine, imidazole, N, N-dimethylamino-4-pyridine, 1,8-diazabicyclo Organic bases such as [5.4.0] undecene-7 (DBU), 1,5-diaza-bicyclo [4.3.0] nonene-5 (DBN), alkali metal hydroxides such as sodium hydroxide Alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, alkaline earth metal carbonates such as barium carbonate and calcium carbonate Alkali metal bicarbonates such as sodium bicarbonate, bicarbonate Alkali metal salts of inorganic acids such as potassium, for example inorganic bases such as 2- or 3-sodium phosphate, 2- or 3-potassium phosphate.
• DBU undecene
• the amount added may be 0.003 to 1 mol, preferably 0.03 to 0.5 mol, more preferably 0.05 to 0.00 mol per mol of GA or GMA. 2 moles.
• the amount of the catalyst is large, a large amount of water is required for removing the catalyst, and it is not economically preferable.
• the amount of the catalyst is small, the reaction is delayed, and it takes a long time to complete the reaction.
• This reaction can be carried out at normal pressure or under pressure, and may be batch or continuous.
• the amount of water used for washing may be any amount that can remove the catalyst used in the reaction, but if the amount of water is large, the target product moves to the aqueous layer and the recovery rate decreases. Therefore, the ratio of water to the washing solvent is preferably 5: 1 to 1: 100, more preferably 2: 1 to 1:20.
• a method for producing an acrylic or methacrylic compound having a hydroxyl group represented by the above formula [3] is represented by the following reaction scheme. That is, by reacting an isocyanatoalkyl acrylate (IAA) or isocyanatoalkyl methacrylate (IAM) represented by the following formula (C) with an amine compound represented by the following formula (D), the desired compound 3 Is manufactured.
• R 5 is a hydrogen atom or a methyl group
• R 6 is a hydroxyl group or a hydroxylalkyl group having 1 to 20 carbon atoms
• R 7 and R 8 are a hydroxylalkyl group having 1 to 20 carbon atoms
• L is alkylene having 2 to 20 carbon atoms.
• the alkyl group having 1 to 20 carbon atoms may be linear or branched. Specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, 1-methyl-n-butyl, 2-methyl- n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, n-hexyl, 1-methyl-n-pentyl, 2-methyl-n-pentyl, 1,1-dimethyl-n- Butyl, 1-ethyl-n-butyl, 1,1,2-trimethyl-n-propyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, Examples include
• the hydroxyalkyl group having 1 to 20 carbon atoms is preferably a hydroxy group substituted at the terminal of the alkyl group, such as hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl, 6 -Hydroxyhexyl, 7-hydroxyheptyl, 8-hydroxyoctyl, 9-hydroxynonyl, 10-hydroxydecyl, 11-hydroxyundecyl, 12-hydroxydodecyl, 13-hydroxytridecyl, 14-hydroxytetradecyl, 15-hydroxy Examples include pentadecyl, 16-hydroxyhexadecyl, 17-hydroxyheptadecyl, 18-hydroxyoctadecyl, 19-hydroxynonadecyl and 20-hydroxyeicosyl.
• alkylene having 2 to 20 carbon atoms examples include divalent groups in which one hydrogen atom is further removed from the above alkyl group having 1 to 20 carbon atoms having 2 or more carbon atoms.
• the amount of IAA or IAM used with respect to the amine compound is not particularly limited, but is preferably 0.9 equivalent to 3.0 equivalent with respect to the amine compound. More preferably, it is 1.0 equivalent to 1.2 equivalent.
• the reaction solvent is not particularly limited as long as it is inert to the reaction.
• hydrocarbons such as hexane, cyclohexane, benzene and toluene; halogens such as carbon tetrachloride, chloroform and 1,2-dichloroethane Hydrocarbons; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; nitriles such as acetonitrile and propionitrile; ethyl acetate and ethyl propionate N-containing aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone; Dimethyl sul
• Sulfur aprotic polar solvent pyridine, pyridines picoline and the like. These solvents may be used alone, or two or more of these may be mixed and used. Among them, a solvent that dissolves IAA and IMA but hardly dissolves compound 3 is preferable in that compound 3 obtained can be easily isolated by filtration.
• solvents are preferably tetrahydrofuran, ethyl acetate, Toluene and acetonitrile are preferable, and tetrahydrofuran is more preferable.
• the amount of the solvent used is not particularly limited, but the reaction may be carried out without using a solvent, and when a solvent is used, the solvent is 0.1 to 100 times by mass with respect to IAA or IAM. May be used.
• the amount is preferably 1 to 10 times by mass, more preferably 2 to 5 times by mass.
• the reaction temperature is not particularly limited, but is, for example, ⁇ 90 to 200 ° C., preferably ⁇ 50 to 150 ° C., and more preferably ⁇ 20 ° C. to 120 ° C.
• the reaction time is usually 0.05 to 200 hours, preferably 0.5 to 100 hours.
• a polymerization inhibitor may be added.
• BHT 2,6-di-tert-butyl-para-cresol
• hydroquinone para-methoxyphenol, etc.
