WO2021033639A1 - Procédé de production d'un film optique - Google Patents

Procédé de production d'un film optique Download PDF

Info

Publication number
WO2021033639A1
WO2021033639A1 PCT/JP2020/030868 JP2020030868W WO2021033639A1 WO 2021033639 A1 WO2021033639 A1 WO 2021033639A1 JP 2020030868 W JP2020030868 W JP 2020030868W WO 2021033639 A1 WO2021033639 A1 WO 2021033639A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
polymerizable liquid
substrate
solvent
mass
Prior art date
Application number
PCT/JP2020/030868
Other languages
English (en)
Japanese (ja)
Inventor
輝 丸山
勇太 高橋
啓祐 小玉
慎平 吉田
聡 矢野口
Original Assignee
富士フイルム株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to JP2021540762A priority Critical patent/JPWO2021033639A1/ja
Priority to KR1020227004249A priority patent/KR20220032587A/ko
Publication of WO2021033639A1 publication Critical patent/WO2021033639A1/fr

Links

Images

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C55/00—Shaping by stretching, e.g. drawing through a die; Apparatus therefor
    • B29C55/02—Shaping by stretching, e.g. drawing through a die; Apparatus therefor of plates or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/16—Chemical modification with polymerisable compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light

Definitions

  • the present invention relates to a method for producing an optical film.
  • the optically anisotropic layer having refractive index anisotropy is applied to various applications such as an antireflection film of a display device and an optical compensation film of a liquid crystal display device.
  • Patent Document 1 as a method of forming an optically anisotropic layer, a rubbing-treated alignment film is formed on a substrate, and a composition containing a liquid crystal compound is applied onto the alignment film to form an optically anisotropic layer. Methods of forming layers are known.
  • the present invention includes the substrate and the optically anisotropic layer, suppresses orientation defects of the optically anisotropic layer, and has excellent adhesion between the substrate and the optically anisotropic layer.
  • An object of the present invention is to provide a method for producing a film.
  • Step 1 of applying an orientation regulating force to the substrate surface and A polymerizable liquid crystal composition containing a polymerizable liquid crystal compound and a solvent is applied onto the substrate to orient the polymerizable liquid crystal compound, and the orientation state of the polymerizable liquid crystal compound is fixed to form an optically anisotropic layer.
  • Has step 2 and A method for producing an optical film wherein the mass change rate determined by the formula (1) is 0.1 to 1.5% by mass. Equation (1)
  • Weight change rate ⁇ (W B -W A) / W A ⁇ ⁇ 100 W A is the dry weight of the substrate, W B is the wet weight of the substrate after immersion of the substrate in the solvent.
  • step 1 is a step of applying a rubbing treatment to the surface of the substrate or a step of applying a stretching treatment to the substrate.
  • step 3 is a step of applying a rubbing treatment to the surface of the substrate or a step of applying a stretching treatment to the substrate.
  • the solvent is selected from the group consisting of an ester solvent, an ether solvent, an amide solvent, a carbonate solvent, and a ketone solvent. ..
  • (4) The optical film according to any one of (1) to (3), wherein the absolute value of the difference between the SP value of the solvent and the SP value of the polymerizable liquid crystal compound is 3.7 MPa 1/2 or less. Production method.
  • a method for producing an optical film which includes a substrate and an optically anisotropic layer, suppresses orientation defects of the optically anisotropic layer, and has excellent adhesion between the substrate and the optically anisotropic layer.
  • light means active light or radiation, for example, the emission line spectrum of a mercury lamp, far ultraviolet rays typified by an excimer laser, extreme ultraviolet rays (EUV light: Extreme Ultraviolet), X rays, ultraviolet rays, and the like. And electron beam (EB: Electron Beam) and the like. Of these, ultraviolet rays are preferable.
  • visible light refers to light having a diameter of 380 to 780 nm. Further, in the present specification, unless otherwise specified, the measurement wavelength is 550 nm.
  • (meth) acrylic is a general term for acrylic and methacrylic
  • (meth) acrylate is a general term for acrylate and methacrylate
  • (meth) acrylamide is a general term for acrylamide and methacrylamide. It is a generic term.
  • the twist angle is preferably more than 0 ° and less than 360 °.
  • a feature of the method for producing an optical film of the present invention is that the substrate to be used and the solvent contained in the polymerizable liquid crystal composition satisfy a predetermined relationship. More specifically, when the substrate to be used and the solvent contained in the polymerizable liquid crystal composition have a predetermined affinity, when the polymerizable liquid crystal composition is applied onto the substrate, a predetermined amount of the solvent is contained inside the substrate. Penetrate. At that time, the polymerizable liquid crystal compound also permeates into the substrate together with the solvent, and when the curing treatment is performed, the optically anisotropic layer partially penetrates into the substrate, and as a result, the substrate and the optically anisotropic layer Adhesion with is improved.
  • the mass change rate described later can be mentioned. If the mass change rate is too low, it means that the solvent does not permeate into the inside of the substrate, and the affinity between the two is inferior, and as a result, the adhesion between the substrate and the optically anisotropic layer is inferior. Further, if the mass change rate is too high, the affinity between the substrate and the solvent is too high, which leads to orientation defects of the optically anisotropic layer.
  • the method for producing an optical film of the present invention has the following steps.
  • Step 1 Applying orientation-regulating force to the substrate surface
  • Step 2 A polymerizable liquid crystal composition containing a polymerizable liquid crystal compound and a solvent is applied onto the substrate to orient the polymerizable liquid crystal compound, and the polymerizable liquid crystal compound is applied.
  • Steps of immobilizing the orientation state of the above to form an optically anisotropic layer Each step will be described in detail below.
  • Step 1 is a step of applying an orientation regulating force to the surface of the substrate.
  • an orientation regulating force capable of inducing an orientation state of the polymerizable liquid crystal compound imparted on the substrate is imparted to the substrate.
  • a transparent substrate is preferable.
  • the transparent substrate is intended to be a substrate having a visible light transmittance of 60% or more, and the transmittance is preferably 80% or more, more preferably 90% or more.
  • the material for forming the substrate a polymer having excellent optical performance transparency, mechanical strength, thermal stability, moisture shielding property, isotropic property and the like is preferable.
  • the polymer film that can be used as a substrate include a cellulose acylate film (for example, a cellulose triacetate film (refractive coefficient 1.48), a cellulose diacetate film, a cellulose acetate butyrate film, and a cellulose acetate propionate film.
  • Polyethylene film such as polyethylene film and polypropylene film, polyester film such as polyethylene terephthalate film and polyethylene naphthalate film, polyether sulfone film, polyacrylic film such as polymethylmethacrylate, polyurethane film, polycarbonate film, polysulfone film, polyether Film, polymethylpentene film, polyether ketone film, (meth) acrylic nitrile film, and polymer film having an alicyclic structure (Norbornene resin (Arton: trade name, JSR), amorphous polyolefin (Zeonex) : Product name, manufactured by Nippon Zeon Co., Ltd.)))).
  • cellulose acylate poly (meth) acrylate, polystyrene, or polycarbonate is preferable.
  • the substrate may contain various additives (eg, optical anisotropy modifiers, wavelength dispersion modifiers, fine particles, plasticizers, UV inhibitors, degradation inhibitors, release agents, etc.). ..
  • the thickness of the substrate is not particularly limited, but is preferably 10 to 200 ⁇ m, more preferably 10 to 100 ⁇ m, and even more preferably 20 to 90 ⁇ m.
  • the substrate may be made of a plurality of laminated sheets.
  • the substrate may be subjected to surface treatments (eg, glow discharge treatment, corona discharge treatment, ultraviolet (UV) treatment, flame treatment) on the surface of the substrate in order to improve adhesion to a layer provided on the substrate.
  • surface treatments eg, glow discharge treatment, corona discharge treatment, ultraviolet (UV) treatment, flame treatment
  • step 1 the method is not particularly limited as long as the orientation regulating force can be applied to the surface of the substrate.
  • the orientation regulating force means a property that can orient the polymerizable liquid crystal compound in the polymerizable liquid crystal composition imparted onto the substrate.
  • a step of applying a rubbing treatment to the surface of the substrate or a step of applying a stretching treatment to the substrate is preferable.
