WO1995007474A1 - Polarisant, plaque polarisante et son procede de production - Google Patents

Polarisant, plaque polarisante et son procede de production Download PDF

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Publication number
WO1995007474A1
WO1995007474A1 PCT/JP1994/001491 JP9401491W WO9507474A1 WO 1995007474 A1 WO1995007474 A1 WO 1995007474A1 JP 9401491 W JP9401491 W JP 9401491W WO 9507474 A1 WO9507474 A1 WO 9507474A1
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WO
WIPO (PCT)
Prior art keywords
photoactive
polarizing element
layer
molecules
polarizing
Prior art date
Application number
PCT/JP1994/001491
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Kunihiro Ichimura
Norio Ishizuki
Junji Toda
Original Assignee
Nippon Kayaku Kabushiki Kaisha
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 Nippon Kayaku Kabushiki Kaisha filed Critical Nippon Kayaku Kabushiki Kaisha
Priority to EP94926376A priority Critical patent/EP0670506B1/en
Priority to US08/428,150 priority patent/US5706131A/en
Priority to HK98102818.9A priority patent/HK1003727B/en
Priority to KR1019950701846A priority patent/KR100327764B1/ko
Priority to DE69433486T priority patent/DE69433486T2/de
Publication of WO1995007474A1 publication Critical patent/WO1995007474A1/ja

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid

Definitions

  • the present invention relates to a novel polarizing element, a polarizing plate, and a method for producing the same.
  • Polarizing elements used in liquid crystal display devices, sunglasses, googles, etc. dissolve or adsorb dichroic molecules in a polymer material such as polyvinyl alcohol, and move the film in one direction. It is manufactured by a method in which dichroic molecules are arranged by stretching them. It is also manufactured by a method in which dichroic molecules are adsorbed on a polymer film stretched in one axis direction. However, the polarization axis of the polarizing element obtained by these methods is fixed in one direction, and only a flat plate can be manufactured. In order to manufacture a variety of display elements including liquid crystal displays, a polarizing element having a fine pattern and exhibiting polarization in an arbitrary direction and a curved polarizing element are required.
  • Multiaxial polarizers with polarization axes in various directions can be manufactured with a single polarizing plate (J.F.Dreyer, C.W.
  • the method for producing a polarizing element by this rubbing treatment involves placing a mask that gives a pattern with a different polarization axis on the substrate to be surface-treated, and only the part not covered with the mask. It is impossible to draw a fine pattern with a different polarization axis because of mechanical rubbing.In the case of a gradation display pattern such as a photograph or a complicated pattern shape, Such a method cannot be applied.
  • the static electricity generated by rubbing absorbs fine dust, causing surface contamination.
  • a method for precisely and finely controlling the polarization axis in an arbitrary direction has not been known so far.
  • the present invention does not require a polymer film stretching operation, and To provide a polarizing element, a polarizing plate, and a method of manufacturing the same capable of drawing a fine polarization pattern.
  • the present inventors have conducted intensive studies in order to achieve the above object, and as a result, provided a photoactive molecular layer that easily changes the molecular axis by linearly polarized light on a substrate, and the molecular layer is formed on the photoactive molecular layer. After irradiating with linearly polarized light in the absorption wavelength range and then providing a dichroic molecular layer on the photoactive molecular layer, they found that dichroic molecules were arranged anisotropically.
  • FIG. 1 is a schematic diagram of an apparatus for providing a photoactive separation layer.
  • Fig. 2 is a schematic view of the irradiation device for visible polarized light.
  • FIG. 3 shows a schematic view of an apparatus for providing a dichroic molecular layer.
  • FIG. 1 (a) indicates a film roll, (b) indicates a polymer solution dish, (c) indicates a dipping roll, and (d) indicates a winding port.
  • FIG. 2 shows a film roll
  • (b) shows an ultra-high pressure mercury lamp
  • (c) shows a polarizing element
  • (d) shows a winding roll.
  • Fig. 3 (a) is the film roll, (b) is the dish for the aqueous solution of dichroic molecules, (c) is the gravure roll, and (d) is the winding roll. Show.
  • the molecular axis is easily changed by linearly polarized light on the substrate.
  • a molecular layer that causes photonization that is, a photoactive molecular layer
  • a dichroic molecular layer is provided on the photoactive molecular layer.
  • dichroic molecules are arranged anisotropically, and have been completed based on that knowledge. That is, the present invention
  • a polarizing element or polarizing plate having a layer containing a photoactive molecule and a layer containing a dichroic molecule in contact with the layer
  • a multiaxial polarizing element or polarizing plate having a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer
  • a three-dimensional display polarizing element or polarizing plate having a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer.
  • the substrate used in the present invention only needs to be a substrate to which the photoactive molecules can be bonded or coated.
