Dichroic dye and liquid crystal composition thereof

Abstract

To provide a compound that shows high light resistance and has a high dichroic ratio and high solubility in host liquid crystals, and a liquid crystal composition, a liquid crystal display device or a light control element having the compound as a constituent.SOLUTION: A compound represented by general formula (1) is provided. (B: a substituted / unsubstituted benzene ring or naphthalene ring. R1, R2: a substituted / unsubstituted C1-C20 alkyl or C2-C30 alkenyl. X1, X2: S or NR4 (R4: a substituted / unsubstituted C1-C20 alkyl or C2-C30 alkenyl). A1, A2: a substituted / unsubstituted C3-C16 hydrocarbon ring or heterocycle. Z1, Z2: CH2O, OCH2 or the like).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to novel dichroic dyes useful as organic electronic materials, pharmaceuticals, and agricultural chemicals, and particularly as materials for liquid crystal display devices, and to liquid crystal compositions using the same. [Background technology]

[0002] Liquid crystal materials are not only used in various display elements that display text, images, and videos, as seen in TVs and smartphones, but are also beginning to be used practically as dimming elements that adjust the transmission of light.

[0003] In particular, when a "guest-host (GH) type liquid crystal composition" in which a dichroic dye is added to a host liquid crystal composition is used, a polarizing plate is not required, and it is expected that a low-cost, highly transmittant light-control element can be realized.

[0004] GH-type liquid crystal compositions have been studied for a long time, and attempts have been made to develop liquid crystal display devices and light-controlling devices that have useful device performance (e.g., large dichroic ratio, high contrast, high solubility in liquid crystal compositions, excellent light resistance, and excellent heat resistance) (see Patent Document 1).

[0005] However, some liquid crystal compositions containing dichroic dyes are not suitable for use in liquid crystal display devices or light-adjusting devices, depending on the components constituting them, and further improvements in performance are required. For example, to obtain a large dichroic ratio, a large amount of dichroic dye must be contained in the liquid crystal composition, which poses a problem of composition solubility, resulting in precipitation of the dichroic dye or liquid crystal compound. In particular, for use as a light-adjusting device, the composition must exhibit a nematic liquid crystal phase over a wide temperature range, but the molecular weight of the dye is larger than that of the liquid crystal compound, posing a problem of solubility at low temperatures.

[0006] To solve the above problems, it is necessary to improve the host liquid crystal composition, but it is also necessary to improve the dichroic dye itself. In particular, to achieve high contrast, the dichroic dye needs to exhibit a large dichroic ratio and high solubility in the host liquid crystal. Many dichroic dyes have been investigated so far, but compounds that exhibit a large dichroic ratio generally have large mesogens and most of them have poor solubility in the host liquid crystal, so further improvements are needed (Non-Patent Documents 1, 2, 3).

[0007] On the other hand, the following compounds having a benzodipyrrolidone skeleton have been reported as dye compounds (Patent Document 2, Non-Patent Document 4), but these compounds also do not have high light resistance, a large dichroic ratio, and high solubility.

[0008] [ka]

[0009] [ka] [Prior art documents] [Patent documents]

[0010] [Patent Document 1] Special Publication No. 2013-534945 [Patent Document 2] Japanese Patent Application Laid-Open No. 2015-40231 [Non-patent literature]

[0011] [Non-Patent Document 1] "Display Materials and Functional Dyes" by Hiroyuki Nakasumi [Non-patent document 2] "Functional Dye Technology" by Hiroyuki Nakasumi [Non-patent document 3] "Dichroic Dyes for Liquid Crystal Displays" by Aleksandr V. Ivashchenko [Non-patent document 4] J. Mater. Chem. C, 2017, 5, 290-300 Summary of the Invention [Problem to be solved by the invention]

[0012] The problem to be solved by the present invention is to provide a compound that exhibits high light resistance, a large dichroic ratio, and high solubility in a host liquid crystal, and also to provide a liquid crystal composition and a liquid crystal display element or a light control element that contain the compound as a constituent member. [Means for solving the problem]

[0013] In order to solve the above problems, the present inventors have investigated various compounds and found that the compound represented by the general formula (1)

[0014] [ka]

[0015] (wherein B is a group represented by general formula (2), (3) or (4)

[0016] [ka]

[0017] wherein the carbon atoms represented by *1 to *4 in the general formula (2), (3) or (4) correspond to the carbon atoms represented by *1 to *4 in the general formula (1), and one or more hydrogen atoms in these groups are not substituted by the substituents L 1 may be replaced by L 1are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl 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 -CH2- are each independently -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, - represents a linear alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms which may be substituted with 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-, provided that oxygen atoms are not directly bonded to each other and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, R 1 and R 2 each independently represents an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- groups in these groups represent -NR 3 may be replaced by -, -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, and a hydrogen atom present in these groups may be replaced by a fluorine atom, wherein R 3 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 30 carbon atoms, in which one -CH2- or two or more non-adjacent -CH2- groups may be replaced by -O-, -S-, -COO-, -OCO-, or -CO-, and a hydrogen atom in these groups may be replaced by a fluorine atom, X 1 and X 2 are each independently -S- or -NR 4 - where R 4represents an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, in which one -CH2- or two or more non-adjacent -CH2- groups may be replaced by -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF-, -C≡C-, or an optionally substituted hydrocarbon ring or heterocycle having 3 to 16 carbon atoms, and a hydrogen atom in these groups may be substituted by a fluorine atom, A 1 and A 2 each independently represents an optionally substituted hydrocarbon ring or heterocycle having 3 to 16 carbon atoms, Z 1 and Z 2 each independently represent -CHO-, -OCH-, -CFO-, -OCF-, -COO-, -OCO-, -CHCH-, -CFCF-, -CH=CH-, -CF=CF-, -N=CH-, -CH=N-, -N=N-, -C≡C- or a single bond, i and j each independently represent an integer of 1 to 4; A 1 and A 2 If there are multiple A's, 1 and A 2 may be the same or different, and Z 1 and Z 2 If there are multiple Z 1 and Z 2 may be the same or different, and multiple R 3 and R 4 If there are multiple R 3 and R 4 may be the same or different.) The present invention also provides a liquid crystal composition containing the compound, and a liquid crystal display device or a light-adjusting device using the liquid crystal composition. [Effects of the Invention]

[0018] The compound represented by general formula (1) provided by the present invention has both a large dichroic ratio and high solubility in a host liquid crystal. In addition, it also has excellent chemical stability at a level that allows it to be used as a device. Therefore, by using the compound represented by general formula (1) as a component of a GH-type liquid crystal composition, it is possible to provide a liquid crystal display device or a light-control device with high contrast. DETAILED DESCRIPTION OF THE INVENTION

[0019] In general formula (1), B is preferably a structure represented by general formula (3) or (4) in order to increase the dichroic ratio, and is preferably a structure represented by general formula (2) in order to emphasize light resistance and solubility in the host liquid crystal. 1 It is also preferred that L 1 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a pentafluorosulfanyl 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, or a thioisocyano group, or one -CH2- or two or more -CH2- are each independently -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OC Preferably, they are linear alkyl groups having 1 to 20 carbon atoms or branched or cyclic alkyl groups having 3 to 20 carbon atoms which may be substituted with O-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, and more preferably, they are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a thioisocyano group, a methyl group, an ethyl group, a propyl group, a methoxy group, an ethoxy group or an acetyl group.

