WO2022234789A1 - 偏光板及び有機ｅｌ表示装置 - Google Patents

偏光板及び有機ｅｌ表示装置 Download PDF

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WO2022234789A1
WO2022234789A1 PCT/JP2022/018910 JP2022018910W WO2022234789A1 WO 2022234789 A1 WO2022234789 A1 WO 2022234789A1 JP 2022018910 W JP2022018910 W JP 2022018910W WO 2022234789 A1 WO2022234789 A1 WO 2022234789A1
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group
light absorption
layer
carbon atoms
film
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PCT/JP2022/018910
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English (en)
French (fr)
Japanese (ja)
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晋也 渡邉
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富士フイルム株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details

Definitions

  • the present invention relates to a polarizing plate and an organic EL (electroluminescence) display device.
  • An organic EL display device is a self-luminous thin display device, and has the advantages of display performance such as high visibility and less dependency on viewing angle compared to a liquid crystal display device (LCD).
  • LCD liquid crystal display device
  • the use of flexible substrates has the potential to realize display devices with shapes that could not be realized so far.
  • the organic EL display device has the excellent features described above.
  • the electrodes are made of a transparent conductive material with a high refractive index, such as ITO (indium tin oxide), and layers with different refractive indexes are laminated, or a metal material with a high reflectance is used. Reflections at their interfaces can cause problems such as reduced contrast and glare due to internal reflection.
  • Patent Document 1 discloses a broadband ⁇ /4 plate (retardation film) and a broadband circularly polarizing plate using the same.
  • An object of the present invention is to provide a polarizing plate that is applied to an organic EL display device and that exhibits a low reflectance when viewed from an oblique direction and suppresses black tint when displaying black.
  • Another object of the present invention is to provide an organic EL display device.
  • the present inventors have applied a light absorption anisotropic layer in which the angle ⁇ between the transmittance central axis and the film normal line is 0 to 45° and the retardation in the thickness direction and the absorption anisotropy are controlled to a circularly polarizing plate. By combining them, the inventors have found that the reflectance and color when viewed from an oblique direction can be improved, and have completed the present invention.
  • a polarizer a light absorption anisotropic layer having at least one dye compound, and a ⁇ /4 retardation film
  • the angle formed by the transmittance central axis of the anisotropic light absorption layer and the normal to the layer plane of the anisotropic light absorption layer is 0 to 45°, and the thickness direction of the anisotropic light absorption layer
  • the phase difference Rth is -20 to -160 nm at a wavelength of 450 nm, a wavelength of 550 nm, and a wavelength of 630 nm
  • a polarizing plate wherein A( ⁇ ) of the light absorption anisotropic layer represented by formula (1) is 20 to 200 nm at any of wavelengths of 450 nm, 550 nm and 630 nm.
  • d is the thickness of the light absorption anisotropic layer
  • kx( ⁇ ) and ky( ⁇ ) are the in-plane orthogonal x-axis and y-axis of the light absorption anisotropic layer, respectively.
  • kz( ⁇ ) is the absorption coefficient for light with wavelength ⁇ in the z-axis direction perpendicular to the plane containing the x-axis and y-axis.
  • the unit of the thickness of the light absorption anisotropic layer represented by d is nm.
  • A( ⁇ ) is 40 to 150 nm at a wavelength of 450 nm, 550 nm and 630 nm.
  • the polarizer, the light absorption anisotropic layer and the ⁇ / 4 retardation film are laminated in this order, or the polarizer, the ⁇ / 4 retardation film and the light absorption anisotropy
  • a polarizing plate that is applied to an organic EL display device and has a low reflectance when viewed from an oblique direction and suppresses black tint when displaying black, and an image display device. can be provided.
  • a numerical range represented by "-" means a range including the numerical values before and after "-" as lower and upper limits.
  • parallel and orthogonal do not mean parallel and orthogonal in a strict sense, but mean a range of ⁇ 5° from parallel or orthogonal.
  • liquid crystalline composition and “liquid crystalline compound” also conceptually includes those that no longer exhibit liquid crystallinity due to curing or the like.
  • each component may be a substance corresponding to each component either singly or in combination of two or more.
  • the content of the component refers to the total content of the substances used in combination unless otherwise specified.
  • (meth)acrylate” is a notation representing “acrylate” or “methacrylate”
  • (meth)acrylic is a notation representing "acrylic” or “methacrylic”
  • (Meth)acryloyl” is a notation representing “acryloyl” or “methacryloyl”.
  • the refractive indices nx and ny are respectively the refractive indices in the in-plane direction of the optical member. is the refractive index in the orthogonal orientation).
  • nz is the refractive index in the thickness direction.
  • Re ( ⁇ ) and Rth ( ⁇ ) represent the in-plane retardation and the thickness direction retardation at the wavelength ⁇ , respectively, and the refractive indices nx, ny, and nz, and the film thickness d ( ⁇ m ), it is represented by the following equations (1) and (2).
  • Formula (1): Re( ⁇ ) (nx ⁇ ny) ⁇ d ⁇ 1000 (nm)
  • Formula (2): Rth( ⁇ ) ((nx+ny)/2 ⁇ nz) ⁇ d ⁇ 1000 (nm)
  • the wavelength ⁇ is 550 nm.
  • the slow axis orientation, Re( ⁇ ), and Rth( ⁇ ) can be measured using, for example, AxoScan OPMF-1 (manufactured by Optoscience).
  • the polarizing plate of the present invention includes a polarizer, a light absorption anisotropic layer having at least one dye compound, and a ⁇ / 4 retardation film, and the transmittance center of the light absorption anisotropic layer
  • the angle formed by the axis and the normal to the layer plane of the anisotropic light absorption layer is 0 to 45°, and the retardation Rth in the thickness direction of the anisotropic light absorption layer is 450 nm, 550 nm, and 630 nm.
  • A( ⁇ ) of the light absorption anisotropic layer represented by the following formula (1) is 20 to 200 nm at a wavelength of 450 nm, a wavelength of 550 nm, and a wavelength of 630 nm.
  • d is the thickness of the anisotropic light absorption layer
  • kx and ky are absorption coefficients for light of wavelength ⁇ in the directions of the x-axis and y-axis that are orthogonal to each other in the plane of the anisotropic light absorption layer.
  • kz is the absorption coefficient for light of wavelength ⁇ in the z-axis direction perpendicular to the plane containing the x-axis and the y-axis.
  • the unit of the thickness of the light absorption anisotropic layer represented by d is nm. Structures included in the polarizing plate of the present invention will be described below.
  • the polarizing plate of the present invention contains a ⁇ /4 retardation film.
  • the ⁇ /4 retardation film is not particularly limited, and may consist of a single optically anisotropic layer, or may consist of a plurality of optically anisotropic layers. That is, the ⁇ /4 retardation film may have a single layer structure or a multilayer structure.
  • the ⁇ /4 retardation film composed of a plurality of optically anisotropic layers for example, the description in paragraphs [0008] to [0053] of JP-A-2014-209219 can be referred to.
  • such a ⁇ /4 retardation film and a light absorption anisotropic film described later may be provided in contact with each other, or another layer may be provided between them.
  • Such a layer includes an adhesive layer and an adhesive layer for securing adhesion.
  • the ⁇ / 4 plate retardation film used in the polarizing plate of the present invention is a film having the function of generating a phase difference of ⁇ / 4, specifically, linearly polarized light with a specific wavelength is circularly polarized (or circularly polarized light into linearly polarized light).
  • the in-plane retardation Re(550) at a wavelength of 550 nm of the ⁇ /4 plate retardation film used in the polarizing plate of the present invention is preferably 100 to 200 nm, more preferably 120 to 160 nm.
  • the ⁇ /4 retardation film has a single layer structure
  • a stretched polymer film specifically, a retardation film having an optically anisotropic layer having a ⁇ /4 function on a support, and the like.
  • a broadband ⁇ /4 plate formed by laminating a ⁇ /4 plate and a ⁇ /2 plate can be mentioned.
  • the polarizing plate of the present invention includes a light absorption anisotropic layer.
  • the angle between the transmittance center axis of the light absorption anisotropic layer and the normal to the layer plane of the light absorption anisotropic layer is 0 to 45°.
  • the central axis of transmittance refers to the angle of inclination with respect to the normal to the layer plane of the anisotropic light absorption layer (the normal direction of the film), and the highest transmittance when the transmittance is measured by changing the inclination direction. means the angle and direction shown.
  • the angle between the central axis of transmittance and the normal to the film is preferably 0 to 10°, more preferably 0 to 5°, even more preferably 0 to 2°.
  • the transmittance when viewed from the front direction can be increased, and the front luminance of the image display device can be increased.
  • AxoScan OPMF-1 manufactured by Optoscience is used to measure the transmittance of the light absorption anisotropic layer for P-polarized light having a wavelength of 550 nm.
  • the azimuth angle at which the transmittance central axis is tilted is first searched, and then the in-plane While changing the polar angle, which is the angle with respect to the normal direction of the light absorption anisotropic layer surface, from ⁇ 70 to 70° in increments of 5° in (a plane that includes the transmittance central axis and is orthogonal to the layer surface), P-polarized light with a wavelength of 550 nm is incident and the transmittance of the light absorption anisotropic layer is measured.
  • the direction with the highest transmittance is defined as the center axis of transmittance.
  • the azimuth angle for changing the polar angle may be in any direction.
  • the light absorption anisotropic layer has at least one dye compound.
  • the dye compound is preferably a dichroic dye compound (hereinafter simply referred to as a dichroic dye) having a different absorption rate depending on the direction. The dye compound will be described in detail later.
  • a mode for controlling the central axis of the transmission axis of the light absorption anisotropic layer a mode in which the dichroic dye is oriented is preferable, and a mode in which the dichroic dye is oriented using the alignment of the liquid crystalline compound is more preferable.
  • An example of the light absorption anisotropic layer that satisfies the relationship regarding the transmittance center axis is a light absorption anisotropic layer in which at least one kind of dichroic dye is oriented perpendicularly to the layer plane of the light absorption anisotropic layer. layer.
  • the technology to orient the dichroic dyes in the desired orientation it is possible to refer to the technology for manufacturing polarizers using dichroic dyes and the technology for manufacturing guest-host liquid crystal cells.
  • the method for producing a dichroic polarizing element described in JP-A-11-305036 and JP-A-2002-090526, and the guest host described in JP-A-2002-099388 and JP-A-2016-027387 The technology used in the manufacturing method of the type liquid crystal display device can also be used in manufacturing the light absorption anisotropic layer used in the present invention.
  • dichroic dye molecules can be oriented as desired along with the orientation of the host liquid crystal.
  • a guest dichroic dye and a rod-like liquid crystalline compound serving as a host liquid crystal are mixed, the host liquid crystal is aligned, and the molecules of the dichroic dye are aligned along the alignment of the liquid crystal molecules.
  • the light absorption anisotropic layer for use in the present invention can be produced by allowing the layers to align and fixing the orientation state.
  • the orientation of the dichroic dye can be fixed by advancing the polymerization of the host liquid crystal, the dichroic dye, or the optionally added polymerizable component.
  • a guest-host type liquid crystal cell itself having a liquid crystal layer containing at least a dichroic dye and a host liquid crystal on a pair of substrates may be used as the light absorption anisotropic layer used in the present invention.
  • the orientation of the host liquid crystal (and the accompanying dichroic dye molecule orientation) can be controlled by an orientation film formed on the inner surface of the substrate, and the orientation state is maintained unless an external stimulus such as an electric field is applied.
  • the light absorption characteristics of the light absorption anisotropic layer used in the present invention can be made constant.