  • a glass plate such as silica glass or hard glass, a quartz plate or the like can be used.
  • ABS resin acetate resin, (meth) acrylic resin, cellulose acetate, chlorinated polyether, ethylene-vinyl acetate copolymer, fluororesin, ionomer, Methyl Pen Temporary, Nylon, Polyamide, Polycarbonate, Polyester Polyesters such as polyethylene terephthalate, polybutylene terephthalate, polyimid, polyolefin sulfide, and polyolefin sulfide , Polyarylsulfone, Polyacrylate, Polyethylene, Polypropylene, Polystyrene, Polysulfone, Vinyl acetate resin, Vinylidene chloride resin, AS resin, vinyl chloride resin, alkyd resin, aryl resin, amino resin, urea resin, melamine
  • the photoactive molecule used in the present invention is a molecule that undergoes a change in molecular axis alignment by linearly polarized light.
  • the change in molecular axis orientation is a phenomenon in which the direction of the molecular axis changes after absorbing the light energy of linearly polarized light.
  • the wavelength of light absorbed by this photoactive molecule is only in the visible light range. It also includes those in the ultraviolet and infrared regions that cannot be observed with the naked eye. When this layer of photoactive molecules is irradiated with linearly polarized light that includes the wavelength range absorbed by the molecules, the molecular axis orientation easily changes.
  • photoactive molecule used in the present invention examples include aromatic compounds such as azobenzene, azonaphthylene, bisazo compound, and formazan.
  • Aromatic azo compounds, and compounds having a basic skeleton of azoxibenzene can be mentioned. Examples of these are provided below, but are not limited.
  • the photogeometric isomers are unstable and immediately return to the original structure, and compounds that show no substantial photoisomerization upon irradiation with light at room temperature.
  • compounds not shown at all can also be used in the present invention, and examples thereof include, but are not limited to, cyanines and melocyanines shown below.
  • photoactive molecules are listed as examples of the basic skeleton of the compound having a double bond group, and these skeletons have a methyl group, an ethyl group, a propyl group, and a butyl group.
  • at least one substituent selected from a dialkylamino group such as an alkoxycarbonyl group, a hydroxy group, a dimethylamino group, a getylamino group, a nitro group, and the like.
  • the photoactive molecule in order to provide a photoactive molecular layer that causes such a reversible molecular axis orientation change on a substrate, the photoactive molecule is physically or chemically used according to the surface characteristics of the substrate.
  • a film in which the photoactive molecules are fixed on the substrate surface that is, a film in which the photoactive molecules are bonded to the substrate surface and a polymer in which the photoactive molecules are bonded are coated as a thin film on the substrate.
  • Those obtained are preferable because their orientation state is stable.
  • a method for binding photoactive molecules to the substrate surface is described.
  • the substrate is made of silica glass
  • the method used for liquid crystal alignment can be adopted (Molecular by J. Cognard).
  • a photoactive molecule solution having the above-mentioned non-aromatic double bond group and the following surface active group dissolved in a solvent is added to the substrate.
  • One method is to apply it to the surface to adsorb and bind photoactive molecules.
  • the surface-active group include a carboxylic acid residue, a malonic acid residue, a carnomoyl group, a tetraalkylammonium group, an alkylpyridinium residue, an alkylquinoline residue, Examples include carboxyl silochromium residues, ester residues, nitrile residues, urea residues, amino groups, hydroxy groups, and betaine residues. . If the photoactive molecule is a liquid, it may be applied directly to the substrate surface.
  • a Langmuir is used in which a photoactive molecule having the above-mentioned surface active group is developed as a monomolecular layer on the water surface, and at least one layer is transferred to a substrate.
  • the arbojet method can be adopted.
  • the surface-active groups include, for example, carboxyl, carbamoyl, amino, ammonium, tetraalkylammonium, and hydroxy. Is preferred.
  • a method of binding a photoactive molecule to a substrate surface via a silyl group there is a method of binding a photoactive molecule to a substrate surface via a silyl group.
  • a method of binding a photoactive molecule having at least one halogen atom or a silyl group substituted by an alkoxy group to the substrate surface or a method having an amino group-containing silyl group.
  • Examples include a method in which a photoactive molecule having a carboxyl group and a acrylyl group is subjected to a condensation reaction or an addition reaction on the substrate surface treated with a releasing agent.
  • the silyl group is introduced into the photoactive molecule in advance, and the surface of the silica glass is treated.
  • silyl group substituted with at least one halogen atom or alkoxy group examples include, for example, a trichlorosilyl group, a trimethoxysilyl group, and a trimethylsilyl group.
  • An ethoxysilyl group examples include, for example, a trichlorosilyl group, a trimethoxysilyl group, and a trimethylsilyl group.
  • An ethoxysilyl group examples of the silylating agent having an amino group.
