WO2008066205A1 - Agent d'alignement de cristaux liquides et élément d'affichage à cristaux liquides - Google Patents

Agent d'alignement de cristaux liquides et élément d'affichage à cristaux liquides Download PDF

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Publication number
WO2008066205A1
WO2008066205A1 PCT/JP2007/073627 JP2007073627W WO2008066205A1 WO 2008066205 A1 WO2008066205 A1 WO 2008066205A1 JP 2007073627 W JP2007073627 W JP 2007073627W WO 2008066205 A1 WO2008066205 A1 WO 2008066205A1
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Prior art keywords
liquid crystal
formula
acetate
group
silicon compound
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PCT/JP2007/073627
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English (en)
Japanese (ja)
Inventor
Kenichi Sumiya
Tsubasa Abe
Eiji Hayashi
Michinori Nishikawa
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Jsr Corporation
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Publication of WO2008066205A1 publication Critical patent/WO2008066205A1/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
    • 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
    • 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups

Definitions

  • Liquid crystal alignment agent and liquid crystal display device Liquid crystal alignment agent and liquid crystal display device
  • the present invention relates to a liquid crystal aligning agent and a liquid crystal display device. More specifically, the liquid crystal alignment property is good, and the liquid crystal alignment state is good without impairing the electric characteristics such as the voltage holding ratio even after driving under a severe environment such as light irradiation or high temperature or for a long time.
  • the present invention relates to a liquid crystal aligning agent and a liquid crystal display device capable of forming a liquid crystal alignment film which is retained and hardly causes an afterimage phenomenon. Background art
  • a liquid crystal alignment film made of polyamic acid, polyimide or the like is formed on the surface of a substrate provided with a transparent conductive film to form a liquid crystal display element substrate.
  • a layer of nematic liquid crystal having positive dielectric anisotropy is formed in the gap to form a cell having a sandwich structure, and the major axes of liquid crystal molecules are continuously formed from one substrate to the other.
  • a TN liquid crystal display element having a so-called twisted nematic (TN) liquid crystal cell is known.
  • STN Small Twisted nematic liquid crystal display devices
  • I PS I n-P l an e Sw itching
  • VA Very Alignment
  • a transmissive liquid crystal display element performs display using change in transmitted light intensity of a light source for backlight from the back of the element when driving the element.
  • the reflection type liquid crystal display device does not use a light source for backlighting, but performs display using a change in the intensity of reflected light from outside such as sunlight when driving the device, and consumes more power than the transmission type. It is considered to be particularly advantageous for outdoor use, as it
  • the liquid crystal alignment film is exposed to the light from the backlight source for a long time.
  • metal halide lamps and other light sources with extremely high illumination intensity are used.
  • the reflection type liquid crystal display element the possibility of being used outdoors is large, and in this case, sunlight including strong ultraviolet light is a light source.
  • the distance through which light passes through the element is longer than in the transmissive type in principle.
  • a liquid crystal dropping method that is, an O D D (O n D D o r F i l l) method is started to be used from the viewpoint of process shortening and yield improvement.
  • the DF method cures ultraviolet light on the necessary part of one side substrate coated with a liquid crystal orientation film.
  • the liquid crystal is dropped to the necessary places, and the other substrate is bonded, and then ultraviolet light is irradiated on the entire surface to cure the sealing agent, thereby producing a liquid crystal cell.
  • the ultraviolet light irradiated is usually as strong as several joules or more per square centimeter. That is, in the liquid crystal display element manufacturing process, the liquid crystal alignment film is exposed to the strong ultraviolet light together with the liquid crystal.
