Liquid crystal composition, display element, and compound

Abstract

The problem to be solved by the present invention is to provide a liquid crystal composition for an active drive display element with improved wavelength dispersion, a display element using the liquid crystal composition, and a compound. The present invention provides a liquid crystal composition for an active drive display element, characterized in that it contains at least one compound (Z), which has a characteristic structure, i.e., a compound (Z) containing a group (ZG) with large wavelength dispersion in a direction perpendicular to the long axis of the molecule, and further provides a display element using the liquid crystal composition. In addition, as compound (Z), a compound represented by general formula (I) is provided.

Description

Technical Field

[0001] The present invention relates to a liquid crystal composition having improved wavelength dispersion, a display element using the liquid crystal composition, and a compound. Background Art

[0002] Vertically aligned liquid crystal display elements are characterized by high contrast and are widely used in products such as televisions. However, there is a problem that the color tone and chromaticity change when the display element is viewed from the front or from an oblique side.

[0003] In a graph plotted with the wavelength λ of the incident light to the liquid crystal composition as the horizontal axis and the refractive index anisotropy (Δn) as the vertical axis, when the shorter the wavelength (λ), the larger the refractive index anisotropy (Δn), the liquid crystal composition can be said to be "positive wavelength dispersion" or "positive dispersion", and when the shorter the wavelength (λ), the smaller the refractive index anisotropy (Δn), the liquid crystal composition can be said to be "reverse wavelength dispersion" or "reverse dispersion". The above problem arises because the driving liquid crystal composition used in the liquid crystal display element is positive dispersion. According to this report, there is a case where, according to the simulation results, the above problem can be solved by using a liquid crystal material with reverse dispersion (Patent Document 1). However, there is no reported example of a liquid crystal composition with reverse dispersion that meets the various physical properties required for display products, and it is required to develop such a liquid crystal composition.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Publication No. 2018-105908 Summary of the invention

[0007] Problems to be solved by the invention

[0008] The problem to be solved by the present invention is to provide a liquid crystal composition for an active drive display element having improved wavelength dispersion, a display element using the liquid crystal composition, and a compound.

[0009] Solution to the problem

[0010] The inventors of the present invention have made intensive research to solve the above-mentioned problems, and have completed the development of a specific liquid crystal composition. That is, the present invention provides a liquid crystal composition for an active drive display element, characterized in that it contains at least one compound (Z) having a group (ZG) in a direction perpendicular to the long axis of the molecule, and the group (ZG) has a large wavelength dispersion, and the present invention provides a display element using the liquid crystal composition, and the compound.

[0011] Effects of the Invention

[0012] When the liquid crystal composition of the present invention is used for a display element, the change in color tone, chromaticity, etc. when the liquid crystal orientation changes due to voltage application is small, and therefore, it is useful as a material for a liquid crystal display element. BRIEF DESCRIPTION OF THE DRAWINGS

[0013] [ Figure 1 ] Figure 1 This is a conceptual diagram of compound (Z).

[0014] [ Figure 2 ] Figure 2 This is a graph conceptually showing the wavelength dispersion of each group (LA, LB, and ZG) constituting the compound (Z).

[0015] [ Figure 3 ] Figure 3 It conceptually shows the structure of compound (Z). DETAILED DESCRIPTION

[0016] The liquid crystal composition of the present invention is a liquid crystal composition for an active drive display element, characterized in that it contains at least one compound (Z) having a group (ZG) in a direction perpendicular to the long axis of the molecule, and the group (ZG) has a large wavelength dispersion. From the viewpoint of changes in hue and chromaticity when the liquid crystal orientation changes due to the application of voltage, the liquid crystal phase temperature range of the liquid crystal composition, the refractive index anisotropy, the dielectric constant anisotropy, the rotational viscosity and the elastic modulus, the compound (Z) is preferably composed of a group (LA and LB) having a small wavelength dispersion and a group (ZG) having a large wavelength dispersion ( Figure 1 ). A graph conceptually showing the wavelength dispersion of each group (LA, LB and ZG) constituting the compound (Z) is shown in FIG. Figure 2 .

[0017] exist Figure 1 In the formula (A), the groups (LA and LB) respectively represent small wavelength dispersion, and the group (ZG) represents large wavelength dispersion. The compound (Z) preferably has the groups (LA and LB) in the direction of the molecular long axis and the group (ZG) in the direction perpendicular to the molecular long axis, wherein the groups (LA and LB) have small wavelength dispersion, and the group (ZG) has large wavelength dispersion. The structure of the compound (Z) is shown conceptually as follows: Figure 3 .

[0018] exist Figure 3In the structure described, each group (LA, LB and ZG) may be bonded by a single bond, a double bond or a triple bond, or may be bonded via a divalent linking group, or may form the same condensed ring system. In addition, the group (ZG) may be bonded at the central part of the group (LA and LB) and the group (ZG), or may be bonded at the end of the group (ZG). Here, the "molecular long axis" in the compound (Z) refers to the axis that coincides with the molecular long axis of the rod-like liquid crystal compound when a liquid crystal composition containing a rod-like liquid crystal compound is added. The so-called "containing groups (LA and LB) having small wavelength dispersion in the direction of the molecular long axis" means that when the compound (Z) is added to a liquid crystal composition containing a rod-like liquid crystal compound, the axis containing the groups (LA and LB) coincides with the molecular long axis of the rod-like liquid crystal compound. More specifically, the compound (Z) is preferably a compound represented by the following general formula (I).

[0019] [Chemistry 1]

[0020]

[0021] (Where R 11 and R 12 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms,

[0022] A 11 and A 13 Each independently represents a group selected from the following formula (A1-1) to formula (A1-11),

[0023] [Chemistry 2]

[0024]

[0025] (where the dotted line indicates the bonding position), 11 When there are multiple, each can be the same or different. 13 When there are multiple, they may be the same or different.

[0026] A 12 represents a group (ZG) having large wavelength dispersion, the group (ZG) is oriented in a direction substantially perpendicular to the molecular long axis of the compound represented by the general formula (I),

[0027] Z 11 and Z 12Each independently represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO- , -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. In the presence of multiple Z 11 In the case of multiple Z 12 In the case of , they can be the same or different.

[0028] m11 and m12 each independently represent an integer from 0 to 5, and m11+m12 represents an integer from 0 to 5).

[0029] In the general formula (I), A 12 A represents a group (ZG) having large wavelength dispersion, and the group (ZG) is oriented in a direction perpendicular to the molecular long axis of the compound represented by the general formula (I). From the viewpoint of changes in hue and chromaticity when the liquid crystal orientation changes due to the application of voltage, the liquid crystal phase temperature range of the liquid crystal composition, the anisotropy of the refractive index, the anisotropy of the dielectric constant, the rotational viscosity and the elastic modulus, A 12 Preferably, it represents a group selected from the following formula (A12-1) to formula (A12-4).

[0030] [Chemistry 3]

[0031]

[0032] (Where the dotted line indicates the bonding position, B 1 represents a 5-membered ring which may further have a condensed ring, B 2 The groups represented by formula (A12-1) to formula (A12-4) may be substituted, and any -CH= may be independently substituted by -N=, and -CH2- may be independently substituted by -O-, -S-, -NR T -(where RT represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms), -CS- or -CO-substituted), A 12 More preferably, it represents a group selected from the following formula (A12-1-1) to formula (A12-4-9).

[0033] [Chemistry 4]

[0034]

[0035] [Chemistry 5]

[0036]

[0037] [Chemistry 6]

[0038]

[0039] [Chemistry 7]

[0040]

[0041] (In the formula, the dotted line indicates the bonding position, these groups can be substituted, any -CH= can be independently replaced by -N=, and -CH2- can be independently replaced by -O-, -S-, -NR T1 -(where R T1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an aromatic group having 6 to 10 carbon atoms, or a heteroaryl group having 3 to 10 carbon atoms), -CS- or -CO-substituted), A 12 More preferably, it represents a group selected from the following formula (A122-1-1) to formula (A122-3-3).

[0042] [Chemistry 8]

[0043]

[0044] (In the formula, the dotted line indicates the bonding position. These groups can be substituted. Any -CH= can be independently substituted by -N=, and -CH2- can be independently substituted by -O-, -S-, -NR T11 -(where R T11 represents an alkyl group having 1 to 5 carbon atoms, an aromatic group having 6 to 9 carbon atoms, or a heteroaryl group having 3 to 9 carbon atoms), -CS- or -CO-), A 12 It is further more preferably a group selected from the following formula (A123-1) to formula (A123-8).

[0045] [Chemistry 9]

[0046]

[0047] (In the formula, the dotted line indicates the bonding position, and these groups are unsubstituted or substituted with one or more substituents L G Replacement, T 1 It represents a group selected from the following formula (T1-1) to formula (T1-6).

[0048] [Chemistry 10]

[0049]

[0050] (In the formula, there is one bond at any position, any -CH= can be independently substituted by -N=, and -CH2- can be independently substituted by -O- or -S-. Here, the term "having one bond at any position" means, for example, in T1-1 and formula (A123-1) to formula (A123-8) 1 In the case of a bond, it means that there is one bond at any position of the formula (T1-1) (hereinafter, in the present invention, having a bond at any position has the same meaning). In addition, these groups are unsubstituted or substituted with one or more substituents L G replace),

[0051] L G represents a halogen atom, a cyano group, a nitro group, a pentafluorosulfanyl group, an amino group which may be substituted, a silyl group which may be substituted, any hydrogen atom which may be substituted by a fluorine atom, and one -CH2- or two or more non-adjacent -CH2- groups each independently represent an alkyl group having 1 to 20 carbon atoms which may be substituted 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-), A 12 More preferably, it represents a group selected from the following formula (A124-1) to formula (A124-4).

[0052] [Chemistry 11]

[0053]

[0054] (In the formula, the dotted line indicates the bonding position, and these groups are unsubstituted or substituted with one or more substituents L G1 Replacement, T 11 It represents a group selected from the following formula (T11-1) to formula (T11-3).

[0055] [Chemistry 12]

[0056]

[0057] (wherein, there is one bond at any position, and these groups are unsubstituted or substituted with one or more substituents L G1 Replacement), L G1 represents a fluorine atom, a chlorine atom, a pentafluorosulfanyl group, any hydrogen atom may be substituted by a fluorine atom, and one -CH2- or two or more non-adjacent -CH2- groups each independently represent an alkyl group having 1 to 10 carbon atoms which may be substituted by -O-, -S-, -COO-, -OCO-, -CH=CH-, -CF=CF- or -C≡C-, A 12 It particularly preferably represents a group selected from the following formula (A125-1) to formula (A125-4).

