Classifications

• • 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
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
  • G02F1/13363—Birefringent elements, e.g. for optical compensation
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
  • G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
  • G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation

Definitions

• the present invention relates to a photoreactive composition suitable for production of an optical element having controlled molecular orientation such as a retardation film or a liquid crystal alignment film, and an optical anisotropic film using the same.
• Patent Document 1 and Patent Document 2 in the side chain type liquid crystal polymer that induces birefringence by light irradiation or light irradiation and heating and cooling, it is produced by a process including an operation of light irradiation or light irradiation and heat treatment.
• a retardation film and a manufacturing method thereof are proposed
• Patent Document 3 proposes a liquid crystal alignment film imparted with a liquid crystal alignment ability by light irradiation and a manufacturing method thereof.
• anisotropy can be imparted by an axially selective photocrosslinking reaction of polymer side chains when irradiated with linearly polarized ultraviolet light after being applied to a substrate and formed into a film. Furthermore, when such a film is heated, since the material itself has liquid crystallinity, the unreacted side chain is aligned along the side chain that has been photocrosslinked selectively, or perpendicular to the direction of the photocrosslinked side chain. The entire film can be molecularly oriented because it is oriented in the direction. Such a film can be used as a retardation film because it exhibits birefringence due to molecular orientation, and when liquid crystal molecules are brought into contact with the film surface, it exhibits the ability to align liquid crystal molecules. It also functions as a membrane.
• these materials can be used in various applications due to the property of molecular orientation by light irradiation and heating.
• the materials proposed in these methods cannot be said to have sufficient photoreactivity, and a longer irradiation time is required.
• the temperature in the heat treatment after the light irradiation is not preferable because a considerable time is required at a high temperature exceeding 150 ° C.
• a material capable of improving photoreactivity and inducing molecular orientation by irradiation with linearly polarized ultraviolet rays for a short time has been proposed, but the temperature in the heat treatment after light irradiation is 150. A considerable time is required at a high temperature exceeding 0 ° C., which is not preferable.
• Japanese Unexamined Patent Publication No. 2002-202409 Japanese Unexamined Patent Publication No. 2003-307618 Japanese Unexamined Patent Publication No. 2002-90750 Japanese Unexamined Patent Publication No. 2007-304215
• An object of the present invention is to provide a photoreactive composition that can also use a low-boiling solvent, and a photoalignment film having a retardation obtained therefrom.
• the present inventor conducted research to achieve the above-mentioned problems, and found that a benzoic acid ester compound having a specific structure in a polymer having a repeating unit derived from a monomer composed of a cinnamic acid compound having a specific structure. It has been found that the above object can be achieved by using a photoreactive composition containing a polymer into which a repeating unit derived from a monomer is introduced, and the present invention has been achieved.
• a light comprising a copolymer having a repeating unit derived from a monomer represented by the following formula (1) and a repeating unit derived from a monomer represented by the following formula (2): Reactive composition.
• X 1 and X 2 are each independently —O—, —O—CO—, —CO—O—, —NH—CO—, or —CO—NH—.
• X 3 is —O—CO— or —CO—O—.
• Y is a group selected from the group consisting of a benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, benzophenone, and phenylbenzoate, and each ring is an alkyl group, an alkoxy group, a halogen atom, a nitro group, or It may be substituted with a cyano group.
• R 1 and R 2 are each independently a hydrogen atom or a methyl group.
• p1 and p2 are each independently an integer of 2 to 12.
• W is a group selected from the group consisting of a benzene ring, a naphthalene ring, and a biphenyl ring, and each ring may be substituted with an alkyl group, an alkoxy group, a halogen atom, a nitro group, or a cyano group.
• Z 1 to Z 4 are each independently a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, or a cyano group.
• the monomer represented by the above formula (1) is a cinnamic acid compound represented by the following formula (3), and the monomer represented by the above formula (2) is benzoic acid represented by the following formula (4).
• X 4 is a single bond, —O—CO—, or —CO—O—.
• m is 0 or 1, and when m is 0, X 4 is a single bond.
• R 2 , p 2 , X 3, and Z 1 to Z 4 are respectively synonymous with those defined in the above formula (2).
• R 3 is a hydrogen atom, an alkyl group, or an alkoxy group.
• m 1 is 1 or 2.
• 4). 4.
