JP2018025752A - Optical anisotropic body - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an optical film that has a little alignment defect and prevents the occurrence of a change in optical characteristic when placed in a high temperature state.SOLUTION: The invention of the present application provided an optical film that includes a structural unit derived from a specific compound, that is, the invention of the present application provides an optical film that includes a structural unit derived from a compound represented by the general formula (I), has a little alignment defect, and prevents the occurrence of a change in optical characteristic when placed in a high temperature state, and provides a display using the optical film as well.SELECTED DRAWING: None

Description

  The present invention relates to an optical film and a display device using the optical film.

  A compound having a polymerizable group (polymerizable compound) is used as a raw material for various films. For example, it is possible to prepare a film-like polymer having a uniform orientation by arranging a polymerizable composition containing 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 display. 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. A polymerizable composition containing the compound is used. In that case, the polymerizable compound to be used is required to bring good physical properties to the polymerizable composition without adversely affecting other properties. Moreover, a film having a cholesteric structure can be produced by adding a chiral compound to such a polymerizable composition, arranging the polymerizable composition in a cholesteric liquid crystal state, and then polymerizing. For the purpose of producing a film having a cholesteric structure, a polymerizable compound that can exist as a liquid crystal phase in a wide temperature range and has high cholesteric orientation is required. In addition, when the polymerizable liquid crystal composition is used industrially, high storage stability is required so that the polymerizable compound in the component does not precipitate even when stored for a long time.

  When the film having the cholesteric structure is used as an optical film for a display device or the like, it is required that there are few orientation defects and the change amount of the selective reflection wavelength is small when placed in a high temperature state. However, conventionally known materials have alignment defects when a polymerizable cholesteric liquid crystal composition is prepared and a film is produced, and the selective reflection wavelength changes greatly when the film is stored at a high temperature. There was a problem of being uncertain (Patent Documents 1 and 2). When a film that easily causes orientation defects or changes the selective reflection wavelength, for example, is used for a display, the brightness of the screen becomes uneven or the color becomes unnatural due to long-term use. Or the target optical characteristics cannot be obtained, and the quality of the display product is greatly deteriorated.

  In addition, a retardation plate used for optical compensation such as a display is required to have few alignment defects and a small amount of change in retardation when placed in a high temperature state. However, conventionally known materials may cause alignment defects when a polymerizable liquid crystal composition is prepared to produce a film, or the phase difference may change greatly when the film is stored at a high temperature. There was a problem (Patent Documents 1 and 2).

WO2005 / 054406A1 WO2016 / 047648A1 publication

  The problem to be solved by the present invention is to provide an optical film that has few alignment defects and hardly changes in optical characteristics when placed in a high temperature state.

  As a result of intensive studies to solve the above problems, the present inventors have led to the development of an optical film containing a structural unit derived from a specific compound. That is, this invention provides the optical film containing the structural unit derived from the compound represented by general formula (I), and also provides the display apparatus using the said optical film.

  The optical film of the present invention is useful as a retardation film, a selective reflection film and the like for display devices because it has few alignment defects and hardly changes in optical characteristics when placed in a high temperature state.

  The present invention provides an optical film containing a structural unit derived from a specific compound, and also provides a display device using the optical film.

  The optical film of the present invention contains a structural unit derived from a compound represented by the following general formula (I).

(In the formula, P ¹ is the following formula (P-1) to formula (P-20)

Represents a group selected from
In R ^S1 , 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 A linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by ═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF— or —C≡C— In which any hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom,
Sp ¹ represents an alkylene group having 1 to 20 carbon atoms, 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,
n11 and n12 each independently represents an integer of 0 to 8,
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 any hydrogen atom in the group is a fluorine atom. One —CH ₂ — or two or more non-adjacent —CH ₂ — may be 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 C _{2 -, - CH 2 CH 2} -COO -, - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - Linear or branched having 1 to 20 carbon atoms which may be substituted by CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF— or —C≡C— Represents an alkyl group, or R ² represents the following formula (I-R2)

(Wherein P ² represents a group selected from the above formulas (P-1) to (P-20);
R ^S2 represents one —CH ₂ — or two or more non-adjacent —CH ₂ — 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 A linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by ═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF— or —C≡C— In which any hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom,
Sp ² represents an alkylene group having 1 to 20 carbon atoms, and when a plurality of Sp ² are present, they may be the same or different,
X ² 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 2} is plurality of They may be different even in the same case that,
k2 represents an integer of 0 to 10,
n21 and n22 each independently represents an integer of 0 to 8. )
However, the general formula (I) does not include an —O—O— bond.

In the general formula (I), P ¹ and P ² present represent a group selected from the formulas (P-1) to (P-20). 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-3), formula (P-8), formula (P P-11) or formula (P-13) is more preferred, formula (P-1), formula (P-2) or formula (P-3) is more preferred, formula (P-1) or formula (P- 2) is particularly preferred.

In the general formula (I), R ^S1 may be any hydrogen atom in the group substituted by a fluorine atom or a chlorine atom, and 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—NH—. , —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF— Alternatively, it represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by -C≡C-. From the viewpoint of easy availability of raw materials, ease of synthesis, liquid crystallinity, a small number of alignment defects, and stability of optical properties, R ^S1 can be substituted with any hydrogen atom in the group by a fluorine atom or a chlorine atom. Well, one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —CO—, —COO—, —OCO— or —O—CO—O—. It preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms that may be substituted by R ¹ , and R ^S1 may be substituted with any hydrogen atom in the group by a fluorine atom. 1 to 10 carbon atoms in which —CH ₂ — or two or more non-adjacent —CH ₂ — may be each independently substituted by —O—, —CO—, —COO— or —OCO—. more preferably represents a linear or branched alkyl group, R ^S1 is Any hydrogen atom may be substituted by fluorine atoms in one -CH 2 _- or nonadjacent two or more -CH 2 _- may be replaced each by independently -O- is More preferably, it represents a linear alkyl group having 1 to 10 carbon atoms, R ^S1 more preferably represents a linear alkyl group having 1 to 3 carbon atoms, and R ^S1 represents a methyl group. Is particularly preferred.

In the general formula (I), Sp ¹ represents an alkylene group having 1 to 20 carbon atoms, and when a plurality of Sp ¹ are present, 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 s} , they may be the same or different and each represents an alkylene group having 2 to 12 carbon atoms. Preferably, it represents an alkylene group having 2 to 10 carbon atoms, more preferably represents an alkylene group having 2 to 8 carbon atoms, and even more preferably represents an alkylene group having 2 to 6 carbon atoms. And particularly preferably an alkylene group having 2 carbon atoms.

In the general formula (I), 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 a single bond. But, they may be the same or different if X ¹ is more present. From the viewpoint of availability of raw materials and ease of synthesis, when there are a plurality of X ^{1 s} , they may be the same or different from each other, —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 —, —CH ₂ CH ₂ —COO—, —CH ₂ CH ₂ —OCO— or a single bond is preferably represented, —O—, —OCH ₂ —, —CH ₂ O _{-, - COO -, - OCO} -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - represents a _CH 2 CH 2 -OCO- or a single bond And more preferably represents -O-, -COO-, -OCO- or a single bond. Preferably, the still more preferred that represents -O- or a single bond, and particularly preferably a single bond.

  In general formula (I), k1 represents an integer of 0 to 10, but preferably represents an integer of 0 to 5, and more preferably represents an integer of 0 to 2, from the viewpoint of ease of synthesis and liquid crystallinity. Preferably, 0 or 1 is more preferable, and 1 is particularly preferable from the viewpoint of low curing shrinkage.

  In the general formula (I), n11 and n12 each independently represents an integer of 0 to 8, but the availability of raw materials, ease of synthesis, liquid crystallinity, few alignment defects, and stability of optical properties From the viewpoint, it is preferable that each independently represents an integer from 0 to 6, more preferably each independently represents an integer from 0 to 4, more preferably each independently represents an integer from 0 to 2, It is particularly preferred that each independently represents 0 or 1. Moreover, when importance is attached to the storage stability when added to the polymerizable composition, it is preferable that n11 and n12 each represent a different integer.

In the general formula (I), 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 an arbitrary group And a fluorine atom may be substituted with 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 -, - From 1 carbon atom which may be substituted by CH ₂ —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF— or —C≡C—. 20 represents a linear or branched alkyl group, or R ² represents the following formula (I-R2)

Represents a group represented by In the case where importance is attached to the flexibility when made into a film, R ² preferably represents a group other than the group represented by the formula (I-R2), and in the case where importance is given to the mechanical strength when made into a film, R ² Preferably represents a group represented by the formula (I-R2).

