JP2017218391A - Polymerizable compound and optical anisotropic body - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polymerizable compound giving such properties when added to a solution comprising a polymerizable composition that the resultant polymerizable composition has high storage stability and can induce a liquid crystal phase alignment in a short time with fewer alignment defects when applied to a substrate, and to provide a polymer obtained by polymerizing the polymerizable composition, and an optical anisotropic body using the polymer.SOLUTION: The present invention provides a compound represented by a general formula (I), a polymerizable composition comprising the compound, a polymer obtained by polymerizing the composition, and an optical anisotropic body using the polymer.SELECTED DRAWING: None

Description

  The present invention relates to a compound having a polymerizable group, a polymerizable composition containing the compound, a polymerizable liquid crystal composition, and an optical anisotropic body using a polymer obtained by polymerizing the polymerizable liquid crystal composition.

  Polymerizable compounds are used in various films. For example, it is possible to produce a film having a uniform orientation by aligning a polymerizable compound in a liquid crystal state and then polymerizing it. Thus, the produced film can be used for a polarizing plate, a phase difference plate, etc. which are required for a liquid crystal display. The polymerizable compound can also be used to produce a film having a cholesteric structure. In particular, a polymerizable liquid crystal compound having a low refractive index anisotropy (Δn) is useful as a material for a film having a cholesteric phase having a narrow selective reflection wavelength width. In many cases, two or more types of polymerizability are required to satisfy the required optical properties, polymerization rate, solubility, melting point, glass transition temperature, film transparency, mechanical strength, surface hardness, heat resistance and light resistance. Compositions consisting of compounds are used. At that time, the polymerizable compound to be used is required to bring good physical properties to the composition without adversely affecting other properties. In particular, when the purpose is to produce a film having a cholesteric structure, a polymerizable compound that can exist as a nematic phase or a cholesteric phase in a wide temperature range and has a high nematic phase or cholesteric phase liquid crystal orientation is required.

  When a polymerizable composition containing a polymerizable compound is used as an optical film material for a display or the like, liquid crystal phase alignment is induced in a short time when the polymerizable composition is applied to a substrate, and alignment defects are few. It is preferable. Further, from the viewpoint of the process, it is preferable that the polymerizable composition in the component does not precipitate even when the polymerizable composition is stored for a long period of time and has high storage stability. However, the conventionally known compounds may cause precipitation when added to the polymerizable composition and stored for a long period of time, or until the liquid crystal phase alignment is induced after the polymerizable composition is applied to the substrate. There was a problem that it took a long time and a problem that many alignment defects occurred (Patent Documents 1 to 4). When a film is produced using a polymerizable composition containing such a polymerizable compound, an additional step for redissolving the precipitate is required, or a step until the liquid crystal phase alignment is induced. There is a problem that a long time is required and that many alignment defects occur. Therefore, development of the polymeric compound which can solve such a problem was calculated | required.

KR10-2015-0037580 publication Japanese Patent Application Laid-Open No. 2005-035985 JP 2011-246365 A JP 2010-270108 A

Receil des Travaux Chimiques des Pays-Bas, 1996, 115, 6, 321-328

  The problem to be solved by the present invention is that it has high storage stability when added to a solution containing a polymerizable composition, and induces liquid crystal phase alignment in a short time when the polymerizable composition is applied to a substrate. And providing a polymerizable composition with few alignment defects. Furthermore, it is providing the polymer obtained by polymerizing the said polymeric composition, and the optical anisotropic body using the said polymer.

  As a result of intensive studies to solve the above problems, the present inventors have developed a polymerizable compound having a mesogenic group containing a specific partial structure. That is, the present invention provides a compound represented by the general formula (I), a polymerizable composition containing the compound, a resin using the compound, a resin additive, an oil, a filter, an adhesive, and an adhesive. Agents, oils and fats, inks, pharmaceuticals, cosmetics, detergents, building materials, packaging materials, liquid crystal materials, organic EL materials, organic semiconductor materials, electronic materials, display elements, electronic devices, communication equipment, automobile parts, aircraft parts, machine parts, Agrochemicals and foods, products using them, polymerizable liquid crystal compositions, polymers obtained by polymerizing the polymerizable liquid crystal compositions, and optical anisotropic bodies using the polymers are provided.

  The compound of the present invention has high storage stability when added to a polymerizable composition containing another polymerizable compound, and when the polymerizable composition is applied to a substrate, the liquid crystal phase alignment is achieved in a short time. Since it is induced and has few alignment defects, it is useful as a constituent member of the polymerizable composition. Moreover, the said polymeric composition is useful for the use of optical materials, such as a phase difference film and a selective reflection film.

  The present invention provides a compound having a specific structure, a polymerizable composition containing the compound, a resin using the compound, a resin additive, an oil, a filter, an adhesive, a pressure-sensitive adhesive, an oil and fat, an ink, Pharmaceuticals, cosmetics, detergents, building materials, packaging materials, liquid crystal materials, organic EL materials, organic semiconductor materials, electronic materials, display elements, electronic devices, communication equipment, automobile parts, aircraft parts, machine parts, agricultural chemicals and foodstuffs and the like Provided are a product used, a polymerizable liquid crystal composition, a polymer obtained by polymerizing the polymerizable liquid crystal composition, and an optical anisotropic body using the polymer.

  The compound of the present invention is represented by the following general formula (I).

(Wherein P ¹ represents a group which is polymerized by radical polymerization, cationic polymerization or anionic polymerization,
Sp ¹ represents a spacer group, and when a plurality of Sp ¹ are present, they may be the same or different,
X ¹ represents —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO. _{-O -, - CO-NH -} , - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 -, - CF 2 S -, - SCF 2 -, - CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ₂ CH ₂ —, —OCO—CH ₂ CH ₂ —, — _{CH 2 CH 2 -COO -, -} CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH = CH- , -N = N -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, ^{X 1} is more present They may be different even in the same case that,
k1 represents an integer of 0 to 10,
A ¹ and A ² are each independently the following formulas (A-1) to (A-9)

(Wherein these groups are unsubstituted or may be substituted by one or more substituents L),
L is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, A diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, — CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO- , —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or carbon atom optionally substituted by —C≡C— Number 1 20 represents a linear or branched alkyl group, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or L is P ^L- (Sp ^L -X ^L ) _kL-. Wherein P ^L represents a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and Sp ^L represents a spacer group or a single bond, but when there are a plurality of Sp ^L they may be different even in the ^same, X L is _{-O -, - S -, -} OCH 2 -, - CH 2 O -, - CO -, - COO -, - OCO -, - CO- S -, - S-CO - , - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 - _{, -CF 2 S -, - SCF} 2 -, - CH = CH-COO -, - CH = CH-O _{CO -, - COO-CH =} CH -, - OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH _{2 -OCO -, - COO-CH} 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH = CH -, - N = N -, - CH = N- N = CH -, - CF = CF -, - C≡C- or represents a single bond, they ^{if X L} there are a plurality may be different even in the same ^(however, P L - (Sp ^L -X ^L ) _kL -does not include an -O-O- bond.), KL represents an integer of 0 to 10, and when a plurality of L are present in a compound, they may be the same or different. Also good.
B ¹ represents expression from the following formula (B-1) (B- 15)

(Wherein, may be replaced by these or groups are unsubstituted or one or more of the above substituents L, L ^B represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, pentafluoro Sul Furanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, the above substituents A phenyl group optionally substituted by L, a benzyloxycarbonyl group substituted by at least one substituent L, a 2-phenylethyloxycarbonyl group optionally substituted by the substituent L, one —CH ₂ -Is -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO- ^{-O-COO -, - CO-} NR 0 -, - NR 0 -CO -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH-, -N = N-, -CR ⁰ = N-, -N = CR ^0- , -CH = CH-, -CF = CF- or -C≡C- (wherein R ⁰ is a hydrogen atom Or an alkyl group having 1 to 8 carbon atoms.), An arbitrary hydrogen atom in the group may be substituted with a fluorine atom, or 1 —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S. —CO—, —O—CO—O—, —CO—NR ⁰ —, —NR ⁰ —CO—, —CH═CH—COO—, —CH═CH—OC O -, - COO-CH = CH -, - OCO-CH = CH -, - N = N -, - CR 0 = N -, - N = CR 0 -, - CH = CH -, - CF = CF- Or a linear, branched or cyclic group having 3 to 20 carbon atoms which may be substituted by —C≡C— (wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms). represents an alkyl group, the carbon atom number of 3 from 20 linear, any hydrogen atom in branched or cyclic alkyl group may be substituted by a fluorine atom, or, L ^B is P ^{LB -} (Sp ^LB -X ^LB ) _kLB- may be represented, where P ^LB represents a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and Sp ^LB represents a spacer group or a single bond, If the Sp ^LB there is more than one, even they are the same May have become ^to, X LB is _{-O -, - S -, -} OCH 2 -, - CH 2 O -, - CO -, - COO -, - OCO -, - CO-S -, - S-CO -, - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 -, - CF 2 S-, _{-SCF 2 -, - CH = CH} -COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH ₂ CH ₂ —, —CH ₂ CH ₂ —COO—, —CH ₂ CH ₂ —OCO—, —COO—CH ₂ —, —OCO—CH ₂ —, —CH ₂ —COO—, —CH ₂ —OCO— , —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond. But if X ^LB there are a plurality thereof may be different even in the same, KLB is an integer of 0 to 10. ) Represents a group selected from
Z ¹ and Z ² are each independently —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —CO—, —COO—, —OCO—, —CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, _{-NH-O -, - O-} NH -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 -, - CF 2 S -, - SCF 2 -, - CH = CH- COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ₂ CH ₂ —, —OCO—CH ₂ CH ₂ —, —CH ₂ CH _{2 -COO -, - CH 2 CH 2} -OCO -, - OCO-CH 2 -, - CH 2 -COO -, - CH = CH -, - N = N-, CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or a single bond,
R ² is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or one —CH ₂ — or adjacent. Two or more —CH ₂ — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO. A straight chain of 1 to 20 carbon atoms which may be substituted by -O-, -CO-NH-, -NH-CO-, -CH = CH-, -CF = CF- or -C≡C- A branched alkyl group is represented, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or R ² is a group represented by — (X ² -Sp ² ) _k2 -P ² ( wherein, P ² is a radical polymerization, polymerization by cationic or anionic polymerization It represents that group, but Sp ² represents a spacer group, they if Sp ² there are a plurality may be different even in the same, ^{X 2} is -O -, - S -, - OCH 2 -, —CH ₂ O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH ₂ —, —CH ₂ S—, —CF ₂ O—, —OCF ₂ —, —CF ₂ S—, —SCF ₂ —, —CH═CH—COO—, —CH═CH—OCO—, — _{COO-CH = CH -, -} OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO- _{, -COO-CH 2 -, -} OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - H = CH -, - N = N -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, the same those ^{if X 2} there are a plurality Or may be different, and k2 represents an integer of 0 to 10), but does not include an —O—O— bond in the general formula. ) A compound represented by

In general formula (I), P ¹ and P ² present each independently represent a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and each independently represents the following formula (P-1) to formula ( P-20)

It is preferable to represent a group selected from: In particular, when ultraviolet polymerization is performed as a polymerization method, the formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-5), formula (P -7), formula (P-11), formula (P-13), formula (P-15) or formula (P-18) are preferred, and formula (P-1), formula (P-2), formula (P-18) P-3), formula (P-8), formula (P-11) or formula (P-13) is more preferred, and formula (P-1), formula (P-2) or formula (P-3) is more preferred. More preferred is formula (P-1) or (P-2).

