US20200012026A1 - Phase difference plate, multilayer phase difference plate, polarizing plate, image display device and polymerizable compound - Google Patents

Phase difference plate, multilayer phase difference plate, polarizing plate, image display device and polymerizable compound Download PDF

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US20200012026A1
US20200012026A1 US16/493,029 US201816493029A US2020012026A1 US 20200012026 A1 US20200012026 A1 US 20200012026A1 US 201816493029 A US201816493029 A US 201816493029A US 2020012026 A1 US2020012026 A1 US 2020012026A1
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group
carbon atoms
phase difference
difference plate
ring
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Masakazu Saito
Kazuhiro Osato
Masashi Aimatsu
Kei Sakamoto
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Zeon Corp
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Zeon Corp
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3016—Polarising elements involving passive liquid crystal elements
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C07D333/10—Thiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/22—Esters containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/24—Esters containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G02F1/133633—Birefringent elements, e.g. for optical compensation using mesogenic materials
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G02F1/133635—Multifunctional compensators
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00634—Production of filters
    • B29D11/00644—Production of filters polarizing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2335/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
    • C08J2335/02—Characterised by the use of homopolymers or copolymers of esters

Definitions

  • the present invention relates to a phase difference plate and a multilayer phase difference plate, a polarizing plate, and an image display device including the phase difference plate, as well as a polymerizable compound.
  • a phase difference plate is widely used as a constituent element of a display device such as a liquid crystal display device and an organic electroluminescent display device.
  • a 1 ⁇ 4 wavelength plate is widely used for the purpose of converting circularly polarized light into linearly polarized light and converting linearly polarized light into circularly polarized light.
  • a liquid crystal material is known as a material constituting such a phase difference plate.
  • a material obtained by rendering a polymerizable liquid crystal compound to be in a liquid crystal state and polymerizing the compound while the liquid crystal state is maintained is known (e.g., Patent literatures 1 and 2).
  • Patent Literature 1 Japanese Patent Application Laid-Open No. 2014-206684 A
  • Patent Literature 2 Japanese Patent Application Laid-Open No. 2006-268033 A (corresponding publication: U.S. Patent Application Publication No. 2009/033835)
  • phase difference plates used in prior art fail to achieve uniform optical effects in a wide wavelength range.
  • an object of the present invention is to provide a phase difference plate, a multilayer phase difference plate, and a polymerizable compound, capable of achieving uniform optical effects in a wide wavelength range.
  • Another object of the present invention is to provide a polarizing plate and an image display device, capable of exhibiting uniform performance in a wide wavelength range.
  • the present inventor has conducted studies to solve the aforementioned problem. As a result, the inventor has found that the aforementioned problem can be solved by a phase difference plate which is formed of a liquid crystal material and has a specific in-plane retardation. In particular, the present inventor has found that such a phase difference plate can particularly be easily produced by using a liquid crystal compound having a specific structure. The present invention has been completed on the basis of such findings.
  • the present invention is as follows.
  • Ar is a divalent aromatic hydrocarbon ring group having D as a substituent, or a divalent aromatic heterocyclic ring group having D as a substituent,
  • D is an organic group of 1 to 67 carbon atoms having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring,
  • Z 1 and Z 2 are each independently a single bond, —O—, —O—CH 2 —, —CH 2 —O—, —O—CH 2 -CH 2 , —CH 2 -CH 2 —O—, —C( ⁇ O)—O—, —O— C( ⁇ O)—, —C( ⁇ O)—S—, —S—C( ⁇ O)—, —NR 21 —C( ⁇ O)—, —C( ⁇ O)—NR 21 —, —CF 2 —O—, —CH 2 -CH 2 —, —CF 2 -CF 2 —, —O—CH 2 -CH 2 —O—, —CH ⁇ CH—C( ⁇ O)—O—, —O—C( ⁇ O)—CH ⁇ CH—, —CH 2 —C( ⁇ O)—O—, —OC( ⁇ O)—CH 2 —, —CH 2 —O—C( ⁇ O)—, —C(
  • a 1 and A 2 , and B 1 and B 2 each independently represent a cyclic aliphatic group optionally having a substituent or an aromatic group optionally having a substituent,
  • Y 1 to Y 4 each independently represent a single bond, —O—, —C( ⁇ O)—, —C( ⁇ O)—O—, —O—C( ⁇ O)—, —NR 22 —C( ⁇ O)—, —C( ⁇ O)—NR 22 —, —OC( ⁇ O)—O—, —NR 22 —C( ⁇ O)—O—, —OC( ⁇ O)—NR 22 —, or —NR 22 —C( ⁇ O)—NR 23
  • R 22 and R 23 each independently represent a hydrogen atom or an alkyl group of 1 to 6 carbon atoms
  • G 1 and G 2 are each independently any of organic groups that are an aliphatic hydrocarbon group of 1 to 20 carbon atoms and a group in which one or more methylene groups (—CH 2 —) contained in an aliphatic hydrocarbon group of 3 to 20 carbon atoms are substituted by —O— or —C( ⁇ O)—, and hydrogen atoms in the organic groups of G 1 and G 2 may be substituted by an alkyl group of 1 to 5 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, or a halogen atom,
  • P 1 and P 2 each independently represent a polymerizable group, and p and q are each independently 0 or 1].
  • an in-plane slow axis of the phase difference plate P 1 is orthogonal to an in-plane slow axis of the phase difference plate P 2 ,
  • phase difference plate P 2 is the phase difference plate according to any one of ⁇ 1> to ⁇ 3>,
  • an in-plane retardation ReP 1 ( ⁇ ) of the phase difference plate P 1 at a wavelength ⁇ nm and an in-plane retardation ReP 2 ( ⁇ ) of the phase difference plate P 2 at the wavelength ⁇ nm satisfy the following formulae (e4) and (e5):
  • ReP1 400/ReP1 (700) ⁇ ReP2 (400) /ReP2 (700) (e5).
  • the phase difference plate P 1 is a stretched product of a film made of a resin containing an alicyclic structure-containing polymer.
  • Ar is a divalent aromatic hydrocarbon ring group having D as a substituent, or a divalent aromatic heterocyclic ring group having D as a substituent,
  • D is an organic group of 1 to 67 carbon atoms having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring,
  • Z 1 and Z 2 are each independently a single bond, —O—, —O—CH 2 —, —CH 2 —O—, —O—CH 2 -CH 2 , —CH 2 -CH 2 —O—, —C( ⁇ O)—O—, —O—C( ⁇ O)—, —C( ⁇ O)—S—, —S—C( ⁇ O)—, —NR 21 —C( ⁇ O)—, —C( ⁇ O)—NR 21 —, —CF 2 —O—, —O—CF 2 —, —CH 2 -CH 2 —, —CF 2 -CF 2 —, —O—CH 2 -CH 2 —O—, —CH ⁇ CH—C( ⁇ O)—O—, —O—C( ⁇ O)—CH ⁇ CH—, —CH 2 —C( ⁇ O)—O—, —O—C( ⁇ O)—CH 2 —, —CH 2 —O—
  • a 1 and A 2 , and B 1 and B 2 each independently represent a cyclic aliphatic group optionally having a substituent or an aromatic group optionally having a substituent,
  • Y 1 to Y 4 each independently represent a single bond, —O—, —C( ⁇ O)—, —C( ⁇ O)—O—, —OC( ⁇ O)—, —NR 22 —C( ⁇ O)—, —C( ⁇ O)—NR 22 —, —O—C( ⁇ O)—O—, —NR 22 —C( ⁇ O)—O—, —O—C( ⁇ O)—NR 22 —, or —NR 22 —C( ⁇ O)—NR 23
  • R 22 and R 23 each independently represent a hydrogen atom or an alkyl group of 1 to 6 carbon atoms
  • G 1 and G 2 are each independently any of organic groups that are an aliphatic hydrocarbon group of 1 to 20 carbon atoms and a group in which one or more methylene groups (—CH 2 —) contained in an aliphatic hydrocarbon group of 3 to 20 carbon atoms are substituted by —O— or —C( ⁇ O)—, and hydrogen atoms in the organic groups of G 1 and G 2 may be substituted by an alkyl group of 1 to 5 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, or a halogen atom,
  • P 1 and P 2 each independently represent a polymerizable group, and p and q are each independently 0 or 1], wherein
  • the number of ⁇ electrons contained in D is 4 to 12.
  • D is a group selected from the group consisting of:
  • R f represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms
  • R g and R g1 represent a hydrogen atom or an organic group of 1 to 30 carbon atoms optionally having a substituent
  • R h and R h1 represent an organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms.
  • a phase difference plate, a multilayer phase difference plate, and a polymerizable compound capable of achieving uniform optical effects in a wide wavelength range
  • a polarizing plate and an image display device capable of exhibiting uniform performance in a wide wavelength range.
  • FIG. 1 is an exploded perspective view illustrating a simulation model assumed in Examples.
  • a “long-length” film refers to a film with the length that is 5 times or more the width, and preferably a film with the length that is 10 times or more the width, and specifically refers to a film having a length that allows a film to be wound up into a rolled shape for storage or transportation.
  • the upper limit of the ratio of the length of the film is not particularly limited, but is 10,000 times or less the width thereof, for example.
  • nx represents a refractive index in a direction in which the maximum refractive index is given among directions perpendicular to the thickness direction of the film (in-plane directions)
  • ny represents a refractive index in a direction, among the above-mentioned in-plane directions of the film, orthogonal to the direction giving nx
  • nz represents a refractive index in the thickness direction of the film
  • d represents the thickness of the film.
  • the measurement wavelength is 550 nm unless otherwise specified.
  • nx is a refractive index in the in-plane direction set as the slow axis direction
  • ny is a refractive index in the in-plane direction orthogonal thereto.
  • the in-plane retardation Re if necessary, a value obtained by performing a processing such as Cauchy fitting to reduce the influence of measurement errors may be adopted.
  • a direction of a constituent element being “parallel”, “perpendicular”, and “orthogonal” may allow an error within the range of not impairing the advantageous effects of the present invention, for example, within a range of ⁇ 5°, unless otherwise specified.
  • polarizing plate and a “wavelength plate” include not only a rigid member but also a flexible member such as a resin film, unless otherwise specified.
  • an angle formed by an optical axis (a transmission axis of a polarizer, a slow axis of a phase difference plate, etc.) of each film in a member including a plurality of films represents an angle when the film is viewed from the thickness direction unless otherwise specified.
  • the adhesive includes not only an adhesive in a narrow sense (an adhesive having a shear storage elastic modulus at 23° C. of 1 MPa to 500 MPa after being irradiated with energy rays or after being heat-treated) but also a tackiness agent having a shear storage elastic modulus at 23° C. of less than 1 MPa, unless otherwise specified.
  • the slow axis of a film refers to a slow axis in a plane of the film, unless otherwise specified.
  • the phase difference plate of the present invention includes a layer of a liquid crystal material oriented in an in-plane direction.
  • liquid crystal material refers to a material obtained by curing a liquid crystal composition containing a liquid crystal compound (i.e., a compound capable of exhibiting, by itself or as a mixture with other substances, a liquid crystal phase).
  • the liquid crystal material may usually include a polymer of a polymerizable liquid crystal compound.
  • a layer of the liquid crystal material being “oriented in the in-plane direction” is a liquid crystal material that, in the layer, has a structure in which the entirety or a part of molecules of the liquid crystal compound is oriented in a certain direction within a plane of the layer.
  • the liquid crystal material oriented in the in-plane direction may be usually obtained by forming a layer of the liquid crystal composition, giving orientation to the liquid crystal compound in the liquid crystal composition, and curing the liquid crystal composition while the orientation is maintained.
  • the orientation of the liquid crystal material may be set to one direction, although the manner of the orientation is not limited thereto.
  • the liquid crystal compound for forming the liquid crystal material has a plurality of mesogens per molecule and these mesogens can be oriented in different directions
  • the liquid crystal material oriented in two or more directions within the plane can be obtained.
  • the layer of the liquid crystal material may be usually a layer formed of the liquid crystal material.
  • the phase difference plate of the present invention may be formed only of the layer of the liquid crystal material or include other layers in addition to the layer of the liquid crystal material.
  • the thickness of the layer of the liquid crystal material is not particularly limited and may be any thickness as long as desired optical characteristics are exhibited.
  • the thickness of the layer of the liquid crystal material may be usually 0.3 to 8 ⁇ m.
  • an in-plane retardation Re( ⁇ ) at a wavelength ⁇ nm satisfies the following formulae (e1) and (e2).
  • the in-plane retardation Re( ⁇ ) of the phase diffirence plate satisfies the formula (e1)
  • a combination of the phase difference plate with another phase difference plate gives a multilayer phase difference plate that can have uniform optical effects in a wide wavelength range.
  • the phase difference plate is combined with another phase difference plate to be used as a multilayer wavelength plate such as a 1 ⁇ 4 wavelength plate, effects close to those obtained by an ideal wavelength plate can be obtained in a wide range or the entire range of the visible light region.
