Method for producing reaction mixture composition, mixture composition, and method for producing mixture composition

Abstract

To achieve an increase in the relative yield of a specific structural isomer in a liquid crystal compound having structural isomers.SOLUTION: The method for producing reaction mixture composition includes a step of reacting a compound represented by Formula (1) with a compound represented by Formula (2) using an organic solvent having a dielectric constant of 30 or more in the presence of a basic compound, thereby obtaining a reaction mixture composition containing a compound represented by Formula (3) and a compound represented by Formula (4), wherein, in area percentage values measured by liquid chromatography for the compounds represented by Formula (3) and Formula (4) in the reaction mixture composition, a value of Formula (3) / (Formula (3)+Formula (4)) is 0.75 or more and less than 0.95, or a value of Formula (4) / (Formula (3)+Formula (4)) is 0.75 or more and less than 0.95. A-Ar-A (1), HO-Ar-OH (2), A-Ar-OH (3), HO-Ar-A (4)SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a method for producing a reactive mixture composition, a mixture composition, and a method for producing a mixture composition. [Background technology]

[0002] Patent Document 1 discloses a liquid crystal compound A-Ar-B obtained by a coupling reaction between a compound constituting a core portion (Ar) and a compound having a structure that will become a side chain portion (A, B). Patent Document 2 also discloses a liquid crystal compound having a similar structure.

[0003] When the compound constituting the core has an asymmetric structure and the two compounds having different structures that form the side chains, the products of the coupling reaction are two structural isomers, i.e., liquid crystal compounds A-Ar-B and B-Ar-A. These structural isomers are known to have different solubility and optical properties. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2019 / 160025 [Patent Document 2] Japanese Patent Application Laid-Open No. 2024-30442 Summary of the Invention [Problem to be solved by the invention]

[0005] There is a demand for utilizing one particular one of these structural isomers in order to obtain desired properties. [Means for solving the problem]

[0006] The present invention includes the following inventions. [Invention 1] The method includes a step of reacting a compound represented by formula (1) with a compound represented by formula (2) in the presence of a basic compound using an organic solvent having a dielectric constant of 30 or more to obtain a reaction mixture composition containing a compound represented by formula (3) and a compound represented by formula (4), A method for producing a reaction mixture composition, wherein, in the area percentage values ​​of the compound represented by formula (3) and the compound represented by formula (4) in the reaction mixture composition measured by liquid chromatography, the value of formula (3) / (formula (3) + formula (4)) is 0.75 or more and less than 0.95, or the value of formula (4) / (formula (3) + formula (4)) is 0.75 or more and less than 0.95.

[0007] A-Ar-A (1) HO-Ar-OH (2) A-Ar-OH (3) HO-Ar-A (4) [A in formula (1), formula (3) and formula (4) is represented by the following formula (5): *-D 1 -(A 1 -E 1 )m-SP 1 -L 1 (5) is expressed as In formula (5), * represents the bonding position with Ar in formula (1), formula (3), or formula (4), m represents an integer of 1 or greater, D 1 represents -C(=O)-O- or -OC(=O)-; E 1 is a single bond, or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 -, or a divalent linking group consisting of two or more thereof, R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; when m is an integer of 2 or more, a plurality of E 1 may be the same or different, A1 represents a divalent aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 6 or more carbon atoms which may have a substituent, and when m is an integer of 2 or more, a plurality of A 1 may be the same or different, SP 1 represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, a linear or branched alkynylene group having 2 to 20 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the alkylene group, the alkenylene group, or the alkynylene group is substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, and Q represents a substituent, L 1 represents a monovalent organic group, Ar in the formulas (1), (2), (3) and (4) is represented by the following formulas (Ar-1) to (Ar-6):

[0008] [ka]

[0009] [In formulas (Ar-1) to (Ar-6), *D 1 Represents the join with; Q 1 is -S-, -O- or -NR 6 - represents R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent, Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; W 1 and W 2 each independently represents -O-, -S-, -CO-, or -NR 6 - represents R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; Y 1represents an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group, Y 2 represents a CN group or an alkyl group having 1 to 12 carbon atoms which may have a substituent, wherein a hydrogen atom contained in the alkyl group is optionally substituted with a halogen atom, and wherein —CH— contained in the alkyl group is optionally substituted with —O—, —CO—, —O—CO— or —CO—O—; Z 1 , Z 2 and Z 3 each independently represents a hydrogen atom, an aliphatic hydrocarbon group or alkoxy group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -NR 6 R 7 or -SR 6 represents Z 1 and Z 2 may be bonded to each other to form an aromatic ring or an aromatic heterocycle, R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Z 4 represents an aliphatic hydrocarbon group or alkoxy group having 2 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -NR 6 R 7 or -SR 6 represents R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Ax represents an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ax and Ay may be bonded to form a ring; Y 3 and Y 4are each independently represented by the following formula (Y 3 -1):

[0010] [ka]

[0011] (Formula (Y 3 -1) Medium, R Y1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is 3 and the substituent X 3 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one -CH2- or two or more non-adjacent -CH2- groups each independently represent -O-, -S-, -CO-, - represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, and any hydrogen atom in the alkyl group may be substituted by a fluorine atom, or -B 31 -F 31 -P 31 (wherein B 31 -CR 8 R 9 -, -CH2-CH2-, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C(=S)-O-, -OC(=S)-, -OC(=S)-O-, -CO-NR 8 -, -NR 8 represents -CO-, -O-CH2-, -CH2-O-, -S-CH2-, -CH2-S- or a single bond, and R 8 and R 9each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; F 31 represents an alkanediyl group having 1 to 12 carbon atoms, and a hydrogen atom contained in the alkanediyl group is represented by -OR 10 or may be substituted with a halogen atom, R 10 represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom, and -CH2- contained in the alkanediyl group may be substituted with -O- or -CO-; P 31 represents a hydrogen atom or a polymerizable group), U 1 represents an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group, any carbon atom of which may be substituted with a heteroatom, and the aromatic hydrocarbon group is substituted with one or more of the above-mentioned substituents X 3 may be substituted by; T 1 -O-, -S-, -COO-, -OCO-, -OCO-O-, -NU 2 -,-N=CU 2 -,-CO-NU 2 -, -OCO-NU 2 - or O-NU 2 - represents U 2 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom), or (E 31 -A 31 ) q -B 31 -F 31 -P 31 and the alkyl group, the cycloalkyl group, the cycloalkenyl group and the aromatic hydrocarbon group are each unsubstituted or substituted with one or more substituents X 3the alkyl group is optionally substituted by the cycloalkyl group or cycloalkenyl group, and one -CH2- or two or more non-adjacent -CH2- in the alkyl group are each independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO2-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-; one -CH2- or two or more non-adjacent -CH2- in the cycloalkyl group or cycloalkenyl group are each independently replaced by -O-, -CO-, -COO-, -OCO- or O-CO-O-; E 31 is the above B 31 is defined similarly to A 31 represents a divalent alicyclic hydrocarbon group having 3 to 16 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group or the aromatic hydrocarbon group is not substituted with a halogen atom, -R 11 , -OR 12 , optionally substituted with a cyano group or a nitro group, R 11 represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms, and R 12 represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom; B 31 , F 31 and P 31 are the B 31 , F 31 and P 31 wherein q represents an integer of 0 to 4; 31 and / or A 31 When there are multiple U, they may be the same or different. 1 and U 2 and may be bonded to form a ring.) A group represented by any one of the following.] [Invention 2] The method for producing a reaction mixture composition according to [Invention 1], wherein the total area percentage value of the compound represented by formula (3) and the compound represented by formula (4) contained in the reaction mixture composition, as measured by liquid chromatography, is more than 50% and less than 98% based on the total area values ​​of the compound represented by formula (1), the compound represented by formula (2), the compound represented by formula (3), and the compound represented by formula (4) contained in the reaction mixture composition.

[0012] [Invention 3] A mixed composition comprising a compound represented by formula (7-1), a compound represented by formula (7-2), and at least one of a compound represented by formula (1) and a compound represented by formula (8), A-Ar-A (1) A-Ar-B (7-1) B-Ar-A (7-2) B-Ar-B (8) A mixed composition in which, when the sum of the area percentage value of the compound represented by formula (7-1) measured by liquid chromatography and the area percentage value of the compound represented by formula (7-2) measured by liquid chromatography is taken as 100%, the ratio of one structural isomer of the compound represented by formula (7-1) and the compound represented by formula (7-2) contained in the mixed composition is more than 75% but less than 95%.

[0013] [A in formula (1), formula (7-1) and formula (7-2) is the following formula (5): *-D 1 -(A 1 -E 1 )m-SP 1 -L 1 (5) is expressed as B in the formula (7-1), the formula (7-2), and the formula (8) is represented by the following formula (6): *-D 2 -(A 2 -E 2 )n-SP 2 -L 2 (6) is expressed as In formula (5) and formula (6), * represents the bonding position with Ar in formula (1), formula (7-1), formula (7-2) or formula (8), m and n each independently represent an integer of 1 or more; D 1 and D 2 each independently represents -C(=O)-O- or -OC(=O)-; E 1 and E 2 are each independently a single bond, or -CO-, -O-, -S-, -C(=S)-, or -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 -, or a divalent linking group consisting of two or more thereof, R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; when m is an integer of 2 or more, a plurality of E 1 may be the same or different, and when n is an integer of 2 or more, there may be a plurality of E 2 may be the same or different, A 1 and A 2 each independently represents a divalent aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 6 or more carbon atoms which may have a substituent, and when m is an integer of 2 or more, a plurality of A 1 may be the same or different, and when n is an integer of 2 or more, there may be a plurality of A 2 may be the same or different, SP 1 and SP 2each independently represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, a linear or branched alkynylene group having 2 to 20 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the alkylene group, the alkenylene group, or the alkynylene group is substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, and Q represents a substituent; L 1 and L 2 each independently represents a monovalent organic group; L 1 and L 2 at least one of the groups is a polymerizable group, A and B are different from each other, Ar in the formula (1), formula (7-1), formula (7-2) and formula (8) is represented by the following formulae (Ar-1) to (Ar-6):

[0014] [ka]

[0015] [In formulas (Ar-1) to (Ar-6), *D 1 or D 2 Represents the join with; Q 1 is -S-, -O- or -NR 6 - represents R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent, Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; W 1 and W 2 each independently represents -O-, -S-, -CO-, or -NR 6 - represents R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; Y 1 represents an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group, Y2 represents a CN group or an alkyl group having 1 to 12 carbon atoms which may have a substituent, wherein a hydrogen atom contained in the alkyl group is optionally substituted with a halogen atom, and wherein —CH— contained in the alkyl group is optionally substituted with —O—, —CO—, —O—CO— or —CO—O—; Z 1 , Z 2 and Z 3 each independently represents a hydrogen atom, an aliphatic hydrocarbon group or alkoxy group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -NR 6 R 7 or -SR 6 represents Z 1 and Z 2 may be bonded to each other to form an aromatic ring or an aromatic heterocycle, R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Z 4 represents an aliphatic hydrocarbon group or alkoxy group having 2 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -NR 6 R 7 or -SR 6 represents R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Ax represents an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ax and Ay may be bonded to form a ring; Y 3 and Y 4 are each independently represented by the following formula (Y 3 -1):

[0016] [ka]

[0017] (Formula (Y 3 -1) Medium, R Y1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is 3 and the substituent X 3 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one -CH2- or two or more non-adjacent -CH2- groups each independently represent -O-, -S-, -CO-, - represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, and any hydrogen atom in the alkyl group may be substituted by a fluorine atom, or -B 31 -F 31 -P 31 (wherein B 31 -CR 8 R 9 -, -CH2-CH2-, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C(=S)-O-, -OC(=S)-, -OC(=S)-O-, -CO-NR 8 -, -NR 8 represents -CO-, -O-CH2-, -CH2-O-, -S-CH2-, -CH2-S- or a single bond, and R 8 and R 9 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; F 31represents an alkanediyl group having 1 to 12 carbon atoms, and a hydrogen atom contained in the alkanediyl group is represented by -OR 10 or may be substituted with a halogen atom, R 10 represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom, and -CH2- contained in the alkanediyl group may be substituted with -O- or -CO-; P 31 represents a hydrogen atom or a polymerizable group), U 1 represents an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group, any carbon atom of which may be substituted with a heteroatom, and the aromatic hydrocarbon group is substituted with one or more of the above-mentioned substituents X 3 may be substituted by; T 1 -O-, -S-, -COO-, -OCO-, -OCO-O-, -NU 2 -,-N=CU 2 -,-CO-NU 2 -, -OCO-NU 2 - or O-NU 2 - represents U 2 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom), or (E 31 -A 31 ) q -B 31 -F 31 -P 31 and the alkyl group, the cycloalkyl group, the cycloalkenyl group and the aromatic hydrocarbon group are each unsubstituted or substituted with one or more substituents X 3the alkyl group is optionally substituted by the cycloalkyl group or cycloalkenyl group, and one -CH2- or two or more non-adjacent -CH2- in the alkyl group are each independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO2-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-; one -CH2- or two or more non-adjacent -CH2- in the cycloalkyl group or cycloalkenyl group are each independently replaced by -O-, -CO-, -COO-, -OCO- or O-CO-O-; E 31 is the above B 31 is defined similarly to A 31 represents a divalent alicyclic hydrocarbon group having 3 to 16 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group or the aromatic hydrocarbon group is not substituted with a halogen atom, -R 11 , -OR 12 , optionally substituted with a cyano group or a nitro group, R 11 represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms, and R 12 represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom; B 31 , F 31 and P 31 are the B 31 , F 31 and P 31 wherein q represents an integer of 0 to 4; 31 and / or A 31 When there are multiple U, they may be the same or different. 1 and U 2 and may be bonded to form a ring.) A group represented by any one of the following.] [Invention 4] The mixed composition according to [Invention 3], wherein the total area percentage value of the compound represented by formula (7-1) and the compound represented by formula (7-2), as measured by liquid chromatography, is more than 50% and less than 98% based on the total area values ​​of the compound represented by formula (1), the compound represented by formula (7-1), the compound represented by formula (7-2), and the compound represented by formula (8) contained in the mixed composition.

[0018] [Invention 5] A in equation (5) 1 The method for producing a reaction mixture composition according to [Invention 1] or [Invention 2], wherein

[0019] [Invention 6] L in equation (5) 1 The method for producing a reaction mixture composition according to [Invention 1] or [Invention 2], wherein

[0020] [Invention 7] A in equation (5) 1 and A in equation (6) 2 are each independently a 1,4-cyclohexanediyl group or a 1,4-phenylenediyl group.

[0021] [Invention 8] L in equation (5) 1 and L in equation (6) 2 and each of the groups is an acryloyloxy group.

[0022] [Invention 9] A method for producing a mixed composition using a reaction mixture composition produced by the method for producing a reaction mixture composition according to any one of [Invention 1], [Invention 2], [Invention 5] and [Invention 6], A method for producing a mixed composition, the method comprising the steps of: mixing the reaction mixture composition with a compound represented by formula (9); reacting the compound represented by formula (3) with the compound represented by formula (9) to produce a compound represented by formula (7-1); and reacting the compound represented by formula (4) with the compound represented by formula (9) to produce a compound represented by formula (7-2), thereby obtaining a mixed composition containing the compound represented by formula (7-1) and the compound represented by formula (7-2).