  • the temperature of the system itself of the liquid crystal display element rises at the time of driving due to the strong light irradiation.
  • the use at high temperature compared to the normal room temperature such as use in the outdoors or installation in a private car while parked Installation environment can be considered.
  • liquid crystal display devices the liquid crystal orientation and voltage after being exposed to a severe environment such as light and heat or after being driven for a long time with the advancement of functions and versatility. Electrical characteristics such as retention, or afterimage characteristics, are required to be further superior to those in the past.
  • resins such as polyimide, polyamide and polyester have been known as materials for liquid crystal alignment films constituting liquid crystal display elements.
  • polyimide Among organic resins, they have been used in many liquid crystal display devices because they exhibit excellent physical properties such as heat resistance, affinity with liquid crystals, and mechanical strength.
  • liquid crystal display devices in recent years are likely to be enhanced in functionality and versatility, and as described above, opportunities for being installed and used in severe environments such as high temperature environments and light irradiation are increasing, and manufacturing processes are also increasing. Process shortening and yield improvement are further required, and, on the other hand, liquid crystal display elements are required to have a longer life. Along with this, display defects and afterimages caused by the insufficient tolerance to the high temperature environment and the light irradiation, which were conventionally within the allowable range, have become unacceptable.
  • the organic resin such as polyamic acid / polyimide which has been widely used as a liquid crystal alignment film in the past is still insufficient in resistance to light and heat. For this reason, there is a need for a new material having good resistance to light and heat as well as the ability to orient the liquid crystal uniformly in the plane of the liquid crystal display element.
  • a silicon compound (A) having four alkoxy groups such as tetraethoxysilane, and three alkoxy groups such as decyltriethoxysilane are exemplified.
  • the co-condensation polysiloxane solution of (A) and (B) is formed by heating and reacting the silicon compound (B) having the compound with an alcohol solvent at a temperature of 50 to 180 under an oxalic acid catalyst, There is disclosed a vertical alignment film obtained by applying this solution as a coating solution to the surface of an electrode substrate and thermally curing the obtained coating film at 80 to 400.
  • the vertical alignment film is excellent in vertical alignment, reproducibility, heat resistance and uniformity, and also excellent in stability as a coating solution.
  • a vertical alignment film or a method for forming the same is not sufficient yet.
  • the vertical alignment agent described in the above-mentioned JP-A-9-210520 has insufficient printability, and there are problems in using it for production.
  • the vertical alignment control force is not sufficient, which may cause display defects.
  • a vertical alignment film is formed with a composition of three components in total including a compound of the following formula (1) and a compound of the following formula (2). It describes what can be done. However, as a result of repeated investigations by the inventor of the present invention, only the compound of the formula (1) or the compound of the formula (1) and the compound 1 of the formula (2) It has been found that the composition of the total of two components is excellent in vertical alignment equivalent to that of the conventional product and shows voltage retention and printability superior thereto. Disclosure of the invention
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a liquid crystal having good printability, excellent vertical alignment, excellent voltage holding ratio characteristics and excellent afterimage characteristics.
  • An object of the present invention is to provide a liquid crystal aligning agent capable of forming an alignment film.
  • Another object of the present invention is to provide a liquid crystal alignment film having the above-mentioned excellent properties using the liquid crystal alignment agent of the present invention and a liquid crystal display device provided with the liquid crystal alignment film.
  • R 1 is an alkyl group
  • R is a methyl group or an ethyl group