[0058] [Chemistry 13]

[0059]

[0060] (Where the dotted line indicates the bonding position, T 12 It represents a group selected from the following formula (T12-1) and formula (T12-2).

[0061] [Chemistry 14]

[0062]

[0063] (wherein, there is one bond at any position, and these groups are unsubstituted or substituted with one or more substituents L G2 Replacement), L G2 represents a fluorine atom, a pentafluorosulfanyl group, or an alkyl group having 1 to 5 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom and one -CH2- may be substituted by -O- or -CH=CH-).

[0064] From the viewpoint of changes in hue and chromaticity when the liquid crystal orientation changes due to applied voltage, the liquid crystal phase temperature range, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, the compound represented by general formula (I) is preferably a compound represented by the following general formula (Ii).

[0065] [Chemistry 15]

[0066]

[0067] (Where R 111 and R 121 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms,

[0068] A111 and A 131 Each independently represents a group selected from the following formula (A11-1) to formula (A11-9).

[0069] [Chemistry 16]

[0070]

[0071] (where the dotted line indicates the bonding position), 111 When there are multiple A 131 In the case of , they can be the same or different.

[0072] A 121 represents a group selected from the above formula (A12-1-1) to formula (A12-4-9),

[0073] Z 111 and Z 121 Each independently represents -OCH2-, -CH2O-, -CH2CH2-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. 111 In the case of multiple Z 121 In the case of , they can be the same or different.

[0074] m111 and m121 each independently represent an integer from 1 to 4, and m111+m121 represents an integer from 1 to 4).

[0075] The compound represented by the general formula (I) is more preferably a compound represented by the following general formula (I-ii).

[0076] [Chemistry 17]

[0077]

[0078] (Where R 112 and R 122 each independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, or an alkenyloxy group having 2 to 3 carbon atoms,

[0079] A 112 and A 132 Each independently represents a group selected from the following formula (A112-1) to formula (A112-7).

[0080] [Chemistry 18]

[0081]

[0082] (where the dotted line indicates the bonding position), 112 When there are multiple A 132 In the case of , they can be the same or different.

[0083] A 122 represents a group selected from the above formula (A122-1-1) to formula (A122-3-3),

[0084] Z 112 and Z 122 Each independently represents -OCH2-, -CH2O-, -CH2CH2-, -COO-, -OCO-, -CF2O-, -OCF2- or a single bond. 112 In the case of multiple Z 122 In the case of , they can be the same or different.

[0085] m112 and m122 each independently represent 1, 2 or 3, and m112+m122 represents an integer from 1 to 4).

[0086] The compound represented by the general formula (I) is more preferably a compound represented by the following general formula (I-iii).

[0087] [Chemistry 19]

[0088]

[0089] (Where R 113 and R 123 each independently represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, or an alkenyl group having 2 to 3 carbon atoms,

[0090] A 113 and A 133 Each independently represents a group selected from the following formula (A113-1) to formula (A113-5).

[0091] [Chemistry 20]

[0092]

[0093] (where the dotted line indicates the bonding position), 113 When there are multiple A 133 In the case of , they can be the same or different.

[0094] A123 represents a group selected from the above formula (A123-1) to formula (A123-8),

[0095] Z 113 and Z 123 Each independently represents -OCH2-, -CH2O-, -CF2O-, -OCF2- or a single bond. 113 In the case of multiple Z 123 In the case of , they can be the same or different.

[0096] m113 and m123 each independently represent 1 or 2, and m113+m123 represents 2, 3 or 4).

[0097] The compound represented by the general formula (I) is more preferably a compound selected from the group consisting of compounds represented by the following general formulae (I-iv-1) to (I-iv-4).

[0098] [Chemistry 21]

[0099]

[0100] (Where R 114 and R 124 each independently represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, or an alkenyl group having 2 or 3 carbon atoms,

[0101] A 114 and A 134 Each independently represents a group selected from the following formula (A114-1) to formula (A114-5).

[0102] [Chemistry 22]

[0103]

[0104] (where the dotted line indicates the bonding position), 114 When there are multiple A 134 In the case of , they can be the same or different.

[0105] A 124 represents a group selected from the above formula (A124-1) to formula (A124-4),

[0106] Z 1141 , Z 1142 , Z 1241 and Z 1242 each independently represents -OCH2-, -CH2O-, -CF2O-, -OCF2- or a single bond).

[0107] The compound represented by the general formula (I) is particularly preferably a compound selected from the group consisting of compounds represented by the following general formula (Iv-1) and general formula (Iv-2).

[0108] [Chemistry 23]

[0109]

[0110] (Where R 115 and R 125 each independently represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, or an alkenyl group having 2 or 3 carbon atoms,

[0111] A 125 represents a group selected from the above formula (A125-1) to formula (A125-4),

[0112] Z 115 and Z 125 each independently represents -OCH2-, -CH2O- or a single bond).

[0113] Specific examples of the compound represented by general formula (I) include compounds represented by the following formulae (I-1) to (I-30).

[0114] [Chemistry 24]

[0115]

[0116] [Chemistry 25]

[0117]

[0118] [Chemistry 26]

[0119]

[0120] [Chemistry 27]

[0121]

[0122] [Chemistry 28]

[0123]

[0124] [Chemistry 29]

[0125]

[0126] [Chemistry 30]

[0127]

[0128] [Chemistry 31]

[0129]

[0130] [Chemistry 32]

[0131]

[0132] [Chemistry 33]

[0133]

[0134] In the case where the liquid crystal composition of the present invention contains a compound represented by the general formula (I), it may contain one compound represented by the general formula (I), or it may contain multiple compounds represented by the general formula (I). In the case where the liquid crystal composition of the present invention contains a compound represented by the general formula (I), the total content of the compound represented by the general formula (I) in the liquid crystal composition is preferably 5% by mass or more and 95% by mass or less, more preferably 6% by mass or more and 40% by mass or less, further preferably 8% by mass or more and 37% by mass or less, further more preferably 12% by mass or more and 33% by mass or less, and particularly preferably 20% by mass or more and 25% by mass or less. Here, "the total content of the compound represented by the general formula (I)" means that when the liquid crystal composition contains one compound represented by the general formula (I), it means the content of the compound represented by the general formula (I), and when the liquid crystal composition contains multiple compounds represented by the general formula (I), it means the total content of the multiple compounds represented by the general formula (I).

[0135] The liquid crystal composition of the present invention preferably contains a compound represented by the following general formula (III).

[0136] [Chemistry 34]

[0137]

[0138] (Where R 31 and R 32 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms,

[0139] A 31 and A 32 Each independently represents a group selected from the following formula (A3-1) to formula (A3-8).

[0140] [Chemistry 35]

[0141]

[0142] (where the dotted line indicates the bonding position), when there are multiple A 32In the case of , they can be the same or different.

[0143] m31 represents an integer from 1 to 4). From the viewpoints of changes in hue and chromaticity when the liquid crystal orientation changes due to applied voltage, the liquid crystal phase temperature range of the liquid crystal composition, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus, the compound represented by the general formula (III) is preferably a compound represented by the following general formula (III-i).

[0144] [Chemistry 36]

[0145]

[0146] (Where R 311 and R 321 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms,

[0147] A 311 and A 321 Each independently represents a group selected from the following formula (A31-1) to formula (A31-6).

[0148] [Chemistry 37]

[0149]

[0150] (where the dotted line indicates the bonding position), when there are multiple A 321 In the case of , they can be the same or different.

[0151] m311 represents an integer of 1 to 3. ), the compound represented by the general formula (III) is more preferably a compound represented by the following general formula (III-ii).

[0152] [Chemistry 38]

[0153]

[0154] (Where R 312 and R 322 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms,

[0155] A 312 and A 322 Each independently represents a group selected from the following formula (A32-1) to formula (A32-4).

[0156] [Chemistry 39]

[0157]

[0158] (where the dotted line indicates the bonding position), when there are multiple A 322 In the case of , they can be the same or different.

[0159] m312 represents 1 or 2. ), the compound represented by the general formula (III) is further preferably a compound represented by the following general formula (III-iii).

[0160] [Chemistry 40]

[0161]

[0162] (Where R 313 and R 323 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms,

[0163] A 313 and A 323 Each independently represents a group selected from the following formula (A33-1) and formula (A33-2).

[0164] [Chemistry 41]

[0165]

[0166] (where the dotted line indicates the bonding position), when there are multiple A 323 In the case of , they can be the same or different.

[0167] m313 represents 1 or 2. ), the compound represented by the general formula (III) is particularly preferably a compound selected from the group consisting of compounds represented by the following general formulas (III-iv-1) to (III-iv-10).

[0168] [Chemistry 42]

[0169]

[0170] [Chemistry 43]

[0171]

[0172] (Where R 314 and R 324 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.)

[0173] In the case where the liquid crystal composition of the present invention contains a compound represented by the general formula (III), it may contain one compound represented by the general formula (III), or it may contain multiple compounds represented by the general formula (III). In the case where the liquid crystal composition of the present invention contains a compound represented by the general formula (III), the total content of the compound represented by the general formula (III) in the liquid crystal composition is preferably 5% by mass or more and 95% by mass or less, more preferably 8% by mass or more and 55% by mass or less, further preferably 10% by mass or more and 50% by mass or less, further more preferably 15% by mass or more and 45% by mass or less, and particularly preferably 20% by mass or more and 40% by mass or less. Here, "the total content of the compound represented by the general formula (III)" means that when the liquid crystal composition contains one compound represented by the general formula (III), it means the content of the compound represented by the general formula (III), and when the liquid crystal composition contains multiple compounds represented by the general formula (III), it means the total content of the multiple compounds represented by the general formula (III).

[0174] The liquid crystal composition of the present invention preferably has a dielectric anisotropy (Δε) of -5.0 or more and -1.0 or less. From the viewpoint of the liquid crystal phase temperature range, driving voltage, rotational viscosity and elastic modulus of the liquid crystal composition, the dielectric anisotropy (Δε) is preferably -4.9 or more and -1.5 or less, more preferably -4.8 or more and -2.0 or less, further preferably -4.7 or more and -2.5 or less, further more preferably -4.6 or more and -2.7 or less, and particularly preferably -4.5 or more and -3.0 or less.

[0175] The liquid crystal composition of the present invention may contain a compound represented by the following general formula (II).