  • the light absorption anisotropic layer used in the present invention it is also possible to prepare polymer films that satisfy the light absorption properties of Specifically, it can be produced by applying a solution of a dichroic dye to the surface of a polymer film and allowing it to permeate into the film.
  • the orientation of the dichroic dye can be adjusted by the orientation of the polymer chains in the polymer film, the properties thereof (chemical and physical properties such as the polymer chains or functional groups possessed by the polymer chains), the coating method, and the like. Details of this method are described in JP-A-2002-090526.
  • the thickness direction retardation Rth of the light absorption anisotropic layer used in the polarizing plate of the present invention is ⁇ 20 to ⁇ 160 nm, and ⁇ 20 to ⁇ 100 nm at any of wavelengths of 450 nm, 550 nm and 630 nm. It is preferably -40 to -80 nm, more preferably -40 to -80 nm.
  • the polarizing plate of the present invention uses a light absorption anisotropic layer that satisfies the above requirements.
  • the degree of absorption anisotropy of the light absorption anisotropic layer can be expressed by various parameters, one example of which is A( ⁇ ) defined below.
  • the light-absorbing anisotropic layer satisfies the relationship described below with respect to A( ⁇ ).
  • A( ⁇ ) ⁇ kz( ⁇ ) ⁇ (kx( ⁇ )+ky( ⁇ ))/2 ⁇ d
  • d is the thickness (unit: nm) of the light absorption anisotropic layer
  • kx( ⁇ ) and ky( ⁇ ) are the in-plane orthogonal x-axes of the light absorption anisotropic layer, respectively.
  • kz( ⁇ ) is an absorption coefficient for light of wavelength ⁇ in the z-axis direction perpendicular to the plane containing the x-axis and the y-axis.
  • the x-axis is the direction in which the refractive index is the largest at wavelength ⁇ (450 nm wavelength, 550 nm wavelength, or 630 nm wavelength)
  • the y-axis is the in-plane direction orthogonal to the x-axis.
  • the absorption coefficient k (kx, ky and kz), also called an attenuation index, is a value related to how much light energy is absorbed in a substance.
  • the real component n of the complex refractive index (n+ik (i is an imaginary unit)) is the so-called refractive index
  • the imaginary component k is the absorption coefficient. Note that k described in the present invention is a physical property value different from the so-called attenuation coefficient ⁇ .
  • the attenuation index and attenuation coefficient are described in detail, for example, in Max Born and Emil Wolf's “Principles of Optics, 7th (expanded) edition", 4.11.2 “Beam propagation in an absorbing maximn”, pp. 218-219. be.
  • the value of A( ⁇ ) is 20 to 200 nm, more preferably 20 to 150 nm, at any of wavelengths of 450 nm, 550 nm and 630 nm. 40 to 150 nm is more preferred, and 40 to 80 nm is even more preferred.
  • the magnitude relationship between the absorption coefficients kx( ⁇ ), ky( ⁇ ), and kz( ⁇ ) can be known from the value of the absorption anisotropy (Diattenuation) of the sample measured using AxosScan of Axometics.
  • the degree of absorption anisotropy A ( ⁇ ) is measured using the above-described measuring device, and the polar angle in the fast axis direction is set within a predetermined range (eg, ⁇ 50 to 5°) at predetermined intervals (eg, every 10°). can be obtained by measuring and fitting Mueller matrices at a plurality of wavelengths ⁇ .
  • the light absorption anisotropic layer used in the present invention preferably has a transmittance of 80% or more, more preferably 85% or more, in the central axis direction of the transmission axis. As a result, the brightness at the center of the viewing angle of the image display device can be increased, and the visibility can be improved.
  • the ⁇ /4 retardation film and the light absorption anisotropic layer are preferably arranged on the same side as viewed from the polarizer. That is, the polarizer, the light absorption anisotropic layer and the ⁇ / 4 retardation film are laminated in this order, or the polarizer, the ⁇ / 4 retardation film and the light absorption anisotropic layer are laminated in this order. It is preferable that More preferably, the polarizer, the light absorption anisotropic layer and the ⁇ /4 retardation film are laminated in this order. By adopting such a configuration, it is possible to reduce the generation of reflected light caused by external light incident from an oblique direction, and suppress the change in color of the reflected light.
  • the components contained in the light absorption anisotropic layer are described below.
  • the light absorption anisotropic layer preferably contains a liquid crystalline compound. That is, it is preferable to form the anisotropic light absorption layer using a composition for forming an anisotropic light absorption layer containing a liquid crystalline compound and a dye compound. By containing the liquid crystalline compound, it is possible to align the dye compound (preferably dichroic dye) with a high degree of alignment while suppressing precipitation of the dye compound (preferably dichroic dye).
  • the liquid crystalline compound is preferably a liquid crystalline compound that does not exhibit dichroism in the visible region.
  • liquid crystal compound it is possible to use either a low-molecular-weight liquid crystal compound or a high-molecular-weight liquid crystal compound, and it is also preferable to use both together.
  • low-molecular-weight liquid crystalline compound refers to a liquid crystalline compound having no repeating unit in its chemical structure.
  • polymeric liquid crystalline compound refers to a liquid crystalline compound having a repeating unit in its chemical structure.
  • low-molecular-weight liquid crystalline compounds examples include liquid crystalline compounds described in JP-A-2013-228706.
  • polymer liquid crystalline compounds examples include thermotropic liquid crystalline polymers described in JP-A-2011-237513.
  • the polymer liquid crystalline compound preferably has a repeating unit having a crosslinkable group at the terminal from the viewpoint of excellent strength (in particular, bending resistance) of the light absorption anisotropic film.
  • the crosslinkable group examples include polymerizable groups described in paragraphs [0040] to [0050] of JP-A-2010-244038. Among these, acryloyl group, methacryloyl group, epoxy group, oxetanyl group, and styryl group are preferred, and acryloyl group and methacryloyl group are more preferred, from the viewpoint of improving reactivity and synthesis suitability.
  • the liquid crystallinity exhibited by the liquid crystalline compound may be either a nematic phase or a smectic phase, or may exhibit both a nematic phase and a smectic phase, and preferably exhibits at least a nematic phase.
  • the smectic phase may be a higher order smectic phase.
  • the higher-order smectic phases referred to herein include smectic B phase, smectic D phase, smectic E phase, smectic F phase, smectic G phase, smectic H phase, smectic I phase, smectic J phase, smectic K phase, and smectic L.
  • a smectic B phase, a smectic F phase, or a smectic I phase is preferable. If the smectic phase exhibited by the liquid crystalline compound is one of these high-order smectic phases, a light absorption anisotropic layer with a higher degree of orientational order can be produced. In addition, a light absorption anisotropic layer formed from a high-order smectic phase having a high degree of orientational order gives a Bragg peak derived from a high-order structure such as a hexatic phase and a crystal phase in X-ray diffraction measurement.
  • the above-mentioned Bragg peak is a peak derived from the plane periodic structure of molecular orientation, and a light absorption anisotropic layer having a periodic interval of 3.0 to 5.0 ⁇ is preferable.
  • the temperature range showing the nematic phase is preferably room temperature (23° C.) to 450° C., and preferably 50 to 400° C. from the viewpoint of handling and production suitability.
  • the content of the liquid crystalline compound is preferably 25 to 2000 parts by mass, more preferably 100 to 1300 parts by mass, with respect to 100 parts by mass of the dye compound (preferably dichroic dye) content, and 200 to 900 parts by mass. is more preferred.
  • the degree of orientation of the dye compound is further improved.
  • the liquid crystalline compound may be contained individually by 1 type, and may be contained 2 or more types. When two or more kinds of liquid crystalline compounds are contained, the content of the liquid crystalline compounds means the total content of the liquid crystalline compounds.
  • the liquid crystalline compound is preferably a polymeric liquid crystalline compound containing a repeating unit represented by the following formula (1L) (hereinafter also referred to as "repeating unit (1L)”) because of its superior degree of orientation.
  • P1 represents the main chain of the repeating unit
  • L1 represents a single bond or a divalent linking group
  • SP1 represents a spacer group
  • M1 represents a mesogenic group
  • T1 represents a terminal group.
  • main chain of the repeating unit represented by P1 include groups represented by the following formulas (P1-A) to (P1-D).
  • a group represented by the following formula (P1-A) is preferable from the viewpoint of diversity and ease of handling.
  • R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 10 carbon atoms. represents an alkoxy group.
  • the alkyl group may be a linear or branched alkyl group, or may be an alkyl group having a cyclic structure (cycloalkyl group).
  • the number of carbon atoms in the alkyl group is preferably 1 to 5.
  • the group represented by formula (P1-A) is preferably one unit of the partial structure of poly(meth)acrylic acid ester obtained by polymerization of (meth)acrylic acid ester.
  • the group represented by formula (P1-B) is preferably an ethylene glycol unit formed by ring-opening polymerization of an epoxy group of a compound having an epoxy group.
  • the group represented by formula (P1-C) is preferably a propylene glycol unit formed by ring-opening polymerization of an oxetane group of a compound having an oxetane group.
  • the group represented by formula (P1-D) is preferably a siloxane unit of polysiloxane obtained by condensation polymerization of a compound having at least one of an alkoxysilyl group and a silanol group.
  • compounds having at least one of an alkoxysilyl group and a silanol group include compounds having a group represented by the formula SiR 4 (OR 5 ) 2 —.
  • R 4 has the same definition as R 4 in (P1-D), and each of a plurality of R 5 independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • L1 is a single bond or a divalent linking group.
  • the divalent linking group represented by L1 includes -C(O)O-, -OC(O)-, -O-, -S-, -C(O)NR 3 -, and -NR 3 C(O). -, -SO 2 -, and -NR 3 R 4 -.
  • R 3 and R 4 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent W (described later).
  • P1 is a group represented by formula (P1-A)
  • L1 is preferably a group represented by -C(O)O- for the reason that the degree of orientation is superior.
  • P1 is a group represented by formulas (P1-B) to (P1-D)
  • L1 is preferably a single bond because the degree of orientation is superior.
  • the spacer group represented by SP1 is at least one selected from the group consisting of an oxyethylene structure, an oxypropylene structure, a polysiloxane structure and an alkylene fluoride structure, for reasons such as the ease of exhibiting liquid crystallinity and the availability of raw materials. It preferably contains a seed structure.
  • the oxyethylene structure represented by SP1 is preferably a group represented by *--(CH 2 --CH 2 O) n1 --*.
  • n1 represents an integer of 1 to 20
  • * represents the bonding position with L1 or M1 in the above formula (1L).
  • n1 is preferably an integer of 2 to 10, more preferably an integer of 2 to 4, and most preferably 3, because the degree of orientation is more excellent.
  • the oxypropylene structure represented by SP1 is preferably a group represented by *-(CH(CH 3 )-CH 2 O) n2 --* because of its superior degree of orientation.
  • n2 represents an integer of 1 to 3
  • * represents the bonding position with L1 or M1.
  • the polysiloxane structure represented by SP1 is preferably a group represented by *-(Si(CH 3 ) 2 -O) n3 -* because of its superior degree of orientation.
  • n3 represents an integer of 6 to 10 * represents the bonding position with L1 or M1.
  • alkylene fluoride structure represented by SP1 is preferably a group represented by *-(CF 2 -CF 2 ) n4 -* because of its superior degree of orientation.
  • n4 represents an integer of 6 to 10
  • * represents the bonding position with L1 or M1.
  • the mesogenic group represented by M1 is a group showing the main skeleton of liquid crystal molecules that contributes to liquid crystal formation.
