Compound, liquid crystal composition, and liquid crystal display element, sensor, liquid crystal lens, optical communication device, and antenna using said liquid crystal composition

Abstract

The present invention addresses the problem of providing: a compound capable of providing a liquid crystal composition having high Tni, large [delta] n, large [delta] [epsilon] r, small tan [delta] iso, and good storability at room temperature; a liquid crystal composition; and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition. Specifically, the liquid crystal composition contains one or more compounds represented by general formula (i), said compounds having a tetracyclic structure,-C = C-as a linking group between the cyclic structures, and an isothiocyanate group (-NCS).

Description

Technical Field

[0001] The present invention relates to a compound, a liquid crystal composition, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device and an antenna using the liquid crystal composition. Background Art

[0002] As a new use of liquid crystals, which are mostly used for display purposes, antennas using liquid crystals for transmitting and receiving radio waves between mobile objects such as cars and communication satellites have attracted much attention. In the past, satellite communications used parabola antennas, but when used in mobile objects such as cars, the parabola antennas must be pointed toward the satellite at all times, requiring a large movable part. However, antennas using liquid crystals can change the direction of transmitting and receiving radio waves through the operation of the liquid crystals inside the panel, so there is no need to move the antenna itself, and the shape of the antenna can also be flat. In addition, in order to achieve global large-capacity and high-speed communications, research on low-orbit satellite constellations using multiple low-orbit satellites is underway. In order to track low-orbit satellites that appear to be always moving from the ground, liquid crystal antennas that can easily change the direction of transmitting and receiving radio waves are useful.

[0003] Generally speaking, for the automatic driving of automobiles, it is necessary to download a large amount of data of high-precision three-dimensional (3D) map information. However, if it is an antenna using liquid crystal, by assembling the antenna in the car, a large amount of data can be downloaded from the communication satellite even without a mechanical movable part. The frequency band used in satellite communication is about 13GHz, which is very different from the frequency used in liquid crystal display applications so far. Therefore, the required physical properties of liquid crystal are also very different. The Δn required for liquid crystal for antenna is, for example, about 0.4, and the operating temperature range is, for example, -20℃ to 120℃.

[0004] In addition, infrared laser image recognition and distance measurement devices using liquid crystals are also attracting attention as sensors for autonomous driving of mobile objects such as automobiles. The Δn required for liquid crystals for such applications is, for example, 0.3 to 0.6, and the operating temperature range is, for example, 10°C to 100°C.

[0005] Furthermore, it is known that many liquid crystal compounds constituting a liquid crystal composition showing a high Δn of 0.2 or more have low compatibility. Therefore, it is also important to select a liquid crystal compound having high compatibility.

[0006] In this regard, as a technology of liquid crystal for antenna, for example, Patent Document 1 can be cited.

[0007] Furthermore, Non-Patent Document 1 proposes the use of a liquid crystal material as a constituent component of a high-frequency device.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: Japanese Patent Application Publication No. 2016-37607

[0011] Non-patent literature

[0012] Non-patent document 1: D. Dolfi, "Electronics Letters", (UK), 1993, Vol. 29, No. 10, pp. 926-928 Summary of the invention

[0013] Problems to be solved by the invention

[0014] The present invention aims to provide a method for providing a ni High, large Δn, Δε r Large, tanδ iso A compound for a liquid crystal composition having a small size and good storage stability at room temperature, a liquid crystal composition, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition.

[0015] Technical means of solving problems

[0016] The present inventors have conducted diligent research and found that one or more liquid crystal compositions containing compounds represented by the general formula (i) having a four-ring structure, -C≡C- as a linking group between the ring structures and an isothiocyanate group (-NCS) can solve the above-mentioned problems, thereby completing the present invention.

[0017] An example of the structure of the present invention for solving the above-mentioned problems is as follows.

[0018] Item 1. A liquid crystal composition comprising one or two or more compounds represented by the following general formula (i).

[0019] [Chemistry 1]

[0020] R i1 -A i1 -Z i1 -A i2 -Z i2 -A i3 -Z i3 -A i4 -NCS (i)

[0021] (In general formula (i),

[0022] R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

[0023] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0024] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0025] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0026] However, oxygen atoms do not bond directly to each other.

[0027] A i1 , A i2 , A i3 and A i4 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms,

[0028] The A i1 , A i2 , A i3 and A i4 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace,

[0029] Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

[0030] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0031] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0032] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0033] However, oxygen atoms do not bond directly to each other.

[0034] In the substituent S i1When there are multiple, these may be the same or different.

[0035] Z i1 , Z i2 and Z i3 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0036] Z i1 , Z i2 and Z i3 At least one representation of -C≡C-,

[0037] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0038] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0039] But oxygen atoms do not bond directly to each other)

[0040] Item 2. The liquid crystal composition according to Item 1, wherein R i1 The alkyl group represents an alkynyl group having 2 to 20 carbon atoms when one or two or more -CH2-CH2- are replaced by -C≡C-.

[0041] Item 3. The liquid crystal composition according to Item 1 or 2, wherein Z i3 It means -C≡C-.

[0042] Item 4. The liquid crystal composition according to any one of Items 1 to 3, further comprising one or two or more compounds represented by the following general formula (ii).

[0043] [Chemistry 2]

[0044]

[0045] (In general formula (ii),

[0046] R ii1 each independently represents an alkyl group having 1 to 20 carbon atoms,

[0047] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0048] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0049] One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms.

[0050] However, oxygen atoms do not bond directly to each other.

[0051] A ii1 and A ii2 Each independently represents a group selected from the group consisting of the following group (a), group (b), group (c) and group (d),

[0052] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- and / or -S-)

[0053] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[0054] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene-2,7-diyl, 2,3-dihydroindane-2,5-diyl, 2,3-dihydroindane-1,5-diyl, 2,3-dihydroindane-3,5-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0055] (d) thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl, benzo[1,2-b:4,5-b']dithiophene-2,6-diyl (one -CH= or two or more -CH= in the above group may be substituted with -N=)

[0056] The A ii1 and Aii2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S ii1 replace,

[0057] Substituent S ii1 represents any one of a halogen atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms,

[0058] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0059] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0060] One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms.

[0061] However, oxygen atoms do not bond directly to each other.

[0062] In the substituent S ii1 When there are multiple, these may be the same or different.

[0063] Z ii1 represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0064] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0065] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0066] Oxygen atoms do not bond directly to each other.

[0067] n ii1 represents an integer from 1 to 4,

[0068] In A ii1 and Z ii1Where there are multiple, these may be the same or different;

[0069] However, the compounds represented by the general formula (i) are excluded)

[0070] Item 5. The liquid crystal composition according to Item 4, wherein the compound represented by the general formula (ii) is selected from the group consisting of compounds represented by the following general formulae (ii-1) to (ii-8).

[0071] [Chemistry 3]

[0072] R ii1 -A ii1 -A ii2 -NCS (ii-1)

[0073]

[0074] R ii1 -A ii1 -A ii1-2 -A ii2 -NCS (ii-5)

[0075]

[0076] R ii1 -A ii1 -A ii1-2 -A ii1-3 -A ii2 -NCS (ii-8)

[0077] (In general formula (ii-1) to general formula (ii-8),

[0078] R ii1 , A ii1 and A ii2 represents the same as R in the general formula (ii) ii1 , A ii1 and A ii2 The same meaning respectively,

[0079] In the general formula (ii-3) to the general formula (ii-8), A ii1-2 and A ii1-3 The definitions of are independently the same as those of A in the general formula (ii). ii1 Same definition as

[0080] Item 6. The liquid crystal composition according to any one of Items 1 to 5, wherein Δn at 25° C. and 589 nm is 0.38 or more.

[0081] Item 7. A liquid crystal display element using the liquid crystal composition according to any one of Items 1 to 6.

[0082] Item 8. The liquid crystal display element according to Item 7, which is driven by an active matrix method or a passive matrix method.

[0083] Item 9. A liquid crystal display element that reversibly switches a dielectric constant by reversibly changing the alignment direction of liquid crystal molecules of the liquid crystal composition according to any one of Items 1 to 6.

[0084] Item 10. A sensor using the liquid crystal composition according to any one of Items 1 to 6.

[0085] Item 11. A liquid crystal lens using the liquid crystal composition according to any one of Items 1 to 6.

[0086] Item 12. An optical communication device using the liquid crystal composition according to any one of Items 1 to 6.

[0087] Item 13. An antenna using the liquid crystal composition according to any one of Items 1 to 6.

[0088] Item 14. The antenna according to Item 13, comprising:

[0089] A first substrate having a plurality of grooves;

[0090] A second substrate, facing the first substrate and provided with a power supply portion;

[0091] A first dielectric layer is disposed between the first substrate and the second substrate;

[0092] a plurality of patch electrodes, arranged corresponding to the plurality of grooves;

[0093] A third substrate, provided with the patch electrode; and

[0094] A liquid crystal layer is disposed between the first substrate and the third substrate.

[0095] The liquid crystal layer contains the liquid crystal composition according to any one of items 1 to 6.

[0096] Item 15. A compound represented by the following general formula (i).

[0097] [Chemistry 4]

[0098] R i1 -A i1 -Z i1 -A i2 -Z i2 -A i3 -Z i3 -A i4 -NCS (i)

[0099] (In general formula (i),

[0100] R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

[0101] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0102] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0103] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0104] However, oxygen atoms do not bond directly to each other.

[0105] A i1 , A i2 , A i3 and A i4 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms,

[0106] The A i1 , A i2 , A i3 and A i4 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace,

[0107] Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

[0108] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0109] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0110] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0111] However, oxygen atoms do not bond directly to each other.

[0112] In the substituent S i1 When there are multiple, these may be the same or different.

[0113] Z i1 , Z i2 and Z i3 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0114] Z i1 , Z i2 and Z i3 At least one representation of -C≡C-,

[0115] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0116] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0117] But oxygen atoms do not bond directly to each other)

[0118] Effects of the Invention

[0119] According to the present invention, a liquid crystal composition having a high Tni, a large Δn, a large Δεr, a small tanδiso, and good storage properties at room temperature can be obtained by using one or more liquid crystal compositions containing compounds represented by the general formula (i) having a four-ring structure, -C≡C- as a linking group between the ring structures, and an isothiocyanate group (-NCS). The liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas. DETAILED DESCRIPTION

[0120] (Compound represented by general formula (i))

[0121] The liquid crystal composition of the present invention contains a compound represented by the general formula (i) having a tetracyclic structure, -C≡C- as a linking group between the ring structures, and an isothiocyanate group (-NCS).

[0122] The liquid crystal composition of the present invention contains one or more compounds represented by the general formula (i) having a tetracyclic structure, -C≡C- as a linking group between the ring structures, and an isothiocyanate group (-NCS).

[0123] [Chemistry 5]

[0124] R i1 -A i1 -Z i1 -A i2 -Z i2 -A i3 -Z i3 -A i4 -NCS (i)

[0125] In the general formula (i), R i1 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

[0126] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0127] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[0128] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0129] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0130] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0131] Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

[0132] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0133] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0134] For example, R i1 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0135] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0136] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0137] In addition, R i1 By substituting one -CH2- in the above alkyl group with -S-, an alkylthio group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[0138] The alkyl sulfhydryl group is a linear, branched or cyclic alkyl sulfhydryl group, and is preferably a linear alkyl sulfhydryl group.

[0139] The alkylthio group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0140] In addition, R i1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0141] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0142] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0143] In addition, R i1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0144] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0145] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0146] The alkynyl group is preferably a group of the following formula (R i1 -A) represents an alkynyl group.

[0147] [Chemistry 6]

[0148]

[0149] Formula (R i1 -A), R i1A It represents an alkyl group having 1 to 18 carbon atoms.

[0150] The alkyl group having 1 to 18 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0151] The alkyl group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms.

[0152] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0153] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0154] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0155] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0156] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0157] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0158] In addition, the formula (R i1 -A), the black dot indicates the direction to A i1 The bond key.

[0159] In addition, R i1 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[0160] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0161] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0162] In addition, R i1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0163] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0164] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0165] In addition, Ri1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[0166] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0167] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0168] As R i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: i1 -1)~Formula (R i1 -46) represented by the base, etc.

[0169] [Chemistry 7]

[0170]

[0171] [Chemistry 8]

[0172]

[0173] Formula (R i1 -1)~Formula (R i1 -46), the black dot indicates the direction to A i1 The bond key.

[0174] In addition, as R i1 From the viewpoint of Δn and compatibility with other liquid crystal compounds, a linear alkyl group having 2 to 6 carbon atoms or a linear alkynyl group having 2 to 8 carbon atoms is preferred.

[0175] In the general formula (i), A i1 , A i2 , A i3 and A i4 Each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms.

[0176] More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms preferably represents a group selected from the group consisting of the following groups (a), (b), (c) and (d),

[0177] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- or -S-)

[0178] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=)

[0179] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0180] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= in the above groups may be substituted with -N=).

[0181] A i1 , A i2 , A i3 and A i4 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace.

[0182] Substituent S i1 It represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.

[0183] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0184] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 3 to 6 carbon atoms.

[0185] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0186] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[0187] One or two or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0188] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0189] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0190] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0191] As a substituent S i1 , preferably a fluorine atom, a linear alkyl group having 1 to 6 carbon atoms, or a linear alkoxy group having 1 to 6 carbon atoms.

[0192] In addition, A i1 , A i2 , A i3 and A i4 At least one of the substituents S i1 replace.

[0193] In addition, A i4 Preferably, at least one substituent S i1 replace.

[0194] In addition, in the substituent S i1 When there are plural, these may be the same or different.

[0195] As A i1 The substituent S in i1 The substitution position is preferably the following formula (A i1 -SP-1)~Formula (A i1 -SP-4) in any one.

[0196] [Chemistry 9]

[0197]

[0198] Formula (A i1 -SP-1)~Formula (A i1 -SP-4), the white dot indicates the direction to R i1 The black dots represent the bonds to Z i1 The bond key.

[0199] As A i2 The substituent S in i1 The substitution position is preferably the following formula (A i2 -SP-1)~Formula (A i2 -SP-4) in any one.

[0200] [Chemistry 10]

[0201]

[0202] Formula (A i2 -SP-1)~Formula (A i2 -SP-4), the white dot indicates the direction of Z i1 The black dots represent the bonds to Z i2 The bond key.

[0203] As A i3 The substituent S in i1 The substitution position is preferably the following formula (A i3 -SP-1)~Formula (A i3 -SP-4) in any one.