[0176] [Chemistry 44]

[0177]

[0178] (Where R 21 and R 22 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms,

[0179] A 21 and A 22 Each independently represents a group selected from the following formula (A2-1) to formula (A2-11).

[0180] [Chemistry 45]

[0181]

[0182] (where the dotted line indicates the bonding position), when there are multiple A 21 In the case of multiple A 22 In the case of , they can be the same or different.

[0183] Z 21 and Z 22 Each independently represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO- , -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. In the presence of multiple Z 21 In the case of multiple Z 22 In the case of , they can be the same or different.

[0184] m21 and m22 each independently represent an integer of 0 to 3, and m21+m22 represents an integer of 1 to 3). From the viewpoint of changes in hue and chromaticity when the liquid crystal orientation changes due to applied voltage, the liquid crystal phase temperature range of the liquid crystal composition, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus, the compound represented by the general formula (II) is preferably a compound represented by the following general formula (II-i).

[0185] [Chemistry 46]

[0186]

[0187] (Where R 211 and R 221 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms,

[0188] A 211 and A 221Each independently represents a group selected from the following formula (A21-1) to formula (A21-9).

[0189] [Chemistry 47]

[0190]

[0191] (where the dotted line indicates the bonding position), when there are multiple A 211 In the case of multiple A 221 In the case of , they can be the same or different.

[0192] Z 211 and Z 221 Each independently represents -OCH2-, -CH2O-, -CH2CH2-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. 211 In the case of multiple Z 221 In the case of , they can be the same or different.

[0193] m211 and m221 each independently represent an integer from 0 to 3, and m211+m221 represents an integer from 1 to 3).

[0194] The compound represented by the general formula (II) is preferably a compound represented by the following general formula (II-ii).

[0195] [Chemistry 48]

[0196]

[0197] (Where R 212 and R 222 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms,

[0198] A 212 and A 222 Each independently represents a group selected from the following formula (A22-1) to formula (A22-7).

[0199] [Chemistry 49]

[0200]

[0201] (where the dotted line indicates the bonding position), when there are multiple A 212In the case of multiple A 222 In the case of , they can be the same or different.

[0202] Z 212 and Z 222 Each independently represents -OCH2-, -CH2O-, -CH2CH2-, -COO-, -OCO-, -CF2O-, -OCF2- or a single bond. 212 In the case of multiple Z 222 In the case of , they can be the same or different.

[0203] m212 and m222 each independently represent 0, 1 or 2, and m212+m222 represents 1 or 2).

[0204] The compound represented by the general formula (II) is more preferably a compound represented by the following general formula (II-iii).

[0205] [Chemistry 50]

[0206]

[0207] (Where R 212 and R 222 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms,

[0208] A 213 and A 223 Each independently represents a group selected from the following formula (A23-1) to formula (A23-5).

[0209] [Chemistry 51]

[0210]

[0211] (where the dotted line indicates the bonding position), when there are multiple A 213 In the case of multiple A 223 In the case of , they can be the same or different.

[0212] Z 213 and Z 223 Each independently represents -OCH2-, -CH2O-, -CH2CH2- or a single bond. 213 In the case of multiple Z 223 In the case of , they can be the same or different.

[0213] m213 and m223 each independently represent 0, 1 or 2, and m213+m223 represents 1 or 2).

[0214] The compound represented by the general formula (II) is particularly preferably a compound selected from the group consisting of compounds represented by the following general formulae (II-iv-1) to (II-iv-8).

[0215] [Chemistry 52]

[0216]

[0217] [Chemistry 53]

[0218]

[0219] (Where R 214 and R 224 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms).

[0220] When the liquid crystal composition of the present invention is used in a PSA, PS-VA, PS-IPS, or PI-Less type liquid crystal display element, it preferably contains a compound represented by the following general formula (IV).

[0221] [Chemistry 54]

[0222]

[0223] (Where P 41 and P 42 each independently represents a group that is polymerized by free radical polymerization, cationic polymerization or anionic polymerization,

[0224] Sp 41 and Sp 42 Each independently represents a spacer or a single bond,

[0225] A 41 and A 42 Each independently represents a group selected from the following formula (A4-1) to formula (A4-9).

[0226] [Chemistry 55]

[0227]

[0228] (Where the dotted line indicates the bonding position, L 4represents a halogen atom, a cyano group, a nitro group, a pentafluorosulfanyl group, an optionally substituted amino group, an optionally substituted silyl group, an alkyl group having 1 to 20 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- may each independently be substituted 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-, or P L -SP L - represented by a group (wherein, P L represents a group that polymerizes by free radical polymerization, cationic polymerization, or anionic polymerization, Sp L represents a spacer or a single bond), in the presence of multiple L 4 In the case of multiple A 42 In the case of , they can be the same or different.

[0229] Z 41 Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO- NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -C H=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. 41 In the case of , they can be the same or different.

[0230] m41 represents an integer of 1 to 4). From the viewpoint of voltage holding ratio, tilt angle stability, and compatibility with a liquid crystal composition, the compound represented by the general formula (IV) preferably contains a compound represented by the following general formula (IV-i).

[0231] [Chemistry 56]

[0232]

[0233] (Where P 411 and P 421 Each independently represents a group selected from the following formula (P-1) to formula (P-20).

[0234] [Chemistry 57]

[0235]

[0236] (where the dotted line indicates the bonding position),

[0237] Sp 411 and Sp 421 Each independently represents a linear or branched alkylene group having 1 to 20 carbon atoms or a single bond, in which any hydrogen atom in the group may be substituted by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- may each independently be substituted by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-,

[0238] A 411 and A 421 Each independently represents a group selected from the following formula (A41-1) to formula (A41-9).

[0239] [Chemistry 58]

[0240]

[0241] (Where the dotted line indicates the bonding position, L 41 represents an alkyl group having 1 to 10 carbon atoms in which a fluorine atom, a chlorine atom, or any hydrogen atom may be substituted by a fluorine atom, and one -CH2- or two or more non-adjacent -CH2- may be independently substituted by -O-, -COO-, -OCO-, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-; or P L -Sp L - represented by a group (wherein, P L Representing the above formula (P-1) to formula (P-20), Sp Lrepresents a straight-chain or branched alkylene group having 1 to 20 carbon atoms or a single bond) in which any hydrogen atom in the group may be substituted by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- groups may be independently substituted by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, and in which a plurality of L 41 In the case of multiple A 421 In the case of , they can be the same or different.

[0242] Z 411 represents -OCH2-, -CH2O-, -CH2CH2-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. 411 In the case of , they can be the same or different.

[0243] m411 represents 1, 2 or 3), and the compound represented by the general formula (IV) more preferably contains a compound represented by the following general formula (IV-ii).

[0244] [Chemistry 59]

[0245]

[0246] (Where P 412 and P 422 Each independently represents a group selected from the group consisting of formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-5), formula (P-7), formula (P-11), formula (P-13), formula (P-15) and formula (P-18),

[0247] Sp 412 and Sp 422 Each independently represents a linear or branched alkylene group having 2 to 12 carbon atoms or a single bond, wherein one -CH2- or two or more non-adjacent -CH2- groups may be independently substituted by -O-, -COO-, -OCO- or -O-CO-O-,

[0248] A 412 and A 422 Each independently represents a group selected from the following formula (A42-1) to formula (A42-7).

[0249] [Chemistry 60]

[0250]

[0251] (Where the dotted line indicates the bonding position, L 42 represents an alkyl group having 1 to 5 carbon atoms, wherein a fluorine atom, any hydrogen atom may be substituted by a fluorine atom, and one -CH2- or two or more non-adjacent -CH2- may be independently substituted by -O-, and in the presence of a plurality of L 42 In the case of multiple A 422 In the case of , they can be the same or different.

[0252] Z 412 represents -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or a single bond. 412 In the case of , they can be the same or different.

[0253] m412 represents 1 or 2), and the compound represented by the general formula (IV) further preferably contains a compound represented by the following general formula (IV-iii).

[0254] [Chemistry 61]

[0255]

[0256] (Where P 413 and P 423 Each independently represents a group selected from the group consisting of formula (P-1), formula (P-2), formula (P-3) and formula (P-18),

[0257] Sp 413 and Sp 423 Each independently represents a linear alkylene group having 2 to 8 carbon atoms or a single bond, in which one -CH2- or two or more non-adjacent -CH2- groups may be independently substituted by -O-,

[0258] A 413 and A 423 Each independently represents a group selected from the following formula (A43-1) to formula (A43-7).

[0259] [Chemistry 62]

[0260]

[0261] (Where the dotted line indicates the bonding position, L 43 represents a fluorine atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 5 carbon atoms in which a hydrogen atom is substituted with a fluorine atom, or an alkoxy group having 1 to 4 carbon atoms in which a hydrogen atom is substituted with a fluorine atom, and in the case where there are a plurality of L 43In the case of multiple A 423 In the case of , they can be the same or different.

[0262] Z 413 Indicates -CH=CH-COO-, -OCO-CH=CH- or a single bond. 413 In the case of , they can be the same or different.

[0263] m413 represents 1 or 2), and the compound represented by the general formula (IV) particularly preferably contains a compound selected from the group consisting of compounds represented by the following general formulae (IV-iv-1) to (IV-iv-5).

[0264] [Chemistry 63]

[0265]

[0266] (Where P 414 and P 424 Each independently represents a group selected from the group consisting of formula (P-1) and formula (P-2),

[0267] Sp 414 and Sp 424 Each independently represents a linear alkylene group having 2 to 5 carbon atoms or a single bond,

[0268] A 414 , A 424 and A 434 Each independently represents a group selected from the following formula (A44-1) to formula (A44-7).

[0269] [Chemistry 64]

[0270]

[0271] (Where the dotted line indicates the bonding position, L 44 represents a fluorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and in the presence of a plurality of L 44 , each may be the same or different).

[0272] Specific examples of the compound represented by the general formula (IV) include compounds represented by the following general formulae (IV-v-1) to (IV-v-15).

[0273] [Chemistry 65]

[0274]

[0275] [Chemistry 66]

[0276]

[0277] [Chemistry 67]

[0278]

[0279] [Chemistry 68]

[0280]

[0281] (Where P 415 and P 425 Each independently represents a group selected from the group consisting of formula (P-1) and formula (P-2),

[0282] Sp 425 represents a straight-chain alkylene group having 2 to 5 carbon atoms).