  • R 2 is an alkyl group, consisting of only the silicon compound represented by the formula (1) and the silicon compound represented by the formula (2)
  • liquid crystal aligning agent characterized by containing a polymer obtained by hydrolyzing and condensing.
  • liquid crystal display device comprising a liquid crystal alignment film obtained from the liquid crystal alignment agent of the present invention.
  • liquid crystal aligning agent may contain, as a solvent, one or more of the following C) preferably containing at least one of the organic solvents shown in each of I)
  • formula (I) is a hydrogen atom, a methyl group, an ethyl group or an acetyl group, R 2 is an alkyl group having 1 to 4 carbon atoms, and n is an integer of 1 to 3,
  • R 3 is a hydrogen atom, a methyl group, a cetyl group or an acetyl group
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • m is an integer of 1 to 3
  • R 5 is an alkyl group having 5 2 carbon atoms.
  • the liquid crystal aligning agent of the present invention contains a hydrolytic condensation product of one component of the formula (1) or a total of two components of a silicon alkoxide of the formula (1) and the formula (2).
  • the hydrolytic condensate is a copolymer obtained by reacting the one or two kinds of alkoxides in the presence of water.
  • examples of the alkyl group of R 1 include a methyl group, a ethyl group, a propyl group and a butyl group.
  • carbon number 1 It is an alkyl group of ⁇ 3.
  • These alkyl groups may be linear or branched, and hydrogen atoms may be further substituted by fluorine atoms or the like.
  • silicon compound (1) represented by the above formula (1) examples include tetramethoxysilane, tetraethoxysilane, tetra-n-hydroxysilane, tetra-iso-pro-disilane, tetra-silane. _ n-buoxysilane, tetra-sec-butoxysilane, tetra-tert_ butoxysilane, etc. may be mentioned. These may be used alone or in combination of two or more.
  • R is a methyl group or an ethyl group.
  • alkyl group for R 2 include the same ones as for R 1 .
  • R is a methyl group or an ethyl group
  • examples of the compound in which R is a methyl group or an ethyl group include methyltrimethoxysilane, methyltriethoxysilane, methyltri n-propoxysilane, methyltri iso-propoxysilane, methyltri n-butoxysilane, methyltri _ sec _ Butoxysilane, methyltri-tert-butoxysilane, ectolytrimethoxysilane, ectolytriethoxysilane, ectolyl-n-propoxysilane, ectolyl-iso-propoxysilane, ectolyl n-butoxysilane, ectolyri-sec-butoxysilane, ⁇ ⁇ ⁇ ⁇ -tert-butoxysilane etc.
  • the hydrolyzed condensate can be obtained by reacting compound (1) or compound (1) with compound (2) and water, and subjecting it to hydrolysis and partial condensation.
  • siloxane bonds formula (1) in - -OR 2 of OR 1 or the formula, (2) A total of 1. 0 to 1.5 moles of water are preferably used per mole.
  • Water is intermittently or continuously added to the organic solvent in which the compound (1) or the compound (1) and the compound (2) are dissolved.
  • a reaction catalyst can be used.
  • the catalyst may be added in advance in an organic solvent, or may be dissolved or dispersed in water at the time of water addition.
  • the reaction temperature at this time is preferably 0 to L 00, more preferably 15 to 80.
  • an alcohol solvent, a ketone solvent, an amide solvent, an ester solvent and an aprotic solvent are used. At least one selected from the group can be used.
  • the alcohol solvent for example, methanol, ethanol, n-propanol, i-propanol, n-butyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butanol, n-pen Evening Nole, i-Pen-Eunol, 2-Methyl-Boonal, sec-Pen-Eunol, t-Pen-Eunol, 3-Methoxy-Benol, n-Hexanol, 2-Methyl-Pen-Eunol, sec-Hexanol 2, 2-butyl alcohol, sec-heptanol, heptanol-13, n-alcohol, 2-ethylhexanol, sec-alcohol, n-nonyl alcohol, 2,6-dimethylhept 4 N-decanol, sec-undecyl alcohol, trimethyl nonyl alcohol, sec-tetradecyl alcohol, sec-
  • Ethylene glycol 1,2-propylene glycol, 1,3-butylene glycol, pentenediol-2, 4 2-methyl pentenediol-2, 4 hexanediol-2, 5, heptanediol
  • Polyhydric alcohol solvents such as 2, 4 and 2-ethyl hexane 1, 3, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol;
  • Ethylene glycol monomethyl ether ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, ethylene glycol monobasic ether, ethylene glycol mono-2-ethyl butyl ether, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono Propyl ether, propylene glycol monobutyl ether, Propylene glycol monomethyl ether, dipropylene glycol monomethyl Edji ether, polyhydric alcohol partial ether solvents such as dipropylene glyco one mono propyl ether.
