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Definitions

• the present invention relates to compounds, liquid crystal compositions, cured products, optically anisotropic substances, and reflective films.
• a compound exhibiting liquid crystallinity (hereinafter, also referred to as “liquid crystal compound”) can be applied to various uses.
• the liquid crystal compound is applied to the production of an optically anisotropic substance represented by a retardation film or the production of a reflective film formed by fixing a cholesteric liquid crystal phase.
• the cholesteric liquid crystal phase is formed by adding a chiral compound to a nematic liquid crystal.
• Patent Document 1 discloses a chiral compound having a helical twisting power (HTP) with respect to a liquid crystal compound.
• HTP helical twisting power
• the chiral compound described in Patent Document 1 shows the degree of change in HTP intensity caused by exposure to light irradiation such as ultraviolet rays (hereinafter, "" It was found that the rate of change in HTP) has not reached the level currently desired.
• an object of the present invention is to provide a compound having an excellent rate of change in HTP due to exposure.
• Another object of the present invention is to provide a liquid crystal composition, a cured product, an optically anisotropic substance, and a reflective film using the above compound.
• at least one of the substituents including the group represented by the general formula (2) is specified in the general formula (1) at the bonding position represented by the above * 1.
• both X 1 and X 2 represent a substituent containing a group represented by the general formula (2), and a group represented by the general formula (2).
• the present invention it is possible to provide a compound having an excellent rate of change in HTP due to exposure. Further, according to the present invention, it is possible to provide a liquid crystal composition, a cured product, an optically anisotropic substance, and a reflective film using the above compound.
• the notation not describing substitution and non-substitution includes a group having a substituent as well as a group having no substituent.
• the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
• the substituent when it is simply referred to as a substituent, includes, for example, the following substituent T.
• the substituent T includes a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heterocyclic group, and a cyano group.
• a halogen atom fluorine atom, chlorine atom, bromine atom, iodine atom, etc.
• Hydroxyl group nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, amino group (including alkylamino group and anilino group), acylamino group, aminocarbonylamino Group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl or arylsulfinyl Group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, aryl or heterocyclic azo group, imide group,
• L T represents a single bond or a divalent linking group.
• P T represents a polymerizable group represented by the general formulas (P-1) to (P-20) described later.
• the divalent linking group represented by L T is not particularly limited, is preferably an alkylene group which may contain a hetero atom, more alkylene groups contain an ⁇ 1 carbon atoms which may 10 oxygen atoms
• Ra represents a hydrogen atom or a methyl group.
• Me represents a methyl group and Et represents an ethyl group.
• those having a hydrogen atom may be further substituted with any of the above-mentioned substituents in the portion of the hydrogen atom in the substituent.
• the bonding direction of the divalent group described in the present specification is not limited unless otherwise specified.
• the position bonded to the L side is * 1 and the N side.
• * 1-CH C (CN) -COO- * 2.
• M is * 1-COO- * 2. It may be * 1-OCO- * 2.
• the characteristic points of the compound represented by the general formula (1) are at least one of X 1 , X 3 , X 5 , and X 7 , and X 2 , X 4. , X 6 and X 8 are substituents containing a group represented by the general formula (2) described later.
• the double bond site specified in the general formula (2) is photoisomerized when exposed to energy irradiation such as ultraviolet rays to cause a structural change. obtain.
• the group represented by the general formula (2) has Y 1 and Y 2 on the same side with respect to the double bond specified in the general formula (2), but when it receives energy irradiation such as ultraviolet rays.
• Y 1 and Y 2 can be photoisomerized so that they are on different sides of the double bond axis to cause a structural change.
• the specific compound has a large structural change due to photoisomerization, and the dihedral angle of the binaphthyl skeleton site is easily changed by this photoisomerization, and as a result, an excellent rate of change in HTP is achieved. ..
• a "binaphthyl skeleton site” is intended to be a structural site (structural site shown below) other than X 1 to X 8 in the general formula (1) described later. That is, it corresponds to a general term for structural parts other than X 1 to X 8 in the general formula (1-1) and the general formula (1-2) described later.
• the specific compound is a compound represented by the general formula (1).
• the portion where the solid line and the broken line are parallel represents a single bond or a double bond.
• the compound represented by the general formula (1) corresponds to the compound represented by the following general formula (1-1) when the portion where the solid line and the broken line are parallel is a single bond, and the solid line.
• the portion where the broken line is parallel to the double bond is a double bond, it corresponds to the compound represented by the following general formula (1-2).
• a compound represented by the general formula (1-2) is preferable.
• general formula (1-1) and X 1 ⁇ X 8 in the general formula (1-2) and X 1 ⁇ X 8 in the general formula (1), and the same meaning.
• X 1 to X 8 independently represent a hydrogen atom or a monovalent substituent.
• the substituents represented by X 1 to X 8 are not particularly limited, and examples thereof include the groups exemplified as the above-mentioned substituent T. However, at least one of X 1 , X 3 , X 5 , and X 7 and at least one of X 2 , X 4 , X 6 , and X 8 are represented by the general formula (2) described later. Represents a substituent containing a group to be treated.
