Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

• the present invention relates to a liquid crystal alignment agent containing polysiloxane obtained by polycondensation of alkoxysilane, a liquid crystal alignment film obtained from the liquid crystal alignment agent, and a liquid crystal display device having the liquid crystal alignment film.
• VA liquid crystal display elements are widely used for large-screen liquid crystal televisions and high-definition mobile applications (display units of digital cameras and mobile phones).
• the VA method includes an MVA method (Multi Vertical Alignment) in which protrusions for controlling the direction in which the liquid crystal is tilted are formed on the TFT substrate or the color filter substrate, and a direction in which the liquid crystal is tilted by an electric field by forming a slit in the ITO electrode of the substrate.
• MVA method Multi Vertical Alignment
• a PVA (Paterned Vertical Alignment) system to be controlled is known.
• VA alignment method is the PSA (Polymer Sustained Alignment) method.
• the PSA system is a technology that has attracted attention in recent years.
• a photopolymerizable compound is added to the liquid crystal, and after the liquid crystal panel is produced, an electric field is applied to irradiate the liquid crystal panel with UV in a state where the liquid crystal is tilted.
• the polymerizable compound is photopolymerized to fix the alignment direction of the liquid crystal, causing a pretilt and improving the response speed.
• a slit is formed in one electrode constituting the liquid crystal panel, and a structure in which a projection such as MVA or a slit such as PVA is not provided in the opposite electrode pattern is operable. It is characterized by simplification and excellent panel transmittance. (See Patent Document 1.)
• an inorganic liquid crystal alignment film material is also known together with an organic liquid crystal alignment film material such as polyimide which has been conventionally used.
• a liquid crystal aligning agent composition containing a reaction product of tetraalkoxysilane, trialkoxysilane, alcohol, and oxalic acid is used as a material for a coating-type inorganic alignment film on an electrode substrate of a liquid crystal display element. It is reported that a liquid crystal alignment film having excellent vertical alignment properties, heat resistance and uniformity is formed. (See Patent Document 2.)
• liquid crystal aligning agent composition containing a reaction product of tetraalkoxysilane, specific trialkoxysilane and water and a specific glycol ether solvent, display defects are prevented and even after long-time driving. It has been reported to form a liquid crystal alignment film with good afterimage characteristics, without reducing the ability to align liquid crystals, and with little reduction in voltage holding ratio against light and heat. (See Patent Document 3)
• JP 2004-302061 A JP 09-281502 A JP 2005-250244 A
• the object of the present invention is to improve the response speed in a PSA type liquid crystal display element even when the amount of the polymerizable compound is small, or even when using a liquid crystal without adding a polymerizable compound, and a good alignment state. It is possible to provide a liquid crystal aligning agent for a liquid crystal display element, a liquid crystal aligning film obtained from the liquid crystal aligning agent, and a liquid crystal display element having the liquid crystal aligning film.
• R 1 Si (OR 2 ) 3 (1) R 1 is a hydrocarbon group having 8 to 30 carbon atoms which may be substituted with a fluorine atom, and R 2 represents an alkyl group having 1 to 5 carbon atoms.
• R 3 Si (OR 4 ) 3 (2) R 3 represents an alkyl group substituted with an acryl group or a methacryl group, and R 4 represents an alkyl group having 1 to 5 carbon atoms.
• R 1 in the formula (1) is a hydrocarbon group having 8 to 22 carbon atoms, and R 2 is methyl or ethyl.
• R 2 is methyl or ethyl.
• the alkoxysilane represented by the formula (2) is 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxy.
• R 5 of the alkoxysilane represented by the formula (3) is a hydrocarbon group having 1 to 6 carbon atoms.
• the alkoxysilane represented by the formula (1) is contained in an amount of 0.1 to 30 mol% in all alkoxysilanes, and the alkoxysilane represented by the formula (2) is 3% in all alkoxysilanes.
• liquid crystal aligning agent according to any one of [1] to [9] is applied, and UV is irradiated in a state where a voltage is applied to a liquid crystal cell in which the liquid crystal is sandwiched between two baked substrates.