[0023] HOOC-(A 2 -E 2 )n-SP 2 -L 2 (9) A-Ar-B (7-1) B-Ar-A (7-2) [In formula (9), n represents an integer of 1 or more, E 2 is a single bond, or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 -, or a divalent linking group consisting of two or more thereof, R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; when n is an integer of 2 or more, a plurality of E 2 may be the same or different, A 2 represents a divalent aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 6 or more carbon atoms which may have a substituent, and when n is an integer of 2 or more, a plurality of A 2 may be the same or different, SP 2represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, a linear or branched alkynylene group having 2 to 20 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the alkylene group, the alkenylene group, or the alkynylene group is substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, and Q represents a substituent, L 2 represents a monovalent organic group, provided that L 2 and L in Eq. (5) 1 at least one of the groups is a polymerizable group, A and Ar in formula (7-1) and formula (7-2) have the same meanings as A and Ar in formula (1), respectively (however, * in formulas (Ar-1) to (Ar-6) represents D 1 or D 2 (representing the bond with B is the following formula (6): *-D 2 -(A 2 -E 2 )n-SP 2 -L 2 (6) is expressed as In formula (6), * represents the bonding position with Ar in formula (7-1) or formula (7-2), D 2 represents -C(=O)-O- or -OC(=O)-; A 2 , E 2 ,n,SP 2 and L 2 are A in equation (9), respectively. 2 , E 2 ,n,SP 2 and L 2 and A and B are different from each other.] [Effects of the Invention]

[0024] A mixed composition containing preferentially one specific structural isomer of the polymerizable liquid crystal compound is obtained. DETAILED DESCRIPTION OF THE INVENTION

[0025] Hereinafter, embodiments of the present invention will be described in detail. Note that the scope of the present invention is not limited to the embodiments described here, and various modifications can be made without departing from the spirit of the present invention.

[0026] <Mixed composition> The mixed composition of the present invention is a mixed composition of liquid crystal compounds containing a compound represented by formula (7-1) (hereinafter also referred to as "compound (7-1)"), a compound represented by formula (7-2) (hereinafter also referred to as "compound (7-2)"), and at least one of a compound represented by formula (1) (hereinafter also referred to as "compound (1)") and a compound represented by formula (8) (hereinafter also referred to as "compound (8)"). The mixed composition of the present invention, which contains compound (7-1) having an asymmetric structure centered on the group represented by Ar in formula (7-1) and compound (7-2) having an asymmetric structure centered on the group represented by Ar in formula (7-2) in a specific quantitative relationship, together with compound (1) having a symmetric structure centered on Ar in formula (1) and / or compound (8) having a symmetric structure centered on Ar in formula (8), has a low phase transition temperature to a liquid crystal phase. This allows film formation without exposure to high temperature conditions, and the resulting optical film is expected to have even better optical properties.

[0027] The method for producing a mixed composition of the present invention can produce a mixed composition in which the total area percentage of the compound represented by formula (7-1) and the compound represented by formula (7-2), measured by liquid chromatography, is greater than 50% and less than 98% based on the total area percentage of the compound represented by formula (1), the compound represented by formula (7-1), the compound represented by formula (7-2), and the compound represented by formula (8) contained in the mixed composition. That is, a mixed composition containing a large amount of the asymmetric structural isomers, compound (7-1) and compound (7-2), can be produced. Furthermore, the method for producing a mixed composition of the present invention can produce a mixed composition containing a selectively large amount of one of the structural isomers, compound (7-1) or compound (7-2), by using an organic solvent with a dielectric constant of 30 or higher. In a mixed composition containing such structural isomers, the optical and mechanical properties of the mixed composition can change depending on which structural isomer is contained in a larger amount. According to the present invention, a mixed composition having specific optical and mechanical properties can be produced by selectively containing a large amount of one of the structural isomers described above.

[0028] In this specification, even if the structure of Ar in formula (1) is asymmetric, the compound is said to be symmetrical in the sense that the structure represented by A in formula (1) bonded to Ar is the same on both sides with Ar at the center. Similarly, even if the structure of Ar in formula (8) is asymmetric, the compound is said to be symmetrical in the sense that the structure represented by B in formula (8) bonded to Ar is the same on both sides with Ar at the center.

[0029] The compound (7-1) contained in the mixed composition of the present invention has a structure represented by formula (7-1). The compound (7-2) contained in the mixed composition of the present invention has a structure represented by formula (7-2).

[0030] A-Ar-B (7-1) B-Ar-A (7-2) Compound (7-1) has an asymmetric structure with the group represented by Ar in formula (7-1) at the center, in which the structures of the two side chains bonded to Ar (i.e., A and B in formula (7-1)) are different from each other. Similarly, compound (7-2) has an asymmetric structure with the group represented by Ar in formula (7-2) at the center, in which the structures of the two side chains bonded to Ar are different from each other. Hereinafter, the group represented by Ar in formula (7-1) and formula (7-2) may also be referred to as the core part, and the two side chains bonded to the core part may also be referred to as the mesogen part. More specifically, A in formula (7-1) and formula (7-2) is a group represented by formula (5): *-D 1 -(A 1 -E 1 )m-SP 1 -L 1 (5) B in formula (7-1) and formula (7-2) has a structure represented by formula (6): *-D 2 -(A 2 -E 2 )n-SP 2 -L 2 (6) Formula (7-1) and Formula (7-2) have a structure represented by the following formula: At least one structure contained in each of the side chains of A and B is an asymmetric structure.

[0031] In formula (5) and formula (6), m and n each independently represent an integer of 1 or more. m and n each independently represent an integer of preferably 1 to 3, more preferably 1 or 2. In formula (5) and formula (6), m and n may be the same or different. In compound (7-1) and compound (7-2), the ring structure contained in A in formula (7-1) and formula (7-2) (i.e., A in formula (5)) 1 and the number of ring structures contained in B in formula (7-1) and formula (7-2) (i.e., A in formula (6) 2The difference between the number of m and n and the number of m and n (groups represented by the formula (7-1) and (7-2)) is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. In a preferred embodiment of the present invention, one of m and n is 1, and the other is 2 or 3. Furthermore, in a more preferred embodiment, one of m and n is 1, and the other is 2. Compounds (7-1) and (7-2), which have an asymmetric structure, can effectively lower the phase transition temperature in a mixed composition with compound (1) and / or compound (8), which have a highly symmetric structure. Although this is not necessarily limited, compounds with a symmetric structure tend to have excellent crystallinity because they can be arranged regularly, and therefore tend to have a relatively high phase transition temperature. When a compound with an asymmetric structure is added to such a compound with a symmetric structure, it is thought that the compound with an asymmetric structure affects the ease of arrangement of the compound, acting in a direction that reduces crystallinity and thereby lowers the phase transition temperature. On the other hand, the higher the ratio of compounds with asymmetric structures relative to compounds with symmetric structures, the more difficult it becomes to maintain the high alignment order achieved by compounds with symmetric structures, and optical properties tend to deteriorate. Therefore, in the past, asymmetric compounds have been difficult to use as the main component of a cured liquid crystal layer (e.g., more than 50 mass % of the total mass of the (polymerizable) liquid crystal compounds constituting the cured liquid crystal film). Although the mechanism is unclear, the mixed composition of the present invention, which contains a high ratio of compounds (7-1) and (7-2) with asymmetric structures, can achieve a significant reduction in phase transition temperature while ensuring excellent optical properties that are ideal for optical films such as retardation plates. Furthermore, in one embodiment of the present invention, when a compound having an asymmetric structure in terms of the number of ring structures contained in each of the side chains A and B is blended, the effect is more likely to be pronounced compared to when a compound having an asymmetric structure (e.g., a case where the asymmetric structure is caused by differences in the length of the alkyl chain) is blended, even though the number of ring structures in each side chain is the same.

[0032] In equations (5) and (6), D 1 and D 2 each independently represents -C(=O)-O- or -OC(=O)-. In formula (5) and formula (6), E 1 and E 2 are each independently a single bond, or -CO-, -O-, -S-, -C(=S)-, or -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 -, or a divalent linking group consisting of two or more thereof, R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms. Examples of the divalent linking group formed by a combination of two or more groups include -CO-O-, -O-CO-, -C(=S)O-, -O-CO-O-, -CR 1 R 2 -CR 1 R 2 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-CR 1 R 2 -,-CO-O-CR 1 R 2 -, -O-CO-CR 1 R 2 -, -CR 1 R 2 -O-CO-CR 1 R 2 -, -CR 1 R 2 -CO-O-CR 1 R 2 -, -NR 5 -CR 1 R 2 -, and -CO-NR 5 - and others. E 1 and E 2 are each independently preferably a single bond, —O—, —CO—O—, —O—CO—, —O—CO—O—, or —CO—NR 5 -, more preferably a single bond, -O-, -CO-O-, or -O-CO-. When m is an integer of 2 or more, a plurality of E 1 may be the same or different, and when n is an integer of 2 or more, there may be a plurality of E 2may be the same or different. When m and n are each an integer of 2 or more, SP 1 or SP 2 E binds to 1 and E 2 are each preferably a single bond, or -O-, -CO-O-, -O-CO-, -C(=S)O-, -O-CO-O-, *-CR 1 R 2 -O-, *-CR 1 R 2 -O-CO- or -NR 5 - and (* is A 1 or A 2 is more preferably a single bond, -O-, -CO-O- or -O-CO-.

[0033] In formula (5) and formula (6), A 1 and A 2 each independently represents a divalent aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 6 or more carbon atoms which may have a substituent. 1 and A 2 Examples of divalent aromatic hydrocarbon groups having 6 or more carbon atoms represented by the formula (a) include aromatic hydrocarbon groups having 6 to 20 carbon atoms, and specific examples thereof include aromatic hydrocarbon groups represented by the formula (a-1) to (a-8) below.

[0034] [ka]

[0035] The above A 1 and A 2 Examples of the divalent alicyclic hydrocarbon group having 6 or more carbon atoms represented by the formula (a) include alicyclic hydrocarbon groups having 6 to 16 carbon atoms, and specific examples include alicyclic hydrocarbon groups represented by the following formulas (a-9) to (a-11).

[0036] [ka]

[0037] Examples of the substituent that the aromatic hydrocarbon group and the alicyclic hydrocarbon group may have include alkyl groups having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; alkoxy groups having 1 to 4 carbon atoms, such as a methoxy group and an ethoxy group; fluoroalkyl groups having 1 to 4 carbon atoms, such as a trifluoromethyl group; a cyano group; a nitro group; and halogen atoms, such as a fluorine atom, a chlorine atom, and a bromine atom.

[0038] A 1 and A 2 is preferably an unsubstituted divalent aromatic hydrocarbon group having 6 to 20 carbon atoms or an unsubstituted alicyclic hydrocarbon group having 6 to 16 carbon atoms, and more preferably a 1,4-cyclohexanediyl group or a 1,4-phenylenediyl group. When m is an integer of 2 or more, a plurality of A 1 may be the same or different, and when n is an integer of 2 or more, there may be a plurality of A 2 may be the same or different.

[0039] In the present invention, A 1 and A 2 are each independently a 1,4-cyclohexanediyl group or a 1,4-phenylenediyl group. 1 is preferably a 1,4-cyclohexanediyl group, and when n is 1, A 2 is preferably a 1,4-cyclohexanediyl group. 1 and D 2 A binds to 1 and A 2 is preferably a 1,4-cyclohexanediyl group or a 1,4-phenylenediyl group, and more preferably a 1,4-cyclohexanediyl group. 1 and D 2 A binds to 1 and A 2 is a 1,4-cyclohexanediyl group,1 and / or A 2 E adjacent to 1 or E 2 A binds to 1 and / or A 2 is a 1,4-phenylenediyl group.

[0040] In equations (5) and (6), SP 1 and SP 2 SP each independently represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, a linear or branched alkynylene group having 2 to 20 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the alkylene group, alkenylene group, or alkynylene group is replaced with -O-, -S-, -NH-, -N(Q)- (Q is a substituent), or -CO-. 1 and SP 2 Examples of linear or branched alkylene groups having 1 to 20 carbon atoms represented by the formula (I) include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group, and a heptylene group. Examples of linear or branched alkenylene groups having 2 to 20 carbon atoms include an ethenylene group, a propenylene group, and a butenylene group. Examples of linear or branched alkynylene groups having 2 to 20 carbon atoms include an ethynylene group.

[0041] SP 1 and SP 2 may be a divalent linking group in which one or more of the -CH2- groups constituting the alkylene group, alkenylene group, and alkynylene group are substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. The substituent represented by Q includes, for example, 1 and A 2 Examples of the substituent that can be possessed by the aromatic hydrocarbon group or alicyclic hydrocarbon group represented by the following formula include the same substituents as those exemplified above.

[0042] SP 1 and SP 2are each independently preferably a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, or a linear or branched alkynylene group having 2 to 20 carbon atoms, more preferably a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, a linear or branched alkenylene group having 2 to 12 carbon atoms, or a linear or branched alkynylene group having 2 to 12 carbon atoms, and even more preferably a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms.

[0043] In formula (5) and formula (6), L 1 and L 2 each independently represents a monovalent organic group; L 1 and L 2 At least one of the groups L is a polymerizable group. Examples of the monovalent organic group include an alkyl group, an aryl group, and a heteroaryl group. 1 or L 2 The monovalent organic group represented by the formula (I) is preferably an alkyl group, more preferably an alkyl group having 1 to 13 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. The alkyl group may be linear, branched, or cyclic, and is preferably linear.

[0044] L 1 and L 2 The polymerizable group represented by the formula (7-1) may be any group capable of polymerizing compound (7-1) and compound (7-2), and specific examples thereof include a vinyl group, a p-stilbene group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, a carboxyl group, a methylcarbonyl group, a hydroxyl group, an amide group, an alkylamino group having 1 to 4 carbon atoms, an amino group, an epoxy group, an oxetanyl group, an aldehyde group, an isocyanate group, a thioisocyanate group, etc. In addition, such a polymerizable group may be a group in which the above-exemplified groups and SP 1 or SP 2 An ether bond or an ester bond may be included to connect L 1 and L 2As the polymerizable group represented by the formula (I), for example, a radically polymerizable group or a cationically polymerizable group suitable for photopolymerization is preferred, and an acryloyl group, a methcroyl group, an acryloyloxy group, or a methacryloyloxy group is particularly preferred in terms of ease of handling and ease of production, and an acryloyl group or an acryloyloxy group is more preferred in terms of high polymerizability, with an acryloyloxy group being even more preferred.

[0045] From the viewpoint that the reactivity (polymerizability) of the compound (7-1) and the compound (7-2) is likely to be high, L 1 and L 2 are preferably both polymerizable groups, and L 1 and L 2 are more preferably an acryloyl group, a methacryloyl group, an acryloyloxy group, or a methacryloyloxy group, and L 1 and L 2 It is more preferable that both of are acryloyloxy groups.

[0046] Specific examples of the structure represented by formula (5) and the structure represented by formula (6) include structures represented by formulas (R-1) to (R-138) below. In the formulas, * represents the bonding position to the group Ar, and n may be, for example, an integer of 1 to 20. The cyclohexane ring may be either a trans or cis form, but is preferably a trans form. Compounds (7-1) and (7-2) have asymmetric structures with the group Ar at the center. Therefore, for example, the structure represented by formula (5) (i.e., A in formulas (7-1) and (7-2)) may have a structure represented by any of formulas (R-1) to (R-31) below, which has one ring structure, and the structure represented by formula (6) (i.e., B in formulas (7-1) and (7-2)) may have a structure represented by any of formulas (R-32) to (R-73) below, which has two ring structures, or a structure represented by any of formulas (R-74) to (R-138) below, which has three ring structures. Alternatively, for example, the structure represented by formula (5) may have a structure represented by any one of the following formulae (R-32) to (R-73) having two ring structures, and the structure represented by formula (6) may have a structure represented by any one of the following formulae (R-74) to (R-138) having three ring structures.

[0047] [ka]

[0048] [ka]

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] In addition, the terminal portion of each of the above structures (for example, -SP in formula (5)) 1 -L 1 The moiety corresponding to (a) may have any of the following structures:

[0062] [ka]

[0063] In a preferred embodiment of the present invention, D in formula (5) constituting compound (7-1) and compound (7-2) 1 , SP 1 and L 1 Each structure represented by the formula (6) constituting the compound (7-1) and the compound (7-2) is represented by the formula (6). 2 , SP 2 and L 2 That is, the structure A represented by formula (5) and the structure B represented by formula (6) are the same as the structures represented by -(A 1 -E 1 )m- and the structure represented by -(A 2 -E 2 )n-. When compound (7-1) and compound (7-2) have such a structure, the molecular structures of compound (7-1) and compound (7-2) contained in the liquid crystal mixture and compound (1) and / or compound (8) are similar or approximate to each other, and the phase transition temperature of the liquid crystal mixture is likely to be effectively lowered. Furthermore, in a liquid crystal mixture in which the molecular structures of the contained compounds are similar or approximate to each other, the liquid crystal compounds have less influence on each other when aligning and are likely to be oriented with high alignment order, which makes it more likely that the optical properties of the resulting liquid crystal cured film are improved.

