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WO2008044644A1 - Agent d'alignement de cristaux liquides contenant du silicium, et film d'alignement de cristaux liquides - Google Patents

Agent d'alignement de cristaux liquides contenant du silicium, et film d'alignement de cristaux liquides Download PDF

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Publication number
WO2008044644A1
WO2008044644A1 PCT/JP2007/069591 JP2007069591W WO2008044644A1 WO 2008044644 A1 WO2008044644 A1 WO 2008044644A1 JP 2007069591 W JP2007069591 W JP 2007069591W WO 2008044644 A1 WO2008044644 A1 WO 2008044644A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
polysiloxane
aligning agent
crystal aligning
carbon atoms
Prior art date
Application number
PCT/JP2007/069591
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English (en)
Japanese (ja)
Inventor
Kenichi Motoyama
Rie Gunji
Kazuki Eguchi
Original Assignee
Nissan Chemical Industries, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to CN2007800375142A priority Critical patent/CN101523280B/zh
Priority to JP2008538706A priority patent/JP5206413B2/ja
Priority to KR1020097006820A priority patent/KR101419962B1/ko
Publication of WO2008044644A1 publication Critical patent/WO2008044644A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G02F1/133719—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films with coupling agent molecules, e.g. silane
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes

Definitions

  • the present invention relates to a liquid crystal alignment agent containing polysiloxane obtained by polycondensation of alkoxysilane and a specific glycol compound, a liquid crystal alignment film obtained from the liquid crystal alignment agent, and the liquid crystal alignment
  • the present invention relates to a liquid crystal display element having a film.
  • Patent Document 2 Japanese Patent Laid-Open No. 09-278724
  • the present invention has the following gist.
  • the polysiloxane (A) used in the present invention must contain an alkoxysilane represented by the following formula (1). It can be obtained by polycondensation of alkoxysilane as an ingredient.
  • Examples of the first organic group include an alkyl group, a perfluoroalkyl group, an alkenyl group, an aryloxyalkyl group, a phenethyl group, a perfluorophenylalkyl group, a phenylaminoalkyl group, Styrylalkyl group, naphthyl group, benzoylalkylalkyl group, alkoxyphenoxyalkyl group, cycloalkylaminoalkyl group, epoxy-cyclic alkyl group, N- (aminoalkyl) aminoalkyl group, N- (aminoalkyl) amino anoalkyl An enethyl group, a bromoalkyl group, a diphenylphosphino group, an N— (methacryloxyhydroxyalkyl) aminoalkyl group, an N— (atyloxyhydroxyalkyl) aminoalkyl group, an optionally substituted and at least one norbornane
  • photosensitive groups Of these, alkyl groups and perfluoroalkyl groups are preferred because they are readily available.
  • the polysiloxane (A) used in the present invention has a plurality of such first organic groups! /, Or may be! /.
  • the first organic group is less than 0.1 mol with respect to 100 mol of the silicon atom of the polysiloxane (A), good liquid crystal alignment may not be obtained. Therefore, 0.1 mol or more is preferable, 0.5 mol or more is more preferable, and 1 mol or more is more preferable. When the amount exceeds 30 mol, the formed liquid crystal alignment film may not be sufficiently cured. Therefore, 30 mol or less is preferable, 22 mol or less is more preferable, and 15 mol or less is more preferable.
  • alkoxysilane represented by the formula (1) dodecyltriethoxysilane, octadecyltriethoxysilane, octyltriethoxysilane, tridecafluorooctyltriethoxysilane, and lan are preferable.
  • the second organic group is an organic group having 1 to 6 carbon atoms.
  • the second organic group include aliphatic hydrocarbons; ring structures such as aliphatic rings, aromatic rings or heterocycles; unsaturated bonds; or heteroatoms such as oxygen atoms, nitrogen atoms and sulfur atoms. It is an organic group having 1 to 3 carbon atoms which may have a branched structure.
  • the second organic group may have a halogen atom, a bur group, an amino group, a glycidoxy group, a mercapto group, a ureido group, a methacryloxy group, an isocyanate group, an attaryloxy group, or the like.
  • the polysiloxane (A) used in the present invention may have one or more second organic groups.
  • alkoxysilane having the second organic group examples include alkoxysilanes represented by the following formula (2).
  • R 3 represents a hydrogen atom, a hydrogen atom, a rogen atom, or an organic group having 1 to 6 carbon atoms
  • R 4 represents a carbon atom number;! To 5 hydrocarbon group, and m represents an integer of 0 to 3. To express. )
  • alkoxysilane in which m is 0 represents tetraalkoxysilane. Tetraalkoxysilane is condensed with alkoxysilane represented by formula (1).
  • polysiloxane (A) it is preferable.
  • Specific examples of the alkoxysilane in which m is 0 in the formula (2) include tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane and the like. Is preferred.
  • R 3 in the formula (2) is an organic group having 1 to 6 carbon atoms, it represents the same group as the second organic group described above.