• Any combination selected from X 1 and X 2 , X 3 and X 4 , X 5 and X 6 , and X 7 and X 8 in that the rate of change of HTP is superior is the general formula (2) described later. It is preferable to represent a substituent containing a group represented by.
• X 1 and X 2 are connected to each other to form a ring in that the rate of change of HTP is more excellent. That is, in the general formula (1), X 1 and X 2 are connected to each other to form a ring, and at least one of X 3 , X 5 , and X 7 and X 4 , X 6 , and X 7 are formed. It is preferable that at least one of X 8 represents a substituent containing a group represented by the general formula (2) described later.
• the ring in which X 1 and X 2 are linked and bonded to each other is not particularly limited, and may be either an aromatic ring or a non-aromatic ring, but a non-aromatic ring is preferable. If X 1 and X 2 are linked together to form a ring, the group X 1 and X 2 are formed by linking each other, for example, * - L S1 -2 divalent aromatic hydrocarbon ring group -L S2- * or * -L S3--2 -valent aliphatic hydrocarbon group-L S4- * is preferable. Note that * represents the bonding position with the binaphthyl skeleton in the general formula (1).
• Examples of the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon ring group include a benzene ring and a naphthalene ring.
• the divalent aliphatic hydrocarbon group may be linear, branched or cyclic.
• the number of carbon atoms is preferably 1 to 12, more preferably 1 to 10, and even more preferably 1 to 6.
• an alkylene group is preferable.
• the hydrogen atom in the aliphatic hydrocarbon group may be substituted with another substituent such as a halogen atom.
• L S1 to L S4 independently represent a single bond or a divalent linking group.
• RD represents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
• the hydrogen atom in the divalent linking group may be substituted with another substituent such as a halogen atom.
• the L S1 and L S 2 may be a single bond, a divalent aliphatic hydrocarbon group (may be linear, branched or cyclic, and preferably have 1 to 20 carbon atoms, for example, an alkylene group or an alkenylene group. , And an alkynylene group.), -O-, -CO-, -CO-NH-, -CH 2 O-, or -COO- is preferable.
• RD represents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
• the hydrogen atom in the divalent linking group may be substituted with another substituent such as a halogen atom.
• L S3 and L S4 single bond, -O-, -CO-, -CO-NH-, or -COO- is preferable.
• Z represents a single bond or —O—.
• Y 1 and Y 2 independently represent a hydrogen atom or a hydrocarbon group containing no aryl group.
• a single bond is preferable because the rate of change of HTP is more excellent.
• the aryl group-free hydrocarbon group represented by Y 1 and Y 2 include an aliphatic hydrocarbon group.
• the aliphatic hydrocarbon group may have a substituent.
• the substituent include the groups exemplified as the above-mentioned Substituent T.
• the aliphatic hydrocarbon group does not have an aryl group as a substituent.
• the aliphatic hydrocarbon group may be linear, branched, or cyclic. Further, the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. When the aliphatic hydrocarbon group represents an unsaturated aliphatic hydrocarbon group, it may have both a double bond and a triple bond. When the aliphatic hydrocarbon group represents an alkenyl group, the number of double bonds in the alkenyl group may be one or two or more. When the aliphatic hydrocarbon group represents an alkynyl group, the number of triple bonds in the alkynyl group may be one or two or more.
• the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3 in that the rate of change in HTP is more excellent. ..
• the number of carbon atoms of the alkenyl group is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 3 in that the rate of change in HTP is more excellent. ..
• the number of carbon atoms of the alkynyl group is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 3 in that the rate of change in HTP is more excellent. ..
• both are hydrogen atoms in that the rate of change of HTP is more excellent.
• * 1 and * 2 represent the coupling position.
• * 1 represents the bond position
• * 2 represents the bond position
• the following general It is preferable to represent the group represented by the formula (2B).
• the group represented by the general formula (2) it is more preferable to represent the group represented by the general formula (2A).
• R 1 represents a hydrogen atom or a substituent.
• the substituent represented by R 1 is not particularly limited, and examples thereof include the group exemplified as the above-mentioned substituent T.
• an aliphatic hydrocarbon group or an aromatic hydrocarbon ring group is preferable.
• the aliphatic hydrocarbon group may be linear, branched or cyclic.
• the number of carbon atoms is preferably 1 to 12, more preferably 1 to 10, and even more preferably 1 to 6.
• an alkyl group is preferable.
• the aliphatic hydrocarbon group may have a substituent.
• substituents include the groups exemplified as the above-mentioned Substituent T.
• aromatic hydrocarbon ring group an aromatic hydrocarbon ring group having 1 to 10 carbon atoms is preferable, and a phenyl group is more preferable.
• the aromatic hydrocarbon ring group may have a substituent. Examples of the substituent include the groups exemplified as the above-mentioned Substituent T, and an alkoxy group and the like are preferable.
• R 2 represents a substituent.
• the substituent represented by R 2 is not particularly limited, and examples thereof include the group exemplified as the above-mentioned substituent T.