  • Noprovir triethoxysilane Aminoprovir triethoxysilane.
  • the operation of binding these photoactive molecules to the substrate surface may be performed in the presence of another silylation agent.
  • silylation agents for this purpose include methyl triethoxy silane, dimethino reject ethoxy silane, trimethyl phenol chloro silane, and ethyl triet.
  • Xyloxysilane Jetinorejet Xyloxylan.Propyl triethoxysilane, butyl triethoxy silane, butyl methyl ethoxy silane, pentyl triethoxy silane, hexyl yl Alkyl such as ethoxysilane (Poly) alkoxysilanes can be mentioned, but not limited thereto.
  • the above-mentioned photoactive compound having a surface active group is adsorbed and bonded to the surface of the substrate.
  • the photoactive molecule may be bound to the active group exposed on the molecular surface by a covalent bond.
  • the photoactive molecule is bonded to the surface layer of the substrate by an acetal bond, an ester bond, or a perylene bond.
  • a photoactive molecule having a covalent bond forming group such as, for example, a formyl group, a macroporous formyl group, or an isocyanate group is prepared, and this is prepared in a solvent that does not dissolve polyvinyl alcohol.
  • the substrate having the polyvinyl alcohol film may be immersed in the solution to react.
  • a catalyst acid such as P-toluenesulfonate may be added for acetalization, or an acid generated in the reaction for esterification / retanification.
  • a base such as triethylamine or pyridin may be added in order to remove nitrogen.
  • a method is described in which a polymer to which a photoactive molecule is bound or a polymer to which a photoactive molecule is added is prepared, and this is applied as a thin film on a substrate.
  • a method for preparing a polymer to which a photoactive molecule is bound will be described. In order to bond the photoactive molecule to the side chain or main chain of a high molecule, a monomer having a photoactive molecule is polymerized or a polymer A photoactive molecule having a reactive residue suitable for its chemical structure is bound to the substance.
  • a photoactive molecule having a (meth) acrylic group having a radical polymerization ability is suitable as a monomer, and the polymerization is performed by polymerization.
  • a polymer in which a photoactive molecule is bonded to a side chain can be easily obtained.
  • a bifunctional monomer having a photoactive molecule The body can be prepared. Examples of the bifunctional monomer include vinyl carboxylate.
  • the polymer compound obtained by bonding the photoactive molecule obtained by the polymerization includes a homopolymer obtained by polymerizing only the monomer having the photoactive molecule, a monomer having the photoactive molecule and another monomer. Any of copolymers obtained by polymerizing a monomer and a monomer may be used. Other monomers include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, butynole (meth) acrylate, and 2-ethylhexyl. (Meta) accredit, etc.
  • the proportion used depends on the structure of the monomer, but it is in the range of 1: 0 to 1:10, more preferably 1: 0 to 1:50.
  • the above-mentioned fourth method can be used.
  • the polymer used Nil alcohol, styrene-maleic anhydride copolymer, polyglycidyl glycerate, or copolymers thereof can be mentioned. Not.
  • a spin coating method is preferable. Further, this kind of polymer may be provided on a substrate by a Langmuir-Blodgett method. Further, the substrate may be immersed in these polymer solutions and adsorbed. A film thickness of 1 m or less is sufficient.
  • the wavelength of the polarized light to be applied is not particularly limited as long as the wavelength is absorbed by the photoactive molecule.
  • Light sources include mercury lamps, xenon lamps, fluorescent lamps, chemical lamps, helium-cadmium lasers, algon lasers, and crypton lamps. Lasers, helium-neon lasers, semiconductor lasers, and even sunlight. The selection may be made according to the absorption wavelength region of the photoactive molecule, the light irradiation time, or the irradiation area.
  • a linearly polarizing element or a linearly polarizing plate In order to obtain linearly polarized light, light emitted from these light sources may be combined with a linearly polarizing element or a linearly polarizing plate.
  • a polarizing element or polarizing plate for this purpose include a prism element such as a grammon prism and a polymer film stretched by dissolving or adsorbing dichroic molecules. Examples include a polarizing element and a polarizing plate.
  • a polarizing element (plate) manufactured by the present invention can also be used.
  • the exposure energy of the linearly polarized light used here varies depending on the wavelength, the structure of the photoactive molecule, the bonding state, the irradiation temperature, and the like, but is preferably in the range of lm JZ cm 2 to 1 OJZ cm 2 .
  • a polarizing element plate is not required if the laser beam itself is linearly polarized light.
  • the photoactive molecular layer may be irradiated with linearly polarized light through a desired mask pattern.
  • the pattern By diverging or condensing linearly polarized light using a lens or the like, the pattern can be greatly enlarged, and conversely, an extremely fine pattern can be obtained.