  • the example in this case is the same as described for the second organic group above.
  • alkoxysilane of the formula (2) specific examples of the alkoxysilane when R 3 is a hydrogen atom or a halogen atom include trimethoxysilane, triethoxysilane, tripropoxysilane, tributoxysilane, chlorotrimethoxy Examples thereof include silane and chlorotriethoxysilane.
  • alkoxysilane represented by the above formula (2) one kind or plural kinds can be used as necessary.
  • the alkoxysilane represented by the formula (2) is 99.9 mol in all alkoxysilanes used to obtain the polysiloxane (A). 0/0, more preferably less preferred instrument 99, 5 mole 0/0 or less, still more preferably 99 mol 0/0. Further, the alkoxysilane represented by the formula (2) is preferably 70 mol% or more, more preferably 78 mol% or more, and still more preferably 85 mol% or more.
  • a method for condensing the polysiloxane (A) used in the present invention is not particularly limited, and examples thereof include a method of hydrolyzing and condensing alkoxysilane in an alcohol or a darlicol solvent.
  • the hydrolysis' condensation reaction may be either partial hydrolysis or complete hydrolysis.
  • complete hydrolysis it is theoretically sufficient to add 0.5 moles of water of all alkoxy groups in the alkoxysilane, but usually an excess of water is swallowed more than 0.5 moles.
  • the amount of water used in the above reaction is a force that can be appropriately selected as desired. Usually, it is 0.5 to 2.5 moles of all alkoxy groups in the alkoxysilane.
  • acids such as hydrochloric acid, sulfuric acid, nitric acid, acetic acid, formic acid, oxalic acid, maleic acid, fumaric acid, ammonia, methylamine, ethylamine, ethanolamine,
  • a catalyst such as an alkali such as triethylamine or a metal salt of an inorganic acid such as hydrochloric acid, sulfuric acid or nitric acid is used.
  • the heating temperature and the heating time can be appropriately selected as desired. Examples thereof include heating and stirring at 50 ° C. for 24 hours, and heating and stirring for 1 hour under reflux.
  • a method of heating and polycondensing a mixture of an alkoxysilane, a solvent and oxalic acid can be mentioned. Specifically, after adding oxalic acid to alcohol in advance to make an alcohol solution of oxalic acid, alkoxysilane is mixed in a state where the solution is heated. In this case, the amount of succinic acid used is generally 0.2 to 2 mol with respect to 1 mol of all alkoxy groups of alkoxysilane. Heating in this method can be performed at a liquid temperature of 50 to 180 ° C., and preferably, for example, several times under reflux in a container equipped with a reflux pipe so that the liquid does not evaporate or volatilize.
  • alkoxysilanes When a plurality of alkoxysilanes are used in obtaining polysiloxane (A) for a sufficient period of time to several tens of hours, they may be mixed as a mixture of alkoxysilanes in advance! / Orchids may be mixed with 7 J-fires.
  • the solvent used for polycondensation of alkoxysilane (hereinafter also referred to as polymerization solvent) is not particularly limited as long as it dissolves alkoxysilane. Even if the alkoxysilane does not dissolve, it may be dissolved as long as the polycondensation reaction of the alkoxysilane proceeds.
  • polymerization solvent an organic solvent having good compatibility with alcohols, glycolenoles, glycol ethers and alcohols is used.
  • polymerization solvent examples include methanol, ethanol, propanol, n-butanol, ethylene glycol, diethylene glycol, propylene glycol and dipro.
  • a polymerization solution of polysiloxane (A) obtained by such a method (hereinafter also referred to as polymerization solution).
  • SiO equivalent concentration 0.5
  • the polymerization solution obtained by the above-mentioned method may be used as the polysiloxane (A) solution as it is, or the solution obtained by the above-mentioned method may be concentrated or added with a solvent as necessary.
  • the solution may be diluted or substituted with another solvent to form a solution of polysiloxane (A).
  • the solvent to be used hereinafter also referred to as additive solvent
  • This solvent is not particularly limited as long as the polysiloxane (A) is uniformly dissolved, and one or a plurality of types can be arbitrarily selected and used.
  • Such an additive solvent include alcohols such as methanol, ethanol, 2-propanol, butanol and diacetone alcohol; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; ethylene glycol, Glyconoles such as diethylene glycol, propylene glycolenole, hexylene glycolenole, etc .; methinoreserosonoleb, ethinore cerosoleneb, butinorecellosonolev, ethinorecanorebitonore, butinorecanolebitonore, ethylene glyconoresimethinore Etherenole, ethyleneglycololecinoleethenore, ethyleneglycoresinpropinoreenotenole, ethyleneglycolenoresbutinoreethenore, diethyleneglycolmonomethylether, diethyleneglycolmonoeth Ether, di
  • the glycol compound (B) used in the present invention has two carbon atoms to which a hydroxy group and a hydrogen atom are bonded, and the two carbon atoms described above are bonded via an aliphatic group which may contain a hetero atom.