[0204] [Chemistry 11]

[0205]

[0206] Formula (A i3 -SP-1)~Formula (A i3 -SP-4), the white dot indicates the Z i2 The black dots represent the bonds to Z i3 The bond key.

[0207] As A i4 The substituent S in i1 The substitution position is preferably the following formula (A i4 -SP-1)~Formula (A i4 -SP-4) in any one.

[0208] [Chemistry 12]

[0209]

[0210] Formula (A i4 -SP-1)~Formula (A i4 -SP-4), the white dot indicates the direction of Z i3 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0211] More specifically, A i1 Preferably, it is represented by the following formula (Ai1 -1)~Formula (A i1 -11).

[0212] [Chemistry 13]

[0213]

[0214] Formula (A i1 -1)~Formula (A i1 -11), the white dot indicates the direction to R i1 The black dots represent the bonds to Z i1 The bond key.

[0215] More specifically, A i2 Preferably, it is represented by the following formula (A i2 -1)~Formula (A i2 -11).

[0216] [Chemistry 14]

[0217]

[0218] Formula (A i2 -1)~Formula (A i2 -11), the white dot indicates the direction Z i1 The black dots represent the bonds to Z i2 More specifically, A i3 Preferably, it is represented by the following formula (A i3 -1)~Formula (A i3 -11).

[0219] [Chemistry 15]

[0220]

[0221] Formula (A i3 -1)~Formula (A i3 -11), the white dot indicates the direction Z i2 The black dots represent the bonds to Z i3 More specifically, A i4 Preferably, it is represented by the following formula (A i4 -1)~Formula (A i4 -11).

[0222] [Chemistry 16]

[0223]

[0224] Formula (A i4 -1)~Formula (A i4 -11), the white dot indicates the direction Z i3The black dots represent the bonds to the isothiocyanate group (-NCS).

[0225] Z i1 , Z i2 and Z i3 Each independently represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0226] Among them, Z i1 , Z i2 and Z i3 At least one representation of -C≡C-.

[0227] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0228] The alkylene group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0229] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0230] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0231] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0232] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted alkylene groups) include the following: i1 / 2 / 3 -1)~Formula(Z i1 / 2 / 3 -24) represented by the base, etc.

[0233] [Chemistry 17]

[0234]

[0235] Formula (Z i1 / 2 / 3 -1)~Formula(Z i1 / 2 / 3 -24), the white dot indicates the direction to A i1 , A i2 or A i3 The black dots indicate the bond to A i2 , A i3 or A i4 The bond key.

[0236] From the perspective of increasing Δn, Z i3 Preferably, the formula (Z i1 / 2 / 3 -4)(-C≡C-).

[0237] As the compound represented by the general formula (i), compounds represented by the following general formulas (i-1) to (i-4) are preferred.

[0238] [Chemistry 18]

[0239]

[0240] In the general formulas (i-1) to (i-4), R i1 , A i1 , A i2 , A i3 and A i4 Each independently represents R i1 , A i1 , A i2 , A i3 and A i4 Same meaning.

[0241] As the compound represented by the general formula (i-1), compounds represented by the following general formulas (i-1-1) to (i-1-20) are preferred.

[0242] [Chemistry 19]

[0243]

[0244] [Chemistry 20]

[0245]

[0246] [Chemistry 21]

[0247]

[0248] [Chemistry 22]

[0249]

[0250] In the general formulas (i-1-1) to (i-1-20), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0251] Specific examples of the compound represented by the general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.8).

[0252] [Chemistry 23]

[0253]

[0254] [Chemistry 24]

[0255]

[0256] Specific examples of the compound represented by the general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.4).

[0257] [Chemistry 25]

[0258]

[0259] Specific examples of the compound represented by general formula (i-1-3) include compounds represented by the following structural formulas (i-1-3.1) to (i-1-3.4).

[0260] [Chemistry 26]

[0261]

[0262] Specific examples of the compound represented by the general formula (i-1-4) include compounds represented by the following structural formulas (i-1-4.1) to (i-1-4.4).

[0263] [Chemistry 27]

[0264]

[0265] Specific examples of the compound represented by general formula (i-1-5) include compounds represented by the following structural formulas (i-1-5.1) to (i-1-5.4).

[0266] [Chemistry 28]

[0267]

[0268] Specific examples of the compound represented by the general formula (i-1-6) include compounds represented by the following structural formulas (i-1-6.1) to (i-1-6.4).

[0269] [Chemistry 29]

[0270]

[0271] Specific examples of the compound represented by general formula (i-1-7) include compounds represented by the following structural formulas (i-1-7.1) to (i-1-7.8).

[0272] [Chemistry 30]

[0273]

[0274] [Chemistry 31]

[0275]

[0276] Specific examples of the compound represented by the general formula (i-1-8) include compounds represented by the following structural formulas (i-1-8.1) to (i-1-8.8).

[0277] [Chemistry 32]

[0278]

[0279] [Chemistry 33]

[0280]

[0281] Specific examples of the compound represented by the general formula (i-1-9) include compounds represented by the following structural formulas (i-1-9.1) to (i-1-9.8).

[0282] [Chemistry 34]

[0283]

[0284] [Chemistry 35]

[0285]

[0286] Specific examples of the compound represented by the general formula (i-1-10) include compounds represented by the following structural formulas (i-1-10.1) to (i-1-10.4).

[0287] [Chemistry 36]

[0288]

[0289] Specific examples of the compound represented by the general formula (i-1-11) include compounds represented by the following structural formulas (i-1-11.1) to (i-1-11.4).

[0290] [Chemistry 37]

[0291]

[0292] Specific examples of the compound represented by the general formula (i-1-12) include compounds represented by the following structural formulas (i-1-12.1) to (i-1-12.8).

[0293] [Chemistry 38]

[0294]

[0295] [Chemistry 39]

[0296]

[0297] Specific examples of the compound represented by the general formula (i-1-13) include compounds represented by the following structural formulas (i-1-13.1) to (i-1-13.8).

[0298] [Chemistry 40]

[0299]

[0300] [Chemistry 41]

[0301]

[0302] Specific examples of the compound represented by general formula (i-1-14) include compounds represented by the following structural formulas (i-1-14.1) to (i-1-14.4).

[0303] [Chemistry 42]

[0304]

[0305] Specific examples of the compound represented by the general formula (i-1-15) include compounds represented by the following structural formulas (i-1-15.1) to (i-1-15.4).

[0306] [Chemistry 43]

[0307]

[0308] Specific examples of the compound represented by the general formula (i-1-16) include compounds represented by the following structural formulas (i-1-16.1) to (i-1-16.4).

[0309] [Chemistry 44]

[0310]

[0311] Specific examples of the compound represented by the general formula (i-1-17) include compounds represented by the following structural formulas (i-1-17.1) to (i-1-17.4).

[0312] [Chemistry 45]

[0313]

[0314] Specific examples of the compound represented by general formula (i-1-18) include compounds represented by the following structural formulas (i-1-19.1) to (i-1-18.4).

[0315] [Chemistry 46]

[0316]

[0317] Specific examples of the compound represented by general formula (i-1-19) include compounds represented by the following structural formulas (i-1-19.1) to (i-1-19.4).

[0318] [Chemistry 47]

[0319]

[0320] Specific examples of the compound represented by the general formula (i-1-20) include compounds represented by the following structural formulas (i-1-20.1) to (i-1-20.4).

[0321] [Chemistry 48]

[0322]

[0323] As the compound represented by the general formula (i-2), compounds represented by the following general formulas (i-2-1) to (i-2-18) are preferred.

[0324] [Chemistry 49]

[0325]

[0326] [Chemistry 50]

[0327]

[0328] [Chemistry 51]

[0329]

[0330] [Chemistry 52]

[0331]

[0332] In the general formulas (i-2-1) to (i-2-18), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0333] Specific examples of the compound represented by the general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.4).

[0334] [Chemistry 53]

[0335]

[0336] Specific examples of the compound represented by general formula (i-2-2) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.8).

[0337] [Chemistry 54]

[0338]

[0339] [Chemistry 55]

[0340]

[0341] Specific examples of the compound represented by the general formula (i-2-3) include compounds represented by the following structural formulas (i-2-3.1) to (i-2-3.8).

[0342] [Chemistry 56]

[0343]

[0344] [Chemistry 57]

[0345]

[0346] Specific examples of the compound represented by general formula (i-2-4) include compounds represented by the following structural formulas (i-2-4.1) to (i-2-4.4).

[0347] [Chemistry 58]

[0348]

[0349] Specific examples of the compound represented by the general formula (i-2-5) include compounds represented by the following structural formulas (i-2-5.1) to (i-2-5.4).

[0350] [Chemistry 59]

[0351]

[0352] Specific examples of the compound represented by the general formula (i-2-6) include compounds represented by the following structural formulas (i-2-6.1) to (i-2-6.4).

[0353] [Chemistry 60]

[0354]

[0355] Specific examples of the compound represented by general formula (i-2-7) include compounds represented by the following structural formulas (i-2-7.1) to (i-2-7.15).

[0356] [Chemistry 61]

[0357]

[0358] [Chemistry 62]

[0359]

[0360] [Chemistry 63]

[0361]

[0362] [Chemistry 64]

[0363]

[0364] [Chemistry 65]

[0365]

[0366] Specific examples of the compound represented by general formula (i-2-8) include compounds represented by the following structural formulas (i-2-8.1) to (i-2-8.8).

[0367] [Chemistry 66]

[0368]

[0369] [Chemistry 67]

[0370]

[0371] Specific examples of the compound represented by the general formula (i-2-9) include compounds represented by the following structural formulas (i-2-9.1) to (i-2-9.4).

[0372] [Chemistry 68]

[0373]

[0374] Specific examples of the compound represented by the general formula (i-2-10) include compounds represented by the following structural formulas (i-2-10.1) to (i-2-10.4).

[0375] [Chemistry 69]

[0376]

[0377] Specific examples of the compound represented by the general formula (i-2-11) include compounds represented by the following structural formulas (i-2-11.1) to (i-2-11.8).

[0378] [Chemistry 70]

[0379]

[0380] [Chemistry 71]

[0381]

[0382] Specific examples of the compound represented by the general formula (i-2-12) include compounds represented by the following structural formulas (i-2-12.1) to (i-2-12.4).

[0383] [Chemistry 72]

[0384]

[0385] Specific examples of the compound represented by the general formula (i-2-13) include compounds represented by the following structural formulas (i-2-13.1) to (i-2-13.4).

[0386] [Chemistry 73]

[0387]

[0388] Specific examples of the compound represented by the general formula (i-2-14) include compounds represented by the following structural formulas (i-2-14.1) to (i-2-14.4).

[0389] [Chemistry 74]

[0390]

[0391] Specific examples of the compound represented by the general formula (i-2-15) include compounds represented by the following structural formulas (i-2-15.1) to (i-2-15.4).

[0392] [Chemistry 75]

[0393]

[0394] Specific examples of the compound represented by the general formula (i-2-16) include compounds represented by the following structural formulas (i-2-16.1) to (i-2-16.4).

[0395] [Chemistry 76]

[0396]

[0397] Specific examples of the compound represented by the general formula (i-2-17) include compounds represented by the following structural formulas (i-2-17.1) to (i-2-17.4).

[0398] [Chemistry 77]

[0399]

[0400] Specific examples of the compound represented by general formula (i-2-18) include compounds represented by the following structural formulas (i-2-18.1) to (i-2-18.4).

[0401] [Chemistry 78]

[0402]

[0403] As the compound represented by the general formula (i-3), compounds represented by the following general formulas (i-3-1) to (i-3-22) are preferred.

[0404] [Chemistry 79]

[0405]

[0406] [Chemistry 80]

[0407]

[0408] [Chemistry 81]

[0409]

[0410] [Chemistry 82]

[0411]

[0412] [Chemistry 83]

[0413]

[0414] [Chemistry 84]

[0415]

[0416] In the general formulas (i-3-1) to (i-3-22), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0417] Specific examples of the compound represented by general formula (i-3-1) include compounds represented by the following structural formulas (i-3-1.1) to (i-3-1.4).

[0418] [Chemistry 85]

[0419]

[0420] Specific examples of the compound represented by general formula (i-3-2) include compounds represented by the following structural formulas (i-3-2.1) to (i-3-2.8).

[0421] [Chemistry 86]

[0422]

[0423] [Chemistry 87]

[0424]

[0425] Specific examples of the compound represented by general formula (i-3-3) include compounds represented by the following structural formulas (i-3-3.1) to (i-3-3.4).

[0426] [Chemistry 88]

[0427]

[0428] Specific examples of the compound represented by general formula (i-3-4) include compounds represented by the following structural formulas (i-3-4.1) to (i-3-4.8).

[0429] [Chemistry 89]

[0430]

[0431] [Chemistry 90]

[0432]

[0433] Specific examples of the compound represented by general formula (i-3-5) include compounds represented by the following structural formulas (i-3-5.1) to (i-3-5.4).

[0434] [Chemistry 91]

[0435]

[0436] Specific examples of the compound represented by the general formula (i-3-6) include compounds represented by the following structural formulas (i-3-6.1) to (i-3-6.24).

[0437] [Chemistry 92]

[0438]

[0439] [Chemistry 93]

[0440]

[0441] [Chemistry 94]

[0442]

[0443] [Chemistry 95]

[0444]

[0445] [Chemistry 96]

[0446]

[0447] Specific examples of the compound represented by general formula (i-3-7) include compounds represented by the following structural formulas (i-3-7.1) to (i-3-7.4).

[0448] [Chemistry 97]

[0449]

[0450] Specific examples of the compound represented by general formula (i-3-8) include compounds represented by the following structural formulas (i-3-8.1) to (i-3-8.23).

[0451] [Chemistry 98]

[0452]

[0453] [Chemistry 99]

[0454]

[0455] [Chemical 100]

[0456]

[0457] [Chemistry 101]

[0458]

[0459] [Chemistry 102]

[0460]

[0461] [Chemistry 103]

[0462]

[0463] Specific examples of the compound represented by general formula (i-3-9) include compounds represented by the following structural formulas (i-3-9.1) to (i-3-9.4).

[0464] [Chemistry 104]

[0465]

[0466] Specific examples of the compound represented by the general formula (i-3-10) include compounds represented by the following structural formulas (i-3-10.1) to (i-3-10.8).

[0467] [Chemistry 105]

[0468]

[0469] [Chemistry 106]

[0470]

[0471] Specific examples of the compound represented by the general formula (i-3-11) include compounds represented by the following structural formulas (i-3-11.1) to (i-3-11.4).

