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WO2019208516A1 - Polymerizable liquid crystal compound, polymerizable liquid crystal composition, polymer, optical film, optically anisotropic body, polarizing plate, display device, and antireflection film - Google Patents

Polymerizable liquid crystal compound, polymerizable liquid crystal composition, polymer, optical film, optically anisotropic body, polarizing plate, display device, and antireflection film Download PDF

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Publication number
WO2019208516A1
WO2019208516A1 PCT/JP2019/017082 JP2019017082W WO2019208516A1 WO 2019208516 A1 WO2019208516 A1 WO 2019208516A1 JP 2019017082 W JP2019017082 W JP 2019017082W WO 2019208516 A1 WO2019208516 A1 WO 2019208516A1
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group
carbon atoms
liquid crystal
ring
substituent
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PCT/JP2019/017082
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French (fr)
Japanese (ja)
Inventor
坂本　圭
久美 奥山
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日本ゼオン株式会社
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Priority to JP2020516352A priority Critical patent/JP7484709B2/en
Priority to CN201980026401.5A priority patent/CN111989317B/en
Priority to KR1020207030013A priority patent/KR20210004998A/en
Publication of WO2019208516A1 publication Critical patent/WO2019208516A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • 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
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • 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
    • 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
    • C08F20/38—Esters containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/11—Anti-reflection coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • the present invention relates to a polymerizable liquid crystal compound capable of forming an optical film and an optical anisotropic body having ideal wavelength dispersion, i.e., reverse wavelength dispersion, exhibiting broadband properties, and exhibiting liquid crystallinity alone. is there.
  • the present invention also relates to a polymerizable liquid crystal composition containing the polymerizable liquid crystal compound.
  • the present invention also relates to a polymer obtained by polymerizing the polymerizable liquid crystal compound.
  • the present invention relates to an optical film and an optical anisotropic body prepared using the polymerizable liquid crystal compound, and a polarizing plate, a display device and an antireflection film using the optical anisotropic body.
  • “showing liquid crystallinity” means “having a liquid crystal phase”. Specific examples of the liquid crystal phase include a nematic phase and a smectic phase.
  • a retardation plate used in various devices such as a flat panel display device includes a 1 ⁇ 4 wavelength plate that converts linearly polarized light into circularly polarized light, a 1 ⁇ 2 wavelength plate that converts a polarization vibration plane of linearly polarized light by 90 degrees, and the like. There is. These retardation plates can accurately give a phase difference of 1 / 4 ⁇ or 1 / 2 ⁇ of a light wavelength to a specific monochromatic light. However, the conventional retardation plate has a problem that polarized light output through the retardation plate is converted into colored polarized light.
  • the material constituting the retardation plate has wavelength dispersion with respect to the retardation, and distribution occurs in the polarization state of each wavelength with respect to white light that is a composite wave in which rays in the visible light range are mixed. This is because it is impossible to adjust the input light to polarization having a phase difference of 1 ⁇ 4 ⁇ or 1 ⁇ 2 ⁇ in all wavelength regions.
  • various studies have been made on a broadband retardation plate capable of giving a uniform retardation to light in a wide wavelength range, that is, a so-called reverse wavelength dispersion plate.
  • the present invention has been made in view of the above circumstances, and can form an ideal wavelength dispersion exhibiting broadband properties, that is, an optical film and an optical anisotropic body having reverse wavelength dispersion, and can be used alone.
  • An object of the present invention is to provide a polymerizable liquid crystal compound exhibiting liquid crystallinity.
  • Another object of the present invention is to provide a polymerizable liquid crystal composition containing the polymerizable liquid crystal compound.
  • Another object of the present invention is to provide a polymer obtained by polymerizing the polymerizable liquid crystal compound.
  • the present invention provides an optical film and an optical anisotropic body prepared using the polymerizable liquid crystal compound, and a polarizing plate, a display device and an antireflection film using the optical anisotropic body. Objective.
  • the present inventors have found that when a predetermined polymerizable liquid crystal compound represented by the following formula (I) is used, an ideal wavelength dispersion exhibiting broadband properties, that is, a reverse wavelength. It has been found that an optical film and an optical anisotropic body having dispersibility can be formed, and that the polymerizable liquid crystal compound exhibits liquid crystallinity alone, and the present invention has been completed.
  • the following polymerizable liquid crystal compound, polymerizable liquid crystal composition, polymer, optical film, optical anisotropic body, polarizing plate, display device, and antireflection film are provided.
  • Ar is represented by any of the following formulas (II-1) to (II-3), and may have one or more substituents other than D.
  • Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Ax represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms
  • Ay represents a hydrogen atom or an organic group having 1 to 30 carbon atoms which may have a substituent
  • Az represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • Az excludes the case of C (Ay) Ax.
  • * represents a position bonded with Z 1 or Z 2.
  • a 1 and A 2 each independently represents a divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent.
  • the chain aliphatic group includes —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, — NR 12 —C ( ⁇ O) —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) — may be present.
  • R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Provided that the carbon atom bonded to Z 1 and the carbon atom bonded to Y 1 or Y 3 of A 1 and the carbon atom bonded to Z 2 and the carbon atom bonded to Y 2 or Y 4 of A 2 are bonded to each other.
  • B 1 and B 2 each independently represent a cyclic aliphatic group which may have a substituent or an aromatic group which may have a substituent.
  • R 13 and R 14 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • G 1 and G 2 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and 1 of a methylene group (—CH 2 —) contained in an aliphatic hydrocarbon group having 3 to 20 carbon atoms.
  • the above is an organic group of any of the groups substituted with —O— or —C ( ⁇ O) —.
  • a hydrogen atom contained in the organic group of G 1 and G 2 may be substituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom.
  • the methylene groups (—CH 2 —) at both ends of G 1 and G 2 are not substituted with —O— or —C ( ⁇ O) —.
  • P 1 and P 2 each independently represent a polymerizable group. p and q each independently represents an integer of 0 to 2. ]
  • a polymerizable composition comprising the polymerizable liquid crystal compound according to [1].
  • a polarizing plate including the optical anisotropic body according to [5] and a polarizing film.
  • a display device comprising the polarizing plate according to [6].
  • a polymerizable liquid crystal compound capable of forming an optical film and an optical anisotropic body having ideal wavelength dispersibility exhibiting broadband properties, that is, reverse wavelength dispersibility, and exhibiting liquid crystallinity alone.
  • the polymeric liquid crystal composition containing the said polymeric liquid crystal compound is provided.
  • polymerizing the said polymeric liquid crystal compound is provided.
  • the “alkyl group” means a chain (straight chain or branched) saturated hydrocarbon group, and the “alkyl group” means a “cyclo saturated hydrocarbon group” "Alkyl group” is not included.
  • the polymerizable liquid crystal compound and the polymerizable liquid crystal composition of the present invention are not particularly limited, and can be used, for example, when preparing the polymer of the present invention.
  • the polymer of the present invention is not particularly limited, and can be used, for example, as a constituent material of the optical film of the present invention and a constituent material of the layer of the optical anisotropic body of the present invention.
  • the optical anisotropic body of this invention is not specifically limited, For example, it can use for preparation of the polarizing plate of this invention.
  • the polarizing plate of this invention is not specifically limited, For example, it can be used for preparation of the display apparatus and antireflection film of this invention.
  • the intermediate body (compound) of the polymeric liquid crystal compound of this invention is not specifically limited, For example, it can be used when preparing the polymeric liquid crystal compound of this invention.
  • polymerizable liquid crystal compound of the present invention is a compound represented by the following formula (I) (hereinafter sometimes referred to as "polymerizable liquid crystal compound (I)"), and a polymer described later. It can be advantageously used in preparing an optical film and an optical anisotropic body.
  • Ar is represented by any of the following formulas (II-1) to (II-3) and may have one or more substituents other than D.
  • the total number of ⁇ electrons contained in the ring structure in Ar is preferably 10 or more, more preferably 12 or more, preferably 60 or less, preferably 48 or less, and 36 or less. It is particularly preferred.
  • “the total number of ⁇ electrons contained in the ring structure in Ar” is the number of ⁇ electrons contained in one ring structure when the number of ring structures contained in Ar is one. This means that when Ar includes a plurality of ring structures, it means the total number of ⁇ electrons of the plurality of ring structures.
  • * represents bonding to Z 1 or Z 2
  • “-” extending from the inside of the ring represents a bonding hand extending from any position of the ring. To express.
  • Examples of the substituent other than D include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms in which one or more hydrogen atoms are substituted with a halogen atom such as a fluorine atom.
  • Alkyl group N-alkylamino group having 1 to 6 carbon atoms, N, N-dialkylamino group having 2 to 12 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylsulfinyl group having 1 to 6 carbon atoms, carboxyl Group, a thioalkyl group having 1 to 6 carbon atoms, an N-alkylsulfamoyl group having 1 to 6 carbon atoms, an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, and the like.
  • -Q- Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • -Ay- Ay represents a hydrogen atom or an organic group having 1 to 30 carbon atoms which may have a substituent.
  • the organic group having 1 to 30 which may have a substituent of Ay include an alkyl group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms which may have a substituent.
  • At least one of —CH 2 — contained is substituted with —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, or —C ( ⁇ O) —.
  • An alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms which may have a substituent, and an aromatic carbon atom having 6 to 30 carbon atoms which may have a substituent hydrocarbon ring group, aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent, -Gy-Yy-Fy, -SO 2 R a -C ( O) -R b, or, -CS-NH-R b, and the like.
  • the alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least one of —CH 2 — contained in the alkyl group having 1 to 20 carbon atoms is —O—, —S—, A group substituted with —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, or —C ( ⁇ O) — (provided that two or more of —O— or —S— are adjacent to each other).
  • alkyl group having 1 to 20 carbon atoms which may have a substituent include, for example, methyl group, ethyl group, n-propyl group, isopropyl Group, n-butyl group, isobutyl group, 1-methylpentyl group, 1-ethylpentyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl Group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n
  • methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group Is preferred.
  • the “optionally substituted alkyl group having 1 to 20 carbon atoms” preferably has 1 to 12 carbon atoms, and more preferably 4 to 10 carbon atoms.
  • substituent in the “optionally substituted alkyl group having 1 to 20 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; carbon such as dimethylamino group N, N-dialkylamino group having 2 to 12 carbon atoms; alkoxy group having 1 to 20 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy C1-C12 alkoxy groups substituted with C1-C12 alkoxy groups such as nitro groups; nitro groups; aromatics having 6-18 carbon atoms such as phenyl groups, 1-naphthyl groups, 2-naphthyl groups, etc.
  • Hydrocarbon ring group carbon such as triazolyl group, pyrrolyl group, furanyl group, thiophenyl group (thienyl group), thiazolyl group, benzothiazol-2-ylthio group, etc.
  • a cyclic group, an aromatic heterocyclic group having 2 to 18 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyloxy group having 3 to 8 carbon atoms, a cyclic ether group having 2 to 12 carbon atoms, and 6 to 6 carbon atoms 14 aryloxy groups are preferred, fluorine atom, cyano group, methoxy group, ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, phenyl group, 1-naphthyl group, 2-naphthyl group Group,
  • R a is an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, which may have a substituent.
  • 18 represents an aromatic hydrocarbon ring group
  • R b is an optionally substituted alkyl group having 1 to 20 carbon atoms and an optionally substituted alkenyl group having 2 to 20 carbon atoms.
  • the number of substituents in the “optionally substituted alkyl group having 1 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • alkenyl group having 2 to 20 carbon atoms which may have a substituent include, for example, a vinyl group, a propenyl group, an isopropenyl group, and a butenyl group.
  • Isobutenyl group pentenyl group, hexenyl group, heptenyl group, octenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonacenyl group, etc. Is mentioned.
  • 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, and a dodecenyl group are preferable.
  • the “optionally substituted alkenyl group having 2 to 20 carbon atoms” preferably has 2 to 12 carbon atoms.
  • substituents in the above “optionally substituted alkenyl group having 2 to 20 carbon atoms” include the substitution in the above “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific example of the group.
  • the number of substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • alkynyl group having 2 to 20 carbon atoms which may have a substituent include, for example, ethynyl group, propynyl group, 2-propynyl group ( Propargyl group), butynyl group, 2-butynyl group, 3-butynyl group, pentynyl group, 2-pentynyl group, hexynyl group, 5-hexynyl group, heptynyl group, octynyl group, 2-octynyl group, nonanyl group, decanyl group, 7-decanyl group, and the like.
  • 2-propynyl group (propargyl group), butynyl group, 2-butynyl group, 3-butynyl group, pentynyl group, 2-pentynyl group, hexynyl group, 5-hexynyl group, heptynyl group, octynyl group, 2- An octynyl group, a nonanyl group, and a decanyl group are preferred.
  • substituents in the above “optionally substituted alkynyl group having 2 to 20 carbon atoms” include substitution in the above “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific example of the group.
  • the number of substituents in the “optionally substituted alkynyl group having 2 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • C3-C12 cycloalkyl group optionally having substituent Specific examples of the “cycloalkyl group having 3 to 12 carbon atoms” in the “cycloalkyl group having 3 to 12 carbon atoms which may have a substituent” include, for example, a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group. Cyclohexyl group, cyclooctyl group, and the like. Among these, a cyclopentyl group and a cyclohexyl group are preferable.
  • substituent in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” include the above-described “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific examples of the substituent.
  • the number of substituents in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • Aromamatic hydrocarbon ring group having 6 to 30 carbon atoms which may have a substituent include, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group and the like can be mentioned. Among these, a phenyl group is preferable.
  • substituent in the “optionally substituted aromatic hydrocarbon ring group having 6 to 30 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; methyl group
  • halogen atoms such as fluorine atom and chlorine atom
  • cyano group such as an ethyl group or a propyl group
  • an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group
  • one or more hydrogen atoms such as a trifluoromethyl group being a fluorine atom or the like
  • a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, and a nitro group are preferable.
  • R a and R b each have the same meaning as described above.
  • the number of substituents in the “aromatic hydrocarbon ring having 6 to 30 carbon atoms which may have a substituent” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent
  • aromatic heterocyclic group having 2 to 30 carbon atoms include, for example, a 1-benzofuranyl group, 2-benzofuranyl group, imidazolyl group, indolyl group, furazanyl group, oxazolyl group, quinolyl group, thiadiazolyl group, thiazolyl group, thiazolopyrazinyl group, thiazolopyridyl group, thiazolopyridazinyl group, thiazolopyrimidinyl group , Thienyl group, triazinyl group, triazolyl group, naphthyridinyl group, pyrazinyl group, pyrazolyl group, pyranyl group, pyridyl group, pyridazinyl group
  • “monocyclic aromatic heterocyclic groups” such as furanyl group, pyranyl group, thienyl group, oxazolyl group, furazanyl group, thiazolyl group, thiadiazolyl group; benzothiazolyl group, benzoxazolyl group, quinolyl group, 1 -Benzofuranyl group, 2-benzofuranyl group, phthalimide group, benzo [c] thienyl group, benzo [b] thienyl group, thiazolopyridyl group, thiazolopyrazinyl group, benzoisoxazolyl group, benzooxadiazolyl group And "a condensed ring aromatic heterocyclic group” such as a benzothiadiazolyl group;
  • substituent in the “optionally substituted aromatic heterocyclic group having 2 to 30 carbon atoms” include the above “optionally substituted aromatic group having 6 to 30 carbon atoms”.
  • substituent in the “hydrocarbon ring group” are the same.
  • the number of substituents in the “aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • R a may have an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms as a substituent.
  • Specific examples of the “alkyl group having 1 to 6 carbon atoms” include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, and the like. Among these, a methyl group and an ethyl group are preferable.
  • C 1-6 alkoxy group examples include, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, t-butoxy group, Examples thereof include an n-pentyloxy group and an n-hexyloxy group.
  • aromatic hydrocarbon ring group having 6 to 18 carbon atoms examples include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group and the like. Among these, a phenyl group is preferable.
  • R a are preferably a phenyl group and a tolyl group.
  • R b has an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkenyl group having 2 to 20 carbon atoms, and a substituent as described above. It represents an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms.
  • alkyl group having 1 to 20 carbon atoms which may have a substituent include, for example, a methyl group, an ethyl group, n- Propyl, isopropyl, n-butyl, isobutyl, 1-methylpentyl, 1-ethylpentyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-to Xyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl
  • substituent in the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; dimethylamino group An N, N-dialkylamino group having 2 to 12 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group, etc., an alkoxy group having 1 to 20 carbon atoms; methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group An alkoxy group having 1 to 12 carbon atoms substituted with an alkoxy group having 1 to 12 carbon atoms such as ethoxyethoxy group; a nitro group; a carbon group having 6 to 18 carbon atoms such as a phenyl group, 1-naphthyl group, 2-naphthyl group, etc.
  • An aromatic hydrocarbon ring group of 2 to 1 carbon atoms such as triazolyl group, pyrrolyl group, furanyl group, thienyl group, thiazolyl group, benzothiazol-2-ylthio group
  • fluorine atom, cyano group, methoxy group, ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, phenyl group, 1-naphthyl group, 2-naphthyl group, benzothiazole A -2-ylthio group is preferred.
  • the number of substituents in the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • alkenyl group having 2 to 20 carbon atoms which may have a substituent as R b
  • Specific examples of “an alkynyl group having 2 to 20 carbon atoms” in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b include “an alkynyl group having 2 to 20 carbon atoms” in the above Ay.
  • Specific examples of the “group” are the same, and preferable examples thereof are also the same as the preferable examples of the “alkynyl group having 2 to 20 carbon atoms” in Ay.
  • substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b are the above-described “optionally substituted alkyl group having 1 to 20 carbon atoms”. Are the same as the specific examples of the substituents.
  • the number of substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • substituent in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” as R b include, for example, a halogen atom such as a fluorine atom or a chlorine atom; a cyano group; An N, N-dialkylamino group having 2 to 12 carbon atoms such as a group; an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group or a propyl group; A nitro group; an aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as a phenyl group, a 1-naphthyl group and a 2-naphthyl group; Among these, halogen atoms such as fluorine atom and chlorine atom; cyano group; alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group and propyl group; carbon number 1 such as methoxy group, ethoxy group
  • aromatic hydrocarbon ring group having 6 to 18 carbon atoms in the “optionally substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms” as R b include, for example, phenyl Group, 1-naphthyl group, 2-naphthyl group, and the like. Among these, a phenyl group is preferable.
  • substituent in the “optionally substituted aromatic hydrocarbon ring having 6 to 18 carbon atoms” as R b include, for example, a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; C 2-12 N, N-dialkylamino group such as dimethylamino group; C 1-20 alkoxy group such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group, methoxyethoxy group, etc.
  • An aromatic heterocycle having 2 to 18 carbon atoms such as a nitro group; a triazolyl group, a pyrrolyl group, a furanyl group, or a thiophenyl group, which is substituted with an alkoxy group having 1 to 12 carbon atoms;
  • --Gy-- Gy is (i) an optionally substituted divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, and (ii) an optionally substituted substituent having 3 to 30 carbon atoms. At least one of —CH 2 — contained in the divalent aliphatic hydrocarbon group is —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O. Substituted with —C ( ⁇ O) —O—, —NR 21 —C ( ⁇ O) —, —C ( ⁇ O) —NR 21 —, —NR 21 —, or —C ( ⁇ O) — An organic group of any of the groups.
  • R 21 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • the “divalent aliphatic hydrocarbon group” is preferably a divalent chain aliphatic hydrocarbon group, and more preferably an alkylene group.
  • substituents in “(i) a divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent” as Gy include, for example, a halogen atom such as a fluorine atom or a chlorine atom.
  • Atom cyano group; N, N-dialkylamino group having 2 to 12 carbon atoms such as dimethylamino group; alkoxy group having 1 to 20 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group , A methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, or the like, an alkoxy group having 1 to 12 carbon atoms substituted by an alkoxy group having 1 to 12 carbon atoms; a nitro group; a trifluoromethyl group, a pentafluoroethyl group, CH And an alkyl group having 1 to 12 carbon atoms in which one or more hydrogen atoms such as 2 CF 3 are substituted with a fluorine atom; a hydroxyl group and the like.
  • a fluorine atom, a cyano group, an alkoxy group having 1 to 20 carbon atoms, and an alkoxy group having 1 to 12 carbon atoms substituted with an alkoxy group having 1 to 12 carbon atoms are preferable, and a fluorine atom, a cyano group, and a methoxy group are preferable.
  • Ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, and ethoxyethoxy group are more preferable.
  • the number of substituents in “(i) a divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent” as Gy may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • --Yy--- Yy represents —O—, —C ( ⁇ O) —, —S—, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —, —O—C ( ⁇ O) —O—. , —C ( ⁇ O) —S—, —SC— ( ⁇ O) —, —NR 22 —C ( ⁇ O) —, —C ( ⁇ O) —NR 22 —, —O—C ( ⁇ O ) —NR 22 —, —NR 22 —C ( ⁇ O) —O—, —N ⁇ N—, or —C ⁇ C—.
  • R 22 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • —O—, —O—C ( ⁇ O) —O—, —O—C ( ⁇ O) —, and —C ( ⁇ O) —O— are preferable.
  • --Fy-- Fy represents an organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
  • the number of carbon atoms of the organic group is preferably 2 or more and 30 or less, more preferably 7 or more and 30 or less, still more preferably 8 or more and 30 or less, and particularly preferably 10 or more and 30 or less. preferable.
  • the “carbon number” of the “organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” of Fy is the carbon of the “organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” itself. Means number and does not include carbon atoms of substituents.
  • Fy is (i) “substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms, wherein at least one hydrogen atom has at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, And an alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group, or (ii) a substituent having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. It is preferably a cyclic group having 2 to 30 carbon atoms which may have When Fy has a plurality of aromatic hydrocarbon rings and / or a plurality of aromatic heterocycles, each may be the same or different.
  • aromatic hydrocarbon ring in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. And an aromatic hydrocarbon ring having 6 to 30 carbon atoms, such as a fluorene ring.
  • aromatic heterocycle in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, 1H-isoindole-1,3 (2H) -dione ring, 1-benzofuran ring, 2-benzofuran ring, acridine ring, isoquinoline ring, imidazole ring, indole ring, oxadiazole ring, oxazole ring, oxazolopyrazine ring, oxazolopyridine ring, oxazolopyridazine ring, oxazolopyrimidine ring, Quinazoline ring, quinoxaline ring, quinoline ring, cinnoline ring, thiadiazole ring, thiazole ring, thiazolopyrazine ring, thiazolopyridine ring, thiazolopyridazine ring, thiazolopyrimidine ring, thioph
  • substituent in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; methyl group, ethyl group, An alkyl group having 1 to 6 carbon atoms such as a propyl group; an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group; one or more hydrogen atoms such as a trifluoromethyl group or a pentafluoroethyl group are fluorine atoms, etc.
  • R b represents the same meaning as described above, and preferred examples thereof are also the same as described above.
  • Fy may have a plurality of substituents selected from the above-described substituents. When Fy has a plurality of substituents, the substituents may be the same or different.
  • (I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring;
  • Specific examples of the “alkyl group having 1 to 18 carbon atoms” in the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” include, for example, a methyl group, an ethyl group, A propyl group, an isopropyl group, etc. are mentioned.
  • (I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring;
  • at least one of the aromatic hydrocarbon ring and the aromatic heterocyclic ring” in the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” means “having 1 to 18 carbon atoms”. It may be directly bonded to the carbon atom of the alkyl group, or —S—, —O—, —C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O).
  • R 23 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • examples of the optionally substituted cyclic group having 2 to 30 carbon atoms having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring include “aromatic groups such as a fluorenyl group and a benzothiazolyl group”.
  • Also included are “a group consisting of an optionally substituted aromatic hydrocarbon ring” and “a group consisting of an optionally substituted aromatic heterocycle having a linking group”.
  • aromatic hydrocarbon ring group in the “optionally substituted aromatic hydrocarbon ring group” include carbon such as phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluorenyl group and the like. And an aromatic hydrocarbon ring group of 6 to 30;
  • substituent in the “optionally substituted aromatic hydrocarbon ring group” include specific examples of the substituent in the above “optionally substituted cyclic group having 2 to 30 carbon atoms”. Same as “Example”.
  • aromatic heterocyclic group in the “optionally substituted aromatic heterocyclic group” include phthalimide group, 1-benzofuranyl group, 2-benzofuranyl group, acridinyl group, isoquinolinyl group, imidazolyl group, Indolyl group, furazanyl group, oxazolyl group, oxazolopyrazinyl group, oxazolopyridinyl group, oxazolopyridazinyl group, oxazolopyrimidinyl group, quinazolinyl group, quinoxalinyl group, quinolyl group, cinnolinyl group, thiadiazolyl group , Thiazolyl group, thiazolopyrazinyl group, thiazolopyridyl group, thiazolopyridazinyl group, thiazolopyrimidinyl group, thienyl group, triazinyl group, triazolyl group,
  • (I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring;
  • Preferred examples of the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” include structures represented by the following formulas (3-1) to (3-11): Is mentioned.
  • the present invention is not limited to the following.
  • “*” represents a position bonded to Yy
  • “ ⁇ ” extending from the inside of the ring represents a bond extending from an arbitrary position on the ring.
  • the groups represented by the following formulas (3-1) to (3-11) may have a substituent.
  • Specific examples of the substituent include the above-mentioned ““ having a substituent. The same as the “specific examples of substituents” in the “cyclic group having 2 to 30 carbon atoms”.
  • the “alkyl group having 1 to 18 carbon atoms” in the “optionally substituted alkyl group having 1 to 18 carbon atoms” may have one or more substituents.
  • the “plural substituents” may be the same as or different from each other. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
  • Examples of “(ii) a cyclic group having 2 to 30 carbon atoms which has at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring and may have a substituent” as Fy include, for example, (ii-1 ) An optionally substituted hydrocarbon ring group having 6 to 30 carbon atoms, having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms; and (ii-2) an aromatic having 6 to 18 carbon atoms.
  • a heterocyclic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring having 2 to 30 carbon atoms, an optionally substituted heterocyclic group having 2 to 30 carbon atoms, and the like Preferably mentioned.
  • hydrocarbon ring group in the above “(ii-1) optionally having a hydrocarbon ring group having 6 to 30 carbon atoms, which has an aromatic hydrocarbon ring having 6 to 30 carbon atoms”.
  • phenyl group (6 carbon atoms), naphthyl group (10 carbon atoms), anthracenyl group (14 carbon atoms), phenanthrenyl group (14 carbon atoms), pyrenyl group (16 carbon atoms), fluorenyl
  • An aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as a group (carbon number 13); an indanyl group (9 carbon atoms); a 1,2,3,4-tetrahydronaphthyl group (10 carbon atoms); Dihydronaphthyl group (10 carbon atoms); and the like.
  • Specific examples of the “(ii-1) at least one hydrocarbon ring group having 6 to 30 carbon atoms, which may have a substituent and having 6 to 30 carbon atoms” include: Examples thereof include groups having structures represented by the following formulas (1-1) to (1-21). The groups having the structures represented by the following formulas (1-1) to (1-21) may have a substituent. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”. In the following formulas (1-1) to (1-21), “-” extending from the inside of the ring represents a bond with Yy extending from any position of the ring.
  • aromatic hydrocarbon ring having 6 to 18 carbon atoms having a substituent having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • aromatic hydrocarbon ring having 6 to 18 carbon atoms having an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • heterocyclic group in the “heterocyclic group having 2 to 30 carbon atoms” include, for example, phthalimide group, 1-benzofuranyl group, 2-benzofuranyl group, acridinyl group, isoquinolinyl group, imidazolyl group, indolyl group, and flazanyl group.
  • “-” extending from the inside of the ring represents a bond with Yy extending from any position of the ring.
  • X 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 —
  • E represents —NR c —, an oxygen atom or a sulfur atom.
  • R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group. (However, in each formula, oxygen atom, sulfur atom, —SO—, and —SO 2 — are not adjacent to each other.)]
  • the “(ii) optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” has one or more substituents. May be. When it has a plurality of substituents, the plurality of substituents may be the same as or different from each other. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
  • Fy is preferably a group having a structure represented by any of the following formulas (i-1) to (i-9), and the following formula (ii-1) A group having a structure represented by any one of (ii-20) is particularly preferred.
  • Ar is a group having a structure represented by (II-2) or (II-3)
  • Fy is a group having a structure represented by any of the following (i-1) to (i-13): It is preferably a group having a structure represented by any of the following formulas (ii-1) to (ii-26).
  • the group having a structure represented by any of the following formulas (i-1) to (i-13) and the following formulas (ii-1) to (ii-26) may have a substituent.
  • Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
  • Y represents the same meaning as described above.
  • “*” represents the position where Yy is bonded, and “ ⁇ ” extends from the inside of the ring. Represents a bond extending from any position of the ring.
  • the total number of ⁇ electrons contained in the ring structure in Fy is preferably 8 or more, more preferably 10 or more, and 20 or less. Preferably, it is 18 or less.
  • Ar is a group having a structure represented by (II-2) or (II-3)
  • the total number of ⁇ electrons contained in the ring structure in Fy is preferably 4 or more, and is 6 or more. More preferably, it is preferably 20 or less, and more preferably 18 or less.
  • -Ax- Ax represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • Ax is preferably any one of the following (1) to (5).
  • hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms examples include groups represented by the following structural formula.
  • the group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later.
  • substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax include a fluorine atom, a chlorine atom, etc.
  • a cyano group an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group or a propyl group; an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group; one such as a trifluoromethyl group
  • An alkoxy group having 1 to 6 carbon atoms such as a propoxy group; a
  • R b and R a are each the same meanings as defined above, the preferred examples are also the same as above.
  • at least one substituent selected from the group consisting of a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms is preferable.
  • “Aromatic hydrocarbon ring having 6 to 30 carbon atoms” in “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax Specific examples include a benzene ring, a naphthalene ring, a fluorene ring, and the like.
  • ring group having at least one aromatic ring selected from the group consisting of (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms as -Ax Heterocyclic group ”
  • Specific examples of the “ring group” include, for example, groups represented by the following structural formulas. The group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later.
  • R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group, and “ ⁇ ” extending from the inside of the ring represents any position of the ring. Represents a bond that extends from ]
  • Specific examples of the substituent of the “cyclic group” include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms”. The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms”. is there.
  • aromatic hydrocarbon ring having 6 to 30 carbon atoms include, for example, benzene ring, naphthalene ring, fluorene ring, anthracene ring and the like.
  • aromatic heterocycle having 2 to 30 carbon atoms in “ring group” include, for example, thiophene ring, furan ring, pyridine ring, pyrazine ring, pyrimidine ring, triazine ring, pyrrole ring, imidazole ring, thiazole ring.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax -
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • Specific examples of the “alkyl group having 1 to 12 carbon atoms” include, for example, methyl group, ethyl group, propyl group, isopropyl group, and the like.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • substituents include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax; The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. The same.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic hydrocarbon ring group having 6 to 30 carbon atoms are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in the above Ay.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic heterocyclic group having 2 to 30 carbon atoms include the same examples as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax -
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • Specific examples of the “alkenyl group having 2 to 12 carbon atoms” include, for example, a vinyl group and an allyl group.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • substituents include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax; The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. The same.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic hydrocarbon ring group having 6 to 30 carbon atoms are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in the above Ay.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic heterocyclic group having 2 to 30 carbon atoms include the same examples as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax - “(5) an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax
  • Specific examples include ethynyl group, propynyl group, and the like.
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • substituents are the same as those of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax.
  • the preferred examples thereof are also the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. .
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic hydrocarbon ring group having 6 to 30 carbon atoms are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in Ay.
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic heterocyclic group having 2 to 30 carbon atoms are the same as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
  • Ax is preferably any one of groups represented by the following structural formula.
  • the group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later. [In each formula, “-” extending from the inside of the ring represents a bond extending from any position of the ring. ]
  • Ax is more preferably any one of the groups represented by the following structural formula.
  • Ax is particularly preferably any one of groups represented by the following structural formula.
  • Ax may have a substituent.
  • substituents of Ax include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group and propyl group; vinyl group, An alkenyl group having 2 to 6 carbon atoms such as an allyl group; an alkyl group having 1 to 6 carbon atoms in which one or more hydrogen atoms such as a trifluoromethyl group are substituted with a halogen atom such as a fluorine atom; An N, N-dialkylamino group having 2 to 12 carbon atoms; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; —OCF 3 ; —C ( ⁇ O) —R b —O—C ( ⁇ O) —R b
  • -Az- Az represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • Az excludes the case of C (Ay) Ax.
  • Az is preferably any of the following (1) and (2).
  • Az is more preferably any one of the groups represented by the following structural formula.
  • R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group.
  • Ar is preferably represented by any of the following formulas (III-1) to (III-6), more preferably the following formula (III-1), the following formula (III-2), the following formula (III) -4) or the following formula (III-5), particularly preferably the following formula (III-1) or the following formula (III-4).
  • the substituent may have an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group.
  • Ax, Ay, Az and Q have the same meaning as described above, and preferred examples thereof are also the same as above, and * represents Z 1 or Z 2. Represents that it is combined with.
  • * represents a position bonded to Ar
  • R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Z 1 and Z 2 are each independently a chemical single bond, —O—, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —, * —CH 2.
  • a 1 and A 2 each independently represents a divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent.
  • the chain aliphatic group includes —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, — NR 12 —C ( ⁇ O) —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) — may be present.
  • —O— or —S— are adjacent to each other is excluded.
  • R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Provided that the carbon atom bonded to Z 1 and the carbon atom bonded to Y 1 or Y 3 of A 1 and the carbon atom bonded to Z 2 and the carbon atom bonded to Y 2 or Y 4 of A 2 are bonded to each other. , —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, —NR 12 —C ( ⁇ O) There is no substitution with —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) —.
  • divalent chain aliphatic group having 1 to 20 carbon atoms in the “divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent” include, for example, , Methylene group, ethylene group, hexamethylene group, propylene group, tetramethylene group, pentamethylene group, hexamethylene group, octamethylene group, decamethylene group [— (CH 2 ) 10 —], etc.
  • Alkylene group vinylene group, 1-methylvinylene group, propenylene group, 1-butenylene group, 2-butenylene group, 1-pentenylene group, 2-pentenylene group, etc., alkenylene group having 2 to 20 carbon atoms; 1,3-pentadienyl group And groups having a conjugated diene having 2 to 20 carbon atoms such as a 1,3-hexadienyl group.
  • a divalent saturated chain aliphatic group having 2 to 20 carbon atoms and a divalent unsaturated chain aliphatic group having 2 to 20 carbon atoms are preferable, and a divalent saturated chain having 3 to 20 carbon atoms.
  • aliphatic aliphatic groups divalent unsaturated chain aliphatic groups having 2 to 20 carbon atoms
  • divalent unsaturated chain aliphatic groups having 2 to 20 carbon atoms vinylene group, propylene group and propylene group.
  • a nylene group and a butenylene group are preferred.
  • the “C 1-20 divalent chain aliphatic group” includes —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, —NR 12 —C ( ⁇ O) —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) — interposed (However, the case where two or more of —O— or —S— are adjacent to each other is excluded).
  • R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and is preferably a hydrogen atom or a methyl group.
  • substituent in the “divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent” include, for example, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Halogen atom carbon number such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyloxy group, etc. 1-6 alkoxy groups; and the like.
  • a fluorine atom, a methoxy group, and an ethoxy group are preferable.
  • B 1 and B 2 each independently represent a cyclic aliphatic group that may have a substituent or an aromatic group that may have a substituent, and have a substituent.
  • a cyclic aliphatic group having 5 to 20 carbon atoms or an aromatic group having 2 to 20 carbon atoms which may have a substituent is preferable.
  • cycloaliphatic group in the “optionally substituted cycloaliphatic group” include cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, cycloheptane, and the like.
  • cycloalkanediyl groups such as 1,4-diyl, cyclooctane-1,5-diyl; carbons such as decahydronaphthalene-1,5-diyl and decahydronaphthalene-2,6-diyl And a bicycloalkanediyl group of 5 to 20;
  • the cycloaliphatic group is preferably a cycloalkanediyl group having 5 to 20 carbon atoms, more preferably a cyclohexanediyl group, and particularly preferably a cyclohexane-1,4-diyl group.
  • the “cycloaliphatic group” may be a trans isomer, a cis isomer, or a mixture of a cis isomer and a trans isomer, but a trans isomer is more preferable.
  • aromatic group in the “aromatic group optionally having substituent (s)” include, for example, 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, An aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as 1,4-naphthylene group, 1,5-naphthylene group, 2,6-naphthylene group, 4,4′-biphenylene group; furan-2,5- And aromatic heterocyclic groups having 2 to 20 carbon atoms such as diyl, thiophene-2,5-diyl, pyridine-2,5-diyl and pyrazine-2,5-diyl.
  • an aromatic hydrocarbon ring group having 6 to 18 carbon atoms is preferable, a phenylene group is more preferable, and a 1,4-phenylene group is particularly preferable.
  • substituents in the “optionally substituted cycloaliphatic group” and the “optionally substituted aromatic group” include, for example, a halogen atom, an alkyl having 1 to 6 carbon atoms. Group, an alkoxy group having 1 to 5 carbon atoms, a nitro group, a cyano group, and the like.
  • the cycloaliphatic group and the aromatic group may have at least one substituent selected from the above-described substituents.
  • each substituent may be the same or different.
  • R 13 and R 14 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Y 1 to Y 4 are preferably each independently a single bond, —O—, —C ( ⁇ O) —O—, or —O—C ( ⁇ O) —, More preferably, they are O—, —C ( ⁇ O) —O—, or —O—C ( ⁇ O) —.
  • G 1 and G 2 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and 1 of a methylene group (—CH 2 —) contained in an aliphatic hydrocarbon group having 3 to 20 carbon atoms.
  • the above is an organic group of any of the groups substituted with —O— or —C ( ⁇ O) —.
  • a hydrogen atom contained in the organic group of G 1 and G 2 may be substituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom.
  • the methylene groups (—CH 2 —) at both ends of G 1 and G 2 are not substituted with —O— or —C ( ⁇ O) —.
  • aliphatic hydrocarbon group having 1 to 20 carbon atoms and the “aliphatic hydrocarbon group having 3 to 20 carbon atoms” include an alkylene group having 1 to 20 carbon atoms and a carbon number, respectively. Examples include 3 to 20 alkylene groups. Among these, n-butylene group, n-hexylene group, n-octylene group, and n-decamethylene group [— (CH 2 ) 10 —] are preferable.
  • P 1 and P 2 each independently represent a polymerizable group.
  • the polymerizable group include a group represented by CH 2 ⁇ CR 31 —C ( ⁇ O) —O— such as acryloyloxy group and methacryloyloxy group (R 31 is a hydrogen atom, methyl group) Or a chlorine atom.), Vinyl group, vinyl ether group, p-stilbene group, acryloyl group, methacryloyl group, carboxyl group, methylcarbonyl group, hydroxyl group, amide group, alkylamino group having 1 to 4 carbon atoms, amino group , Epoxy group, oxetanyl group, aldehyde group, isocyanate group or thioisocyanate group.
  • a group represented by CH 2 ⁇ CR 31 —C ( ⁇ O) —O— is preferable, and a group represented by CH 2 ⁇ CH—C ( ⁇ O) —O— (acryloyloxy group), A group represented by CH 2 ⁇ C (CH 3 ) —C ( ⁇ O) —O— (methacryloyloxy group) is more preferred, and an acryloyloxy group is particularly preferred.
  • ⁇ P, q> p and q each independently represents an integer of 0 to 2.
  • p and q are each independently 1.
  • B 1 and B 2 in the aforementioned formula (I) are preferably each independently an aromatic group which may have a substituent.
  • An aromatic group having 6 to 18 carbon atoms which may have a group is more preferable, and a phenylene group is particularly preferable.
  • the polymerizable compound (I) is not particularly limited, but has a symmetric structure centered on Ar (that is, Z 1 and Z 2 , A 1 and A 2 , Y 1 and Y 2 , B 1 and B 2 , n and m, Y 3 and Y 4 , G 1 and G 2 , and P 1 and P 2 are preferably the same (symmetric about Ar).
  • the above-described polymerizable liquid crystal compound (I) can be synthesized by combining known synthetic reactions. That is, various documents (for example, International Publication No. 2012/141245, International Publication No. 2012/147904, International Publication No. 2014/010325, International Publication No. 2013/046871, International Publication No. 2014/061709, International Publication No. 2014/126113, International Publication No. 2015/064698, International Publication No. 2015-140302, International Publication No. 2015/129654, International Publication No. 2015/141784, International Publication No. 2016/159193, International Publication No. 2012 / 169424, International Publication No. 2012/176679, International Publication No. 2015/122385 and the like.