  • Liquid crystal molecules exhibit liquid crystallinity, which is an intermediate state (mesophase) between a crystalline state and an isotropic liquid state.
  • mesogenic group for example, "Flussige Kristalle in Tabellen II” (VEB Manual Verlag fur Grundstoff Industrie, Leipzig, 1984), especially the descriptions on pages 7 to 16 and Liquid Crystal Handbook Editorial Committee ed., Liquid Crystal Handbook (Maruzen, 2000), especially the description in Chapter 3.
  • the mesogenic group is preferably, for example, a group having at least one cyclic structure selected from the group consisting of aromatic hydrocarbon groups, heterocyclic groups and alicyclic groups.
  • the mesogenic group preferably has an aromatic hydrocarbon group, more preferably has 2 to 4 aromatic hydrocarbon groups, and has 3 aromatic hydrocarbon groups for the reason that the degree of orientation is better. is more preferred.
  • the mesogenic group As the mesogenic group, the following formula (M1-A) or the following formula (M1-B) is used from the viewpoint of liquid crystal development, adjustment of the liquid crystal phase transition temperature, availability of raw materials and synthesis suitability, and superior degree of orientation.
  • a group represented by is preferable, and a group represented by formula (M1-B) is more preferable.
  • A1 is a divalent group selected from the group consisting of aromatic hydrocarbon groups, heterocyclic groups and alicyclic groups. These groups may be substituted with an alkyl group, a fluorinated alkyl group, an alkoxy group, or a substituent W (described later).
  • the divalent group represented by A1 is preferably a 4- to 6-membered ring. Also, the divalent group represented by A1 may be monocyclic or condensed. * represents the binding position with SP1 or T1.
  • the divalent aromatic hydrocarbon group represented by A1 includes a phenylene group, a naphthylene group, a fluorene-diyl group, an anthracene-diyl group and a tetracene-diyl group.
  • a phenylene group or a naphthylene group is preferred, and a phenylene group is more preferred, from the viewpoint of properties and the like.
  • the divalent heterocyclic group represented by A1 may be either aromatic or non-aromatic, but from the viewpoint of further improving the degree of orientation, it is preferably a divalent aromatic heterocyclic group.
  • Atoms other than carbon constituting the divalent aromatic heterocyclic group include a nitrogen atom, a sulfur atom and an oxygen atom.
  • the aromatic heterocyclic group has a plurality of non-carbon ring-constituting atoms, these may be the same or different.
  • divalent aromatic heterocyclic groups include, for example, pyridylene group (pyridine-diyl group), pyridazine-diyl group, imidazole-diyl group, thienylene (thiophene-diyl group), quinolylene group (quinoline-diyl group ), isoquinolylene group (isoquinoline-diyl group), oxazole-diyl group, thiazole-diyl group, oxadiazole-diyl group, benzothiazole-diyl group, benzothiadiazole-diyl group, phthalimide-diyl group, thienothiazole-diyl group , thiazolothiazole-diyl group, thienothiophene-diyl group, and thienooxazole-diyl group.
  • pyridylene group pyridine-diy
  • divalent alicyclic group represented by A1 examples include a cyclopentylene group and a cyclohexylene group.
  • a1 represents an integer of 1-10. When a1 is 2 or more, multiple A1s may be the same or different.
  • A2 and A3 are each independently a divalent group selected from the group consisting of aromatic hydrocarbon groups, heterocyclic groups and alicyclic groups. Specific examples and preferred embodiments of A2 and A3 are the same as those of A1 in formula (M1-A), so description thereof is omitted.
  • a2 represents an integer of 1 to 10, and when a2 is 2 or more, multiple A2 may be the same or different, and multiple A3 may be the same or different.
  • a plurality of LA1 may be the same or different.
  • a2 is preferably an integer of 2 or more, more preferably 2, because the degree of orientation is better.
  • LA1 is a divalent linking group.
  • each of the plurality of LA1 is independently a single bond or a divalent linking group, and at least one of the plurality of LA1 is a divalent linking group.
  • a2 is 2 or more, each of the plurality of LA1 is independently a single bond or a divalent linking group, and at least one of the plurality of LA1 is a divalent linking group.
  • a2 is 2, it is preferable that one of the two LA1s is a divalent linking group and the other is a single bond because the degree of orientation is superior.
  • M1 include the following structures.
  • Ac represents an acetyl group.
  • Terminal groups represented by T1 include a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, alkoxycarbonyloxy group having 1 to 10 carbon atoms, alkoxycarbonyl group having 1 to 10 carbon atoms (ROC(O)-: R is an alkyl group), acyloxy group having 1 to 10 carbon atoms, acylamino group having 1 to 10 carbon atoms , an alkoxycarbonylamino group having 1 to 10 carbon atoms, a sulfonylamino group having 1 to 10 carbon atoms, a sulfamoyl group having 1 to 10 carbon atoms, a carbamoyl group having 1 to 10 carbon atoms, a sulfinyl group having 1 to 10 carbon
  • (meth)acryloyloxy group-containing group for example, -LA (L represents a single bond or a linking group. Specific examples of the linking group are the same as L1 and SP1 described above.
  • A is (meth) represents an acryloyloxy group).
  • T1 is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 5 carbon atoms, and even more preferably a methoxy group, because the degree of orientation is superior. These terminal groups may be further substituted with these groups or the crosslinkable groups described above.
  • the number of atoms in the main chain of T1 is preferably from 1 to 20, more preferably from 1 to 15, even more preferably from 1 to 10, and particularly preferably from 1 to 7, because the degree of orientation is superior.
  • the degree of orientation of the light absorption anisotropic layer is further improved.
  • the "main chain" in T1 means the longest molecular chain that binds to M1, and hydrogen atoms are not counted in the number of atoms in the main chain of T1.
  • T1 is an n-butyl group
  • the number of atoms in the main chain is 4
  • T1 is a sec-butyl group
  • the number of atoms in the main chain is 3.
  • the content is preferably 20 to 100% by mass with respect to 100% by mass of all repeating units in the polymer liquid crystalline compound, since the degree of orientation is more excellent.
  • the content of each repeating unit contained in the polymer liquid crystalline compound is calculated based on the charged amount (mass) of each monomer used to obtain each repeating unit.
  • the repeating unit (1L) may be contained singly or in combination of two or more in the polymer liquid crystalline compound. Among them, it is preferable that two kinds of repeating units (1L) are contained in the polymer liquid crystalline compound for the reason that the degree of orientation is more excellent.
  • the terminal group represented by T1 in one (repeating unit A) is an alkoxy group, and in the other (repeating unit B), the orientation degree is more excellent.
  • the terminal group represented by T1 is preferably a group other than an alkoxy group.
  • the terminal group represented by T1 in the repeating unit B is preferably an alkoxycarbonyl group, a cyano group, or a (meth)acryloyloxy group-containing group for the reason that the degree of orientation is better, and an alkoxycarbonyl group or a cyano more preferably a group.
  • the ratio (A/B) between the content of the repeating unit A in the liquid crystalline polymer compound and the content of the repeating unit B in the liquid crystalline polymer compound is 50/50 for the reason that the degree of orientation is more excellent. 95/5 is preferred, 60/40 to 93/7 is more preferred, and 70/30 to 90/10 is even more preferred.
  • the polymer liquid crystalline compound may have a repeating unit having no mesogenic group.
  • Repeating units having no mesogenic group include repeating units in which M1 in formula (1L) is a single bond.
  • the degree of orientation is more excellent, and therefore the amount is more than 0% by mass and 30% by mass or less with respect to 100% by mass of all repeating units possessed by the polymer liquid crystalline compound. is preferable, and more than 10% by mass and 20% by mass or less is more preferable.
  • the weight-average molecular weight (Mw) of the polymer liquid crystalline compound is preferably 1,000 to 500,000, more preferably 2,000 to 300,000, because the degree of orientation is better.
  • the Mw of the liquid crystalline polymer compound is within the above range, the liquid crystalline polymer compound can be easily handled.
  • the weight average molecular weight (Mw) of the polymer liquid crystalline compound is preferably 10,000 or more, more preferably 10,000 to 300,000.
  • the weight average molecular weight (Mw) of the polymer liquid crystalline compound is preferably less than 10,000, more preferably 2,000 or more and less than 10,000.
  • the weight average molecular weight and number average molecular weight in the present invention are values measured by a gel permeation chromatography (GPC) method.
  • the substituent W in the present specification will be explained.
  • the substituent W include an alkyl group (preferably an alkyl group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably an alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, isopropyl group, tert-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, and cyclohexyl group), alkenyl group (preferably having 2 to 20 carbon atoms) , more preferably an alkenyl group having 2 to 12 carbon atoms, particularly preferably an alkenyl group having 2 to 8 carbon atoms, such as a vinyl group, an aryl group, a 2-butenyl group, and a 3-pentenyl group), alkynyl a group (preferably an
  • sulfonylamino group preferably 1 to 20 carbon atoms, more preferably carbon 1 to 10, particularly preferably 1 to 6 carbon atoms, such as methanesulfonylamino group and benzenesulfonylamino group
  • sulfamoyl group preferably 0 to 20 carbon atoms, more preferably carbon Number 0 to 10, particularly preferably 0 to 6 carbon atoms, examples include sulfamoyl group, methylsulfamoyl group, dimethylsulfamoyl group, and phenylsulfamoyl group), carbamoyl group (preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 6 carbon atoms, such as unsubstituted carbamoyl group, methyl
  • an alkylthio group preferably having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms, such as a methylthio group and an ethylthio group
  • Arylthio group preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as a phenylthio group
  • a sulfonyl group preferably having 1 to 1 carbon atoms) 20, more preferably 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms, such as mesyl group and tosyl group
  • sulfinyl group preferably 1 to 20 carbon atoms, more preferably 1 to 20 carbon atoms
  • hydroxy group mercapto group, halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, and iodine atom), cyano group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, azo group, a heterocyclic group (preferably a heterocyclic group having 1 to 30 carbon atoms, more preferably a heterocyclic group having 1 to 12 carbon atoms, for example, a heterocyclic group having a heteroatom such as a nitrogen atom, an oxygen atom, a sulfur atom, etc.) , for example, an epoxy group, an oxetanyl group, an imidazolyl group, a pyridyl group, a quinolyl group, a furyl group, a piperidyl group, a morpholino group, a maleimide group, a benzoxazolyl group, a benzimidazo
  • the light absorption anisotropic layer contains a dye compound.
  • the dye compound is preferably a dichroic dye compound (dichroic dye).
  • Dichroic dyes are not particularly limited, and include visible light absorbing substances (organic dichroic dyes, dichroic azo compounds), light emitting substances (fluorescent substances, phosphorescent substances), ultraviolet absorbing substances, infrared absorbing substances, nonlinear optical substances. , carbon nanotubes, inorganic substances (for example, quantum rods), and the like, and conventionally known dichroic dyes can be used.
  • the dichroic dye means a dye compound having different absorbance depending on the direction.
  • a particularly preferred dichroic dye is a dichroic azo dye compound.
  • the dichroic azo dye compound is not particularly limited, and conventionally known dichroic azo dyes can be used, but the compounds described below are preferably used.
  • a dichroic azo dye compound means an azo dye compound having different absorbance depending on the direction.
  • the dichroic azo dye compound may or may not exhibit liquid crystallinity.
  • the dichroic azo dye compound When the dichroic azo dye compound exhibits liquid crystallinity, it may exhibit nematicity or smecticity.
  • the temperature range showing the liquid crystal phase is preferably room temperature (about 20 to 28°C) to 300°C, and more preferably 50 to 200°C from the viewpoint of handleability and production suitability.