[0283] In order to improve its storage stability, a stabilizer may also be added to the liquid crystal composition of the present invention. As usable stabilizers, for example, hydroquinones, hydroquinone monoalkyl ethers, tert-butyl catechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, etc. may be cited. Relative to the composition, the amount added when using the stabilizer is preferably in the range of 0.005% to 1% by mass, more preferably 0.02% to 0.8% by mass, and further preferably 0.03% to 0.5% by mass. In addition, one stabilizer may be used, or two or more stabilizers may be used in combination. As stabilizers, compounds represented by the following general formula (X1) may be cited.

[0284] [Chemistry 69]

[0285]

[0286] (Where Sp x1 represents an alkylene group having 1 to 20 carbon atoms or a single bond, in which one -CH2- or two or more non-adjacent -CH2- may be independently substituted 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 A x1 It represents a group selected from the following formula (Ax1-1) to formula (Ax1-8).

[0287] [Chemistry 70]

[0288]

[0289] (where the dotted line indicates the bonding position), when there are multiple A x1 In the case of , they can be the same or different.

[0290] Z x1 Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO- NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -C H=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. x1 In the case of , each may be the same or different, mx1 represents 0 or 1, and mx2 represents an integer from 0 to 4).

[0291] From the viewpoint of voltage holding ratio and compatibility with a liquid crystal composition, the compound represented by the general formula (X1) is preferably a compound represented by the following general formula (X1-i).

[0292] [Chemistry 71]

[0293]

[0294] (Where Sp x11 represents an alkylene group having 1 to 20 carbon atoms or a single bond, wherein one -CH2- or two or more non-adjacent -CH2- groups may be independently substituted by -O-, -COO- or -OCO-, x11 represents a group selected from the following formula (Ax11-1) and formula (Ax11-2),

[0295] [Chemistry 72]

[0296]

[0297] (where the dotted line indicates the bonding position), when there are multiple A x11 In the case of , they can be the same or different.

[0298] Z x11 represents -COO-, -OCO-, -OCO-CH2CH2-, -CH2CH2-COO- or a single bond. x11 In the case of , they can be the same or different.

[0299] mx11 means 0 or 1,

[0300] mx21 represents 0 or 1), and the compound represented by the general formula (X1) is particularly preferably a compound represented by the following general formula (X1-ii-1) to general formula (X1-ii-4).

[0301] [Chemistry 73]

[0302]

[0303] (Where Sp x12 represents an alkylene group having 1 to 20 carbon atoms or a single bond).

[0304] In addition, compounds represented by the following general formula (X2) can be mentioned.

[0305] [Chemistry 74]

[0306]

[0307] (Where R x21 , R x22 , R x23 and R x24 each independently represents a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms,

[0308] Sp x21 、Sp x22 、Sp x23 and Sp x24 Each independently represents a spacer or a single bond,

[0309] mx21 means 0 or 1,

[0310] mx22 means 0 or 1,

[0311] mx23 means 0 or 1).

[0312] From the viewpoint of voltage holding ratio and compatibility with a liquid crystal composition, the compound represented by the general formula (X2) is preferably a compound represented by the following general formula (X2-i).

[0313] [Chemistry 75]

[0314]

[0315] (Where R x211 , R x221 , R x231 and R x241 each independently represents a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms,

[0316] Sp x211 、Sp x221 、Sp x231 and Sp x241 Each independently represents a linear or branched alkylene group having 1 to 20 carbon atoms or a single bond, in which any hydrogen atom in the group may be substituted by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- may each independently be substituted by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-,

[0317] mx211 means 0 or 1,

[0318] mx221 means 0 or 1,

[0319] mx231 represents 0 or 1), and the compound represented by the general formula (X2) is more preferably a compound represented by the following general formula (X2-ii).

[0320] [Chemistry 76]

[0321]

[0322] (Where R x212 and R x222 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms,

[0323] Sp x212 and Sp x222 Each independently represents a linear alkylene group having 1 to 10 carbon atoms or a single bond, wherein one -CH2- or two or more non-adjacent -CH2- groups may be independently substituted by -O-, -COO- or -OCO-,

[0324] mx212 represents 0 or 1), and the compound represented by the general formula (X2) is particularly preferably a compound represented by the following general formula (X2-iii).

[0325] [Chemistry 77]

[0326]

[0327] (Where R x213 and Rx223 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms,

[0328] Sp x213 represents a linear alkylene group having 1 to 10 carbon atoms in which one -CH2- or two or more non-adjacent -CH2- groups may be independently substituted with -COO- or -OCO-).

[0329] The liquid crystal composition of the present invention preferably has a refractive index anisotropy at a wavelength of 450 nm (Δn(450)) divided by a refractive index anisotropy at a wavelength of 550 nm (Δn(550)) (Δn(450) / Δn(550)) that satisfies the following formula (Formula 1):

[0330] Δn(450) / Δn(550)<1.10 (Formula 1).

[0331] From the viewpoint of changes in hue and chromaticity when the liquid crystal orientation changes due to applied voltage, the liquid crystal phase temperature range of the liquid crystal composition, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus, Δn(450) / Δn(550) is preferably greater than 0.72 and less than 1.06, more preferably greater than 0.74 and less than 1.02, further preferably greater than 0.76 and less than 0.98, further more preferably greater than 0.78 and less than 0.94, and particularly preferably greater than 0.80 and less than 0.90.

[0332] The liquid crystal composition of the present invention preferably has a refractive index anisotropy at a wavelength of 650 nm (Δn(650)) divided by a refractive index anisotropy at a wavelength of 550 nm (Δn(550)) (Δn(650) / Δn(550)) that satisfies the following formula (Formula 2):

[0333] 0.90<Δn(650) / Δn(550)<1.50 (Formula 2).

[0334] From the viewpoint of changes in hue and chromaticity when the liquid crystal orientation changes due to applied voltage, the liquid crystal phase temperature range of the liquid crystal composition, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus, Δn(650) / Δn(550) is preferably greater than 0.95 and less than 1.45, more preferably greater than 1.00 and less than 1.40, further preferably greater than 1.05 and less than 1.35, further more preferably greater than 1.10 and less than 1.30, and particularly preferably greater than 1.16 and less than 1.20.

[0335] The liquid crystal composition of the present invention is preferably used in a display element. In a liquid crystal unit sandwiched between two substrates having transparent electrodes, in an ECB (Electronic Controlled Birefringence) mode in which the transmittance is changed by changing the birefringence of the liquid crystal, the transmittance changes according to the following formula under a configuration of orthogonal polarization polarizers.

[0336] Liquid crystal azimuth angle: The angle relative to the transmission axis (OR absorption axis) of the polarizer is best when it is set to 45 degrees according to the following formula.

[0337] [Number 1]

[0338]

[0339] T: penetration rate

[0340] Ψ: Liquid crystal azimuth

[0341] λ: wavelength

[0342] d: unit thickness

[0343] In this formula, as a parameter that changes when a voltage is applied to the liquid crystal layer, there is Δn of the liquid crystal composition. As long as the Δn divided by the wavelength λ of the light source, that is, Δn / λ, can be kept constant at any wavelength, light is transmitted at the same ratio at each wavelength (each color), and the chromaticity shift of the liquid crystal display element does not occur, which is ideal. In the present invention, the ring structure contained in 1,4-cyclohexylene, decalin-2,6-diyl and 1,3-dioxane-2,5-diyl can be any of the trans-isomers and cis-isomers. From the perspective of liquid crystal properties, it is preferred that the content of each trans-isomer is greater than the content of the cis-isomer, and it is more preferred that the content of the trans-isomer in the ring structure is 80% or more, and it is further preferred that the content of the trans-isomer in the ring structure is 90% or more, and it is further preferred that the content of the trans-isomer in the ring structure is 95% or more, and it is particularly preferred that the content of the trans-isomer in the ring structure is 98% or more. In the present invention, the following notation (CY-1) means a trans-isomer and / or a cis-isomer of 1,4-cyclohexylene.

[0344] [Chemistry 78]

[0345]

[0346] (In the formula, the dotted line indicates the bonding position), and the following notation (CY-1-t) and notation (CY-2-t) mean the trans isomer of 1,4-cyclohexylene.

[0347] [Chemistry 79]

[0348]

[0349] (Where the dotted lines represent the bonding positions).

[0350] In the present invention, "having a bond at any position" means having a desired number of bonds at any position. For example, in the case of a monovalent group, it means having one bond at any position. Specifically, for example, in the following formula (ex-sub):

[0351] [Chemistry 80]

[0352]

[0353] When the group represented is a monovalent group and has a bonding bond at any position, it means a group selected from the following formula (ex-sub-1) to formula (ex-sub-3).

[0354] [Chemistry 81]

[0355]

[0356] (Where the dotted lines represent the bonding positions).

[0357] Furthermore, in the present invention, each element may be substituted with the isotope of the same element.

[0358] The compound of the present invention is a compound represented by the following general formula (I).

[0359] [Chemistry 82]

[0360]

[0361] (Where R 11 and R 12 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms,

[0362] A 11 and A 13 Each independently represents a group selected from the following formula (A1-1) to formula (A1-11).

[0363] [Chemistry 83]

[0364]

[0365] (where the dotted line indicates the bonding position), 11 When there are multiple, each can be the same or different. 13 When there are multiple, they may be the same or different.

[0366] A 12represents a group containing a group (ZG) having large wavelength dispersion, wherein the group (ZG) having large wavelength dispersion is oriented in a direction substantially perpendicular to the molecular long axis of the compound represented by the general formula (I),

[0367] Z 11 and Z 12 Each independently represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO- , -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. In the presence of multiple Z 11 In the case of multiple Z 12 In the case of , each may be the same or different, m11 and m12 each independently represent an integer from 0 to 5, and m11+m12 represents an integer from 0 to 5).

[0368] The compound represented by the general formula (I) is a compound (Z) having a group (ZG) in a direction perpendicular to the long axis of the molecule, and the group (ZG) has a large wavelength dispersion. The compound represented by the general formula (I) can improve the wavelength dispersion of the liquid crystal composition.

[0369] The details of the compound represented by the general formula (I) are as described in the section of the above liquid crystal composition.

[0370] Example

[0371] The present invention is further described below with reference to examples, but the present invention is not limited to these examples. In addition, the "%" in the compositions of the following examples and comparative examples refers to "mass %". In each process, when treating substances that are unstable to oxygen and / or water, it is preferred to operate in an inert gas such as nitrogen or argon. The purity of each compound was determined by UPLC (Waters ACQUITY UPLC, BEH C 18(100×2.1mm×1.7μm), acetonitrile / water or acetonitrile / water containing 0.1% formic acid, PDA, column temperature 40°C), GPC (Shimadzu HPLC Prominence, Shodex KF-801 (300mm×8mm×6μm) + KF-802 (300mm×8mm×6μm), tetrahydrofuran, RI, UV (254nm), column temperature 40°C), GC (Agilent6890A, J&W DB-1, 30m×0.25mm×0.25μm, carrier gas He, FID, 100°C (1min)→heating 10°C / min→300°C (12min)) or 1 The results were confirmed by H NMR (JEOL, 400 MHz).