[0064] In formula (5) and formula (6), the group is represented by any one of the following formulas (Ar-1) to (Ar-6). The groups represented by formulas (Ar-1) to (Ar-5) are common in that they give the polymerizable liquid crystal compounds represented by formulas (7-1) and (7-2) a bulky molecular structure in the direction intersecting with the long axis direction, the absorption wavelength in the short axis direction becomes long, and the retardation generated by the aligned liquid crystal molecules usually has reverse wavelength dispersion. The group represented by formula (Ar-6) often causes the retardation generated by the aligned liquid crystal molecules to have positive wavelength dispersion.

[0065] [ka]

[0066] The total number N of π electrons contained in the divalent linking group containing an aromatic hydrocarbon ring or an aromatic heterocycle represented by formula (Ar-1) to formula (Ar-6) π is preferably 12 or more, more preferably 16 or more, even more preferably 18 or more, and particularly preferably 20 or more. It is also preferably less than 36, more preferably 32 or less, even more preferably 30 or less, and particularly preferably 26 or less.

[0067] In formulas (Ar-1) to (Ar-6), * represents D in formula (5) or formula (6). 1 or D 2 Represents the connection part with. In formula (Ar-1), Q 1 is -S-, -O- or -NR 6 - represents R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent. In formulas (Ar-3) and (Ar-4), Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.

[0068] In formula (Ar-2), W 1 and W 2 each independently represents -O-, -S-, -CO-, or -NR 6 - represents R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.

[0069] In formula (Ar-1), Y 1 represents an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group. 2represents a CN group or an alkyl group having 1 to 12 carbon atoms which may have a substituent. Here, a hydrogen atom contained in the alkyl group may be substituted with a halogen atom, and -CH2- contained in the alkyl group may be substituted with -O-, -CO-, -O-CO- or -CO-O-.

[0070] In formulas (Ar-1) to (Ar-6), Z 1 , Z 2 and Z 3 each independently represents a hydrogen atom, an aliphatic hydrocarbon group or alkoxy group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -NR 6 R 7 or -SR 6 represents Z 1 and Z 2 may be bonded to each other to form an aromatic ring or a heteroaromatic ring. 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0071] In formula (Ar-6), Z 4 represents an aliphatic hydrocarbon group or alkoxy group having 2 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -NR 6 R 7 or -SR 6 Represents R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0072] In formulas (Ar-3) and (Ar-4), Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ax and Ay may be bonded to form a ring.

[0073] In formula (Ar-1), Y 1 is preferably an aromatic hydrocarbon group or aromatic heterocyclic group which may have a substituent, and is more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent. The aromatic hydrocarbon group or aromatic heterocyclic group which may have a substituent is preferably an optionally substituted polycyclic aromatic hydrocarbon group or polycyclic aromatic heterocyclic group. In this specification, "polycyclic aromatic hydrocarbon group" means an aromatic hydrocarbon group having at least two aromatic rings, and examples thereof include a fused aromatic hydrocarbon group formed by condensing two or more aromatic rings and an aromatic hydrocarbon group formed by bonding two or more aromatic rings. The term "polycyclic aromatic heterocyclic group" refers to an aromatic heterocyclic group having at least one heteroaromatic ring and at least one ring selected from the group consisting of aromatic rings and heteroaromatic rings, and includes aromatic heterocyclic groups formed by condensing one or more aromatic heterocyclic rings with one or more rings selected from the group consisting of aromatic rings and heteroaromatic rings, and aromatic heterocyclic groups formed by bonding at least one heteroaromatic ring with at least one ring selected from the group consisting of aromatic rings and heteroaromatic rings.

[0074] Examples of the substituent that the aromatic hydrocarbon group or aromatic heterocyclic group may have include a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, a nitroso group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a carboxy group, a fluoroalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylsulfanyl group having 1 to 6 carbon atoms, an N-alkylamino group having 1 to 4 carbon atoms, an N,N-dialkylamino group having 2 to 8 carbon atoms, a sulfamoyl group, an N-alkylsulfamoyl group having 1 to 6 carbon atoms, and an N,N-dialkylsulfamoyl group having 2 to 12 carbon atoms.

[0075] The groups represented by formulae (Ar-1) to (Ar-4) may be groups described in, for example, JP-A Nos. 2011-207765, 2008-107767, and WO 2014 / 010325.

[0076] In formula (Ar-5), Y 3 and Y 4 are each independently represented by the following formula (Y 3 -1):

[0077] [ka]

[0078] The group is selected from groups represented by the following formula: Formula (Y 3 -1) Medium, R Y1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. The alkyl group may have one or more substituents X 3 may be substituted by

[0079] Substituent X 3 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one -CH2- or two or more non-adjacent -CH2- groups each independently represent -O-, -S-, -CO-, - represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, and any hydrogen atom in the alkyl group may be substituted by a fluorine atom, or -B 31 -F 31 -P 31 B may be a group represented by the following formula: 31 -CR 8 R 9-, -CH2-CH2-, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C(=S)-O-, -OC(=S)-, -OC(=S)-O-, -CO-NR 8 -, -NR 8 represents -CO-, -O-CH2-, -CH2-O-, -S-CH2-, -CH2-S- or a single bond, and R 8 and R 9 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; F 31 represents an alkanediyl group having 1 to 12 carbon atoms, and a hydrogen atom contained in the alkanediyl group is represented by -OR 10 or may be substituted with a halogen atom, R 10 represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom, and -CH2- contained in the alkanediyl group may be substituted with -O- or -CO-; P 31 represents a hydrogen atom or a polymerizable group.

[0080] Substituent X 3 is preferably a fluorine atom, a chlorine atom, —CF3, —OCF3 or a cyano group. Y1 is preferably an alkyl group having 1 to 6 carbon atoms that is unsubstituted or substituted with a hydrogen atom or one or more fluorine atoms, and more preferably a hydrogen atom.

[0081] Formula (Y 3 -1) Medium, U 1 represents an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group. Any carbon atom in the aromatic hydrocarbon group may be substituted with a heteroatom, and U 1 is an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. 3 may be substituted by

[0082] U 1In terms of improving wavelength dispersion, U is preferably an organic group having an aromatic heterocycle in which one or more carbon atoms are substituted with a heteroatom. 1 is more preferably an organic group having an aromatic heterocycle that is a condensed ring of a 5-membered ring and a 6-membered ring, since the oriented liquid crystal molecules have good wavelength dispersion and exhibit high birefringence.

[0083] Formula (Y 3 -1) Medium, T 1 -O-, -S-, -COO-, -OCO-, -OCO-O-, -NU 2 -,-N=CU 2 -,-CO-NU 2 -, -OCO-NU 2 - or O-NU 2 - represents U 2 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom), or (E 31 -A 31 ) q -B 31 -F 31 -P 31 The alkyl group, the cycloalkyl group, the cycloalkenyl group and the aromatic hydrocarbon group are each unsubstituted or substituted with one or more substituents X 3The alkyl group may be substituted with the cycloalkyl group or cycloalkenyl group. One -CH2- or two or more non-adjacent -CH2- groups in the alkyl group may each independently be replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO2-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-, and one -CH2- or two or more non-adjacent -CH2- groups in the cycloalkyl group or cycloalkenyl group may each independently be replaced by -O-, -CO-, -COO-, -OCO-, or O-CO-O-. 31 is the above B 31 is defined similarly to A 31 represents a divalent alicyclic hydrocarbon group having 3 to 16 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group or the aromatic hydrocarbon group is not substituted with a halogen atom, -R 11 , -OR 12 , optionally substituted with a cyano group or a nitro group. 11 represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms, and R 12 represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom. 31 , F 31 and P 31 are the B 31 , F 31 and P 31 and q represents an integer of 0 to 4. 31 and / or A 31 When there are a plurality of, they may be the same or different.

[0084] T 1 -O-, -S-, -N=CU are preferred because of their good birefringence and ease of synthesis. 2 -or- NU 2- is preferred, and -O-, -S- or -NU is preferred because it is easy to improve the wavelength dispersion and birefringence of the aligned liquid crystal molecules. 2 - is more preferable.

[0085] U 2 is one or more of the substituents X 3 and one -CH2- or two or more non-adjacent -CH2- may each independently be replaced by -O-, -CO-, -COO-, -OCO- or -O-CO-O-.

[0086] Among them, U 2 From the viewpoints of birefringence and solvent solubility, it is more preferable that is a linear alkyl group having 1 to 20 carbon atoms in which a hydrogen atom may be substituted with a fluorine atom, and in which one -CH2- or two or more non-adjacent -CH2- groups may each independently be substituted with -O-, -CO-, -COO-, or -OCO-.

[0087] U 1 and U 2 may be bonded to form a ring. In that case, for example, -NU 1 U 2 or -N=CU 1 U 2 Examples of the cyclic group include a cyclic group represented by the following formula: Among formulas (Ar-1) to (Ar-6), a group represented by any of formulas (Ar-1) to (Ar-5) is preferred, a group represented by any of formulas (Ar-1), (Ar-3) and (Ar-4) is more preferred, and a group represented by formula (Ar-1) is even more preferred.

[0088] The compound (7-1) and the compound (7-2) are usually polymerizable liquid crystal compounds, and it is preferable that the liquid crystal cured film obtained by orienting and polymerizing the compound (7-1) alone and the liquid crystal cured film obtained by orienting and polymerizing the compound (7-2) alone are polymerizable liquid crystal compounds that exhibit so-called reverse wavelength dispersion.

[0089] The mixed composition of the present invention contains at least one of compound (1) and compound (8) in addition to compound (7-1) and compound (7-2). Compound (1) is a compound having a structure represented by A in formula (7-1) or formula (7-2) (i.e., a structure represented by formula (5)) on both sides of Ar, which constitutes compound (7-1) or compound (7-2), and has a bilaterally symmetrical structure centered on Ar. Similarly, compound (8) is a compound having a structure represented by B in formula (7-1) or formula (7-2) (i.e., a structure represented by formula (6)) on both sides of Ar, which has a bilaterally symmetrical structure centered on Ar. Compound (1) and compound (8) are each preferably polymerizable compounds. Compound (1) and compound (8) may each be a liquid crystal compound or a non-liquid crystal compound. However, from the viewpoint of improving optical properties, it is preferable that at least one of compounds (1) and (8) contained in addition to compounds (7-1) and (7-2) is a liquid crystal compound. It is more preferable that all of the compounds corresponding to compounds (1), (7-1), (7-2), and (8) contained in the mixed composition are liquid crystal compounds. It is even more preferable that all of the compounds corresponding to compounds (1), (7-1), (7-2), and (8) are polymerizable liquid crystal compounds. The mixed composition of the present invention may contain a plurality of polymerizable liquid crystal compounds corresponding to compounds (1), (7-1), (7-2), and / or (8).

[0090] In the mixed composition of the present invention, the total area percentage of compounds (7-1) and (7-2) measured by liquid chromatography is, for example, greater than 50% but less than 98% of the total area values ​​of compounds (1), (7-1), (7-2), and (8) contained in the mixed composition. Here, in this specification, "area percentage" refers to the ratio of the peak area of ​​the target compound to the total peak area of ​​compounds (1), (7-1), (7-2), and (8). When the total area percentage of compounds (7-1) and (7-2) exceeds 50%, the phase transition temperature of the mixed composition is likely to be sufficiently lowered, allowing for the production of a cured liquid crystal film at a lower processing temperature. This suppresses damage and alignment defects caused by heating at high temperatures, enabling film production without reducing the inherent optical properties of the polymerizable liquid crystal compound used, resulting in a cured liquid crystal film with excellent optical properties. Although asymmetric liquid crystal compounds may be disadvantageous compared to symmetric liquid crystal compounds, for example, in terms of wavelength dispersion (particularly reverse wavelength dispersion) of the resulting cured liquid crystal film, by containing asymmetric compounds (7-1) and (7-2) in an area percentage of more than 50% and symmetric compounds (1) and / or (8) in a specific balance as described above, it is possible to impart optical properties superior to those of a cured liquid crystal film obtained by orienting and polymerizing a single symmetric compound, which is generally believed to exhibit stronger reverse wavelength dispersion. From the viewpoint of further enhancing such effects, in the present invention, the total area percentage of compounds (7-1) and (7-2) is preferably 55% or more, more preferably 60% or more, even more preferably 65% ​​or more, particularly preferably 70% or more, and may be, for example, 75% or more. The upper limit of the total area percentage value of the compound (7-1) and the compound (7-2) may be, for example, 90% or less, or 85% or less.Furthermore, it is particularly preferable that the area percentage value of either compound (7-1) or compound (7-2) is more than 50% and less than 98%, and the lower limit of this range may be 55% or more, more preferably 60% or more, even more preferably 65% ​​or more, particularly preferably 70% or more, for example, 75% or more.

[0091] In addition, when the mixed composition of the present invention contains multiple compounds corresponding to compound (1), compound (7-1), compound (7-2), and / or compound (8), the total area percentage value of compound (7-1) and compound (7-2) is calculated based on the peak area of ​​all compounds (7-1) and all compounds (7-2) relative to the total peak area of ​​all compounds (1), all compounds (7-1), all compounds (7-2), and all compounds (8). The area percentage value can be calculated based on the peak area measured by liquid chromatography, and in detail, can be measured and calculated by the method described in the Examples below.

[0092] The mixed composition of the present invention contains a combination of compound (7-1) and compound (7-2) with compound (1) and / or compound (8), and the total area percentage of compound (7-1) and compound (7-2) exceeds 50%, thereby significantly reducing the phase transition temperature to a liquid crystal phase compared to, for example, when a compound having a highly symmetric structure, such as compound (1) or compound (8), is used alone, or when the area percentage of a compound having a highly symmetric structure exceeds 50%. For example, when a liquid crystal phase transition temperature (nematic phase transition temperature) of a mixed composition of compound (7-1) and compound (7-2) with compound (1) and / or compound (8) constituting the mixed composition of the present invention is a liquid crystal mixture capable of producing a liquid crystal cured film exhibiting reverse wavelength dispersion, the liquid crystal phase transition temperature (nematic phase transition temperature) is preferably 120°C or lower, more preferably 115°C or lower, and may be, for example, 110°C or lower, or even 105°C or lower. The phase transition temperature (nematic phase transition temperature) of the mixed composition is usually 25°C or higher, preferably 40°C or higher, and more preferably 50°C or higher.

[0093] In one embodiment of the present invention, the mixed composition of the present invention can reduce the phase transition temperature (nematic phase transition temperature) of compound (1) or compound (8) alone by preferably 5° C. or more, more preferably 10° C. or more, even more preferably 15° C. or more, and particularly preferably 20° C. or more, and may in some cases be reduced by, for example, 30° C. or more, or even 35° C. or more. Furthermore, compared to a mixed composition containing compound (1) and / or compound (8) together with compound (7-1) and compound (7-2), but in which the total area percentage of compound (7-1) and compound (7-2) is 50% or less, the phase transition temperature can be reduced by preferably 5° C. or more, more preferably 10° C. or more, and may in some cases be reduced by, for example, 15° C. or more, or even 20° C. or more.

[0094] In the present invention, the liquid crystal phase transition temperature can be measured using, for example, a polarizing microscope equipped with a temperature control stage, a differential scanning calorimeter (DSC), a thermogravimetric differential thermal analyzer (TG-DTA), etc. When a plurality of liquid crystal compounds are contained, the phase transition temperature refers to a temperature measured using a mixture of liquid crystal compounds obtained by mixing compounds corresponding to Compound (1), Compound (7-1), Compound (7-2), and Compound (8) constituting the mixed composition with all liquid crystal compounds other than the compounds corresponding to Compound (1), Compound (7-1), Compound (7-2), and Compound (8) in the same ratio as the composition in the mixed composition.