  • ketone solvent for example, acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, jetyl ketone, methyl-isobutyl ketone, methyl n-pentyl ketone, ethyl n-butyl ketone, methyl mono-e-hexyl ketone G-I-Butyl ketone, trimethylnonanone, cyclohexanone, 2-hexanone, methylcyclohexanone, 2,4 pentanedione, fastetonic acetone, fastethophenone, phenchone, etc., as well as acetylase, 2, 4 —Hexanedione, 2, 4-heptandione, 3, 5-heptandione, 2, 4-octanedione, 3, 5-octane
  • ketone solvents may be mentioned. These ketone solvents may be used alone or in combination of two or more.
  • amide solvent for example, formamide, N-methylformamide, N, N-dimethylformamide, N-ethylformamide, N, N- jetylformamide, acetoamide, N-methylacetoamide, N, N-dimethylaceamide De, N-Ethylacetoamide, N, N-Getyl Ascetoamide, N-Methylpropionamide, N-Methylpyrrolidone, N_Formylmorpholine, N_Formyl Piperidin, N-Formylpyrrolidine, N-A And cetyl morpholine, N-acetyl piperidine, N-acetyl pyrrolidine and the like.
  • amide solvents may be used alone or in combination of two or more.
  • ester solvent for example, jetyl carbonate, ethylene carbonate, propylene carbonate, jetyl carbonate, methyl acetate, ethyl acetate, heptyl lactone, ⁇ -valerolactone, n-propyl acetate, n-propyl acetate, i-propyl acetate, n- acetate Butyl, i-butyl acetate, sec-butyl acetate, n-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate, methylpentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, cyclo acetate Xyl, methylcyclohexyl, acetate n-nonyl, methyl acetoacetate, ethyl acetate, ethyl acetate,
  • ester solvents may be used alone or in combination of two or more.
  • aprotic solvents include: acetonitrile, dimethyl sulfoxide, N, N, ⁇ ′, N′—tetraethyl sulfamide, hexamethyl phosphate triamide, ⁇ -methyl morpholine, ⁇ -methyl vinylol, ⁇ -ethyl vinyl, -Methyl- ⁇ 3 _ pyrroline, ⁇ -methylbiperidine, ⁇ -ethyl piperidine, ⁇ , ⁇ ⁇ ⁇ ⁇ -dimethylbiperazine, ⁇ -methylimidazole, ⁇ -methyl-4-piperidone, ⁇ -methyl-2-piperidone, ⁇ -methyl- 2 —Pyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyltetrahydro-2 (1 H) monopyrimidinone and the like can be mentioned.
  • a catalyst is preferably used.
  • the following metal chelate compounds, organic acids, inorganic acids, organic bases and inorganic bases can be mentioned.
  • metal chelate compounds for example, triethoxy 'mono (acetyl acetate) titanium, tree ⁇ ⁇ -propoxy mono (acetyl acetate) titanium, tree i-propoxy mono (acetyl acetate) titanium, tri — N mono-butoxy mono (acetyl assetonato) titanium, tri-sec ⁇ butoxy * mono (acet ylacetonato) titanium, tri _ t butoxy 'mono (acetyl isocyanate) titanium, diethoxy bis ( (Acetyl Assert) ⁇ ⁇ ) Titanium, di-n- propoxy bis (acetyl acetate) Titanium, Ze-ip propoxy bis (acetyl acetate) Titanium, di- n- butoxy 'bis (Acetyl Assertato) Titanium, G-sec -Butoxy Bis (Acetyl A-Certnat) Titanium, G-T Butoxy bis (acetyl a
  • Aluminum chelate compounds such as aluminum squirrel (acetyl acetonato) aluminum, aluminum squirrel (acetylacetoate)
  • organic acid examples include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacic acid, Gallic acid, butyric acid, melittic acid, halakidonic acid, mykimic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linoleic acid, salicylic acid, benzoic acid, P-aminobenzoic acid, P
  • -Toluenesulfonic acid benzenesulfonic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid, formic acid, fumaric acid, citric acid, tartaric acid and the like can be mentioned.
  • inorganic acids examples include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid and phosphoric acid.
  • organic base examples include pyridine, pyrrole, piperazin, pyrrolidine, piperine, picoline, dimethylamine, triethylamine, monoethanolamine, diethanolamine, dimethylmonoethanolamine, monomethyl diethanolamine, triethanolamine, Diazabicyclo ocrans, diasbicyclononane, diasbicycloundecene, tetramethylammonium hydrooxide and the like can be mentioned.
  • Examples of the inorganic base include ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide and the like.
  • metal chelate compounds, organic acids and inorganic acids are preferable, and titanium chelate compounds and organic acids can be mentioned more preferably. These may be used alone or in combination of two or more.
  • the amount of the catalyst used is preferably 0.01 to 10 parts by weight with respect to 100 parts by weight of the compound (1), or a combination of the compound (1) and the compound (2) (in terms of completely hydrolyzed condensate) More preferably, it is in the range of 0.001 to 1 part by weight.