In the general formula (I), Sp ¹ and existing Sp ² each independently represent a spacer group, but when there are a plurality of Sp ^1, they may be the same or different, and there are a plurality of Sp ² They may be the same or different. From the viewpoint of liquid crystallinity, availability of raw materials, and ease of synthesis, when there are a plurality of Sp ¹ and Sp ² present, they may be the same or different from each other, and each independently represents one − CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CO—, —COO—, —OCO. -, - CO-S -, - S-CO -, - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O- _{, -OCF 2 -, - CF 2} S -, - SCF 2 -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - _{COO-CH 2 CH 2 -,} - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 _{-OCO -, - COO-CH 2} -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH = CH -, - N = N -, - CH = N-N ═CH—, —CF═CF— or —C≡C— is preferably an alkylene group having 1 to 20 carbon atoms, and when there are a plurality of Sp ¹ and Sp ² present, They may be the same or different, and each independently represents one —CH ₂ — or two or more non-adjacent —CH ₂ — each independently —O—, —COO—, —OCO. Represents an alkylene group having 1 to 20 carbon atoms which may be replaced by-, -OCO-O-, -CO-NH-, -NH-CO-, -CH = CH- or -C≡C-. more preferably, each identical if Sp ² that Sp ¹ and there are plurality of It may be different even, each independently one -CH ₂ - or nonadjacent two or more -CH ₂ - are each independently -O -, - COO -, - OCO- or More preferably, it represents a linear alkylene group having 1 to 20 carbon atoms which may be replaced by -OCO-O-, and when there are a plurality of Sp ¹ and Sp ² present, they may be the same or different. even if well, each independently one -CH 2 _- or nonadjacent two or more -CH 2 _- from a good 1 -C be replaced by the each independently -O- 12 of It is even more preferred that it represents a linear alkylene group, and when there are a plurality of Sp ¹ and Sp ² present, they may be the same or different and each independently represents a straight chain having 1 to 12 carbon atoms. Especially represents a chain alkylene group preferable.

In general formula (I), X ¹ and X ² present are each independently —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CO—, —COO—, —OCO—, -CO-S -, - S- CO -, - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - _{OCF 2 -, - CF 2 S} -, - SCF 2 -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - COO- _{CH 2 CH 2 -, - OCO} -CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 _{-COO -, - CH 2 -OCO -} , - CH = CH -, - N = N -, - CH = N-N = CH -, - CF = C -, - C≡C- or represents a single bond, they if X ¹ there are a plurality may be the same or different and they if X ² there are a plurality or different may be the same May be. From the viewpoint of availability of the ease and synthetic ease of raw material, X ¹ directly bonded to A ¹ of X ^1, and, X ² is directly bonded with A ² of the present X ² are each independently - _{OCH 2 -, - CH 2 O} -, - COO -, - OCO -, - CO-S -, - S-CO -, - OCO-O -, - CO-NH -, - NH-CO-, _{-COO-CH 2 CH 2 -,} - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - it is preferable to represent a _CH 2 CH 2 -OCO- or a single bond, -OCH each independently _{2 -, - CH 2 O -} , - COO -, - OCO -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO- or _-CH 2 CH ₂ - it is more preferable that represent OCO-, each independently -OCH ₂ -, - CH ₂ -, - more preferably representing a COO- or -OCO-, it is particularly preferable to represent each independently -COO- or -OCO-.

Further, from the viewpoint of easy availability of raw materials and ease of synthesis, X ¹ that is not directly bonded to A ¹ among X ¹ and X ² that is not directly bonded to A ² among X ^{2 that} are present are: In the case where a plurality of groups are present, they may be the same or different, and each independently represents —O—, —S—, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, — CO-S -, - S- CO -, - OCO-O -, - CO-NH -, - NH-CO -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - It preferably represents CH ₂ CH ₂ —COO—, —CH ₂ CH ₂ —OCO— or a single bond, and each independently represents —O—, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO. _{-, - COO-CH 2 CH} 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -CO More preferably, it represents O—, —CH ₂ CH ₂ —OCO— or a single bond, and each independently represents more preferably —O—, —COO—, —OCO— or a single bond, and each independently It is even more preferable to represent —O— or a single bond, and it is particularly preferable to represent —O—.

In general formula (I), k1 and existing k2 each independently represent an integer of 0 to 10, but from the viewpoint of ease of synthesis and liquid crystallinity, each independently represents an integer of 0 to 5. Preferably, each independently represents an integer of 0 to 2, more preferably each independently represents 0 or 1, and each represents 1 from the viewpoint of low curing shrinkage when formed into a film. It is particularly preferred.
However, in the general formula (I), P ^1- (Sp ¹ -X ¹ ) _k1 -and the existing-(X ² -Sp ² ) _k2 -P ² do not include an -O-O- bond.

In the general formula (I), A ¹ and A ² are each independently unsubstituted or may be substituted by one or more substituents L. The following formula (A-1) to formula (A-9) )

Represents a group selected from: From the viewpoints of availability of raw materials, ease of synthesis, liquid crystallinity, storage stability, liquid crystal phase alignment and alignment defects, the above may be unsubstituted or substituted with one or more substituents L It is preferable to represent a group selected from formula (A-1) to formula (A-7), which is unsubstituted or may be substituted by one or more substituents L. It is more preferable to represent a group selected from formula (A-6) to formula (A-1) or formula (A-) which is unsubstituted or may be substituted by one or more substituents L. It is more preferable to represent a group selected from 2), and it is further preferable to represent a group represented by the above formula (A-1) which may be unsubstituted or substituted by one or more substituents L. More preferably (Here, the preferred group of the substituent L is preferably the substituent L below. Is the same as have group.), And particularly preferably a group represented by unsubstituted above formula (A-1).

In the general formula (I), the substituent L is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino. Group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one —CH ₂ — or two or more —CH ₂ — that are not adjacent to each other independently. -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO -, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C − Represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or the substituent L is P ^{L - (Sp L -X L)} kL - group may represent represented by, but they may be the same or different when a substituent L in the compound there are multiple. From the viewpoint of liquid crystallinity and ease of synthesis, the substituent L is a fluorine atom, chlorine atom, pentafluorosulfuranyl group, nitro group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, or any A hydrogen atom may be substituted with a fluorine atom, and one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —CO—, — 1 to 20 carbon atoms which may be substituted by a group selected from COO—, —OCO—, —O—CO—O—, —CH═CH—, —CF═CF— or —C≡C—. It is preferable to represent a linear or branched alkyl group, and the substituent L may be a fluorine atom, a chlorine atom, or an arbitrary hydrogen atom may be substituted with a fluorine atom, and one —CH ₂ — or adjacent group may be substituted. not two or more -CH ₂ - More preferably, each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted with a group selected from —O—, —COO— or —OCO—. More preferably, L represents a fluorine atom, a chlorine atom, or an arbitrary hydrogen atom, a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, which may be substituted with a fluorine atom. L particularly preferably represents a fluorine atom, a chlorine atom, or a linear alkyl group or linear alkoxy group having 1 to 8 carbon atoms. The substitution group L _{^{P L - (Sp L -X L}} ) kL - may represent a group represented by ^but, P ^L, Sp L, preferred structure of ^{X L} and kL, respectively ^P 1, Sp ¹ , the same as the preferred structure of X ¹ and k ¹ .

In the general formula (I), B ¹ is unsubstituted or may be substituted by one or more of the above substituents L. The following formulas (B-1) to (B-15)

Represents a group selected from: From the viewpoint of availability of raw materials, ease of synthesis, liquid crystallinity, refractive index anisotropy, storage stability, liquid crystal phase alignment and alignment defects, it is unsubstituted or is substituted by one or more substituents L. It preferably represents a group selected from the above formulas (B-1) to (B-12) which may be substituted, and may be unsubstituted or substituted by one or more substituents L. It is more preferable to represent a group selected from the above formulas (B-1) to (B-5), which is unsubstituted or may be substituted by one or more of the above substituents L. More preferably, it represents a group selected from B-1) to formula (B-3) or formula (B-5), which may be unsubstituted or substituted by one or more of the above substituents L And further represents a group selected from formula (B-1) or formula (B-2). Preferred, and particularly preferably a group selected from unsubstituted above formula (B-1) or Formula (B-2).