[0095] The mixed composition of the present invention may contain liquid crystal compounds other than Compound (1), Compound (7-1), Compound (7-2), and Compound (8) (hereinafter also referred to as "other liquid crystal compounds"), so long as the total area percentage of Compound (7-1) and Compound (7-2) exceeds 50% and the effects of the present invention are obtained. Examples of such liquid crystal compounds include the compounds described in Sections 3.2 Nonchiral Rod-Shaped Liquid Crystal Molecules and 3.3 Chiral Rod-Shaped Liquid Crystal Molecules of Chapter 3, Molecular Structure and Liquid Crystallinity, of "Liquid Crystal Handbook" (edited by the Liquid Crystal Handbook Editorial Committee, published by Maruzen Co., Ltd. on October 30, 2000), the compounds described in JP 2010-31223 A, and polymerizable liquid crystal compounds that can exhibit reverse wavelength dispersion when formed into a liquid crystal cured film or polymerizable liquid crystal compounds that can exhibit positive wavelength dispersion, as described in JP 2011-207765 A and Japanese Patent No. 5962760 A.

[0096] When the mixed composition of the present invention contains other liquid crystal compounds, the content of the other liquid crystal compounds is preferably 15 parts by mass or less, more preferably 10 parts by mass or less, and even more preferably 5 parts by mass or less, relative to 100 parts by mass of the total of compound (1), compound (7-1), compound (7-2), and compound (8). In particular, if the content of liquid crystal compounds having molecular structures significantly different from those of compound (1), compound (7-1), compound (7-2), and / or compound (8) is too high, phase separation is likely to occur, which may impair the appearance or make it difficult to ensure high optical properties. Therefore, it is preferable that the liquid crystal compounds constituting the mixed composition of the present invention are substantially composed of liquid crystal compounds having structures similar to those of compound (7-1) and compound (7-2).

[0097] The term "similar" refers to a case where the compound has a structure common to, for example, side chain A (i.e., the structure represented by formula (5)), side chain B (i.e., the structure represented by formula (6)), and the moiety represented by Ar in compound (7-1). The term "substantially composed of" refers to the content of compounds corresponding to compounds (1), (7-1), (7-2), and (8) being 90% by mass or more relative to the total mass of the compounds corresponding to compounds (1), (7-1), (7-2), and (8) and all other liquid crystal compounds contained in the mixed composition. In one embodiment of the present invention, the mixed composition does not contain any liquid crystal compounds other than compounds corresponding to compounds (1), (7-1), (7-2), and / or (8).

[0098] The mixed composition of the present invention may consist solely of compound (7-1) and compound (7-2), and compound (1) and / or compound (8). From the viewpoint of improving reactivity and handleability when polymerizing compound (7-1) and compound (7-2), and compound (1) and / or compound (8) to obtain a liquid crystal cured film, the mixed composition of the present invention may further contain components such as a photopolymerization initiator, an organic solvent, a polymerization inhibitor, a photosensitizer, and a leveling agent in addition to compound (1), compound (7-1), compound (7-2), and compound (8).

[0099] When the mixed composition of the present invention contains, in addition to Compound (1), Compound (7-1), Compound (7-2), and Compound (8), additional components as described above, the total mass of Compound (1), Compound (7-1), Compound (7-2), and Compound (8) in the mixed composition of the present invention may be, for example, 70 to 99.5 parts by mass, preferably 80 to 99 parts by mass, more preferably 85 to 98 parts by mass, and even more preferably 90 to 95 parts by mass, per 100 parts by mass of the solid content of the mixed composition. A total mass of Compound (1), Compound (7-1), Compound (7-2), and Compound (8) within the above range is advantageous in terms of the alignment of the resulting liquid crystal cured film. The solid content of the mixed composition refers to the amount of all components in the mixed composition excluding volatile components such as organic solvents.

[0100] The mixed composition of the present invention may contain a polymerization initiator. The polymerization initiator is a compound capable of initiating a polymerization reaction of a polymerizable compound or the like, and is preferably a photopolymerization initiator that generates active radicals by the action of light, from the viewpoint of being independent of the phase state of the thermotropic liquid crystal.

[0101] As the photopolymerization initiator, any known photopolymerization initiator can be used as long as it is a compound that can initiate the polymerization reaction of the polymerizable compound.Specific examples include photopolymerization initiators that can generate active radicals or acids under the action of light, and among these, photopolymerization initiators that generate radicals under the action of light are preferred.The photopolymerization initiators can be used alone or in combination of two or more.

[0102] As the photopolymerization initiator, known photopolymerization initiators can be used. For example, photopolymerization initiators that generate active radicals include self-cleavage-type benzoin compounds, acetophenone compounds, hydroxyacetophenone compounds, α-aminoacetophenone compounds, oxime ester compounds, acylphosphine oxide compounds, and azo compounds. Hydrogen-abstraction-type benzophenone compounds, alkylphenone compounds, benzoin ether compounds, benzil ketal compounds, dibenzosuberone compounds, anthraquinone compounds, xanthone compounds, thioxanthone compounds, halogenoacetophenone compounds, dialkoxyacetophenone compounds, halogenobisimidazole compounds, halogenotriazine compounds, and triazine compounds. As photopolymerization initiators that generate acids, iodonium salts and sulfonium salts can be used. From the viewpoint of excellent reaction efficiency at low temperatures, self-cleavage type photopolymerization initiators are preferred, and acetophenone compounds, hydroxyacetophenone compounds, α-aminoacetophenone compounds, and oxime ester compounds are particularly preferred.

[0103] The content of the photopolymerization initiator is usually 0.1 to 20 parts by mass, preferably 1 to 15 parts by mass, and more preferably 1 to 10 parts by mass, relative to 100 parts by mass of the total amount of polymerizable compounds contained in the mixed composition. Within the above range, the reaction of the polymerizable group proceeds sufficiently and the alignment of the liquid crystal compound is unlikely to be disturbed. In this specification, the term "polymerizable compound" refers to a compound having at least one polymerizable group.

[0104] In the present invention, the mixed composition preferably contains an organic solvent because it is usually applied to a substrate, etc. in a state of being dissolved in the organic solvent. The organic solvent is preferably a solvent that can dissolve compound (7-1), compound (7-2), and compound (1) and / or compound (8), etc., and is also preferably a solvent that is inert to the polymerization reaction of these compounds. Examples of organic solvents include alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, ethylene glycol methyl ether, ethylene glycol butyl ether, 1-methoxy-2-propanol, 2-butoxyethanol, and propylene glycol monomethyl ether; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate, and ethyl lactate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone, and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane, and heptane; alicyclic hydrocarbon solvents such as ethylcyclohexane; aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; ether solvents such as tetrahydrofuran and dimethoxyethane; chlorine-containing solvents such as chloroform and chlorobenzene; and amide solvents such as dimethylacetamide, dimethylformamide, N-methyl-2-pyrrolidone (NMP), and 1,3-dimethyl-2-imidazolidinone. These organic solvents can be used alone or in combination of two or more. Among these, alcohol solvents, ester solvents, ketone solvents, chlorine-containing solvents, amide solvents and aromatic hydrocarbon solvents are more preferred.

[0105] The content of the organic solvent in the mixed composition is preferably 50 to 98 parts by mass, more preferably 50 to 95 parts by mass, per 100 parts by mass of the mixed composition. Therefore, the solid content per 100 parts by mass of the mixed composition is preferably 2 to 50 parts by mass, more preferably 5 to 50 parts by mass. When the solid content is 50 parts by mass or less, the viscosity of the mixed composition is low, which tends to result in a film having a substantially uniform thickness upon application and less unevenness. The solid content can be appropriately determined taking into consideration the thickness of the cured film to be produced.

[0106] In order to stably proceed with the polymerization reaction, the mixed composition may contain a polymerization inhibitor, which can control the degree of progress of the polymerization reaction of the polymerizable compound.

[0107] Examples of the polymerization inhibitor include radical scavengers such as hydroquinone, alkoxy group-containing hydroquinone, alkoxy group-containing catechol (e.g., butylcatechol, etc.), pyrogallol, and 2,2,6,6-tetramethyl-1-piperidinyloxy radical; thiophenols; β-naphthylamines, and β-naphthols.

[0108] The content of the polymerization inhibitor is usually 0.01 to 10 parts by mass, preferably 0.1 to 5 parts by mass, and more preferably 0.1 to 3 parts by mass, relative to 100 parts by mass of the total amount of the polymerizable compounds. When the content of the polymerization inhibitor is within the above range, polymerization can be carried out without disturbing the alignment of the polymerizable liquid crystal compound.

[0109] The mixed composition may contain a sensitizer. The sensitizer is preferably a photosensitizer. Examples of the sensitizer include xanthone compounds such as xanthone and thioxanthone (e.g., 2,4-diethylthioxanthone, 2-isopropylthioxanthone, etc.); anthracene compounds such as anthracene and alkoxy group-containing anthracene (e.g., dibutoxyanthracene, etc.); phenothiazine, rubrene, etc.

[0110] When the mixed composition contains a sensitizer, the polymerization reaction of the polymerizable compound contained in the mixed composition can be further accelerated. The content of the photosensitizer is usually 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, and more preferably 0.1 to 3 parts by mass, relative to 100 parts by mass of the total amount of the polymerizable compound.

[0111] The mixed composition may contain a leveling agent. The leveling agent is an additive that adjusts the fluidity of the composition and has the function of making the film obtained by applying the composition flatter, and examples thereof include organic modified silicone oil-based, polyacrylate-based, and perfluoroalkyl-based leveling agents. Among them, polyacrylate-based and perfluoroalkyl-based leveling agents are preferred.

[0112] The content of the leveling agent in the mixed composition is preferably 0.01 to 5 parts by mass, more preferably 0.05 to 3 parts by mass, relative to 100 parts by mass of the total amount of the polymerizable compounds. When the content of the leveling agent is within the above range, it becomes easy to horizontally align the compounds (7-1) and (7-2), and the like, and the obtained cured film tends to be smoother. When the content of the leveling agent relative to the polymerizable compounds exceeds the above range, the obtained cured film tends to be uneven. The mixed composition may contain two or more types of leveling agents.

[0113] <Method of manufacturing mixed composition> The mixed composition of the present invention can be prepared by adding additives such as a solvent, a photopolymerization initiator, a polymerization inhibitor, a photosensitizer, or a leveling agent to compound (7-1) and compound (7-2), and compound (1) and / or compound (8), as necessary, and stirring and mixing them at a predetermined temperature.

[0114] Compound (1), compound (7-1), compound (7-2), and compound (8), which constitute the mixed composition of the present invention, can be produced by appropriately combining, depending on their structures, known organic synthesis reactions (e.g., condensation reaction, esterification reaction, Williamson reaction, Ullmann reaction, Wittig reaction, Schiff base formation reaction, benzylation reaction, Sonogashira reaction, Suzuki-Miyaura reaction, Negishi reaction, Kumada reaction, Hiyama reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, aldol reaction, etc.) described in Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, New Experimental Chemistry Course, etc. Specifically, for example, according to the method for producing a polymerizable liquid crystal compound described in JP-A-2010-31223, the desired compound (1), compound (7-1), compound (7-2), or compound (8) can be separately prepared by an esterification reaction between an alcohol compound and a carboxylic acid compound, each having a structure corresponding to the structure of the desired compound (1), compound (7-1), compound (7-2), or compound (8).

[0115] The mixed composition of the present invention containing compound (7-1) and compound (7-2) at an area percentage value of more than 50% can also be prepared by mixing compound (7-1) and compound (7-2) separately prepared by the above-mentioned method with compound (1) and / or compound (8) in a desired ratio such that the area percentage value of compound (7-1) and compound (7-2) exceeds 50%. However, the mixed composition of the present invention in which the total area percentage value of compound (7-1) and compound (7-2) having an asymmetric structure with Ar at the center exceeds 50% can be prepared, for example, by mixing compound (1) and compound (7-2): HO-Ar-OH (2) [Ar in formula (2) has the same meaning as Ar in formula (1) above.] The reaction mixture composition can be prepared as an intermediate material by a method including a step of reacting a compound represented by formula (3) (hereinafter also referred to as "compound (3)") with a compound represented by formula (4) (hereinafter also referred to as "compound (4)") in the presence of a basic compound to obtain a reaction mixture composition containing a compound represented by formula (3) (hereinafter also referred to as "compound (3)") and a compound represented by formula (4) (hereinafter also referred to as "compound (4)").

[0116] A-Ar-OH (3) HO-Ar-A (4) [A and Ar in formula (3) and formula (4) have the same meanings as A and Ar in formula (1) above, respectively.] When compound (7-1) and compound (7-2), which have been prepared separately, are mixed with compound (1) and / or compound (8), compound (7-1) and compound (7-2) must be isolated. For example, when compound (7-1) and compound (7-2) are produced by the conventional production method described below, theoretically, less than 50% of the compound is obtained. Therefore, an even more complicated purification step is required to isolate compound (7-1) and compound (7-2). The method of the present invention does not require such a complicated purification step, and therefore the desired mixed composition can be produced more efficiently. Furthermore, when an alcohol compound capable of forming the core portion (the structure corresponding to Ar in formulas (7-1) and (7-2)) of compounds (7-1) and (7-2), such as compound (2), is combined by an esterification reaction with two or more carboxylic acid compounds having structures that form the side chain portions (mesogenic portions) of compounds (7-1) and (7-2) and that have different structures, a mixed composition in which the total area percentage of compounds (7-1) and (7-2) exceeds 50% is theoretically not obtained. However, the method including the step of obtaining a reaction mixed composition containing compounds (3) and (4) from compounds (1) and (2) makes it easy to simply and efficiently prepare a mixed preparation containing compounds (7-1) and (7-2) at a high ratio of more than 50%.

[0117] The present invention includes a step (hereinafter also referred to as "step (i)") of reacting a compound represented by formula (1) with a compound represented by formula (2) in the presence of a basic compound to obtain a reaction mixture composition containing a compound represented by formula (3) and a compound represented by formula (4). Step (i) can also be said to be a method for producing a reaction mixture composition.

[0118] In the method for producing a reaction mixture composition according to the present invention, the area percentage values ​​of compound (3) and compound (4) in the reaction mixture composition, as measured by liquid chromatography, are such that the value of compound (3) / (compound (3) + compound (4)) is 0.75 or more but less than 0.95, or the value of compound (4) / (compound (3) + compound (4)) is 0.75 or more but less than 0.95. The content of compound (3) or compound (4) in the reaction mixture composition can be adjusted by adjusting the core structure (the structure corresponding to Ar in formulas (1) and (2)) of compound (1) and compound (2) used in step (i), the reaction conditions in step (i), the solvent and additives used in step (i), and other factors. By obtaining a reaction mixture composition that selectively contains a higher amount of either compound (3) or compound (4), it is possible to produce a mixture composition that selectively contains a higher amount of a specific structural isomer of compound (7-1) or compound (7-2), as described below.

[0119] The method for producing a reaction mixture composition includes, for example, a compound represented by formula (3) and a compound represented by formula (4), wherein the total area percentage value of the compound represented by formula (3) and the compound represented by formula (4) in the reaction mixture composition, as measured by liquid chromatography, is more than 50% and less than 98% based on the total area values ​​of the compound represented by formula (1), the compound represented by formula (2), the compound represented by formula (3), and the compound represented by formula (4) contained in the reaction mixture composition.

[0120] Step (i) will now be described in detail. A-Ar-A (1) HO-Ar-OH (2) A-Ar-OH (3) HO-Ar-A (4) A and Ar in formula (1), formula (2), formula (3) and formula (4) have the same meanings as A and Ar in formula (1) above, respectively, and are determined depending on the final desired structures of compound (7-1) and compound (7-2).

[0121] Compound (1) can be produced by synthesizing and bonding compounds by appropriately combining known organic synthesis reactions depending on the structure of the compound. Specifically, for example, it can be prepared from a compound having a structure corresponding to the structure of the desired compound (1) according to the method described in JP-A-2010-31223.

[0122] The alcohol compound (2) may be any compound in which two hydroxy groups are bonded to Ar corresponding to the group Ar in the desired compound (3) and compound (4).