  • the light absorption anisotropic layer contains at least one dye compound having a maximum absorption wavelength in the wavelength range of 560 to 700 nm (hereinafter, “first dichroic azo dye compound”) and at least one dye compound having a maximum absorption wavelength in the wavelength range of 455 nm or more and less than 560 nm (hereinafter also abbreviated as “second dichroic azo dye compound”).
  • first dichroic azo dye compound at least one dye compound having a maximum absorption wavelength in the wavelength range of 455 nm or more and less than 560 nm
  • second dichroic azo dye compound Specifically, it has at least a dichroic azo dye compound represented by formula (3) described later and a dichroic azo dye compound represented by formula (4) described later. more preferably.
  • dichroic azo dye compounds may be used in combination.
  • dichroic azo dye compound and at least one dye compound having a maximum absorption wavelength in the wavelength range of 380 nm or more and less than 455 nm (hereinafter also abbreviated as "third dichroic azo dye compound”). is preferred.
  • the dichroic azo dye compound preferably has a crosslinkable group from the viewpoint of better pressure resistance.
  • the crosslinkable group include a (meth)acryloyl group, an epoxy group, an oxetanyl group, a styryl group, etc. Among them, a (meth)acryloyl group is preferred.
  • the first dichroic azo dye compound is preferably a compound having a chromophore as a nucleus and a side chain bonded to the terminal of the chromophore.
  • the chromophore include aromatic ring groups (e.g., aromatic hydrocarbon groups, aromatic heterocyclic groups), azo groups and the like, and structures having both an aromatic ring group and an azo group are preferred.
  • a bisazo structure having an aromatic heterocyclic group (preferably a thienothiazole group) and two azo groups is more preferred.
  • the side chain is not particularly limited, and includes groups represented by L3, R2 or L4 in formula (3) described below.
  • the first dichroic azo dye compound is a dichroic azo dye compound having a maximum absorption wavelength in the wavelength range of 560 to 700 nm. and more preferably a dichroic azo dye compound having a maximum absorption wavelength in the range of 560 to 640 nm.
  • the maximum absorption wavelength (nm) of the dichroic azo dye compound in this specification is a solution of the dichroic azo dye compound dissolved in a good solvent, and is measured with a spectrophotometer at a wavelength of 380 to 800 nm. It is determined from the UV-visible spectrum in the range.
  • the first dichroic azo dye compound is preferably a compound represented by the following formula (3) for the reason that the degree of orientation of the light absorption anisotropic layer to be formed is further improved. .
  • Ar1 and Ar2 each independently represent an optionally substituted phenylene group or an optionally substituted naphthylene group, preferably a phenylene group.
  • R1 is a hydrogen atom, an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkylcarbonyl group.
  • alkyloxycarbonyl group alkyloxycarbonyl group, acyloxy group, alkyl carbonate group, alkylamino group, acylamino group, alkylcarbonylamino group, alkoxycarbonylamino group, alkylsulfonylamino group, alkylsulfamoyl group, alkylcarbamoyl group, alkylsulfinyl group, alkyl It represents a ureido group, an alkylphosphoamide group, an alkylimino group, or an alkylsilyl group.
  • R1 is a group other than a hydrogen atom
  • R1' represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms. In each group, when a plurality of R1' are present, they may be the same or different.
  • R2 and R3 are each independently a hydrogen atom, an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, an alkoxy group, an acyl group, an alkyl represents an oxycarbonyl group, an alkylamide group, an alkylsulfonyl group, an aryl group, an arylcarbonyl group, an arylsulfonyl group, an aryloxycarbonyl group, or an arylamide group; —CH 2 — constituting the alkyl group is —O—, —S—, —C(O)—, —C(O)—O—, —O—C(O)—, —C(O) -S-, -S-C(O)-, -Si(CH 3 ) 2 -O-Si(CH 3 ) 2 -, -NR2'-, -NR2'-CO-, -CO-NR2'-, -, -
  • R2 and R3 are groups other than hydrogen atoms
  • R2' represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms. In each group, when there are multiple R2's, they may be the same or different.
  • R2 and R3 may combine with each other to form a ring, or R2 or R3 may combine with Ar2 to form a ring.
  • R1 is preferably an electron-withdrawing group
  • R2 and R3 are preferably groups with low electron-donating properties.
  • R1 include an alkylsulfonyl group, an alkylcarbonyl group, an alkyloxycarbonyl group, an acyloxy group, an alkylsulfonylamino group, an alkylsulfamoyl group, an alkylsulfinyl group, an alkylureido group, and the like.
  • R2 and R3 include groups having the following structures. The group having the structure below is shown in the above formula (3) in a form containing the nitrogen atom to which R2 and R3 are bonded.
  • first dichroic azo dye compound examples include but are not limited thereto.
  • the second dichroic azo dye compound is a different compound from the first dichroic azo dye compound, specifically in its chemical structure.
  • the second dichroic azo dye compound is preferably a compound having a chromophore that is the nucleus of the dichroic azo dye compound and a side chain that binds to the terminal of the chromophore.
  • Specific examples of the chromophore include aromatic ring groups (e.g., aromatic hydrocarbon groups, aromatic heterocyclic groups), azo groups and the like, and structures having both an aromatic hydrocarbon group and an azo group are preferred. , a bisazo or trisazo structure having an aromatic hydrocarbon group and two or three azo groups is more preferred.
  • the side chain is not particularly limited, and includes groups represented by R4, R5 or R6 in formula (4) described below.
  • the second dichroic azo dye compound is a dichroic azo dye compound having a maximum absorption wavelength in the range of wavelength 455 nm or more and less than 560 nm.
  • a dichroic azo dye compound having a maximum absorption wavelength in the range of 555 nm is preferable, and a dichroic azo dye compound having a maximum absorption wavelength in the wavelength range of 455 to 550 nm is more preferable.
  • first dichroic azo dye compound having a maximum absorption wavelength of 560 to 700 nm and a second dichroic azo dye compound having a maximum absorption wavelength of 455 nm or more and less than 560 nm light absorption anisotropy It becomes easier to adjust the color tone of the layer.
  • the second dichroic azo dye compound is preferably a compound represented by the formula (4) from the viewpoint of further improving the degree of orientation of the light absorption anisotropic layer.
  • n 1 or 2.
  • Ar3, Ar4 and Ar5 are each independently a phenylene group optionally having substituent(s), a naphthylene group optionally having substituent(s) or a heterocyclic group optionally having substituent(s) represents a cyclic group.
  • Heterocyclic groups can be either aromatic or non-aromatic. Atoms other than carbon constituting the aromatic heterocyclic group include a nitrogen atom, a sulfur atom and an oxygen atom. When the aromatic heterocyclic group has a plurality of non-carbon ring-constituting atoms, these may be the same or different.
  • aromatic heterocyclic groups include, for example, pyridylene group (pyridine-diyl group), pyridazine-diyl group, imidazole-diyl group, thienylene (thiophene-diyl group), quinolylene group (quinoline-diyl group), and isoquinolylene.
  • R4 is the same as that of R1 in formula (3).
  • definitions of R5 and R6 are the same as those of R2 and R3 in formula (3).
  • R4 is preferably an electron-withdrawing group
  • R5 and R6 are preferably groups with low electron-donating properties.
  • specific examples in which R4 is an electron-withdrawing group are the same as specific examples in which R1 is an electron-withdrawing group
  • R5 and R6 are groups with low electron-donating properties.
  • R2 and R3 are low electron-donating groups, specific examples are the same as the specific examples.
  • the logP value is an index that expresses the hydrophilic and hydrophobic properties of a chemical structure.
  • the absolute value of the difference between the logP value of the side chain of the first dichroic azo dye compound and the logP value of the side chain of the second dichroic azo dye compound (hereinafter also referred to as "logP difference"). is preferably 2.30 or less, more preferably 2.0 or less, still more preferably 1.5 or less, and particularly preferably 1.0 or less. If the logP difference is 2.30 or less, the affinity between the first dichroic azo dye compound and the second dichroic azo dye compound increases, making it easier to form an array structure. The degree of orientation of the anisotropic layer is further improved.
  • the side chain of the first dichroic azo dye compound and the second dichroic azo dye compound means a group that binds to the end of the chromophore described above.
  • the first dichroic azo dye compound is a compound represented by formula (3)
  • R1, R2 and R3 in formula (3) are side chains
  • the second dichroic azo dye When the compound is represented by formula (4), R4, R5 and R6 in formula (4) are side chains.
  • R1 and R4 At least one of the logP value difference between R1 and R5, the logP value difference between R2 and R4, and the logP value difference between R2 and R5 preferably fulfilled.
  • the logP value is an index that expresses the hydrophilicity and hydrophobicity of the chemical structure, and is sometimes called the hydrophilicity/hydrophobicity parameter.
  • LogP values can be calculated using software such as ChemBioDraw Ultra or HSPiP (Ver.4.1.07). Also, OECD Guidelines for the Testing of Chemicals, Sections 1, Test No. It can also be obtained experimentally by the method of 117 or the like. In the present invention, unless otherwise specified, the value calculated by inputting the structural formula of the compound into HSPiP (Ver.4.1.07) is employed as the logP value.
  • the third dichroic azo dye compound is a dichroic azo dye compound other than the first dichroic azo dye compound and the second dichroic azo dye compound, specifically, the first dichroic azo dye compound
  • the chemical structure is different from that of the chromatic azo dye compound and the second dichroic azo dye compound. If the composition for forming an anisotropic light absorption layer contains the third dichroic azo dye compound, there is an advantage that the color of the anisotropic light absorption layer can be easily adjusted.
  • the maximum absorption wavelength of the third dichroic azo dye compound is 380 nm or more and less than 455 nm, preferably 385 to 454 nm.
  • the third dichroic azo dye compound preferably contains a dichroic azo dye represented by the following formula (6).
  • a and B each independently represent a crosslinkable group.
  • a and b each independently represent 0 or 1. Both a and b are preferably 0 in terms of the degree of orientation of the light absorption anisotropic layer.
  • Ar 1 represents a (n1+2)-valent aromatic hydrocarbon group or heterocyclic group
  • Ar 2 represents a (n2+2)-valent aromatic hydrocarbon group or heterocyclic group
  • Ar 3 represents ( represents an n3+2)-valent aromatic hydrocarbon group or heterocyclic group
  • R 1 , R 2 and R 3 each independently represent a monovalent substituent.
  • n1 ⁇ 2 the plurality of R1 may be the same or different
  • n2 ⁇ 2 the plurality of R2 may be the same or different
  • n3 ⁇ 2. may be the same or different from each other.
  • k represents an integer of 1-4.
  • Examples of the crosslinkable groups represented by A and B in formula (6) include polymerizable groups described in paragraphs [0040] to [0050] of JP-A-2010-244038.
  • acryloyl group, methacryloyl group, epoxy group, oxetanyl group, and styryl group are preferred from the viewpoint of improving reactivity and synthesis aptitude, and acryloyl group and methacryloyl group are preferred from the viewpoint of further improving solubility. more preferred.
  • L2 represents a monovalent substituent
  • L2 represents a single bond or a divalent linking group
  • the monovalent substituent represented by L 1 and L 2 includes a group introduced to increase the solubility of the dichroic dye, or an electron-donating or electron-donating group introduced to adjust the color tone of the dye.
  • Groups with attractive properties are preferred.
  • an alkyl group preferably an alkyl group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, and cyclohexyl group, etc.), alkenyl group (preferably an alkenyl group having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as vinyl, ally
  • a phosphate amide group (preferably having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms, such as a diethyl phosphate amide group, a phenyl phosphate amide group, etc.