  • the multilayer phase difference plate obtained by combining the phase difference plate satisfying the aforementioned formula (e1) with other phase difference plates can easily achieve such a linear correlation. Further, the uniform optical effects can be achieved in a wide wavelength range in a thin phase difference plate by satisfying the aforementioned formula (e2).
  • the left side of the formula (e1) of a given phase difference plate i.e. a value of ⁇ Re( 400 )-Re( 550 ) ⁇ / ⁇ Re( 550 )-Re( 700 ) ⁇
  • a linear index of the given phase difference plate may be referred to as a linear index of the given phase difference plate.
  • the linear index of the phase difference plate of the present invention is 2.90 or less, preferably 2.4 or less, and further preferably 2.0 or less.
  • An ideal multilayer phase difference plate can be constituted if the linear index is exactly 1.
  • the lower limit of the linear index may be set to, for example, 1 or more.
  • phase difference plate of the present invention satisfies the following formula (e3).
  • the value of Re( 400 )/Re( 700 ) is preferably 1.50 or more, more preferably 1.70 or more, and further preferably 1.90 or more.
  • the upper limit of the value of Re( 400 )/Re( 700 ) is not particularly limited, but it may be set to, for example, 3.5 or less.
  • the phase difference plate of the present invention may be produced by curing a liquid crystal composition containing a liquid crystal compound. More specifically, the phase difference plate may be produced by forming a layer of the liquid crystal composition, giving orientation to the liquid crystal compound in the liquid crystal composition, and curing the liquid crystal composition while the orientation is maintained, to thereby form a liquid crystal material.
  • the liquid crystal material may contain a polymer of a liquid crystal compound represented by the following general formula (I). That is, as a preferable example of the liquid crystal compound for producing the phase difference plate of the present invention, a polymerizable liquid crystal compound represented by the following general formula (I) may be mentioned.
  • Ar is a divalent aromatic hydrocarbon ring group having D as a substituent, or a divalent aromatic heterocyclic ring group having D as a substituent.
  • the number of D's in one Ar is usually one.
  • the aromatic hydrocarbon ring group and aromatic heterocyclic ring group constituting Ar may have another substituent in addition to D.
  • D is an organic group of 1 to 67 carbon atoms, preferably 2 to 67 carbon atoms, having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. That is, D may be a group composed only of an aromatic ring, and may be an organic group having both an aromatic ring and a structure other than an aromatic ring.
  • D may be an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, or any other organic group.
  • aromatic hydrocarbon ring group refers to a moiety of a molecule that includes an aromatic hydrocarbon ring and is connected to the remainder of the molecule via a bond, and in which the bond is a bond that extends from the aromatic hydrocarbon ring of that moiety directly to the remainder.
  • an alkylphenyl group is an aromatic hydrocarbon ring group.
  • a phenylalkyl group is an organic group having an aromatic hydrocarbon ring, it is an organic group other than an aromatic hydrocarbon ring group.
  • aromatic heterocyclic ring group refers to a moiety of a molecule that includes an aromatic heterocyclic ring and is connected to the remainder of the molecule via a bond, and in which the bond is a bond that extends from the aromatic heterocyclic ring of that moiety directly to the remainder.
  • Examples of the divalent aromatic hydrocarbon ring group constituting Ar may include a 1,4-phenylene group, a 1,3-phenylene group, a 1,4-naphthylene group, a 2,6-naphthylene group, a 1,5-naphthylene group, an anthracenyl-9,10-diyl group, an anthracenyl-1,4-diyl group, and an anthracenyl-2,6-diyl group.
  • a 1,4-phenylene group a 1,4-naphthylene group, and a 2,6-naphthylene group are preferable, and a 1,4-phenylene group is particularly preferable.
  • Examples of the divalent aromatic heterocyclic ring group constituting Ar may include a benzothiazole-4,7-diyl group, a 1,2-benzisothiazole-4,7-diyl group, a benzoxazole-4,7-diyl group, an indole-4,7-diyl group, a benzimidazole-4,7-diyl group, a benzopyrazole-4,7-diyl group, a 1-benzofuran-4,7-diyl group, a 2-benzofuran-4,7-diyl group, a benzo[1,2-d:4,5-d′]dithiazolyl-4,8-diyl group, a benzo[1,2-d:5,4-d′]dithiazolyl-4,8-diyl group, a benzothiophenyl-4,7-diyl group, a 1H-isoindole-1,3(2H)-
  • the divalent aromatic heterocyclic ring group may include a benzothiazole-4,7-diyl group, a benzoxazole-4,7-diyl group, a 1-benzofuran-4,7-diyl group, a 2-benzofuran-4,7-diyl group, a benzo[1,2-d:4,5-d′]dithiazolyl-4,8-diyl group, a benzo[1,2-d:5,4-d′]dithiazolyl-4,8-diyl group, a benzothiophenyl-4,7-diyl group, a 1H-isoindole-1,3(2H)-dione-4,7-diyl group, a benzo[1,2-b:5,4-b′]dithiophenyl-4,8-diyl group, a benzo[1,2-b:4,5-b′]dithiophenyl-4,
  • the aromatic hydrocarbon ring group and the aromatic heterocyclic ring group constituting Ar may have a substituent R 0 described later in addition to D.
  • aromatic ring means a cyclic structure having aromaticity in a broad sense in accordance with the Huckel law. That is, the term means a cyclic conjugate structure having (4n+2) ⁇ electrons, and a cyclic structure typified by thiophene, furan, benzothiazole, and the like in which a lone pair of electrons of heteroatom such as sulfur, oxygen, nitrogen, and the like is involved in a ⁇ electron system to thereby exhibit aromaticity.
  • the number of ⁇ electrons contained in the Ar is usually 20 or less, and preferably 8 or more and 12 or less.
  • the number of ⁇ electrons contained in the aromatic ring constituting Ar is usually 20 or less, preferably 8 or more and 18 or less, and particularly preferably 8 or more and 12 or less, per aromatic ring.
  • “the number of ⁇ electrons” included in the aromatic ring constituting Ar means the total number of ⁇ electrons which adds in the number of ⁇ electrons included in the aromatic ring of the substituent.
  • aromatic hydrocarbon ring constituting D may include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, and a fluorene ring.
  • a benzene ring, a naphthalene ring, and an anthracene ring are preferable as the aromatic hydrocarbon ring.
  • aromatic heterocyclic rings constituting D may include a 1H-isoindole-1,3(2H)-dione ring, a 1-benzofuran ring, a 2-benzofuran ring, an acridine ring, an isoquinoline ring, an imidazole ring, an indole ring, an oxadiazole ring, an oxazole ring, an oxazolopyrazine ring, an oxazolopyridine ring, an oxazolopyridazine ring, an oxazolopyrimidine ring, a quinazoline ring, a quinoxaline ring, a quinoline ring, a cinnoline ring, a thiadiazole ring, a thiazole ring, a thiazolopyrazine ring, a thiazolopyridine ring, a thiazolopyridazine ring,
  • aromatic heterocyclic ring a monocyclic aromatic heterocyclic ring such as a furan ring, a pyran ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a thiazole ring, and a thiadiazole ring
  • a condensed aromatic heterocyclic ring such as a benzothiazole ring, a benzoxazole ring, a quinoline ring, a 1-benzofuran ring, a 2-benzofuran ring, a 1H-isoindole-1,3(2H)-dione ring, a benzo[c]thiophene ring, a benzo[b]thiophene ring, a thiazolopyridine ring, a thiazolopyrazine ring, a benzoisoxazol ring, a benzoxadiazole ring, and a
  • (D-3) a group represented by —C(R f ) ⁇ N—N(R g )R h ,
  • (D-4) a group represented by —C(R f ) ⁇ N—N ⁇ C(R g1 )R h , and
  • (D-5) a group represented by —C(R f ) ⁇ N—N ⁇ R h1 .
  • R f represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • R g and R g1 each independently represent a hydrogen atom or an organic group of 1 to 30 carbon atoms optionally having a substituent.
  • Examples of the organic group of 1 to 30 carbon atoms and the substituent thereof may include the same examples as those listed as the specific examples of the organic group of 1 to 30 carbon atoms and the substituent thereof for Ay, which will be described later.
  • Rh represents an organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms.
  • Specific examples of R h may include the same examples as those listed as the specific examples of the organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms for Ax, which will be described later.
  • Rhl represents an organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms.
  • Specific examples of Rhl may include the same examples as those listed as the specific examples of the organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms for Az, which will be described later.
  • the aromatic hydrocarbon ring group in a case where D is (D-1) the aromatic hydrocarbon ring group optionally having a substituent may include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a fluorenyl group.
  • aromatic hydrocarbon ring group a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable.
  • the aromatic heterocyclic ring group in a case where D is (D-2) may include a phthalimido group, a 1-benzofuranyl group, a 2-benzofuranyl group, an acridinyl group, an isoquinolinyl group, an imidazolyl group, an indolinyl group, a flazanyl group, an oxazolyl group, an oxazolopyrazinyl group, an oxazolopyridinyl group, an oxazolopyridazinyl group, an oxazolopyrimidinyl group, a quinazolinyl group, a quinoxalinyl group, a quinolyl group, a cinnolinyl group, a thiadiazolyl group, a thiazolyl group, a thiazolopyrazinyl group, a thiazolopyridyl
  • a monocyclic aromatic heterocyclic ring group such as a furanyl group, a pyranyl group, a thienyl group, an oxazolyl group, a flazanyl group, a thiazolyl group, and a thiadiazolyl group
  • a condensed aromatic heterocyclic ring group such as a benzothiazolyl group, a benzoxazolyl group, a quinolyl group, a 1-benzofuranyl group, a 2-benzofuranyl group, a phthalimido group, a benzo[c]thienyl group, a benzo[b]thienyl group, a thiazolopyridyl group, a thiazolopyrazinyl group, a benzoisoxazolyl group, a benzoxadiazolyl group and a benzothiazolyl group are preferable.
  • Examples of the organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms as the constituent element of (D-3) to (D-5) may include an indanyl group, an indenyl group, a 1,2,3,4-tetrahydronaphthyl group, a 1,4-dihydronaphthyl group, a 1,2-dihydronaphthyl group, a 1,3-benzodioxonyl group, a 1,4-benzodioxanyl group, a 2,3-dihydrobenzofuranyl group, a 1,3-dihydroisobenzofuranyl group, a 3,4-dihydro-1H-2-benzopyran group, a 3,4-dihydro-2H-1-benzopyranyl group, a 4H-1-benzopyranyl group, a 2H-1-
  • an indanyl group an indenyl group, a 1,2,3,4-tetrahydronaphthyl group, a 1,4-dihydronaphthyl group, a 1,2-dihydronaphthyl group, a 1,3-benzodioxonyl group, a 1,4-benzodioxanyl group, 3,4-dihydro-1H-2-benzopyran, a 3,4-dihydro-2H-1-benzopyranyl group, a 4H-1-benzopyranyl group, a 2H-1-benzopyranyl group, a 1H-2-benzopyranyl group, a 4-oxo-4H-1-benzopyranyl group, a 4-chromanone group, a dihydropyranyl group, a tetrahydropyranyl group, a dihydrofuranyl group, and a tetrahydrofuranyl group are preferable.
  • the aromatic hydrocarbon ring and the aromatic heterocyclic ring constituting D (for example, the aromatic hydrocarbon ring constituting (D-1), the aromatic heterocyclic ring constituting (D-2), and the aromatic hydrocarbon ring and the aromatic heterocyclic ring constituting (D-3) to (D-5)), and the aromatic hydrocarbon ring group and the aromatic heterocyclic ring group, which are D, and the organic group having at least one aromatic ring selected from the group consisting of the aromatic hydrocarbon ring of 6 to 30 carbon atoms and the aromatic heterocyclic ring of 2 to 30 carbon atoms, which are D, may have a substituent.
  • the number of the substituents may be one or plural per one ring. When a ring has a plurality of substituents, they may be the same as or different from one another.
  • Examples of such a substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkenyl group of 2 to 6 carbon atoms such as a vinyl group and an allyl group; a halogenated alkyl group of 1 to 6 carbon atoms such as a trifluoromethyl group; an N,N-dialkylamino group of 1 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; —OCF 3 ; —C( ⁇ O)—
  • R b1 represents an alkyl group of 1 to 20 carbon atoms optionally having a substituent, an alkenyl group of 2 to 20 carbon atoms optionally having a substituent, a cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent, or an aromatic hydrocarbon ring group of 5 to 12 carbon atoms optionally having a substituent.
  • R a represents an alkyl group of 1 to 12 carbon atoms such as a methyl group or an ethyl group; or an aromatic hydrocarbon ring group of 6 to 20 carbon atoms optionally having, as a substituent, an alkyl group of 1 to 6 carbon atoms or an alkoxy group of 1 to 6 carbon atoms, such as a phenyl group, a 4-methylphenyl group, or a 4-methoxyphenyl group.
  • a halogen atom a cyano group, a nitro group, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, and a halogenated alkyl group of 1 to 6 carbon atoms are preferable.