• the organic solvent is a low boiling point solvent having a boiling point of 60 to 170 ° C. 7). 7.
• the temperature in the heat treatment performed subsequent to the light irradiation treatment necessary for expressing the phase difference can be controlled, and this temperature can be greatly reduced.
• the plastic material having low heat resistance it can be used as a base material, and a solvent having a low boiling point can be used as a solvent necessary for forming the retardation layer.
• a retardation film having excellent characteristics formed on a plastic film having low heat resistance which has been difficult in the past, and orientation of molecules such as a polarization diffraction element at low temperature It is possible to manufacture an optical element or a liquid crystal alignment film in which control is performed.
• a copolymer having a repeating unit derived from the monomer represented by the above formula (1) and a repeating unit derived from the monomer represented by the above formula (2) Contains a polymer.
• X 1 , X 2 , Y, Z 1 to Z 4 , R 1 , R 2 , W, p1, and p2 are as defined above.
• X 1 and X 2 are each preferably —O—, —O—CO—, —CO—O—
• Y is a benzene ring, naphthalene ring, biphenyl ring, furan ring, respectively.
• Z 1 to Z 4 are preferably a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, and W is preferably a benzene ring or a biphenyl ring.
• p1 and p2 are preferably 4 to 10.
• the monomer represented by the above formula (1) include monomers having the following structure.
• preferred specific examples of the monomer represented by the formula (2) include monomers having the following structure.
• the copolymer having is represented by the following formula (5).
• X 1 , X 2 , X 3 , Y, Z 1 to Z 4 , R 1 , R 2 , W, p1, and p2 each include the above formula (1).
• the ratio of n / m is the ratio of (repeating unit derived from the monomer represented by the above formula (1)) / (repeating unit derived from the monomer represented by the above formula (2)).
• the molar ratio of n / m is preferably 10/90 to 80/20, and particularly preferably 20/80 to 50/50.
• the copolymer having a repeating unit derived from the monomer represented by the above formula (1) and a repeating unit derived from the monomer represented by the above formula (2) preferably has a number average molecular weight. 1000 to 100,000, and preferably 5000 to 30,000. If this number average molecular weight is smaller than the above range, molecular orientation cannot be induced, and if it is larger than the above range, the production becomes extremely difficult and the solubility in a low boiling point solvent decreases. It is not preferable.
• the copolymer having a crosslinkable monomer for improving heat resistance to such an extent that liquid crystallinity is not impaired, a photosensitive monomer that does not impair liquid crystallinity, or liquid crystalline Monomers and the like for adjusting the expression temperature can be copolymerized.
• the cross-linkable monomer include the following phenoplast type and epoxy group-containing compounds.
• epoxy group-containing compound examples include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1 , 6-hexanediol diglycidyl ether, glycerin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, 1,3,5,6-tetraglycidyl-2,4-hexanediol, N, N, N ′ , N ′,-tetraglycidyl-m-xylenediamine, 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, N, N, N ′, N ′,-tetraglycidyl Such as 4,4'-d
• the amount used is preferably 0.1 to 30 parts by mass, more preferably 100 parts by mass of the resin component contained in the liquid crystal aligning agent. Is 0.5 to 20 parts by mass. If the amount used is less than 0.1 parts by mass, the effect of improving heat resistance cannot be expected, and if it exceeds 30 parts by mass, the liquid crystallinity may be impaired.
• the photosensitive monomer include polymerizable compounds having the following structure or a derivative thereof in the side chain.
• the amount used is the sum of the repeating unit derived from the monomer represented by the formula (1) and the repeating unit derived from the monomer represented by the formula (2) / the photosensitive monomer. ) Is preferably 95/5 to 50/50, more preferably 95/5 to 80/20. If the ratio is less than 95/5, the effect of improving the photosensitivity cannot be expected, and if it exceeds 50/50, the liquid crystallinity may be impaired.
• the monomer for adjusting the liquid crystalline expression temperature include a polymerizable compound having a structure that becomes a liquid crystal mesogen structure alone, such as biphenyl and phenylbenzoate as shown below. And polymerizable compounds having a structure such that a liquid crystal mesogen structure is formed by hydrogen bonding of side chains such as benzoic acid.
