CN113167955B - Method for manufacturing optical laminated film roller and optical laminated film roller - Google Patents
Method for manufacturing optical laminated film roller and optical laminated film roller Download PDFInfo
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- CN113167955B CN113167955B CN201980078635.4A CN201980078635A CN113167955B CN 113167955 B CN113167955 B CN 113167955B CN 201980078635 A CN201980078635 A CN 201980078635A CN 113167955 B CN113167955 B CN 113167955B
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Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3016—Polarising elements involving passive liquid crystal elements
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/36—Successively applying liquids or other fluent materials, e.g. without intermediate treatment
- B05D1/38—Successively applying liquids or other fluent materials, e.g. without intermediate treatment with intermediate treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/02—Physical, chemical or physicochemical properties
- B32B7/023—Optical properties
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/13363—Birefringent elements, e.g. for optical compensation
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
Abstract
The present invention addresses the problem of providing a method for manufacturing an optical laminated film roll, which is excellent in the handling operation of manufacturing an optical laminated film. The method for manufacturing the optical laminated film roller comprises the following steps: a first coating step of coating a long support to be carried with a binder composition containing a binder and a photo-alignment polymer to form a first coating film (1); a pressure-sensitive adhesive layer forming step of forming a pressure-sensitive adhesive layer after the 1 st coating step; a second coating step of directly coating the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound on the pressure-sensitive adhesive layer to form a second coating film having a width larger than the width of the pressure-sensitive adhesive layer; an optically anisotropic layer forming step of forming an optically anisotropic layer having a width wider than that of the adhesive layer after the 2 nd coating step to produce an optical laminated film; and a winding step of winding the optical laminated film into a roll shape to produce an optical laminated film roll after the optical anisotropic layer forming step.
Description
Technical Field
The present invention relates to a method for manufacturing an optical laminated film roll and an optical laminated film roll.
Background
A retardation plate made of an optically anisotropic material is used for display devices such as liquid crystal display devices, organic electroluminescence (hereinafter, abbreviated as "EL") display devices, touch panels, and brightness enhancement films.
Since these display devices have a structure in which layers having different refractive indices are stacked, it is known that external light is reflected at the interface of each layer, and problems such as a decrease in contrast and reflection occur.
Therefore, in these display devices (particularly, liquid crystal display devices, organic EL display devices, and the like), in order to suppress adverse effects caused by external light reflection, circularly polarizing plates each composed of a phase difference plate and a polarizing film have been conventionally used.
For example, patent document 1 describes "a liquid crystal composition containing a liquid crystal compound and a polymer which does not have liquid crystallinity and generates a polar group by at least one action of light or an acid. "([ claim 1 ]), and a phase difference plate, a (circularly) polarizing plate and an image display device having at least 1 optically anisotropic layer formed from the liquid crystal composition are described ([ claim 7] to [ claim 12 ]).
Further, patent document 1 describes a polar group-forming polymer (polarity-converting polymer) contained in a liquid crystal composition, wherein the "polarity-converting polymer contained in the liquid crystal composition has: a leveling function of smoothing the surface when the liquid crystal composition is coated on a support to form a retardation plate; and a function of forming a surface concentrated layer containing a large amount of a polar conversion polymer by transferring to the air interface side of the underlying optically anisotropic layer in place of an alignment film separately formed between the optically anisotropic layers when producing a retardation plate having a plurality of optically anisotropic layers. The liquid crystal film also has an alignment film function of forming a polar group in the polar conversion polymer by the action of light such as ultraviolet rays or the action of an acid, and imparting an alignment function to the surface concentrated layer by rubbing or the like to align the liquid crystal compound to be the upper optically anisotropic layer. Further, by generating the polar group, the surface sticky feeling can be suppressed or the dishing at the time of coating the upper optically anisotropic layer can be reduced. In addition, it is possible to impart solubility resistance to the liquid crystalline compound or the coating solvent used, or to improve the interaction with the liquid crystalline compound, and to significantly improve the function of the alignment film. "([0055]).
Prior art documents
Patent document
Patent document 1: japanese patent laid-open publication No. 2004-277525
Disclosure of Invention
Technical problem to be solved by the invention
The present inventors have confirmed that, when the liquid crystal composition described in patent document 1 is confirmed, as described above, a surface concentrated layer containing a large amount of a polarity-switching polymer can be used as an alignment film, but it is necessary to subject the surface concentrated layer to a rubbing treatment in order to impart an alignment function.
Therefore, the present inventors have studied to impart an alignment function (restraining force) to a surface concentrated layer by applying a photo-alignment treatment to the surface concentrated layer using a novel polymer in which a photo-alignment group is further introduced into a polarity-switching polymer.
As a result of the study, the present inventors confirmed that the following problems exist: in the case of producing an optical laminated film by forming an upper layer (optically anisotropic layer) on the surface of a base layer (pressure-sensitive adhesive layer) formed using a composition containing a novel polymer, if a portion exposing the surface of the base layer remains, when the obtained optical laminated film is wound into a roll shape, the exposed portion is adhered to the back surface of a support or the like existing 1 week before, and the optical laminated film cannot be transported during use.
Accordingly, an object of the present invention is to provide a method for manufacturing an optical laminated film roll, which can manufacture an optical laminated film roll excellent in the operation of conveying an optical laminated film, and an optical laminated film roll.
Means for solving the technical problem
The present inventors have conducted intensive studies to achieve the above object, and as a result, have found that: by making the width of the optically anisotropic layer formed adjacent to the upper layer of the adhesive layer wider than the width of the adhesive layer, an optical laminated film roll excellent in the handling operation of the optical laminated film can be produced.
That is, the following configuration has been found to solve the above problems.
[1] A method for manufacturing a roll of an optical laminate film having an adhesive layer formed using an adhesive composition containing an adhesive and a photo-alignment polymer, and an optically anisotropic layer provided on the adhesive layer,
the optically anisotropic layer is formed by using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound,
the adhesive layer and the optically anisotropic layer are laminated adjacent to each other,
the method for manufacturing the optical laminated film roller comprises the following steps:
a first coating step of coating a long support to be carried with a binder composition containing a binder and a photo-alignment polymer to form a first coating film;
a pressure-sensitive adhesive layer forming step of forming a pressure-sensitive adhesive layer after the 1 st coating step;
an action step of causing at least 1 selected from the group consisting of light, heat, acid, and alkali to act;
a light irradiation step of irradiating polarized light or unpolarized light;
a second coating step of directly coating the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound on the pressure-sensitive adhesive layer to form a second coating film having a width larger than the width of the pressure-sensitive adhesive layer;
an optically anisotropic layer forming step of forming an optically anisotropic layer having a width larger than the width of the adhesive layer after the 2 nd coating step to produce an optical laminated film; and
a winding step of winding the optical layered film into a roll shape to produce an optical layered film roll after the optical anisotropic layer forming step,
the action step is a step performed between the adhesive layer forming step and the 2 nd coating step or performed simultaneously with the adhesive layer forming step or the 2 nd coating step,
the light irradiation step is a step performed between the pressure-sensitive adhesive layer formation step and the 2 nd application step or simultaneously with the pressure-sensitive adhesive layer formation step or the 2 nd application step,
the photo-alignment polymer is a photo-alignment polymer having a repeating unit A containing a cleavage group that is decomposed by at least 1 action selected from the group consisting of light, heat, acid, and base to generate a polar group,
the repeating unit A has a cleavage group on the side chain and has a fluorine atom or a silicon atom on the side closer to the terminal than the cleavage group of the side chain,
the following condition 1 or condition 2 is satisfied.
Condition 1: the photo-alignment layer contains a repeating unit B containing a photo-alignment group in addition to the repeating unit A.
Condition 2: the repeating unit a includes a photo-alignment group on the main chain side of the cleavage group of the side chain.
[2] The method for producing an optical laminated film roll according to [1], wherein,
the action step is a step of acting light and is performed simultaneously with the adhesive layer formation step,
the light irradiation step is a step performed between the pressure-sensitive adhesive layer formation step and the 2 nd application step.
[3] An optical laminated film roll which is a roll of an optical laminated film having an adhesive layer formed using an adhesive composition containing an adhesive and a photo-alignment polymer, and an optically anisotropic layer provided on the adhesive layer,
the optically anisotropic layer is formed by using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound,
the adhesive layer and the optically anisotropic layer are laminated adjacent to each other,
the optically anisotropic layer is laminated so as to cover the surface and end faces of the pressure-sensitive adhesive layer.
Effects of the invention
According to the present invention, it is possible to provide a method for manufacturing an optical laminated film roll, which is capable of manufacturing an optical laminated film roll having excellent operation for transporting an optical laminated film, and an optical laminated film roll.
Detailed Description
The present invention will be described in detail below.
The following description of the constituent elements is made based on the exemplary embodiments of the present invention, but the present invention is not limited to such embodiments.
In the present specification, the numerical range represented by "to" means a range including numerical values described before and after "to" as a lower limit value and an upper limit value.