  • Examples of the above-mentioned Ar may include a phenylene group substituted with a group represented by a formula —C(R f ) ⁇ N—N(R g )R h , a phenylene group substituted with a group represented by a formula —C(R f ) ⁇ N—N ⁇ C(R g1 )R h , a phenylene group substituted with a group represented by a formula —C(R f ) ⁇ N—N ⁇ R h1 , a naphthylene group substituted with a group represented by a formula —C(R f ) ⁇ N—N(R g )R h , a naphthylene group substituted with a group represented by a formula —C(R f ) ⁇ N—N ⁇ C(R g1 )R h , a naphthylene group substituted with a group represented by a formula —C(R f )
  • Ar a group represented by any of the following formulae (IIa-1) to (IIa-7), formulae (IIb-1) to (IIb-7), and formulae (IIc-1) to (IIc-7) is preferable.
  • Ax represents an organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms,
  • Ay represents a hydrogen atom or an organic group of 1 to 30 carbon atoms optionally having a substituent
  • Az represents an organic group having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms,
  • aromatic rings in Ax and Ax may have a substituent
  • Q represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms.
  • examples of the alkyl group of 1 to 6 carbon atoms in Q may include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
  • R 0 represents a halogen atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, and a tertiary butyl group; an alkenyl group of 2 to 6 carbon atoms; a halogenated alkyl group of 1 to 6 carbon atoms; an N,N-dialkylamino group of 2 to 12 carbon atoms; an alkoxy group of 1 to 6 carbon atoms; a nitro group; —C( ⁇ O)—R a1 ; —C( ⁇ O)—O—R a1 ; or —SO 2 R a1 , and R a1 represents an aliphatic hydrocarbon group of 1 to 12 carbon atoms.
  • the plurality of R 0 s may be the same as or different from one another.
  • a halogen atom, a cyano group, an alkyl group of 1 to 6 carbon atoms, a halogenated alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, and a nitro group are preferable from the viewpoint of improving solubility.
  • n1 is 0 to 3
  • n2 is 0 to 4
  • n3 is 0 or 1
  • Specific examples of the aliphatic hydrocarbon group of 1 to 12 carbon atoms as examples of R a1 may include an alkyl group of 1 to 12 carbon atoms such as a methyl group and an ethyl group, an alkenyl group of 1 to 12 carbon atoms such as a vinyl group, an aryl group, and a butenyl group, and an alkynyl group of 1 to 12 carbon atoms such as a propynyl group, a butynyl group, and a pentynyl group.
  • An alkyl group of 1 to 12 carbon atoms is preferable.
  • formulae (iia-1), (iia-2), (iia-10), and (iia-12), formulae (iib-1), (iib-2), (iib-10), and (iib-12), and formulae (iic-1), (iic-2), (iic-10), and (iic-12) are particularly preferable.
  • Ax may have a plurality of aromatic rings, and may have an aromatic hydrocarbon ring and an aromatic heterocyclic ring. When a plurality of aromatic hydrocarbon rings and aromatic heterocyclic ring are present, they may be the same as or different from one another.
  • Examples of the aromatic hydrocarbon ring in Ax may include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, and a fluorene ring.
  • a benzene ring, a naphthalene ring, and an anthracene ring are preferable.
  • Examples of the aromatic heterocyclic ring in Ax may include a 1H-isoindole-1,3(2H)-dione ring, a 1-benzofuran ring, a 2-benzofuran ring, an acridine ring, an isoquinoline ring, an imidazole ring, an indole ring, an oxadiazole ring, an oxazole ring, an oxazolopyrazine ring, an oxazolopyridine ring, an oxazolopyridazyl ring, an oxazolopyrimidine ring, a quinazoline ring, a quinoxaline ring, a quinoline ring, a cinnoline ring, a thiadiazole ring, a triazole ring, a thiazolopyrazine ring, a thiazolopyridine ring, a thiazolopyridazine ring,
  • aromatic heterocyclic ring a monocyclic aromatic heterocyclic ring such as a furan ring, a pyran ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a thiazole ring, and a thiadiazole ring; and a condensed aromatic heterocyclic ring such as a benzothiazole ring, a benzoxazole ring, a quinoline ring, a 1-benzofuran ring, a 2-benzofuran ring, a 1H-isoindole-1,3(2H)-dione ring, a benzo[c]thiophene ring, a benzo[b]thiophene ring, a thiazolopyridine ring, a thiazolopyrazine ring, a benzoisoxazol ring, a benzoxadiazole ring, and a
  • the aromatic ring in Ax may have a substituent.
  • a substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkenyl group of 2 to 6 carbon atoms such as a vinyl group and an allyl group; a halogenated alkyl group of 1 to 6 carbon atoms such as a trifluoromethyl group; an N,N-dialkylamino group of 2 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; —
  • R b represents an alkyl group of 1 to 20 carbon atoms optionally having a substituent, an alkenyl group of 2 to 20 carbon atoms optionally having a substituent, a cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent, or an aromatic hydrocarbon ring group of 5 to 12 carbon atoms optionally having a substituent.
  • R a represents the same meanings as described above.
  • substituent of the aromatic ring in Ax a halogen atom, a cyano group, an alkyl group of 1 to 6 carbon atoms, and an alkoxy group of 1 to 6 carbon atoms are preferable.
  • Ax may have a plurality of substituents selected from the substituents described above.
  • the substituents may be the same as or different from one another.
  • Examples of the alkyl group of 1 to 20 carbon atoms in a case where R b is the alkyl group of 1 to 20 carbon atoms optionally having a substituent may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a 1-methylpentyl group, a 1-ethylpentyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tride
  • Examples of the alkenyl group of 2 to 20 carbon atoms in a case where R b is the alkenyl group of 2 to 20 carbon atoms optionally having a substituent may include a vinyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a decenyl group, an undecenyl group, a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, a nonadenyl group, and an icosenyl group.
  • the number of substituents in a case where R b is the alkyl group of 1 to 20 carbon atoms having a substituent and in a case where R b is the alkenyl group of 2 to 20 carbon atoms having a substituent may be one or plural. When a plurality of substituents are included, they may be the same as or different from one another.
  • the substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an N,N-dialkylamino group of 2 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 20 carbon atoms such as a methoxy group, an ethoxy group, an isopropoxy group, and a butoxy group; an alkoxy group of 1 to 12 carbon atoms substituted with an alkoxy group of 1 to 12 carbon atoms such as a methoxymethoxy group and a methoxyethoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; an aromatic heterocyclic ring group such as a triazolyl group, a pyrrolyl group, a furanyl group, a thiophenyl group, and a benzothiazole-2-
  • a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkoxy group of 1 to 20 carbon atoms such as a methoxy group, an ethoxy group, an isopropoxy group, and a butoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; an aromatic heterocyclic ring group of 2 to 20 carbon atoms such as a furanyl group and a thiophenyl group; a cycloalkyl group of 3 to 8 carbon atoms such as a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group; and a fluoroalkyl group of 1 to 12 carbon atoms, in which one or more hydrogen atoms are substituted by a fluorine atom, such as
  • Examples of the cycloalkyl group of 3 to 12 carbon atoms in a case where R b is the cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclooctyl group. Among these, a cyclopentyl group and a cyclohexyl group are preferable.
  • R b is the cycloalkyl group of 3 to 12 carbon atoms having a substituent
  • the number of substituents may be one or plural. When a plurality of substituents are included, they may be the same as or different from one another.
  • the substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an N,N-dialkylamino group of 2 to 12 carbon atoms such as a dimethylamino group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; and an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group.
  • a halogen atom such as a fluorine atom and a chlorine atom
  • a cyano group an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group
  • an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group
  • a nitro group an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group
  • Examples of the aromatic hydrocarbon ring group of 5 to 12 carbon atoms in a case where R b is the aromatic hydrocarbon ring group of 5 to 12 carbon atoms optionally having a substituent may include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. Among these, a phenyl group is preferable.
  • the number of substituents in a case where R b has 5 to 12 carbon atoms having a substituent may be one or plural. When a plurality of substituents are included, they may be the same as or different from one another.
  • the substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an N,N-dialkylamino group of 2 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 20 carbon atoms such as a methoxy group, an ethoxy group, an isopropoxy group, and a butoxy group; an alkoxy group of 1 to 12 carbon atoms substituted with an alkoxy group of 1 to 12 carbon atoms such as a methoxymethoxy group and a methoxyethoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphth
  • substituent of the aromatic hydrocarbon ring group of 5 to 12 carbon atoms one or more substituents selected from a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkoxy group of 1 to 20 carbon atoms such as a methoxy group, an ethoxy group, an isopropoxy group, and a butoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; an aromatic heterocyclic ring group of 2 to 20 carbon atoms such as a furanyl group and a thiophenyl group; a cycloalkyl group of 3 to 8 carbon atoms such as a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group; a fluoroalkyl group of 1 to 12 carbon atoms, in which one or more substituents selected from
  • the aromatic ring in Ax may have a plurality of the same or different substituents, and two adjacent substituents may be bonded together to form a ring.
  • the ring formed may be a single ring or a fused polycycle ring, and may be an unsaturated ring or a saturated ring.
  • the “number of carbon atoms” of the aromatic hydrocarbon ring having 6 to 30 carbon atoms and the aromatic heterocyclic ring of 2 to 30 carbon atoms included in Ax means the number of carbon atoms of the ring itself, which does not include the carbon atoms of the substituent bonded to the ring.
  • Ax may include the following (Ax-1) to (Ax-5).
  • (Ax-1) a hydrocarbon ring group of 6 to 40 carbon atoms having one or more aromatic hydrocarbon rings each having 6 to 30 carbon atoms,
  • (Ax-2) a heterocyclic ring group of 2 to 40 carbon atoms having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms,
  • (Ax-3) an alkyl group of 1 to 12 carbon atoms substituted with one or more of an aromatic hydrocarbon ring group of 6 to 30 carbon atoms and an aromatic heterocyclic ring group of 2 to 30 carbon atoms,
  • (Ax-4) an alkenyl group of 2 to 12 carbon atoms substituted with one or more of an aromatic hydrocarbon ring group of 6 to 30 carbon atoms and an aromatic heterocyclic ring group of 2 to 30 carbon atoms, and
  • (Ax-5) An alkynyl group of 2 to 12 carbon atoms substituted with one or more of an aromatic hydrocarbon ring group of 6 to 30 carbon atoms and an aromatic heterocyclic ring group of 2 to 30 carbon atoms.
  • aromatic hydrocarbon ring in (Ax-1) may include the same examples as those listed as the specific examples of the aromatic hydrocarbon ring in Ax.
  • hydrocarbon ring group in (Ax-1) may include an aromatic hydrocarbon ring group of 6 to 30 carbon atoms (such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a fluorenyl group), an indanyl group, an indenyl group, a 1,2,3,4-tetrahydronaphtyl group, a 1,4-dihydronaphthyl group, and a 1,2-dihydronaphthyl group.
  • aromatic hydrocarbon ring and the aromatic heterocyclic ring in (Ax-2) may include the same examples as those listed as the specific examples of the aromatic hydrocarbon ring and the aromatic heterocyclic ring in Ax.
  • specific examples of the heterocyclic ring group in (Ax-2) may include an aromatic heterocyclic ring group of 2 to 30 carbon atoms (such as a phthalimido group, a 1-benzofuranyl group, a 2-benzofuranyl group, an acridinyl group, an isoquinolinyl group, an imidazolyl group, an indolinyl group, a flazanyl group, an oxazolyl group, an oxazolopyrazinyl group, an oxazolopyridinyl group, an oxazolopyridazinyl group, an oxazolopyrimidinyl group, a quinazolinyl group, a quinoxalinyl group, a quinolyl group,
  • alkyl group of 1 to 12 carbon atoms in (Ax-3) may include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • aromatic hydrocarbon ring group of 6 to 30 carbon atoms and the aromatic heterocyclic ring group of 2 to 30 carbon atoms in (Ax-3) may include the same examples as those listed as the specific examples of them in (Ax-1) and (Ax-2).
  • alkenyl group of 2 to 12 carbon atoms in (Ax-4) may include a vinyl group and an allyl group.
  • aromatic hydrocarbon ring group of 6 to 30 carbon atoms and the aromatic heterocyclic ring group of 2 to 30 carbon atoms in (Ax-4) may include the same examples as those listed as the specific examples of them in (Ax-1) and (Ax-2).
  • alkynyl group of 2 to 12 carbon atoms in (Ax-5) may include an ethynyl group and a propynyl group.
  • aromatic hydrocarbon ring group of 6 to 30 carbon atoms and the aromatic heterocyclic ring group of 2 to 30 carbon atoms in (Ax-5) may include the same examples as those listed as the specific examples of them in (Ax-1) and (Ax-2).
  • (Ax-1) to (Ax-5) are those in which the organic groups as those listed above additionally have one or a plurality of substituents. When a plurality of substituents are included, they may be the same as or different from one another.