• the amount used is (total of repeating units derived from the monomer represented by the above formula (1) and repeating units derived from the monomer represented by the above formula (2)) / single photosensitive amount Body) is preferably 95/5 to 20/80, more preferably 95/5 to 50/50. If the ratio is less than 95/5, the effect of adjusting the liquid crystal expression temperature cannot be expected, and if it exceeds 30/70, the sensitivity of the photoreaction may be impaired.
• a copolymer having a repeating unit derived from the monomer represented by the above formula (1) and a repeating unit derived from the monomer represented by the above formula (2) is copolymerized.
• the monomer include industrially available monomers capable of radical polymerization reaction. Specific examples of these monomers include unsaturated carboxylic acid, acrylic ester compound, methacrylic ester compound, maleimide compound, acrylonitrile, maleic anhydride, styrene compound, vinyl compound and the like.
• the unsaturated carboxylic acid include acrylic acid, methacrylic acid (acrylic acid and methacrylic acid are collectively referred to as (meth) acrylic acid), itaconic acid, maleic acid, and fumaric acid.
• Specific examples of the (meth) acrylic acid ester compound include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, benzyl (meth) acrylate, naphthyl (meth) acrylate, anthryl (meth) acrylate, anne Tolylmethyl (meth) acrylate, phenyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, 2-methoxy Ethyl (meth) acrylate, methoxy
• vinyl compound examples include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, propyl vinyl ether and the like.
• styrene compound examples include styrene, methylstyrene, chlorostyrene, and bromostyrene.
• maleimide compound examples include maleimide, N-methylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide and the like.
• the manufacturing method of the copolymer which has a repeating unit derived from the monomer represented by the said Formula (1) of this invention, and a repeating unit derived from the monomer represented by the said Formula (2) It is not particularly limited, and a general-purpose method that is handled industrially can be used. Specifically, it can be produced by cationic polymerization, radical polymerization, or anionic polymerization. Of these, radical polymerization is particularly preferred from the viewpoint of ease of reaction control.
• the polymerization initiator for radical polymerization known radical thermal polymerization initiators, radical photopolymerization initiators, known reversible addition-fragmentation chain transfer (RAFT) polymerization reagents, and the like can be used.
• the amount of the polymerization initiator used is preferably 0.1 to 10 mol% with respect to the monomer (1 mol) represented by the above formula (1).
• the above-mentioned radical thermal polymerization initiator is a compound that generates radicals by heating to a decomposition temperature or higher.
• radical thermal polymerization initiators include ketone peroxides (such as methyl ethyl ketone peroxide and cyclohexanone peroxide), diacyl peroxides (such as acetyl peroxide and benzoyl peroxide), hydroperoxides (peroxides).
• a radical thermal polymerization initiator can be used individually by 1 type, and can
• the radical photopolymerization initiator is a compound that initiates radical polymerization by light irradiation.
• radical photopolymerization initiators include benzophenone, Michler's ketone, 4,4′-bis (diethylamino) benzophenone, xanthone, thioxanthone, isopropyl xanthone, 2,4-diethylthioxanthone, 2-ethylanthraquinone, acetophenone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-2-methyl-4′-isopropylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, isopropyl benzoin ether, isobutyl benzoin ether, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, camphorquinone, benzanthrone, 2-methyl-1- [4- (methylthio) phenyl] -2-
• the radical polymerization method using the above-described radical thermal polymerization initiator is not particularly limited, and known emulsion polymerization method, suspension polymerization method, dispersion polymerization method, precipitation polymerization method, bulk polymerization method, solution polymerization method, etc. This method can be used.
• the photoreactive composition of the present invention includes a copolymer having a repeating unit derived from the monomer represented by the formula (1) and a repeating unit derived from the monomer represented by the formula (2).
• it preferably contains an organic solvent that dissolves the copolymer.
• a thin film can be easily formed from the photoreactive composition of the present invention by adding a polymer solution containing such an organic solvent.
• the content of the organic solvent in the photoreactive composition of the present invention is preferably 99.7 to 60% by mass, particularly preferably 99.5 to 70% by mass. By setting it as this content, it can be set as the solution of a preferable viscosity for forming a thin film easily from the photoreactive composition of this invention.
• the organic solvent contained in the photoreactive composition of the present invention is not particularly limited as long as it is an organic solvent that dissolves the resin component.