• Liquid crystal display element [13] A liquid crystal display element in which the liquid crystal aligning agent according to any one of [1] to [9] is applied, the liquid crystal is sandwiched between two baked substrates, and UV is irradiated in a state where a voltage is applied. Production method.
• liquid crystal aligning agent of the present invention in the PSA type liquid crystal display element, even when the amount of the polymerizable compound added to the liquid crystal is small, or when the liquid crystal without adding the polymerizable compound is used, A liquid crystal alignment film for a liquid crystal display element and a liquid crystal display element having the liquid crystal alignment film capable of improving the response speed and obtaining a good alignment state can be obtained.
• This invention is a liquid crystal aligning agent containing the polysiloxane obtained by polycondensing the alkoxysilane containing the alkoxysilane represented by Formula (1), and the alkoxysilane represented by Formula (2).
• R 1 Si (OR 2 ) 3 (1) R 1 is a hydrocarbon group having 8 to 30 carbon atoms which may be substituted with a fluorine atom, and R 2 represents an alkyl group having 1 to 5 carbon atoms.
• “substituted” “May be substituted” means “substituted or unsubstituted”.
• R 3 Si (OR 4 ) 3 (2) R 3 represents an alkyl group substituted with an acryl group or a methacryl group, and R 4 represents an alkyl group having 1 to 5 carbon atoms.)
• R 1 of the alkoxysilane represented by the formula (1) has 8 to 30 carbon atoms which may be substituted with fluorine, preferably 8 to 22 and particularly preferably 10 carbon atoms.
• the hydrocarbon group is not particularly limited as long as it has an effect of vertically aligning liquid crystals. Examples thereof include an alkyl group, a fluoroalkyl group, an alkenyl group, a phenethyl group, a styrylalkyl group, a naphthyl group, and a fluorophenylalkyl group.
• alkoxysilanes in which R 1 is an alkyl group or a fluoroalkyl group are preferable because they are relatively inexpensive and easily available as commercial products.
• alkoxysilane in which R 1 is an alkyl group is preferable.
• the polysiloxane used in the present invention may have a plurality of these specific organic groups.
• R 2 of the alkoxysilane represented by the formula (1) is an alkyl group having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms. More preferably, R 2 is a methyl group or an ethyl group.
• octyltrimethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, decyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxysilane, heptadecyltrimethoxysilane Heptadecyltriethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, nonadecyltrimethoxysilane, nonadecyltriethoxysilane, undecyltriethoxysilane, or undecyltrimethoxysilane is preferred.
• the above-mentioned alkoxysilane represented by the formula (1) having a specific organic group is preferably 0.1 mol% or more in order to obtain good liquid crystal alignment in all alkoxysilanes used for obtaining polysiloxane. More preferably, it is 0.5 mol% or more. More preferably, it is 1 mol% or more. Further, in order to obtain sufficient curing characteristics of the liquid crystal alignment film to be formed, 30 mol% or less is preferable. More preferably, it is 22 mol% or less.
• alkoxysilane R 3 represented by (hereinafter, also referred to as a second specific organic groups) R 3 is an alkyl group substituted with an acrylic group or methacrylic group.
• the number of substituted hydrogen atoms is one or more, preferably one.
• the number of carbon atoms of the alkyl group is preferably 1-30, more preferably 1-10. More preferably, it is 1-5.
• R 4 of the alkoxysilane represented by the formula (2) is the same as the definition of R 2 in the above formula (1), and a preferable group of R 4 is the same as that of R 2 .
• alkoxysilane represented by Formula (2) is not limited to these.
• 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, methacryloxymethyltrimethoxysilane, methacryloxymethyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxy Examples include silane, acryloxyethyltrimethoxysilane, acryloxyethyltriethoxysilane, and the like.
• the alkoxysilane represented by the formula (2) having the second specific organic group obtains polysiloxane. Therefore, 3 mol% or more is preferable in all alkoxysilanes used for this purpose. More preferably, it is 5 mol% or more. More preferably, it is 10 mol% or more. Moreover, in order to fully harden the liquid crystal aligning film formed, 60 mol% or less is preferable.
