JP2004004944A - Polarizing element, polarizing plate and their manufacturing method - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new polarizing element, a polarizing plate and their manufacturing method. <P>SOLUTION: The polarizing element or the polarizing plate has a layer having optically activated molecules and a layer including dichroic molecules and coming into contact with the former layer, and the dichroic molecule is a compound having a hydrophilic substitutional group and is in a solid state. For example, a gradation display polarizing element (plate), a multi-axis polarizing element (plate) and a curved surface polarizing element (plate) are formed in a large amount by a simple manufacturing method, and various visible display devices, for example, a stereoscopic display polarizing element (plate) or the like can be manufactured by combining the polarizing elements (plates) each other or combining the polarizing element (plate) with a conventional linearly polarizing plate. <P>COPYRIGHT: (C)2004,JPO

Description

The present invention relates to a novel polarizing element, a polarizing plate, and a method for manufacturing the same.

Polarizing elements used in liquid crystal display devices, sunglasses, goggles, etc. dissolve or adsorb dichroic molecules in a polymer substance such as polyvinyl alcohol, and stretch the film in one direction to arrange dichroic molecules. It is manufactured by the method. It is also manufactured by a method in which dichroic molecules are adsorbed on a uniaxially stretched polymer film. 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 various display elements including a liquid crystal display, a polarizing element or a polarizing element having a fine pattern and exhibiting polarization in an arbitrary direction is required.

Conventionally, for this purpose, Non-Patent Document 1 proposes a method of adsorbing dichroic molecules on the surface of glass or a polymer film after rubbing the surface of the film with a cloth or paper in one direction. I have. According to this method, the dichroic molecules are aligned in the direction defined by the rubbing direction. Therefore, if the rubbing treatment is performed on the substrate surface in different directions in advance, the polarization axes can be changed in various directions by one polarizing plate. Non-Patent Document 2 describes that a multiaxial polarizing element having the following can be manufactured. However, the method of manufacturing a polarizing element by this rubbing treatment involves placing a mask that gives a pattern having a different polarization axis on a substrate to be subjected to surface treatment, and mechanically rubbing only a portion not covered with the mask. It is impossible to draw fine patterns with different axes. In the case of a gradation display pattern such as a photograph or a complicated pattern, such a method cannot be applied. Furthermore, in the rubbing treatment on the polymer surface, static electricity generated by rubbing causes fine dust to be adsorbed, thereby causing surface contamination. Thus, a method of precisely and finely controlling the polarization axis in an arbitrary direction has not been known so far.

On the other hand, in order to manufacture a polarizing element or a polarizing plate having a curved surface such as sunglasses or ski goggles, the polarizing element on a flat plate had to be processed by applying heat or force. In addition, high-quality products are very expensive because they require the work of enclosing them in a resin or bonding them together.

JP-A-1-161202 JP-A-1-172906 JP-A-1-172907 JP-A-1-183602 JP-A-1-248105 JP-A-1-265205 J. F. Dryer (JF Dreyer), Journal of Physics and Colloid Chemistry (J. Phys. Colloid @ Chem.), P. 52, 808 (1948). JF Dreyer, CW Ertel, Glass Industry, 29, 197 (1948), Toshiaki Nose, Rumiko Yamaguchi, Susumu Sato, IEICE Transactions, J71-C, 1188 (1988) "Molecular Crystals and Liquid Crystals", Supplement 1 (1982), J. Cognard, p.

The object of the present invention is to provide a polarizing element, a polarizing plate and a method for manufacturing the same, which do not require a stretching operation of a polymer film and can draw an extremely fine polarization pattern.

The present inventors have conducted intensive studies 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 provided a wavelength range in which the molecular layer absorbs. When a dichroic molecule layer was provided on the photoactive molecular layer after irradiating linearly polarized light containing, the dichroic molecules were found to be arranged anisotropically.

The present invention has been completed based on this finding. That is, the present invention
(1) A compound having a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent, and the dichroic molecule is in a solid state. Polarizing element or polarizing plate,
(2) The polarizing element or polarizing plate according to (1), wherein a layer having photoactive molecules is provided on the substrate, and a protective layer is provided on the layer containing dichroic molecules.
(3) The photoactive molecule is a molecule containing at least one double bond selected from non-aromatic C ＝ C, non-aromatic C ＝ N, and non-aromatic N ＝ N ( 1) or (2) the polarizing element or polarizing plate,
(4) the polarizing element or polarizing plate according to (1), wherein the hydrophilic substituent is a sulfonic acid group, an amino group, or a hydroxyl group;
(5) the polarizing element or the polarizing plate according to (2), wherein the substrate is flat or curved;
(6) After irradiating the layer having photoactive molecules on the substrate with linearly polarized light, a layer containing a solid-state dichroic molecule having a hydrophilic substituent is provided on the photoactive molecule layer. A method for manufacturing a polarizing element or a polarizing plate,
(7) The method for producing a polarizing element or polarizing plate according to (6), wherein the layer having photoactive molecules on the substrate is subjected to a corona discharge treatment or an ultraviolet irradiation treatment.
(8) a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent, and the dichroic molecule is in a solid state A gradation display polarizing element or polarizing plate,
(9) After irradiating the layer having photoactive molecules on the substrate with linearly polarized light through a mask having shading, a dichroic molecule in a solid state having a hydrophilic substituent is formed on the photoactive molecule layer. A method for producing a polarizing element or a polarizing plate, comprising providing a layer containing
(10) a compound having a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent, and the dichroic molecule is in a solid state; Multi-axial polarizing element or polarizing plate,
(11) irradiating the layer having photoactive molecules on the substrate with two or more linearly polarized lights having different polarization axes, and then dichroic solid state having a hydrophilic substituent on the photoactive molecule layer A method for producing a multiaxial polarizing element or a polarizing plate, comprising providing a layer containing molecules,
(12) a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent, and the dichroic molecule is in a solid state Stereoscopic display polarizing element or polarizing plate,
About.