• Specific examples thereof include N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylcaprolactam, 2-pyrrolidone, N-ethylpyrrolidone, N-vinylpyrrolidone, dimethyl sulfoxide, Tetramethylurea, pyridine, dimethylsulfone, hexamethylsulfoxide, ⁇ -butyrolactone, 3-methoxy-N, N-dimethylpropanamide, 3-ethoxy-N, N-dimethylpropanamide, 3-butoxy-N, N-dimethyl Propanamide, 1,3-dimethyl-imidazolidinone, ethyl amyl ketone, methyl nonyl ketone, methyl ethyl ketone, methyl isoamyl
• the photo-alignment film obtained from the photoreactive composition of the present invention when used as a liquid crystal alignment film, when firing at a low temperature, if there is a large amount of residual solvent after firing, the orientation of the liquid crystal and the adhesion to the substrate will be Since the liquid crystal cell may deteriorate and the electrical characteristics of the liquid crystal cell may deteriorate, it is preferable to use an organic solvent having a low boiling point or a high vapor pressure.
• organic solvents include ethyl amyl ketone, methyl nonyl ketone, methyl ethyl ketone, methyl isoamyl ketone, methyl isopropyl ketone, cyclohexanone, ethylene carbonate, propylene carbonate, diglyme, 4-hydroxy-4-methyl-2-pentanone, isopropyl Alcohol, methoxymethylpentanol, methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, butyl carbitol, ethyl carbitol, ethyl carbitol acetate, ethylene glycol, ethylene glycol monoacetate, ethylene glycol monoisopropyl ether, Ethylene glycol monobutyl ether, propylene glycol, propylene glycol Monoacetate, propylene glycol monomethyl
• the photoreactive composition of the present invention can further contain a photosensitizer as an additive.
• a photosensitizer as an additive.
• these photosensitizers colorless sensitizers and triplet sensitizers are preferable.
• the photosensitizer include aromatic nitro compounds, coumarins (7-diethylamino-4-methylcoumarin, 7-hydroxy4-methylcoumarin), ketocoumarins, carbonyl biscoumarins, aromatic 2-hydroxyketones, and amino-substituted compounds.
• Aromatic 2-hydroxy ketones (2-hydroxybenzophenone, mono- or di-p- (dimethylamino) -2-hydroxybenzophenone), acetophenone, anthraquinone, xanthone, thioxanthone, benzanthrone, thiazoline (2-benzoylmethylene-3 -Methyl- ⁇ -naphthothiazoline, 2- ( ⁇ -naphthoylmethylene) -3-methylbenzothiazoline, 2- ( ⁇ -naphthoylmethylene) -3-methylbenzothiazoline, 2- (4-biphenoylmethylene)- 3-methylbenzothiazo 2- ( ⁇ -naphthoylmethylene) -3-methyl- ⁇ -naphthothiazoline, 2- (4-biphenoylmethylene) -3-methyl- ⁇ -naphthothiazoline, 2- (4-biphenoylmethylene) -3-methyl- ⁇ -
• aromatic 2-hydroxyketone (benzophenone), coumarin, ketocoumarin, carbonylbiscoumarin, acetophenone, anthraquinone, xanthone, thioxanthone, and acetophenone ketal are preferable.
• the photoreactive composition of the present invention includes a dielectric material for the purpose of changing electrical characteristics such as dielectric constant and conductivity of the liquid crystal alignment film as long as the effects of the present invention are not impaired.
• a crosslinkable compound may be added for the purpose of increasing the hardness and density of the film when formed into a liquid crystal alignment film.
• a surfactant such as a fluorine-based surfactant, a silicone-based surfactant, and a nonionic surfactant may be added.
• F-Top 301, EF303, EF352 manufactured by Tochem Products
• MegaFuck F171, F173, R-30 manufactured by DIC
• Florard FC430, FC431 manufactured by Sumitomo 3M
• Asahi Examples include Guard AG710 (manufactured by Asahi Glass Co., Ltd.), Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by AGC Seimi Chemical Co., Ltd.).
• the surfactant is preferably contained in an amount of 0.01 to 2 parts by weight, more preferably 0.01 to 1 part by weight, based on 100 parts by weight of the copolymer contained in the photoreactive composition of the present invention. Is done.
• the compound that improves the adhesion between the liquid crystal alignment film and the substrate include the following functional silane-containing compounds.