  • the glycol compound (B) contains a heteroatom! / It means a glycol compound having a number of consecutive carbon atoms excluding heteroatoms from 3 to 6.
  • diethylene glycol has a continuous carbon number of 4, and is a particularly preferred specific example of the glycol compound (B).
  • the glycol compound (B) is not particularly limited as long as it is a compound as described above. Specific examples thereof include 1,3-propanediol, 1,3-butanediol, 1,4-butanediol. 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 2,4pentanediol, 1,6hexanediol, diethyleneglycolanol, dipropylene glycol and the like.
  • glycol compound (B) Since such a glycol compound (B) is usually in a liquid state, it can also be used as a solvent. Therefore, it may be added later to the polysiloxane (A) synthesized with another solvent, which may be used as all or part of the polymerization solvent or additive solvent for polycondensation of the polysiloxane (A). .
  • the glycol compound (B) used in the present invention is used in an amount of 100 mass in total, in which the silicon atoms of all alkoxysilanes used to obtain the polysiloxane (A) are converted to SiO.
  • the glycol compound ( ⁇ ) used in the present invention can easily improve the water repellency of the liquid crystal alignment film, and can reduce the organic groups of the polysiloxane ( ⁇ ) in the liquid crystal aligning agent. As described above, a liquid crystal alignment film having high density, high hardness, good liquid crystal alignment properties, and excellent coating properties can be obtained.
  • a solvent (C) which is a solvent having a hydroxy group and having a structure different from that of the glycol compound (B) can also be used.
  • solvent (C) examples include methanol, ethanol, 2-propanol, butanol
  • Alcohols such as diacetone alcohol, ethylene glycol, 1,2-propanedio Glycols such as 3-pentanediol and 2-methyl-2,4-pentanediol.
  • Ethylene glycol monolechinenoatenore Ethylene glyconole monoethylenoatenore, Ethylene glyconole monopropenoatenore, Ethylene glyconomonomonobutenoreatenore, Propylene glyconole monomethinoatenore, Propylene glyconole monoethanolate, propylene glyconole monopropinoreateenore, propylene glyconole monobutinoleatenore and other glyconoreatenoles, propylene glycolenolemonomethinoatenoate acetate, propylene glycol monoacetate Ethyl ether acetate, Ethylene glycol monomethyl ether acetate, Ethylene glycol
  • the solvent (C) used in the present invention is a polysulfide synthesized with another solvent that may be used as all or part of the polymerization solvent or additive solvent for polycondensation of the polysiloxane (A). You may add to siloxane (A) later.
  • solvents (C) 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.
  • the amount of the solvent (C) used is 0 with respect to 100 parts by mass as a total of the silicon atoms of all alkoxysilanes used for obtaining the polysiloxane (A) converted to SiO.
  • glycol compound ( ⁇ ) and the solvent (C) for example, inorganic fine particles, methaoxane oligomers, metalloxane polymers, leveling agents, and even surfactants may be included. Good.
  • the inorganic fine particles are particularly preferably those in a colloidal solution in which fine particles such as silica fine particles, alumina fine particles, titania fine particles, and magnesium fluoride fine particles are preferred.
  • the Lloyd solution may be one obtained by dispersing inorganic fine particle powder in a dispersion medium, or a commercially available colloid 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 -0.2 m, more preferably 0.001 -0.1 lrn.
  • the transparency of the cured film formed using the prepared coating liquid may be reduced. Mention may be made of solvents.
  • the colloidal solution it is preferable that pH or pKa is adjusted to !! to 10! /, From the viewpoint of the stability of the coating solution for film formation! /. More preferably, it is 2-7.
  • Examples of the organic solvent used for the dispersion medium of the colloid solution include methanol, isopropyl alcohol, butanol, ethylene glycol, propylene glycol, butanediol, pentadiol, hexylene glycol, diethylene glycol and dipropylene glycol.
  • Alcohol such as ethylene glycol monopropyl ether, ketones such as methyl ethyl ketone and methylisobutyl ketone, aromatic hydrocarbons such as toluene and xylene, dimethylhonolemamide, dimethylacetamide, N Examples thereof include amides such as methylpyrrolidone, esters such as ethyl acetate, butyl acetate and butyrolatatatone, and ethers such as tetrahydrofuran and 1,4-dioxane. Of these, alcohols and ketones are preferred. These organic solvents can be used alone or in combination of two or more as a dispersion medium.
  • the 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 and metalloxane polymer may be commercially available or may be obtained from monomers such as metal alkoxides, nitrates, hydrochlorides, and carboxylates by a conventional method such as hydrolysis.
  • the refractive index of the cured film can be improved or the photosensitivity can be imparted by containing a metalloxane oligomer or a metalloxane polymer.
  • the polysiloxane (A) can be used simultaneously with the synthesis of the polysiloxane (A). (A) may be added later.