[0123] In step (i), the reaction between compound (1) and compound (2) is carried out in the presence of a basic compound. Although not necessarily limited to the following reaction, in the presence of a basic compound, a hydrogen atom of one of the hydroxyl groups (-OH) bonded to Ar in compound (2) is abstracted to form a transition state, resulting in one molecule of OH-Ar-O. - attacks one molecule of compound (1) and one side chain A (i.e., *-D 1 -(A 1 -E 1 )m-SP 1 -L 1 〕(-OCO- or -COO-)D 1 It is presumed that a nucleophilic substitution reaction occurs in relation to the Ar in compound (2), resulting in the production of two molecules of compound (3). The hydrogen atom of one of the hydroxyl groups (-OH) bonded to Ar in compound (2) is abstracted, resulting in a transition state, and one molecule of - O-Ar-OH nucleophilically attacks one molecule of compound (1), and one side chain A (i.e., *-D 1 -(A 1 -E 1 )m-SP1 -L 1 〕(-OCO- or -COO-)D 1 It is presumed that a nucleophilic substitution reaction occurs between the two molecules of compound (4).

[0124] The reaction yields two molecules of compound (3), two molecules of compound (4), or one molecule of compound (3) and one molecule of compound (4) from one molecule of symmetrical compound (1). Compound (3) and compound (4) are suitable intermediates for producing compounds (7-1) and (7-2). By reacting a reaction mixture composition containing compounds (3) and (4) with a compound represented by formula (9) (described below) having a structure corresponding to side chain B, which is different from side chain A in compound (1), the mixture composition of the present invention containing compounds (7-1) and (7-2) having a bilaterally asymmetric structure with a high area percentage of more than 50% can be produced simply and efficiently.

[0125] In step (i), the basic compound may be appropriately selected from known basic compounds, as long as it is capable of abstracting hydrogen from one of the hydroxy groups bonded to Ar in compound (2) and initiating and proceeding the nucleophilic substitution reaction between compound (1) and compound (2). The basic compound may be an inorganic basic compound or an organic basic compound, and may be used alone or in combination of two or more. From the viewpoints of more efficiently proceeding the reaction between compound (1) and compound (2) and facilitating the production of a reaction mixture composition containing compound (3) and compound (4) in high proportions, the basic compound in step (i) is preferably a basic compound having an ionization constant (pKa) of 7 or more.

[0126] The ionization constant (pKa), also known as the acid dissociation constant, is the equilibrium constant Ka in the dissociation reaction in which hydrogen ions are released from an acid, expressed as a negative common logarithm. The ionization constant of a base is the ionization constant (acid dissociation constant) of the conjugate acid of that base. In this specification, the ionization constant of a basic compound is determined by the pH-dependent solubility method.

[0127] The basic compound used in step (i) preferably has a pKa of 7.5 or more, more preferably 8 or more, and even more preferably 9 or more, and although the upper limit is not particularly limited, it is usually 17 or less, preferably 15 or less, and more preferably 13.5 or less. When the pKa of the basic compound is within the above range, the reaction between compound (1) and compound (2) tends to proceed efficiently, and a reaction mixture composition containing compound (3) and compound (4) in high proportions is easily obtained.

[0128] Specific examples of the basic compound used in step (i) include N,N-dimethylaminopyridine (pKa: 9.7), diazabicycloundecene (pKa: 13.5), triethanolamine (pKa: 10.75), N-methylmorpholine (pKa: 7.38), 1,4-diazabicyclo[2.2.2]octane (pKa: 8.7), N,N-diisopropylethylamine (pKa: 10.98), potassium tert-butoxide (pKa: 17), etc. Among these, N,N-dimethylaminopyridine, diazabicycloundecene, and triethanolamine are preferred, and N,N-dimethylaminopyridine and diazabicycloundecene are more preferred.

[0129] The amount of the basic compound used in step (i) may be appropriately determined depending on the type of basic compound used, the desired ratio of compound (3) and compound (4) in the reaction mixture composition, and other factors. For example, the amount is preferably 0.01 moles or more, more preferably 0.05 moles or more, even more preferably 0.1 moles or more, and is preferably 10 moles or less, more preferably 5 moles or less, even more preferably 3 moles or less, and particularly preferably 1 mole or less, per mole of compound (2). When the amount of the basic compound is within the above range, the reaction between compound (1) and compound (2) proceeds efficiently, making it easier to obtain a reaction mixture composition containing a high proportion of compound (3) and compound (4). When multiple basic compounds are used, it is preferable that the total content of basic compounds having a pKa of 7 or more be within the above range.

[0130] In step (i), the reaction between compound (1) and compound (2) is carried out in the presence of an organic solvent having a dielectric constant of 30 or greater. The solvent used in step (i) may be the same as or different from the organic solvent constituting the mixed composition of the present invention, as long as it has a dielectric constant of 30 or greater. Examples of organic solvents having a dielectric constant of 30 or greater include N-methyl-2-pyrrolidone (NMP), dimethylacetamide (DMAc), dimethylformamide (DMF), dimethyl sulfoxide, sulfolane, and acetonitrile. From the viewpoint of the solubility of compound (1), compound (2), and the resulting compounds (3) and (4), N-methyl-2-pyrrolidone (NMP) and dimethylacetamide (DMAc) are preferred as the solvent used in step (i). The above solvents may be used alone or in combination.

[0131] The amount of the solvent used is not particularly limited, but is, for example, 1 part by mass or more, preferably 1.2 parts by mass or more, relative to 1 part by mass of compound (1) so that each compound can be sufficiently dissolved and the reaction can proceed efficiently, and is usually 50 parts by mass or less, preferably 30 parts by mass or less, more preferably 20 parts by mass or less, to avoid using an excessive amount of solvent.

[0132] The reaction between compound (1) and compound (2) may be carried out using an additive, if necessary. For example, the reaction may be carried out in the presence of a polymerization inhibitor to prevent polymerization. Examples of polymerization inhibitors include 2,6-di-tert-butyl-p-cresol (BHT), 2,2'-methylenebis(6-tert-butyl-p-cresol), triphenyl phosphite, tris(nonylphenyl) phosphite, and phenothiazine. When a polymerization inhibitor is used, the amount added is preferably 0.01 moles or more, more preferably 0.05 moles or more, and preferably 1.0 molar equivalent or less, per mole of compound (1).

[0133] The reaction of compound (1) with compound (2) can be carried out in a state where compound (1), compound (2), a basic compound, and, if necessary, a solvent, additives, etc. are mixed. The conditions for the reaction can be appropriately determined depending on the types of compounds used, the scale of the reaction, and the like.

[0134] In one embodiment of the production method of the present invention, the reaction temperature of compound (1) and compound (2) is preferably 0° C. to 80° C., more preferably 20° C. to 60° C. When the reaction temperature is within the above range, the reaction of compound (1) and compound (2) proceeds easily, and the target compound can be obtained more safely due to the mild conditions.

[0135] The reaction time may be determined depending on the type and ratio of compounds used, the reaction temperature, and other factors. Depending on factors such as the reaction scale, the reaction time is preferably 10 minutes to 48 hours, and more preferably 10 minutes to 24 hours. In the present invention, the reaction time between compound (1) and compound (2) begins when compound (1), compound (2), and the basic compound begin to coexist, and ends when the reaction between compound (1) and compound (2) stops / completes. The progress of the reaction can be confirmed by analytical means such as high-performance liquid chromatography, thin-layer chromatography, or gas chromatography.

[0136] The structure of the resulting compound can be identified by measuring NMR spectrum, IR spectrum, mass spectrum, etc., elemental analysis, etc. The total area percentage of compounds (3) and (4) in the reaction mixture composition containing compounds (3) and (4) obtained in step (i), as measured by liquid chromatography, is preferably more than 50% and less than 98% based on the total area percentage of compounds (1), (2), (3), and (4) contained in the reaction mixture composition. When the reaction mixture composition contains compounds (3) and (4) in an amount greater than 50% in terms of total area percentage, the reaction mixture composition can be used as an intermediate material to obtain a mixture composition of the present invention containing more than 50% area percentage of compounds (7-1) and (7-2). By controlling the progress of the reaction between compound (1) and compound (2) in step (i) and adjusting the amounts of compound (1) and compound (2) in addition to compound (3) and compound (4) in the resulting reaction mixture composition, a mixture composition of the present invention containing a high proportion of compound (7-1) and compound (7-2) as well as the required amount of compound (1) and / or compound (8) can be obtained through step (ii) described below. The amounts of compound (3) and compound (4) contained in the reaction mixture composition can be appropriately determined depending on the blend ratio of compound (7-1) and compound (7-2) in the final desired mixture composition of the present invention containing compound (7-1) and compound (7-2), and may be, for example, 55% or more, 60% or more, 65% or more, or 70% or more, or may be, for example, 90% or less, or 85% or less. For example, the area percentage of either compound (3) or compound (4) may be greater than 50% and less than 98%, with the lower limit of this range being 55% or greater, more preferably 60% or greater, even more preferably 65% ​​or greater, and particularly preferably 70% or greater, for example, 75% or greater. For example, in a reaction mixture composition that can be used as an intermediate for a mixture composition in which the total area percentage of compounds (7-1) and (7-2) is 75%, the total area percentage content of compounds (3) and (4) is preferably 75% or greater. A reaction mixture composition containing compounds (3) and (4) in such a ratio is suitable as an intermediate material for obtaining the mixture composition of the present invention, which has a low phase transition temperature.The area percentage value can be calculated based on the peak area measured by liquid chromatography, in the same manner as described above for the mixed composition of the present invention.

[0137] A reaction mixture composition containing compound (3) and compound (4) obtained in step (i), and a compound of formula (9): HOOC-(A 2 -E 2 )n-SP 2 -L 2 (9) (hereinafter, also referred to as "compound (9)"), and reacting compound (3) and compound (4) with compound (9) (hereinafter, also referred to as "step (ii)"), the mixed composition of the present invention containing compound (7-1) and compound (7-2) can be produced. Step (i) and step (ii) can be carried out continuously, or, for example, the reaction mixture obtained in step (i) can be temporarily stored, and then step (ii) can be carried out discontinuously from step (i) (batch method). Carrying out step (i) and step (ii) continuously is preferable from the viewpoint of production efficiency and workability, for example, because purification and extraction operations are not necessary. Carrying out step (i) and step (ii) discontinuously is also preferable from the viewpoint of obtaining a high-purity product, for example, because the amount of impurities generated in step (i) carried over to step (ii) can be reduced.

[0138] A in equation (9) 2 , E 2 ,n,SP 2 and L 2 are the A in the above formula (6), respectively. 2 , E 2 ,n,SP 2 and L 2 and is determined depending on the final desired structures of the compound (7-1) and the compound (7-2).

[0139] Compound (9) can be produced by synthesizing and bonding compounds by appropriately combining known organic synthesis reactions depending on the structure of the compound. Specifically, for example, it can be prepared from a compound having a structure corresponding to the structure of the desired compound (9) according to the method described in JP-A-2010-31223.

[0140] The reaction of compound (3) and compound (4) with compound (9) in the reaction mixture is an esterification reaction, which is preferably carried out in the presence of a condensing agent. By carrying out the esterification reaction in the presence of a condensing agent, the esterification reaction can be carried out efficiently and quickly.

[0141] Examples of the condensing agent used in step (ii) include 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-para-toluenesulfonate, dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (water-soluble carbodiimide: commercially available as WSC), bis(2,6-diisopropyl) carbodiimide compounds such as bis(trimethylsilyl)carbodiimide and bis(trimethylsilyl)carbodiimide, 2-methyl-6-nitrobenzoic anhydride, 2,2'-carbonylbis-1H-imidazole, 1,1'-oxalyldiimidazole, diphenylphosphoryl azide, 1-(4-nitrobenzenesulfonyl)-1H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate ester, 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N,N',N'-tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate, N-(1,2,2,2-tetrachloroethoxycarbonyloxy)succinimide, N-carbobenzoxysuccinimide, O-(6-chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, O-(6-chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 2-bromo-1-ethylpyridinium tetrafluoroborate, 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate, 2-chloro-1-methylpyridinium iodide, 2-chloro-1-methylpyridinium para-toluenesulfonate, 2-fluoro-1-methylpyridinium para-toluenesulfonate, trichloroacetic acid pentachlorophenyl ester, and the like.From the viewpoints of reactivity, cost, and solvents that can be used, the condensing agent is preferably dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, bis(2,6-diisopropylphenyl)carbodiimide, bis(trimethylsilyl)carbodiimide, bisisopropylcarbodiimide, or 2,2'-carbonylbis-1H-imidazole.

[0142] The amount of the condensing agent used in the esterification reaction of compound (3) and compound (4) with compound (9) can be appropriately determined depending on the types of compound (3), compound (4), and compound (9), the type of condensing agent, etc. For example, it is usually 1.0 to 1.5 moles per mole of the mixture of compound (3) and compound (4).

[0143] The esterification reaction may be carried out in the presence of a catalyst. Examples of the catalyst include N,N-dimethylaminopyridine, N,N-dimethylaniline, and dimethylammonium pentafluorobenzenesulfonate. The amount of the catalyst used is preferably 0.01 to 0.5 moles per mole of the mixture of compound (3) and compound (4).

[0144] The esterification reaction of compound (3) and compound (4) with compound (9) in step (ii) is usually carried out in a solvent. The solvent may be the same as or different from the solvent used in step (i). From the viewpoints of reaction yield and productivity, the solvent used in step (ii) is preferably a non-polar organic solvent such as pentane, hexane, heptane, toluene, xylene, benzene, chlorobenzene, chloroform, or dichloromethane. These solvents may be used alone or in combination.

[0145] The amount of compound (9) used is preferably 0.5 to 2.5 mol, more preferably 0.75 to 2.0 mol, and even more preferably 1.0 to 1.3 mol, per mol of the mixture of compound (3) and compound (4), from the viewpoint of easily obtaining desired amounts of compound (7-1) and compound (7-2) in good yield.

[0146] The amount of the solvent used is not particularly limited, but is preferably 1 to 100 parts by mass, more preferably 5 to 70 parts by mass, and even more preferably 10 to 50 parts by mass, per 1 part by mass of the total of compound (3), compound (4), and compound (9).

[0147] The temperature of the esterification reaction in step (ii) is preferably -20 to 120°C, more preferably -20 to 60°C, and even more preferably -10 to 20°C, from the viewpoints of reaction yield and productivity. The time period for the esterification reaction is preferably 1 minute to 72 hours, more preferably 1 to 48 hours, and even more preferably 1 to 24 hours, from the viewpoints of reaction yield and productivity. In the present invention, the reaction time of compound (3) and compound (4) with compound (9) is defined as the start point when compound (3) and compound (4) begin to coexist with compound (9), and the end point is defined as the time period when the reaction of compound (3) and compound (4) with compound (9) is stopped / completed. The progress of the reaction can be confirmed by analytical means such as high-performance liquid chromatography, thin-layer chromatography, or gas chromatography.

[0148] The structure of the obtained compound can be identified by measurement of NMR spectrum, IR spectrum, mass spectrum, etc., elemental analysis, etc. After completion of the reaction, if necessary, treatments and operations that can be used in organic synthetic chemistry, such as post-treatments such as filtration, neutralization, extraction, and washing with water, and isolation treatments such as distillation and crystallization, can be carried out to obtain a mixed composition of the present invention containing compound (7-1) and compound (7-2) as a mixture of liquid crystal compounds. The mixed composition thus obtained can be used as a mixed composition for forming a retardation film by adding necessary components such as the organic solvent and photopolymerization initiator described above.

[0149] In the method for producing a mixed composition of the present invention, by adjusting the amount of compound (9) used in step (ii), the entire amount of compound (3) contained in the reaction mixture composition can react with compound (9). Similarly, the entire amount of compound (4) contained in the reaction mixture composition can react with compound (9). When the entire amounts of compound (3) and compound (4) react with compound (9), in the method for producing a mixed composition of the present invention, for example, the area percentage values ​​of compound (7-1) and compound (7-2) in the mixed composition measured by liquid chromatography are such that the value of compound (7-1) / (compound (7-1) + compound (7-2)) is 0.75 or more and less than 0.95, or the value of compound (7-2) / (compound (7-1) + compound (7-2)) is 0.75 or more and less than 0.95.