  • the polymerizable liquid crystal composition contains at least a polymerizable liquid crystal compound (I) and a polymerization initiator.
  • the polymerizable liquid crystal composition is useful as a raw material for producing the polymer, optical film, and optical anisotropic body of the present invention, as will be described later. According to the polymerizable liquid crystal composition of the present invention, it is possible to satisfactorily produce an optical film or the like having ideal wavelength dispersion exhibiting broadband properties, that is, reverse wavelength dispersion.
  • a polymerization initiator is mix
  • a radical polymerization initiator, an anionic polymerization initiator, a cationic polymerization initiator, etc. are mentioned.
  • radical polymerization initiator a thermal radical generator which is a compound that generates an active species capable of initiating polymerization of a polymerizable liquid crystal compound by heating; visible light, ultraviolet light (i-line etc.), far ultraviolet light, Any of radical photogenerators, which are compounds that generate active species capable of initiating polymerization of a polymerizable liquid crystal compound upon exposure to exposure light such as an electron beam or X-ray, can be used. It is preferred to use.
  • Photoradical generators include acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, ⁇ -diketone compounds, polynuclear quinone compounds , Xanthone compounds, diazo compounds, imide sulfonate compounds, and the like. These compounds are components that generate active radicals or active acids or both active radicals and active acids upon exposure.
  • a photoradical generator can be used individually by 1 type or in combination of 2 or more types.
  • acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, And 1- [4- (phenylthio) phenyl] -octane-1,2-dione 2- (O-benzoyloxime).
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2 , 2'-bis (2-bromophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4-dichlorophenyl) -4,4', 5,5'-tetraphenyl-1 , 2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimi
  • the hydrogen donor means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure.
  • the hydrogen donor mercaptan compounds, amine compounds and the like defined below are preferable.
  • mercaptan compounds include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-2,5-dimethyl.
  • An aminopyridine etc. can be mentioned.
  • amine compounds include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, ethyl-4-dimethylaminobenzoate, Examples include 4-dimethylaminobenzoic acid and 4-dimethylaminobenzonitrile.
  • triazine compound examples include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2- (5 -Methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloromethyl)- s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxyphenyl) ethenyl -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl)
  • O-acyloxime compounds include 1- [4- (phenylthio) phenyl] -heptane-1,2-dione 2- (O-benzoyloxime), 1- [4- (phenylthio) phenyl]- Octane-1,2-dione 2- (O-benzoyloxime), 1- [4- (benzoyl) phenyl] -octane-1,2-dione 2- (O-benzoyloxime), 1- [9-ethyl- 6- (2-Methylbenzoyl) -9H-carbazol-3-yl] -ethanone 1- (O-acetyloxime), 1- [9-ethyl-6- (3-methylbenzoyl) -9H-carbazole-3- Yl] -ethanone 1- (O-acetyloxime), 1- (9-ethyl-6-benzoyl-9H-carbazol-3-yl) -ethanone 1- (O-acetyloxime), 1-
  • anionic polymerization initiator examples include alkyl lithium compounds; monolithium salts or monosodium salts such as biphenyl, naphthalene, and pyrene; polyfunctional initiators such as dilithium salts and trilithium salts;
  • Examples of the cationic polymerization initiator include proton acids such as sulfuric acid, phosphoric acid, perchloric acid and trifluoromethanesulfonic acid; Lewis acids such as boron trifluoride, aluminum chloride, titanium tetrachloride and tin tetrachloride; A combined system of a group onium salt or an aromatic onium salt and a reducing agent.
  • polymerization initiators can be used singly or in combination of two or more.
  • the blending ratio of the polymerization initiator is usually 0.1 to 30 parts by mass, preferably 0.1 to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. 5 to 10 parts by mass.
  • the polymerizable liquid crystal composition preferably contains a surfactant in order to adjust the surface tension.
  • the surfactant is not particularly limited, but a nonionic surfactant is usually preferable.
  • commercially available products may be used.
  • nonionic surfactants that are oligomers containing fluorine-containing groups, hydrophilic groups, and lipophilic groups, such as Surflon manufactured by AGC Seimi Chemical Co., Ltd.
  • these surfactants may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
  • the blending ratio of the surfactant is usually 0.01 to 10 parts by mass, preferably 0 with respect to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. .01 to 2 parts by mass.
  • the polymerizable liquid crystal composition may further contain other components in addition to the polymerizable liquid crystal compound, the polymerization initiator, and the surfactant as long as the effects of the present invention are not affected.
  • Other components include metals, metal complexes, dyes, pigments, fluorescent materials, phosphorescent materials, leveling agents, thixotropic agents, gelling agents, polysaccharides, ultraviolet absorbers, infrared absorbers, antioxidants, ion exchange resins, Examples thereof include metal oxides such as titanium oxide.
  • other components include other copolymerizable monomers. Specifically, it is not particularly limited.
  • the polymerizable liquid crystal composition is usually prepared by mixing and dissolving a predetermined amount of a polymerizable liquid crystal compound, a polymerization initiator, and other components blended as required in an appropriate organic solvent. Can do.
  • Organic solvents to be used include ketones such as cyclopentanone, cyclohexanone and methyl ethyl ketone; acetate esters such as butyl acetate and amyl acetate; halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane; 1,4-dioxane, cyclopentylmethyl And ethers such as ether, tetrahydrofuran, tetrahydropyran, and 1,3-dioxolane;
  • ketones such as cyclopentanone, cyclohexanone and methyl ethyl ketone
  • acetate esters such as butyl acetate and amyl acetate
  • halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane
  • 1,4-dioxane 1,4-dioxane
  • cyclopentylmethyl And ethers such as
  • polymer of the present invention is obtained by polymerizing the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition.
  • “polymerization” means a chemical reaction in a broad sense including a crosslinking reaction in addition to a normal polymerization reaction.
  • the polymer of the present invention usually has a monomer unit derived from the polymerizable liquid crystal compound (I) (for example, the repeating unit (I) ′).
  • Y 1 to Y 4 , A 1 , A 2 , B 1 , B 2 , G 1 , G 2 , p, and q in the formula (I) ′ have the same meaning as described above, and preferred examples thereof Is the same.
  • R 31 is a hydrogen atom, a methyl group, or a chlorine atom, and among them, a hydrogen atom or a methyl group is preferable.
  • the polymer of the present invention is prepared using the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition, it can be favorably used as a constituent material for optical films and the like. .
  • the polymer of the present invention is not particularly limited, and can be used in any shape according to the application such as a film shape, a powder shape, or a layer shape in which powders are aggregated.
  • the polymer film can be used favorably as a constituent material of the optical film and optical anisotropic body described later, and the polymer powder can be used for paints, anti-counterfeit articles, security articles, etc.
  • the layer made of polymer powder can be used favorably as a constituent material of the optical anisotropic body.
  • the polymer of the present invention ( ⁇ ) was subjected to a polymerization reaction of the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition in the presence of a suitable organic solvent. Then, the target polymer is isolated, and the resulting polymer is dissolved in an appropriate organic solvent to prepare a solution. After coating the solution on an appropriate substrate and drying the resulting coating, ( ⁇ ) The above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition is dissolved in an organic solvent, and this solution is applied onto a substrate by a known coating method. After coating, it can be suitably produced by a method of performing a polymerization reaction by removing the solvent and then heating or irradiating active energy rays.
  • the polymerizable liquid crystal compound (I) described above may be polymerized alone.
  • the organic solvent used for the polymerization reaction in the method ( ⁇ ) is not particularly limited as long as it is inactive.
  • aromatic hydrocarbons such as toluene, xylene and mesitylene
  • ketones such as cyclohexanone, cyclopentanone and methyl ethyl ketone
  • acetate esters such as butyl acetate and amyl acetate
  • halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane
  • ethers such as cyclopentyl methyl ether, tetrahydrofuran and tetrahydropyran;
  • those having a boiling point of 60 to 250 ° C. are preferable and those having a temperature of 60 to 150 ° C. are more preferable from the viewpoint of excellent handleability.
  • an organic solvent for dissolving the isolated polymer and an organic solvent used in the method ( ⁇ ) include acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, Ketone solvents such as cyclohexanone; ester solvents such as butyl acetate and amyl acetate; halogenated hydrocarbon solvents such as dichloromethane, chloroform and dichloroethane; tetrahydrofuran, tetrahydropyran, 1,2-dimethoxyethane, 1,4-dioxane, Ether solvents such as cyclopentyl methyl ether and 1,3-dioxolane; N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, N-methylpyrrolidone (N-methyl-2-pyrrolidone), etc.
  • Non-proton Polar solvent such as
  • a known and commonly used material can be used regardless of organic or inorganic.
  • the organic material include polycycloolefins (for example, ZEONEX, ZEONOR (registered trademark; manufactured by ZEON CORPORATION), ARTON (registered trademark; manufactured by JSR), and APPEL (registered trademark; manufactured by Mitsui Chemicals)),
  • examples of the organic material include polycycloolefins (for example, ZEONEX, ZEONOR (registered trademark; manufactured by ZEON CORPORATION), ARTON (registered trademark; manufactured by JSR), and APPEL (registered trademark; manufactured by Mitsui Chemicals))
  • examples include polyethylene terephthalate, polycarbonate, polyimide, polyamide, polymethyl methacrylate, polystyrene, polyvinyl chloride, polytetrafluoroethylene, cellulose, cellulose triacetate, polyethersulfone, etc.
  • inorganic materials include silicon, glass, cal
  • the substrate used may be a single layer or a laminate.
  • a substrate made of an organic material is preferable, and a resin film obtained by forming an organic material into a film is more preferable.
  • substrate the board
  • a known method can be used as a method of applying a polymer solution to a substrate in the method ( ⁇ ) and a method of applying a solution for polymerization reaction to a substrate in the method ( ⁇ ).
  • curtain coating method, extrusion coating method, roll coating method, spin coating method, dip coating method, bar coating method, spray coating method, slide coating method, print coating method, gravure coating method, die coating method A cap coating method or the like can be used.
  • the drying temperature is not particularly limited as long as the solvent can be removed from the solvent, but the lower limit temperature is preferably 50 ° C. or higher from the viewpoint that a constant temperature can be stably obtained, and is 70 ° C. or higher. More preferably.
  • the upper limit temperature of the drying temperature is preferably 200 ° C. or less, more preferably 195 ° C. or less, from the viewpoint of a range that does not adversely affect the substrate.
  • Examples of a method for polymerizing the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition include a method of irradiating active energy rays, a thermal polymerization method, and the like.
  • the method of irradiating with active energy rays is preferable because the reaction proceeds at.
  • a method of irradiating light such as ultraviolet rays is preferable because the operation is simple.
  • the temperature at which the light such as ultraviolet rays is irradiated is not particularly limited as long as the liquid crystal phase can be maintained. However, the lower limit temperature is 15 ° C. or more from the viewpoint that the photopolymerization can proceed stably.
  • the temperature is 20 ° C. or higher.
  • the upper limit temperature for irradiating light such as ultraviolet rays is preferably 200 ° C. or lower, and more preferably 195 ° C. or lower, from the viewpoint of not adversely affecting the substrate.
  • the temperature at the time of light irradiation is preferably 100 ° C. or less.
  • the light irradiation intensity is usually in the range of 1 W / m 2 to 10 kW / m 2 , preferably in the range of 5 W / m 2 to 2 kW / m 2 .
  • the dose of ultraviolet rays is preferably 0.1 mJ / cm 2 or more, more preferably 0.5 mJ / cm 2 or more, preferably 5000 mJ / cm 2 or less, more preferably 4000 mJ / cm 2 or less.
  • the polymer obtained as described above can be used by being transferred from the substrate, separated from the substrate and used alone, or as a constituent material of an optical film or the like without being separated from the substrate. You can also The polymer peeled from the substrate can be used after being pulverized by a known method to form a powder.
  • the number average molecular weight of the polymer of the present invention obtained as described above is preferably 500 to 500,000, more preferably 5,000 to 300,000. If the number average molecular weight is in such a range, it is desirable because high hardness can be obtained and handleability is excellent.
  • the number average molecular weight of the polymer can be measured by gel permeation chromatography (GPC) using monodispersed polystyrene as a standard sample and tetrahydrofuran as an eluent.
  • the optical film of the present invention is formed using the polymer and / or polymerizable liquid crystal compound of the present invention, and includes a layer having an optical function.
  • the optical function means simple transmission, reflection, refraction, birefringence and the like.
  • the optical film of the present invention is an optical film comprising the polymer of the present invention as a main constituent material of the layer having an optical function, or the layer having an optical function is the polymerizable liquid crystal of the present invention. It can be an optical film containing a compound.
  • the occupation ratio of the polymer of the present invention is more than 50% by mass when all the components of the layer having an optical function are 100% by mass. is there.
  • the polymerizable liquid crystal compound of the present invention is added in an amount of 0.01% by mass when the total components of the layer having an optical function are 100% by mass. % Or more.
  • the optical film of the present invention is in the form (alignment substrate / (alignment film) / optical film) formed on the alignment substrate which may have an alignment film, and a transparent substrate film different from the alignment substrate.
  • the optical film may be transferred in any form (transparent substrate film / optical film), or in the case where the optical film is self-supporting, it may be in any form of an optical film single layer (optical film).
  • the alignment film and the alignment substrate the same substrate and alignment film as the optical anisotropic body described later can be used as the alignment film and the alignment substrate.
  • the optical film of the present invention is obtained by applying (A) a solution containing the polymerizable liquid crystal compound of the present invention or a solution of the polymerizable liquid crystal composition onto an alignment substrate, drying the obtained coating film, and subjecting to heat treatment. (Liquid crystal orientation), a method of performing light irradiation and / or heat treatment (polymerization), and (B) a liquid crystalline polymer obtained by polymerizing the polymerizable liquid crystal compound or polymerizable liquid crystal composition of the present invention. Or a solution containing the polymerizable liquid crystal compound of the present invention and a resin is applied on the alignment substrate, and the resulting coating is obtained. It can be produced by a method of drying the membrane.
  • the optical film of the present invention can be used for optical anisotropic bodies, alignment films for liquid crystal display elements, color filters, low-pass filters, light polarizing prisms, various optical filters, and the like.
  • the optical film of the present invention can be obtained from the phase difference at a wavelength of 400 nm to 800 nm measured with Mueller Matrix Polarimeter Axoscan.
  • the following ⁇ value and ⁇ value are preferably within a predetermined range. Specifically, the ⁇ value is preferably 0.70 to 0.99, and more preferably 0.75 to 0.90. Further, the ⁇ value is preferably 1.00 to 1.25, and more preferably 1.01 to 1.20.
  • ⁇ (phase difference at 450 nm) / (phase difference at 550 nm)
  • ⁇ (phase difference at 650 nm) / (phase difference at 550 nm)
  • the optical anisotropic body of this invention has a layer which uses the polymer of this invention as a constituent material.
  • the optical anisotropic body of the present invention can be obtained, for example, by forming an alignment film on a substrate and further forming a layer (liquid crystal layer) made of the polymer of the present invention on the alignment film.
  • the optically anisotropic body of the present invention may be one in which a layer made of the polymer of the present invention (liquid crystal layer) is directly formed on a substrate, or a layer made of the polymer of the present invention (liquid crystal layer). It may consist of only.
  • the polymer layer may be a film polymer or a powder polymer aggregate.
  • the alignment film is formed on the surface of the substrate in order to regulate the alignment of the polymerizable liquid crystal compound in one direction in the plane.
  • the alignment film is formed by applying a solution containing a polymer such as polyimide, polyvinyl alcohol, polyester, polyarylate, polyamideimide, or polyetherimide (alignment film composition) onto a substrate, drying the film, and then unidirectionally. It can be obtained by rubbing treatment.
  • the thickness of the alignment film is preferably 0.001 to 5 ⁇ m, and more preferably 0.001 to 1.0 ⁇ m.
  • the rubbing treatment method is not particularly limited, and examples thereof include a method of rubbing the alignment film in a certain direction with a roll made of a synthetic fiber such as nylon or a natural fiber such as cotton or a felt.
  • a method of regulating the alignment in one direction in the plane can be provided by a method of irradiating the surface of the alignment film with polarized ultraviolet rays.
  • Examples of the substrate on which the alignment film is formed include a glass substrate and a substrate made of a synthetic resin film.
  • the synthetic resin include acrylic resin, polycarbonate resin, polyethersulfone resin, polyethylene terephthalate resin, polyimide resin, polymethyl methacrylate resin, polysulfone resin, polyarylate resin, polyethylene resin, polystyrene resin, polyvinyl chloride resin, and cellulose diacetate. , Cellulose triacetate, and thermoplastic resins such as alicyclic olefin polymers.
  • Examples of the alicyclic olefin polymer include cyclic olefin random multicomponent copolymers described in JP-A No. 05-310845, US Pat. No. 5,179,171, JP-A No. 05-97978, and US Pat. No. 5,202,388. And hydrogenated polymers described in Japanese Patent Application Laid-Open No. 11-124429 (International Publication No. 99/20676), and thermoplastic dicyclopentadiene ring-opening polymers and hydrogenated products thereof. .
  • the same method as described in the section of the polymer of the present invention (the above ( ⁇ ) and ( ⁇ )) may be used. Can be mentioned.
  • the thickness of the obtained liquid crystal layer is not particularly limited, but is usually 1 to 10 ⁇ m.
  • phase difference plate a viewing angle expansion plate, etc.
  • viewing angle expansion plate etc.
  • the optical anisotropic body of the present invention is obtained from a phase difference at a wavelength of 400 nm to 800 nm measured with Mueller Matrix Polarimeter Axoscan.
  • the following ⁇ value and ⁇ value are preferably within a predetermined range. Specifically, the ⁇ value is preferably 0.70 to 0.99, and more preferably 0.75 to 0.90.
  • the ⁇ value is preferably 1.00 to 1.25, more preferably 1.01 to 1.25.
  • ⁇ (phase difference at 450 nm) / (phase difference at 550 nm)
  • ⁇ (phase difference at 650 nm) / (phase difference at 550 nm)
  • the polarizing plate of the present invention comprises the optical anisotropic body of the present invention and a polarizing film.
  • Specific examples of the polarizing plate of the present invention include those in which the optical anisotropic body of the present invention is laminated on a polarizing film directly or via another layer (glass plate or the like).
  • the manufacturing method of the polarizing film is not particularly limited.
  • a method for producing a PVA-based polarizing film a method of stretching uniaxially after iodine ions are adsorbed on a PVA-based film, a method of adsorbing iodine ions after stretching a uniaxially stretched PVA-based film, A method of simultaneously performing iodine ion adsorption and uniaxial stretching, a method of stretching a uniaxial film after dyeing a PVA film with a dichroic dye, a method of dyeing a dichroic dye after stretching a PVA film uniaxially, a PVA system
  • staining with a dichroic dye and uniaxial stretching to a film is mentioned.
  • a method for producing a polyene polarizing film a method of heating and dehydrating in the presence of a dehydration catalyst after stretching a PVA film uniaxially, a method of stretching a polyvinyl chloride film uniaxially and then in the presence of a dehydrochlorination catalyst And a known method such as heating and dehydrating.
  • the polarizing film and the optical anisotropic body of the present invention may be in contact with each other via an adhesive layer made of an adhesive (including an adhesive).
  • the average thickness of the adhesive layer is usually 0.01 ⁇ m to 30 ⁇ m, preferably 0.1 ⁇ m to 15 ⁇ m.
  • the adhesive layer is preferably a layer having a tensile fracture strength according to JIS K7113 of 40 MPa or less.
  • Adhesives constituting the adhesive layer include acrylic adhesives, urethane adhesives, polyester adhesives, polyvinyl alcohol adhesives, polyolefin adhesives, modified polyolefin adhesives, polyvinyl alkyl ether adhesives, rubber adhesives, vinyl chloride Vinyl acetate adhesive, styrene / butadiene / styrene copolymer (SBS copolymer) adhesive, hydrogenated product (SEBS copolymer) adhesive, ethylene / vinyl acetate copolymer, ethylene-styrene copolymer, etc.
  • SBS copolymer vinyl chloride Vinyl acetate adhesive
  • SEBS copolymer hydrogenated product
  • Ethylene adhesives and acrylic ester adhesives such as ethylene / methyl methacrylate copolymers, ethylene / methyl acrylate copolymers, ethylene / ethyl methacrylate copolymers and ethylene / ethyl acrylate copolymers, etc. Is mentioned.
  • the polarizing plate of the present invention uses the optical anisotropic body of the present invention, it has excellent in-plane uniformity of optical characteristics while having reverse wavelength dispersion.
  • a display device provided with a panel and an antireflection film can be suitably produced.
  • the panel include a liquid crystal panel and an organic electroluminescence panel.
  • the display device include a flat panel display device including a polarizing plate and a liquid crystal panel, and an organic electroluminescence display device including a liquid crystal panel and an organic electroluminescence panel.
  • the polymerizable liquid crystal compound of the present invention and the intermediate that can be used for the preparation of the polymerizable liquid crystal compound are WO 2012/141245, WO 2012/147904, WO 2014/010325, and WO 2013/046781, International Publication No. 2014/126113, International Publication No. 2015/025793, Japanese Patent Application Laid-Open No. 2015-140302, International Publication No. 2015/129654, International Publication No. 2015/141784, International Publication No. 2016 / It can be synthesized with reference to No. 159193.
  • the structure of an intermediate that can be used for the preparation of the polymerizable liquid crystal compound of the present invention is represented, for example, by the following general formula (X-1).
  • P 1 , G 1 , Y 3 , B 1 , Y 1 , A 1 , p each represents the same meaning as described above, and preferred examples thereof also represent the P 1 , G 1 , Y 3 , B 1 , Y 1 , A 1 , p are the same as the preferred examples, and FG represents a hydroxyl group or a carboxyl group.
  • Y are as defined above Y 1, Y 2, the preferred embodiment is also the same as the preferred examples of the Y 1, Y 2, a are as defined above a 1, a 2, The preferred examples are the same as the preferred examples of A 1 and A 2 . ]
  • a compound represented by the general formula (X1) (hereinafter referred to as “compound (X1)”) and a compound represented by the general formula (X2) (hereinafter referred to as “compound (X2)”) are present in a base.
  • compound (X1) a compound represented by the general formula (X2)
  • compound (X2) a compound represented by the general formula (X2)
  • compound (X) By reacting under the above conditions, a compound represented by the general formula (X) (hereinafter referred to as “compound (X)”) can be obtained.
  • the amount of compound (X1) used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of compound (X2). More preferably, it is usually 1.5 molar equivalents or less, and more preferably 1.3 molar equivalents or less.
  • Examples of the base used include tertiary amines such as triethylamine, pyridine, diisopropylethylamine, and N, N-dimethyl-4-aminopyridine;
  • the amount of the base used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of compound (X2). Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
  • the compound (X) can be obtained by reacting the compound (X1) having a hydroxyl group with a dicarboxylic acid using a dehydrating condensing agent.
  • the amount of compound (X1) used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of dicarboxylic acid. Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
  • the condensing agent to be used examples include dehydrating condensing agents such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride;
  • the amount of the condensing agent to be used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of the dicarboxylic acid. Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
  • an activator such as N, N-dimethyl-4-aminopyridine may be used in combination.
  • the compound (X) can be obtained by reacting the compound (X1) having a hydroxyl group with a strong base such as NaH and then reacting with an acid anhydride.
  • the amount of strong base such as NaH is usually 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, and usually 3 moles, based on the usage amount of compound (X1). It is preferably not more than the equivalent, preferably not more than 1.5 molar equivalent, more preferably not more than 1.3 molar equivalent.
  • an activator such as N, N-dimethyl-4-aminopyridine may be used in combination.
  • any one of the compounds represented by the general formulas (Y1) to (Y3) (hereinafter referred to as “compounds (Y1) to (Y3)”) and the compounds represented by the general formulas (Y4) to (Y6) (Hereinafter referred to as “compounds (Y4) to (Y6)”) to react with the compound represented by general formula (Y) (hereinafter referred to as “general formula (Y)”).
  • “-” extending from the inside of the ring represents a bond extending from any position of the ring.
  • Ax, Ay and Az each have the same meaning as described above, and preferred examples thereof are also the same as described above.
  • the compound represented by the following formula (I) ′′ is obtained by reacting the compound (X) obtained as described above with the compound (Y).
  • Ar, A 1 , A 2 , B 1 , B 2 , Y 1 , Y 2 , Y 3 , Y 4 , G 1 , G 2 , P 1 , P 2 , p, q are , Each having the same meaning as described above, and preferred examples thereof are also the same as described above.
  • the intermediate B synthesized in Step 2 2.50 g (6.77 mmol) and N-methyl-2-pyrrolidone: 100 mL were placed in a nitrogen stream. did. Thereto was added 13.49 g (37.21 mmol) of Intermediate C synthesized in Step 3 above. Next, 0.909 g (7.44 mmol) of N, N-dimethyl-4-aminopyridine was added. Subsequently, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride: 8.56 g (44.66 mmol) was added over 5 minutes while maintaining the internal temperature of the reaction solution at 20 ° C.
  • the structure of the target product was identified by 1 H-NMR.
  • a three-necked reactor equipped with a thermometer was charged with 4.1 g of sodium hydride (oil-based) (2.67 g (55.58 mmol) as pure sodium hydride) and 75 mL of THF in a nitrogen stream. It was set as the solution. Thereto was dissolved 13.35 g (50.53 mmol) of 4- (6-acryloyloxy-hex-1-yloxy) phenol (manufactured by DKSH) in 75 mL of THF and added as a solution.
  • the structure of the target product was identified by 1 H-NMR.
  • the substrate was placed on a hot plate, heated from 50 ° C. to 200 ° C., and then cooled again to 50 ° C. Changes in the structure of the structure when the temperature was raised or lowered were observed with a deflection optical microscope (Nikon Corporation, ECLIPSE LV100POL type).
  • the measured phase transition temperatures are shown in Table 1 below.
  • C represents Crystal
  • N represents Nematic
  • I represents Isotropic.
  • Crystal means that the test compound is in a solid phase
  • Nematic means that the test compound is in a nematic liquid crystal phase
  • Isotropic means that the test compound is in an isotropic liquid phase. Show. From Table 1, it can be seen that the polymerizable liquid crystal compounds 1 to 3 exhibit liquid crystallinity.

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Abstract

The present invention provides a polymerizable liquid crystal compound which exhibits liquid crystallinity by itself, and which is capable of forming an optically anisotropic body and an optical film that have ideal wavelength dispersion showing wide band properties, namely reverse wavelength dispersion. A polymerizable liquid crystal compound according to the present invention is represented by formula (I). (In formula (I), Ar represents a group that is expressed by one of formulae (II-1)-(II-3).)

Description

重合性液晶化合物、重合性液晶組成物、高分子、光学フィルム、光学異方体、偏光板、表示装置、並びに、反射防止フィルムPolymerizable liquid crystal compound, polymerizable liquid crystal composition, polymer, optical film, optical anisotropic body, polarizing plate, display device, and antireflection film
　本発明は、広帯域性を示す理想的な波長分散性、即ち逆波長分散性を有する光学フィルムおよび光学異方体を形成可能であり、且つ、単独で液晶性を示す重合性液晶化合物に関するものである。
　また、本発明は、上記重合性液晶化合物を含む重合性液晶組成物に関するものである。
　また、本発明は、上記重合性液晶化合物を重合して得られる高分子に関するものである。
　さらに、本発明は、上記重合性液晶化合物を使用して調製された光学フィルムおよび光学異方体、並びに、当該光学異方体を用いた偏光板、表示装置、および反射防止フィルムに関するものである。
　なお、本明細書において、「液晶性を示す」とは、「液晶相を有する」ことを意味する。液晶相の具体例としては、例えば、ネマチック相、スメクチック相などが挙げられる。 The present invention relates to a polymerizable liquid crystal compound capable of forming an optical film and an optical anisotropic body having ideal wavelength dispersion, i.e., reverse wavelength dispersion, exhibiting broadband properties, and exhibiting liquid crystallinity alone. is there.
The present invention also relates to a polymerizable liquid crystal composition containing the polymerizable liquid crystal compound.
The present invention also relates to a polymer obtained by polymerizing the polymerizable liquid crystal compound.
Furthermore, the present invention relates to an optical film and an optical anisotropic body prepared using the polymerizable liquid crystal compound, and a polarizing plate, a display device and an antireflection film using the optical anisotropic body. .
Note that in this specification, “showing liquid crystallinity” means “having a liquid crystal phase”. Specific examples of the liquid crystal phase include a nematic phase and a smectic phase.
　フラットパネル表示装置等の各種装置において用いられている位相差板には、直線偏光を円偏光に変換する１／４波長板や直線偏光の偏光振動面を９０度変換する１／２波長板等がある。これらの位相差板は、ある特定の単色光に対しては正確に光線波長の１／４λあるいは１／２λの位相差を与えることが可能なものである。
　しかしながら、従来の位相差板には、位相差板を通過して出力される偏光が有色の偏光に変換されてしまうという問題があった。これは、位相差板を構成する材料が位相差について波長分散性を有し、可視光域の光線が混在する合成波である白色光に対しては各波長の偏光状態に分布が生じることから、入力光を全ての波長領域において正確な１／４λあるいは１／２λの位相差の偏光に調整することが不可能であることに起因する。
　このような問題を解決するため、広い波長域の光に対して均一な位相差を与え得る広帯域位相差板、いわゆる逆波長分散性を有する位相差板が種々検討されている。 A retardation plate used in various devices such as a flat panel display device includes a ¼ wavelength plate that converts linearly polarized light into circularly polarized light, a ½ wavelength plate that converts a polarization vibration plane of linearly polarized light by 90 degrees, and the like. There is. These retardation plates can accurately give a phase difference of 1 / 4λ or 1 / 2λ of a light wavelength to a specific monochromatic light.
However, the conventional retardation plate has a problem that polarized light output through the retardation plate is converted into colored polarized light. This is because the material constituting the retardation plate has wavelength dispersion with respect to the retardation, and distribution occurs in the polarization state of each wavelength with respect to white light that is a composite wave in which rays in the visible light range are mixed. This is because it is impossible to adjust the input light to polarization having a phase difference of ¼λ or ½λ in all wavelength regions.
In order to solve such a problem, various studies have been made on a broadband retardation plate capable of giving a uniform retardation to light in a wide wavelength range, that is, a so-called reverse wavelength dispersion plate.
　一方、モバイルパソコン、携帯電話等携帯型の情報端末の高機能化および普及に伴い、フラットパネル表示装置の厚みを極力薄く抑えることが求められてきている。その結果、構成部材である位相差板の薄層化も求められている。
　薄層化の方法としては、低分子重合性化合物を含有する重合性組成物をフィルム基材に塗布して光学フィルムを形成することにより位相差板を作製する方法が、近年では最も有効な方法とされている。そのため、優れた逆波長分散性を有する光学フィルムを形成可能な重合性化合物またはそれを用いた重合性組成物の開発が多く行われている。 On the other hand, with the advancement and widespread use of portable information terminals such as mobile personal computers and mobile phones, it has been required to keep the thickness of flat panel display devices as thin as possible. As a result, it is also required to reduce the thickness of the retardation plate that is a constituent member.
As a method for thinning, a method of producing a retardation plate by applying a polymerizable composition containing a low molecular weight polymerizable compound to a film substrate to form an optical film is the most effective method in recent years. It is said that. Therefore, many developments of a polymerizable compound capable of forming an optical film having excellent reverse wavelength dispersion or a polymerizable composition using the same are carried out.
　具体的には、広い波長域において一様の偏光変換が可能な偏光板、位相差板等の光学フィルムの製造に使用される重合性化合物が提供されてきた（例えば、特許文献１参照）。 Specifically, polymerizable compounds used for the production of optical films such as polarizing plates and retardation plates capable of uniform polarization conversion in a wide wavelength range have been provided (see, for example, Patent Document 1).
国際公開第２０１５／０２５７９３号International Publication No. 2015/025793
　しかしながら、特許文献１に記載されたような、従来の重合性化合物は、単独では、液晶性を示すものではなかった。液晶性を得るために他の化合物を加える必要があるが、最終的に得られる光学フィルムは、加えた材料の光学特性をも加味されたものとなってしまう問題があった。 However, the conventional polymerizable compound as described in Patent Document 1 alone does not exhibit liquid crystallinity. Although it is necessary to add other compounds in order to obtain liquid crystallinity, the optical film finally obtained has a problem that the optical characteristics of the added material are taken into consideration.
　本発明は、上記した実情に鑑みてなされたものであり、広帯域性を示す理想的な波長分散性、即ち逆波長分散性を有する光学フィルムおよび光学異方体を形成可能であり、且つ、単独で液晶性を示す重合性液晶化合物を提供することを目的とする。
　また、本発明は、上記重合性液晶化合物を含む重合性液晶組成物を提供することを目的とする。
　また、本発明は、上記重合性液晶化合物を重合して得られる高分子を提供することを目的とする。
　さらに、本発明は、上記重合性液晶化合物を使用して調製された光学フィルムおよび光学異方体、並びに、当該光学異方体を用いた偏光板、表示装置および反射防止フィルムを提供することを目的とする。 The present invention has been made in view of the above circumstances, and can form an ideal wavelength dispersion exhibiting broadband properties, that is, an optical film and an optical anisotropic body having reverse wavelength dispersion, and can be used alone. An object of the present invention is to provide a polymerizable liquid crystal compound exhibiting liquid crystallinity.
Another object of the present invention is to provide a polymerizable liquid crystal composition containing the polymerizable liquid crystal compound.
Another object of the present invention is to provide a polymer obtained by polymerizing the polymerizable liquid crystal compound.
Furthermore, the present invention provides an optical film and an optical anisotropic body prepared using the polymerizable liquid crystal compound, and a polarizing plate, a display device and an antireflection film using the optical anisotropic body. Objective.
　本発明者らは、上記課題を解決すべく鋭意研究した結果、下記式（Ｉ）で示される所定の重合性液晶化合物を使用すれば、広帯域性を示す理想的な波長分散性、即ち逆波長分散性を有する光学フィルムおよび光学異方体を形成可能であり、且つ、重合性液晶化合物が単独で液晶性を示すことを見出し、本発明を完成するに至った。
　かくして本発明によれば、下記に示す重合性液晶化合物、重合性液晶組成物、高分子、光学フィルム、光学異方体、偏光板、表示装置、並びに、反射防止フィルムが提供される。 As a result of intensive studies to solve the above problems, the present inventors have found that when a predetermined polymerizable liquid crystal compound represented by the following formula (I) is used, an ideal wavelength dispersion exhibiting broadband properties, that is, a reverse wavelength. It has been found that an optical film and an optical anisotropic body having dispersibility can be formed, and that the polymerizable liquid crystal compound exhibits liquid crystallinity alone, and the present invention has been completed.
Thus, according to the present invention, the following polymerizable liquid crystal compound, polymerizable liquid crystal composition, polymer, optical film, optical anisotropic body, polarizing plate, display device, and antireflection film are provided.
　〔１〕　下記式（Ｉ）で示される重合性液晶化合物。
Figure JPOXMLDOC01-appb-C000003
 〔式（Ｉ）中、
　Ａｒは、下記式（ＩＩ－１）～（ＩＩ－３）の何れかで表され、Ｄ以外の置換基を１つ以上有していてもよい。
Figure JPOXMLDOC01-appb-C000004
 （式（ＩＩ－１）～（ＩＩ－３）中、Ｄは、－Ｃ（Ｑ）＝Ｎ－Ｎ（Ａｙ）Ａｘ、－Ｃ（Ｑ）＝Ｎ－Ｎ＝Ｃ（Ａｙ）Ａｘ、または、－Ｃ（Ｑ）＝Ｎ－Ｎ＝Ａｚを表す。
　Ｑは、水素原子または炭素数１～６のアルキル基を表し、
　Ａｘは、炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する有機基を表し、
　Ａｙは、水素原子、または、置換基を有していてもよい炭素数１～３０の有機基を表し、
　Ａｚは、炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する有機基を表す。ここで、Ａｚは、Ｃ（Ａｙ）Ａｘである場合を除くものとする。
　ただし、＊は、Ｚ１またはＺ２と結合する位置を表す。）
　Ｚ１およびＺ２は、それぞれ独立して、化学的な単結合、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｓ－、－Ｓ－Ｃ（＝Ｏ）－、－ＮＲ１１－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１１－、＊－ＣＨ２－Ｏ－、＊－ＣＨ２－ＣＨ２－Ｏ－、＊－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ２－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ２－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ＝ＣＨ－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ＝ＣＨ－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ＝Ｎ－、＊－Ｃ（ＣＨ３）＝Ｎ－、－Ｎ＝Ｎ－を表す。ここで、＊はＡｒと結合する位置を表し、Ｒ１１は、水素原子または炭素数１～６のアルキル基を表す。
　Ａ１およびＡ２は、それぞれ独立して、置換基を有していてもよい炭素数１～２０の二価の鎖状脂肪族基を表す。前記鎖状脂肪族基には、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１２－、－ＮＲ１２－、または、－Ｃ（＝Ｏ）－が介在していてもよい。ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く。ここで、Ｒ１２は、水素原子または炭素数１～６のアルキル基を表す。ただし、Ａ１の、Ｚ１に結合する炭素原子およびＹ１もしくはＹ３に結合する炭素原子、並びに、Ａ２の、Ｚ２に結合する炭素原子およびＹ２もしくはＹ４に結合する炭素原子が、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１２－、－ＮＲ１２－、または、－Ｃ（＝Ｏ）－に置換されることはない。
　Ｂ１およびＢ２は、それぞれ独立して、置換基を有していてもよい環状脂肪族基、または、置換基を有していてもよい芳香族基を表す。
　Ｙ１～Ｙ４は、それぞれ独立して、単結合、－Ｏ－、－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－ＮＲ１３－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１３－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１３－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－ＮＲ１３－、または、－ＮＲ１３－Ｃ（＝Ｏ）－ＮＲ１４－を表す。ここで、Ｒ１３およびＲ１４は、それぞれ独立して、水素原子または炭素数１～６のアルキル基を表す。
　Ｇ１およびＧ２は、それぞれ独立して、炭素数１～２０の脂肪族炭化水素基、および、炭素数３～２０の脂肪族炭化水素基に含まれるメチレン基（－ＣＨ２－）の１以上が－Ｏ－または－Ｃ（＝Ｏ）－に置換された基のいずれかの有機基である。なお、Ｇ１およびＧ２の前記有機基に含まれる水素原子は、炭素数１～５のアルキル基、炭素数１～５のアルコキシ基、または、ハロゲン原子に置換されていてもよい。ただし、Ｇ１およびＧ２の両末端のメチレン基（－ＣＨ２－）が、－Ｏ－または－Ｃ（＝Ｏ）－に置換されることはない。
　Ｐ１およびＰ２は、それぞれ独立して、重合性基を表す。
　ｐおよびｑは、それぞれ独立して、０～２の整数を表す。〕 [1] A polymerizable liquid crystal compound represented by the following formula (I).
Figure JPOXMLDOC01-appb-C000003
 [In formula (I),
Ar is represented by any of the following formulas (II-1) to (II-3), and may have one or more substituents other than D.
Figure JPOXMLDOC01-appb-C000004
 (In the formulas (II-1) to (II-3), D is -C (Q) = NN (Ay) Ax, -C (Q) = NN = C (Ay) Ax, or -C (Q) = NN = Az.
Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Ax represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms,
Ay represents a hydrogen atom or an organic group having 1 to 30 carbon atoms which may have a substituent,
Az represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms. Here, Az excludes the case of C (Ay) Ax.
However, * represents a position bonded with Z 1 or Z 2. )
Z 1 and Z 2 are each independently a chemical single bond, —O—, —C (═O) —O—, —O—C (═O) —, —C (═O) —S. -, - S-C (= O) -, - NR 11 -C (= O) -, - C (= O) -NR 11 -, * - CH 2 -O -, * - CH 2 -CH 2 - O -, * - CH 2 -C (= O) -O -, * - CH 2 -O-C (= O) -, * - CH 2 -CH 2 -C (= O) -O -, * - CH 2 —CH 2 —O—C (═O) —, * —CH═CH—C (═O) —O—, * —CH═CH—O—C (═O) —, * —CH═N -, * -C (CH 3 ) = N-, -N = N-. Here, * represents a position bonded to Ar, and R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
A 1 and A 2 each independently represents a divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent. The chain aliphatic group includes —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O—C (═O) —O—, — NR 12 —C (═O) —, —C (═O) —NR 12 —, —NR 12 —, or —C (═O) — may be present. However, the case where two or more of —O— or —S— are adjacent to each other is excluded. Here, R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Provided that the carbon atom bonded to Z 1 and the carbon atom bonded to Y 1 or Y 3 of A 1 and the carbon atom bonded to Z 2 and the carbon atom bonded to Y 2 or Y 4 of A 2 are bonded to each other. , —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O—C (═O) —O—, —NR 12 —C (═O) There is no substitution with —, —C (═O) —NR 12 —, —NR 12 —, or —C (═O) —.