  • a processing method widely adopted as a liquid crystal alignment processing step of an LCD (liquid crystal display) can be applied. That is, a method of obtaining an orientation regulating force by rubbing the surface of the substrate with paper, gauze, felt, rubber, nylon fiber, polyester fiber, or the like in a certain direction can be used.
  • the direction of the rubbing treatment is not particularly limited, and the optimum direction is appropriately selected according to the direction in which the polymerizable liquid crystal compound is desired to be oriented.
  • the method of stretching treatment is not particularly limited, and examples thereof include a method using a known stretching machine such as a tenter stretching machine.
  • the stretching direction is not particularly limited, and the optimum direction is appropriately selected according to the direction in which the polymerizable liquid crystal compound is desired to be oriented.
  • the draw ratio can be appropriately set within a range in which an orientation restricting force is generated on the surface of the support.
  • the alignment film is not arranged on the substrate. That is, the substrate and the optically anisotropic layer described later are in direct contact with each other.
  • the alignment film is a film formed on the substrate only for aligning the liquid crystal compound.
  • step 2 a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound and a solvent is applied onto the substrate obtained in step 1, the polymerizable liquid crystal compound is oriented, and the orientation state of the polymerizable liquid crystal compound is fixed.
  • step 2 a step of forming an optically anisotropic layer. By carrying out this step, an optical film having a substrate and an optically anisotropic layer arranged on the substrate is formed.
  • the materials contained in the polymerizable liquid crystal composition used in this step will be described in detail, and then the procedure of the step will be described in detail.
  • the polymerizable liquid crystal composition contains a polymerizable liquid crystal compound.
  • the polymerizable liquid crystal compound is a liquid crystal compound having a polymerizable group.
  • the type of the polymerizable liquid crystal compound is not particularly limited. In general, liquid crystal compounds can be classified into rod-shaped type (rod-shaped liquid crystal compound) and disk-shaped type (discotic liquid crystal compound) according to their shape. Further, the liquid crystal compound can be classified into a low molecular weight type and a high molecular weight type.
  • a polymer generally refers to a polymer having a degree of polymerization of 100 or more (polymer physics / phase transition dynamics, by Masao Doi, p. 2, Iwanami Shoten, 1992).
  • any liquid crystal compound can be used, but it is preferable to use a polymerizable rod-shaped liquid crystal compound or a polymerizable disk-shaped liquid crystal compound, and it is more preferable to use a polymerizable rod-shaped liquid crystal compound.
  • Two or more kinds of polymerizable rod-shaped liquid crystal compounds, two or more kinds of polymerizable disk-shaped liquid crystal compounds, or a mixture of the polymerizable rod-shaped liquid crystal compound and the polymerizable disk-shaped liquid crystal compound may be used.
  • the polymerizable rod-shaped liquid crystal compound for example, those described in claim 1 of JP-A No. 11-513019 and paragraphs 0026 to 0098 of JP-A-2005-289980 can be preferably used.
  • polymerizable disk-shaped liquid crystal compound for example, those described in paragraphs 0020 to 0067 of JP-A-2007-108732 and paragraphs 0013 to 0108 of JP-A-2010-2404038 can be preferably used.
  • the type of the polymerizable group contained in the polymerizable liquid crystal compound is not particularly limited, and a functional group capable of an addition polymerization reaction is preferable, a polymerizable ethylenically unsaturated group or a ring-polymerizable group is more preferable, and a (meth) acryloyl group, A vinyl group, a styryl group, or an allyl group is more preferable.
  • the optically anisotropic layer produced in the present invention is a layer formed by fixing a polymerizable liquid crystal compound (polymerizable rod-shaped liquid crystal compound or polymerizable disk-shaped liquid crystal compound) by polymerization or the like. Therefore, it is no longer necessary to exhibit liquid crystallinity after forming a layer.
  • the content of the polymerizable liquid crystal compound in the polymerizable liquid crystal composition is not particularly limited, but is preferably 50% by mass or more, more preferably 70% by mass or more, based on the total solid content in the polymerizable liquid crystal composition.
  • the upper limit is not particularly limited, but it is often 90% by mass or less.
  • the solid content means a component capable of forming an optically anisotropic layer from which the solvent has been removed, and is a solid content even if the property is liquid.
  • the polymerizable liquid crystal composition contains a solvent.
  • the solvent is not particularly limited as long as the solvent has a mass change rate within a predetermined range in relation to the substrate to be used.
  • the solvent include ester-based solvents, ether-based solvents, amide-based solvents, carbonate-based solvents, ketone-based solvents, aliphatic hydrocarbon-based solvents, alicyclic hydrocarbon-based solvents, aromatic hydrocarbon-based solvents, and halogenation.
  • Examples include carbon-based solvents, water, and alcohol-based solvents.
  • At least one of the points that the adhesion between the substrate and the optically anisotropic layer is more excellent and the point that the orientation defect of the optically anisotropic layer is further suppressed can be obtained (hereinafter, simply “book”. It is also referred to as “the effect of the invention is more excellent"), and an ester solvent, an ether solvent, an amide solvent, a carbonate solvent, or a ketone solvent is preferable.
  • an ester solvent for example, isobutyl acetate, isopropyl acetate, n-butyl acetate and tert-butyl acetate
  • a ketone solvent for example, methyl isobutyl ketone
  • an ether solvent for example
  • the suitable solvents exemplified above eg, methyl isobutyl ketone, tert-butyl acetate, or n-butyl acetate
  • the boiling point of the solvent is not particularly limited, but is preferably more than 50 ° C. Further, only one type of solvent may be used, or two or more types may be mixed and used.
  • the SP value (solubility parameter) of the solvent is not particularly limited, but the SP value of the above-mentioned polymerizable liquid crystal compound and the SP value of the solvent are different from each other in that the effect of the present invention is more excellent and the polymerizable liquid crystal compound is easily dissolved.
  • the absolute value of the difference is preferably 3.7 MPa 1/2 or less.
  • the lower limit is not particularly limited, but it is often more than 0 MPa 1/2.
  • the difference between the SP value of the polymerizable liquid crystal compound and the SP value of the mixed solvent may be within the above range.
  • the SP value of the polymerizable liquid crystal compound is the same as that for obtaining the SP value of the mixed solvent of each polymerizable liquid crystal compound.
  • the SP value is a value calculated by the Hoy method, and the Hoy method is described in POLYMERHANDBOOKFOURTHETION.
  • the mass change rate determined by the formula (1) is 0.1 to 1.5% by mass. That is, the solvent and the substrate are selected so as to satisfy the relationship of the above formula (1). Among them, the mass change rate is preferably 0.5 to 1.5% by mass because the effect of the present invention is more excellent.
  • the mass change rate is less than 0.1% by mass, the solvent cannot swell the substrate, the polymerizable liquid crystal compound does not easily penetrate into the substrate, and the adhesion between the substrate and the optically anisotropic layer is poor.
  • the mass change rate exceeds 1.5% by mass the solvent swells the substrate too much, and the polymerizable liquid crystal compound permeates too much into the substrate, resulting in orientation defects of the optically anisotropic layer.
  • Weight change rate ⁇ (W B -W A) / W A ⁇ ⁇ 100
  • W A is the dry weight of the substrate
  • W B is the wet weight of the substrate after immersion of the substrate in the solvent (solvent contained in the polymerizable liquid crystal composition).
  • the measurement method of the dry weight W A of the substrate is to cut the substrate in a vertical 40 mm ⁇ horizontal 40 mm, dried for 30 minutes at 100 ° C. oven substrate obtained by cutting, drying treatment is performed for the substrate mass and dry mass W a.
  • the method of measuring the wet weight W B of the substrate first, put 10 cc (solvent used as components contained in the polymerizable liquid crystal composition) The solvent used in the glass vial (capacity 15 cc), 50 Heat to ° C. Next, the dried substrate obtained in the above procedure was immersed in a solvent heated to 50 ° C. for 2 minutes, then the substrate was taken out, and the droplets on the removed substrate were taken out using a Kim towel. wiping, measuring the wet weight W B of the resulting substrate.
  • a mixed solvent in the polymerizable liquid crystal composition contains (two or more solvents are solvents obtained by mixing a predetermined amount ratio), when measuring the wet weight W B, the polymerizable liquid crystal composition The above measurement is performed using the contained mixed solvent.