  • Examples of such a substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkenyl group of 2 to 6 carbon atoms such as a vinyl group and an allyl group; a halogenated alkyl group of 1 to 6 carbon atoms such as a trifluoromethyl group; an N,N-dialkylamino group of 2 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; —OCF 3 ; —C( ⁇ O)—
  • substituent in (Ax-1) to (Ax-5) one or more substituents selected from a halogen atom, a cyano group, an alkyl group of 1 to 6 carbon atoms, and an alkoxy group of 1 to 6 carbon atoms are preferable.
  • ⁇ represents a bond with an N atom (i.e., the N atom bonded to Ax in the formulae (IIa-1) to (IIa-7) and formulae (IIb-1) to (IIb-7)) extending from any optional position in the ring.
  • hydrocarbon ring group in (Ax-1) may include groups represented by the following formulae (1-1) to (1-20), and aromatic hydrocarbon ring groups of 6 to 30 carbon atoms represented by the formulae (1-9) to (1-20) and the like are preferable.
  • heterocyclic ring group in (Ax-2) may include groups represented by the following formulae (2-1) to (2-51), and aromatic heterocyclic ring groups of 2 to 30 carbon atoms represented by the formulae (2-12) to (2-51) and the like are preferable.
  • ⁇ represents —CH 2 —, —NR c —, an oxygen atom, a sulfur atom, —SO—, or —SO 2 —,
  • Y and Z each independently represent —NR c —, an oxygen atom, a sulfur atom, —SO—, or —SO 2 —, and
  • E represents —NR c —, an oxygen atom, or a sulfur atom.
  • R c represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group. (However, in each of the formulae, the oxygen atom, sulfur atom, —SO—, and —SO 2 —each are not adjacent to each other.)]
  • alkyl group in (Ax-3) may include groups represented by the following formulae (3-1) to (3-8).
  • alkenyl group in (Ax-4) may include groups represented by the following formulae (4-1) to (4-5).
  • alkynyl group in (Ax-5) may include groups represented by the following formulae (5-1) to (5-2).
  • Ax further include one or a plurality of substituents on the ring may also be included in the example of Ax.
  • the plurality of substituents may be the same as or different from one another.
  • Examples of such a substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkenyl group of 2 to 6 carbon atoms such as a vinyl group and an allyl group; a halogenated alkyl group of 1 to 6 carbon atoms such as a trifluoromethyl group and a pentafluoroethyl group; an N,N-dialkylamino group of 2 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group;
  • R b and R a have the same meanings as described above.
  • a substituent in Ax a halogen atom, a cyano group, an alkyl group of 1 to 6 carbon atoms, and an alkoxy group of 1 to 6 carbon atoms are preferable.
  • Ax is preferably an aromatic hydrocarbon ring group of 6 to 30 carbon atoms or an aromatic heterocyclic ring group of 2 to 30 carbon atoms.
  • Ax is an aromatic hydrocarbon ring group of 6 to 20 carbon atoms or an aromatic heterocyclic ring group of 4 to 20 carbon atoms, and it is further more preferable that Ax is any of the groups represented by the above-described formula (2-3), and formula (2-13), formula (2-15), and formula (2-30).
  • the aforementioned ring may have one or a plurality of substituents.
  • the plurality of substituents may be the same as or different from one another.
  • substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkenyl group of 2 to 6 carbon atoms such as a vinyl group and an allyl group; a halogenated alkyl group of 1 to 6 carbon atoms such as a trifluoromethyl group and a pentafluoroethyl group; an N,N-dialkylamino group of 1 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an eth
  • R b and R a have the same meanings as described above.
  • a halogen atom As a substituent in the aforementioned ring, a halogen atom, a cyano group, an alkyl group of 1 to 6 carbon atoms, and an alkoxy group of 1 to 6 carbon atoms are preferable.
  • Groups represented by the following formulae (III-1) to (III-7) are more preferable as Ax.
  • R 2 to R 12 each independently represent a hydrogen atom, a halogen atom, an alkyl group of 1 to 6 carbon atoms, a cyano group, a nitro group, a fluoroalkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, —OCF 3 , or —C( ⁇ O)—O—R b
  • R b represents an alkyl group of 1 to 20 carbon atoms optionally having a substituent, an alkenyl group of 2 to 20 carbon atoms optionally having a substituent, a cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent, or an aromatic hydrocarbon ring group of 5 to 12 carbon atoms optionally having a substituent.
  • R 2 to R 12 are a hydrogen atom, or one or more of R 2 to R 12 are an alkoxy group of 1 to 6 carbon atoms optionally having a substituent and the remainder is a hydrogen atom.
  • C—R 2 to C—R 5 may be the same as or different from one another, and one or more of C—R 2 to C—R 5 constituting the ring may be replaced with a nitrogen atom.
  • Specific examples of the group in which one or more of C—R 2 to C—R 5 of the group represented by the aforementioned formula (III) are replaced with a nitrogen atom may include structures represented by the following formulae (III-1-1) to (III-1-8). However, the group in which one or more of C-R 2 to C-R 5 are replaced with a nitrogen atom is not limited thereto.
  • Ay is an organic group of 1 to 30 carbon atoms optionally having a substituent
  • examples of such an organic group may include, but are not limited to, an alkyl group of 1 to 20 carbon atoms optionally having a substituent, an alkenyl group of 2 to 20 carbon atoms optionally having a substituent, an alkynyl group of 2 to 20 carbon atoms optionally having a substituent, a cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent, —SO 2 R a , —C( ⁇ O)—R b , —CS—NH—R b , an aromatic hydrocarbon ring group of 6 to 30 carbon atoms optionally having a substituent, and an aromatic heterocyclic ring group of 2 to 30 carbon atoms optionally having a substituent.
  • R a and R b have the same meanings as described above.
  • alkyl group of 1 to 20 carbon atoms in a case where Ay is the alkyl group of 1 to 20 carbon atoms optionally having a substituent specific examples of the alkenyl group of 2 to 20 carbon atoms in a case where Ay is the alkenyl group of 2 to 20 carbon atoms optionally having a substituent
  • specific examples of the cycloalkyl group of 3 to 12 carbon atoms in a case where Ay is the cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent may include the same examples as those listed as the specific examples of the alkyl group of 1 to 20 carbon atoms in a case where R b is the alkyl group of 1 to 20 carbon atoms optionally having a substituent, the specific examples of the alkenyl group of 2 to 20 carbon atoms in a case where R b is the alkenyl group of 2 to 20 carbon atoms optionally having a substituent, and the specific examples of the alkenyl group
  • the number of carbon atoms of the alkyl group of 1 to 20 carbon atoms in the alkyl group of 1 to 20 carbon atoms optionally having a substituent is preferably 1 to 12
  • the number of carbon atoms of the alkenyl group of 2 to 20 carbon atoms in the alkenyl group of 2 to 20 carbon atoms optionally having a substituent is preferably 2 to 12
  • the number of carbon atoms of the cycloalkyl group of 3 to 12 carbon atoms in the cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent is preferably 3 to 10.
  • alkynyl group of 2 to 20 carbon atoms in a case where Ay is the alkynyl group of 2 to 20 carbon atoms optionally having a substituent may include an ethynyl group, a propynyl group, a 2-propynyl group (propargyl group), a butynyl group, a 2-butynyl group, a 3-butynyl group, a pentinyl group, a 2-pentinyl group, a hexynyl group, a 5-hexynyl group, a heptynyl group, an octynyl group, a 2-octinyl group, a nonanyl group, a decanyl group, and a 7-decanyl group.
  • Ay is the alkyl group of 1 to 20 carbon atoms optionally having a substituent
  • Ay is the alkenyl group of 2 to 20 carbon atoms optionally having a substituent
  • Ay is the cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent
  • Ay is the alkynyl group of 2 to 20 carbon atoms optionally having a substituent
  • the number of the substituents may be one or plural.
  • a plurality of substituents are included, they may be the same as or different from one another.
  • Examples of the substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an N,N-dialkylamino group of 2 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 20 carbon atoms such as a methoxy group, an ethoxy group, an isopropoxy group, and a butoxy group; an alkoxy group of 1 to 12 carbon atoms substituted with an alkoxy group of 1 to 12 carbon atoms such as a methoxymethoxy group and a methoxyethoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; an aromatic heterocyclic ring group of 2 to 20 carbon atoms such as a triazoryl group, a pyrrolyl group, a furanyl group, and a thiophenyl group;
  • Examples of the aromatic hydrocarbon ring group, the aromatic heterocyclic ring group, and the substituent in a case where Ay is the aromatic hydrocarbon ring group of 6 to 30 carbon atoms optionally having a substituent and in a case where Ay is the aromatic heterocyclic ring group of 2 to 30 carbon atoms optionally having a substituent may include the same examples as those listed as the specific examples of them included in Ax.
  • the number of substituents may be one or plural. When a plurality of substituents are included, they may be the same as or different from one another.
  • the number of carbon atoms of the aromatic hydrocarbon ring group in these examples is preferably 6 to 20, more preferably 6 to 18, and still more preferably 6 to 12.
  • the number of carbon atoms of the aromatic heterocyclic ring group in these examples is preferably 2 to 20, and more preferably 2 to 18.
  • Ay is preferably a hydrogen atom, an alkyl group of 1 to 20 carbon atoms optionally having a substituent, an alkenyl group of 2 to 20 carbon atoms optionally having a substituent, an alkynyl group of 2 to 20 carbon atoms optionally having a substituent, a cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent, an aromatic hydrocarbon ring group of 6 to 18 carbon atoms optionally having a substituent, or an aromatic heterocyclic ring group of 2 to 18 carbon atoms optionally having a substituent.
  • Ay is more preferably a hydrogen atom, an alkyl group of 1 to 18 carbon atoms optionally having a substituent, an alkenyl group of 2 to 18 carbon atoms optionally having a substituent, an alkynyl group of 2 to 18 carbon atoms optionally having a substituent, a cycloalkyl group of 3 to 10 carbon atoms optionally having a substituent, an aromatic hydrocarbon ring group of 6 to 12 carbon atoms optionally having a substituent, or an aromatic heterocyclic ring group of 2 to 18 carbon atoms optionally having a substituent.
  • an alkyl group of 1 to 18 carbon atoms optionally having a substituent is particularly preferable as Ay
  • an alkyl group of 2 to 12 carbon atoms optionally having a substituent is particularly more preferable.
  • Examples of Az may include the following (Az-6) to (Az-7):
  • (Az-7) a heterocyclic ring group of 2 to 40 carbon atoms having one or more aromatic rings selected from the group consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms and an aromatic heterocyclic ring of 2 to 30 carbon atoms.
  • hydrocarbon ring group in (Az-6) may include structures represented by the following formulae (6-1) to (6-12), and aromatic hydrocarbon ring groups of 6 to 30 carbon atoms represented by the formulae (6-1), (6-3) to (6-4), and (6-7) to (6-12) are preferable.
  • heterocyclic ring group in (Az-7) may include structures represented by the following formulae (7-1) to (7-30), and aromatic heterocyclic ring groups of 2 to 30 carbon atoms represented by the formulae (7-1) to (7-11) are preferable.
  • ⁇ represents —CH 2 —, —NR c —, an oxygen atom, a sulfur atom, —SO—, or —SO 2 —,
  • Y and Z each independently represent —NR c —, an oxygen atom, a sulfur atom, —SO—, or —SO 2 —, and
  • E represents —NR c —, an oxygen atom, or a sulfur atom.
  • R c represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group. (However, in each of the formulae, the oxygen atom, sulfur atom, —SO—, and —SO 2 — each are not adjacent to each other.)]
  • the preferable examples of the above-mentioned Az further include one or a plurality of substituents on the ring may also be included in the example of Az.
  • the plurality of substituents may be the same as or different from one another.
  • Examples of such a substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkenyl group of 2 to 6 carbon atoms such as a vinyl group and an allyl group; a halogenated alkyl group of 1 to 6 carbon atoms such as a trifluoromethyl group; an N,N-dialkylamino group of 1 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; —OCF 3 ; —C( ⁇ O)—
  • R b and R a have the same meanings as described above.
  • a substituent in the aforementioned ring in Az a halogen atom, a cyano group, an alkyl group of 1 to 6 carbon atoms, and an alkoxy group of 1 to 6 carbon atoms are preferable.
  • Az is preferably a hydrocarbon ring group of 6 to 40 carbon atoms having one or more aromatic hydrocarbon ring group of 6 to 30 carbon atoms or a hydrocarbon ring group heterocyclic ring group of 2 to 40 carbon atoms having one or more aromatic heterocyclic rings of 2 to 30 carbon atoms.
  • Az is more preferably a hydrocarbon ring group of 6 to 40 carbon atoms having one or more aromatic hydrocarbon rings of 6 to 30 carbon atoms, and more preferably any of the groups represented by the above-described formula (6-1), formula (6-3), formula (6-4), formula (6-10), and formula (7-1) to formula (7-9).
  • the aforementioned ring may have one or a plurality of substituents.
  • the plurality of substituents may be the same as or different from one another.