[0372] (Example 1) Preparation of the compound represented by formula (I-1)

[0373] [Chemistry 84]

[0374]

[0375] (Example 1-1)

[0376] [Chemistry 85]

[0377]

[0378] 2.5 g of the compound represented by formula (I-1-1) was dissolved in 35 mL of dichloromethane, and 2.3 g of boron tribromide was slowly added thereto at room temperature. After stirring at room temperature for 2 hours, 30 mL of water was added and stirred for a while. The organic layer was extracted by liquid separation, washed with saturated brine, and dried by adding anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain 2.1 g of the compound represented by formula (I-1-2).

[0379] MS (EI): m / z = 271

[0380] (Example 1-2)

[0381] [Chemistry 86]

[0382]

[0383] The compound 50g represented by the formula (I-1-3) and diazabicyclo [2.2.2] octane (DABCO) 23g are dissolved in 300mL of dichloromethane and cooled in an ice bath under nitrogen. A solution obtained by dissolving 23.6g of methanesulfonic acid chloride in 50mL of dichloromethane is slowly added dropwise thereto. After the addition is completed, 100mL of water is added for liquid separation after stirring at room temperature for 3 hours. The organic layer is washed several times with dilute hydrochloric acid, then washed with saturated sodium bicarbonate aqueous solution, and then washed with saturated brine. After adding anhydrous sodium sulfate to the organic layer and drying it, the solvent is removed by distillation under reduced pressure to obtain 63g of the compound represented by the formula (I-1-4).

[0384] MS (EI): m / z = 316

[0385] (Example 1-3)

[0386] [Chemistry 87]

[0387]

[0388] While suspending 2.1g of the compound represented by the previously synthesized formula (I-1-2), 5.5g of the compound represented by the formula (I-1-4), and 5.6g of cesium carbonate in 35mL of acetone, stirring was performed and the temperature was raised until reflux occurred. The reaction was allowed to proceed for about 5 hours, and the temperature was lowered to room temperature after the reaction was confirmed to be complete. After adding 50mL of toluene and 100mL of water to dissolve the solid, liquid separation was performed. 30mL of toluene was added to the water layer for elution, and after washing it with the previous organic layer with dilute hydrochloric acid several times, it was washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate to dry it, the solvent was removed by reduced pressure distillation. The obtained solid was dissolved in toluene, and the eluted product was obtained by passing through a silica gel column. The obtained solid was heated and dissolved in a mixed solvent of toluene and ethanol for recrystallization to obtain 3.4g of the compound represented by the target formula (I-1).

[0389] MS (EI): m / z = 683

[0390] (Example 2) Preparation of the compound represented by formula (I-2)

[0391] [Chemistry 88]

[0392]

[0393] (Example 2-1)

[0394] [Chemistry 89]

[0395]

[0396] While suspending 3.0 g of the compound represented by the previously synthesized formula (I-2-2), 7.6 g of the compound represented by the formula (I-1-4), and 7.8 g of cesium carbonate in 47 mL of acetone, stir and raise the temperature until reflux occurs. The reaction is carried out for about 5 hours, and the temperature is lowered to room temperature after the reaction is confirmed to be completed. 60 mL of toluene and 100 mL of water are added thereto to dissolve the solid and then separate the liquids. 40 mL of toluene is added to the water layer for elution, and after washing it with the previous organic layer with dilute hydrochloric acid several times, it is washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate to dry it, the solvent is removed by vacuum distillation. The obtained solid is dissolved in toluene and the eluted product is obtained by passing through a silica gel column. The obtained solid is heated and dissolved in a mixed solvent of toluene and ethanol for recrystallization to obtain 4.5 g of the compound represented by the target formula (I-2).

[0397] MS (EI): m / z = 689

[0398] (Example 3) Preparation of the compound represented by formula (I-3)

[0399] [Chemistry 90]

[0400]

[0401] (Example 3-1)

[0402] [Chemistry 91]

[0403]

[0404] Dissolve 30 g of the compound represented by formula (I-3-1) in 150 mL of THF and cool to -78 degrees under nitrogen. Slowly drop 86 mL of 1.9 mol / L tert-butyl lithium solution therein and stir for 30 minutes. Slowly drop a solution of 36 g of 4'-propyl-[1,1'-bis(cyclohexane)]-4-one dissolved in 72 mL of THF. After stirring for 30 minutes, add 100 mL of water, return the temperature to room temperature, and separate the liquids. Wash the organic layer with saturated brine, add saturated sodium sulfate and dry it. Remove the solvent by distillation under reduced pressure to obtain 51 g of a solid.

[0405] MS (EI): m / z = 655

[0406] (Example 3-2)

[0407] [Chemistry 92]

[0408]

[0409] The compound 51g represented by the previously obtained formula (I-3-2) and 1.3g of p-toluenesulfonic acid are dissolved in 100mL of toluene and heated with stirring. The solvent is appropriately distilled off to remove water. The reaction is carried out until the water removed by distillation disappears. After cooling to room temperature, 50mL of water is added and liquid separation is carried out, and then washed with saturated sodium bicarbonate aqueous solution, and then washed with saturated saline. Anhydrous sodium sulfate is added to dry it, and the solvent is removed by distillation under reduced pressure to obtain a solid. It is dissolved in toluene containing hexane, and a precipitate is obtained by a silica gel column. The obtained solid is recrystallized using a mixed solvent of hexane and ethanol to obtain 43g of the compound represented by formula (I-3-3).

[0410] MS (EI): m / z = 619

[0411] (Example 3-3)

[0412] [Chemistry 93]

[0413]

[0414] The obtained compound 43g represented by the formula (I-3-3) is dissolved in a mixed solvent of THF and ethanol, 5% palladium carbon (palladium carbon) 1g is added thereto, and a hydrogen pressure of 1Mpa is applied. After confirming the completion of the reaction, the system is replaced with nitrogen and then filtered to remove palladium. Toluene containing hexane is added to the solid obtained by vacuum distillation to remove the solvent and dissolved, and a precipitate is obtained by passing through a silica gel column. It is recrystallized with a hexane mixed solvent containing ethanol, and then recrystallized multiple times with a hexane solvent containing toluene to obtain 5.2g of the compound represented by the formula (I-3).

[0415] MS (EI): m / z = 623

[0416] (Example 4) Preparation of the compound represented by formula (I-4)

[0417] [Chemistry 94]

[0418]

[0419] (Example 4-1)

[0420] [Chemistry 95]

[0421]

[0422] While suspending 3.0 g of the compound represented by formula (I-4-1), 7.8 g of the compound represented by formula (I-1-4) and 8.1 g of cesium carbonate in 60 mL of acetone, stir and raise the temperature until reflux occurs. The reaction is carried out for about 5 hours, and the temperature is lowered to room temperature after the reaction is confirmed to be completed. 60 mL of toluene and 100 mL of water are added thereto to dissolve the solid and then separate the liquids. 40 mL of toluene is added to the water layer for elution, and after washing it with the previous organic layer with dilute hydrochloric acid several times, it is washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying it, the solvent is removed by reduced pressure distillation. The obtained solid is dissolved in toluene, and the eluted product is obtained by passing through a silica gel column. The obtained solid is heated and dissolved in a mixed solvent of toluene and ethanol for recrystallization to obtain 4.3 g of the compound represented by the target formula (I-4).

[0423] MS (EI): m / z = 682

[0424] (Example 5) Preparation of the compound represented by formula (I-5)

[0425] [Chemistry 96]

[0426]

[0427] (Example 5-1)

[0428] [Chemistry 97]

[0429]

[0430] Under nitrogen, 15g of the compound represented by formula (I-5-1), 7.1g of 2-thiophenephoronic acid, and 1.9g of tetrakis(triphenylphosphine)palladium(0) were dissolved in 120mL of THF, 55mL of 1mol / L potassium carbonate aqueous solution was added thereto, the temperature was raised to 60 degrees and stirred for 4 hours. The temperature was lowered to room temperature, toluene and water were added for liquid separation, the organic layer was washed with dilute hydrochloric acid, washed with saturated sodium bicarbonate aqueous solution, and then washed with saturated brine. Anhydrous sodium sulfate was added and dried, and the solvent was removed by reduced pressure distillation to obtain a solid. It was dissolved in toluene and the precipitate was obtained by a silica gel column. Recrystallization was performed using a mixed solvent of ethanol and toluene to obtain 11.2g of the compound represented by formula (I-5-2).

[0431] MS (EI): m / z = 276

[0432] (Example 5-2)

[0433] [Chemistry 98]

[0434]

[0435] 11.2g of the compound represented by formula (I-5-2) was dissolved in 50mL of dichloromethane, and 10g of boron tribromide was slowly added thereto at room temperature. After stirring at room temperature for 2 hours, 30mL of water was added and stirred for a while. The organic layer was extracted by liquid separation, washed with saturated brine, and then anhydrous sodium sulfate was added and dried. The solvent was removed by distillation under reduced pressure to obtain 9.5g of the compound represented by formula (I-5-3).

[0436] MS (EI): m / z = 248

[0437] (Example 5-3)

[0438] [Chemistry 99]

[0439]

[0440] While suspending 4.5g of the compound represented by formula (I-5-3), 11.5g of the compound represented by formula (I-1-4) and 11.8g of cesium carbonate in 100mL of acetone, stir and raise the temperature until reflux occurs. The reaction is carried out for about 5 hours, and the temperature is lowered to room temperature after the reaction is confirmed to be completed. 80mL of toluene and 100mL of water are added thereto to dissolve the solid and then separate the liquids. 40mL of toluene is added to the water layer for elution, and after washing it with the previous organic layer with dilute hydrochloric acid several times, it is washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying it, the solvent is removed by reduced pressure distillation. The obtained solid is dissolved in toluene, and the eluted product is obtained by passing through a silica gel column. The obtained solid is heated and dissolved in a mixed solvent of toluene and ethanol for recrystallization to obtain 4.9g of the compound represented by the target formula (I-5).