In the above formula (B-1) and formula ^(B-2), L B represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group An amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, a phenyl group that may be substituted by the substituent L, at least 1 Benzyloxycarbonyl group substituted by two substituents L, 2-phenylethyloxycarbonyl group optionally substituted by the substituent L, one —CH ₂ — is —S—, —CO—, —COO -, - OCO -, - CO -S -, - S-CO -, - OCO-O -, - CO-NR 0 -, - ^{R 0 -CO -, - CH =} CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - N = N -, - CR 0 = N- , —N═CR ⁰ —, —CH═CH—, —CF═CF—, or —C≡C— (wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms). And any hydrogen atom in the group may be substituted with a fluorine atom, or an alkyl group having 2 carbon atoms, or one —CH ₂ — or two or more —CH ₂ that are not adjacent to each other. -Are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR. ^{0 -, - NR 0 -CO -} , - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-C H = CH-, -N = N-, -CR ⁰ = N-, -N = CR ^0- , -CH = CH-, -CF = CF- or -C≡C- (wherein R ⁰ is hydrogen) Represents a linear, branched or cyclic alkyl group having 3 to 20 carbon atoms which may be substituted by an atom or an alkyl group having 1 to 8 carbon atoms. linear, any hydrogen atom in branched or cyclic alkyl group may be substituted by a fluorine atom, or, ^{L B} is ^P LB ^- represents a group represented by _- ^{(Sp _LB} -X _^LB) kLB . Raw material availability, ease of synthesis, liquid-crystalline, refractive index anisotropy, storage stability, in view of the liquid crystal phase orientation and alignment defect, L ^B is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, Pentafluorosulfuranyl group, nitro group, cyano group, dimethylamino group, diethylamino group, diisopropylamino group, phenyl group which may be substituted by the above substituent L, 2-phenyl which may be substituted by the above substituent L Ethyloxycarbonyl group, one —CH ₂ — is —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, — CO—NR ⁰ —, —NR ⁰ —CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —N═N— , -CR ⁰ = N-, -N = CR ^0— , —CH═CH—, —CF═CF—, or —C≡C— (wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), Arbitrary hydrogen atoms in the group may be substituted with fluorine atoms, an alkyl group having 2 carbon atoms, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR ^0- , -NR ^{0 -CO -, - CH = CH} -COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - N = N -, - CR 0 = N-, ^{-N = CR 0 -, - CH} = CH -, - CF = CF- or -C≡C- (a in the formula, ^{R 0} is a hydrogen or C 1 -C 8 Represents a straight chain, branched or cyclic alkyl group having 3 to 20 carbon atoms in which any hydrogen atom in the group may be substituted with a fluorine atom. preferably, ^{L B} is a fluorine atom, a chlorine atom, a nitro group, a cyano group, the substituent phenyl group which may be substituted by L, 1 single -CH ₂ - is -CO -, - COO -, - OCO-, -O-CO-O-, -CO-NR ^0- , -NR ⁰ -CO-, -CH = CH-COO-, -OCO-CH = CH-, -CR ⁰ = N-, -N = CR ⁰ —, —CH═CH—, —CF═CF—, or —C≡C— (wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms). Aralkyl having 2 carbon atoms in which any hydrogen atom may be replaced by a fluorine atom Group, or one -CH ₂ - or nonadjacent two or more -CH ₂ - independently are each -O -, - CO -, - COO -, - OCO -, - O-CO- O-, -CO-NR ^0- , -NR ⁰ -CO-, -CH = CH-COO-, -OCO-CH = CH-, -CR ⁰ = N-, -N = CR ^0- , -CH = CH—, —CF═CF— or —C≡C— (wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms). It is more preferable that it represents a linear, branched or cyclic alkyl group having 3 to 20 carbon atoms, in which any hydrogen atom in the group may be substituted with a fluorine atom, L ^B is a fluorine atom, a chlorine atom, a nitro group, a cyano group, the substituent phenyl group which may be substituted by a L, a linear or branched alkyl group having a carbon number of 13 to 20, carbon atoms 6 19 A linear or branched alkoxy group, wherein one —CH ₂ — is —CO—, —COO—, —OCO—, —O—CO—O—, —CO—NR ⁰ —, —NR ⁰ —CO -, - CH = CH-COO -, - OCO-CH = CH -, - CR 0 = N -, - N = CR 0 -, - CH = CH -, - CF = CF- or -C≡C- ( in the table, the alkyl group of R ⁰ is a hydrogen or C 1 -C 8 wherein .) Has been replaced by further addition -CH being substituted by the groups 2 _- and non-adjacent one -CH 2 _- or nonadjacent two or more -CH 2 _- is -O - may be substituted by, any hydrogen atom in the group may be substituted by a fluorine atom, more preferably represents a linear or branched alkyl group having 2 to 20 carbon atoms, L ^B is A fluorine atom, a chlorine atom, a nitro group, a cyano group, a phenyl group which may be substituted by the above-described substituent L, a linear or branched alkyl group having 13 to 20 carbon atoms, a straight chain having 6 to 19 carbon atoms Or branched alkoxy group, one —CH ₂ — is —CO—, —COO—, —OCO—, —CO—NR ⁰ —, —NR ⁰ —CO—, —CR ⁰ ═N— or —N = CR ⁰ - (wherein, ^{R 0} is a hydrogen atom Is replaced by the -O- _- is substituted by representing) an alkyl group having 1 to 8 carbon atoms, further addition one -CH 2 _-. Or nonadjacent two or more -CH 2 At best, any hydrogen atom in the group may be substituted by a fluorine atom, still more preferably it represents a straight-chain or branched alkyl group having 2 to 20 carbon atoms, L ^B is a fluorine atom, Cyano group, phenyl group, one —CH ₂ — is —CO—, —COO—, —OCO—, —CO—NR ⁰ —, —NR ⁰ —CO—, —CR ⁰ ═N— or —N═ Substituted with CR ⁰ — (wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), and in addition, one —CH ₂ — or two or more not adjacent to each other of -CH ₂ - it may be replaced by -O-, carbon It is particularly preferred that the child number 2 represents a linear or branched alkyl group of 10.

Among the groups represented by B ¹ in the general formula (I), the group represented by the above formula (B-1) is more specifically represented by the following formula (B-1-1) to formula ( B-1-11)

(Wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R ³¹ represents one —CH ₂ — or two or more non-adjacent —CH ₂ — being —O—. Represents a linear or branched alkyl group having 1 to 20 carbon atoms in which any hydrogen atom in the group may be substituted with a fluorine atom, and R ³² represents a hydrogen atom, one —CH ₂ — or two or more non-adjacent —CH ₂ — may be substituted with —O—, and any hydrogen atom in the group may be substituted with a fluorine atom. 20 represents a linear or branched alkyl group.) Among the groups represented by B ¹ in the general formula (I), the group represented by the above formula (B-2) is preferable. More specifically, as the group to be used, the following formulas (B-2-1) to (B-2-9)

(Wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R ³¹ represents one —CH ₂ — or two or more non-adjacent —CH ₂ — being —O—. Represents a linear or branched alkyl group having 1 to 20 carbon atoms in which any hydrogen atom in the group may be substituted with a fluorine atom, and R ³² represents a hydrogen atom, one —CH ₂ — or two or more non-adjacent —CH ₂ — may be substituted with —O—, and any hydrogen atom in the group may be substituted with a fluorine atom. It represents a group selected from 20 linear or branched alkyl groups.

In the general formula (I), Z ¹ and Z ² are each independently —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —CO—, —COO—. , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-,- NH—CO—NH—, —NH—O—, —O—NH—, —SCH ₂ —, —CH ₂ S—, —CF ₂ O—, —OCF ₂ —, —CF ₂ S—, —SCF ₂ -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 _{-, - CH 2 CH 2 -COO} -, - CH 2 CH 2 -OCO -, - OCO-CH 2 -, - CH 2 -COO -, - CH CH -, - N = N -, - CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or a single bond. Z ¹ and Z ² are each independently —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CF ₂ O from the viewpoint of liquid crystallinity, availability of raw materials, and ease of synthesis. _{-, - OCF 2 -, -} CH 2 CH 2 -, - CF 2 CF 2 -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = _{CH -, - COO-CH 2} CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO -, - CH = CH -, - CF = CF- , —C≡C— or a single bond is preferred, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH _{2 -, - COO-CH 2 CH} 2 -, - OCO-CH 2 CH 2 -, - CH 2 C _{2 -COO -, - CH 2 CH} 2 -OCO -, - CH = CH -, - C≡C- or is more preferably a single _{bond, -OCH 2 -, - CH 2} O -, - COO-, More preferably, it represents —OCO—, —CF ₂ O—, —OCF ₂ — or a single bond, and further represents —OCH ₂ —, —CH ₂ O—, —COO—, —OCO— or a single bond. More preferably, it represents -COO- or -OCO-.

In the general formula (I), R ² represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or one — CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—. 1 carbon atom which may be substituted by CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-, -CF = CF- or -C≡C- To 20 straight-chain or branched alkyl groups, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or R ² represents — (X ² —Sp ² ) _k2 —P. ² represents a group represented by ² ; When importance is attached to the flexibility when the film is formed, R ² preferably represents a group other than the group represented by-(X ² -Sp ² ) _k2 -P ² , and the mechanical strength when the film is formed is determined. In the case of emphasis, R ² preferably represents a group represented by — (X ² —Sp ² ) _k2 —P ² .

When R ² represents a group other than the group represented by — (X ² —Sp ² ) _k ² —P ² , R ² represents a hydrogen atom, a fluorine atom, a chlorine atom, from the viewpoint of liquid crystallinity and ease of synthesis. A cyano group, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —CO—, —COO—, —OCO—, —O—CO. Linear or branched having 1 to 12 carbon atoms which may be substituted by —O—, —CO—NH—, —NH—CO—, —CH═CH—, —CF═CF— or —C≡C— Preferably, it represents an alkyl group, and R ² is a hydrogen atom, a fluorine atom, a chlorine atom, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—. , -CO-, -COO-, -OCO- or -O-CO-O- More preferably represents a straight-chain or branched alkyl group of atoms from 1 to 12, R ² is a hydrogen atom, a fluorine atom, a chlorine atom, or a straight-chain alkyl group or straight chain alkoxy group having 1 to 12 carbon atoms It is more preferable that R ² represents a linear alkyl group having 1 to 12 carbon atoms or a linear alkoxy group, and it is particularly preferable.
When R ² represents a group represented by — (X ² —Sp ² ) _k2 —P ² , preferred structures of P ² , Sp ² , X ² and k ² are P ¹ , Sp ¹ and X, respectively. It is the same as the preferable structure which ¹ and k1 employ | adopt.

  Examples of the compound represented by the general formula (I) include the following general formula (I-i)

(Wherein P ¹ , P ² , Sp ¹ , Sp ² , X ¹ , X ² , k ¹ , k ² , A ¹ , A ² , B ¹ , Z ¹ and Z ² are each P ¹ in the general formula (I)) , P ² , Sp ¹ , Sp ² , X ¹ , X ² , k ¹ , k ² , A ¹ , A ² , B ¹ , Z ^1, and Z ² ) are preferred. General formula (I-i-i)

(In the formula, P ¹ , P ² , Sp ¹ , Sp ² , A ¹ , A ² , B ¹ , Z ¹ and Z ² are respectively P ¹ , P ² , Sp ¹ , Sp ² in the general formula (I), The compounds represented by A ¹ , A ² , B ¹ , Z ¹ and Z ² are more preferable. The following general formula (I-i-i)

^{(Wherein, P 1, P 2, Sp} 1 and Sp ² each represent the same meaning as ^{P 1, P 2,} Sp 1 and Sp ² in the general formula ^{(I), B 11} or is unsubstituted 1 Represents a group selected from the above formulas (B-1) to (B-5) which may be substituted by two or more substituents L, and Z ¹¹ and Z ²¹ each independently represent —OCH ₂ —, — A compound represented by CH ₂ O—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ — or a single bond) is more preferred, and the following general formula (I-i-i-) ii) or general formula (I-i-i-ii)

^{(Wherein, P 1, P 2, Sp} 1 and Sp ² each represent the same meaning as ^{P 1, P 2,} Sp 1 and Sp ² in the general formula ^{(I), B 11} or is unsubstituted 1 More preferably, a compound represented by the above formula (B-1) to (B-5) which may be substituted by two or more substituents L) is represented by the following general formula ( I-i-i-i-i) to general formula (I-i-i-i-ix)

^{(Wherein, P 1, P 2, Sp 1} , Sp 2 and L each represents the same meaning as ^{P 1, P 2, Sp 1} , Sp 2 and L in the general formula ^{(I), L B1} is fluorine atom, Chlorine atom, nitro group, cyano group, phenyl group which may be substituted by the above substituent L, linear or branched alkyl group having 13 to 20 carbon atoms, linear or branched group having 6 to 19 carbon atoms -Like alkoxy group, one —CH ₂ — is —CO—, —COO—, —OCO—, —CO—NR ⁰ —, —NR ⁰ —CO—, —CR ⁰ = N— or —N═CR ⁰ -(Wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), and in addition, one —CH ₂ — or two or more non-adjacent — CH 2 _- is may be replaced by -O-, arbitrary hydrogen atoms in the group There may be substituted by a fluorine atom, the compound represented by the representative.) A linear or branched alkyl group having 2 to 20 carbon atoms is more preferred.