• Preferred substituents represented by R 2 include the same substituents represented by R 1 in the above-mentioned general formula (2A).
• the carbonyl carbon specified in the general formula (2) is not bonded to —O—.
• the substituent represented by R 1 in the general formula (2A) has the general formula (2).
• the atom bonded to the carbonyl carbon specified in) is preferably not an oxygen atom (ether oxygen).
• the group represented by the general formula (2) represents the group represented by the general formula (2B)
• the atom to which * 2 is bonded in the general formula (2B) is not an oxygen atom (ether oxygen). Is preferable.
• the rate of change of HTP is more excellent
• the carbonyl carbon specified in the general formula (2) is a hydrocarbon which may have a substituent. It is preferably bonded to a heterocyclic group which may have a ring group or a substituent. That is, the substituent containing the group represented by the general formula (2) is preferably a substituent containing the group represented by the following general formula (3).
• A represents a hydrocarbon ring group which may have a substituent or a heterocyclic group which may have a substituent.
• the hydrocarbon ring group include an aliphatic hydrocarbon ring group and an aromatic hydrocarbon ring group.
• the number of ring members of the hydrocarbon ring constituting the hydrocarbon ring group is not particularly limited, but is preferably 5 to 10.
• the aliphatic hydrocarbon ring constituting the aliphatic hydrocarbon ring group may have either a monocyclic structure or a polycyclic structure.
• the aliphatic hydrocarbon ring has a polycyclic structure
• the number of carbon atoms in the aliphatic hydrocarbon ring is not particularly limited, but is preferably 5 to 10, more preferably 5 or 6.
• Specific examples of the aliphatic hydrocarbon ring include a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a norbornene ring, and an adamantane ring.
• the aromatic hydrocarbon ring constituting the aromatic hydrocarbon ring group may have either a monocyclic structure or a polycyclic structure.
• the aromatic hydrocarbon ring has a polycyclic structure, it is preferable that at least one of the rings contained in the polycyclic structure is a 5-membered ring or more.
• the number of carbon atoms in the aromatic hydrocarbon ring is not particularly limited, but 6 to 18 is preferable, and 6 to 10 is more preferable.
• aromatic hydrocarbon ring examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a fluorene ring.
• a benzene ring or a naphthalene ring is preferable, and a benzene ring is more preferable.
• heterocyclic group examples include an aliphatic heterocyclic group and an aromatic heterocyclic group.
• the number of ring members of the heterocycle constituting the heterocyclic group is not particularly limited, but is often 5 to 10.
• the aliphatic heterocycle constituting the aliphatic heterocyclic group may have either a monocyclic structure or a polycyclic structure. When the aliphatic heterocycle has a polycyclic structure, it is preferable that at least one of the rings contained in the polycyclic structure is a 5-membered ring or more.
• the hetero atom contained in the aliphatic heterocycle include a nitrogen atom, an oxygen atom, and a sulfur atom.
• the number of ring members of the aliphatic heterocycle is not particularly limited, but is preferably 5 to 10.
• Specific examples of the aliphatic heterocycle include an oxolane ring, an oxane ring, a piperidine ring, and a piperazine ring.
• the aliphatic heterocycle may be a ring in which -CH 2- is substituted with -CO-, and examples thereof include a phthalimide ring.
• the aromatic heterocycle constituting the aromatic heterocyclic group may have either a monocyclic structure or a polycyclic structure. When the aromatic heterocycle has a polycyclic structure, it is preferable that at least one of the rings contained in the polycyclic structure is a 5-membered ring or more.
• hetero atom contained in the aromatic heterocyclic group examples include a nitrogen atom, an oxygen atom, and a sulfur atom.
• the number of ring members of the aromatic heterocycle is not particularly limited, but is preferably 5 to 18.
• Specific examples of the aromatic heterocycle include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a thiophene ring, a thiazole ring, and an imidazole ring.
• the hydrocarbon ring group and the heterocyclic group represented by A may further have a substituent.
• the substituent is not particularly limited, and examples thereof include the group exemplified as the above-mentioned Substituent T.
• R 3 represents a hydrogen atom or a substituent.
• the substituent represented by R 3 is not particularly limited, and examples thereof include the group exemplified as the above-mentioned substituent T, and an alkoxy group and the like are preferable.
• the group adjacent to Z has a hydrocarbon ring group or a substituent which may have a substituent, as compared with the case where Z is a single bond. Even if it is a heterocyclic group which may be present, the flatness of the mesogen moiety is difficult to improve, and the rate of change of HTP is not large.
• At least one of the substituents including the group represented by the above general formula (2) is the binding position represented by * 1 in the general formula (1) in that the rate of change of HTP is excellent. It is preferably linked to the binaphthyl skeletal site specified therein. That is, the substituent containing the group represented by the general formula (2) includes a substituent containing the group represented by the general formula (2A) or a group represented by the general formula (3A). Substituents are preferable, and they are preferably linked to the binaphthyl skeleton site specified in the general formula (1) at the binding position represented by * 1 in the general formula (2A) and the general formula (3A). ..