[0472] [Chemistry 107]

[0473]

[0474] Specific examples of the compound represented by the general formula (i-3-12) include compounds represented by the following structural formulas (i-3-12.1) to (i-3-12.4).

[0475] [Chemistry 108]

[0476]

[0477] Specific examples of the compound represented by general formula (i-3-13) include compounds represented by the following structural formulas (i-3-13.1) to (i-3-13.4).

[0478] [Chemistry 109]

[0479]

[0480] Specific examples of the compound represented by general formula (i-3-14) include compounds represented by the following structural formulas (i-3-14.1) to (i-3-14.4).

[0481] [Chemistry 110]

[0482]

[0483] Specific examples of the compound represented by general formula (i-3-15) include compounds represented by the following structural formulas (i-3-15.1) to (i-3-15.8).

[0484] [Chemistry 111]

[0485]

[0486] [Chemistry 112]

[0487]

[0488] Specific examples of the compound represented by the general formula (i-3-16) include compounds represented by the following structural formulas (i-3-16.1) to (i-3-16.4).

[0489] [Chemistry 113]

[0490]

[0491] Specific examples of the compound represented by the general formula (i-3-17) include compounds represented by the following structural formulas (i-3-17.1) to (i-3-17.4).

[0492] [Chemistry 114]

[0493]

[0494] Specific examples of the compound represented by general formula (i-3-18) include compounds represented by the following structural formulas (i-3-18.1) to (i-3-18.4).

[0495] [Chemistry 115]

[0496]

[0497] Specific examples of the compound represented by general formula (i-3-19) include compounds represented by the following structural formulas (i-3-19.1) to (i-3-19.8).

[0498] [Chemistry 116]

[0499]

[0500] [Chemistry 117]

[0501]

[0502] Specific examples of the compound represented by the general formula (i-3-20) include compounds represented by the following structural formulas (i-3-20.1) to (i-3-20.4).

[0503] [Chemistry 118]

[0504]

[0505] Specific examples of the compound represented by the general formula (i-3-21) include compounds represented by the following structural formulas (i-3-21.1) to (i-3-21.4).

[0506] [Chemistry 119]

[0507]

[0508] Specific examples of the compound represented by general formula (i-3-22) include compounds represented by the following structural formula (i-3-22.1).

[0509] [Chemistry 120]

[0510]

[0511] As the compound represented by the general formula (i-4), a compound represented by the following general formula (i-4-1) is preferred.

[0512] [Chemistry 121]

[0513]

[0514] In the general formula (i-4-1), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0515] Specific examples of the compound represented by general formula (i-4-1) include compounds represented by the following structural formulas (i-4-1.1) to (i-4-1.3).

[0516] [Chemistry 122]

[0517]

[0518] General formula (i), general formula (i-1) to general formula (i-4), general formula (i-1-1) to general formula (i-1-20), general formula (i-2-1) to general formula (i-2-18), general formula (i-3-1) to general formula (i-3-22), general formula (i-4-1), structural formula (i-1-1.1) to structural formula (i-1-1.8), structural formula (i-1-2.1) to structural formula (i-1-2.4), structural formula (i-1-3.1) to structural formula (i-1-3.4), structural formula (i-1-4.1) to structural formula (i-1-4.4), structural formula (i-1-5.1) to structural formula (i-1-5.4), structural formula (i-1-6.1) to structural formula (i-1-6. 4), structural formula (i-1-7.1) to structural formula (i-1-7.8), structural formula (i-1-8.1) to structural formula (i-1-8.8), structural formula (i-1-9.1) to structural formula (i-1-9.8), structural formula (i-1-10.1) to structural formula (i-1-10.4), structural formula (i-1-11.1) to structural formula (i-1-11.4), structural formula (i-1-12.1) to structural formula (i-1-12.8), structural formula (i-1-13.1) to structural formula (i-1-13.8), structural formula (i-1-14.1) to structural formula (i-1-14.4), structural formula (i-1-15.1) to structural formula (i-1-15.4), Structural formula (i-1-16.1) to (i-1-16.4), Structural formula (i-1-17.1) to (i-1-17.4), Structural formula (i-1-18.1) to (i-1-18.4), Structural formula (i-1-19.1) to (i-1-19.4), Structural formula (i-1-20.1) to (i-1-20.4), Structural formula (i-2-1.1) to (i-2-1.4), Structural formula (i-2-2.1) to (i-2-2.8), Structural formula (i-2-3.1) to (i-2-3.8), Structural formula (i-2-4.1) to (i-2-4.4), Structural formula (i -2-5.1) ~ structural formula (i-2-5.4), structural formula (i-2-6.1) ~ structural formula (i-2-6.4), structural formula (i-2-7.1) ~ structural formula (i-2-7.15), structural formula (i-2-8.1) ~ structural formula (i-2-8.8), structural formula (i-2-9.1) ~ structural formula (i-2-9.4), structural formula (i-2-10.1) ~ structural formula (i-2-10.4), structural formula (i-2-11.1) ~ structural formula (i-2-11.8), structural formula (i-2-12.1) ~ structural formula (i-2-12.4), structural formula (i-2-13.1) ~ structural formula (i-2-13.4), structural formula (i-2-14.1)~Structural formula (i-2-14.4), structural formula (i-2-15.1)~Structural formula (i-2-15.4), structural formula (i-2-16.1)~Structural formula (i-2-16.4), structural formula (i-2-17.1)~Structural formula (i-2-17.4), structural formula (i-2-18.1)~Structural formula (i-2-18.4), structural formula (i-3-1.1)~Structural formula (i-3-1.4), structural formula (i-3-2.1)~Structural formula (i-3-2.8), structural formula (i-3-3.1)~Structural formula ( i-3-3.4), structural formula (i-3-4.1) to structural formula (i-3-4.8), structural formula (i-3-5.1) to structural formula (i-3-5.4), structural formula (i-3-6.1) to structural formula (i-3-6.24), structural formula (i-3-7.1) to structural formula (i-3-7.4), structural formula (i-3-8.1) to structural formula (i-3-8.23), structural formula (i-3-9.1) to structural formula (i-3-9.4), structural formula (i-3-10.1) to structural formula (i-3-10.8), structural formula ( i-3-11.1) to (i-3-11.4), (i-3-12.1) to (i-3-12.4), (i-3-13.1) to (i-3-13.4), (i-3-14.1) to (i-3-14.4), (i-3-15.1) to (i-3-15.8), (i-3-16.1) to (i-3-16.4), (i-3-17.1) to (i-3-17.4), (i-3-18.1) to (i-3-18.4), The types of compounds represented by formula (i-18.1) to formula (i-3-18.4), formula (i-3-19.1) to formula (i-3-19.8), formula (i-3-20.1) to formula (i-3-20.4), formula (i-3-21.1) to formula (i-3-21.4), formula (i-3-22.1) or formula (i-4-1.1) to formula (i-4-1.3) used in the liquid crystal composition are one or more, preferably one to ten, preferably one to five, and preferably one to three. .

[0519] General formula (i), general formula (i-1) to general formula (i-4), general formula (i-1-1) to general formula (i-1-20), general formula (i-2-1) to general formula (i-2-18), general formula (i-3-1) to general formula (i-3-22), general formula (i-4-1), structural formula (i-1-1.1) to structural formula (i-1-1.8), structural formula (i-1-2.1) to structural formula (i-1-2.4), structural formula (i-1-3.1) to structural formula (i-1-3.4), structural formula (i-1-4.1) to structural formula (i-1-4.4), structural formula (i-1-5.1) to structural formula (i-1-5.4), structural formula (i-1-6.1) to structural formula (i-1-6. 4), structural formula (i-1-7.1) to structural formula (i-1-7.8), structural formula (i-1-8.1) to structural formula (i-1-8.8), structural formula (i-1-9.1) to structural formula (i-1-9.8), structural formula (i-1-10.1) to structural formula (i-1-10.4), structural formula (i-1-11.1) to structural formula (i-1-11.4), structural formula (i-1-12.1) to structural formula (i-1-12.8), structural formula (i-1-13.1) to structural formula (i-1-13.8), structural formula (i-1-14.1) to structural formula (i-1-14.4), structural formula (i-1-15.1) to structural formula (i-1-15.4), Structural formula (i-1-16.1) to (i-1-16.4), Structural formula (i-1-17.1) to (i-1-17.4), Structural formula (i-1-18.1) to (i-1-18.4), Structural formula (i-1-19.1) to (i-1-19.4), Structural formula (i-1-20.1) to (i-1-20.4), Structural formula (i-2-1.1) to (i-2-1.4), Structural formula (i-2-2.1) to (i-2-2.8), Structural formula (i-2-3.1) to (i-2-3.8), Structural formula (i-2-4.1) to (i-2-4.4), Structural formula (i -2-5.1) ~ structural formula (i-2-5.4), structural formula (i-2-6.1) ~ structural formula (i-2-6.4), structural formula (i-2-7.1) ~ structural formula (i-2-7.15), structural formula (i-2-8.1) ~ structural formula (i-2-8.8), structural formula (i-2-9.1) ~ structural formula (i-2-9.4), structural formula (i-2-10.1) ~ structural formula (i-2-10.4), structural formula (i-2-11.1) ~ structural formula (i-2-11.8), structural formula (i-2-12.1) ~ structural formula (i-2-12.4), structural formula (i-2-13.1) ~ structural formula (i-2-13.4), structural formula (i-2-14.1)~Structural formula (i-2-14.4), structural formula (i-2-15.1)~Structural formula (i-2-15.4), structural formula (i-2-16.1)~Structural formula (i-2-16.4), structural formula (i-2-17.1)~Structural formula (i-2-17.4), structural formula (i-2-18.1)~Structural formula (i-2-18.4), structural formula (i-3-1.1)~Structural formula (i-3-1.4), structural formula (i-3-2.1)~Structural formula (i-3-2.8), structural formula (i-3-3.1)~Structural formula (i-3-3.4 )、Structural formula (i-3-4.1) ~ structural formula (i-3-4.8), structural formula (i-3-5.1) ~ structural formula (i-3-5.4), structural formula (i-3-6.1) ~ structural formula (i-3-6.24), structural formula (i-3-7.1) ~ structural formula (i-3-7.4), structural formula (i-3-8.1) ~ structural formula (i-3-8.23), structural formula (i-3-9.1) ~ structural formula (i-3-9.4), structural formula (i-3-10.1) ~ structural formula (i-3-10.8), structural formula (i-3-11.1) ~ structural formula (i-3-11.4), structural formula (i-3-12.1) to structural formula (i-3-12.4), structural formula (i-3-13.1) to structural formula (i-3-13.4), structural formula (i-3-14.1) to structural formula (i-3-14.4), structural formula (i-3-15.1) to structural formula (i-3-15.8), structural formula (i-3-16.1) to structural formula (i-3-16.4), structural formula (i-3-17.1) to structural formula (i-3-17.4), structural formula (i-3-18.1) to structural formula (i-3-18.4 ), the lower limit of the total content of the compounds represented by the structural formula (i-3-19.1) to the structural formula (i-3-19.8), the structural formula (i-3-20.1) to the structural formula (i-3-20.4), the structural formula (i-3-21.1) to the structural formula (i-3-21.4), the structural formula (i-3-22.1) or the structural formula (i-4-1.1) to the structural formula (i-4-1.3) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, and preferably 15% by mass or more. .

[0520] General formula (i), general formula (i-1) to general formula (i-4), general formula (i-1-1) to general formula (i-1-20), general formula (i-2-1) to general formula (i-2-18), general formula (i-3-1) to general formula (i-3-22), general formula (i-4-1), structural formula (i-1-1.1) to structural formula (i-1-1.8), structural formula (i-1-2.1) to structural formula (i-1-2.4), structural formula (i-1-3.1) to structural formula (i-1-3.4), structural formula (i-1-4.1) to structural formula (i-1-4.4), structural formula (i-1-5.1) to structural formula (i-1-5.4), structural formula (i-1-6.1) to structural formula (i-1-6. 4), structural formula (i-1-7.1) to structural formula (i-1-7.8), structural formula (i-1-8.1) to structural formula (i-1-8.8), structural formula (i-1-9.1) to structural formula (i-1-9.8), structural formula (i-1-10.1) to structural formula (i-1-10.4), structural formula (i-1-11.1) to structural formula (i-1-11.4), structural formula (i-1-12.1) to structural formula (i-1-12.8), structural formula (i-1-13.1) to structural formula (i-1-13.8), structural formula (i-1-14.1) to structural formula (i-1-14.4), structural formula (i-1-15.1) to structural formula (i-1-15.4), Structural formula (i-1-16.1) to (i-1-16.4), Structural formula (i-1-17.1) to (i-1-17.4), Structural formula (i-1-18.1) to (i-1-18.4), Structural formula (i-1-19.1) to (i-1-19.4), Structural formula (i-1-20.1) to (i-1-20.4), Structural formula (i-2-1.1) to (i-2-1.4), Structural formula (i-2-2.1) to (i-2-2.8), Structural formula (i-2-3.1) to (i-2-3.8), Structural formula (i-2-4.1) to (i-2-4.4), Structural formula (i -2-5.1) ~ structural formula (i-2-5.4), structural formula (i-2-6.1) ~ structural formula (i-2-6.4), structural formula (i-2-7.1) ~ structural formula (i-2-7.15), structural formula (i-2-8.1) ~ structural formula (i-2-8.8), structural formula (i-2-9.1) ~ structural formula (i-2-9.4), structural formula (i-2-10.1) ~ structural formula (i-2-10.4), structural formula (i-2-11.1) ~ structural formula (i-2-11.8), structural formula (i-2-12.1) ~ structural formula (i-2-12.4), structural formula (i-2-13.1) ~ structural formula (i-2-13.4), structural formula (i-2-14.1)~Structural formula (i-2-14.4), structural formula (i-2-15.1)~Structural formula (i-2-15.4), structural formula (i-2-16.1)~Structural formula (i-2-16.4), structural formula (i-2-17.1)~Structural formula (i-2-17.4), structural formula (i-2-18.1)~Structural formula (i-2-18.4), structural formula (i-3-1.1)~Structural formula (i-3-1.4), structural formula (i-3-2.1)~Structural formula (i-3-2.8), structural formula (i-3-3.1)~Structural formula (i-3-3.4), structural formula ( i-3-4.1) ~ structural formula (i-3-4.8), structural formula (i-3-5.1) ~ structural formula (i-3-5.4), structural formula (i-3-6.1) ~ structural formula (i-3-6.24), structural formula (i-3-7.1) ~ structural formula (i-3-7.4), structural formula (i-3-8.1) ~ structural formula (i-3-8.23), structural formula (i-3-9.1) ~ structural formula (i-3-9.4), structural formula (i-3-10.1) ~ structural formula (i-3-10.8), structural formula (i-3-11.1) ~ structural formula (i-3-11.4), Structural formula (i-3-12.1) to structural formula (i-3-12.4), structural formula (i-3-13.1) to structural formula (i-3-13.4), structural formula (i-3-14.1) to structural formula (i-3-14.4), structural formula (i-3-15.1) to structural formula (i-3-15.8), structural formula (i-3-16.1) to structural formula (i-3-16.4), structural formula (i-3-17.1) to structural formula (i-3-17.4), structural formula (i-3-18.1) to structural formula (i-3-18.4), structural formula (i-3-19.1) to structural formula The upper limit of the total content of the compounds represented by formula (i-3-19.8), structural formula (i-3-20.1) to structural formula (i-3-20.4), structural formula (i-3-21.1) to structural formula (i-3-21.4), structural formula (i-3-22.1) or structural formula (i-4-1.1) to structural formula (i-4-1.3) in 100% by mass of the liquid crystal composition is preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less. .