  The compounds represented by the above general formula (I-i-i-i-i) to general formula (I-i-i-i-iv) are represented by the following general formula (I-i-i). -I-i-1) to general formula (I-i-i-i-iv-2)

^{(Wherein, P 1, P 2, Sp} 1, Sp 2 and L each represents the same meaning in the general formula (I) and ^{P 1, P 2, Sp 1} , Sp 2 and L, ^{R 0} is a hydrogen atom or Represents an alkyl group having 1 to 8 carbon atoms, and R ³¹ represents one —CH ₂ — or two or more non-adjacent —CH ₂ — may be substituted by —O—, Represents a linear or branched alkyl group having 1 to 20 carbon atoms in which a hydrogen atom may be substituted with a fluorine atom, and R ³² represents a hydrogen atom, one —CH ₂ — or not adjacent 2. A linear or branched alkyl group having 1 to 20 carbon atoms in which one or more —CH ₂ — may be substituted with —O—, and any hydrogen atom in the group may be substituted with a fluorine atom. And a compound represented by the general formula (I-i-i-i-v) i), general formula (I-ii-ii-vii), general formula (I-ii-ii-viii) or general formula (I-ii-ii-ix) Is particularly preferred.

  In the compound represented by the general formula (I-ii-ii-ix) to the general formula (I-ii-ii-ix), -I-i-1) to the compound represented by the general formula (I-i-i-i-iv-2) is more preferable, and the general formula (I-i-i-i-i) -1) to general formula (I-ii-ii-i-9) are more preferred, and general formula (I-ii-ii-i-5), general formula The compounds represented by (I-i-i-i-i-6) and general formula (I-i-i-i-i-9) are even more preferred, and general formula (I-i- Compounds represented by i-i-i-5) and general formula (Ii-i-i-i-6) are particularly preferred.

  From the viewpoint of liquid crystallinity, 1,4-cyclohexylene group, tetrahydropyran-2,5-diyl group, 1,3-dioxane-2,5-diyl contained in the compound represented by the general formula (I) The group, tetrahydronaphthalene-2,6-diyl group and decahydronaphthalene-2,6-diyl group may be either one of cis- and trans-forms or a mixture of both. From this point of view, the trans isomer is preferably the main component, and only the trans isomer is particularly preferable.

  Specifically, as the compound represented by the general formula (I), compounds represented by the following formulas (I-1) to (I-80) are preferable.

The compound of this invention can be manufactured with the following manufacturing methods.
(Production method 1) Production of a compound represented by the following formula (S-10)

^{(Wherein, P 1, P 2, Sp} 1, Sp 2 and ^{L B} each represent the same meaning as ^{P 1, P 2, Sp 1} , Sp 2 and ^{L B} in the general formula (I), PG is protecting group And halogen represents a halogen atom or a halogen equivalent.)
The carboxyl group of the compound represented by the formula (S-1) is protected with a protecting group (PG). The protecting group (PG) is not particularly limited as long as it can be stably protected until the deprotection step. For example, GREEN'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS ((Fourth Edition), PETER GM. Protecting groups (PG) mentioned in WUTS, THEODORA W. GREENE, John Wiley & Sons, Inc., Publication) and the like are preferred. Specific examples of the protecting group include a tetrahydropyranyl group, a tert-butyl group, a methoxymethyl group, an ethoxymethyl group, a methyl group, an ethyl group, and a benzyl group.

  The protecting group (PG) of the compound represented by the formula (S-2) is deprotected. The reaction conditions for deprotection are not particularly limited as long as they give the compound represented by formula (S-3), but those listed in the above-mentioned literature are preferable. It is also possible to obtain a compound represented by the formula (S-3) by protecting only one carboxyl group of the compound represented by the formula (S-1) with a protecting group (PG).

  The compound represented by the formula (S-5) can be obtained by reacting the compound represented by the formula (S-3) with the compound represented by the formula (S-4) in the presence of a base. Examples of the base include potassium carbonate, cesium carbonate, triethylamine and the like.

  The protecting group (PG) of the compound represented by the formula (S-5) is deprotected. The reaction conditions for deprotection are not particularly limited as long as they give the compound represented by the formula (S-6), but those listed in the above-mentioned literature are preferable.

  The compound represented by the formula (S-8) can be obtained by reacting the compound represented by the formula (S-6) with the compound represented by the formula (S-7). As the reaction conditions, for example, a method using a condensing agent or a compound represented by the formula (S-6) is converted to an acid chloride, mixed acid anhydride or carboxylic acid anhydride, and then represented by the general formula (S-7). The method of making it react with a compound in base presence is mentioned. When a condensing agent is used, examples of the condensing agent include N, N′-dicyclohexylcarbodiimide, N, N′-diisopropylcarbodiimide, and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride. Examples of the base include triethylamine and diisopropylethylamine.

A compound represented by formula (S-10) is reacted with a compound represented by formula (S-9) by a method similar to the method of the previous step. Can be obtained.
(Production method 2) Production of a compound represented by the following formula (S-17)

  The carboxyl group of the compound represented by formula (S-11) is reduced. The conditions for the reduction reaction are not particularly limited as long as they give the compound represented by the formula (S-12), and examples thereof include borane-tetrahydrofuran complex.

  A compound represented by the formula (S-14) can be obtained by reacting the compound represented by the formula (S-12) with a compound represented by the formula (S-13). Examples of the reaction conditions include Mitsunobu reaction. Alternatively, the hydroxyl group of the compound represented by the formula (S-12) is changed to a methanesulfoxy group or p-toluenesulfoxy group, and then reacted with the compound represented by the formula (S-13) in the presence of a base. It is also possible to make it. Examples of the base include potassium carbonate, cesium carbonate, potassium phosphate and the like.

  The protecting group (PG) of the compound represented by the formula (S-14) is deprotected. The reaction conditions for deprotection are not particularly limited as long as they give the compound represented by the formula (S-15), but those listed in the above-mentioned literature are preferable.

  The compound represented by the formula (S-17) can be obtained by reacting the compound represented by the formula (S-15) with a compound represented by the formula (S-16) in the presence of a base. Examples of the base include potassium carbonate, cesium carbonate, triethylamine and the like.

  Examples of reaction conditions other than those described in each step of production method 1 and production method 2 include, for example, an experimental chemistry course (edited by the Chemical Society of Japan, published by Maruzen Co., Ltd.), Organic Synthesis (John Wiley & Sons, Inc., Publication), and Bilstein Handbook of. Organic Chemistry (Beilstein-Institut fuer Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co.K), Fiesers' Reagents for Organic Synthesis (John Wiley & Sons, Inc.) conditions or SciFind described in the literature such as r (Chemical Abstracts Service, American Chemical Society) or Reaxys conditions provided from the online search services (Elsevier Ltd.) and the like.

  In each step, a reaction solvent can be appropriately used. The solvent is not particularly limited as long as it gives the target compound. For example, isopropyl alcohol, ethylene glycol, methanol, ethanol, chloroform, dichloromethane, 1,2-dichloroethane, acetone, acetonitrile, N, N-dimethylformamide, N , N-dimethylacetamide, dimethyl sulfoxide, diethyl ether, ethylene glycol monoethyl ether, xylene, ethyl acetate, 1,4-dioxane, tetrahydrofuran, pyridine, 1-methyl-2-pyrrolidinone, toluene, hexane, cyclohexane, heptane, methyl Examples include isobutyl ketone, tert-butyl methyl ether, and methyl ethyl ketone. When the reaction is carried out in an organic solvent and water two-phase system, a phase transfer catalyst can be added. Examples of the phase transfer catalyst include benzyltrimethylammonium chloride, polyoxyethylene (20) sorbitan monolaurate [Tween 20], sorbitan monooleate [Span 80], and the like.

  In each step, purification can be performed as necessary. Examples of the purification method include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid separation treatment. When using a purification agent, silica gel, alumina, activated carbon, activated clay, celite, zeolite, mesoporous silica, carbon nanotube, carbon nanohorn, Bincho charcoal, charcoal, graphene, ion exchange resin, acid clay, silicon dioxide, diatomaceous earth, Examples include perlite, cellulose, organic polymer, and porous gel.

  The compound of the present invention is preferably used for nematic liquid crystal compositions, smectic liquid crystal compositions, chiral smectic liquid crystal compositions and cholesteric liquid crystal compositions, and particularly preferably used for chiral smectic liquid crystal compositions and cholesteric liquid crystal compositions. . In the liquid crystal composition using the reactive compound of the present invention, a compound other than the present invention may be added.

  Specifically, the other polymerizable compound used by mixing with the polymerizable compound of the present invention is represented by the general formula (X-11).

And / or general formula (X-12)

(Wherein P ¹¹ , P ¹² and P ¹³ each independently represent a group which is polymerized by radical polymerization, cationic polymerization or anionic polymerization, and Sp ¹¹ , Sp ¹² and Sp ¹³ are each independently a single bond or a carbon atom. Represents an alkylene group of 1 to 20, but one —CH ₂ — or two or more non-adjacent —CH ₂ — is replaced by —O—, —COO—, —OCO—, —OCOO—. X ¹¹ , X ¹² and X ¹³ are each independently —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CO—, —COO—, —OCO—, — CO-S -, - S- CO -, - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF _{2 -, - CF 2 S -} , - SCF 2 -, - CH = CH-COO -, - CH = H-OCO -, - COO- CH = CH -, - OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH ₂ CH ₂ —OCO—, —COO—CH ₂ —, —OCO—CH ₂ —, —CH ₂ —COO—, —CH ₂ —OCO—, —CH═CH—, —CF═CF—, —C≡ C— or a single bond, and Z ¹¹ and Z ¹² are each independently —O—, —S—, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CO—, — CO-S -, - S- CO -, - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF _{2 -, - CF 2 S -} , - SCF 2 -, - CH 2 CH 2 -, - CH 2 CF 2 -, - CF 2 CH 2 -, —CF ₂ CF ₂ —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ₂ CH ₂ —, —OCO _{-CH 2 CH 2 -, - CH} 2 CH 2 -COO -, - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 - OCO-, -CH = CH-, -CF = CF-, -C≡C- or a single bond, and A ¹¹ , A ¹² , A ¹³ and A ¹⁴ are each independently a 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6 A diyl group or 1,3-dioxane-2,5 -Represents a diyl group, but A ¹¹ , A ¹² , A ¹³ and A ¹⁴ are each independently unsubstituted or an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a halogen atom, a cyano group Or a nitro group, R ¹¹ may be a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or One —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—. , -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH- , -OCO-CH = CH- A linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by —CH═CH—, —CF═CF— or —C≡C—, and m11 and m12 are 0, 1, 2 or 3 However, when m11 and / or m12 represents 2 or 3, two or three A ¹¹ , A ¹³ , Z ¹¹ and / or Z ¹² may be the same or different. ) Is preferred, and the case where P ¹¹ , P ¹² and P ¹³ are acrylic groups or methacrylic groups is particularly preferred. Specifically, the compound represented by the general formula (X-11) is represented by the general formula (X-11a).