When R ² represents a group other than the group represented by formula (I-R2), R ² represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or 1 from the viewpoint of liquid crystallinity and ease of synthesis. number of -CH ₂ - or nonadjacent two or more -CH ₂ - are each independently -O -, - CO -, - COO -, - OCO -, - OCO-O -, - CO To represent a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by —NH—, —NH—CO—, —CH═CH—, —CF═CF— or —C≡C—. Preferably, R ² is a hydrogen atom, a fluorine atom, a chlorine atom, or one —CH ₂ — or two or more non-adjacent —CH ₂ —, each independently —O—, —CO—, — 1 to 12 carbon atoms which may be substituted by COO-, -OCO- or -O-CO-O- More preferably represents a straight-chain or branched alkyl group, R ² represents a hydrogen atom, a fluorine atom, a chlorine atom, or, more preferably represent a straight chain alkyl group or straight chain alkoxy group having 1 to 12 carbon atoms, R ² particularly preferably represents a linear alkyl group having 1 to 12 carbon atoms or a linear alkoxy group.

When R ² represents a group represented by the formula (I-R2), preferred structures of P ² , R ^S2 , Sp ² , X ² , k ² , n 21 and n 22 are P ¹ , R ^S1 , sp ^{1, X 1,} k1, is similar to the preferred structure employed in n11 and n12.

In the general formula (I), M ¹ represents a group represented by the following formula (I-M1).

A ¹ and A ² are each independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2,5-diyl group. , Pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1 , 3-dioxane-2,5-diyl groups, these groups may be unsubstituted or substituted by one or more substituents L, but they are the same when there are multiple A ¹ Or different. In view of ease of synthesis, availability of raw materials, and liquid crystallinity, A ¹ and A ² are each independently unsubstituted or may be substituted with one or more substituents L -Preferably represents a phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, naphthalene-2,6-diyl group, each independently Formula (A-1) to Formula (A-13)

It is further preferable to represent a group selected from the group consisting of: (1) to (A-8) and (A-13) independently when the importance of low refractive index anisotropy is emphasized. It is even more preferable to represent a group selected from the formula (A-1) to the formula (A-5), and it is even more preferable to represent a group selected from the formula (A-13). It is even more preferable to represent a group selected from Formula (A-1) to Formula (A-4) and Formula (A-13), and each independently represents Formula (A-1) and Formula (A-2). ) Or a group selected from formula (A-13).
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 represents the following formula (I-RL):

In the case where a plurality of L are present in the compound, they may be the same or different. 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. More preferably, L represents a fluorine atom, a chlorine atom, or a linear alkyl group or linear alkoxy group having 1 to 8 carbon atoms, and the substituent L is a fluorine atom, a chlorine atom, a methyl group or a methoxy group. It is particularly preferred to represent a group. When L represents a group represented by the formula (I-RL), preferred structures of P ^L , R ^SL , Sp ^L , X ^L , kL, nL 1 and nL 2 are P ¹ , R ^S1 , Sp respectively. ¹ , X ¹ , k1, n11 and n12 are the same as the preferred structures adopted.
Z ¹ represents —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 -, - COO-} CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH CH -, - N = N -, - CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, Z ^{When a} plurality of ¹ are present, they may be the same or different. 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-.
m1 represents an integer of 0 to 5, but from the viewpoint of solubility in a solvent and liquid crystallinity, it preferably represents an integer of 0 to 4, more preferably an integer of 1 to 4, 4 is more preferable, and 2 or 4 is particularly preferable.

  The compound represented by the general formula (I) may be a chiral compound. In that case, the following general formula (IC)

^{(Wherein, P 1, R S1, Sp} 1, X 1, k1, n11, n12 and ^{M 1} are each ^{P 1,} R ^S1 in the general formula ^{(I), Sp 1, X} 1, k1, n11, n12 and M ¹ represents the same meaning, ^* C represents an asymmetric carbon atom, R ^2C represents a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, cyano group, nitro group, isocyano Group, thioisocyano group, or any hydrogen atom in the group may be substituted with a fluorine atom, and 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—. Represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by R ^2C , or R ^2C is represented by the following formula (I-R2-C):

(In the formula, P ² , R ^S2 , Sp ² , X ² , k ² , n 21 and n 22 have the same meanings as P ² , R S ² , Sp ² , X ² , X ² , k ² , n 21 and n 22 in the general formula (I), respectively. And a compound represented by ^* C represents an asymmetric carbon atom) is preferable. The preferred structure of each group is the same as described above.

  As a compound represented by general formula (I), the following general formula (IA)

(In the formula, P ¹ and M ¹ each have the same meaning as P ¹ and M ¹ in the general formula (I), and Sp ¹¹ and X ¹¹ each have the same meaning as Sp ¹ and X ¹ in the general formula (I). represents, n111 and n121 represents 0 or 1 each independently is, n111 + n121 represents ^{1, R 21} is the following formula (I-R2-a)

(Wherein, ^{P 2} has the same meaning as ^{P 2} in formula (I), ^{Sp 21} and ^{X 21} are as defined Sp ² and ^{X 2} each in the general formula (I), each n211 and n221 Independently represents 0 or 1, but n211 + n221 represents 1.). It is preferable that it is a compound represented by this. Especially when emphasis on storage stability when added to the polymerizable composition, in the general formula (I-A), n111 represents 0, n121 represents ^{1, R 21} has the formula (I-R2-A) It is preferable that n211 represents 1 and n221 represents 0. In the case where importance is attached to the ease of synthesis and the availability of raw materials, the compound represented by the general formula (I) is represented by the following general formula (IA-11).

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ represent the same meaning) and the following general formula (IA-22)

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ represent the same meanings) and the following general formula (IA-12)

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ represent the same meanings) and the following general formula (IA-21)

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), It is preferably a mixture with a compound represented by Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ ), and represented by the following general formula (IA-111)

(Wherein, ^{P 1} and ^{P 2} each represent a formula (I-A) or the same meaning as ^{P 1} and ^{P 2} in the general formula ^(I-R2-A), A 11, A 12 and ^{A 21} are each Independently represents a 1,4-phenylene group or a 1,4-cyclohexylene group, these groups may be unsubstituted or substituted by one or more substituents L, Z ¹¹ and Z ¹² Each independently represents —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —COO—, —OCO—, —CO—NH—, —NH—CO—, —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- or a single bond) the compound represented by And the following general formula (IA-221)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ¹² each represent the same meaning as A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ^{12 in} general formula (IA-111), and the following general formula (I -A-121)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ¹² each represent the same meaning as A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ^{12 in} general formula (IA-111), and the following general formula (I -A-211)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ¹² represent the same meaning as A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ^{12 in the} general formula (IA-111), respectively) or a mixture represented by the following general formula (IA-112)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ and A ²¹ each independently represents a 1,4-phenylene group or a 1,4-cyclohexylene group, but these groups may be unsubstituted or substituted by one or more substituents L. , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are each independently —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —COO—, —OCO—, —CO—NH—, — NH—CO—, —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 Or a single bond. A compound represented by), the general formula (I-A-222)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or the general formula (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are respectively A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z in the general formula (IA-112). represents the same meaning as ¹³ and ^{Z 14.} a compound represented by), the general formula (I-a-122)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or the general formula (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are respectively A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z in the general formula (IA-112). ¹³ and Z ¹⁴ have the same meaning.) And the following general formula (IA-212)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or the general formula (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are respectively A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z in the general formula (IA-112). more preferably is a mixture of a compound represented by the representative.) the same meaning as ¹³ and ^{Z 14,} the following general formula (I-a-1111)

Wherein W ¹ and W ² each independently represent a hydrogen atom, a methyl group, a trifluoromethyl group or a fluorine atom, and A ¹²¹ represents a 1,4-phenylene group or a 1,4-cyclohexylene group. , These groups may be unsubstituted or substituted by one or more substituents L, and Z ¹¹¹ and Z ¹²¹ are each independently —OCH ₂ —, —CH ₂ O—, —COO— or -OCO-) and the following general formula (IA-2211)

(The same meaning as ^{W 1, W 2, A 121} , Z 111 and ^{Z 121} in the ^{formula, W 1, W 2, A} 121, Z 111 and ^{Z 121} are each formula (I-A-1111). And a compound represented by the following general formula (IA-1211)

(The same meaning as ^{W 1, W 2, A 121} , Z 111 and ^{Z 121} in the ^{formula, W 1, W 2, A} 121, Z 111 and ^{Z 121} are each formula (I-A-1111). ) And the following general formula (IA-2111)

(The same meaning as ^{W 1, W 2, A 121} , Z 111 and ^{Z 121} in the ^{formula, W 1, W 2, A} 121, Z 111 and ^{Z 121} are each formula (I-A-1111). ) Or a compound represented by the following general formula (IA-1121)

Wherein W ¹ and W ² each independently represent a hydrogen atom, a methyl group, a trifluoromethyl group or a fluorine atom, and A ¹²¹ and A ^{141 each} represent a 1,4-phenylene group or a 1,4-cyclohexylene group. Wherein these groups may be unsubstituted or substituted by one or more substituents L, and Z ¹¹¹ , Z ¹²¹ , Z ¹³¹ and Z ¹⁴¹ are each independently —OCH ₂ —, — CH ₂ O—, —COO— or —OCO— is represented, and L ¹ represents a fluorine atom, a chlorine atom, or a linear alkyl group or linear alkoxy group having 1 to 8 carbon atoms. Compound with the following general formula (IA-2221)