• para-methoxyphenol para-methoxyphenol
• the addition amount in the case of adding a polymerization inhibitor is not particularly limited, but is preferably 0.00001 mol to 0.1 mol with respect to the number of moles of the acrylic ester compound (IAA) or the methacrylic ester compound (IAM). Is 0.001 to 0.01 mol.
• Catalysts may be added to shorten the reaction time, examples of which include benzyltrimethylammonium chloride (BTMAC), benzyltriethylammonium chloride (BTEAC), benzyltrimethylammonium bromide (BTMAB), benzyltriethylammonium bromide (BTEAB). ), Quaternary ammonium salts such as tetrabutylammonium chloride (TBAC) and tetrabutylammonium bromide (TBAB), and quaternary phosphonium salts such as tetraphenylphosphonium bromide (TPPB).
• BTMAC benzyltrimethylammonium chloride
• BTEAC benzyltriethylammonium chloride
• BTMAB benzyltrimethylammonium bromide
• BTEAB benzyltriethylammonium bromide
• Quaternary ammonium salts such as
• a base catalyst may be added, and examples thereof include triethylamine, trimethylamine, tripropylamine, tributylamine, diisopropylethylamine, pyridine, imidazole, N, N-dimethylamino-4-pyridine, 1,8-diazabicyclo Organic bases such as [5.4.0] undecene-7 (DBU), 1,5-diaza-bicyclo [4.3.0] nonene-5 (DBN), alkali metal hydroxides such as sodium hydroxide Alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, alkaline earth metal carbonates such as barium carbonate and calcium carbonate Alkali metal bicarbonates such as sodium bicarbonate, bicarbonate Alkali metal salts of inorganic acids such as potassium, for example inorganic bases such as 2- or 3-sodium phosphate, 2- or 3-potassium phosphate.
• DBU undecene
• the amount added may be 0.001 to 1 mol, preferably 0.005 to 0.5 mol, more preferably 0.01 to 0.00 mol per mol of IAA or IAM. 2 moles.
• This reaction can be carried out at normal pressure or under pressure, and may be batch or continuous.
• the precipitated compound 3 crystals are collected by filtration and washed with a solvent such as tetrahydrofuran or ethyl acetate to obtain the target compound.
• a solvent such as tetrahydrofuran or ethyl acetate.
• GMA glycidyl methacrylate 2HM-PA: 2,2-bis (hydroxymethyl) propionic acid
• BHT 2,6-di-tert-butyl-p-cresol
• BTMAC benzyltriethylammonium chloride
• BTEAC benzyltriethylammonium chloride
• TPPB tetraphenyl Phosphonium bromide
• DMF dimethylformamide
• Example 2 The same operation as Example 1 was implemented until the water washing operation, and the following operation was performed after water washing. 803.0 g of PGME and 262.2 g of magnesium sulfate were added to the organic layer after washing twice, and after stirring for 1 hour, the magnesium sulfate was filtered. The filtrate was distilled off at 45 ° C. with an evaporator at 100 Torr. Concentrate until no more to give 1102.2 g of solution. This solution was confirmed to be a 52.9 wt% solution of GMA-2HM-PAE from the results of quantitative analysis by high performance liquid chromatography.
• Example 3 Under a nitrogen stream, DMF 1350.0 g, GMA 458.2 g (3.22 mol) and 2HM-PA 528.8 g (3.94 mol), BHT 4.6 g (20.87 mmol), BTMAC 13.5 g (72. 70 mmol) was charged at room temperature, heated to 80 ° C. with magnetic stirring, and stirred for 24 hours. After confirming that GMA was less than 0.5 area%, DMF was concentrated. To the DMF concentrate, 4101.0 g of ethyl acetate was added, followed by 4059.0 g of pure water, washed with water in a separatory funnel, and the aqueous layer was discarded.
• Example 4 A series of operations were carried out in the same manner as in Example 1. Only the catalyst was changed to BTMAC, and the mixture was heated and stirred for 21 hours. As a result of analyzing the reaction solution by high performance liquid chromatography, it was confirmed that GMA was 0.5 area% or less.
• Example 5 A series of operations were carried out in the same manner as in Example 1. The catalyst was changed to TPPB, and the mixture was heated and stirred for 21 hours. As a result of analyzing the reaction solution by high performance liquid chromatography, it was confirmed that GMA was 0.5 area% or less.
• Example 6 A series of operations were carried out in the same manner as in Example 1, except that only the catalyst was changed to BTMAC, and the amount of catalyst was 0.025 mol relative to the number of moles of GMA. As a result of analyzing the reaction solution by high performance liquid chromatography after 21 hours, it was confirmed that 17.5 area% GMA remained and GMA was 0.5 area% or less after 44 hours. It was.
• Example 7 Each cured film forming composition of Example 7 and Comparative Example 1 was prepared with the composition shown in Table 2. Next, a cured film was formed using each cured film forming composition, and adhesion, orientation sensitivity, pattern formability, and transmittance were evaluated for each of the obtained cured films.