The substrate used in the present invention may be any substrate to which the photoactive molecules can be bound or applied. For example, a glass plate such as silica-based glass or hard glass, a quartz plate, an ABS resin, an acetal resin, (meta) Acrylic resin, cellulose acetate, chlorinated polyether, ethylene-vinyl acetate copolymer, fluorine resin, ionomer, methylpentene polymer, nylon, polyamide, polycarbonate, polyethylene terephthalate, polyester such as polybutylene terephthalate, polyimide, polyphenylene oxide, polyphenylene Sulfide, polyallyl sulfone, polyarylate, polyethylene, polypropylene, polystyrene, polysulfone, vinyl acetate resin, vinylidene chloride resin, AS resin, vinyl chloride resin, alkyd resin, allyl resin, amide Plastic plates and sheets (films) of various materials such as resin, urea resin, melamine resin, epoxy resin, phenol resin, unsaturated polyester resin, silicone resin, polyurethane, and the like, or silicon oxide, tin oxide, indium oxide on their surfaces And a metal oxide such as aluminum oxide, titanium oxide, chromium oxide, zinc oxide, silicon nitride, silicon carbide, or the like. Alternatively, a substrate (film) whose surface is coated with a highly reflective metal thin film can also be used. These substrates may be not only planar substrates but also curved substrates.

光 The photoactive molecule used in the present invention is a molecule that undergoes a change in molecular axis alignment by linearly polarized light. Here, 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. As the photoactive molecule for this purpose, a molecule containing at least one double bond selected from C ＝ C, C ＝ N, and N ＝ N, and the double bond is non-aromatic, is effectively used. You. The wavelengths of light absorbed by the photoactive molecules are not limited to those in the visible light region, but include those in the ultraviolet and infrared regions that are not observed by the naked eye. When the layer of the photoactive molecule is irradiated with linearly polarized light including the wavelength range absorbed by the molecule, the molecular axis orientation easily changes.

分子 The change in the molecular axis orientation caused by the irradiation of linearly polarized light is interpreted as follows. That is, in the ground state of ethylene, which is the simplest molecule having a non-aromatic double bond, two carbon atoms and four hydrogen atoms are in the same plane, whereas in the photoexcited state, two pairs are present. It is well known that the planes formed by the H—C—H atomic groups have a twisted structure orthogonal to each other. Similarly, the photoactive molecule used in the present invention is such that in the photoexcited state, the planarity formed by the double bond disappears, and the molecular axis orientation changes in the process of returning to the ground state through a torsion structure that accompanies it. It is estimated to be. Therefore, the change in molecular axis orientation proceeds without causing a change in molecular structure due to geometrical isomerization before and after light irradiation. For example, most azobenzene compounds having a non-aromatic N = N bond cause a photogeometric isomerization reaction from a trans form to a cis form by ultraviolet light, but the cis form to the trans form for longer wavelength light. It is well known that photogeometric isomerization hardly occurs because conversion to the body takes precedence.

It is also known that the photoisomerization reaction may not be substantially observed because the change from the cis form to the trans form occurs rapidly rapidly. A compound having a non-aromatic C = N bond can be a geometric isomer upon irradiation with light, but since it is unstable, it quickly returns to its thermodynamically stable original structure. No photoisomerization is observed. Furthermore, many compounds having a non-aromatic C ＝ C bond cause a photogeometric isomerization reaction. However, as in the case of azobenzene, light having a wavelength in a wavelength range suitable for isomerization from cis to trans isomer is used. No substantial geometric isomerization is observed. However, even when such an apparent photoisomerization reaction does not occur, a change in molecular axis orientation easily occurs by irradiation with linearly polarized light, so that a compound having such properties can be used as the photoactive molecule of the present invention. .

具体 Specific examples of the photoactive molecule used in the present invention are shown below. Examples of the compound having a non-aromatic N = N bond include aromatic azo compounds such as azobenzene, azonaphthalene, bisazo compound, and formazan, and compounds having azoxybenzene as a basic skeleton. Examples of these are shown below, but not limited.

化合物 Examples of the compound having a non-aromatic C ＝ N bond include aromatic Schiff bases and aromatic hydrazones. Examples of these are shown below, but not limited.

化合物 Examples of the compound having a non-aromatic CＣC bond include polyene, stilbene, stilbazole, stilbazolium, cinnamic acid, indigo, thioindigo, and hemithioindigo. Examples of these are shown below, but not limited.

Compounds that return to the original structure immediately due to unstable photogeometric isomers and that show no substantial photoisomerization reaction by light irradiation at room temperature, and compounds that do not show any photogeometric isomerization reaction Can also be used in the present invention, and include, for example, cyanines and merocyanines shown below, but are not limited thereto.

Further, a compound having a non-aromatic C ＝ C bond or C ＝ N bond in the spiro ring, and other photoactive molecules that reversibly change the molecular structure by light irradiation, such as the following spiropyran, spiropyran Oxazines can also be used. Although these are different from the above-mentioned molecular structure, reversible spiro ring opening / closing reactions are caused by the action of light due to the non-aromatic C 結合 C bond or CＮN bond contained in the molecule. It is considered that an axial orientation change occurs.

These photoactive molecules are listed as examples of the basic skeleton of the compound having a double bond group, and these skeletons have an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, and a hexyl group. Group, methoxy group, ethoxy group, propoxy group, butoxy group, alkoxy group, allyl group, allyloxy group, cyano group, methoxycarbonyl group, ethoxycarbonyl group, etc., alkoxycarbonyl group, hydroxy group, dimethylamino group, diethylamino group And at least one substituent selected from a dialkylamino group, a nitro group and the like. In particular, C1 to C6 alkyl groups, C1 to C6 alkoxy groups, cyano groups, and C1 to C6 alkoxycarbonyl groups which give structures similar to liquid crystal molecules are preferred.

In the present invention, in order to provide a photoactive molecule layer that causes such a reversible molecular axis orientation change on a substrate, the photoactive molecule is physically or chemically bonded to the substrate surface according to the surface characteristics of the substrate. There are a method and a method of preparing a polymer to which a photoactive molecule is bound or a polymer to which the photoactive molecule is added, and applying this as a thin film on a substrate. The one in which the photoactive molecule is fixed on the substrate surface, that is, the one in which the photoactive molecule is bonded to the substrate surface and the one in which the polymer in which the photoactive molecule is bonded is coated as a thin film on the substrate, have the orientation. The state is stable and preferable.

(1) First, a method for bonding photoactive molecules to the substrate surface will be described. Non-Patent Document 3 describes that for this purpose, for example, if the substrate is silyl glass, a method used for liquid crystal alignment can be employed.