[ method for producing optical layered film roll ]
The method for producing an optical laminate film roll according to the present invention (hereinafter, also simply referred to as "the method for producing the present invention") is a method for producing a roll of an optical laminate film having a pressure-sensitive adhesive layer formed using a pressure-sensitive adhesive composition containing a pressure-sensitive adhesive and a photo-alignment polymer, and an optically anisotropic layer provided on the pressure-sensitive adhesive layer, the optically anisotropic layer being formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound, and the pressure-sensitive adhesive layer and the optically anisotropic layer being laminated adjacent to each other.
Further, the manufacturing method of the present invention includes:
a first coating step of coating a long support to be carried with a binder composition containing a binder and a photo-alignment polymer to form a first coating film;
an adhesive layer forming step of forming an adhesive layer after the 1 st coating step;
an action step of causing at least 1 selected from the group consisting of light, heat, acid, and alkali to act;
a light irradiation step of irradiating polarized light or unpolarized light;
a second coating step of directly coating the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound on the pressure-sensitive adhesive layer to form a second coating film having a width larger than the width of the pressure-sensitive adhesive layer;
an optically anisotropic layer forming step of forming an optically anisotropic layer having a width wider than that of the adhesive layer after the 2 nd coating step to produce an optical laminated film; and
and a winding step of winding the optical layered film into a roll shape after the optical anisotropic layer forming step to produce an optical layered film roll.
Here, the working step is a step performed between the pressure-sensitive adhesive layer forming step and the 2 nd coating step or simultaneously with the pressure-sensitive adhesive layer forming step or the 2 nd coating step, and the light irradiation step is a step performed between the pressure-sensitive adhesive layer forming step and the 2 nd coating step or simultaneously with the pressure-sensitive adhesive layer forming step or the 2 nd coating step.
In the production method of the present invention, the photo-alignment polymer is a photo-alignment polymer having a repeating unit a including a cleavage group that is decomposed by at least 1 action selected from the group consisting of light, heat, acid, and base to generate a polar group, and the repeating unit a has the cleavage group on a side chain and a fluorine atom or a silicon atom on a terminal side of the cleavage group on the side chain, and satisfies the following condition 1 or condition 2.
Condition 1: the photo-alignment layer contains a repeating unit B containing a photo-alignment group in addition to the repeating unit A.
Condition 2: the repeating unit a includes a photo-alignment group on the main chain side of the cleavage group of the side chain.
In the present invention, as described above, the width of the optically anisotropic layer formed adjacent to the upper layer of the pressure-sensitive adhesive layer is made wider than the width of the pressure-sensitive adhesive layer, whereby an optical laminated film roll excellent in the handling operation of the optical laminated film can be produced.
The details of the present invention are not clear, but the present inventors presume as follows.
First, in the production method of the present invention, in consideration of coatability of the composition for an optically anisotropic layer provided on an upper layer of a barrier layer (hereinafter, also referred to as "upper layer coatability"), at least 1 kind selected from the group consisting of light, heat, acid, and alkali is allowed to act on a photo-alignment polymer biased on the air interface side of the barrier layer to generate a polar group.
Therefore, if the portion of the surface of the barrier layer exposed after the formation of the optically anisotropic layer remains, the portion is likely to adhere to the back surface of the support or the like existing 1 week before the winding into a roll shape due to the presence of the polar group, and as a result, the handling of the optical laminated film is poor.
Accordingly, it is considered that in the production method of the present invention, the width of the optically anisotropic layer is made wider than the width of the adhesive layer, thereby preventing the surface of the adhesive layer having a polar group from being exposed, and as a result, the adhesion can be suppressed when the adhesive layer is wound into a roll shape.
The first coating step 1, the pressure-sensitive adhesive layer forming step, the working step, the light irradiation step, the second coating step 2, the optically anisotropic layer forming step, the winding step, and any of the steps included in the production method of the present invention will be described below.
[1 st coating Process ]
The 1 st coating step is a step of forming a 1 st coating film by coating a long support to be carried with a binder composition containing a binder and a photo-alignment polymer.
< support body >
Examples of the support include a polymer film that can be wound around a backup roll.
Examples of the material of the polymer film include cellulose-based polymers; acrylic polymers having an acrylate polymer such as polymethyl methacrylate and polymers containing a lactone ring; a thermoplastic norbornene-based polymer; a polycarbonate-series polymer; polyester polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene polymers such AS polystyrene and acrylonitrile-styrene copolymer (AS resin); polyolefin polymers such as polyethylene, polypropylene, and ethylene-propylene copolymers; vinyl chloride-based polymers; amide polymers such as nylon and aromatic polyamide; an imide polymer; a sulfone-based polymer; polyether sulfone polymers; polyether ether ketone polymers; polyphenylene sulfide-based polymers; vinylidene chloride-based polymers; a vinyl alcohol polymer; a vinyl butyral polymer; an aryl ester polymer; polyoxymethylene polymers; an epoxy-based polymer; or a polymer obtained by mixing these polymers.
The thickness of the support is not particularly limited, but is preferably 5 to 200. Mu.m, more preferably 10 to 100. Mu.m, and still more preferably 20 to 90 μm.
< adhesive composition >
The binder composition applied to the support is not particularly limited as long as it contains a binder and a photo-alignment polymer described later, but may contain a polymerization initiator, a photo-acid generator, a solvent, and the like.
(Binder)
The binder contained in the binder composition is not particularly limited, and may be a resin that is simply dried and cured (hereinafter, also referred to as "resin binder") such as a resin having no polymerization reactivity, or may be a polymerizable compound.
{ resin binder }
Specific examples of the resin binder include epoxy resins, diallyl phthalate resins, silicone resins, phenol resins, unsaturated polyester resins, polyimide resins, polyurethane resins, melamine resins, urea resins, ionomer resins, ethylene ethyl acrylate resins, acrylonitrile styrene acrylate copolymer resins, acrylonitrile styrene resins, acrylonitrile chlorinated polyethylene styrene copolymer resins, ethylene vinyl acetate copolymer resins, ethylene-vinyl alcohol copolymer resins, acrylonitrile butadiene styrene copolymer resins, vinyl chloride resins, chlorinated polyethylene resins, polyvinylidene chloride resins, cellulose acetate resins, vinyl fluoride resins, polyoxymethylene resins, polyamide resins, polyarylate resins, thermoplastic polyurethane elastomers, polyether ether ketone resins, polyether sulfone resins, polyethylene, polypropylene, polycarbonate resins, polystyrene maleic acid copolymer resins, polystyrene acrylic acid copolymer resins, polyphenylene ether resins, polyphenylene sulfide resins, polybutadiene resins, polybutylene terephthalate resins, acrylic resins, methacrylic acid resins, methylpentene resins, polylactic acid, polybutylene succinate resins, butyral resins, formal resins, polyvinyl alcohol, polyvinyl pyrrolidone, ethyl cellulose, cellulose acetate resins, and carboxyl methyl cellulose resins, and gelatin resins.
{ polymerizable Compound }
Examples of the polymerizable compound include epoxy monomers, acrylic monomers, and oxetanyl monomers, and among them, epoxy monomers and acrylic monomers are preferable.
In the present invention, a polymerizable liquid crystal compound may be used as the polymerizable compound.
Examples of the epoxy group-containing monomer of the epoxy monomer include bisphenol a type epoxy resin, bisphenol F type epoxy resin, brominated bisphenol a type epoxy resin, bisphenol S type epoxy resin, diphenyl ether type epoxy resin, p-phenylene bisphenol type epoxy resin, naphthalene type epoxy resin, biphenyl type epoxy resin, fluorene type epoxy resin, phenol novolac type epoxy resin, o-cresol novolac type epoxy resin, trihydroxyphenyl methane type epoxy resin, 3 functional type epoxy resin, tetraphenylolethane type epoxy resin, dicyclopentadiene phenol type epoxy resin, hydrogenated bisphenol a type epoxy resin, bisphenol a core-containing polyhydric alcohol type epoxy resin, polypropylene glycol type epoxy resin, glycidyl ester type epoxy resin, glycidylamine type epoxy resin, glyoxal type epoxy resin, alicyclic type epoxy resin, heterocyclic type epoxy resin, and the like.
Examples of the acrylic monomer and the methacrylic acid ester monomer as the acrylic monomer, and the 3-functional monomer include trimethylolpropane triacrylate, trimethylolpropane PO (propylene oxide) modified triacrylate, trimethylolpropane EO (ethylene oxide) modified triacrylate, trimethylolpropane trimethacrylate, and pentaerythritol triacrylate. Examples of the 4-or more functional monomer and oligomer include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, and the like.
The polymerizable liquid crystal compound is not particularly limited, and for example, a compound capable of performing any of homeotropic alignment, uniform alignment, hybrid alignment, and cholesteric alignment can be used.
Here, the liquid crystal compound can be generally classified into a rod type and a disk type from its shape. In addition, they are of the low-molecular and high-molecular type, respectively. The polymer generally refers to a polymer having a polymerization degree of 100 or more (polymer physical/phase transition kinetics, earth well is known from Japan, 2 pages, rock book store (Iwanami Shoten), 1992). In the present invention, any liquid crystal compound can also be used, but preferably a rod-like liquid crystal compound (hereinafter, also simply referred to as "CLC") or a discotic liquid crystal compound (hereinafter, also simply referred to as "DLC") is used, and preferably a monomer or a relatively low molecular weight liquid crystal compound having a polymerization degree of less than 100 is used.