[0020] X 1 and X2 is preferably an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- groups in these groups are preferably substituted by -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-. In order to increase the solubility in the host liquid crystal, -NR 4 -, where R 4 is preferably an unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, more preferably an unsubstituted linear or branched alkyl group having 4 to 20 carbon atoms, and particularly preferably an unsubstituted branched alkyl group having 4 to 20 carbon atoms. Furthermore, when light resistance is important, -S- is preferred.

[0021] R 1 and R 2 are preferably each independently an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, and it is also preferred that one -CH2- or two or more non-adjacent -CH2- groups in these groups are replaced by -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -CH=CH-, -CF=CF-, or -C≡C-. In order to increase the solubility in the host liquid crystal, they are each independently preferably an unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, more preferably an unsubstituted linear or branched alkyl group having 4 to 20 carbon atoms, and particularly preferably an unsubstituted branched alkyl group having 4 to 20 carbon atoms.

[0022] A 1 and A 2 From the viewpoints of increasing the absorption wavelength, improving dichroism, and improving solubility in a liquid crystal composition, it is preferable that each independently represent an optionally substituted hydrocarbon ring or heterocycle having 3 to 16 carbon atoms. (a) a 1,4-cyclohexylene group (in which one —CH— or two or more non-adjacent —CH— groups may be replaced by —O— or —S—). (b) a 1,4-phenylene group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by -N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (these groups contain The hydrogen atoms in the naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be substituted with -N=. (d) a thiophene-2,5-diyl group, a thiophene-2,4-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, or a thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= groups in this group may be replaced by -N=). and these groups are unsubstituted or have one or more substituents L 2 It is also preferred that the substituted group is L 2are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a pentafluorosulfanyl 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 -CH2- are each independently -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH- Preferably, they are linear alkyl groups having 1 to 20 carbon atoms or branched or cyclic alkyl groups having 3 to 20 carbon atoms which may be substituted with OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, and more preferably, they are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a thioisocyano group, a methyl group, an ethyl group, a propyl group, a methoxy group, an ethoxy group or an acetyl group. Also, A 1 and A 2 As a preferred structure of

[0023] [ka]

[0024] Preferably, R represents a group selected from eare each independently preferably a methyl group, an ethyl group, a propyl group, a 2-propyl group, a butyl group, a 2-butyl group, a methoxy group, an ethoxy group, a methylthio group, an ethylthio group, a dimethylamino group, a diethylamino group, a cyano group, a nitro group, a fluorine atom, or a chlorine atom. Specifically, in order to increase the solubility in the host liquid crystal, a trans-1,4-cyclohexylene group, an unsubstituted 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 2-alkyl-1,4-phenylene group, a 3-alkyl-1,4-phenylene group, an unsubstituted thiophene-2,5-diyl group, an unsubstituted thiophene-2,4-diyl group, a 4-alkyl-thiophene-2,5-diyl group, or a 5-alkyl-thiophene-2,4-diyl group is preferred. In this case, A 1 and A 2 When there are multiple A's, 1 and A 2 In order to increase the dichroic ratio, it is preferable that each of them is an unsubstituted 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, an unsubstituted thiophene-2,5-diyl group, an unsubstituted thiophene-2,4-diyl group, an unsubstituted naphthalene-2,6-diyl group, or an unsubstituted naphthalene-1,4-diyl group.

[0025] In addition, in order to increase the solubility in the host liquid crystal, R e preferably represents a methyl group, an ethyl group, a propyl group, a fluorine atom or a chlorine atom, and more preferably represents a methyl group, an ethyl group or a fluorine atom. e is preferably an electron-donating substituent, more preferably a methoxy group, an ethoxy group, a dimethylamino group or a diethylamino group, and particularly preferably a methoxy group, an ethoxy group or a dimethylamino group.

[0026] Z 1 and Z 2are each independently preferably -CHO-, -OCH-, -CHCH- or a single bond, more preferably -CHCH- or a single bond, in order to increase the solubility in the host liquid crystal. In order to increase the dichroic ratio, -CH=CH-, -CF=CF-, -N=CH-, -CH=N-, -N=N-, -C≡C- or a single bond is preferred, and -CH=CH-, -N=N-, -C≡C- or a single bond is more preferred. In order to exhibit high light fastness, a single bond is preferred.

[0027] In order to increase the solubility in the host liquid crystal, i and j are each independently preferably 1 or 2. In order to increase the dichroic ratio, i and j are preferably 2, 3, or 4, and more preferably 3 or 4.

[0028] In general formula (1), from the viewpoint of the stability of the compound, it is preferable that oxygen atoms are not directly bonded to each other and / or that oxygen atoms are not directly bonded to sulfur atoms.

[0029] The compound represented by the general formula (1) has a skeleton such as benzodipyrrolidone in its structure, and has R 1 and R 2 and alkyl groups represented by A 1 and A 2 These features make the entire compound closer to a rod-like structure, which improves the solubility in liquid crystal compositions and enhances the dichroism when used as a dye. 1 and A 2 When the ring is an aromatic ring, the conjugated system of π electrons spreads throughout the molecule, which is effective in shifting the light absorption wavelength to a longer wavelength.

[0030] The compound represented by general formula (1) is represented by the following formulas (1-A) to (1-F):

[0031] [ka]

[0032] (In the formula, R 1 , R 2 , X 1 , X 2 , A 1 , A 2 , Z 1 , Z 2 , i and j are R in general formula (1), 1 , R 2 , X 1 , X 2 , A 1 , A 2 , Z 1 , Z 2 , i and j have the same meaning.

[0033] Among the compounds of general formula (1), the compounds represented by the following general formulae (1-1) to (1-96) are particularly preferred.

[0034] [ka]

[0035] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0036] [ka]

[0037] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0038] [ka]

[0039] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0040] [ka]

[0041] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0042] [ka]

[0043] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0044] [ka]

[0045] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0046] [ka]

[0047] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0048] [ka]

[0049] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0050] [ka]

[0051] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0052] [ka]

[0053] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0054] [ka]

[0055] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as

[0056] [ka]

[0057] (In the formula, R 1 , R 2 and R 4 is R in general formula (1) 1 , R 2 and R 4 It has the same meaning as (Manufacturing method) In the present invention, among the compounds represented by general formula (1), X 1 and X 2 Ga-NR 4 The compound represented by formula (I) can be prepared as follows: Of course, the gist and scope of the present invention are not limited to these preparation examples. General formula (1-a)

[0058] [ka]

[0059] (In the formula, Y a1 and Y a2 each independently represents a bromine atom, a chlorine atom, an iodine atom, or a trifluoromethanesulfonyloxy group; R 4 is R represented by general formula (1) 4 The compound represented by general formula (1-a) can be produced by the method described in non-patent document (Dyes and Pigments, 162 (2019) 883-887). The compound represented by general formula (1-a) can be produced by the method described in general formula (1-b)

[0060] [ka]

[0061] (In the formula, A b is A in general formula (1) 1 or A 2 and Z b is Z in general formula (1) 1 or Z 2 b represents i-1 or j-1 in the general formula (1), R b is R in general formula (1) 1 or R 2 It has the same meaning as Y b teeth

[0062] [ka]

[0063] (In the formula, R i1 and R i2 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, which may be linear or branched; E i1 One or more hydrogen atoms in the group may each independently be substituted with a methyl group -(CH) pi -, and pi represents 2, 3, or 4.) in the presence of a transition metal catalyst and a base, the target compound represented by general formula (1) can be produced.