  • the polymerizable liquid crystal composition may contain components other than the above-mentioned polymerizable liquid crystal compound and solvent.
  • the polymerizable liquid crystal composition may contain a polymerization initiator.
  • the polymerization initiator include known polymerization initiators, photopolymerization initiators and thermal polymerization initiators, and photopolymerization initiators are preferable.
  • the content of the polymerization initiator in the polymerizable liquid crystal composition is not particularly limited, but is preferably 0.01 to 20% by mass, preferably 0.5 to 10% by mass, based on the total solid content in the polymerizable liquid crystal composition. Is more preferable.
  • the polymerizable liquid crystal composition may contain a polymerizable monomer different from the polymerizable liquid crystal compound.
  • the polymerizable monomer include a radically polymerizable compound and a cationically polymerizable compound, and a polyfunctional radically polymerizable monomer is preferable.
  • the polymerizable monomer include the polymerizable monomers described in paragraphs 0018 to 0020 in JP-A-2002-296423.
  • the polymerizable monomer is preferably a non-liquid crystal monomer (a monomer that does not exhibit liquid crystallinity).
  • the content of the polymerizable monomer in the polymerizable liquid crystal composition is not particularly limited, but is preferably 1 to 50% by mass, more preferably 5 to 30% by mass, based on the total mass of the polymerizable liquid crystal compound.
  • the polymerizable liquid crystal composition may contain a surfactant.
  • the surfactant include conventionally known compounds, but fluorine-based compounds are preferable. Specifically, for example, the compounds described in paragraphs 0028 to 0056 of JP-A-2001-330725 and the compounds described in paragraphs 0069 to 0126 of JP-A-2005-062673 can be mentioned.
  • the polymerizable liquid crystal composition may contain a polymer.
  • the polymer include cellulose esters.
  • examples of the cellulose ester include those described in paragraph 0178 in JP-A-2000-155216.
  • the content of the polymer in the polymerizable liquid crystal composition is not particularly limited, but is preferably 0.1 to 10% by mass, more preferably 0.1 to 8% by mass, based on the total mass of the polymerizable liquid crystal compound.
  • the polymerizable liquid crystal composition may contain an additive (orientation control agent) that promotes horizontal orientation or vertical orientation in order to bring the liquid crystal compound into a horizontal or vertical orientation state.
  • an additive orientation control agent
  • the polymerizable liquid crystal composition further contains a compound selected from the group consisting of a boronic acid compound and a (meth) acrylamide monomer, which is more effective in the present invention.
  • the boronic acid compound has a structure in which one or more hydroxyl groups of boric acid are substituted with an organic group such as a hydrocarbon group.
  • Examples of the boronic acid compound include a compound represented by the formula (A).
  • R 1 and R 2 are independently hydrogen atoms, an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a substituent. It represents a heteroaryl group which may have a group, and a hydrogen atom is preferable.
  • the aliphatic hydrocarbon group include an alkyl group and an alkenyl group.
  • R 1 and R 2 may be connected to each other to form a ring.
  • X represents a single bond or a divalent linking group.
  • the divalent linking group a divalent aliphatic hydrocarbon group which may have a substituent, an arylene group which may have a substituent, a heteroarylene which may have a substituent, and the like. Examples thereof include -O-, -CO-, -NH-, or a group in which two or more of these are combined.
  • Z represents a group capable of reacting with the polymerizable group of the polymerizable liquid crystal compound, and the polymerizable group is preferable.
  • the definition of a polymerizable group is the same as the definition of a polymerizable group contained in a polymerizable liquid crystal compound.
  • the (meth) acrylamide monomer is a monomer having a (meth) acrylamide group.
  • the number of (meth) acrylamide groups in the (meth) acrylamide monomer is not particularly limited, but may be 1 or more, and may be 2 or more.
  • As the (meth) acrylamide monomer a polyfunctional (meth) acrylamide monomer having two or more (meth) acrylamide groups is preferable.
  • As the (meth) acrylic monomer a compound represented by the formula (B) is preferable. Equation (B) YLY Y represents a (meth) acrylamide group.
  • L represents a divalent linking group.
  • Examples of the divalent linking group represented by L include the groups exemplified by the divalent linking group represented by X described above, which may have a substituent and may have a substituent of —O instead of the methylene group.
  • a divalent aliphatic hydrocarbon group which may contain-, -CO-, or -NH- is preferable.
  • the polymerizable liquid crystal composition may further contain a chiral agent.
  • the polymerizable liquid crystal composition contains a chiral agent, the polymerizable liquid crystal compound can be twisted or oriented along the spiral axis.
  • the type of chiral auxiliary is not particularly limited. Use any of the known chiral agents (for example, "Liquid Crystal Device Handbook” edited by the 142nd Committee of the Japan Society for the Promotion of Science, Chapter 3, 4-3, TN, Chiral Auxiliary for STN, p. 199, 1989). Can be done.
  • the spiral-inducing force (HTP) of the chiral agent is a factor indicating the spiral orientation ability represented by the following formula (X).
  • Formula (X) HTP 1 / (length of spiral pitch (unit: ⁇ m) ⁇ concentration of chiral auxiliary to liquid crystal compound (mass%)) [ ⁇ m -1 ]
  • the chiral agent may be a photosensitive chiral agent whose spiral-inducing force changes with light irradiation (hereinafter, also simply referred to as “chiral agent A”).
  • the chiral agent A may be liquid crystal or non-liquid crystal.
  • the chiral agent A generally contains an asymmetric carbon atom in many cases.
  • the chiral agent A may be an axial asymmetric compound or a planar asymmetric compound that does not contain an asymmetric carbon atom.
  • the chiral agent A may have a polymerizable group.
  • the chiral agent A may be a chiral agent whose spiral-inducing force is increased or decreased by light irradiation. Of these, a chiral agent whose spiral inducing force is reduced by light irradiation is preferable.
  • “increase and decrease of spiral-inducing force” means increase / decrease when the initial spiral direction (before light irradiation) of chiral agent A is "positive". Therefore, when the spiral inducing force continues to decrease due to light irradiation and the spiral direction becomes "negative" beyond 0 (that is, a spiral in the spiral direction opposite to the initial (before light irradiation) spiral direction is induced). (Case) also falls under the category of "chiral agent with reduced spiral inducing force".
  • Examples of the chiral agent A include so-called photoreactive chiral agents.
  • the photoreactive chiral agent is a compound having a chiral portion and a photoreactive portion whose structure is changed by light irradiation, and for example, the twisting force of the liquid crystal compound is significantly changed according to the irradiation amount.
  • a compound having at least a photoisomerization site is preferable, and the photoisomerization site is more preferably having a photoisomerizable double bond.
  • the photoisomerization site having a photoisomerizable double bond is a cinnamoyl site, a chalcone site, an azobenzene site or a azobenzene site in that photoisomerization is likely to occur and the difference in spiral-induced force before and after light irradiation is large.
  • the stilbene moiety is preferred, and the cinnamoyl moiety, chalcone moiety or stilbene moiety is more preferred in that it absorbs less visible light.
  • the photoisomerization site corresponds to the photoreaction site whose structure is changed by the above-mentioned light irradiation.
  • the polymerizable liquid crystal composition may contain two or more kinds of chiral agents A, or a chiral agent whose spiral inducing force does not change by irradiation with at least one kind of chiral agent A and at least one kind of light (hereinafter, simply "chiral”). It may also contain “agent B”).
  • the chiral agent B may be liquid crystal or non-liquid crystal.
  • the chiral agent B generally contains an asymmetric carbon atom in many cases.
  • the chiral agent B may be an axial asymmetric compound or a planar asymmetric compound that does not contain an asymmetric carbon atom.
  • the chiral agent B may have a polymerizable group.
  • As the chiral agent B a known chiral agent can be used.
  • the chiral agent B is preferably a chiral agent that induces a spiral in the opposite direction to the above-mentioned chiral agent A. That is, for example, when the spiral induced by the chiral agent A is in the right direction, the spiral induced by the chiral agent B is in the left direction.
  • the absolute value of the weighted average helical twisting power of the chiral agent is preferably 0.0 ⁇ 1.9 .mu.m -1, more preferably 0.0 ⁇ 1.5 ⁇ m -1, 0.0 ⁇ 1 . It is more preferably 0 ⁇ m -1 , particularly preferably 0.0 to 0.5 ⁇ m -1 , and most preferably zero.