  • metalloxane oligomers and metalloxane polymers include Methyl silicate 51, Methyl silicate 53A, Ethyl silicate 40, Ethyl silicate 48, EMS-485, SS-101 manufactured by Colcoat Co., Ltd.
  • siloxane oligomers such as siloxane polymers and titanoxane oligomers such as titanium n-butoxide tetramer manufactured by Kanto Chemical Co., Inc. These may be used alone or in combination of two or more.
  • leveling agent and surfactant known ones can be used, and commercially available products are particularly preferred because they are easily available.
  • the method of mixing the above-mentioned other components with polysiloxane (A) is not particularly limited, either at the same time as or after the solution of polysiloxane (A) and daricol compound (B). .
  • the method for preparing the liquid crystal aligning agent of the present invention is not particularly limited. If the polysiloxane (A) and the glycol compound (B), and if necessary, the solvent (C) and / or other components are uniformly mixed,
  • the polysiloxane (A) is polycondensed in a solvent, and thus is obtained in a solution state.
  • the method of using the polysiloxane (A) polymerization solution as described above as it is is simple.
  • Polymerization solvent power of polysiloxane (A) In the case of the glycol compound (B), the glycol compound (B) may not be added later.
  • the polysiloxane (A) solution does not contain the glycol compound (B), the glycol compound (B) can be added and used when preparing the liquid crystal aligning agent.
  • the solvent (C) when used in combination, it may be used as a polymerization solvent or an additive solvent when synthesizing the polysiloxane (A), and mixed when preparing the liquid crystal aligning agent. Use it,
  • the polysiloxane (A) is converted into SiO in the silicon atoms of all alkoxysilanes used to obtain the polysiloxane (A) in the liquid crystal aligning agent.
  • the SiO equivalent concentration is 0.5 to 20% by mass, preferably 0.5 to 15% by mass, particularly preferably
  • the solvent used for adjusting the SiO equivalent concentration is a polymerization solution of polysiloxane (A).
  • the liquid crystal aligning agent of the present invention is applied with a force S to form a cured film by performing drying and baking after coating on a substrate.
  • the transfer printing method is widely used industrially from the viewpoint of productivity, which includes spin coating method, printing method, ink jet method, spray method, roll coating method, etc.
  • the liquid crystal aligning agent of this invention is also used suitably.
  • the drying process after applying the liquid crystal aligning agent is not necessarily required, but the time from application to baking is constant for each substrate! /, N! /, Or is not baked immediately after coating. In some cases, it is preferable to include a drying step.
  • the drying means 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. For example, 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 form a cured film.
  • the firing temperature can be performed at any temperature of 100 ° C to 350 ° C, but preferably (up to 140 ° C to 300 ° C, more preferably (up to 150 ° C to 230 ° C, More preferably (1-60 ° C to 220 ° C.
  • the baking time can be any time from 5 minutes to 240 minutes, preferably 10 to 90 minutes, more preferably 20 to 90 minutes Heating is usually performed using a publicly known method such as a hot plate, hot air circulating oven, IR oven, belt furnace, etc.
  • the polysiloxane (A) in the liquid crystal alignment film undergoes polycondensation in the firing step.
  • it is not necessary to completely polycondense unless the effects of the present invention are impaired.
  • firing at a temperature of 10 ° C or higher is preferable than the heat treatment temperature required for the liquid crystal cell manufacturing process, such as curing of the sealant! /.
  • the thickness of the cured film can be selected as necessary.
  • the thickness of the cured film is 5nm or less
  • the above case is preferable because the reliability of the liquid crystal display element is easily obtained. More preferably, it is 10 nm or more. Further, the case of 300 nm or less is preferable because the power consumption of the liquid crystal display element does not become extremely large. More preferably, it is 150 nm or less.
  • Such a cured film can be used as it is as a liquid crystal alignment film.
  • the cured film is rubbed, irradiated with polarized light or light of a specific wavelength, or treated with an ion beam or the like.
  • a liquid crystal alignment film can also be used.
  • the liquid crystal alignment film of the present invention formed by the method as described above is considered to have a structure in which the specific organic group of polysiloxane (A) is unevenly distributed in the vicinity of the surface layer of the liquid crystal alignment film. This can be confirmed by measuring the water contact angle of the liquid crystal alignment film of the present invention. This is presumed to be due to the effect of the Daricol compound (B) which is a component of the liquid crystal aligning agent of the present invention. When the Daricol compound (B) is contained in the liquid crystal aligning agent, the glycol compound (B) The water contact angle can be increased as compared with the case where no water is contained.
  • the specific organic group of the polysiloxane (A) is unevenly distributed near the surface layer of the liquid crystal alignment film due to the effect of the glycol compound (B), so that the liquid crystal molecules are unidirectionally, particularly in the vertical direction. It is considered that the effect of being easily oriented is achieved. Therefore, since the liquid crystal alignment film of the present invention exhibits high water repellency, good liquid crystal vertical alignment can be obtained.