[0064] The transition metal catalyst used may be any that favorably promotes the reaction, but is preferably tetrakis(triphenylphosphine)palladium(0), palladium(II) acetate, bis(triphenylphosphine)palladium(II) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, or bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride, and more preferably tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, or bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride. Furthermore, to favorably promote the reaction, a phosphine-based ligand such as triphenylphosphine may be added as needed.

[0065] The reaction solvent used may be any solvent that allows the reaction to proceed favorably, but is preferably an ether solvent such as tetrahydrofuran, diethyl ether, or tert-butyl methyl ether, an alcohol solvent such as methanol, ethanol, or propanol, or an aromatic solvent such as benzene, toluene, or xylene, and more preferably tetrahydrofuran, ethanol, or toluene. Furthermore, water may be used as needed to allow the reaction to proceed favorably.

[0066] The base to be used may be any base as long as it allows the reaction to proceed favorably, but carbonates such as potassium carbonate, sodium carbonate, and cesium carbonate, and phosphates such as tripotassium phosphate and potassium dihydrogen phosphate are preferred, with potassium carbonate, cesium carbonate, and tripotassium phosphate being more preferred.

[0067] The reaction temperature may be any temperature that allows the reaction to proceed favorably, but is preferably from room temperature to the reflux temperature of the solvent used, more preferably from 40°C to the reflux temperature of the solvent, and particularly preferably from 60°C to the reflux temperature of the solvent. Among the compounds represented by general formula (1), X 1 and X2 The compound in which is -S- can be prepared as follows. General formula (1-c)

[0068] [ka]

[0069] (In the formula, Y c1 and Y c2 each independently represents a bromine atom, a chlorine atom, an iodine atom or a trifluoromethanesulfonyloxy group, and B has the same meaning as B in general formula (1). The compound represented by general formula (1-c) can be produced by the method described in a non-patent document (Chemistry Letters, 1983, 905-908). The compound represented by general formula (1-d)

[0070] [ka]

[0071] (In the formula, A d is A in general formula (1) 1 or A 2 and Z d is Z in general formula (1) 1 or Z 2 d represents i or j in general formula (1), R d is R in general formula (1) 1 or R 2 It has the same meaning as Y b represents Y in general formula (1-b). b The compound represented by the general formula (1) can be produced by reacting a compound represented by the general formula (1) with a compound represented by the general formula (1) in the presence of a transition metal catalyst and a base.

[0072] The transition metal catalyst used may be any that favorably promotes the reaction, but is preferably tetrakis(triphenylphosphine)palladium(0), palladium(II) acetate, bis(triphenylphosphine)palladium(II) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, or bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride, and more preferably tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, or bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride. Furthermore, to favorably promote the reaction, a phosphine-based ligand such as triphenylphosphine may be added as needed.

[0073] The reaction solvent used may be any solvent that allows the reaction to proceed favorably, but is preferably an ether solvent such as tetrahydrofuran, diethyl ether, or tert-butyl methyl ether, an alcohol solvent such as methanol, ethanol, or propanol, or an aromatic solvent such as benzene, toluene, or xylene, and more preferably tetrahydrofuran, ethanol, or toluene. Furthermore, water may be used as needed to allow the reaction to proceed favorably.

[0074] The base to be used may be any base as long as it allows the reaction to proceed favorably, but carbonates such as potassium carbonate, sodium carbonate, and cesium carbonate, and phosphates such as tripotassium phosphate and potassium dihydrogen phosphate are preferred, with potassium carbonate, cesium carbonate, and tripotassium phosphate being more preferred.

[0075] The reaction temperature may be any temperature that allows the reaction to proceed favorably, but is preferably from room temperature to the reflux temperature of the solvent used, more preferably from 40°C to the reflux temperature of the solvent, and particularly preferably from 60°C to the reflux temperature of the solvent. In the liquid crystal composition of the present invention, if the content of the compound represented by general formula (1) is small, its effect will not be exhibited, so the lower limit of the content in the composition is preferably 1% by mass or more (hereinafter, "%" in the composition means "% by mass"), more preferably 2% or more, and more preferably 3% or more. Furthermore, since a high content can cause problems such as precipitation, the upper limit of the content is preferably 7% or less, more preferably 6% or less. The compound represented by general formula (1) can be used alone, or two or more compounds can be used simultaneously.

[0076] As such, as a preferred representative example of a compound that can be used in combination with the compound represented by general formula (1), the composition provided by the present invention contains at least one compound represented by general formula (1) as its first component, and it is particularly preferred that the composition contains at least one of the following second to fourth components as other components.

[0077] That is, the second component is a so-called p-type liquid crystal compound having a positive dielectric anisotropy, and examples thereof include compounds represented by the following general formula (LC1) and general formula (LC2).

[0078] [ka]

[0079] (In the formula, R LC11 and R LC21 each independently represents an alkyl group having 1 to 15 carbon atoms, one or more -CH2- in the alkyl group may be substituted by -O-, -CH=CH-, -CO-, -OCO-, -COO- or -C≡C- so that an oxygen atom is not directly adjacent to the alkyl group, and one or more hydrogen atoms in the alkyl group may be optionally substituted by a halogen atom; A LC11 , and A LC21 are each independently one of the following structures:

[0080] [ka]

[0081] (In the structure, one or more -CH2- in the cyclohexylene group may be substituted with an oxygen atom, one or more -CH= in the 1,4-phenylene group may be substituted with an -N=, and one or more hydrogen atoms in the structure may be substituted with a fluorine atom, a chlorine atom, -CF3 or -OCF3), and X LC11 , X LC12 , X LC21 ~X LC23 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, -CF3 or -OCF3, and Y LC11 and Y LC21 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, -CF3, -OCH2F, -OCHF2 or -OCF3, Z LC11 and Z LC21 each independently represents a single bond, -CH=CH-, -CF=CF-, -C≡C-, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O-, -COO- or -OCO-; m LC11 and m LC21 each independently represents an integer of 1 to 4, and A LC11 , A LC21 , Z LC11 and Z LC21 If there are multiple, they may be the same or different.) R LC11 and R LC21 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, further preferably a linear group, and most preferably an alkenyl group having the following structure:

[0082] [ka]

[0083] (In the formula, the right end is bonded to the ring structure.) A LC11 and A LC21 are each preferably independently of each other the following structures:

[0084] [ka]

[0085] Y LC11 and Y LC21 are each independently preferably a fluorine atom, a cyano group, -CF3 or -OCF3, more preferably a fluorine atom or -OCF3, and particularly preferably a fluorine atom.

[0086] Z LC11 and Z LC21 is preferably a single bond, -CH2CH2-, -COO-, -OCO-, -OCH2-, -CH2O-, -OCF2- or -CF2O-, more preferably a single bond, -CH2CH2-, -OCH2-, -OCF2- or -CF2O-, and more preferably a single bond, -OCH2- or -CF2O-.

[0087] m LC11 and m LC21 is preferably 1, 2 or 3, and 1 or 2 is preferred when emphasis is placed on storage stability at low temperatures and response speed, and 2 or 3 is preferred to improve the upper limit of the nematic phase upper limit temperature.