  • the absolute value of the weighted average spiral inducing force of the chiral auxiliary is in the above range, as will be described later, two or more layers having different optical characteristics along the thickness direction depending on the manufacturing conditions of the optically anisotropic layer. It is easy to form an optically anisotropic layer having.
  • the weighted average spiral inducing force of the chiral auxiliary is the spiral inducing force of each chiral auxiliary and the concentration of each chiral agent with respect to the polymerizable liquid crystal compound when two or more kinds of chiral agents are contained in the polymerizable liquid crystal composition. It represents the total value of the product of (mass%) divided by the total concentration (mass%) of the chiral auxiliary with respect to the polymerizable liquid crystal compound. For example, when two kinds of chiral agents (chiral agent X and chiral agent Y) are used in combination, it is represented by the following formula (Y).
  • the spiral-inducing force is a negative value. That is, for example, if helical twisting power of the chiral agent of 10 [mu] m -1, when the spiral direction of the spiral, which is induced by the chiral agent is a right-handed represents a helical twisting power as 10 [mu] m -1. On the other hand, when the spiral direction of the spiral induced by the chiral agent is left-handed, the spiral-inducing force is expressed as -10 ⁇ m -1.
  • the content of the chiral agent A in the polymerizable liquid crystal composition is not particularly limited, but is 5.0% by mass or less with respect to the total mass of the polymerizable liquid crystal compound in that the polymerizable liquid crystal compound is easily oriented uniformly. Is preferable, 3.0% by mass or less is more preferable, 2.0% by mass or less is further preferable, less than 1.0% by mass is particularly preferable, 0.8% by mass or less is more particularly preferable, and 0.5% by mass or less. Is the most preferable.
  • the lower limit is not particularly limited, but is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and further preferably 0.05% by mass or more.
  • the chiral auxiliary A may be used alone or in combination of two or more. When two or more of the above chiral agents A are used in combination, the total content is preferably within the above range.
  • the content of the chiral agent B in the polymerizable liquid crystal composition is not particularly limited, but is 5.0% by mass or less with respect to the total mass of the polymerizable liquid crystal compound in that the polymerizable liquid crystal compound is likely to be uniformly oriented. Is preferable, 3.0% by mass or less is more preferable, 2.0% by mass or less is further preferable, less than 1.0% by mass is particularly preferable, 0.8% by mass or less is more particularly preferable, and 0.5% by mass or less. Is the most preferable.
  • the lower limit is not particularly limited, but is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and further preferably 0.05% by mass or more.
  • the chiral agent B may be used alone or in combination of two or more. When two or more of the above chiral agents B are used in combination, the total content is preferably within the above range.
  • the total content of the chiral auxiliary (total content of all chiral agents) in the polymerizable liquid crystal composition is preferably 5.0% by mass or less, preferably 4.0% by mass, based on the total mass of the polymerizable liquid crystal compound.
  • the following is more preferable, 2.0% by mass or less is further preferable, and 1.0% by mass or less is particularly preferable.
  • the lower limit is not particularly limited, but is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and further preferably 0.05% by mass or more.
  • step 2 first, the polymerizable liquid crystal composition is applied onto the substrate to form a composition layer.
  • the polymerizable liquid crystal composition is applied directly onto the substrate.
  • the polymerizable liquid crystal composition is applied so that the surface of the substrate is in contact with the polymerizable liquid crystal composition.
  • the coating method is not particularly limited, and examples thereof include a wire bar coating method, an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, and a die coating method. If necessary, after the composition is applied, a treatment for drying the composition layer applied on the substrate may be carried out. By carrying out a drying treatment, the solvent can be removed from the composition layer.
  • the film thickness of the composition layer is not particularly limited, but is preferably 0.1 to 20 ⁇ m, more preferably 0.2 to 15 ⁇ m, and even more preferably 0.5 to 10 ⁇ m.
  • the polymerizable liquid crystal compound in the composition layer is oriented.
  • the treatment for orienting the polymerizable liquid crystal compound is not particularly limited, but heat treatment is preferable.
  • the heat treatment conditions the optimum conditions are selected according to the polymerizable liquid crystal compound used.
  • the heating temperature is often 10 to 250 ° C, more often 40 to 150 ° C, and even more often 50 to 130 ° C.
  • the heating time is often 0.1 to 60 minutes, and more often 0.2 to 5 minutes.
  • the orientation of the polymerizable liquid crystal compound depends on the material in the composition layer. Examples of the orientation state include homogenius orientation. When the composition layer contains a chiral agent, the polymerizable liquid crystal compound is twist-oriented along a spiral axis extending along the thickness direction of the composition layer.
  • the orientation state of the polymerizable liquid crystal compound is fixed to form an optically anisotropic layer.
  • the method for immobilizing the orientation state is not particularly limited, and the composition layer is subjected to a curing treatment to react the polymerizable groups in the polymerizable liquid crystal compound to form an optically anisotropic layer (cured layer). There is a way to do it.
  • the method of curing treatment is not particularly limited, and examples thereof include photo-curing treatment and thermosetting treatment. Among them, the light irradiation treatment is preferable, and the ultraviolet irradiation treatment is more preferable.
  • a light source such as an ultraviolet lamp is used for ultraviolet irradiation.
  • the irradiation amount of light (for example, ultraviolet rays) is not particularly limited, but is generally preferably about 100 to 800 mJ / cm 2.
  • the orientation state of the polymerizable liquid crystal compound is fixed.
  • examples of the optically anisotropic layer include a layer formed by immobilizing a homogeneously oriented polymerizable liquid crystal compound.
  • a layer formed by immobilizing a polymerizable liquid crystal compound twist-oriented having a spiral axis in the thickness direction can be mentioned.
  • the "fixed” state means a state in which the orientation of the liquid crystal compound is maintained. It is not limited to that, and specifically, in the temperature range of 0 to 50 ° C., and more severely, -30 to 70 ° C., the layer has no fluidity, and is oriented by an external field or an external force. It is preferable that the fixed orientation form can be kept stable without causing a change. In the optically anisotropic layer, it is no longer necessary for the composition in the layer to finally exhibit liquid crystallinity.
  • the optically anisotropic layer may have a single-layer structure or a multi-layer structure.
  • the multi-layer structure means a structure in which two or more layers having different optical characteristics are laminated.
  • steps A to E are carried out to produce an optically anisotropic layer having two layers having different optical characteristics in one coating step. be able to.
  • Step A A chiral agent containing at least a chiral agent A and a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound are applied onto a substrate to form a composition layer.
  • Step B Heat treatment is performed on the composition layer.
  • Step C After step B, the composition layer is irradiated with light under the condition of an oxygen concentration of 1% by volume or more.
  • Step D After step C, the composition layer is heat-treated.
  • Step E After step D, the composition layer is cured to fix the orientation of the polymerizable liquid crystal compound, and the optically anisotropic layer. The procedure of each of the above steps will be described in detail below.
  • Step A Since the procedure of step A is the same as that of step 1, it is omitted.
  • the polymerizable liquid crystal composition used in step A contains at least the chiral agent A. As will be described later, the polymerizable liquid crystal composition may contain a chiral agent B.
  • Step B The procedure of step B is not particularly limited, and examples thereof include a method of orienting the polymerizable liquid crystal compound of step 2 described above.
  • Step C Step C will be described below with reference to the drawings.
  • the polymerizable liquid crystal composition contains two types of chiral agents, chiral agent A and chiral agent B, and the absolute value of the weighted average spiral inducing force of the chiral agent in the composition layer formed by step A.
  • a case where is 0 will be typically described.