[0150] That is, in the mixed composition of the present invention, when the sum of the area percentage value of compound (7-1) measured by liquid chromatography and the area percentage value of compound (7-2) measured by liquid chromatography is taken as 100%, the proportion of one of the structural isomers of compound (7-1) and compound (7-2) contained in the mixed composition is greater than 75% and less than 95%. Thus, according to the method for producing a mixed composition of the present invention, a mixed composition can be produced that preferentially contains a specific structural isomer of compound (7-1) and compound (7-2) in a larger amount. The proportion of one of the structural isomers of compound (7-1) and compound (7-2) is preferably 80% or more. The upper limit of the proportion of one of the structural isomers of compound (7-1) and compound (7-2) may be, for example, 90% or less, or even 85% or less.

[0151] The method for producing the mixed composition of the present invention may involve carrying out the following steps (ib) and (ii-b) instead of the above steps (i) and (ii). Step (ib) is the same as step (i) except that a compound represented by formula (8) is used instead of the compound represented by formula (1). That is, step (ib) is a step in which a compound represented by formula (8) and a compound represented by formula (2) are reacted in the presence of a basic compound using an organic solvent having a dielectric constant of 30 or more.

[0152] In step (ib), a compound represented by formula (8) is reacted with a compound represented by formula (2) to obtain a reaction mixture composition containing a compound represented by the following formula (3-b) and a compound represented by formula (4-b).

[0153] B-Ar-OH (3-b) HO-Ar-B (4-b) [In formula (3-b) and formula (4-b), Ar and B have the same meanings as above, respectively.] In step (ib), in the area percentage values ​​of the compound represented by formula (3-b) and the compound represented by formula (4-b) in the reaction mixture composition measured by liquid chromatography, the value of formula (3-b) / (formula (3-b) + formula (4-b)) is 0.75 or more and less than 0.95, or the value of formula (4-b) / (formula (3-b) + formula (4-b)) is 0.75 or more and less than 0.95.

[0154] Step (ii-b) is the same as step (ii), except that the compound represented by formula (3) is replaced with the compound represented by formula (3-b), the compound represented by formula (4-b) is replaced with the compound represented by formula (4), and the compound represented by formula (10) is replaced with the compound represented by formula (9). That is, step (ii-b) is a process of reacting the compound represented by formula (3-b) with the compound represented by formula (10) to produce the compound represented by formula (7-2), and reacting the compound represented by formula (4-b) with the compound represented by formula (10) to produce the compound represented by formula (7-1), thereby obtaining a mixed composition containing the compound represented by formula (7-1) and the compound represented by formula (7-2). The mixed composition obtained by performing step (ii-b) may contain at least one of the compound represented by formula (1) and the compound represented by formula (8), in addition to the compound represented by formula (7-1) and the compound represented by formula (7-2).

[0155] HOOC-(A 1 -E 1 )m-SP 1 -L 1 (10) [In formula (10), all symbols have the same meanings as above.] Step (ib) and step (ii-b) may be carried out continuously or discontinuously, similarly to the case where step (i) and step (ii) are carried out above.

[0156] It can also be said that the above steps (ib) and (ii-b) are the same as steps (i) and (ii) in which the structure represented by A in each compound is interchanged with the structure represented by B. It can also be said that step (ib) is the same as step (i) in which the structure represented by A in each compound is interchanged with the structure represented by B in the compound in step (ii).

[0157] <Retardation film> Because the mixed composition of the present invention has a low phase transition temperature, use of the mixed composition of the present invention makes it possible to form a film at low temperatures without deteriorating the optical properties that the liquid crystal compound can inherently exhibit, making it easier to obtain a cured liquid crystal film with excellent optical properties. Therefore, the present invention also relates to a retardation film comprising a cured product of the mixed composition of the present invention, which is a liquid crystal cured film obtained by curing the mixed composition in an aligned state. A retardation film made from the cured product of the mixed composition can fully exhibit the optical properties that the liquid crystal compound used can inherently exhibit, and can be a retardation film with high optical performance.

[0158] The cured liquid crystal film constituting the retardation film of the present invention may be composed of an oriented homopolymer of compound (7-1) and compound (7-2) and a homopolymer of compound (1) and / or compound (8), or may be composed of an oriented copolymer of a mixture of compound (7-1) and compound (7-2) and compound (1) and / or compound (8). Because the polymerization reaction is easy and a uniform cured liquid crystal film is easily obtained, the cured liquid crystal film constituting the retardation film of the present invention is preferably composed of an oriented copolymer of a mixture of compound (7-1) and compound (7-2) and compound (1) and / or compound (8).

[0159] In one embodiment of the present invention, the retardation film of the present invention is a cured product of the mixed composition of the present invention, and preferably satisfies the optical properties represented by the following formulas (a), (b), and (c): Such a liquid crystal cured film is usually a cured product obtained by curing compound (7-1) and compound (7-2), and compound (1) and / or compound (8), in a state where they are aligned horizontally relative to the plane of the liquid crystal cured film (hereinafter also referred to as a "horizontally aligned liquid crystal cured film").

[0160] Re(450) / Re(550)≦1.00 (a) 1.00≦Re(650) / Re(550) (b) 100nm≦Re(550)≦180nm (c) (In the formula, Re(λ) represents the in-plane retardation value of the cured liquid crystal film at a wavelength of λ nm, and Re=(nx(λ)-ny(λ))×d (d represents the thickness of the cured liquid crystal film, nx represents the principal refractive index at a wavelength of λ nm in a direction parallel to the plane of the cured liquid crystal film in an index ellipsoid formed by the cured liquid crystal film, and ny represents the refractive index at a wavelength of λ nm in a direction parallel to the plane of the cured liquid crystal film and perpendicular to the direction of nx in an index ellipsoid formed by the cured liquid crystal film).) When the horizontally aligned liquid crystal cured film satisfies formulas (a) and (b), the horizontally aligned liquid crystal cured film exhibits a so-called reverse wavelength dispersion, in which the in-plane retardation value at short wavelengths is smaller than the in-plane retardation value at long wavelengths. To improve the reverse wavelength dispersion and further improve the optical properties of the retardation film, Re(450) / Re(550) is preferably 0.70 or more, more preferably 0.72 or more, even more preferably 0.75 or more, and is preferably 0.90 or less, more preferably 0.87 or less, even more preferably 0.85 or less, and particularly preferably 0.83 or less. Furthermore, Re(650) / Re(550) is preferably 1.00 or more, more preferably 1.01 or more, and even more preferably 1.02 or more.

[0161] The in-plane retardation value can be adjusted by the thickness d of the horizontally aligned liquid crystal cured film. Since the in-plane retardation value is determined by the above formula Re(λ)=(nx(λ)-ny(λ))×d, a desired in-plane retardation value (Re(λ): in-plane retardation value of the horizontally aligned liquid crystal cured film at a wavelength λ (nm)) can be obtained by adjusting the three-dimensional refractive index and the film thickness d.

[0162] Furthermore, when the horizontally aligned liquid crystal cured film satisfies formula (c), the retardation film containing the horizontally aligned liquid crystal cured film functions as a λ / 4 plate, and is excellent in the effect of improving the front reflection hue (the effect of suppressing coloration) when an elliptically polarizing plate including the retardation film containing the liquid crystal cured film is applied to an optical display, etc. A more preferable range of the in-plane retardation value is 120 nm≦Re(550)≦170 nm, and an even more preferable range is 130 nm≦Re(550)≦150 nm.

[0163] The retardation film of the present invention can be produced, for example, by a method including the steps of forming a coating film of the mixed composition of the present invention, drying the coating film, and aligning polymerizable liquid crystal compounds in the mixed composition, including compound (7-1) and compound (7-2) (hereinafter, the compounds capable of constituting a cured liquid crystal film, contained in the mixed composition, are also collectively referred to simply as “polymerizable liquid crystal compounds”), and polymerizing the polymerizable liquid crystal compounds by light irradiation while maintaining the aligned state, to form a cured liquid crystal film.

[0164] The coating film of the mixed composition can be formed by applying the mixed composition onto a substrate or an alignment film. The substrate can be appropriately selected from substrates known in the art, such as glass substrates and resin film substrates. The alignment film can be appropriately selected from alignment films commonly used in the production of optical films (particularly retardation films), such as alignment films containing an orientable polymer, photo-alignment films, groove alignment films having a concavo-convex pattern or a plurality of grooves on the surface, and stretched films stretched in the alignment direction.

[0165] Examples of a method for applying the mixed composition to a substrate or the like include known methods such as coating methods such as spin coating, extrusion, gravure coating, die coating, bar coating, and applicator methods, and printing methods such as flexography.

[0166] The solvent is then removed by drying or the like to form a dried coating film. Examples of drying methods include natural drying, forced air drying, heat drying, and reduced-pressure drying. In this case, by heating the coating film obtained from the mixed composition, the solvent can be dried and removed from the coating film, and the polymerizable liquid crystal compound can be aligned in a desired direction (e.g., horizontal or vertical) relative to the coating film plane. The heating temperature for the coating film can be determined appropriately taking into account the materials of the polymerizable liquid crystal compound used and the substrate on which the coating film is formed. However, in order to transition the polymerizable liquid crystal compound to a liquid crystal phase state, a temperature above the liquid crystal phase transition temperature is usually required. To achieve the desired alignment state while removing the solvent contained in the mixed composition, the mixed composition can be heated, for example, to a temperature above the liquid crystal phase transition temperature (smectic phase transition temperature or nematic phase transition temperature) of the polymerizable liquid crystal compound contained in the mixed composition.

[0167] The mixed composition of the present invention contains at least compound (7-1) and compound (7-2) and compound (1) and / or compound (8), and can usually undergo a liquid crystal phase transition at a temperature lower than the temperature at which each compound alone transitions to a liquid crystal phase. Therefore, in the production of a retardation film using the mixed composition of the present invention, not only can a retardation film with excellent optical properties be obtained, but excessive consumption of thermal energy can be suppressed, thereby improving production efficiency. Furthermore, since the liquid crystal phase transition can be achieved by heating at a relatively low temperature, there is also the advantage that the range of support substrates on which the mixed composition is applied is broadened.

[0168] The heating time can be appropriately determined depending on the heating temperature, the type of polymerizable liquid crystal compound contained, the type and boiling point of the solvent, and the amount thereof, but is usually 15 seconds to 10 minutes, and preferably 0.5 to 5 minutes.

[0169] The removal of the solvent from the coating film may be carried out simultaneously with or separately from heating the liquid crystal compound contained in the mixed composition to a temperature above the liquid crystal phase transition temperature. However, from the viewpoint of improving productivity, simultaneous removal is preferred. Before heating the polymerizable liquid crystal compound to a temperature above the liquid crystal phase transition temperature, a pre-drying step may be carried out to adequately remove the solvent from the coating film obtained from the mixed composition under conditions that do not polymerize the polymerizable liquid crystal compound contained in the coating film. Drying methods in such a pre-drying step include natural drying, forced air drying, heat drying, and reduced pressure drying. The drying temperature (heating temperature) in the drying step can be appropriately determined depending on the type of polymerizable liquid crystal compound used, the type and boiling point of the solvent, and the amount thereof.

[0170] Next, the resulting dried coating film is polymerized by light irradiation while maintaining the orientation of the polymerizable liquid crystal compound, thereby forming a liquid crystal cured film, which is a polymer of the polymerizable liquid crystal compound present in the desired orientation. The mixed composition of the present invention can be highly polymerized by irradiation with high-intensity light such as ultraviolet light while minimizing damage to the polymerizable liquid crystal compound, so photopolymerization is typically used as the polymerization method. In photopolymerization, the light irradiated onto the dried coating film is appropriately selected depending on the type of polymerization initiator contained in the dried coating film and the type and amount of polymerizable liquid crystal compound. Specific examples include one or more types of light selected from the group consisting of visible light, ultraviolet light, infrared light, X-rays, α-rays, β-rays, and γ-rays, as well as actinic electron beams. Among these, ultraviolet light is preferred because it allows for easy control of the polymerization reaction and allows the use of photopolymerization equipment widely used in the field. It is preferable to select the types of polymerizable liquid crystal compound and polymerization initiator contained in the mixed composition so that they can be photopolymerized by ultraviolet light. Furthermore, the polymerization temperature can be controlled by irradiating the dried coating film with light while cooling it with an appropriate cooling means. By adopting such a cooling means, polymerization of the polymerizable liquid crystal compound can be carried out at a lower temperature, and even if a substrate with relatively low heat resistance is used, a liquid crystal cured film can be appropriately formed. Furthermore, the polymerization reaction can be accelerated by increasing the polymerization temperature within a range in which defects due to heat during light irradiation (such as deformation of the substrate due to heat) do not occur. During photopolymerization, a patterned cured film can also be obtained by performing masking and development.

[0171] The thickness of the liquid crystal cured film can be appropriately selected depending on the display device to which it is applied, etc. It is preferably 0.2 to 3 μm, more preferably 0.2 to 2 μm. Examples of the light source for the actinic energy rays include a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a xenon lamp, a halogen lamp, a carbon arc lamp, a tungsten lamp, a gallium lamp, an excimer laser, an LED light source emitting light in a wavelength range of 380 to 440 nm, a chemical lamp, a black light lamp, a microwave-excited mercury lamp, and a metal halide lamp.

[0172] The UV irradiation intensity is usually 10 to 3,000 mW / cm 2 The ultraviolet irradiation intensity is preferably an intensity in a wavelength region effective for activating a photopolymerization initiator. The light irradiation time is usually 0.1 seconds to 10 minutes, preferably 0.1 seconds to 5 minutes, more preferably 0.1 seconds to 3 minutes, and even more preferably 0.1 seconds to 1 minute. When irradiating once or multiple times with such ultraviolet irradiation intensity, the cumulative light amount is 10 to 3,000 mJ / cm. 2 , preferably 50 to 2,000 mJ / cm 2 , more preferably 100 to 1,000 mJ / cm 2 is.

[0173] <Circular polarizer> The present invention includes a circular polarizing plate comprising the retardation film of the present invention. The circular polarizing plate of the present invention generally comprises a polarizing film.

[0174] The polarizing film is a film having a polarizing function, and examples thereof include a stretched film having adsorbed thereon a dye having absorption anisotropy, a film containing a film coated with a dye having absorption anisotropy as a polarizer, etc. As such a polarizing film, for example, known polarizing films used in circular polarizing plates, such as those described in JP-A-2013-33249 and JP-A-2013-200445, can be used.

[0175] The circular polarizing plate of the present invention is configured to include the retardation film of the present invention and a polarizing film, and can be obtained, for example, by laminating the retardation film of the present invention and a polarizing film via an adhesive layer, a pressure-sensitive adhesive layer, etc. In one embodiment of the present invention, when the retardation film of the present invention and a polarizing film are laminated, they are preferably laminated so that the angle formed between the slow axis (optical axis) of the liquid crystal cured film constituting the retardation film and the absorption axis of the polarizing film is 45±5°.

[0176] The circular polarizing plate of the present invention may have a structure similar to that of a conventional general circular polarizing plate, or a polarizing film and a retardation film, such as a pressure-sensitive adhesive layer (sheet) for attaching the circular polarizing plate to a display element or the like constituting an image display device, or a protective film used for protecting the surface of a polarizing film or a retardation film from scratches or dirt.

[0177] The circularly polarizing plate of the present invention can be used in various display devices. A display device is a device having a display element, and includes a light-emitting element or a light-emitting device as a light source. Examples of display devices include liquid crystal display devices, organic electroluminescent (EL) display devices, inorganic electroluminescent (EL) display devices, flexible image displays, touch panel display devices, electron emission displays (e.g., field emission displays (FEDs) and surface field emission displays (SEDs)), electronic paper (display devices using electronic ink or electrophoretic elements), plasma display devices, projection display devices (e.g., grating light valve (GLV) displays and displays having digital micromirror devices (DMDs)), and piezoelectric ceramic displays. Liquid crystal display devices include transmissive liquid crystal display devices, semi-transmissive liquid crystal display devices, reflective liquid crystal display devices, direct-view liquid crystal display devices, and projection liquid crystal display devices. These display devices may display two-dimensional images or three-dimensional images. In particular, the circular polarizer of the present invention is suitable for use in organic electroluminescent (EL) display devices and inorganic electroluminescent (EL) display devices. These display devices (optical displays) can exhibit good image display characteristics by being provided with the circular polarizing plate of the present invention, which has excellent optical properties. [Example]

[0178] The present invention will be described in more detail below with reference to the following examples. In the examples, "%" and "parts" mean "% by mass" and "parts by mass", respectively, unless otherwise specified. The HPLC measurement used for analyzing each compound may be performed under any conditions as long as the peaks derived from each polymerizable liquid crystal compound can be separated. An example of the HPLC measurement conditions is shown below.