B 1 and B 2 each independently represent a cyclic aliphatic group which may have a substituent or an aromatic group which may have a substituent.
Y 1 to Y 4 are each independently a single bond, —O—, —C (═O) —, —C (═O) —O—, —O—C (═O) —, —NR 13. —C (═O) —, —C (═O) —NR 13 —, —O—C (═O) —O—, —NR 13 —C (═O) —O—, —O—C (= O) —NR 13 — or —NR 13 —C (═O) —NR 14 —. Here, R 13 and R 14 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
G 1 and G 2 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and 1 of a methylene group (—CH 2 —) contained in an aliphatic hydrocarbon group having 3 to 20 carbon atoms. The above is an organic group of any of the groups substituted with —O— or —C (═O) —. Note that a hydrogen atom contained in the organic group of G 1 and G 2 may be substituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom. However, the methylene groups (—CH 2 —) at both ends of G 1 and G 2 are not substituted with —O— or —C (═O) —.
P 1 and P 2 each independently represent a polymerizable group.
p and q each independently represents an integer of 0 to 2. ]
　〔２〕　前記〔１〕に記載の重合性液晶化合物を含む、重合性組成物。 [2] A polymerizable composition comprising the polymerizable liquid crystal compound according to [1].
　〔３〕　前記〔１〕に記載の重合性液晶化合物を重合して得られる、高分子。 [3] A polymer obtained by polymerizing the polymerizable liquid crystal compound according to [1].
　〔４〕　前記〔３〕に記載の高分子を構成材料とする、光学フィルム。 [4] An optical film comprising the polymer described in [3] as a constituent material.
　〔５〕　前記〔３〕に記載の高分子を構成材料とする層を有する、光学異方体。 [5] An optically anisotropic body having a layer containing the polymer described in [3] as a constituent material.
　〔６〕　前記〔５〕に記載の光学異方体および偏光フィルムを含む、偏光板。 [6] A polarizing plate including the optical anisotropic body according to [5] and a polarizing film.
　〔７〕　前記〔６〕に記載の偏光板を備える、表示装置。 [7] A display device comprising the polarizing plate according to [6].
　〔８〕　前記〔６〕に記載の偏光板を含む、反射防止フィルム。 [8] An antireflection film including the polarizing plate according to [6].
　本発明によれば、広帯域性を示す理想的な波長分散性、即ち逆波長分散性を有する光学フィルムおよび光学異方体を形成可能であり、且つ、単独で液晶性を示す重合性液晶化合物が提供される。
　また、本発明によれば、上記重合性液晶化合物を含む重合性液晶組成物が提供される。
　また、本発明によれば、上記重合性液晶化合物を重合して得られる高分子が提供される。
　さらに、本発明によれば、上記重合性液晶化合物を使用して調製された光学フィルムおよび光学異方体、並びに、当該光学異方体を用いた偏光板、表示装置および反射防止フィルムが提供される。 According to the present invention, there is provided a polymerizable liquid crystal compound capable of forming an optical film and an optical anisotropic body having ideal wavelength dispersibility exhibiting broadband properties, that is, reverse wavelength dispersibility, and exhibiting liquid crystallinity alone. Provided.
Moreover, according to this invention, the polymeric liquid crystal composition containing the said polymeric liquid crystal compound is provided.
Moreover, according to this invention, the polymer obtained by superposing | polymerizing the said polymeric liquid crystal compound is provided.
Furthermore, according to the present invention, there are provided an optical film and an optical anisotropic body prepared using the polymerizable liquid crystal compound, and a polarizing plate, a display device and an antireflection film using the optical anisotropic body. The
　以下、本発明を詳細に説明する。なお、本発明において、「置換基を有していてもよい」とは、「無置換の、または、置換基を有する」の意味である。また、一般式中に含まれるアルキル基や芳香族炭化水素環基等の有機基が置換基を有する場合、当該置換基を有する有機基の炭素数には、置換基の炭素数を含まないものとする。例えば、炭素数６～１８の芳香族炭化水素環基が置換基を有する場合、炭素数６～１８の芳香族炭化水素環基の炭素数には、このような置換基の炭素数を含まないものとする。一方、「Ａｒ中の環構造に含まれるπ電子の数」および「Ｆｙ中の環構造に含まれるπ電子の数」には、置換基に含まれている環構造のπ電子も含まれるものとする。さらに、本発明において、「アルキル基」とは、鎖状（直鎖状または分岐状）の飽和炭化水素基を意味し、「アルキル基」には、環状の飽和炭化水素基である、「シクロアルキル基」は含まれないものとする。 Hereinafter, the present invention will be described in detail. In the present invention, “may have a substituent” means “unsubstituted or have a substituent”. In addition, when an organic group such as an alkyl group or aromatic hydrocarbon ring group contained in the general formula has a substituent, the number of carbons of the organic group having the substituent does not include the number of carbons of the substituent And For example, when the aromatic hydrocarbon ring group having 6 to 18 carbon atoms has a substituent, the carbon number of the aromatic hydrocarbon ring group having 6 to 18 carbon atoms does not include the carbon number of such a substituent. Shall. On the other hand, “the number of π electrons included in the ring structure in Ar” and “the number of π electrons included in the ring structure in Fy” include the π electrons of the ring structure included in the substituent. And Furthermore, in the present invention, the “alkyl group” means a chain (straight chain or branched) saturated hydrocarbon group, and the “alkyl group” means a “cyclo saturated hydrocarbon group” "Alkyl group" is not included.
　ここで、本発明の重合性液晶化合物、重合性液晶組成物は、特に限定されることなく、例えば本発明の高分子を調製する際に用いることができる。
　更に、本発明の高分子は、特に限定されることなく、例えば本発明の光学フィルムの構成材料および本発明の光学異方体が有する層の構成材料として用いることができる。また、本発明の光学異方体は、特に限定されることなく、例えば本発明の偏光板の作製に用いることができる。更に、本発明の偏光板は、特に限定されることなく、例えば本発明の表示装置および反射防止フィルムの作製に用いることができる。
　また、本発明の重合性液晶化合物の中間体（化合物）は、特に限定されることなく、例えば本発明の重合性液晶化合物を調製する際に用いることができる。 Here, the polymerizable liquid crystal compound and the polymerizable liquid crystal composition of the present invention are not particularly limited, and can be used, for example, when preparing the polymer of the present invention.
Furthermore, the polymer of the present invention is not particularly limited, and can be used, for example, as a constituent material of the optical film of the present invention and a constituent material of the layer of the optical anisotropic body of the present invention. Moreover, the optical anisotropic body of this invention is not specifically limited, For example, it can use for preparation of the polarizing plate of this invention. Furthermore, the polarizing plate of this invention is not specifically limited, For example, it can be used for preparation of the display apparatus and antireflection film of this invention.
Moreover, the intermediate body (compound) of the polymeric liquid crystal compound of this invention is not specifically limited, For example, it can be used when preparing the polymeric liquid crystal compound of this invention.
（１）重合性液晶化合物
　本発明の重合性液晶化合物は、下記式（Ｉ）で示される化合物（以下、「重合性液晶化合物（Ｉ）」ということがある。）であり、後述する高分子、光学フィルムおよび光学異方体を調製する際に有利に用いることができる。
Figure JPOXMLDOC01-appb-C000005
 (1) Polymerizable liquid crystal compound The polymerizable liquid crystal compound of the present invention is a compound represented by the following formula (I) (hereinafter sometimes referred to as "polymerizable liquid crystal compound (I)"), and a polymer described later. It can be advantageously used in preparing an optical film and an optical anisotropic body.
Figure JPOXMLDOC01-appb-C000005
＜Ａｒ＞
　ここで、式（Ｉ）中、Ａｒは下記式（ＩＩ－１）～（ＩＩ－３）の何れかで表され、Ｄ以外の置換基を１つ以上有していてもよい。Ａｒ中の環構造に含まれるπ電子の総数は、１０以上であることが好ましく、１２以上であることがより好ましく、６０以下であることが好ましく、４８以下であることが好ましく、３６以下であることが特に好ましい。ここで、「Ａｒ中の環構造に含まれるπ電子の総数」とは、Ａｒ中に含まれている環構造が１つである場合は、その１つの環構造に含まれるπ電子の数を意味し、Ａｒ中に環構造が複数含まれている場合は、その複数の環構造のπ電子の総数を意味する。
Figure JPOXMLDOC01-appb-C000006
 （上記式（ＩＩ－１）～（ＩＩ－３）中、＊は、Ｚ１あるいはＺ２と結合することを表し、環内部からのびる「－」は、環の任意の位置からのびる結合手を表す。） <Ar>
Here, in the formula (I), Ar is represented by any of the following formulas (II-1) to (II-3) and may have one or more substituents other than D. The total number of π electrons contained in the ring structure in Ar is preferably 10 or more, more preferably 12 or more, preferably 60 or less, preferably 48 or less, and 36 or less. It is particularly preferred. Here, “the total number of π electrons contained in the ring structure in Ar” is the number of π electrons contained in one ring structure when the number of ring structures contained in Ar is one. This means that when Ar includes a plurality of ring structures, it means the total number of π electrons of the plurality of ring structures.
Figure JPOXMLDOC01-appb-C000006
 (In the above formulas (II-1) to (II-3), * represents bonding to Z 1 or Z 2, and “-” extending from the inside of the ring represents a bonding hand extending from any position of the ring. To express.)
＜＜Ｄ＞＞
　Ｄは、－Ｃ（Ｑ）＝Ｎ－Ｎ（Ａｙ）Ａｘ、－Ｃ（Ｑ）＝Ｎ－Ｎ＝Ｃ（Ａｙ）Ａｘ、または、－Ｃ（Ｑ）＝Ｎ－Ｎ＝Ａｚを表す。 << D >>
D represents -C (Q) = NN (Ay) Ax, -C (Q) = NN = C (Ay) Ax, or -C (Q) = NN = Az.
　Ｄ以外の置換基としては、例えば、ハロゲン原子、シアノ基、ニトロ基、炭素数１～６のアルキル基、１個以上の水素原子がフッ素原子等のハロゲン原子で置換された炭素数１～６のアルキル基、炭素数１～６のＮ－アルキルアミノ基、炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基、炭素数１～６のアルコキシ基、炭素数１～６のアルキルスルフィニル基、カルボキシル基、炭素数１～６のチオアルキル基、炭素数１～６のＮ－アルキルスルファモイル基、炭素数２～１２のＮ，Ｎ－ジアルキルスルファモイル基、などが挙げられる。 Examples of the substituent other than D include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms in which one or more hydrogen atoms are substituted with a halogen atom such as a fluorine atom. Alkyl group, N-alkylamino group having 1 to 6 carbon atoms, N, N-dialkylamino group having 2 to 12 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylsulfinyl group having 1 to 6 carbon atoms, carboxyl Group, a thioalkyl group having 1 to 6 carbon atoms, an N-alkylsulfamoyl group having 1 to 6 carbon atoms, an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, and the like.
－Ｑ－
　Ｑは、水素原子または炭素数１～６のアルキル基を表す。
　炭素数１～６のアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、などが挙げられる。 -Q-
Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
－Ａｙ－
　Ａｙは、水素原子、または、置換基を有していてもよい炭素数１～３０の有機基を表す。
　Ａｙの置換基を有していてもよい１～３０の有機基の具体例としては、置換基を有していてもよい炭素数１～２０のアルキル基、炭素数１～２０のアルキル基に含まれる－ＣＨ２－の少なくとも一つが、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、または、－Ｃ（＝Ｏ）－に置換された基（ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く）、置換基を有していてもよい炭素数２～２０のアルケニル基、置換基を有していてもよい炭素数２～２０のアルキニル基、置換基を有していてもよい炭素数３～１２のシクロアルキル基、置換基を有していてもよい炭素数６～３０の芳香族炭化水素環基、置換基を有していてもよい炭素数２～３０の芳香族複素環基、－Ｇｙ－Ｙｙ－Ｆｙ、－ＳＯ２Ｒａ、－Ｃ（＝Ｏ）－Ｒｂ、または、－ＣＳ－ＮＨ－Ｒｂ、などが挙げられる。
　これらの中でも、置換基を有していてもよい炭素数１～２０のアルキル基、炭素数１～２０のアルキル基に含まれる－ＣＨ２－の少なくとも一つが、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、または、－Ｃ（＝Ｏ）－に置換された基（ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く）、置換基を有していてもよい炭素数３～１２のシクロアルキル基、置換基を有していてもよい炭素数６～３０の芳香族炭化水素環基、置換基を有していてもよい炭素数２～３０の芳香族複素環基、または、－Ｇｙ－Ｙｙ－Ｆｙが好ましく、
　置換基を有していてもよい炭素数１～２０のアルキル基、炭素数１～２０のアルキル基に含まれる－ＣＨ２－の少なくとも一つが、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、または、－Ｃ（＝Ｏ）－に置換された基（ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く）、または、－Ｇｙ－Ｙｙ－Ｆｙが特に好ましい。 -Ay-
Ay represents a hydrogen atom or an organic group having 1 to 30 carbon atoms which may have a substituent.
Specific examples of the organic group having 1 to 30 which may have a substituent of Ay include an alkyl group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms which may have a substituent. At least one of —CH 2 — contained is substituted with —O—, —S—, —O—C (═O) —, —C (═O) —O—, or —C (═O) —. A group having 2 to 20 carbon atoms which may have a substituent, or a substituent (excluding the case where two or more of —O— or —S— are adjacent to each other) An alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms which may have a substituent, and an aromatic carbon atom having 6 to 30 carbon atoms which may have a substituent hydrocarbon ring group, aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent, -Gy-Yy-Fy, -SO 2 R a -C (= O) -R b, or, -CS-NH-R b, and the like.
Among these, the alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least one of —CH 2 — contained in the alkyl group having 1 to 20 carbon atoms is —O—, —S—, A group substituted with —O—C (═O) —, —C (═O) —O—, or —C (═O) — (provided that two or more of —O— or —S— are adjacent to each other). A cycloalkyl group having 3 to 12 carbon atoms which may have a substituent, an aromatic hydrocarbon ring group having 6 to 30 carbon atoms which may have a substituent, a substituent An aromatic heterocyclic group having 2 to 30 carbon atoms which may have a group, or -Gy-Yy-Fy,
At least one of —CH 2 — contained in the optionally substituted alkyl group having 1 to 20 carbon atoms and the alkyl group having 1 to 20 carbon atoms is —O—, —S—, —O—C. A group substituted by (═O) —, —C (═O) —O—, or —C (═O) — (provided that two or more of —O— or —S— are adjacent to each other). Or -Gy-Yy-Fy is particularly preferable.
－－前記「置換基を有していてもよい炭素数１～２０のアルキル基」－－
　前記「置換基を有してもよい炭素数１～２０のアルキル基」における「炭素数１～２０のアルキル基」の具体例としては、例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、１－メチルペンチル基、１－エチルペンチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－へキシル基、イソヘキシル基、ｎ－ヘプチル基、ｎ－オクチル基、ｎ－ノニル基、ｎ－デシル基、ｎ－ウンデシル基、ｎ－ドデシル基、ｎ－トリデシル基、ｎ－テトラデシル基、ｎ－ペンタデシル基、ｎ－ヘキサデシル基、ｎ－ヘプタデシル基、ｎ－オクタデシル基、ｎ－ノナデシル基、およびｎ－イコシル基、などが挙げられる。これらの中でも、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－へキシル基、ｎ－ヘプチル基、ｎ－オクチル基、ｎ－ノニル基、ｎ－デシル基が好ましい。
　「置換基を有してもよい炭素数１～２０のアルキル基」の炭素数は、１～１２であることが好ましく、４～１０であることがより好ましい。 --- "Alkyl group having 1 to 20 carbon atoms which may have a substituent"-
Specific examples of the “alkyl group having 1 to 20 carbon atoms” in the “optionally substituted alkyl group having 1 to 20 carbon atoms” include, for example, methyl group, ethyl group, n-propyl group, isopropyl Group, n-butyl group, isobutyl group, 1-methylpentyl group, 1-ethylpentyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl Group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group Group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, and the like. Among these, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group Is preferred.
The “optionally substituted alkyl group having 1 to 20 carbon atoms” preferably has 1 to 12 carbon atoms, and more preferably 4 to 10 carbon atoms.
　前記「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の具体例としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基、ブトキシ基等の炭素数１～２０のアルコキシ基；メトキシメトキシ基、メトキシエトキシ基、エトキシメトキシ基、エトキシエトキシ基等の、炭素数１～１２のアルコキシ基で置換された炭素数１～１２のアルコキシ基；ニトロ基；フェニル基、１－ナフチル基、２－ナフチル基等の炭素数６～１８の芳香族炭化水素環基；トリアゾリル基、ピロリル基、フラニル基、チオフェニル基（チエニル基）、チアゾリル基、ベンゾチアゾール－２－イルチオ基等の、炭素数２～１８の芳香族複素環基；シクロプロピル基、シクロペンチル基、シクロヘキシル基等の炭素数３～８のシクロアルキル基；シクロペンチルオキシ基、シクロヘキシルオキシ基等の炭素数３～８のシクロアルキルオキシ基；テトラヒドロフラニル基、テトラヒドロピラニル基、ジオキソラニル基、ジオキサニル基等の炭素数２～１２の環状エーテル基；フェノキシ基、ナフトキシ基等の炭素数６～１４のアリールオキシ基；トリフルオロメチル基、ペンタフルオロエチル基、ＣＨ２ＣＦ３等の１個以上の水素原子がフッ素原子で置換された炭素数１～１２のアルキル基；ベンゾフリル基；ベンゾピラニル基；ベンゾジオキソリル基；ベンゾジオキサニル基；水酸基；－ＳＯ２Ｒａ；－ＳＲｂ；－ＳＲｂで置換された炭素数１～１２のアルコキシ基；などが挙げられる。これらの中でも、フッ素原子、シアノ基、炭素数１～２０のアルコキシ基、炭素数１～１２のアルコキシ基で置換された炭素数１～１２のアルコキシ基、炭素数６～１８の芳香族炭化水素環基、炭素数２～１８の芳香族複素環基、炭素数３～８のシクロアルキル基、炭素数３～８のシクロアルキルオキシ基、炭素数２～１２の環状エーテル基、炭素数６～１４のアリールオキシ基が好ましく、フッ素原子、シアノ基、メトキシ基、エトキシ基、ブトキシ基、メトキシメトキシ基、メトキシエトキシ基、エトキシメトキシ基、エトキシエトキシ基、フェニル基、１－ナフチル基、２－ナフチル基、ベンゾチアゾール－２－イルチオ基がより好ましい。
　なおここで、Ｒａは、炭素数１～６のアルキル基、または、炭素数１～６のアルキル基若しくは炭素数１～６のアルコキシ基を置換基として有していてもよい炭素数６～１８の芳香族炭化水素環基を表し、Ｒｂは、置換基を有していてもよい炭素数１～２０のアルキル基、置換基を有していてもよい炭素数２～２０のアルケニル基、置換基を有していてもよい炭素数３～１２のシクロアルキル基、または置換基を有していてもよい炭素数６～１８の芳香族炭化水素環基を表す。
　前記「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the “optionally substituted alkyl group having 1 to 20 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; carbon such as dimethylamino group N, N-dialkylamino group having 2 to 12 carbon atoms; alkoxy group having 1 to 20 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy C1-C12 alkoxy groups substituted with C1-C12 alkoxy groups such as nitro groups; nitro groups; aromatics having 6-18 carbon atoms such as phenyl groups, 1-naphthyl groups, 2-naphthyl groups, etc. Hydrocarbon ring group; carbon such as triazolyl group, pyrrolyl group, furanyl group, thiophenyl group (thienyl group), thiazolyl group, benzothiazol-2-ylthio group, etc. An aromatic heterocyclic group having 2 to 18 carbon atoms; a cycloalkyl group having 3 to 8 carbon atoms such as cyclopropyl group, cyclopentyl group and cyclohexyl group; a cycloalkyloxy having 3 to 8 carbon atoms such as cyclopentyloxy group and cyclohexyloxy group A cyclic ether group having 2 to 12 carbon atoms such as a tetrahydrofuranyl group, a tetrahydropyranyl group, a dioxolanyl group or a dioxanyl group; an aryloxy group having 6 to 14 carbon atoms such as a phenoxy group or a naphthoxy group; a trifluoromethyl group; An alkyl group having 1 to 12 carbon atoms in which one or more hydrogen atoms such as a pentafluoroethyl group and CH 2 CF 3 are substituted with a fluorine atom; a benzofuryl group; a benzopyranyl group; a benzodioxolyl group; a benzodioxanyl group ; hydroxyl; -SO 2 R a; -SR b ; -SR b carbon atoms which is substituted with 1-1 An alkoxy group; and the like. Among these, a fluorine atom, a cyano group, an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 12 carbon atoms substituted with an alkoxy group having 1 to 12 carbon atoms, and an aromatic hydrocarbon having 6 to 18 carbon atoms A cyclic group, an aromatic heterocyclic group having 2 to 18 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyloxy group having 3 to 8 carbon atoms, a cyclic ether group having 2 to 12 carbon atoms, and 6 to 6 carbon atoms 14 aryloxy groups are preferred, fluorine atom, cyano group, methoxy group, ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, phenyl group, 1-naphthyl group, 2-naphthyl group Group, benzothiazol-2-ylthio group is more preferred.
Here, R a is an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, which may have a substituent. 18 represents an aromatic hydrocarbon ring group, and R b is an optionally substituted alkyl group having 1 to 20 carbon atoms and an optionally substituted alkenyl group having 2 to 20 carbon atoms. Represents an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms.
The number of substituents in the “optionally substituted alkyl group having 1 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－前記「置換基を有していてもよい炭素数２～２０のアルケニル基」－－
　前記「置換基を有してもよい炭素数２～２０のアルケニル基」における「炭素数２～２０のアルケニル基」の具体例としては、例えば、ビニル基、プロペニル基、イソプロペニル基、ブテニル基、イソブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、デセニル基、ウンデセニル基、ドデセニル基、トリデセニル基、テトラデセニル基、ペンタデセニル基、ヘキサデセニル基、ヘプタデセニル基、オクタデセニル基、ノナデセニル基、イコセニル基、などが挙げられる。これらの中でも、ビニル基、プロペニル基、イソプロペニル基、ブテニル基、イソブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、デセニル基、ウンデセニル基、ドデセニル基が好ましい。
　前記「置換基を有していてもよい炭素数２～２０のアルケニル基」の炭素数は、２～１２であることが好ましい。 --- "Alkenyl group having 2 to 20 carbon atoms which may have a substituent"-
Specific examples of the “alkenyl group having 2 to 20 carbon atoms” in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” include, for example, a vinyl group, a propenyl group, an isopropenyl group, and a butenyl group. , Isobutenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonacenyl group, etc. Is mentioned. Among these, 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, and a dodecenyl group are preferable.
The “optionally substituted alkenyl group having 2 to 20 carbon atoms” preferably has 2 to 12 carbon atoms.
　前記「置換基を有していてもよい炭素数２～２０のアルケニル基」における置換基の具体例は、前記「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の具体例と同じである。
　前記「置換基を有していてもよい炭素数２～２０のアルケニル基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the above “optionally substituted alkenyl group having 2 to 20 carbon atoms” include the substitution in the above “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific example of the group.
The number of substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－前記「置換基を有していてもよい炭素数２～２０のアルキニル基」－－
　前記「置換基を有していてもよい炭素数２～２０のアルキニル基」における「炭素数２～２０のアルキニル基」の具体例としては、例えば、エチニル基、プロピニル基、２－プロピニル基（プロパルギル基）、ブチニル基、２－ブチニル基、３－ブチニル基、ペンチニル基、２－ペンチニル基、ヘキシニル基、５－ヘキシニル基、ヘプチニル基、オクチニル基、２－オクチニル基、ノナニル基、デカニル基、７－デカニル基、などが挙げられる。これらの中でも、２－プロピニル基（プロパルギル基）、ブチニル基、２－ブチニル基、３－ブチニル基、ペンチニル基、２－ペンチニル基、ヘキシニル基、５－ヘキシニル基、ヘプチニル基、オクチニル基、２－オクチニル基、ノナニル基、デカニル基が好ましい。 --- "Alkynyl group having 2 to 20 carbon atoms which may have a substituent"-
Specific examples of the “alkynyl group having 2 to 20 carbon atoms” in the “optionally substituted alkynyl group having 2 to 20 carbon atoms” include, for example, ethynyl group, propynyl group, 2-propynyl group ( Propargyl group), butynyl group, 2-butynyl group, 3-butynyl group, pentynyl group, 2-pentynyl group, hexynyl group, 5-hexynyl group, heptynyl group, octynyl group, 2-octynyl group, nonanyl group, decanyl group, 7-decanyl group, and the like. Among these, 2-propynyl group (propargyl group), butynyl group, 2-butynyl group, 3-butynyl group, pentynyl group, 2-pentynyl group, hexynyl group, 5-hexynyl group, heptynyl group, octynyl group, 2- An octynyl group, a nonanyl group, and a decanyl group are preferred.
　前記「置換基を有していてもよい炭素数２～２０のアルキニル基」における置換基の具体例は、前記「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の具体例と同じである。
　前記「置換基を有していてもよい炭素数２～２０のアルキニル基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the above “optionally substituted alkynyl group having 2 to 20 carbon atoms” include substitution in the above “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific example of the group.
The number of substituents in the “optionally substituted alkynyl group having 2 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－前記「置換基を有していてもよい炭素数３～１２のシクロアルキル基」－－
　前記「置換基を有していてもよい炭素数３～１２のシクロアルキル基」における「炭素数３～１２のシクロアルキル基」の具体例としては、例えば、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロオクチル基、などが挙げられる。これらの中でも、シクロペンチル基、シクロヘキシル基が好ましい。 ---- "C3-C12 cycloalkyl group optionally having substituent"-
Specific examples of the “cycloalkyl group having 3 to 12 carbon atoms” in the “cycloalkyl group having 3 to 12 carbon atoms which may have a substituent” include, for example, a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group. Cyclohexyl group, cyclooctyl group, and the like. Among these, a cyclopentyl group and a cyclohexyl group are preferable.
　前記「置換基を有していてもよい炭素数３～１２のシクロアルキル基」における置換基の具体例は、前記「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の具体例と同じである。
　前記「置換基を有していてもよい炭素数３～１２のシクロアルキル基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” include the above-described “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific examples of the substituent.
The number of substituents in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－前記「置換基を有していてもよい炭素数６～３０の芳香族炭化水素環基」－－
　前記「置換基を有していてもよい炭素数６～３０の芳香族炭化水素環基」における「炭素数６～３０の芳香族炭化水素環基」の具体例としては、例えば、フェニル基、１－ナフチル基、２－ナフチル基、などが挙げられる。これらの中でも、フェニル基が好ましい。 --- "Aromatic hydrocarbon ring group having 6 to 30 carbon atoms which may have a substituent"-
Specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in the “optionally substituted aromatic hydrocarbon ring group having 6 to 30 carbon atoms” include, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group and the like can be mentioned. Among these, a phenyl group is preferable.
　前記「置換基を有していてもよい炭素数６～３０の芳香族炭化水素環基」における置換基の具体例としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基；ビニル基、アリル基等の炭素数２～６のアルケニル基；トリフルオロメチル基等の１個以上の水素原子がフッ素原子等のハロゲン原子で置換された炭素数１～６のアルキル基；ジメチルアミノ基等の炭素数１～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基等の炭素数１～６のアルコキシ基；ニトロ基；－ＯＣＦ３；－Ｃ（＝Ｏ）－Ｒｂ；－Ｏ－Ｃ（＝Ｏ）－Ｒｂ；－Ｃ（＝Ｏ）－Ｏ－Ｒｂ；－ＳＯ２Ｒａ；などが挙げられる。これらの中でも、フッ素原子、シアノ基、メチル基、エチル基、プロピル基、トリフルオロメチル基、メトキシ基、エトキシ基、ニトロ基が好ましい。
　なおここで、ＲａおよびＲｂは、それぞれ、前記同じ意味を表す。
　前記「置換基を有していてもよい炭素数６～３０の芳香族炭化水素環基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the “optionally substituted aromatic hydrocarbon ring group having 6 to 30 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; methyl group An alkyl group having 1 to 6 carbon atoms such as an ethyl group or a propyl group; an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group; one or more hydrogen atoms such as a trifluoromethyl group being a fluorine atom or the like An alkyl group having 1 to 6 carbon atoms substituted with a halogen atom; an N, N-dialkylamino group having 1 to 12 carbon atoms such as a dimethylamino group; and 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, or an isopropoxy group —OCF 3 ; —C (═O) —R b ; —O—C (═O) —R b ; —C (═O) —O—R b ; —SO 2 R a And the like. Among these, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, and a nitro group are preferable.
Here, R a and R b each have the same meaning as described above.
The number of substituents in the “aromatic hydrocarbon ring having 6 to 30 carbon atoms which may have a substituent” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－前記「置換基を有していてもよい炭素数２～３０の芳香族複素環基」－－
　前記「置換基を有していてもよい炭素数２～３０の芳香族複素環基」における「炭素数２～３０の芳香族複素環基」の具体例としては、例えば、１－ベンゾフラニル基、２－ベンゾフラニル基、イミダゾリル基、インドリル基、フラザニル基、オキサゾリル基、キノリル基、チアジアゾリル基、チアゾリル基、チアゾロピラジニル基、チアゾロピリジル基、チアゾロピリダジニル基、チアゾロピリミジニル基、チエニル基、トリアジニル基、トリアゾリル基、ナフチリジニル基、ピラジニル基、ピラゾリル基、ピラニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピロリル基、フタラジニル基、フラニル基、ベンゾ［ｃ］チエニル基、ベンゾ［ｂ］チエニル基、ベンゾイソオキサゾリル基、ベンゾイソチアゾリル基、ベンゾイミダゾリル基、ベンゾオキサジアゾリル基、ベンゾオキサゾリル基、ベンゾチアジアゾリル基、ベンゾチアゾリル基、ベンゾトリアジニル基、ベンゾトリアゾリル基、およびベンゾピラゾリル基、などが挙げられる。これらの中でも、フラニル基、ピラニル基、チエニル基、オキサゾリル基、フラザニル基、チアゾリル基、チアジアゾリル基等の「単環の芳香族複素環基」；ベンゾチアゾリル基、ベンゾオキサゾリル基、キノリル基、１－ベンゾフラニル基、２－ベンゾフラニル基、フタルイミド基、ベンゾ［ｃ］チエニル基、ベンゾ［ｂ］チエニル基、チアゾロピリジル基、チアゾロピラジニル基、ベンゾイソオキサゾリル基、ベンゾオキサジアゾリル基、ベンゾチアジアゾリル基等の「縮合環の芳香族複素環基」；などが好ましい。 -"Aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent"-
Specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in the “optionally substituted aromatic heterocyclic group having 2 to 30 carbon atoms” include, for example, a 1-benzofuranyl group, 2-benzofuranyl group, imidazolyl group, indolyl group, furazanyl group, oxazolyl group, quinolyl group, thiadiazolyl group, thiazolyl group, thiazolopyrazinyl group, thiazolopyridyl group, thiazolopyridazinyl group, thiazolopyrimidinyl group , Thienyl group, triazinyl group, triazolyl group, naphthyridinyl group, pyrazinyl group, pyrazolyl group, pyranyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrrolyl group, phthalazinyl group, furanyl group, benzo [c] thienyl group, benzo [b ] Thienyl group, benzisoxazolyl group, benzisothiazolyl group, benzimidazo Group, benzoxadiazolyl group, a benzoxazolyl group, benzothiadiazolyl group, a benzothiazolyl group, benzotriazinyl group, benzotriazolyl group, and benzo pyrazolyl group, and the like. Among these, “monocyclic aromatic heterocyclic groups” such as furanyl group, pyranyl group, thienyl group, oxazolyl group, furazanyl group, thiazolyl group, thiadiazolyl group; benzothiazolyl group, benzoxazolyl group, quinolyl group, 1 -Benzofuranyl group, 2-benzofuranyl group, phthalimide group, benzo [c] thienyl group, benzo [b] thienyl group, thiazolopyridyl group, thiazolopyrazinyl group, benzoisoxazolyl group, benzooxadiazolyl group And "a condensed ring aromatic heterocyclic group" such as a benzothiadiazolyl group;
　前記「置換基を有していてもよい炭素数２～３０の芳香族複素環基」における置換基の具体例は、前記「置換基を有していてもよい炭素数６～３０の芳香族炭化水素環基」における置換基の具体例と同じである。
　前記「置換基を有していてもよい炭素数２～３０の芳香族複素環基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the “optionally substituted aromatic heterocyclic group having 2 to 30 carbon atoms” include the above “optionally substituted aromatic group having 6 to 30 carbon atoms”. Specific examples of the substituent in the “hydrocarbon ring group” are the same.
The number of substituents in the “aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－Ｒａ－－
　Ｒａは、前述したように、炭素数１～６のアルキル基、または、炭素数１～６のアルキル基若しくは炭素数１～６のアルコキシ基を置換基として有していてもよい炭素数６～１８の芳香族炭化水素環基を表す。
　「炭素数１～６のアルキル基」の具体例としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、などが挙げられる。これらの中でも、メチル基、エチル基が好ましい。
　「炭素数１～６のアルコキシ基」の具体例としては、例えば、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基、ｎ－ブトキシ基、ｓｅｃ－ブ卜キシ基、ｔ－ブトキシ基、ｎーペンチルオキシ基、ｎーへキシルオキシ基、などが挙げられる。
　「炭素数６～１８の芳香族炭化水素環基」の具体例としては、例えば、フェニル基、１－ナフチル基、２－ナフチル基、などが挙げられる。これらの中でも、フェニル基が好ましい。
　Ｒａの具体例としては、フェニル基、トリル基が好ましい。 --R a-
As described above, R a may have an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms as a substituent. Represents 18 to 18 aromatic hydrocarbon ring groups.
Specific examples of the “alkyl group having 1 to 6 carbon atoms” include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, and the like. Among these, a methyl group and an ethyl group are preferable.
Specific examples of the “C 1-6 alkoxy group” include, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, t-butoxy group, Examples thereof include an n-pentyloxy group and an n-hexyloxy group.
Specific examples of the “aromatic hydrocarbon ring group having 6 to 18 carbon atoms” include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group and the like. Among these, a phenyl group is preferable.
Specific examples of R a are preferably a phenyl group and a tolyl group.
－－Ｒｂ－－
　Ｒｂは、前述したように、置換基を有していてもよい炭素数１～２０のアルキル基、置換基を有していてもよい炭素数２～２０のアルケニル基、置換基を有していてもよい炭素数３～１２のシクロアルキル基、または、置換基を有していてもよい炭素数６～１８の芳香族炭化水素環基を表す。 --R b ---
R b has an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkenyl group having 2 to 20 carbon atoms, and a substituent as described above. It represents an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms.
－－－Ｒｂとしての「置換基を有していてもよい炭素数１～２０のアルキル基」－－－
　Ｒｂとしての「置換基を有していてもよい炭素数１～２０のアルキル基」における「炭素数１～２０のアルキル基」の具体例としては、例えば、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、１－メチルペンチル基、１－エチルペンチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－へキシル基、イソヘキシル基、ｎ－ヘプチル基、ｎ－オクチル基、ｎ－ノニル基、ｎ－デシル基、ｎ－ウンデシル基、ｎ－ドデシル基、ｎ－トリデシル基、ｎ－テトラデシル基、ｎ－ペンタデシル基、ｎ－ヘキサデシル基、ｎ－ヘプタデシル基、ｎ－オクタデシル基、ｎ－ノナデシル基、およびｎ－イコシル基、などが挙げられる。
　Ｒｂとしての「置換基を有してもよい炭素数１～２０のアルキル基」の炭素数は、１～１２であることが好ましく、４～１０であることがより好ましい。 --- "Alkyl group having 1 to 20 carbon atoms which may have a substituent" as R b ---
Specific examples of the “alkyl group having 1 to 20 carbon atoms” in the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b include, for example, a methyl group, an ethyl group, n- Propyl, isopropyl, n-butyl, isobutyl, 1-methylpentyl, 1-ethylpentyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-to Xyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl N-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, and the like.
The number of carbon atoms of the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b is preferably 1 to 12, and more preferably 4 to 10.
　Ｒｂとしての「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の具体例としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基、ブトキシ基等の炭素数１～２０のアルコキシ基；メトキシメトキシ基、メトキシエトキシ基、エトキシメトキシ基、エトキシエトキシ基等の、炭素数１～１２のアルコキシ基で置換された炭素数１～１２のアルコキシ基；ニトロ基；フェニル基、１－ナフチル基、２－ナフチル基等の炭素数６～１８の芳香族炭化水素環基；トリアゾリル基、ピロリル基、フラニル基、チエニル基、チアゾリル基、ベンゾチアゾール－２－イルチオ基等の、炭素数２～１８の芳香族複素環基；シクロプロピル基、シクロペンチル基、シクロヘキシル基等の炭素数３～８のシクロアルキル基；シクロペンチルオキシ基、シクロヘキシルオキシ基等の炭素数３～８のシクロアルキルオキシ基；テトラヒドロフラニル基、テトラヒドロピラニル基、ジオキソラニル基、ジオキサニル基等の炭素数２～１２の環状エーテル基；フェノキシ基、ナフトキシ基等の炭素数６～１４のアリールオキシ基；トリフルオロメチル基、ペンタフルオロエチル基、－ＣＨ２ＣＦ３等の、１個以上の水素原子がフッ素原子で置換された炭素数１～１２のアルキル基；ベンゾフリル基；ベンゾピラニル基；ベンゾジオキソリル基；ベンゾジオキサニル基；などが挙げられる。これらの中でも、フッ素原子、シアノ基、メトキシ基、エトキシ基、ブトキシ基、メトキシメトキシ基、メトキシエトキシ基、エトキシメトキシ基、エトキシエトキシ基、フェニル基、１－ナフチル基、２－ナフチル基、ベンゾチアゾール－２－イルチオ基が好ましい。
　Ｒｂとしての「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; dimethylamino group An N, N-dialkylamino group having 2 to 12 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group, etc., an alkoxy group having 1 to 20 carbon atoms; methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group An alkoxy group having 1 to 12 carbon atoms substituted with an alkoxy group having 1 to 12 carbon atoms such as ethoxyethoxy group; a nitro group; a carbon group having 6 to 18 carbon atoms such as a phenyl group, 1-naphthyl group, 2-naphthyl group, etc. An aromatic hydrocarbon ring group of 2 to 1 carbon atoms such as triazolyl group, pyrrolyl group, furanyl group, thienyl group, thiazolyl group, benzothiazol-2-ylthio group An aromatic heterocyclic group having 8; a cycloalkyl group having 3 to 8 carbon atoms such as a cyclopropyl group, a cyclopentyl group and a cyclohexyl group; a cycloalkyloxy group having 3 to 8 carbon atoms such as a cyclopentyloxy group and a cyclohexyloxy group; Cyclic ether groups having 2 to 12 carbon atoms such as nyl group, tetrahydropyranyl group, dioxolanyl group, dioxanyl group; aryloxy groups having 6 to 14 carbon atoms such as phenoxy group and naphthoxy group; trifluoromethyl group, pentafluoroethyl An alkyl group having 1 to 12 carbon atoms in which one or more hydrogen atoms are substituted with a fluorine atom, such as a group, —CH 2 CF 3 ; a benzofuryl group; a benzopyranyl group; a benzodioxolyl group; a benzodioxanyl group; Etc. Among these, fluorine atom, cyano group, methoxy group, ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, phenyl group, 1-naphthyl group, 2-naphthyl group, benzothiazole A -2-ylthio group is preferred.
The number of substituents in the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－－Ｒｂとしての「置換基を有していてもよい炭素数２～２０のアルケニル基」－－－
　Ｒｂとしての「置換基を有していてもよい炭素数２～２０のアルケニル基」における「炭素数２～２０のアルキニル基」の具体例は、前記Ａｙにおける「炭素数２～２０のアルキニル基」の具体例と同じであり、その好適例も前記Ａｙにおける「炭素数２～２０のアルキニル基」の好適例と同じである。 --- "Alkenyl group having 2 to 20 carbon atoms which may have a substituent" as R b ---
Specific examples of “an alkynyl group having 2 to 20 carbon atoms” in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b include “an alkynyl group having 2 to 20 carbon atoms” in the above Ay. Specific examples of the “group” are the same, and preferable examples thereof are also the same as the preferable examples of the “alkynyl group having 2 to 20 carbon atoms” in Ay.