• the alkoxysilane represented by the formula (1) is preferably contained in the total alkoxysilane used in an amount of 0.1 to 30 mol%, particularly preferably 2 to 20 mol%, and the formula (2) It is preferable that 3 to 60 mol%, particularly preferably 5 to 30 mol% is contained in all alkoxysilanes used.
• the alkoxysilane represented by following formula (3) other than the alkoxysilane represented by Formula (1) and Formula (2) can be used. Since the alkoxysilane represented by the formula (3) can impart various characteristics to the polysiloxane, one or more kinds can be selected and used according to the required characteristics.
• R 5 is a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hetero atom, a halogen atom, an amino group, a glycidoxy group, a mercapto group, an isocyanate group or a ureido group.
• R 6 represents an alkyl group having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, and n represents an integer of 0 to 3, preferably 0 to 2.
• R 5 of the alkoxysilane represented by the formula (3) is a hydrogen atom or an organic group having 1 to 6 carbon atoms (hereinafter also referred to as a third organic group).
• the third organic group include aliphatic hydrocarbons; ring structures such as aliphatic rings, aromatic rings and heterocycles; unsaturated bonds; and heteroatoms such as oxygen atoms, nitrogen atoms and sulfur atoms. It is a hydrocarbon having 1 to 16, more preferably 1 to 12, and particularly preferably 1 to 6 carbon atoms which may be contained and may have a branched structure.
• This hydrocarbon may be substituted with a halogen atom, amino group, glycidoxy group, mercapto group, isocyanate group, ureido group or the like.
• a halogen atom amino group, glycidoxy group, mercapto group, isocyanate group, ureido group or the like.
• R 5 is a hydrogen atom
• specific examples of the alkoxysilane when R 5 is a hydrogen atom include trimethoxysilane, triethoxysilane, tripropoxysilane, tributoxysilane and the like.
• alkoxysilane of the formula (3) specific examples of the alkoxysilane when R 5 is a third organic group include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, and ethyltriethoxysilane.
• the polysiloxane used in the present invention is a kind of the alkoxysilane represented by the above formula (3) as long as the effect of the present invention is not impaired for the purpose of improving the adhesion with the substrate and the affinity with the liquid crystal molecules. Or you may have multiple types.
• the alkoxysilane represented by the formula (3) the alkoxysilane in which n is 0 is tetraalkoxysilane. Tetraalkoxysilane is preferable for obtaining the polysiloxane of the present invention because it easily condenses with the alkoxysilane represented by the formulas (1) and (2).
• the alkoxysilane in which n is 0 in the formula (3) tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane or tetrabutoxysilane is more preferable, and tetramethoxysilane or tetraethoxysilane is particularly preferable.
• the amount of the alkoxysilane represented by the formula (3) is 10 to 96.9 mol% in the total alkoxysilane used for obtaining the polysiloxane. It is preferable that More preferably, it is 35 to 99.8 mol%.
• the method for obtaining the polysiloxane used in the present invention is not particularly limited. In the present invention, it is obtained by condensing an alkoxysilane having the above-mentioned formulas (1) and (2) as essential components in an organic solvent. Usually, polysiloxane is obtained as a solution obtained by polycondensation of such alkoxysilanes and uniformly dissolved in an organic solvent. Examples of the method for polycondensing the alkoxysilane include a method of hydrolyzing and condensing the alkoxysilane in a solvent such as alcohol or glycol. At that time, the hydrolysis / condensation reaction may be either partial hydrolysis or complete hydrolysis.
• acids such as hydrochloric acid, sulfuric acid, nitric acid, acetic acid, formic acid, succinic acid, maleic acid, fumaric acid; ammonia, methylamine, ethylamine, ethanolamine
• a catalyst such as alkali such as triethylamine
• metal salt such as hydrochloric acid, sulfuric acid and nitric acid.
• the hydrolysis / condensation reaction can be further promoted by heating the solution in which the alkoxysilane is dissolved. At that time, the heating temperature and the heating time can be appropriately selected as desired. For example, heating and stirring at 50 ° C.