[0179] (Measurement conditions) Measurement equipment: HPLC LC-10AT (Shimadzu Corporation) Column: L-Column ODS (inner diameter 3.0 mm, length 150 mm, particle size 3 μm) Temperature: 40℃ Mobile phase A: 0.1%(v / v)-TFA / water Mobile phase B: 0.1% (v / v)-TFA / acetonitrile Gradient: 0min 50%-B 30min 100%-B 60min 100%-B 60.01min 50%-B 75min 50%-B Flow rate: 0.5mL / min Injection volume: 5μL Detection wavelength: 350 nm <Synthesis of Compound (P3-1)> Compound (1-1a) was synthesized with reference to Patent Document (JP 2019-3177 A). Compound (1-2a) was synthesized with reference to Patent Document (JP 2010-31223 A). Compound (P3-1) was synthesized from Compound (1-1a) and Compound (1-2a).

[0180] [ka]

[0181] <Synthesis of Compound (P1-1)> Compound (1-3a) was synthesized with reference to patent document (WO 2022 / 181518). Compound (P1-1) was synthesized from compound (1-1a) and compound (1-3a) with reference to patent document (JP 2010-31223 A).

[0182] [ka]

[0183] <Synthesis of Compound (P1-2)> Compound (1-4a) was synthesized with reference to a patent document (WO 2022 / 181518). Compound (P1-2) was synthesized from compound (1-1a) and compound (1-4a) with reference to a patent document (JP 2010-31223 A).

[0184] [ka]

[0185] <Synthesis of Compound (1-5a)> 43.0 g of compound (1-3a), 0.5 g of DMF, and 57.0 g of toluene were mixed, and 24.2 g of thionyl chloride was added dropwise over 1 hour. Subsequently, a solution of 16.9 g of 4-hydroxybenzoic acid, 21.5 g of pyridine, and 200 g of THF was added dropwise and the mixture was incubated at room temperature for 2 hours. The resulting reaction solution was diluted with toluene, washed with 20% aqueous sulfuric acid, water, and saturated aqueous sodium bicarbonate, and then purified by column chromatography to obtain 24.5 g of compound (1-5a).

[0186] [ka]

[0187] <Synthesis of Compound (P1-3)> Compound (P1-3) was synthesized from compound (1-1a) and compound (1-5a) with reference to a patent document (JP 2010-31223 A).

[0188] [ka]

[0189] [Example 1] <Synthesis of Mixture Composition (1)> A 300 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen and a compound (1-1a) 5.0 g synthesized with reference to a patent document (JP 2019-3177 A), a compound (P3-1) 17.2 g synthesized with reference to a patent document (JP 2010-31223 A), DMAP (N,N-dimethylaminopyridine, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) 0.4 g (approximately 0.2 mol per mole of compound (1-1a)), BHT (dibutylhydroxytoluene, manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) 0.2 g, and N-methylpyrrolidone (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) 70 g (approximately 4 parts by mass per part by mass of compound (P3-1)) were added and mixed, and the mixture was reacted at 50 ° C. for 4 hours. After the reaction was completed, 100 g of toluene (manufactured by Nacalai Tesque) was added, and then three times the amount of water as N-methylpyrrolidone was added and extracted to obtain a toluene solution. 6.8 g of compound (1-3a) synthesized with reference to a patent document (International Publication No. 2022 / 181518) was added to the toluene solution, and 2.9 g of IPC (diisopropylcarbodiimide, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was further added using a dropping funnel, and these were reacted overnight at 0 ° C. After the reaction was completed, insoluble components were removed by filtration. The solution was added dropwise to 300 g of methanol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) in an amount three times the mass of toluene contained in the solution, causing solids to precipitate. Subsequently, the precipitated solid was removed by filtration, washed three times with 10 g of methanol, and then dried under reduced pressure at 30 ° C. to obtain 26.3 g of mixed composition (1).

[0190] The ratio of the polymerizable liquid crystal compound (P1-1), the polymerizable liquid crystal compound (P2-1a), the polymerizable liquid crystal compound (P2-1b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (1) was measured by high performance liquid chromatography, and the result was (P1-1):(P2-1a):(P2-1b):(P3-1) = 3.7:65.6:20.2:10.5.

[0191] In Example 1, compound (P3-1) corresponds to compound (1) in step (i), compound (1-1a) corresponds to compound (2) in step (i), compound (1-3a) corresponds to compound (9) in step (ii), compound (P1-1) corresponds to compound (8), and compounds (P2-1a) and (P2-1b) correspond to compounds (7-1) and (7-2), respectively.

[0192] [ka]

[0193] [Example 2] <Synthesis of Mixture Composition (2)> The reaction was carried out in the same manner as in Example 1, except that N-methylpyrrolidone was replaced with N,N-dimethylacetamide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), to obtain 26.3 g of a mixed composition (2).

[0194] The ratio of the polymerizable liquid crystal compound (P1-1), the polymerizable liquid crystal compound (P2-1a), the polymerizable liquid crystal compound (P2-1b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (2) was measured by high performance liquid chromatography, and the result was (P1-1):(P2-1a):(P2-1b):(P3-1) = 3.5:64.8:20.1:11.6.

[0195] [Example 3] <Synthesis of Mixture (3)> The reaction was carried out in the same manner as in Example 1, except that 0.4 g of DMAP was changed to 1.2 g of DBU (diazabicycloundecene, manufactured by Tokyo Chemical Industry Co., Ltd.) (approximately 0.5 mol per 1 mol of compound (1-1a)), to obtain 26.2 g of mixed composition (3).

[0196] The ratio of the polymerizable liquid crystal compound (P1-1), the polymerizable liquid crystal compound (P2-1a), the polymerizable liquid crystal compound (P2-1b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (3) was measured by high performance liquid chromatography, and the result was (P1-1):(P2-1a):(P2-1b):(P3-1) = 0.0:79.4:17.6:3.0.

[0197] [Example 3'] <Synthesis of Mixture Composition (3')> A 300 mL four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 5.0 g of compound (1-1a) synthesized with reference to a patent document (JP 2019-3177 A), 13.5 g of compound (P1-1), 1.2 g of DBU (approximately 0.5 moles per mole of compound (1-1a)), 0.2 g of BHT, and 70 g of N-methylpyrrolidone (approximately 5 parts by mass per part by mass of compound (P1-1)) were added and mixed, and reacted at 50 ° C. for 4 hours. After the reaction was completed, 100 g of toluene (manufactured by Nacalai Tesque) was added, and then extracted with water in an amount three times the amount of N-methylpyrrolidone to obtain a toluene solution. 9.6 g of compound (1-2a) was added to the toluene solution, and 2.9 g of IPC was further added using a dropping funnel, and the mixture was reacted overnight at 0 ° C. After the reaction was completed, insoluble components were removed by filtration. The solution was added dropwise to 300 g of methanol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) in an amount three times the mass of the toluene contained in the solution to precipitate a solid. The precipitated solid was then filtered, washed three times with 10 g of methanol, and dried under reduced pressure at 30°C to obtain 26.3 g of mixed composition (3').

[0198] The ratio of polymerizable liquid crystal compound (P1-1), polymerizable liquid crystal compound (P2-1a), polymerizable liquid crystal compound (P2-1b), and polymerizable liquid crystal compound (P3-1) in mixed composition (3') was measured by high performance liquid chromatography, and the result was (P1-1):(P2-1a):(P2-1b):(P3-1) = 3.0:17.6:79.4:0.0.

[0199] In Example 3', compound (P1-1) corresponds to compound (8) in step (ib), compound (1-1a) corresponds to compound (2) in step (ib), compound (1-2a) corresponds to compound (10) in step (ii-b), compound (P3-1) corresponds to compound (1), and compounds (P2-1a) and (P2-1b) correspond to compounds (7-1) and (7-2), respectively.

[0200] [ka]

[0201] [Example 4] <Synthesis of Mixture (4)> A reaction was carried out in the same manner as in Example 1, except that the compound (1-3a) was changed to the compound (1-4a), to obtain a mixed composition (4).

[0202] The ratio of the polymerizable liquid crystal compound (P1-2), the polymerizable liquid crystal compound (P2-2a), the polymerizable liquid crystal compound (P2-2b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (4) was measured by high performance liquid chromatography, and the result was (P1-2):(P2-2a):(P2-2b):(P3-1) = 3.6:65.6:20.2:10.6.

[0203] In Example 4, compound (P3-1) corresponds to compound (1) in step (i), compound (1-1a) corresponds to compound (2) in step (i), compound (1-4a) corresponds to compound (9) in step (ii), compound (P1-2) corresponds to compound (8), and compounds (P2-2a) and (P2-2b) correspond to compounds (7-1) and (7-2), respectively.

[0204] [ka]

[0205] [Example 5] <Synthesis of Mixture (5)> A reaction was carried out in the same manner as in Example 2, except that the compound (1-3a) was changed to the compound (1-4a), to obtain a mixed composition (5).

[0206] The ratio of the polymerizable liquid crystal compound (P1-2), the polymerizable liquid crystal compound (P2-2a), the polymerizable liquid crystal compound (P2-2b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (5) was measured by high performance liquid chromatography, and the result was (P1-2):(P2-2a):(P2-2b):(P3-1) = 3.4:64.8:20.1:11.7.

[0207] [Example 6] <Synthesis of Mixture (6)> A reaction was carried out in the same manner as in Example 3, except that the compound (1-3a) was changed to the compound (1-4a), to obtain a mixed composition (6).

[0208] The ratio of the polymerizable liquid crystal compound (P1-2), the polymerizable liquid crystal compound (P2-2a), the polymerizable liquid crystal compound (P2-2b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (6) was measured by high performance liquid chromatography, and the result was (P1-2):(P2-2a):(P2-2b):(P3-1) = 0.0:79.4:17.6:3.0.

[0209] [Example 6'] <Synthesis of Mixture (6')> A reaction was carried out in the same manner as in Example 3', except that the compound (P1-1) was changed to the compound (P1-2), to obtain a mixed composition (6').

[0210] The ratio of the polymerizable liquid crystal compound (P1-2), the polymerizable liquid crystal compound (P2-2a), the polymerizable liquid crystal compound (P2-2b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (6) was measured by high performance liquid chromatography, and the result was (P1-2):(P2-2a):(P2-2b):(P3-1)=3.0:17.6:79.4:0.0.

[0211] In Example 6', compound (P1-2) corresponds to compound (8) in step (ib), compound (1-1a) corresponds to compound (2) in step (ib), compound (1-2a) corresponds to compound (10) in step (ii-b), compound (P3-1) corresponds to compound (1), and compounds (P2-2a) and (P2-2b) correspond to compounds (7-1) and (7-2), respectively.

[0212] [Example 7] <Synthesis of Mixture (7)> A reaction was carried out in the same manner as in Example 1, except that the compound (1-3a) was changed to the compound (1-5a), to obtain a mixed composition (7).

[0213] The ratio of the polymerizable liquid crystal compound (P1-3), the polymerizable liquid crystal compound (P2-3a), the polymerizable liquid crystal compound (P2-3b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (7) was measured by high performance liquid chromatography, and the result was (P1-3):(P2-3a):(P2-3b):(P3-1) = 4.2:66.0:20.3:9.5.

[0214] In Example 7, compound (P3-1) corresponds to compound (1) in step (i), compound (1-1a) corresponds to compound (2) in step (i), compound (1-5a) corresponds to compound (9) in step (ii), compound (P1-3) corresponds to compound (8), and compounds (P2-3a) and (P2-3b) correspond to compounds (7-1) and (7-2), respectively.

[0215] [ka]

[0216] [Example 8] <Synthesis of Mixture (8)> A reaction was carried out in the same manner as in Example 2, except that the compound (1-3a) was changed to the compound (1-5a), to obtain a mixed composition (8).

[0217] The ratio of the polymerizable liquid crystal compound (P1-3), the polymerizable liquid crystal compound (P2-3a), the polymerizable liquid crystal compound (P2-3b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (8) was measured by high performance liquid chromatography, and the result was (P1-3):(P2-3a):(P2-3b):(P3-1) = 4.0:65.3:20.3:10.5.

[0218] [Example 9] <Synthesis of Mixture (9)> A reaction was carried out in the same manner as in Example 3, except that the compound (1-3a) was changed to the compound (1-5a), to obtain a mixed composition (9).

[0219] The ratio of the polymerizable liquid crystal compound (P1-3), the polymerizable liquid crystal compound (P2-3a), the polymerizable liquid crystal compound (P2-3b), and the polymerizable liquid crystal compound (P3-1) in the mixed composition (9) was measured by high performance liquid chromatography, and the result was (P1-3):(P2-3a):(P2-3b):(P3-1) = 0.0:79.7:17.7:2.7.

[0220] [Example 9'] <Synthesis of Mixture (9')> A reaction was carried out in the same manner as in Example 3', except that the compound (P1-1) was changed to the compound (P1-3), to obtain a mixed composition (9').

[0221] The ratio of polymerizable liquid crystal compound (P1-3), polymerizable liquid crystal compound (P2-3a), polymerizable liquid crystal compound (P2-3b), and polymerizable liquid crystal compound (P3-1) in mixed composition (9') was measured by high performance liquid chromatography, and the result was (P1-3):(P2-3a):(P2-3b):(P3-1) = 2.7:17.7:79.7:0.0.

[0222] In Example 9', compound (P1-3) corresponds to compound (8) in step (ib), compound (1-1a) corresponds to compound (2) in step (ib), compound (1-2a) corresponds to compound (10) in step (ii-b), compound (P3-1) corresponds to compound (1), and compounds (P2-3a) and (P2-3b) correspond to compounds (7-1) and (7-2), respectively.

[0223] [Comparative Examples 1 to 5] Each mixed composition was obtained by carrying out the reaction in the same manner as in Example 1, except that the solvent used was changed as shown in Table 1. The ratio of each polymerizable liquid crystal compound in the mixed composition is as shown in Table 2.

[0224] Comparative Example 6 Each mixed composition was obtained by carrying out the reaction in the same manner as in Example 3, except that the solvent used was changed as shown in Table 1. The ratio of each polymerizable liquid crystal compound in the mixed composition is as shown in Table 2.

[0225] Comparative Example 7 A mixed composition was obtained by carrying out a reaction in the same manner as in Example 4, except that the solvent used was changed as shown in Table 3. The ratio of each polymerizable liquid crystal compound in the mixed composition is as shown in Table 4.

[0226] [Comparative Example 8] A mixed composition was obtained by carrying out a reaction in the same manner as in Example 6, except that the solvent used was changed as shown in Table 3. The ratio of each polymerizable liquid crystal compound in the mixed composition is as shown in Table 4.

[0227] [Comparative Examples 9 to 12] The reaction was carried out in the same manner as in Example 7, except that the solvent used was changed as shown in Table 5, and the ratio of each polymerizable liquid crystal compound in each mixed composition was as shown in Table 6.

[0228] [Comparative Example 13] A mixed composition was obtained by carrying out a reaction in the same manner as in Example 9, except that the solvent used was changed as shown in Table 5. The ratio of each polymerizable liquid crystal compound in the mixed composition is as shown in Table 6.

[0229] [Hydrolysis resistance test] Mixed composition (1) was purified by silica gel column chromatography using chloroform and methanol as developing solvents to obtain compounds (P1-1), (P2-1a), (P2-1b), and (P3-1), respectively. Mixed compositions (4) and (7) were also purified in the same manner to obtain compounds (P1-2), (P1-3), (P2-2a), (P2-2b), (P2-3a), and (P2-3b).

[0230] 100 mg of each compound (P1-1), (P1-2), (P1-3), (P2-1a), (P2-1b), (P2-2a), (P2-2b), (P2-3a), (P2-3b), and (P3-1) was dissolved in a 10% v / v water / dimethylacetamide solution and heated and stirred at 90°C for 68 hours. After the reaction was completed, the residual percentage of each component was calculated by HPLC. The residual percentage of each component was then calculated using the residual percentage of each component and the ratio of each component in the composition listed in Tables 2, 4, and 6. A higher residual percentage indicates higher hydrolysis resistance.