• a film having a thickness of 1.0 ⁇ m was formed. This film was exposed at 1000 mJ / cm 2 to polymerize the polymerizable liquid crystal to produce a retardation material. A crosscut (1 mm ⁇ 1 mm ⁇ 100 squares) was put into the retardation material on the obtained substrate using a cutter knife, and then a cellophane tape was attached. Next, when the cellophane tape was peeled off, the number of squares remaining in the retardation material on the substrate where the polymerized polymerizable liquid crystal film was not peeled off on the lower cured film was counted. The evaluation results are “initial” and are shown in Table 2 in the form of (number of cells remaining without peeling off the film) / 100. Adhesiveness was judged to be good when 90 or more squares remained without peeling off the film, that is, 90/100 to 100/100.
• Each of the cured film forming compositions of Examples and Comparative Examples was spin-coated on an alkali glass at 2000 rpm for 30 seconds using a spin coater, and then heated and dried in a thermal circulation oven at a temperature of 110 ° C. for 120 seconds to obtain a cured film. Formed. Each cured film was vertically irradiated with 313 nm linearly polarized light to form an alignment material. On the alignment material on the substrate, a polymerizable liquid crystal solution RMS03-013C for horizontal alignment manufactured by Merck Co., Ltd. was applied using a spin coater, and then pre-baked on a hot plate at 60 ° C. for 60 seconds to obtain a film thickness.
• a 1.0 ⁇ m coating film was formed.
• the coating film on this substrate was exposed at 1000 mJ / cm 2 to produce a retardation material.
• the retardation material on the prepared substrate is sandwiched between a pair of polarizing plates, the state of retardation property development in the retardation material is observed, and the exposure amount of polarized UV necessary for the alignment material to exhibit liquid crystal alignment is determined. It was.
• the evaluation results are summarized in Table 2 later.
• the alignment materials formed using each of the cured film forming compositions of Examples 1 to 3 and Comparative Example each have an exposure amount of polarized UV necessary to exhibit liquid crystal alignment of 20 mJ / cm 2 to 40 mJ. The value was as low as / cm 2 , indicating good alignment sensitivity.
• a polymerizable liquid crystal solution RMS03-013C for horizontal alignment manufactured by Merck Co., Ltd. was applied using a spin coater, and then pre-baked on a hot plate at 60 ° C. for 60 seconds to form a film.
• a coating film having a thickness of 1.0 ⁇ m was formed.
• the coating film on this substrate was exposed at 1000 mJ / cm 2 to prepare a patterned retardation material in which two types of regions having different retardation characteristics were regularly arranged.
• the patterned phase difference material on the produced substrate was observed using a polarizing microscope, and evaluation was made with ⁇ indicating that the phase difference pattern was formed without alignment defects, and ⁇ indicating that the alignment defects were observed. The evaluation results are shown later in Table 3.
• the cured film obtained using the cured film forming composition of Example 7 maintained high adhesion even after high temperature and high humidity treatment, and exhibited excellent adhesion durability.
• the cured film obtained using the cured film-forming composition of Comparative Example 1 was difficult to maintain the initial adhesion after the high temperature and high humidity treatment.
• the alignment material obtained using the cured film-forming composition of Example 7 was polarized UV necessary for exhibiting liquid crystal alignment properties, similar to the alignment material obtained using the cured film-forming composition of Comparative Example.
• the amount of exposure are both a low and 20mJ / cm 2 ⁇ 40mJ / cm 2, it showed a good alignment sensitivity.
• the alignment material obtained using the cured film-forming composition of Example 7 showed good pattern-forming properties, similar to the alignment material obtained using the cured film-forming composition of the comparative example.
• the cured film obtained using the cured film-forming composition of Example 7 was 100% of light having a wavelength of 400 nm, similarly to the cured film obtained using the cured film-forming composition of the comparative example.
• the transmittance was shown and good light transmission characteristics were exhibited.
• the compound of the present invention has the effect of improving the adhesion durability of the cured film-forming composition, and also affects the properties such as light transmittance and pattern formability. It was confirmed not to give.
• Example 8 Synthesis of 2- (3- (1,3-dihydroxy-2- (hydroxymethyl) propan-2-yl) ureido) ethyl methacrylate Under a nitrogen stream, THF (tetrahydrofuran) 100 ml, THAM (trishydroxymethylaminomethane) 2.42 g (20.0 mmol) and BHT (2,6-di-tert-butyl-p-cresol) 33.0 mg (0. 150 mmol) was charged at 25 ° C., and 3.26 g (21.0 mmol) of 2-IEM (2-isocyanatoethyl methacrylate) was added with stirring with a magnetic stirrer.
• THF tetrahydrofuran
• THAM trishydroxymethylaminomethane
• BHT 2,6-di-tert-butyl-p-cresol
• the compound of the present invention improves the performance of a cured film obtained by adding it to a resin composition used in the field of displays such as a television using a liquid crystal panel and in the semiconductor field, and has characteristics such as transparency. Is useful as an additive or the like that does not affect.

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