• a method of heating and polycondensing a mixture of alkoxysilane, a solvent and oxalic acid can be mentioned. Specifically, after adding oxalic acid to alcohol in advance to obtain an alcohol solution of oxalic acid, the alkoxysilane is mixed while the solution is heated. In that case, the amount of succinic acid used is preferably 0.2 to 2 mol with respect to 1 mol of all alkoxy groups of the alkoxysilane. Heating in this method can be performed at a liquid temperature of 50 to 180 ° C. Preferably, it is a method of heating for several tens of minutes to several tens of hours under reflux so that evaporation or volatilization of the liquid does not occur.
• the alkoxysilanes may be mixed in advance, or multiple types of alkoxysilanes may be mixed in sequence.
• the solvent used for polycondensation of alkoxysilane (hereinafter also referred to as polymerization solvent) is not particularly limited as long as it can dissolve alkoxysilane. Moreover, even when alkoxysilane does not melt
• Such a polymerization solvent include alcohols such as methanol, ethanol, propanol, butanol and diacetone alcohol: ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1 , 5-pentanediol, 2,4-pentanediol, 2,3-pentanediol, 1,6-hexanediol, and other glycols: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether Ethylene glycol monobutyl ether
• the polysiloxane polymerization solution (hereinafter also referred to as polymerization solution) obtained by the above method is a concentration obtained by converting silicon atoms of all alkoxysilanes charged as raw materials into SiO 2 (hereinafter referred to as SiO 2 conversion concentration). ) Is preferably 20% by mass or less, more preferably 5 to 15% by mass. By selecting an arbitrary concentration within this concentration range, gel formation can be suppressed and a homogeneous solution can be obtained.
• the polymerization solution obtained by the above method may be used as a polysiloxane solution as it is, or if necessary, the solution obtained by the above method may be concentrated or diluted by adding a solvent. Or may be substituted with another solvent to form a polysiloxane solution.
• the solvent to be used hereinafter also referred to as additive solvent
• the additive solvent is not particularly limited as long as the polysiloxane is uniformly dissolved, and one kind or plural kinds can be arbitrarily selected and used.
• Such an additive solvent include, in addition to the solvents mentioned as examples of the polymerization solvent described above, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; esters such as methyl acetate, ethyl acetate, and ethyl lactate. Can be mentioned. These solvents can improve the applicability when the liquid crystal aligning agent is applied onto the substrate by adjusting the viscosity of the liquid crystal aligning agent, or by spin coating, flexographic printing, ink jetting or the like.
• liquid crystal aligning agent of the present invention other components other than polysiloxane, such as inorganic fine particles, metalloxane oligomers, metalloxane polymers, leveling agents, and further surfactants, etc., as long as the effects of the present invention are not impaired. May be included.
• inorganic fine particles fine particles such as silica fine particles, alumina fine particles, titania fine particles, and magnesium fluoride fine particles are preferable, and those in the state of a colloidal solution are particularly preferable.
• This colloidal solution may be a dispersion of inorganic fine particles in a dispersion medium, or a commercially available colloidal solution.
• the inclusion of inorganic fine particles makes it possible to impart the surface shape of the formed cured film and other functions.
• the inorganic fine particles preferably have an average particle size of 0.001 to 0.2 ⁇ m, more preferably 0.001 to 0.1 ⁇ m. When the average particle diameter of the inorganic fine particles exceeds 0.2 ⁇ m, the transparency of the cured film formed using the prepared coating liquid may be lowered.
• the dispersion medium for the inorganic fine particles include water and organic solvents.
• the colloidal solution it is preferable that the pH or pKa is adjusted to 1 to 10 from the viewpoint of the stability of the coating solution for forming a film. More preferably, it is 2-7.
• organic solvent used for the dispersion medium of the colloidal solution examples include alcohols such as methanol, propanol, butanol, ethylene glycol, propylene glycol, butanediol, pentanediol, hexylene glycol, diethylene glycol, dipropylene glycol, and ethylene glycol monopropyl ether; Ketones such as methyl ethyl ketone and methyl isobutyl ketone; aromatic hydrocarbons such as toluene and xylene; amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone; esters such as ethyl acetate, butyl acetate and ⁇ -butyrolactone; Examples include ethers such as tetrahydrofuran and 1,4-dioxane.