  • substituent may include a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; an alkyl group of 1 to 6 carbon atoms such as a methyl group, an ethyl group, and a propyl group; an alkenyl group of 2 to 6 carbon atoms such as a vinyl group and an allyl group; a halogenated alkyl group of 1 to 6 carbon atoms such as a trifluoromethyl group and a pentafluoroethyl group; an N,N-dialkylamino group of 1 to 12 carbon atoms such as a dimethylamino group; an alkoxy group of 1 to 6 carbon atoms such as a methoxy group, an eth
  • R b and R a have the same meanings as described above.
  • a halogen atom As a substituent in the aforementioned ring, a halogen atom, a cyano group, an alkyl group of 1 to 6 carbon atoms, and an alkoxy group of 1 to 6 carbon atoms are preferable.
  • R 2 to R 5 and R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 each independently represent a hydrogen atom, a halogen atom, an alkyl group of 1 to 6 carbon atoms, a cyano group, a nitro group, a fluoroalkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, —OCF 3 , or —C( ⁇ O)—O—R b
  • R b represents an alkyl group of 1 to 20 carbon atoms optionally having a substituent, an alkenyl group of 2 to 20 carbon atoms optionally having a substituent, a cycloalkyl group of 3 to 12 carbon atoms optionally having a substituent, or an aromatic hydrocarbon ring group of 5 to 12 carbon atoms optionally having a substituent.
  • R 2 to R 11 are a hydrogen atom, or one or more of R 2 to R 11 are an alkoxy group of 1 to 6 carbon atoms optionally having a substituent and the remainder is a hydrogen atom.
  • Z 1 and Z 2 are each independently a single bond, —O—, —O—CH 2 —, —CH 2 —O—, —O—CH 2 -CH 2 , —CH 2 -CH 2 —O—, —C( ⁇ O)—O—, —O—C( ⁇ O)—, —C( ⁇ O)—S—, —S—C( ⁇ O)—, —NR 21 —C( ⁇ O)—, —C( ⁇ O)—NR 21 —, —CF 2 —O—, —O—CF 2 —, —CH 2 -CH 2 —, —CF 2 -CF 2 —, —O—CH 2 -CH 2 —O—, —CH ⁇ CH—C( ⁇ O)—O—, —O—C( ⁇ O)—CH ⁇ CH—, —CH 2 —C( ⁇ O)—O—, —O—C( ⁇ O)—CH 2 —, —O—C( ⁇ O
  • Z 1 and Z 2 are each independently —C( ⁇ O)—O— or —O—C( ⁇ O)—.
  • G 1 and G 2 are each independently any of organic groups that are an aliphatic hydrocarbon group of 1 to 20 carbon atoms and a group in which one or more methylene groups (—CH 2 —) contained in an aliphatic hydrocarbon group of 3 to 20 carbon atoms are substituted by —O— or —C( ⁇ O)—, and hydrogen atoms in the organic groups of G 1 and G 2 may be substituted with one or more substituents selected from the group consisting of an alkyl group of 1 to 5 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, and a halogen atom.
  • substitution of the methylene group by —O— or —C( ⁇ O)— is preferably substitution of a methylene group other than the methylene group directly connected to any of P 1 , P 2 , Y 3 , and Y 4 .
  • a group in which one of methylene groups (—CH 2 —) in an aliphatic hydrocarbon group of three carbon atoms is substituted by —O— is preferably —CH 2 —O—CH 2 —.
  • —O— preferably does not substitute for the continuous methylene groups in the aliphatic hydrocarbon group (i.e., does not form the structure of —O—O—)
  • —C( ⁇ O)— preferably does not substitute for the continuous methylene groups in the aliphatic hydrocarbon group (i.e., does not form the structure of —C( ⁇ O)—C( ⁇ O)—).
  • G 1 and G 2 are an aliphatic hydrocarbon group of 1 to 20 carbon atoms
  • specific examples thereof are not particularly limited but may include a chain aliphatic hydrocarbon group such as an alkylene group of 1 to 20 carbon atoms, an alkenylene group of 1 to 20 carbon atoms, and an alkynylene group of 1 to 20 carbon atoms.
  • the number of carbon atoms of the aliphatic hydrocarbon group described above is preferably 3 to 12, and more preferably 4 to 10.
  • an alkylene group of 1 to 20 carbon atoms optionally being substituted with a fluorine atom or a group represented by —(CH 2 ) j —C( ⁇ O)—O—(CH 2 ) k — optionally being substituted with a fluorine atom (in which j and k each represent an integer of 2 to 12 and preferably represent an integer of 2 to 8) is preferable.
  • an alkylene group of 2 to 12 carbon atoms optionally being substituted with a fluorine atom is more preferable
  • an unsubstituted alkylene group of 2 to 12 carbon atoms is more preferable
  • a group represented by —(CH 2 ) 1 — is particularly preferable.
  • a 1 , A 2 , B 1 , and B 2 each independently represent a cyclic aliphatic group optionally having a substituent or an aromatic group optionally having a substituent, and a cyclic aliphatic group of 5 to 20 carbon atoms optionally having a substituent or an aromatic group of 2 to 20 carbon atoms optionally having a substituent is preferable.
  • cyclic aliphatic group may include a cycloalkanediyl group of 5 to 20 carbon atoms such as a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, a cycloheptane-1,4-diyl group, and a cyclooctane-1,5-diyl group; and a bicycloalkanediyl group of 5 to 20 carbon atoms such as a decahydronaphthalene-1,5-diyl group, and a decahydronaphthalene-2,6-diyl group.
  • a cycloalkanediyl group of 5 to 20 carbon atoms such as a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, a cycloheptane-1,4-diyl
  • cyclic aliphatic group a cycloalkanediyl group of 5 to 20 carbon atoms optionally being substituted is preferable, a cyclohexanediyl group is more preferable, and a cyclohexane-1,4-diyl group represented by the following formula (a) is particularly preferable.
  • the cyclic aliphatic group may be a trans isomer represented by the formula (a1), a cis isomer represented by the formula (a2), or a mixture of a cis isomer and a trans isomer, and a trans isomer represented by the formula (a1) is more preferable.
  • the aromatic group may include an aromatic hydrocarbon ring group of 6 to 20 carbon atoms such as a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a 1,4-naphthylene group, a 1,5-naphthylene group, a 2,6-naphthylene group, and a 4,4′-biphenylene group; and an aromatic heterocyclic ring group of 2 to 20 carbon atoms such as a furan-2,5-diyl group, a thiophene-2,5-diyl group, a pyridine-2,5-diyl group, and a pyrazine-2,5-diyl group.
  • an aromatic hydrocarbon ring group of 6 to 20 carbon atoms is preferable, a phenylene group is more preferable, and a 1,4-phenylene group represented by the following formula (b) is particularly preferable.
  • Examples of the substituents of the cyclic aliphatic group and the aromatic group may include a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom: an alkyl group of 1 to 6 carbon atoms such as a methyl group and an ethyl group; an alkoxy group of 1 to 5 carbon atoms such as a methoxy group and an isopropoxy group; a nitro group; and a cyano group.
  • the cyclic aliphatic group, the cyclic aliphatic group of 5 to 20 carbon atoms, the aromatic group, and the aromatic group of 2 to 20 carbon atoms may have one or more substituents selected from the substituents described above. When a plurality of substituents are included, the respective substituents may be the same as or different from one another.
  • Y 1 to Y 4 each independently represent a single bond, —O—, —C( ⁇ O)—, —C( ⁇ O)—O—, —O—C( ⁇ O)—, —NR 22 —C( ⁇ O)—, —C( ⁇ O)—NR 22 —, —O—C( ⁇ O)—, —NR 22 —C( ⁇ O)—O—, —O—C( ⁇ O)—NR 22 —, or —NR 22 —C( ⁇ O)—NR 23 —.
  • R 22 and R 23 each independently represent a hydrogen atom or an alkyl group of 1 to 6 carbon atoms.
  • Y 1 to Y 4 are each independently —O—, —C( ⁇ O)—, 13 C( ⁇ O)—O—, —O—C( ⁇ O)—O—, or —O—C( ⁇ O)—.
  • Y 1 and Y 2 When a plurality of Y 1 and Y 2 are present, they may be the same as or different from one another.
  • one of P 1 and P 2 represents a hydrogen atom or a polymerizable group, and the other of P 1 and P 2 represents a polymerizable group.
  • P 1 and P 2 each independently represent a polymerizable group.
  • R 1 represents a hydrogen atom, a methyl group, or a chlorine atom
  • a group represented by CH 2 ⁇ CR 1 —C( ⁇ O)—O— as shown in the following formula (IV) is preferable, CH 2 ⁇ CH—C( ⁇ O)—O—(acryloyloxy group) and CH 2 ⁇ C(CH 3 )—C( ⁇ O)—O—(methacryloyloxy group) are more preferable, and acryloyloxy group is further more preferable.
  • two R 1 's are present in the polymerizable compound (I) they may be the same as or different from each other.
  • P 1 and P 2 may be different from each other, and are preferably the same polymerizable group.
  • R 1 represents a hydrogen atom, a methyl group, or a chlorine atom.
  • p and q are each independently 0 to 2, and are each independently preferably 0 or 1.
  • liquid crystal compound represented by the formula (I) may include compounds represented by the formulae LC1 to LC3 below.
  • the liquid crystal compound represented by the formula (I) may be prepared by combining synthetic techniques described in literatures such as, for example, International Publication Nos. 2012/141245, 2012/147904, 2014/010325, and 2014/126113, and other known synthetic techniques.
  • the liquid crystal composition used for producing the phase difference plate of the present invention may be produced by mixing a liquid crystal compound such as those described above, a photopolymerization initiator, a surfactant, an organic solvent, and other optional components.
  • the photopolymerization initiator may be appropriately selected in accordance with the type of the polymerizable group of the polymerizable compound in the liquid crystal composition.
  • a radical polymerization initiator may be used if the polymerizable group is a radical polymerizable group
  • an anionic polymerization initiator may be used if the polymerizable group is an anionic polymerizable group
  • a cationic polymerization initiator may be used if the polymerizable group is a cationic polymerizable group.
  • radical polymerization initiator may include a photo-radical generator which is a compound that generates an active species capable of initiating polymerization of a polymerizable compound by light irradiation.
  • Examples of the photo-radical generator may include an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, an O-acyloxime-based compound, an onium salt-based compound, a benzoin-based compound, a benzophenone-based compound, an ⁇ -diketone-based compound, a polynuclear quinone-based compound, a xanthone-based compound, a diazo-based compound, and an imidosulfonate-based compound, which are described in International Publication No. 2012/147904.
  • anionic polymerization initiator may include an alkyllithium compound; a monolithium salt or a monosodium salt of biphenyl, naphthalene, pyrene and the like; and a multifunctional initiator such as a dilithium salt and a tri-lithium salt.
  • Examples of the cationic polymerization initiator may include a protonic acid such as sulfuric acid, phosphoric acid, perchloric acid, and trifluoromethanesulfonic acid; a Lewis acid such as boron trifluoride, aluminum chloride, titanium tetrachloride, and tin tetrachloride; and an aromatic onium salt or a combination system of an aromatic onium salt and a reducing agent.
  • a protonic acid such as sulfuric acid, phosphoric acid, perchloric acid, and trifluoromethanesulfonic acid
  • a Lewis acid such as boron trifluoride, aluminum chloride, titanium tetrachloride, and tin tetrachloride
  • an aromatic onium salt or a combination system of an aromatic onium salt and a reducing agent such as boron trifluoride, aluminum chloride, titanium tetrachloride, and tin tetrachloride
  • photopolymerization initiators may include product name: Irgacure 907, product name: Irgacure 184, product name: Irgacure 369, product name: Irgacure 651, product name: Irgacure 819, product name: Irgacure 907, product name: Irgacure 379, product name: Irgacure 379EG, and product name: Irgacure OXE02, which are manufactured by BASF; and product name: Adeca Optomer N1919 manufactured by ADEKA Corporation.
  • photopolymerization initiators one type thereof may be solely used, and two or more types thereof may also be used in combination at any ratio.
  • the ratio of the photopolymerization initiator is preferably 0.1 part by weight to 10 parts by weight, and more preferably 1.0 part by weight to 7.0 parts by weight, relative to 100 parts by weight of the polymerizable compound.
  • use thereof may be practiced with the total weight thereof falling within the above-described range.
  • the surfactant is not particularly limited, and is preferably a nonionic surfactant. Commercially available products may be used as the nonionic surfactant. For example, a nonionic surfactant which is an oligomer with a molecular weight of several thousands may be used.
  • surfactants may include PolyFox “PF-151N”, “PF-636”, “PF-6320”, “PF-656”, “PF-6520”, “PF-3320”, “PF-651”, and “PF-652” available from OMNOVA; Ftergent “FTX-209F”, “FTX-208G”, “FTX-204D”, and “601AD” available from NEOS; Surflon “KH-40” and “S-420” available from AGC Seimi Chemical Co., Ltd.; and “MEGAFACE F-562” available from DIC Corporation.
  • the surfactant one type thereof may be solely used, and two or more types thereof may also be used in combination at any ratio.