Wherein W ¹ , W ² , A ¹²¹ , A ¹⁴¹ , Z ¹¹¹ , Z ¹²¹ , Z ¹³¹ , Z ^141, and L ¹ are W ¹ , W ² , A ^{121 in the} general formula (IA-1121), respectively. , A ¹⁴¹ , Z ¹¹¹ , Z ¹²¹ , Z ¹³¹ , Z ^141, and L ¹ ), and the following general formula (IA-1221)

Wherein W ¹ , W ² , A ¹²¹ , A ¹⁴¹ , Z ¹¹¹ , Z ¹²¹ , Z ¹³¹ , Z ^141, and L ¹ are W ¹ , W ² , A ^{121 in the} general formula (IA-1121), respectively. , A ¹⁴¹ , Z ¹¹¹ , Z ¹²¹ , Z ¹³¹ , Z ^141, and L ¹ have the same meanings) and the following general formula (IA-2121)

Wherein W ¹ , W ² , A ¹²¹ , A ¹⁴¹ , Z ¹¹¹ , Z ¹²¹ , Z ¹³¹ , Z ^141, and L ¹ are W ¹ , W ² , A ^{121 in the} general formula (IA-1121), respectively. , A ¹⁴¹ , Z ¹¹¹ , Z ¹²¹ , Z ¹³¹ , Z ^141, and L ¹ are more preferably a mixture with a compound represented by the following general formula (IA-11111): )

(Wherein W ¹¹ and W ²¹ each independently represents a hydrogen atom or a methyl group) and the following general formula (IA-22111)

(Wherein W ¹¹ and W ²¹ each represent the same meaning as W ¹¹ and W ²¹ in formula (IA-11111)), and the following formula (IA-12111) )

(Wherein W ¹¹ and W ²¹ each represent the same meaning as W ¹¹ and W ²¹ in formula (IA-1111)), or a mixture with a compound represented by the following formula (IA -11211)

(Wherein W ¹¹ and W ²¹ each independently represent a hydrogen atom or a methyl group, and L ¹¹ represents a fluorine atom, a chlorine atom, or a methyl group or a methoxy group) and the following: General formula (IA-22221)

(Wherein W ¹¹ , W ²¹ and L ¹¹ represent the same meanings as W ¹¹ , W ²¹ and L ¹¹ in general formula (IA-11211), respectively), and the following general formula (IA-12111)

(Wherein W ¹¹ , W ²¹ and L ¹¹ represent the same meanings as W ¹¹ , W ²¹ and L ¹¹ in general formula (IA-11211), respectively), and the following general formula (IA-21211)

It is a mixture of ^{(wherein, W 11,} W ²¹ and ^{L 11} are each general formula (. Represents the same meaning as ^{W 11, W 21} and ^{L 11} in the I-A-11211)) a compound represented by Is particularly preferred.

  Further, from the viewpoint of liquid crystallinity, 1,4-cyclohexylene group, 1,3-dioxane-2,5-diyl group and decahydronaphthalene-2,6-included in the compound represented by the general formula (I) The diyl group may be either a cis isomer or a trans isomer, or a mixture of both, but from the viewpoint of liquid crystallinity, the trans isomer is preferably the main component, and only the trans isomer. Is particularly preferred. The same applies to the following compounds.

  The optical film of the present invention preferably has a nematic phase, a smectic phase, a chiral smectic phase, or a cholesteric phase structure, more preferably has a chiral smectic phase or a cholesteric phase structure, and particularly preferably has a cholesteric phase structure.

  Although the compound represented by the said general formula (I) may be used 1 type, or 2 or more types, when manufacturing an optical film, the total content of the said polymeric compound used when manufacturing an optical film is used. It is preferable to contain 1-99 mass% among the total amount of the polymeric compound to be used, it is more preferable to contain 10-90 mass%, and it is especially preferable to contain 20-80 mass%. When placing importance on the orientation of the obtained optical film, the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less, and particularly preferably 60% by mass or less. Moreover, when importance is attached to the storage stability of the liquid crystal composition, the lower limit is preferably 20% by mass or more, more preferably 30% by mass or more, and particularly preferably 40% by mass or more. In addition, when the compound represented by the general formula (I) is a chiral compound, the total content of the chiral compound represented by the general formula (I) used in producing the optical film is the same as that for producing the optical film. Of the total amount of the polymerizable compounds used in this case, the content is preferably 0.1 to 80% by mass, more preferably 1 to 70% by mass, and particularly preferably 5 to 50% by mass.

  In addition to the compound represented by the general formula (I), other compounds may be added as the material for the optical film of the present invention. Other polymerizable compounds used by mixing with the compound represented by the general formula (I) include the following general formula (II)

(Wherein P ³ and P ⁴ each independently represent a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization;
Sp ³ and Sp ⁴ each independently represent a spacer group. When a plurality of Sp ³ are present, they may be the same or different, and when a plurality of Sp ⁴ are present, they may be the same. May be different,
X ³ and X ⁴ 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—, —C≡C— or a single bond. But they if X ³ there are a plurality may be the same or different and they if X ⁴ there are a plurality may be the same or different and
k3 and k4 each independently represents an integer of 0 to 10,
A ³ and A ⁴ are each independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2,5-diyl group. , Pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1 , 3-dioxane-2,5-diyl groups, these groups may be unsubstituted or substituted by one or more substituents L, but they are the same when there are multiple A ³ Can be different,
Z ² represents —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 -, - COO-} CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH CH -, - N = N -, - CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, Z ^{When two} or more ² exist, they may be the same or different,
m2 represents an integer of 0 to 5. ) Is preferred. However, the compound represented by the general formula (II) does not include the compound represented by the general formula (I).

In the general formula (II), P ³ and P ⁴ each independently represent a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization, and each independently represents the above formula (P-1) to formula (P- It is preferable to represent a group selected from 20). 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 (II), Sp ³ and Sp ⁴ each independently represent a spacer group. When a plurality of Sp ³ are present, they may be the same or different, and when a plurality of Sp ⁴ are present. They may be the same or different. From the viewpoint of liquid crystallinity, availability of raw materials, and ease of synthesis, Sp ³ and Sp ⁴ may be the same or different when there are a plurality of them. Each independently of one —CH ₂ — or two or more non-adjacent —CH ₂ — may be 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 -, - SC _{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 -, - Represents an alkylene group having 1 to 20 carbon atoms which may be replaced by CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF— or —C≡C—. In the case where a plurality of Sp ³ and Sp ⁴ are present, they may be the same or different, and each independently represents one —CH ₂ — or two or more —CH ₂ — that are not adjacent to each other. Are each independently -O-, -COO-, -OCO-, -OCO-O- , —CO—NH—, —NH—CO—, —CH═CH— or —C≡C—, more preferably represents an alkylene group having 1 to 20 carbon atoms which may be replaced by Sp ³ and Sp. ⁴ may be the same or different when there are a plurality of ⁴ and each independently represents one —CH ₂ — or two or more non-adjacent —CH ₂ — each independently —O More preferably, it represents a linear alkylene group having 1 to 20 carbon atoms which may be replaced by-, -COO-, -OCO- or -OCO-O-, and when there are a plurality of Sp ³ and Sp ⁴ Each may be the same or different, and may each independently represent one —CH ₂ — or two or more non-adjacent —CH ₂ — each independently replaced by —O—. Good linear alkylene group having 1 to 12 carbon atoms Even more preferably it represents, Sp ³ and Sp ⁴ may be different even each identical in the presence of two or more, may represent a linear alkylene group having 1 to 12 carbon atoms each independently Particularly preferred.

In the general formula (II), X ³ and X ⁴ 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-, C≡C- or represents a single bond, they if X ³ there are a plurality may be different even in the same, X ⁴ may be those when the plurality of different may be the same . From the viewpoint of easy availability of raw materials and ease of synthesis, when there are a plurality of X ³ and X ^4, 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 -, - CH 2 CH 2 -COO -, - it is preferable to represent a _CH 2 CH 2 -OCO- or a single bond, each independently -O _{-, - OCH 2 -, -} CH 2 O -, - COO -, - OCO -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH more preferably represents an ₂ CH ₂ -OCO- or a single bond, each independently -O -, - OO -, - OCO- or more preferably a single bond, even more preferably represent each independently -O- or a single bond, and particularly preferably each represent -O-.

  In general formula (II), k3 and k4 each independently represent an integer of 0 to 10, but from the viewpoint of ease of synthesis and liquid crystallinity, it is preferable that each independently represents an integer of 0 to 5, More 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. Particularly preferred.

However, in the general formula ^{(II), P 3 - (} Sp 3 -X 3) k3 - and ^{- (X ₄} -Sp _⁴⁾ k4 in -P ⁴ does not contain -O-O- bond.

In the general formula (II), preferred structures of A ³ , A ⁴ , Z ² and m ² are the same as the preferred structures adopted by A ¹ , A ² , Z ¹ and m ¹ in the general formula (I), respectively. The preferred structure for L is the same as described above.