　Ｒｂとしての「置換基を有していてもよい炭素数２～２０のアルケニル基」における置換基の具体例は、前記「置換基を有していてもよい炭素数１～２０のアルキル基」における置換基の具体例と同じである。
　Ｒｂとしての「置換基を有していてもよい炭素数２～２０のアルケニル基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b are the above-described “optionally substituted alkyl group having 1 to 20 carbon atoms”. Are the same as the specific examples of the substituents.
The number of substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－－Ｒｂとしての「置換基を有していてもよい炭素数３～１２のシクロアルキル基」－－－
　Ｒｂとしての「置換基を有していてもよい炭素数３～１２のシクロアルキル基」における「炭素数３～１２のシクロアルキル基」の具体例は、前記Ａｙにおける「炭素数３～１２のシクロアルキル基」の具体例と同じであり、その好適例もＡｙにおける「炭素数３～１２のシクロアルキル基」の好適例と同じである。 --- "C3-C12 cycloalkyl group optionally having substituent" as R b ---
Specific examples of the "cycloalkyl group having 3 to 12 carbon atoms" in the "cycloalkyl group 1-3 carbon atoms which may have a substituent 12" as R b, the number "carbon in the Ay 3-12 Specific examples of the “cycloalkyl group of” and the preferred examples thereof are also the same as the preferred examples of the “cycloalkyl group having 3 to 12 carbon atoms” in Ay.
　Ｒｂとしての「置換基を有していてもよい炭素数３～１２のシクロアルキル基」における置換基の具体例としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基；メトキシ基、エトキシ基、イソプロポキシ基等の炭素数１～６のアルコキシ基；ニトロ基；フェニル基、１－ナフチル基、２－ナフチル基等の炭素数６～１８の芳香族炭化水素環基；などが挙げられる。これらの中でも、フッ素原子、塩素原子等のハロゲン原子；シアノ基；メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基；メトキシ基、エトキシ基、イソプロポキシ基等の炭素数１～６のアルコキシ基；ニトロ基；フェニル基、１－ナフチル基、２－ナフチル基等の炭素数６～１８の芳香族炭化水素環基；が好ましい。 Specific examples of the substituent in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” as R b include, for example, a halogen atom such as a fluorine atom or a chlorine atom; a cyano group; An N, N-dialkylamino group having 2 to 12 carbon atoms such as a group; an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group or a propyl group; A nitro group; an aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as a phenyl group, a 1-naphthyl group and a 2-naphthyl group; Among these, halogen atoms such as fluorine atom and chlorine atom; cyano group; alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group and propyl group; carbon number 1 such as methoxy group, ethoxy group and isopropoxy group A nitro group; an aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as a phenyl group, a 1-naphthyl group, and a 2-naphthyl group;
－－－Ｒｂとしての「置換基を有していてもよい炭素数６～１８の芳香族炭化水素環基」－－－
　Ｒｂとしての「置換基を有してもよい炭素数６～１８の芳香族炭化水素環基」における「炭素数６～１８の芳香族炭化水素環基」の具体例としては、例えば、フェニル基、１－ナフチル基、２－ナフチル基、などが挙げられる。これらの中でも、フェニル基が好ましい。 --- “R 6 b 18 C 18 -C aromatic hydrocarbon ring group which may have a substituent” as R b ---
Specific examples of the “aromatic hydrocarbon ring group having 6 to 18 carbon atoms” in the “optionally substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms” as R b include, for example, phenyl Group, 1-naphthyl group, 2-naphthyl group, and the like. Among these, a phenyl group is preferable.
　Ｒｂとしての「置換基を有してもよい炭素数６～１８の芳香族炭化水素環基」における置換基の具体例としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基、ブトキシ基等の炭素数１～２０のアルコキシ基；メトキシメトキシ基、メトキシエトキシ基等の、炭素数１～１２のアルコキシ基で置換された炭素数１～１２のアルコキシ基；ニトロ基；トリアゾリル基、ピロリル基、フラニル基、チオフェニル基等の、炭素数２～１８の芳香族複素環基；シクロプロピル基、シクロペンチル基、シクロヘキシル基等の炭素数３～８のシクロアルキル基；シクロペンチルオキシ基、シクロヘキシルオキシ基等の炭素数３～８のシクロアルキルオキシ基；テトラヒドロフラニル基、テトラヒドロピラニル基、ジオキソラニル基、ジオキサニル基等の炭素数２～１２の環状エーテル基；フェノキシ基、ナフトキシ基等の炭素数６～１４のアリールオキシ基；トリフルオロメチル基、ペンタフルオロエチル基、－ＣＨ２ＣＦ３等の、１個以上の水素原子がフッ素原子で置換された炭素数１～１２のアルキル基；－ＯＣＦ３；ベンゾフリル基；ベンゾピラニル基；ベンゾジオキソリル基；ベンゾジオキサニル基；などが挙げられる。
　これらの中でも、フッ素原子、塩素原子等のハロゲン原子；シアノ基；メトキシ基、エトキシ基、イソプロポキシ基、ブトキシ基等の炭素数１～２０のアルコキシ基；ニトロ基；トリアゾリル基、ピロリル基、フラニル基、チオフェニル基等の、炭素数２～１８の芳香族複素環基；シクロプロピル基、シクロペンチル基、シクロヘキシル基等の炭素数３～８のシクロアルキル基；トリフルオロメチル基、ペンタフルオロエチル基、－ＣＨ２ＣＦ３等の、１個以上の水素原子がフッ素原子で置換された炭素数１～１２のアルキル基；および－ＯＣＦ３；からなる群から選ばれる少なくとも１つの置換基が好ましい。
　Ｒｂとしての「置換基を有していてもよい炭素数６～１８の芳香族炭化水素環基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in the “optionally substituted aromatic hydrocarbon ring having 6 to 18 carbon atoms” as R b include, for example, a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; C 2-12 N, N-dialkylamino group such as dimethylamino group; C 1-20 alkoxy group such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group, methoxyethoxy group, etc. An aromatic heterocycle having 2 to 18 carbon atoms, such as a nitro group; a triazolyl group, a pyrrolyl group, a furanyl group, or a thiophenyl group, which is substituted with an alkoxy group having 1 to 12 carbon atoms; A group: a cycloalkyl group having 3 to 8 carbon atoms such as a cyclopropyl group, a cyclopentyl group or a cyclohexyl group; a carbon such as a cyclopentyloxy group or a cyclohexyloxy group A cycloalkyloxy group having 3 to 8 carbon atoms; a cyclic ether group having 2 to 12 carbon atoms such as tetrahydrofuranyl group, tetrahydropyranyl group, dioxolanyl group and dioxanyl group; an aryl having 6 to 14 carbon atoms such as phenoxy group and naphthoxy group An oxy group; an alkyl group having 1 to 12 carbon atoms in which one or more hydrogen atoms are substituted with a fluorine atom, such as a trifluoromethyl group, a pentafluoroethyl group, and —CH 2 CF 3 ; —OCF 3 ; a benzofuryl group; Benzopyranyl group; benzodioxolyl group; benzodioxanyl group;
Among these, halogen atoms such as fluorine atom and chlorine atom; cyano group; alkoxy group having 1 to 20 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group; nitro group; triazolyl group, pyrrolyl group, furanyl An aromatic heterocyclic group having 2 to 18 carbon atoms such as a thiophenyl group; a cycloalkyl group having 3 to 8 carbon atoms such as a cyclopropyl group, a cyclopentyl group and a cyclohexyl group; a trifluoromethyl group, a pentafluoroethyl group, Preference is given to at least one substituent selected from the group consisting of C 1-12 alkyl groups in which one or more hydrogen atoms have been replaced by fluorine atoms, such as —CH 2 CF 3 ; and —OCF 3 ;
The number of substituents in the “optionally substituted aromatic hydrocarbon ring having 6 to 18 carbon atoms” as R b may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
－－Ｇｙ－－
　Ｇｙは、（ｉ）置換基を有していてもよい炭素数１～３０の２価の脂肪族炭化水素基、および、（ｉｉ）置換基を有していてもよい炭素数３～３０の２価の脂肪族炭化水素基に含まれる－ＣＨ２－の少なくとも一つが、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ２１－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ２１－、－ＮＲ２１－、または、－Ｃ（＝Ｏ）－に置換された基のいずれかの有機基である。ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く。Ｒ２１は、水素原子または炭素数１～６のアルキル基を表す。
　前記「２価の脂肪族炭化水素基」は、２価の鎖状の脂肪族炭化水素基であることが好ましく、アルキレン基であることがより好ましい。 --Gy--
Gy is (i) an optionally substituted divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, and (ii) an optionally substituted substituent having 3 to 30 carbon atoms. At least one of —CH 2 — contained in the divalent aliphatic hydrocarbon group is —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O. Substituted with —C (═O) —O—, —NR 21 —C (═O) —, —C (═O) —NR 21 —, —NR 21 —, or —C (═O) — An organic group of any of the groups. However, the case where two or more of —O— or —S— are adjacent to each other is excluded. R 21 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
The “divalent aliphatic hydrocarbon group” is preferably a divalent chain aliphatic hydrocarbon group, and more preferably an alkylene group.
　Ｇｙとしての「（ｉ）置換基を有していてもよい炭素数１～３０の２価の脂肪族炭化水素基」における置換基の具体例としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基、ブトキシ基等の炭素数１～２０のアルコキシ基；メトキシメトキシ基、メトキシエトキシ基、エトキシメトキシ基、エトキシエトキシ基等の、炭素数１～１２のアルコキシ基で置換された炭素数１～１２のアルコキシ基；ニトロ基；トリフルオロメチル基、ペンタフルオロエチル基、ＣＨ２ＣＦ３等の１個以上の水素原子がフッ素原子で置換された炭素数１～１２のアルキル基；水酸基などが挙げられる。これらの中でも、フッ素原子、シアノ基、炭素数１～２０のアルコキシ基、炭素数１～１２のアルコキシ基で置換された炭素数１～１２のアルコキシ基が好ましく、フッ素原子、シアノ基、メトキシ基、エトキシ基、ブトキシ基、メトキシメトキシ基、メトキシエトキシ基、エトキシメトキシ基、エトキシエトキシ基がより好ましい。
　Ｇｙとしての「（ｉ）置換基を有していてもよい炭素数１～３０の２価の脂肪族炭化水素基」における置換基の数は、一つでもよく、複数でもよい。複数の置換基を有する場合、それらは互いに同一であってもよいし、異なっていてもよい。 Specific examples of the substituent in “(i) a divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent” as Gy include, for example, a halogen atom such as a fluorine atom or a chlorine atom. Atom: cyano group; N, N-dialkylamino group having 2 to 12 carbon atoms such as dimethylamino group; alkoxy group having 1 to 20 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group , A methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, or the like, an alkoxy group having 1 to 12 carbon atoms substituted by an alkoxy group having 1 to 12 carbon atoms; a nitro group; a trifluoromethyl group, a pentafluoroethyl group, CH And an alkyl group having 1 to 12 carbon atoms in which one or more hydrogen atoms such as 2 CF 3 are substituted with a fluorine atom; a hydroxyl group and the like. Among these, a fluorine atom, a cyano group, an alkoxy group having 1 to 20 carbon atoms, and an alkoxy group having 1 to 12 carbon atoms substituted with an alkoxy group having 1 to 12 carbon atoms are preferable, and a fluorine atom, a cyano group, and a methoxy group are preferable. Ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, and ethoxyethoxy group are more preferable.
The number of substituents in “(i) a divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent” as Gy may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
　Ｇｙとしての「（ｉｉ）置換基を有していてもよい炭素数３～３０の２価の脂肪族炭化水素基」における置換基の具体例、好適例、および数としては、それぞれ、Ｇｙとしての「（ｉ）置換基を有していてもよい炭素数１～３０の２価の脂肪族炭化水素基」における置換基の具体例、好適例、および数と同様である。 Specific examples, preferred examples, and numbers of substituents in “(ii) a divalent aliphatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent” as Gy are as follows: Specific examples, preferred examples, and numbers of substituents in “(i) a divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent” in
－－Ｙｙ－－
　Ｙｙは、－Ｏ－、－Ｃ（＝Ｏ）－、－Ｓ－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－Ｃ（＝Ｏ）－Ｓ－、－Ｓ－Ｃ（＝Ｏ）－、－ＮＲ２２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ２２－、－Ｏ－Ｃ（＝Ｏ）－ＮＲ２２－、－ＮＲ２２－Ｃ（＝Ｏ）－Ｏ－、－Ｎ＝Ｎ－、または、－Ｃ≡Ｃ－を表す。ここで、Ｒ２２は、水素原子または炭素数１～６のアルキル基を表す。これらの中でも、－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、が好ましい。 --Yy--
Yy represents —O—, —C (═O) —, —S—, —C (═O) —O—, —O—C (═O) —, —O—C (═O) —O—. , —C (═O) —S—, —SC— (═O) —, —NR 22 —C (═O) —, —C (═O) —NR 22 —, —O—C (═O ) —NR 22 —, —NR 22 —C (═O) —O—, —N═N—, or —C≡C—. Here, R 22 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Among these, —O—, —O—C (═O) —O—, —O—C (═O) —, and —C (═O) —O— are preferable.
－－Ｆｙ－－
　Ｆｙは、芳香族炭化水素環および芳香族複素環の少なくとも一方を有する有機基を表す。
　有機基の炭素数としては、２以上３０以下であることが好ましく、７以上３０以下であることがより好ましく、８以上３０以下であることがさらにより好ましく、１０以上３０以下であることが特に好ましい。 --Fy--
Fy represents an organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
The number of carbon atoms of the organic group is preferably 2 or more and 30 or less, more preferably 7 or more and 30 or less, still more preferably 8 or more and 30 or less, and particularly preferably 10 or more and 30 or less. preferable.
　Ｆｙの「芳香族炭化水素環および芳香族複素環の少なくとも一方を有する有機基」の「炭素数」は、「芳香族炭化水素環および芳香族複素環の少なくとも一方を有する有機基」自体の炭素数を意味し、置換基の炭素原子を含まない。 The “carbon number” of the “organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” of Fy is the carbon of the “organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” itself. Means number and does not include carbon atoms of substituents.
　Ｆｙは、（ｉ）「少なくとも一つの水素原子が芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基で置換され、且つ、前記環状基以外の置換基を有していてもよい炭素数１～１８のアルキル基」、または、（ｉｉ）「芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基」であることが好ましい。
　Ｆｙが、複数の芳香族炭化水素環および／または複数の芳香族複素環を有する場合は、それぞれが同じであっても異なっていてもよい。 Fy is (i) “substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms, wherein at least one hydrogen atom has at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, And an alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group, or (ii) a substituent having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. It is preferably a cyclic group having 2 to 30 carbon atoms which may have
When Fy has a plurality of aromatic hydrocarbon rings and / or a plurality of aromatic heterocycles, each may be the same or different.
　前記「置換基を有していてもよい炭素数２～３０の環状基」における「芳香族炭化水素環」の具体例としては、例えば、ベンゼン環、ナフタレン環、アントラセン環、フェナントレン環、ピレン環、フルオレン環等の、炭素数６～３０の芳香族炭化水素環が挙げられる。 Specific examples of the “aromatic hydrocarbon ring” in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. And an aromatic hydrocarbon ring having 6 to 30 carbon atoms, such as a fluorene ring.
　前記「置換基を有していてもよい炭素数２～３０の環状基」における「芳香族複素環」の具体例としては、例えば、１Ｈ－イソインドール－１，３（２Ｈ）－ジオン環、１－ベンゾフラン環、２－ベンゾフラン環、アクリジン環、イソキノリン環、イミダゾール環、インドール環、オキサジアゾール環、オキサゾール環、オキサゾロピラジン環、オキサゾロピリジン環、オキサゾロピリダジン環、オキサゾロピリミジン環、キナゾリン環、キノキサリン環、キノリン環、シンノリン環、チアジアゾール環、チアゾール環、チアゾロピラジン環、チアゾロピリジン環、チアゾロピリダジン環、チアゾロピリミジン環、チオフェン環、トリアジン環、トリアゾール環、ナフチリジン環、ピラジン環、ピラゾール環、ピラノン環、ピラン環、ピリジン環、ピリダジン環、ピリミジン環、ピロール環、フェナントリジン環、フタラジン環、フラン環、ベンゾ［ｂ］チオフェン環、ベンゾ［ｃ］チオフェン環、ベンゾイソオキサゾール環、ベンゾイソチアゾール環、ベンゾイミダゾール環、ベンゾオキサジアゾール環、ベンゾオキサゾール環、ベンゾチアジアゾール環、ベンゾチアゾール環、ジベンゾチオフェン環、ベンゾトリアジン環、ベンゾトリアゾール環、ベンゾピラゾール環、ペンゾピラノン環、キサンテン環等の炭素数２～３０の芳香複素環；などが挙げられる。 Specific examples of the “aromatic heterocycle” in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, 1H-isoindole-1,3 (2H) -dione ring, 1-benzofuran ring, 2-benzofuran ring, acridine ring, isoquinoline ring, imidazole ring, indole ring, oxadiazole ring, oxazole ring, oxazolopyrazine ring, oxazolopyridine ring, oxazolopyridazine ring, oxazolopyrimidine ring, Quinazoline ring, quinoxaline ring, quinoline ring, cinnoline ring, thiadiazole ring, thiazole ring, thiazolopyrazine ring, thiazolopyridine ring, thiazolopyridazine ring, thiazolopyrimidine ring, thiophene ring, triazine ring, triazole ring, naphthyridine ring, Pyrazine ring, pyrazole ring, pyranone ring, pyran ring, pyri Ring, pyridazine ring, pyrimidine ring, pyrrole ring, phenanthridine ring, phthalazine ring, furan ring, benzo [b] thiophene ring, benzo [c] thiophene ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring , Benzoxadiazole ring, benzoxazole ring, benzothiadiazole ring, benzothiazole ring, dibenzothiophene ring, benzotriazine ring, benzotriazole ring, benzopyrazole ring, benzopyranone ring, xanthene ring, etc. Ring; and the like.
　前記「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基；ビニル基、アリル基等の炭素数２～６のアルケニル基；トリフルオロメチル基、ペンタフルオロエチル基等の１個以上の水素原子がフッ素原子等のハロゲン原子で置換された炭素数１～６のアルキル基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基等の炭素数１～６のアルコキシ基；ニトロ基；－ＯＣＦ３；－Ｃ（＝Ｏ）－Ｒｂ；－Ｃ（＝Ｏ）－Ｏ－Ｒｂ；－Ｏ－Ｃ（＝Ｏ）－Ｒｂ；などが挙げられる。Ｒｂは、前記と同じ意味を表し、その好適例も前記と同じである。
　なお、Ｆｙは、上述した置換基から選ばれる複数の置換基を有していてもよい。Ｆｙが複数の置換基を有する場合、置換基は同一でも相異なっていてもよい。 Specific examples of the substituent in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; methyl group, ethyl group, An alkyl group having 1 to 6 carbon atoms such as a propyl group; an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group; one or more hydrogen atoms such as a trifluoromethyl group or a pentafluoroethyl group are fluorine atoms, etc. An alkyl group having 1 to 6 carbon atoms substituted with a halogen atom of 1 to 6; an N, N-dialkylamino group having 2 to 12 carbon atoms such as a dimethylamino group; 6 alkoxy group; nitro group; —OCF 3 ; —C (═O) —R b ; —C (═O) —O—R b ; —O—C (═O) —R b ; . R b represents the same meaning as described above, and preferred examples thereof are also the same as described above.
Note that Fy may have a plurality of substituents selected from the above-described substituents. When Fy has a plurality of substituents, the substituents may be the same or different.
　Ｆｙとしての「（ｉ）少なくとも一つの水素原子が芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基で置換され、且つ、前記環状基以外の置換基を有していてもよい炭素数１～１８のアルキル基」における「炭素数１～１８のアルキル基」の具体例としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、などが挙げられる。 “(I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring; Specific examples of the “alkyl group having 1 to 18 carbon atoms” in the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” include, for example, a methyl group, an ethyl group, A propyl group, an isopropyl group, etc. are mentioned.
　Ｆｙとしての「（ｉ）少なくとも一つの水素原子が芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基で置換され、且つ、前記環状基以外の置換基を有していてもよい炭素数１～１８のアルキル基」における「芳香族炭化水素環および芳香族複素環の少なくとも一方」は、「炭素数１～１８のアルキル基」の炭素原子に直接結合していてもよいし、－Ｓ－、－Ｏ－、－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－Ｃ（＝Ｏ）－Ｓ－、－Ｓ－Ｃ（＝Ｏ）－、－ＮＲ２３－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ２３等の連結基を介して炭素数１～１８のアルキル基の炭素原子に結合していてもよい。ここで、Ｒ２３は、水素原子または炭素数１～６のアルキル基を表す。
　即ち、芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基としては、フルオレニル基、ベンゾチアゾリル基のような、「芳香族炭化水素環および芳香族複素環の少なくとも一方を有する基」、「置換されていてもよい芳香族炭化水素環基」、「置換されていてもよい芳香族複素環基」、「連結基を有する置換されていてもよい芳香族炭化水素環よりなる基」、「連結基を有する置換されていてもよい芳香族複素環よりなる基」も含まれる。 “(I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring; In addition, “at least one of the aromatic hydrocarbon ring and the aromatic heterocyclic ring” in the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” means “having 1 to 18 carbon atoms”. It may be directly bonded to the carbon atom of the alkyl group, or —S—, —O—, —C (═O) —, —C (═O) —O—, —O—C (═O). —, —O—C (═O) —O—, —C (═O) —S—, —S—C (═O) —, —NR 23 —C (═O) —, —C (═O ) It may be bonded to a carbon atom of an alkyl group having 1 to 18 carbon atoms via a linking group such as —NR 23 . Here, R 23 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
That is, examples of the optionally substituted cyclic group having 2 to 30 carbon atoms having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring include “aromatic groups such as a fluorenyl group and a benzothiazolyl group”. A group having at least one of a hydrocarbon ring and an aromatic heterocyclic ring, an “optionally substituted aromatic hydrocarbon ring group”, an “optionally substituted aromatic heterocyclic group”, and a “linking group”. Also included are “a group consisting of an optionally substituted aromatic hydrocarbon ring” and “a group consisting of an optionally substituted aromatic heterocycle having a linking group”.
　前記「置換されていてもよい芳香族炭化水素環基」における「芳香族炭化水素環基」の具体例としては、フェニル基、ナフチル基、アントラセニル基、フェナントレニル基、ピレニル基、フルオレニル基等の炭素数６～３０の芳香族炭化水素環基；などが挙げられる。 Specific examples of the “aromatic hydrocarbon ring group” in the “optionally substituted aromatic hydrocarbon ring group” include carbon such as phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluorenyl group and the like. And an aromatic hydrocarbon ring group of 6 to 30;
　前記「置換されていてもよい芳香族炭化水素環基」における置換基の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。 Specific examples of the substituent in the “optionally substituted aromatic hydrocarbon ring group” include specific examples of the substituent in the above “optionally substituted cyclic group having 2 to 30 carbon atoms”. Same as “Example”.
　前記「置換されていてもよい芳香族複素環基」における「芳香族複素環基」の具体例としては、フタルイミド基、１－ベンゾフラニル基、２－ベンゾフラニル基、アクリジニル基、イソキノリニル基、イミダゾリル基、インドリル基、フラザニル基、オキサゾリル基、オキサゾロピラジニル基、オキサゾロピリジニル基、オキサゾロピリダジニル基、オキサゾロピリミジニル基、キナゾリニル基、キノキサリニル基、キノリル基、シンノリニル基、チアジアゾリル基、チアゾリル基、チアゾロピラジニル基、チアゾロピリジル基、チアゾロピリダジニル基、チアゾロピリミジニル基、チエニル基、トリアジニル基、トリアゾリル基、ナフチリジニル基、ピラジニル基、ピラゾリル基、ピラノニル基、ピラニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピロリル基、フェナントリジニル基、フタラジニル基、フラニル基、ベンゾ［ｃ］チエニル基、ベンゾイソオキサゾリル基、ベンゾイソチアゾリル基、ベンゾイミダゾリル基、ベンゾオキサジアゾリル基、ベンゾオキサゾリル基、ベンゾチアジアゾリル基、ベンゾチアゾリル基、ベンゾチエニル基、ベンゾトリアジニル基、ベンゾトリアゾリル基、ベンゾピラゾリル基、ペンゾピラノニル基等の炭素数２～３０の芳香族複素環基；などが挙げられる。 Specific examples of the “aromatic heterocyclic group” in the “optionally substituted aromatic heterocyclic group” include phthalimide group, 1-benzofuranyl group, 2-benzofuranyl group, acridinyl group, isoquinolinyl group, imidazolyl group, Indolyl group, furazanyl group, oxazolyl group, oxazolopyrazinyl group, oxazolopyridinyl group, oxazolopyridazinyl group, oxazolopyrimidinyl group, quinazolinyl group, quinoxalinyl group, quinolyl group, cinnolinyl group, thiadiazolyl group , Thiazolyl group, thiazolopyrazinyl group, thiazolopyridyl group, thiazolopyridazinyl group, thiazolopyrimidinyl group, thienyl group, triazinyl group, triazolyl group, naphthyridinyl group, pyrazinyl group, pyrazolyl group, pyranonyl group, Pyranyl group, pyridyl group, pyridazinyl , Pyrimidinyl group, pyrrolyl group, phenanthridinyl group, phthalazinyl group, furanyl group, benzo [c] thienyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzoimidazolyl group, benzooxadiazolyl group, benzooxa Aromatic heterocyclic groups having 2 to 30 carbon atoms such as zolyl group, benzothiadiazolyl group, benzothiazolyl group, benzothienyl group, benzotriazinyl group, benzotriazolyl group, benzopyrazolyl group, benzopyranonyl group; Is mentioned.
　前記「置換されていてもよい芳香族複素環基」における「置換基」の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。 Specific examples of the “substituent” in the “optionally substituted aromatic heterocyclic group” include those of the substituent in the “optionally substituted cyclic group having 2 to 30 carbon atoms”. It is the same as “Specific Example”.
　前記「連結基を有する置換されていてもよい芳香族炭化水素環よりなる基」および／または前記「連結基を有する置換されていてもよい芳香族複素環よりなる基」の具体例としては、フェニルチオ基、ナフチルチオ基、アントラセニルチオ基、フェナントレニルチオ基、ピレニルチオ基、フルオレニルチオ基、フェニルオキシ基、ナフチルオキシ基、アントラセニルオキシ基、フェナントレニルオキシ基、ピレニルオキシ基、フルオレニルオキシ基、ベンゾイソオキサゾリルチオ基、ベンゾイソチアゾリルチオ基、ベンゾオキサジアゾリルチオ基、ベンゾオキサゾリルチオ基、ベンゾチアジアゾリルチオ基、ベンゾチアゾリルチオ基、ベンゾチエニルチオ基、ベンゾイソオキサゾリルオキシ基、ベンゾイソチアゾリルオキシ基、ベンゾオキサジアゾリルオキシ基、ベンゾオキサゾリルオキシ基、ベンゾチアジアゾリルオキシ基、ベンゾチアゾリルオキシ基、ベンゾチエニルオキシ基、などが挙げられる。 Specific examples of the “group consisting of an optionally substituted aromatic hydrocarbon ring having a linking group” and / or the “group consisting of an optionally substituted aromatic heterocyclic ring having a linking group” include: Phenylthio, naphthylthio, anthracenylthio, phenanthrenylthio, pyrenylthio, fluorenylthio, phenyloxy, naphthyloxy, anthracenyloxy, phenanthrenyloxy, pyrenyloxy, fluorenyl Oxy group, benzoisoxazolylthio group, benzoisothiazolylthio group, benzoxiadiazolylthio group, benzoxazolylthio group, benzothiadiazolylthio group, benzothiazolylthio group, benzothienylthio group, benzoiso Oxazolyloxy group, benzoisothiazolyloxy group, benzox Diazo Lil oxy group, benzoxazolyl group, benzothiadiazolyl group, benzothiazolyl group, benzothienyl group, and the like.
　前記「連結基を有する置換されていてもよい芳香族炭化水素環よりなる基」および前記「連結基を有する置換されていてもよい芳香族複素環よりなる基」が有し得る「置換基」の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。 The “substituent” that the “group consisting of an optionally substituted aromatic hydrocarbon ring having a linking group” and the “group consisting of an optionally substituted aromatic heterocyclic ring having a linking group” may have. Specific examples of are the same as the above-mentioned “specific examples of substituents in the“ cyclic group having 2 to 30 carbon atoms which may have a substituent ””.
　Ｆｙとしての「（ｉ）少なくとも一つの水素原子が芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基で置換され、且つ、前記環状基以外の置換基を有していてもよい炭素数１～１８のアルキル基」の好ましい具体例としては、下記式（３－１）～（３－１１）で表される構造が挙げられる。
　但し、本発明は、以下に示すものに限定されるものではない。なお、下記式（３－１）～（３－１１）中、「＊」はＹｙと結合する位置を表し、環内部からのびる「－」は、環の任意の位置からのびる結合手を表す。なお、下記式（３－１）～（３－１１）で表される基は置換基を有していてもよく、その置換基の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。
Figure JPOXMLDOC01-appb-C000007
 “(I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring; Preferred examples of the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” include structures represented by the following formulas (3-1) to (3-11): Is mentioned.
However, the present invention is not limited to the following. In the following formulas (3-1) to (3-11), “*” represents a position bonded to Yy, and “−” extending from the inside of the ring represents a bond extending from an arbitrary position on the ring. The groups represented by the following formulas (3-1) to (3-11) may have a substituent. Specific examples of the substituent include the above-mentioned ““ having a substituent. The same as the “specific examples of substituents” in the “cyclic group having 2 to 30 carbon atoms”.
Figure JPOXMLDOC01-appb-C000007
　Ｆｙとしての「（ｉ）芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基で置換され、且つ、前記環状基以外の置換基を有していてもよい炭素数１～１８のアルキル基」における「炭素数１～１８のアルキル基」は、１以上の置換基を有していてもよい。「炭素数１～１８のアルキル基」が複数の置換基を有する場合は、この「複数の置換基」は互いに同一でも相異なっていてもよい。その置換基の具体例としては、前記「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。 As Fy, “(i) substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, and other than the above cyclic group The “alkyl group having 1 to 18 carbon atoms” in the “optionally substituted alkyl group having 1 to 18 carbon atoms” may have one or more substituents. When the “alkyl group having 1 to 18 carbon atoms” has a plurality of substituents, the “plural substituents” may be the same as or different from each other. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
　Ｆｙとしての「（ｉｉ）芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基」としては、例えば、（ｉｉ－１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、置換基を有していてもよい炭素数６～３０の炭化水素環基、（ｉｉ－２）炭素数６～１８の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、置換基を有していてもよい炭素数２～３０の複素環基、などが好適に挙げられる。 Examples of “(ii) a cyclic group having 2 to 30 carbon atoms which has at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring and may have a substituent” as Fy include, for example, (ii-1 ) An optionally substituted hydrocarbon ring group having 6 to 30 carbon atoms, having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms; and (ii-2) an aromatic having 6 to 18 carbon atoms. A heterocyclic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring having 2 to 30 carbon atoms, an optionally substituted heterocyclic group having 2 to 30 carbon atoms, and the like Preferably mentioned.
　前記「（ｉｉ－１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、置換基を有していてもよい炭素数６～３０の炭化水素環基」における「炭化水素環基」の具体例としては、例えば、フェニル基（炭素数６）、ナフチル基（炭素数１０）、アントラセニル基（炭素数１４）、フェナントレニル基（炭素数１４）、ピレニル基（炭素数１６）、フルオレニル基（炭素数１３）等の炭素数６～１８の芳香族炭化水素環基；インダニル基（炭素数９）；１，２，３，４－テトラヒドロナフチル基（炭素数１０）；１，４－ジヒドロナフチル基（炭素数１０）；などが挙げられる。 The “hydrocarbon ring group” in the above “(ii-1) optionally having a hydrocarbon ring group having 6 to 30 carbon atoms, which has an aromatic hydrocarbon ring having 6 to 30 carbon atoms”. As specific examples, for example, phenyl group (6 carbon atoms), naphthyl group (10 carbon atoms), anthracenyl group (14 carbon atoms), phenanthrenyl group (14 carbon atoms), pyrenyl group (16 carbon atoms), fluorenyl An aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as a group (carbon number 13); an indanyl group (9 carbon atoms); a 1,2,3,4-tetrahydronaphthyl group (10 carbon atoms); Dihydronaphthyl group (10 carbon atoms); and the like.
　前記「（ｉｉ－１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、置換基を有していてもよい炭素数６～３０の炭化水素環基」の具体例としては、例えば、下記式（１－１）～（１－２１）で表される構造の基が挙げられる。
　下記式（１－１）～（１－２１）で表される構造の基は置換基を有していてもよい。その置換基の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。
　なお、下記式（１－１）～（１－２１）中、環内部からのびる「－」は、環の任意の位置からのびるＹｙとの結合手を表す。
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000009
 Specific examples of the “(ii-1) at least one hydrocarbon ring group having 6 to 30 carbon atoms, which may have a substituent and having 6 to 30 carbon atoms” include: Examples thereof include groups having structures represented by the following formulas (1-1) to (1-21).
The groups having the structures represented by the following formulas (1-1) to (1-21) may have a substituent. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
In the following formulas (1-1) to (1-21), “-” extending from the inside of the ring represents a bond with Yy extending from any position of the ring.
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000009
　前記「（ｉｉ－２）炭素数６～１８の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、置換基を有していてもよい炭素数２～３０の複素環基」における「複素環基」としては、例えば、フタルイミド基、１－ベンゾフラニル基、２－ベンゾフラニル基、アクリジニル基、イソキノリニル基、イミダゾリル基、インドリル基、フラザニル基、オキサゾリル基、オキサゾロピラジニル基、オキサゾロピリジニル基、オキサゾロピリダジニル基、オキサゾロピリミジニル基、キナゾリニル基、キノキサリニル基、キノリル基、シンノリニル基、チアジアゾリル基、チアゾリル基、チアゾロピラジニル基、チアゾロピリジニル基、チアゾロピリダジニル基、チアゾロピリミジニル基、チエニル基、トリアジニル基、トリアゾリル基、ナフチリジニル基、ピラジニル基、ピラゾリル基、ピラノニル基、ピラニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピロリル基、フェナントリジニル基、フタラジニル基、フラニル基、ベンゾ［ｃ］チエニル基、ベンゾイソオキサゾリル基、ベンゾイソチアゾリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアジアゾリル基、ベンゾチアゾリル基、ベンゾチオフェニル基、ベンゾトリアジニル基、ベンゾトリアゾリル基、ベンゾピラゾリル基、ペンゾピラノニル基等の炭素数２～１８の芳香族複素環基；キサンテニル基；２，３－ジヒドロインドリル基；９，１０－ジヒドロアクリジニル基；１，２，３，４－テトラヒドロキノリル基；ジヒドロピラニル基；テトラヒドロピラニル基；ジヒドロフラニル基；テトラヒドロフラニル基；などが挙げられる。 And (ii) having a substituent having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms. Examples of the “heterocyclic group” in the “heterocyclic group having 2 to 30 carbon atoms” include, for example, phthalimide group, 1-benzofuranyl group, 2-benzofuranyl group, acridinyl group, isoquinolinyl group, imidazolyl group, indolyl group, and flazanyl group. , Oxazolyl group, oxazolopyrazinyl group, oxazolopyridinyl group, oxazolopyridazinyl group, oxazolopyrimidinyl group, quinazolinyl group, quinoxalinyl group, quinolyl group, cinnolinyl group, thiadiazolyl group, thiazolyl group, thia Zolopyrazinyl group, thiazolopyridinyl group, thiazolopyridazinyl group, thiazolopyrimidinyl group Thienyl, triazinyl, triazolyl, naphthyridinyl, pyrazinyl, pyrazolyl, pyranonyl, pyranyl, pyridyl, pyridazinyl, pyrimidinyl, pyrrolyl, phenanthridinyl, phthalazinyl, furanyl, benzo [ c] thienyl group, benzisoxazolyl group, benzisothiazolyl group, benzimidazolyl group, benzoxazolyl group, benzothiadiazolyl group, benzothiazolyl group, benzothiophenyl group, benzotriazinyl group, benzotriazolyl An aromatic heterocyclic group having 2 to 18 carbon atoms, such as a sulfur group, a benzopyrazolyl group, a benzopyranonyl group; a xanthenyl group; a 2,3-dihydroindolyl group; a 9,10-dihydroacridinyl group; , 4-tetrahydroquinolyl group; dihydropyranyl group; Tiger tetrahydropyranyl group; dihydrofuranyl group; a tetrahydrofuranyl group; and the like.
　前記「（ｉｉ－２）炭素数６～１８の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、置換基を有していてもよい炭素数２～３０の複素環基」の具体例としては、下記式（２－１）～（２－５１）で表される構造の基が挙げられる。
　下記式（２－１）～（２－５１）で表される構造の基は置換基を有していてもよい。その置換基の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。
　なお、下記式（２－１）～（２－５１）中、環内部からのびる「－」は、環の任意の位置からのびるＹｙとの結合手を表す。
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000013
 〔各式中、Ｘは、－ＣＨ２－、－ＮＲｃ－、酸素原子、硫黄原子、－ＳＯ－または－ＳＯ２－を表し、
　ＹおよびＺは、それぞれ独立して、－ＮＲｃ－、酸素原子、硫黄原子、－ＳＯ－または－ＳＯ２－を表し、
　Ｅは、－ＮＲｃ－、酸素原子または硫黄原子を表す。
　ここで、Ｒｃは、水素原子、または、メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基を表す。（但し、各式中において酸素原子、硫黄原子、－ＳＯ－、－ＳＯ２－は、それぞれ隣接しないものとする。）〕 And (ii) having a substituent having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms. Specific examples of the “heterocyclic group having 2 to 30 carbon atoms” include groups having structures represented by the following formulas (2-1) to (2-51).
The groups having the structures represented by the following formulas (2-1) to (2-51) may have a substituent. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
In the following formulas (2-1) to (2-51), “-” extending from the inside of the ring represents a bond with Yy extending from any position of the ring.
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000013
 [In each formula, X 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 —;
E represents —NR c —, an oxygen atom or a sulfur atom.
Here, R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group. (However, in each formula, oxygen atom, sulfur atom, —SO—, and —SO 2 — are not adjacent to each other.)]
　前記「（ｉｉ）芳香族炭化水素環および芳香族複素環の少なくとも一方を有する、置換基を有していてもよい炭素数２～３０の環状基」は、１以上の置換基を有していてもよい。複数の置換基を有する場合は、複数の置換基は互いに同一でも相異なっていてもよい。その置換基の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。 The “(ii) optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” has one or more substituents. May be. When it has a plurality of substituents, the plurality of substituents may be the same as or different from each other. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
　Ａｒが（ＩＩ－１）である場合、Ｆｙは、下記式（ｉ－１）～（ｉ－９）のいずれかで表される構造の基であることが好ましく、下記式（ｉｉ－１）～（ｉｉ－２０）のいずれかで表される構造の基であることが特に好ましい。
　Ａｒが（ＩＩ－２）または（ＩＩ－３）で表される構造の基である場合、Ｆｙは、下記（ｉ－１）～（ｉ－１３）のいずれかで表される構造の基であることが好ましく、下記式（ｉｉ－１）～（ｉｉ－２６）のいずれかで表される構造の基であることが特に好ましい。なお、下記式（ｉ－１）～（ｉ－１３）及び下記式（ｉｉ－１）～（ｉｉ－２６）のいずれかで表される構造の基は置換基を有していてもよい。その置換基の具体例としては、前記「「置換基を有していてもよい炭素数２～３０の環状基」における置換基の具体例」と同じである。また、式（ｉ－４）、（ｉｉ－６）および（ｉｉ－７）中、Ｙは、前記と同じ意味を表す。また、下記式（ｉ－１）～（ｉ－１３）及び下記式（ｉｉ－１）～（ｉｉ－２６）中、「＊」はＹｙと結合する位置を表し、環内部からのびる「－」は、環の任意の位置からのびる結合手を表す。
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000018
 When Ar is (II-1), Fy is preferably a group having a structure represented by any of the following formulas (i-1) to (i-9), and the following formula (ii-1) A group having a structure represented by any one of (ii-20) is particularly preferred.
When Ar is a group having a structure represented by (II-2) or (II-3), Fy is a group having a structure represented by any of the following (i-1) to (i-13): It is preferably a group having a structure represented by any of the following formulas (ii-1) to (ii-26). The group having a structure represented by any of the following formulas (i-1) to (i-13) and the following formulas (ii-1) to (ii-26) may have a substituent. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”. In the formulas (i-4), (ii-6) and (ii-7), Y represents the same meaning as described above. Further, in the following formulas (i-1) to (i-13) and the following formulas (ii-1) to (ii-26), “*” represents the position where Yy is bonded, and “−” extends from the inside of the ring. Represents a bond extending from any position of the ring.