[0088] General formula (LC1) is represented by the following general formulas (LC1-a) to (LC1-c):

[0089] [ka]

[0090] (In the formula, R LC11 , Y LC11 , X LC11 and X LC12 are each independently R in general formula (LC1). LC11 , Y LC11 , X LC11 and XLC12 It has the same meaning as A LC1a1 , A LC1a2 and A LC1b1 represents a trans-1,4-cyclohexylene group, a tetrahydropyran-2,5-diyl group, or a 1,3-dioxane-2,5-diyl group, and X LC1b1 , X LC1b2 , X LC1c1 ~X LC1c4 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, -CF3 or -OCF3.

[0091] R LC11 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.

[0092] X LC11 ~X LC1c4 are each independently preferably a hydrogen atom or a fluorine atom.

[0093] Y LC11 are each preferably independently a fluorine atom, —CF3 or —OCF3.

[0094] In addition, general formula (LC1) can be expressed by the following general formulas (LC1-d) to (LC1-m):

[0095] [ka]

[0096] (In the formula, R LC11 , Y LC11 , X LC11 and X LC12 are each independently R in general formula (LC1). LC11 , Y LC11 , X LC11 and X LC12 It has the same meaning as A LC1d1 , ALC1f1 , A LC1g1 , A LC1j1 , A LC1k1 , A LC1k2 , A LC1m1 ~A LC1m3 represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group, a tetrahydropyran-2,5-diyl group, or a 1,3-dioxane-2,5-diyl group; X LC1d1 , X LC1d2 , X LC1f1 , X LC1f2 , X LC1g1 , X LC1g2 , X LC1h1 , X LC1h2 , X LC1i1 , X LC1i2 , X LC1j1 ~X LC1j4 , X LC1k1 , X LC1k2 , X LC1m1 and X LC1m2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, -CF3 or -OCF3, Z LC1d1 , Z LC1e1 , Z LC1j1 , Z LC1k1 , Z LC1m1 are preferably one or more compounds selected from the group consisting of compounds represented by the formula (I), wherein each independently represents a single bond, -CH=CH-, -CF=CF-, -C≡C-, -CHCH-, -(CH)-, -OCH-, -CHO-, -OCF-, -CFO-, -COO- or -OCO-.

[0097] R LC11 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.

[0098] X LC11 ~X LC1m2 are each independently preferably a hydrogen atom or a fluorine atom.

[0099] Y LC11are each preferably independently a fluorine atom, —CF3 or —OCF3.

[0100] Z LC1d1 ~Z LC1m1 are each independently preferably -CF2O- or -OCH2-. General formula (LC2) is represented by the following general formula (LC2-a) to general formula (LC2-g):

[0101] [ka]

[0102] (In the formula, R LC21 , Y LC21 , X LC21 ~X LC23 are each independently R in general formula (LC2). LC21 , Y LC21 , X LC21 ~X LC23 and X LC2d1 ~X LC2d4 , X LC2e1 ~X LC2e4 , X LC2f1 ~X LC2f4 and X LC2g1 ~X LC2g4 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, -CF3 or -OCF3, Z LC2a1 , Z LC2b1 , Z LC2c1 , Z LC2d1 , Z LC2e1 , Z LC2f1 and Z LC2g1 are preferably one or more compounds selected from the group consisting of compounds represented by the formula (I), wherein each independently represents a single bond, -CH=CH-, -CF=CF-, -C≡C-, -CHCH-, -(CH)-, -OCH-, -CHO-, -OCF-, -CFO-, -COO- or -OCO-.

[0103] R LC21are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.

[0104] X LC21 ~X LC2g4 are each independently preferably a hydrogen atom or a fluorine atom, Y LC21 are each preferably independently a fluorine atom, —CF3 or —OCF3.

[0105] Z LC2a1 ~Z LC2g4 are each independently preferably -CF2O- or -OCH2-.

[0106] The third component is a so-called n-type liquid crystal compound having negative dielectric anisotropy, and examples thereof include compounds represented by the following general formulae (LC3) to (LC5).

[0107] [ka]

[0108] (In the formula, R LC31 , R LC32 , R LC41 , R LC42 , R LC51 and R LC52 each independently represents an alkyl group having 1 to 15 carbon atoms, one or more -CH2- in the alkyl group may be substituted by -O-, -CH=CH-, -CO-, -OCO-, -COO- or -C≡C- so that an oxygen atom is not directly adjacent to the alkyl group, and one or more hydrogen atoms in the alkyl group may be optionally substituted by a halogen atom; A LC31 , A LC32 , A LC41 , A LC42 , A LC51 and A LC52 are each independently one of the following structures:

[0109] [ka]

[0110] (in which one or more -CH2- in the cyclohexylene group may be substituted with an oxygen atom, one or more -CH= in the 1,4-phenylene group may be substituted with an -N=, and one or more hydrogen atoms in the structure may be substituted with a fluorine atom, a chlorine atom, -CF3 or -OCF3), and Z LC31 , Z LC32 , Z LC41 , Z LC42 , Z LC51 and Z LC51 each independently represents a single bond, -CH=CH-, -C≡C-, -CHCH-, -(CH)-, -COO-, -OCH-, -CHO-, -OCF- or -CFO-; Z 5 represents -CH2- or an oxygen atom, and X LC41 represents a hydrogen atom or a fluorine atom, m LC31 , m LC32 , m LC41 , m LC42 , m LC51 and m LC52 each independently represents 0 to 3, m LC31 +m LC32 , m LC41 +m LC42 and m LC51 +m LC52 is 1, 2 or 3, and A LC31 ~A LC52 , Z LC31 ~Z LC52 If there are multiple, they may be the same or different.) R LC31 ~R LC52 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, and the alkenyl group most preferably has the following structure:

[0111] [ka]

[0112] (In the formula, the right end is bonded to the ring structure.) A LC31 ~A LC52 are each preferably independently the following structure:

[0113] [ka]

[0114] Z LC31 ~Z LC51 are preferably each independently a single bond, -CH2O-, -COO-, -OCO-, -CH2CH2-, -CF2O-, -OCF2- or -OCH2-.

[0115] General formula (LC3) is represented by the following general formula (LC3-a) and general formula (LC3-b):

[0116] [ka]

[0117] (In the formula, R LC31 , R LC32 , A LC31 and Z LC31 are each independently R in general formula (LC3). LC31 , R LC32 , A LC31 and Z LC31 and X LC3b1 ~X LC3b6 represents a hydrogen atom or a fluorine atom, and X LC3b1 and X LC3b2 or X LC3b3 and X LC3b4 At least one combination of these represents a fluorine atom, and m LC3a1 is 1, 2 or 3, and m LC3b1 represents 0 or 1, A LC31 and Z LC31When a plurality of are present, they may be the same or different, provided that, in general formula (LC3-a), compounds selected from the group represented by general formula (LC3-b) are excluded. R LC31 and R LC32 preferably each independently represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms.

[0118] A LC31 preferably represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group, a tetrahydropyran-2,5-diyl group, or a 1,3-dioxane-2,5-diyl group, and more preferably represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group.

[0119] Z LC31 preferably represents a single bond, -CH2O-, -COO-, -OCO- or -CH2CH2-, and more preferably represents a single bond.

[0120] As the general formula (LC3-a), the following general formulas (LC3-a1) to (LC3-a4) are preferred.