  • a heterocyclic group preferably a heterocyclic group having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, for example, a heterocyclic group having a heteroatom such as a nitrogen atom, an oxygen atom, and a sulfur atom, such as , imidazolyl group, pyridyl group, quinolyl group, furyl group, piperidyl group, morpholino group, benzoxazolyl group, benzimidazolyl group, and benzthiazolyl group),
  • a silyl group preferably a silyl group having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably a silyl group having 3 to 24 carbon atoms, such as a trimethylsilyl group and a triphenylsilyl group
  • halogen atoms e.g.
  • a hydroxy group, a mercapto group, a cyano group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, an azo group, and the like can be used.
  • These substituents may be further substituted by these substituents.
  • when it has two or more substituents they may be the same or different.
  • they may be bonded to each other to form a ring.
  • R B (OR A ) na — groups, which are groups in which an alkoxy group is substituted with an alkyl group.
  • R A represents an alkylene group having 1 to 5 carbon atoms
  • R B represents an alkyl group having 1 to 5 carbon atoms
  • na is 1 to 10 (preferably 1 to 5, more preferably 1 to 3) represents an integer.
  • the monovalent substituents represented by L 1 and L 2 include alkyl groups, alkenyl groups, alkoxy groups, and groups in which these groups are further substituted with these groups (for example, R B —(OR A ) na — group) is preferred, and alkyl groups, alkoxy groups, and groups in which these groups are further substituted with these groups (for example, R B —(OR A ) na described above). - group) is more preferred.
  • Examples of divalent linking groups represented by L 1 and L 2 include -O-, -S-, -CO-, -COO-, -OCO-, -O-CO-O-, -CO-NR N —, —O—CO—NR N —, —NR N —CO—NR N —, —SO 2 —, —SO—, an alkylene group, a cycloalkylene group, an alkenylene group, and two of these groups The group which combined above etc. is mentioned. Among these, a group obtained by combining an alkylene group and one or more groups selected from the group consisting of -O-, -COO-, -OCO- and -O-CO-O- is preferred.
  • RN represents a hydrogen atom or an alkyl group. When there are multiple RNs , the multiple RNs may be the same or different.
  • the number of atoms in the main chain of at least one of L 1 and L 2 is preferably 3 or more, more preferably 5 or more. Preferably, the number is 7 or more, and particularly preferably 10 or more.
  • the upper limit of the number of atoms in the main chain is preferably 20 or less, more preferably 12 or less.
  • the number of atoms in the main chain of at least one of L 1 and L 2 is preferably 1 to 5.
  • the “main chain” in L 1 means the “O” atom that connects L 1 and “A”, It refers to a moiety, and "the number of atoms in the main chain” refers to the number of atoms constituting the moiety.
  • the “main chain” in L 2 means the “O” atom that connects L 2 and “B”.
  • the number of atoms in the main chain refers to the number of atoms constituting the moiety.
  • the “number of atoms in the main chain” does not include the number of branched chain atoms, which will be described later.
  • the number of atoms in the main chain in L1 means the number of atoms in L1 that does not contain branched chains.
  • the " number of atoms in the main chain” in L2 refers to the number of atoms in L2 not including branched chains.
  • the number of atoms in the main chain of L 1 is 5 (the number of atoms in the dotted frame on the left side of the following formula (D1))
  • the main chain of L 2 The number of atoms of is 5 (the number of atoms in the dotted frame on the right side of formula (D1) below).
  • the number of atoms in the main chain of L 1 is 7 (the number of atoms in the dotted frame on the left side of the formula (D10) below), and the number of atoms in the main chain of L 2 is The number is 5 (the number of atoms in the dotted frame on the right side of formula (D10) below).
  • L 1 and L 2 may have a branched chain.
  • the “branched chain” in L 1 means that the “O” atom that connects L 1 in formula (6) and “A” are directly connected. It means the part other than the part necessary for
  • the “branched chain” in L 2 means that the “O” atom that connects L 2 in formula (6) and “B” are directly connected It means the part other than the part necessary for
  • the “branched chain” in L 1 means the longest atomic chain extending starting from the “O” atom connected to L 1 in formula (6) (that is, the main chain).
  • the “branched chain” in L2 means the longest atomic chain extending from the “O” atom connecting L2 in formula (6) (i.e. main chain).
  • the number of atoms in the branched chain is preferably 3 or less. When the number of branched chain atoms is 3 or less, there is an advantage that the degree of orientation of the light absorption anisotropic layer is further improved.
  • the number of branched chain atoms does not include the number of hydrogen atoms.
  • Ar 1 is (n1+2)-valent (e.g., trivalent when n1 is 1)
  • Ar 2 is (n2+2)-valent (e.g., trivalent when n2 is 1)
  • Ar 3 represents an (n3+2)-valent (for example, trivalent when n3 is 1) aromatic hydrocarbon group or heterocyclic group.
  • each of Ar 1 to Ar 3 can be rephrased as a divalent aromatic hydrocarbon group or a divalent heterocyclic group substituted with n1 to n3 substituents (R 1 to R 3 described later).
  • the divalent aromatic hydrocarbon group represented by Ar 1 to Ar 3 may be monocyclic or have a condensed ring structure of two or more rings.
  • the ring number of the divalent aromatic hydrocarbon group is preferably 1 to 4, more preferably 1 to 2, and even more preferably 1 (that is, a phenylene group) from the viewpoint of further improving the solubility.
  • the divalent aromatic hydrocarbon group include a phenylene group, an azulene-diyl group, a naphthylene group, a fluorene-diyl group, anthracene-diyl group and a tetracene-diyl group, which further improve solubility. From this point of view, a phenylene group and a naphthylene group are preferable, and a phenylene group is more preferable.
  • Specific examples of the third dichroic dye compound are shown below, but the present invention is not limited to these. In the following specific examples, n represents an integer of 1-10.
  • a structure in which the third dye does not have a radically polymerizable group is preferable from the viewpoint of excellent orientation of the light absorption anisotropic layer. Examples include the following structures.
  • the third dichroic azo dye compound is more preferably a dichroic dye having a structure represented by the following formula (1-1) in that the degree of orientation of the light absorption anisotropic layer is particularly excellent. .
  • R 1 , R 3 , R 4 , R 5 , n1, n3, L 1 and L 2 are defined respectively as R 1 , R 3 , R 4 and R 5 in formula (3) , n1, n3 , L1 and L2.
  • definitions of R 21 and R 22 are each independently the same as R 2 in formula (3).
  • definitions of n21 and n22 are independently the same as n2 in formula (3).
  • n1+n21+n22+n3 ⁇ 1, and n1+n21+n22+n3 is preferably 1-9, more preferably 1-5.
  • the content of the dichroic dye is preferably 10 to 30% by mass with respect to the total solid mass of the light absorption anisotropic layer. , more preferably 15 to 30% by mass, and even more preferably 18 to 28% by mass. If the content of the dichroic dye is within the above range, it is possible to obtain an anisotropic light absorption layer with a high degree of orientation even when the anisotropic light absorption layer is a thin film. Therefore, it is easy to obtain a light absorption anisotropic layer having excellent flexibility.
  • the content of the first dichroic azo dye compound is preferably 40 to 90 parts by mass with respect to 100 parts by mass of the total dichroic dye content in the composition for forming a light absorption anisotropic layer, and 45 parts by mass. ⁇ 75 parts by mass is more preferred.
  • the content of the second dichroic azo dye compound is preferably 6 to 50 parts by mass with respect to 100 mass of the total dichroic dye content in the composition for forming a light absorption anisotropic layer, and 8 to 50 parts by mass. 35 parts by mass is more preferable.
  • the content of the third dichroic azo dye compound is preferably 3 to 35 parts by mass with respect to the content of 100 mass of the dichroic azo dye compound in the composition for forming the light absorption anisotropic layer, and 5 ⁇ 30 parts by mass is more preferable.
  • the content ratio of the first dichroic azo dye compound, the second dichroic azo dye compound, and the optionally used third dichroic azo dye compound is the light absorption anisotropy It can be arbitrarily set in order to adjust the color tone of the layer.
  • the content ratio of the second dichroic azo dye compound to the first dichroic azo dye compound is in terms of moles , is preferably 0.1 to 10, more preferably 0.2 to 5, and particularly preferably 0.3 to 0.8. If the content ratio of the second dichroic azo dye compound to the first dichroic azo dye compound is within the above range, the degree of orientation is enhanced.
  • the total solid content means the components capable of forming an anisotropic organic film, excluding the solvent. In addition, even if the property of the said component is liquid, it is calculated as solid content.
  • the anisotropic light absorption layer in the present invention can be produced using, for example, the composition for forming an anisotropic light absorption layer containing the dye compound.
  • the composition for forming an anisotropic light absorption layer may contain components other than the dye compound, for example, a liquid crystalline compound, a solvent, a vertical alignment agent, an interface modifier, a polymerizable component, a polymerization initiator (e.g., radical polymerization initiator) and the like.
  • the light absorption anisotropic layer in the present invention contains a solid component other than the liquid component (solvent etc.) or a component derived from the solid component.
  • the composition for forming a light absorption anisotropic layer will be described below.
  • the liquid crystalline compound and dye compound are as described above.
  • the composition for forming a light absorption anisotropic layer of the present invention preferably contains a solvent from the viewpoint of workability and the like.
  • solvents include ketones (e.g., acetone, 2-butanone, methylisobutyl ketone, cyclopentanone, cyclohexanone, etc.), ethers (e.g., dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentylmethyl ether, tetrahydropyran, and dioxolane, etc.), aliphatic hydrocarbons (e.g., hexane, etc.), alicyclic hydrocarbons (e.g., cyclohexane, etc.), aromatic hydrocarbons (e.g., benzene, toluene, xylene, trimethylbenzene, etc.) ), halogenated carbons (e.g., dichloromethane,
  • solvents may be used singly or in combination of two or more.
  • ketones especially cyclopentanone and cyclohexanone
  • ethers especially tetrahydrofuran, cyclopentyl methyl ether, tetrahydropyran and dioxolane
  • amides especially dimethylformamide, dimethyl Acetamide, N-methylpyrrolidone and N-ethylpyrrolidone
  • the content of the solvent is preferably 80 to 99% by mass, preferably 83 to 99% by mass, based on the total mass of the composition for forming an anisotropic light absorption layer. 98% by mass is more preferable, and 85 to 96% by mass is even more preferable.
  • the content of the solvent means the total content of the solvents.
  • the composition for forming a light absorption anisotropic layer may contain a polymerizable component.
  • Polymerizable components include compounds containing acrylates (eg, acrylate monomers).
  • the light absorption anisotropic layer in the present invention contains polyacrylate obtained by polymerizing the compound containing the acrylate.
  • Examples of the polymerizable component include compounds described in paragraph 0058 of JP-A-2017-122776.
  • the content of the polymerizable component is the same as the dichroic dye compound and the liquid crystalline compound in the composition for forming a light absorption anisotropic layer. 3 to 20 parts by mass is preferable for a total of 100 parts by mass.
  • the composition for forming a light absorption anisotropic layer preferably contains a vertical alignment agent.
  • Vertical alignment agents include boronic acid compounds and onium salts.
  • a compound represented by formula (30) is preferable as the boronic acid compound.
  • R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
  • R3 represents a substituent containing a ( meth)acryl group.
  • Specific examples of boronic acid compounds include boronic acid compounds represented by general formula (I) described in paragraphs 0023 to 0032 of JP-A-2008-225281. As the boronic acid compound, compounds exemplified below are also preferable.
  • ring A represents a quaternary ammonium ion consisting of a nitrogen-containing heterocyclic ring.