  • the ratio of the surfactant is preferably 0.001 part by weight to 10 parts by weight, and more preferably 0.001 part by weight to 0.1 part by weight, relative to 100 parts by weight of the polymerizable compound.
  • the organic solvent may include a hydrocarbon solvent such as cyclopentane and cyclohexane; a ketone solvent such as cyclopentanone, cyclohexanone, methyl ethyl ketone, acetone, and methyl isobutyl ketone; an acetic acid ester solvent such as butyl acetate and amyl acetate; a halogenated hydrocarbon solvent such as chloroform, dichloromethane, and dichloroethane; an ether solvent such as 1,4-dioxane, cyclopentylmethyl ether, tetrahydrofuran, tetrahydropyran, 1,3-dioxolane, and 1,2-dimethoxyethane; an aromatic hydrocarbon solvent such as toluene, xylene, and mesitylene; and a mixture thereof.
  • a hydrocarbon solvent such as cyclopentane and cyclohexane
  • the boiling point of the solvent is preferably 60° C. to 250° C., and more preferably 60° C. to 150° C., from the viewpoint of excellent handling properties.
  • the amount of the solvent used is preferably 100 parts by weight to 1000 parts by weight relative to 100 parts by weight of the polymerizable compound.
  • the liquid crystal composition may further contain optional components such as metal, a metal complex, a dye, a pigment, a fluorescent material, a phosphorescent material, a leveling agent, a thixotropic agent, a gelling agent, polysaccharides, an ultraviolet absorber, an infrared absorber, an antioxidant, an ion exchange resin, a metal oxide such as titanium oxide, and the like.
  • the ratio of each of such optional additives is preferably 0.1 part by weight to 20 parts by weight relative to 100 parts by weight of the polymerizable compound.
  • the layer of the liquid crystal composition may be formed by applying the liquid crystal composition onto the surface of the support body.
  • a support body having a surface capable of expressing an orientation regulating force to the liquid crystal compound may be appropriately selected.
  • a variety of support bodies such as a substrate of a resin film, a glass plate, or the like, to the surface of which an orientation regulating force is imparted by rubbing treatment, those to the surface of which an orientation regulating force is imparted by stretching treatment, and those on the surface of which a layer having an orientation regulating force is provided may be used.
  • a phase difference plate P 1 (to be described later) having a surface with an orientation regulating force may also be used.
  • the application operation may be performed by, for example, a bar coating using a wire bar, a gravure coating using a gravure roller, a die coating using a coating dies, and other methods such as a curtain coating method, an extrusion coating method, a roll coating method, a spin coating method, a dip coating method, a spray coating method, a slide coating method, a print coating method, a gap coating method, and a dipping method.
  • the thickness of the layer of the liquid crystal composition may be appropriately adjusted to obtain a phase difference plate having desired thickness and optical characteristics.
  • the orientation of the liquid crystal compound in the liquid crystal composition may be performed by leaving the layer of the liquid crystal composition in an environment controlled to an appropriate temperature.
  • an orientation treatment may be achieved by placing a layer of a liquid crystal composition in a 65-110° C. environment for 5 seconds to 2 minutes and then further leaving it for 5 seconds to 2 hours at a room temperature to 45° C.
  • the method for curing the liquid crystal composition is not particularly limited, and a method suitable for the liquid crystal composition to be treated may be appropriately selected.
  • the liquid crystal compound and/or a polymerization initiator include a compound capable of initiating polymerization by irradiation with ultraviolet rays
  • the liquid crystal compound can be polymerized by irradiation with ultraviolet rays to achieve curing.
  • the multilayer phase difference plate of the present invention includes a phase difference plate P 1 and a phase difference plate P 2 , and, of these, the phase difference plate P 2 is the aforementioned phase difference plate of the present invention.
  • an in-plane slow axis of the phase difference plate P 1 is orthogonal to an in-plane slow axis of the phase difference plate P 2 .
  • the in-plane retardation of the multilayer phase difference plate is composed as a difference between the phase difference of the phase difference plate P 1 and the phase difference of the phase difference plate P 2 .
  • ReP 1 ( ⁇ ) and ReP 2 ( ⁇ ) satisfy the following formulae (e4) and (e5).
  • the multilayer phase difference plate can function as a wavelength plate such as a 1 ⁇ 4 wavelength plate having a slow axis in the same direction as that of the in-plane slow axis of the phase difference plate P 1 .
  • a wavelength plate having a wavelength distribution with little deviation from an ideal distribution can be easily constituted.
  • ReP 1 ( ⁇ ) satisfies the following formula (e6).
  • the value of ReP 1 (400)/ReP 1 (700) is less than 1.10.
  • the value of ReP 1 (400)/ReP 1 (700) is preferably 1.08 or less, and more preferably 1.06 or less, and is preferably 0.95 or more, and more preferably 1.00 or more.
  • phase difference plate P 1 satisfying the formula (e6) can be easily constituted using a known material such as a stretched product of a film made of a resin containing an alicyclic structure-containing polymer.
  • ReP 1 ( ⁇ ) and ReP 2 ( ⁇ ) satisfy the following formula (e7).
  • the multilayer phase difference plate of the present invention may be preferably constituted as a 1 ⁇ 4 wavelength plate. More specifically, the multilayer phase difference plate may be constituted as a 1 ⁇ 4 wavelength plate which has a slow axis in the same direction as the slow axis direction of the phase difference plate P 1 and a wavelength distribution with little deviation from an ideal distribution.
  • the value of ReP 1 (550)-ReP 2 (550) is preferably more than 90 nm, and more preferably 120 nm or more, and is preferably less than 160 nm, and more preferably 150 nm or less.
  • each of ReP 1 ( ⁇ ) and ReP 2 ( ⁇ ) may be adjusted to a desired phase difference by adjusting a film formation method such as a material, thickness, and stretching ratio of the phase difference plate P 1 and the phase difference plate P 2 . Further, it is preferable that ReP 1 ( ⁇ ) and ReP 2 ( ⁇ ) of the multilayer phase difference plate satisfy the following formulae (e8) and (e9).
  • the phase difference plate P 1 can function as a 1 ⁇ 2 wavelength plate and the phase difference plate P 2 can function as a 1 ⁇ 4 wavelength plate. Further, the multilayer phase difference plate formed by combining them can function as a 1 ⁇ 4 wavelength plate having a wavelength distribution with little deviation from an ideal distribution.
  • the value of ReP 1 (550) is preferably 180 nm or more, and more preferably 220 nm or more, and is preferably 350 nm or less, and more preferably 300 nm or less.
  • the value of ReP 2 (550) is preferably 90 nm or more, and more preferably 120 nm or more, and is preferably 160 nm or less, and more preferably 150 nm or less.
  • the material constituting the phase difference plate P 1 is not particularly limited, and any material that can be used for optical applications and satisfies the above-described requirements may be used.
  • the phase difference plate P 1 is a stretched product of a film of a resin containing an alicyclic structure-containing polymer. By stretching the film of the resin containing an alicyclic structure-containing polymer, the phase difference plate P 1 described above can be easily obtained, and as a result, the multilayer phase difference plate of the present invention can be easily produced.
  • the film of the resin containing an alicyclic structure-containing polymer may be a film composed of a resin containing an alicyclic structure-containing polymer.
  • the alicyclic structure-containing polymer is a polymer having an alicyclic structure in a repeating unit, and is usually an amorphous polymer.
  • the alicyclic structure-containing polymer any of a polymer containing an alicyclic structure in a main chain and a polymer containing an alicyclic structure in a side chain may be used.
  • Examples of the alicyclic structure may include a cycloalkane structure and a cycloalkene structure, and a cycloalkane structure is preferable from the viewpoint of thermal stability and the like.
  • the number of carbon atoms constituting the repeating unit of one alicyclic structure is not particularly limited, and is preferably 4 or more, more preferably 5 or more, and particularly preferably 6 or more, and is preferably 30 or less, more preferably 20 or less, and particularly preferably 15 or less.
  • the ratio of the repeating units having an alicyclic structure in the alicyclic structure-containing polymer may be appropriately selected depending on the purpose of use, and is preferably 50% by weight or more, more preferably 70% by weight or more, and particularly preferably 90% by weight or more. By increasing the number of repeating units having an alicyclic structure as described above, heat resistance of the film can be increased.
  • Examples of the alicyclic structure-containing polymer may include (1) a norbornene polymer, (2) a monocyclic olefin polymer, (3) a cyclic conjugated diene polymer, (4) a vinyl alicyclic hydrocarbon polymer, and hydrogenated products thereof.
  • a norbornene polymer is more preferable from the viewpoint of transparency and moldability.
  • Examples of the norbornene polymer may include a ring-opening polymer of a norbornene monomer, a ring-opening copolymer of a norbornene monomer and another monomer capable of ring-opening copolymerization therewith, and hydrogenated products thereof; an addition polymer of a norbornene monomer, and an addition copolymer of a norbornene monomer and another monomer capable of copolymerization therewith.
  • a hydrogenated product of a ring-opening polymer of a norbornene monomer is particularly preferable.
  • the alicyclic structure-containing polymers described above are selected from publicly known polymers disclosed, for example, in Japanese Patent Application Laid-Open No. 2002-321302 A.
  • the weight-average molecular weight (Mw) of the alicyclic structure-containing polymer is preferably 10,000 to 100,000, more preferably 25,000 to 80,000, and even more preferably 25,000 to 50,000. When the weight-average molecular weight falls within such a range, mechanical strength and moldability of the film are highly balanced and suitable.
  • the weight-average molecular weight may be measured as a polyisoprene-equivalent value (or a polystyrene-equivalent value when the solvent is toluene) by gel permeation chromatography (hereinafter abbreviated as “GPC”) using cyclohexane (or toluene when the resin is not dissolved in cyclohexane) as a solvent.
  • GPC gel permeation chromatography
  • the molecular weight distribution (weight-average molecular weight (Mw)/number-average molecular weight (Mn)) of the alicyclic structure-containing polymer is preferably 1 or more, and more preferably 1.2 or more, and is preferably 10 or less, more preferably 4 or less, and particularly preferably 3.5 or less.
  • the resin containing the alicyclic structure-containing polymer may be composed only of the alicyclic structure-containing polymer.
  • the resin may contain any blending agent as long as the advantageous effects of the present invention are not significantly impaired.
  • optional components may include blending agents such as an ultraviolet absorber; an inorganic particulate; a stabilizer such as an antioxidant, a thermal stabilizer, and a near infrared absorber; a resin modifier such as a lubricant, and a plasticizer; a colorant such as a dye and a pigment; and an aging inhibitor.
  • one type thereof may be solely used, and two or more types thereof may also be used in combination at any ratio.
  • the ratio of the alicyclic structure-containing polymer in the resin containing the alicyclic structure-containing polymer is preferably 70% by weight or more, and more preferably 80% by weight or more.
  • Suitable specific examples of the resin containing an alicyclic structure-containing polymer may be “ZEONOR” manufactured by ZEON Corporation.
  • the substrate film may be a single layer film including only one layer, or may be a multilayer film including two or more layers.
  • the substrate film is a multilayer film including a first surface layer, an intermediate layer containing an ultraviolet absorber, and a second surface layer in this order in the thickness direction thereof. That is, it is preferable that the substrate film includes a first surface layer formed of a thermoplastic resin containing a polymer having an alicyclic structure, an intermediate layer formed of a thermoplastic resin containing a polymer having an alicyclic structure and an ultraviolet absorber, and a second surface layer formed of a thermoplastic resin containing a polymer having an alicyclic structure in this order in the thickness direction.
  • the first surface layer and the second surface layer can suppress bleed-out of the ultraviolet absorber contained in the intermediate layer.
  • the multilayer phase difference plate of the present invention when the multilayer phase difference plate of the present invention is incorporated into a polarizing plate and an image display device, it is possible to suppress deterioration of the phase difference plate P 2 and the image display device due to ultraviolet rays.
  • the first surface layer and the second surface layer do not include an ultraviolet absorber.
  • the polymer contained in the first surface layer, the polymer contained in the intermediate layer, and the polymer contained in the second surface layer may be the same as or different from one another. Therefore, the thermoplastic resin contained in the first surface layer and the thermoplastic resin contained in the second surface layer may be different from one another, but are preferably the same because therewith the layers can be easily formed.
  • the first surface layer and the second surface layer are formed of the same thermoplastic resin as the thermoplastic resin contained in the intermediate layer except that they do not contain an ultraviolet absorber.
  • the ultraviolet absorber may include an organic ultraviolet absorber such as a triazine-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, a benzotriazole-based ultraviolet absorber, and an acrylonitrile-based ultraviolet absorber.
  • an organic ultraviolet absorber such as a triazine-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, a benzotriazole-based ultraviolet absorber, and an acrylonitrile-based ultraviolet absorber.
  • a triazine-based ultraviolet absorber is preferable from the viewpoint of excellent ultraviolet absorption performance in the vicinity of a wavelength of 380 nm.
  • the ultraviolet absorber preferably has a molecular weight of 400 or more.
  • the triazine-based ultraviolet absorber a compound having a 1,3,5-triazine ring may preferably be used.