  • step B a composition layer 12 in which the polymerizable liquid crystal compound LC is homogenically oriented is formed on the substrate 10.
  • FIG. 1 is a schematic cross-sectional view of the substrate 10 and the composition layer 12. In the composition layer 12 shown in FIG.
  • the chiral agent A and the chiral agent B are present at the same concentration, the spiral direction induced by the chiral agent A is left-handed, and the chiral agent B induces the chiral agent B.
  • the spiral direction is right-handed.
  • the absolute value of the spiral inducing force of the chiral agent A and the absolute value of the spiral inducing force of the chiral agent B are assumed to be the same.
  • step C under the condition that the oxygen concentration is 1% by volume or more, light is emitted from the direction opposite to the composition layer 12 side of the substrate 10 (the direction of the white arrow in FIG. 2). Irradiate.
  • the light irradiation is carried out from the substrate 10 side in FIG. 2, it may be carried out from the composition layer 12 side.
  • the surface of the upper region 12B is on the air side, so that the upper region 12B
  • the oxygen concentration in the lower region 12A is high, and the oxygen concentration in the lower region 12A is low. Therefore, when the composition layer 12 is irradiated with light, the polymerization of the polymerizable liquid crystal compound easily proceeds in the lower region 12A, and the orientation state of the polymerizable liquid crystal compound is fixed.
  • the chiral agent A is also present in the lower region 12A, and the chiral agent A is also exposed to light, and the spiral inducing force changes.
  • the orientation state of the polymerizable liquid crystal compound is fixed in the lower region 12A, the orientation of the liquid crystal compound is even if the step D of heat-treating the light-irradiated composition layer, which will be described later, is performed. There is no change in state.
  • the oxygen concentration is high in the upper region 12B, even if light irradiation is performed, the polymerization of the polymerizable liquid crystal compound is inhibited by oxygen, and the polymerization is difficult to proceed.
  • step D heat treatment
  • step C the orientation state of the polymerizable liquid crystal compound is likely to be fixed in the substrate-side region (lower region) of the composition layer. Further, in the region of the composition layer opposite to the substrate side (upper region), the solidification of the oriented state of the polymerizable liquid crystal compound is difficult to proceed, and the spiral inducing force changes depending on the exposed chiral agent A. It will be in the state of.
  • Step C is carried out under the condition that the oxygen concentration is 1% by volume or more.
  • the oxygen concentration is preferably 2% by volume or more, more preferably 5% by volume or more, in that layers having different orientation states of the polymerizable liquid crystal compound are easily formed in the optically anisotropic layer.
  • the upper limit is not particularly limited, but 100% by volume can be mentioned.
  • the irradiation intensity of light irradiation in step C is not particularly limited and can be appropriately determined based on the spiral inducing force of the chiral agent A.
  • the irradiation amount of light irradiation in the step C is not particularly limited, but is preferably 300 mJ / cm 2 or less, and more preferably 200 mJ / cm 2 or less, in that a predetermined optically anisotropic layer is easily formed.
  • the lower limit, in terms of easy predetermined optical anisotropic layer is formed is preferably 10 mJ / cm 2 or more, 30 mJ / cm 2 or more is more preferable.
  • the light irradiation in step C is preferably carried out at 15 to 70 ° C. (preferably 15 to 50 ° C.).
  • the light used for light irradiation may be the light that the chiral agent A is exposed to. That is, the light used for light irradiation is not particularly limited as long as it is an active ray or radiation that changes the spiral inducing force of the chiral agent A.
  • the emission line spectrum of a mercury lamp far ultraviolet rays typified by an excimer laser, and poles. Examples include ultraviolet rays, X-rays, ultraviolet rays, and electron beams. Of these, ultraviolet rays are preferable.
  • Step D is a step of heat-treating the composition layer after step C.
  • the orientation state of the liquid crystal compound changes in the region where the spiral inducing force of the chiral auxiliary A in the composition layer subjected to light irradiation has changed.
  • the orientation state of the polymerizable liquid crystal compound is fixed in the lower region 12A as shown in FIG.
  • the polymerization of the polymerizable liquid crystal compound is difficult to proceed, and the orientation state of the polymerizable liquid crystal compound is not fixed.
  • the spiral inducing force of the chiral agent A changes.
  • the force for twisting the polymerizable liquid crystal compound changes in the upper region 12B as compared with the state before light irradiation. This point will be described in more detail.
  • the chiral agent A and the chiral agent B are present in the composition layer 12 shown in FIG. 1 at the same concentration, the spiral direction induced by the chiral agent A is left-handed, and the chiral agent B causes the composition layer 12.
  • the induced spiral direction is right-handed.
  • the absolute value of the spiral-inducing force of the chiral agent A and the absolute value of the spiral-inducing force of the chiral agent B are the same. Therefore, the weighted average spiral inducing force of the chiral agent in the composition layer before light irradiation is 0.
  • the vertical axis represents “the spiral inducing force of the chiral agent ( ⁇ m -1 ) ⁇ the concentration of the chiral agent (mass%)”, and the farther the value is from zero, the greater the spiral inducing force.
  • the horizontal axis represents "light irradiation amount (mJ / cm 2 )”.
  • the relationship between the chiral agent A and the chiral agent B in the composition layer before light irradiation corresponds to the time when the light irradiation amount is 0, and "the spiral inducing force of the chiral auxiliary A ( ⁇ m -1 ) ⁇ "
  • the absolute value of "concentration of chiral auxiliary A (mass%)” and “spiral-inducing force of chiral agent B ( ⁇ m -1 ) x concentration of chiral agent B (% by mass)” correspond to the same state. That is, the spiral-inducing forces of both the chiral agent A that induces left-handed winding and the chiral agent B that induces right-handed winding cancel each other out.
  • the composition layer 12 after the step C in which such a change in the weighted average spiral inducing force is generated is heat-treated to promote the reorientation of the liquid crystal compound, as shown in FIG. 5, the upper side is shown.
  • the polymerizable liquid crystal compound LC is twist-oriented along a spiral axis extending along the thickness direction of the composition layer 12.
  • the polymerization of the polymerizable liquid crystal compound proceeds during step C and the orientation state of the polymerizable liquid crystal compound is fixed, so that the polymerizable liquid crystal compound is polymerizable. The reorientation of the liquid crystal compound does not proceed.
  • step D by carrying out the step D, a plurality of regions having different orientation states of the polymerizable liquid crystal compound are formed along the thickness direction of the composition layer.
  • the degree of twisting of the polymerizable liquid crystal compound LC can be appropriately adjusted depending on the type of chiral agent A used, the exposure amount in step C, and the like.
  • the present invention is not limited to this embodiment.
  • a chiral agent whose spiral inducing force is increased by light irradiation may be used as the chiral agent A.
  • the spiral inducing force induced by the chiral agent A increases due to light irradiation, and the liquid crystal compound is twisted or oriented in the turning direction induced by the chiral auxiliary A.
  • the mode in which the chiral agent A and the chiral agent B are used in combination has been described, but the mode is not limited to this mode.
  • it may be an embodiment using two kinds of chiral agents A.
  • the chiral agent A1 that induces left-handed winding and the chiral agent A2 that induces right-handed winding may be used in combination.
  • the chiral agents A1 and A2 may be chiral agents whose spiral inducing force increases or chiral agents whose spiral inducing force decreases, respectively.
  • a chiral agent that induces left-handed winding and whose spiral-inducing force increases by light irradiation and a chiral agent that induces right-handed winding and whose spiral-inducing force decreases by light irradiation are used in combination. You may.
  • the optimum conditions are selected according to the liquid crystal compound used.
  • the heating temperature is preferably a temperature for heating from the state of step C, often 35 to 250 ° C, more often 50 to 150 ° C, and more than 50 ° C and 150 ° C or less. Even more, especially at 60-130 ° C.
  • the heating time is often 0.01 to 60 minutes, and more often 0.03 to 5 minutes.
  • the absolute value of the weighted average spiral inducing force of the chiral agent in the composition layer after light irradiation is not particularly limited, but the weighted average spiral inducing force of the chiral agent in the composition layer after light irradiation and before light irradiation.