[0231] [Table 1]

[0232] [Table 2]

[0233] [Table 3]

[0234] [Table 4]

[0235] [Table 5]

[0236] [Table 6]

[0237] In the table, an upward arrow "↑" indicates the same as above. The charging order "A→B" indicates a production method including step (i) of reacting a symmetrical compound (1) having a structure represented by A with compound (2), i.e., a production method that performs steps (i) and (ii). The charging order "B→A" indicates a production method including step (ib) of reacting a symmetrical compound (8) having a structure represented by B with compound (2), i.e., a production method that performs steps (ib) and (ii-b).

Claims

1. The method includes a step of reacting a compound represented by formula (1) with a compound represented by formula (2) in the presence of a basic compound using an organic solvent having a dielectric constant of 30 or more to obtain a reaction mixture composition containing a compound represented by formula (3) and a compound represented by formula (4), A method for producing a reaction mixture composition, wherein, in the area percentage values ​​of the compound represented by formula (3) and the compound represented by formula (4) in the reaction mixture composition measured by liquid chromatography, the value of formula (3) / (formula (3) + formula (4)) is 0.75 or more and less than 0.95, or the value of formula (4) / (formula (3) + formula (4)) is 0.75 or more and less than 0.

95. A-Ar-A (1) HO-Ar-OH (2) A-Ar-OH (3) HO-Ar-A (4) [A in formula (1), formula (3) and formula (4) is represented by the following formula (5): *-D １ -(A １ -E １ )m-SP １ -L １ (5) is expressed as In formula (5), * represents the bonding position to Ar in formula (1), formula (3), or formula (4), m represents an integer of 1 or more; D １ represents —C(═O)—O— or —O—C(═O)—; E １ represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; when m is an integer of 2 or more, a plurality of E １ may be the same or different, A １ represents a divalent aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 6 or more carbon atoms which may have a substituent, and when m is an integer of 2 or more, a plurality of A １ may be the same or different, SP １ represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, a linear or branched alkynylene group having 2 to 20 carbon atoms, or —CH which constitutes the alkylene group, the alkenylene group, or the alkynylene group. ２ represents a divalent linking group in which one or more -'s are substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, and Q represents a substituent; L １ represents a monovalent organic group, Ar in the formulas (1), (2), (3) and (4) is represented by the following formulas (Ar-1) to (Ar-6): 【Chemistry 1】 [In formulas (Ar-1) to (Ar-6), * is D １ Represents the bond with; Q １ is —S—, —O— or —NR ６ represents -, and R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent, Q ２ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; W １ and W ２ each independently represents —O—, —S—, —CO—, or —NR ６ represents -, and R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; Y １ represents an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group, Y ２ represents a CN group or an alkyl group having 1 to 12 carbon atoms which may have a substituent, a hydrogen atom contained in the alkyl group may be substituted with a halogen atom, and a —CH ２ - may be substituted by -O-, -CO-, -O-CO- or -CO-O-; Z １ , Z ２ and Z ３ each independently represents a hydrogen atom, an aliphatic hydrocarbon group or alkoxy group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, or —NR ６ R ７ or -SR ６ represents Z １ and Z ２ may be bonded to each other to form an aromatic ring or an aromatic heterocycle, R ６ and R ７ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Z ４ represents an aliphatic hydrocarbon group or alkoxy group having 2 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -NR ６ R ７ or -SR ６ represents R ６ and R ７ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Ax represents an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ax and Ay may be bonded to form a ring; Y ３ and Y ４ are each independently represented by the following formula (Y ３ -1): 【Chemistry 2】 (Formula (Y ３ -1) Middle R Ｙ１ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is ３ and the substituent X ３ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one —CH ２ - or two or more non-adjacent -CH ２ each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO-S—, —S-CO—, —O-CO-O—, —CO-NH—, —NH-CO—, —CH═CH-COO—, —CH═CH-OCO—, —COO-CH═CH—, —OCO-CH═CH—, —CH═CH—, —CF═CF- or —C≡C—, and any hydrogen atom in the alkyl group may be replaced by a fluorine atom, or —B ３１ -F ３１ -P ３１ (wherein B ３１ is -CR ８ R ９ -, -CH ２ -CH ２ -, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C(=S)-O-, -O-C(=S)-, -O-C(=S)-O-, -CO-NR ８ -, -NR ８ -CO-, -O-CH ２ -, -CH ２ —O—, —S—CH ２ -, -CH ２ represents —S— or a single bond, and R ８ and R ９ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; F ３１ represents an alkanediyl group having 1 to 12 carbon atoms, and a hydrogen atom contained in the alkanediyl group is -OR １０ or may be substituted with a halogen atom, R １０ represents an alkyl group having 1 to 4 carbon atoms, a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom, and —CH ２ - may be replaced by -O- or -CO-; P ３１ represents a hydrogen atom or a polymerizable group), U １ represents an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group, any carbon atom of which may be substituted with a heteroatom, and the aromatic hydrocarbon group is substituted with one or more of the above-mentioned substituents X ３ may be substituted by T １ is -O-, -S-, -COO-, -OCO-, -OCO-O-, -NU ２ -, -N=CU ２ --, --CO-NU ２ --, --OCO-NU ２ - or O-NU ２ - represents U ２ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom), or (E ３１ -A ３１ ) ｑ -B ３１ -F ３１ -P ３１ and the alkyl group, the cycloalkyl group, the cycloalkenyl group and the aromatic hydrocarbon group are each unsubstituted or substituted with one or more substituents X ３ and the alkyl group may be substituted by the cycloalkyl group or the cycloalkenyl group, and one —CH ２ - or two or more non-adjacent -CH ２ - each independently represents -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, or -SO ２ -, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, and one -CH in the cycloalkyl group or cycloalkenyl group may be replaced by ２ - or two or more non-adjacent -CH ２ Each - may be independently replaced by -O-, -CO-, -COO-, -OCO- or O-CO-O-; ３１ is the above B ３１ is defined similarly to A ３１ represents a divalent alicyclic hydrocarbon group having 3 to 16 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group or the aromatic hydrocarbon group is not substituted with a halogen atom, —R １１ , -OR １２ , optionally substituted with a cyano group or a nitro group, R １１ represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; R １２ represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom; B ３１ , F ３１ and P ３１ are the B ３１ , F ３１ and P ３１ q represents an integer of 0 to 4; E ３１ and / or A ３１ When there are a plurality of U, they may be the same or different. １ and U ２ may be bonded to form a ring.) is a group represented by the following formula: is a group represented by any one of the following:

2. 2. The method for producing a reaction mixture composition according to claim 1, wherein the total area percentage values ​​of the compound represented by formula (3) and the compound represented by formula (4) contained in the reaction mixture composition, as measured by liquid chromatography, is more than 50% and less than 98% based on the total area values ​​of the compound represented by formula (1), the compound represented by formula (2), the compound represented by formula (3), and the compound represented by formula (4) contained in the reaction mixture composition.

3. A mixed composition containing a compound represented by formula (7-1), a compound represented by formula (7-2), and at least one of a compound represented by formula (1) and a compound represented by formula (8), A-Ar-A (1) A-Ar-B (7-1) B-Ar-A (7-2) B-Ar-B (8) A mixed composition in which, when the sum of the area percentage value of the compound represented by formula (7-1) measured by liquid chromatography and the area percentage value of the compound represented by formula (7-2) measured by liquid chromatography is taken as 100%, the ratio of one structural isomer of the compound represented by formula (7-1) and the compound represented by formula (7-2) contained in the mixed composition is more than 75% and less than 95%. [A in formula (1), formula (7-1) and formula (7-2) is a group represented by the following formula (5): *-D １ -(A １ -E １ )m-SP １ -L １ (5) is expressed as B in the formulas (7-1), (7-2) and (8) is represented by the following formula (6): *-D ２ -(A ２ -E ２ )n-SP ２ -L ２ (6) is expressed as In formula (5) and formula (6), * represents the bonding position with Ar in formula (1), formula (7-1), formula (7-2) or formula (8), m and n each independently represent an integer of 1 or more; D １ and D ２ each independently represents —C(═O)—O— or —O—C(═O)—, E １ and E ２ each independently represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; when m is an integer of 2 or more, a plurality of E １ may be the same or different, and when n is an integer of 2 or more, a plurality of E ２ may be the same or different, A １ and A ２ each independently represents a divalent aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 6 or more carbon atoms which may have a substituent, and when m is an integer of 2 or more, a plurality of A １ may be the same or different, and when n is an integer of 2 or more, ２ may be the same or different, SP １ and SP ２ each independently represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, a linear or branched alkynylene group having 2 to 20 carbon atoms, or —CH ２ represents a divalent linking group in which one or more -'s are substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, and Q represents a substituent; L １ and L ２ each independently represents a monovalent organic group; １ and L ２ at least one of the groups is a polymerizable group, A and B are different from each other, Ar in the formula (1), formula (7-1), formula (7-2) and formula (8) is represented by the following formulas (Ar-1) to (Ar-6): 【Transformation 3】 [In formulas (Ar-1) to (Ar-6), * is D １ or D ２ Represents the bond with; Q １ is —S—, —O— or —NR ６ represents -, and R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent, Q ２ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; W １ and W ２ each independently represents —O—, —S—, —CO—, or —NR ６ represents -, and R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent; Y １ represents an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group, Y ２ represents a CN group or an alkyl group having 1 to 12 carbon atoms which may have a substituent, a hydrogen atom contained in the alkyl group may be substituted with a halogen atom, and a —CH ２ - may be substituted by -O-, -CO-, -O-CO- or -CO-O-; Z １ , Z ２ and Z ３ each independently represents a hydrogen atom, an aliphatic hydrocarbon group or alkoxy group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, or —NR ６ R ７ or -SR ６ represents Z １ and Z ２ may be bonded to each other to form an aromatic ring or an aromatic heterocycle, R ６ and R ７ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Z ４ represents an aliphatic hydrocarbon group or alkoxy group having 2 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -NR ６ R ７ or -SR ６ represents R ６ and R ７ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Ax represents an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles; Ax and Ay may be bonded to form a ring; Y ３ and Y ４ are each independently represented by the following formula (Y ３ -1): 【Chemistry 4】 (Formula (Y ３ -1) Middle R Ｙ１ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is ３ and the substituent X ３ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one —CH ２ - or two or more non-adjacent -CH ２ each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO-S—, —S-CO—, —O-CO-O—, —CO-NH—, —NH-CO—, —CH═CH-COO—, —CH═CH-OCO—, —COO-CH═CH—, —OCO-CH═CH—, —CH═CH—, —CF═CF- or —C≡C—, and any hydrogen atom in the alkyl group may be replaced by a fluorine atom, or —B ３１ -F ３１ -P ３１ (wherein B ３１ is -CR ８ R ９ -, -CH ２ -CH ２ -, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C(=S)-O-, -O-C(=S)-, -O-C(=S)-O-, -CO-NR ８ -, -NR ８ -CO-, -O-CH ２ -, -CH ２ —O—, —S—CH ２ -, -CH ２ represents —S— or a single bond, and R ８ and R ９ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; F ３１ represents an alkanediyl group having 1 to 12 carbon atoms, and a hydrogen atom contained in the alkanediyl group is -OR １０ or may be substituted with a halogen atom, R １０ represents an alkyl group having 1 to 4 carbon atoms, a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom, and —CH ２ - may be replaced by -O- or -CO-; P ３１ represents a hydrogen atom or a polymerizable group), U １ represents an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group, any carbon atom of which may be substituted with a heteroatom, and the aromatic hydrocarbon group is substituted with one or more of the above-mentioned substituents X ３ may be substituted by T １ is -O-, -S-, -COO-, -OCO-, -OCO-O-, -NU ２ -, -N=CU ２ --, --CO-NU ２ --, --OCO-NU ２ - or O-NU ２ - represents U ２ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom), or (E ３１ -A ３１ ) ｑ -B ３１ -F ３１ -P ３１ and the alkyl group, the cycloalkyl group, the cycloalkenyl group and the aromatic hydrocarbon group are each unsubstituted or substituted with one or more substituents X ３ and the alkyl group may be substituted by the cycloalkyl group or the cycloalkenyl group, and one —CH ２ - or two or more non-adjacent -CH ２ - each independently represents -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, or -SO ２ -, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, and one -CH in the cycloalkyl group or cycloalkenyl group may be replaced by ２ - or two or more non-adjacent -CH ２ Each - may be independently replaced by -O-, -CO-, -COO-, -OCO- or O-CO-O-; ３１ is the above B ３１ is defined similarly to A ３１ represents a divalent alicyclic hydrocarbon group having 3 to 16 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group or the aromatic hydrocarbon group is not substituted with a halogen atom, —R １１ , -OR １２ , optionally substituted with a cyano group or a nitro group, R １１ represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; R １２ represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a fluorine atom; B ３１ , F ３１ and P ３１ are the B ３１ , F ３１ and P ３１ q represents an integer of 0 to 4; E ３１ and / or A ３１ When there are a plurality of U, they may be the same or different. １ and U ２ may be bonded to form a ring.) is a group represented by the following formula: is a group represented by any one of the following:

4. The mixed composition according to claim 3, wherein the total area percentage value of the compound represented by formula (7-1) and the compound represented by formula (7-2), as measured by liquid chromatography, is more than 50% and less than 98% based on the total area values ​​of the compound represented by formula (1), the compound represented by formula (7-1), the compound represented by formula (7-2), and the compound represented by formula (8) contained in the mixed composition.

5. A in formula (5) １ The method for producing a reaction mixture composition according to claim 1 or 2, wherein is a 1,4-cyclohexanediyl group or a 1,4-phenylenediyl group.

6. L in formula (5) １ The method for producing a reaction mixture composition according to claim 1 or 2, wherein is an acryloyloxy group.

7. A in formula (5) １ and A in formula (6) ２ The mixed composition according to claim 3 or 4, wherein each of is independently a 1,4-cyclohexanediyl group or a 1,4-phenylenediyl group.

8. L in formula (5) １ and L in formula (6) ２ The mixed composition according to claim 3 or 4, wherein each of the groups is an acryloyloxy group.

9. A method for producing a mixed composition using the reaction mixture composition produced by the method for producing a reaction mixture composition according to claim 1 or 2, comprising the steps of: A method for producing a mixed composition, the method comprising the steps of: mixing the reaction mixture composition with a compound represented by formula (9); reacting the compound represented by formula (3) with the compound represented by formula (9) to produce a compound represented by formula (7-1); and reacting the compound represented by formula (4) with the compound represented by formula (9) to produce a compound represented by formula (7-2), thereby obtaining a mixed composition containing the compound represented by formula (7-1) and the compound represented by formula (7-2). HOOC-(A ２ -E ２ )n-SP ２ -L ２ (9) A-Ar-B (7-1) B-Ar-A (7-2) [In formula (9), n represents an integer of 1 or more; E ２ represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms; when n is an integer of 2 or more, a plurality of E ２ may be the same or different, A ２ represents a divalent aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 6 or more carbon atoms which may have a substituent, and when n is an integer of 2 or more, a plurality of A ２ may be the same or different, SP ２ represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 2 to 20 carbon atoms, a linear or branched alkynylene group having 2 to 20 carbon atoms, or —CH which constitutes the alkylene group, the alkenylene group, or the alkynylene group. ２ represents a divalent linking group in which one or more -'s are substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, and Q represents a substituent; L ２ represents a monovalent organic group, provided that L ２ and L in formula (5) １ at least one of the groups is a polymerizable group, A and Ar in formula (7-1) and formula (7-2) respectively have the same meanings as A and Ar in formula (1) (however, * in formulas (Ar-1) to (Ar-6) represents D １ or D ２ and B is represented by the following formula (6): *-D ２ -(A ２ -E ２ )n-SP ２ -L ２ (6) is expressed as In formula (6), * represents the bonding position with Ar in formula (7-1) or formula (7-2), D ２ represents —C(═O)—O— or —O—C(═O)—; A ２ , E ２ ,n,SP ２ and L ２ are A in formula (9), respectively. ２ , E ２ ,n,SP ２ and L ２ and A and B are different from each other.]

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