• metalloxane oligomer and metalloxane polymer single or composite oxide precursors such as silicon, titanium, aluminum, tantalum, antimony, bismuth, tin, indium, and zinc are used.
• the metalloxane oligomer or metalloxane polymer may be a commercially available product or may be obtained from a monomer such as a metal alkoxide, nitrate, hydrochloride, or carboxylate by a conventional method such as hydrolysis.
• metalloxane oligomers and metalloxane polymers include siloxane oligomers or siloxanes such as methyl silicate 51, methyl silicate 53A, ethyl silicate 40, ethyl silicate 48, EMS-485, SS-101 manufactured by Colcoat Co.
• examples thereof include titanoxane oligomers such as polymers and titanium-n-butoxide tetramer manufactured by Kanto Chemical Co., Inc. You may use these individually or in mixture of 2 or more types.
• a leveling agent, surfactant, etc. can use a well-known thing, and since a commercial item is easy to acquire especially, it is preferable.
• the method of mixing the above-mentioned other components with polysiloxane may be simultaneous with or after polysiloxane, and is not particularly limited.
• the liquid crystal aligning agent of this invention melt
• a solvent selected from the group consisting of the above-mentioned polysiloxane polymerization solvent and additive solvent is used as the solvent.
• the content of polysiloxane in the liquid crystal aligning agent is preferably 0.5 to 15% by mass, more preferably 1 to 6% by mass in terms of SiO 2 equivalent concentration. Be in the range of such terms of SiO 2 concentration, easily obtained a desired film thickness by a single coating, easy pot life sufficient solution is obtained.
• the method for preparing the liquid crystal aligning agent of the present invention is not particularly limited.
• the polysiloxane used in the present invention may be in a state where other components added as necessary are uniformly mixed. Since polysiloxane is usually polycondensed in a solvent, it is convenient to use the polysiloxane solution as it is or to add other components to the polysiloxane solution as necessary. Furthermore, the most convenient method is to use the polysiloxane polymerization solution as it is. Moreover, when adjusting content of polysiloxane in a liquid crystal aligning agent, the solvent chosen from the group which consists of the polymerization solvent and addition solvent of the polysiloxane mentioned above can be used.
• the liquid crystal aligning film of this invention is obtained using the said liquid crystal aligning agent.
• the cured film obtained by drying and baking can also be used as a liquid crystal aligning film as it is.
• the cured film is rubbed, irradiated with polarized light or light of a specific wavelength, or treated with an ion beam, or a voltage is applied to the liquid crystal display element after filling the liquid crystal as a PSA alignment film It is also possible to irradiate with UV. In particular, it is useful to use as an alignment film for PSA.
• the substrate on which the liquid crystal aligning agent is applied is not particularly limited as long as it is a highly transparent substrate, but a substrate in which a transparent electrode for driving liquid crystal is formed on the substrate is preferable.
• Specific examples include glass plate, polycarbonate, poly (meth) acrylate, polyethersulfone, polyarylate, polyurethane, polysulfone, polyether, polyetherketone, trimethylpentene, polyolefin, polyethylene terephthalate, (meth) acrylonitrile, tri
• a substrate in which a transparent electrode is formed on a plastic plate such as acetyl cellulose, diacetyl cellulose, and acetate butyrate cellulose.
• Examples of the method for applying the liquid crystal aligning agent include spin coating, printing, ink jet, spraying, roll coating, and the like.In terms of productivity, the transfer printing method is widely used industrially.
• the present invention is also preferably used.
• the drying process after applying the liquid crystal aligning agent is not necessarily required, but if the time from application to baking is not constant for each substrate, or if baking is not performed immediately after application, a drying process is included. Is preferred.
• the drying is not particularly limited as long as the solvent is removed to such an extent that the shape of the coating film is not deformed by transporting the substrate or the like.
• a method of drying on a hot plate at a temperature of 40 ° C. to 150 ° C., preferably 60 ° C. to 100 ° C., for 0.5 to 30 minutes, preferably 1 to 5 minutes can be mentioned.