[0121] [ka]

[0122] (In the formula, R LC31 and R LC32 are each independently R in general formula (LC3). LC31 and R LC32 It has the same meaning as R LC31 and R LC32 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, and R LC31 represents an alkyl group having 1 to 7 carbon atoms, and RLC32 More preferably, represents an alkoxy group having 1 to 7 carbon atoms.

[0123] General formula (LC3-b) preferably represents the following general formulae (LC3-b1) to (LC3-b12), more preferably general formulae (LC3-b1), (LC3-b6), (LC3-b8), and (LC3-b11), even more preferably general formulae (LC3-b1) and (LC3-b6), and most preferably general formula (LC3-b1).

[0124] [ka]

[0125] (In the formula, R LC31 and R LC32 are each independently R in general formula (LC3). LC31 and R LC32 It has the same meaning as R LC31 and R LC32 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, and R LC31 represents an alkyl group having 2 or 3 carbon atoms, and R LC32 More preferably, represents an alkyl group having 2 carbon atoms.

[0126] General formula (LC4) is the following general formula (LC4-a) to general formula (LC4-c), and general formula (LC5) is the following general formula (LC5-a) to general formula (LC5-c):

[0127] [ka]

[0128] (In the formula, R LC41 , R LC42 and X LC41 are each independently R in general formula (LC4). LC41 , R LC42and X LC41 It has the same meaning as R LC51 and R LC52 are each independently R in general formula (LC5). LC51 and R LC52 and Z LC4a1 , Z LC4b1 , Z LC4c1 , Z LC5a1 , Z LC5b1 and Z LC5c1 are each independently a single bond, -CH=CH-, -C≡C-, -CHCH-, -(CH)-, -COO-, -OCH-, -CHO-, -OCF- or -CFO-.

[0129] R LC41 , R LC42 , R LC51 and R LC52 preferably each independently represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms.

[0130] Z LC4a1 ~Z LC5c1 preferably each independently represent a single bond, -CH2O-, -COO-, -OCO- or -CH2CH2-, more preferably a single bond.

[0131] The fourth component is a so-called non-polar liquid crystal compound having a dielectric anisotropy of about 0, and examples thereof include compounds represented by the following general formula (LC6).

[0132] [ka]

[0133] (In the formula, R LC61 and R LC62each independently represents an alkyl group having 1 to 15 carbon atoms, one or more -CH2- in the alkyl group may be substituted by -O-, -CH=CH-, -CO-, -OCO-, -COO- or -C≡C- so that an oxygen atom is not directly adjacent to the alkyl group, one or more hydrogen atoms in the alkyl group may be optionally substituted with a halogen atom, A LC61 ~A LC63 are each independently

[0134] [ka]

[0135] (in which one or more -CH2CH2- in the cyclohexylene group may be substituted with -CH=CH-, -CF2O-, or -OCF2-, and one or more CH groups in the 1,4-phenylene group may be substituted with a nitrogen atom), and Z LC61 and Z LC62 each independently represents a single bond, -CH=CH-, -C≡C-, -CH2CH2-, -(CH2)4-, -COO-, -OCH2-, -CH2O-, -OCF2- or -CF2O-, m Lc6 represents 0 to 3, excluding the compounds represented by general formulae (LC1) to (LC5) and general formula (i). R LC61 and R LC62 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, and the alkenyl group most preferably has the following structure:

[0136] [ka]

[0137] (In the formula, the right end is bonded to the ring structure.) A LC61 ~A LC63 are each preferably independently the following structure:

[0138] [ka]

[0139] Z LC61 and Z LC62 are each preferably independently a single bond, -CH2CH2-, -COO-, -OCH2-, -CH2O-, -OCF2- or -CF2O-.

[0140] General formula (LC6) is a general formula (LC6-a) to a general formula (LC6-m)

[0141] [ka]

[0142] (In the formula, R LC61 and R LC62 and each independently represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms.

[0143] A GH-type liquid crystal display element or a light-control element using a liquid crystal composition containing the compound of the present invention is useful because it has high contrast and can be used even at low temperatures, and can be applied to devices for outdoor use as well as indoor use. [Example]

[0144] The present invention will be described in further detail below with reference to examples, but the present invention is not limited to these examples. Furthermore, "%" in the compositions of the following examples and comparative examples means "% by mass." The phase transition temperatures were measured using a polarizing microscope equipped with a temperature-control stage and a differential scanning calorimeter (DSC).

[0145] The following abbreviations are used to describe compounds. THF: tetrahydrofuran, DMF: N,N-dimethylformamide Me: methyl group, Et: ethyl group, Pr: n-propyl group, Bu: n-butyl group The dichroic ratio and light resistance of the GH-type liquid crystal composition were evaluated by sealing the composition in a glass test panel with a cell thickness of 3.5 μm and AL1051 as a horizontal alignment film. The dichroic ratio (R) was calculated as follows: Using linearly polarized light as the light source for the transmittance meter, the transmittance at the maximum absorption wavelength when the orientation direction of the test panel was parallel to the linearly polarized light was defined as A0, and the transmittance at the maximum absorption wavelength when the test panel was rotated so that the orientation direction was perpendicular to the linearly polarized light was defined as A90. The dichroic ratio (R) was calculated from the formula R=A0 / A90. The light resistance was measured by 500W / m2 SUNTEST (manufactured by ATLAS) on the test panel. 2 The color tone after two weeks of irradiation with light was visually compared with the color tone of an unirradiated test panel, and the evaluation was made based on whether or not a change in color tone was observed. The solubility of the GH type liquid crystal composition was evaluated by placing about 1 g of the liquid crystal composition in a vial, visually observing it at room temperature for one month, and determining whether or not precipitation occurred. Example 1: Preparation of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(5-(2-ethylhexyl)-2-thienyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole

[0146] [ka]

[0147] (1-1) Under dry nitrogen, N,N'-bis(2-ethylhexyl)-3,7-bis(4-bromophenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole (1.1 g, prepared by the method described in J. Mater. Chem. C, 2017, 5, 290-300), 2-[5-(2-ethylhexyl)-2-thienyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.0 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride (11 mg), 2 mol / L aqueous potassium carbonate solution (3 mL), and THF (10 mL) were mixed and heated to 65°C. After stirring for 4 hours under heating, the mixture was cooled to room temperature, and water (30 mL) and toluene (30 mL) were added and the mixture was separated. The organic layer was washed twice with saturated brine (30 mL) and then dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallized from a mixed solvent of acetone and ethanol to give N,N'-bis(2-ethylhexyl)-3,7-bis(4-(5-(2-ethylhexyl)-2-thienyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole (1.0 g). Phase transition temperature: Cr 209 Iso λ max : 528nm (dichloromethane) MS m / z: 950[M + ] 1 HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.74(4H,d,J=8.4Hz),7.66(4H,d,J=8.4Hz),7.21(2H,d,J=3.2Hz),6.76(2H,d,J=3.6Hz), 6.40(2H,s),3.60-3.47(4H,m),2.77(4H,d,J=6.4Hz),1.78-1.75(2H,m),1.64-1.60(2H,m),1.47-1.32(32H,m),0.97-0.88(24H,m) Example 2: Preparation of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(6-(2-ethylhexyloxy)-2-naphthyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole

[0148] [ka]