  • the liquid crystal alignment film of the present invention has a small amount of the specific organic group contained in the polysiloxane (A) which is a component of the liquid crystal alignment agent of the present invention! Therefore, it has high liquid crystal vertical alignment and high hardness with high density.
  • the liquid crystal alignment film is obtained from the liquid crystal aligning agent of the present invention having excellent coating properties, it also has an effect of high uniformity. Therefore, a liquid crystal display element with high reliability and high image quality can be provided.
  • the specific organic group possessed by the polysiloxane (A) is 0 ⁇ ;!-30 moles per 100 moles of the silicon atom possessed by the polysiloxane (A). Even so, the obtained liquid crystal alignment film exhibits good liquid crystal vertical alignment with high water repellency, high hardness with high density, and excellent uniformity.
  • the liquid crystal display element of the present invention can be obtained by forming a liquid crystal alignment film on a substrate by the method described above 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 is fixed with a sealant with a spacer interposed therebetween, and liquid crystal is injected and sealed.
  • the size of the spacer used is a force of 1 to 30 micrometers, preferably 2 to 10 micrometers.
  • the method for injecting liquid crystal is not particularly limited, and examples thereof include a vacuum method in which liquid crystal is injected after reducing the pressure inside the manufactured liquid crystal cell, and a dropping method in which sealing is performed after liquid crystal is dropped.
  • 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.
  • Specific examples include glass plate, polycarbonate, poly (meth) acrylate, polyether sulfone, polyarylate, polyurethane, polysulfone, polyether, polyether ketone, trimethylpentene, polyolefin, polyethylene terephthalate, (meth) attaly.
  • substrates on which a transparent electrode is formed on a plastic plate such as nitrile, triacetyl cellulose, diacetyl cellulose, and acetate butyrate cellulose.
  • a high-functional device such as a TFT-type device
  • a device 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 element it is common to use a substrate as described above.
  • an opaque substrate such as a silicon wafer can be used if only one substrate is used. It is. At that time, a material such as aluminum that reflects light can be used for the electrode formed on the substrate.
  • the liquid crystal alignment film obtained by using the liquid crystal aligning agent of the present invention has high density with high density, high water repellency, and good liquid crystal vertical alignment.
  • a liquid crystal alignment film having excellent uniformity can be obtained.
  • an element produced using the liquid crystal alignment film has good accumulated charge characteristics.
  • a 1 L four-necked reaction flask equipped with a thermometer and a reflux tube was charged with 163.9 g of HG, 163.9 g of TEOS, and 13.9 g of C12, and stirred to prepare a solution of an alkoxysilane monomer.
  • an oxalic acid solution in which HG82. Lg, water 74. lg and 0.8 g of oxalic acid as a catalyst were mixed in advance was added dropwise at room temperature over 30 minutes, and stirred at room temperature for 30 minutes after the completion of the addition. Then, after heating for 1 hour under reflux, the product was allowed to cool and a polycondensation with a solid content concentration in terms of SiO of 10% by mass was performed.
  • Table 10 shows the solvent composition by mixing and stirring the amounts of HG, BCS and solvent (X) shown in Table 1 to 10 g of the polysiloxane solution (Kl) obtained in Synthesis Example 1.
  • liquid crystal aligning agents (KL1 to KL7) having a solid content concentration force of mass% in terms of Si 2 O were obtained.
  • a 1 L four-necked reaction flask equipped with a thermometer and a reflux tube was charged with 163.3 g of BCS, 13.9 g of TEOS and 13.9 g of C12, and stirred to prepare an alkoxysilane monomer solution.
  • To this solution was added dropwise an oxalic acid solution in which 80 g of BSC, 82. lg of water, 74. lg of water and 0.8 g of oxalic acid as a catalyst were mixed over 30 minutes at room temperature, and stirred at room temperature for 30 minutes after completion of the addition. did . Then, after heating for 1 hour under reflux, the product was allowed to cool and a polycondensation with a solid content concentration in terms of SiO of 10% by mass was performed.
  • a liquid crystal aligning agent (KL8) having a solid content concentration of 4% by mass was obtained.
  • BCS15.Og was mixed with 10 g of the polysiloxane solution (K2) obtained in Synthesis Example 2 and stirred to obtain a liquid crystal aligning agent (KM2) having an SiO equivalent solid content concentration force of mass%.
  • a polysiloxane solution (K3) was obtained.
  • DEG15.Og was mixed with 10 g of the polysiloxane solution (K3) obtained in Synthesis Example 3 and stirred to obtain a liquid crystal aligning agent (KL9) having an SiO equivalent solid content concentration force of mass%.
  • a liquid crystal aligning agent (KL10) having a solid content concentration of 4% by mass was obtained.
  • a polysiloxane solution (K4) was obtained.
  • a liquid crystal aligning agent (KL11) having a solid content concentration of 4% by mass was obtained.