• the substituent containing the group represented by the general formula (2) is preferably the substituent represented by the following general formula (2-1), and is represented by the following general formula (2-2). Substituents are preferred.
• L A represents a single bond or a divalent linking group.
• W A represents a group represented by the above-mentioned general formula general formula (2A) or (2B).
• Examples of the divalent linking group represented by L A it is not particularly limited, for example, divalent aliphatic hydrocarbon group (linear, branched, and branched and cyclic carbon atoms 1 to 20 is preferable, and examples thereof include an alkylene group.
• an alkenylene group or an alkynylene group may be used), an arylene group, -O-, -S-, -SO 2- , -NR.
• R 1 represents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
• the hydrogen atom in the divalent linking group may be substituted with another substituent such as a halogen atom.
• L A represents a divalent linking group
• Z in the general formula (2A) or (2B) represents a single bond
• the formula in the L A It is preferable that the bonding atom with the carbonyl carbon specified in 2A) or (2B) is not an oxygen atom (ether oxygen).
• W A is preferably a group represented by the general formula (2A).
• L B represents a single bond or a divalent linking group.
• W B represents a group represented by the above-mentioned general formula general formula (3A) or (3B).
• Examples of the divalent linking group represented by L B are not particularly limited, for example, divalent aliphatic hydrocarbon group (linear, branched, and branched and cyclic carbon atoms 1 to 20 is preferable, and examples thereof include an alkylene group. In addition, an alkenylene group or an alkynylene group may be used), an arylene group, -O-, -S-, -SO 2- , -NR.
• R 1 represents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
• the hydrogen atom in the divalent linking group may be substituted with another substituent such as a halogen atom.
• W B is preferably a group represented by the general formula (3A).
• the specific compound can be synthesized by a known method.
• the specific compound may be R-form or S-form, or may be a mixture of R-form and S-form.
• the specific compound can be applied to various uses and is preferably used as a so-called chiral compound.
• a cholesteric liquid crystal phase can be formed by using a liquid crystal composition obtained by mixing a specific compound and a liquid crystal compound.
• the liquid crystal composition will be described in detail below.
• the specific liquid crystal composition includes a specific compound and a liquid crystal compound.
• various components essential or optionally contained in the specific liquid crystal composition will be described.
• the specific liquid crystal composition contains a specific compound.
• the specific compound is as described above.
• the content of the specific compound in the specific liquid crystal composition is not particularly limited, but is preferably 1 to 20% by mass, more preferably 2 to 15% by mass, based on the total mass of the liquid crystal compound in the composition. It is more preferably to 10% by mass.
• the specific liquid crystal composition one specific compound may be used alone, or two or more specific compounds may be used. When two or more kinds are used, it is preferable that the total content is within the above range.
• the specific liquid crystal composition contains a liquid crystal compound.
• the liquid crystal compound is a compound other than the specific compound and means a compound exhibiting liquid crystallinity. Further, “the compound exhibits liquid crystallinity” means that the compound has a property of expressing an intermediate phase between the crystalline phase (low temperature side) and the isotropic phase (high temperature side) when the temperature is changed. Intended.
• the optical anisotropy and fluidity derived from the liquid crystal phase are confirmed by observing the compound under a polarizing microscope while heating or lowering the temperature of the compound with a hot stage system FP90 manufactured by Metertredo. it can.
• the liquid crystal compound is not particularly limited as long as it has liquid crystal properties, and examples thereof include rod-shaped nematic liquid crystal compounds.
• rod-shaped nematic liquid crystal compounds include azomethines, azoxys, cyanobiphenyls, cyanophenyl esters, benzoic acid esters, cyclohexanecarboxylic acid phenyl esters, cyanophenylcyclohexanes, cyano-substituted phenylpyrimidines, and alkoxy-substituted compounds.
• Examples thereof include phenylpyrimidines, phenyldioxans, trans, and alkenylcyclohexylbenzonitriles. Not only low molecular weight liquid crystal compounds but also high molecular weight liquid crystal compounds can be used.
• the liquid crystal compound may be polymerizable or non-polymerizable, and is preferably polymerizable.
• a liquid crystal compound having one or more polymerizable groups is preferable, and a liquid crystal compound having two or more polymerizable groups is more preferable, because the cholesteric liquid crystal phase can be fixed. Liquid crystal compounds having a group are more preferable.
• Rod-shaped liquid crystal compounds having no polymerizable group are described in various documents (for example, Y. Goto et.al., Mol. Cryst. Liq. Cryst. 1995, Vol. 260, pp.23-28). is there.
• the polymerizable rod-shaped liquid crystal compound is obtained by introducing a polymerizable group into the rod-shaped liquid crystal compound.
• the polymerizable group include an unsaturated polymerizable group, an epoxy group, and an aziridinyl group, and an unsaturated polymerizable group is preferable, and an ethylenically unsaturated polymerizable group is more preferable.
• the polymerizable group can be introduced into the molecule of the rod-shaped liquid crystal compound by various methods.