[0149] (2-1) 2-Bromo-6-hydroxynaphthalene (15 g), potassium carbonate (18.6 g), and 2-ethylhexyl bromide (19.5 g) were suspended in DMF (75 mL) and stirred at 80 °C for 8 hours. After cooling to room temperature, water (150 mL) and toluene (100 mL) were added and the mixture was separated. The organic layer was washed twice with saturated brine (50 mL) and then dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallized from a mixed solvent of methanol and acetone to yield 2-bromo-6-(2-ethylhexyloxy)naphthalene (18 g). 1 HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.90(1H,d,J=1.6Hz),7.63(1H,d,J=9.2Hz) ,7.58(1H,d,J=8.8Hz),7.49(1H,d,J=2.4Hz),7.47(1H,d,J=2.0Hz),7.16(1H,dd,J1= 9.0Hz,J2=2.4Hz),7.09(1H,d,J=2.4Hz),3.94(2H,d,J=4.4Hz),1.78(1H,sep,J=6.0H z),1.55-1.41(4H,m),1.38-1.31(4H,m),0.96(3H,t,J=7.6Hz),0.90(3H,t,J=7.2Hz) (2-2) Under dry nitrogen, a solution of 2-bromo-6-(2-ethylhexyloxy)naphthalene (10 g) obtained in step 2-1 dissolved in dry THF (20 mL) was added to a solution of metallic magnesium (0.86 g) suspended in dry THF (2 mL) at a rate that allowed the solvent to gently reflux. The reaction solution was stirred under reflux for 5 hours, then ice-cooled, and a solution of trimethylboric acid (4.0 g) dissolved in dry THF (8 mL) was slowly added. The mixture was then stirred at room temperature for 1 hour. The mixture was cooled again on ice, and 10% hydrochloric acid (30 mL) was slowly added, followed by the addition of ethyl acetate (50 mL) and separation. The organic layer was washed twice with saturated brine (30 mL) and dried over anhydrous sodium sulfate. After drying, the sodium sulfate was removed by filtration, and the mixture was concentrated under reduced pressure to obtain crude 6-(2-ethylhexyloxy)-2-naphthylboronic acid (A, 8.4 g). This intermediate was used in the next step without further purification. (2-3) The subsequent steps were carried out in the same manner as in Example 1, except that A obtained in step 2-2 was used instead of 2-[5-(2-ethylhexyl)-2-thienyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, thereby obtaining N,N'-bis(2-ethylhexyl)-3,7-bis(4-(6-(2-ethylhexyloxy)-2-naphthyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole. Phase transition temperature: Cr 250 Iso λ max : 510nm (dichloromethane) 1 HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=8.02(2H,d,J=1.2Hz),7.87-7.82(7H,m),7.82-7.72(7H,m),7.21-7.16(4H,m),6.45(2H ,s),3.99(4H,d,J=6.4Hz),3.63-3.50(4H,m),1.86-1.77(4H,m),1.63-1.38(32H,m),0.98(12H,t,J=7.6Hz),0.94-0.90(12H,m) (Example 3) Preparation of N,N'-dipentyl-3,7-bis(4-(5-(2-ethylhexyl)-2-thienyl)phenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole

[0150] [ka]

[0151] (3-1) 3,7-bis(4-bromophenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole (1.0 g, prepared by the method described in Dyes and Pigments 162 (2019) 883-887), 5-iodopentane (1.5 g), and potassium carbonate (1.3 g) were suspended in DMF (10 mL) and stirred at 50 °C for 5 hours. After cooling to room temperature, the reaction mixture was added to water (100 mL), and the precipitate was collected by filtration. The obtained solid was purified by silica gel column chromatography and then recrystallized from a mixed solvent of acetone and methanol to obtain 0.45 g of N,N'-dipentyl-3,7-bis(4-bromophenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole. The steps from (3-2) onwards were carried out in the same manner as in Example 1 to obtain N,N'-dipentyl-3,7-bis(4-(5-(2-ethylhexyl)-2-thienyl)phenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole. Phase transition temperature: Cr 196 Iso MS m / z: 916[M + ] λ max :622nm (dichloromethane) 1HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.81(4H,d,J=8.0Hz),7.65(4H,d,J=8.0Hz),7.36(2H,d,J=9.6Hz),7.27(2H,d,J=10Hz),7.27(2H,d,J=3. 6Hz),6.75(2H,d,J=3.6Hz),4.16-4.12(4H,m),2.77(4H,d,J=6.4Hz),1.8 3-1.74(4H,m),1.66-1.55(4H,m),1.42-1.25(22H,m),0.95-0.88(18H,m) Example 4: Preparation of 3,7-bis(6-(2-ethylhexyl)-2-naphthyl)-2H,6H-benzo[1,2-b:4,5-b′]dithiophene-2,6-dione

[0152] [ka]

[0153] (4-1) 3,7-bis(6-(2-ethylhexyl)-2-naphthyl)-2H,6H-benzo[1,2-b:4,5-b′]dithiophene-2,6-dione was obtained in the same manner as in Example 2, except that 3,7-dibromo-2H,6H-benzo[1,2-b:4,5-b′]dithiophene-2,6-dione (prepared by the method described in Chemistry Letters, 1983, pp. 905-908) was used. MS m / z: 728 [M + ] λ max :643nm (dichloromethane) 1 HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.93(2H,d,J=1.5Hz),7.83-7.71(10H,m),7.18(2H,s),3.93(4H,d,J=4. 6Hz),1.77(2H,sep,J=6.2Hz),1.55-1.41(8H,m),1.38-1.31(8H,m),0.94(6H,t,J=7.3Hz),0.88(6H,t,J=7.1Hz) (Examples 5 to 8) The compounds of Examples 5 to 8 were synthesized in the same manner as in Examples 1 to 4.

[0154] [ka]

[0155] (Example 9) Preparation of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole

[0156] [ka]

[0157] N,N'-bis(2-ethylhexyl)-3,7-bis(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole was obtained in the same manner as in Examples 1 to 4. Phase transition temperature: Cr 212 N 340 Iso MS m / z: 1262 [M + ] λ max : 494nm (dichloromethane) 1HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.80(dd,J1=29.7Hz,J2=8.7Hz,8H),7.59(d, J=1.8Hz,2H),7.51(dd,J1=7.8Hz,J2=1.8Hz,2H),7.29(d,J=7.8Hz,2H),7.19(t,J=7.8 Hz,2H),6.99-7.07(m,4H),6.46(s,2H),3.51-3.64(m,4H),2.62(q,J=7.5Hz,4H),2.53(tt,J1=12.1Hz,J2=3.1Hz,2H) ,1.94(dd,J1=26.8Hz,J2=11.2Hz,8H),1.79-1.85(m,2H),1.22-1.50(m,38H),1.03-1.18(m,10H),0.89-0.99(m,18H) Example 10: Preparation of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(2-ethylhexyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole

[0158] [ka]

[0159] In the same manner as in Examples 1 to 4, N,N'-bis(2-ethylhexyl)-3,7-bis(4-(2-ethylhexyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole was obtained. Phase transition temperature: Cr 64 Iso MS m / z: 798[M + ] λ max : 583nm (dichloromethane) 1HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.87(d,J=3.7Hz,2H),6.83(d,J=4.1Hz,2H),6.56(s,2H) ,3.56(dq,J1=24.5Hz,J2=7.2Hz,4H),2.81(d,J=6.9Hz,4H),1.80(t,J=5.7Hz,2H),1.64(t,J=5.9 Hz,2H),1.35-1.45(m,18H),1.30(t,J=3.9Hz,14H),0.97(t,J=7.3 Hz,6H),0.93-0.88(m,18H) Example 11: Preparation of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(4-hexyl-2-thienyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole

[0160] [ka]

[0161] In the same manner as in Examples 1 to 4, N,N'-bis(2-ethylhexyl)-3,7-bis(4-(4-hexyl-2-thienyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole was obtained. Phase transition temperature: Cr 218 Iso MS m / z: 906 [M + ] λ max :688nm (dichloromethane) 1 HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.94 (d,J=4.1Hz,2H),7.13(d,J=3.7Hz,2H),7.07(d,J=3.2Hz,2H),6.70(d,J=3.2Hz,2H),6.54(s,2H),3.51-3.63(m,4H),2.80(t,J=7.5Hz,4H),1.79 (t,J=5.5Hz,2H),1.65-1.73(m,4H),1.27-1.50(m,28H),1.00(t,J=7.3Hz,6H),0.93-0.88(m,12H) (Example 12) Preparation of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole

[0162] [ka]

[0163] N,N'-bis(2-ethylhexyl)-3,7-bis(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole was obtained in the same manner as in Examples 1 to 4. Phase transition temperature: Cr 233 N 320 Iso MS m / z: 1274[M + ] λ max :638nm (dichloromethane) 1 HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=8.04(d,J=3.2Hz,2H),7.61(s,2H),7.51(d,J=8.2 Hz,2H),7.41-7.42(m,2H),7.21(d,J=7.8Hz,2H),7.15(t,J=7.8Hz,2H),7.0 4(d,J=8.2Hz,2H),6.99(d,J=11.4Hz,2H),6.64(s,2H),3.58-3.62(m,4H),2 .50-2.60(m,6H),1.94(q,J=12.2Hz,8H),1.83(t,J=5.7Hz,2H),1.23-1.50( m,38H),1.12(q,J=7.3Hz,8H),1.03(t,J=7.3Hz,8H),0.91(t,J=6.6Hz,12H) (Example 13) Preparation of N,N'-dipentyl-3,7-bis(4-(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)-2-thienyl)phenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole

[0164] [ka]

[0165] N,N'-dipentyl-3,7-bis(4-(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)-2-thienyl)phenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole was obtained in the same manner as in Examples 1 to 4. Phase transition temperature: Cr 313 Iso MS m / z: 1392 [M + ] λ max :624nm (dichloromethane) 1 HNMR (400MHz, CDCl3, TMS internal standard): δ(ppm)=7.82(dd,J1=50.8Hz,J2=8.2Hz,8H),7.52-7.60(m,4H),7.31-7.43(m,8H),7.15-7.24(m,4H),6.99-7.06(m,4H) ,4.19(t,J=7.3Hz,4H),2.50-2.62(m,6H),1.90-1.99(m,4H),1.82(s,2H),1 .44-1.59(m,8H),1.27-1.38(m,26H),1.00-1.18(m,6H),0.82-0.97(m,18H) (Examples 14 to 18) The compounds of Examples 14 to 18 were synthesized in the same manner as in Examples 9 to 13.

[0166] [ka]

[0167] (Example 19) Preparation of Liquid Crystal Composition-1 Host liquid crystal (H) consisting of the following composition

[0168] [ka]

[0169] was prepared. A liquid crystal composition (MA) was prepared consisting of 98% of this base liquid crystal (H) and 2% of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(5-(2-ethylhexyl)-2-thienyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole obtained in Example 1. The optical properties of this composition (MA) were measured and the results were as follows.

[0170] λ max :553nm Dichroic ratio: 3.8 The prepared liquid crystal composition (MA) maintained a uniform nematic liquid crystal state for one month at room temperature.

[0171] Furthermore, when a light resistance test was carried out for two weeks using the liquid crystal composition (MA), it was confirmed that the color did not change.

[0172] (Example 20) Preparation of liquid crystal composition-2 A liquid crystal composition (MB) was prepared consisting of 99% of the base liquid crystal (H) and 1% of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(6-(2-ethylhexyloxy)-2-naphthyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole obtained in Example 2. The optical properties of this composition (MB) were measured and the results were as follows.

[0173] λ max :527nm Dichroic ratio: 4.4 The prepared liquid crystal composition (MB) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, when a light resistance test was carried out using the liquid crystal composition (MB), it was confirmed that the color did not change for two weeks. (Example 21) Preparation of Liquid Crystal Composition-3 A liquid crystal composition (MC) was prepared consisting of 99% of the base liquid crystal (H) and 1% of 3N,N'-dipentyl-3,7-bis(4-(5-(2-ethylhexyl)-2-thienyl)phenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole obtained in Example 3. The optical properties of this composition (MC) were measured and the results were as follows.

[0174] λ max :642nm Dichroic ratio: 5.5 The prepared liquid crystal composition (MC) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, a light resistance test was carried out using the liquid crystal composition (MC), and it was confirmed that the color did not change for two weeks. (Example 22) Preparation of liquid crystal composition-4 A liquid crystal composition (MD) was prepared consisting of 98% of the base liquid crystal (H) and 2% of 3,7-bis(6-(2-ethylhexyl)-2-naphthyl)-2H,6H-benzo[1,2-b:4,5-b']dithiophene-2,6-dione obtained in Example 4. The optical properties of this composition (MD) were measured and the results were as follows.

[0175] λ max :659nm Dichroic ratio: 5.1 The prepared liquid crystal composition (MD) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, a light resistance test was carried out using the liquid crystal composition (MD), and it was confirmed that the color did not change for two weeks. (Example 23) Preparation of liquid crystal composition - 5 A liquid crystal composition (ME) was prepared consisting of 98% of the base liquid crystal (H) and 2% of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)phenyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole obtained in Example 9. The optical properties of this composition (ME) were measured and the results were as follows.

[0176] λ max :518nm Dichroic ratio: 4.5 The prepared liquid crystal composition (ME) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, when a light resistance test was carried out using the liquid crystal composition (ME), it was confirmed that the color did not change for two weeks. (Example 24) Preparation of liquid crystal composition-6 A liquid crystal composition (MF) was prepared consisting of 98% of the base liquid crystal (H) and 2% of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(2-ethylhexyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole obtained in Example 10. The optical properties of this composition (MF) were measured and the results were as follows.

[0177] λ max :596nm Dichroic ratio: 2.9 The prepared liquid crystal composition (MF) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, when a light resistance test was carried out using the liquid crystal composition (MF), it was confirmed that the color did not change for two weeks. (Example 25) Preparation of Liquid Crystal Composition-7 A liquid crystal composition (MG) was prepared consisting of 98% of the base liquid crystal (H) and 2% of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(4-hexyl-2-thienyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole obtained in Example 11. The optical properties of this composition (MG) were measured and the results were as follows.

[0178] λ max :688nm Dichroic ratio: 4.2 The prepared liquid crystal composition (MG) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, when a light resistance test was carried out using the liquid crystal composition (MG), it was confirmed that the color did not change for two weeks. (Example 26) Preparation of liquid crystal composition-8 A liquid crystal composition (MJ) was prepared consisting of 98% of the base liquid crystal (H) and 2% of N,N'-bis(2-ethylhexyl)-3,7-bis(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)-2-thienyl)-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole obtained in Example 12. The optical properties of this composition (MJ) were measured and the results were as follows.