Specific examples of the polymerizable group of the polymerizable liquid crystal compound include an acryloyl group, a methacryloyl group, an epoxy group, and a vinyl group.
By polymerizing such a polymerizable liquid crystal compound, the alignment of the liquid crystal compound can be fixed. In addition, after the liquid crystal compound is fixed by polymerization, it is no longer necessary to exhibit liquid crystallinity.
As the rod-like liquid crystal compound, for example, the compounds described in the technical means 1 of japanese patent application laid-open No. 11-513019 or paragraphs [0026] to [0098] of japanese patent application laid-open No. 2005-289980 can be preferably used, and as the disk-like liquid crystal compound, for example, the compounds described in paragraphs [0020] to [0067] of japanese patent application laid-open No. 2007-108732 or paragraphs [0013] to [0108] of japanese patent application laid-open No. 2010-244038 can be preferably used, but the liquid crystal compound is not limited thereto.
In the present invention, as the polymerizable liquid crystal compound, a reverse wavelength dispersion liquid crystal compound can be used.
In the present specification, the term "liquid crystal compound having reverse wavelength dispersibility" means that when the in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced using the liquid crystal compound is measured, the Re value becomes equal to or higher as the measurement wavelength becomes longer.
The reverse wavelength-dispersive liquid crystal compound is not particularly limited as long as it is a compound capable of forming a reverse wavelength-dispersive thin film as described above, and examples thereof include a compound represented by the general formula (I) described in japanese patent application laid-open No. 2008-297210 (in particular, a compound described in paragraphs [0034] to [0039 ]), a compound represented by the general formula (1) described in japanese patent application laid-open No. 2010-403082 (in particular, a compound described in paragraphs [0067] to [0073 ]), and a compound represented by the general formula (1) described in japanese patent application laid-open No. 2016-0812016 (in particular, a compound described in paragraphs [0043] to [0055 ]), and the like.
Further, compounds described in paragraphs [0027] to [0100] of Japanese patent application laid-open No. 2011-006360, paragraphs [0028] to [0125] of Japanese patent application laid-open No. 2011-006361, paragraphs [0034] to [0298] of Japanese patent application laid-open No. 2012-207765, paragraphs [0016] to [0345] of Japanese patent application laid-open No. 2012-077055, paragraphs [0017] to [0072] of WO12/141245, paragraphs [0021] to [0088] of WO12/147904, and paragraphs [0028] to [0115] of WO14/147904 can be used.
(photo-alignment Polymer)
The photo-alignment polymer contained in the binder composition (hereinafter, also referred to as "the photo-alignment polymer of the present invention" in the present specification) is a photo-alignment polymer having a repeating unit a containing a cleavage group that is decomposed by at least 1 action selected from the group consisting of light, heat, acid, and base to generate a polar group.
In the photo-alignment polymer of the present invention, the repeating unit a has a cleavage group in a side chain, and has a fluorine atom or a silicon atom at a terminal side of the cleavage group in the side chain.
The photo-alignment polymer of the present invention has a photo-alignment group so as to satisfy the following condition 1 or condition 2.
Condition 1: the photo-alignment layer contains a repeating unit B containing a photo-alignment group in addition to the repeating unit A.
Condition 2: the repeating unit a includes a photo-alignment group on the main chain side of the cleavage group of the side chain.
The "polar group" contained in the repeating unit a means a group having at least 1 or more hetero atoms or halogen atoms, and specific examples thereof include a hydroxyl group, a carbonyl group, a carboxyl group, an amino group, a nitro group, an ammonium group, a cyano group, and the like. Among them, hydroxyl group and carboxyl group are preferable.
The "polar group-forming cleavage group" means a group which forms the above-mentioned polar group by cleavage, but includes a group which forms a polar group by reacting with an oxygen molecule after radical cleavage in the present invention.
When the photo-alignment polymer of the present invention satisfies condition 1, it is preferable that the repeating unit a is a repeating unit represented by the following formula (1) or a repeating unit represented by the following formula (2-1) or (2-2), and the repeating unit B is a repeating unit represented by the following formula (3) or a repeating unit represented by the following formula (4-1) or (4-2), from the viewpoint that unevenness in film thickness of the pressure-sensitive adhesive layer (hereinafter, also referred to as "wind unevenness") caused by drying wind during drying can be more suppressed.
Among them, it is more preferable that the repeating unit a is a repeating unit represented by the following formula (1) and the repeating unit B is a repeating unit represented by the following formula (3).
[ chemical formula 1]
In the above formulae (1) and (2-1) and (3) and (4-1), R 1 Represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and a plurality of R in the formulae (1) and (3) 1 May be the same or different.
As R 1 Preferably a hydrogen atom or a methyl group.
And, in the above formulae (1), (2-1) and (2-2), X 1 And X 2 Each independently represents a single bond or a 2-valent linking group, RK represents a cleavage group, and RL represents a 1-valent organic group containing a fluorine atom or a silicon atom.
X in the above formulae (1), (2-1) and (2-2) 1 And X 2 Examples of the 2-valent linking group include those selected from the group consisting of a linear, branched or cyclic alkylene group having 1 to 10 carbon atoms which may have a substituent, an arylene group having 6 to 12 carbon atoms which may have a substituent, an ether group (-O-), a carbonyl group (- = O) -), and a divalent or divalent organic group which may have a substituentAt least 1 or more of the group of substituted imino (-NH-).
Examples of the substituent which the alkylene group, arylene group and imino group may have include an alkyl group, an alkoxy group, a halogen atom and a hydroxyl group.
The alkyl group is preferably a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclohexyl group and the like), still more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group or an ethyl group.
The alkoxy group is, for example, preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group, or the like), still more preferably an alkoxy group having 1 to 4 carbon atoms, and particularly preferably a methoxy group or an ethoxy group.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and among them, a fluorine atom and a chlorine atom are preferable.
Examples of the linear alkylene group include a linear, branched or cyclic alkylene group having 1 to 10 carbon atoms, and specific examples thereof include a methylene group, a vinyl group, a propylene group, a butylene group, a pentylene group, a hexylene group, and a decylene group.
Specific examples of the branched alkylene group include dimethylmethylene, methylvinyl, 2-dimethylpropylene, and 2-ethyl-2-methylpropylene.
Specific examples of the cyclic alkylene group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclodecyl group, an adamantan-diyl group, a norbornane-diyl group, and an exo-tetrahydrodicyclopentadiene-diyl group, and among them, a cyclohexyl group is preferable.
Specific examples of the arylene group having 6 to 12 carbon atoms include phenylene, xylylene, biphenylene, naphthylene, and 2,2' -methylenebiphenyl, and among them, phenylene is preferable.
Examples of the cleavage group represented by RK in the above formulae (1), (2-1) and (2-2) include cleavage groups (bonds) represented by any of the following formulae (RK-1) to (RK-13).
[ chemical formula 2]
In the above formulae (rk-1) to (rk-13), 1 represents the same as X in the formulae (1), (2-1) and (2-2) 1 And X 2 2 represents a bonding position not bonded with X in the formulae (1), (2-1) and (2-2) 1 And X 2 R represents independently a hydrogen atom or a 1-valent organic group, respectively.
Examples of the 1-valent organic group represented by R include a linear or cyclic alkyl group having 1 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms which may have a substituent.
Further, the anion moiety in the above formulae (rk-10) and (rk-11) does not affect the cleavage, and is not particularly limited, and an inorganic anion or an organic anion may be used.
Specific examples of the inorganic anion include halide ions such as chloride ion and bromide ion; sulfonate anions and the like.
Specific examples of the organic anion include carboxylate anions such as acetate anion; organic sulfonate anions such as methane sulfonate anion and p-toluene sulfonate anion, and the like.
In the present invention, among these cleavage groups, in the case of using light to cleave it, from the viewpoint of quantum efficiency, the cleavage group represented by the above formula (rk-1) is preferred, and in the case of using acid to cleave it, from the viewpoint of cleavage rate, the cleavage group represented by the above formula (rk-9) is preferred.
Examples of the 1-valent organic group containing a fluorine atom or a silicon atom, which is represented by RL in the above formulas (1), (2-1) and (2-2), include an alkyl group having 1 to 20 carbon atoms and having a fluorine atom as a substituent, and an alkenyl group having 2 to 20 carbon atoms.
And, in the above formulas (3), (4-1) and (4-2), X 1 Represents a single bond or a 2-valent linking group, and RO represents a photo-alignment group.
X in the above formulae (3), (4-1) and (4-2) 1 The 2-valent linking group represented by the formula (1), (2-1) and (2-2) includes, for example, a linking group with X in the above formula 1 The same groups.