[0521] Regarding solubility, Δn and / or Δε rFrom the perspective of general formula (i), general formula (i-1) to general formula (i-4), general formula (i-1-1) to general formula (i-1-20), general formula (i-2-1) to general formula (i-2-18), general formula (i-3-1) to general formula (i-3-22), general formula (i-4-1), structural formula (i-1-1.1) to structural formula (i-1-1.8), structural formula (i-1-2.1) to structural formula (i-1-2.4), structural formula (i-1-3.1) to structural formula (i-1-3.4), structural formula (i-1-4.1) to structural formula (i-1-4.4), structural formula (i-1-5.1) to structural formula (i-1-5.4), structural formula (i-1-6.1) to structural formula (i-1-6.2) 1-6.4), structural formula (i-1-7.1) to structural formula (i-1-7.8), structural formula (i-1-8.1) to structural formula (i-1-8.8), structural formula (i-1-9.1) to structural formula (i-1-9.8), structural formula (i-1-10.1) to structural formula (i-1-10.4), structural formula (i-1-11.1) to structural formula (i-1-11.4), structural formula (i-1-12.1) to structural formula (i-1-12.8), structural formula (i-1-13.1) to structural formula (i-1-13.8), structural formula (i-1-14.1) to structural formula (i-1-14.4), structural formula (i-1-15.1) to structural formula (i-1-15. 4), structural formula (i-1-16.1) to structural formula (i-1-16.4), structural formula (i-1-17.1) to structural formula (i-1-17.4), structural formula (i-1-18.1) to structural formula (i-1-18.4), structural formula (i-1-19.1) to structural formula (i-1-19.4), structural formula (i-1-20.1) to structural formula (i-1-20.4), structural formula (i-2-1.1) to structural formula (i-2-1.4), structural formula (i-2-2.1) to structural formula (i-2-2.8), structural formula (i-2-3.1) to structural formula (i-2-3.8), structural formula (i-2-4.1) to structural formula (i-2-4.4), structural formula (i-2-5.1) to (i-2-5.4), (i-2-6.1) to (i-2-6.4), (i-2-7.1) to (i-2-7.15), (i-2-8.1) to (i-2-8.8), (i-2-9.1) to (i-2-9.4), (i-2-10.1) to (i-2-10.4), (i-2-11.1) to (i-2-11.8), (i-2-12.1) to (i-2-12.4), (i-2-13.1) to (i-2-13.4), (i-2-14.1)~Structural formula (i-2-14.4), structural formula (i-2-15.1)~Structural formula (i-2-15.4), structural formula (i-2-16.1)~Structural formula (i-2-16.4), structural formula (i-2-17.1)~Structural formula (i-2-17.4), structural formula (i-2-18.1)~Structural formula (i-2-18.4), structural formula (i-3-1.1)~Structural formula (i-3-1.4), structural formula (i-3-2.1)~Structural formula (i-3-2.8), structural formula (i-3-3.1)~Structural formula (i-3 -3.4), structural formula (i-3-4.1) to structural formula (i-3-4.8), structural formula (i-3-5.1) to structural formula (i-3-5.4), structural formula (i-3-6.1) to structural formula (i-3-6.24), structural formula (i-3-7.1) to structural formula (i-3-7.4), structural formula (i-3-8.1) to structural formula (i-3-8.23), structural formula (i-3-9.1) to structural formula (i-3-9.4), structural formula (i-3-10.1) to structural formula (i-3-10.8), structural formula (i-3-11 .1)~Structural formula (i-3-11.4), structural formula (i-3-12.1)~Structural formula (i-3-12.4), structural formula (i-3-13.1)~Structural formula (i-3-13.4), structural formula (i-3-14.1)~Structural formula (i-3-14.4), structural formula (i-3-15.1)~Structural formula (i-3-15.8), structural formula (i-3-16.1)~Structural formula (i-3-16.4), structural formula (i-3-17.1)~Structural formula (i-3-17.4), structural formula (i-3-18.1)~Structural formula The total content of the compounds represented by formula (i-3-18.4), structural formula (i-3-19.1) to structural formula (i-3-19.8), structural formula (i-3-20.1) to structural formula (i-3-20.4), structural formula (i-3-21.1) to structural formula (i-3-21.4), structural formula (i-3-22.1) or structural formula (i-4-1.1) to structural formula (i-4-1.3) in 100% by mass of the liquid crystal composition is preferably 1% by mass to 35% by mass, preferably 1% by mass to 30% by mass, and preferably 3% by mass to 25% by mass.

[0522] The compound represented by the general formula (i) (including subordinate concepts) can be synthesized using known synthesis methods, and several methods are exemplified below.

[0523] (Preparation method 1) Preparation of a compound represented by the following formula (S-7)

[0524] [Chemistry 123]

[0525]

[0526] (In general formula (S-1) to general formula (S-7), R i1 and S i1 represents the same as R in the general formula (i) i1 and S i1 Same meaning)

[0527] First, bis(pinacolato)diboron is reacted with the compound represented by the general formula (S-1), thereby obtaining the compound represented by the general formula (S-2).

[0528] Examples of the reaction method include a method of Suzuki coupling in the presence of a metal catalyst and a base.

[0529] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0530] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0531] Specific examples of the base include potassium acetate, potassium carbonate, potassium phosphate, and cesium carbonate.

[0532] Next, the compound represented by the general formula (S-2) is reacted with the compound represented by the general formula (S-3), thereby obtaining the compound represented by the general formula (S-4).

[0533] Examples of the reaction method include a method of Suzuki coupling in the presence of a metal catalyst and a base.

[0534] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0535] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0536] Specific examples of the base include potassium carbonate, potassium phosphate, and cesium carbonate.

[0537] Furthermore, by reacting the compound represented by the general formula (S-4) with the compound represented by the general formula (S-5), a compound represented by the general formula (S-6) can be obtained.

[0538] Examples of the reaction method include a method of Suzuki coupling in the presence of a metal catalyst and a base.

[0539] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0540] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0541] Specific examples of the base include potassium carbonate, potassium phosphate, and cesium carbonate.

[0542] Finally, the amino group of the compound represented by the general formula (S-6) is reacted with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, thiophosgene, or the like to obtain the target compound represented by the general formula (S-7).

[0543] (Preparation method 2) Preparation of a compound represented by the following formula (S-13)

[0544] [Chemistry 124]

[0545]

[0546] (In general formula (S-8) to general formula (S-13), R i1 and S i1 represents the same as R in the general formula (i) i1 and S i1 Same meaning)

[0547] First, bis(pinacolato)diboron is reacted with the compound represented by the general formula (S-8), thereby obtaining the compound represented by the general formula (S-9).

[0548] Examples of the reaction method include a method of Suzuki coupling in the presence of a metal catalyst and a base.

[0549] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0550] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0551] Specific examples of the base include potassium acetate, potassium carbonate, potassium phosphate, and cesium carbonate.

[0552] Next, by reacting 1-bromo-4-iodobenzene with the compound represented by the general formula (S-9), a compound represented by the general formula (S-10) can be obtained.

[0553] Examples of the reaction method include a method of Suzuki coupling in the presence of a metal catalyst and a base.

[0554] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0555] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0556] Specific examples of the base include potassium carbonate, potassium phosphate, and cesium carbonate.

[0557] Furthermore, by reacting the compound represented by the general formula (S-10) with the compound represented by the general formula (S-11), the compound represented by the general formula (S-12) can be obtained.

[0558] Examples of the reaction method include a method of Suzuki coupling in the presence of a metal catalyst and a base.

[0559] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0560] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0561] Specific examples of the base include potassium carbonate, potassium phosphate, and cesium carbonate.

[0562] Finally, the amino group of the compound represented by the general formula (S-12) is reacted with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, thiophosgene, or the like to obtain the target compound represented by the general formula (S-13).

[0563] (Preparation method 3) Preparation of a compound represented by the following formula (S-19)

[0564] [Chemistry 125]

[0565]

[0566] (In general formula (S-14) to general formula (S-19), R i1 and S i1 represents the same as R in the general formula (i) i1 and S i1 Same meaning)

[0567] First, a compound represented by the general formula (S-14) is reacted with a compound represented by the general formula (S-15) to obtain a compound represented by the general formula (S-16).

[0568] As a reaction method, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base is mentioned, for example.

[0569] Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0570] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0571] Specific examples of the copper catalyst include copper (I) iodide.

[0572] Specific examples of the base include triethylamine and diisopropylamine.

[0573] Next, the compound represented by the general formula (S-16) is reacted with the compound represented by the general formula (S-17), thereby obtaining the compound represented by the general formula (S-18).

[0574] Examples of the reaction method include a method of Suzuki coupling in the presence of a metal catalyst and a base.

[0575] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0576] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0577] Specific examples of the base include potassium carbonate, potassium phosphate, and cesium carbonate.

[0578] Finally, the amino group of the compound represented by the general formula (S-18) is reacted with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, thiophosgene, or the like to obtain the target compound represented by the general formula (S-19).

[0579] (Compound represented by general formula (ii))

[0580] Regarding solubility, Δn and / or Δε r From the viewpoint of , the liquid crystal composition of the present invention preferably contains one or two or more compounds represented by the following general formula (ii) having an isothiocyanate group (—NCS).

[0581] [Chemistry 126]

[0582]

[0583] In the general formula (ii), R ii1 It represents an alkyl group having 1 to 20 carbon atoms.

[0584] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0585] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0586] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0587] In addition, one or more -CH2-CH2- in the alkyl group may be substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0588] Furthermore, one or two or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[0589] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0590] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0591] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0592] For example, R ii1 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0593] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0594] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0595] In addition, R ii1 By substituting one -CH2- in the above alkyl group with -S-, an alkylthio group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[0596] The alkyl sulfhydryl group is a linear, branched or cyclic alkyl sulfhydryl group, and is preferably a linear alkyl sulfhydryl group.

[0597] The alkylthio group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0598] In addition, R ii1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0599] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0600] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0601] In addition, R ii1By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0602] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0603] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0604] The alkynyl group is preferably a group of the following formula (R ii1 -A) represents an alkynyl group.

[0605] [Chemistry 127]

[0606]

[0607] Formula (R ii1 -A), R ii1A It represents an alkyl group having 1 to 18 carbon atoms.

[0608] The alkyl group having 1 to 18 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0609] The alkyl group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms.

[0610] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0611] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0612] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0613] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0614] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0615] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0616] In addition, the formula (R ii1 -A), the black dot indicates the direction to Aii1 The bond key.

[0617] In addition, R ii1 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[0618] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0619] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0620] In addition, R ii1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0621] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0622] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0623] In addition, R ii1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[0624] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0625] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0626] As R ii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: ii1 -1)~Formula (R ii1 -56) etc.

[0627] [Chemistry 128]

[0628]

[0629] [Chemistry 129]

[0630]

[0631] Formula (R ii1 -1)~Formula (R ii1-56), the black dot indicates the direction to A ii1 The bond key.

[0632] In R ii1 When the ring structure to which the bond is a phenyl group (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. ii1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.

[0633] In addition, as R ii1 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and the chain is preferably straight.

[0634] In addition, as R ii1 From the viewpoint of solubility, preferably, it is a straight-chain or branched alkyl group having 2 to 8 carbon atoms, a straight-chain alkoxy group having 2 to 8 carbon atoms, a straight-chain halogenated alkoxy group having 1 to 8 carbon atoms, a straight-chain alkynyl group having 2 to 8 carbon atoms or a straight-chain alkylthio group having 1 to 6 carbon atoms.

[0635] In the general formula (ii), A ii1 and A ii2 Each independently represents a group selected from the group consisting of the following group (a), group (b), group (c) and group (d),

[0636] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- and / or -S-)

[0637] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[0638] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene-2,7-diyl, 2,3-dihydroindane-2,5-diyl , 2,3-dihydroindane-1,5-diyl, 2,3-dihydroindane-3,5-diyl (one -CH= or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0639] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl, benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl (one —CH═ or two or more —CH═ in the above groups may be substituted by —N═).

[0640] A ii1 and A ii2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S ii1 replace.

[0641] Substituent S ii1 It represents any one of a halogen atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms.

[0642] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0643] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0644] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[0645] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0646] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0647] Furthermore, one or two or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[0648] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0649] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0650] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0651] For example, the substituent S ii1 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0652] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0653] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0654] In addition, the substituent S ii1 By substituting one -CH2- in the above alkyl group with -S-, an alkylthio group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[0655] The alkyl sulfhydryl group is a linear, branched or cyclic alkyl sulfhydryl group, and is preferably a linear alkyl sulfhydryl group.

[0656] The alkylthio group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0657] In addition, the substituent S ii1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0658] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0659] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0660] In addition, the substituent S ii1By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0661] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0662] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0663] In addition, the substituent S ii1 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[0664] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0665] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0666] In addition, the substituent S ii1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0667] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0668] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0669] In addition, the substituent S ii1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[0670] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0671] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0672] As a substituent S ii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the formula (S ii1R -1)~Formula(S ii1R -36) represented by the base, etc.

[0673] [Chemistry 130]

[0674]

[0675] Formula (S ii1R -1)~Formula(S ii1R -36), the black dot indicates the direction to A ii1 or A ii2 The bond key.

[0676] As a substituent S ii1 , preferably a linear alkyl group having 1 to 6 carbon atoms, a fluorine atom or a chlorine atom.

[0677] In addition, A ii1 At least one or A ii2 Preferably, at least one substituent S ii1 The substitution is preferably substitution with a halogen atom, and preferably substitution with a fluorine atom.