• the coating film formed by applying the liquid crystal aligning agent by the above method can be baked to obtain a cured film.
• the firing temperature can be any temperature of 100 ° C. to 350 ° C., preferably 140 ° C. to 300 ° C., more preferably 150 ° C. to 230 ° C., and still more preferably 160 ° C. to 220 ° C. It is. Firing can be performed at an arbitrary time of 5 minutes to 240 minutes. The time is preferably 10 to 90 minutes, more preferably 20 to 90 minutes.
• a generally known method such as a hot plate, a hot air circulation oven, an IR oven, a belt furnace or the like can be used.
• the polysiloxane in the liquid crystal alignment film undergoes polycondensation in the firing step.
• firing is preferably performed at a temperature higher by 10 ° C. or more than the heat treatment temperature required for the liquid crystal cell production process, such as curing of the sealant.
• the thickness of the cured film can be selected as necessary, but is preferably 5 nm or more, more preferably 10 nm or more, because the reliability of the liquid crystal display element can be easily obtained.
• the thickness of the cured film is preferably 300 nm or less, more preferably 150 nm or less, the power consumption of the liquid crystal display element does not become extremely large, which is suitable.
• the liquid crystal display element of the present invention can be obtained by forming a liquid crystal alignment film on a substrate by the above method and then preparing a liquid crystal cell by a known method.
• a method is generally employed in which a pair of substrates on which a liquid crystal alignment film is formed are fixed with a sealant with a spacer interposed therebetween, and liquid crystal is injected and sealed.
• the size of the spacer used is 1 to 30 ⁇ m, preferably 2 to 10 ⁇ m.
• the method for injecting the liquid crystal is not particularly limited, and examples thereof include a vacuum method for injecting liquid crystal after the inside of the manufactured liquid crystal cell is decompressed, and a dropping method for sealing after dropping the liquid crystal.
• a liquid crystal to which a small amount (typically 0.2 to 1% by weight) of a photopolymerizable compound is used is used as the liquid crystal to be used.
• the polymerizable compound is polymerized and crosslinked in situ, thereby increasing the response speed of the liquid crystal display.
• the applied voltage is 5 to 30 Vp-p, preferably 5 to 20 Vp-p.
• the UV irradiation amount to be irradiated is 1 to 60 J, but is preferably 40 J or less. The smaller the UV irradiation amount, the lowering of reliability due to the destruction of the members constituting the liquid crystal display can be suppressed, and the UV irradiation time It is preferable because the manufacturing tact can be increased by reducing.
• the substrate used for the liquid crystal display element is not particularly limited as long as it is a highly transparent substrate, but is usually a substrate on which a transparent electrode for driving liquid crystal is formed.
• a specific example is the same as the substrate described in [Liquid crystal alignment film].
• a substrate that can be used in a PSA type liquid crystal cell a standard electrode pattern such as PVA or MVA or a projection pattern can be used.
• the PSA type liquid crystal display can operate even in a structure in which a line / slit electrode pattern of 1 to 10 ⁇ m is formed on one side substrate and no slit pattern or projection pattern is formed on the opposite substrate.
• the liquid crystal display can simplify the manufacturing process and obtain high transmittance.
• a high-performance element such as a TFT type element
• an element in which an element such as a transistor is formed between an electrode for driving a liquid crystal and a substrate is used.
• a transmissive liquid crystal display element it is common to use a substrate as described above.
• an opaque substrate such as a silicon wafer may be used. Is possible.
• a material such as aluminum that reflects light may be used for the electrode formed on the substrate.
• TEOS tetraethoxysilane
• C18 octadecyltriethoxysilane
• ACPS 3-acryloxypropyltrimethoxysilane
• HG 2-methyl-2,4-pentanediol (also known as hexylene glycol)
• BCS 2-butoxyethanol
• UPS 3-ureidopropyltriethoxysilane
• MPMS 3-methacryloxypropyltrimethoxysilane
• ⁇ Execution synthesis example 1> In a 200 mL (liter) four-necked reaction flask equipped with a thermometer and reflux tube, 22.5 g HG, 7.5 g BCS, 28.3 g TEOS, 1.7 g C18, and 14.14 ACPS. 1 g was mixed to prepare an alkoxysilane monomer solution. To this solution, 11.2 g of HG, 3.7 g of BCS, 10.8 g of water, and 0.2 g of oxalic acid as a catalyst were added dropwise over 30 minutes at room temperature.