The photo-alignment group represented by RO in the above formulas (3), (4-1) and (4-2) is a group having a photo-alignment function of deriving a realignment or anisotropic chemical reaction by irradiation with light having anisotropy (for example, plane polarized light, etc.), and is preferably a photo-alignment group that generates at least one of dimerization and isomerization by the action of light, from the reasons that uniformity of alignment is excellent and thermal stability or chemical stability is also good.
Specific examples of the photo-alignment group that dimerizes by the action of light include, for example, a group having a skeleton of at least 1 derivative selected from the group consisting of cinnamic acid derivatives (m.schadt et al, j.appl.phys., vol.31, no.7, page 2155 (1992)), coumarin derivatives (m.schadt et al, nature, vol.381, page 212 (1996)), chalcone derivatives (jungle, lecture of the crystal symposium, 2AB03 (1997)), maleimide derivatives, and benzophenone derivatives (y.k.jang et al, SID int.symposistone Digest, P-53 (1997)).
On the other hand, as the photo-alignment group which is isomerized by the action of light, specifically, there may be preferably mentioned, for example, at least one compound having a skeleton selected from the group consisting of azobenzene compounds (k.ichimura et al, mol.crystal.liq.cryst., 298, 221 (1997)), stilbene compounds (j.g.victor and j.m.torkelson, macromolecules,20,2241 (1987)), spiropyran compounds (k.ichimura et al, chemistry Letters, page 1063 (1992)), k.ichimura et al, thin Solid Films, vol.235, page 101 (1993)), cinnamic acid compounds (k.ichimura et al, macromolecules,30, 903 (1997)), and hydrazono- β -ketoester compounds (s.yamamura et al, liquid Crystals, page 13, page 2, 189 (1993)).
Among them, the photo-alignment group is preferably a group having a skeleton of at least 1 derivative selected from the group consisting of a cinnamic acid derivative, a coumarin derivative, a chalcone derivative, a maleimide derivative, an azobenzene compound, a stilbene compound, and a spiropyran compound, and more preferably a group having a skeleton of a cinnamic acid derivative or a coumarin derivative.
When the photo-alignment polymer of the present invention satisfies condition 1 and is cleaved with an acid, it is preferable that the repeating unit a is a repeating unit represented by formula (7) and the repeating unit B is a repeating unit represented by formula (8) from the viewpoint of cleavage rate and ease of synthesis.
[ chemical formula 3]
In the above formula (7), R 1 Represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R represents a hydrogen atom or a 1-valent organic group, and each of the plurality of R may be the same or different.
In the formula (7), X represents a hydrogen atom or a fluorine atom, and ma and na each independently represent an integer of 1 to 20.
Examples of the 1-valent organic group represented by R include a linear or cyclic alkyl group having 1 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms which may have a substituent.
In the above formula (8), R is 1 Represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, L 1 Represents a 2-valent linking group. R 2 、R 3 、R 4 、R 5 And R 6 Each independently represents a hydrogen atom or a substituent, R 2 、R 3 、R 4 、R 5 And R 6 Adjacent 2 groups in (b) may be bonded to form a ring.
As the above formula(7) R in (1) 1 Preferably a hydrogen atom or a methyl group.
R in the formula (7) is preferably a hydrogen atom.
In the above formula (7), ma is preferably 1 or 2,na, and is preferably 3 to 7.
Further, X in the above formula (7) is preferably a fluorine atom.
The repeating unit A represented by the above formula (7) includes, for example, a repeating unit obtained by polymerizing any one of monomers represented by the following formulae (7-1) to (7-6).
[ chemical formula 4]
As R in the above formula (8) 1 Preferably a hydrogen atom or a methyl group.
L in the above formula (8) 1 The 2-valent linking group represented is preferably a 2-valent linking group formed by combining at least 2 or more groups selected from the group consisting of a linear, branched or cyclic alkylene group having 1 to 18 carbon atoms which may have a substituent, an arylene group having 6 to 12 carbon atoms which may have a substituent, an ether group (-O-), a carbonyl group (-C (= 0) -) and an imino group (-NH-) which may have a substituent, from the viewpoint that the photoalignability group easily interacts with the liquid crystal compound and the alignment property of the optically anisotropic layer formed as an upper layer (hereinafter, also referred to as "liquid crystal alignment property") is more excellent.
Examples of the substituent which the alkylene group, arylene group and imino group may have include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a cyano group, a carboxyl group, an alkoxycarbonyl group and a hydroxyl group.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and among them, a fluorine atom and a chlorine atom are preferable.
The alkyl group is preferably a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclohexyl group and the like), still more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group or an ethyl group.
The alkoxy group is, for example, preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group, or the like), still more preferably an alkoxy group having 1 to 4 carbon atoms, and particularly preferably a methoxy group or an ethoxy group.
Examples of the aryl group include aryl groups having 6 to 12 carbon atoms, and specific examples thereof include phenyl, α -methylphenyl, and naphthyl groups, and among these, phenyl groups are preferable.
Examples of the aryloxy group include a phenoxy group, a naphthoxy group, an imidazolyloxy group, a benzimidazolyloxy group, a pyridin-4-yloxy group, a pyrimidyloxy group, a quinazolinyloxy group, a purinyloxy group, and a thiophen-3-yloxy group.
Examples of the alkoxycarbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group.
Examples of the linear alkylene group include a methylene group, a vinyl group, a propylene group, a butylene group, a pentylene group, a hexylene group, a decylene group, an undecylene group, a dodecenyl group, a tridecylene group, a tetradecylene group, a pentadecenyl group, a hexadecylene group, a heptadecenyl group, and an octadecylene group.
Specific examples of the branched alkylene group include dimethylmethylene, methylvinyl, 2-dimethylpropylene, and 2-ethyl-2-methylpropylene.
Specific examples of the cyclic alkylene group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclodecyl group, an adamantan-diyl group, a norbornane-diyl group, and an exo-tetrahydrodicyclopentadiene-diyl group, and among them, a cyclohexyl group is preferable.
Specific examples of the arylene group having 6 to 12 carbon atoms include phenylene, xylylene, biphenylene, naphthylene, and 2,2' -methylenebiphenyl, and among them, phenylene is preferable.
Wherein L in the above formula (8) is 1 The 2-valent linking group is preferably a 2-valent linking group containing a nitrogen atom and a cycloalkane ring, because the liquid crystal alignment properties are more excellent. In the present invention, a part of carbon atoms constituting the cycloalkane ring may be substituted with a heteroatom selected from the group consisting of nitrogen, oxygen and sulfur. When a part of carbon atoms constituting the cycloalkane ring is substituted with a nitrogen atom, the carbon atoms may not have a nitrogen atom different from the cycloalkane ring.
The cycloalkane ring is preferably a cycloalkane ring having 6 or more carbon atoms, and specific examples thereof include a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclododecane ring, and the like.
In the present invention, it is preferable that L1 in the above formula (8) is a 2-valent linking group represented by any one of the following formulae (11) to (20) from the viewpoint of further improving the liquid crystal alignment properties.
[ chemical formula 5]
In the formulae (11) to (20), 1 represents a bonding position to a carbon atom constituting the main chain in the formula (8), and 2 represents a bonding position to a carbon atom constituting the carbonyl group in the formula (8).
Among the 2-valent linking groups represented by any of the above formulae (11) to (20), the 2-valent linking group represented by any of the above formulae (12), (13), (17) and (18) is preferable from the viewpoint of a good balance between solubility in a solvent used in forming the pressure-sensitive adhesive layer and solvent resistance of the obtained pressure-sensitive adhesive layer.
Then, for R in the above formula (8) 2 、R 3 、R 4 、R 5 And R 6 The substituent represented by one embodiment of (1) will be described. R in the above formula (8) 2 、R 3 、R 4 、R 5 And R 6 The case where the hydrogen atom may be a hydrogen atom instead of the substituent is as described above.
From the viewpoint that the photo-alignment group easily interacts with the liquid crystal compound and the liquid crystal alignment property is more excellent, R in the above formula (8) is preferable 2 、R 3 、R 4 、R 5 And R 6 The substituents represented by one embodiment of (1) are each independently a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear halogenated alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a cyano group, an amino group or a group represented by the following formula (10).
[ chemical formula 6]
In the formula (10), R represents a bonding position with the benzene ring in the formula (8) 9 Represents an organic group having a valence of 1.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and among them, a fluorine atom and a chlorine atom are preferable.
The linear, branched or cyclic alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms as the linear alkyl group, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group and the like.
The branched alkyl group is preferably an alkyl group having 3 to 6 carbon atoms, and specific examples thereof include an isopropyl group, a tert-butyl group and the like.
The cyclic alkyl group is preferably an alkyl group having 3 to 6 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group.
The linear halogenated alkyl group having 1 to 20 carbon atoms is preferably a fluoroalkyl group having 1 to 4 carbon atoms, and specific examples thereof include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group and the like, and among them, a trifluoromethyl group is preferable.