• the number of polymerizable groups contained in the polymerizable rod-shaped liquid crystal compound is preferably 1 to 6, more preferably 1 to 3, and even more preferably 2.
• Two or more kinds of polymerizable rod-shaped liquid crystal compounds may be used in combination. When two or more kinds of polymerizable rod-shaped liquid crystal compounds are used in combination, the orientation temperature can be lowered.
• liquid crystal compound a compound represented by the following general formula (LC) is preferable.
• P 11 and P 12 each independently represent a hydrogen atom or a polymerizable group. However, at least one of P 11 and P 12 represents a polymerizable group.
• L 11 and L 12 each independently represent a single bond or a divalent linking group.
• a 11 to A 15 each represent an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent independently.
• Z 11 to Z 14 each independently represent a single bond or a divalent linking group.
• m 3 and m 4 independently represent an integer of 0 or 1, respectively.
• the polymerizable group represented by P 11 and P 12 is not particularly limited, but as a suitable specific example, it is represented by the above-mentioned general formulas (P-1) to (P-20). Polymerizable groups can be mentioned.
• the polymerizable groups represented by P 11 and P 12 represent the above-mentioned general formulas (P-1) to (P-20)
• * in the general formulas (P-1) to (P-20) Represents the connection position with L 11 or L 12 .
• P 11 and P 12 is preferably representative of at least one one of polymerizable group, and more preferably both P 11 and P 12 represents a polymerizable group.
• the divalent linking group represented by L 11 and L 12 is not particularly limited, and is, for example, a linear or branched alkylene group having 1 to 20 carbon atoms and a carbon number of carbon atoms.
• 1 to 20 linear or branched alkylene groups one or more -CH 2 -s are -O-, -S-, -NH-, -N (CH 3 )-, -CO- , Or a linking group selected from the group consisting of groups substituted with -COO-.
• the divalent linking group represented by L 11 and L 12 one or two or more -CH 2- in a linear or branched alkylene group having 1 to 20 carbon atoms is -O-. Substituted groups are preferred.
• a 11 to A 15 each represent an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may independently have a substituent.
• the number of ring members of the aromatic hydrocarbon ring group is not particularly limited, but is, for example, 5 to 10.
• the aromatic hydrocarbon ring constituting the aromatic hydrocarbon ring group may have either a monocyclic structure or a polycyclic structure.
• the number of carbon atoms in the aromatic hydrocarbon ring is not particularly limited, but 6 to 18 is preferable, and 6 to 10 is more preferable.
• Specific examples of the aromatic hydrocarbon ring include a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a fluorene ring. Of these, a benzene ring is preferable.
• the aromatic hydrocarbon ring constitutes an aromatic hydrocarbon ring group by removing two hydrogen atoms on the ring.
• the number of ring members of the aromatic heterocyclic group is, for example, 5 to 10.
• the aromatic heterocycle constituting the aromatic heterocyclic group may have either a monocyclic structure or a polycyclic structure.
• Examples of the hetero atom contained in the aromatic heterocyclic group include a nitrogen atom, an oxygen atom and a sulfur atom.
• the number of carbon atoms in the aromatic heterocycle is not particularly limited, but is preferably 5 to 18.
• Specific examples of the aromatic heterocycle include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a thiophene ring, a thiazole ring, and an imidazole ring.
• the aromatic heterocycle constitutes an aromatic heterocyclic group by removing two hydrogen atoms on the ring.
• the aromatic hydrocarbon ring group and the aromatic heterocyclic group may have a substituent.
• the type of the substituent is not particularly limited, and examples thereof include known substituents. Examples thereof include halogen atom, alkyl group, alkoxy group, aryl group, hydroxyl group, amino group, carboxyl group, sulfonamide group, N-sulfonylamide group, acyl group, acyloxy group, cyano group, nitro group and alkoxycarbonyl group. Be done.
• Each of the above groups may be further substituted with a substituent.
• the hydrogen atom in the alkyl group may be substituted with a fluorine atom.
• the number of substituents is not particularly limited, and the aromatic hydrocarbon ring group and the aromatic heterocyclic group may have one substituent or may have a plurality of substituents.
• the substituent is preferably a fluorine atom, a chlorine atom, a fluoroalkyl group, an alkoxy group, or an alkyl group, and fluoro is preferable, because the solubility of the compound represented by the general formula (LC) is further improved. It is more preferably an alkyl group, an alkoxy group, or an alkyl group.
• the number of carbon atoms in the fluoroalkyl group and the alkyl group and the number of carbon atoms in the alkyl group in the alkoxy group are not particularly limited, but 1 to 10 is preferable, 1 to 5 is more preferable, and 1 to 3 is further preferable. Is particularly preferable.
• the fluoroalkyl group is a group in which at least one hydrogen atom in the alkyl group is substituted with a fluorine atom, and it is preferable that all hydrogen atoms are substituted with a fluorine atom (so-called perfluoroalkyl group). preferable).
• a 11 to A 15 are preferably an aromatic hydrocarbon ring group which may have a substituent, and more preferably a phenylene group bonded at the 1-position and the 4-position.