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000018
　Ａｒが（ＩＩ－１）である場合、Ｆｙ中の環構造に含まれるπ電子の総数は、８以上であることが好ましく、１０以上であることがより好ましく、また、２０以下であることが好ましく、１８以下であることがより好ましい。Ａｒが（ＩＩ－２）または（ＩＩ－３）で表される構造の基である場合、Ｆｙ中の環構造に含まれるπ電子の総数は、４以上であることが好ましく、６以上であることがより好ましく、また、２０以下であることが好ましく、１８以下であることがより好ましい。 When Ar is (II-1), the total number of π electrons contained in the ring structure in Fy is preferably 8 or more, more preferably 10 or more, and 20 or less. Preferably, it is 18 or less. When Ar is a group having a structure represented by (II-2) or (II-3), the total number of π electrons contained in the ring structure in Fy is preferably 4 or more, and is 6 or more. More preferably, it is preferably 20 or less, and more preferably 18 or less.
－Ａｘ－
　Ａｘは、炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する有機基を表す。 -Ax-
Ax represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
　Ａｘは、下記（１）～（５）の何れかであることが好ましい。
（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基
（２）炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、炭素数２～４０の複素環基
（３）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数１～１２のアルキル基
（４）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルケニル基
（５）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルキニル基 Ax is preferably any one of the following (1) to (5).
(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and 2 to 30 carbon atoms A heterocyclic group having 2 to 40 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic heterocyclic rings of (3) an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and 2 to 30 carbon atoms An alkyl group having 1 to 12 carbon atoms substituted with at least one aromatic heterocyclic group, (4) an aromatic hydrocarbon ring group having 6 to 30 carbon atoms, and an aromatic heterocyclic group having 2 to 30 carbon atoms Substituted with at least one alkenyl group having 2 to 12 carbon atoms and (5) an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms In addition, an alkynyl group having 2 to 12 carbon atoms
－Ａｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」－
　Ａｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」における「炭素数６～４０の炭化水素環基」の具体例としては、例えば、下記構造式で表される基、などが挙げられる。下記構造式で表される基は、置換基を有していてもよい。置換基の具体例としては、後述する「Ａｘが有する置換基の具体例」と同じである。
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000020
 -"(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms" as Ax-
Specific examples of “hydrocarbon ring group having 6 to 40 carbon atoms” in “(1) hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax Examples include groups represented by the following structural formula. The group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later.
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000020
　Ａｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の具体例としては、フッ素原子、塩素原子等のハロゲン原子；シアノ基；メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基；ビニル基、アリル基等の炭素数２～６のアルケニル基；トリフルオロメチル基等の１個以上の水素原子がフッ素原子等のハロゲン原子で置換された炭素数１～６のアルキル基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基等の炭素数１～６のアルコキシ基；ニトロ基；フェニル基、ナフチル基等の炭素数６～２０の芳香族炭化水素環基；－ＯＣＦ３；－Ｃ（＝Ｏ）－Ｒｂ；－Ｏ－Ｃ（＝Ｏ）－Ｒｂ；－Ｃ（＝Ｏ）－Ｏ－Ｒｂ；－ＳＯ２Ｒａ；等が挙げられる。ここで、ＲｂおよびＲａは、それぞれ、前記と同じ意味を表し、その好適例も前記と同じである。
　これらの中でも、ハロゲン原子、シアノ基、炭素数１～６のアルキル基、および炭素数１～６のアルコキシ基からなる群より選択される少なくとも一つの置換基が好ましい。 Specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax include a fluorine atom, a chlorine atom, etc. A cyano group; an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group or a propyl group; an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group; one such as a trifluoromethyl group An alkyl group having 1 to 6 carbon atoms in which the above hydrogen atom is substituted with a halogen atom such as a fluorine atom; an N, N-dialkylamino group having 2 to 12 carbon atoms such as a dimethylamino group; a methoxy group, an ethoxy group, an iso An alkoxy group having 1 to 6 carbon atoms such as a propoxy group; a nitro group; an aromatic hydrocarbon ring group having 6 to 20 carbon atoms such as a phenyl group and a naphthyl group; —OCF 3 ; —C (═O) —R b ; -O-C (= O) -R b -C (= O) -O-R b; -SO 2 R a; and the like. Wherein, R b and R a are each the same meanings as defined above, the preferred examples are also the same as above.
Among these, at least one substituent selected from the group consisting of a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms is preferable.
　Ａｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」における「炭素数６～３０の芳香族炭化水素環」の具体例としては、例えば、ベンゼン環、ナフタレン環、フルオレン環などが挙げられる。 “Aromatic hydrocarbon ring having 6 to 30 carbon atoms” in “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax Specific examples include a benzene ring, a naphthalene ring, a fluorene ring, and the like.
－Ａｘとしての「（２）炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、炭素数２～４０の複素環基」－
　Ａｘとしての「（２）炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、炭素数２～４０の複素環基」の具体例としては、例えば、下記構造式で表される基、などが挙げられる。下記構造式で表される基は、置換基を有していてもよい。置換基の具体例としては、後述する「Ａｘが有する置換基の具体例」と同じである。
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000028
 -(2) having at least one aromatic ring selected from the group consisting of (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms as -Ax Heterocyclic group ”
A (2) a complex having 2 to 40 carbon atoms having at least one aromatic ring selected from the group consisting of (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms as Ax Specific examples of the “ring group” include, for example, groups represented by the following structural formulas. The group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later.
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000028
〔各式中、Ｒは、水素原子、または、メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基を表し、また、環内部からのびる「－」は、環の任意の位置からのびる結合手を表す。〕 [In each formula, R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group, and “−” extending from the inside of the ring represents any position of the ring. Represents a bond that extends from ]
　Ａｘとしての「（２）炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、炭素数２～４０の複素環基」の置換基の具体例としては、「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の具体例と同じであり、その好適例も「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の好適例と同じである。 A (2) a complex having 2 to 40 carbon atoms having at least one aromatic ring selected from the group consisting of (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms as Ax Specific examples of the substituent of the “cyclic group” include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms”. The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms”. is there.
　Ａｘとしての「（２）炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、炭素数２～４０の複素環基」における「炭素数６～３０の芳香族炭化水素環」の具体例としては、例えば、ベンゼン環、ナフタレン環、フルオレン環、アントラセン環などが挙げられる。 A (2) a complex having 2 to 40 carbon atoms having at least one aromatic ring selected from the group consisting of (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms as Ax Specific examples of the “aromatic hydrocarbon ring having 6 to 30 carbon atoms” in the “ring group” include, for example, benzene ring, naphthalene ring, fluorene ring, anthracene ring and the like.
　Ａｘとしての「（２）炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、炭素数２～４０の複素環基」における「炭素数２～３０の芳香族複素環」の具体例としては、例えば、チオフェン環、フラン環、ピリジン環、ピラジン環、ピリミジン環、トリアジン環、ピロール環、イミダゾール環、チアゾール環、オキサゾール環、ベンゾチアゾール環、ベンゾオキサゾール環などが挙げられる。 A (2) a complex having 2 to 40 carbon atoms having at least one aromatic ring selected from the group consisting of (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms as Ax Specific examples of “aromatic heterocycle having 2 to 30 carbon atoms” in “ring group” include, for example, thiophene ring, furan ring, pyridine ring, pyrazine ring, pyrimidine ring, triazine ring, pyrrole ring, imidazole ring, thiazole ring. Oxazole ring, benzothiazole ring, benzoxazole ring and the like.
－Ａｘとしての「（３）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数１～１２のアルキル基」－
　Ａｘとしての「（３）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数１～１２のアルキル基」における「炭素数１～１２のアルキル基」の具体例としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、などが挙げられる。 -(3) an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax -
In “(3) an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the “alkyl group having 1 to 12 carbon atoms” include, for example, methyl group, ethyl group, propyl group, isopropyl group, and the like.
　Ａｘとしての「（３）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数１～１２のアルキル基」の置換基の具体例としては、Ａｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の具体例と同じであり、その好適例もＡｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の好適例と同じである。 “(3) an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the substituent include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax; The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. The same.
　Ａｘとしての「（３）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数１～１２のアルキル基」における「炭素数６～３０の芳香族炭化水素環基」の具体例としては、前記Ａｙでの「炭素数６～３０の芳香族炭化水素環基」の具体例と同じものが挙げられる。 In “(3) an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in the above Ay.
　Ａｘとしての「（３）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数１～１２のアルキル基」における「炭素数２～３０の芳香族複素環基」の具体例としては、前記Ａｙでの「炭素数２～３０の芳香族複素環基」の具体例と同じものが挙げられる。 In “(3) an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” include the same examples as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
　－Ａｘとしての「（４）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルケニル基」－
　Ａｘとしての「（４）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルケニル基」における「炭素数２～１２のアルケニル基」の具体例としては、例えば、ビニル基、アリル基、などが挙げられる。 -(4) an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax -
In “(4) an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the “alkenyl group having 2 to 12 carbon atoms” include, for example, a vinyl group and an allyl group.
　Ａｘとしての「（４）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルケニル基」の置換基の具体例としては、Ａｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の具体例と同じであり、その好適例もＡｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の好適例と同じである。 “(4) an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the substituent include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax; The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. The same.
　Ａｘとしての「（４）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルケニル基」における「炭素数６～３０の芳香族炭化水素環基」の具体例としては、前記Ａｙでの「炭素数６～３０の芳香族炭化水素環基」の具体例と同じものが挙げられる。 In “(4) an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in the above Ay.
　Ａｘとしての「（４）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルケニル基」における「炭素数２～３０の芳香族複素環基」の具体例としては、前記Ａｙでの「炭素数２～３０の芳香族複素環基」の具体例と同じものが挙げられる。 In “(4) an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” include the same examples as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
－Ａｘとしての「（５）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルキニル基」－
　Ａｘとしての「（５）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルキニル基」の具体例としては、例えば、エチニル基、プロピニル基、などが挙げられる。 -(5) an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax -
“(5) an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples include ethynyl group, propynyl group, and the like.
　Ａｘとしての「（５）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルキニル基」の置換基の具体例としては、Ａｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基と同じであり、その好適例もＡｘとしての「（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基」の置換基の好適例と同じである。 “(5) an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Specific examples of the substituent are the same as those of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. The preferred examples thereof are also the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. .
　Ａｘとしての「（５）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルキニル基」における「炭素数６～３０の芳香族炭化水素環基」としては、前記Ａｙでの「炭素数６～３０の芳香族炭化水素環基」の具体例と同じものが挙げられる。 In “(5) an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in Ay.
　Ａｘとしての「（５）炭素数６～３０の芳香族炭化水素環基および炭素数２～３０の芳香族複素環基の少なくとも１つで置換された、炭素数２～１２のアルキニル基」における「炭素数２～３０の芳香族複素環基」としては、前記Ａｙでの「炭素数２～３０の芳香族複素環基」の具体例と同じものが挙げられる。 In “(5) an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax Examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” are the same as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
　Ａｘは、下記構造式で表される基のいずれかであることが好ましい。下記構造式で表される基は、置換基を有していてもよい。置換基の具体例としては、後述する「Ａｘが有する置換基の具体例」と同じである。
Figure JPOXMLDOC01-appb-C000029
 〔各式中、環内部からのびる「－」は、環の任意の位置からのびる結合手を表す。〕 Ax is preferably any one of groups represented by the following structural formula. The group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later.
Figure JPOXMLDOC01-appb-C000029
 [In each formula, “-” extending from the inside of the ring represents a bond extending from any position of the ring. ]
　また、Ａｘは、下記構造式で表される基のいずれかであることがより好ましい。
Figure JPOXMLDOC01-appb-C000030
 Ax is more preferably any one of the groups represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000030
　さらに、Ａｘは、下記構造式で表される基のいずれかであることが特に好ましい。
Figure JPOXMLDOC01-appb-C000031
 Further, Ax is particularly preferably any one of groups represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000031
　Ａｘは、置換基を有していてもよい。「Ａｘが有する置換基の具体例」としては、例えば、フッ素原子、塩素原子等のハロゲン原子；シアノ基；メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基；ビニル基、アリル基等の炭素数２～６のアルケニル基；トリフルオロメチル基等の１個以上の水素原子がフッ素原子等のハロゲン原子で置換された炭素数１～６のアルキル基；ジメチルアミノ基等の炭素数２～１２のＮ，Ｎ－ジアルキルアミノ基；メトキシ基、エトキシ基、イソプロポキシ基等の炭素数１～６のアルコキシ基；ニトロ基；－ＯＣＦ３；－Ｃ（＝Ｏ）－Ｒｂ；－Ｏ－Ｃ（＝Ｏ）－Ｒｂ；－Ｃ（＝Ｏ）－Ｏ－Ｒｂ；－ＳＯ２Ｒａ；などが挙げられる。ここで、Ｒｂ及びＲａは、それぞれ、前記と同じ意味を表し、その好適例も前記と同じである。
　これらの中でも、ハロゲン原子；シアノ基；炭素数１～６のアルキル基；および炭素数１～６のアルコキシ基からなる群から選ばれる少なくとも一つの置換基が好ましい。 Ax may have a substituent. Examples of the “substituents of Ax” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group and propyl group; vinyl group, An alkenyl group having 2 to 6 carbon atoms such as an allyl group; an alkyl group having 1 to 6 carbon atoms in which one or more hydrogen atoms such as a trifluoromethyl group are substituted with a halogen atom such as a fluorine atom; An N, N-dialkylamino group having 2 to 12 carbon atoms; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; —OCF 3 ; —C (═O) —R b —O—C (═O) —R b ; —C (═O) —O—R b ; —SO 2 R a ; Wherein, R b and R a are each the same meanings as defined above, the preferred examples are also the same as above.
Among these, at least one substituent selected from the group consisting of a halogen atom; a cyano group; an alkyl group having 1 to 6 carbon atoms; and an alkoxy group having 1 to 6 carbon atoms is preferable.
－Ａｚ－
　Ａｚは、炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する有機基を表す。ここで、Ａｚは、Ｃ（Ａｙ）Ａｘである場合を除くものとする。 -Az-
Az represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms. Here, Az excludes the case of C (Ay) Ax.
　Ａｚは、下記（１）および（２）のいずれかであることが好ましい。
（１）少なくとも一つの炭素数６～３０の芳香族炭化水素環を有する、炭素数６～４０の炭化水素環基；
（２）炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する、炭素数２～４０の複素環基。 Az is preferably any of the following (1) and (2).
(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms;
(2) A heterocyclic group having 2 to 40 carbon atoms having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
　Ａｚは、下記構造式で表される基のいずれかであることがより好ましい。
Figure JPOXMLDOC01-appb-C000032
 〔各式中、Ｒは、水素原子、または、メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基を表す。〕 Az is more preferably any one of the groups represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000032
 [In each formula, R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group. ]
　Ａｒは、好ましくは、下記式（ＩＩＩ－１）～（ＩＩＩ－６）の何れかで表され、より好ましくは、下記式（ＩＩＩ－１）、下記式（ＩＩＩ－２）、下記式（ＩＩＩ－４）、または下記式（ＩＩＩ－５）で表され、特に好ましくは、下記式（ＩＩＩ－１）または下記式（ＩＩＩ－４）で表される。ここで、置換基として、メチル基、エチル基、プロピル基等の炭素数１～６のアルキル基を有していてもよい。
Figure JPOXMLDOC01-appb-C000033
 （上記式（ＩＩＩ－１）～（ＩＩＩ－６）中、Ａｘ、Ａｙ、ＡｚおよびＱは、前記と同じ意味を表し、その好適例も前記と同じであり、＊は、Ｚ１あるいはＺ２と結合することを表す。） Ar is preferably represented by any of the following formulas (III-1) to (III-6), more preferably the following formula (III-1), the following formula (III-2), the following formula (III) -4) or the following formula (III-5), particularly preferably the following formula (III-1) or the following formula (III-4). Here, the substituent may have an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group.
Figure JPOXMLDOC01-appb-C000033
 (In the above formulas (III-1) to (III-6), Ax, Ay, Az and Q have the same meaning as described above, and preferred examples thereof are also the same as above, and * represents Z 1 or Z 2. Represents that it is combined with.)
＜Ｚ１，Ｚ２＞
　Ｚ１およびＺ２は、それぞれ独立して、化学的な単結合、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｓ－、－Ｓ－Ｃ（＝Ｏ）－、－ＮＲ１１－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１１－、＊－ＣＨ２－Ｏ－、＊－ＣＨ２－ＣＨ２－Ｏ－、＊－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ２－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ２－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ＝ＣＨ－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ＝ＣＨ－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ＝Ｎ－、＊－Ｃ（ＣＨ３）＝Ｎ－、－Ｎ＝Ｎ－を表す。ここで、＊はＡｒと結合する位置を表し、Ｒ１１は、水素原子または炭素数１～６のアルキル基を表す。
　これらの中でも、Ｚ１およびＺ２は、それぞれ独立して、化学的な単結合、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ２－Ｏ－、＊－ＣＨ２－ＣＨ２－Ｏ－、＊－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ２－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、または＊－ＣＨ２－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－であることが好ましく、化学的な単結合、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ２－Ｏ－、＊－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、または＊－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－であることがより好ましく、化学的な単結合、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、または－Ｏ－Ｃ（＝Ｏ）－であることが最も好ましい。 <Z 1 , Z 2 >
Z 1 and Z 2 are each independently a chemical single bond, —O—, —C (═O) —O—, —O—C (═O) —, —C (═O) —S. -, - S-C (= O) -, - NR 11 -C (= O) -, - C (= O) -NR 11 -, * - CH 2 -O -, * - CH 2 -CH 2 - O -, * - CH 2 -C (= O) -O -, * - CH 2 -O-C (= O) -, * - CH 2 -CH 2 -C (= O) -O -, * - CH 2 —CH 2 —O—C (═O) —, * —CH═CH—C (═O) —O—, * —CH═CH—O—C (═O) —, * —CH═N -, * -C (CH 3 ) = N-, -N = N-. Here, * represents a position bonded to Ar, and R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Among these, Z 1 and Z 2 are each independently a chemical single bond, —O—, —C (═O) —O—, —O—C (═O) —, * —CH 2. -O -, * - CH 2 -CH 2 -O -, * - CH 2 -C (= O) -O -, * - CH 2 -O-C (= O) -, * - CH 2 -CH 2 —C (═O) —O— or * —CH 2 —CH 2 —O—C (═O) — is preferable, and a chemical single bond, —O—, —C (═O) — O -, - O-C ( = O) -, * - CH 2 -O -, * - CH 2 -C (= O) -O-, or * -CH 2 -O-C (= O) - in More preferably, it is most preferably a chemical single bond, —O—, —C (═O) —O—, or —O—C (═O) —.
＜Ａ１，Ａ２＞
　Ａ１およびＡ２は、それぞれ独立して、置換基を有していてもよい炭素数１～２０の二価の鎖状脂肪族基を表す。前記鎖状脂肪族基には、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１２－、－ＮＲ１２－、または、－Ｃ（＝Ｏ）－が介在していてもよい。ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く。ここで、Ｒ１２は、水素原子または炭素数１～６のアルキル基を表す。ただし、Ａ１の、Ｚ１に結合する炭素原子およびＹ１もしくはＹ３に結合する炭素原子、並びに、Ａ２の、Ｚ２に結合する炭素原子およびＹ２もしくはＹ４に結合する炭素原子が、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１２－、－ＮＲ１２－、または、－Ｃ（＝Ｏ）－に置換されることはない。 <A 1 ,A 2>
A 1 and A 2 each independently represents a divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent. The chain aliphatic group includes —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O—C (═O) —O—, — NR 12 —C (═O) —, —C (═O) —NR 12 —, —NR 12 —, or —C (═O) — may be present. However, the case where two or more of —O— or —S— are adjacent to each other is excluded. Here, R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Provided that the carbon atom bonded to Z 1 and the carbon atom bonded to Y 1 or Y 3 of A 1 and the carbon atom bonded to Z 2 and the carbon atom bonded to Y 2 or Y 4 of A 2 are bonded to each other. , —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O—C (═O) —O—, —NR 12 —C (═O) There is no substitution with —, —C (═O) —NR 12 —, —NR 12 —, or —C (═O) —.
　前記「置換基を有していてもよい炭素数１～２０の二価の鎖状脂肪族基」における「炭素数１～２０の二価の鎖状脂肪族基」の具体例としては、例えば、メチレン基、エチレン基、卜リメチレン基、プロピレン基、テ卜ラメチレン基、ペンタメチレン基、ヘキサメチレン基、オクタメチレン基、デカメチレン基〔－（ＣＨ２）１０－〕等の、炭素数１～２０のアルキレン基；ビニレン基、１ーメチルビニレン基、プロペニレン基、１－ブテニレン基、２－ブテニレン基、１ーペンテニレン基、２－ペンテニレン基等の、炭素数２～２０のアルケニレン基；１，３－ペンタジエニル基、１，３－ヘキサジエニル基等の炭素数２～２０の共役ジエンを有する基、等が挙げられる。これらの中でも、炭素数２～２０の二価の飽和鎖状脂肪族基、炭素数２～２０の二価の不飽和鎖状脂肪族基が好ましく、炭素数３～２０の二価の飽和鎖状脂肪族基、炭素数２～２０の二価の不飽和鎖状脂肪族基が更に好ましく、炭素数２～２０の二価の不飽和鎖状脂肪族基が特に好ましく、ビニレン基、プロぺニレン基、ブテニレン基が最も好ましい。
　また、前記「炭素数１～２０の二価の鎖状脂肪族基」には、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１２－、－ＮＲ１２－、または、－Ｃ（＝Ｏ）－が介在していてもよい（ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く。）。ここで、Ｒ１２は、水素原子または炭素数１～６のアルキル基を表し、水素原子またはメチル基であることが好ましい。前記「炭素数１～２０の二価の鎖状脂肪族基」に介在する基としては、－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｃ（＝Ｏ）－が好ましい。
　これらの基が介在する「炭素数１～２０の二価の鎖状脂肪族基」の具体例としては、－ＣＨ２－ＣＨ２－Ｏ－ＣＨ２－ＣＨ２－、－ＣＨ２－ＣＨ２－Ｓ－ＣＨ２－ＣＨ２－、－ＣＨ２－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－ＣＨ２－ＣＨ２－、－ＣＨ２－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－ＣＨ２－ＣＨ２－、－ＣＨ２－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－ＣＨ２－、－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－Ｏ－ＣＨ２－ＣＨ２－、－ＣＨ２－ＣＨ２－ＮＲ１２－Ｃ（＝Ｏ）－、－ＣＨ２－ＣＨ２－Ｃ（＝Ｏ）－ＮＲ１２－ＣＨ２－、－ＣＨ２－ＮＲ１２－ＣＨ２－ＣＨ２－、－ＣＨ２－Ｃ（＝Ｏ）－ＣＨ２－、などが挙げられる。 Specific examples of the “divalent chain aliphatic group having 1 to 20 carbon atoms” in the “divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent” include, for example, , Methylene group, ethylene group, hexamethylene group, propylene group, tetramethylene group, pentamethylene group, hexamethylene group, octamethylene group, decamethylene group [— (CH 2 ) 10 —], etc. Alkylene group; vinylene group, 1-methylvinylene group, propenylene group, 1-butenylene group, 2-butenylene group, 1-pentenylene group, 2-pentenylene group, etc., alkenylene group having 2 to 20 carbon atoms; 1,3-pentadienyl group And groups having a conjugated diene having 2 to 20 carbon atoms such as a 1,3-hexadienyl group. Among these, a divalent saturated chain aliphatic group having 2 to 20 carbon atoms and a divalent unsaturated chain aliphatic group having 2 to 20 carbon atoms are preferable, and a divalent saturated chain having 3 to 20 carbon atoms. More preferred are aliphatic aliphatic groups, divalent unsaturated chain aliphatic groups having 2 to 20 carbon atoms, particularly preferred are divalent unsaturated chain aliphatic groups having 2 to 20 carbon atoms, vinylene group, propylene group and propylene group. Most preferred are a nylene group and a butenylene group.
The “C 1-20 divalent chain aliphatic group” includes —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O—C (═O) —O—, —NR 12 —C (═O) —, —C (═O) —NR 12 —, —NR 12 —, or —C (═O) — interposed (However, the case where two or more of —O— or —S— are adjacent to each other is excluded). Here, R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and is preferably a hydrogen atom or a methyl group. Examples of the group intervening in the “divalent chain aliphatic group having 1 to 20 carbon atoms” include —O—, —O—C (═O) —, —C (═O) —O—, —C (= O)-is preferred.
These groups is mediated specific examples of the "divalent chain aliphatic group having 1 to 20 carbon atoms" is, -CH 2 -CH 2 -O-CH 2 -CH 2 -, - CH 2 -CH 2 -S-CH 2 -CH 2 -, - CH 2 -CH 2 -O-C (= O) -CH 2 -CH 2 -, - CH 2 -CH 2 -C (= O) -O-CH 2 - CH 2 -, - CH 2 -CH 2 -C (= O) -O-CH 2 -, - CH 2 -O-C (= O) -O-CH 2 -CH 2 -, - CH 2 -CH 2 -NR 12 -C (= O) - , - CH 2 -CH 2 -C (= O) -NR 12 -CH 2 -, - CH 2 -NR 12 -CH 2 -CH 2 -, - CH 2 -C (═O) —CH 2 — and the like.
　前記「置換基を有していてもよい炭素数１～２０の二価の鎖状脂肪族基」における置換基の具体例としては、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子；メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基、ｎ－ブトキシ基、ｓｅｃ－ブ卜キシ基、ｔ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－へキシルオキシ基等の炭素数１～６のアルコキシ基；などが挙げられる。これらの中でも、フッ素原子、メトキシ基、エトキシ基が好ましい。 Specific examples of the substituent in the “divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent” include, for example, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Halogen atom: carbon number such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyloxy group, etc. 1-6 alkoxy groups; and the like. Among these, a fluorine atom, a methoxy group, and an ethoxy group are preferable.
＜Ｂ１，Ｂ２＞
　Ｂ１およびＢ２は、それぞれ独立して、置換基を有していてもよい環状脂肪族基、または、置換基を有していてもよい芳香族基を表し、置換基を有していてもよい炭素数５～２０の環状脂肪族基、または、置換基を有していてもよい炭素数２～２０の芳香族基が好ましい。 <B 1, B 2>
B 1 and B 2 each independently represent a cyclic aliphatic group that may have a substituent or an aromatic group that may have a substituent, and have a substituent. A cyclic aliphatic group having 5 to 20 carbon atoms or an aromatic group having 2 to 20 carbon atoms which may have a substituent is preferable.
　前記「置換基を有していてもよい環状脂肪族基」における「環状脂肪族基」の具体例としては、例えば、シクロペンタン－１，３－ジイル、シクロヘキサン－１，４－ジイル、シクロヘプタン－１，４－ジイル、シクロオクタン－１，５－ジイル等の炭素数５～２０のシクロアルカンジイル基；デカヒドロナフタレン－１，５－ジイル、デカヒドロナフタレン－２，６－ジイル等の炭素数５～２０のビシクロアルカンジイル基；などが挙げられる。これらの中でも、環状脂肪族基としては、炭素数５～２０のシクロアルカンジイル基が好ましく、シクロヘキサンジイル基がより好ましく、シクロヘキサン－１，４－ジイル基が特に好ましい。前記「環状脂肪族基」は、トランス体であっても、シス体であっても、或いは、シス体とトランス体の混合物であってもよいが、トランス体がより好ましい。 Specific examples of the “cycloaliphatic group” in the “optionally substituted cycloaliphatic group” include cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, cycloheptane, and the like. C1-C20 cycloalkanediyl groups such as 1,4-diyl, cyclooctane-1,5-diyl; carbons such as decahydronaphthalene-1,5-diyl and decahydronaphthalene-2,6-diyl And a bicycloalkanediyl group of 5 to 20; Among these, the cycloaliphatic group is preferably a cycloalkanediyl group having 5 to 20 carbon atoms, more preferably a cyclohexanediyl group, and particularly preferably a cyclohexane-1,4-diyl group. The “cycloaliphatic group” may be a trans isomer, a cis isomer, or a mixture of a cis isomer and a trans isomer, but a trans isomer is more preferable.
　前記「置換基を有していてもよい芳香族基」における「芳香族基」の具体例としては、例えば、１，２－フェニレン基、１，３－フェニレン基、１，４－フェニレン基、１，４－ナフチレン基、１，５－ナフチレン基、２，６－ナフチレン基、４，４’－ビフェニレン基等の、炭素数６～１８の芳香族炭化水素環基；フラン－２，５－ジイル、チオフェン－２，５－ジイル、ピリジン－２，５－ジイル、ピラジン－２，５－ジイル等の、炭素数２～２０の芳香族複素環基；などが挙げられる。これらの中でも、炭素数６～１８の芳香族炭化水素環基が好ましく、フェニレン基がより好ましく、、１，４－フェニレン基が特に好ましい。 Specific examples of the “aromatic group” in the “aromatic group optionally having substituent (s)” include, for example, 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, An aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as 1,4-naphthylene group, 1,5-naphthylene group, 2,6-naphthylene group, 4,4′-biphenylene group; furan-2,5- And aromatic heterocyclic groups having 2 to 20 carbon atoms such as diyl, thiophene-2,5-diyl, pyridine-2,5-diyl and pyrazine-2,5-diyl. Among these, an aromatic hydrocarbon ring group having 6 to 18 carbon atoms is preferable, a phenylene group is more preferable, and a 1,4-phenylene group is particularly preferable.
　前記「置換基を有していてもよい環状脂肪族基」および前記「置換基を有していてもよい芳香族基」における置換基としては、例えば、ハロゲン原子、炭素数１～６のアルキル基、炭素数１～５のアルコキシ基、ニトロ基、シアノ基、などが挙げられる。
　前記環状脂肪族基および前記芳香族基は、上述した置換基から選ばれる少なくとも１つの置換基を有していてもよい。なお、置換基を複数有する場合は、各置換基は同一でも相異なっていてもよい。 Examples of the substituent in the “optionally substituted cycloaliphatic group” and the “optionally substituted aromatic group” include, for example, a halogen atom, an alkyl having 1 to 6 carbon atoms. Group, an alkoxy group having 1 to 5 carbon atoms, a nitro group, a cyano group, and the like.
The cycloaliphatic group and the aromatic group may have at least one substituent selected from the above-described substituents. In addition, when it has two or more substituents, each substituent may be the same or different.
＜Ｙ１～Ｙ４＞
　Ｙ１～Ｙ４は、それぞれ独立して、単結合、－Ｏ－、－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－ＮＲ１３－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１３－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１３－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－ＮＲ１３－、または、－ＮＲ１３－Ｃ（＝Ｏ）－ＮＲ１４－を表す。ここで、Ｒ１３およびＲ１４は、それぞれ独立して、水素原子または炭素数１～６のアルキル基を表す。
　これらの中でも、Ｙ１～Ｙ４は、それぞれ独立して、単結合、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、または－Ｏ－Ｃ（＝Ｏ）－であることが好ましく、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、または－Ｏ－Ｃ（＝Ｏ）－であることがより好ましい。 <Y 1 to Y 4 >
Y 1 to Y 4 are each independently a single bond, —O—, —C (═O) —, —C (═O) —O—, —O—C (═O) —, —NR 13. —C (═O) —, —C (═O) —NR 13 —, —O—C (═O) —O—, —NR 13 —C (═O) —O—, —O—C (= O) —NR 13 — or —NR 13 —C (═O) —NR 14 —. Here, R 13 and R 14 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Among these, Y 1 to Y 4 are preferably each independently a single bond, —O—, —C (═O) —O—, or —O—C (═O) —, More preferably, they are O—, —C (═O) —O—, or —O—C (═O) —.
＜Ｇ１，Ｇ２＞
　Ｇ１およびＧ２は、それぞれ独立して、炭素数１～２０の脂肪族炭化水素基、および、炭素数３～２０の脂肪族炭化水素基に含まれるメチレン基（－ＣＨ２－）の１以上が－Ｏ－または－Ｃ（＝Ｏ）－に置換された基のいずれかの有機基である。なお、Ｇ１およびＧ２の前記有機基に含まれる水素原子は、炭素数１～５のアルキル基、炭素数１～５のアルコキシ基、または、ハロゲン原子に置換されていてもよい。ただし、Ｇ１およびＧ２の両末端のメチレン基（－ＣＨ２－）が、－Ｏ－または－Ｃ（＝Ｏ）－に置換されることはない。 <G 1, G 2>
G 1 and G 2 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and 1 of a methylene group (—CH 2 —) contained in an aliphatic hydrocarbon group having 3 to 20 carbon atoms. The above is an organic group of any of the groups substituted with —O— or —C (═O) —. Note that a hydrogen atom contained in the organic group of G 1 and G 2 may be substituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom. However, the methylene groups (—CH 2 —) at both ends of G 1 and G 2 are not substituted with —O— or —C (═O) —.
　前記「炭素数１～２０の脂肪族炭化水素基」および前記「炭素数３～２０の脂肪族炭化水素基」の具体例としては、それぞれ、炭素数１～２０のアルキレン基、および、炭素数３～２０のアルキレン基が挙げられる。
　これらの中でも、ｎ－ブチレン基、ｎ－へキシレン基、ｎ－オクチレン基、ｎ－デカメチレン基〔－（ＣＨ２）１０－〕、が好ましい。 Specific examples of the “aliphatic hydrocarbon group having 1 to 20 carbon atoms” and the “aliphatic hydrocarbon group having 3 to 20 carbon atoms” include an alkylene group having 1 to 20 carbon atoms and a carbon number, respectively. Examples include 3 to 20 alkylene groups.
Among these, n-butylene group, n-hexylene group, n-octylene group, and n-decamethylene group [— (CH 2 ) 10 —] are preferable.
＜Ｐ１，Ｐ２＞
　Ｐ１およびＰ２は、それぞれ独立して、重合性基を表す。
　前記重合性基の具体例としては、例えば、アクリロイルオキシ基、メタクリロイルオキシ基等のＣＨ２＝ＣＲ３１－Ｃ（＝Ｏ）－Ｏ－で表される基（Ｒ３１は、水素原子、メチル基、または塩素原子を表す。）、ビニル基、ビニルエーテル基、ｐ－スチルベン基、アクリロイル基、メタクリロイル基、カルボキシル基、メチルカルボニル基、水酸基、アミド基、炭素数１～４のアルキルアミノ基、アミノ基、エポキシ基、オキセタニル基、アルデヒド基、イソシアネート基またはチオイソシアネート基などが挙げられる。これらの中でも、ＣＨ２＝ＣＲ３１－Ｃ（＝Ｏ）－Ｏ－で表される基が好ましく、ＣＨ２＝ＣＨ－Ｃ（＝Ｏ）－Ｏ－で表される基（アクリロイルオキシ基）、ＣＨ２＝Ｃ（ＣＨ３）－Ｃ（＝Ｏ）－Ｏ－で表される基（メタクリロイルオキシ基）がより好ましく、アクリロイルオキシ基が特に好ましい。 <P 1 , P 2 >
P 1 and P 2 each independently represent a polymerizable group.
Specific examples of the polymerizable group include a group represented by CH 2 ═CR 31 —C (═O) —O— such as acryloyloxy group and methacryloyloxy group (R 31 is a hydrogen atom, methyl group) Or a chlorine atom.), Vinyl group, vinyl ether group, p-stilbene group, acryloyl group, methacryloyl group, carboxyl group, methylcarbonyl group, hydroxyl group, amide group, alkylamino group having 1 to 4 carbon atoms, amino group , Epoxy group, oxetanyl group, aldehyde group, isocyanate group or thioisocyanate group. Among these, a group represented by CH 2 ═CR 31 —C (═O) —O— is preferable, and a group represented by CH 2 ═CH—C (═O) —O— (acryloyloxy group), A group represented by CH 2 ═C (CH 3 ) —C (═O) —O— (methacryloyloxy group) is more preferred, and an acryloyloxy group is particularly preferred.
＜ｐ，ｑ＞
　ｐおよびｑは、それぞれ独立して、０～２の整数を表す。
　これらの中でも、ｐおよびｑは、それぞれ独立して、１であることが好ましい。
　ｐおよびｑの両方が１である場合、前述した式（Ｉ）中のＢ１およびＢ２は、それぞれ独立して、置換基を有していてもよい芳香族基であることが好ましく、置換基を有していてもよい炭素数６～１８の芳香族基であることがより好ましく、フェニレン基が特に好ましい。 <P, q>
p and q each independently represents an integer of 0 to 2.
Among these, it is preferable that p and q are each independently 1.
When both p and q are 1, B 1 and B 2 in the aforementioned formula (I) are preferably each independently an aromatic group which may have a substituent. An aromatic group having 6 to 18 carbon atoms which may have a group is more preferable, and a phenylene group is particularly preferable.
　また、重合性化合物（Ｉ）は、特に限定されるものではないが、Ａｒを中心とした対称構造を有する（即ち、Ｚ１とＺ２、Ａ１とＡ２、Ｙ１とＹ２、Ｂ１とＢ２、ｎとｍ、Ｙ３とＹ４、Ｇ１とＧ２、Ｐ１とＰ２が、それぞれ同一である（Ａｒを中心として対称である））ことが好ましい。 The polymerizable compound (I) is not particularly limited, but has a symmetric structure centered on Ar (that is, Z 1 and Z 2 , A 1 and A 2 , Y 1 and Y 2 , B 1 and B 2 , n and m, Y 3 and Y 4 , G 1 and G 2 , and P 1 and P 2 are preferably the same (symmetric about Ar).
　上述した重合性液晶化合物（Ｉ）は、既知の合成反応を組み合わせて合成することができる。即ち、様々な文献（例えば、国際公開第２０１２／１４１２４５号、国際公開第２０１２／１４７９０４号、国際公開第２０１４／０１０３２５号、国際公開第２０１３／０４６７８１号、国際公開第２０１４／０６１７０９号、国際公開第２０１４／１２６１１３号、国際公開第２０１５／０６４６９８号、国際公開第２０１５－１４０３０２号、国際公開第２０１５／１２９６５４号、国際公開第２０１５／１４１７８４号、国際公開第２０１６／１５９１９３号、国際公開第２０１２／１６９４２４号、国際公開第２０１２／１７６６７９号、国際公開第２０１５／１２２３８５号等に記載の方法を参照して合成できる。 The above-described polymerizable liquid crystal compound (I) can be synthesized by combining known synthetic reactions. That is, various documents (for example, International Publication No. 2012/141245, International Publication No. 2012/147904, International Publication No. 2014/010325, International Publication No. 2013/046871, International Publication No. 2014/061709, International Publication No. 2014/126113, International Publication No. 2015/064698, International Publication No. 2015-140302, International Publication No. 2015/129654, International Publication No. 2015/141784, International Publication No. 2016/159193, International Publication No. 2012 / 169424, International Publication No. 2012/176679, International Publication No. 2015/122385 and the like.
（２）重合性液晶組成物
　上記重合性液晶組成物は、少なくとも重合性液晶化合物（Ｉ）と、重合開始剤とを含有する。
　なお、上記重合性液晶組成物は、後述するように、本発明の高分子、光学フィルム、光学異方体の製造原料として有用である。そして、本発明の重合性液晶組成物によれば、広帯域性を示す理想的な波長分散性、即ち逆波長分散性を有する光学フィルム等を良好に製造することができる。 (2) Polymerizable liquid crystal composition The polymerizable liquid crystal composition contains at least a polymerizable liquid crystal compound (I) and a polymerization initiator.
The polymerizable liquid crystal composition is useful as a raw material for producing the polymer, optical film, and optical anisotropic body of the present invention, as will be described later. According to the polymerizable liquid crystal composition of the present invention, it is possible to satisfactorily produce an optical film or the like having ideal wavelength dispersion exhibiting broadband properties, that is, reverse wavelength dispersion.
　ここで、重合開始剤は、重合性液晶組成物に含まれている重合性液晶化合物（Ｉ）の重合反応をより効率的に行う観点から配合される。
　そして、用いる重合開始剤としては、ラジカル重合開始剤、アニオン重合開始剤、カチオン重合開始剤等が挙げられる。 Here, a polymerization initiator is mix | blended from a viewpoint of performing the polymerization reaction of polymerizable liquid crystal compound (I) contained in the polymerizable liquid crystal composition more efficiently.
And as a polymerization initiator to be used, a radical polymerization initiator, an anionic polymerization initiator, a cationic polymerization initiator, etc. are mentioned.