  • EtOH15.Og was mixed with 10 g of the polysiloxane solution (K4) obtained in Synthesis Example 4 and stirred to obtain a liquid crystal aligning agent (KM3) having a SiO equivalent solid content concentration force mass%.
  • a liquid crystal aligning agent having a converted solid content concentration of 4% by mass was obtained as 12 to! 0 ⁇ 5 and 1 ⁇ [4].
  • HG124.4 g, BCS41.5 g, TEOS164.9 g and C11.5 g were charged into a 1 L four-necked reaction flask equipped with a thermometer and a reflux tube, and stirred to dissolve the alkoxysilane monomer. A liquid was prepared. To this solution, an oxalic acid solution in which 62.2 g of HG, 20.7 g of BCS, 74. lg of water and 0.8 g of oxalic acid as a catalyst were mixed in advance was added dropwise over 30 minutes at room temperature. did. After heating for 1 hour under reflux, it is allowed to cool and solidify in terms of SiO.
  • a liquid crystal aligning agent (KM5) having a concentration of 4% by mass was obtained.
  • a polysiloxane solution (K7) having a concentration of 2 parts by mass of 12% by mass was obtained.
  • a liquid crystal aligning agent (KM6) having a concentration of 4% by mass was obtained.
  • a liquid crystal aligning agent (KM7) having a concentration of 4% by mass was obtained.
  • a 1 L four-necked reaction flask equipped with a thermometer and a reflux tube was charged with 123.2 g of HG, 41.lg of BCS, 164.9 g of TEOS and 13.9 g of C12, and stirred to prepare a solution of an alkoxysilane monomer.
  • an oxalic acid solution in which 61.6 g of HG, 20.5 g of BCS, 74. lg of water and 0.8 g of oxalic acid as a catalyst were mixed in advance was added dropwise over 30 minutes at room temperature, and stirred at room temperature for 30 minutes after completion of the addition. did. After heating at 65 ° C for 1 hour, it is allowed to cool and solidify in terms of SiO.
  • HG10.2g, BCS2.8g and DEG2.0g were added to 10g of the polysiloxane solution (K9) obtained in Synthesis Example 9 and mixed.
  • a liquid crystal aligning agent (KM9) having a concentration of 4 parts by mass was obtained.
  • a liquid crystal aligning agent (KM10) having a concentration of 4 parts by mass was obtained.
  • a liquid crystal aligning agent (KM11) having a concentration of 4 parts by mass was obtained.
  • a liquid crystal aligning agent (KL23) having a solid content concentration force of mass% by mass of SiO was obtained.
  • a liquid crystal aligning agent (KM12) having a concentration of 4 parts by mass was obtained.
  • HG130.lg, BCS43.4g, TEOS147.6g, C12.13.9g, MPS8.18g and MAPSIO.4g were charged into a 1L four-necked reaction flask equipped with a thermometer and a reflux tube. A solution of the monomer was prepared. To this solution, an oxalic acid solution in which HG65.1 g, BCS21.7 g, water 69.4 g and oxalic acid 0.8 g as a catalyst were mixed in advance was added dropwise over 30 minutes at room temperature, and 30 minutes after completion of the addition at room temperature. Stir. Then, after heating for 1 hour under reflux, the mixture is allowed to cool and a polysiloxane solution with a SiO equivalent solid content concentration of 10% by mass (K1
  • a liquid crystal aligning agent (KM13) having a concentration of 4 parts by mass was obtained.
  • a liquid crystal aligning agent (KM14) having a form fraction concentration of 4% by mass was obtained.
  • a liquid crystal aligning agent (KL26) having a degree of 4% by mass was obtained.
  • a liquid crystal aligning agent (KL27) having a solid content concentration of 4% by mass was obtained.
  • the liquid crystal aligning agents KM1 to KM16 were subjected to pressure filtration with a membrane filter having a pore diameter of 0.45 micrometers, and then formed into a film on a glass substrate with a transparent ITO electrode by spin coating.
  • This substrate was dried on an 80 ° C hot plate for 5 minutes and then baked in a hot air circulation clean oven at 180 ° C for 60 minutes to form a liquid crystal alignment film having a thickness of about 80 nm. Further, the water contact angle of the liquid crystal alignment film was measured by the method described later. The results are shown in Table 3.
  • the liquid crystal alignment agents are 1, 3-Pr DO, 1, 3-— BDO, 1, 4-— BDO, 1, 3-— PeDO, 1, 6— HDO, It has been found that the inclusion of specific glycol compounds such as DEG and DPG increases the water contact angle of the film during film formation compared to the case of using a liquid crystal aligning agent not containing it.
  • specific glycol compounds such as DEG and DPG
  • polysiloxa This is also clear from the comparison between Examples 1 to 7 and Comparative Example 1 using Kl of the solution. That is, it was found that the water repellency of the film can be easily increased by containing the specific glycol compound as a liquid crystal aligning agent.