As a first method for bonding a photoactive molecule to the substrate surface, a photoactive molecule solution having the above-mentioned non-aromatic double bond group and the following surface active group dissolved in a solvent is applied to the substrate surface. Then, a method of adsorbing and binding the photoactive molecule can be mentioned. Examples of surface active groups include carboxylic acid residues, malonic acid residues, carbamoyl groups, tetraalkylammonium groups, alkylpyridinium residues, alkylquinolinium residues, carboxylatochromium residues, ester residues, and nitrile residues. Groups, urea residues, amino groups, hydroxyl groups, betaine residues and the like. When the photoactive molecule is a liquid, it may be applied directly to the substrate surface.

{Circle around (2)} As a second method, a Langmuir-Blodgett method in which the above-described photoactive molecules having surface active groups are developed as a monomolecular layer on the water surface and at least one layer is transferred onto a substrate can be adopted. For this purpose, as the surface active group, for example, a carboxyl group, a carbamoyl group, an amino group, an ammonium group, a tetraalkylammonium group, and a hydroxyl group are preferable.

A third method is to bind a photoactive molecule to the substrate surface via a silyl group. Specifically, for example, a method of binding a photoactive molecule having a silyl group substituted with at least one halogen atom or an alkoxy group to a substrate surface, or a method in which a carboxyl group or a carboxyl group is added to a substrate surface treated with a silylating agent having an amino group. Examples include a method of subjecting a photoactive molecule having an acrylic group to a condensation reaction or an addition reaction. In the former method, the silyl group is introduced into the photoactive molecule in advance, and the surface of the silica glass is treated. Examples of the silyl group substituted with at least one halogen atom or alkoxy group include a trichlorosilyl group, a trimethoxysilyl group, and a triethoxysilyl group. In the latter method, examples of the silylating agent having an amino group include aminopropyltrichlorosilane, aminobutyltrichlorosilane, aminopropyltrimethoxysilane, and aminopropyltriethoxysilane. The operation of binding these photoactive molecules to the substrate surface may be performed in the presence of another silylation agent. Examples of the silylation treatment agent for this, methyltriethoxysilane, dimethyldiethoxysilane, trimethylchlorosilane, ethyltriethoxysilane, diethyldiethoxysilane, propyltriethoxysilane, butyltriethoxysilane, butylmethyldiethoxysilane, Alkyl (poly) alkoxysilanes such as pentyltriethoxysilane and hexyltriethoxysilane can be exemplified, but not limited thereto.

As a fourth method, when the polymer substance forms the substrate itself or the substrate surface layer, the photoactive compound having the surface active group is adsorbed and bonded to the substrate surface, or The photoactive molecule may be bound to the exposed active group by a covalent bond. In the latter case, for example, when the polymer substance is polyvinyl alcohol, the photoactive molecule is bonded to the surface layer of the substrate by an acetal bond, an ester bond or a urethane bond. For this purpose, for example, a photoactive molecule having a covalent bond-forming group such as a formyl group, a chloroformyl group or an isocyanate group is prepared, and this is dissolved in a solvent that does not dissolve polyvinyl alcohol. May be immersed in the reaction. In order to increase the treatment reaction rate, a catalyst acid such as p-toluenesulfonic acid may be added for acetalization, and triethylamine or triethylamine for removing acid generated in the reaction for esterification or urethane formation. A base such as pyridine may be added.

Next, a method of preparing a polymer to which a photoactive molecule is bound or a polymer to which a photoactive molecule is added, and applying the polymer as a thin film on a substrate will be described. First, a method for preparing a polymer having a photoactive molecule bound thereto will be described. In order to bind the photoactive molecule to the side chain or main chain of the polymer, a monomer having the photoactive molecule is polymerized, or the polymer substance has a reactive residue suitable for its chemical structure. Attach photoactive molecules.

In the former polymerization method, in particular, a photoactive molecule having a (meth) acryl group having radical polymerization ability is suitable as a monomer, and a polymer having a photoactive molecule bonded to a side chain by polymerization is easily used. Is obtained. In the case of a polymer obtained by a polycondensation reaction of polyester, polyamide, polyimide or the like or a polyaddition reaction of polyurethane or the like, a bifunctional monomer having a photoactive molecule may be prepared. Examples of the bifunctional monomer include vinyl cinnamate. The polymer compound obtained by polymerizing photoactive molecules obtained by polymerization is a homopolymer obtained by polymerizing only a monomer having a photoactive molecule, or a copolymer obtained by polymerizing a monomer having a photoactive molecule and another monomer. May be any of Examples of the other monomer include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate. By changing the ratio of the monomer having a photoactive molecule to another monomer, the amount of the photoactive molecule in the polymer can be adjusted. The proportion used depends on the structure of the monomer, but is in the range of 1: 0 to 1: 100, more preferably 1: 0 to 1:50.

(4) In the latter case, in which a photoactive molecule having a reactive residue suitable for its chemical structure is bonded to a polymer substance, the above-described fourth method can be used. Examples of the polymer used include, but are not limited to, polyvinyl alcohol, styrene-maleic anhydride copolymer, polyglycidyl methacrylate or a copolymer thereof.

(4) As a method of providing such a polymer thin film having a photoactive molecule in the main chain or side chain on the substrate surface, a spin coating method is preferable. Further, such a polymer may be provided on a substrate by a Langmuir-Blodgett method. Further, the substrate may be immersed and adsorbed in these polymer solutions. A film thickness of 1 μm or less is sufficient.

(4) A method using a polymer to which a photoactive molecule is added will be described. This method is a method in which a photoactive molecule is dissolved or uniformly dispersed in a polymer in advance, and this is applied in a thin film form on the substrate surface. In this case, the polymer and the photoactive molecule must be insoluble in the solvent used for the dichroic molecule solution described below. As the polymer, for example, polyimides are preferable since they are insoluble in solvents such as water and alcohols, but are not limited thereto.