  • a laser is used as the light source and the laser beam itself is linearly polarized, an extremely fine pattern can be freely formed by combining with a polarization plane rotating element such as a Faraday element. Can draw.
  • dichroic molecules By simply adsorbing dichroic molecules to the photoactive molecular layer having molecular axes arranged in a certain direction obtained in this way, that is, only by providing a dichroic molecular layer on the photoactive molecular layer,
  • the molecular axis of the dichroic molecule is aligned in the direction of the molecular axis of the photoactive molecule, that is, in the direction defined by the polarization axis of the linearly polarized light applied to the photoactive molecular layer, and the polarization axis is fixed. It was surprising that the properties of a polarizing element (plate) were exhibited.
  • the dichroic molecule used in the present invention is a compound exhibiting polarizability by being arranged in a certain direction by itself or as an aggregate.
  • a compound having an aromatic ring structure is preferable.
  • Aromatic ring structures include benzene, naphtalin, anthracene, and phenanthrene, as well as thiazole, pyridin, and pyrimidene.
  • Gin, pyridazine, pyrazine, key Heterocycles such as phosphorus and quaternary salts thereof, and condensed rings thereof with benzene and naphthalene are particularly preferred.
  • a hydrophilic substituent such as a sulfonate group, an amino group or a hydroxyl group is introduced into these aromatic rings.
  • dichroic molecules examples include azo dyes, stilbene dyes, pyrazolone dyes, triphenylmethane dyes quinoline dyes, oxazine dyes, and thiazine dyes.
  • Dye-based compounds such as dyes and anthraquinone dyes can be given. Water-soluble compounds are preferred, but not limited thereto.Hydrophilic substituents such as sulfonate, amino, and hydroxyl groups are introduced into these dichroic molecules. This is preferred.
  • dichroic molecules include C.I.
  • the dichroic molecule alone or a mixture of two or more of the above dichroic molecules is dissolved in a hydrophilic solvent such as water methanol or ethanol or a water-containing solvent thereof.
  • a hydrophilic solvent such as water methanol or ethanol or a water-containing solvent thereof.
  • the concentration is preferably about 0.1 to 10 wZw%, more preferably about 0.5 to 5 wZw%.
  • a surfactant can be added to this solution.
  • any of a cation-based, a nonionic-based, and an anionic-based surfactant can be used, but a nonionic surfactant is preferable.
  • the solution of the dichroic molecule is dropped on the surface of the substrate, and then a layer of the dichroic molecule having a uniform thickness is provided all over the substrate or by a spin coating method.
  • a substrate having a photoactive molecule layer irradiated with linearly polarized light is immersed in the dichroic molecule solution, and then the substrate is pulled up. In order to obtain a uniform concentration of dichroic molecules, it is preferable to keep the pulling rate constant.
  • the thickness of the dichroic molecular layer is preferably thinner from the viewpoint of improving the polarization characteristics, for example, 10 mm or less, particularly preferably 0.1 to 2 mm.
  • the substrate to which the molecule solution is attached is dried to form a solid-state dichroic molecular layer, whereby the polarizing element (plate) of the present invention is obtained. Drying conditions vary depending on the type of solvent, type of dichroic molecule, amount of applied dichroic molecule solution, concentration of dichroic molecule, etc., but the temperature is room temperature to 10 ° 0 ° C, preferably room temperature to 50 ° C, humidity of 20 to 80% RH, preferably 30 to 70% RH.
  • the anisotropically adsorbed dichroic molecular layer prepared in this way is in a solid state, for example, amorphous or crystalline, but the dichroic molecular layer is generally inferior in mechanical strength.
  • a protective layer is provided on the surface. This protective layer is usually formed by coating the dichroic molecular layer with an ultraviolet-curable or thermosetting transparent polymer film, or by using a transparent film such as polyester film or cellulose acetate film. It is provided by a coating method such as laminating with a polymer film.
  • the polarizing element (plate) of the present invention it is possible to further enhance the polarization characteristics by subjecting the photoactive molecular layer to corona discharge treatment or ultraviolet irradiation.
  • the corona discharge treatment is preferably performed on the photoactive molecular layer and before the irradiation of linearly polarized light, but is not particularly limited.
  • various commercially available corona discharge treatment machines can be applied.
  • Conditions for the corona discharge treatment include the type of substrate on which the photoactive molecular layer is provided, the composition and thickness of the photoactive molecular layer, and the composition and film thickness of the dichroic molecular layer applied after the corona discharge treatment.
  • the energy density is 20 to 400 W ⁇ min'm— 2 , preferably 50 to 30 W, for each treatment. It is about 0 W ⁇ min, m- 2 . If one process is not enough, it can be performed two or more times. Further, it is preferable that the ultraviolet irradiation is performed on the photoactive molecular layer and before the linearly polarized light irradiation, but this is not particularly limited.