  • a liquid crystal cell was prepared by the method described later using the liquid crystal aligning agent KL18 obtained in Preparation Example 24.
  • the liquid crystal alignment of the obtained liquid crystal cell was confirmed by the method described later. The results are shown in Table 4.
  • the liquid crystal cell prepared by the above-mentioned [Creation of liquid crystal cell] method was observed with a polarizing microscope, and the alignment state of the liquid crystal was confirmed.
  • the entire liquid crystal cell is free of defects and shows a uniform alignment state, it was marked as ⁇ , and when alignment defects were found in a part of the liquid crystal cell and when it was not vertically aligned, it was marked as X.
  • Table 4 The results are shown in Table 4.
  • the liquid crystal aligning agent KL19 obtained in Preparation Example 26 or the liquid crystal aligning agent KL 20 obtained in Preparation Example 28 was subjected to pressure filtration with a membrane filter having a pore diameter of 0.45 micrometers, and then applied to a glass substrate with an ITO transparent electrode.
  • a film was formed by spin coating and printing.
  • the substrate was dried on a hot plate at 80 ° C for 5 minutes and then baked for 60 minutes with a 180 ° C hot air circulating clean oven to form a liquid crystal alignment film having a thickness of about 80 nm.
  • the applicability in obtaining the film was evaluated by the methods described later (applicability for spin coating, applicability for flexographic printing).
  • the pencil hardness was measured by the method described later.
  • a liquid crystal cell was prepared from the substrate with a liquid crystal alignment film according to the above-described method for preparing a liquid crystal cell, and the accumulated charge was measured by the method described later. The results are shown in Table 5.
  • liquid crystal aligning agent KM9 obtained in Preparation Example 29 or liquid crystal aligning agent KM 8 obtained in Preparation Example 27 Using liquid crystal aligning agent KM9 obtained in Preparation Example 29 or liquid crystal aligning agent KM 8 obtained in Preparation Example 27, a method for measuring coatability, pencil hardness, and accumulated charge as described in Examples 28 to 29 later. It went by. The results are shown in Table 5.
  • the liquid crystal alignment films obtained from Examples 28 to 29 and Comparative Examples 17 to 18 were measured by a pencil hardness test method (JIS K5400). The results are shown in Table 5.
  • the liquid crystal aligning agent was filtered using a chromatodisc (pore diameter 0.45 micrometer), and then formed into a film on a glass substrate with an ITO transparent electrode by spin coating.
  • This board is hot at 80 ° C After drying on the plate for 5 minutes, it was baked for 60 minutes in a 180 ° C hot air circulation clean oven to form a liquid crystal alignment film with a film thickness of about 80 nm.
  • the cured film has good pinholes with no unevenness, ⁇ with some pinholes with unevenness, and pinholes with unevenness on the entire surface. X is the case.
  • Table 5 The results are shown in Table 5.
  • a rectangular wave of 30Hz / ⁇ 2.8V with DC 10V superimposed on the liquid crystal cell is temperature 23
  • the applicability of the liquid crystal alignment film composed of a liquid crystal alignment agent that does not contain a specific glycol compound such as DEG (Comparative Example 17) as the liquid crystal alignment agent is determined regardless of whether spin coating or flexographic printing is used. Hall 'Unevenness was seen and found not enough. It was also found that the lead pencil hardness of the film was as low as H. Furthermore, the accumulated charge is also 20 hours after DC application and DC off. The amount of change after 10 minutes s It was found that the accumulated charge release rate was slow.
  • the liquid crystal alignment film comprising a liquid crystal aligning agent (Example 28) containing a specific solvent such as DEG has a coating property regardless of spin coating method “flexographic printing”. 'No irregularity was found, and it turned out to be sufficient. It was also found that the pencil hardness of the film was as high as 6H. In addition, the absolute value of the accumulated charge also decreased significantly immediately after DC application for 20 hours and 10 minutes after DC off, indicating that the accumulated charge release rate was fast. In other words, it is assumed that the problem of image sticking and afterimages can be reduced as element characteristics.
  • the liquid crystal aligning agent of the present invention contains a specific solvent, so that it is easier to increase the water repellency of the film during film formation than when a liquid crystal aligning agent not containing it is used. As a result, it is possible to form a liquid crystal alignment film having high density and high hardness and good liquid crystal alignment. Furthermore, since the liquid crystal aligning agent of the present invention is excellent in coating properties, it is possible to obtain a highly uniform liquid crystal aligning film. Therefore, a highly reliable high-quality liquid crystal display element can be provided.
  • the long-chain alkyl group-containing silane used to obtain a liquid crystal aligning film exhibiting the desired water repellency It is economical because the amount of use can be reduced. Therefore, it can be suitably used in various liquid crystal alignment elements, particularly in the vertical alignment type (VA). It can also be used in other polarizing films, retardation films, and alignment films for viewing angle widening films. It should be noted that the entire contents of the specification, claims, and abstract of the Japanese Patent Application No. 2006-275713 filed on October 6, 2006 are hereby incorporated by reference herein. And that is what we take in.