  • X represents an anion.
  • L 1 represents a divalent linking group.
  • L2 represents a single bond or a divalent linking group.
  • Y 1 represents a divalent linking group having a 5- or 6-membered ring as a partial structure.
  • Z represents a divalent linking group having 2 to 20 alkylene groups as a partial structure.
  • P 1 and P 2 each independently represent a monovalent substituent having a polymerizable ethylenically unsaturated bond.
  • onium salts include onium salts described in paragraphs 0052 to 0058 of JP-A-2012-208397, onium salts described in paragraphs 0024-0055 of JP-A-2008-026730, and JP-A Onium salts described in 2002-037777 can be mentioned.
  • the content of the vertical alignment agent in the composition is preferably 0.1 to 400% by mass, more preferably 0.5 to 350% by mass, based on the total mass of the liquid crystalline compound.
  • the vertical alignment agents may be used alone or in combination of two or more. When two or more vertical alignment agents are used, the total amount thereof is preferably within the above range.
  • the composition for forming a light absorption anisotropic layer preferably contains the following leveling agent.
  • the composition for forming an anisotropic light absorption layer contains a leveling agent, surface roughening due to drying air applied to the surface of the anisotropic light absorption layer is suppressed, and the dichroic dye is oriented more uniformly.
  • the leveling agent is not particularly limited, and is preferably a leveling agent containing fluorine atoms (fluorine leveling agent) or a leveling agent containing silicon atoms (silicone leveling agent), more preferably a fluorine leveling agent.
  • fluorine-based leveling agents include fatty acid esters of polyvalent carboxylic acids in which a portion of the fatty acid is substituted with a fluoroalkyl group, and polyacrylates having fluoro substituents.
  • fatty acid esters of polyvalent carboxylic acids in which a portion of the fatty acid is substituted with a fluoroalkyl group
  • polyacrylates having fluoro substituents in particular, when a rod-shaped compound is used as the dichroic dye and the liquid crystalline compound, from the viewpoint of promoting the vertical alignment of the dichroic dye and the liquid crystalline compound, leveling containing a repeating unit derived from the compound represented by formula (40) agents are preferred.
  • R 0 represents a hydrogen atom, a halogen atom, or a methyl group.
  • L represents a divalent linking group. L is preferably an alkylene group having 2 to 16 carbon atoms, and any —CH 2 — that is not adjacent in the alkylene group is substituted with —O—, —COO—, —CO—, or —CONH—. may n represents an integer from 1 to 18;
  • the leveling agent having repeating units derived from the compound represented by formula (40) may further contain other repeating units.
  • Other repeating units include repeating units derived from the compound represented by formula (41).
  • R 11 represents a hydrogen atom, a halogen atom, or a methyl group.
  • X represents an oxygen atom, a sulfur atom, or -N(R 13 )-.
  • R 13 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 12 represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aromatic group.
  • the number of carbon atoms in the alkyl group is preferably 1-20.
  • the alkyl group may be linear, branched, or cyclic. Further, examples of substituents that the alkyl group may have include a poly(alkyleneoxy) group and a polymerizable group. The definition of the polymerizable group is as described above.
  • repeating units derived from the compound represented by formula (40) is preferably 10 to 90 mol %, more preferably 15 to 95 mol %, based on the total repeating units contained in the leveling agent.
  • repeating units derived from the compound represented by formula (41) is preferably 10 to 90 mol %, more preferably 5 to 85 mol %, based on the total repeating units contained in the leveling agent.
  • the leveling agent also includes a leveling agent containing repeating units derived from the compound represented by formula (42) instead of repeating units derived from the compound represented by formula (40) described above.
  • R2 represents a hydrogen atom, a halogen atom, or a methyl group.
  • L2 represents a divalent linking group.
  • n represents an integer from 1 to 18;
  • leveling agent examples include compounds exemplified in paragraphs 0046 to 0052 of JP-A-2004-331812 and compounds described in paragraphs 0038-0052 of JP-A-2008-257205.
  • the content of the leveling agent in the composition for forming an anisotropic light absorption layer is preferably 0.001 to 10% by mass, more preferably 0.01 to 5% by mass, based on the total mass of the liquid crystalline compound.
  • a leveling agent may be used independently and may be used in combination of 2 or more type. When two or more leveling agents are used, the total amount thereof is preferably within the above range.
  • the composition for forming a light absorption anisotropic layer preferably contains a polymerization initiator.
  • the polymerization initiator is not particularly limited, it is preferably a compound having photosensitivity, that is, a photopolymerization initiator.
  • Various compounds can be used as the photopolymerization initiator without any particular limitation. Examples of photoinitiators include ⁇ -carbonyl compounds (US Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (US Pat. No. 2,448,828), ⁇ -hydrocarbon-substituted aromatic acyloins, compounds (US Pat. No. 2,722,512), polynuclear quinone compounds (US Pat.
  • photopolymerization initiator commercially available products can also be used, and BASF Irgacure-184, Irgacure-907, Irgacure-369, Irgacure-651, Irgacure-819, Irgacure-OXE-01 and Irgacure- OXE-02 and the like.
  • the content of the polymerization initiator is the above dye compound (preferably a dichroic dye) in the composition for forming a light absorption anisotropic layer. It is preferably 0.01 to 30 parts by mass, more preferably 0.1 to 15 parts by mass, based on a total of 100 parts by mass of the above liquid crystalline compound (eg, polymer liquid crystalline compound).
  • the content of the polymerization initiator is 0.01 parts by mass or more, the durability of the light absorption anisotropic film is improved, and when it is 30 parts by mass or less, the orientation degree of the light absorption anisotropic layer is be better.
  • a polymerization initiator may be used individually by 1 type, or may use 2 or more types together. When two or more polymerization initiators are included, the total amount is preferably within the above range.
  • the method for forming the anisotropic light absorption layer is not particularly limited, and the step of applying the composition for forming an anisotropic light absorption layer to form a coating film (hereinafter also referred to as the “coating film forming step”). and a step of orienting the liquid crystalline component or dichroic dye contained in the coating film (hereinafter also referred to as an “orientation step”), in this order.
  • the liquid crystalline component is a component containing not only the liquid crystalline compound described above but also a dichroic dye having liquid crystallinity when the dichroic dye described above has liquid crystallinity.
  • the coating film forming step is a step of applying a composition for forming a light absorption anisotropic layer to form a coating film.
  • a composition for forming a light absorption anisotropic layer containing the above-mentioned solvent, or by using a liquid such as a melt by heating the composition for forming a light absorption anisotropic layer, It becomes easy to apply the composition for forming a light-absorbing anisotropic layer.
  • Specific examples of the coating method of the composition for forming a light-absorbing anisotropic layer include roll coating, gravure printing, spin coating, wire bar coating, extrusion coating, direct gravure coating, and reverse coating. Known methods such as a gravure coating method, a die coating method, a spray method, and an inkjet method can be used.
  • the alignment step is a step of orienting the liquid crystalline component contained in the coating film. Thereby, a light absorption anisotropic layer is obtained.
  • the orientation step may include drying. Components such as the solvent can be removed from the coating film by the drying treatment.
  • the drying treatment may be performed by a method of leaving the coating film at room temperature for a predetermined period of time (for example, natural drying), or by a method of heating and/or blowing air.
  • the liquid crystalline component contained in the composition for forming a light absorption anisotropic layer may be oriented by the coating film forming step or drying treatment described above.
  • the coating film is dried to remove the solvent from the coating film, thereby obtaining the anisotropic light absorption.
  • a coating film (that is, a light absorption anisotropic film) is obtained.
  • the transition temperature of the liquid crystalline component contained in the coating film to the liquid crystal phase is preferably 10 to 250°C, more preferably 25 to 190°C, from the standpoint of production suitability.
  • the transition temperature is 10° C. or higher, cooling treatment or the like for lowering the temperature to the temperature range where the liquid crystal phase is exhibited is not required, which is preferable.
  • the transition temperature is 250° C. or less, a high temperature is not required even when the isotropic liquid state is converted to an isotropic liquid state at a temperature higher than the temperature range in which the liquid crystal phase is once exhibited. This is preferable because it can reduce deformation, deterioration, and the like.
  • the orientation step preferably includes heat treatment.
  • the liquid crystalline component contained in the coating film can be oriented, so that the coating film after heat treatment can be suitably used as a light absorption anisotropic film.
  • the heat treatment is preferably from 10 to 250° C., more preferably from 25 to 190° C., from the standpoint of suitability for production.
  • the heating time is preferably 1 to 300 seconds, more preferably 1 to 60 seconds.
  • the orientation step may have a cooling treatment performed after the heat treatment.
  • the cooling process is a process of cooling the coated film after heating to about room temperature (20 to 25° C.). Thereby, the orientation of the liquid crystalline component contained in the coating film can be fixed.
  • a cooling means is not particularly limited, and a known method can be used. Through the above steps, a light absorption anisotropic film can be obtained. In this embodiment, drying treatment, heat treatment, and the like are mentioned as methods for orienting the liquid crystalline component contained in the coating film.
  • the method for forming the anisotropic light absorption layer may include a step of curing the anisotropic light absorption layer (hereinafter also referred to as a “curing step”) after the alignment step.
  • the curing step is carried out by heating and/or light irradiation (exposure), for example, when the light absorption anisotropic layer has a crosslinkable group (polymerizable group).
  • the curing step is preferably carried out by light irradiation.
  • Various light sources such as infrared light, visible light, and ultraviolet light can be used as the light source for curing, but ultraviolet light is preferred.
  • ultraviolet rays may be irradiated while being heated during curing, or ultraviolet rays may be irradiated through a filter that transmits only specific wavelengths.
  • the heating temperature during exposure is preferably 25 to 140° C., depending on the transition temperature of the liquid crystalline component contained in the liquid crystal film to the liquid crystal phase.
  • the exposure may be performed in a nitrogen atmosphere.
  • radical polymerization it is preferable to perform exposure in a nitrogen atmosphere because inhibition of polymerization by oxygen is reduced.
  • the thickness of the light absorption anisotropic layer to be formed is not particularly limited, but is preferably 100 to 8000 nm, more preferably 300 to 5000 nm, from the viewpoint of flexibility when the laminate of the present invention described later is used in a polarizing element. more preferred.
  • the polarizing plate of the present invention contains a polarizer.
  • the polarizer is not particularly limited, and conventionally known polarizers can be used.
  • the polarizer may be, for example, a polarizer horizontally oriented by dyeing polyvinyl alcohol or other polymer resin with a dichroic dye and stretching it, or a light absorption anisotropic layer of the present invention.
  • a polarizer in which a dichroic dye is horizontally oriented by utilizing the orientation of a liquid crystalline compound may be used, but a polarizer in which a dichroic dye is oriented using the orientation of a liquid crystal without stretching is available. Especially preferred.
  • a polarizer in which a dichroic dye is oriented using the orientation of a liquid crystal can be made very thin with a thickness of about 0.1 to 5 ⁇ m, as described in JP-A-2019-194685. It is difficult to crack when bent, has little thermal deformation, and has excellent durability even in a polarizing plate having a high transmittance of more than 50% as described in Japanese Patent No. 6483486. have advantages. Taking advantage of these advantages, the polarizing plate of the present invention using a polarizer in which a dichroic dye is oriented by utilizing the orientation of liquid crystals can be used for applications requiring high brightness, small size and light weight, and applications for fine optical systems. , molding applications for curved parts, and applications for flexible parts.
  • the polarizing plate of the invention may have a transparent substrate film.
  • the transparent substrate film is preferably arranged on the surface of the anisotropic light absorption layer opposite to the surface on which the polarizer is provided.