[0678] In addition, in the substituent S ii1 When there are plural, these may be the same or different.

[0679] As A ii1 The substituent S in ii1 The substitution position is preferably the following formula (A ii1 -SP-1)~Formula (A ii1 -SP-12).

[0680] [Chemistry 131]

[0681]

[0682] [Chemistry 132]

[0683]

[0684] Formula (A ii1 -SP-1)~Formula (A ii1 -SP-12), the white dot indicates the direction to R ii1 or Z ii1 The black dots represent the bonds to Z ii1 The bond key.

[0685] As A ii2 The substituent S in ii1 The substitution position is preferably the following formula (A ii2 -SP-1)~Formula (A ii2 -SP-8).

[0686] [Chemistry 133]

[0687]

[0688] Formula (Aii2 -SP-1)~Formula (A ii2 -SP-8), the white dot indicates the direction of Z ii1 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0689] More specifically, A ii1 Preferably, it is represented by the following formula (A ii1 -1)~Formula (A ii1 -34).

[0690] [Chemistry 134]

[0691]

[0692] [Chemistry 135]

[0693]

[0694] Formula (A ii1 -1)~Formula (A ii1 -34), the white dot indicates the direction to R ii1 or Z ii1 The black dots represent the bonds to Z ii1 The bond key.

[0695] More specifically, A ii2 Preferably, it is represented by the following formula (A ii2 -1)~Formula (A ii2 -10).

[0696] [Chemistry 136]

[0697]

[0698] Formula (A ii2 -1)~Formula (A ii2 -10), the white dot indicates the direction of Z ii1 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0699] In the general formula (ii), Z ii1 It represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0700] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0701] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0702] However, when the alkylene group having 1 to 20 carbon atoms is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0703] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0704] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: ii1 -1)~Formula(Z ii1 -24) represented by the base, etc.

[0705] [Chemistry 137]

[0706]

[0707] Formula (Z ii1 -1)~Formula(Z ii1 -24), the white dot indicates the direction to A ii1 The black dots indicate the bond to A ii1 or A ii2 The bond key.

[0708] In the general formula (ii), n ii1 It represents an integer of 1-4, preferably 1-2.

[0709] In n ii1 When Δn and / or Δε is 1, r From the point of view of Z ii1 Preferably, it represents a single bond or -C≡C-.

[0710] In addition, in n ii1 When Δn and / or Δε is 2, r From the point of view of Z ii1 Preferably, it represents a single bond or -C≡C-.

[0711] In addition, in the general formula (ii), in A ii1 and Z ii1 When there are plural numbers, these may be the same or different.

[0712] However, among the compounds represented by the general formula (ii), the compounds represented by the general formula (i) (including subordinate concepts) are excluded.

[0713] As the compound represented by the general formula (ii), compounds represented by the following general formulas (ii-1) to (ii-8) are preferred.

[0714] [Chemistry 138]

[0715] R ii1 -A ii1 -A ii2 -NCS (ii-1)

[0716]

[0717] R ii1 -A ii1 -A ii1 -2-A ii2 -NCS (ii-5)

[0718]

[0719] R ii1 -A ii1 -A ii1 -2-A ii1-3 -A ii2 -NCS (ii-8)

[0720] In the general formulas (ii-1) to (ii-8), R ii1 , A ii1 and A ii2 represents the same as R in the general formula (ii) ii1 , A ii1 and A ii2 The same meaning respectively.

[0721] In the general formula (ii-3) to the general formula (ii-8), A ii1-2 and A ii1-3 The definitions of are independently the same as those of A in the general formula (ii). ii1 The definition is the same.

[0722] As the compound represented by the general formula (ii-1), compounds represented by the following general formulas (ii-1-1) to (ii-1-4) are preferred.

[0723] [Chemistry 139]

[0724]

[0725] In the general formulas (ii-1-1) to (ii-1-4), R ii1 and Sii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0726] Specific examples of the compound represented by the general formula (ii-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.4).

[0727] [Chemistry 140]

[0728]

[0729] Specific examples of the compound represented by the general formula (ii-1-2) include compounds represented by the following structural formulas (ii-1-2.1) to (ii-1-2.6).

[0730] [Chemistry 141]

[0731]

[0732] Specific examples of the compound represented by the general formula (ii-1-3) include compounds represented by the following structural formulas (ii-1-3.1) to (ii-1-3.3).

[0733] [Chemistry 142]

[0734]

[0735] Specific examples of the compound represented by the general formula (ii-1-4) include compounds represented by the following structural formulas (ii-1-4.1) to (ii-1-4.3).

[0736] [Chemistry 143]

[0737]

[0738] As the compound represented by the general formula (ii-2), compounds represented by the following general formulas (ii-2-1) to (ii-2-14) are preferred.

[0739] [Chemistry 144]

[0740]

[0741] [Chemistry 145]

[0742]

[0743] [Chemistry 146]

[0744]

[0745] In the general formulas (ii-2-1) to (ii-2-14), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0746] Specific examples of the compound represented by the general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.4).

[0747] [Chemistry 147]

[0748]

[0749] Specific examples of the compound represented by general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.10).

[0750] [Chemistry 148]

[0751]

[0752] Specific examples of the compound represented by the general formula (ii-2-3) include compounds represented by the following structural formulas (ii-2-3.1) to (ii-2-3.3).

[0753] [Chemistry 149]

[0754]

[0755] Specific examples of the compound represented by general formula (ii-2-4) include compounds represented by the following structural formulas (ii-2-4.1) to (ii-2-4.8).

[0756] [Chemistry 150]

[0757]

[0758] Specific examples of the compound represented by the general formula (ii-2-5) include compounds represented by the following structural formulas (ii-2-5.1) to (ii-2-5.4).

[0759] [Chemistry 151]

[0760]

[0761] Specific examples of the compound represented by the general formula (ii-2-6) include compounds represented by the following structural formulas (ii-2-6.1) to (ii-2-6.4).

[0762] [Chemistry 152]

[0763]

[0764] Specific examples of the compound represented by the general formula (ii-2-7) include compounds represented by the following structural formulas (ii-2-7.1) to (ii-2-7.3).

[0765] [Chemistry 153]

[0766]

[0767] Specific examples of the compound represented by general formula (ii-2-8) include compounds represented by the following structural formulas (ii-2-8.1) to (ii-2-8.3).

[0768] [Chemistry 154]

[0769]

[0770] Specific examples of the compound represented by the general formula (ii-2-9) include compounds represented by the following structural formulas (ii-2-9.1) to (ii-2-9.4).

[0771] [Chemistry 155]

[0772]

[0773] Specific examples of the compound represented by the general formula (ii-2-10) include compounds represented by the following structural formulas (ii-2-10.1) to (ii-2-10.4).

[0774] [Chemistry 156]

[0775]

[0776] Specific examples of the compound represented by the general formula (ii-2-11) include compounds represented by the following structural formulas (ii-2-11.1) to (ii-2-11.3).

[0777] [Chemistry 157]

[0778]

[0779] Specific examples of the compound represented by general formula (ii-2-12) include compounds represented by the following structural formulas (ii-2-12.1) to (ii-2-12.3).

[0780] [Chemistry 158]

[0781]

[0782] Specific examples of the compound represented by general formula (ii-2-13) include compounds represented by the following structural formulas (ii-2-13.1) to (ii-2-13.3).

[0783] [Chemistry 159]

[0784]

[0785] Specific examples of the compound represented by general formula (ii-2-14) include compounds represented by the following structural formula (ii-2-14.1).

[0786] [Chemistry 160]

[0787]

[0788] As the compound represented by the general formula (ii-3), compounds represented by the following general formulas (ii-3-1) to (ii-3-22) are preferred.

[0789] [Chemistry 161]

[0790]

[0791] [Chemistry 162]

[0792]

[0793] [Chemistry 163]

[0794]

[0795] In the general formulas (ii-3-1) to (ii-3-22), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0796] Specific examples of the compound represented by general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.4).

[0797] [Chemistry 164]

[0798]

[0799] Specific examples of the compound represented by general formula (ii-3-2) include compounds represented by the following structural formulas (ii-3-2.1) to (ii-3-2.4).

[0800] [Chemistry 165]

[0801]

[0802] Specific examples of the compound represented by general formula (ii-3-3) include compounds represented by the following structural formulas (ii-3-3.1) to (ii-3-3.7).

[0803] [Chemistry 166]

[0804]

[0805] [Chemistry 167]

[0806]

[0807] Specific examples of the compound represented by general formula (ii-3-4) include compounds represented by the following structural formulas (ii-3-4.1) to (ii-3-4.5).

[0808] [Chemistry 168]

[0809]

[0810] Specific examples of the compound represented by general formula (ii-3-5) include compounds represented by the following structural formulas (ii-3-5.1) to (ii-3-5.7).

[0811] [Chemistry 169]

[0812]

[0813] Specific examples of the compound represented by general formula (ii-3-6) include compounds represented by the following structural formulas (ii-3-6.1) to (ii-3-6.3).

[0814] [Chemistry 170]

[0815]

[0816] Specific examples of the compound represented by the general formula (ii-3-7) include compounds represented by the following structural formulas (ii-3-7.1) to (ii-3-7.6).

[0817] [Chemistry 171]

[0818]

[0819] Specific examples of the compound represented by general formula (ii-3-8) include compounds represented by the following structural formulas (ii-3-8.1) to (ii-3-8.3).

[0820] [Chemistry 172]

[0821]

[0822] Specific examples of the compound represented by general formula (ii-3-9) include compounds represented by the following structural formulas (ii-3-9.1) to (ii-3-9.4).

[0823] [Chemistry 173]

[0824]

[0825] Specific examples of the compound represented by the general formula (ii-3-10) include compounds represented by the following structural formulas (ii-3-10.1) to (ii-3-10.3).

[0826] [Chemistry 174]

[0827]

[0828] Specific examples of the compound represented by the general formula (ii-3-11) include compounds represented by the following structural formulas (ii-3-11.1) to (ii-3-11.3).

[0829] [Chemistry 175]

[0830]

[0831] Specific examples of the compound represented by general formula (ii-3-12) include compounds represented by the following structural formulas (ii-3-12.1) to (ii-3-12.3).

[0832] [Chemistry 176]

[0833]

[0834] Specific examples of the compound represented by general formula (ii-3-13) include compounds represented by the following structural formulas (ii-3-13.1) to (ii-3-13.4).

[0835] [Chemistry 177]

[0836]

[0837] Specific examples of the compound represented by the general formula (ii-3-14) include compounds represented by the following structural formulas (ii-3-14.1) to (ii-3-14.3).

[0838] [Chemistry 178]

[0839]

[0840] Specific examples of the compound represented by general formula (ii-3-15) include compounds represented by the following structural formulas (ii-3-15.1) to (ii-3-15.3).

[0841] [Chemistry 179]

[0842]

[0843] Specific examples of the compound represented by general formula (ii-3-16) include compounds represented by the following structural formulas (ii-3-16.1) to (ii-3-16.3).

[0844] [Chemistry 180]

[0845]

[0846] Specific examples of the compound represented by general formula (ii-3-17) include compounds represented by the following structural formulas (ii-3-17.1) to (ii-3-17.3).

[0847] [Chemistry 181]

[0848]

[0849] Specific examples of the compound represented by general formula (ii-3-18) include compounds represented by the following structural formulas (ii-3-18.1) to (ii-3-18.3).

[0850] [Chemistry 182]

[0851]

[0852] Specific examples of the compound represented by general formula (ii-3-19) include compounds represented by the following structural formulas (ii-3-19.1) to (ii-3-19.3).

[0853] [Chemistry 183]

[0854]

[0855] Specific examples of the compound represented by the general formula (ii-3-20) include compounds represented by the following structural formulas (ii-3-20.1) to (ii-3-20.3).

[0856] [Chemistry 184]

[0857]

[0858] Specific examples of the compound represented by the general formula (ii-3-21) include compounds represented by the following structural formulas (ii-3-21.1) to (ii-3-21.4).

[0859] [Chemistry 185]

[0860]

[0861] Specific examples of the compound represented by the general formula (ii-3-22) include compounds represented by the following structural formulas (ii-3-22.1) to (ii-3-22.3).

[0862] [Chemistry 186]

[0863]

[0864] As the compound represented by the general formula (ii-4), compounds represented by the following general formulas (ii-4-1) to (ii-4-30) are preferred.

[0865] [Chemistry 187]

[0866]

[0867] [Chemistry 188]

[0868]

[0869] [Chemistry 189]

[0870]

[0871] [Chemistry 190]

[0872]

[0873] In the general formulas (ii-4-1) to (ii-4-30), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0874] Specific examples of the compound represented by general formula (ii-4-1) include compounds represented by the following structural formulas (ii-4-1.1) to (ii-4-1.4).

[0875] [Chemistry 191]

[0876]

[0877] Specific examples of the compound represented by general formula (ii-4-2) include compounds represented by the following structural formulas (ii-4-2.1) to (ii-4-2.4).

[0878] [Chemistry 192]

[0879]

[0880] Specific examples of the compound represented by the general formula (ii-4-3) include compounds represented by the following structural formulas (ii-4-3.1) to (ii-4-3.8).

[0881] [Chemistry 193]

[0882]

[0883] [Chemistry 194]

[0884]

[0885] Specific examples of the compound represented by general formula (ii-4-4) include compounds represented by the following structural formulas (ii-4-4.1) to (ii-4-4.5).

[0886] [Chemistry 195]

[0887]

[0888] Specific examples of the compound represented by general formula (ii-4-5) include compounds represented by the following structural formula (ii-4-5.1).

[0889] [Chemistry 196]

[0890]

[0891] Specific examples of the compound represented by the general formula (ii-4-6) include compounds represented by the following structural formulas (ii-4-6.1) to (ii-4-6.5).

[0892] [Chemistry 197]

[0893]

[0894] Specific examples of the compound represented by general formula (ii-4-7) include compounds represented by the following structural formula (ii-4-7.1).

[0895] [Chemistry 198]

[0896]

[0897] Specific examples of the compound represented by general formula (ii-4-8) include compounds represented by the following structural formulas (ii-4-8.1) to (ii-4-8.4).

[0898] [Chemistry 199]

[0899]

[0900] Specific examples of the compound represented by the general formula (ii-4-9) include compounds represented by the following structural formulas (ii-4-9.1) to (ii-4-9.4).

[0901] [Chemistry 200]

[0902]

[0903] Specific examples of the compound represented by the general formula (ii-4-10) include compounds represented by the following structural formulas (ii-4-10.1) to (ii-4-10.4).