  • the wavelength of the ultraviolet light used is not particularly limited. For example, far ultraviolet light having a wavelength of 300 nm or less is preferable. Also, UV Irradiation is preferably performed under a stream of oxygen. Various types of commercially available ultraviolet irradiation can be applied as an apparatus for performing ultraviolet irradiation.
  • the conditions for UV irradiation depend on the type of substrate on which the photoactive molecular layer is provided, the composition and thickness of the photoactive molecular layer, and the composition and thickness of the dichroic molecular layer applied after UV irradiation. Although different, an irradiation time of at least several minutes is sufficient.
  • the polarizing element (plate) of the present invention can be provided with a polarizing layer having an arbitrary axis on a free curved surface without applying external stress.
  • the photoactive molecular layer used in the present invention is provided on a curved surface such as sunglasses or goggles, and after irradiating linearly polarized light, a dichroic molecular layer is provided.
  • Polarizers (plates) such as glasses and goggles can be made.
  • the polarizing element (plate) of the present invention can be provided with a gradation having its own shading or a pattern having many polarization axes in the manufacturing process.
  • a gradation-displaying polarization element (plate) with a gradation uses linearly polarized light that passes through a mask pattern with shading or a negative film of a photograph. It can be manufactured more.
  • the (plate) can be manufactured by irradiating different parts with linearly polarized light having different polarization axes when printing a polarization pattern on the photoactive molecular layer.
  • a stereoscopic display polarizing element can be manufactured.
  • What is stereoscopic display is two-dimensional The three-dimensional representation of photos, figures, pictures, etc., drawn by using a special technique. For example, there is a method of viewing printed matter drawn in red or blue through eyeglasses with the left and right lenses colored red or blue, respectively, or a method of shifting the focus of the eyes to make it look three-dimensional. is there.
  • polarizing element (plate) of the present invention can draw fine patterns having the same or different polarization axes, and is therefore suitable for producing a stereoscopic display polarizing element (plate).
  • a polarizing element (plate) for the left eye and a right eye is required.
  • Exposure to linearly polarized light through the desired mask pattern or negative film of the photograph, respectively, may print the polarization pattern on the photoactive molecular layer.
  • the offset angle is, for example, ⁇ 45 degrees, ⁇ 90 degrees, ⁇ 135 degrees.
  • Luminous rate (%) ⁇ ( ⁇ 2 - ⁇ ,) / ( ⁇ 2 + ⁇ ) ⁇ 1/2 / 100
  • the light source shall be a 50 O W / h ultra-high pressure mercury lamp, be visible light (> 400 nm) with a power-in letter, and be linearly polarized through a polarizer.
  • the linearly polarized light is irradiated for 1 minute at a room temperature from a distance of 50 cm onto the coated surface of the substrate placed parallel to the polarization axis of the polarizing plate.
  • the polarizing element of the present invention is dried at 25 ° C and 50% RH.
  • the transmittance, polarization ratio and average polarization ratio (/ 0: average polarization ratio at each wavelength) when ( ⁇ 1) is obtained are as follows.
  • Example 4 Polymerization was carried out in the same manner as in Example 1 by dissolving acryloyloxyazobenzene and methyl methacrylate in benzene at a molar ratio of 1: 9 to obtain a 20-weight solution. I do. A solution consisting of 10 parts of the obtained polymer and 90 parts of toluene was hardened. After spin-coating on glass and drying by heating at 105 ° C. for 10 minutes, linearly polarized light is applied in the same manner as in Example 1. Then, C.I.D irect B 1 ue 675 5 parts and C.I.D irect
  • the polarizing element (plate) of the invention is obtained.
  • the polarization ratio and the average polarization ratio are as follows.
  • Example 2 In the same manner as in Example 1, a polymer of methacrylic acid ester having benzylidene aniline in the side chain was synthesized, and 10 parts of this polymer and 90 parts of toluene were synthesized. The resulting solution is spin-coated on a hard glass and dried by heating at 105 ° C for 10 minutes. This The surface of the substrate is irradiated with linearly polarized light obtained by combining a light from an ultra-high pressure mercury lamp with a Katto filter (> 340 nm) and a polarizer. Then, a dye solution is applied and dried in the same manner as in Example 2 to obtain a polarizing element (plate) of the present invention.
  • Example 6 Polarizing element (plate) using polyvinylidene dendrite film
  • Example 1 0.1 part of the polymer containing azobenzene used in Example 1 And 99.9 parts of toluene are spin-coated on a polyvinylidene fluoride film, and dried by heating at 105 ° C for 10 minutes.
  • the substrate was irradiated with linearly polarized light, coated with a dye solution, dried at 25 ° C. and 50% RH, and the coated surface was coated with a polyethylene
  • the polarizing element (plate) of the present invention is obtained by laminating with a rate film.