  As a compound represented by general formula (II), the following general formula (II-A)

(In the formula, P ³ , P ⁴ , Sp ³ , Sp ⁴ , X ³ , X ⁴ , k ³ and k ⁴ are respectively P ³ , P ⁴ , Sp ³ , Sp ⁴ , X ³ , X ⁴ in the general formula (II)). , K3 and k4 have the same meanings, and A ³¹ , A ³² and A ⁴¹ each independently represent a 1,4-phenylene group or a 1,4-cyclohexylene group, but are these groups unsubstituted? Or may be substituted by one or more substituents L, and Z ²¹ and Z ²² are each independently —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —COO—, —OCO—. , —CO—NH—, —NH—CO—, —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 Is preferably a compound represented by the representative.) The _-CH 2 _CH 2 -OCO- or a single bond, general formula (II-A-1)

(In the formula, P ³ , P ⁴ , Sp ³ , Sp ⁴ , X ³ , X ⁴ , k ³ and k ⁴ are respectively P ³ , P ⁴ , Sp ³ , Sp ⁴ , X ³ , X ⁴ in the general formula (II)). , K3 and k4, and A ³²¹ represents a 1,4-phenylene group or a 1,4-cyclohexylene group, but these groups are unsubstituted or substituted by one or more substituents L Z ²¹¹ and Z ²²¹ each independently represent —OCH ₂ —, —CH ₂ O—, —COO—, —OCO— or a single bond, and r represents an integer of 0 to 4. Is more preferable, and the following general formula (II-A-11)

(In the formula, P ³ , P ⁴ , Sp ³ , Sp ⁴ , X ³ , X ⁴ , k ³ and k ⁴ are respectively P ³ , P ⁴ , Sp ³ , Sp ⁴ , X ³ , X ⁴ in the general formula (II)). , K3 and k4 have the same meanings, and r represents an integer of 0 to 4.), and the following general formula (II-A-111)

(Wherein, W ¹ and W ² each independently represent a hydrogen atom, a methyl group, a trifluoromethyl group, or a fluorine atom, and k31 and k41 each represent an integer of 2 to 10). preferable.

  The compound represented by the general formula (II), more preferably the compound represented by the general formula (II-A), more preferably the compound represented by the general formula (II-A-11), particularly preferably the general The compound represented by the formula (II-A-111) may be used alone or in combination of two or more, but the total content of the polymerizable compound used when producing the optical film produces the optical film. It is preferable to contain 1-99 mass% among the total amount of the polymeric compound used in the case, It is more preferable to contain 10-90 mass%, It is especially preferable to contain 20-80 mass%. When placing importance on the orientation of the obtained optical film, the lower limit is preferably 20% by mass or more, more preferably 30% by mass or more, and particularly preferably 40% by mass or more. In the case where importance is attached to the storage stability of the liquid crystal composition, the upper limit value is preferably 80% by mass or less, more preferably 70% by mass or less, and particularly preferably 60% by mass or less.

  As other compounds represented by the general formula (II), the following formulas (X-1-1) to (X-1-) are used for the purpose of adjusting the cholesteric orientation, the liquid crystal phase temperature range, the surface hardness of the film, and the like. 3)

In the formula, W ¹⁰¹ and W ¹⁰² each independently represents a hydrogen atom, a methyl group, a trifluoromethyl group or a fluorine atom, and k101 and k102 represent an integer of 2 to 10). You can also

  Further, as other compounds, the following formulas (X-1-4) to (X-1-7)

^{(Wherein, W 101} and ^{W 102} are each independently hydrogen atom, a methyl group, a trifluoromethyl group or a fluorine atom, K101 and k102 is an integer of from 2 to ^{10, R 101} represents a hydrogen atom, a carbon atom A compound represented by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms is preferred.

  The optical film of the present invention may be further produced using a chiral compound. The chiral compound may be used alone or in combination of two or more, but the total content of the chiral compound used when producing the optical film is 1 with respect to the total amount of polymerizable compounds used when producing the optical film. The content is preferably 0.1 to 30% by mass, more preferably 1 to 20% by mass, and particularly preferably 5 to 10% by mass.

  As the chiral compound, a chiral compound having an isosorbide structure or a binaphthyl structure is preferable, and the following formulas (X-2-1) to (X-2-3)

(Wherein L represents the same meaning as L in formula (I), r represents an integer of 0 to 4, t represents an integer of 0 to 2, A ¹⁰¹ , A ¹⁰² , A ¹⁰³ and A ¹⁰⁴ Each independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group or a naphthalene-2,6-diyl group, these groups being unsubstituted or substituted by one or more substituents L Z ¹⁰¹ , Z ¹⁰² , Z ¹⁰³ , Z ¹⁰⁴ , Z ¹⁰⁵ and Z ¹⁰⁶ may each independently represent —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CF _{2. O -, - OCF 2 -,} - CH = CH-COO -, - 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 -, - C≡C- or a single bond, m101, M102, M103 and m104 represents an integer of 0 to ^{5, B 101} is a 1,4-phenylene group, 1,4-cyclohexylene group or a naphthalene-2,6 , 6-diyl groups, these groups may be unsubstituted or substituted by one or more substituents L, or B ¹⁰¹ may be one —CH ₂ — or not adjacent 2 Or more of —CH ₂ — are each independently —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH— or —C. R represents an alkylene group having 1 to 20 carbon atoms which may be replaced by C-, and R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or Any hydrogen atom in the group is fluorine May be substituted by the child, one -CH ₂ - or nonadjacent two or more -CH ₂ - are each independently _{-O -, - OCH 2 -,} - CH 2 O -, - CO -, -COO-, -OCO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -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 — Represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by COO—, —CH ₂ —OCO—, —CH═CH—, —CF═CF— or —C≡C—. , ^{or, R 102, R 103, R} 104 and ^{R 105} are each independently ^{P 101 (Sp} ₁₀₁ ^-X ₁₀₁₎ k101 - group represented by ^{(wherein, P 101} represents a group capable of polymerization by free radical polymerization, cationic polymerization or anionic ^{polymerization, Sp 101} each represents a spacer ^{group, Sp 101} is plurality of And they may be the same or different, and X ¹⁰¹ 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 a single bond, but when there are a plurality of X ^101, they may be the same or different. K101 represents an integer of 0 to 10. ). ), And more specifically, the following formulas (X-2-1-1) to (X-2-3-2)

(Wherein L represents the same meaning as L in formula (I), r represents an integer of 0 to 4, and W ¹⁰³ and W ¹⁰⁴ each independently represent a hydrogen atom, a methyl group, a trifluoromethyl group, or represents a fluorine atom, K103 and k104 is an integer of from 2 to ^{10, R 106} and ^{R 107} is an alkoxy group of a hydrogen atom, an alkyl group or 1 to 10 carbon atoms number from 1 to 10 carbon ^{atoms, R 108} And R ¹⁰⁹ represents an alkyl group having 1 to 10 carbon atoms.).

  It is also possible to add a polymerizable compound that does not exhibit liquid crystallinity to the polymerizable composition used in producing the optical film 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).

  Moreover, although it is possible to polymerize without using the polymerizable composition photopolymerization initiator used in producing the optical film of the present invention, a photopolymerization initiator may be added depending on the purpose. In that case, the concentration of the photopolymerization initiator is preferably from 0.1 to 15 parts by mass, and from 0.2 to 10 parts by mass, with respect to 100 parts by mass of the total amount of polymerizable compounds used when producing the optical film. Mass parts are more preferred, and 0.4 to 8 parts by mass are even more preferred. 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 polymerizable composition used when producing the optical film 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. The addition amount in the case of using a stabilizer is preferably in the range of 0.005 parts by mass to 1 part by mass with respect to 100 parts by mass of the total amount of polymerizable compounds used for producing the optical film, and 0.02 mass. Part to 0.8 parts by mass is more preferable, and 0.03 parts to 0.5 parts by mass is even 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.

  In addition, the polymerizable composition used when producing the optical film of the present invention is used for applications such as films, optical elements, functional pigments, pharmaceuticals, cosmetics, coating agents, and synthetic resins. In some cases, metal, metal complex, dye, pigment, pigment, fluorescent material, phosphorescent material, surfactant, leveling agent, thixotropic agent, gelling agent, polysaccharide, ultraviolet absorber, infrared absorber depending on the purpose Further, antioxidants, ion exchange resins, metal oxides such as titanium oxide, and the like can be added.

The polymer obtained by polymerizing the polymerizable composition used when producing the optical film of the present invention can be used for various applications. For example, a polymer obtained by polymerizing the polymerizable composition used in producing the optical film 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 is, for example, a substrate obtained by rubbing a polymerizable composition used for producing the optical film of the present invention with a cloth, a substrate on which an organic thin film is formed, or SiO ₂ is obliquely deposited. It can be produced by polymerizing the polymerizable composition after being supported on a substrate having an alignment film or sandwiched between substrates.

  Examples of the method for supporting the polymerizable composition on the substrate include spin coating, die coating, extrusion coating, roll coating, wire bar coating, gravure coating, spray coating, dipping, and a printing method. 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 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 polymerizing the polymerizable composition used for producing the optical film of the present invention, it is desirable that the polymerization proceeds rapidly, and 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 with which the liquid crystal state of the polymeric composition used when producing the optical film 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 deteriorates. When the intensity is 2 W / cm ² or more, the polymerizable crystal compound or the polymerizable composition There is a risk that things will deteriorate.