Wherein W ¹¹ and W ¹² each independently represent a hydrogen atom or a methyl group, Sp ¹⁴ and Sp ¹⁵ each independently represent an alkylene group having 2 to 18 carbon atoms, and X ¹⁴ and X ¹⁵ each independently to -O -, - COO -, - OCO- or a single ^{bond, Z 13} and ^{Z 14} are each independently represents a -COO- or ^{-OCO-, a 15,} a ¹⁶ and ^{a 17} are each independently And may be unsubstituted or substituted by a fluorine atom, a chlorine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms. , A 4-phenylene group) is preferable, and the following formulas (X-11a-1) to (X-11a-4)

(Wherein, W ¹¹ , W ¹² , Sp ¹⁴ and Sp ¹⁵ represent the same meaning as in the general formula (X-11a)) are particularly preferable. In the above formulas (X-11a-1) to (X-11a-4), compounds in which Sp ¹⁴ and Sp ¹⁵ are each independently an alkylene group having 2 to 8 carbon atoms are particularly preferable.

  In addition, preferable bifunctional polymerizable compounds include those represented by the following general formulas (X-11b-1) to (X-11b-3):

(Wherein W ¹³ and W ¹⁴ each independently represent a hydrogen atom or a methyl group, and Sp ¹⁶ and Sp ¹⁷ each independently represent an alkylene group having 2 to 18 carbon atoms). Is mentioned. In the above formulas (X-11b-1) to (X-11b-3), compounds in which Sp ¹⁶ and Sp ¹⁷ are each independently an alkylene group having 2 to 8 carbon atoms are particularly preferable.

  Specific examples of the compound represented by the general formula (X-12) include the following general formula (X-12-1) to formula (X-12-7).

(In the formula, P ¹⁴ represents a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and Sp ¹⁸ represents a single bond or an alkylene group having 1 to 20 carbon atoms, but one —CH ₂ — or Two or more non-adjacent —CH ₂ — may be replaced by —O—, —COO—, —OCO—, —O—CO—O—, and X ¹⁶ is a single bond, —O—, — Represents COO— or —OCO—, Z ¹⁵ represents a single bond, —COO— or —OCO—, and L ¹¹ represents a fluorine atom, a chlorine atom, one —CH ₂ — or two or more not adjacent to each other. Each of —CH ₂ — independently represents a linear or branched alkyl group having 1 to 10 carbon atoms which may be independently replaced by —O—, —COO—, or —OCO—, and s11 represents 0 to 4 represents an integer, R ¹² is a hydrogen atom, a fluorine atom, a chlorine atom Cyano group, nitro group, one -CH ₂ - or nonadjacent two or more -CH ₂ - independently are each -O -, - S -, - CO -, - COO -, - OCO- , -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-,- Linear or branched having 1 to 20 carbon atoms which may be replaced by COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF— or —C≡C— And a compound represented by the following formula:

  A polymerizable compound that does not exhibit liquid crystallinity can be added to the polymerizable liquid crystal composition containing the compound of the present invention to such an extent that the liquid crystallinity of the composition is not significantly impaired. Specifically, any compound that is recognized as a polymer-forming monomer or polymer-forming oligomer in this technical field can be used without particular limitation. Specific examples include those described in “Photocuring Technology Data Book, Materials (Monomer, Oligomer, Photopolymerization Initiator)” (supervised by Kunihiro Ichimura, Kiyosuke Kato, Technonet).

  The compound of the present invention can be polymerized without using a photopolymerization initiator, but a photopolymerization initiator may be added depending on the purpose. In this case, the concentration of the photopolymerization initiator is preferably 0.1% by mass to 15% by mass, more preferably 0.2% by mass to 10% by mass, and 0.4% by mass to 8% by mass with respect to the compound of the present invention. % Is more preferable. Examples of the photopolymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, and acylphosphine oxides. Specific examples of the photopolymerization initiator include 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (IRGACURE 907), benzoic acid [1- [4- (phenylthio) benzoyl] heptylidene]. Amino (IRGACURE OXE 01) etc. are mentioned. Examples of the thermal polymerization initiator include azo compounds and peroxides. Specific examples of the thermal polymerization initiator include 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis (isobutyronitrile) and the like. One type of polymerization initiator may be used, or two or more types of polymerization initiators may be used in combination.

  In addition, a stabilizer can be added to the liquid crystal composition of the present invention in order to improve its storage stability. Examples of the stabilizer that can be used include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, and the like. It is done. When the stabilizer is used, the addition amount is preferably in the range of 0.005% by mass to 1% by mass, more preferably 0.02% by mass to 0.8% by mass, and 0.03% by mass with respect to the composition. To 0.5% by mass is more preferable. One kind of stabilizer may be used, or two or more kinds of stabilizers may be used in combination. Specifically, as the stabilizer, the formula (X-13-1) to the formula (X-13-35)

(Wherein n represents an integer of 0 to 20) is preferred.

  Further, when the polymerizable liquid crystal composition containing the compound of the present invention is used for applications such as films, optical elements, functional pigments, pharmaceuticals, cosmetics, coating agents, synthetic resins, Depending on the purpose, metals, metal complexes, dyes, pigments, dyes, fluorescent materials, phosphorescent materials, surfactants, leveling agents, thixotropic agents, gelling agents, polysaccharides, ultraviolet absorbers, infrared absorbers, antioxidants Further, metal oxides such as ion exchange resin and titanium oxide can be added.

The polymer obtained by polymerizing the polymerizable liquid crystal composition containing the compound of the present invention can be used for various applications. For example, a polymer obtained by polymerizing a polymerizable liquid crystal composition containing the compound of the present invention without orientation can be used as a light scattering plate, a depolarizing plate, and a moire fringe prevention plate. Moreover, the polymer obtained by superposing | polymerizing after orientating has optical anisotropy, and is useful. Such an optical anisotropic body includes, for example, a substrate obtained by rubbing a polymerizable liquid crystal composition containing the compound of the present invention with a cloth, a substrate on which an organic thin film is formed, or an alignment film on which SiO ₂ is obliquely deposited. It can be produced by polymerizing the polymerizable liquid crystal composition after it is supported on a substrate having it or sandwiched between substrates.

  Examples of the method for supporting the polymerizable liquid crystal composition on the substrate include spin coating, die coating, extrusion coating, roll coating, wire bar coating, gravure coating, spray coating, dipping, and printing. . Further, an organic solvent may be added to the polymerizable liquid crystal composition during coating. As the organic solvent, hydrocarbon solvents, halogenated hydrocarbon solvents, ether solvents, alcohol solvents, ketone solvents, ester solvents, aprotic solvents and the like can be used. The solvent is toluene or hexane, the halogenated hydrocarbon solvent is methylene chloride, the ether solvent is tetrahydrofuran, acetoxy-2-ethoxyethane or propylene glycol monomethyl ether acetate, and the alcohol solvent is methanol, ethanol or Isopropanol, acetone, methyl ethyl ketone, cyclohexanone, γ-butyl lactone or N-methylpyrrolidinone as the ketone solvent, ethyl acetate or cellosolve as the ester solvent, dimethyl as the aprotic solvent It can be mentioned formamide or acetonitrile. These may be used alone or in combination, and may be appropriately selected in consideration of the vapor pressure and the solubility of the polymerizable liquid crystal composition. As a method for volatilizing the added organic solvent, natural drying, heat drying, reduced pressure drying, or reduced pressure heat drying can be used. In order to further improve the applicability of the polymerizable liquid crystal material, it is also effective to provide an intermediate layer such as a polyimide thin film on the substrate or to add a leveling agent to the polymerizable liquid crystal material. The method of providing an intermediate layer such as a polyimide thin film on a substrate is effective for improving the adhesion between a polymer obtained by polymerizing a polymerizable liquid crystal material and the substrate.

  Examples of the alignment treatment other than the above include use of fluid alignment of a liquid crystal material, use of an electric field or a magnetic field. These orientation means may be used alone or in combination. Furthermore, a photo-alignment method can be used as an alignment treatment method instead of rubbing. As a shape of the substrate, in addition to a flat plate, a curved surface may be included as a constituent part. The material which comprises a board | substrate can be used regardless of an organic material and an inorganic material. Examples of the organic material used as the substrate material include polyethylene terephthalate, polycarbonate, polyimide, polyamide, polymethyl methacrylate, polystyrene, polyvinyl chloride, polytetrafluoroethylene, polychlorotrifluoroethylene, polyarylate, polysulfone, and triacetyl. Cellulose, cellulose, polyetheretherketone and the like can be mentioned, and examples of the inorganic material include silicon, glass and calcite.

When the polymerizable liquid crystal composition containing the compound of the present invention is polymerized, it is desirable that the polymerization proceeds rapidly. Therefore, a method of polymerizing by irradiating active energy rays such as ultraviolet rays or electron beams is preferable. When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used. Further, when the polymerization is carried out with the liquid crystal composition sandwiched between two substrates, at least the substrate on the irradiation surface side must have appropriate transparency to the active energy rays. Moreover, after polymerizing only a specific part using a mask at the time of light irradiation, the orientation state of the unpolymerized part is changed by changing conditions such as an electric field, a magnetic field, or temperature, and further irradiation with active energy rays is performed. Then, it is possible to use a means for polymerization. Moreover, it is preferable that the temperature at the time of irradiation exists in the temperature range by which the liquid crystal state of the polymeric liquid crystal composition of this invention is hold | maintained. In particular, when an optical anisotropic body is to be produced by photopolymerization, the polymerization is carried out at a temperature as close to room temperature as possible from the viewpoint of avoiding unintentional induction of thermal polymerization, that is, typically at a temperature of 25 ° C. It is preferable to make it. The intensity of the active energy ray is preferably 0.1 mW / cm ^{2 to 2} W / cm ² . When the intensity is 0.1 mW / cm ² or less, a great amount of time is required to complete the photopolymerization and the productivity is deteriorated. When the intensity is 2 W / cm ² or more, the polymerizable liquid crystal compound or the polymerizable liquid crystal is used. There is a risk that the composition will deteriorate.