  • the liquid crystal aligning agent of the present invention is preferably obtained by dissolving or dispersing the above-mentioned hydrolytic condensate in an organic solvent.
  • organic solvents represented by the following formulas (1), (II) and (III) are used as the organic solvent.
  • formula (I) is a hydrogen atom, a methyl group, an ethyl group or an acetyl group
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • n is an integer of 1 to 3.
  • R 3 is a hydrogen atom, a methyl group, an ethyl group or an acetyl group
  • R 4 is an alkyl group having 1 to 4 carbon atoms
  • m is an integer of 1 to 3.
  • R 5 is an alkyl group having 2 to 5 carbon atoms.
  • ethylene glycol monopropyl ether, ethylene glycol monobutyl ether (butyl sequestrate) and ethylene glycol monoamyl ether are preferable.
  • n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, sec-butyl acetate, n-pentyl acetate and sec-pentyl acetate are preferable.
  • surfactant examples include nonionic surfactants, anionic surfactants, cationic surfactants and amphoteric surfactants. Furthermore, silicone surfactants, polyalkylene oxide surfactants, fluorine-containing surfactants and the like are listed. Can be
  • the liquid crystal aligning agent of the present invention may contain a functional silane-containing compound or an epoxy group-containing compound from the viewpoint of improving the adhesion to the substrate surface.
  • functional silane-containing compounds include, for example, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 2-aminobutylbitrimethoxysilane, 2-aminopropyltriethoxysilane, N- (2-amino Ethyl)-3-aminopropyl trimethoxysilane, N-(2- aminoethyl)-1 -aminopropylmethyldimethoxysilane, 3- ureido provirtrimethoxysilane, 3- ureidopropyltriethoxysilane, N-1 Ethoxycarbonyl mono-3-aminopropyl trimethoxysilane, N-hydroxycarbonyl-3-aminopropyltriethoxysilane, N-tri
  • epoxy group-containing compound for example, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol Diglycidyl ether, 1,6-hexanediol diglycidyl ether, daricerine didicidyl ether, 2,2-dibromoneopentyl glycaryl ether, 1,3,5,6-tetraglycidyl ester 2,4 —Hexanediol, N, N, ⁇ ', ⁇ ' —Tetraglycidyl_m-xylenediamine, 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, N, N, ⁇ ′, ⁇ ′-tetraglycidyl 4,4′-dia
  • the ratio of the polymer which is the reaction product in the liquid crystal aligning agent of the present invention to the solvent is selected in consideration of viscosity, volatility and the like, but the ratio of the polymer in the liquid crystal aligning agent (solid content concentration) It is a S I_ ⁇ 2 concentration of silicon atoms in terms of S I_ ⁇ 2 contained in the polymer, preferably from 0.0 to 7 0 wt% Deari, more preferably 0.0 5-6 0 weight %, More preferably 1 to 30% by weight.
  • the liquid crystal aligning agent of the present invention is preferably applied to the surface of a substrate by, for example, a roll coating method, a spinner method, a printing method or the like, and then dried by heating to obtain a liquid crystal alignment film
  • the thickness of the coating film may be too small to obtain a good liquid crystal alignment film. If the solid content concentration exceeds 70% by weight, the film thickness of the coating film becomes too large to obtain a good liquid crystal alignment film, and the viscosity of the liquid crystal alignment agent increases and the coating characteristics become worse. May be inferior.
  • a liquid crystal display element can be produced, for example, by the following method using the liquid crystal aligning agent of the present invention.
  • the liquid crystal aligning agent of the present invention is applied to one surface of a substrate provided with a patterned transparent conductive film by, for example, a roll coating method, a spinner method, a printing method, an ink jet method or the like. Then, a coated film is formed by heating the coated surface.
  • the atmosphere for the coating and heating steps can be carried out in an inert gas such as nitrogen, helium or argon, and can be carried out in an atmosphere mixed with a reducing gas such as hydrogen if necessary.
  • the substrate for example, glass such as float glass, soda glass, etc .; a transparent substrate made of plastic such as polyethylene terephthalate, polybutyl terephthalate, polyether sulfone, methyl methacrylate, polycarbonate and the like may be used. it can.
  • a transparent substrate made of plastic such as polyethylene terephthalate, polybutyl terephthalate, polyether sulfone, methyl methacrylate, polycarbonate and the like may be used. it can.