• ⁇ Execution synthesis example 2> In a 200 mL four-necked reaction flask equipped with a thermometer and a reflux tube, 21.1 g of HG, 7.0 g of BCS, 19.2 g of TEOS, 1.7 g of C18, and 23.4 g of ACPS were mixed. Then, a solution of the alkoxysilane monomer was prepared. To this solution, 10.5 g of HG, 3.5 g of BCS, 10.8 g of water, and 0.9 g of oxalic acid as a catalyst were added dropwise over 30 minutes at room temperature.
• ⁇ Execution synthesis example 3> In a 200 mL four-necked reaction flask equipped with a thermometer and a reflux tube, 20.2 g of HG, 6.7 g of BCS, 27.9 g of TEOS, 1.7 g of C18, and 17.4 g of MPMS were mixed. Then, a solution of the alkoxysilane monomer was prepared. To this solution, 10.0 g of HG, 3.4 g of BCS, 10.8 g of water and 0.9 g of oxalic acid as a catalyst were added dropwise over 30 minutes at room temperature.
• Example 1 The liquid crystal aligning agent [K1] obtained in Synthesis Example 1 was spin-coated on the ITO surface of an ITO electrode substrate on which an ITO electrode pattern having a pixel size of 100 ⁇ m ⁇ 300 ⁇ m and a line / space of 5 ⁇ m was formed. After drying on an 80 ° C. hot plate for 5 minutes, baking was performed in a hot air circulation oven at 180 ° C. for 30 minutes to form a liquid crystal alignment film having a thickness of 100 nm. The liquid crystal aligning agent [K1] obtained in Synthesis Example 1 is spin-coated on the ITO surface on which no electrode pattern is formed, dried on an 80 ° C. hot plate for 5 minutes, and then heated in a 180 ° C.
• Example 2> The response speed was measured in the same manner as in Example 1 except that the polymerizable compound added to the liquid crystal MLC-6608 was changed to 0.05% by weight. The results are shown in Table 1.
• Example 3> The response speed was measured in the same manner as in Example 1 except that the polymerizable compound added to the liquid crystal MLC-6608 was changed to 0.02% by weight. The results are shown in Table 1.
• Example 4 The response speed was measured in the same manner as in Example 1 except that the polymerizable compound was not added to the liquid crystal MLC-6608. The results are shown in Table 1.
• Example 5> A liquid crystal cell was produced in the same manner as in Example 4 except that the liquid crystal aligning agent [K1] was changed to the liquid crystal aligning agent [K2] obtained in Example Synthesis Example 2, and the response speed was measured. The results are shown in Table 1.
• Example 6> A liquid crystal cell was prepared in the same manner as in Example 4 except that the liquid crystal alignment treatment agent [K1] was changed to the liquid crystal alignment treatment agent [K3] obtained in Example Synthesis Example 3, and the response speed was measured. The results are shown in Table 1.
• the response speed after UV irradiation was the same as when the polymerizable compound was 0.2% by weight. Improved. Furthermore, even when the polymerizable compound was 0.02% by weight, the response speed was improved. Furthermore, the response speed was improved even when a liquid crystal to which no polymerizable compound was added was used. In Examples 5 and 6, the response speed was greatly improved in the liquid crystal to which no polymerizable compound was added. On the other hand, in the comparative example, the response speed was not improved when the polymerizable compound was reduced or when the liquid crystal was not added.
• the liquid crystal display device manufactured using the liquid crystal aligning agent of the present invention can improve the response speed and obtain a good alignment state even when the polymerizable compound is reduced in the PSA alignment method.
• PSA type TFT liquid crystal display elements TN liquid crystal display elements, VA liquid crystal display elements, and the like.

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• 2010
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