  The optical anisotropic body obtained by polymerization can be subjected to a heat treatment for the purpose of reducing initial characteristic changes and achieving stable characteristic expression. The heat treatment temperature is preferably in the range of 50 to 250 ° C., and the heat treatment time is preferably in the range of 30 seconds to 12 hours.

  The optical anisotropic body manufactured by such a method may be peeled off from the substrate and used alone or without being peeled off. Further, the obtained optical anisotropic bodies may be laminated or bonded to another substrate for use.

EXAMPLES Hereinafter, although an Example is given and this invention is further described, this invention is not limited to these Examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by mass”. When handling a substance unstable to oxygen and / or moisture in each step, it is preferable to work in an inert gas such as nitrogen gas or argon gas. In addition to the operations specifically described below, as necessary, operations such as quenching, separation / extraction, neutralization, washing, separation, purification, drying, concentration, etc. that are commonly performed among those skilled in the art May be performed.
Example 1 Production of Compound Represented by Formula (I-1)

  Under a nitrogen atmosphere, 20.0 g of the compound represented by the formula (I-1-1), 8.8 g of tert-butyl alcohol, 1.3 g of N, N-dimethylaminopyridine, and 100 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 16.3 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 8 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 5% hydrochloric acid and brine. Purification was performed by column chromatography (silica gel, dichloromethane) to obtain 20.8 g of a compound represented by the formula (I-1-2).

  To the reaction vessel, 20.8 g of the compound represented by the formula (I-1-2), 200 mL of methanol, and 30 mL of 25% aqueous sodium hydroxide solution were added and heated and stirred at 60 ° C. Cool and add chloroform. 10% hydrochloric acid was added to adjust the pH of the aqueous layer to 4 to 5, followed by liquid separation treatment. The organic layer was washed with brine and dried over sodium sulfate. The insoluble material was filtered through celite, and the solvent was evaporated and dried to obtain 17.7 g of a compound represented by the formula (I-1-3).

  In a reaction vessel, 5.0 g of the compound represented by formula (I-1-3), 4.2 g of the compound represented by formula (I-1-4), 4.5 g of potassium carbonate, 20 mL of N, N-dimethylformamide. And heated and stirred at 90 ° C. for 8 hours. Dilute with dichloromethane and wash with water. Purification was performed by column chromatography (silica gel, dichloromethane / hexane) to obtain 6.7 g of a compound represented by the formula (I-1-5).

  To the reaction vessel, 6.7 g of the compound represented by the formula (I-1-5), 25 mL of dichloromethane, and 15 mL of formic acid were added and heated at 40 ° C. for 8 hours. After the solvent was distilled off, it was diluted with ethyl acetate and washed with water and brine. Purification was performed by column chromatography (alumina, ethyl acetate) to obtain 4.6 g of a compound represented by the formula (I-1-6).

Under a nitrogen atmosphere, 3.0 g of the compound represented by formula (I-1-6), 0.7 g of the compound represented by formula (I-1-7), N, N-dimethylaminopyridine,. 1 g and 40 mL of dichloromethane were added. While cooling with ice, 1.4 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. After recrystallization (dichloromethane / methanol), purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 2.5 g of a compound represented by the formula (I-1). .
LCMS: 769 [M + 1]
Example 2 Production of Compound Represented by Formula (I-2)

Under a nitrogen atmosphere, 3.0 g of the compound represented by the formula (I-2-1), 0.8 g of the compound represented by the formula (I-2-2), N, N-dimethylaminopyridine,. 1 g and 40 mL of dichloromethane were added. While cooling with ice, 1.4 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. After recrystallization (dichloromethane / methanol), purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 2.9 g of the compound represented by the formula (I-2). .
LCMS: 785 [M + 1]
Example 3 Production of Compound Represented by Formula (I-3)

  In a reaction vessel equipped with a Dean-Stark apparatus, 5.0 g of the compound represented by the formula (I-3-1), 3.9 g of the compound represented by the formula (I-3-2), 0.1 g of dibutyltin oxide, toluene 90 mL was added and heated to reflux for 8 hours while replacing the toluene. After toluene was distilled off, purification was performed by column chromatography (silica gel, ethyl acetate / hexane) to obtain 6.9 g of a compound represented by the formula (I-3-3).

Under a nitrogen atmosphere, 3.0 g of the compound represented by the formula (I-3-4), 1.2 g of the compound represented by the formula (I-3-3), N, N-dimethylaminopyridine,. 1 g and 40 mL of dichloromethane were added. While cooling with ice, 1.4 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. After recrystallization (dichloromethane / methanol), purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 2.8 g of a compound represented by the formula (I-3). .
LCMS: 873 [M + 1]
Example 4 Production of Compound Represented by Formula (I-4)

Under a nitrogen atmosphere, 3.0 g of the compound represented by the formula (I-4-1), 0.5 g of the compound represented by the formula (I-4-2), N, N-dimethylaminopyridine,. 1 g and 40 mL of dichloromethane were added. While cooling with ice, 1.4 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. After recrystallization (dichloromethane / methanol), purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 1.7 g of a compound represented by the formula (I-4). .
LCMS: 733 [M + 1]
Example 5 Production of Compound Represented by Formula (I-5)

Under a nitrogen atmosphere, 3.0 g of the compound represented by the formula (I-5-1), 0.9 g of the compound represented by the formula (I-5-2), N, N-dimethylaminopyridine,. 1 g and 40 mL of dichloromethane were added. While cooling with ice, 1.4 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. After recrystallization (dichloromethane / methanol), purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 2.9 g of the compound represented by the formula (I-5). .
LCMS: 803 [M + 1]
Example 6 Production of Compound Represented by Formula (I-6)

  To a reaction vessel equipped with a Dean-Stark apparatus, 15.0 g of a compound represented by the formula (I-6-1), 7.1 g of acrylic acid, 0.8 g of p-toluenesulfonic acid monohydrate, and 150 mL of toluene were added. The mixture was heated to reflux for 8 hours while removing water. After washing with a saturated aqueous sodium hydrogen carbonate solution and brine, the solvent was distilled off to obtain 17.8 g of a compound represented by the formula (I-6-2).

  In a reaction vessel, 3.0 g of the compound represented by the formula (I-6-2), 3.1 g of the compound represented by the formula (I-6-3), 2.8 g of potassium carbonate, 20 mL of N, N-dimethylformamide And heated and stirred at 90 ° C. for 10 hours. Diluted with dichloromethane and washed with water and brine. Purification was performed by column chromatography (alumina, dichloromethane / hexane) to obtain 4.5 g of a compound represented by the formula (I-6-4).

  To the reaction vessel, 4.5 g of the compound represented by the formula (I-6-4), 20 mL of tetrahydrofuran, 20 mL of methanol and 1 mL of concentrated hydrochloric acid were added and stirred at room temperature for 7 hours. Dilute with ethyl acetate and wash with water and brine. Purification was performed by column chromatography (alumina, ethyl acetate) to obtain 3.5 g of a compound represented by the formula (I-6-5).

  Under a nitrogen atmosphere, 3.0 g of the compound represented by formula (I-6-5), 1.0 g of the compound represented by formula (I-6-6), N, N-dimethylaminopyridine,. 1 g and 40 mL of dichloromethane were added. While cooling with ice, 1.8 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) to obtain 1.5 g of a compound represented by the formula (I-6-7).

  In a reaction vessel equipped with a Dean-Stark apparatus, 15.0 g of the compound represented by the formula (I-6-8), 11.9 g of 2-fluoroacrylic acid, 0.8 g of p-toluenesulfonic acid monohydrate, 150 mL of toluene And heated to reflux for 8 hours while removing water. After washing with a saturated aqueous sodium hydrogen carbonate solution and brine, the solvent was distilled off to obtain 18.9 g of a compound represented by the formula (I-6-9).

  In a reaction vessel, 3.0 g of the compound represented by formula (I-6-9), 3.5 g of the compound represented by formula (I-6-10), 3.2 g of potassium carbonate, 20 mL of N, N-dimethylformamide And heated and stirred at 90 ° C. for 10 hours. Diluted with dichloromethane and washed with water and brine. Purification was performed by column chromatography (alumina, dichloromethane / hexane) to obtain 5.0 g of a compound represented by the formula (I-6-11).

  To the reaction vessel were added 5.0 g of the compound represented by the formula (I-6-11), 20 mL of tetrahydrofuran, 20 mL of methanol and 1 mL of concentrated hydrochloric acid, and the mixture was stirred at room temperature for 7 hours. Dilute with ethyl acetate and wash with water and brine. Purification was performed by column chromatography (alumina, ethyl acetate) to obtain 3.8 g of a compound represented by the formula (I-6-12).

Under a nitrogen atmosphere, 1.5 g of the compound represented by the formula (I-6-7), 1.0 g of the compound represented by the formula (I-6-12), N, N-dimethylaminopyridine,. 1 g and 20 mL of dichloromethane were added. While cooling with ice, 0.4 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 1.7 g of a compound represented by the formula (I-6).
LCMS: 821 [M + 1]
Example 7 Production of Compound Represented by Formula (I-7)

  In a reaction vessel, 10.0 g of the compound represented by the formula (I-7-1), 9.4 g of the compound represented by the formula (I-7-2), 24.1 g of potassium carbonate, 100 mL of N, N-dimethylformamide And heated and stirred at 90 ° C. for 20 hours. The reaction was cooled and poured into 5% hydrochloric acid. Extracted with ethyl acetate and washed with water and brine. Purification was performed by column chromatography (silica gel, ethyl acetate / hexane) to obtain 6.9 g of a compound represented by the formula (I-7-3).

  Under a nitrogen atmosphere, 3.0 g of the compound represented by the formula (I-7-3), 3.6 g of the compound represented by the formula (I-7-4), N, N-dimethylaminopyridine 1 g and 20 mL of dichloromethane were added. While cooling with ice, 1.5 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane / hexane) to obtain 3.2 g of a compound represented by the formula (I-7-5).

  Under a nitrogen atmosphere, 3.2 g of the compound represented by the formula (I-7-5), 1.1 g of the compound represented by the formula (I-7-6), N, N-dimethylaminopyridine,. 1 g and 20 mL of dichloromethane were added. While cooling with ice, 0.8 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane / hexane) to obtain 3.4 g of a compound represented by the formula (I-7-7).