  • Specific examples of the triazine-based ultraviolet absorber may include 2-(4,6-diphenyl-1,3,5-triazine-2-yl)-5-[(hexyl)oxy]-phenol, and 2,4-bis(2-hydroxy-4-butoxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazine.
  • Commercially available products of the triazine-based ultraviolet absorber may include, for example, “Tinuvin 1577” (manufactured by Chiba Specialty Chemicals, Inc.).
  • Examples of the benzotriazole-based ultraviolet absorber may include 2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol], 2-(3,5-di-tert-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2H-benzotriazol-2-yl)-p-crezole, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-benzotriazole-2-yl-4,6-di-tert-butylphenol, 2-[5-chloro(2H)-benzotriazol-2-yl]-4-methyl-6-(tert-butyl)phenol, 2-(2H-benzotriazol-2-yl)-4,6-di-tert-butylphenol, 2-(2H-benzotriazol-2-yl)-4
  • ultraviolet absorbers one type thereof may be solely used, and two or more types thereof may also be used in combination at any ratio.
  • the amount of the ultraviolet absorber is preferably 1% by weight or more, and more preferably 3% by weight or more, and is preferably 8% by weight or less, and more preferably 6% by weight or less.
  • the amount of the ultraviolet absorber refers to the total amount of these ultraviolet absorbers.
  • the amount of the ultraviolet absorber By setting the amount of the ultraviolet absorber to be equal to or more than the lower limit of the aforementioned range, transmission of ultraviolet rays having a wavelength of 200 nm to 370 nm can be effectively suppressed, and by setting the amount to be equal to or less than the upper limit, the yellow tint of the film can be suppressed, so that deterioration of the color tone can be suppressed. Further, when the amount of the ultraviolet absorber is confined within the aforementioned range, the resin does not contain a large amount of the ultraviolet absorber, and it is thereby possible to suppress deterioration of the heat resistance of the thermoplastic resin.
  • Examples of the method for producing a thermoplastic resin containing an ultraviolet absorber and a polymer having an alicyclic structure may include a method for blending an ultraviolet absorber into a polymer having an alicyclic structure before production of a substrate film by a melt extrusion method; a method using a master batch containing a high concentration of an ultraviolet absorber; and a method for blending an ultraviolet absorber into a polymer having an alicyclic structure upon producing a substrate film by a melt extrusion method.
  • the dispersibility of the ultraviolet absorber can be sufficiently enhanced by setting the amount of the ultraviolet absorber within the aforementioned range.
  • the method for molding the resin containing an alicyclic structure-containing polymer into the shape of a film is not particularly limited, and a known method such as an extrusion molding method or the like may be adopted.
  • a long-length film can be continuously molded, which is preferable from the viewpoint of production efficiency.
  • the method of stretching the film to produce a stretched product is not either particularly limited, and examples of the stretching operation may include stretching in a lengthwise direction of the long-length film, stretching in the width direction, stretching in the oblique direction, and combinations thereof.
  • the thickness of the film, the stretching ratio, and the thickness of the stretched product after the stretching may be appropriately adjusted within respective ranges by which a desired phase difference plate P 1 is obtained.
  • the glass transition temperature of the thermoplastic resin is preferably 80° C. or higher, more preferably 100° C. or higher, and still more preferably 120° C. or higher, and is preferably 250° C. or lower, and more preferably 180° C. or lower.
  • the substrate film includes the first surface layer, the intermediate layer, and the second surface layer
  • the glass transition temperature TgA of the thermoplastic resin contained in the intermediate layer and the glass transition temperature TgB of the thermoplastic resin contained in the first surface layer and the second surface layer satisfy the relationship of TgB-TgA ⁇ 15° C.
  • the light transmittance of the substrate film at a wavelength of 380 nm is preferably 10% or less, more preferably 5% or less, and particularly preferably 1% or less.
  • the light transmittance of the substrate film at a wavelength of 280 nm to 370 nm is preferably 1.5% or less, and more preferably 1% or less.
  • the light transmittance may be measured by using a spectrophotometer according to JISK0115.
  • the polarizing plate of the present invention includes the multilayer phase difference plate of the present invention described above and a linear polarizer. Further, the image display device of the present invention includes the polarizing plate of the present invention described above.
  • the polarizing plate of the present invention may include, as an optional constituent element, a protective film for protecting the polarizer and an adhesive layer for effecting adhesion thereof.
  • the protective film is usually disposed on both sides of the polarizer directly or via an adhesive layer.
  • the polarizing plate may be configured such that the protective film is omitted and the linear polarizer is protected by the multilayer phase difference plate instead of the protective film.
  • the polarizing plate of the present invention which includes the multilayer phase difference plate in addition to the linear polarizer, can be used as a constituent element of an optical member capable of achieving uniform optical effects in a wide wavelength range.
  • the polarizing plate of the present invention may be used as an antireflection film in an image display device.
  • the polarizing plate preferably used as the antireflection film may include the one with a layer configuration of (phase difference plate P 2 )/(phase difference plate P 1 )/(linear polarizer), in which the transmission axis of the linear polarizer and the slow axis of the phase difference plate P 1 have a relationship of 40° to 50°, preferably 44° to 46°, typically 45°, with respect to each other and the multilayer phase difference plate functions as the 1 ⁇ 4 wavelength plate.
  • a polarizing plate When such a polarizing plate is disposed in the image display device at a position closer to a viewing side than elements constituting pixels with a surface of the polarizing plate on a linear polarizer side directing toward the viewing side, light, which is made incident from the outside of the device and reflected in the inside of the device, can be prevented from being emitted to the outside of the device and viewed by an observer. Further, when the multilayer phase difference plate of the present invention is included as the phase difference plate, such an antireflection effect can be uniformly obtained in a wide wavelength range.
  • optical characteristics of the phase difference plates P 1 and P 2 may be appropriately adjusted so as to minimize a reflectance Y value of the reflected light in the visible light region.
  • the reflectance Y value may be obtained by the following formula (e10).
  • S( ⁇ ) represents a spectral distribution of incident light
  • R( ⁇ ) represents a spectral distribution of reflectance
  • y( ⁇ ) represents the y value in the color-matching function.
  • the structure was identified by 1 H-NMR.
  • the organic layer was washed twice with 200 ml of the saturated aqueous solution of sodium hydrogen carbonate. Subsequently, the organic layer was collected, dried over anhydrous sodium sulfate, and filtered to remove sodium sulfate. After the solvent was removed by evaporation from the filtrate using the rotary evaporator, a residue thus obtained was dissolved in 30 ml of tetrahydrofuran (THF). To this solution, 300 ml of hexane was added to precipitate a solid, and the precipitated solid was separated by filtration.
  • THF tetrahydrofuran
  • the organic layer was washed with 300 ml of the saturated aqueous solution of sodium hydrogen carbonate and then further washed with 100 ml of a saturated aqueous solution of sodium chloride.
  • the organic layer was collected, dried over anhydrous sodium sulfate, and filtered to remove sodium sulfate.
  • the solvent was removed by evaporation from the filtrate using the rotary evaporator to obtain a yellow oil.
  • the structure of the intended product was identified by 1 H-NMR.
  • the organic layer was washed with 300 ml of the saturated aqueous solution of sodium hydrogen carbonate and then further washed with 100 ml of the saturated aqueous solution of sodium chloride.
  • the organic layer was collected, dried over anhydrous sodium sulfate, and filtered to remove sodium sulfate.
  • the solvent was removed by evaporation from the filtrate using the rotary evaporator to obtain a yellow oil.
  • the measured phase transition temperatures are shown in Table 1 below.
  • C refers to “Crystal”, “Nematic”, and “Isotropic”, respectively.
  • the term “Crystal” herein means that a test compound is in a solid phase
  • the term “Nematic” means that a test compound is in a nematic liquid crystal phase
  • the term “Isotropic” means that a test compound is in an isotropic liquid phase.
  • Liquid crystal compound compound LC1 synthesized in Synthesis Example 1 (number of ⁇ electrons 10) 21.0 parts by weight.
  • the mixture was stirred in a light-shielding bottle at 60° C. for 1.0 hour. After completion of the stirring, the mixture was allowed to stand at the room temperature to be cooled down. The mixture cooled down to the room temperature was passed through a membrane filter of 0.45 ⁇ m. In this manner, the liquid crystal composition was prepared.
  • “ZEONOR film” manufactured by ZEON Corporation was prepared.
  • This support body was a long-length film having a thickness of 47 ⁇ m.
  • the glass transition temperature (Tg) of the resin constituting the film was 126° C.
  • This support body had a phase difference, and the in-plane retardation Re of the support body at a wavelength of 550 nm was 141 nm and the in-plane slow axis direction of the support body was inclined at an angle of 45° with respect to the width direction of the support body.
  • the liquid crystal composition obtained in (1-1) was applied onto one surface of the support body obtained in (1-2).
  • the application was performed by a bar coating using a wire bar of count No.03.
  • the support body was placed in an oven at 65° C. to perform a heating treatment for 2 minutes. After drying, the support body was allowed to stand at the room temperature for 1 hour. In this manner, the liquid crystal compound in the layer of the liquid crystal composition was oriented.
  • the layer of the liquid crystal composition was irradiated with ultraviolet rays.
  • the irradiation of ultraviolet rays was performed at an exposure of 150 mJ/cm 2 or more using H-Bulb (manufactured by Heraeus Noblelight GmbH).
  • H-Bulb manufactured by Heraeus Noblelight GmbH.
  • the layer of the liquid crystal composition was cured to produce the phase difference plate P 2 , and a multilayer product (i) having a layer configuration of (support body)/(phase difference plate P 2 ) was obtained.
  • the phase difference plate P 2 thus obtained had a film thickness of 1.67
  • a surface of the multilayer product thus obtained on a side of the phase difference plate P 2 was bonded to a glass substrate via an adhesive, and the support body was peeled off. In this manner, a multilayer product (ii) of (glass substrate)/(adhesive layer)/(phase difference plate P 2 ) was obtained.
  • the in-plane retardation Re of the phase difference plate P 2 on the multilayer product (ii) obtained in (1-3) was measured.
  • a phase difference meter manufactured by Axometrics, Inc. was used for the measurement.
  • the measurement results thus obtained showed the wavelength distribution which generally followed the Cauchy distribution formula, although there were some fluctuations in the measurement values possibly due to interference of the film.
  • thermoplastic resin (COP1) containing an alicyclic structure-containing polymer manufactured by ZEON Corporation, glass transition temperature of 123° C.
  • LA-31 benzotriazole-based ultraviolet absorber
  • the amount of the ultraviolet absorber in the thermoplastic resin (J1) was 5.2% by weight.
  • the thermoplastic resin (J1) described above was fed to a hopper mounted on the uniaxial extruder. Then, the thermoplastic resin (J1) was melted, and the melted thermoplastic resin (J1) was supplied to a multi-manifold die at an outlet temperature of the extruder of 280° C. and a rotation speed of a gear pump of the extruder of 10 rpm.
  • the die lip of the multi-manifold die had an arithmetic surface roughness Ra of 0.1 ⁇ m.
  • thermoplastic resin (COP1) containing the same alicyclic structure-containing polymer as that used in the production of the thermoplastic resin (J1) was fed to a hopper mounted on the uniaxial extruder. Then, the thermoplastic resin (COP1) was melted, and the melted thermoplastic resin (COP1) was supplied to the multi-manifold die described above at the outlet temperature of the extruder of 285° C. and the rotation speed of the gear pump of the extruder of 4 rpm.
  • thermoplastic resin (COP1) The melted thermoplastic resin (COP1), the melted thermoplastic resin (J1) containing the ultraviolet absorber, and the melted thermoplastic resin (COP1) were each discharged from the multi-manifold die at 280° C. and casted on a cooling roll whose temperature was adjusted to 150° C. to obtain a pre-stretch film. Upon discharging the resins, the air gap amount was set to 50 mm. Further, as a method for casting the discharged resins on the cooling roll, edge pinning was adopted.
  • the pre-stretch film thus obtained was a multilayer film of three-layered structure including a resin layer formed of the thermoplastic resin (COP1) with a thickness of 15 ⁇ m, a resin layer formed of the thermoplastic resin (J1) containing the ultraviolet absorber with a thickness of 40 ⁇ m, and a resin layer formed of the thermoplastic resin (COP1) with a thickness of 15 ⁇ m in this order. Further, the pre-stretch film had a width of 1,400 mm and a total thickness of 70 ⁇ m. The pre-stretch film thus obtained was subjected to a trimming treatment in which both end portions of the pre-stretch film in the width direction were trimmed by 50 mm to trim the width thereof to 1,300 mm.
  • the pre-stretch film described above was stretched in a diagonal direction that was not parallel or perpendicular to the lengthwise direction of the pre-stretch film under conditions of a stretching temperature of 140° C. and a stretching rate of 20 m/min to obtain a stretched film as a substrate film.