Next, the operation of irradiating the photoactive molecular layer provided on the substrate with linearly polarized light will be described. The wavelength of the polarized light to be applied is not particularly limited as long as the wavelength is absorbed by the photoactive molecule. For example, not only visible light but also light in the ultraviolet or infrared region may be used. The light source may be any of a mercury lamp, a xenon lamp, a fluorescent lamp, a chemical lamp, a helium-cadmium laser, an argon laser, a krypton laser, a helium-neon laser, a semiconductor laser, and even sunlight, and may absorb light-active molecules. The selection may be made according to the wavelength region, light irradiation time, irradiation area, or the like. 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. Examples of the polarizing element and the polarizing plate for this purpose include a prism element such as a Glan-Thompson prism and a polarizing element and a polarizing plate made of a polymer film stretched by dissolving or adsorbing dichroic molecules. Furthermore, 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 1 mJ / cm2 to 10 J / cm2. When a laser is used as a light source, a polarizing element (plate) is not required if the laser beam itself is linearly polarized.

焼 き In order to print the polarization pattern on the photoactive molecular layer, the photoactive molecular layer may be irradiated with linearly polarized light through a desired mask pattern. By diverging or condensing linearly polarized light using a lens or the like, the pattern can be greatly enlarged, or conversely, can be made into an extremely fine pattern. Also, when a laser is used as a light source and the laser beam itself is linearly polarized, an extremely fine pattern can be freely drawn by combining with a polarization plane rotating element such as a Faraday element. Further, since the change of the molecular axis orientation due to the linear polarization of the photoactive molecule is reversible, the pattern can be freely overwritten by irradiating linear polarization having a different polarization axis for each mask pattern. If one polarizing element (plate) having a complicated pattern is manufactured, the polarizing element (plate) having a complicated pattern, which has been conventionally difficult, can be formed by using the polarizing element (plate) as a mask pattern. A large number can be produced by a simple method called linearly polarized light irradiation.

The dichroic molecules are simply adsorbed on the photoactive molecular layer having the molecular axes arranged in a certain direction obtained in this way, that is, only by providing the dichroic molecular layer on the photoactive molecular layer, the two-color The molecular axes of the polar molecules are arranged in the direction of arrangement of the molecular axes of the photoactive molecules, that is, in the direction defined by the polarization axis of the linearly polarized light applied to the photoactive molecule layer, and the polarization axis is fixed. It was surprising that the property as) was exhibited. In the conventional method, it is presumed that when rubbing is performed on the surface of glass or a polymer film, dye molecules are arranged along fine grooves generated on the surface. However, in the present invention, without the formation of such grooves, the arrangement of the photoactive molecules themselves defines the arrangement of the dichroic molecules adsorbed thereon.

二 The dichroic molecule used in the present invention is a compound exhibiting a polarizing property when arranged in a certain direction by itself or in an aggregate, and for example, a compound having an aromatic ring structure is preferable. As the aromatic ring structure, in addition to benzene, naphthalene, anthracene, and phenanthrene, thiazole, pyridine, pyrimidine, pyridazine, pyrazine, quinoline and other heterocycles or quaternary salts thereof, and furthermore, benzene, naphthalene, and the like Is particularly preferred. Further, it is preferable that a hydrophilic substituent such as a sulfonic acid group, an amino group, or a hydroxyl group is introduced into these aromatic rings.

Examples of dichroic molecules include dye compounds such as azo dyes, stilbene dyes, pyrazolone dyes, triphenylmethane dyes, quinoline dyes, oxazine dyes, thiazine dyes, and anthraquinone dyes. it can. Water-soluble ones are preferred, but not limited thereto. Further, it is preferable that a hydrophilic substituent such as a sulfonic acid group, an amino group, or a hydroxyl group is introduced into these dichroic molecules. Specific examples of dichroic molecules include, for example, C.I. I. Direct \ Blue \ 67, C.I. I. Direct \ Blue \ 90, C.I. I. Direct @ Green @ 59, C.I. I. Direct Violet 48, C.I. I. Direct @ Red @ 39, C.I. I. Direct @ Red @ 79, C.I. I. Direct Red 81, C.I. I. Direct Red 83, C.I. I. Direct Red 89, C.I. I. Direct \ Orange \ 39, C.I. I. Direct @ Orange @ 72, C.I. I. Acid {Red} 37 and the like, and further, dyes and the like described in Patent Literature 1, Patent Literature 2, Patent Literature 3, Patent Literature 4, Patent Literature 5, and Patent Literature 6 are disclosed. The structures of typical dyes are shown below.

Next, a method for anisotropically adsorbing these dichroic molecules to the photoactive molecular layer on the substrate irradiated with linearly polarized light will be described. The above dichroic molecule alone or a mixture of two or more is dissolved in a hydrophilic solvent such as water, methanol, ethanol or the like or a water-containing solvent thereof. The concentration is preferably about 0.1 to 10 w / w%, more preferably about 0.5 to 5 w / w%. Also, a surfactant can be added to this solution. As the surfactant, any of cationic, nonionic and anionic surfactants can be used, but nonionic surfactants are preferred. Next, after the dichroic molecule solution is dropped on the substrate surface, a dichroic molecule layer having a uniform thickness is provided by a coater or a spin coating method. Alternatively, a substrate having a photoactive molecular layer irradiated with linearly polarized light is immersed in the solution of dichroic molecules, and is then pulled up. In order to obtain a uniform concentration of dichroic molecules, it is preferable to keep the pulling speed constant. The thickness of the dichroic molecular layer is preferably thinner from the viewpoint of improving the polarization characteristics, and is preferably, for example, 10 μm or less, particularly preferably 0.1 to 2 μm.

(4) The substrate to which the dichroic molecule solution is attached is dried to form a solid state dichroic molecular layer, thereby obtaining the polarizing element (plate) of the present invention. Drying conditions vary depending on the type of solvent, type of dichroic molecule, amount of solution of dichroic molecule applied, concentration of dichroic molecule, etc., but the temperature is from room temperature to 100 ° C, preferably from room temperature to 50 ° C. The humidity is preferably about 20 to 80% RH, more preferably about 30 to 70% RH.

The anisotropically adsorbed dichroic molecular layer prepared in this manner is in a solid state, for example, such as amorphos and crystals, but the dichroic molecular layer usually has poor mechanical strength, so a protective layer is formed on the surface. Is provided. This protective layer is usually formed by coating a dichroic molecular layer with a UV-curable or thermosetting transparent polymer film, or laminating with a transparent polymer film such as a polyester film or a cellulose acetate film. It is provided by a coating method.