• the divalent linking group represented by Z 11 to Z 14 is not particularly limited, and for example, a divalent aliphatic hydrocarbon group (linear, branched chain, and cyclic) is used. Any of them may be used, and the number of carbon atoms is preferably 1 to 20, and examples thereof include an alkylene group. In addition, an alkenylene group and an alquinylene group may be used), —O—, —S.
• R 1 represents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
• the hydrogen atom in the divalent linking group may be substituted with another substituent such as a halogen atom.
• m 3 and m 4 independently represent an integer of 0 or 1, and 0 is preferable.
• the compound represented by the general formula (LC) can be synthesized by a known method. Specific examples of the compound represented by the above general formula (LC) are shown below, but the present invention is not limited thereto.
• the compound represented by the general formula (LC) may be used alone or in combination of two or more.
• the content of the liquid crystal compound in the specific liquid crystal composition is preferably 5 to 99% by mass, more preferably 25 to 98% by mass, still more preferably 75 to 98% by mass, based on the total solid content of the composition.
• the solid content is intended to be a component other than the solvent in the composition. If it is not a solvent, even if it is a liquid component, it is regarded as a solid content.
• the specific liquid crystal composition one liquid crystal compound may be used alone, or two or more liquid crystal compounds may be used. When two or more kinds are used, it is preferable that the total content is within the above range.
• the specific liquid crystal composition may contain a polymerization initiator.
• the polymerization initiator include a photopolymerization initiator and a thermal polymerization initiator, and among them, a photopolymerization initiator capable of initiating a polymerization reaction by irradiation with ultraviolet rays is preferable.
• the photopolymerization initiator include alkylphenone compounds, ⁇ -carbonyl compounds, acidoin ethers, ⁇ -hydrocarbon-substituted aromatic acidoine compounds, polynuclear quinone compounds, phenazine compounds, and oxadiazole compounds.
• the alkylphenone compound for example, IRGACURE 907 or the like is used.
• the content of the polymerization initiator in the composition is not particularly limited, but is preferably 0.1 to 20% by mass with respect to the total mass of the liquid crystal compound. -8% by mass is more preferable.
• the specific liquid crystal composition one type of polymerization initiator may be used alone, or two or more types may be used. When two or more kinds are used, it is preferable that the total content is within the above range.
• the specific liquid crystal composition may contain a surfactant that contributes to the formation of a stable or rapid liquid crystal phase (eg, nematic phase, cholesteric phase).
• a surfactant that contributes to the formation of a stable or rapid liquid crystal phase (eg, nematic phase, cholesteric phase).
• the surfactant include a fluorine-containing (meth) acrylate-based polymer, a compound represented by the general formulas (X1) to (X3) described in WO2011 / 162291, and paragraphs 882 to 0090 of JP2014-119605.
• the compound represented by the general formula (I) described in the above, and the compounds described in paragraphs 0020 to 0031 of JP-A-2013-47204 (Patent No. 5774518) can be mentioned.
• horizontal orientation means the molecular axis of the liquid crystal compound (when the liquid crystal compound is a rod-shaped liquid crystal compound, it corresponds to the long axis of the liquid crystal compound) and the surface of the layer of the composition (although it means that the liquid crystal surfaces are parallel, it does not require that they are strictly parallel, and in the present specification, it means an orientation in which the inclination angle formed with the liquid crystal surface is less than 20 degrees.
• the spiral axis deviates from the film surface normal, resulting in a decrease in reflectance or fingerprinting. It is not preferable because a pattern is generated and haze is increased or diffractivity is exhibited.
• fluorine-containing (meth) acrylate-based polymer that can be used as a surfactant include the polymers described in paragraphs 0018 to 0043 of JP-A-2007-272185.
• the content of the surfactant is not particularly limited, but is preferably 0.001 to 10% by mass, preferably 0.05 to 3% by mass, based on the total mass of the liquid crystal compound. % Is more preferable.
• the specific liquid crystal composition one type of surfactant may be used alone, or two or more types may be used. When two or more kinds are used, it is preferable that the total content is within the above range.
• the specific liquid crystal composition may contain a solvent.
• the solvent preferably can dissolve each component of the composition.
• methyl ethyl ketone, cyclohexanone, and a mixed solvent thereof and the like can be mentioned.
• the content of the solvent in the specific liquid crystal composition is preferably an amount having a solid content concentration of 5 to 50% by mass, and more preferably 10 to 40% by mass. preferable.
• one kind of solvent may be used alone, or two or more kinds of solvents may be used. When two or more kinds are used, it is preferable that the total content is within the above range.
• the specified liquid crystal composition includes antioxidants, ultraviolet absorbers, sensitizers, stabilizers, plasticizers, chain transfer agents, polymerization inhibitors, defoamers, leveling agents, thickeners, and flame retardants. , Dispersants, polymerizable monomers, and other additives such as colorants such as dyes and pigments may be included.
• the present invention also includes a cured product obtained by curing a specific liquid crystal composition.
• the method for curing (polymerizing and curing) the specific liquid crystal composition is not particularly limited, and a known method can be adopted.