  • the absolute value of the difference between the weighted average helical twisting power preferably 0.05 .mu.m -1 or more, more preferably 0.05 ⁇ 10.0 [mu] m -1, more preferably 0.1 ⁇ 10.0 [mu] m -1.
  • the procedure of step E is not particularly limited, and examples thereof include the curing treatment performed in step 2 described above.
  • the optically anisotropic layer formed is a layer formed by fixing the orientation state of the homogeneously oriented polymerizable liquid crystal compound from the substrate side. It includes two layers, one is a layer formed by fixing the orientation state of the polymerizable liquid crystal compound twisted and oriented along a spiral axis extending along the thickness direction. That is, the formed optically anisotropic layer has a multi-layer structure.
  • optical film having a substrate and an optically anisotropic layer arranged on the substrate is produced.
  • the substrate and the optically anisotropic layer are in direct contact with each other.
  • the obtained optical film can be applied to various uses, and examples thereof include an optical compensation film for optically compensating a liquid crystal cell and an antireflection film used in a display device such as an organic electroluminescence display device.
  • the above-mentioned optical film may be used as a circular polarizing plate in combination with a polarizer.
  • the polarizer may be a member having a function of converting natural light into specific linearly polarized light, and examples thereof include an absorption type polarizer.
  • the type of the polarizer is not particularly limited, and a commonly used polarizer can be used, and examples thereof include an iodine-based polarizer, a dye-based polarizer using a dichroic dye, and a polyene-based polarizer.
  • Iodine-based polarizers and dye-based polarizers are generally produced by adsorbing iodine or a dichroic dye on polyvinyl alcohol and stretching it.
  • a protective film may be arranged on one side or both sides of the polarizer.
  • the method for producing the circular polarizing plate is not particularly limited, and a known method can be adopted. For example, a method of adhering an optical film and a polarizer via an adhesive layer can be mentioned.
  • the circularly polarizing plate can be suitably applied as an antireflection film for an organic EL display device.
  • Example 1> Preparation of Cellulose Achillate Film (Substrate)
  • the following components are put into a mixing tank, stirred, heated at 90 ° C. for 10 minutes, filtered through a filter paper having an average pore size of 34 ⁇ m and a sintered metal filter having an average pore size of 10 ⁇ m, and subjected to cellulose acylate dope (hereinafter, simply “” Also called “dope”) was manufactured.
  • Cellulose acylate dope ⁇ Cellulose acylate (acetyl substitution degree 2.86, viscosity average degree of polymerization 310) 100 parts by mass sugar ester compound 1 (shown in chemical formula (S4)) 6.0 parts by mass sugar ester compound 2 (shown in chemical formula (S5)) 2.0 parts by mass silica particle dispersion (AEROSIL R972, Nippon Aerosil Co., Ltd.) Made) 0.1 parts by mass Solvent (methylene chloride / methanol / butanol) Predetermined amount ⁇
  • the above-mentioned doping was cast using a drum film forming machine.
  • the above-mentioned doping for forming the core layer so as to be in contact with the metal substrate cooled to 0 ° C. and the above-mentioned doping for forming the surface layer on the core layer were co-cast from the die, and then obtained.
  • the film was peeled off.
  • the drum was made of SUS (Steel Use Stainless).
  • the film stripped from the drum was dried at 30-40 ° C. for 20 minutes during transfer. Next, the obtained film was carried by roll and post-dried by zone heating. Then, the obtained film was knurled and then wound up. The film thickness of the obtained cellulose acylate film was 40 ⁇ m.
  • the cellulose acylate film produced above was continuously subjected to a rubbing treatment.
  • the longitudinal direction of the long film and the conveying direction were parallel, and the angle formed by the film longitudinal direction (conveying direction) and the rotation axis of the rubbing roller was 74.5 °.
  • the film longitudinal direction (conveyance direction) is 90 ° and the counterclockwise direction is represented by a positive value with respect to the film width hand direction (0 °) when observed from the film side, the rotation axis of the rubbing roller is 15. It was .5 °.
  • the position of the rotation axis of the rubbing roller was a position rotated by 74.5 ° clockwise with respect to the longitudinal direction of the film.
  • the following polymerizable liquid crystal composition (1) was applied onto the rubbing-treated cellulose acylate film using a Gieser coating machine, and the film on which the coating film was formed was heated at 80 ° C. for 60 seconds. Then, the coating film was irradiated with ultraviolet rays (70 mJ / cm 2 ) under air (oxygen concentration: about 20% by volume) at 30 ° C. using a 365 nm LED lamp (manufactured by Acroedge Co., Ltd.). Next, after heating the obtained coating film at 80 ° C.
  • the oxygen concentration was set to 100 ppm under nitrogen purging, and ultraviolet rays were applied to the coating film at 80 ° C. using a metal halide lamp (manufactured by Eye Graphics Co., Ltd.). After irradiation (500 mJ / cm 2 ), an optically anisotropic layer in which the orientation of the liquid crystal compound was fixed was formed, and an optical film (F-1) was prepared.
  • Rod-shaped liquid crystal compound (A) (hereinafter, a mixture of liquid crystal compounds. The following numerical value (%) represents the mass ratio of each liquid crystal compound.)
  • Polymer (A) (In the formula, the numerical value described in each repeating unit represents the content (mass%) of each repeating unit with respect to all repeating units.)
  • Polymer (B) (In the formula, the numerical value described in each repeating unit represents the content (mass%) of each repeating unit with respect to all repeating units.)
  • Example 2 An optical film (F-2) was prepared according to the same procedure as in Example 1 except that methyl isobutyl ketone was used instead of n-butyl acetate.
  • Example 3 An optical film (F-3) was prepared according to the same procedure as in Example 1 except that tert-butyl acetate was used instead of n-butyl acetate.
  • Example 4 The optical film (F-4) was subjected to the same procedure as in Example 1 except that a solvent in which n-butyl acetate (309 parts by mass) and methyl ethyl ketone (16 parts by mass) were mixed was used instead of n-butyl acetate.
  • a solvent in which n-butyl acetate (309 parts by mass) and methyl ethyl ketone (16 parts by mass) were mixed was used instead of n-butyl acetate.
  • Example 5 An optical film (F-5) was prepared according to the same procedure as in Example 4 except that 3 parts by mass of the polymerizable monomer (A) was added to the polymerizable liquid crystal composition (1).
  • Example 6 An optical film (F-6) was prepared according to the same procedure as in Example 4 except that 3 parts by mass of the polymerizable monomer (B) was added to the polymerizable liquid crystal composition (1).
  • Example 7 An optical film (F-7) was produced according to the same procedure as in Example 1 except that the polymerizable liquid crystal composition (2) was used instead of the polymerizable liquid crystal composition (1).
  • ⁇ Polymerizable liquid crystal composition (2) ⁇ ⁇ The following disc-shaped liquid crystal compound (A) 80 parts by mass ⁇ The following disc-shaped liquid crystal compound (B) 20 parts by mass ⁇ Ethylene oxide-modified trimethylolpropantriacrylate (V # 360, manufactured by Osaka Organic Chemical Co., Ltd.) 5 mass Part-Photopolymerization initiator (Irgacure 907, manufactured by Ciba Japan) 4 parts by mass-Pyridinium salt (A) 1.2 parts by mass-Polymer (A) 0.2 parts by mass-Polymer (B) 0.1% by mass Part ⁇ Polymer (C) 0.1 part by mass ⁇ n-butyl acetate 211 parts by mass ⁇ -
  • a and b represent the content (mass%) of each repeating unit with respect to all the repeating units, a represents 90% by mass, and b represents 10% by mass.
  • Example 8 An optical film (F-8) was produced according to the same procedure as in Example 1 except that the polymerizable liquid crystal composition (3) was used instead of the polymerizable liquid crystal composition (1).
  • n-butyl acetate as a solvent
  • methyl isobutyl is used as a solvent.
  • the above measurement was performed using ketone.
  • Cross-cut test A cross-cut test (a grid tape peeling test) based on JIS D0202-1988 was carried out on the optically anisotropic layer of the obtained optical film. Of the 100 squares formed by cutting in a grid pattern on the optically anisotropic layer, the number of squares peeled off by attaching and peeling cellophane tape (“CT24”, manufactured by Nichiban Co., Ltd.) is counted as follows. It was evaluated according to the criteria of.
  • S The number of squares to be peeled is 0 "A”: The number of squares to be peeled is 1 to 30 "B”: The number of squares to be peeled is 31 to 50 "C”: The number of squares to be peeled is 51 or more
  • the "ratio [%]” column in the “solvent 1" and “solvent 2” columns represents the mass ratio (%) of each solvent to the total mass of the solvent 1 and the solvent 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Mechanical Engineering (AREA)
  • Theoretical Computer Science (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)