The alkoxy group having 1 to 20 carbon atoms is preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 6 to 18 carbon atoms, and still more preferably an alkoxy group having 6 to 14 carbon atoms. Specific examples thereof include preferably methoxy group, ethoxy group, n-butoxy group, methoxyethoxy group, n-hexyloxy group, n-octyloxy group, n-decyloxy group, n-dodecyloxy group, and n-tetradecyloxy group, and among these, n-hexyloxy group, n-octyloxy group, n-decyloxy group, n-dodecyloxy group, and n-tetradecyloxy group are more preferable.
The aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 12 carbon atoms, and specific examples thereof include a phenyl group, an α -methylphenyl group, and a naphthyl group, and among these, a phenyl group is preferred.
The aryloxy group having 6 to 20 carbon atoms is preferably an aryloxy group having 6 to 12 carbon atoms, and specific examples thereof include a phenoxy group, a 2-naphthoxy group and the like, and among them, a phenoxy group is preferable.
Examples of the amino group include a primary amino group (-NH) 2 ) (ii) a Secondary amino groups such as methylamino; tertiary amino groups such as a group having a nitrogen atom of a dimethylamino group, a diethylamino group, a dibenzylamino group, or a nitrogen-containing heterocyclic compound (e.g., pyrrolidine, piperidine, or piperazine) as a connecting bond.
With respect to the group represented by the above formula (10), R in the above formula (10) is 9 Examples of the 1-valent organic group include linear or cyclic alkyl groups having 1 to 20 carbon atoms.
The linear alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, and an n-propyl group, and among them, a methyl group or an ethyl group is preferred.
The cyclic alkyl group is preferably an alkyl group having 3 to 6 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and the like, and among them, a cyclohexyl group is preferable.
R in the above formula (10) 9 The 1-valent organic group represented may be a group in which a plurality of the above-described linear alkyl groups and cyclic alkyl groups are combined directly or via a single bond.
In the present invention, R in the above formula (8) is preferable because the photo-alignment group easily interacts with the liquid crystal compound and the liquid crystal alignment property is more excellent 2 、R 3 、R 4 、R 5 And R 6 At least R in 4 The substituent is preferably R, because it improves the linearity of the photo-alignment copolymer obtained, facilitates the interaction with the liquid crystal compound, and improves the liquid crystal alignment 2 、R 3 、R 5 And R 6 All represent hydrogen atoms.
In the present invention, R in the above formula (8) is preferable from the viewpoint of improving the reaction efficiency when the obtained pressure-sensitive adhesive layer is irradiated with light 4 Are electron donating substituents.
Here, the electron-donating substituent (electron-donating group) means a substituent having a Hammett value (Hammett substituent constant σ p) of 0 or less, and examples thereof include an alkyl group, a halogenated alkyl group, and an alkoxy group among the above substituents.
Among them, alkoxy groups are preferable, and alkoxy groups having 6 to 16 carbon atoms are more preferable, and alkoxy groups having 7 to 10 carbon atoms are even more preferable, because film thickness unevenness (wind unevenness) can be further suppressed and liquid crystal alignment properties are further improved.
Examples of the repeating unit B represented by the above formula (8) include repeating units obtained by polymerizing any one of monomers represented by the following formulae (8-1) to (8-6).
[ chemical formula 7]
When the photo-alignment polymer of the present invention satisfies the condition 1, the photo-alignment polymer may have other repeating units in addition to the repeating unit a and the repeating unit B.
Examples of the monomer (radical polymerizable monomer) forming such another repeating unit include an acrylate compound, a methacrylate compound, a maleimide compound, an acrylamide compound, acrylonitrile, maleic anhydride, a styrene compound, and a vinyl compound.
Specific examples of the photo-alignment polymer of the present invention satisfying condition 1 include copolymers using any one of the monomers represented by the above formulas (7-1) to (7-6), any one of the monomers represented by the above formulas (8-1) to (8-6), and any other repeating unit, and among them, copolymers represented by the following formulas C-1 to C-5 are preferable.
[ chemical formula 8]
On the other hand, when the photo-alignment polymer of the present invention satisfies condition 2, it is preferable that the repeating unit a is a repeating unit represented by the following formula (5) or a repeating unit represented by the following formula (6-1) or (6-2) from the viewpoint of the liquid crystal alignment property of the optically anisotropic layer formed on the upper layer.
Among them, the repeating unit a is more preferably a repeating unit represented by the following formula (5).
[ chemical formula 9]
In the above formulae (5) and (6-1), R 1 Represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and a plurality of R in the formula (5) 1 May be the same or different.
As R 1 Preferably a hydrogen atom or a methyl group.
And, in the above formulae (5), (6-1) and (6-2), X 1 、X 2 And X 3 Each independently represents a single bond or a 2-valent linking group.
Here, X in the above formulae (5), (6-1) and (6-2) is defined as 1 、X 2 And X 3 Examples of the 2-valent linking group include those represented by the above formulas (1), (2-1) and (2-2) 1 The same groups.
In the above formulae (5), (6-1) and (6-2), RK represents a cleavage group.
Examples of the cleavage group represented by RK in the formulae (5), (6-1) and (6-2) include cleavage groups (bonds) represented by any of the formulae (RK-1) to (RK-13) described above, which are the same as RK in the formulae (1), (2-1) and (2-2). In the above formulae (rk-1) to (rk-13), 1 represents X in the formulae (5), (6-1) and (6-2) 3 And X 2 2 represents a bonding position not bonded to X in the above formulae (5), (6-1) and (6-2) 3 And X 2 R represents independently a hydrogen atom or a 1-valent organic group, respectively.
In the formulae (5), (6-1) and (6-2), RO represents a photo-alignment group.
Examples of the photo-alignment group include the same photo-alignment groups represented by RO in the above formulas (3), (4-1) and (4-2).
Specific examples of the photo-alignment polymer of the present invention satisfying condition 2 include polymers represented by the following formulas H-1 to H-3.
[ chemical formula 10]
The weight average molecular weight (Mw) of the photo-alignment polymer of the present invention is preferably 1000 to 500000, more preferably 1500 to 400000, and particularly preferably 2000 to 300000.
The number average molecular weight (Mn) of the photo-alignment polymer of the present invention is preferably 500 to 250000, more preferably 1000 to 200000, and particularly preferably 1500 to 150000.
The degree of dispersion (Mw/Mn) of the photo-alignment polymer of the present invention is preferably 1.00 to 20.00, more preferably 1.00 to 18.00, and particularly preferably 1.00 to 16.00.
The weight average molecular weight and the number average molecular weight are values measured by Gel Permeation Chromatography (GPC) under the following conditions.
[ eluent ] Tetrahydrofuran (THF)
[ device name ] Ecosec HLC-8220GPC (manufactured by TOSOH CORPORATION)
[ column ] TSKgel SuperHZM-H, TSKgel SuperHZ4000, TSKgel SuperHZM200 (manufactured by TOSOH CORPORATION)
[ column temperature ]40 deg.C
[ flow Rate ]50ml/min
(polymerization initiator)
When a polymerizable compound is used as the adhesive, the adhesive composition preferably contains a polymerization initiator.
Such a polymerization initiator is not particularly limited, and depending on the form of the polymerization reaction, a thermal polymerization initiator and a photopolymerization initiator may be mentioned.
In the present invention, a photopolymerization initiator capable of initiating a polymerization reaction by ultraviolet irradiation is preferable.
Examples of the photopolymerization initiator include an α -carbonyl compound (described in each of U.S. Pat. Nos. 2367661 and 2367670), an acyloin ether (described in each of U.S. Pat. Nos. 2448828), an α -hydrocarbon-substituted aromatic acyloin compound (described in U.S. Pat. No. 2722512), a polynuclear quinone compound (described in each of U.S. Pat. Nos. 3046127 and 2951758), a combination of a triarylimidazole dimer and p-aminophenyl ketone (described in U.S. Pat. No. 3549367), an acridine and phenazine compound (described in each of Japanese patent application laid-open Nos. 60-105667 and 4239850), an oxadiazole compound (described in U.S. Pat. No. 4212912912912970), and an acylphosphine oxide compound (described in Japanese patent publication No. Sho 63-040040029, japanese patent publication No. 5-9234, japanese patent application laid-open No. 10-09570288, japanese patent publication No. 10-029997), and the like.
(photoacid generators)
When the photo-alignment polymer is a polymer having a specific group having a valence of 1 including a cleavage group which is decomposed by the action of an acid to generate a polar group, the binder composition preferably contains a photo-acid generator.
The photoacid generator is preferably a compound that generates an acid by reaction with an activating light having a wavelength of 300nm or longer, preferably 300 to 450nm, but is not limited to its chemical structure. The photoacid generator that is not directly sensitive to the activating light having a wavelength of 300nm or longer can be preferably used in combination with a sensitizer as long as it is a compound that generates an acid by being sensitive to the activating light having a wavelength of 300nm or longer when used in combination with the sensitizer. The photoacid generator used in the present invention is preferably a photoacid generator that generates an acid having a pKa of 4 or less, more preferably a photoacid generator that generates an acid having a pKa of 3 or less, and most preferably a photoacid generator that generates an acid having a pKa of 2 or less. In the present invention, the pKa substantially refers to the pKa in water at 25 ℃. The case where the measurement cannot be performed in water means a case where the measurement is performed with a solvent suitable for the measurement. Specifically, the pKa described in the chemical review and the like can be referred to. The acid having a pKa of 3 or less is preferably a sulfonic acid or a phosphonic acid, and more preferably a sulfonic acid.