  The optical anisotropic body obtained by polymerization can be subjected to 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. Normal post-treatment is an operation performed to obtain a target compound from a reaction solution, and is usually performed among those skilled in the art such as reaction quenching, liquid separation / extraction, neutralization, washing, drying, and concentration. Means work.
(Synthesis example 1) Manufacture of the mixture (A-1) comprised by the compound represented by Formula (A-1-3) from Formula (A-1-1).

  In a reaction vessel, 5.0 g of the compound (mixture) represented by the formula (A-1-a), 4.2 g of succinic anhydride, 0.5 g of N, N-dimethylaminopyridine, 2,6-di-tert-butyl -25 mg of -4-methylphenol and 40 mL of dichloromethane were added and stirred with heating at 40 ° C. for 12 hours. After cooling, 40 mL of water was added and stirred at room temperature for 1 hour. After separation treatment, it was washed successively with 5% hydrochloric acid and saturated brine. After drying with sodium sulfate, the solvent was distilled off to obtain 8.4 g of a compound (mixture) represented by the formula (A-1-b).

  8.4 g of a compound (mixture) represented by the formula (A-1-b) in a reaction vessel, 42 mg of 2,6-di-tert-butyl-4-methylphenol, 24 mL of ethyl acetate, 8 mL of N, N-dimethylacetamide Was added. After cooling to 5 ° C., 4.6 g of thionyl chloride was added dropwise, and the mixture was stirred at 5 ° C. for 1 hour. A solution prepared by dissolving 5.0 g of 2- (4-hydroxyphenyl) ethanol in 25 mL of N, N-dimethylacetamide was added dropwise and stirred at room temperature for 12 hours. The reaction solution was poured into water, extracted with ethyl acetate, and then washed sequentially with 5% hydrochloric acid, water and brine. After drying with sodium sulfate, the solvent was distilled off to obtain 12.1 g of a compound (mixture) represented by the formula (A-1-c).

To the reaction vessel, 1.0 g of trans-1,4-cyclohexanedicarboxylic acid, 1.3 g of methanesulfonic acid chloride, 5 mL of tetrahydrofuran, and 5 mL of N, N-dimethylacetamide were added. Triethylamine 1.2g was dripped and it stirred at room temperature for 2 hours. A solution prepared by dissolving 4.1 g of the compound (mixture) represented by the formula (A-1-c) and 20 mg of 2,6-di-tert-butyl-4-methylphenol in 12 mL of tetrahydrofuran was added dropwise. Triethylamine 1.2g was dripped and it stirred at room temperature for 12 hours. The reaction solution was poured into water, extracted with dichloromethane, and washed successively with 5% hydrochloric acid and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain a compound (mixture) represented by the formula (A-1).
LCMS: m / z 837 [M + 1]
Synthesis Example 2 Production of Mixture (A-2) Consists of Compounds Represented by Formula (A-2-3) to Formula (A-2-3)

  In the same manner as in Synthesis Example 1, except that the compound (mixture) represented by the formula (A-1-a) was replaced with the compound (mixture) represented by the formula (A-2-a), the formula (A A compound (mixture) represented by -2-b) was produced.

  Under a nitrogen atmosphere, 3.0 g of the compound (mixture) represented by the formula (A-2-b), 2.4 g of 4-tetrahydropyranyloxyphenol, 0.1 g of N, N-dimethylaminopyridine, dichloromethane in a reaction vessel 30 mL was added. While cooling with ice, 1.7 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 8 hours. After washing with 1% hydrochloric acid, water and brine, purification was performed by column chromatography (alumina, dichloromethane) to obtain 4.1 g of a compound (mixture) represented by the formula (A-2-c).

  To the reaction vessel, 4.1 g of a compound (mixture) represented by the formula (A-2-c), 20 mL of tetrahydrofuran, and 20 mL of methanol were added. Concentrated hydrochloric acid 0.2mL was added and it stirred at room temperature for 8 hours. After diluting with ethyl acetate, it was washed with water and brine. Purification was performed by column chromatography (silica gel, ethyl acetate) to obtain 3.0 g of a compound (mixture) represented by the formula (A-2-d).

In the same manner as in Synthesis Example 1, except that the compound (mixture) represented by the formula (A-1-c) was replaced with the compound (mixture) represented by the formula (A-2-d), the formula (A -2) was produced (mixture).
LCMS: m / z 809 [M + 1]
(Synthesis Example 3) Production of mixture (A-3) composed of compounds represented by formula (A-3-3) to formula (A-3-3)

  Under a nitrogen atmosphere, 20.0 g of the compound represented by the formula (A-3-a), 14.3 g of diisopropylethylamine, and 200 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 10.0 g of acryloyl chloride was added dropwise and stirred at room temperature for 6 hours. The reaction solution was poured into water and subjected to a liquid separation treatment, and then washed sequentially with a mixed solvent of methanol and water and brine. Purification was performed by column chromatography (silica gel, ethyl acetate) to obtain 11.5 g of a compound (mixture) represented by the formula (A-3-b).

In the same manner as in Synthesis Example 2, except that the compound (mixture) represented by the formula (A-2-a) was replaced with the compound (mixture) represented by the formula (A-3-b), the formula (A The compound (mixture) represented by -3) was produced.
LCMS: m / z 809 [M + 1]
Synthesis Example 4 Production of Compound Represented by Formula (A-4)

  To the reaction vessel is added 5.0 g of the compound represented by the formula (A-4-a), 2.4 g of 3-chloropropanol, 5.3 g of potassium carbonate, and 40 mL of N, N-dimethylformamide, and the mixture is heated at 90 ° C. for 12 hours. Stir. After cooling and pouring into water, the mixture was extracted with ethyl acetate. Washed sequentially with water and brine. Purification was performed by column chromatography (alumina, ethyl acetate) to obtain 5.2 g of a compound represented by the formula (A-4-b).

A compound represented by the formula (A-4) is represented by the same method except that the compound represented by the formula (A-3-a) is replaced by a compound represented by the formula (A-4-c) in Synthesis Example 3. A compound was prepared.
LCMS: m / z 925 [M + 1]
(Synthesis example 5) Manufacture of the mixture (A-5) comprised by the compound represented by Formula (A-5-3) from Formula (A-5-1).

  In the same manner as in Synthesis Example 3 except that the compound represented by the formula (A-3-a) is replaced with the compound represented by the formula (A-5-a), the compound represented by the formula (A-5-c) The represented compound (mixture) was prepared.

  Under a nitrogen atmosphere, 5.0 g of the compound represented by the formula (A-5-d), 3.5 g of the compound represented by the formula (A-5-e), 3.9 g of potassium carbonate, 50 mL of ethanol, Water (30 mL) and tetrakis (triphenylphosphine) palladium (0) (0.4 g) were added, and the mixture was heated to reflux for 12 hours. After cooling, it was diluted with ethyl acetate and washed with 5% hydrochloric acid, water and brine. Purification was performed by column chromatography (alumina, ethyl acetate) and recrystallization (toluene / ethanol) to obtain 4.3 g of a compound represented by the formula (A-5-f).

In Synthesis Example 1, the compound (mixture) represented by the formula (A-1-b) is converted into the compound (mixture) represented by the formula (A-5-c), and 2- (4-hydroxyphenyl) ethanol is represented by the formula. A compound (mixture) represented by the formula (A-5) was produced by the same method except that the compound represented by (A-5-f) was replaced.
LCMS: m / z 947 [M + 1]
(Synthesis Example 6) Production of a mixture (A-6) composed of a compound represented by the formula (A-6-3) from the formula (A-6-1)

  In the same manner as in Synthesis Example 3 except that the compound represented by the formula (A-3-a) is replaced by the compound represented by the formula (A-6-a), the compound represented by the formula (A-6-c) The represented compound (mixture) was prepared.

  In Synthesis Example 1, the compound represented by the formula (A-1-b) is converted into the compound (mixture) represented by the formula (A-6-c), and 2- (4-hydroxyphenyl) ethanol is trans-4- A compound (mixture) represented by the formula (A-6-d) was produced by the same method except that (2-hydroxyethyl) cyclohexanol was used.

  To the reaction vessel, 9.0 g of trans-1,4-cyclohexanedicarboxylic acid, 2.0 g of methanesulfonic acid chloride, 20 mL of tetrahydrofuran, and 20 mL of N, N-dimethylacetamide were added. Triethylamine 1.8g was dripped and it stirred at room temperature for 2 hours. A solution prepared by dissolving 6.3 g of the compound (mixture) represented by the formula (A-6-d) and 20 mg of 2,6-di-tert-butyl-4-methylphenol in 12 mL of tetrahydrofuran was added dropwise. After adding 0.6 g of N, N-dimethylaminopyridine, 1.8 g of triethylamine was added dropwise, followed by stirring at room temperature for 12 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and washed successively with 5% hydrochloric acid and brine. Purification was performed by column chromatography (silica gel, ethyl acetate) and recrystallization (ethyl acetate / hexane) to obtain 6.8 g of a compound (mixture) represented by the formula (A-6-e).