Abstract

La présente invention concerne un procédé de production d'un film optique qui comprend un substrat et une couche optiquement anisotrope, tout en présentant une excellente adhérence entre le substrat et la couche optiquement anisotrope, et qui est supprimé dans des défauts d'alignement de la couche optiquement anisotrope. Un procédé de production d'un film optique selon la présente invention comprend : une étape 1 pour conférer une surface de substrat à une force de commande d'alignement ; et une étape 2 dans laquelle une composition de cristaux liquides polymérisable, qui contient un composé de cristaux liquides polymérisable et un solvant, est appliqué sur un substrat et le composé de cristaux liquides polymérisable est aligné, puis l'état d'alignement du composé de cristaux liquides polymérisable est immobilisé, formant ainsi une couche optiquement anisotrope. Par rapport à ce procédé de production d'un film optique, le rapport de changement de masse tel que déterminé par la formule (1) est de 0,1 % en masse à 1,5 % en masse　Formule (1) : (Rapport de changement de masse) = ((WB – WA)/WA) × 100. Dans la formule, WA représente la masse sèche du substrat et WB représente la masse humide du substrat après avoir été immergé dans le solvant.
PCT/JP2020/030868 2019-08-16 2020-08-14 Procédé de production d'un film optique WO2021033639A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2021540762A JPWO2021033639A1 (fr) 2019-08-16 2020-08-14
KR1020227004249A KR20220032587A (ko) 2019-08-16 2020-08-14 광학 필름의 제조 방법