Examples of the photoacid generator include onium salt compounds, trichloromethyl s-triazines, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, imide sulfonate compounds, and oxime sulfonate compounds. Among them, onium salt compounds, imide sulfonate compounds and oxime sulfonate compounds are preferable, and onium salt compounds and oxime sulfonate compounds are particularly preferable. The photoacid generator can be used alone in1 kind or in combination of 2 or more kinds.
(solvent)
The pressure-sensitive adhesive composition preferably contains a solvent from the viewpoint of workability of forming the pressure-sensitive adhesive layer and the like.
Specific examples of the solvent include ketones (e.g., acetone, 2-butanone, methyl isobutyl ketone, cyclohexanone), ethers (e.g., dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g., hexane, etc.), alicyclic hydrocarbons (e.g., cyclohexane, etc.), aromatic hydrocarbons (e.g., toluene, xylene, trimethylbenzene, etc.), halogenated carbons (e.g., dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.), esters (e.g., methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), amides (e.g., dimethylformamide, dimethylacetamide, etc.), and 1 kind of these may be used alone or 2 or more kinds may be used in combination.
(coating method)
The method of applying the adhesive composition to the support is not particularly limited, and specific examples of the application method include a spin coating method, an air knife coating method, a curtain coating method, a roll coating method, a wire bar coating method, a gravure coating method, and a die coating method.
[ adhesive layer Forming Process ]
The pressure-sensitive adhesive layer forming step is a step of forming a pressure-sensitive adhesive layer after the 1 st coating step, and can be formed by applying a curing treatment (irradiation of ultraviolet rays (light irradiation treatment) or heating treatment) to the 1 st coating film obtained in the 1 st coating step.
The conditions of the curing treatment are not particularly limited, and in polymerization by light irradiation, ultraviolet rays are preferably used. The irradiation dose is preferably 10mJ/cm 2 ～50J/cm 2 More preferably 20mJ/cm 2 ～5J/cm 2 More preferably 30mJ/cm 2 ～3J/cm 2 Particularly preferably 50 to 1000mJ/cm 2 . Further, the polymerization reaction may be carried out under heating to accelerate the polymerization reaction.
[ working procedure ]
The action step is a step of causing at least 1 selected from the group consisting of light, heat, acid and base to act.
In addition, the working step is a step performed between the pressure-sensitive adhesive layer forming step and the 2 nd coating step or simultaneously with the pressure-sensitive adhesive layer forming step or the 2 nd coating step, from the viewpoint of ensuring coatability when forming the optically anisotropic layer as the upper layer.
Here, "between the pressure-sensitive adhesive layer forming step and the 2 nd coating step" means that the pressure-sensitive adhesive layer formed in the pressure-sensitive adhesive layer forming step (for example, thermal polymerization) is subjected to an action step (for example, a step of causing light to act) before the 2 nd coating step is performed.
The term "simultaneously with the pressure-sensitive adhesive layer forming step" means that the pressure-sensitive adhesive layer forming step, for example, a step of forming a pressure-sensitive adhesive layer by polymerization of an olefin monomer that generates photoradicals, polymerization of an epoxy monomer that generates photoacid, or the like, and an action step (for example, a step of acting light) are performed simultaneously. That is, it means that light for polymerizing the adhesive layer and light for cleavage cause 2 actions at the same time.
The phrase "simultaneously with the 2 nd coating step" means that the applying step (for example, the step of applying heat) is simultaneously performed when the 2 nd coating step is performed on the pressure-sensitive adhesive layer formed in the pressure-sensitive adhesive layer forming step (for example, photopolymerization).
Among them, it is preferable to perform the light action simultaneously with the pressure-sensitive adhesive layer formation step from the viewpoint of simplifying the process.
Examples of the method of applying light include a method of irradiating the pressure-sensitive adhesive layer with ultraviolet light. As the light source, a lamp emitting ultraviolet rays such as a high-pressure mercury lamp or a metal halide lamp can be used. The dose of irradiation is preferably 10mJ/cm 2 ～50J/cm 2 More preferably 20mJ/cm 2 ～5J/cm 2 More preferably 30mJ/cm 2 ～3J/cm 2 Particularly preferably 50 to 1000mJ/cm ２ 。
Examples of the method of applying heat include a method of heating the pressure-sensitive adhesive layer. The heating temperature is preferably 50 to 200 ℃, more preferably 60 to 150 ℃, and particularly preferably 70 to 130 ℃.
Examples of the method of allowing the acid to act include a method of adding an acid to the adhesive layer in advance, a method of adding a photoacid generator to the adhesive layer and generating an acid using light as a trigger, a method of adding a thermal acid generator to the adhesive layer and generating an acid using heat as a trigger, and the like. Among these, methods using a photoacid generator and a thermal acid generator are preferable.
Examples of the method of causing the alkali to act include a method of adding an alkali to the pressure-sensitive adhesive layer in advance, a method of adding a photobase generator to the pressure-sensitive adhesive layer to generate an alkali using light as a trigger, a method of adding a thermal base generator to the pressure-sensitive adhesive layer to generate an alkali using heat as a trigger, and the like. Among them, a method using a photobase generator and a thermal base generator is preferable.
[ light irradiation step ]
The light irradiation step is a step of irradiating polarized light or unpolarized light, that is, a step of forming an adhesive layer to which an alignment regulating force is applied.
In order to secure coatability when forming the optically anisotropic layer as the upper layer, the light irradiation step is performed between the pressure-sensitive adhesive layer forming step and the 2 nd coating step or simultaneously with the pressure-sensitive adhesive layer forming step or the 2 nd coating step.
Here, "between the pressure-sensitive adhesive layer forming step and the 2 nd coating step" means that the pressure-sensitive adhesive layer formed in the pressure-sensitive adhesive layer forming step (for example, thermal polymerization) is subjected to an irradiation step (for example, a step of irradiating polarized light) before the 2 nd coating step is performed.
The term "simultaneously with the pressure-sensitive adhesive layer forming step" means that a step of forming a pressure-sensitive adhesive layer, for example, a step of forming a pressure-sensitive adhesive layer by polymerization of an olefin monomer that generates photoradicals and polymerization of an epoxy monomer that generates photoacid, and an irradiation step (for example, a step of irradiating polarized light) are simultaneously performed. That is, it means that light for polymerizing the adhesive layer and light for alignment cause 2 actions at the same time.
The phrase "simultaneously with the 2 nd coating step" means that the irradiation step (for example, a step of irradiating polarized light) is simultaneously performed when the 2 nd coating step is performed on the pressure-sensitive adhesive layer formed in the pressure-sensitive adhesive layer forming step (for example, photopolymerization).
Among these, the step performed between the pressure-sensitive adhesive layer forming step and the 2 nd coating step is preferable.
The polarized light to be irradiated in the light irradiation step is not particularly limited, and examples thereof include linearly polarized light, circularly polarized light, and elliptically polarized light, and preferably linearly polarized light.
The unpolarized light to be irradiated is also referred to as unpolarized light, and preferably the surface of the coating film is irradiated from an oblique direction. The "inclination direction" is not particularly limited as long as it is a direction inclined by a polar angle θ (0 < θ < 90 °) with respect to the normal direction of the coating film surface, and can be appropriately selected according to the purpose, and θ is preferably 20 to 80 °.
As a method of performing light irradiation, for example, a method of irradiating polarized ultraviolet rays is preferable, and specifically, a method of using a polarizing plate (for example, an iodine polarizing plate, a dichroic dye polarizing plate, a wire grid polarizing plate, or the like); a method using a prism-based element (e.g., a Glan-Thomson prism or the like) or a reflective polarizer using the Brewster angle; a method of using light emitted from a laser light source having polarized light, and the like.
Here, the light source for ultraviolet irradiation is not particularly limited as long as it is a light source that generates ultraviolet light, and for example, a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a carbon arc lamp, a metal halide lamp, a xenon lamp, or the like can be used.
[2 nd coating Process ]
The 2 nd coating step is a 2 nd coating film step of directly coating a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound on the pressure-sensitive adhesive layer to form a coating film having a width larger than the width of the pressure-sensitive adhesive layer.
Examples of the polymerizable liquid crystal compound include the same compounds as those described as the binder component of the binder composition.
The "width of the adhesive layer" refers to the width of the adhesive layer formed on the support, and refers to the width in the direction perpendicular to the carrying direction of the support.
The method of applying the polymerizable liquid crystal composition containing a polymerizable liquid crystal compound is not particularly limited, and the same method as in the first application step 1 can be exemplified.
[ procedure for Forming optically Anisotropic layer ]
The optically anisotropic layer forming step is a step of forming an optically anisotropic layer having a width larger than the width of the adhesive layer after the 2 nd coating step to produce an optical laminated film, and can be formed by subjecting the 2 nd coating film obtained in the 2 nd coating step to a curing treatment (irradiation of ultraviolet rays (light irradiation treatment) or heating treatment).