  To the reaction vessel, 3.4 g of the compound represented by the formula (I-7-7), 15 mL of dichloromethane, and 10 mL of formic acid were added and heated at 40 ° C. for 8 hours. After the solvent was distilled off, the resulting solid was washed with water and dried to obtain 2.9 g of a compound represented by the formula (I-7-8).

Under a nitrogen atmosphere, 2.9 g of the compound represented by the formula (I-7-8), 0.5 g of the mixture represented by the formula (I-7-9), N, N-dimethylaminopyridine,. 1 g and 20 mL of dichloromethane were added. While cooling with ice, 0.6 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 2.6 g of a compound represented by the formula (I-7).
LCMS: 909 [M + 1]
Example 8 Production of Compound Represented by Formula (I-8)

  To a reaction vessel equipped with a Dean-Stark apparatus, 5.0 g of a compound represented by the formula (I-8-1), 3.9 g of propanol, 0.3 g of p-toluenesulfonic acid monohydrate and 50 mL of toluene are added, and water is added. The mixture was heated to reflux for 8 hours while removing water. Purification was performed by column chromatography (silica gel, ethyl acetate / hexane) to obtain 5.1 g of a compound represented by the formula (I-8-2).

  Under a nitrogen atmosphere, 17.7 g of the compound represented by the formula (I-8-3) and 100 mL of tetrahydrofuran were added to the reaction vessel. While cooling with ice, 103 mL of 0.9 mol / L borane-tetrahydrofuran complex was added dropwise and stirred for 1 hour. After 5% hydrochloric acid was added dropwise, the mixture was extracted with ethyl acetate and washed with brine. By drying with sodium sulfate and distilling off the solvent, 14.9 g of a compound represented by the formula (I-8-4) was obtained.

  Under a nitrogen atmosphere, 10.0 g of the compound represented by the formula (I-8-4), 10.1 g of the compound represented by the formula (I-8-5), N, N-dimethylaminopyridine,. 3 g, 80 mL dichloromethane was added. While cooling with ice, 7.1 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) to obtain 15.4 g of a compound represented by the formula (I-8-6).

  To the reaction vessel, 15.4 g of the compound represented by the formula (I-8-6), 40 mL of dichloromethane, and 40 mL of formic acid were added and heated at 40 ° C. for 8 hours. Dilute with ethyl acetate and wash with water and brine. Purification was performed by column chromatography (silica gel, dichloromethane / ethyl acetate) to obtain 12.0 g of a compound represented by the formula (I-8-7).

  Under a nitrogen atmosphere, 3.0 g of the compound represented by the formula (I-8-2), 5.4 g of the compound represented by the formula (I-8-7), N, N-dimethylaminopyridine 2 g, 50 mL dichloromethane was added. While cooling with ice, 2.3 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) to obtain 4.1 g of a compound represented by the formula (I-8-8).

  Under a nitrogen atmosphere, 4.1 g of the compound represented by the formula (I-8-8), 1.8 g of the compound represented by the formula (I-8-9), N, N-dimethylaminopyridine. 1 g and 50 mL of dichloromethane were added. While cooling with ice, 1.2 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (alumina, dichloromethane) to obtain 4.6 g of a compound represented by the formula (I-8-10).

  To the reaction vessel, 4.6 g of the compound represented by the formula (I-8-10), 20 mL of tetrahydrofuran, 20 mL of methanol and 1 mL of concentrated hydrochloric acid were added and stirred at room temperature for 7 hours. Dilute with ethyl acetate and wash with water and brine. Purification was performed by column chromatography (alumina, ethyl acetate) to obtain 3.8 g of a compound represented by the formula (I-8-11).

  Under a nitrogen atmosphere, 5.0 g of the compound represented by the formula (I-8-12), 0.2 g of pyridinium p-toluenesulfonate, and 30 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 3.8 g of 3,4-dihydro-2H-pyran was added and stirred. After washing with a saturated aqueous sodium hydrogen carbonate solution and brine, purification was performed by column chromatography (alumina, dichloromethane) to obtain 7.6 g of a compound represented by the formula (I-8-13).

  To the reaction vessel was added 4.1 g of the compound represented by the formula (I-8-14), 20 mL of tetrahydrofuran, and 1.1 g of sodium hydride, and the mixture was stirred at room temperature for 1 hour. A solution prepared by dissolving 7.6 g of the compound represented by the formula (I-8-13) in 20 mL of tetrahydrofuran was dropped, and the mixture was heated and stirred at 50 ° C. for 8 hours. The reaction mixture was poured into ice water and extracted with dichloromethane. Purification was performed by column chromatography (alumina, hexane) to obtain 7.3 g of a compound represented by the formula (I-8-15).

  30 mL of formic acid and 30 mL of dichloromethane were added to the reaction vessel, and 15 mL of 35% aqueous hydrogen peroxide was added dropwise and stirred. A solution prepared by dissolving 7.3 g of the compound represented by the formula (I-8-15) in 20 mL of dichloromethane was dropped, and the mixture was heated and stirred at 40 ° C. for 6 hours. After washing with water and brine, purification was performed by column chromatography (alumina, hexane) to obtain 6.1 g of a compound represented by the formula (I-8-16).

  To the reaction vessel, 6.1 g of the compound represented by the formula (I-8-16), 30 mL of methanol, 30 mL of tetrahydrofuran, and 1 mL of concentrated hydrochloric acid were added and stirred at room temperature for 5 hours. After dilution with dichloromethane, it was washed with water and brine. Purification was performed by column chromatography (silica gel, dichloromethane / hexane) to obtain 4.0 g of a compound represented by the formula (I-8-17).

Under a nitrogen atmosphere, 3.8 g of a compound represented by the formula (I-8-11), 1.2 g of a compound represented by the formula (I-8-17), N, N-dimethylaminopyridine 1 g and 50 mL of dichloromethane were added. While cooling with ice, 0.8 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 3.9 g of a compound represented by the formula (I-8).
LCMS: 885 [M + 1]
Example 9 Production of Compound Represented by Formula (I-9)

  Under a nitrogen atmosphere, 5.0 g of the compound represented by the formula (I-9-1), 3.3 g of the compound represented by the formula (I-9-2), N, N-dimethylaminopyridine 1 g and 50 mL of dichloromethane were added. While cooling with ice, 3.5 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) to obtain 6.3 g of a compound represented by the formula (I-9-3).

  To the reaction vessel, 6.3 g of the compound represented by the formula (I-9-3), 15 mL of dichloromethane, and 10 mL of formic acid were added and heated at 40 ° C. for 8 hours. After diluting with ethyl acetate, it was washed with water and brine. Purification was performed by column chromatography (silica gel, dichloromethane / ethyl acetate) to obtain 4.7 g of a compound represented by the formula (I-9-4).

  In a nitrogen atmosphere, 4.7 g of the compound represented by the formula (I-9-4), 2.7 g of the compound represented by the formula (I-9-5), N, N-dimethylaminopyridine 1 g and 50 mL of dichloromethane were added. While cooling with ice, 2.5 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) to obtain 3.5 g of a compound represented by the formula (I-9-6).

  Under a nitrogen atmosphere, 3.5 g of the compound represented by the formula (I-9-6), 1.9 g of the compound represented by the formula (I-9-7), N, N-dimethylaminopyridine, and. 1 g and 50 mL of dichloromethane were added. While cooling with ice, 1.3 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 4.3 g of a compound represented by the formula (I-9-8).

  To the reaction vessel, 4.3 g of the compound represented by the formula (I-9-8), 15 mL of dichloromethane, and 10 mL of formic acid were added and heated at 40 ° C. for 8 hours. After diluting with ethyl acetate, it was washed with water and brine. Purification by column chromatography (silica gel, dichloromethane / ethyl acetate) and recrystallization (ethyl acetate / hexane) gave 3.5 g of a compound represented by the formula (I-9-9).

Under a nitrogen atmosphere, 3.5 g of the compound represented by the formula (I-9-9), 1.3 g of the compound represented by the formula (I-9-10), N, N-dimethylaminopyridine,. 1 g and 50 mL of dichloromethane were added. While cooling with ice, 0.9 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 3.3 g of a compound represented by the formula (I-9).
LCMS: 775 [M + 1]
Example 10 Production of Compound Represented by Formula (I-10)

  Under a nitrogen atmosphere, 14.9 g of the compound represented by the formula (I-10-1), 7.2 g of pyridine, and 150 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 8.8 g of methanesulfonyl chloride was added dropwise and stirred at room temperature for 3 hours. Poured into water and washed sequentially with 5% hydrochloric acid and brine. Purification was performed by column chromatography (silica gel, hexane / ethyl acetate) and recrystallization (acetone / hexane) to obtain 16.3 g of a compound represented by the formula (I-10-2).

  In a reaction vessel, 5.0 g of the compound represented by formula (I-10-2), 2.5 g of the compound represented by formula (I-10-3), 7.1 g of potassium carbonate, 70 mL of N, N-dimethylformamide And heated and stirred at 90 ° C. for 15 hours. The reaction was cooled and poured into 5% hydrochloric acid. Extracted with ethyl acetate and washed with water and brine. Purification by column chromatography (silica gel, hexane / ethyl acetate) and recrystallization (hexane / ethyl acetate) gave 2.9 g of the compound represented by the formula (I-10-4).

  Under a nitrogen atmosphere, 2.9 g of a compound represented by the formula (I-10-4), 1.7 g of a compound represented by the formula (I-10-5), N, N-dimethylaminopyridine 1 g and 50 mL of dichloromethane were added. While cooling with ice, 1.3 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 3.6 g of a compound represented by the formula (I-10-6).

  3.6 g of the compound represented by formula (I-10-6), 20 mL of dichloromethane, and 20 mL of formic acid were added to the reaction vessel, and the mixture was heated at 40 ° C. for 8 hours. After diluting with ethyl acetate, it was washed with water and brine. Purification by column chromatography (silica gel, dichloromethane / ethyl acetate) and recrystallization (ethyl acetate / hexane) gave 2.9 g of the compound represented by the formula (I-10-7).

Under a nitrogen atmosphere, 2.9 g of a compound represented by the formula (I-10-7), 0.9 g of a compound represented by the formula (I-10-8), N, N-dimethylaminopyridine 1 g and 40 mL of dichloromethane were added. While cooling with ice, 0.9 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 10 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 1% hydrochloric acid, water and brine. Purification by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) gave 2.9 g of the compound represented by the formula (I-10).
LCMS: 597 [M + 1]
A compound represented by the formula (I-11) to the formula (I-80) was produced by combining the same method as described above and a known method.
(Examples 11-30, Comparative Examples 1-8)
Compounds represented by formula (I-1) to formula (I-10) described in Example 1 to Example 10, compound (R-1) described in Patent Document 1, compound described in Patent Document 2 (R- 2) The compound (R-3) described in Patent Document 3 and the compound (R-4) described in Patent Document 4 were evaluated compounds.