[0441] MS (EI): m / z = 688

[0442] (Example 6) Preparation of the compound represented by formula (I-6)

[0443] [Chemical 100]

[0444]

[0445] (Example 6-1)

[0446] [Chemistry 101]

[0447]

[0448] While suspending 4.5g of the compound represented by formula (I-6-1), 11.6g of the compound represented by formula (I-1-4) and 17.9g of cesium carbonate in 100mL of acetone, stir and raise the temperature until reflux occurs. The reaction is carried out for about 5 hours, and the temperature is lowered to room temperature after the reaction is confirmed to be completed. 80mL of toluene and 100mL of water are added thereto to dissolve the solid and then separate the liquids. 40mL of toluene is added to the water layer for elution, and after washing it with the previous organic layer with dilute hydrochloric acid several times, it is washed with saturated sodium bicarbonate aqueous solution and saturated brine. After adding anhydrous sodium sulfate and drying it, the solvent is removed by distillation under reduced pressure. The obtained solid is dissolved in toluene, and the eluted product is obtained by passing through a silica gel column. The obtained solid is heated and dissolved in a mixed solvent of toluene and ethanol for recrystallization to obtain 8.8g of the compound represented by formula (I-6-2).

[0449] MS (EI): m / z = 684

[0450] (Example 6-2)

[0451] [Chemistry 102]

[0452]

[0453] Under nitrogen, 8.8 g of the compound represented by formula (I-6-2), 4.2 g of the compound represented by formula (I-6-3), and 1.5 g of tetrakis(triphenylphosphine)palladium(0) were dissolved in 500 mL of THF, 58 mL of 1 mol / L potassium carbonate aqueous solution was added thereto, the temperature was raised to 60 degrees and stirred for 8 hours. The temperature dropped to room temperature, toluene and water were added to separate the liquids, the organic layer was washed with dilute hydrochloric acid, washed with saturated sodium bicarbonate aqueous solution, and then washed with saturated brine. Anhydrous sodium sulfate was added and dried, and the solvent was removed by vacuum distillation to obtain a solid. It was dissolved in toluene and the precipitate was obtained by passing through a silica gel column. Recrystallization was performed using a mixed solvent of ethanol and toluene to obtain 5.2 g of the compound represented by formula (I-6).

[0454] MS (EI): m / z = 808

[0455] (Example 7) Preparation of the compound represented by formula (I-7)

[0456] [Chemistry 103]

[0457]

[0458] (Example 7-1)

[0459] [Chemistry 104]

[0460]

[0461] According to the same method as in Example 3, the compound represented by formula (I-7) was produced from the compound represented by formula (I-7-1).

[0462] MS (EI): m / z = 594

[0463] (Example 8) Preparation of the compound represented by formula (I-8)

[0464] [Chemistry 105]

[0465]

[0466] (Example 8-1)

[0467] [Chemistry 106]

[0468]

[0469] According to the same method as in Example 3, a compound represented by formula (I-8) was produced from the compound represented by formula (I-8-1).

[0470] MS (EI): m / z = 614

[0471] (Example 9) Preparation of the compound represented by formula (I-9)

[0472] [Chemistry 107]

[0473]

[0474] (Example 9-1)

[0475] [Chemistry 108]

[0476]

[0477] According to the same method as in Example 3, a compound represented by formula (I-9) was produced from the compound represented by formula (I-9-1).

[0478] MS (EI): m / z = 629

[0479] (Example 10) Preparation of the compound represented by formula (I-10)

[0480] [Chemistry 109]

[0481]

[0482] (Example 10-1)

[0483] [Chemistry 110]

[0484]

[0485] According to the same method as in Example 3, a compound represented by formula (I-10) was produced from a compound represented by formula (I-10-1).

[0486] MS (EI): m / z = 445

[0487] (Example 11) Preparation of the compound represented by formula (I-11)

[0488] [Chemistry 111]

[0489]

[0490] (Example 11-1)

[0491] [Chemistry 112]

[0492]

[0493] According to the same method as in Example 3, a compound represented by formula (I-11) was produced from a compound represented by formula (I-11-1).

[0494] MS (EI): m / z = 395

[0495] (Example 12) Preparation of the compound represented by formula (I-12)

[0496] [Chemistry 113]

[0497]

[0498] (Example 12-1)

[0499] [Chemistry 114]

[0500]

[0501] According to the same method as in Example 3, the compound represented by formula (I-12) was produced from the compound represented by formula (I-12-1).

[0502] MS (EI): m / z = 446

[0503] (Example 13) Preparation of the compound represented by formula (I-13)

[0504] [Chemistry 115]

[0505]

[0506] (Example 13-1)

[0507] [Chemistry 116]

[0508]

[0509] According to the same method as in Example 3, a compound represented by formula (I-13) was produced from the compound represented by formula (I-13-1).

[0510] MS (EI): m / z = 355

[0511] (Example 14) Preparation of the compound represented by formula (I-22)

[0512] [Chemistry 117]

[0513]

[0514] (Example 14-1)

[0515] [Chemistry 118]

[0516]

[0517] According to the same method as in Example 3, the compound represented by formula (I-22) was produced from the compound represented by formula (I-22-1).

[0518] MS (EI): m / z = 597

[0519] (Example 15) Preparation of the compound represented by formula (I-24)

[0520] [Chemistry 119]

[0521]

[0522] (Example 15-1)

[0523] [Chemistry 120]

[0524]

[0525] According to the same method as in Example 3, a compound represented by formula (I-24) was produced from the compound represented by formula (I-24-1).

[0526] MS (EI): m / z = 622

[0527] (Example 16) Preparation of the compound represented by formula (I-25)

[0528] [Chemistry 121]

[0529]

[0530] (Example 16-1)

[0531] [Chemistry 122]

[0532]

[0533] According to the same method as in Example 3, a compound represented by formula (I-25) was produced from the compound represented by formula (I-25-1).

[0534] MS (EI): m / z = 586

[0535] (Example 17) Preparation of the compound represented by formula (I-26)

[0536] [Chemistry 123]

[0537]

[0538] (Example 17-1)

[0539] [Chemistry 124]

[0540]

[0541] According to the same method as in Example 3, a compound represented by formula (I-26) was produced from the compound represented by formula (I-26-1).

[0542] MS (EI): m / z = 648

[0543] (Example 18) Preparation of the compound represented by formula (I-28)

[0544] [Chemistry 125]

[0545]

[0546] (Example 18-1)

[0547] [Chemistry 126]

[0548]

[0549] According to the same method as in Example 3, a compound represented by formula (I-28) was produced from the compound represented by formula (I-28-1).

[0550] MS (EI): m / z = 630

[0551] (Example 19) Preparation of the compound represented by formula (I-14)

[0552] [Chemistry 127]

[0553]

[0554] (Example 19-1)

[0555] [Chemistry 128]

[0556]

[0557] According to the same method as in Example 1, a compound represented by formula (I-14) was produced from a compound represented by formula (I-14-1), a compound represented by formula (I-14-2), and a compound represented by formula (I-14-3).

[0558] MS (EI): m / z = 648

[0559] (Example 20) Preparation of the compound represented by formula (I-15)

[0560] [Chemistry 129]

[0561]

[0562] (Example 20-1)

[0563] [Chemistry 130]

[0564]

[0565] The compound represented by formula (I-15) was produced by the same method as in Example 1 from the compound represented by formula (I-15-1), the compound represented by formula (I-15-2), and the compound represented by formula (I-15-3).

[0566] MS (EI): m / z = 746

[0567] (Example 21) Preparation of the compound represented by formula (I-16)

[0568] [Chemistry 131]

[0569]

[0570] (Example 21-1)

[0571] [Chemistry 132]

[0572]

[0573] According to the same method as in Example 1, the compound represented by the formula (I-16-1) and the compound represented by the formula (I-16-2) to the compound represented by the formula (I-16) were produced.

[0574] MS (EI): m / z = 686

[0575] (Example 22) Preparation of the compound represented by formula (I-17)

[0576] [Chemistry 133]

[0577]

[0578] (Example 22-1)

[0579] [Chemistry 134]

[0580]

[0581] According to the same method as in Example 1, a compound represented by formula (I-17-1), a compound represented by formula (I-17-2), and a compound represented by formula (I-17-3) to a compound represented by formula (I-17) were produced.

[0582] MS (EI): m / z = 608

[0583] (Example 23) Preparation of the compound represented by formula (I-18)

[0584] [Chemistry 135]

[0585]

[0586] (Example 23-1)

[0587] [Chemistry 136]

[0588]

[0589] According to the same method as in Example 1, a compound represented by formula (I-18-1), a compound represented by formula (I-18-2), and a compound represented by formula (I-18-3) to a compound represented by formula (I-18) were produced.

[0590] MS (EI): m / z = 670

[0591] (Example 24) Preparation of the compound represented by formula (I-21)

[0592] [Chemistry 137]

[0593]

[0594] (Example 24-1)

[0595] [Chemistry 138]

[0596]

[0597] According to the same method as in Example 1, a compound represented by formula (I-21) was produced from a compound represented by formula (I-21-1) and a compound represented by formula (I-21-2).

[0598] MS (EI): m / z = 693

[0599] (Example 25) Preparation of the compound represented by formula (I-27)

[0600] [Chemistry 139]

[0601]

[0602] (Example 25-1)

[0603] [Chemistry 140]

[0604]

[0605] According to the same method as in Example 1, a compound represented by formula (I-27) was produced from a compound represented by formula (I-27-1) and a compound represented by formula (I-27-2).

[0606] MS (EI): m / z = 786

[0607] (Example 26) Preparation of the compound represented by formula (I-29)

[0608] [Chemistry 141]

[0609]

[0610] (Example 26-1)

[0611] [Chemistry 142]

[0612]

[0613] According to the same method as in Example 1, a compound represented by formula (I-29) was produced from a compound represented by formula (I-29-1) and a compound represented by formula (I-29-2).

[0614] MS (EI): m / z = 736

[0615] (Example 27) Preparation of the compound represented by formula (I-30)

[0616] [Chemistry 143]

[0617]

[0618] (Example 27-1)

[0619] [Chemistry 144]

[0620]

[0621] According to the same method as in Example 1, a compound represented by formula (I-30) was produced from a compound represented by formula (I-30-1) and a compound represented by formula (I-30-2).