  • Example 7 Gradation display polarizing element (plate)
  • a solution consisting of 10 parts of the polymer having an azobenzene group obtained in Example 1 and 90 parts of toluene is spin-coated on hard glass, and dried by heating at 105 ° C. for 10 minutes.
  • a mask pattern with a gradually changing contrast is placed on the coating surface of this substrate, and a Katto fountain letter (> 340) is applied to the light from the ultra-high pressure mercury lamp.
  • the linearly polarized light obtained by combining the polarizer and the polarizer is irradiated at room temperature for 1 minute from a distance of 50 cm.
  • the dye solution is applied and dried in the same manner as in Example 1 to obtain the polarizing element (plate) of the present invention. Observing this device through a separately prepared polarizing plate, a mask pattern image with a contrast can be obtained in stages. Then, when the polarizing plate is rotated, an image in which the brightness is inverted every 90 degrees is obtained.
  • a solution consisting of 10 parts of the polymer having an azobenzene group obtained in Example 1 and 90 parts of toluene is spin-coated on hard glass, and dried by heating at 105 with the mixture for 10 minutes. Then, the negative film shown in the photograph was placed on the substrate, and the same as in Example 1 was performed. Irradiate the visible polarized light obtained by the above method at room temperature from a distance of 50 cm for 1 minute. The dye solution is applied and dried in the same manner as in Example 1 to obtain the polarizing element (plate) of the present invention. Observing this substrate through a separately prepared polarizing plate gives a negative film image. When the polarizing plate is rotated 90 degrees, the light and dark are inverted, and a positive image is obtained.
  • a triacetyl cell orifice is immersed in a solution of 1 part of the polymer having an azobenzene group obtained in Example 1 and 99 parts of toluene, and pulled up. After air drying in the air, linearly polarized light obtained in the same manner as in Example 1 was irradiated on the above substrate placed parallel to the polarization axis of the polarizing plate for 1 minute at a room temperature from a distance of 50 cm. I do. Next, after rotating the polarization axis by 90 degrees, the mask pattern is placed on the above substrate, and visible light polarized light is irradiated for 1 minute from a distance of 50 cm at room temperature.
  • Example 2 The same biolett as in Example 1 An aqueous solution of the dye is spin-coated on the above substrate, and dried at 25 ° C and 50% RH to obtain the polarizing element (plate) of the present invention.
  • the polarizing element plate
  • an image of the mask pattern can be obtained with a light and dark contrast.
  • the polarizing plate is rotated, an image whose light and darkness are inverted every 90 degrees is obtained.
  • a triacetyl cell mouth-film is immersed in a solution of 1 part of the polymer having an azobenzene group obtained in Example 1 and 99 parts of toluene, and the solution is pulled up. Air drying in air After that, the linearly polarized light obtained in the same manner as in Example 1 is irradiated for 1 minute at a room temperature from a distance of 50 cm onto the substrate placed parallel to the polarization axis of the polarizing plate. Next, after rotating the polarization axis by 45 degrees, a strip-shaped mask pattern is placed on the right side of the above substrate, the left side is hidden so as not to be exposed, and from a distance of 50 cm at room temperature.
  • the polarizer When the polarizer is rotated 90 degrees, the left-hand geometric pattern image disappears and the right-hand strip image is obtained as an inverted image.
  • the plate When the plate is rotated 135 degrees, the striped image on the right disappears and the geometrical pattern on the left is obtained as an inverted image, and the polarizing plate is turned 180 degrees. When turned, the geometric pattern image on the left disappears, and the stripe image on the right is obtained, which is the same as the first image.
  • Example 1 Multi-axis polarizing element (plate)
  • FIG. 1 is a schematic view of an apparatus for providing a photoactive molecular layer. Triacetyl cell mouth The film is set in the phenolic roll of (a) and the polymer solution in the dish of (b) (consisting of 1 part of the polymer obtained in Example 1 and 99 parts of toluene) Then, immerse while rotating the dipping roll (c), air-dry, and take up with the winding roll (d).
  • FIG. 2 is a schematic diagram of a visible polarized light irradiation device.
  • a film with a photoactive molecular layer provided on (a) is set, and the ultra-high pressure mercury lamp in (b) and visible light polarized from the polarizing element in (c) are illuminated. ) Take up the roll.
  • the polarizing element in (c) can obtain linearly polarized light with a width of 2 cm.
  • the polarizing axis is switched between parallel and perpendicular to the side of the film every time the film moves 2 cm. .
  • FIG. 3 is a schematic view of an apparatus for providing a dichroic molecular layer.
  • (a) Set the film provided with the photoactive molecular layer irradiated with polarized light, and (b) dipped in the aqueous solution of dichroic molecules in the dish using the gravure roll of (c). Transfer onto film. After that, it is naturally dried in 25, and then it is wound up with the winding opening in (d).