6.8 g of a compound (mixture) represented by the formula (A-6-e) in a reaction vessel, 7 mg of 2,6-di-tert-butyl-4-methylphenol, 35 mL of ethyl acetate, 14 mL of N, N-dimethylacetamide Was added. The mixture was cooled to 5 ° C., 2.7 g of thionyl chloride was added dropwise, and the mixture was stirred at 5 ° C. for 1 hour. 2.0 g of N, N-diisopropylethylamine was added dropwise. A solution prepared by dissolving 0.9 g of 2-methyl-1,4-hydroquinone in 5 mL of tetrahydrofuran and 0.2 g of N, N-dimethylaminopyridine were added. At 5 ° C., 4.7 g of N, N-diisopropylethylamine was added dropwise and stirred at room temperature for 5 hours. The reaction solution was poured into water, extracted with dichloromethane, and then washed sequentially with 5% hydrochloric acid, water and brine. Purification by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) gave 6.9 g of a compound (mixture) represented by the formula (A-6).
LCMS: m / z 1193 [M + 1]
(Synthesis example 7) Manufacture of the mixture (A-7) comprised by the compound represented by Formula (A-7-3) from Formula (A-7-1)

In the same manner as in Synthesis Example 6 except that the compound (mixture) represented by the formula (A-6-d) was replaced with the compound (mixture) represented by the formula (A-7-a), the formula (A The compound (mixture) represented by -7) was produced.
LCMS: m / z 1097 [M + 1]
(Synthesis Example 8) Production of a mixture (A-8) composed of a compound represented by the formula (A-8-3) from the formula (A-8-1)

  A compound (mixture) represented by the formula (A-8-b) was produced by the same method except that 2- (4-hydroxyphenyl) ethanol was replaced with 1,4-butanediol in Synthesis Example 1.

In Synthesis Example 6, the compound (mixture) represented by the formula (A-6-d) is changed to the compound (mixture) represented by the formula (A-8-b), and 2-methyl-1,4-hydroquinone is added to 2 A compound (mixture) represented by the formula (A-8) was produced by the same method except that -acetyl-1,4-hydroquinone was used.
LCMS: m / z 1029 [M + 1]
(Synthesis example 9) Manufacture of the mixture (A-9) comprised by the compound represented by Formula (A-9-3) from Formula (A-9-1).

  In Synthesis Example 3, the compound represented by the formula (A-3-a) was replaced with the compound represented by the formula (A-9-a), and 4-tetrahydropyranyloxyphenol was replaced with 4-hydroxybenzaldehyde. A compound (mixture) represented by the formula (A-9-d) was produced by the same method.

  An aqueous solution in which 5.0 g of a compound (mixture) represented by the formula (A-9-d), 20 mL of methanol, and 1.6 g of sodium dihydrogen phosphate dihydrate are dissolved in 20 mL of water in a reaction vessel, 30% excess 2.3 g of hydrogen oxide water was added. An aqueous solution in which 1.5 g of sodium chlorite was dissolved in 15 mL of water was dropped, and the mixture was heated and stirred at 50 ° C. for 10 hours. After cooling, water was added and extracted with ethyl acetate. After washing with 5% hydrochloric acid and brine, it was dried over sodium sulfate and the solvent was distilled off to obtain 4.2 g of a compound (mixture) represented by the formula (A-9-e).

In Synthesis Example 1, the compound (mixture) represented by the formula (A-1-c) is represented by 4,4′-dihydroxybiphenyl, and trans-1,4-cyclohexanedicarboxylic acid is represented by the formula (A-9-e). A compound (mixture) represented by the formula (A-9) was produced by the same method except that the compound was replaced with the above compound.
LCMS: m / z 963 [M + 1]
(Synthesis Example 10) Production of a mixture (A-10) composed of a compound represented by the formula (A-10-3) to the formula (A-10-3)

In Synthesis Example 6, the compound represented by the formula (A-6-a) is changed to the compound represented by the formula (A-10-a), acryloyl chloride is changed to methacryloyl chloride, and trans-4- (2-hydroxyethyl) is changed. A compound (mixture) represented by the formula (A-10) was prepared in the same manner except that cyclohexanol was replaced with ethylene glycol and 2-methyl-1,4-hydroquinone was replaced with methyl 2,5-dihydroxybenzoate. Manufactured.
LCMS: m / z 1077 [M + 1]
(Synthesis example 11) Manufacture of the mixture (B-1) comprised by the compound represented by Formula (B-1-1) and Formula (B-1-2).

To the reaction vessel, trans-4- (trans-4-propylcyclohexyl) cyclohexanecarboxylic acid (3.0 g), methanesulfonic acid chloride (1.4 g), tetrahydrofuran (20 mL), and N, N-dimethylacetamide (20 mL) were added. Triethylamine 1.3g was dripped and it stirred at room temperature for 2 hours. A solution prepared by dissolving 4.2 g of the compound (mixture) represented by the formula (B-1-a) and 20 mg of 2,6-di-tert-butyl-4-methylphenol in 12 mL of tetrahydrofuran was added dropwise. After adding 0.6 g of N, N-dimethylaminopyridine, 1.5 g of triethylamine was added dropwise, followed by stirring at room temperature for 12 hours. The reaction solution was poured into water, extracted with dichloromethane, and washed successively with 5% hydrochloric acid and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 4.9 g of a compound (mixture) represented by the formula (B-1).
LCMS: m / z 585 [M + 1]
(Synthesis example 12) Manufacture of the mixture (B-2) comprised by the compound represented by Formula (B-2-1) and Formula (B-2-2)

  In the same manner as in Synthesis Example 6 except that the compound represented by the formula (A-6-d) was replaced with the compound represented by the formula (B-2-a), the compound represented by the formula (B-2-b) The represented compound (mixture) was prepared.

In a reaction vessel, 5.0 g of the compound (mixture) represented by the formula (B-2-b), 7 mg of 2,6-di-tert-butyl-4-methylphenol, 35 mL of ethyl acetate, 14 mL of N, N-dimethylacetamide Was added. The mixture was cooled to 5 ° C., 1.5 g of thionyl chloride was added dropwise, and the mixture was stirred at 5 ° C. for 1 hour. 2.0 g of N, N-diisopropylethylamine was added dropwise. A solution in which 2.5 g of 4- (trans-4-pentylcyclohexyl) phenol was dissolved in 5 mL of tetrahydrofuran and 0.2 g of N, N-dimethylaminopyridine were added. At 5 ° C., 4.7 g of N, N-diisopropylethylamine was added dropwise and stirred at room temperature for 5 hours. The reaction solution was poured into water, extracted with dichloromethane, and then washed sequentially with 5% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 5.9 g of a compound (mixture) represented by the formula (B-2).
LCMS: m / z 719 [M + 1]
(Synthesis example 13) Manufacture of the mixture (B-3) comprised by the compound represented by Formula (B-3-1) and Formula (B-3-2).

  In the same manner as in Synthesis Example 9 except that the compound (mixture) represented by the formula (A-9-c) was replaced with the compound (mixture) represented by the formula (B-3-a), the formula (B A compound (mixture) represented by -3-c) was produced.

  A compound represented by the formula (B-3-d) was produced by the method described in JP2013-253041A.

In Synthesis Example 12, the compound (mixture) represented by the formula (B-2-b) is converted into a compound (mixture) represented by the formula (B-3-c) and 4- (trans-4-pentylcyclohexyl) phenol. A compound (mixture) represented by the formula (B-3) was produced by the same method except that was replaced with a compound represented by the formula (B-3-d).
LCMS: m / z 625 [M + 1]
(Synthesis example 14) Manufacture of the mixture (B-4) comprised by the compound represented by Formula (B-4-1) and Formula (B-4-2).

  To the reaction vessel was added 5.0 g of the compound represented by the formula (B-4-a), 4.6 g of 3-chloropropanol, 8.5 g of potassium carbonate, and 50 mL of N, N-dimethylformamide, and the mixture was heated and stirred at 90 ° C. for 12 hours. did. The reaction mixture was poured into water and extracted with dichloromethane. Purification was performed by column chromatography (silica gel, dichloromethane) to obtain 5.9 g of a compound represented by the formula (B-4-b).

  In Synthesis Example 4, the compound (mixture) represented by the formula (A-4-c) is represented by the formula (A-4-b) to the compound (mixture) represented by the formula (B-4-c). The compound (mixture) represented by the formula (B-4-f) was produced by the same method except that the compound represented by the formula (B-4-b) was replaced.