[0622] MS (EI): m / z = 724

[0623] (Example 28) Preparation of the compound represented by formula (I-20)

[0624] [Chemistry 145]

[0625]

[0626] (Example 28-1)

[0627] [Chemistry 146]

[0628]

[0629] Under a nitrogen atmosphere, 5.0 g of the compound represented by formula (I-20-1), 9.0 g of the compound represented by formula (I-20-2), 0.2 g of 4-dimethylaminopyridine, and 100 mL of dichloromethane were added to the reaction container. While cooling in an ice bath, 5.6 g of diisopropylcarbodiimide was added dropwise and stirred at room temperature for 8 hours. The precipitated solid was removed by filtration, and the filtrate was washed with 5% hydrochloric acid, water and brine in sequence, and the solvent was removed by distillation under reduced pressure. The obtained solid was dissolved in toluene and the precipitate was obtained by passing through a silica gel column. The obtained solid was heated and dissolved in a mixed solvent of toluene and ethanol for recrystallization to obtain 8.0 g of the compound represented by the target formula (I-20).

[0630] MS (EI): m / z = 660

[0631] (Example 29) Preparation of the compound represented by formula (I-23)

[0632] [Chemistry 147]

[0633]

[0634] (Example 29-1)

[0635] [Chemistry 148]

[0636]

[0637] According to the same method as in Example 28, a compound represented by formula (I-23) was produced from a compound represented by formula (I-23-1) and a compound represented by formula (I-23-2).

[0638] MS (EI): m / z = 683

[0639] (Example 30 to Example 41, Comparative Example 1 to Comparative Example 4)

[0640] In the examples, the following abbreviations are used to describe the liquid crystal compounds.

[0641] (Ring structure)

[0642] [Chemistry 149]

[0643]

[0644] (Side chain structure and link structure)

[0645] [Table 1]

[0646] The record in the formula Substituents and linkers represented 1- <![CDATA[CH3-]]> 2- <![CDATA[C2H5-]]> 3- <![CDATA[n-C3H7-]]> 4- <![CDATA[n-C4H9-]]> 5- <![CDATA[n-C5H 11 -]]> V- <![CDATA[CH2=CH-]]> V2- <![CDATA[CH2=CH-CH2-CH2-]]> 1V2- <![CDATA[CH3-CH=CH-CH2-CH2- <!-- 52 -->]]> -1 <![CDATA[-CH3]]> -2 <![CDATA[-C2H5]]> -3 <![CDATA[-n-C3H7]]> -4 <![CDATA[-n-C4H9]]> -5 <![CDATA[-n-C5H 11 ]]> -O1 <![CDATA[-O-CH3]]> -O2 <![CDATA[-O-C2H5]]> -O3 <![CDATA[-O-n-C3H7]]> -O4 <![CDATA[-O-n-C4H9]]> -O5 <![CDATA[-O-n-C5H 11 ]]> -V <![CDATA[-CH=CH2]]> -V1 <![CDATA[-CH=CH-CH3]]> -2V <![CDATA[-CH2-CH2-CH=CH2]]> -F -F -OCF3 <![CDATA[-OCF3]]> -CN -CN - single bond -E- -COO- -1- <![CDATA[-CH2CH2-]]> -CFFO- <![CDATA[-CF2O-]]> -T- -C≡C- -O1- <![CDATA[-OCH2-]]> -1O- <![CDATA[-CH2O-]]>

[0647] In the examples, the properties measured are as follows: Unless otherwise specified, the measurements were based on the method specified in JEITA ED-2521B.

[0648] Δn: refractive index anisotropy at 25°C @589nm

[0649] Δε: Dielectric anisotropy at 25°C

[0650] In the test cell, the following evaluations were performed using the liquid crystal composition to which the compound of the present invention was added.

[0651] (Method for producing a liquid crystal evaluation cell)

[0652] First, the liquid crystal composition described in this embodiment was injected into a liquid crystal cell containing an ITO-attached substrate by vacuum injection, wherein the ITO-attached substrate was a substrate coated with a polyimide alignment film that induced vertical alignment at a cell gap of 3.5 μm and then subjected to a rubbing treatment. JALS2096 manufactured by JSR Corporation was used as a vertical alignment film forming material.

[0653] After the injection was completed, polarizing plates were attached to the front and back surfaces of the cell so as to be 45 degrees different from the liquid crystal orientation direction (= rubbing direction) and to be under cross polarization.

[0654] (Measurement of Chromaticity Change)

[0655] Between the upper and lower electrodes of the liquid crystal cell, AC voltages were applied in the order of 0 V to 10 V, the transmission wavelength spectrum at each voltage was measured from the front of the cell, and the cell chromaticity under the light source D65 was calculated.

[0656] At this time, the amount of change Δdelta between the chromaticity of 0V and the chromaticity of 10V (x, y) is calculated by the following formula, and the cases where the values ​​fall within the respective ranges are defined as ◎○△×.

[0657] The color coordinates of 0V are (x0, y0)

[0658] The color coordinates of 10 are (x10, y10)

[0659] [Number 2]

[0660]

[0661] [Table 2]

[0662] determination Δdelta ◎ ＜0.05 ○ 0.05～0.07 △ 0.07～0.09 × ＞0.09

[0663] The measurement results are shown in the following table.

[0664] [Table 3]

[0665] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 3-Cy-Cy-2 18 22 3-Cy-Cy-4 8 10 3-Cy-Cy-5 3-Cy-Cy-V 24 21 2-Cy-Cy-V1 6 3-Cy-Cy-V1 9 6 3-Cy-Ph-O1 5 3-Ph-Ph-1 13 9 3 3-Ph-Ph-O1 3-Cy-Cy-Ph-1 3-Cy-Ph-Ph-2 6 5 3 5-Cy-Ph-Ph-2 4 3-Cy-1O-Ph5-O1 6 3-Cy-1O-Ph5-O2 7 5 1V-Cy-1O-Ph5-O2 6 2-Cy-Cy-1O-Ph5-O2 14 12 3-Cy-Cy-1O-Ph5-O2 3 10 V-Cy-Cy-1O-Ph5-O2 4 1V-Cy-Cy-1O-Ph5-O2 6 3-Cy-Ph-Ph5-O3 6 10 3-Cy-Ph-Ph5-O2 10 3-Cy-Ph-Ph5-O4 7 6 4-Cy-Ph-Ph5-03 8 2-Ph-2-Ph-Ph5-O2 - 5 3-Ph-2-Ph-Ph5-O2 - 5 3-Cy-Ph5-O2 8 3-Ph-Ph5-O2 - 8 8 5-Ph-Ph5-O2 9 2-Cy-Cy-Ph5-O2 15 2-Cy-Cy-Ph5-O3 15 3-Cy-Cy-Ph5-O3 8 4-Cy-Cy-Ph5-O2 6 3-Ph-Ph5-Ph-1 4 3-Ph-Ph5-Ph-2 - 8 9 I-6 I-5 I-4 total 100 100 100 100 Δn 0.111 0.115 0.105 0.107 Δε -3.19 -3 -3.8 -2.9 The degree of chromaticity change × × × ×

[0666] [Table 4]

[0667] Embodiment 30 Embodiment 31 Embodiment 32 Embodiment 33 3-Cy-Cy-2 18 22 3-Cy-Cy-4 8 10 3-Cy-Cy-5 3-Cy-Cy-V 24 21 2-Cy-Cy-V1 6 3-Cy-Cy-V1 9 6 3-Cy-Ph-O1 5 3-Ph-Ph-1 13 9 3 3-Ph-Ph-O1 3-Cy-Cy-Ph-1 3-Cy-Ph-Ph-2 6 5 3 5-Cy-Ph-Ph-2 4 3-Cy-1O-Ph5-O1 6 3-Cy-1O-Ph5-O2 7 5 1V-Cy-1O-Ph5-O2 6 2-Cy-Cy-1O-Ph5-O2 14 12 3-Cy-Cy-1O-Ph5-O2 3 10 V-Cy-Cy-1O-Ph5-O2 4 1V-Cy-Cy-1O-Ph5-O2 6 3-Cy-Ph-Ph5-O3 6 - 3-Cy-Ph-Ph5-O2 - 3-Cy-Ph-Ph5-O4 - 6 4-Cy-Ph-Ph5-O3 - 2-Ph-2-Ph-Ph5-O2 - - 3-Ph-2-Ph-Ph5-O2 - - 3-Cy-Ph5-O2 - 3-Ph-Ph5-O2 - 8 8 5-Ph-Ph5-O2 9 2-Cy-Cy-Ph5-O2 - 2-Cy-Cy-Ph5-O3 15 3-Cy-Cy-Ph5-O3 8 4-Cy-Cy-Ph5-O2 6 3-Ph-Ph5-Ph-1 4 3-Ph-Ph5-Ph-2 - 8 9 I-6 15 20 10 23 I-5 I-4 total 100 100 100 100 Δn 0.102 0.112 0.096 0.101 De -3 -2.8 -3.6 -2.9 Degree of chromaticity change ○ ◎ △ ◎

[0668] [Table 5]

[0669] Example 34 Example 35 Example 36 Example 37 3-Cy-Cy-2 3 12 3-Cy-Cy-4 8 - 3-Cy-Cy-5 3-Cy-Cy-V 10 - 2-Cy-Cy-V1 6 3-Cy-Cy-V1 9 6 3-Cy-Ph-O1 5 3-Ph-Ph-1 13 9 3 3-Ph-Ph-O1 3-Cy-Cy-Ph-1 3-Cy-Ph-Ph-2 6 5 3 5-Cy-Ph-Ph-2 4 3-Cy-1O-Ph5-O1 6 3-Cy-1O-Ph5-O2 7 5 1V-Cy-1O-Ph5-O2 6 2-Cy-Cy-1O-Ph5-O2 14 12 3-Cy-Cy-1O-Ph5-O2 3 10 V-Cy-Cy-1O-Ph5-O2 4 1V-Cy-Cy-1O-Ph5-O2 6 3-Cy-Ph-Ph5-O3 6 10 3-Cy-Ph-Ph5-O2 10 3-Cy-Ph-Ph5-O4 7 6 4-Cy-Ph-Ph5-O3 8 2-Ph-2-Ph-Ph5-O2 - 5 3-Ph-2-Ph-Ph5-O2 - 5 3-Cy-Ph5-O2 8 3-Ph-Ph5-O2 - 8 8 5-Ph-Ph5-O2 9 2-Cy-Cy-Ph5-O2 15 2-Cy-Cy-Ph5-O3 15 3-Cy-Cy-Ph5-O3 8 4-Cy-Cy-Ph5-O2 6 3-Ph-Ph5-Ph-1 4 3-Ph-Ph5-Ph-2 - 8 9 I-6 I-5 15 20 14 21 I-4 Total 100 100 100 100 Δn 0.108 0.116 0.104 0.103 Δε -3.1 -2.9 -3.6 -2.8 Degree of chromaticity change ○ ◎ ○ ◎