  • the aqueous solution of dichroic molecules in the dish of (b) was prepared by adding 1 part of emulgen 108 to 10 parts of the violet dye (C.I. Use one diluted with some distilled water.
  • the light source uses a 500 WZh ultra-high pressure mercury lamp, a cut-off filter to make visible light (> 400 nm), and a polarizing plate with a polarization axis of -45 degrees. Through to be linearly polarized light. This linearly polarized light is irradiated for 1 minute at a room temperature from a distance of 50 cm onto one coated surface of the above substrate placed parallel to the polarization axis of the polarizing plate. Then, place the left eye mask with the polarization axis at 45 degrees and irradiate for 1 minute.
  • the dye solution is applied and dried in the same manner as in Example 1 to obtain the polarizing element (plate) for the left eye of the present invention.
  • the polarization axis of the polarizing plate is set to 0 °, and another substrate is irradiated with visible-polarized light at a distance of 50 cm for 1 minute.
  • a dye solution is applied and dried in the same manner as in Example 1 to obtain a polarizing element (plate) for the right eye of the present invention.
  • These two substrates are superimposed to form a three-dimensional display polarizing element, and a lens for glasses is used.
  • Example 13 Curved polarizing element (plate) A watch glass made of hard glass was immersed in a solution containing 10 parts of the polymer having an azobenzene group obtained in Example 1 and 90 parts of toluene, and heated at 105 ° C for 10 minutes. Dry and irradiate with linearly polarized light in the same manner as in Example 1.
  • a black dye (B lackl) 10 consisting of C.I.D irect O range 72, C.I.D irect Blue 67, and C.I.D irect Green 51 is added with 10 parts of emulgen 10 8 was spin-coated those with aqueous solution was diluted with distilled water 8 9 parts added 1 part, to obtain a polarizing element of the present invention (plate) was dried at 2 5 D C, 5 0% RH conditions When this substrate is observed through a polarizing plate, a light and dark contrast appears. Then, when the polarizing plate is rotated, the light and darkness are inverted every 90 degrees, and the behavior is the same as that of a normal polarizing plate.
  • the average single-plate transmittance Y s of the polarizing element (plate) of this is a 3 0%.
  • the average polarization rate p is 7 8.8%.
  • a solution of 10 parts of the polymer containing azobenzene obtained in Example 1 and 90 parts of toluene is spin-coated on a commercially available spectacle lens, and dried by heating at 105 ° C. for 10 minutes.
  • a black lamp (BL) of 40 W is made into linearly polarized light through a polarizing plate, and irradiated at room temperature for 10 minutes on the coated surface of the above-mentioned spectacle lens placed parallel to the polarizing axis of the polarizing plate.
  • the dye aqueous solution of Example 13 is spin-coated on the irradiated surface, and dried under the conditions of 25 ° C. and 50% RH to obtain the polarizing element (plate) of the present invention.
  • the average single-plate transmittance Y s of this polarizing element (plate) is 32%,
  • the average polarization ratio P is 77.1%.
  • Example 15 Curved polarizing element (plate)
  • a solution consisting of 10 parts of the polymer obtained in Example 2 and 90 parts of toluene is spin-coated on a commercially available spectacle lens, heated at 105 and dried for 10 minutes. Irradiation with linearly polarized light is carried out in the same manner as in Example 13, and a dye solution is applied and dried to obtain a polarizing element (plate) of the present invention. Average single ItaToru over rate Y s 4 2 of this polarizing element (plate). 1%, the average polarization rate p is 7 5.6% Der Ru o
  • Example 18 Curved polarizing element (plate)
  • Example 13 Heat and dry at 105 ° C for 10 minutes. Then, in the same manner as in Example 13, the coated surface on the spectacle lens is irradiated with linearly polarized light, and a dye aqueous solution is applied and dried to obtain a polarizing element (plate) of the present invention.
  • the average single-plate transmittance Y s of this polarizing element (plate) is 324%, and the average polarization p is 76.3%.
  • the average single-plate transmittance Y s of this polarizing element (plate) is 35%, and the average polarization p is 93%.
  • a photoactive molecule having a hydroxy group is esterified with a methacrylic-Like-Like mouth to form a monomer, and is subjected to radial polymerization in the same manner as in Example 1 to obtain a polymer.
  • This polymer solution is applied to the film substrate surface in the same manner as in Example 1, dried to form a thin film, and subjected to a corona discharge treatment under the conditions shown in Table 3.
  • irradiation with linearly polarized light is performed, and an aqueous pigment solution is applied and dried to obtain a polarizing element (plate) of the present invention.
  • Table 3 shows the average single-plate transmittance Y s and the average polarization ratio P of this polarizing element (plate).