偏光 When manufacturing the polarizing element (plate) of the present invention, the polarization properties can be further enhanced by performing corona discharge treatment or ultraviolet irradiation on the photoactive molecular layer. 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. As the apparatus for performing the corona discharge treatment, various commercially available corona discharge treatment machines can be applied. The conditions of the corona discharge treatment vary depending on conditions such as the type of the substrate provided with the photoactive molecular layer, the composition and thickness of the photoactive molecular layer, and the composition and thickness of the dichroic molecular layer applied after the corona discharge treatment. In one treatment, the energy density is about 20 to 400 W · min · m−2, preferably about 50 to 300 W · min · m−2. If one process is insufficient, the process can be performed two or more times. The ultraviolet irradiation is preferably performed on the photoactive molecular layer and before the linearly polarized light irradiation, but not particularly limited thereto. The wavelength of the ultraviolet light to be used is not particularly limited, but for example, far ultraviolet light of 300 nm or less is preferable. The ultraviolet irradiation is preferably performed under an oxygen stream. Various types of commercially available ultraviolet irradiation can be applied as an apparatus for performing ultraviolet irradiation. The conditions for UV irradiation vary depending on the type of substrate on which the photoactive molecular layer is provided, the composition and thickness of the photoactive molecular layer, the composition and thickness of the dichroic molecular layer applied after UV irradiation, and the like. A few minutes at the longest is sufficient.

偏光 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. For example, 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 to provide polarized sunglasses or goggles having an arbitrary polarization axis. A polarizing element (plate) can be produced.

(4) The polarizing element (plate) of the present invention can be provided with a gradation having its own density or a pattern having a large number of polarization axes during the manufacturing process. A gradation display polarizing element (plate) to which gradation is imparted can be manufactured by using linearly polarized light through a mask pattern having shading or a photographic negative film when printing a polarization pattern on the photoactive molecular layer. In addition, a multiaxial polarizing element (plate) having a large number of polarization axes can be manufactured by irradiating different portions with linearly polarized light having different polarization axes when printing a polarization pattern on the photoactive molecular layer.

立体 Using the polarizing element (plate) of the present invention, a stereoscopic display polarizing element (plate) can be manufactured. The three-dimensional display is to express a two-dimensionally drawn photograph, figure, picture, or the like three-dimensionally by using a special technique. For example, there is a method of viewing a printed matter drawn in red or blue through spectacles in which the left and right lenses are colored red or blue, respectively, or a method of shifting the focus of the eyes to make it appear three-dimensional. There is also a method of obtaining a stereoscopic image by passing an image obtained by using a polarization projection apparatus through polarizing elements (plates) having different polarization axes on the left and right. There is not yet a method for obtaining a stereoscopic image by viewing through a polarizing element (plate). In order to display a graphic or a pattern, it is necessary to provide a polarization characteristic only in a certain limited range or to have two or more polarization axes on one plane. The polarizing element (plate) of the present invention can draw fine patterns having the same or different polarization axes, and thus is suitable for producing a stereoscopic display polarizing element (plate). In order to manufacture this stereoscopic display polarizing element (plate), a polarizing element (plate) for the left eye and a right eye is required. Exposure to linear polarization through a desired mask pattern or photographic negative film may be performed to print the polarization pattern on the photoactive molecular layer. At this time, if the polarization axes of the linearly polarized light are shifted for the left eye and the right eye, corresponding polarizing elements (plates) can be manufactured. It is preferable that the offset angle is, for example, ± 45 degrees, ± 90 degrees, ± 135 degrees. By arranging or overlapping these polarizing elements (plates) at a predetermined distance, a stereoscopic display polarizing element (plate) can be manufactured. In addition, when a left-eye mask and a right-eye mask formed by fine dots are used, a left-eye image and a right-eye image having different polarization axes can be printed on a single polarizing element (plate).

Hereinafter, the present invention including a method for synthesizing a compound having a photoactive molecule will be described in more detail with reference to Examples, but the present invention is not limited to these Examples. In the examples, parts are by weight unless otherwise specified. The polarization ratio was calculated by the following formula.
Polarization ratio (%) = {(Y2−Y1) / (Y2 + Y1)} 1/2 × 100
(Y2: parallel transmittance (%), Y1: orthogonal transmittance (%))

Example 1
4-Methacryloyloxyazobenzene is dissolved in benzene to make a 20% by weight solution, and polymerization is carried out at 60 ° C. for 12 hours under degassing using azobisisobutyronitrile as an initiator. A solution comprising 10 parts of the obtained polymer having azobenzene and 90 parts of toluene is spin-coated on hard glass. This substrate is dried by heating at 105 ° C. for 10 minutes.

(4) A 500 W / h ultra-high pressure mercury lamp is used as a light source. This 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.

C. I. 1 part of Emulgen 108 (nonionic surfactant: manufactured by Kao Corporation) is added to 10 parts of Direct Blue 67 parts and diluted with 89 parts of distilled water to obtain an aqueous solution. This dye aqueous solution is spin-coated on the linearly polarized light irradiation surface of the substrate, and then dried at 25 ° C. and 50% RH to obtain the polarizing element (plate) of the present invention.

観 察 When this substrate is observed through a polarizing plate, a bright and dark contrast appears. Then, when the polarizing plate is rotated, the brightness is inverted every 90 degrees, and the same behavior as a normal polarizing plate is exhibited. Single-plate transmittance at each wavelength of this polarizing element (plate), average single-plate transmittance (Ys: average of single-plate transmittance at each wavelength), and the polarization axes of the two polarizing elements (plates) are parallel (Y2). The transmittance, the polarization and the average polarization (ρ: average of the polarization at each wavelength) when the light is orthogonal (Y1) are as follows.

Example 2
4-Methacryloyloxyazobenzene and methyl methacrylate are dissolved in benzene in a molar ratio of 1: 9 to form a 20% by weight solution, and polymerization is carried out in the same manner as in Example 1. A solution comprising 10 parts of the obtained polymer and 90 parts of toluene is spin-coated on hard glass, dried by heating at 105 ° C. for 10 minutes, and irradiated with linearly polarized light in the same manner as in Example 1. Then, on the surface irradiated with the linearly polarized light, C.I. I. Direct Blue 675 and C.I. I. Direct Orange 725 parts were mixed, 1 part of Emulgen 108 (manufactured by Kao Corporation) was added, and a dye aqueous solution diluted with 89 parts of distilled water was spin-coated, dried at 25 ° C. and 50% RH and dried. The polarizing element (plate) of the invention is obtained. Single-plate transmittance, average single-plate transmittance at each wavelength of the polarizing element (plate), transmittance, polarization rate and average polarization when the polarizing axes of the two polarizing elements (plates) are parallel and orthogonal. The rates are as follows:

Example 3
In the same manner as in Example 1, a polymer of methacrylic acid ester having benzylideneaniline in the side chain was synthesized, and a solution consisting of 10 parts of this polymer and 90 parts of toluene was spin-coated on hard glass. Heat and dry for a minute. On the coated surface of this substrate, light from an ultra-high pressure mercury lamp is irradiated with linearly polarized light obtained by combining a cutoff 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.