  • the transparent conductive film provided on one surface of a substrate made of tin oxide (S N_ ⁇ 2) NESA film (US PPG registered trademark), etc. can be used.
  • I TO film made of indium tin monoxide oxidation (I n 2 ⁇ 3 -S n0 2), the path evening training of the transparent conductive film, The photo etching method or the method using a mask in advance is used.
  • a functional silane-containing compound, a functional titanium-containing compound, etc. can also be applied.
  • the heating temperature after application of the liquid crystal aligning agent is a temperature at which deformation of the substrate material does not occur, preferably 20 to 300, and more preferably 120 to 300.
  • a heat source for the heat treatment for example, a hot air furnace, an infrared heating furnace, a hot plate and the like can be mentioned.
  • the film thickness of the coating film to be formed is preferably 0.001 to 1 m, more preferably 0.50 to 0.5 / m.
  • liquid crystal orientation angle can be controlled by rubbing the surface of the formed coating film surface.
  • thermosetting sealant in a suitable pattern on the periphery of one of the substrates.
  • Two substrates are placed opposite to each other via a gap (cell gap) so that the directions of liquid crystal alignment in each liquid crystal alignment film are orthogonal or antiparallel, and after the two substrates are bonded, Heat to cure the sealant.
  • the liquid crystal is injected and filled in the cell gap partitioned by the substrate surface and the sealing agent, and the injection holes are sealed to constitute a liquid crystal cell.
  • the liquid crystal dropping method that is, the DFDF (On e Dr op F i 1 1) method can also be used for the step of bonding liquid crystal from the bonding of the two substrates.
  • a liquid crystal alignment film is applied, and a UV curable sealant is applied in a suitable pattern on one side of the substrate to which the liquid crystal alignment ability is given as described above, and the liquid crystal is dropped on the necessary places.
  • a UV curable sealant is applied in a suitable pattern on one side of the substrate to which the liquid crystal alignment ability is given as described above, and the liquid crystal is dropped on the necessary places.
  • the ultraviolet light irradiation is not limited to the entire surface exposure, and appropriate methods such as mask exposure and scan exposure can be used.
  • a polarizing plate is formed on the outer surface of the liquid crystal cell, that is, on the other surface side of each substrate constituting the liquid crystal cell, and a liquid crystal alignment film in which the polarization direction is formed on one surface of the substrate.
  • the liquid crystal display element can be obtained by bonding the liquid crystal alignment direction or the alignment direction perpendicular to the liquid crystal alignment direction.
  • liquid crystals examples include nematic type liquid crystals and smectic type liquid crystals, among which nematic type liquid crystals are preferable.
  • Schiff base type liquid crystals azoxy type liquid crystals, biphenyl type liquid crystals, phenylcyclohexane type liquid crystals, ester type liquid crystals, A phenyl liquid crystal, a biphenylcyclohexane liquid crystal, a pyrimidin liquid crystal, a dioxane liquid crystal, a bicyclooctane liquid crystal, a cubane liquid crystal, or the like can be used.
  • liquid crystals may be marketed as, for example, cholesteryl chloride, cholesteryl nonaate, cholesteryl carbonate such as cholesteryl carbonate, or as "C-15" or “CB-15” (product of Merck). It is also possible to use it by adding a chiral agent or the like.
  • ferroelectric liquid crystals such as .p-hydroxybenzylidene-p-amino-2-methylbutyl cinnamate can also be used.
  • a polarizing plate As a polarizing plate to be bonded to the outer surface of a liquid crystal cell, a polarizing plate called a H film which absorbs iodine while stretching and orienting polyvinyl alcohol is sandwiched between a cellulose acetate protective film or a H film itself And a polarizing plate made of Practical example
  • the liquid crystal aligning agent R-2 was obtained by adding 5. 6 g of tellurium and filtering with a membrane filter filter having a pore diameter of 0.2 m.
  • the liquid crystal aligning agent of the present invention gives a liquid crystal alignment film which is excellent in storage stability, excellent in vertical alignment, and less in decrease in voltage holding ratio due to light or heat.