In Synthesis Example 13, the compound (mixture) represented by the formula (B-3-b) is represented by the formula (B-3-d) to the compound (mixture) represented by the formula (B-4-f). A compound (mixture) represented by the formula (B-4) was produced by the same method except that 4-cyano-4′-hydroxybiphenyl was substituted.
LCMS: m / z 628 [M + 1]
(Synthesis Example 15) Production of mixture (B-5) composed of compounds represented by formula (B-5-1) and formula (B-5-2)

  In Synthesis Example 12, the compound (mixture) represented by the formula (B-2-a) is converted into tert-butyl trans-4-hydroxycyclohexanecarboxylate, and trans-1,4-cyclohexanedicarboxylic acid is converted into trans-4- (trans A compound represented by the formula (B-5-b) was produced in the same manner except that it was replaced with (-4-ethylcyclohexyl) cyclohexanecarboxylic acid.

  To the reaction vessel were added 5.0 g of the compound represented by the formula (B-5-b), 25 mL of dichloromethane, and 25 mL of formic acid, and the mixture was heated and stirred at 40 ° C. for 10 hours. The solvent was distilled off and dispersed and washed with diisopropyl ether to obtain 3.9 g of a compound represented by the formula (B-5-c).

In the same manner as in Synthesis Example 11, except that trans-4- (trans-4-propylcyclohexyl) cyclohexanecarboxylic acid is replaced by a compound represented by the formula (B-5-c), the formula (B-5) is used. The compound represented was prepared.
LCMS: m / z 697 [M + 1]
(Synthesis Example 16) Production of mixture (B-6) composed of compounds represented by formula (B-6-1) and formula (B-6-2)

A compound represented by the formula (B-6-b) was produced by the method described in JP-A-11-147853. In Synthesis Example 9, the compound represented by the formula (A-9-c) is represented by the compound represented by the formula (B-6-a), and 4-hydroxybenzaldehyde is represented by the formula (B-6-b). A compound represented by the formula (B-6) was produced by the same method except that the compound was replaced.
LCMS: m / z 543 [M + 1]
Synthesis Example 17 Production of Compound Represented by Formula (C-1)

  In the same manner as in Synthesis Example 1, except that the compound represented by the formula (A-1-a) is replaced by the compound represented by the formula (C-1-a), the formula (C-1-d) The compound represented was prepared.

  To the reaction vessel were added 5.0 g of the compound represented by the formula (C-1-d), 20 mL of tetrahydrofuran, 20 mL of methanol, and 0.2 mL of concentrated hydrochloric acid, and the mixture was stirred at room temperature for 8 hours. After diluting with ethyl acetate, it was washed with water and brine. Purification was performed by column chromatography (silica gel, hexane / ethyl acetate) to obtain 3.7 g of a compound represented by the formula (C-1-e).

Under a nitrogen atmosphere, 3.7 g of the compound represented by the formula (C-1-e), 1.6 g of diisopropylethylamine, and 40 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 1.0 g of acryloyl chloride was added dropwise and stirred at room temperature for 6 hours. The reaction solution was poured into water and subjected to a liquid separation treatment, and then washed sequentially with 1% hydrochloric acid and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 2.9 g of a compound represented by the formula (C-1).
LCMS: m / z 837 [M + 1]
Synthesis Example 18 Production of compound represented by formula (C-2)

A compound represented by the formula (C-2) was synthesized in the same manner as in Synthesis Example 17 except that the compound represented by the formula (C-1-a) was replaced with a compound represented by the formula (C-2-a). A compound was prepared.
LCMS: m / z 837 [M + 1]
Synthesis Example 19 Production of compound represented by formula (C-3)

  Under a nitrogen atmosphere, 5.0 g of the compound represented by the formula (C-3-a), 6.0 g of diisopropylethylamine, and 40 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 3.1 g of acryloyl chloride was added dropwise and stirred at room temperature for 6 hours. The reaction solution was poured into water and subjected to a liquid separation treatment, and then washed sequentially with 1% hydrochloric acid and brine. Purification was performed by column chromatography (silica gel, hexane / ethyl acetate) to obtain 5.3 g of a compound represented by the formula (C-3-b).

  To the reaction vessel were added 5.3 g of the compound represented by the formula (C-3-b), 20 mL of tetrahydrofuran, 20 mL of methanol, and 0.2 mL of concentrated hydrochloric acid, and the mixture was stirred at room temperature for 8 hours. After diluting with ethyl acetate, it was washed with water and brine. Purification by column chromatography (silica gel, hexane / ethyl acetate) gave 2.9 g of the compound represented by the formula (C-3-c).

In the same manner as in Synthesis Example 1 except that the compound (mixture) represented by the formula (A-1-a) was replaced with the compound represented by the formula (C-3-c), the formula (C-3) The compound represented by these was manufactured.
LCMS: m / z 837 [M + 1]
Synthesis Example 20 Production of Compound Represented by Formula (C-4)

A compound represented by the formula (C-4) was synthesized in the same manner as in Synthesis Example 19 except that the compound represented by the formula (C-3-a) was replaced with a compound represented by the formula (C-4-a). A compound was prepared.
LCMS: m / z 837 [M + 1]
(Synthesis example 21) Manufacture of the mixture (A-11) comprised by the compound represented by Formula (A-11-4) from Formula (A-11-1).

  A compound (mixture) represented by the formula (A-11-a) was produced in the same manner as in Synthesis Example 7.

In a reaction vessel, 5.0 g of the compound (mixture) represented by the formula (A-11-a), 7 mg of 2,6-di-tert-butyl-4-methylphenol, 35 mL of ethyl acetate, 14 mL of N, N-dimethylacetamide Was added. The mixture was cooled to 5 ° C., 1.4 g of thionyl chloride was added dropwise, and the mixture was stirred at 5 ° C. for 1 hour. 2.0 g of N, N-diisopropylethylamine was added dropwise. A solution prepared by dissolving 0.8 g of trimethylhydroquinone in 5 mL of tetrahydrofuran and 0.2 g of N, N-dimethylaminopyridine were added. At 5 ° C., 4.7 g of N, N-diisopropylethylamine was added dropwise and stirred at room temperature for 5 hours. The reaction solution was poured into water, extracted with dichloromethane, and then washed sequentially with 5% hydrochloric acid, water and brine. Purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) to obtain 4.5 g of a compound (mixture) represented by the formula (A-11).
LCMS: m / z 1125 [M + 1]
(Examples 1 to 156, Comparative Examples 1 to 16)
A compound and / or a mixture represented by formula (A-1) to formula (C-4) described in Synthesis Example 1 to Synthesis Example 21, a compound (R-1) described in Patent Document 1, and described in Patent Document 2 The compound (R-2) was evaluated.

  As other bifunctional polymerizable compounds, compounds represented by the following formulas (D-1) to (D-12) are used, and as other monofunctional polymerizable compounds, the following formulas (E-1) to formulas are used. The compounds represented by (E-8) are represented by the following formulas (F-1) to (F-3) and formulas (F-5) to (F-7) as other chiral compounds. As compounds and compound (F-4), LC756 (manufactured by BASF) is used, and as other additives, compounds represented by the following formulas (G-1) to (G-3) and compounds (G-4) ) Polypropylene (weight average molecular weight 1275) was used.

  Each composition which added the compound and / or mixture which were represented to said Formula (A-1-1) to Formula (F-7) by the composition ratio as described in the following table to the light-shielding reaction apparatus provided with the stirring apparatus. 100 parts, 300 parts of methyl ethyl ketone, 100 parts of cyclohexanone, 0.1 part of p-methoxyphenol, 2 parts of IRGACURE819 (manufactured by BASF), and the following formulas (G-1) to (G-3) As a compound or a compound (G-4), polypropylene (weight average molecular weight 1275) is added in parts by weight as shown in the table below, and the mixture is heated and stirred at 50 ° C. for 1 hour, to Examples 1 to 156 and Comparative Examples 1 to 16. A coating solution for the polymerizable composition to be used was obtained.

A coating solution of the polymerizable composition was applied on the rubbed PET at room temperature using a bar coater # 4, and then dried at 80 ° C. for 2 minutes. Then, after leaving at room temperature for 2 minutes, UV irradiation (500 mJ / cm ² ) was performed. About the obtained film, the orientation defect was evaluated by polarizing microscope observation. 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.

  From the table, it can be seen that the optical film of the present invention has fewer alignment defects than the optical film of the comparative example. Next, each optical film was heat-treated at 120 ° C. for 5 hours. For the optical films having the cholesteric orientation obtained in Example 1 to Example 48 and Comparative Example 1 to Comparative Example 4, the absolute value of the change amount of the central value of the selective reflection wavelength before and after the heat treatment was measured. For the optical films having homogeneous orientation obtained in Examples 49 to 78 and Comparative Examples 5 to 8, the absolute value of the change amount of the phase difference Re before and after the heat treatment was measured. The results are shown in the table below.

  From the table, it can be seen that the optical film of the present invention has a smaller amount of change in the selective reflection wavelength or phase difference after the heat treatment than the optical film of the comparative example. From the above results, the optical film of the present invention has few alignment defects, and hardly changes in optical characteristics when placed in a high temperature state. Therefore, it is useful as a retardation film, a selective reflection film, etc. for display devices. .