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2019149419 2019-08-16
JP2019-149419 2019-08-16
JP2019175987 2019-09-26
JP2019-175987 2019-09-26
JP2019-177831 2019-09-27
JP2019177831 2019-09-27

Publications (1)

Publication Number Publication Date
WO2021033639A1 true WO2021033639A1 (fr) 2021-02-25

Family

ID=74661087

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/030868 WO2021033639A1 (fr) 2019-08-16 2020-08-14 Procédé de production d'un film optique

Country Status (3)

Country Link
JP (1) JPWO2021033639A1 (fr)
KR (1) KR20220032587A (fr)
WO (1) WO2021033639A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014156981A1 (fr) * 2013-03-29 2014-10-02 富士フイルム株式会社 Procédé de fabrication de film à décalage de phase
JP2014191313A (ja) * 2013-03-28 2014-10-06 Fujifilm Corp 位相差フィルムの製造方法
WO2014189041A1 (fr) * 2013-05-21 2014-11-27 富士フイルム株式会社 Plaque polarisante et procédé pour sa production, et matériau de film optique
WO2015016297A1 (fr) * 2013-08-01 2015-02-05 富士フイルム株式会社 Procédé de production d'une plaque de polarisation
WO2015046399A1 (fr) * 2013-09-27 2015-04-02 富士フイルム株式会社 Procédé de fabrication de plaque polarisante
WO2016136231A1 (fr) * 2015-02-25 2016-09-01 富士フイルム株式会社 Stratifié et film optique
WO2016171169A1 (fr) * 2015-04-21 2016-10-27 日本ゼオン株式会社 Film multicouche et son procédé de fabrication, procédé de fabrication de corps de transfert optiquement anisotrope, couche optiquement anisotrope, élément optiquement anisotrope, et corps stratifié optique
JP2016197219A (ja) * 2015-04-06 2016-11-24 富士フイルム株式会社 積層体及び光学フィルム
US9625752B1 (en) * 2013-07-15 2017-04-18 William Marsh Rice University Responsive liquid crystal elastomers for enhanced cell sheet alignment

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6482891B2 (ja) 2015-02-16 2019-03-13 日東電工株式会社 光学フィルムの製造方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014191313A (ja) * 2013-03-28 2014-10-06 Fujifilm Corp 位相差フィルムの製造方法
WO2014156981A1 (fr) * 2013-03-29 2014-10-02 富士フイルム株式会社 Procédé de fabrication de film à décalage de phase
WO2014189041A1 (fr) * 2013-05-21 2014-11-27 富士フイルム株式会社 Plaque polarisante et procédé pour sa production, et matériau de film optique
US9625752B1 (en) * 2013-07-15 2017-04-18 William Marsh Rice University Responsive liquid crystal elastomers for enhanced cell sheet alignment
WO2015016297A1 (fr) * 2013-08-01 2015-02-05 富士フイルム株式会社 Procédé de production d'une plaque de polarisation
WO2015046399A1 (fr) * 2013-09-27 2015-04-02 富士フイルム株式会社 Procédé de fabrication de plaque polarisante
WO2016136231A1 (fr) * 2015-02-25 2016-09-01 富士フイルム株式会社 Stratifié et film optique
JP2016197219A (ja) * 2015-04-06 2016-11-24 富士フイルム株式会社 積層体及び光学フィルム
WO2016171169A1 (fr) * 2015-04-21 2016-10-27 日本ゼオン株式会社 Film multicouche et son procédé de fabrication, procédé de fabrication de corps de transfert optiquement anisotrope, couche optiquement anisotrope, élément optiquement anisotrope, et corps stratifié optique

Also Published As

Publication number Publication date
KR20220032587A (ko) 2022-03-15
JPWO2021033639A1 (fr) 2021-02-25

Similar Documents

Publication Publication Date Title
KR20220098710A (ko) 광흡수 이방성막, 3차원 광흡수 이방성막 및 그 제조 방법
JP6667983B2 (ja) 積層体およびその製造方法、偏光板、液晶表示装置、有機ｅｌ表示装置
JP2004029824A (ja) ポリマー化液晶材料を含む膜の製造方法
JP5720795B2 (ja) パターン位相差フィルム及びその製造方法
CN102211439B (zh) 制备层压膜的方法,层压膜和热屏蔽部件
JP2004046194A (ja) 光学補償子の製造方法
WO2021182248A1 (fr) Composition, procédé de production de film optique et film optique
WO2021033634A1 (fr) Film optique
JP2016012031A (ja) 複層フィルムの製造方法、位相差フィルム、円偏光板、及び、有機エレクトロルミネッセンス表示装置
JP6146935B2 (ja) 位相差フィルムの製造方法
JP2006243025A (ja) 液晶用配向膜および該配向膜より得られる液晶性光学フィルム
JP2004046195A (ja) 光学補償子の製造方法
JP2004206100A (ja) 配向膜用組成物、配向膜の製造方法、及び光学素子の製造方法
JP2006292910A (ja) 楕円偏光板の製造方法および楕円偏光板を用いた画像表示装置
JP7217359B2 (ja) 光学フィルム、円偏光板、有機エレクトロルミネッセンス表示装置
WO2021033639A1 (fr) Procédé de production d'un film optique
WO2021033640A1 (fr) Composition de cristaux liquides, film optique, plaque de polarisation circulaire pour affichage électroluminescent organique, et procédé de production de couche optiquement anisotrope
JP5714435B2 (ja) 光学素子の製造方法
JP2006259038A (ja) 楕円偏光板の製造方法および楕円偏光板を用いた画像表示装置
JP6335294B2 (ja) 光学機能性層作製用組成物、光学機能性層を含む光学フィルムの製造方法、および光学フィルム
WO2021033631A1 (fr) Procédé de production de couche anisotrope optique, procédé de production de stratifié, procédé de production de couche anisotrope optique équipée d'un polariseur, procédé de production de stratifié équipé d'un polariseur, composition et couche anisotrope optique
WO2022176884A1 (fr) Procédé de production de film optique
JP6045421B2 (ja) 位相差フィルムの製造方法
JP2006243653A (ja) 楕円偏光板の製造方法および楕円偏光板を用いた画像表示装置
KR101074185B1 (ko) 광경화성 콜레스테릭 액정과 광경화성 네마틱 액정을포함하는 반사형 편광필름 및 그 제조방법

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20855420

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20227004249

Country of ref document: KR

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2021540762

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20855420

Country of ref document: EP

Kind code of ref document: A1