　ラジカル重合開始剤としては、加熱することにより、重合性液晶化合物の重合を開始し得る活性種が発生する化合物である熱ラジカル発生剤；や、可視光線、紫外線（ｉ線など）、遠紫外線、電子線、Ｘ線等の露光光の露光により、重合性液晶化合物の重合を開始しえる活性種が発生する化合物である光ラジカル発生剤；のいずれも使用可能であるが、光ラジカル発生剤を使用するのが好適である。 As the radical polymerization initiator, a thermal radical generator which is a compound that generates an active species capable of initiating polymerization of a polymerizable liquid crystal compound by heating; visible light, ultraviolet light (i-line etc.), far ultraviolet light, Any of radical photogenerators, which are compounds that generate active species capable of initiating polymerization of a polymerizable liquid crystal compound upon exposure to exposure light such as an electron beam or X-ray, can be used. It is preferred to use.
　光ラジカル発生剤としては、アセトフェノン系化合物、ビイミダゾール系化合物、トリアジン系化合物、Ｏ－アシルオキシム系化合物、オニウム塩系化合物、ベンゾイン系化合物、ベンゾフェノン系化合物、α－ジケトン系化合物、多核キノン系化合物、キサントン系化合物、ジアゾ系化合物、イミドスルホナート系化合物等を挙げることができる。これらの化合物は、露光によって活性ラジカルまたは活性酸、あるいは活性ラジカルと活性酸の両方を発生する成分である。光ラジカル発生剤は、一種単独で、あるいは２種以上を組み合わせて用いることができる。 Photoradical generators include acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, α-diketone compounds, polynuclear quinone compounds , Xanthone compounds, diazo compounds, imide sulfonate compounds, and the like. These compounds are components that generate active radicals or active acids or both active radicals and active acids upon exposure. A photoradical generator can be used individually by 1 type or in combination of 2 or more types.
　アセトフェノン系化合物の具体例としては、２－ヒドロキシ－２－メチル－１－フェニルプロパン－１－オン、２－メチル－１－〔４－（メチルチオ）フェニル〕－２－モルフォリノプロパン－１－オン、２－ベンジル－２－ジメチルアミノ－１－（４－モルフォリノフェニル）ブタン－１－オン、１－ヒドロキシシクロヘキシル・フェニルケトン、２，２－ジメトキシ－１，２－ジフェニルエタン－１－オン、１－〔４－（フェニルチオ）フェニル〕－オクタン－１，２－ジオン２－（Ｏ－ベンゾイルオキシム）等を挙げることができる。 Specific examples of acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, And 1- [4- (phenylthio) phenyl] -octane-1,2-dione 2- (O-benzoyloxime).
　ビイミダゾール系化合物の具体例としては、２，２’－ビス（２－クロロフェニル）－４，４’，５，５’－テトラキス（４－エトキシカルボニルフェニル）－１，２’－ビイミダゾール、２，２’－ビス（２－ブロモフェニル）－４，４’，５，５’－テトラキス（４－エトキシカルボニルフェニル）－１，２’－ビイミダゾール、２，２’－ビス（２－クロロフェニル）－４，４’，５，５’－テトラフェニル－１，２’－ビイミダゾール、２，２’－ビス（２，４－ジクロロフェニル）－４，４’，５，５’－テトラフェニル－１，２’－ビイミダゾール、２，２’－ビス（２，４，６－トリクロロフェニル）－４，４’，５，５’－テトラフェニル－１，２’－ビイミダゾール、２，２’－ビス（２－ブロモフェニル）－４，４’，５，５’－テトラフェニル－１，２’－ビイミダゾール、２，２’－ビス（２，４－ジブロモフェニル）－４，４’，５，５’－テトラフェニル－１，２’－ビイミダゾール、２，２’－ビス（２，４，６－トリブロモフェニル）－４，４’，５，５’－テトラフェニル－１，２’－ビイミダゾール等を挙げることができる。 Specific examples of the biimidazole compound include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2 , 2'-bis (2-bromophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4-dichlorophenyl) -4,4', 5,5'-tetraphenyl-1 , 2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′- Bis (2-bromophenyl) -4,4 ' 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4-dibromophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-bi Examples thereof include imidazole and 2,2′-bis (2,4,6-tribromophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole.
　なお、本発明においては、光重合開始剤（光ラジカル発生剤）としてビイミダゾール系化合物を用いる場合、水素供与体を併用することが、感度をさらに改良することができる点で好ましい。
　ここで、「水素供与体」とは、露光によりビイミダゾール系化合物から発生したラジカルに対して、水素原子を供与することができる化合物を意味する。水素供与体としては、下記で定義するメルカプタン系化合物、アミン系化合物等が好ましい。 In the present invention, when a biimidazole compound is used as a photopolymerization initiator (photo radical generator), it is preferable to use a hydrogen donor in view of further improving sensitivity.
Here, the “hydrogen donor” means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure. As the hydrogen donor, mercaptan compounds, amine compounds and the like defined below are preferable.
　メルカプタン系化合物の具体例としては、２－メルカプトベンゾチアゾール、２－メルカプトベンゾオキサゾール、２－メルカプトベンゾイミダゾール、２，５－ジメルカプト－１，３，４－チアジアゾール、２－メルカプト－２，５－ジメチルアミノピリジン等を挙げることができる。アミン系化合物としては、４，４’－ビス（ジメチルアミノ）ベンゾフェノン、４，４’－ビス（ジエチルアミノ）ベンゾフェノン、４－ジエチルアミノアセトフェノン、４－ジメチルアミノプロピオフェノン、エチル－４－ジメチルアミノベンゾエート、４－ジメチルアミノ安息香酸、４－ジメチルアミノベンゾニトリル等を挙げることができる。 Specific examples of mercaptan compounds include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-2,5-dimethyl. An aminopyridine etc. can be mentioned. Examples of amine compounds include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, ethyl-4-dimethylaminobenzoate, Examples include 4-dimethylaminobenzoic acid and 4-dimethylaminobenzonitrile.
　トリアジン系化合物の具体例としては、２，４，６－トリス（トリクロロメチル）－ｓ－トリアジン、２－メチル－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－〔２－（５－メチルフラン－２－イル）エテニル〕－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－〔２－（フラン－２－イル）エテニル〕－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－〔２－（４－ジエチルアミノ－２－メチルフェニル）エテニル〕－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－〔２－（３，４－ジメトキシフェニル）エテニル〕－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－（４－メトキシフェニル）－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－（４－エトキシスチリル）－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－（４－ｎ－ブトキシフェニル）－４，６－ビス（トリクロロメチル）－ｓ－トリアジン等のハロメチル基を有するトリアジン系化合物を挙げることができる。 Specific examples of the triazine compound include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2- (5 -Methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloromethyl)- s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxyphenyl) ethenyl -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-ethoxys) Triazine-based compounds having a halomethyl group such as ryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine Can be mentioned.
　Ｏ－アシルオキシム系化合物の具体例としては、１－〔４－（フェニルチオ）フェニル〕－ヘプタン－１，２－ジオン２－（Ｏ－ベンゾイルオキシム）、１－〔４－（フェニルチオ）フェニル〕－オクタン－１，２－ジオン２－（Ｏ－ベンゾイルオキシム）、１－〔４－（ベンゾイル）フェニル〕－オクタン－１，２－ジオン２－（Ｏ－ベンゾイルオキシム）、１－［９－エチル－６－（２－メチルベンゾイル）－９Ｈ－カルバゾール－３－イル］－エタノン１－（Ｏ－アセチルオキシム）、１－［９－エチル－６－（３－メチルベンゾイル）－９Ｈ－カルバゾール－３－イル］－エタノン１－（Ｏ－アセチルオキシム）、１－（９－エチル－６－ベンゾイル－９Ｈ－カルバゾール－３－イル）－エタノン１－（Ｏ－アセチルオキシム）、エタノン－１－［９－エチル－６－（２－メチル－４－テトラヒドロフラニルベンゾイル）－９Ｈ－カルバゾール－３－イル］－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－（２－メチル－４－テトラヒドロピラニルベンゾイル）－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－（２－メチル－５－テトラヒドロフラニルベンゾイル）－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－（２－メチル－５－テトラヒドロピラニルベンゾイル）－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－｛２－メチル－４－（２，２－ジメチル－１，３－ジオキソラニル）ベンゾイル｝－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）、エタノン－１－［９－エチル－６－（２－メチル－４－テトラヒドロフラニルメトキシベンゾイル）－９Ｈ－カルバゾール－３－イル］－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－（２－メチル－４－テトラヒドロピラニルメトキシベンゾイル）－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－（２－メチル－５－テトラヒドロフラニルメトキシベンゾイル）－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）、エタノン－１－［９－エチル－６－（２－メチルベンゾイル）－９Ｈ－カルバゾール－３－イル］－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－（２－メチル－５－テトラヒドロピラニルメトキシベンゾイル）－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）、エタノン－１－〔９－エチル－６－｛２－メチル－４－（２，２－ジメチル－１，３－ジオキソラニル）メトキシベンゾイル｝－９Ｈ－カルバゾール－３－イル〕－１－（Ｏ－アセチルオキシム）等を挙げることができる。 Specific examples of O-acyloxime compounds include 1- [4- (phenylthio) phenyl] -heptane-1,2-dione 2- (O-benzoyloxime), 1- [4- (phenylthio) phenyl]- Octane-1,2-dione 2- (O-benzoyloxime), 1- [4- (benzoyl) phenyl] -octane-1,2-dione 2- (O-benzoyloxime), 1- [9-ethyl- 6- (2-Methylbenzoyl) -9H-carbazol-3-yl] -ethanone 1- (O-acetyloxime), 1- [9-ethyl-6- (3-methylbenzoyl) -9H-carbazole-3- Yl] -ethanone 1- (O-acetyloxime), 1- (9-ethyl-6-benzoyl-9H-carbazol-3-yl) -ethanone 1- (O-acetyloxime), Tanone-1- [9-ethyl-6- (2-methyl-4-tetrahydrofuranylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl- 6- (2-Methyl-4-tetrahydropyranylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-5) -Tetrahydrofuranylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-5-tetrahydropyranylbenzoyl) -9H- Carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- {2-methyl-4- (2,2-dimethyl-1,3-dio Solanyl) benzoyl} -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-4-tetrahydrofuranylmethoxybenzoyl) -9H-carbazole -3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-4-tetrahydropyranylmethoxybenzoyl) -9H-carbazol-3-yl] -1 -(O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-5-tetrahydrofuranylmethoxybenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), Ethanone-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime) Ethanone-1- [9-ethyl-6- (2-methyl-5-tetrahydropyranylmethoxybenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9 -Ethyl-6- {2-methyl-4- (2,2-dimethyl-1,3-dioxolanyl) methoxybenzoyl} -9H-carbazol-3-yl] -1- (O-acetyloxime) Can do.
　また、光ラジカル発生剤として、市販品をそのまま用いることもできる。具体例としては、ＢＡＳＦ社製の、商品名：Ｉｒｇａｃｕｒｅ９０７、商品名：Ｉｒｇａｃｕｒｅ１８４、商品名：Ｉｒｇａｃｕｒｅ３６９、商品名：Ｉｒｇａｃｕｒｅ６５１、商品名：Ｉｒｇａｃｕｒｅ８１９、商品名：Ｉｒｇａｃｕｒｅ９０７、および、商品名：ＩｒｇａｃｕｒｅＯＸＥ０２、並びに、ＡＤＥＫＡ社製の、商品名：アデカアークルズＮ１９１９Ｔ等が挙げられる。 Also, commercially available products can be used as they are as photo radical generators. As specific examples, trade names: Irgacure 907, trade names: Irgacure 184, trade names: Irgacure 369, trade names: Irgacure 651, trade names: Irgacure 819, trade names: Irgacure 907, and trade names: Irgacure AX Product name: ADEKA ARKLES N1919T, etc.
　前記アニオン重合開始剤としては、アルキルリチウム化合物；ビフェニル、ナフタレン、ピレン等の、モノリチウム塩またはモノナトリウム塩；ジリチウム塩やトリリチウム塩等の多官能性開始剤；等が挙げられる。 Examples of the anionic polymerization initiator include alkyl lithium compounds; monolithium salts or monosodium salts such as biphenyl, naphthalene, and pyrene; polyfunctional initiators such as dilithium salts and trilithium salts;
　また、前記カチオン重合開始剤としては、硫酸、リン酸、過塩素酸、トリフルオロメタンスルホン酸等のプロトン酸；三フッ化ホウ素、塩化アルミニウム、四塩化チタン、四塩化スズのようなルイス酸；芳香族オニウム塩または芳香族オニウム塩と、還元剤との併用系；が挙げられる。 Examples of the cationic polymerization initiator include proton acids such as sulfuric acid, phosphoric acid, perchloric acid and trifluoromethanesulfonic acid; Lewis acids such as boron trifluoride, aluminum chloride, titanium tetrachloride and tin tetrachloride; A combined system of a group onium salt or an aromatic onium salt and a reducing agent.
　これらの重合開始剤は一種単独で、または二種以上を組み合わせて用いることができる。 These polymerization initiators can be used singly or in combination of two or more.
　なお、上記重合性液晶組成物において、重合開始剤の配合割合は、重合性液晶組成物に含まれる重合性液晶化合物１００質量部に対し、通常、０．１～３０質量部、好ましくは０．５～１０質量部である。 In the above polymerizable liquid crystal composition, the blending ratio of the polymerization initiator is usually 0.1 to 30 parts by mass, preferably 0.1 to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. 5 to 10 parts by mass.
　また、上記重合性液晶組成物には、表面張力を調整するために、界面活性剤を配合するのが好ましい。当該界面活性剤としては、特に限定はないが、通常、ノニオン系界面活性剤が好ましい。当該ノニオン系界面活性剤としては、市販品を用いればよく、例えば、含フッ素基、親水性基、および親油性基含有オリゴマーであるノニオン系界面活性剤、例えば、ＡＧＣセイミケミカル社製のサーフロンシリーズ（Ｓ２４２、Ｓ２４３、Ｓ３８６、Ｓ６１１、Ｓ６５１など）、ＤＩＣ社製のメガファックシリーズ（Ｆ２５１、Ｆ５５４、Ｆ５５６、Ｆ５６２、ＲＳ－７５、ＲＳ－７６－Ｅなど）、ネオス社製のフタージェントシリーズ（ＦＴＸ６０１ＡＤ、ＦＴＸ６０２Ａ、ＦＴＸ６０１ＡＤＨ２、ＦＴＸ６５０Ａなど）等が挙げられる。また、これらの界面活性剤は、１種類を単独で用いてもよく、２種類以上を任意の比率で組み合わせて用いてもよい。
　ここで、上記重合性液晶組成物において、界面活性剤の配合割合は、重合性液晶組成物に含まれる重合性液晶化合物１００質量部に対し、通常、０．０１～１０質量部、好ましくは０．０１～２質量部である。 The polymerizable liquid crystal composition preferably contains a surfactant in order to adjust the surface tension. The surfactant is not particularly limited, but a nonionic surfactant is usually preferable. As the nonionic surfactant, commercially available products may be used. For example, nonionic surfactants that are oligomers containing fluorine-containing groups, hydrophilic groups, and lipophilic groups, such as Surflon manufactured by AGC Seimi Chemical Co., Ltd. Series (S242, S243, S386, S611, S651, etc.), DIC's MegaFuck series (F251, F554, F556, F562, RS-75, RS-76-E, etc.), Neos' footagent series ( FTX601AD, FTX602A, FTX601ADH2, FTX650A, etc.). Moreover, these surfactants may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
Here, in the polymerizable liquid crystal composition, the blending ratio of the surfactant is usually 0.01 to 10 parts by mass, preferably 0 with respect to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. .01 to 2 parts by mass.
　更に、上記重合性液晶組成物には、重合性液晶化合物、重合開始剤、界面活性剤の他、本発明の効果に影響が出ない範囲で、他の成分が更に含まれていてもよい。他の成分としては、金属、金属錯体、染料、顔料、蛍光材料、燐光材料、レベリング剤、チキソ剤、ゲル化剤、多糖類、紫外線吸収剤、赤外線吸収剤、抗酸化剤、イオン交換樹脂、酸化チタン等の金属酸化物等が挙げられる。
　また、他の成分としては、他の共重合可能な単量体も挙げられる。具体的には、特に限定されるものではなく、例えば、４－（２－メタクリロイルオキシエチルオキシ）安息香酸－４’－メトキシフェニル、４－（６－メタクリロイルオキシヘキシルオキシ）安息香酸ビフェニル、４－（２－アクリロイルオキシエチルオキシ）安息香酸－４’－シアノビフェニル、４－（２－メタクリロリルオキシエチルオキシ）安息香酸－４’－シアノビフェニル、４－（２－メタクリロリルオキシエチルオキシ）安息香酸－３’，４’－ジフルオロフェニル、４－（２－メタクリロイルオキシエチルオキシ）安息香酸ナフチル、４－アクリロイルオキシ－４’－デシルビフェニル、４－アクリロイルオキシ－４’－シアノビフェニル、４－（２－アクリロイルオキシエチルオキシ）－４’－シアノビフェニル、４－（２－メタクリロイルオキシエチルオキシ）－４’－メトキシビフェニル、４－（２－メタクリロイルオキシエチルオキシ）－４’－（４’’－フルオロベンジルオキシ）－ビフェニル、４－アクリロイルオキシ－４’－プロピルシクロヘキシルフェニル、４－メタクリロイル－４’－ブチルビシクロヘキシル、４－アクリロイル－４’－アミルトラン、４－アクリロイル－４’－（３，４－ジフルオロフェニル）ビシクロヘキシル、４－（２－アクリロイルオキシエチル）安息香酸（４－アミルフェニル）、４－（２－アクリロイルオキシエチル）安息香酸（４－（４’－プロピルシクロヘキシル）フェニル）、商品名「ＬＣ－２４２」（ＢＡＳＦ社製）、トランス－１，４－ビス［４－［６－（アクリロイルオキシ）ヘキシルオキシ］フェニル］シクロヘキサンジカルボキシレート、並びに、特開２００７－００２２０８号公報、特開２００９－１７３８９３号公報、特開２００９－２７４９８４号公報、特開２０１０－０３０９７９号公報、特開２０１０－０３１２２３号公報、特開２０１１－００６３６０号公報および特開２０１０－２４４３８号公報、国際公開第２０１２／１４１２４５号、国際公開第２０１２／１４７９０４号、国際公開第２０１２／１６９４２４号、国際公開第２０１２／７６６７９号、国際公開第２０１３／１８０２１７号、国際公開第２０１４／０１０３２５号、国際公開第２０１４／０６１７０９号、国際公開第２０１４／０６５１７６号、国際公開第２０１４／１２６１１３号、国際公開第２０１５／０２５７９３号、国際公開第２０１５／０６４６９８号、国際公開第２０１５／１２２３８４号、国際公開第２０１５／１２２３８５号に開示されている化合物等の共重合可能な単量体が挙げられる。
　これらの他の成分の配合割合は、重合性液晶化合物に含まれる重合性液晶化合物１００質量部に対し、通常、０．００５～５０質量部である。 Furthermore, the polymerizable liquid crystal composition may further contain other components in addition to the polymerizable liquid crystal compound, the polymerization initiator, and the surfactant as long as the effects of the present invention are not affected. Other components include metals, metal complexes, dyes, pigments, fluorescent materials, phosphorescent materials, leveling agents, thixotropic agents, gelling agents, polysaccharides, ultraviolet absorbers, infrared absorbers, antioxidants, ion exchange resins, Examples thereof include metal oxides such as titanium oxide.
In addition, other components include other copolymerizable monomers. Specifically, it is not particularly limited. For example, 4- (2-methacryloyloxyethyloxy) benzoic acid-4′-methoxyphenyl, 4- (6-methacryloyloxyhexyloxy) benzoic acid biphenyl, 4- (2-acryloyloxyethyloxy) benzoic acid-4′-cyanobiphenyl, 4- (2-methacrylolyloxyethyloxy) benzoic acid-4′-cyanobiphenyl, 4- (2-methacrylolyloxyethyloxy) Benzoic acid-3 ′, 4′-difluorophenyl, 4- (2-methacryloyloxyethyloxy) benzoic acid naphthyl, 4-acryloyloxy-4′-decylbiphenyl, 4-acryloyloxy-4′-cyanobiphenyl, 4- (2-acryloyloxyethyloxy) -4′-cyanobiphenyl, 4- (2-methacrylic) Yloxyethyloxy) -4′-methoxybiphenyl, 4- (2-methacryloyloxyethyloxy) -4 ′-(4 ″ -fluorobenzyloxy) -biphenyl, 4-acryloyloxy-4′-propylcyclohexylphenyl, 4-methacryloyl-4′-butylbicyclohexyl, 4-acryloyl-4′-amyltran, 4-acryloyl-4 ′-(3,4-difluorophenyl) bicyclohexyl, 4- (2-acryloyloxyethyl) benzoic acid ( 4-Amylphenyl), 4- (2-acryloyloxyethyl) benzoic acid (4- (4′-propylcyclohexyl) phenyl), trade name “LC-242” (manufactured by BASF), trans-1,4-bis [4- [6- (acryloyloxy) hexyloxy] phenyl] cyclohexanedicar Boxylate and JP 2007-002208 A, JP 2009-173893 A, JP 2009-274984 A, JP 2010-030979 A, JP 2010-031223 A, JP 2011-006360 A. Gazette and Japanese Patent Application Laid-Open No. 2010-24438, International Publication No. 2012/141245, International Publication No. 2012/147904, International Publication No. 2012/169424, International Publication No. 2012/76679, International Publication No. 2013/180217, International Publication No. 2014/010325, International Publication No. 2014/061709, International Publication No. 2014/065176, International Publication No. 2014/126113, International Publication No. 2015/025793, International Publication No. 2015/064698, International Publication First No. 015/122384, copolymerizable monomers such as compounds disclosed in WO 2015/122385 and the like.
The mixing ratio of these other components is usually 0.005 to 50 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal compound.
　上記重合性液晶組成物は、通常、重合性液晶化合物、重合開始剤、および、所望により配合される他の成分等の所定量を、適当な有機溶媒に混合・溶解させることにより、調製することができる。 The polymerizable liquid crystal composition is usually prepared by mixing and dissolving a predetermined amount of a polymerizable liquid crystal compound, a polymerization initiator, and other components blended as required in an appropriate organic solvent. Can do.
　用いる有機溶媒としては、シクロペンタノン、シクロヘキサノン、メチルエチルケトン等のケトン類；酢酸ブチル、酢酸アミル等の酢酸エステル類；クロロホルム、ジクロロメタン、ジクロロエタン等のハロゲン化炭化水素類；１，４－ジオキサン、シクロペンチルメチルエーテル、テトラヒドロフラン、テトラヒドロピラン、１，３－ジオキソラン等のエーテル類；等が挙げられる。 Organic solvents to be used include ketones such as cyclopentanone, cyclohexanone and methyl ethyl ketone; acetate esters such as butyl acetate and amyl acetate; halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane; 1,4-dioxane, cyclopentylmethyl And ethers such as ether, tetrahydrofuran, tetrahydropyran, and 1,3-dioxolane;
（３）高分子
　本発明の高分子は、上述した重合性液晶化合物（Ｉ）または上述した重合性液晶組成物を重合して得られるものである。
　ここで、「重合」とは、通常の重合反応のほか、架橋反応を含む広い意味での化学反応を意味するものとする。
　そして、本発明の高分子は、通常、重合性液晶化合物（Ｉ）に由来する単量体単位（例えば、繰り返し単位（Ｉ）’）を有している。
　以下に、一例として、Ｐ１およびＰ２としてＣＨ２＝ＣＲ３１－Ｃ（＝Ｏ）－Ｏ－で表される重合性基を有する重合性化合物（Ｉ）を用いた場合の繰り返し単位（Ｉ）’の構造を示す。
Figure JPOXMLDOC01-appb-C000034
 〔式（Ｉ）’中のＡｒ、Ｙ１～Ｙ４、Ａ１、Ａ２、Ｂ１、Ｂ２、Ｇ１、Ｇ２、ｐ、およびｑは、前記と同じ意味であり、その好適例も同じである。Ｒ３１は、水素原子、メチル基、または、塩素原子であり、中でも、水素原子またはメチル基であることが好ましい。〕 (3) Polymer The polymer of the present invention is obtained by polymerizing the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition.
Here, “polymerization” means a chemical reaction in a broad sense including a crosslinking reaction in addition to a normal polymerization reaction.
The polymer of the present invention usually has a monomer unit derived from the polymerizable liquid crystal compound (I) (for example, the repeating unit (I) ′).
Hereinafter, as an example, a repeating unit (I) when a polymerizable compound (I) having a polymerizable group represented by CH 2 ═CR 31 —C (═O) —O— as P 1 and P 2 is used (I ) 'Structure.
Figure JPOXMLDOC01-appb-C000034
 [Ar, Y 1 to Y 4 , A 1 , A 2 , B 1 , B 2 , G 1 , G 2 , p, and q in the formula (I) ′ have the same meaning as described above, and preferred examples thereof Is the same. R 31 is a hydrogen atom, a methyl group, or a chlorine atom, and among them, a hydrogen atom or a methyl group is preferable. ]
　なお、本発明の高分子は、上述した重合性液晶化合物（Ｉ）、または、上述した重合性液晶組成物を用いて調製しているので、光学フィルム等の構成材料として良好に用いることができる。 In addition, since the polymer of the present invention is prepared using the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition, it can be favorably used as a constituent material for optical films and the like. .
　また、本発明の高分子は、特に限定されることなく、フィルム状、粉体状、粉体が集合した層状などの用途に応じた任意の形状にして使用することができる。
　具体的には、高分子のフィルムは、後述する光学フィルムおよび光学異方体の構成材料として良好に用いることができ、高分子の粉は、塗料、偽造防止物品、セキュリティ物品等に利用することができ、高分子の粉よりなる層は、光学異方体の構成材料として良好に用いることができる。 In addition, the polymer of the present invention is not particularly limited, and can be used in any shape according to the application such as a film shape, a powder shape, or a layer shape in which powders are aggregated.
Specifically, the polymer film can be used favorably as a constituent material of the optical film and optical anisotropic body described later, and the polymer powder can be used for paints, anti-counterfeit articles, security articles, etc. The layer made of polymer powder can be used favorably as a constituent material of the optical anisotropic body.
　そして、本発明の高分子は、具体的には、（α）適当な有機溶媒の存在下、上述した重合性液晶化合物（Ｉ）、または、上述した重合性液晶組成物の重合反応を行った後、目的とする高分子を単離し、得られる高分子を適当な有機溶媒に溶解して溶液を調製し、この溶液を適当な基板上に塗工して得られた塗膜を乾燥後、所望により加熱することにより得る方法、（β）上述した重合性液晶化合物（Ｉ）、または、上述した重合性液晶組成物を有機溶媒に溶解し、この溶液を、公知の塗工法により基板上に塗布した後、脱溶媒し、次いで加熱または活性エネルギー線を照射することにより重合反応を行う方法等により好適に製造することができる。なお、上述した重合性液晶化合物（Ｉ）を単独で重合してもよい。 Specifically, the polymer of the present invention (α) was subjected to a polymerization reaction of the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition in the presence of a suitable organic solvent. Then, the target polymer is isolated, and the resulting polymer is dissolved in an appropriate organic solvent to prepare a solution. After coating the solution on an appropriate substrate and drying the resulting coating, (Β) The above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition is dissolved in an organic solvent, and this solution is applied onto a substrate by a known coating method. After coating, it can be suitably produced by a method of performing a polymerization reaction by removing the solvent and then heating or irradiating active energy rays. The polymerizable liquid crystal compound (I) described above may be polymerized alone.
　前記（α）の方法において重合反応に用いる有機溶媒としては、不活性なものであれば、特に制限されない。例えば、トルエン、キシレン、メシチレン等の芳香族炭化水素；シクロヘキサノン、シクロペンタノン、メチルエチルケトン等のケトン類；酢酸ブチル、酢酸アミル等の酢酸エステル類；クロロホルム、ジクロロメタン、ジクロロエタン等のハロゲン化炭化水素類；シクロペンチルメチルエーテル、テトラヒドロフラン、テトラヒドロピラン等のエーテル類；等が挙げられる。
　これらの中でも、取り扱い性に優れる観点から、沸点が６０～２５０℃のものが好ましく、６０～１５０℃のものがより好ましい。 The organic solvent used for the polymerization reaction in the method (α) is not particularly limited as long as it is inactive. For example, aromatic hydrocarbons such as toluene, xylene and mesitylene; ketones such as cyclohexanone, cyclopentanone and methyl ethyl ketone; acetate esters such as butyl acetate and amyl acetate; halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane; And ethers such as cyclopentyl methyl ether, tetrahydrofuran and tetrahydropyran;
Among these, those having a boiling point of 60 to 250 ° C. are preferable and those having a temperature of 60 to 150 ° C. are more preferable from the viewpoint of excellent handleability.
　また、前記（α）の方法において、単離した高分子を溶解するための有機溶媒、および、前記（β）の方法で用いる有機溶媒としては、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロペンタノン、シクロヘキサノン等のケトン系溶剤；酢酸ブチル、酢酸アミル等のエステル系溶剤；ジクロロメタン、クロロホルム、ジクロロエタン等のハロゲン化炭化水素系溶剤；テトラヒドロフラン、テトラヒドロピラン、１，２－ジメトキシエタン、１，４－ジオキサン、シクロペンチルメチルエーテル、１，３－ジオキソラン等のエーテル系溶剤；Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、ジメチルスルホキシド、γ－ブチロラクトン、Ｎ－メチルピロリドン（Ｎ－メチル－２－ピロリドン）等の非プロトン性極性溶剤；等が挙げられる。これらの中でも、取り扱いが容易な点から、溶媒の沸点が６０～２００℃のものが好ましい。これらの溶剤は単独でも用いてもよく、２種以上を組み合わせて用いてもよい。 In the method (α), an organic solvent for dissolving the isolated polymer and an organic solvent used in the method (β) include acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, Ketone solvents such as cyclohexanone; ester solvents such as butyl acetate and amyl acetate; halogenated hydrocarbon solvents such as dichloromethane, chloroform and dichloroethane; tetrahydrofuran, tetrahydropyran, 1,2-dimethoxyethane, 1,4-dioxane, Ether solvents such as cyclopentyl methyl ether and 1,3-dioxolane; N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, γ-butyrolactone, N-methylpyrrolidone (N-methyl-2-pyrrolidone), etc. Non-proton Polar solvent; and the like. Among these, those having a boiling point of 60 to 200 ° C. are preferable from the viewpoint of easy handling. These solvents may be used alone or in combination of two or more.
　前記（α）および（β）の方法において用いる基板としては、有機、無機を問わず、公知慣用の材質のものを使用することができる。例えば、有機材料としては、ポリシクロオレフィン〔例えば、ゼオネックス、ゼオノア（登録商標；日本ゼオン社製）、アートン（登録商標；ＪＳＲ社製）、および、アペル（登録商標；三井化学社製）〕、ポリエチレンテレフタレート、ポリカーボネート、ポリイミド、ポリアミド、ポリメタクリル酸メチル、ポリスチレン、ポリ塩化ビニル、ポリテトラフルオロエチレン、セルロース、三酢酸セルロース、ポリエーテルスルホン等が挙げられ、無機材料としては、シリコン、ガラス、方解石等が挙げられる。
　また、用いる基板は、単層のものであっても、積層体であってもよい。
　基板としては、有機材料からなる基板が好ましく、有機材料をフィルム状にした樹脂フィルムが更に好ましい。
　なお、基板としては、後述する光学異方体の作製に用いられる基板等も挙げられる。 As the substrate used in the methods (α) and (β), a known and commonly used material can be used regardless of organic or inorganic. For example, examples of the organic material include polycycloolefins (for example, ZEONEX, ZEONOR (registered trademark; manufactured by ZEON CORPORATION), ARTON (registered trademark; manufactured by JSR), and APPEL (registered trademark; manufactured by Mitsui Chemicals)), Examples include polyethylene terephthalate, polycarbonate, polyimide, polyamide, polymethyl methacrylate, polystyrene, polyvinyl chloride, polytetrafluoroethylene, cellulose, cellulose triacetate, polyethersulfone, etc., and inorganic materials include silicon, glass, calcite, etc. Is mentioned.
The substrate used may be a single layer or a laminate.
As the substrate, a substrate made of an organic material is preferable, and a resin film obtained by forming an organic material into a film is more preferable.
In addition, as a board | substrate, the board | substrate etc. which are used for preparation of the optical anisotropic body mentioned later are mentioned.
　また、（α）の方法において高分子の溶液を基板に塗布する方法、および、（β）の方法において重合反応用の溶液を基板に塗布する方法としては、公知の方法を用いることができる。具体的には、例えば、カーテンコーティング法、押し出しコーティング法、ロールコーティング法、スピンコーティング法、ディップコーティング法、バーコーティング法、スプレーコーティング法、スライドコーティング法、印刷コーティング法、グラビアコーティング法、ダイコーティング法、キャップコーティング法等を用いることができる。 In addition, a known method can be used as a method of applying a polymer solution to a substrate in the method (α) and a method of applying a solution for polymerization reaction to a substrate in the method (β). Specifically, for example, curtain coating method, extrusion coating method, roll coating method, spin coating method, dip coating method, bar coating method, spray coating method, slide coating method, print coating method, gravure coating method, die coating method A cap coating method or the like can be used.
　更に、前記（α）および（β）の方法における乾燥または脱溶媒の方法としては、自然乾燥、加熱乾燥、減圧乾燥、減圧加熱乾燥等を用いることができる。
　乾燥温度は、溶媒を脱溶媒することができれば、特に制限はないが、下限温度に関しては、一定の温度を安定的に得られるという観点から、５０℃以上であることが好ましく、７０℃以上であることがより好ましい。
　乾燥温度の上限温度に関しては、基板に悪影響を与えない範囲という観点から、２００℃以下であることが好ましく、１９５℃以下であることがより好ましい。 Furthermore, as a method of drying or solvent removal in the methods (α) and (β), natural drying, heat drying, reduced pressure drying, reduced pressure heat drying and the like can be used.
The drying temperature is not particularly limited as long as the solvent can be removed from the solvent, but the lower limit temperature is preferably 50 ° C. or higher from the viewpoint that a constant temperature can be stably obtained, and is 70 ° C. or higher. More preferably.
The upper limit temperature of the drying temperature is preferably 200 ° C. or less, more preferably 195 ° C. or less, from the viewpoint of a range that does not adversely affect the substrate.
　また、上述した重合性液晶化合物（Ｉ）または上述した重合性液晶組成物を重合させる方法としては、活性エネルギー線を照射する方法や熱重合法等が挙げられるが、加熱を必要とせず、室温で反応が進行することから活性エネルギー線を照射する方法が好ましい。なかでも、操作が簡便なことから、紫外線等の光を照射する方法が好ましい。
　紫外線等の光を照射する温度は、液晶相を維持できる温度であれば、特に制限はないが、下限温度に関しては、光重合を安定的に進行させることができるという観点から、１５℃以上であることが好ましく、２０℃以上であることがより好ましい。
　紫外線等の光を照射する温度の上限温度に関しては、基板に悪影響を与えない範囲という観点から、２００℃以下であることが好ましく、１９５℃以下であることがより好ましい。 Examples of a method for polymerizing the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition include a method of irradiating active energy rays, a thermal polymerization method, and the like. The method of irradiating with active energy rays is preferable because the reaction proceeds at. Among these, a method of irradiating light such as ultraviolet rays is preferable because the operation is simple.
The temperature at which the light such as ultraviolet rays is irradiated is not particularly limited as long as the liquid crystal phase can be maintained. However, the lower limit temperature is 15 ° C. or more from the viewpoint that the photopolymerization can proceed stably. It is preferable that the temperature is 20 ° C. or higher.
The upper limit temperature for irradiating light such as ultraviolet rays is preferably 200 ° C. or lower, and more preferably 195 ° C. or lower, from the viewpoint of not adversely affecting the substrate.
　ここで、光の照射時の温度は、１００℃以下とすることが好ましい。光照射強度は、通常、１Ｗ／ｍ２～１０ｋＷ／ｍ２の範囲、好ましくは５Ｗ／ｍ２～２ｋＷ／ｍ２の範囲である。紫外線の照射量は、好ましくは０．１ｍＪ／ｃｍ２以上、より好ましくは０．５ｍＪ／ｃｍ２以上であり、好ましくは５０００ｍＪ／ｃｍ２以下、より好ましくは４０００ｍＪ／ｃｍ２以下である。 Here, the temperature at the time of light irradiation is preferably 100 ° C. or less. The light irradiation intensity is usually in the range of 1 W / m 2 to 10 kW / m 2 , preferably in the range of 5 W / m 2 to 2 kW / m 2 . The dose of ultraviolet rays is preferably 0.1 mJ / cm 2 or more, more preferably 0.5 mJ / cm 2 or more, preferably 5000 mJ / cm 2 or less, more preferably 4000 mJ / cm 2 or less.
　上述のようにして得られた高分子は、基板から転写して使用することも、基板から剥離して単体で使用することも、基板から剥離せずにそのまま光学フィルム等の構成材料等として使用することもできる。
　また、基板から剥離した高分子は、既知の方法で粉砕して粉体状にしてから使用することもできる。 The polymer obtained as described above can be used by being transferred from the substrate, separated from the substrate and used alone, or as a constituent material of an optical film or the like without being separated from the substrate. You can also
The polymer peeled from the substrate can be used after being pulverized by a known method to form a powder.
　以上のようにして得られる本発明の高分子の数平均分子量は、好ましくは５００～５００，０００、更に好ましくは５，０００～３００，０００である。該数平均分子量がかかる範囲にあれば、高い硬度が得られ、取り扱い性にも優れるため望ましい。高分子の数平均分子量は、単分散のポリスチレンを標準試料とし、テトラヒドロフランを溶離液としてゲルパーミエーションクロマトグラフィー（ＧＰＣ）により測定することができる。 The number average molecular weight of the polymer of the present invention obtained as described above is preferably 500 to 500,000, more preferably 5,000 to 300,000. If the number average molecular weight is in such a range, it is desirable because high hardness can be obtained and handleability is excellent. The number average molecular weight of the polymer can be measured by gel permeation chromatography (GPC) using monodispersed polystyrene as a standard sample and tetrahydrofuran as an eluent.
　そして、本発明の高分子によれば、広帯域性を示す理想的な波長分散性、即ち逆波長分散性を有する光学フィルム等を得ることができる。 And according to the polymer of the present invention, it is possible to obtain an optical film or the like having ideal wavelength dispersion exhibiting broadband properties, that is, reverse wavelength dispersion.
（４）光学フィルム
　本発明の光学フィルムは、本発明の高分子および／又は重合性液晶化合物を用いて形成され、光学的な機能を有する層を含む。光学的な機能とは、単なる透過、反射、屈折、複屈折などを意味する。そして、本発明の光学フィルムは、本発明の高分子を光学的な機能を有する層の主たる構成材料とする光学フィルムであるか、或いは、光学的な機能を有する層が本発明の重合性液晶化合物を含有する光学フィルムでありうる。好ましくは、本発明の高分子を構成材料とする光学フィルムは、光学的な機能を有する層の全構成成分を１００質量％とした場合に本発明の高分子の占有割合が５０質量％超である。また、好ましくは、本発明の重合性液晶化合物を含む光学フィルムは、光学的な機能を有する層の全構成成分を１００質量％とした場合に、本発明の重合性液晶化合物を０．０１質量％以上含有する。 (4) Optical film The optical film of the present invention is formed using the polymer and / or polymerizable liquid crystal compound of the present invention, and includes a layer having an optical function. The optical function means simple transmission, reflection, refraction, birefringence and the like. The optical film of the present invention is an optical film comprising the polymer of the present invention as a main constituent material of the layer having an optical function, or the layer having an optical function is the polymerizable liquid crystal of the present invention. It can be an optical film containing a compound. Preferably, in the optical film comprising the polymer of the present invention as a constituent material, the occupation ratio of the polymer of the present invention is more than 50% by mass when all the components of the layer having an optical function are 100% by mass. is there. Preferably, in the optical film containing the polymerizable liquid crystal compound of the present invention, the polymerizable liquid crystal compound of the present invention is added in an amount of 0.01% by mass when the total components of the layer having an optical function are 100% by mass. % Or more.
　ここで、本発明の光学フィルムは、配向膜を有していてもよい配向基板上に形成されたままの形態（配向基板／（配向膜）／光学フィルム）、配向基板とは異なる透明基板フィルム等に光学フィルムを転写した形態（透明基板フィルム／光学フィルム）、または、光学フィルムに自己支持性がある場合には光学フィルム単層形態（光学フィルム）のいずれの形態であってもよい。
　なお、配向膜および配向基板としては、後述する光学異方体と同じ基板および配向膜を用いることができる。 Here, the optical film of the present invention is in the form (alignment substrate / (alignment film) / optical film) formed on the alignment substrate which may have an alignment film, and a transparent substrate film different from the alignment substrate. The optical film may be transferred in any form (transparent substrate film / optical film), or in the case where the optical film is self-supporting, it may be in any form of an optical film single layer (optical film).