[0904] [Chemistry 201]

[0905]

[0906] Specific examples of the compound represented by the general formula (ii-4-11) include compounds represented by the following structural formulas (ii-4-11.1) to (ii-4-11.5).

[0907] [Chemistry 202]

[0908]

[0909] Specific examples of the compound represented by general formula (ii-4-12) include compounds represented by the following structural formulas (ii-4-12.1) to (ii-4-12.5).

[0910] [Chemistry 203]

[0911]

[0912] Specific examples of the compound represented by the general formula (ii-4-13) include compounds represented by the following structural formulas (ii-4-13.1) to (ii-4-13.4).

[0913] [Chemistry 204]

[0914]

[0915] Specific examples of the compound represented by general formula (ii-4-14) include compounds represented by the following structural formulas (ii-4-14.1) to (ii-4-14.4).

[0916] [Chemistry 205]

[0917]

[0918] Specific examples of the compound represented by the general formula (ii-4-15) include compounds represented by the following structural formulas (ii-4-15.1) to (ii-4-15.6).

[0919] [Chemistry 206]

[0920]

[0921] Specific examples of the compound represented by general formula (ii-4-16) include compounds represented by the following structural formulas (ii-4-16.1) to (ii-4-16.3).

[0922] [Chemistry 207]

[0923]

[0924] Specific examples of the compound represented by the general formula (ii-4-17) include compounds represented by the following structural formulas (ii-4-17.1) to (ii-4-17.3).

[0925] [Chemistry 208]

[0926]

[0927] Specific examples of the compound represented by the general formula (ii-4-18) include compounds represented by the following structural formulas (ii-4-18.1) to (ii-4-18.4).

[0928] [Chemistry 209]

[0929]

[0930] Specific examples of the compound represented by the general formula (ii-4-19) include compounds represented by the following structural formulas (ii-4-19.1) to (ii-4-19.8).

[0931] [Chemistry 210]

[0932]

[0933] [Chemistry 211]

[0934]

[0935] Specific examples of the compound represented by the general formula (ii-4-20) include compounds represented by the following structural formulas (ii-4-20.1) to (ii-4-20.4).

[0936] [Chemistry 212]

[0937]

[0938] Specific examples of the compound represented by the general formula (ii-4-21) include compounds represented by the following structural formulas (ii-4-21.1) to (ii-4-21.4).

[0939] [Chemistry 213]

[0940]

[0941] Specific examples of the compound represented by general formula (ii-4-22) include compounds represented by the following structural formulas (ii-4-22.1) to (ii-4-22.3).

[0942] [Chemistry 214]

[0943]

[0944] Specific examples of the compound represented by the general formula (ii-4-23) include compounds represented by the following structural formulas (ii-4-23.1) to (ii-4-23.3).

[0945] [Chemistry 215]

[0946]

[0947] Specific examples of the compound represented by general formula (ii-4-24) include compounds represented by the following structural formulas (ii-4-24.1) to (ii-4-24.3).

[0948] [Chemistry 216]

[0949]

[0950] Specific examples of the compound represented by general formula (ii-4-25) include compounds represented by the following structural formulas (ii-4-25.1) to (ii-4-25.3).

[0951] [Chemistry 217]

[0952]

[0953] Specific examples of the compound represented by general formula (ii-4-26) include compounds represented by the following structural formulas (ii-4-26.1) to (ii-4-26.3).

[0954] [Chemistry 218]

[0955]

[0956] Specific examples of the compound represented by the general formula (ii-4-27) include compounds represented by the following structural formulas (ii-4-27.1) to (ii-4-27.2).

[0957] [Chemistry 219]

[0958]

[0959] Specific examples of the compound represented by general formula (ii-4-28) include compounds represented by the following structural formulas (ii-4-28.1) to (ii-4-28.2).

[0960] [Chemistry 220]

[0961]

[0962] Specific examples of the compound represented by general formula (ii-4-29) include compounds represented by the following structural formulas (ii-4-29.1) to (ii-4-29.4).

[0963] [Chemistry 221]

[0964]

[0965] Specific examples of the compound represented by the general formula (ii-4-30) include compounds represented by the following structural formulas (ii-4-30.1) to (ii-4-30.2).

[0966] [Chemistry 222]

[0967]

[0968] As the compound represented by the general formula (ii-5), compounds represented by the following general formulas (ii-5-1) to (ii-5-8) are preferred.

[0969] [Chemistry 223]

[0970]

[0971] [Chemistry 224]

[0972]

[0973] In the general formulas (ii-5-1) to (ii-5-8), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0974] Specific examples of the compound represented by the general formula (ii-5-1) include compounds represented by the following structural formulas (ii-5-1.1) to (ii-5-1.4).

[0975] [Chemistry 225]

[0976]

[0977] Specific examples of the compound represented by general formula (ii-5-2) include compounds represented by the following structural formulas (ii-5-2.1) to (ii-5-2.4).

[0978] [Chemistry 226]

[0979]

[0980] Specific examples of the compound represented by general formula (ii-5-3) include compounds represented by the following structural formula (ii-5-3.1).

[0981] [Chemistry 227]

[0982]

[0983] Specific examples of the compound represented by general formula (ii-5-4) include compounds represented by the following structural formulas (ii-5-4.1) to (ii-5-4.3).

[0984] [Chemistry 228]

[0985]

[0986] Specific examples of the compound represented by general formula (ii-5-5) include compounds represented by the following structural formulas (ii-5-5.1) to (ii-5-5.3).

[0987] [Chemistry 229]

[0988]

[0989] Specific examples of the compound represented by general formula (ii-5-6) include compounds represented by the following structural formulas (ii-5-6.1) to (ii-5-6.3).

[0990] [Chemistry 230]

[0991]

[0992] Specific examples of the compound represented by general formula (ii-5-7) include compounds represented by the following structural formulas (ii-5-7.1) to (ii-5-7.3).

[0993] [Chemistry 231]

[0994]

[0995] Specific examples of the compound represented by general formula (ii-5-8) include compounds represented by the following structural formulas (ii-5-8.1) to (ii-5-8.3).

[0996] [Chemistry 232]

[0997]

[0998] As the compound represented by the general formula (ii-6), compounds represented by the following general formulas (ii-6-1) to (ii-6-36) are preferred.

[0999] [Chemistry 233]

[1000]

[1001] [Chemistry 234]

[1002]

[1003] [Chemistry 235]

[1004]

[1005] [Chemistry 236]

[1006]

[1007] [Chemistry 237]

[1008]

[1009] In the general formula (ii-6-1) to the general formula (ii-6-36), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[1010] Specific examples of the compound represented by general formula (ii-6-1) include compounds represented by the following structural formulas (ii-6-1.1) to (ii-6-1.4).

[1011] [Chemistry 238]

[1012]

[1013] Specific examples of the compound represented by general formula (ii-6-2) include compounds represented by the following structural formulas (ii-6-2.1) to (ii-6-2.4).

[1014] [Chemistry 239]

[1015]

[1016] Specific examples of the compound represented by the general formula (ii-6-3) include compounds represented by the following structural formulas (ii-6-3.1) to (ii-6-3.8).

[1017] [Chemistry 240]

[1018]

[1019] [Chemistry 241]

[1020]

[1021] Specific examples of the compound represented by general formula (ii-6-4) include compounds represented by the following structural formulas (ii-6-4.1) to (ii-6-4.4).

[1022] [Chemistry 242]

[1023]

[1024] Specific examples of the compound represented by the general formula (ii-6-5) include compounds represented by the following structural formulas (ii-6-5.1) to (ii-6-5.4).

[1025] [Chemistry 243]

[1026]

[1027] Specific examples of the compound represented by general formula (ii-6-6) include compounds represented by the following structural formulas (ii-6-6.1) to (ii-6-6.2).

[1028] [Chemistry 244]

[1029]

[1030] Specific examples of the compound represented by general formula (ii-6-7) include compounds represented by the following structural formulas (ii-6-7.1) to (ii-6-7.8).

[1031] [Chemistry 245]

[1032]

[1033] [Chemistry 246]

[1034]

[1035] Specific examples of the compound represented by general formula (ii-6-8) include compounds represented by the following structural formulas (ii-6-8.1) to (ii-6-8.9).

[1036] [Chemistry 247]

[1037]

[1038] [Chemistry 248]

[1039]

[1040] Specific examples of the compound represented by the general formula (ii-6-9) include compounds represented by the following structural formulas (ii-6-9.1) to (ii-6-9.4).

[1041] [Chemistry 249]

[1042]

[1043] Specific examples of the compound represented by the general formula (ii-6-10) include compounds represented by the following structural formulas (ii-6-10.1) to (ii-6-10.4).

[1044] [Chemistry 250]

[1045]

[1046] Specific examples of the compound represented by the general formula (ii-6-11) include compounds represented by the following structural formulas (ii-6-11.1) to (ii-6-11.4).

[1047] [Chemistry 251]

[1048]

[1049] Specific examples of the compound represented by the general formula (ii-6-12) include compounds represented by the following structural formulas (ii-6-12.1) to (ii-6-12.4).

[1050] [Chemistry 252]

[1051]

[1052] Specific examples of the compound represented by the general formula (ii-6-13) include compounds represented by the following structural formulas (ii-6-13.1) to (ii-6-13.20).

[1053] [Chemistry 253]

[1054]

[1055] [Chemistry 254]

[1056]

[1057] [Chemistry 255]

[1058]

[1059] [Chemistry 256]

[1060]

[1061] [Chemistry 257]

[1062]

[1063] Specific examples of the compound represented by general formula (ii-6-14) include compounds represented by the following structural formulas (ii-6-14.1) to (ii-6-14.4).

[1064] [Chemistry 258]

[1065]

[1066] Specific examples of the compound represented by general formula (ii-6-15) include compounds represented by the following structural formula (ii-6-15.1).

[1067] [Chemistry 259]

[1068]

[1069] Specific examples of the compound represented by the general formula (ii-6-16) include compounds represented by the following structural formulas (ii-1-16.1) to (ii-6-16.5).

[1070] [Chemistry 260]

[1071]

[1072] Specific examples of the compound represented by the general formula (ii-6-17) include compounds represented by the following structural formulas (ii-6-17.1) to (ii-6-17.4).

[1073] [Chemistry 261]

[1074]

[1075] Specific examples of the compound represented by general formula (ii-6-18) include compounds represented by the following structural formulas (ii-6-18.1) to (ii-6-18.8).

[1076] [Chemistry 262]

[1077]

[1078] [Chemistry 263]

[1079]

[1080] Specific examples of the compound represented by general formula (ii-6-19) include compounds represented by the following structural formulas (ii-6-19.1) to (ii-6-19.4).

[1081] [Chemistry 264]

[1082]

[1083] Specific examples of the compound represented by the general formula (ii-6-20) include compounds represented by the following structural formulas (ii-6-20.1) to (ii-6-20.4).

[1084] [Chemistry 265]

[1085]

[1086] Specific examples of the compound represented by the general formula (ii-6-21) include compounds represented by the following structural formulas (ii-6-21.1) to (ii-6-21.4).

[1087] [Chemistry 266]

[1088]

[1089] Specific examples of the compound represented by general formula (ii-6-22) include compounds represented by the following structural formulas (ii-6-22.1) to (ii-6-22.14).

[1090] [Chemistry 267]

[1091]

[1092] [Chemistry 268]

[1093]

[1094] [Chemistry 269]

[1095]

[1096] Specific examples of the compound represented by the general formula (ii-6-23) include compounds represented by the following structural formulas (ii-6-23.1) to (ii-6-23.10).

[1097] [Chemistry 270]

[1098]

[1099] [Chemistry 271]

[1100]

[1101] Specific examples of the compound represented by general formula (ii-6-24) include compounds represented by the following structural formulas (ii-6-24.1) to (ii-6-24.2).

[1102] [Chemistry 272]

[1103]

[1104] Specific examples of the compound represented by the general formula (ii-6-25) include compounds represented by the following structural formulas (ii-6-25.1) to (ii-6-25.5).

[1105] [Chemistry 273]

[1106]

[1107] Specific examples of the compound represented by general formula (ii-6-26) include compounds represented by the following structural formulas (ii-6-26.1) to (ii-6-26.2).

[1108] [Chemistry 274]

[1109]

[1110] Specific examples of the compound represented by general formula (ii-6-27) include compounds represented by the following structural formula (ii-6-27.1).

[1111] [Chemistry 275]

[1112]

[1113] Specific examples of the compound represented by general formula (ii-6-28) include compounds represented by the following structural formulas (ii-6-28.1) to (ii-6-28.5).

[1114] [Chemistry 276]

[1115]

[1116] Specific examples of the compound represented by general formula (ii-6-29) include compounds represented by the following structural formula (ii-6-29.1).

[1117] [Chemistry 277]

[1118]

[1119] Specific examples of the compound represented by general formula (ii-6-30) include compounds represented by the following structural formula (ii-6-30.1).

[1120] [Chemistry 278]

[1121]

[1122] Specific examples of the compound represented by general formula (ii-6-31) include compounds represented by the following structural formulas (ii-6-31.1) to (ii-6-31.5).

[1123] [Chemistry 279]

[1124]

[1125] Specific examples of the compound represented by general formula (ii-6-32) include compounds represented by the following structural formula (ii-6-32.1).

[1126] [Chemistry 280]

[1127]

[1128] Specific examples of the compound represented by general formula (ii-6-33) include compounds represented by the following structural formulas (ii-6-33.1) to (ii-6-33.4).

[1129] [Chemistry 281]

[1130]

[1131] Specific examples of the compound represented by general formula (ii-6-34) include compounds represented by the following structural formulas (ii-6-34.1) to (ii-6-34.3).

[1132] [Chemistry 282]

[1133]

[1134] Specific examples of the compound represented by general formula (ii-6-35) include compounds represented by the following structural formulas (ii-6-35.1) to (ii-6-35.4).

[1135] [Chemistry 283]

[1136]

[1137] Specific examples of the compound represented by general formula (ii-6-36) include compounds represented by the following structural formulas (ii-6-36.1) to (ii-6-36.3).

[1138] [Chemistry 284]

[1139]

[1140] As the compound represented by the general formula (ii-7), a compound represented by the following general formula (ii-7-1) is preferred.

[1141] [Chemistry 285]

[1142]

[1143] In the general formula (ii-7-1), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[1144] Specific examples of the compound represented by general formula (ii-7-1) include compounds represented by the following structural formula (ii-7-1.1).

[1145] [Chemistry 286]

[1146]

[1147] As the compound represented by the general formula (ii-8), compounds represented by the following general formulas (ii-8-1) to (ii-8-2) are preferred.