[0179] λ max :652nm Dichroic ratio: 3.3 The prepared liquid crystal composition (MJ) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, a light resistance test was carried out using the liquid crystal composition (MJ), and it was confirmed that the color did not change for two weeks. (Example 27) Preparation of liquid crystal composition-9 A liquid crystal composition (MK) was prepared consisting of 98% of the base liquid crystal (H) and 2% of N,N'-dipentyl-3,7-bis(4-(4-(3-ethyl-4-(2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl)phenyl)-2-thienyl)phenyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole obtained in Example 13. The optical properties of this composition (MK) were measured and the results were as follows.

[0180] λ max :646nm Dichroic ratio: 4.9 The prepared liquid crystal composition (MK) maintained a uniform nematic liquid crystal state for more than one month at room temperature. Furthermore, when a light resistance test was carried out using the liquid crystal composition (MK), it was confirmed that the color did not change for two weeks.

[0181] (Comparative Example 1) Preparation of Liquid Crystal Composition-10 The parent liquid crystal (H) 99% and N,N'-dimethyl-3,7-diphenyl-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole described in JP 2015-40231 A

[0182] [ka]

[0183] A liquid crystal composition (ML) containing 1% of the compound (ML) was prepared. The optical properties of the composition (ML) were measured and the results were as follows:

[0184] λ max :465nm Dichroic ratio: 1.9 In addition, the prepared liquid crystal composition (ML) was observed to precipitate dye after 3 days at room temperature. Furthermore, when a light resistance test was carried out using the liquid crystal composition (ML), a change in color was confirmed after 7 days.

[0185] (Comparative Example 2) Preparation of Liquid Crystal Composition-11 The parent liquid crystal (H) 99% and N,N'-bis(2-ethylhexyl)-3,7-diphenyl-2,6-dioxo-1,2,5,6-tetrahydrobenzo[1,2-b:4,5-b']dipyrrole described in J. Mater. Chem. C, 2017, 5, 290-300

[0186] [ka]

[0187] A liquid crystal composition (MM) containing 1% of the methyl group was prepared. The optical properties of the composition (MM) were measured and the results were as follows:

[0188] λ max :470nm Dichroic ratio: 1.8 In addition, the prepared liquid crystal composition (MM) was observed to have precipitated dye after 10 days at room temperature.

[0189] Furthermore, when a light resistance test was carried out using the liquid crystal composition (MM), a change in color was confirmed after 7 days.

[0190] Comparing the dichroic ratio, solubility, and lightfastness of Examples 19 to 27 with those of Comparative Examples 1 and 2, it is found that the compounds of the present invention have a larger dichroic ratio, higher solubility, and higher lightfastness than the compounds of Comparative Examples 1 and 2. In particular, the compounds of Examples 21, 22, and 27 of the present invention maintain high solubility while exhibiting extremely large dichroic ratios. This demonstrates that the compounds of the present invention are characterized by having both a large dichroic ratio and high solubility.

Claims

1. General formula (1) 【Chemical 1】 (wherein B is a group represented by general formula (2), (3) or (4) 【Chemistry 2】 wherein the carbon atoms represented by *1 to *4 in the general formula (2), (3) or (4) correspond to the carbon atoms represented by *1 to *4 in the general formula (1), and one or more hydrogen atoms in these groups are selected from the groups represented by the substituents L １ may be replaced by L １ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl 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 -CH ２ each independently represents a linear alkyl group having 1 to 20 carbon atoms which may be substituted by —O—, —S—, —CO—, —CS—, —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-, but the oxygen atoms are not directly bonded to each other and any hydrogen atom in the alkyl group may be substituted by a fluorine atom, R １ and R ２ each independently represents an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, and one —CH ２ - or two or more non-adjacent -CH ２ -is-NR ３ -, -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, and a hydrogen atom present in these groups may be substituted by a fluorine atom, ３ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 30 carbon atoms, and one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced by -O-, -S-, -COO-, -OCO- or -CO-, and a hydrogen atom in these groups may be replaced by a fluorine atom; X １ and X ２ are each independently —S— or —NR ４ -, where R ４ represents an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, and one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced by -O-, -S-, -CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH═CH-, -CF═CF-, -C≡C-, or an optionally substituted hydrocarbon ring or heterocycle having 3 to 16 carbon atoms, and a hydrogen atom in these groups may be substituted by a fluorine atom, A １ and A ２ each independently represents an optionally substituted hydrocarbon ring or heterocycle having 3 to 16 carbon atoms, Z １ and Z ２ are each independently -CH ２ O-, -OCH ２ -, -CF ２ O-, -OCF ２ -, -COO-, -OCO-, -CH ２ CH ２ -, -CF ２ CF ２ represents -, -CH=CH-, -CF=CF-, -N=CH-, -CH=N-, -N=N-, -C≡C- or a single bond, i and j each independently represent an integer of 1 to 4; A １ and A ２ If there are multiple A's, １ and A ２ may be the same or different, Z １ and Z ２ If there are multiple Z １ and Z ２ may be the same or different, and multiple R ３ and R ４ If there are multiple R ３ and R ４ may be the same or different.) A liquid crystal composition containing one or more compounds represented by the following formula:

2. In general formula (1), R １ and R ２ 2. The liquid crystal composition according to claim 1, wherein each independently represents an alkyl group having 3 to 20 carbon atoms, an alkoxy group having 3 to 20 carbon atoms, or an alkylamino group having 3 to 20 carbon atoms.

3. In general formula (1), A １ and A ２ are each independently (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced with -O- or -S-.) (b) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (these groups contain A hydrogen atom in the naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be substituted with a fluorine atom or a chlorine atom, and one -CH= or two or more -CH= in the naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be substituted with a -N=. (d) a thiophene-2,5-diyl group, a thiophene-2,4-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, or a thieno[3,2-b]thiophene-2,5-diyl group (one —CH= or two or more non-adjacent —CH= groups in this group may be replaced by —N=). These groups are unsubstituted or have one or more substituents L ２ may be replaced by L ２ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl 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 -CH ２ 3. The liquid crystal composition according to claim 1, wherein each - independently represents a linear alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms which may be substituted with -O-, -S-, -CO-, -CS-, -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-, wherein oxygen atoms are not directly bonded to each other and any hydrogen atom in the alkyl group may be substituted with a fluorine atom.

4. In general formula (1), X １ and X ２ The liquid crystal composition according to claim 1 , wherein each independently represents —S—.

5. In general formula (1), X １ and X ２ are each independently -NR ４ The liquid crystal composition according to claim 1 , wherein

6. The compound represented by general formula (1) is represented by the following formulas (1-A) to (1-F): 【Chemistry 3】 (In the formula, R １ , R ２ , X １ , X ２ , A １ , A ２ , Z １ , Z ２ , i and j are R in general formula (1) １ , R ２ , X １ , X ２ , A １ , A ２ , Z １ , Z ２ 6. The liquid crystal composition according to claim 1, wherein i and j have the same meanings as those of the compound represented by any one of the following formulas:

7. A liquid crystal display element or a dimming element using a liquid crystal composition described in any one of claims 1 to 6.

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