The conditions of the curing treatment are not particularly limited, and in polymerization by light irradiation, ultraviolet rays are preferably used. The irradiation dose is preferably 10mJ/cm 2 ～50J/cm 2 More preferably 20mJ/cm 2 ～5J/cm 2 More preferably 30mJ/cm 2 ～3J/cm 2 Particularly preferably 50 to 1000mJ/cm 2 . Further, the polymerization reaction may be carried out under heating to accelerate the polymerization reaction.
[ coiling procedure ]
The winding step is a step of winding the optical layered film into a roll shape after the optical anisotropic layer forming step to produce an optical layered film roll.
Here, the method of winding into a roll shape is not particularly limited, and examples thereof include a method of winding around a core using a carrier roll.
[ other treatment procedures ]
The production method of the present invention may further include a treatment step of subjecting the surface of the pressure-sensitive adhesive layer to plasma treatment or corona discharge treatment before the 2 nd coating step, in addition to any of the above-described action steps.
The plasma treatment may be performed by vacuum glow discharge, atmospheric glow discharge, or the like, and other methods include frame plasma treatment and the like. For example, the methods described in Japanese patent application laid-open Nos. 6-123062, 11-293011, and 11-005857 can be used.
The corona discharge treatment can be carried out by any conventionally known method, for example, the methods disclosed in Japanese patent application laid-open No. 48-005043, japanese patent application laid-open No. 47-051905, japanese patent application laid-open No. 47-028067, japanese patent application laid-open No. 49-083767, japanese patent application laid-open No. 51-041770, japanese patent application laid-open No. 51-131576, and Japanese patent application laid-open No. 2001-272503.
[ optical laminated film roll ]
The optical laminated film roll of the present invention (hereinafter, also referred to as "the film roll of the present invention") is a roll of an optical laminated film having a pressure-sensitive adhesive layer formed using a pressure-sensitive adhesive composition containing a pressure-sensitive adhesive and a photo-alignment polymer, and an optically anisotropic layer provided on the pressure-sensitive adhesive layer, wherein the optically anisotropic layer is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound, the pressure-sensitive adhesive layer and the optically anisotropic layer are laminated adjacent to each other, and the optically anisotropic layer is laminated so as to cover the surface and end faces of the pressure-sensitive adhesive layer.
[ adhesive layer ]
The pressure-sensitive adhesive layer of the film roll of the present invention is a layer formed using a pressure-sensitive adhesive composition containing a pressure-sensitive adhesive and a photo-alignment polymer.
Here, the adhesive composition and the method of forming the adhesive layer are the same as those described in the above-described production method of the present invention.
The pressure-sensitive adhesive layer is a layer that is provided as a base layer of the optically anisotropic layer, and therefore is in a state after the working step and the light irradiation step described in the above-described production method of the present invention.
Therefore, the photo-alignment polymer contained in the adhesive layer is a homopolymer having a repeating unit including a polar group and a photo-alignment group or a copolymer having a repeating unit including a polar group and a repeating unit including a photo-alignment group.
In the present invention, the thickness of the pressure-sensitive adhesive layer is not particularly limited, but is preferably 0.1 to 10 μm, and more preferably 0.5 to 5 μm.
[ optically anisotropic layer ]
The optically anisotropic layer of the film roll of the present invention is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound as described above, and is laminated so as to cover the surface and end faces of the pressure-sensitive adhesive layer.
Examples of the polymerizable liquid crystal composition for forming the optically anisotropic layer include a composition in which a polymerizable liquid crystal compound described as an optional component in the above-mentioned adhesive composition, a polymerization initiator, a solvent, and the like are blended.
The method for forming the optically anisotropic layer is the same as the method described in the above-described manufacturing method of the present invention.
The surface and end faces of the pressure-sensitive adhesive layer refer to surfaces exposed when the polymerizable liquid crystal composition is applied, and for example, when the pressure-sensitive adhesive layer is formed on a support, the surface and end faces refer to the back surface of the pressure-sensitive adhesive layer, that is, the entire surface area except the interface with the support.
In the present invention, the thickness of the optically anisotropic layer is not particularly limited, but is preferably 0.1 to 10 μm, and more preferably 0.5 to 5 μm.
Examples
The present invention will be described in further detail below with reference to examples. The materials, the amounts used, the ratios, the contents of the processes, the process procedures, and the like shown in the following examples can be appropriately modified without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed restrictively by the examples shown below.
[ example 1]
[ production of support ]
< production of cellulose acylate film 1 >
(preparation of concentrated cellulose acylate solution for core layer)
The following composition was put into a mixing tank and stirred to dissolve the components, thereby preparing a cellulose acetate solution used as a dope of the cellulose acylate for the core layer.
Compound F
[ chemical formula 11]
(preparation of concentrated cellulose acylate solution for outer layer)
A cellulose acetate solution used as the outer layer cellulose acylate dope was prepared by adding 10 parts by mass of the following matting agent solution to 90 parts by mass of the above core layer cellulose acylate dope.
(production of cellulose acylate film 1)
After the core layer cellulose acylate dope and the outer layer cellulose acylate dope were filtered with a filter paper having an average pore size of 34 μm and a sintered metal filter having an average pore size of 10 μm, 3 layers of the core layer cellulose acylate dope and the outer layer cellulose acylate dopes disposed on both sides thereof were simultaneously cast onto a roll at 20 ℃ (endless belt casting machine).
Thereafter, peeling was performed in a state where the solvent content was approximately 20 mass%, both ends of the film in the width direction were fixed by tenter clips, and the film was dried while being stretched at a stretch ratio of 1.1 times in the transverse direction.
Then, the film was carried between rolls of a heat treatment apparatus and dried, thereby producing a cellulose acylate film 1 having a thickness of 40 μm and a width of 1340 mm.
The cellulose acylate film 1 thus prepared was passed through a dielectric heating roll having a temperature of 60 ℃ to raise the surface temperature of the film to 40 ℃ and then applied by a bar coater in an amount of 14ml/m 2 An alkali solution having the following composition was applied to one surface of the film, and the film was heated to 110 ℃.
Then, it was carried under a steam type far infrared heater made by NORITAKE CO., LIMITED for 10 seconds.
Next, a bar coater was also used at 3ml/m 2 Coated with pure water.
Subsequently, water washing by a spray coater and dehydration by an air knife were repeated 3 times, and the resulting product was carried to a drying zone at 70 ℃ and dried for 10 seconds to prepare an alkali saponification-treated cellulose acylate film as a support.
[ formation of alignment layer Y1 ]
An alignment layer coating solution having the following composition was continuously applied to the long cellulose acetate film saponified as described above using a wire rod # 14. After the application, the coating was dried with warm air at 60 ℃ for 60 seconds and further dried with warm air at 100 ℃ for 120 seconds. IN the following composition, the "polymerization initiator (IN 1)" represents a photopolymerization initiator (IRGACURE 2959, manufactured by BASF).
(in the following structural formula, the ratio is a molar ratio)
[ chemical formula 12]
[ preparation of adhesive layer (liquid Crystal layer) ]
A solution for forming a pressure-sensitive adhesive layer (liquid crystal layer) was prepared by dissolving the following rod-shaped liquid crystal compound a (80 parts by mass), the following rod-shaped liquid crystal compound B (20 parts by mass), a photopolymerization initiator (IRGACURE 819, manufactured by BASF corporation) (3 parts by mass), the following vertical alignment agent a (1 part by mass), the following vertical alignment agent B (0.5 part by mass), and the following photo-alignment polymer a (3.0 parts by mass) in 215 parts by mass of methyl ethyl ketone. The prepared solution for forming an adhesive layer was applied to the alignment layer with a wire bar of #3.0 to form a 1 st coating film.
Thereafter, the carrying was resumed, and as shown in table 1 below, the 1 st coating film was dried by heating at 70 ℃ for 60 seconds (drying treatment).
Then, the oxygen concentration is set to beAn ambient gas of 1.0 vol% or less was purged with nitrogen gas, and irradiated with 365nm UV (ultraviolet) -LED (light emitting diode) at a surface temperature of 40 ℃ 2 Ultraviolet rays (ultraviolet irradiation treatment 1).
Next, as shown in Table 1 below, as a step serving as a working step, a 313nm UV-LED was irradiated with an irradiation dose of 1000mJ/cm at a surface temperature of 25 ℃ 2 Ultraviolet rays (ultraviolet irradiation treatment 2).
By these treatments, an adhesive layer having a film thickness of about 1 μm and a width of 1284mm was formed.
[ chemical formula 13]
Rod-like liquid crystalline compound a:
rod-like liquid crystalline compound B:
vertical alignment agent a:
vertical alignment agent B:
photo-alignment polymer a:
[ light irradiation Process ]
At room temperature, on the obtainedThe resulting adhesive layer was irradiated at 25mJ/cm 2 UV light (ultra-high pressure mercury lamp; UL750; manufactured by HOYA) passed through a cable grid polarizer (wavelength: 313 nm) imparts orientation restriction.