In addition, as the alignment film and the alignment substrate, the same substrate and alignment film as the optical anisotropic body described later can be used.
　そして、本発明の光学フィルムは、（Ａ）本発明の重合性液晶化合物を含む溶液、または、重合性液晶組成物の溶液を配向基板上に塗布し、得られた塗膜を乾燥し、熱処理（液晶の配向）、並びに、光照射および／または加熱処理（重合）を行う方法や、（Ｂ）本発明の重合性液晶化合物、または重合性液晶組成物を重合して得られる液晶性高分子の溶液を配向基板上に塗布し、任意に得られた塗膜を乾燥する方法や、（Ｃ）本発明の重合性液晶化合物および樹脂を含む溶液を配向基板上に塗布し、得られた塗膜を乾燥する方法により製造することができる。 The optical film of the present invention is obtained by applying (A) a solution containing the polymerizable liquid crystal compound of the present invention or a solution of the polymerizable liquid crystal composition onto an alignment substrate, drying the obtained coating film, and subjecting to heat treatment. (Liquid crystal orientation), a method of performing light irradiation and / or heat treatment (polymerization), and (B) a liquid crystalline polymer obtained by polymerizing the polymerizable liquid crystal compound or polymerizable liquid crystal composition of the present invention. Or a solution containing the polymerizable liquid crystal compound of the present invention and a resin is applied on the alignment substrate, and the resulting coating is obtained. It can be produced by a method of drying the membrane.
　本発明の光学フィルムは、光学異方体、液晶表示素子用配向膜、カラーフィルター、ローパスフィルター、光偏光プリズム、各種光フィルター等に用いることができる。 The optical film of the present invention can be used for optical anisotropic bodies, alignment films for liquid crystal display elements, color filters, low-pass filters, light polarizing prisms, various optical filters, and the like.
　なお、本発明の光学フィルムは、Ｍｕｅｌｌｅｒ　Ｍａｔｒｉｘ　Ｐｏｌａｒｉｍｅｔｅｒ　Ａｘｏｓｃａｎで測定した波長４００ｎｍ～８００ｎｍにおける位相差から求められる。下記α値およびβ値が所定の範囲内にあることが好ましい。具体的には、α値は、０．７０～０．９９であることが好ましく、０．７５～０．９０であることがより好ましい。また、β値は、１．００～１．２５であることが好ましく、１．０１～１．２０であることがより好ましい。
α＝（４５０ｎｍにおける位相差）／（５５０ｎｍにおける位相差）
β＝（６５０ｎｍにおける位相差）／（５５０ｎｍにおける位相差） The optical film of the present invention can be obtained from the phase difference at a wavelength of 400 nm to 800 nm measured with Mueller Matrix Polarimeter Axoscan. The following α value and β value are preferably within a predetermined range. Specifically, the α value is preferably 0.70 to 0.99, and more preferably 0.75 to 0.90. Further, the β value is preferably 1.00 to 1.25, and more preferably 1.01 to 1.20.
α = (phase difference at 450 nm) / (phase difference at 550 nm)
β = (phase difference at 650 nm) / (phase difference at 550 nm)
（５）光学異方体
　本発明の光学異方体は、本発明の高分子を構成材料とする層を有する。
　本発明の光学異方体は、例えば、基板上に配向膜を形成し、該配向膜上に、さらに、本発明の高分子からなる層（液晶層）を形成することによって、得ることができる。なお、本発明の光学異方体は、基板上に本発明の高分子からなる層（液晶層）を直接形成したものであってもよいし、本発明の高分子からなる層（液晶層）のみからなるものであってもよい。
　なお、高分子からなる層は、フィルム状の高分子からなるものであってもよいし、粉体状の高分子の集合体であってもよい。 (5) Optical anisotropic body The optical anisotropic body of this invention has a layer which uses the polymer of this invention as a constituent material.
The optical anisotropic body of the present invention can be obtained, for example, by forming an alignment film on a substrate and further forming a layer (liquid crystal layer) made of the polymer of the present invention on the alignment film. . The optically anisotropic body of the present invention may be one in which a layer made of the polymer of the present invention (liquid crystal layer) is directly formed on a substrate, or a layer made of the polymer of the present invention (liquid crystal layer). It may consist of only.
The polymer layer may be a film polymer or a powder polymer aggregate.
　ここで、配向膜は、重合性液晶化合物を面内で一方向に配向規制するために基板の表面に形成される。
　配向膜は、ポリイミド、ポリビニルアルコール、ポリエステル、ポリアリレート、ポリアミドイミド、ポリエーテルイミド等のポリマーを含有する溶液（配向膜用組成物）を基板上に膜状に塗布し、乾燥させ、そして一方向にラビング処理等することで、得ることができる。
　配向膜の厚さは０．００１～５μｍであることが好ましく、０．００１～１．０μｍであることがさらに好ましい。 Here, the alignment film is formed on the surface of the substrate in order to regulate the alignment of the polymerizable liquid crystal compound in one direction in the plane.
The alignment film is formed by applying a solution containing a polymer such as polyimide, polyvinyl alcohol, polyester, polyarylate, polyamideimide, or polyetherimide (alignment film composition) onto a substrate, drying the film, and then unidirectionally. It can be obtained by rubbing treatment.
The thickness of the alignment film is preferably 0.001 to 5 μm, and more preferably 0.001 to 1.0 μm.
　ラビング処理の方法は、特に制限されないが、例えばナイロン等の合成繊維、木綿等の天然繊維からなる布やフェルトを巻き付けたロールで一定方向に配向膜を擦る方法が挙げられる。ラビング処理した時に発生する微粉末（異物）を除去して配向膜の表面を清浄な状態とするために、ラビング処理後に配向膜をイソプロピルアルコール等によって洗浄することが好ましい。
　また、ラビング処理する方法以外に、配向膜の表面に偏光紫外線を照射する方法によっても、面内で一方向に配向規制する機能を持たせることができる。 The rubbing treatment method is not particularly limited, and examples thereof include a method of rubbing the alignment film in a certain direction with a roll made of a synthetic fiber such as nylon or a natural fiber such as cotton or a felt. In order to remove fine powder (foreign matter) generated during the rubbing treatment and clean the surface of the alignment film, it is preferable to clean the alignment film with isopropyl alcohol or the like after the rubbing treatment.
In addition to the rubbing method, a method of regulating the alignment in one direction in the plane can be provided by a method of irradiating the surface of the alignment film with polarized ultraviolet rays.
　配向膜を形成する基板としては、ガラス基板、合成樹脂フィルムからなる基板等が挙げられる。前記合成樹脂としては、アクリル樹脂、ポリカーボネート樹脂、ポリエーテルスルホン樹脂、ポリエチレンテレフタレート樹脂、ポリイミド樹脂、ポリメチルメタクリレート樹脂、ポリスルホン樹脂、ポリアリレート樹脂、ポリエチレン樹脂、ポリスチレン樹脂、ポリ塩化ビニル樹脂、二酢酸セルロース、三酢酸セルロース、および、脂環式オレフィンポリマーなどの熱可塑性樹脂が挙げられる。 Examples of the substrate on which the alignment film is formed include a glass substrate and a substrate made of a synthetic resin film. Examples of the synthetic resin include acrylic resin, polycarbonate resin, polyethersulfone resin, polyethylene terephthalate resin, polyimide resin, polymethyl methacrylate resin, polysulfone resin, polyarylate resin, polyethylene resin, polystyrene resin, polyvinyl chloride resin, and cellulose diacetate. , Cellulose triacetate, and thermoplastic resins such as alicyclic olefin polymers.
　脂環式オレフィンポリマーとしては、特開平０５－３１０８４５号公報、米国特許第５１７９１７１号明細書に記載されている環状オレフィンランダム多元共重合体、特開平０５－９７９７８号公報、米国特許第５２０２３８８号明細書に記載されている水素添加重合体、特開平１１－１２４４２９号公報（国際公開９９／２０６７６号）に記載されている熱可塑性ジシクロペンタジエン系開環重合体およびその水素添加物等が挙げられる。 Examples of the alicyclic olefin polymer include cyclic olefin random multicomponent copolymers described in JP-A No. 05-310845, US Pat. No. 5,179,171, JP-A No. 05-97978, and US Pat. No. 5,202,388. And hydrogenated polymers described in Japanese Patent Application Laid-Open No. 11-124429 (International Publication No. 99/20676), and thermoplastic dicyclopentadiene ring-opening polymers and hydrogenated products thereof. .
　本発明において、配向膜上に本発明の高分子からなる液晶層を形成する方法としては、前記本発明の高分子の項で記載したのと同じ方法（前記（α）および（β））が挙げられる。
　得られる液晶層の厚みは、特に制限はないが、通常１～１０μｍである。 In the present invention, as a method for forming the liquid crystal layer comprising the polymer of the present invention on the alignment film, the same method as described in the section of the polymer of the present invention (the above (α) and (β)) may be used. Can be mentioned.
The thickness of the obtained liquid crystal layer is not particularly limited, but is usually 1 to 10 μm.
　なお、本発明の光学異方体の一種としては、特に限定されることなく、位相差板、視野角拡大板等が挙げられる。 In addition, as a kind of optical anisotropic body of this invention, a phase difference plate, a viewing angle expansion plate, etc. are mentioned, without being specifically limited.
　なお、本発明の光学異方体は、Ｍｕｅｌｌｅｒ　Ｍａｔｒｉｘ　Ｐｏｌａｒｉｍｅｔｅｒ　Ａｘｏｓｃａｎで測定した波長４００ｎｍ～８００ｎｍにおける位相差から求められる。下記α値およびβ値が所定の範囲内にあることが好ましい。具体的には、α値は、０．７０～０．９９であることが好ましく、０．７５～０．９０であることがより好ましい。また、β値は、１．００～１．２５であることが好ましく、１．０１～１．２５であることがより好ましい。
α＝（４５０ｎｍにおける位相差）／（５５０ｎｍにおける位相差）
β＝（６５０ｎｍにおける位相差）／（５５０ｎｍにおける位相差） The optical anisotropic body of the present invention is obtained from a phase difference at a wavelength of 400 nm to 800 nm measured with Mueller Matrix Polarimeter Axoscan. The following α value and β value are preferably within a predetermined range. Specifically, the α value is preferably 0.70 to 0.99, and more preferably 0.75 to 0.90. The β value is preferably 1.00 to 1.25, more preferably 1.01 to 1.25.
α = (phase difference at 450 nm) / (phase difference at 550 nm)
β = (phase difference at 650 nm) / (phase difference at 550 nm)
（６）偏光板等
　本発明の偏光板は、本発明の光学異方体および偏光フィルムを含むものである。
　本発明の偏光板の具体例としては、偏光フィルム上に、直接またはその他の層（ガラス板等）を介して、本発明の光学異方体が積層されてなるものが挙げられる。 (6) Polarizing plate etc. The polarizing plate of the present invention comprises the optical anisotropic body of the present invention and a polarizing film.
Specific examples of the polarizing plate of the present invention include those in which the optical anisotropic body of the present invention is laminated on a polarizing film directly or via another layer (glass plate or the like).
　偏光フィルムの製造方法は特に限定されない。ＰＶＡ系の偏光フィルムを製造する方法としては、ＰＶＡ系フィルムにヨウ素イオンを吸着させた後に一軸に延伸する方法、ＰＶＡ系フィルムを一軸に延伸した後にヨウ素イオンを吸着させる方法、ＰＶＡ系フィルムへのヨウ素イオン吸着と一軸延伸とを同時に行う方法、ＰＶＡ系フィルムを二色性染料で染色した後に一軸に延伸する方法、ＰＶＡ系フィルムを一軸に延伸した後に二色性染料で染色する方法、ＰＶＡ系フィルムへの二色性染料での染色と一軸延伸とを同時に行う方法が挙げられる。また、ポリエン系の偏光フィルムを製造する方法としては、ＰＶＡ系フィルムを一軸に延伸した後に脱水触媒存在下で加熱・脱水する方法、ポリ塩化ビニル系フィルムを一軸に延伸した後に脱塩酸触媒存在下で加熱・脱水する方法などの公知の方法が挙げられる。 The manufacturing method of the polarizing film is not particularly limited. As a method for producing a PVA-based polarizing film, a method of stretching uniaxially after iodine ions are adsorbed on a PVA-based film, a method of adsorbing iodine ions after stretching a uniaxially stretched PVA-based film, A method of simultaneously performing iodine ion adsorption and uniaxial stretching, a method of stretching a uniaxial film after dyeing a PVA film with a dichroic dye, a method of dyeing a dichroic dye after stretching a PVA film uniaxially, a PVA system The method of performing simultaneously dyeing | staining with a dichroic dye and uniaxial stretching to a film is mentioned. In addition, as a method for producing a polyene polarizing film, a method of heating and dehydrating in the presence of a dehydration catalyst after stretching a PVA film uniaxially, a method of stretching a polyvinyl chloride film uniaxially and then in the presence of a dehydrochlorination catalyst And a known method such as heating and dehydrating.
　本発明の偏光板においては、偏光フィルムと本発明の光学異方体とが、接着剤（粘着剤を含む）からなる接着層を介して接していてもよい。接着層の平均厚みは、通常０．０１μｍ～３０μｍ、好ましくは０．１μｍ～１５μｍである。前記接着層は、ＪＩＳ　Ｋ７１１３による引張破壊強度が４０ＭＰａ以下となる層であることが好ましい。 In the polarizing plate of the present invention, the polarizing film and the optical anisotropic body of the present invention may be in contact with each other via an adhesive layer made of an adhesive (including an adhesive). The average thickness of the adhesive layer is usually 0.01 μm to 30 μm, preferably 0.1 μm to 15 μm. The adhesive layer is preferably a layer having a tensile fracture strength according to JIS K7113 of 40 MPa or less.
　接着層を構成する接着剤としては、アクリル接着剤、ウレタン接着剤、ポリエステル接着剤、ポリビニルアルコール接着剤、ポリオレフィ系接着剤、変性ポリオレフィン接着剤、ポリビニルアルキルエーテル接着剤、ゴム接着剤、塩化ビニル・酢酸ビニル接着剤、スチレン・ブタジエン・スチレン共重合体（ＳＢＳ共重合体）接着剤、その水素添加物（ＳＥＢＳ共重合体）接着剤、エチレン・酢酸ビニル共重合体およびエチレン－スチレン共重合体などのエチレン接着剤、並びに、エチレン・メタクリル酸メチル共重合体、エチレン・アクリル酸メチル共重合体、エチレン・メタクリル酸エチル共重合体およびエチレン・アクリル酸エチル共重合体などのアクリル酸エステル接着剤などが挙げられる。 Adhesives constituting the adhesive layer include acrylic adhesives, urethane adhesives, polyester adhesives, polyvinyl alcohol adhesives, polyolefin adhesives, modified polyolefin adhesives, polyvinyl alkyl ether adhesives, rubber adhesives, vinyl chloride Vinyl acetate adhesive, styrene / butadiene / styrene copolymer (SBS copolymer) adhesive, hydrogenated product (SEBS copolymer) adhesive, ethylene / vinyl acetate copolymer, ethylene-styrene copolymer, etc. Ethylene adhesives, and acrylic ester adhesives such as ethylene / methyl methacrylate copolymers, ethylene / methyl acrylate copolymers, ethylene / ethyl methacrylate copolymers and ethylene / ethyl acrylate copolymers, etc. Is mentioned.
　本発明の偏光板は、本発明の光学異方体を用いていることから、逆波長分散性を有しながら、光学特性の面内均一性に優れるものである。 Since the polarizing plate of the present invention uses the optical anisotropic body of the present invention, it has excellent in-plane uniformity of optical characteristics while having reverse wavelength dispersion.
　また、本発明の偏光板を用いることにより、パネルを備える表示装置、反射防止フィルムを好適に製造することができる。前記パネルとしては、液晶パネル、有機エレクトロルミネッセンスパネルが挙げられる。前記表示装置としては、偏光板と液晶パネルとを備えるフラットパネル表示装置、液晶パネルと有機エレクトロルミネッセンスパネルとを備える有機エレクトロルミネッセンス表示装置が挙げられる。 Moreover, by using the polarizing plate of the present invention, a display device provided with a panel and an antireflection film can be suitably produced. Examples of the panel include a liquid crystal panel and an organic electroluminescence panel. Examples of the display device include a flat panel display device including a polarizing plate and a liquid crystal panel, and an organic electroluminescence display device including a liquid crystal panel and an organic electroluminescence panel.
（７）化合物（中間体）
　本発明の重合性液晶化合物および該重合性液晶化合物の調製に使用し得る中間体は、国際公開第２０１２／１４１２４５号、国際公開第２０１２／１４７９０４号、国際公開第２０１４／０１０３２５号、国際公開第２０１３／０４６７８１号、国際公開第２０１４／１２６１１３号、国際公開第２０１５／０２５７９３号、特開２０１５－１４０３０２号公報、国際公開第２０１５／１２９６５４号、国際公開第２０１５／１４１７８４号、国際公開第２０１６／１５９１９３号を参考に合成することができる。 (7) Compound (intermediate)
The polymerizable liquid crystal compound of the present invention and the intermediate that can be used for the preparation of the polymerizable liquid crystal compound are WO 2012/141245, WO 2012/147904, WO 2014/010325, and WO 2013/046781, International Publication No. 2014/126113, International Publication No. 2015/025793, Japanese Patent Application Laid-Open No. 2015-140302, International Publication No. 2015/129654, International Publication No. 2015/141784, International Publication No. 2016 / It can be synthesized with reference to No. 159193.
　本発明の重合性液晶化合物の調製に使用し得る中間体の構造は、例えば、下記一般式（Ｘ－１）で表される。
Figure JPOXMLDOC01-appb-C000035
 〔一般式（Ｘ－１）中、Ｐ１、Ｇ１、Ｙ３、Ｂ１、Ｙ１、Ａ１、ｐは、それぞれ、前記と同じ意味を表し、その好適例も、それぞれ、前記Ｐ１、Ｇ１、Ｙ３、Ｂ１、Ｙ１、Ａ１、ｐの好適例と同じであり、ＦＧは水酸基またはカルボキシル基を表す。〕 The structure of an intermediate that can be used for the preparation of the polymerizable liquid crystal compound of the present invention is represented, for example, by the following general formula (X-1).
Figure JPOXMLDOC01-appb-C000035
 [In the general formula (X-1), P 1 , G 1 , Y 3 , B 1 , Y 1 , A 1 , p each represents the same meaning as described above, and preferred examples thereof also represent the P 1 , G 1 , Y 3 , B 1 , Y 1 , A 1 , p are the same as the preferred examples, and FG represents a hydroxyl group or a carboxyl group. ]
　また、本願明細書の実施例にて用いられている中間体Ｃ，Ｄの構造を示す下記一般式（Ｘ）は、以下の方法（ｉ），（ｉｉ），（ｉｉｉ）で合成が可能である。
Figure JPOXMLDOC01-appb-C000036
 ［一般式（Ｘ）中、Ｐは前記Ｐ１、Ｐ２と同じ意味を表し、その好適例も前記Ｐ１、Ｐ２の好適例と同じであり、Ｇは前記Ｇ１、Ｇ２と同じ意味を表し、その好適例も前記Ｇ１、Ｇ２の好適例と同じであり、Ｂは前記Ｂ１、Ｂ２と同じ意味を表し、その好適例も前記Ｂ１、Ｂ２の好適例と同じであり、Ｙは前記Ｙ１、Ｙ２と同じ意味を表し、その好適例も前記Ｙ１、Ｙ２の好適例と同じであり、Ａは前記Ａ１、Ａ２と同じ意味を表し、その好適例も前記Ａ１、Ａ２の好適例と同じである。］ The following general formula (X) showing the structure of intermediates C and D used in the examples of the present specification can be synthesized by the following methods (i), (ii) and (iii). is there.
Figure JPOXMLDOC01-appb-C000036
 [In General Formula (X), P represents the same meaning as P 1 and P 2, and its preferred examples are the same as the preferred examples of P 1 and P 2 , and G is the same as G 1 and G 2. The meanings are also the same as the preferred examples of G 1 and G 2 , B is the same as B 1 and B 2, and the preferred examples are also preferred examples of B 1 and B 2. are the same, Y are as defined above Y 1, Y 2, the preferred embodiment is also the same as the preferred examples of the Y 1, Y 2, a are as defined above a 1, a 2, The preferred examples are the same as the preferred examples of A 1 and A 2 . ]
（ｉ）酸ハライド、混合酸無水物によるエステル化反応
Figure JPOXMLDOC01-appb-C000037
 ［式中、Ｐ、Ｇ、Ｂ、Ｙ、Ａは、それぞれ、前記と同じ意味を表し、その好適例も前記と同じであり、Ｌは、ハロゲン原子、メタンスルホニルオキシ基、ベンゼンスルホニルオキシ基、またはトルエンスルホニルオキシ基を表す。］ (I) Esterification reaction with acid halide and mixed acid anhydride
Figure JPOXMLDOC01-appb-C000037
 [Wherein, P, G, B, Y, A each represents the same meaning as described above, and preferred examples thereof are also the same as described above, and L represents a halogen atom, a methanesulfonyloxy group, a benzenesulfonyloxy group, Or represents a toluenesulfonyloxy group. ]
　一般式（Ｘ１）で表される化合物（以下、「化合物（Ｘ１）」とする）と、一般式（Ｘ２）で表される化合物（以下、「化合物（Ｘ２）」とする）とを塩基存在下にて反応させて、一般式（Ｘ）で表される化合物（以下、「化合物（Ｘ）」とする）を得ることができる。 A compound represented by the general formula (X1) (hereinafter referred to as “compound (X1)”) and a compound represented by the general formula (X2) (hereinafter referred to as “compound (X2)”) are present in a base. By reacting under the above conditions, a compound represented by the general formula (X) (hereinafter referred to as “compound (X)”) can be obtained.
　化合物（Ｘ１）の使用量は、化合物（Ｘ２）の使用量を基準として、通常、０．１モル当量以上であり、０．５モル当量以上であることが好ましく、０．８モル当量以上であることがより好ましく、また、通常、１．５モル当量以下であり、１．３モル当量以下であることがより好ましい。 The amount of compound (X1) used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of compound (X2). More preferably, it is usually 1.5 molar equivalents or less, and more preferably 1.3 molar equivalents or less.
　使用する塩基としては、例えば、トリエチルアミン、ピリジン、ジイソプロピルエチルアミン、Ｎ，Ｎ－ジメチル－４－アミノピリジン等の３級アミン類；などが挙げられる。
　使用する塩基の使用量は、化合物（Ｘ２）の使用量を基準として、通常０．１モル当量以上であり、０．５モル当量以上であることが好ましく、０．８モル当量以上であることがより好ましく、また、通常、１．５モル当量以下であり、１．３モル当量以下であることが好ましい。 Examples of the base used include tertiary amines such as triethylamine, pyridine, diisopropylethylamine, and N, N-dimethyl-4-aminopyridine;
The amount of the base used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of compound (X2). Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
（ｉｉ）縮合剤を用いるエステル化反応
Figure JPOXMLDOC01-appb-C000038
 ［式中、Ｐ、Ｇ、Ｂ、Ｙ、Ａは、それぞれ、前記と同じ意味を表し、その好適例も前記と同じである。］ (Ii) Esterification reaction using a condensing agent
Figure JPOXMLDOC01-appb-C000038
 [Wherein, P, G, B, Y, and A each have the same meaning as described above, and preferred examples thereof are also the same as described above. ]
　水酸基を有する化合物（Ｘ１）と、ジカルボン酸とを脱水縮合剤を用いて反応させて、化合物（Ｘ）を得ることができる。 The compound (X) can be obtained by reacting the compound (X1) having a hydroxyl group with a dicarboxylic acid using a dehydrating condensing agent.
　化合物（Ｘ１）の使用量は、ジカルボン酸の使用量を基準として、通常、０．１モル当量以上であり、０．５モル当量以上であることが好ましく、０．８モル当量以上であることがより好ましく、また、通常、１．５モル当量以下であり、１．３モル当量以下であることが好ましい。 The amount of compound (X1) used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of dicarboxylic acid. Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
　使用する縮合剤としては、例えば、ジシクロヘキシルカルボジイミド、ジイソプロピルカルボジイミド、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩等の脱水縮合剤；などが挙げられる。
　使用する縮合剤の使用量は、ジカルボン酸の使用量を基準として、通常、０．１モル当量以上であり、０．５モル当量以上であることが好ましく、０．８モル当量以上であることがより好ましく、また、通常、１．５モル当量以下であり、１．３モル当量以下であることが好ましい。またここで、Ｎ，Ｎ－ジメチル－４－アミノピリジン等の活性化剤を併用することもできる。 Examples of the condensing agent to be used include dehydrating condensing agents such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride;
The amount of the condensing agent to be used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of the dicarboxylic acid. Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less. Here, an activator such as N, N-dimethyl-4-aminopyridine may be used in combination.
（ｉｉｉ）酸無水物を用いるエステル化反応
Figure JPOXMLDOC01-appb-C000039
 ［式中、Ｐ、Ｇ、Ｂ、Ｙ、Ａは、それぞれ、前記と同じ意味を表し、その好適例も前記と同じである。］ (Iii) Esterification reaction using acid anhydride
Figure JPOXMLDOC01-appb-C000039
 [Wherein, P, G, B, Y, and A each have the same meaning as described above, and preferred examples thereof are also the same as described above. ]
　水酸基を有する化合物（Ｘ１）と、ＮａＨ等の強塩基とを反応させた後、酸無水物を反応させて、化合物（Ｘ）を得ることができる。 The compound (X) can be obtained by reacting the compound (X1) having a hydroxyl group with a strong base such as NaH and then reacting with an acid anhydride.
　ＮａＨ等の強塩基の使用量は、化合物（Ｘ１）の使用量を基準として、通常、０．５モル当量以上であり、０．８モル当量以上であることが好ましく、また、通常、３モル当量以下であり、１．５モル当量以下であることが好ましく、１．３モル当量以下であることがより好ましい。またここで、Ｎ，Ｎ－ジメチル－４－アミノピリジン等の活性化剤を併用することもできる。 The amount of strong base such as NaH is usually 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, and usually 3 moles, based on the usage amount of compound (X1). It is preferably not more than the equivalent, preferably not more than 1.5 molar equivalent, more preferably not more than 1.3 molar equivalent. Here, an activator such as N, N-dimethyl-4-aminopyridine may be used in combination.
　本願明細書の実施例にて用いられている中間体Ｂ，Ｅの構造を示す下記一般式（Ｙ）は、例えば、以下の方法により合成が可能である。
ＨＯ－Ａｒ－ＯＨ・・・一般式（Ｙ）
　式中、Ａｒは、前記と同じ意味を表し、その好適例も前記と同じである。 The following general formula (Y) indicating the structure of intermediates B and E used in the examples of the present specification can be synthesized by, for example, the following method.
HO—Ar—OH: General formula (Y)
In the formula, Ar represents the same meaning as described above, and preferred examples thereof are also the same as described above.
　一般式（Ｙ１）～（Ｙ３）で表される化合物（以下、それぞれ、「化合物（Ｙ１）～（Ｙ３）」とする）のいずれかと、一般式（Ｙ４）～（Ｙ６）で表される化合物（以下、それぞれ、「化合物（Ｙ４）～（Ｙ６）」とする）のいずれかとを反応させて、一般式（Ｙ）で表される化合物（以下、「一般式（Ｙ）」とする）を得ることができる。
Figure JPOXMLDOC01-appb-C000040
 　上記式（Ｙ１）～（Ｙ３）中、環内部からのびる「－」は、環の任意の位置からのびる結合手を表す。 Any one of the compounds represented by the general formulas (Y1) to (Y3) (hereinafter referred to as “compounds (Y1) to (Y3)”) and the compounds represented by the general formulas (Y4) to (Y6) (Hereinafter referred to as “compounds (Y4) to (Y6)”) to react with the compound represented by general formula (Y) (hereinafter referred to as “general formula (Y)”). Obtainable.
Figure JPOXMLDOC01-appb-C000040
 In the above formulas (Y1) to (Y3), “-” extending from the inside of the ring represents a bond extending from any position of the ring.
Ｈ２Ｎ－Ｎ（Ａｙ）Ａｘ・・・一般式（Ｙ４）
Ｈ２Ｎ－Ｎ＝Ｃ（Ａｙ）Ａｘ・・・一般式（Ｙ５）
Ｈ２Ｎ－Ｎ＝Ａｚ・・・一般式（Ｙ６）
　上記式（Ｙ４）～（Ｙ６）中、Ａｘ、Ａｙ、Ａｚは、それぞれ、前記と同じ意味を表し、その好適例も前記と同じである。 H 2 NN (Ay) Ax: General formula (Y4)
H 2 N—N═C (Ay) Ax—General formula (Y5)
H 2 N—N = Az General formula (Y6)
In the above formulas (Y4) to (Y6), Ax, Ay and Az each have the same meaning as described above, and preferred examples thereof are also the same as described above.
　上述したように得られた化合物（Ｘ）と化合物（Ｙ）を反応させて、下記式（Ｉ）’’で示される化合物が得られる。
Figure JPOXMLDOC01-appb-C000041
 　式（Ｉ）’’中、Ａｒ、Ａ１、Ａ２、Ｂ１、Ｂ２、Ｙ１、Ｙ２、Ｙ３、Ｙ４、Ｇ１、Ｇ２、Ｐ１、Ｐ２、ｐ、ｑは、それぞれ、前記と同じ意味を表し、その好適例も前記と同じである。 The compound represented by the following formula (I) ″ is obtained by reacting the compound (X) obtained as described above with the compound (Y).
Figure JPOXMLDOC01-appb-C000041
 In formula (I) ″, Ar, A 1 , A 2 , B 1 , B 2 , Y 1 , Y 2 , Y 3 , Y 4 , G 1 , G 2 , P 1 , P 2 , p, q are , Each having the same meaning as described above, and preferred examples thereof are also the same as described above.
　以下、本発明を、実施例によりさらに詳細に説明する。但し、本発明は以下の実施例により何ら制限されるものではない。 Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited by the following examples.
（合成例１）重合性液晶化合物１の合成
Figure JPOXMLDOC01-appb-C000042
 (Synthesis Example 1) Synthesis of polymerizable liquid crystal compound 1
Figure JPOXMLDOC01-appb-C000042
ステップ１：中間体Ａの合成
Figure JPOXMLDOC01-appb-C000043
 Step 1: Synthesis of Intermediate A
Figure JPOXMLDOC01-appb-C000043
　中間体Ａを、特開２０１６－１９０８１８号公報を参考にして合成した。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 Intermediate A was synthesized with reference to JP-A No. 2016-190818.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３，ＴＭＳ，δｐｐｍ）：７．６０（ｄｄ，１Ｈ，Ｊ＝１．０Ｈｚ，８．０Ｈｚ）、７．５３（ｄｄ，１Ｈ，Ｊ＝　１．０Ｈｚ，８．０Ｈｚ）、７．２７（ｄｄｄ，１Ｈ，Ｊ＝１．０Ｈｚ，８．０Ｈｚ，８．０Ｈｚ）、７．０６（ｄｄｄ，１Ｈ，Ｊ＝１．０Ｈｚ，８．　０Ｈｚ，８．０Ｈｚ）、４．２２（ｓ，２Ｈ）、３．７４（ｔ，２Ｈ，Ｊ＝７．５Ｈｚ）、１．６９－１．７６（ｍ，２Ｈ）、１．２９－１．４２（ｍ，６Ｈ）、０．８９（ｔ，３Ｈ，Ｊ＝７．０Ｈｚ）。 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): 7.60 (dd, 1 H, J = 1.0 Hz, 8.0 Hz), 7.53 (dd, 1 H, J = 1.0 Hz, 8. 0 Hz), 7.27 (ddd, 1H, J = 1.0 Hz, 8.0 Hz, 8.0 Hz), 7.06 (ddd, 1H, J = 1.0 Hz, 8.0 Hz, 8.0 Hz), 4 .22 (s, 2H), 3.74 (t, 2H, J = 7.5 Hz), 1.69-1.76 (m, 2H), 1.29-1.42 (m, 6H), 0 .89 (t, 3H, J = 7.0 Hz).
ステップ２：中間体Ｂの合成
Figure JPOXMLDOC01-appb-C000044
 Step 2: Synthesis of Intermediate B
Figure JPOXMLDOC01-appb-C000044
　温度計を備えた３ロ反応器において、窒素気流中、前記ステップ１で合成した中間体Ａ：３．６１ｇ（１４．４８ｍｍｏｌ）および２，５－ジヒドロキシベンズアルデヒド：２．００ｇ（１４．４８ｍｍｏｌ）を、メタノール：４０ｍＬに溶解させた。この溶液に、（±）－１０－カンファ一スルホン酸：０．３３６ｇ　（１．４５ｍｍｏｌ）を加え、全容を５０℃で１時間撹拌した。反応終了後、生じた固体をろ過によって取得し、メタノールで洗浄後、減圧乾燥させることで黄色固体として中間体Ｂを４．２２ｇ得た。収率は７８．９％であった。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 In a 3-reactor equipped with a thermometer, in a nitrogen stream, intermediate A synthesized in Step 1 (3.61 g, 14.48 mmol) and 2,5-dihydroxybenzaldehyde: 2.00 g (14.48 mmol) were added. , Methanol: dissolved in 40 mL. To this solution, (±) -10-camphor monosulfonic acid: 0.336 g (1.45 mmol) was added, and the whole volume was stirred at 50 ° C. for 1 hour. After completion of the reaction, the resulting solid was obtained by filtration, washed with methanol, and dried under reduced pressure to obtain 4.22 g of Intermediate B as a yellow solid. The yield was 78.9%.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＤＭＳＯ－ｄ６，ＴＭＳ，δｐｐｍ）：９．３８（ｓ，１Ｈ）、８．９７（ｓ，１Ｈ）、８．１４（ｓ，１Ｈ）、７．８３（ｄｄ，１Ｈ，Ｊ＝１．０Ｈｚ，８．０Ｈｚ）、７．６０（ｄｄ，１Ｈ，Ｊ＝０．５Ｈｚ，８．０Ｈｚ）、７．３３（ｄｄｄ，１Ｈ，Ｊ＝０．５Ｈｚ，８．０Ｈｚ，８．０Ｈｚ）、７．１４－７．１８（ｍ，２Ｈ）、６．７５（ｄ，１Ｈ，Ｊ＝８．５Ｈｚ）、６．７０（ｄｄ，１Ｈ，Ｊ＝３．０Ｈｚ，８．５Ｈｚ）、４．３２（ｔ，２Ｈ，７．５Ｈｚ）、１．６７（ｔｔ，２Ｈ，Ｊ＝７．０Ｈｚ、７．５Ｈｚ）、１．２４－１．４０（ｍ，６Ｈ）、０．８６（ｔ，３Ｈ，Ｊ＝７．５Ｈｚ）。 1 H-NMR (500 MHz, DMSO-d 6 , TMS, δ ppm): 9.38 (s, 1H), 8.97 (s, 1H), 8.14 (s, 1H), 7.83 (dd, 1H, J = 1.0 Hz, 8.0 Hz), 7.60 (dd, 1 H, J = 0.5 Hz, 8.0 Hz), 7.33 (ddd, 1 H, J = 0.5 Hz, 8.0 Hz) 8.0 Hz), 7.14-7.18 (m, 2H), 6.75 (d, 1 H, J = 8.5 Hz), 6.70 (dd, 1 H, J = 3.0 Hz, 8.5 Hz) ), 4.32 (t, 2H, 7.5 Hz), 1.67 (tt, 2H, J = 7.0 Hz, 7.5 Hz), 1.24-1.40 (m, 6H), 0.86 (T, 3H, J = 7.5 Hz).
ステップ３：中間体Ｃの合成
Figure JPOXMLDOC01-appb-C000045
 Step 3: Synthesis of Intermediate C
Figure JPOXMLDOC01-appb-C000045
　温度計を備えた３口反応器において、窒素気流中、フマリルクロリド：１２．００ｇ（７８．４５ｍｍｏｌ）およびクロロホルム：１２０ｍＬを入れ、均一な溶液とした。そこへ、４－（６－アクリロイルオキシ－ヘクス－１－イルオキシ）フェノール（ＤＫＳＨ社製）：１０．３７ｇ（３９．２３ｍｍｏｌ）を加えた。次いで、トリエチルアミン：８．７３ｇ（８６．３０ｍｍｏｌ）を加え、１時間攪拌した。反応終了後、反応液に０．５Ｎ塩酸水溶液：５００ｍＬを加え、クロロホルム：５００ｍＬで２回抽出した。有機層を集め、無水硫酸ナトリウムで乾燥させ、硫酸ナトリウムをろ別した。ロータリーエバポレーターにてろ液から溶媒を蒸発除去した後、得られた残留物をシリカゲルカラムクロマトグラフィー（トルエン：酢酸エチル＝９：１（容積比））により精製することで、中間体Ｃを黄色固体として４．０１ｇ得た。収率は２８．２％であった。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 In a three-necked reactor equipped with a thermometer, fumaryl chloride: 12.00 g (78.45 mmol) and chloroform: 120 mL were placed in a nitrogen stream to obtain a uniform solution. 4- (6-acryloyloxy-hex-1-yloxy) phenol (manufactured by DKSH) was added thereto to 10.37 g (39.23 mmol). Next, 8.73 g (86.30 mmol) of triethylamine was added and stirred for 1 hour. After completion of the reaction, 0.5N aqueous hydrochloric acid solution: 500 mL was added to the reaction solution, and the mixture was extracted twice with chloroform: 500 mL. The organic layer was collected, dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. After removing the solvent from the filtrate by evaporation on a rotary evaporator, the resulting residue was purified by silica gel column chromatography (toluene: ethyl acetate = 9: 1 (volume ratio)) to give Intermediate C as a yellow solid. 4.01 g was obtained. The yield was 28.2%.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＤＭＳＯ－ｄ６，ＴＭＳ，δｐｐｍ）：１３．３５（ｓ，１Ｈ）、７．１０－７．１４（ｍ，２Ｈ）、６．９４－６．９８（ｍ，２Ｈ）、６．８５－６．９１（ｍ，２Ｈ）、６．３２（ｄｄ，１Ｈ，Ｊ＝１．５Ｈｚ，１７．０Ｈｚ）、６．１７（ｄｄ，１Ｈ，Ｊ＝１０．５Ｈｚ，１７．０Ｈｚ）、５．９３（ｄｄ，１Ｈ，Ｊ＝１．５Ｈｚ，１０．５Ｈｚ）、４．１１（ｔ，２Ｈ，Ｊ＝６．５Ｈｚ）、３．９６（ｔ，２Ｈ，Ｊ＝６．５Ｈｚ）、１．７２（ｔｔ，２Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．６４（ｔｔ，２Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．３６－１．４７（ｍ，４Ｈ）。 1 H-NMR (500 MHz, DMSO-d 6 , TMS, δ ppm): 13.35 (s, 1H), 7.10-7.14 (m, 2H), 6.94-6.98 (m, 2H) ), 6.85-6.91 (m, 2H), 6.32 (dd, 1H, J = 1.5 Hz, 17.0 Hz), 6.17 (dd, 1H, J = 10.5 Hz, 17. 0 Hz), 5.93 (dd, 1 H, J = 1.5 Hz, 10.5 Hz), 4.11 (t, 2 H, J = 6.5 Hz), 3.96 (t, 2 H, J = 6.5 Hz) ) 1.72 (tt, 2H, J = 6.5 Hz, 7.0 Hz), 1.64 (tt, 2H, J = 6.5 Hz, 7.0 Hz), 1.36-1.47 (m, 4H).