  Further, compound (X-1) described in JP-A No. 2004-175728: 30%, compound (X-2) described in JP-A No. 2004-231638: 20%, compound described in JP-A No. 2005-179557 A liquid crystal composition composed of (X-3): 45% and compound (X-4): 5% described in JP-A No. 2004-175728 was used as a base liquid crystal (X).

  In order to evaluate the storage stability, a polymerizable liquid crystal composition was prepared by adding the compound to be evaluated to the base liquid crystal (X) in increments of 5% from 10% to 60% and heating and dissolving at 70 ° C. . After the prepared polymerizable liquid crystal composition is stored at 25 ° C. for 5 weeks, the maximum addition concentration of the compound to be evaluated at which no crystal precipitation occurs is described in the table below.

  From the above results, the compounds represented by formula (I-1) to formula (I-10) of the present invention are all compared with the compounds represented by comparative compounds (R-1) to (R-4). Thus, it can be seen that the storage stability is equivalent or better.

  The polyimide solution for alignment film was applied to a glass substrate having a thickness of 0.7 mm using a spin coating method, dried at 100 ° C. for 10 minutes, and then baked at 200 ° C. for 60 minutes to obtain a coating film. The obtained coating film was rubbed. The rubbing treatment was performed using a commercially available rubbing apparatus.

  11.87% of the base liquid crystal (X), 7.91% of the compound to be evaluated (40% based on the total content of the base liquid crystal (X) and the compound), photopolymerization initiator Irgacure 907 (manufactured by BASF) Was mixed with 0.20%, 4-methoxyphenol 0.02% and cyclohexanone 80.00%. This coating solution was applied to a rubbed glass substrate using a bar coater (No. 9), and then placed on a hot plate at 100 ° C. to evaporate the solvent. A cholesteric liquid crystal phase was induced with the evaporation of the solvent. The alignment speed until the cholesteric liquid crystal phase was induced was compared. ◯ when the cholesteric liquid crystal phase was induced almost simultaneously with the evaporation of the solvent, △ when the cholesteric liquid crystal phase was induced a little later, and x when the cholesteric liquid crystal phase was induced later. . In addition, alignment defects were evaluated for the obtained cholesteric liquid crystal phase by observation with a polarizing microscope. The coating film was divided into an area of 10 squares × 10 squares, for a total of 100 squares, and the number of squares in which orientation defects occurred was counted. It means that there are few orientation defects, so that a value is small. The results are shown in the table below.

  In Comparative Example 7, no cholesteric liquid crystal phase was induced. From the above results, the compounds represented by formula (I-1) to formula (I-10) of the present invention are all compared with the compounds represented by comparative compounds (R-1) to (R-4). Thus, it is understood that the time until the cholesteric liquid crystal phase is induced is short, and the obtained cholesteric liquid crystal phase has few alignment defects.

  From the above results, all the compounds represented by the formulas (I-1) to (I-10) of the present invention were compared with the comparative compound (R-1) to the comparative compound (R-4). When added to a solution containing the composition, it has high storage stability. When the polymerizable composition is applied to a substrate, liquid crystal phase alignment is induced in a short time, and alignment defects are few. Therefore, the compound of the present invention is useful as a constituent member of the polymerizable composition. Moreover, the optical anisotropic body using the polymeric liquid crystal composition containing the compound of this invention is useful for uses, such as an optical film.

Claims (8)

The following general formula (I)

(Wherein P ¹ represents a group which is polymerized by radical polymerization, cationic polymerization or anionic polymerization,
Sp ¹ represents a spacer group, and when a plurality of Sp ¹ are present, they may be the same or different,
X ¹ represents —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO. _{-O -, - CO-NH -} , - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 -, - CF 2 S -, - SCF 2 -, - CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ₂ CH ₂ —, —OCO—CH ₂ CH ₂ —, — _{CH 2 CH 2 -COO -, -} CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH = CH- , -N = N -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, ^{X 1} is more present They may be different even in the same case that,
k1 represents an integer of 0 to 10,
A ¹ and A ² are each independently the following formulas (A-1) to (A-9)

(Wherein these groups are unsubstituted or may be substituted by one or more substituents L),
L is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, A diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, — CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO- , —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or carbon atom optionally substituted by —C≡C— Number 1 20 represents a linear or branched alkyl group, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or L is P ^L- (Sp ^L -X ^L ) _kL-. Wherein P ^L represents a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and Sp ^L represents a spacer group or a single bond, but when there are a plurality of Sp ^L they may be different even in the ^same, X L is _{-O -, - S -, -} OCH 2 -, - CH 2 O -, - CO -, - COO -, - OCO -, - CO- S -, - S-CO - , - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 - _{, -CF 2 S -, - SCF} 2 -, - CH = CH-COO -, - CH = CH-O _{CO -, - COO-CH =} CH -, - OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH _{2 -OCO -, - COO-CH} 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH = CH -, - N = N -, - CH = N- N = CH -, - CF = CF -, - C≡C- or represents a single bond, they ^{if X L} there are a plurality may be different even in the same ^(however, P L - (Sp ^L -X ^L ) _kL -does not include an -O-O- bond.), KL represents an integer of 0 to 10, and when a plurality of L are present in a compound, they may be the same or different. Also good.
B ¹ represents expression from the following formula (B-1) (B- 15)

(Wherein, may be replaced by these or groups are unsubstituted or one or more of the above substituents L, L ^B represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, pentafluoro Sul Furanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, the above substituents A phenyl group optionally substituted by L, a benzyloxycarbonyl group substituted by at least one substituent L, a 2-phenylethyloxycarbonyl group optionally substituted by the substituent L, one —CH ₂ -Is -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO- ^{-O-COO -, - CO-} NR 0 -, - NR 0 -CO -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH-, -N = N-, -CR ⁰ = N-, -N = CR ^0- , -CH = CH-, -CF = CF- or -C≡C- (wherein R ⁰ is a hydrogen atom Or an alkyl group having 1 to 8 carbon atoms.), An arbitrary hydrogen atom in the group may be substituted with a fluorine atom, or 1 —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S. —CO—, —O—CO—O—, —CO—NR ⁰ —, —NR ⁰ —CO—, —CH═CH—COO—, —CH═CH—OC O -, - COO-CH = CH -, - OCO-CH = CH -, - N = N -, - CR 0 = N -, - N = CR 0 -, - CH = CH -, - CF = CF- Or a linear, branched or cyclic group having 3 to 20 carbon atoms which may be substituted by —C≡C— (wherein R ⁰ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms). represents an alkyl group, the carbon atom number of 3 from 20 linear, any hydrogen atom in branched or cyclic alkyl group may be substituted by a fluorine atom, or, L ^B is P ^{LB -} (Sp ^LB -X ^LB ) _kLB- may be represented, where P ^LB represents a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and Sp ^LB represents a spacer group or a single bond, If the Sp ^LB there is more than one, even they are the same May have become ^to, X LB is _{-O -, - S -, -} OCH 2 -, - CH 2 O -, - CO -, - COO -, - OCO -, - CO-S -, - S-CO -, - O-CO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 -, - CF 2 S-, _{-SCF 2 -, - CH = CH} -COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH ₂ CH ₂ —, —CH ₂ CH ₂ —COO—, —CH ₂ CH ₂ —OCO—, —COO—CH ₂ —, —OCO—CH ₂ —, —CH ₂ —COO—, —CH ₂ —OCO— , —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond. But if X ^LB there are a plurality thereof may be different even in the same, KLB is an integer of 0 to 10. ) Represents a group selected from
Z ¹ and Z ² are each independently —O—, —S—, —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —CO—, —COO—, —OCO—, —CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, _{-NH-O -, - O-} NH -, - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 -, - CF 2 S -, - SCF 2 -, - CH = CH- COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ₂ CH ₂ —, —OCO—CH ₂ CH ₂ —, —CH ₂ CH _{2 -COO -, - CH 2 CH 2} -OCO -, - OCO-CH 2 -, - CH 2 -COO -, - CH = CH -, - N = N-, CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or a single bond,
R ² is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or one —CH ₂ — or adjacent. Two or more —CH ₂ — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO. A straight chain of 1 to 20 carbon atoms which may be substituted by -O-, -CO-NH-, -NH-CO-, -CH = CH-, -CF = CF- or -C≡C- A branched alkyl group is represented, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or R ² is a group represented by — (X ² -Sp ² ) _k2 -P ² ( wherein, P ² is a radical polymerization, polymerization by cationic or anionic polymerization It represents that group, but Sp ² represents a spacer group, they if Sp ² there are a plurality may be different even in the same, ^{X 2} is -O -, - S -, - OCH 2 -, —CH ₂ O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH ₂ —, —CH ₂ S—, —CF ₂ O—, —OCF ₂ —, —CF ₂ S—, —SCF ₂ —, —CH═CH—COO—, —CH═CH—OCO—, — _{COO-CH = CH -, -} OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO- _{, -COO-CH 2 -, -} OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - H = CH -, - N = N -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, the same those ^{if X 2} there are a plurality Or may be different, and k2 represents an integer of 0 to 10), but does not include an —O—O— bond in the general formula.
) A compound represented by In general formula (I), P ¹ and P ² present are each independently the following formulas (P-1) to (P-20):

The compound according to claim 1, which represents a group selected from: In the general formula (I), Sp ¹ and existing Sp ² are each independently one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, — _{S -, - OCH 2 -,} - CH 2 O -, - CO -, - COO -, - OCO -, - CO-S -, - S-CO -, - OCO-O -, - CO-NH _{-, - NH-CO -,} - SCH 2 -, - CH 2 S -, - CF 2 O -, - OCF 2 -, - CF 2 S -, - SCF 2 -, - CH = CH-COO -, - CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ₂ CH ₂ —, —OCO—CH ₂ CH ₂ —, —CH ₂ CH ₂ —COO—, _{-CH 2 CH 2 -OCO -, -} COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH -OCO -, - CH = CH - , - N = N -, - CH = N-N = CH -, - CF = CF- or -C≡C- in replaced by from Good 1 to 20 carbon atoms in the The compound according to claim 1 or 2, which represents an alkylene group.   The polymeric composition containing the compound as described in any one of Claims 1-3.   The polymeric liquid crystal composition containing the compound as described in any one of Claims 1-3.   A polymer obtained by polymerizing the composition according to claim 4.   An optical anisotropic body using the polymer according to claim 6.   A resin, a resin additive, an oil, a filter, an adhesive, an adhesive, a fat, an ink, a pharmaceutical, a cosmetic, a detergent, a building material, a packaging material using the compound according to any one of claims 1 to 3. , Liquid crystal materials, organic EL materials, organic semiconductor materials, electronic materials, display elements, electronic devices, communication equipment, automobile parts, aircraft parts, machine parts, agricultural chemicals and foods, and products using them.