Embodiment 4. FIG. Production of Polarizing Element (Plate) Using Polymer Film Having Stilbene A polymer of methacrylic acid ester having 6-hexyloxystilbene in the side chain is synthesized, and a solution comprising 10 parts of this polymer and 90 parts of toluene is hardened. Spin-coat on glass and heat dry at 105 ° C for 10 minutes. After irradiating with linearly polarized light in the same manner as in Example 3, 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.

Embodiment 5 FIG. Synthesis of Polarizing Element Using Polymer Film Having Spiropyran A polymer of methacrylic acid ester having 6-nitroindolinospirobenzopyran in the side chain was synthesized, and a solution comprising 10 parts of this polymer and 90 parts of toluene was hardened. Spin-coat on glass and heat dry at 105 ° C for 10 minutes. After irradiating linearly polarized light on the coated surface of this substrate in the same manner as in Example 3, 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.

Embodiment 6 FIG. Polarizing element (plate) using polyvinylidene fluoride film
A solution comprising 0.1 part of the polymer containing azobenzene used in Example 1 and 99.9 parts of toluene is spin-coated on a polyvinylidene fluoride film, and dried by heating at 105 ° C. for 10 minutes. In the same manner as in Example 1, after irradiating the substrate with linearly polarized light, applying a dye solution, drying it under the conditions of 25 ° C. and 50% RH, and laminating the coated surface with a polyethylene terephthalate film, the polarizing element of the present invention (Plate).

Embodiment 7 FIG. Gradation display polarizer (plate)
A solution comprising 10 parts of the azobenzene group-containing polymer 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 whose contrast is changed stepwise is placed on the coated surface of the substrate, and linearly polarized light obtained by combining a cut-off filter (> 340 nm) and a polarizer with light from an ultra-high pressure mercury lamp is placed on the mask pattern. Irradiate 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. When this element is observed through a separately prepared polarizing plate, an image of a mask pattern having a stepwise contrast is obtained. Then, when the polarizing plate is rotated, an image in which the brightness is inverted every 90 degrees is obtained.

Embodiment 8 FIG. Gradation display polarizer (plate)
A solution comprising 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. Then, a negative film of the photograph is placed on the above-mentioned substrate, and a visible ray 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. 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. Observation of this substrate through a separately prepared polarizing plate yields a photographic negative film image. Further, when the polarizing plate is rotated by 90 degrees, light and dark are inverted, and a positive image is obtained.

Embodiment 9 FIG. Multi-axis polarizing element (plate)
A triacetylcellulose film is immersed in a solution comprising 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, the substrate is irradiated with linearly polarized light obtained in the same manner as in Example 1 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 90 degrees, the mask pattern is placed on the substrate and irradiated with visible-polarized light at a room temperature at a distance of 50 cm for 1 minute. The same aqueous solution of violet dye as in Example 1 was spin-coated on the substrate, and then dried under the conditions of 25 ° C. and 50% RH to obtain the polarizing element (plate) of the present invention. When this substrate is observed through a separately prepared polarizing plate, an image of the mask pattern can be obtained with a bright and dark contrast. Then, when the polarizing plate is rotated, an image in which the brightness is inverted every 90 degrees is obtained.

Embodiment 10 FIG. Multi-axis polarizing element (plate)
A triacetylcellulose film is immersed in a solution comprising 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, the substrate is irradiated with linearly polarized light obtained in the same manner as in Example 1 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 stripe-shaped mask pattern is placed on the right side of the substrate, the left side is hidden so as not to be exposed, and visible ray polarized light is irradiated for 1 minute from a distance of 50 cm at room temperature. After the polarization axis is further rotated by 45 degrees, a geometric mask pattern is placed on the left side of the substrate, and the right side is hidden, and linearly polarized light is irradiated for one minute. The same aqueous solution of violet dye as in Example 1 is spin-coated on the substrate, and then dried under the conditions of 25 ° C. and 50% RH to obtain the polarizing element (plate) of the present invention. When this substrate is observed through a separately prepared polarizing plate, a striped image is obtained on the right side. When the polarizing plate is rotated by 45 degrees, the striped image disappears, and a geometric pattern image is obtained on the left instead. When the polarizing plate is rotated by 90 degrees, the geometric pattern image on the left disappears, and the stripe image on the right is obtained as an inverted image. When the polarizing plate is rotated by 135 degrees, the striped image on the right disappears and the geometric image on the left is obtained as an inverted image. Then, when the polarizing plate is rotated by 180 degrees, the geometric pattern image on the left disappears, and a stripe image on the right is obtained, which is the same as the first image.

Embodiment 11 FIG. Multi-axis polarizing element (plate)
Using the apparatus shown in FIGS. 1 to 3, a continuous multi-axis polarizing element (plate) in the form of a strip is formed. FIG. 1 is a schematic diagram of an apparatus for providing a photoactive molecular layer. The triacetyl cellulose film is set on the film roll of (a), and (c) is immersed in the polymer solution (consisting of 1 part of the polymer obtained in Example 1 and 99 parts of toluene) in the dish of (b). The roll is immersed while rotating, air-dried, and wound by the winding roll (d).

FIG. 2 is a schematic view of a visible polarized light irradiation device. A film provided with a photoactive molecular layer is set on (a), and is irradiated with visible light polarized light obtained from an ultra-high pressure mercury lamp in (b) and a polarizing element in (c), and wound with a winding roll in (d). take. The polarizing element of (c) can obtain linearly polarized light having a width of 2 cm, and the polarization axis is switched between parallel and perpendicular to the side of the film every time the film is moved by 2 cm.