ステップ４：重合性液晶化合物１の合成
Figure JPOXMLDOC01-appb-C000046
 Step 4: Synthesis of polymerizable liquid crystal compound 1
Figure JPOXMLDOC01-appb-C000046
　温度計を備えた３口反応器に、窒素気流中、前記ステップ２で合成した中間体Ｂ：２．５０ｇ（６．７７ｍｍｏｌ）およびＮ－メチル－２－ピロリドン：１００ｍＬを入れ、均一な溶液とした。そこへ、前記ステップ３で合成した中間体Ｃ：１３．４９ｇ（３７．２１ｍｍｏｌ）を加えた。次いで、Ｎ，Ｎ－ジメチル－４－アミノピリジン：０．９０９ｇ（７．４４ｍｍｏｌ）を加えた。次いで、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩：８．５６ｇ（４４．６６ｍｍｏｌ）を、反応液内温を２０℃～３０℃に保持しながら、５分間かけて加えた後、全容を２５℃でさらに３時間攪拌した。反応終了後、反応液に飽和食塩水：５００ｍＬを加え、酢酸エチル：５００ｍＬで２回抽出した。有機層を集め、無水硫酸ナトリウムで乾燥させ、硫酸ナトリウムをろ別した。ロータリーエバポレーターにてろ液から溶媒を蒸発除去した後、得られた残留物をシリカゲルカラムクロマトグラフィー（ＴＨＦ：クロロホルム＝１：２０（容積比））により精製することで、重合性液晶化合物１を黄色固体として３．２４ｇ得た。収率は４５．３％であった。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 In a 3-necked reactor equipped with a thermometer, the intermediate B synthesized in Step 2: 2.50 g (6.77 mmol) and N-methyl-2-pyrrolidone: 100 mL were placed in a nitrogen stream. did. Thereto was added 13.49 g (37.21 mmol) of Intermediate C synthesized in Step 3 above. Next, 0.909 g (7.44 mmol) of N, N-dimethyl-4-aminopyridine was added. Subsequently, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride: 8.56 g (44.66 mmol) was added over 5 minutes while maintaining the internal temperature of the reaction solution at 20 ° C. to 30 ° C. Thereafter, the whole volume was further stirred at 25 ° C. for 3 hours. After completion of the reaction, 500 mL of saturated brine was added to the reaction solution, and extracted twice with 500 mL of ethyl acetate. The organic layer was collected, dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. After evaporating and removing the solvent from the filtrate with a rotary evaporator, the obtained residue was purified by silica gel column chromatography (THF: chloroform = 1: 20 (volume ratio)), whereby polymerizable liquid crystal compound 1 was converted into a yellow solid. As a result, 3.24 g was obtained. The yield was 45.3%.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３，ＴＭＳ，δｐｐｍ）：７．８６（ｄ，１Ｈ，Ｊ＝２．５Ｈｚ）、７．６６－７．６８（ｍ，３Ｈ）、７．２２－７．３６（ｍ，７Ｈ）、７．１６（ｄｄ，１Ｈ，Ｊ＝１．０Ｈｚ，７．５Ｈｚ）、７．０５－７．１８（ｍ，４Ｈ）、６．９０－６．９４（ｍ，４Ｈ）、６．４１（ｄｄ，２Ｈ，Ｊ＝１．５Ｈｚ，１７．５Ｈｚ）、６．１３（ｄｄ，２Ｈ，Ｊ＝１０．５Ｈｚ，１７．５Ｈｚ）、５．８３（ｄｄ，２Ｈ，Ｊ＝１．５Ｈｚ，１０．５Ｈｚ）、４．３１（ｔ，２Ｈ，Ｊ＝７．５Ｈｚ）、４．１８（ｔ，４Ｈ，Ｊ＝６．５Ｈｚ）、３．９６８（ｔ，２Ｈ，Ｊ＝６．５Ｈｚ）、３．９６６（ｔ，２Ｈ，Ｊ＝６．５Ｈｚ）、１．８１（ｔｔ，４Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．７０－１．７５（ｍ，６Ｈ）、１．２８－１．５６（ｍ，１４Ｈ）、０．８６（ｔ，３Ｈ，Ｊ＝７．０Ｈｚ）。   1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): 7.86 (d, 1H, J = 2.5 Hz), 7.66-7.68 (m, 3H), 7.22-7.36 (M, 7H), 7.16 (dd, 1H, J = 1.0 Hz, 7.5 Hz), 7.05-7.18 (m, 4H), 6.90-6.94 (m, 4H) 6.41 (dd, 2H, J = 1.5 Hz, 17.5 Hz), 6.13 (dd, 2H, J = 10.5 Hz, 17.5 Hz), 5.83 (dd, 2H, J = 1) .5 Hz, 10.5 Hz), 4.31 (t, 2H, J = 7.5 Hz), 4.18 (t, 4H, J = 6.5 Hz), 3.968 (t, 2H, J = 6. 5 Hz), 3.966 (t, 2H, J = 6.5 Hz), 1.81 (tt, 4H, J = 6.5 Hz, 7.0 Hz), 1.70-1. 5 (m, 6H), 1.28-1.56 (m, 14H), 0.86 (t, 3H, J = 7.0Hz).
（合成例２）重合性液晶化合物２の合成
Figure JPOXMLDOC01-appb-C000047
 (Synthesis Example 2) Synthesis of polymerizable liquid crystal compound 2
Figure JPOXMLDOC01-appb-C000047
ステップ１：中間体Ｄの合成
Figure JPOXMLDOC01-appb-C000048
 Step 1: Synthesis of Intermediate D
Figure JPOXMLDOC01-appb-C000048
　中間体Ｄを、国際公開第２０１４／０１０３２５号を参考にして合成した。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 Intermediate D was synthesized with reference to WO 2014/010325.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＤＭＳＯ－ｄ６，ＴＭＳ，δｐｐｍ）：７．６６（ｄｄ、１Ｈ、Ｊ＝１．０Ｈｚ、８．０Ｈｚ）、７．３６（ｄｄ、１Ｈ、Ｊ＝１．０Ｈｚ、８．０Ｈｚ）、７．２０（ｄｔ、１Ｈ、Ｊ＝１．０Ｈｚ、７．５Ｈｚ）、６．９９（ｄｔ、１Ｈ、Ｊ＝１．０Ｈｚ，７．５Ｈｚ）、５．４０（ｓ、２Ｈ）、３．３１（ｓ、３Ｈ）。 1 H-NMR (500 MHz, DMSO-d 6 , TMS, δ ppm): 7.66 (dd, 1 H, J = 1.0 Hz, 8.0 Hz), 7.36 (dd, 1 H, J = 1.0 Hz, 8.0 Hz), 7.20 (dt, 1H, J = 1.0 Hz, 7.5 Hz), 6.99 (dt, 1H, J = 1.0 Hz, 7.5 Hz), 5.40 (s, 2H) ) 3.31 (s, 3H).
ステップ２：中間体Ｅの合成
Figure JPOXMLDOC01-appb-C000049
 Step 2: Synthesis of Intermediate E
Figure JPOXMLDOC01-appb-C000049
　温度計を備えた３つロ反応器において、窒素気流中、前記ステップ１で合成した中間体Ｄ：２．６０ｇ（１４．４８ｍｍｏｌ）および２，５－ジヒドロキシベンズアルデヒド：２．００ｇ（１４．４８ｍｍｏｌ）を、メタノール：４０ｍＬに溶解させた。この溶液に、（±）－１０－カンファ一スルホン酸：０．３３６ｇ（１．４５ｍｍｏｌ）を加え、全容を５０℃で１時間撹拌した。反応終了後、生じた固体をろ過によって取得し、メタノールで洗浄後、減圧乾燥させることで黄色固体として中間体Ｅを３．２６ｇ得た。収率は７５．２％であった。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 In a three-reactor equipped with a thermometer, in a nitrogen stream, intermediate D synthesized in Step 1 above: 2.60 g (14.48 mmol) and 2,5-dihydroxybenzaldehyde: 2.00 g (14.48 mmol) Was dissolved in methanol: 40 mL. To this solution, (±) -10-camphor monosulfonic acid: 0.336 g (1.45 mmol) was added, and the whole volume was stirred at 50 ° C. for 1 hour. After completion of the reaction, the resulting solid was obtained by filtration, washed with methanol, and dried under reduced pressure to obtain 3.26 g of Intermediate E as a yellow solid. The yield was 75.2%.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３，ＴＭＳ，δｐｐｍ）：９．７６（ｓ，１Ｈ）、７．７７（ｓ，１Ｈ）、７．６８－７．７０（ｍ，２Ｈ）、７．３７（ｄｄｄ，１Ｈ，Ｊ＝１．０Ｈｚ、７．５Ｈｚ、８．５Ｈｚ）、７．１８－７．２４（ｍ，２Ｈ）、６．９４（ｄ，１Ｈ，Ｊ＝９．０Ｈｚ）、６．８２（ｄｄ，１Ｈ，Ｊ＝３．０Ｈｚ，９．０Ｈｚ）、６．７８（ｄ，１Ｈ，Ｊ＝３．０Ｈｚ）、３．８１（ｄ，３Ｈ，Ｊ＝０．５Ｈｚ）。 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): 9.76 (s, 1H), 7.77 (s, 1H), 7.68-7.70 (m, 2H), 7.37 ( ddd, 1H, J = 1.0 Hz, 7.5 Hz, 8.5 Hz), 7.18-7.24 (m, 2H), 6.94 (d, 1H, J = 9.0 Hz), 6.82 (Dd, 1H, J = 3.0 Hz, 9.0 Hz), 6.78 (d, 1H, J = 3.0 Hz), 3.81 (d, 3H, J = 0.5 Hz).
ステップ３：重合性液晶化合物２の合成
Figure JPOXMLDOC01-appb-C000050
 Step 3: Synthesis of polymerizable liquid crystal compound 2
Figure JPOXMLDOC01-appb-C000050
　温度計を備えた３口反応器に、窒素気流中、前記ステップ２で合成した中間体Ｅ：２．５０ｇ（８．３５ｍｍｏｌ）およびＮ－メチル－２－ピロリドン：１００ｍＬを入れ、均一な溶液とした。そこへ、前記合成例１のステップ３で合成した中間体Ｃ：１６．６５ｇ（４５．９３ｍｍｏｌ）を加えた。次いで、Ｎ，Ｎ－ジメチル－４－アミノピリジン：１．１２ｇ（９．１９ｍｍｏｌ）を加えた。次いで、１－エチル－３－（３―ジメチルアミノプロピル）カルボジイミド塩酸塩：１０．５７ｇ（５５．１２ｍｍｏｌ）を、反応液内温を２０℃～３０℃に保持しながら、５分間かけて加えた後、全容を２５℃でさらに３時間攪拌した。反応終了後、反応液に飽和食塩水：５００ｍＬを加え、酢酸エチル：５００ｍＬで２回抽出した。有機層を集め、無水硫酸ナトリウムで乾燥させ、硫酸ナトリウムをろ別した。ロータリーエバポレーターにてろ液から溶媒を蒸発除去した後、得られた残留物をシリカゲルカラムクロマトグラフィー（ＴＨＦ：クロロホルム＝１：２０（容積比））により精製することで、重合性液晶化合物２を黄色固体として２．２２ｇ得た。収率は２６．９％であった。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 A 3-necked reactor equipped with a thermometer was charged with 2.50 g (8.35 mmol) of the intermediate E synthesized in Step 2 and 100 mL of N-methyl-2-pyrrolidone: 100 mL in a nitrogen stream. did. Thereto was added Intermediate C: 16.65 g (45.93 mmol) synthesized in Step 3 of Synthesis Example 1. Next, 1.12 g (9.19 mmol) of N, N-dimethyl-4-aminopyridine was added. Subsequently, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride: 10.57 g (55.12 mmol) was added over 5 minutes while maintaining the internal temperature of the reaction solution at 20 ° C. to 30 ° C. Thereafter, the whole volume was further stirred at 25 ° C. for 3 hours. After completion of the reaction, 500 mL of saturated brine was added to the reaction solution, and extracted twice with 500 mL of ethyl acetate. The organic layer was collected, dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. After evaporating and removing the solvent from the filtrate using a rotary evaporator, the obtained residue was purified by silica gel column chromatography (THF: chloroform = 1: 20 (volume ratio)), whereby the polymerizable liquid crystal compound 2 was converted into a yellow solid. As a result, 2.22 g was obtained. The yield was 26.9%.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３，ＴＭＳ，δｐｐｍ）：７．８７（ｄ，１Ｈ，２．５Ｈｚ）、７．６６－７．６８（ｍ，３Ｈ）、７．２３－７．３６（ｍ，７Ｈ）、７．１６－７．２０（ｍ，１Ｈ）、７．０５－７．１１（ｍ，４Ｈ）、６．９０－６．９４（ｍ，４Ｈ）、６．４３（ｄｄ，２Ｈ，Ｊ＝１．５Ｈｚ，１７．５Ｈｚ）、６．１３（ｄｄ，２Ｈ，Ｊ＝１０．５Ｈｚ，１７．５Ｈｚ）、５．８３（ｄｄ，２Ｈ，Ｊ＝１．５Ｈｚ，１０．５Ｈｚ）、４．１８（ｔ，４Ｈ，Ｊ＝６．５Ｈｚ）、３．９６８（ｔ，２Ｈ，Ｊ＝６．５Ｈｚ）、３．９６６（ｔ，２Ｈ，Ｊ＝６．５Ｈｚ）、３．７６（ｓ，３Ｈ）、１．８１（ｔｔ，４Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．７２（ｔｔ，４Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．４３－１．５６（ｍ，８Ｈ）。 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): 7.87 (d, 1H, 2.5 Hz), 7.66-7.68 (m, 3H), 7.23-7.36 (m 7H), 7.16-7.20 (m, 1H), 7.05-7.11 (m, 4H), 6.90-6.94 (m, 4H), 6.43 (dd, 2H) , J = 1.5 Hz, 17.5 Hz), 6.13 (dd, 2H, J = 10.5 Hz, 17.5 Hz), 5.83 (dd, 2H, J = 1.5 Hz, 10.5 Hz), 4.18 (t, 4H, J = 6.5 Hz), 3.968 (t, 2H, J = 6.5 Hz), 3.966 (t, 2H, J = 6.5 Hz), 3.76 (s 3H), 1.81 (tt, 4H, J = 6.5 Hz, 7.0 Hz), 1.72 (tt, 4H, J = 6.5 Hz, 7.0 Hz), 1 43-1.56 (m, 8H).
（合成例３）重合性液晶化合物３の合成
Figure JPOXMLDOC01-appb-C000051
 (Synthesis Example 3) Synthesis of polymerizable liquid crystal compound 3
Figure JPOXMLDOC01-appb-C000051
ステップ１：中間体Ｆの合成
Figure JPOXMLDOC01-appb-C000052
 Step 1: Synthesis of intermediate F
Figure JPOXMLDOC01-appb-C000052
　温度計を備えた３口反応器に、窒素気流中、水素化ナトリウム（油性）：４．１ｇ（水素化ナトリウム純分として２．６７ｇ（５５．５８ｍｍｏｌ））およびＴＨＦ：７５ｍＬを入れ、均一な溶液とした。そこへ、４－（６－アクリロイルオキシ－ヘクス－１－イルオキシ）フェノール（ＤＫＳＨ社製）：１３．３５ｇ（５０．５３ｍｍｏｌ）をＴＨＦ：７５ｍＬに溶解させ、溶液として加えた。次いで、無水マレイン酸：５．００ｇ（５０．５３ｍｍｏｌ）を加えたのち、Ｎ，Ｎ－ジメチル－４－アミノピリジン：６．７９ｇ（５５．５８ｍｍｏｌ）を加え、３時間攪拌した。反応終了後、反応液に０．２Ｎ塩酸水溶液：５００ｍＬを加え、酢酸エチル：５００ｍＬで抽出した。その後、有機層を飽和食塩水：５００ｍＬで洗浄した。有機層を集め、無水硫酸ナトリウムで乾燥させ、硫酸ナトリウムをろ別した。ロータリーエバポレーターにてろ液から溶媒を蒸発除去した後、得られた残留物をシリカゲルカラムクロマトグラフィー（トルエン：ＴＨＦ＝８：２（容積比））により精製することで、中間体Ｆを黄色固体として５．８５ｇ得た。収率は３２．０％であった。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 A three-necked reactor equipped with a thermometer was charged with 4.1 g of sodium hydride (oil-based) (2.67 g (55.58 mmol) as pure sodium hydride) and 75 mL of THF in a nitrogen stream. It was set as the solution. Thereto was dissolved 13.35 g (50.53 mmol) of 4- (6-acryloyloxy-hex-1-yloxy) phenol (manufactured by DKSH) in 75 mL of THF and added as a solution. Next, after adding 5.00 g (50.53 mmol) of maleic anhydride, 6.79 g (55.58 mmol) of N, N-dimethyl-4-aminopyridine was added and stirred for 3 hours. After completion of the reaction, 0.2N aqueous hydrochloric acid solution: 500 mL was added to the reaction solution, and the mixture was extracted with ethyl acetate: 500 mL. Then, the organic layer was washed with 500 mL of saturated saline. The organic layer was collected, dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. After removing the solvent from the filtrate by evaporation on a rotary evaporator, the resulting residue was purified by silica gel column chromatography (toluene: THF = 8: 2 (volume ratio)) to give Intermediate F as a yellow solid. .85 g was obtained. The yield was 32.0%.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３，ＴＭＳ，δｐｐｍ）：７．１３（ｄ，１Ｈ，Ｊ＝１６．０Ｈｚ）、７．０２－７．０８（ｍ，３Ｈ）、６．８８－６．９２（ｍ，２Ｈ）、６．４１（ｄｄ，１Ｈ，Ｊ＝１．５Ｈｚ，１７．５Ｈｚ）、６．１２（ｄｄ，１Ｈ，Ｊ＝１０．５Ｈｚ，１７．５Ｈｚ）、５．８２（ｄｄ，１Ｈ，Ｊ＝１．５Ｈｚ，１０．５Ｈｚ）、４．１８（ｔ，２Ｈ，６．５Ｈｚ）、３．９５（ｔ，２Ｈ，６．５Ｈｚ）、１．８０（ｔｔ，２Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．７２（ｔｔ，２Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．４２－１．５５（ｍ，４Ｈ）。 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): 7.13 (d, 1H, J = 16.0 Hz), 7.02-7.08 (m, 3H), 6.88-6.92 (M, 2H), 6.41 (dd, 1H, J = 1.5 Hz, 17.5 Hz), 6.12 (dd, 1H, J = 10.5 Hz, 17.5 Hz), 5.82 (dd, 1H, J = 1.5 Hz, 10.5 Hz), 4.18 (t, 2H, 6.5 Hz), 3.95 (t, 2H, 6.5 Hz), 1.80 (tt, 2H, J = 6) .5 Hz, 7.0 Hz), 1.72 (tt, 2H, J = 6.5 Hz, 7.0 Hz), 1.42-1.55 (m, 4H).
ステップ２：重合性液晶化合物３の合成
Figure JPOXMLDOC01-appb-C000053
 Step 2: Synthesis of polymerizable liquid crystal compound 3
Figure JPOXMLDOC01-appb-C000053
　温度計を備えた３口反応器に、窒素気流中、前記合成例１のステップ２で合成した中間体Ｂ：２．５０ｇ（６．７７ｍｍｏｌ）およびＮ－メチル－２－ピロリドン：１００ｍＬを入れ、均一な溶液とした。そこへ、前記ステップ１で合成した中間体Ｆ：１３．４９ｇ（３７．２１ｍｍｏｌ）を加えた。次いで、Ｎ，Ｎ－ジメチル－４－アミノピリジン：０．９０９ｇ（７．４４ｍｍｏｌ）を加えた。次いで、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩：８．５６ｇ（４４．６６ｍｍｏｌ）を、反応液内温を２０℃～３０℃に保持しながら、５分間かけて加えた後、全容を２５℃でさらに３時間攪拌した。反応終了後、反応液に飽和食塩水：５００ｍＬを加え、酢酸エチル：５００ｍＬで２回抽出した。有機層を集め、無水硫酸ナトリウムで乾燥させ、硫酸ナトリウムをろ別した。ロータリーエバポレーターにてろ液から溶媒を蒸発除去した後、得られた残留物をシリカゲルカラムクロマトグラフィー（ＴＨＦ：クロロホルム＝１：２０（容積比））により精製することで、重合性液晶化合物３を黄色固体として３．５３ｇ得た。収率は４９．３％であった。
　目的物の構造は１Ｈ－ＮＭＲで同定した。 A 3-necked reactor equipped with a thermometer was charged with 2.50 g (6.77 mmol) of intermediate B synthesized in Step 2 of Synthesis Example 1 and 100 mL of N-methyl-2-pyrrolidone in a nitrogen stream, A uniform solution was obtained. Thereto was added Intermediate F: 13.49 g (37.21 mmol) synthesized in Step 1 above. Next, 0.909 g (7.44 mmol) of N, N-dimethyl-4-aminopyridine was added. Subsequently, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride: 8.56 g (44.66 mmol) was added over 5 minutes while maintaining the internal temperature of the reaction solution at 20 ° C. to 30 ° C. Thereafter, the whole volume was further stirred at 25 ° C. for 3 hours. After completion of the reaction, 500 mL of saturated brine was added to the reaction solution, and extracted twice with 500 mL of ethyl acetate. The organic layer was collected, dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. After evaporating and removing the solvent from the filtrate with a rotary evaporator, the obtained residue was purified by silica gel column chromatography (THF: chloroform = 1: 20 (volume ratio)), whereby the polymerizable liquid crystal compound 3 was converted into a yellow solid. As a result, 3.53 g was obtained. The yield was 49.3%.
The structure of the target product was identified by 1 H-NMR.
　１Ｈ－ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３，ＴＭＳ，δｐｐｍ）：７．８６（ｄ，１Ｈ，Ｊ＝２．５Ｈｚ）、７．６６－７．６８（ｍ，３Ｈ）、７．２３－７．３６（ｍ，７Ｈ）、７．１５－７．１８（ｍ，１Ｈ）、７．０５－７．１８（ｍ，４Ｈ）、６．９０－６．９４（ｍ，４Ｈ）、６．４１（ｄｄ，２Ｈ，Ｊ＝１．５Ｈｚ，１７．５Ｈｚ）、６．１３（ｄｄ，２Ｈ，Ｊ＝１０．５Ｈｚ，１７．５Ｈｚ）、５．８３（ｄｄ，２Ｈ，Ｊ＝１．５Ｈｚ，１０．５Ｈｚ）、４．３１（ｔ，２Ｈ）、４．１８（ｔ，４Ｈ）、３．９６９（ｔ，２Ｈ）、３．９６６（ｔ，２Ｈ）、１．８１（ｔｔ，４Ｈ，Ｊ＝６．５Ｈｚ，７．０Ｈｚ）、１．７０－１．７５（ｍ，６Ｈ）、１．２６－１．５６（ｍ，１４Ｈ）、０．８６（ｔ，３Ｈ，７．０Ｈｚ）。 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): 7.86 (d, 1H, J = 2.5 Hz), 7.66-7.68 (m, 3H), 7.23-7.36 (M, 7H), 7.15-7.18 (m, 1H), 7.05-7.18 (m, 4H), 6.90-6.94 (m, 4H), 6.41 (dd , 2H, J = 1.5 Hz, 17.5 Hz), 6.13 (dd, 2H, J = 10.5 Hz, 17.5 Hz), 5.83 (dd, 2H, J = 1.5 Hz, 10.5 Hz) ), 4.31 (t, 2H), 4.18 (t, 4H), 3.969 (t, 2H), 3.966 (t, 2H), 1.81 (tt, 4H, J = 6. 5Hz, 7.0Hz), 1.70-1.75 (m, 6H), 1.26-1.56 (m, 14H), 0.86 (t, 3H, 7.0Hz)
＜相転移温度の測定＞
　重合性液晶化合物１～３のぞれぞれを５ｍｇ計量し、固体状態のまま、ラビング処理を施したポリイミド配向膜付きのガラス基板（Ｅ．Ｈ．Ｃ．Ｃｏ．，Ｌｔｄ．製、商品名：配向処理ガラス基板）２枚に挟んだ。この基板をホットプレート上に載せ、５０℃から２００℃まで昇温した後、再び５０℃まで降温した。昇温、降温する際の組織構造の変化を偏向光学顕微鏡（ニコン社製、ＥＣＬＩＰＳＥ　ＬＶ１００ＰＯＬ型）で観察した。 <Measurement of phase transition temperature>
5 mg of each of the polymerizable liquid crystal compounds 1 to 3 is weighed, and a glass substrate with a polyimide alignment film that has been subjected to a rubbing treatment in the solid state (manufactured by EHC Co., Ltd., trade name) : Orientated glass substrate) sandwiched between two sheets. The substrate was placed on a hot plate, heated from 50 ° C. to 200 ° C., and then cooled again to 50 ° C. Changes in the structure of the structure when the temperature was raised or lowered were observed with a deflection optical microscope (Nikon Corporation, ECLIPSE LV100POL type).
　測定した相転移温度を下記表１に示す。
　表１中、「Ｃ」はＣｒｙｓｔａｌ、「Ｎ」はＮｅｍａｔｉｃ、「Ｉ」はＩｓｏｔｒｏｐｉｃをそれぞれ表す。ここで、Ｃｒｙｓｔａｌとは、試験化合物が固相にあることを、Ｎｅｍａｔｉｃとは、試験化合物がネマチック液晶相にあることを、Ｉｓｏｔｒｏｐｉｃとは、試験化合物が等方性液体相にあることを、それぞれ示す。
　表１より、重合性液晶化合物１～３が液晶性を示すことが分かる。 The measured phase transition temperatures are shown in Table 1 below.
In Table 1, “C” represents Crystal, “N” represents Nematic, and “I” represents Isotropic. Here, “Crystal” means that the test compound is in a solid phase, “Nematic” means that the test compound is in a nematic liquid crystal phase, and “Isotropic” means that the test compound is in an isotropic liquid phase. Show.
From Table 1, it can be seen that the polymerizable liquid crystal compounds 1 to 3 exhibit liquid crystallinity.
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054
＜重合性液晶組成物の調製＞
（実施例１～３）
　合成例１～３で得た重合性液晶化合物１～３のそれぞれを２．０ｇと、光重合開始剤としてのアデカアークルズＮ１９１９Ｔ（ＡＤＥＫＡ社製）８６ｍｇと、界面活性剤としてのメガファックＦ－５６２（ＤＩＣ株式会社製）を１質量％含むシクロペンタノンおよび１，３－ジオキソランの混合溶媒（混合比（質量比）：シクロペンタノン／１，３－ジオキソラン＝４／６）６００ｍｇとを、別途調製した、１，３－ジオキソラン４．１ｇおよびシクロペンタノン２．７４ｇの混合溶媒に溶解させた。この溶液を０．４５μｍの細孔径を有するディスポーサブルフィルターでろ過し、重合性液晶組成物１～３をそれぞれ得た。 <Preparation of polymerizable liquid crystal composition>
(Examples 1 to 3)
2.0 g of each of the polymerizable liquid crystal compounds 1 to 3 obtained in Synthesis Examples 1 to 3, 86 mg of Adeka Arkles N1919T (manufactured by ADEKA) as a photopolymerization initiator, and MegaFac F- as a surfactant 600 mg of a mixed solvent of cyclopentanone and 1,3-dioxolane containing 1% by mass of 562 (manufactured by DIC Corporation) (mixing ratio (mass ratio): cyclopentanone / 1,3-dioxolane = 4/6), It was dissolved in a separately prepared mixed solvent of 4.1 g of 1,3-dioxolane and 2.74 g of cyclopentanone. This solution was filtered through a disposable filter having a pore diameter of 0.45 μm to obtain polymerizable liquid crystal compositions 1 to 3, respectively.
＜光学特性の評価＞
（ｉ）重合性組成物による液晶層の形成
　ラビング処理されたポリイミド配向膜の付与された透明ガラス基板（商品名：配向処理ガラス基板；Ｅ．Ｈ．Ｃ．Ｃｏ．，Ｌｔｄ．製）に、上述のようにして得られた重合性組成物１～３のそれぞれを＃６のバーコーターを使用して塗布し、塗膜を得た。得られた塗膜を、下記表２に示す温度で１分間乾燥した後、表２に示す温度で１分間配向処理し、液晶層を形成した。
（ｉｉ）光学異方体の形成
　上記（ｉ）で作製した液晶層のそれぞれを塗布面側から２０００ｍＪ／ｃｍ２の紫外線を表２に示す露光温度にて照射して重合させ、波長分散測定用の試料である透明ガラス基板付光学異方体をそれぞれ得た。ここで、光学異方体（液晶性高分子膜）の膜厚は、それぞれの透明ガラス基板付光学異方体に針で傷をつけ、その段差を表面形状測定装置ＤＥＫＴＡＫＩ５０型（株式会社アルバック製）で測定して計測した。結果を表２に示す。
（ｉｉｉ）位相差の測定
　上記（ｉｉ）で得られた試料のそれぞれにつき、波長４００ｎｍから８００ｎｍ間の位相差を、Ｍｕｅｌｌｅｒ　Ｍａｔｒｉｘ　Ｐｏｌａｒｉｍｅｔｅｒ　Ａｘｏｓｃａｎ（Ａｘｏｍｅｔｒｉｃｓ社製）を用いて測定した。波長５５０ｎｍにおける位相差を表２に示す。
（ｉｖ）波長分散の評価
　測定した位相差を用いて以下のように算出される波長分散比α，βの値から波長分散を評価した。結果を表２に示す。
α＝（４５０ｎｍにおける位相差値）／（５５０ｎｍにおける位相差値）
β＝（６５０ｎｍにおける位相差値）／（５５０ｎｍにおける位相差値）
（ｖ）５５０ｎｍにおけるΔｎの計算
　５５０ｎｍにおけるΔｎをそれぞれ下記の式より算出した。結果を表２に示す。
Δｎ＝（５５０ｎｍにおける位相差値；ｎｍ）／（光学異方体の膜厚；μｍ）／１０００ <Evaluation of optical properties>
(I) Formation of liquid crystal layer by polymerizable composition A transparent glass substrate (trade name: alignment glass substrate; manufactured by EHC Co., Ltd.) provided with a rubbed polyimide alignment film, Each of the polymerizable compositions 1 to 3 obtained as described above was applied using a # 6 bar coater to obtain a coating film. The obtained coating film was dried at a temperature shown in Table 2 for 1 minute, and then subjected to an alignment treatment at a temperature shown in Table 2 for 1 minute to form a liquid crystal layer.
(Ii) Formation of optical anisotropic body Each of the liquid crystal layers prepared in (i) above is polymerized by irradiating with 2000 mJ / cm 2 of ultraviolet light at the exposure temperature shown in Table 2 from the coated surface side. Each of the optical anisotropic bodies with a transparent glass substrate, which is a sample of the above, was obtained. Here, the film thickness of the optically anisotropic body (liquid crystalline polymer film) is scratched with a needle on each optically anisotropic body with a transparent glass substrate, and the step is measured with a surface shape measuring device DEKTAKI50 type (manufactured by ULVAC, Inc.). ) And measured. The results are shown in Table 2.
(Iii) Measurement of phase difference For each of the samples obtained in (ii) above, the phase difference between wavelengths from 400 nm to 800 nm was measured using Mueller Matrix Polarimeter Axoscan (manufactured by Axometrics). Table 2 shows the phase difference at a wavelength of 550 nm.
(Iv) Evaluation of wavelength dispersion Using the measured phase difference, the wavelength dispersion was evaluated from the values of the wavelength dispersion ratios α and β calculated as follows. The results are shown in Table 2.
α = (phase difference value at 450 nm) / (phase difference value at 550 nm)
β = (phase difference value at 650 nm) / (phase difference value at 550 nm)
(V) Calculation of Δn at 550 nm Δn at 550 nm was calculated from the following formula. The results are shown in Table 2.
Δn = (phase difference value at 550 nm; nm) / (film thickness of optical anisotropic body; μm) / 1000
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055
　広帯域性を示す理想的な波長分散性、即ち逆波長分散性を示す場合、αは１より小となり、βは１より大となる。表２より、実施例１～３の重合性液晶化合物１～３から製造される光学異方体は、いずれも広帯域性を示す理想的な波長分散性、即ち逆波長分散性を有していることが分かる。 In the case of an ideal wavelength dispersion exhibiting broadband characteristics, that is, reverse wavelength dispersion, α is smaller than 1 and β is larger than 1. From Table 2, all of the optical anisotropic bodies produced from the polymerizable liquid crystal compounds 1 to 3 of Examples 1 to 3 have ideal wavelength dispersion exhibiting broadband properties, that is, reverse wavelength dispersion. I understand that.

Claims (8)

  1. 　下記式（Ｉ）で示される重合性液晶化合物。
    Figure JPOXMLDOC01-appb-C000001
     〔式（Ｉ）中、
    　Ａｒは、下記式（ＩＩ－１）～（ＩＩ－３）の何れかで表され、Ｄ以外の置換基を１つ以上有していてもよい。
    Figure JPOXMLDOC01-appb-C000002
     （式（ＩＩ－１）～（ＩＩ－３）中、Ｄは、－Ｃ（Ｑ）＝Ｎ－Ｎ（Ａｙ）Ａｘ、－Ｃ（Ｑ）＝Ｎ－Ｎ＝Ｃ（Ａｙ）Ａｘ、または、－Ｃ（Ｑ）＝Ｎ－Ｎ＝Ａｚを表す。
    　Ｑは、水素原子または炭素数１～６のアルキル基を表し、
    　Ａｘは、炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する有機基を表し、
    　Ａｙは、水素原子、または、置換基を有していてもよい炭素数１～３０の有機基を表し、
    　Ａｚは、炭素数６～３０の芳香族炭化水素環および炭素数２～３０の芳香族複素環からなる群から選ばれる少なくとも一つの芳香環を有する有機基を表す。ここで、Ａｚは、Ｃ（Ａｙ）Ａｘである場合を除くものとする。
    　ただし、＊は、Ｚ１またはＺ２と結合する位置を表す。）
    　Ｚ１およびＺ２は、それぞれ独立して、化学的な単結合、－Ｏ－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｓ－、－Ｓ－Ｃ（＝Ｏ）－、－ＮＲ１１－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１１－、＊－ＣＨ２－Ｏ－、＊－ＣＨ２－ＣＨ２－Ｏ－、＊－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ２－ＣＨ２－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ２－ＣＨ２－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ＝ＣＨ－Ｃ（＝Ｏ）－Ｏ－、＊－ＣＨ＝ＣＨ－Ｏ－Ｃ（＝Ｏ）－、＊－ＣＨ＝Ｎ－、＊－Ｃ（ＣＨ３）＝Ｎ－、－Ｎ＝Ｎ－を表す。ここで、＊はＡｒと結合する位置を表し、Ｒ１１は、水素原子または炭素数１～６のアルキル基を表す。
    　Ａ１およびＡ２は、それぞれ独立して、置換基を有していてもよい炭素数１～２０の二価の鎖状脂肪族基を表す。前記鎖状脂肪族基には、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１２－、－ＮＲ１２－、または、－Ｃ（＝Ｏ）－が介在していてもよい。ただし、－Ｏ－または－Ｓ－がそれぞれ２以上隣接して介在する場合を除く。ここで、Ｒ１２は、水素原子または炭素数１～６のアルキル基を表す。ただし、Ａ１の、Ｚ１に結合する炭素原子およびＹ１もしくはＹ３に結合する炭素原子、並びに、Ａ２の、Ｚ２に結合する炭素原子およびＹ２もしくはＹ４に結合する炭素原子が、－Ｏ－、－Ｓ－、－Ｏ－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１２－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１２－、－ＮＲ１２－、または、－Ｃ（＝Ｏ）－に置換されることはない。
    　Ｂ１およびＢ２は、それぞれ独立して、置換基を有していてもよい環状脂肪族基、または、置換基を有していてもよい芳香族基を表す。
    　Ｙ１～Ｙ４は、それぞれ独立して、単結合、－Ｏ－、－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、－ＮＲ１３－Ｃ（＝Ｏ）－、－Ｃ（＝Ｏ）－ＮＲ１３－、－Ｏ－Ｃ（＝Ｏ）－Ｏ－、－ＮＲ１３－Ｃ（＝Ｏ）－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－ＮＲ１３－、または、－ＮＲ１３－Ｃ（＝Ｏ）－ＮＲ１４－を表す。ここで、Ｒ１３およびＲ１４は、それぞれ独立して、水素原子または炭素数１～６のアルキル基を表す。
    　Ｇ１およびＧ２は、それぞれ独立して、炭素数１～２０の脂肪族炭化水素基、および、炭素数３～２０の脂肪族炭化水素基に含まれるメチレン基（－ＣＨ２－）の１以上が－Ｏ－または－Ｃ（＝Ｏ）－に置換された基のいずれかの有機基である。なお、Ｇ１およびＧ２の前記有機基に含まれる水素原子は、炭素数１～５のアルキル基、炭素数１～５のアルコキシ基、または、ハロゲン原子に置換されていてもよい。ただし、Ｇ１およびＧ２の両末端のメチレン基（－ＣＨ２－）が、－Ｏ－または－Ｃ（＝Ｏ）－に置換されることはない。
    　Ｐ１およびＰ２は、それぞれ独立して、重合性基を表す。
    　ｐおよびｑは、それぞれ独立して、０～２の整数を表す。〕     A polymerizable liquid crystal compound represented by the following formula (I).
    Figure JPOXMLDOC01-appb-C000001
     [In formula (I),
    Ar is represented by any of the following formulas (II-1) to (II-3), and may have one or more substituents other than D.
    Figure JPOXMLDOC01-appb-C000002
     (In the formulas (II-1) to (II-3), D is -C (Q) = NN (Ay) Ax, -C (Q) = NN = C (Ay) Ax, or -C (Q) = NN = Az.
    Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
    Ax represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms,
    Ay represents a hydrogen atom or an organic group having 1 to 30 carbon atoms which may have a substituent,
    Az represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms. Here, Az excludes the case of C (Ay) Ax.
    However, * represents a position bonded with Z 1 or Z 2. )
    Z 1 and Z 2 are each independently a chemical single bond, —O—, —C (═O) —O—, —O—C (═O) —, —C (═O) —S. -, - S-C (= O) -, - NR 11 -C (= O) -, - C (= O) -NR 11 -, * - CH 2 -O -, * - CH 2 -CH 2 - O -, * - CH 2 -C (= O) -O -, * - CH 2 -O-C (= O) -, * - CH 2 -CH 2 -C (= O) -O -, * - CH 2 —CH 2 —O—C (═O) —, * —CH═CH—C (═O) —O—, * —CH═CH—O—C (═O) —, * —CH═N -, * -C (CH 3 ) = N-, -N = N-. Here, * represents a position bonded to Ar, and R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
    A 1 and A 2 each independently represents a divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent. The chain aliphatic group includes —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O—C (═O) —O—, — NR 12 —C (═O) —, —C (═O) —NR 12 —, —NR 12 —, or —C (═O) — may be present. However, the case where two or more of —O— or —S— are adjacent to each other is excluded. Here, R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Provided that the carbon atom bonded to Z 1 and the carbon atom bonded to Y 1 or Y 3 of A 1 and the carbon atom bonded to Z 2 and the carbon atom bonded to Y 2 or Y 4 of A 2 are bonded to each other. , —O—, —S—, —O—C (═O) —, —C (═O) —O—, —O—C (═O) —O—, —NR 12 —C (═O) There is no substitution with —, —C (═O) —NR 12 —, —NR 12 —, or —C (═O) —.
    B 1 and B 2 each independently represent a cyclic aliphatic group which may have a substituent or an aromatic group which may have a substituent.
    Y 1 to Y 4 are each independently a single bond, —O—, —C (═O) —, —C (═O) —O—, —O—C (═O) —, —NR 13. —C (═O) —, —C (═O) —NR 13 —, —O—C (═O) —O—, —NR 13 —C (═O) —O—, —O—C (= O) —NR 13 — or —NR 13 —C (═O) —NR 14 —. Here, R 13 and R 14 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
    G 1 and G 2 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and 1 of a methylene group (—CH 2 —) contained in an aliphatic hydrocarbon group having 3 to 20 carbon atoms. The above is an organic group of any of the groups substituted with —O— or —C (═O) —. Note that a hydrogen atom contained in the organic group of G 1 and G 2 may be substituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom. However, the methylene groups (—CH 2 —) at both ends of G 1 and G 2 are not substituted with —O— or —C (═O) —.
    P 1 and P 2 each independently represent a polymerizable group.
    p and q each independently represents an integer of 0 to 2. ]
  2. 　請求項１に記載の重合性液晶化合物を含む、重合性液晶組成物。 A polymerizable liquid crystal composition comprising the polymerizable liquid crystal compound according to claim 1.
  3. 　請求項１に記載の重合性液晶化合物を重合して得られる、高分子。 A polymer obtained by polymerizing the polymerizable liquid crystal compound according to claim 1.
  4. 　請求項３に記載の高分子を構成材料とする、光学フィルム。 An optical film comprising the polymer according to claim 3 as a constituent material.
  5. 　請求項３に記載の高分子を構成材料とする層を有する、光学異方体。 An optical anisotropic body having a layer comprising the polymer according to claim 3 as a constituent material.
  6. 　請求項５に記載の光学異方体および偏光フィルムを含む、偏光板。 A polarizing plate comprising the optical anisotropic body according to claim 5 and a polarizing film.
  7. 　請求項６に記載の偏光板を備える、表示装置。 A display device comprising the polarizing plate according to claim 6.
  8. 　請求項６に記載の偏光板を含む、反射防止フィルム。 An antireflection film comprising the polarizing plate according to claim 6.
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