Claims (15)

The following general formula (I)

(In the formula, P ¹ is the following formula (P-1) to formula (P-20)

Represents a group selected from
In R ^S1 , 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 A linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by ═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF— or —C≡C— In which any hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom,
Sp ¹ represents an alkylene group having 1 to 20 carbon atoms, 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,
n11 and n12 each independently represents an integer of 0 to 8,
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 any hydrogen atom in the group is a fluorine atom. One —CH ₂ — or two or more non-adjacent —CH ₂ — may be 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 C _{2 -, - CH 2 CH 2} -COO -, - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - Linear or branched having 1 to 20 carbon atoms which may be substituted by CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF— or —C≡C— Represents an alkyl group, or R ² represents the following formula (I-R2)

(Wherein P ² represents a group selected from the above formulas (P-1) to (P-20);
R ^S2 represents one —CH ₂ — or two or more non-adjacent —CH ₂ — 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 A linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by ═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF— or —C≡C— In which any hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom,
Sp ² represents an alkylene group having 1 to 20 carbon atoms, and when a plurality of Sp ² are present, they may be the same or different,
X ² 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 2} is plurality of They may be different even in the same case that,
k2 represents an integer of 0 to 10,
n21 and n22 each independently represents an integer of 0 to 8. ) Represents a group represented by
M ¹ is the following formula (I-M1)

(In the formula, A ¹ and A ² are each independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2, 5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6- Represents a diyl group or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted by one or more substituents L, but there are multiple A ¹ In this case, they may be the same or different, and L is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, Mel Script group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, Chioisoshiano group, or one -CH 2 _- or nonadjacent two or more -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 a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by -C≡C-, wherein any hydrogen atom in the alkyl group may be substituted by a fluorine atom, Or, L is the following formula (I-RL)

(In the formula, P ^L represents a group selected from the above formulas (P-1) to (P-20), and R ^SL represents one —CH ₂ — or two or more —CH that are not adjacent to each other. _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═ Represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by CF- or -C≡C-, wherein any hydrogen atom in the alkyl group is substituted with a fluorine atom or a chlorine atom may be, Sp ^L represents an alkylene group having 1 to 20 carbon atoms, they if Sp ^L there are multiple same A well be different ^also, X L is _-O in _{-, - 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 bond, if X ^L there are a plurality thereof may be different even in the same, kL is an integer from 0 to 10, an integer from 0 independently each nL1 and nL2 8 )), When a plurality of L are present in the compound, they may be the same or different,
Z ¹ represents —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 -, - COO-} CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH CH -, - N = N -, - CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, Z ^When there are multiple 1s, they may be the same or different,
m1 represents an integer of 0 to 5. ) Represents a group represented by The optical film containing the structural unit derived from the compound represented by this. Furthermore, the following general formula (II)

(Wherein P ³ and P ⁴ each independently represent a group that is polymerized by radical polymerization, cationic polymerization, or anionic polymerization;
Sp ³ and Sp ⁴ each independently represent a spacer group. When a plurality of Sp ³ are present, they may be the same or different, and when a plurality of Sp ⁴ are present, they may be the same. May be different,
X ³ and X ⁴ 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—, —C≡C— or a single bond. But they if X ³ there are a plurality may be the same or different and they if X ⁴ there are a plurality may be the same or different and
k3 and k4 each independently represents an integer of 0 to 10,
A ³ and A ⁴ are each independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2,5-diyl group. , Pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1 , 3-dioxane-2,5-diyl groups, these groups may be unsubstituted or substituted by one or more substituents L, but they are the same when there are multiple A ³ Can be different,
Z ² represents —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 -, - COO-} CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH CH -, - N = N -, - CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, Z ^{When two} or more ² exist, they may be the same or different,
m2 represents an integer of 0 to 5. The optical film of Claim 1 containing the structural unit derived from the compound represented by this. The compound represented by the general formula (I) is represented by the following general formula (IA)

(In the formula, P ¹ and M ¹ each have the same meaning as P ¹ and M ¹ in the general formula (I), and Sp ¹¹ and X ¹¹ each have the same meaning as Sp ¹ and X ¹ in the general formula (I). represents, n111 and n121 represents 0 or 1 each independently is, n111 + n121 represents ^{1, R 21} is the following formula (I-R2-a)

(Wherein, ^{P 2} has the same meaning as ^{P 2} in formula (I), ^{Sp 21} and ^{X 21} are as defined Sp ² and ^{X 2} each in the general formula (I), each n211 and n221 Independently represents 0 or 1, but n211 + n221 represents 1.). The optical film of Claim 1 or Claim 2 represented by this. In the general formula (I-A), n111 represents 0, n121 represents 1 ^represents a ^{group R 21} is represented by the formula (I-R2-A), n211 represents 1, the n221 is 0 The optical film according to claim 3 represented. The following general formula (IA-11)

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), A structural unit derived from a compound represented by Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ ), and the following general formula (IA-22)

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), A structural unit derived from a compound represented by Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ ), and the following general formula (IA-12)

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ represent the same meanings) and the following general formula (IA-21)

(In the formula, P ¹ , P ² , Sp ¹¹ , Sp ²¹ , X ¹¹ , X ²¹ and M ¹ are respectively P ¹ , P ² in the general formula (IA) or (I-R2-A), the optical film according to ^{sp 11, sp 21, X 11} , X 21 and ^{M 1} represent the same meaning as.) claim 3 containing a structural unit derived from a compound represented by. The following general formula (IA-111)

(Wherein, ^{P 1} and ^{P 2} each represent a formula (I-A) or the same meaning as ^{P 1} and ^{P 2} in the general formula ^(I-R2-A), A 11, A 12 and ^{A 21} are each Independently represents a 1,4-phenylene group or a 1,4-cyclohexylene group, these groups may be unsubstituted or substituted by one or more substituents L, Z ¹¹ and Z ¹² Each independently represents —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —COO—, —OCO—, —CO—NH—, —NH—CO—, —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- or a single bond) the compound represented by And the following general formula (IA-221)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ¹² each represents the same meaning as A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ^{12 in the} general formula (IA-111), and a structural unit derived from the following: General formula (IA-121)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ¹² each represents the same meaning as A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ^{12 in the} general formula (IA-111), and a structural unit derived from the following: General formula (IA-211)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ¹² each contain a structural unit derived from a compound represented by the formula (IA-111) having the same meaning as A ¹¹ , A ¹² , A ²¹ , Z ¹¹ and Z ¹² ). The optical film according to claim 3. The following general formula (IA-112)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ and A ²¹ each independently represents a 1,4-phenylene group or a 1,4-cyclohexylene group, but these groups may be unsubstituted or substituted by one or more substituents L. , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are each independently —OCH ₂ —, —CH ₂ O—, —CH ₂ CH ₂ —, —COO—, —OCO—, —CO—NH—, — NH—CO—, —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 Or a single bond. A structural unit derived from the compound represented by), the general formula (I-A-222)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or the general formula (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are respectively A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z in the general formula (IA-112). represents the same meaning as ¹³ and ^{Z 14.} a structural unit derived from the compound represented by), the general formula (I-a-122)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or the general formula (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are respectively A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z in the general formula (IA-112). represents the same meaning as ¹³ and ^{Z 14.} a structural unit derived from the compound represented by), the general formula (I-a-212)

(In the formula, P ¹ and P ² represent the same meaning as P ¹ and P ² in the general formula (IA) or the general formula (I-R2-A), respectively), A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are respectively A ¹¹ , A ¹² , A ¹³ , A ¹⁴ , A ²¹ , Z ¹¹ , Z ¹² , Z in the general formula (IA-112). the optical film according to claim 3 containing a structural unit derived from a compound represented by the representative.) the same meaning as ¹³ and Z ^14.   Furthermore, the optical film as described in any one of Claims 1-7 containing the structural unit derived from a chiral compound.   The optical film according to any one of claims 1 to 8, which has a cholesteric structure. The compound represented by the general formula (I) is represented by the following general formula (IC)

^{(Wherein, P 1, R S1, n11} , n12, Sp 1, X 1, P 1 in k1 and ^{M 1} are each the general formula ^{(I), R S1, n11} , n12, Sp 1, X 1, k1 and M ¹ represents the same meaning, ^* C represents an asymmetric carbon atom, R ^2C represents a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, cyano group, nitro group, isocyano Group, thioisocyano group, or any hydrogen atom in the group may be substituted with a fluorine atom, and 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—. Represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by R ^2C , or R ^2C is represented by the following formula (I-R2-C):

(Wherein P ² , R ^S2 , n21, n22, Sp ² , X ² and k2 have the same meaning as P ² , R ^S2 , n21, n22, Sp ² , X ² and k2 in the general formula (I), respectively. The optical film according to claim 1, represented by: ^* C represents an asymmetric carbon atom.   The compound represented by the general formula (I) according to claim 1.   The compound represented by general formula (IA-111), general formula (IA-221), general formula (IA-121) or general formula (IA-211) according to claim 6. .   The compound represented by general formula (IA-112), general formula (IA-222), general formula (IA-122) or general formula (IA-212) according to claim 7 .   The laminated film using the optical film as described in any one of Claims 1-10.   The display apparatus provided with the optical film as described in any one of Claims 1-10, or the laminated | multilayer film as described in Claim 14.