  • the stretched film thus obtained was a multilayer film of three-layered structure including a first surface layer formed of the thermoplastic resin (COP1) with a thickness of 8 ⁇ m, an intermediate layer formed of the thermoplastic resin (J1) containing the ultraviolet absorber with a thickness of 31 ⁇ m, and a second surface layer formed of the thermoplastic resin (COP1) with a thickness of 8 ⁇ m in this order.
  • the stretched film had a width of 1,330 mm, a thickness of 47 ⁇ m, and a slow axis inclined at an angle of 45° with respect to the lengthwise direction of the stretched film.
  • the stretched film had an in-plane retardation at a measurement wavelength 550 nm of 100 nm, a light transmittance at a measurement wavelength 380 nm of 0.02%, and a refractive index of 1.53.
  • the in-plane retardation ReP 1 ( ⁇ ) of this film at each wavelength ⁇ was measured and subjected to the Cauchy fitting to calculate a relationship between the wavelength ⁇ and ReP 1 ( ⁇ )/ReP 1 (550).
  • the specific method thereof was the same as that performed in (1-4) for the phase difference plate P 2 .
  • the result is shown in Table 2. In the following calculation, this value was used as the in-plane retardation ReP 1 ( ⁇ ) of the phase difference plate P 1 at each wavelength ⁇ .
  • the antireflection film was disposed on a reflection plate causing ideal mirror reflection, and the reflectance Y value obtained when light incident on the antireflection film was discharged from the antireflection film was calculated.
  • the layer configuration of the antireflection film was (phase difference plate P 2 )/(phase difference plate P 1 )/(linear polarizer) in the order from the side closer to the reflection plate.
  • the slow axis of the phase difference plate P 2 was set to the direction orthogonal to the direction of the slow axis of the phase difference plate P 1 . Further, the slow axis of the phase difference plate P 1 was inclined at an angle of 45° with respect to the absorption axis of the linear polarizer.
  • the combination of the phase difference plate P 2 and the phase difference plate P 1 is assumed to be equivalent to a single phase difference plate Ps.
  • the slow axis direction of the phase difference plate Ps is set to the same direction as that of the phase difference plate P 1
  • a ratio R( ⁇ ) of the reflected light with respect to the incident light at the wavelength ⁇ is as presented by the following formula (e11) assuming that the polarizing plate has an ideal polarization effect.
  • R ⁇ ( ⁇ ) S ⁇ ( ⁇ ) ⁇ ( cos ⁇ ( ⁇ ⁇ 2 ⁇ ⁇ RePs ⁇ ( ⁇ ) ⁇ ) ) 2 ( e11 )
  • S( ⁇ ) represents a spectral distribution of the incident light and was set to 1 at all wavelengths in the present simulation.
  • the reflectance Y value was approximately calculated by the following formula (e12).
  • the value of RePs( ⁇ ) at each wavelength was obtained from values of ReP 1 ( ⁇ )/ReP 1 (550) and ReP 2 ( ⁇ )/ReP 2 (550) shown in Table 2 and values of ReP 1 (550) and ReP 2 (550) in the combinations thus set.
  • the function y( ⁇ ) is a function of the wavelength ⁇ and the y value of the color matching function, and the values shown in Table 2 were adopted.
  • a phase difference plate P 2 was obtained and an in-plane retardation Re thereof was measured by the same operation as that of (1-1) to (1-4) of Example 1 except that the compound LC2 (the number of ⁇ electrons was 12) synthesized in Synthesis Example 2 was used instead of the compound LC1 synthesized in Synthesis Example 1 as the liquid crystal compound of (1a).
  • a phase difference plate P 2 was obtained and an in-plane retardation Re thereof was measured by the same operation as that of (1-1) to (1-4) of Example 1 except that the compound LC3 (the number of ⁇ electrons was 12) synthesized in Synthesis Example 3 was used instead of the compound LC1 synthesized in Synthesis Example 1 as the liquid crystal compound of (1a).
  • the Cauchy fitting and simulation were performed in a case where this 1 ⁇ 4 wavelength plate was adopted as the phase difference plate P 2 . That is, the simulation and the like were performed by the same operation as that of (1-5) to (1-7) of Example 1 except that values of Re(450)/Re(550), Re(550)/Re(550), and Re(650)/Re(550) were set to 1.10, 1.00, and 0.95, respectively.
  • Table 2 and Table 3 The results are shown in Table 2 and Table 3.
  • a phase difference plate P 2 was obtained and an in-plane retardation Re thereof was measured by the same operation as that of (1-1) to (1-4) of Example 1 except that the liquid crystal compound represented by the following formula LC4 was used instead of the compound LC1 synthesized in Synthesis Example 1 as the liquid crystal compound of (1a).
  • a phase difference plate P 2 was obtained and an in-plane retardation Re thereof was measured by the same operation as that of (1-1) to (1-4) of Example 1 except that the liquid crystal compound represented by the following formula LC5 was used instead of the compound LC1 synthesized in Synthesis Example 1 as the liquid crystal compound of (1a) and the temperature of the oven was set to 100° C.
  • Example 1 to Example 3 where the linear index of the phase difference plate P 2 was less than 2.90, the deviation from the ideal distribution was significantly small and, as a result, the minimum reflectance Y value was also significantly small. Further, in Example 1 and Example 2, where ReP 2 (400)/ReP 2 (700) was 1.50 or more, the optimum value of ReP 2 (550) was as small as approximately that of the 1 ⁇ 4 wavelength plate.
  • the phase difference plate having such a phase difference value can be made with a reduced thickness, can be easily produced, and therefore can be usefully employed.
  • the sunglass-readability refers to performance of the display device which allows a user to recognize a uniform image at a variety of angles with little change in the visibility.
  • a simulation model 10 includes a liquid crystal display device 110 and sunglasses 120 , and the liquid crystal display device 110 includes a phase difference plate 110 P 1 , a phase difference plate 110 P 2 , and a panel 111 in the order from the viewing side.
  • the sunglasses 120 , the phase difference plate 110 P 1 , the phase difference plate 110 P 2 , and the panel 111 are disposed in parallel.
  • the sunglasses 120 are an ideal polarizing film having the absorption axis in a direction of an arrow A 120 .
  • the panel 111 As the panel 111 , a commercially available liquid crystal display device (product name “iPad Air”, manufactured by Apple Inc.) was used, and spectra obtained by displaying white image on the display surface were subjected to the simulation.
  • the panel 111 includes a linear polarizer having the absorption axis in a direction of an arrow A 111 on the viewing side of the panel 111 , and thus light discharged from the panel 111 is linearly polarized light.
  • Broken lines B 110 P 1 and B 110 P 2 represent directions at which the arrow A 111 direction is projected on the phase difference plates 110 P 1 and 110 P 2 , respectively.
  • ⁇ P 1 represents an angle formed by the broken line B 110 P 1 and a slow axis direction A 110 P 1 of the phase difference plate P 1
  • ⁇ P 2 represents an angle formed by the broken line B 110 P 2 and a slow axis direction A 110 P 2 of the phase difference plate P 2
  • ⁇ P 1 was set to 45° and ⁇ P 2 was set to 135°.
  • the viewing direction was set to a direction having a polar angle of 0° (a direction shown by a broken line B 120 ) with respect to the display surface of the liquid crystal display device 110 .
  • L*, a*, and b* of light discharged from the liquid crystal display device 110 and passed through the sunglasses 120 were each calculated when the liquid crystal display device 110 is rotated about the broken line B 120 as an axis such that an azimuth angle (an angle formed by the absorption axis A 111 of the panel 111 and the absorption axis A 120 of the sunglasses 120) was changed in increments of 5° in a range of 0° to 360, while the position of the sunglasses 120 is fixed. Subsequently, L 0 *, a 0 *, and b 0 * of light discharged from the liquid crystal display device 110 in a case without the existence the sunglasses 120 were calculated.
  • a phase difference plate P 2 was obtained, and values of the linear index, ReP 2 (400)/ReP 2 (700), and Re( ⁇ )/Re(550) at each wavelength were obtained in the phase difference plate P 2 by the same operation as that of (1-1) to (1-5) of Example 1 except for the following change. The results are shown in Table 4 and Table 5.
  • Example 5 The simulation was performed by the same method as that in Example 4 using as the phase difference plate P 2 the one obtained in (5-1) instead of the one obtained in (1-4) in Example 1 to calculate ⁇ E*(Max-Min). The result is shown in Table 5.
  • a phase difference plate P 2 was obtained and values of the linear index, ReP 2 (400)/ReP 2 (700), and Re( ⁇ )/Re(550) at each wavelength were obtained in the phase difference plate P 2 by the same operation as that of (1-1) to (1-5) of Example 1 except for the following change. The results are shown in Table 4 and Table 5.
  • Example 5 The simulation was performed by the same method as that in Example 4 using as the phase difference plate P 2 the one obtained in (6-1) instead of the one obtained in (1-4) in Example 1 to calculate ⁇ E*(Max-Min). The result is shown in Table 5.
  • Example 4 to Example 6 where the value of Re(400)/Re(700) is greater than 1.13 and the linear index of the phase difference plate P 2 is less than 2.90, the phase difference plate capable of constituting the liquid crystal display device having high sunglass-readability can be constituted.

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US20220043366A1 (en) * 2020-08-07 2022-02-10 Konica Minolta, Inc. Photoresponsive polymer

Families Citing this family (4)

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JP7334047B2 (ja) * 2019-03-13 2023-08-28 日東電工株式会社 画像表示装置および該画像表示装置に用いられる円偏光板
JP7310513B2 (ja) * 2019-09-30 2023-07-19 日本ゼオン株式会社 積層体及びその製造方法、並びに光学フィルム
JPWO2021261277A1 (zh) * 2020-06-23 2021-12-30
WO2021261344A1 (ja) * 2020-06-26 2021-12-30 日東電工株式会社 位相差層付偏光板、および、それを用いた画像表示装置

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW412656B (en) * 1996-04-26 2000-11-21 Hitachi Ltd Liquid crystal display
JP2000147260A (ja) * 1998-11-06 2000-05-26 Fuji Photo Film Co Ltd 位相差板
JP2001337207A (ja) * 2000-03-21 2001-12-07 Sumitomo Chem Co Ltd 前方散乱シート、それを用いた積層シート及び液晶表示装置
JP2002321302A (ja) 2001-04-26 2002-11-05 Nippon Zeon Co Ltd 脂環式構造含有重合体樹脂積層体
JP2003279733A (ja) * 2002-03-20 2003-10-02 Toray Ind Inc 位相差フィルム及び位相差板
JP4410092B2 (ja) * 2004-12-09 2010-02-03 日東電工株式会社 光学フィルム、バックライトシステムおよび液晶表示装置
WO2006098162A1 (en) 2005-02-25 2006-09-21 Fujifilm Corporation Optical compensation sheet, polarizing plate and liquid crystal display
JP4856981B2 (ja) 2005-02-25 2012-01-18 富士フイルム株式会社 光学補償シート、偏光板および液晶表示装置
JP5016568B2 (ja) * 2007-08-20 2012-09-05 富士フイルム株式会社 光学補償フィルム、その製造方法、並びにそれを用いた偏光板及び液晶表示装置
TWI486688B (zh) * 2009-11-30 2015-06-01 Fujifilm Corp Ｖａ型液晶顯示裝置
CN103459438B (zh) * 2011-04-15 2015-09-23 日本瑞翁株式会社 可聚合性化合物、可聚合性组合物、高分子及光学各向异性体
KR101891573B1 (ko) 2011-04-27 2018-08-24 제온 코포레이션 중합성 화합물, 중합성 조성물, 고분자, 및 광학 이방체
JP5967092B2 (ja) * 2011-07-29 2016-08-10 日本ゼオン株式会社 光学異方体の波長分散調整方法及び重合性組成物
WO2013146633A1 (ja) * 2012-03-30 2013-10-03 日本ゼオン株式会社 位相差フィルム積層体およびその製造方法、ならびに液晶表示装置
JP5880226B2 (ja) * 2012-04-03 2016-03-08 日本ゼオン株式会社 重合性化合物の製造方法
EP2871192B1 (en) 2012-07-09 2018-06-20 Zeon Corporation Polymerizable compound, polymerizable composition, polymer, optically anisotropic body, and method for producing polymerizable compound
WO2014126113A1 (ja) 2013-02-15 2014-08-21 日本ゼオン株式会社 重合性化合物、重合性組成物、高分子、及び光学異方体
JP2014206684A (ja) 2013-04-15 2014-10-30 大日本印刷株式会社 光学フィルム、光学フィルム用転写体、画像表示装置
JP6255395B2 (ja) * 2013-06-06 2017-12-27 富士フイルム株式会社 光学シート部材及びそれを用いた画像表示装置
JP6531935B2 (ja) * 2014-12-17 2019-06-19 Dic株式会社 重合性化合物及び光学異方体
JP2016139055A (ja) * 2015-01-28 2016-08-04 Ｊｘエネルギー株式会社 位相差板、位相差板を用いた積層偏光板、および位相差板を用いた表示装置

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220043366A1 (en) * 2020-08-07 2022-02-10 Konica Minolta, Inc. Photoresponsive polymer

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