[0670] [Table 6]

[0671] Example 38 Example 39 Example 40 Example 41 3-Cy-Cy-2 3 12 3-Cy-Cy-4 8 - 3-Cy-Cy-5 3-Cy-Cy-V 10 - 2-Cy-Cy-V1 6 3-Cy-Cy-V1 9 6 3-Cy-Ph-O1 5 3-Ph-Ph-1 13 9 3 3-Ph-Ph-O1 3-Cy-Cy-Ph-1 3-Cy-Ph-Ph-2 6 5 3 5-Cy-Ph-Ph-2 4 3-Cy-1O-Ph5-O1 6 3-Cy-1O-Ph5-O2 7 5 1V-Cy-1O-Ph5-O2 6 2-Cy-Cy-1O-Ph5-O2 14 12 3-Cy-Cy-1O-Ph5-O2 3 10 V-Cy-Cy-1O-Ph5-O2 4 1V-Cy-Cy-1O-Ph5-O2 6 3-Cy-Ph-Ph5-O3 6 10 3-Cy-Ph-Ph5-O2 10 3-Cy-Ph-Ph5-O4 7 6 4-Cy-Ph-Ph5-O3 8 2-Ph-2-Ph-Ph5-O2 - 5 3-Ph-2-Ph-Ph5-O2 - 5 3-Cy-Ph5-O2 8 3-Ph-Ph5-O2 - 8 8 5-Ph-Ph5-O2 9 2-Cy-Cy-Ph5-O2 15 2-Cy-Cy-Ph5-O3 15 3-Cy-Cy-Ph5-O3 8 4-Cy-Cy-Ph5-O2 6 3-Ph--Ph5-Ph-1 4 3-Ph-Ph5-Ph-2 - 8 9 I-6 I-5 I-4 15 20 14 21 Total 100 100 100 100 Δn 0.109 0.118 0.102 0.105 Δε -3 -3.1 -3.7 -3 Degree of chromaticity change △ ○ △ ○

[0672] Thus, in the liquid crystal composition added with the compound of the present invention, the chromaticity change caused by the applied voltage is suppressed. From the above results, it can be seen that the liquid crystal composition of the present invention is useful as a material for liquid crystal display elements because the changes in color tone and chromaticity when the liquid crystal orientation changes due to the applied voltage are small when used for display elements.

Claims

1. A liquid crystal composition for an active drive display element, characterized in that: Containing at least one compound (Z) having a group ZG in a direction perpendicular to the long axis of the molecule, wherein the group ZG has a large wavelength dispersion property, The compound (Z) is a compound selected from the group consisting of compounds represented by the following general formula (I-iv-1) and general formula (I-iv-4), [Chemistry 10] In the formula, R 114 and R 124 each independently represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, or an alkenyl group having 2 or 3 carbon atoms, A 114 and A 134 Each independently represents a group selected from the following formula (A114-1) to formula (A114-5), [Chemistry 11] In the formula, the dotted line indicates the bonding position. 114 When there are multiple A 134 In the case of , they can be the same or different. A 124 represents a group selected from the following formula (A124-1) to formula (A124-4), [Chemistry 12] In the formula, the dotted line indicates the bonding position, and these groups are unsubstituted or substituted with one or more substituents L G1 Replacement, T 11 represents a group selected from the following formula (T11-1) to formula (T11-3), [Chemistry 13] In the formula, there is one bond at any position, and these groups are unsubstituted or substituted with one or more substituents L G1 replace, L G1 represents a fluorine atom, a chlorine atom, a pentafluorosulfanyl group, an alkyl group having 1 to 10 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- may each independently be substituted by -O-, -S-, -COO-, -OCO-, -CH=CH-, -CF=CF- or -C≡C-, Z 1141 , Z 1142 , Z 1241 and Z 1242 Each independently represents -OCH2-, -CH2O- or a single bond.

2. The liquid crystal composition according to claim 1, wherein Containing a compound represented by the following general formula (III), [Chemistry 14] In the formula, R 31 and R 32 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms, A 31 and A 32 Each independently represents a group selected from the following formula (A3-1) to formula (A3-10), [Chemistry 15] In the formula, the dotted line represents the bonding position. 32 In the case of , they can be the same or different. m31 represents an integer from 1 to 4.

3. The liquid crystal composition according to claim 2, wherein: The total content of the compound represented by the general formula (III) is 5 mass % or more and 95 mass % or less.

4. The liquid crystal composition according to claim 1, wherein Contains a compound represented by the following general formula (III-i), [Chemistry 16] In the formula, R 311 and R 321 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms, A 311 and A 321 Each independently represents a group selected from the following formula (A31-1) to formula (A31-6), [Chemistry 17] In the formula, the dotted line represents the bonding position. 321 In the case of , they can be the same or different. m311 represents an integer from 1 to 3.

5. The liquid crystal composition according to claim 4, wherein A compound selected from the group consisting of compounds represented by the following general formula (III-iv-1) to general formula (III-iv-10), [Chemistry 18] [Chemistry 19] In the formula, R 314 and R 324 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.

6. The liquid crystal composition according to claim 5, wherein The dielectric anisotropy Δε is not less than -5.0 and not more than -1.

0.

7. The liquid crystal composition according to claim 6, wherein Containing a compound represented by the following general formula (II), [Chemistry 20] In the formula, R 21 and R 22 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms, A 21 and A 22 Each independently represents a group selected from the following formula (A2-1) to formula (A2-11), [Chemistry 21] In the formula, the dotted line represents the bonding position. 21 In the case of multiple A 22 In the case of , they can be the same or different. Z 21 and Z 22 Each independently represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO- , -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. In the presence of multiple Z 21 In the case of multiple Z 22 In the case of , they can be the same or different. m21 and m22 each independently represent an integer from 0 to 3, and m21+m22 represents an integer from 1 to 3.

8. The liquid crystal composition according to claim 7, wherein: Contains a compound represented by the following general formula (II-i), [Chemistry 22] In the formula, R 211 and R 221 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms, A 211 and A 221 Each independently represents a group selected from the following formula (A21-1) to formula (A21-9), [Chemistry 23] In the formula, the dotted line represents the bonding position. 211 In the case of multiple A 221 In the case of , they can be the same or different. Z 211 and Z 221 Each independently represents -OCH2-, -CH2O-, -CH2CH2-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH=CH-COO-, -OCO-CH=CH-, -CH=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. 211 In the case of multiple Z 221 In the case of , they can be the same or different. m211 and m221 each independently represent an integer from 0 to 3, and m211+m221 represents an integer from 1 to 3.

9. The liquid crystal composition according to claim 8, wherein A compound selected from the group consisting of compounds represented by the following general formula (II-iv-1) to general formula (II-iv-8), [Chemistry 24] [Chemistry 25] In the formula, R 214 and R 224 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.

10. The liquid crystal composition according to claim 9, wherein Containing a compound represented by the following general formula (IV), [Chemistry 26] Where P 41 and P 42 each independently represents a group that is polymerized by free radical polymerization, cationic polymerization or anionic polymerization, Sp 41 and Sp 42 Each independently represents a spacer or a single bond, A 41 and A 42 Each independently represents a group selected from the following formula (A4-1) to formula (A4-9), [Chemistry 27] In the formula, the dotted line indicates the bonding position, L 4 represents a halogen atom, a cyano group, a nitro group, a pentafluorosulfanyl group, an optionally substituted amino group, an optionally substituted silyl group, an alkyl group having 1 to 20 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- may each independently be substituted 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-, or P L -Sp L -represented by a group, wherein P L represents a group that polymerizes by free radical polymerization, cationic polymerization, or anionic polymerization, Sp L Indicates a spacer or a single bond. 4 In the case of multiple A 42 In the case of , they can be the same or different. Z 41 Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO- NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -C H=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. 41 In the case of , they can be the same or different. m41 represents an integer from 1 to 4.

11. The liquid crystal composition according to claim 10, wherein Contains a compound represented by the following general formula (X1), [Chemistry 28] Where, Sp x1 represents an alkylene group having 1 to 20 carbon atoms or a single bond, in which one -CH2- or two or more non-adjacent -CH2- may be independently substituted 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 A x1 represents a group selected from the following formula (Ax1-1) to formula (Ax1-8), [Chemistry 29] In the formula, the dotted line represents the bonding position. x1 In the case of , they can be the same or different. Z x1 Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO- NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -C H=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or a single bond. x1 In the case of , they can be the same or different. mx1 means 0 or 1, mx2 represents an integer from 0 to 4.

12. The liquid crystal composition according to claim 11, wherein Contains a compound represented by the following general formula (X2), [Chemistry 30] In the formula, R x21 , R x22 , R x23 and R x24 each independently represents a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, Sp x21 、Sp x22 、Sp x23 and Sp x24 Each independently represents a spacer or a single bond, mx21 means 0 or 1, mx22 means 0 or 1, mx23 means 0 or 1.

13. The liquid crystal composition according to claim 12, wherein: The value Δn(450) / Δn(550) obtained by dividing the refractive index anisotropy Δn(450) at a wavelength of 450 nm by the refractive index anisotropy Δn(550) at a wavelength of 550 nm satisfies the following formula (Formula 1): Δn(450) / Δn(550)<1.10 (Formula 1).

14. The liquid crystal composition according to claim 12, wherein: The value Δn(650) / Δn(550) obtained by dividing the refractive index anisotropy Δn(650) at a wavelength of 650 nm by the refractive index anisotropy Δn(550) at a wavelength of 550 nm satisfies the following formula (Formula 2): 0.90<Δn(650) / Δn(550)<1.50 (Formula 2). 15 . A display element comprising the liquid crystal composition according to claim 1 .

16. A compound, characterized in that Represented by general formula (I), [Chemistry 31] In the formula, R 11 and R 12 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms, A 11 and A 13 Each independently represents a group selected from the following formula (A1-1) to formula (A1-5), [Chemistry 32] In the formula, the dotted line indicates the bonding position. 11 When there are multiple, each can be the same or different. 13 When there are multiple, they may be the same or different. A 12 represents a group containing a group ZG having large wavelength dispersion, wherein the group ZG having large wavelength dispersion is oriented in a direction substantially perpendicular to the molecular long axis of the compound represented by the general formula (I), Z 11 and Z 12 Each independently represents -OCH2-, -CH2O- or a single bond. 11 In the case of multiple Z 12 In the case of , they can be the same or different. m11 and m12 each independently represent 1 or each independently represent 2.

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