  • a known transparent resin film, transparent resin plate, transparent resin sheet, or the like can be used, and there is no particular limitation.
  • transparent resin films include cellulose acylate films (e.g., cellulose triacetate film (refractive index: 1.48), cellulose diacetate film, cellulose acetate butyrate film, cellulose acetate propionate film), cyclic olefin resin films, and polyethylene.
  • Terephthalate film polyethersulfone film, polyacrylic resin film, polyurethane resin film, polyester film, polycarbonate film, polysulfone film, polyether film, polymethylpentene film, polyetherketone film, and (meth)acrylonitrile film etc. can be used.
  • a cellulose acylate film which is highly transparent, has a low optical birefringence, is easy to manufacture, and is generally used as a protective film for polarizing plates, is preferred, and a cellulose triacetate film is particularly preferred.
  • the thickness of the transparent substrate film is usually 20-100 ⁇ m.
  • the polarizing plate of the invention may have an alignment film between the transparent substrate film and the light absorption anisotropic layer.
  • the alignment film may be any layer as long as the dye compound (preferably dichroic dye) can be oriented in a desired state on the alignment film.
  • the alignment film for example, a film formed from a polyfunctional acrylate compound or polyvinyl alcohol may be used.
  • the polarizing plate of the present invention preferably has a barrier layer together with the light absorption anisotropic layer.
  • the barrier layer is also called a gas barrier layer (oxygen barrier layer), and protects the polarizing plate member of the present invention from gases such as oxygen in the atmosphere, moisture, or compounds contained in adjacent layers.
  • the polarizing plate of the invention may have a refractive index adjusting layer.
  • the polarizing plate of the present invention may have a problem of internal reflection due to the high refractive index of the light absorption anisotropic layer. In that case, it is preferable that the refractive index adjusting layer is present.
  • the refractive index adjusting layer is a layer arranged so as to be in contact with the light absorption anisotropic layer, and preferably has an in-plane average refractive index of 1.55 to 1.70 at a wavelength of 550 nm. That is, it is preferably a refractive index adjustment layer for performing so-called index matching.
  • the polarizing plate of the present invention may contain a color tone adjusting layer containing at least one kind of color tone adjusting dye compound.
  • the coloring compound for color adjustment contained in the color adjustment layer is preferably in a non-oriented state.
  • the amount of dye in the light absorption anisotropic layer is adjusted, the change in color when viewed from an oblique direction with respect to the central axis of transmittance may increase.
  • This tint adjustment layer may have only the function of the tint adjustment layer alone, or may have the functions integrated with those of other layers.
  • the absorption peak wavelength of the colorant compound for color adjustment contained in the color adjustment layer used in the present invention is preferably 500 to 650 nm, more preferably 550 to 600 nm.
  • Color adjusting dye compounds contained in the color adjusting layer include, for example, azo, methine, anthraquinone, triarylmethane, oxazine, azomethine, phthalocyanine, porphyrin, perylene, pyrrolopyrrole, and squarylium.
  • Azo, phthalocyanine and anthraquinone are preferred, and anthraquinone is particularly preferred, from the viewpoint of excellent corrugation, heat resistance and light resistance.
  • coloring compound for color adjustment used in the present invention are shown below, but the present invention is not limited to these.
  • An example of the method for producing the polarizing plate of the present invention includes a step of coating the composition for forming an alignment film on the transparent substrate film to form an alignment film, and applying the composition for forming an anisotropic light absorption layer.
  • a step of applying a composition for forming a barrier layer to obtain a laminate, a step of bonding a separately prepared polarizer to the barrier layer side of the laminate, and a separately formed ⁇ / 4 retardation film is laminated.
  • a method including the step of laminating on the transparent substrate film side of the body in this order is mentioned.
  • a polarizing plate having a polarizer, a barrier layer, a light absorption anisotropic layer, an alignment film, a transparent substrate film, and a ⁇ /4 retardation film in this order is obtained by carrying out the above steps.
  • the polarizer, the light absorption anisotropic layer, and the ⁇ / 4 retardation film, a barrier layer, an oriented film, and a transparent substrate film in addition to the polarizer, the light absorption anisotropic layer, and the ⁇ / 4 retardation film, a barrier layer, an oriented film, and a transparent substrate film.
  • a step of forming members other than the barrier layer, the alignment film, and the transparent substrate film may be included.
  • Each step can be carried out according to a known method and is not particularly limited.
  • the order of each step may be changed as long as the polarizing plate can be formed.
  • the lamination or the like in the method for manufacturing the polarizing plate is performed using an adhesive layer. That is, the polarizing plate of the invention may have an adhesive layer.
  • the adhesive layer in the present invention is preferably a transparent and optically isotropic adhesive like those used in ordinary liquid crystal display devices, and usually a pressure-sensitive adhesive is used.
  • the adhesive layer in the present invention includes a base material (adhesive), conductive particles, and optionally thermally expandable particles, as well as a cross-linking agent (e.g., isocyanate-based cross-linking agent, epoxy-based cross-linking agent, etc.). , tackifiers (e.g., rosin derivative resins, polyterpene resins, petroleum resins, oil-soluble phenolic resins, etc.), plasticizers, fillers, anti-aging agents, surfactants, UV absorbers, light stabilizers, antioxidants, etc. Appropriate additives may be blended.
  • a cross-linking agent e.g., isocyanate-based cross-linking agent, epoxy-based cross-linking agent, etc.
  • tackifiers e.g., rosin derivative resins, polyterpene resins, petroleum resins, oil-soluble phenolic resins, etc.
  • plasticizers e.g., rosin derivative resins, poly
  • the thickness of the adhesive layer is usually 20-500 ⁇ m, preferably 20-250 ⁇ m. If the thickness is less than 20 ⁇ m, the required adhesion and reworkability may not be obtained, and if the thickness exceeds 500 ⁇ m, the adhesive may protrude or ooze out from the peripheral edges of the image display device.
  • the protective member for example, a configuration in which conductive particles are added to the configuration of the heat-peelable pressure-sensitive adhesive sheet described in Japanese Patent Application Laid-Open No. 2003-292916 can be applied.
  • a commercial product such as "Riva Alpha” manufactured by Nitto Denko Co., Ltd., in which conductive particles are dispersed on the surface of the adhesive layer, may be used.
  • the lamination or the like in the method for manufacturing the polarizing plate is performed by an adhesive layer. That is, the polarizing plate of the invention may have an adhesive layer.
  • An adhesive layer refers to a layer containing an adhesive.
  • the adhesive used in the present invention preferably develops adhesiveness by drying or reaction after bonding.
  • a polyvinyl alcohol-based adhesive (PVA-based adhesive) develops adhesiveness when dried, making it possible to bond materials together.
  • curable adhesives that exhibit adhesiveness through reaction include active energy ray curable adhesives such as (meth)acrylate adhesives and cationic polymerization curable adhesives.
  • (Meth)acrylate means acrylate and/or methacrylate.
  • the curable component in the (meth)acrylate adhesive includes, for example, a compound having a (meth)acryloyl group and a compound having a vinyl group.
  • Compounds having an epoxy group or an oxetanyl group can also be used as cationic polymerization curing adhesives.
  • the compound having an epoxy group is not particularly limited as long as it has at least two epoxy groups in the molecule, and various commonly known curable epoxy compounds can be used.
  • Preferred epoxy compounds include compounds having at least two epoxy groups and at least one aromatic ring in the molecule (aromatic epoxy compounds), and compounds having at least two epoxy groups in the molecule, at least one of which Examples include compounds (alicyclic epoxy compounds) formed between two adjacent carbon atoms constituting an alicyclic ring.
  • an ultraviolet curable adhesive that is cured by ultraviolet irradiation is preferably used.
  • Each layer of the adhesive layer and the adhesive layer is treated with UV absorbers such as salicylic acid ester compounds, benzophenol compounds, benzotriazole compounds, cyanoacrylate compounds, and nickel complex compounds. It may be a material having absorptive ability or the like.
  • Attachment of the adhesive layer and adhesive layer to the film can be performed by an appropriate method.
  • a base polymer or a composition thereof is dissolved or dispersed in a suitable solvent such as toluene and ethyl acetate alone or in a mixture to prepare a pressure-sensitive adhesive solution of about 10 to 40% by weight.
  • a method of directly attaching it to the object to be laminated by an appropriate development method such as a casting method or a coating method
  • a method of forming an adhesive layer on the separator according to the above method and applying it to the object to be laminated A method of transferring to the top and the like can be mentioned.
  • the adhesive layer and adhesive layer can also be provided on the object to be bonded as superimposed layers of different compositions or types. Also, the adhesive layer and the adhesive layer may be provided on both sides of the opposing surfaces of the object to be bonded. When the adhesive layer or adhesive layer is provided on both sides of the object to be laminated, the adhesive layer or adhesive layer provided on both sides may be the same layer, or may be a layer with different composition, type, thickness, etc. good.
  • the object to be laminated may be subjected to surface modification treatment for the purpose of improving adhesiveness, etc., before attaching the adhesive and pressure-sensitive adhesive.
  • Specific treatments include corona treatment, plasma treatment, primer treatment, saponification treatment, and the like.
  • the organic EL display device of the present invention is a display device in which a light-emitting layer or a plurality of organic compound thin films including a light-emitting layer are formed between a pair of electrodes of an anode and a cathode. It has a polarizing plate, and the polarizing plate is arranged so that the polarizer is on the viewing side of the ⁇ /4 retardation film.
  • the organic EL display device of the present invention has a polarizer, a ⁇ / 4 retardation film, and an anisotropic light absorption layer in this order from the viewing side, or a polarizer, an anisotropic light absorption layer, and a ⁇ /4 retardation film in this order, or a light absorption anisotropic layer, a polarizer, and a ⁇ /4 retardation film in this order.
  • the organic EL display device preferably has a structure including an organic EL display element including the organic compound thin film described above and a polarizing plate.
  • the organic compound thin film may have a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a protective layer, and the like. It may be provided with the function of Each layer such as an electrode and an organic compound thin film of an organic EL display device can be formed by known materials and methods.
  • the organic EL display device of the present invention has improved reflectance and color when viewed obliquely.
  • Example 1 (Formation of alignment film)
  • the surface of a cellulose acylate film (40 ⁇ m thick TAC film; TG40, Fuji Film Co., Ltd.) was saponified with an alkaline solution, and the following alignment film forming composition 1 was applied thereon with a wire bar to form a coating film.
  • the TAC film on which the coating film was formed was dried with hot air at 60° C. for 60 seconds and further with hot air at 100° C. for 120 seconds to form an alignment film AL1, and TAC film 1 with an alignment film was obtained.
  • the film thickness was 1 ⁇ m.
  • composition P1 for forming light absorption anisotropic layer Dichroic dye D-1 0.63 parts by mass Dichroic dye D-2 0.17 parts by mass Dichroic dye D-3 1.13 parts by mass Polymer liquid crystalline compound P-1 8. 18 parts by weight IRGACUREOXE-02 (manufactured by BASF) 0.16 parts by weight Compound E-1 0.12 parts by weight Compound E-2 0.12 parts by weight Surfactant F-1 0.005 parts by weight Cyclopentanone 85.00 parts by mass Benzyl alcohol 4.50 parts by mass ⁇
  • barrier layer B1 On the light absorption anisotropic layer P1 of the obtained TAC film P1, the following barrier layer forming composition B1 was continuously applied with a wire bar to form a coating film. Next, the support with the coating film formed thereon was dried with hot air at 60° C. for 60 seconds and further with hot air at 100° C. for 120 seconds to form a barrier layer B1, thereby obtaining an optical film P1.