[1148] [Chemistry 287]

[1149]

[1150] In the general formula (ii-8-1) to the general formula (ii-8-2), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[1151] Specific examples of the compound represented by general formula (ii-8-1) include compounds represented by the following structural formulas (ii-8-1.1) to (ii-8-1.3).

[1152] [Chemistry 288]

[1153]

[1154] Specific examples of the compound represented by general formula (ii-8-2) include compounds represented by the following structural formulas (ii-8-2.1) to (ii-8-2.6).

[1155] [Chemistry 289]

[1156]

[1157] General formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-4), general formula (ii-2-1) to general formula (ii-2-14), general formula (ii-3-1) to general formula (ii-3-22), general formula (ii-4-1) to general formula (ii-4-30), general formula (ii-5-1) to general formula (ii-5-8), general formula (ii-6-1) to general formula (ii-6-36), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii-1-2. 6), structural formula (ii-1-3.1) to structural formula (ii-1-3.3), structural formula (ii-1-4.1) to structural formula (ii-1-4.3), structural formula (ii-2-1.1) to structural formula (ii-2-1.4), structural formula (ii-2-2.1) to structural formula (ii-2-2.10), structural formula (ii-2-3.1) to structural formula (ii-2-3.3), structural formula (ii-2-4.1) to structural formula (ii-2-4.8), structural formula (ii-2-5.1) to structural formula (ii-2-5.4), structural formula (ii-2-6.1) to structural formula (ii-2-6.4), structural formula (ii-2-7.1) to structural formula (ii-2-7.2) i-2-7.3), structural formula (ii-2-8.1) to structural formula (ii-2-8.3), structural formula (ii-2-9.1) to structural formula (ii-2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-2-11.1) to structural formula (ii-2-11.3), structural formula (ii-2-12.1) to structural formula (ii-2-12.3), structural formula (ii-2-13.1) to structural formula (ii-2-13.3), structural formula (ii-2-14.1), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (i i-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.6), structural formula (ii-3-8.1) to structural formula (ii-3-8.3), structural formula (ii-3-9.1) to structural formula (ii-3-9.4), structural formula (ii-3-10.1) to structural formula (ii-3-10.3), structural formula (ii-3-11.1) ~ Structural formula (ii-3-11.3), Structural formula (ii-3-12.1) ~ Structural formula (ii-3-12.3), Structural formula (ii-3-13.1) ~ Structural formula (ii-3-13.4), Structural formula (ii-3-14.1) ~ Structural formula (ii-3-14.3), Structural formula (ii-3-15.1) ~ Structural formula (ii-3-15.3), Structural formula (ii-3-16.1) ~ Structural formula (ii-3-16.3), Structural formula (ii-3-17.1) ~ Structural formula (ii-3-17.3), Structural formula (ii-3-18.1) ~ Structural formula (ii-3-18.3), Structural formula (ii-3-19.1) ~ Structural formula (ii-3-19.3) ii-3-19.3), structural formula (ii-3-20.1) to structural formula (ii-3-20.3), structural formula (ii-3-21.1) to structural formula (ii-3-21.4), structural formula (ii-3-22.1) to structural formula (ii-3-22.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.2) -4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4-10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.4) ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-4-27.1) to structural formula (ii-4-27.2), structural formula (ii-4-28.1) to structural formula (ii-4-28.2), structural formula (ii-4-29.1) to structural formula (ii-4-29.4), structural formula (ii-4-30.1) to structural formula (ii-4-30.2), structural formula (ii-5-1.1) to structural formula (ii-5-1.4), structural formula (ii -5-2.1) ~ Structural formula (ii-5-2.4), Structural formula (ii-5-3.1), Structural formula (ii-5-4.1) ~ Structural formula (ii-5-4.3), Structural formula (ii-5-5.1) ~ Structural formula (ii-5-5.3), Structural formula (ii-5-6.1) ~ Structural formula (ii-5-6.3), Structural formula (ii-5-7.1) ~ Structural formula (ii-5-7.3), Structural formula (ii-5-8.1) ~ Structural formula (ii-5-8.3), Structural formula (ii-6-1.1) ~ Structural formula (ii-6-1.4), Structural formula (ii-6-2.1) ~ Structural formula (ii-6-2.4), Structural formula (ii-6-3.1) ~ Structural formula Structural formula (ii-6-3.8), structural formula (ii-6-4.1) to structural formula (ii-6-4.4), structural formula (ii-6-5.1) to structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii -6-12.1) ~ Structural formula (ii-6-12.4), Structural formula (ii-6-13.1) ~ Structural formula (ii-6-13.20), Structural formula (ii-6-14.1) ~ Structural formula (ii-6-14.4), Structural formula (ii-6-15.1), Structural formula (ii-1-16.1) ~ Structural formula (ii-6-16.5), Structural formula (ii-6-17.1) ~ Structural formula (ii-6-17.4), Structural formula (ii-6-18.1) ~ Structural formula (ii-6-18.8), Structural formula (ii-6-19.1) ~ Structural formula (ii-6-19.4), Structural formula (ii-6-20.1) ~ Structural formula (ii-6-20.4), structural formula (ii-6-21.1) to structural formula (ii-6-21.4), structural formula (ii-6-22.1) to structural formula (ii-6-22.14), structural formula (ii-6-23.1) to structural formula (ii-6-23.10), structural formula (ii-6-24.1) to structural formula (ii-6-24.2), structural formula (ii-6-25.1) to structural formula (ii-6-25.5), structural formula (ii-6-26.1) to structural formula (ii-6-26.2), structural formula (ii-6-27.1), structural formula (ii-6-28.1) to structural formula (ii-6-28.5), structural formula (ii-6-29.1), structural formula (ii-6-30.1), structural formula (ii-6-31 The compounds represented by formula (ii-1) to formula (ii-6-31.5), formula (ii-6-32.1), formula (ii-6-33.1) to formula (ii-6-33.4), formula (ii-6-34.1) to formula (ii-6-34.3), formula (ii-6-35.1) to formula (ii-6-35.4), formula (ii-6-36.1) to formula (ii-6-36.3), formula (ii-7-1.1), formula (ii-8-1.1) to formula (ii-8-1.3) or formula (ii-8-2.1) to formula (ii-8-2.6) are used in the liquid crystal composition in one or more kinds, preferably one to twenty kinds, and preferably two to fifteen kinds. .

[1158] General formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-4), general formula (ii-2-1) to general formula (ii-2-14), general formula (ii-3-1) to general formula (ii-3-22), general formula (ii-4-1) to general formula (ii-4-30), general formula (ii-5-1) to general formula (ii-5-8), general formula (ii-6-1) to general formula (ii-6-36), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii-1-2. 6), structural formula (ii-1-3.1) to structural formula (ii-1-3.3), structural formula (ii-1-4.1) to structural formula (ii-1-4.3), structural formula (ii-2-1.1) to structural formula (ii-2-1.4), structural formula (ii-2-2.1) to structural formula (ii-2-2.10), structural formula (ii-2-3.1) to structural formula (ii-2-3.3), structural formula (ii-2-4.1) to structural formula (ii-2-4.8), structural formula (ii-2-5.1) to structural formula (ii-2-5.4), structural formula (ii-2-6.1) to structural formula (ii-2-6.4), structural formula (ii-2-7.1) to structural formula (ii-2-7.2) i-2-7.3), structural formula (ii-2-8.1) to structural formula (ii-2-8.3), structural formula (ii-2-9.1) to structural formula (ii-2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-2-11.1) to structural formula (ii-2-11.3), structural formula (ii-2-12.1) to structural formula (ii-2-12.3), structural formula (ii-2-13.1) to structural formula (ii-2-13.3), structural formula (ii-2-14.1), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (i i-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.6), structural formula (ii-3-8.1) to structural formula (ii-3-8.3), structural formula (ii-3-9.1) to structural formula (ii-3-9.4), structural formula (ii-3-10.1) to structural formula (ii-3-10.3), structural formula (ii-3-11.1) ~ Structural formula (ii-3-11.3), Structural formula (ii-3-12.1) ~ Structural formula (ii-3-12.3), Structural formula (ii-3-13.1) ~ Structural formula (ii-3-13.4), Structural formula (ii-3-14.1) ~ Structural formula (ii-3-14.3), Structural formula (ii-3-15.1) ~ Structural formula (ii-3-15.3), Structural formula (ii-3-16.1) ~ Structural formula (ii-3-16.3), Structural formula (ii-3-17.1) ~ Structural formula (ii-3-17.3), Structural formula (ii-3-18.1) ~ Structural formula (ii-3-18.3), Structural formula (ii-3-19.1) ~ Structural formula (ii-3-19.3) ii-3-19.3), structural formula (ii-3-20.1) to structural formula (ii-3-20.3), structural formula (ii-3-21.1) to structural formula (ii-3-21.4), structural formula (ii-3-22.1) to structural formula (ii-3-22.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.2) -4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4-10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.4) ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-4-27.1) to structural formula (ii-4-27.2), structural formula (ii-4-28.1) to structural formula (ii-4-28.2), structural formula (ii-4-29.1) to structural formula (ii-4-29.4), structural formula (ii-4-30.1) to structural formula (ii-4-30.2), structural formula (ii-5-1.1) to structural formula (ii-5-1.4), structural formula (ii -5-2.1) ~ Structural formula (ii-5-2.4), Structural formula (ii-5-3.1), Structural formula (ii-5-4.1) ~ Structural formula (ii-5-4.3), Structural formula (ii-5-5.1) ~ Structural formula (ii-5-5.3), Structural formula (ii-5-6.1) ~ Structural formula (ii-5-6.3), Structural formula (ii-5-7.1) ~ Structural formula (ii-5-7.3), Structural formula (ii-5-8.1) ~ Structural formula (ii-5-8.3), Structural formula (ii-6-1.1) ~ Structural formula (ii-6-1.4), Structural formula (ii-6-2.1) ~ Structural formula (ii-6-2.4), Structural formula (ii-6-3.1) ~ Structural formula Structural formula (ii-6-3.8), structural formula (ii-6-4.1) to structural formula (ii-6-4.4), structural formula (ii-6-5.1) to structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii -6-12.1) ~ Structural formula (ii-6-12.4), Structural formula (ii-6-13.1) ~ Structural formula (ii-6-13.20), Structural formula (ii-6-14.1) ~ Structural formula (ii-6-14.4), Structural formula (ii-6-15.1), Structural formula (ii-1-16.1) ~ Structural formula (ii-6-16.5), Structural formula (ii-6-17.1) ~ Structural formula (ii-6-17.4), Structural formula (ii-6-18.1) ~ Structural formula (ii-6-18.8), Structural formula (ii-6-19.1) ~ Structural formula (ii-6-19.4), Structural formula (ii-6-20.1) ~ Structural formula (ii-6-20.4), structural formula (ii-6-21.1) to structural formula (ii-6-21.4), structural formula (ii-6-22.1) to structural formula (ii-6-22.14), structural formula (ii-6-23.1) to structural formula (ii-6-23.10), structural formula (ii-6-24.1) to structural formula (ii-6-24.2), structural formula (ii-6-25.1) to structural formula (ii-6-25.5), structural formula (ii-6-26 .1)~Structural formula (ii-6-26.2), structural formula (ii-6-27.1), structural formula (ii-6-28.1)~Structural formula (ii-6-28.5), structural formula (ii-6-29.1), structural formula (ii-6-30.1), structural formula (ii-6-31.1)~Structural formula (ii-6-31.5), structural formula (ii-6-32.1), structural formula (ii-6-33.1)~Structural formula (ii-6-33. 4), the lower limit of the total content of the compounds represented by structural formula (ii-6-34.1) to structural formula (ii-6-34.3), structural formula (ii-6-35.1) to structural formula (ii-6-35.4), structural formula (ii-6-36.1) to structural formula (ii-6-36.3), structural formula (ii-7-1.1), structural formula (ii-8-1.1) to structural formula (ii-8-1.3) or structural formula (ii-8-2.1) to structural formula (ii-8-2.6) in 100 mass% of the liquid crystal composition is preferably 1 mass% or more, preferably 5 mass% or more, preferably 10 mass% or more, preferably 15 mass% or more, preferably 20 mass% or more, preferably 25 mass% or more, preferably 30 mass% or more, preferably 35 mass% or more, preferably 40 mass% or more, preferably 45 mass% or more, preferably 75 mass% or more, preferably 80 mass% or more, and preferably 85 mass% or more. .