  • PET represents polyethylene glycol
  • TAC represents triacetylcellulose
  • PP represents polypropylene
  • p-HAB represents p-hydroxyazobenzene
  • 0-HAB represents 0-HAB.
  • o Hydroxyazobenzene
  • HCA stands for hydroxysianoazobenzene
  • HS stands for p—hydroxystilbene.
  • a solution consisting of 10 parts of the azobenzene-containing polymer obtained in Example 1 and 90 parts of toluene is spin-coated on a glass plate, heated at 105 for 10 minutes and dried.
  • This glass plate was irradiated with UV Ozone Cleaner NL — 11 from Japan Laser Electronics Co., Ltd. (Lamp output 0.7 W, main peak wavelengths 1885 nm and 254 nm, Place in a channel at a distance of 10 cm) and treat for 5 minutes in an oxygen stream.
  • linearly polarized light is applied, and a dye aqueous solution is applied and dried to obtain a polarizing element (plate) of the present invention.
  • the average single-plate transmittance Y s of the polarizing element (plate) of This 3 2%, the average polarization rate p is 8 9%.
  • polarizing element (plate) of the present invention photoactive molecules are previously bound or dispersed in the surface layer of the substrate, and then linearly polarized light having a wavelength absorbed by the photoactive molecules is irradiated. It is obtained by adsorbing one or more dichroic molecules on the active molecular layer.
  • a polarizing element (plate) By such a photochemical method, The reason that a polarizing element (plate) can be obtained is that the photoactive molecules, whose molecular axes are arranged in a certain direction by linearly polarized light irradiation, are adsorbed onto the photoactive molecules. It is thought that it is to regulate.
  • the transmittance and the polarization can be further increased by corona discharge treatment or UV irradiation of the photoactive molecular layer.
  • a polarizing element can be obtained only by adsorbing dichroic molecules to photoactive molecules irradiated with linearly polarized light, so that a large-area polarizing element can be easily formed without the need for stretching operation. . It is possible to manufacture not only flat products but also curved products. Further, the structures of the dichroic molecules used are various, and a polarizing element having an arbitrary color tone can be produced by selecting dichroic molecules alone or a mixture thereof. Furthermore, since the manufacturing method is a photochemical method, it is possible to easily manufacture a polarizing element having an extremely fine and complicated pattern, which was impossible with the conventional method.
  • the orientation of the photoactive molecule is reversible, and the orientation of the molecular axis of the photoactive molecule can be arbitrarily changed by rotating the linear polarization axis. Therefore, a desired pattern can be printed by overwriting by irradiating a plurality of linearly polarized lights having different polarization axes, and the correction is easy.
  • a layer of solid dichroic molecules is provided thereon, the arrangement of the photoactive molecules does not change any longer even when irradiated with linearly polarized light having a different polarization axis, and is stable for a long time. To standardize. Industrial applicability
  • a gradation display polarizing element (plate), a multi-axis polarizing element (plate), and a curved polarizing element (plate) can be mass-produced by a simple manufacturing method.
  • various visible display devices such as a three-dimensional display polarizing element (plate) can be manufactured.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polarising Elements (AREA)
PCT/JP1994/001491 1993-09-10 1994-09-09 Polarisant, plaque polarisante et son procede de production WO1995007474A1 (fr)

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Application Number Priority Date Filing Date Title
EP94926376A EP0670506B1 (en) 1993-09-10 1994-09-09 Polarizer, polarizing plate and process for production thereof
US08/428,150 US5706131A (en) 1993-09-10 1994-09-09 Polarizing element, polarizing plate, and process for production thereof
HK98102818.9A HK1003727B (en) 1993-09-10 1994-09-09 Polarizer, polarizing plate and process for production thereof
KR1019950701846A KR100327764B1 (ko) 1993-09-10 1994-09-09 편광소자,편광판및그제조방법
DE69433486T DE69433486T2 (de) 1993-09-10 1994-09-09 Polarisator,polarisationsplatte und verfahren zu deren herstellung

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JP24856093 1993-09-10
JP5/248560 1993-09-10
JP34449693 1993-12-20
JP5/344496 1993-12-20
JP3200594 1994-02-04
JP6/32005 1994-02-04

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EP0670506B1 (en) 2004-01-14
SG78243A1 (en) 2001-02-20
EP0670506A1 (en) 1995-09-06
TW243499B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1995-03-21
KR950704705A (ko) 1995-11-20
CN1050672C (zh) 2000-03-22
DE69433486T2 (de) 2004-10-14
EP0670506A4 (en) 1997-12-03
DE69433486D1 (de) 2004-02-19
US5706131A (en) 1998-01-06
EP1275988A3 (en) 2006-03-22
HK1049372A1 (en) 2003-05-09
KR100327764B1 (ko) 2002-06-26
HK1003727A1 (en) 1998-11-06
EP1275988A2 (en) 2003-01-15

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