  • the film thickness of the barrier layer was 0.5 ⁇ m.
  • ⁇ (Barrier layer-forming composition B1) ⁇ ⁇ Modified polyvinyl alcohol PVA-1 3.80 parts by mass ⁇ IRGACURE 2959 0.20 parts by mass ⁇ Water 70 parts by mass ⁇ Methanol 30 parts by mass ⁇ ⁇
  • a composition PA1 for forming a photo-alignment film having the following composition was continuously applied on a film of the same type as the TAC film described above with a wire bar to form a coating film.
  • the TAC film on which the coating film was formed was dried with hot air at 140°C for 120 seconds, and then the coating film was irradiated with polarized ultraviolet rays (10 mJ/cm 2 , using an ultra-high pressure mercury lamp) to obtain a thickness of 0.2 ⁇ m. to obtain a TAC film with a photo-alignment film.
  • Composition A-1 having the following composition was applied onto the photo-alignment film PA1 of the TAC film with a photo-alignment film using a bar coater to form a coating film.
  • the coating film formed on the photo-alignment film PA1 is heated to 120°C with warm air, then cooled to 60°C, and then irradiated with ultraviolet rays of 100 mJ/cm 2 at a wavelength of 365 nm using a high-pressure mercury lamp in a nitrogen atmosphere.
  • the orientation of the liquid crystalline compound is fixed, and the ⁇ / 4 retardation layer A1 ( ⁇ / 4 position A TAC film A1 having a retardation film) was produced.
  • the ⁇ /4 retardation layer A1 had a thickness of 2.5 ⁇ m and Re(550) of 144 nm. Also, the ⁇ /4 retardation layer A1 satisfied the relationship Re(450) ⁇ Re(550) ⁇ Re(650). In the ⁇ /4 retardation layer, Re(450)/Re(550) was 0.82.
  • composition A-1 ⁇ 43.50 parts by mass of polymerizable liquid crystalline compound LA-1 below 43.50 parts by mass of polymerizable liquid crystalline compound LA-2 below 8.00 parts by mass of polymerizable liquid crystalline compound LA-3 below Polymerizable liquid crystal below 5.00 parts by mass of the chemical compound LA-4 ⁇ 0.55 parts by mass of the following polymerization initiator PI-1 ⁇ 0.20 parts by mass of the following leveling agent T-1 ⁇ 235.00 parts by mass of cyclopentanone ⁇
  • An acrylate-based polymer was prepared according to the following procedure. 95 parts by weight of butyl acrylate and 5 parts by weight of acrylic acid are polymerized by a solution polymerization method in a reaction vessel equipped with a cooling tube, a nitrogen inlet tube, a thermometer and a stirring device, and the average molecular weight is 2,000,000 and the molecular weight distribution (Mw/ An acrylate polymer A1 having Mn) of 3.0 was obtained.
  • This composition was applied using a die coater to a separate film surface-treated with a silicone-based release agent and dried for 1 minute at 90° C. to obtain an acrylate-based pressure-sensitive adhesive sheet 1 .
  • the film thickness was 15 ⁇ m and the storage modulus was 0.1 MPa.
  • UV adhesive composition having the following composition was prepared.
  • ⁇ UV adhesive composition ⁇ ⁇ CEL2021P (manufactured by Daicel) 70 parts by mass ⁇ 1,4-Butanediol diglycidyl ether 20 parts by mass ⁇ 2-Ethylhexyl glycidyl ether 10 parts by mass ⁇ CPI-100P 2.25 parts by mass ⁇ ⁇
  • a polarizer 1 having a thickness of 8 ⁇ m and one surface of which is exposed was produced in the same manner as the polarizing plate 02 with a single-sided protective film described in WO 2015/166991.
  • the surface of the polarizer 1 where the polarizer is exposed and the barrier layer B1 side of the optical film P1 including the light absorption anisotropic layer P1 prepared above were bonded together with the pressure-sensitive adhesive sheet 1 described above.
  • the TAC film side of the optical film P1 containing the light absorption anisotropic layer P1 and the ⁇ / 4 retardation layer A1 side of the TAC film A1 containing the ⁇ / 4 retardation layer A1 are combined with the UV adhesive composition
  • An object was coated, bonded together, and cured by UV irradiation at 600 mJ/cm 2 to form a UV adhesive layer.
  • the thickness of the UV adhesive layer was 3 ⁇ m.
  • Each surface to be bonded with the UV adhesive was subjected to corona treatment.
  • the photo-alignment film PA1 and TAC film 1 on the ⁇ /4 retardation layer A1 side were removed to obtain a polarizing plate C1.
  • the layer structure of the polarizing plate C1 is, in order from the polarizer 1 side, the polarizer 1, the adhesive sheet 1, the barrier layer B1, the light absorption anisotropic layer P1, the alignment film AL1, the TAC film, the UV adhesive layer, and ⁇ /4 retardation layer A1.
  • Example 2 A polarizing plate C2 of Example 2 was produced in the same manner as in Example 1, except that the thickness of the light absorption anisotropic layer P1 in the optical film P1 of Example 1 was changed to 0.18 ⁇ m.
  • Example 3 A polarizing plate C3 was produced in the same manner as in Example 1, except that the thickness of the light absorption anisotropic layer P1 in the optical film P1 of Example 1 was changed to 0.70 ⁇ m.
  • Example 4 In the preparation of the polarizing plate C1 of Example 1, the polarizer 1 and the TAC film A1 are bonded together with a UV adhesive so that the exposed surface of the polarizer of the polarizer 1 and the surface of the ⁇ /4 retardation layer A1 face each other. After removing the photo-alignment film PA1 and TAC film 1, the surface of the ⁇ / 4 retardation layer A1 on the side opposite to the polarizer 1 side and the surface of the optical film P1 on the barrier layer B1 side are adhered. A polarizing plate C4 was obtained by sticking so that the agent sheet 1 faced each other.
  • the layer structure of the polarizing plate C1 is, in order from the polarizer 1 side, the polarizer 1, the UV adhesive layer, the ⁇ /4 retardation layer A1, the adhesive sheet 1, the barrier layer B1, and the light absorption anisotropic layer P1.
  • a polarizing plate C4 was produced in the same manner as in Example 1, except that the alignment film AL1 and the TAC film were used.
  • Example 5 In the preparation of the polarizing plate C1 of Example 1, the optical film P1 and the polarizer 1 are placed together so that the surface of the optical film P1 on the TAC film 1 side faces the surface of the polarizer 1 where the polarizer is exposed. pasted with an adhesive, and then pasted with a UV adhesive so that the surface of the polarizer 1 opposite to the optical film P1 side faces the surface of the ⁇ /4 retardation layer A1 of the TAC film A1, The photo-alignment film PA1 and TAC film 1 were removed to obtain a polarizing plate C5.
  • the layer structure of the polarizing plate C1 is, in order from the barrier layer B1 side, the barrier layer B1, the light absorption anisotropic layer P1, the alignment film AL1, the TAC film 1, the UV adhesive, the polarizer 1, the UV adhesive layer, A polarizing plate C5 was produced in the same manner as in Example 1, except that the ⁇ /4 retardation layer A1 was used.
  • Example 1 In the production of the polarizing plate C1 of Example 1, the polarizing plate was produced without using the optical film P1. That is, in the same manner as in Example 1, except that the layer structure of the polarizing plate C1 is, in order from the polarizer 1 side, the polarizer 1, the UV adhesive layer, and the ⁇ / 4 retardation layer A1. C6 was produced.
  • composition P1 for forming an anisotropic light absorption layer was changed to the composition P2 for forming an anisotropic light absorption layer described below, and the film thickness was changed to 0.5 ⁇ m.
  • a polarizing plate C7 was produced in the same manner as in Example 1.
  • the composition P2 for forming an anisotropic light absorption layer contained no dye compound.
  • Composition of Composition P2 for Forming Light-Absorbing Anisotropic Layer 8.18 parts by mass of the polymer liquid crystal compound P-1 IRGACUREOXE-02 (manufactured by BASF) 0.16 parts by mass 0.12 parts by mass of the compound E-1 0.12 parts by mass of the compound E-2 Part ⁇
  • Example 3 A polarizing plate C8 was produced in the same manner as in Example 1, except that the thickness of the light absorption anisotropic layer in the optical film P1 of Example 1 was changed to 0.09 ⁇ m.
  • a polarizing plate C9 was produced in the same manner as in Example 1, except that the film thickness of the light absorption anisotropic layer in the optical film P1 of Example 1 was changed to 1.20 ⁇ m.
  • Example 5 A polarizing plate C10 was produced in the same manner as in Example 1, except that the thickness of the light absorption anisotropic layer in the optical film P1 of Example 1 was changed to 3.50 ⁇ m.
  • the polarization characteristics of the obtained anisotropic light absorption layer were measured at the wavelength ⁇ at the polar angle in the in-plane slow axis direction of the anisotropic light absorption layer. It was obtained by measuring while changing the direction.
  • the wavelength ⁇ means a wavelength of 450 nm, a wavelength of 550 nm, or a wavelength of 630 nm.
  • Axoscan manufactured by Axometics is used as the measuring device, and the Mueller matrix is measured every 5° from -70 to 70° in the in-plane slow axis direction, and the degree A of the absorption anisotropy is measured. , was obtained by fitting The value of A( ⁇ ) represented by the above formula was obtained at three wavelengths of 450 nm, 550 nm, and 630 nm.
  • the Rth of the anisotropic light absorption layer including the anisotropic light absorption layer was 450 nm and the wavelength
  • the value of A( ⁇ ) is from 20 to 200 nm at all of the wavelengths of 450 nm, 550 nm and 630 nm
  • the display performance is excellent. was confirmed (Examples 1 to 5).
  • the Rth of the optically anisotropic absorption layer is within the above range but the A is not within the above range (Comparative Example 2), and the configuration where both Rth and A are not within the above range (Comparative Examples 3 to 5) was confirmed to be inferior in display performance.

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  • Engineering & Computer Science (AREA)
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  • Optics & Photonics (AREA)
  • Polarising Elements (AREA)
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Cited By (1)

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WO2025004914A1 (ja) * 2023-06-30 2025-01-02 富士フイルム株式会社 有機エレクトロルミネッセンス表示装置

Citations (4)

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Publication number Priority date Publication date Assignee Title
JP2018022153A (ja) * 2016-07-21 2018-02-08 富士フイルム株式会社 積層体及び液晶表示装置
WO2019235355A1 (ja) * 2018-06-04 2019-12-12 富士フイルム株式会社 表示装置
WO2020095831A1 (ja) * 2018-11-09 2020-05-14 住友化学株式会社 垂直配向液晶硬化膜およびそれを含む積層体
WO2020175569A1 (ja) * 2019-02-27 2020-09-03 富士フイルム株式会社 光学異方性膜、積層体、円偏光板、表示装置

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
JP2018022153A (ja) * 2016-07-21 2018-02-08 富士フイルム株式会社 積層体及び液晶表示装置
WO2019235355A1 (ja) * 2018-06-04 2019-12-12 富士フイルム株式会社 表示装置
WO2020095831A1 (ja) * 2018-11-09 2020-05-14 住友化学株式会社 垂直配向液晶硬化膜およびそれを含む積層体
WO2020175569A1 (ja) * 2019-02-27 2020-09-03 富士フイルム株式会社 光学異方性膜、積層体、円偏光板、表示装置

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025004914A1 (ja) * 2023-06-30 2025-01-02 富士フイルム株式会社 有機エレクトロルミネッセンス表示装置

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