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  • Liquid Crystal (AREA)

Abstract

L'invention concerne un agent d'alignement de cristaux liquides, comprenant un produit polymérisé produit par hydrolyse d'un composé de silicium représenté par la formule (1) seule, ou d'un mélange d'un composé de silicium représenté par la formule (1) et d'un composé de silicium représenté par la formule (2), et par condensation du produit d'hydrolyse. Le composé de silicium représenté par la formule (2) est présent dans le mélange dans une quantité d'au plus 0,5 mole par mole de la quantité totale du composé de silicium représenté par la formule (1) et du composé de silicium représenté par la formule (2). L'agent d'alignement de cristaux liquides offre une longue durée de stockage, une propriété caractéristique d'alignement vertical et une réduction limitée du taux de maintien de tension due à la lumière ou à la chaleur. Si(OR1)4 (1) [où R1 représente un groupe alkyle] RSi(OR2)3 (2) [où R représente un groupe méthyle ou éthyle ; et R2 représente un groupe alkyle]
PCT/JP2007/073627 2006-12-01 2007-11-30 Agent d'alignement de cristaux liquides et élément d'affichage à cristaux liquides WO2008066205A1 (fr)

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JP2006-326070 2006-12-01
JP2006326070 2006-12-01

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WO2008066205A1 true WO2008066205A1 (fr) 2008-06-05

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
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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JPS54161959A (en) * 1978-06-13 1979-12-22 Hitachi Ltd Liquid crystal display device
JPH07318945A (ja) * 1994-03-30 1995-12-08 Nissan Chem Ind Ltd 液晶配向処理基板及びその製造方法
JP2004061911A (ja) * 2002-07-30 2004-02-26 Jsr Corp 液晶配向剤および液晶配向膜の形成法

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
JPS54161959A (en) * 1978-06-13 1979-12-22 Hitachi Ltd Liquid crystal display device
JPH07318945A (ja) * 1994-03-30 1995-12-08 Nissan Chem Ind Ltd 液晶配向処理基板及びその製造方法
JP2004061911A (ja) * 2002-07-30 2004-02-26 Jsr Corp 液晶配向剤および液晶配向膜の形成法

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
KR20110104535A (ko) * 2008-12-25 2011-09-22 닛산 가가쿠 고교 가부시키 가이샤 잉크젯 도포용 액정 배향제, 액정 배향막 및 액정 표시 소자
CN102317848A (zh) * 2008-12-25 2012-01-11 日产化学工业株式会社 喷墨涂布用液晶取向剂、液晶取向膜及液晶显示元件
TWI457370B (zh) * 2008-12-25 2014-10-21 Nissan Chemical Ind Ltd The ink-jet coating agent with the liquid crystal, the liquid crystal alignment film and a liquid crystal display element
KR101708949B1 (ko) 2008-12-25 2017-02-21 닛산 가가쿠 고교 가부시키 가이샤 잉크젯 도포용 액정 배향제, 액정 배향막 및 액정 표시 소자
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
TWI458758B (zh) * 2008-12-26 2014-11-01 Nissan Chemical Ind Ltd Liquid crystal alignment agent for inkjet coating, liquid crystal alignment film and liquid crystal display element
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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TW200835984A (en) 2008-09-01
TWI437329B (zh) 2014-05-11

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