FIG. 3 is a schematic view of an apparatus for providing a dichroic molecular layer. A film provided with a photoactive molecular layer irradiated with polarized light is set on (a), and is transferred onto the film using a gravure roll (c) immersed in an aqueous solution of dichroic molecules in a dish (b). . After being naturally dried at 25 ° C. as it is, it is wound up by a winding roll (d). As the aqueous solution of dichroic molecules in the dish of (b), one obtained by adding 1 part of Emulgen 108 to 10 parts of violet dye (CI Direct Blue 67) and diluting with 89 parts of distilled water is used.

Observation of the completed film-shaped multi-axis polarizing element (plate) through a separately prepared polarizing plate yields an image of 2 cm bright and dark stripes. When the polarizing plate is rotated 90 degrees, the bright and dark stripes are inverted. Is obtained. It can be seen that this is a biaxial polarizing element (plate) having a width of 2 cm and orthogonal axes.

Embodiment 12 FIG. Stereoscopic display polarizing element (plate)
A solution comprising 1 part of the polymer having an azobenzene group obtained in Example 1 and 99 parts of toluene is spin-coated on two triacetyl cellulose (TAC) films, and dried by heating at 105 ° C. for 10 minutes. A 500 W / h ultra-high pressure mercury lamp is used as a light source, and visible light is emitted by a cut-off filter (> 400 nm), and linearly polarized light is passed through a polarizing plate having a polarization axis of -45 degrees. The linearly polarized light is irradiated at room temperature for 1 minute from a distance of 50 cm onto a coating surface of one of the substrates placed parallel to the polarization axis of the polarizing plate. Then, a mask for the left eye is set with the polarization axis at 45 degrees, and irradiation is performed for one minute. The dye solution is applied and dried in the same manner as in Example 1 to obtain the left-eye polarizing element (plate) of the present invention.

Next, the polarization axis of the polarizing plate is set to 0 °, and another substrate is irradiated with visible-ray polarized light from a distance of 50 cm for 1 minute. Next, the polarization axis is set to 90 degrees, a mask for the right eye is placed, and visible light polarized light is irradiated for 1 minute. The dye solution is applied and dried in the same manner as in Example 1 to obtain the right-eye polarizing element (plate) of the present invention.

When these two substrates are superimposed on each other to form a three-dimensional display polarizing element, and a polarizing plate having -45 degrees on the left and 0 degrees on the right is pasted on the lens part of the glasses, an image emerges and becomes three-dimensional. Image is obtained.

Embodiment 13 FIG. Curved polarizing element (plate)
A watch glass made of hard glass was immersed in a solution consisting of 10 parts of the polymer having an azobenzene group obtained in Example 1 and 90 parts of toluene, heated at 105 ° C. for 10 minutes, and dried. Irradiate linearly polarized light by the method. Then, C.I. I. Direct Orange 72, C.I. I. Direct Blue 67, C.I. I. To 10 parts of a black dye (Black 1) made of Direct Green 51, 1 part of Emulgen 108 was added, diluted with 89 parts of distilled water to form an aqueous solution, and spin-coated, dried at 25 ° C. and 50% RH. The polarizing element (plate) of the present invention is obtained. When this substrate is observed through a polarizing plate, a light and dark contrast appears. Then, when the polarizing plate is rotated, the brightness is inverted every 90 degrees, and the same behavior as a normal polarizing plate is exhibited. The average single-plate transmittance Ys of this polarizing element (plate) is 30%, and the average polarization ratio ρ is 78.8%.

Embodiment 14 FIG. Curved polarizing element (plate)
A solution comprising 10 parts of the azobenzene-containing polymer 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 40 W / h black lamp (BL) is linearly polarized through a polarizing plate, and irradiated at room temperature for 10 minutes on the coated surface of the 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 Ys of this polarizing element (plate) is 32%, and the average polarization ratio ρ is 77.1%.

Embodiment 15 FIG. Curved polarizing element (plate)
A solution comprising 10 parts of the polymer obtained in Example 2 and 90 parts of toluene is spin-coated on a commercially available spectacle lens, and dried by heating at 105 ° C. for 10 minutes. Next, in the same manner as in Example 13, irradiation with linearly polarized light was performed, and a dye solution was applied and dried to obtain a polarizing element (plate) of the present invention. The average single-plate transmittance YS of this polarizing element (plate) is 42.1%, and the average polarization ratio ρ is 75.6%.

Embodiment 16 FIG. Curved polarizing element (plate)
2-Methacryloyloxyazobenzene is dissolved in benzene to form a 20% by weight solution, and polymerization is carried out at 60 ° C. for 12 hours under degassing using azobisisobutyronitrile as an initiator. A solution consisting of 10 parts of the polymer having azobenzene and 90 parts of toluene is spin-coated on a commercially available spectacle lens, and dried by heating at 105 ° C. for 10 minutes. Next, in the same manner as in Example 13, the coating 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 Ys of the polarizing element (plate) is 29.5%, and the average polarizing rate ρ is 70.2%.

Embodiment 17 FIG. Curved polarizing element (plate)
(4′-methacryloyloxy) -4-cyanoazobenzene is dissolved in benzene to form a 20% by weight solution, and polymerization is carried out at 60 ° C. for 12 hours under degassing using azobisisobutyronitrile as an initiator. A solution comprising 10 parts of the obtained polymer having cyanoazobenzene and 90 parts of THF is spin-coated on a commercially available spectacle lens, and dried by heating at 105 ° C. for 10 minutes. Next, in the same manner as in Example 13, the coating 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 Ys of this polarizing element (plate) is 28.1%, and the average polarization ratio ρ is 68.9%.

Embodiment 18 FIG. Curved polarizing element (plate)
4-Methacryloyloxystilbene is dissolved in benzene to form a 20% by weight solution, and polymerized at 60 ° C. for 12 hours under degassing using azobisisobutyronitrile as an initiator. A solution comprising 10 parts of the obtained polymer having azobenzene and 90 parts of toluene is spin-coated on a commercially available spectacle lens, and dried by heating at 105 ° C. for 10 minutes. Next, in the same manner as in Example 13, the coating 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 Ys of this polarizing element (plate) is 32.4%, and the average polarization ratio ρ is 76.3%.