• an optically anisotropic film having excellent characteristics can be obtained from the photoreactive composition of the present invention.
• the production of the optically anisotropic film is preferably carried out as follows. .
• the photoreactive composition of the present invention is applied to a substrate to form a coating film.
• the coating film is usually formed by a spin coating method, a printing method, an ink jet method, a bar coating method, a gravure coating method, or the like.
• the drying is usually performed at 40 to 150 ° C. for 1 to 15 minutes, preferably at 50 to 110 ° C. for 1 to 5 minutes.
• the thickness of the coating film is usually 0.02 to 5.0 ⁇ m, preferably 0.02 to 2.0 ⁇ m.
• the substrate for forming the coating film of the photoreactive composition is not particularly limited as long as it is a highly transparent substrate, and a plate-like to film-like one is used.
• the material of the base material ceramics such as glass, silicon nitride, and silicon wafer, plastics such as acrylic resin, polycarbonate resin, triacetyl cellulose resin, polyethylene terephthalate resin, and cycloolefin resin can be used.
• acrylic resin polycarbonate resin
• triacetyl cellulose resin polyethylene terephthalate resin
• cycloolefin resin cycloolefin resin
• the coating film of the photoreactive composition can then be oriented and imparted with anisotropy by irradiation treatment with polarized ultraviolet rays.
• polarized ultraviolet rays those having a wavelength of preferably 200 to 400 nm, particularly preferably 254 to 365 nm are used.
• the irradiation amount is preferably 1 to 10000 mJ, particularly preferably 1 to 500 mJ.
• the irradiation with polarized ultraviolet rays may be performed while heating the coating film preferably at 10 to 150 ° C., particularly preferably at 20 to 120 ° C.
• the coating film of the photoreactive composition formed on the substrate is then subjected to heat treatment.
• the heat treatment is preferably performed at 50 to 150 ° C. for 1 to 30 minutes, particularly preferably at 70 to 120 ° C. for 1 to 15 minutes.
• the upper limit of the heating temperature is selected depending on the substrate to be used, and the lower limit is selected depending on the liquid crystalline expression temperature of the polymer.
• a thin film of a photoreactive composition can be produced on a substrate.
• the film thickness of the thin film of the photoreactive composition is preferably 20 to 5000 nm, and more preferably 20 to 2000 nm.
• Polymer 2 was obtained by performing the same operation as in Synthesis Example 4 except that the ratio of Formula (1) and Formula (2) in Synthesis Example 4 was 40:60.
• the molecular weight of this polymer 2 was Mn: 27000, and this polymer 2 exhibited liquid crystallinity in the temperature range of 53 to 132 ° C.
• Polymer 3 was obtained by performing the same operation as in Synthesis Example 4 except that the ratio of Formula (1) and Formula (2) in Synthesis Example 4 was 20:80.
• the molecular weight of this polymer 3 was Mn: 43000, and this polymer 3 exhibited liquid crystallinity in the temperature range of 43 to 119 ° C.
• Example 1 The polymer 1 (0.3 g) obtained in Synthesis Example 4 is dissolved in tetrahydrofuran (14.7 ml) and spin-coated on a glass substrate with a thickness of about 190 nm, whereby a side chain polymer film is formed on the substrate. Formed. After measuring the ultraviolet absorption spectrum using this substrate, the side chain type polymer film was irradiated with ultraviolet rays having a wavelength of 300 nm or less cut and converted into linearly polarized light using a Grand Taylor prism.
• the side-chain polymer film on the substrate thus obtained was used to measure the ultraviolet absorption spectrum, and the side-chain polymer film was measured in a direction perpendicular to the UV absorbance in the direction parallel to the polarization direction of the irradiated polarized UV light.
• ⁇ A which is the difference from the ultraviolet absorbance, was evaluated.
• ⁇ A reaches a maximum of 0.15 at 314 nm when irradiated with polarized ultraviolet rays at a wavelength of 365 nm in an amount of 70 mJ.
• Example 2 Polymer 2 (0.3 g) obtained in Synthesis Example 5 was used, except that the irradiation amount of polarized ultraviolet rays was 5 mJ (the irradiation amount at which ⁇ A was 25% of the maximum value of ⁇ A), and the heating temperature was 95 ° C. In the same manner as in Example 1, irradiation with polarized ultraviolet rays and subsequent heat treatment were performed. As a result, ⁇ A before and after the heat treatment was greatly amplified, the degree of orientation was 0.58 at 314 nm, and the birefringence at that time was 0.12.