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Abstract

L'invention concerne un agent d'alignement de cristaux liquides contenant du silicium qui permet de former un film d'alignement de cristaux liquides présentant de bonnes propriétés d'alignement de cristaux liquides et une dureté élevée, et d'excellentes propriétés de revêtement en vue d'une impression flexographique ou d'applications similaires ; un film d'alignement de cristaux liquides élaboré en utilisant l'agent d'alignement de cristaux liquides contenant du silicium ; et un élément d'affichage à cristaux liquides de grande fiabilité et de qualité d'image élevée. L'agent d'alignement de cristaux liquides comprend le polysiloxane (A) et le composé glycolique (B) suivants. Polysiloxane (A) : un polysiloxane généré par la polycondensation d'un composant alcoxysilane comprenant au moins un alcoxysilane représenté par la formule (1). R1nSi(OR2)4-n (1) [dans laquelle R1 représente un groupe organique portant 7 à 30 atomes de carbone ; R2 représente un groupe hydrocarboné portant 1 à 5 atomes de carbone ; et n représente un entier de 1 à 3]. Composé glycolique (B) : un composé glycolique qui porte deux atomes de carbone, chacun ayant un groupe hydroxyle et un atome d'hydrogène attachés, et qui présente une structure telle que les deux atomes de carbone sont liés l'un à l'autre par l'intermédiaire d'un groupe aliphatique qui peut contenir un hétéroatome et qui porte 3 à 6 atomes de carbone contigus.
PCT/JP2007/069591 2006-10-06 2007-10-05 Agent d'alignement de cristaux liquides contenant du silicium, et film d'alignement de cristaux liquides WO2008044644A1 (fr)

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KR1020097006820A KR101419962B1 (ko) 2006-10-06 2007-10-05 규소계 액정 배향제 및 액정 배향막

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WO2009148099A1 (fr) * 2008-06-04 2009-12-10 日産化学工業株式会社 Agent d’orientation de cristaux liquides à base de silicium, film orienté de cristaux liquides et élément d’affichage à cristaux liquides
WO2010074261A1 (fr) * 2008-12-25 2010-07-01 日産化学工業株式会社 Matière d'alignement de cristaux liquides pour revêtement à jet d'encre, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides
WO2010074264A1 (fr) * 2008-12-26 2010-07-01 日産化学工業株式会社 Agent d'alignement de cristaux liquides pour revêtement à jet d'encre, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides
CN101812304A (zh) * 2009-02-19 2010-08-25 Jsr株式会社 液晶取向剂、液晶显示元件及其制造方法
WO2010126108A1 (fr) * 2009-05-01 2010-11-04 日産化学工業株式会社 Agent d'orientation de cristaux liquides sur silicium, couche mince orientée cristaux liquides et élément d'affichage à cristaux liquides
JP5459228B2 (ja) * 2009-01-07 2014-04-02 日産化学工業株式会社 インクジェット塗布用液晶配向剤、液晶配向膜及び液晶表示素子
TWI452067B (zh) * 2009-12-01 2014-09-11 Nissan Chemical Ind Ltd Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components
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KR20160068869A (ko) 2013-10-10 2016-06-15 닛산 가가쿠 고교 가부시키 가이샤 조성물, 액정 배향 처리제, 액정 배향막 및 액정 표시 소자
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KR101708949B1 (ko) 2008-12-25 2017-02-21 닛산 가가쿠 고교 가부시키 가이샤 잉크젯 도포용 액정 배향제, 액정 배향막 및 액정 표시 소자
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JP5459229B2 (ja) * 2008-12-26 2014-04-02 日産化学工業株式会社 インクジェット塗布用液晶配向剤、液晶配向膜及び液晶表示素子
WO2010074264A1 (fr) * 2008-12-26 2010-07-01 日産化学工業株式会社 Agent d'alignement de cristaux liquides pour revêtement à jet d'encre, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides
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CN102414605A (zh) * 2009-05-01 2012-04-11 日产化学工业株式会社 硅系液晶取向剂、液晶取向膜及液晶显示元件
JP5605359B2 (ja) * 2009-05-01 2014-10-15 日産化学工業株式会社 ケイ素系液晶配向剤、液晶配向膜及び液晶表示素子
JP2014219684A (ja) * 2009-05-01 2014-11-20 日産化学工業株式会社 ケイ素系液晶配向剤
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WO2010126108A1 (fr) * 2009-05-01 2010-11-04 日産化学工業株式会社 Agent d'orientation de cristaux liquides sur silicium, couche mince orientée cristaux liquides et élément d'affichage à cristaux liquides
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JPWO2016068103A1 (ja) * 2014-10-31 2017-08-10 住友化学株式会社 撥水撥油コーティング組成物
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