Embodiment 19 FIG. Corona discharge treatment A solution composed of 10 parts of the azobenzene-containing polymer obtained in Example 1 and 90 parts of toluene is spin-coated on a TAC film, heated at 105 ° C. for 10 minutes, and dried. Corona discharge treatment is performed on the film at a moving speed of 12 m / sec and a set energy of 150 W · min · m −2. Next, in the same manner as in Example 13, 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 Ys of this polarizing element (plate) is 35%, and the average polarization ratio ρ is 93%.

Embodiment 20-24. Corona discharge treatment A photoactive molecule having a hydroxy group is esterified with methacryloyl chloride to obtain a monomer, and radical polymerization is performed in the same manner as in Example 1 to obtain a polymer. This polymer solution is applied to the surface of the film substrate in the same manner as in Example 1, dried and thinned, and then subjected to corona discharge treatment under the conditions shown in Table 3. Next, in the same manner as in Example 13, irradiation with linearly polarized light was performed, and an aqueous dye solution was applied and dried to obtain a polarizing element (plate) of the present invention. Table 3 shows the average single-plate transmittance YS and the average polarization ρ of this polarizing element (plate). In the table, PET is polyethylene terephthalate, TAC is triacetyl cellulose, PP is polypropylene, p-HAB is p-hydroxyazobenzene, o-HAB is o-hydroxyazobenzene, HCA is hydroxycyanoazobenzene, HS Means p-hydroxystilbene.

Embodiment 25 FIG. Ultraviolet treatment A solution comprising 10 parts of the azobenzene-containing polymer obtained in Example 1 and 90 parts of toluene is spin-coated on a glass plate, and heated at 105 ° C. for 10 minutes and dried. This glass plate is placed in a chamber of UV Ozone Cleaner NL-UV253 (Lamp output 0.7 W, main peak wavelengths 185 nm and 254 nm, irradiation distance 10 cm) manufactured by Nippon Laser Electronics Co., Ltd., and is treated for 5 minutes under an oxygen stream. Next, in the same manner as in Example 13, 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 Ys of this polarizing element (plate) is 32%, and the average polarization ratio ρ is 89%.

In the polarizing element (plate) of the present invention, a photoactive molecule is previously bound or dispersed on a substrate surface layer, and then linearly polarized light including a wavelength absorbed by the photoactive molecule is irradiated. Alternatively, it is obtained by adsorbing two or more dichroic molecules. The reason that a polarizing element (plate) can be obtained by such a photochemical method is that solid-state dichroic molecules in which photoactive molecules having a molecular axis arranged in a certain direction are adsorbed thereon by linearly polarized light irradiation. This is considered to define the arrangement direction of the molecular axis. The transmittance and the polarization can be further increased by corona discharge treatment or UV irradiation of the photoactive molecular layer.
According to the present invention, a polarizing element can be obtained only by adsorbing a dichroic molecule to a photoactive molecule irradiated with linearly polarized light, so that a polarizing element having a large area can be easily produced without requiring a stretching operation. Not only flat ones but also curved ones can be manufactured. Further, the structures of dichroic molecules used are various, and a polarizing element having an arbitrary color tone can be manufactured by selecting dichroic molecules alone or a mixture thereof. Furthermore, since the manufacturing method is a photochemical method, a polarizing element having an extremely fine and complicated pattern, which has been impossible with the conventional method, can be easily manufactured. In particular, before the dichroic molecules are adsorbed, the orientation of the photoactive molecules is reversible, and the orientation direction of the molecular axes of the photoactive molecules can be arbitrarily changed by rotating the linear polarization axis. A desired pattern can be printed by overwriting by irradiating a plurality of different linearly polarized lights, and correction is easy. When the layer of solid dichroic molecules is provided thereon, the molecular arrangement of the photoactive molecules is stabilized for a long time without change even when irradiated with linearly polarized light having a different polarization axis. Therefore, according to the present invention, for example, a large number of gradation display polarizing elements (plates), multi-axis polarizing elements (plates), and curved surface polarizing elements (plates) can be produced by a simple manufacturing method. Alternatively, various visible display devices such as a three-dimensional display polarizing element (plate) can be manufactured by combining with a conventional linear polarizing plate.

FIG. 1 is a schematic diagram of an apparatus for providing a photoactive separation layer. FIG. 2 is a schematic view of an irradiation device for visible polarized light. FIG. 3 is a schematic view of an apparatus for providing a dichroic molecular layer.

Claims (12)

A polarized light having a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent, and the dichroic molecule is in a solid state. Element or polarizing plate. The polarizing element or the polarizing plate according to claim 1, wherein a layer having photoactive molecules is provided on the substrate, and a protective layer is provided on the layer containing dichroic molecules. The photoactive molecule is a molecule containing at least one double bond selected from non-aromatic C = C, non-aromatic C = N, and non-aromatic N = N. 2. The polarizing element or polarizing plate of item 2. The polarizing element or the polarizing plate according to claim 1, wherein the hydrophilic substituent is a sulfonic acid group, an amino group, or a hydroxyl group. 3. The polarizing element or polarizing plate according to claim 2, wherein the substrate is flat or curved. After irradiating the layer having photoactive molecules on the substrate with linearly polarized light, a layer containing a solid-state dichroic molecule having a hydrophilic substituent is provided on the photoactive molecule layer. A method for producing an element or a polarizing plate. 7. The method for producing a polarizing element or a polarizing plate according to claim 6, wherein the layer having photoactive molecules on the substrate is subjected to a corona discharge treatment or an ultraviolet irradiation treatment. A layer containing a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent and the dichroic molecule is in a solid state. Toning display polarizing element or polarizing plate. After irradiating the layer having photoactive molecules on the substrate with linearly polarized light through a mask having shading, a layer containing dichroic molecules in a solid state having a hydrophilic substituent is formed on the photoactive molecule layer. A method for producing a polarizing element or a polarizing plate. A compound having a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent, and the dichroic molecule is in a solid state. Axial polarizing element or polarizing plate. The layer having photoactive molecules on the substrate is irradiated with two or more linearly polarized lights having different polarization axes, and then, the dichroic molecules in the solid state having a hydrophilic substituent are included on the photoactive molecule layer. A method for producing a multiaxial polarizing element or a polarizing plate, comprising providing a layer. A solid having a layer having a photoactive molecule and a layer containing a dichroic molecule in contact with the layer, wherein the dichroic molecule is a compound having a hydrophilic substituent, and the dichroic molecule is in a solid state; Display polarizing element or polarizing plate.

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