• the liquid crystal compound can be immobilized in an oriented state, and a so-called optically anisotropic substance or a layer formed by immobilizing a cholesteric liquid crystal phase can be formed.
• steps X to Z will be described in detail.
• Step X is a step of bringing the substrate into contact with the specific liquid crystal composition to form a composition layer on the substrate.
• the type of substrate used is not particularly limited, and examples thereof include known substrates (for example, resin substrates, glass substrates, ceramic substrates, semiconductor substrates, and metal substrates).
• the method of bringing the substrate into contact with the specific liquid crystal composition is not particularly limited, and examples thereof include a method of applying the specific liquid crystal composition on the substrate and a method of immersing the substrate in the specific liquid crystal composition.
• a drying treatment may be carried out in order to remove the solvent from the composition layer on the substrate, if necessary. Further, heat treatment may be carried out in order to promote the orientation of the liquid crystal compound and bring it into the state of the liquid crystal phase.
• Step Y is a step of exposing the composition layer using i-rays (wavelength 365 nm) or the like. It is preferable that the specific compound undergoes photoisomerization by the exposure treatment and the HTP thereof changes. In this exposure process, the degree of change in HTP can also be adjusted by appropriately adjusting the exposure amount and / or the exposure wavelength. After the exposure, heat treatment may be further carried out in order to further promote the orientation of the liquid crystal compound and bring it into the state of the liquid crystal phase. That is, heat treatment may be carried out to adjust the orientation of the liquid crystal compound.
• the spiral pitch (and thus the selective reflection wavelength, etc.) of the liquid crystal phase obtained here reflects the HTP adjusted in the above-mentioned exposure process.
• Step Z is a step of applying a hardening treatment to the composition layer that has undergone the step Y.
• the method of the curing treatment is not particularly limited, and examples thereof include a photocuring treatment and a thermosetting treatment. Of these, photocuring treatment is preferable.
• the specific liquid crystal composition preferably contains a photopolymerization initiator.
• the wavelength of the light irradiated in the photocuring treatment is preferably different from the wavelength of the light used in the above-mentioned exposure treatment, and the photopolymerization initiator is sensitive to the wavelength of the light used in the exposure treatment. It is preferable not to show.
• a layer formed by immobilizing the cholesteric liquid crystal phase is formed.
• the layer formed by immobilizing the cholesteric liquid crystal phase no longer needs to exhibit liquid crystallinity. More specifically, for example, the state in which the cholesteric liquid crystal phase is "immobilized” is the most typical and preferable mode in which the orientation of the liquid crystal compound which is the cholesteric liquid crystal phase is maintained. More specifically, in the temperature range of 0 to 50 ° C., usually 0 to 50 ° C., and -30 to 70 ° C. under more severe conditions, the layer has no fluidity and the orientation morphology is not changed by an external field or an external force. , It is preferable that the fixed orientation form can be kept stable.
• the specific liquid crystal composition can be applied to various uses. For example, using a specific liquid crystal composition, a polarizing element, a reflective film (reflective layer), an antireflection film, a viewing angle compensation film, holography, security, a sensor, and a mirror for real image projection (front projection), which are constituent elements of an optical element, are used. , Rear projection), virtual image projection mirror, decorative sheet, heat shield sheet, light shield sheet, screen, optical variant, alignment film, etc. can be formed.
• a cured product can be obtained by subjecting the specific liquid crystal composition to a curing treatment (light irradiation treatment, heat treatment, etc.), and the cured product is a component of the optical element.
• Polarizing element, reflective film (reflective layer), antireflection film, viewing angle compensation film, holography, security, sensor, real image projection mirror (front projection, rear projection), virtual image projection mirror, decorative sheet, shield It can be suitably applied to a heat sheet, a light-shielding sheet, a screen, an optical variant, an alignment film and the like.
• the optical anisotropy is intended to be a substance having optical anisotropy.
• the reflective film corresponds to a layer formed by fixing the cholesteric liquid crystal phase, and can reflect light in a predetermined reflection band.
• sodium bisulfite water sodium bisulfite (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 21.7 g, water 290 mL), water 325 mL, sodium hydrogen carbonate water (sodium hydrogen carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 13.0 g).
• Water 300 mL
• dried over magnesium sulfate distilled off under reduced pressure, and transferred to a three-necked flask.
• DMF N, N-dimethylformamide, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• potassium carbonate manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• butyl acetate manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• dibromomethane manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• the obtained solution was washed with 100 mL of 10% layered water, 200 mL of water and 343 mL of 10% saline solution, respectively.
• the obtained solution was dried over magnesium sulfate, and then the solvent was distilled off from the solution under reduced pressure.
• Compound CE-1 is a compound described in US Patent Publication No. 2014/0264168, and was synthesized according to the method described in the same document.
• Compound CE-2 is a compound described in JP-A-2007-176927, and was synthesized according to the method described in the same document.
• Compound CE-3 is a compound described in US Patent Publication No. 2014/0160420 and was synthesized according to the method described in the same contribution.
• the structures of the compounds CE-1 to CE-3, which are comparative compounds, are shown below.