• Example 3 Polymer 3 (0.3 g) obtained in Synthesis Example 6 was used, the amount of irradiation with polarized ultraviolet rays was 8 mJ (the amount of irradiation with which ⁇ A was 33% of the maximum value of ⁇ A), and the heating temperature was 85 ° C. In the same manner as in Example 1, irradiation with polarized ultraviolet rays and subsequent heat treatment were performed. As a result, ⁇ A before and after the heat treatment was greatly amplified, the degree of orientation was 0.48 at 314 nm, and the birefringence at that time was 0.16.
• Example 4 Polymer 1 (0.3 g) obtained in Synthesis Example 4 was dissolved in a mixed solvent of propylene glycol monomethyl ether and cyclohexanone (volume ratio 7: 3, 2.7 ml), and a thickness of about 800 nm was formed on the acrylic film.
• the side chain type polymer film was formed on the film by coating with (1).
• the film on which this polymer film was formed was irradiated with 20 mJ of ultraviolet rays converted to linearly polarized light of 313 nm using a Grand Taylor prism. Thereafter, this substrate was heated to 100 ° C. in a hot air circulating oven, and the side chain type polymer film was held as it was for 10 minutes as a liquid crystal alignment layer. Then, it cooled to room temperature and obtained the film which has a side chain type polymer film (film thickness of 800 nm) in which anisotropy was introduced in the film. The birefringence of this film was 0.08.
• Example 5 Polymer 2 (0.3 g) obtained in Synthesis Example 5 was dissolved in a mixed solvent of propylene glycol monomethyl ether and cyclohexanone (volume ratio 7: 3, 2.7 ml), and irradiated with 10 mJ of ultraviolet rays converted to linearly polarized light. Except for the above, a film having a side chain polymer film having anisotropy introduced therein was obtained in the same manner as in Example 4. The birefringence of this film was 0.074.
• Example 6 Polymer 4 (0.3 g) obtained in Synthesis Example 7 was dissolved in a mixed solvent of propylene glycol monomethyl ether acetate and cyclohexanone (volume ratio 7: 3, 2.7 ml) and irradiated with 7 mJ of ultraviolet light converted to linearly polarized light. Except for the above, a film having a side chain polymer film having anisotropy introduced therein was obtained in the same manner as in Example 4. The birefringence of this film was 0.056.
• Example 7 Polymer 1 (0.3 g) obtained in Synthesis Example 4 was dissolved in a mixed solvent of propylene glycol monomethyl ether and cyclohexanone (volume ratio 3: 7, 4.7 ml) to obtain a liquid crystal aligning agent (A).
• the liquid crystal aligning agent (A) was applied to a glass substrate by a spin coating method, and then dried on a hot plate at 50 ° C. for 5 minutes to obtain a polymer film having a thickness of 80 nm.
• This polymer film was irradiated with 4 mJ of ultraviolet rays converted to 313 nm linearly polarized light using a Grand Taylor prism. Thereafter, this substrate was heated to 100 ° C.
• Example 8 Polymer 2 (0.3 g) obtained in Synthesis Example 5 was used, except that the irradiation amount of polarized ultraviolet rays was 5 mJ (the irradiation amount at which ⁇ A was 25% of the maximum value of ⁇ A), and the heating temperature was 95 ° C. Produced a liquid crystal cell in the same manner as in Example 7. The results are summarized in Table 1.
• Example 9 Polymer 3 (0.3 g) obtained in Synthesis Example 6 was used, the amount of irradiation with polarized ultraviolet rays was 8 mJ (the amount of irradiation with which ⁇ A was 33% of the maximum value of ⁇ A), and the heating temperature was 85 ° C. Produced a liquid crystal cell in the same manner as in Example 7. The results are summarized in Table 1.
• the photo-alignment film and retardation film formed from the photoreactive composition of the present invention can be formed on a plastic having low heat resistance, it is widely used as an optical element or liquid crystal alignment film with controlled molecular orientation. It can be used and has high industrial utility.
• the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2012-250558 filed on November 14, 2012 are incorporated herein as the disclosure of the specification of the present invention. Is.

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