[ production of optically Anisotropic layer (Upper layer) ]
The following rod-like liquid crystal compound a (80 parts by mass), the following rod-like liquid crystal compound B (20 parts by mass), a photopolymerization initiator (IRGACURE 907, manufactured by BASF) (3 parts by mass), a sensitizer (KAYACURE DETX, nippon Kayaku co., manufactured by ltd.) (1 part by mass), and the following horizontal alignment agent (0.3 part by mass) were dissolved in methyl ethyl ketone (193 parts by mass) to prepare a solution for forming an optically anisotropic layer. The solution for forming an optically anisotropic layer was applied to the adhesive layer provided with the orientation function by a cable bar coater #2.2 to form a 2 nd coating film having a width wider than the width of the adhesive layer, and the resultant was heated at 60 ℃ for 2 minutes, and irradiated with an irradiation dose of 300mJ/cm using a 160W/cm gas-cooled metal halide lamp (EYE GRAPHICS co., ltd.) while purging nitrogen gas so that the atmosphere gas had an oxygen concentration of 1.0 vol% or less while maintaining 60 ℃ in a state of being heated at 60 ℃ 2 The optically anisotropic layer (width: 1318 mm) was formed by the ultraviolet ray of (2) to prepare an optical laminated film.
Then, the produced optical laminated film was wound into a roll shape to produce an optical laminated film roll.
[ chemical formula 14]
Rod-like liquid crystal compound a:
rod-like liquid crystalline compound B:
horizontal orientation agent
[ example 2]
An optical laminated film roll was produced in the same manner as in example 1, except that the irradiation amount in the ultraviolet irradiation treatment 1 was changed to values shown in table 1 below and the ultraviolet irradiation treatment 2 was not performed.
[ example 3]
An optical laminated film roll was produced in the same manner as in example 1, except that the following photo-alignment polymer B was used instead of the photo-alignment polymer a.
[ chemical formula 15]
Photo-alignment polymer B:
[ example 4]
An optical laminated film roll was produced in the same manner as in example 1 except that the photo-alignment polymer C described below was used in place of the photo-alignment polymer a, a binder layer (liquid crystal layer) forming solution containing 3 parts by mass of a thermal acid generator (Sun Aid SI-B3A, manufactured by SANSHIN CHEMICAL INDUSTRY co., ltd.) was used, and heat treatment (heat treatment 2) of annealing at a surface temperature of 120 ℃ for 30 seconds was performed in place of the ultraviolet irradiation treatment 2.
[ chemical formula 16]
Photo-alignment polymer C:
[ example 5]
An optical laminated film roll was produced in the same manner as in example 1, except that the same pressure-sensitive adhesive layer (liquid crystal layer) forming solution as in example 4 was used and the following treatments were performed to form a pressure-sensitive adhesive layer.
First, as shown in table 1 below, the 1 st coating film was dried by heating at 70 ℃ for 60 seconds (drying treatment).
Next, as a step serving also as a working step, a heat treatment (heat treatment 1) was performed in which annealing was performed for 30 seconds under a condition that the surface temperature was 120 ℃.
Subsequently, as shown in Table 1 below, a 365nm UV (ultraviolet) -LED (light emitting diode) was irradiated with an irradiation dose of 500mJ/cm at a surface temperature of 40 ℃ by using a 365nm UV-LED (light emitting diode) while purging nitrogen gas so as to form an atmosphere gas having an oxygen concentration of 1.0 vol% or less 2 Ultraviolet rays (ultraviolet irradiation treatment 1).
By these treatments, an adhesive layer having a film thickness of about 1 μm was formed.
[ example 6]
An optical laminated film roll was produced in the same manner as in example 1, except that the pressure-sensitive adhesive layer was formed by the following method.
[ production of adhesive layer ]
An adhesive layer forming solution was prepared by dissolving an epoxy monomer (CEL 2021P, manufactured by DAICEL CORPORATION) (100 parts by mass), a thermal acid generator (Sun Aid SI-B3A, manufactured by sanshi CHEMICAL INDUSTRY co., ltd.) (3.0 parts by mass), and the photo-alignment polymer C (2.0 parts by mass) in methyl ethyl ketone (300 parts by mass). The prepared solution for forming an adhesive layer was applied to the alignment layer with a #3.0 wire rod to form a 1 st coating film.
Thereafter, the carrying was resumed, and as shown in table 1 below, the 1 st coating film was dried by heating at 70 ℃ for 60 seconds (drying treatment).
Next, as a step serving also as a working step, a heat treatment of annealing was performed for 60 seconds at a surface temperature of 130 ℃ to form a pressure-sensitive adhesive layer having a thickness of about 1 μm.
[ example 7]
An optical laminated film roll was produced in the same manner as in example 4, except that the following photoacid generator (B-1-1) was used in place of the thermal acid generator (Sun Aid SI-B3A, SANSHIN CHEMICAL input co., ltd.).
[ chemical formula 17]
[ example 8]
An optical laminate film roll was produced in the same manner as in example 6, except that the photoacid generator (B-1-1) was used instead of the thermal acid generator (Sun Aid SI-B3A, SANSHIN CHEMICAL input co., ltd.).
[ example 9]
An optical laminated film roll was produced in the same manner as in example 7, except that the following photo-alignment polymer D was used instead of the photo-alignment polymer C.
[ chemical formula 18]
Photo-alignment polymer D:
comparative example 1
An optical laminated film roll was produced in the same manner as in example 1 except that, when the optically anisotropic layer was formed, the 2 nd coating film having a width smaller than the width of the pressure-sensitive adhesive layer was formed to produce an optically anisotropic layer (width: 1270 mm).
[ transporting operation ]
The optical laminate film was carried by being conveyed from the end of the wound optical laminate film roll, and adhesiveness at this time was evaluated.
< evaluation criteria >
A: when transported, no adhesion of the optical laminate film was observed.
B: during the conveyance, adhesion between the portion of the surface of the barrier layer and the back surface of the support was observed, and the conveyance was affected.
As is clear from the results shown in table 1, when the optically anisotropic layer having a width narrower than the width of the adhesive layer was formed, the conveying operation was poor (comparative example 1).
In contrast, it is found that the transfer operation is excellent when the optically anisotropic layer having a width larger than the width of the pressure-sensitive adhesive layer is formed (examples 1 to 9).
Claims (3)
1. A method for manufacturing an optical laminated film roll, the method being a method for manufacturing a roll of an optical laminated film, the optical laminated film having an adhesive layer formed using an adhesive composition containing an adhesive and a photo-alignment polymer, and an optically anisotropic layer provided on the adhesive layer, the optically anisotropic layer being formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound, the adhesive layer and the optically anisotropic layer being laminated adjacent to each other, the method comprising: a first coating step of coating a long support to be carried with a binder composition containing a binder and a photo-alignment polymer to form a first coating film; a pressure-sensitive adhesive layer forming step of forming a pressure-sensitive adhesive layer after the 1 st coating step; an action step of causing at least 1 selected from the group consisting of light, heat, acid, and alkali to act; a light irradiation step of irradiating polarized light or unpolarized light; a second coating step of directly coating a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound on the pressure-sensitive adhesive layer to form a second coating film having a width larger than the width of the pressure-sensitive adhesive layer; an optically anisotropic layer forming step of forming an optically anisotropic layer having a width wider than that of the adhesive layer after the 2 nd coating step to produce an optical laminated film; and a winding step of winding the optical laminate film into a roll shape after the optically anisotropic layer forming step to produce an optical laminate film roll, wherein the light irradiation step is a step performed between the adhesive layer forming step and the 2 nd coating step or performed simultaneously with the adhesive layer forming step or the 2 nd coating step, the photo-alignment polymer is a photo-alignment polymer having a repeating unit a containing a cleavage group which is decomposed by an action of at least 1 selected from the group consisting of light, heat, acid, and alkali to generate a polar group, the repeating unit a has the cleavage group on a side chain and has a fluorine atom or a silicon atom on a side closer to a terminal than the cleavage group of the side chain, and the photo-alignment polymer satisfies the following condition 1 or condition 2, condition 1: a repeating unit B including a photo-alignment group in addition to the repeating unit a, and condition 2: the repeating unit A includes a photo-alignment group on the main chain side of the cleavage group of the side chain.
2. The method of manufacturing an optical laminated film roll according to claim 1, wherein the acting step is a step of acting light and is performed simultaneously with the pressure-sensitive adhesive layer forming step, and the light irradiation step is a step performed between the pressure-sensitive adhesive layer forming step and the 2 nd coating step.
3. An optical laminate film roll, which is a roll of an optical laminate film having an adhesive layer formed using an adhesive composition containing an adhesive and a photo-alignment polymer, and an optically anisotropic layer provided on the adhesive layer, wherein the optically anisotropic layer is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound, the adhesive layer and the optically anisotropic layer are laminated adjacent to each other, the width of the optically anisotropic layer is wider than the width of the adhesive layer, and the optically anisotropic layer is laminated so as to cover the surface and end faces of the adhesive layer.
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