• ⁇ Preparation of liquid crystal layer 1> A polyimide alignment film material SE-130 (manufactured by Nissan Chemical Industries, Ltd.) was applied onto the washed glass substrate to form a coating film. After firing the obtained coating film, a substrate with an alignment film was produced by rubbing treatment. 40 ⁇ L of the above composition was spin-coated on the rubbing-treated surface of the alignment film under the conditions of 1500 rpm for 10 seconds, and then heat-dried at 90 ° C. for 1 minute to form a composition layer.
• the obtained composition layer was subjected to a central reflection wavelength at room temperature (23 ° C.) using a microscope (manufactured by Nikon Corporation, ECLIPSE E600-POL) and a spectrophotometer (manufactured by Shimadzu Corporation, UV-3100 (PC)).
• HTP initial HTP
• HTP (average refractive index of liquid crystal compound) / ⁇ (concentration of chiral compound with respect to liquid crystal compound (mass%)) ⁇ (center reflection wavelength) ⁇ [ ⁇ m -1 ]
• the average refractive index of the liquid crystal compound was calculated on the assumption that it was 1.55.
• the rate of change in HTP was evaluated based on the following criteria. Evaluation A is the most preferable. The results are shown in Table 1.
• HTP increase rate is 160% or more
• B HTP increase rate is 120% or more and less than 160%
• C HTP increase rate is 80% or more and less than 120%
• D HTP increase rate is 50% or more and less than 80%
• E HTP increase rate is 30% or more and less than 50%
• F HTP increase rate is less than 30%
• G HTP does not increase.
• the "substituent position of the substituent containing the group represented by the general formula (2)” is any of X 1 to X 8 in which the substitution position of the substituent containing the group represented by the general formula (2) is X 1 to X 8 . Indicates whether it is. In the table, “X” is omitted. That is, for example, "5, 6" in Example 1 means that the substitution positions of the substituents including the group represented by the general formula (2) are X 5 and X 6 . In Table 1, in the column "whether or not the substituent containing the group represented by the general formula (2) corresponds to the substituent containing the group represented by the general formula (3)", "A" is general.
• the substituent containing the group represented by (2) is represented, and at least one of the substituents containing the group represented by the general formula (2) is at the bonding position represented by * 1 in the substituent. It can be confirmed that the rate of increase in HTP is superior when it is directly connected to the Np ring. From the comparison of Example 1 and Example 9, Example 11 and Example 19 and Example 20, the substituent containing the group represented by the general formula (2) is formed in the Np ring at the bonding position represented by * 1. When directly connected, it can be confirmed that the rate of increase in HTP is superior.
• Comparative Example 1 did not satisfy the desired requirement because the comparative compound CE-1 had only one substituent containing a group represented by the general formula (2).
• Comparative Examples 2 and 3 since the two hydrogen atoms on the double bond in the comparative compounds CE-2 and CE-3 are on different sides with respect to the axis of the double bond (comparative compound CE). -2, CE-3 corresponds to the transformer structure), did not meet the desired requirements.
• Surfactant S-1 is a compound described in Japanese Patent No. 5774518 and has the following structure.
• a polyimide alignment film material SE-130 (manufactured by Nissan Chemical Industries, Ltd.) was applied onto the washed glass substrate to form a coating film. After firing the obtained coating film, a substrate with an alignment film was produced by rubbing treatment. A composition layer was formed by spin-coating 40 ⁇ L of the above-mentioned liquid crystal composition on the rubbing-treated surface of the alignment film under the conditions of a rotation speed of 1500 rpm for 10 seconds, and dried (aged) at 90 ° C. for 1 minute. The liquid crystal compounds in the composition layer were oriented (in other words, in the state of the cholesteric liquid crystal phase).
• the composition layer in which the liquid crystal compound is oriented light having a wavelength of 365 nm is emitted from a light source (UVP, 2UV, transilluminator) at 3.0 mW / cm 2 through a mask having an opening. Irradiation was performed for 30 seconds at the irradiation intensity of (corresponding to the process of changing HTP). Due to the difference between the opening and the non-opening of the mask, the composition layer is in a state in which there are a portion irradiated with light having a wavelength of 365 nm and a portion not irradiated with light. Subsequently, the composition layer was aged at 90 ° C. for 1 minute to adjust the orientation of the liquid crystal compound.
• a light source UVP, 2UV, transilluminator
• the composition layer is cured by irradiating the composition layer with ultraviolet rays (manufactured by HOYA-SCHOTT, EXCURE 3000-W, 315 nm) at an irradiation amount of 500 mJ / cm 2 at 25 ° C. in a nitrogen atmosphere with the mask removed.
• the treatment was carried out to obtain a reflective film (corresponding to a layer formed by immobilizing a cholesteric liquid crystal phase).
• the obtained reflective film has a short wavelength at a portion irradiated with light having a wavelength of 365 nm and a long wavelength reflection at a portion not irradiated, and the selective reflection wavelengths are different (the pitch of the spiral of the cholesteric layer is different). confirmed.

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