[1159] General formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-4), general formula (ii-2-1) to general formula (ii-2-14), general formula (ii-3-1) to general formula (ii-3-22), general formula (ii-4-1) to general formula (ii-4-30), general formula (ii-5-1) to general formula (ii-5-8), general formula (ii-6-1) to general formula (ii-6-36), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii-1-2. 6), structural formula (ii-1-3.1) to structural formula (ii-1-3.3), structural formula (ii-1-4.1) to structural formula (ii-1-4.3), structural formula (ii-2-1.1) to structural formula (ii-2-1.4), structural formula (ii-2-2.1) to structural formula (ii-2-2.10), structural formula (ii-2-3.1) to structural formula (ii-2-3.3), structural formula (ii-2-4.1) to structural formula (ii-2-4.8), structural formula (ii-2-5.1) to structural formula (ii-2-5.4), structural formula (ii-2-6.1) to structural formula (ii-2-6.4), structural formula (ii-2-7.1) to structural formula (ii-2-7.2) i-2-7.3), structural formula (ii-2-8.1) to structural formula (ii-2-8.3), structural formula (ii-2-9.1) to structural formula (ii-2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-2-11.1) to structural formula (ii-2-11.3), structural formula (ii-2-12.1) to structural formula (ii-2-12.3), structural formula (ii-2-13.1) to structural formula (ii-2-13.3), structural formula (ii-2-14.1), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (i i-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.6), structural formula (ii-3-8.1) to structural formula (ii-3-8.3), structural formula (ii-3-9.1) to structural formula (ii-3-9.4), structural formula (ii-3-10.1) to structural formula (ii-3-10.3), structural formula (ii-3-11.1) ~ Structural formula (ii-3-11.3), Structural formula (ii-3-12.1) ~ Structural formula (ii-3-12.3), Structural formula (ii-3-13.1) ~ Structural formula (ii-3-13.4), Structural formula (ii-3-14.1) ~ Structural formula (ii-3-14.3), Structural formula (ii-3-15.1) ~ Structural formula (ii-3-15.3), Structural formula (ii-3-16.1) ~ Structural formula (ii-3-16.3), Structural formula (ii-3-17.1) ~ Structural formula (ii-3-17.3), Structural formula (ii-3-18.1) ~ Structural formula (ii-3-18.3), Structural formula (ii-3-19.1) ~ Structural formula (ii-3-19.3) ii-3-19.3), structural formula (ii-3-20.1) to structural formula (ii-3-20.3), structural formula (ii-3-21.1) to structural formula (ii-3-21.4), structural formula (ii-3-22.1) to structural formula (ii-3-22.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.2) -4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4-10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.4) ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-4-27.1) to structural formula (ii-4-27.2), structural formula (ii-4-28.1) to structural formula (ii-4-28.2), structural formula (ii-4-29.1) to structural formula (ii-4-29.4), structural formula (ii-4-30.1) to structural formula (ii-4-30.2), structural formula (ii-5-1.1) to structural formula (ii-5-1.4), structural formula (ii -5-2.1) ~ Structural formula (ii-5-2.4), Structural formula (ii-5-3.1), Structural formula (ii-5-4.1) ~ Structural formula (ii-5-4.3), Structural formula (ii-5-5.1) ~ Structural formula (ii-5-5.3), Structural formula (ii-5-6.1) ~ Structural formula (ii-5-6.3), Structural formula (ii-5-7.1) ~ Structural formula (ii-5-7.3), Structural formula (ii-5-8.1) ~ Structural formula (ii-5-8.3), Structural formula (ii-6-1.1) ~ Structural formula (ii-6-1.4), Structural formula (ii-6-2.1) ~ Structural formula (ii-6-2.4), Structural formula (ii-6-3.1) ~ Structural formula Structural formula (ii-6-3.8), structural formula (ii-6-4.1) to structural formula (ii-6-4.4), structural formula (ii-6-5.1) to structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii -6-12.1) ~ Structural formula (ii-6-12.4), Structural formula (ii-6-13.1) ~ Structural formula (ii-6-13.20), Structural formula (ii-6-14.1) ~ Structural formula (ii-6-14.4), Structural formula (ii-6-15.1), Structural formula (ii-1-16.1) ~ Structural formula (ii-6-16.5), Structural formula (ii-6-17.1) ~ Structural formula (ii-6-17.4), Structural formula (ii-6-18.1) ~ Structural formula (ii-6-18.8), Structural formula (ii-6-19.1) ~ Structural formula (ii-6-19.4), Structural formula (ii-6-20.1) ~ Structural formula (ii-6-20.4), structural formula (ii-6-21.1) to structural formula (ii-6-21.4), structural formula (ii-6-22.1) to structural formula (ii-6-22.14), structural formula (ii-6-23.1) to structural formula (ii-6-23.10), structural formula (ii-6-24.1) to structural formula (ii-6-24.2), structural formula (ii-6-25.1) to structural formula (ii-6-25.5), structural formula (ii-6-25.6) i-6-26.1)~Structural formula (ii-6-26.2), structural formula (ii-6-27.1), structural formula (ii-6-28.1)~Structural formula (ii-6-28.5), structural formula (ii-6-29.1), structural formula (ii-6-30.1), structural formula (ii-6-31.1)~Structural formula (ii-6-31.5), structural formula (ii-6-32.1), structural formula (ii-6-33.1)~Structural formula The upper limit of the total content of the compounds represented by formula (ii-6-33.4), formula (ii-6-34.1) to formula (ii-6-34.3), formula (ii-6-35.1) to formula (ii-6-35.4), formula (ii-6-36.1) to formula (ii-6-36.3), formula (ii-7-1.1), formula (ii-8-1.1) to formula (ii-8-1.3) or formula (ii-8-2.1) to formula (ii-8-2.6) in 100% by mass of the liquid crystal composition is preferably 95% by mass or less, preferably 90% by mass or less, preferably 55% by mass or less, preferably 50% by mass or less, preferably 45% by mass or less, preferably 40% by mass or less, preferably 35% by mass or less, preferably 25% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less. .

[1160] Regarding solubility, Δn and / or Δε rFrom the perspective of general formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-4), general formula (ii-2-1) to general formula (ii-2-14), general formula (ii-3-1) to general formula (ii-3-22), general formula (ii-4-1) to general formula (ii-4-30), general formula (ii-5-1) to general formula (ii-5-8), general formula (ii-6-1) to general formula (ii-6-36), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii -1-2.6), structural formula (ii-1-3.1) to structural formula (ii-1-3.3), structural formula (ii-1-4.1) to structural formula (ii-1-4.3), structural formula (ii-2-1.1) to structural formula (ii-2-1.4), structural formula (ii-2-2.1) to structural formula (ii-2-2.10), structural formula (ii-2-3.1) to structural formula (ii-2-3.3), structural formula (ii-2-4.1) to structural formula (ii-2-4.8), structural formula (ii-2-5.1) to structural formula (ii-2-5.4), structural formula (ii-2-6.1) to structural formula (ii-2-6.4), structural formula (ii-2-7.1) to structural formula Formula (ii-2-7.3), structural formula (ii-2-8.1) to structural formula (ii-2-8.3), structural formula (ii-2-9.1) to structural formula (ii-2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-2-11.1) to structural formula (ii-2-11.3), structural formula (ii-2-12.1) to structural formula (ii-2-12.3), structural formula (ii-2-13.1) to structural formula (ii-2-13.3), structural formula (ii-2-14.1), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (ii-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.6), structural formula (ii-3-8.1) to structural formula (ii-3-8.3), structural formula (ii-3-9.1) to structural formula (ii-3-9.4), structural formula (ii-3-10.1) to structural formula (ii-3-10.3), structural formula (ii-3-11.1) ~ Structural formula (ii-3-11.3), Structural formula (ii-3-12.1) ~ Structural formula (ii-3-12.3), Structural formula (ii-3-13.1) ~ Structural formula (ii-3-13.4), Structural formula (ii-3-14.1) ~ Structural formula (ii-3-14.3), Structural formula (ii-3-15.1) ~ Structural formula (ii-3-15.3), Structural formula (ii-3-16.1) ~ Structural formula (ii-3-16.3), Structural formula (ii-3-17.1) ~ Structural formula (ii-3-17.3), Structural formula (ii-3-18.1) ~ Structural formula (ii-3-18.3), Structural formula (ii-3-19.1) ~ Structural formula (ii-3-19.3) ii-3-19.3), structural formula (ii-3-20.1) to structural formula (ii-3-20.3), structural formula (ii-3-21.1) to structural formula (ii-3-21.4), structural formula (ii-3-22.1) to structural formula (ii-3-22.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.2) -4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4-10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.4) ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-4-27.1) to structural formula (ii-4-27.2), structural formula (ii-4-28.1) to structural formula (ii-4-28.2), structural formula (ii-4-29.1) to structural formula (ii-4-29.4), structural formula (ii-4-30.1) to structural formula (ii-4-30.2), structural formula (ii-5-1.1) to structural formula (ii-5-1.4), structural formula (ii -5-2.1) ~ Structural formula (ii-5-2.4), Structural formula (ii-5-3.1), Structural formula (ii-5-4.1) ~ Structural formula (ii-5-4.3), Structural formula (ii-5-5.1) ~ Structural formula (ii-5-5.3), Structural formula (ii-5-6.1) ~ Structural formula (ii-5-6.3), Structural formula (ii-5-7.1) ~ Structural formula (ii-5-7.3), Structural formula (ii-5-8.1) ~ Structural formula (ii-5-8.3), Structural formula (ii-6-1.1) ~ Structural formula (ii-6-1.4), Structural formula (ii-6-2.1) ~ Structural formula (ii-6-2.4), Structural formula (ii-6-3.1) ~ Structural formula Structural formula (ii-6-3.8), structural formula (ii-6-4.1) to structural formula (ii-6-4.4), structural formula (ii-6-5.1) to structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii -6-12.1) ~ Structural formula (ii-6-12.4), Structural formula (ii-6-13.1) ~ Structural formula (ii-6-13.20), Structural formula (ii-6-14.1) ~ Structural formula (ii-6-14.4), Structural formula (ii-6-15.1), Structural formula (ii-1-16.1) ~ Structural formula (ii-6-16.5), Structural formula (ii-6-17.1) ~ Structural formula (ii-6-17.4), Structural formula (ii-6-18.1) ~ Structural formula (ii-6-18.8), Structural formula (ii-6-19.1) ~ Structural formula (ii-6-19.4), Structural formula (ii-6-20.1) ~ Structural formula (ii-6-20.4), structural formula (ii-6-21.1) to structural formula (ii-6-21.4), structural formula (ii-6-22.1) to structural formula (ii-6-22.14), structural formula (ii-6-23.1) to structural formula (ii-6-23.10), structural formula (ii-6-24.1) to structural formula (ii-6-24.2), structural formula (ii-6-25.1) to structural formula (ii-6-25.5), structural formula (ii-6-26.1) to structural formula (ii-6-26.2), structural formula (ii-6-27.1), structural formula (ii-6-28.1) to structural formula (ii-6-28.5), structural formula (ii-6-29.1), structural formula (ii-6-30.1), structural formula (ii-6-31.1) to structural formula (ii-6-31.5 The total content of the compounds represented by formula (ii-6-32.1), formula (ii-6-33.1) to formula (ii-6-33.4), formula (ii-6-34.1) to formula (ii-6-34.3), formula (ii-6-35.1) to formula (ii-6-35.4), formula (ii-6-36.1) to formula (ii-6-36.3), formula (ii-7-1.1), formula (ii-8-1.1) to formula (ii-8-1.3) or formula (ii-8-2.1) to formula (ii-8-2.6) in 100% by mass of the liquid crystal composition is preferably 1% to 95% by mass, preferably 5% to 90% by mass, preferably 5% to 55% by mass, and preferably 10% to 45% by mass. .

[1161] The compound represented by the general formula (ii) (including subordinate concepts) can be synthesized using a known synthesis method.

[1162] (Other compounds)

[1163] In terms of Δn and / or Δε r From the viewpoint of , the liquid crystal composition of the present invention may further contain one or more compounds represented by the following general formula (vt) having at least one -C≡C- as a linking group.

[1164] [Chemistry 290]

[1165]

[1166] In the general formula (vt), R vt1 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

[1167] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1168] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[1169] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1170] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1171] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[1172] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1173] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1174] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1175] For example, R vt1 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[1176] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1177] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1178] In addition, R vt1 By substituting one -CH2- in the above alkyl group with -S-, an alkylthio group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[1179] The alkyl sulfhydryl group is a linear, branched or cyclic alkyl sulfhydryl group, and is preferably a linear alkyl sulfhydryl group.

[1180] The alkylthio group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.

[1181] In addition, R vt1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[1182] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[1183] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1184] In addition, R vt1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[1185] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[1186] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1187] In addition, R vt1 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[1188] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[1189] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1190] In addition, R vt1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[1191] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[1192] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1193] In addition, R vt1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[1194] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[1195] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1196] As R vt1Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: vt1 -1)~Formula (R vt1 -36) represented by the base, etc.

[1197] [Chemistry 291]

[1198]

[1199] Formula (R vt1 -1)~Formula (R vt1 -36), the black dot indicates the direction to A vt1 The bond key.

[1200] When the reliability of the entire liquid crystal composition is emphasized, R vt1 It is preferably an alkyl group having 1 to 12 carbon atoms. When the reduction in viscosity of the entire liquid crystal composition is important, R vt1 An alkenyl group having 2 to 8 carbon atoms is preferred.

[1201] In R vt1 When the ring structure to which the bond is a phenyl group (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. vt1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.

[1202] In addition, as R vt1 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and the chain is preferably straight.

[1203] In addition, as R vt1 In view of solubility, a linear alkyl group having 2 to 6 carbon atoms or a linear alkylthio group having 1 to 6 carbon atoms is preferred.

[1204] In the general formula (vt), R vt2 It represents any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, or an alkyl group having 1 to 20 carbon atoms.

[1205] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1206] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1207] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1208] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1209] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[1210] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1211] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1212] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1213] For example, R vt2 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[1214] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1215] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1216] In addition, R vt2 By substituting one -CH2- in the above alkyl group with -S-, an alkylthio group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[1217] The alkyl sulfhydryl group is a linear, branched or cyclic alkyl sulfhydryl group, and is preferably a linear alkyl sulfhydryl group.

[1218] The alkylthio group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.

[1219] In addition, R vt2 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[1220] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[1221] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1222] In addition, R vt2 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[1223] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[1224] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1225] In addition, R vt2 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[1226] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[1227] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1228] In addition, R vt2 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[1229] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[1230] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1231] In addition, R vt2 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[1232] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[1233] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1234] As R vt2Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: vt2 -1)~Formula (R vt2 -36) represented by the base, etc.

[1235] [Chemistry 292]

[1236]

[1237] Formula (R vt2 -1)~Formula (R vt2 -36), the black dot indicates the direction to A vt3 The bond key.

[1238] In R vt2 When the ring structure to which the bond is a phenyl group (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. vt2 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.

[1239] In addition, as R vt2 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and the chain is preferably straight.

[1240] In addition, as R vt2 , in terms of solubility, Δn and / or Δε r From the viewpoint of the above, a fluorine atom, a cyano group, a linear alkyl group having 2 to 6 carbon atoms, a linear alkoxy group having 1 to 6 carbon atoms, or a linear alkylthio group having 1 to 6 carbon atoms is preferred.

[1241] In the general formula (vt), A vt1 , A vt2 and A vt3 Each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms.

[1242] More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms preferably represents a group selected from the group consisting of the following groups (a), (b), (c) and (d),

[1243] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- or -S-)

[1244] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[1245] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[1246] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more -CH= in the above groups may be substituted with -N=).

[1247] A vt1 , A vt2 and A vt3 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S vt1 replace.

[1248] Substituent S vt1 It represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.

[1249] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1250] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 3 to 6 carbon atoms.

[1251] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[1252] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[1253] One or two or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[1254] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1255] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1256] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1257] As a substituent S vt1 , preferably a fluorine atom or a linear alkyl group having 1 to 3 carbon atoms.

[1258] In addition, A vt1 , A vt2 and A vt3 At least one of the substituents S vt1 replace.

[1259] In addition, A vt1 Preferably, at least one substituent S vt1 replace.

[1260] In addition, in the substituent S vt1 When there are plural, these may be the same or different.

[1261] As A vt1 The substituent S in vt1 The substitution position is preferably the following formula (A vt1 -SP-1)~Formula (A vt1 -SP-3).

[1262] [Chemistry 293]

[1263]

[1264] Formula (A vt1 -SP-1)~Formula (A vt1 -SP-3), the white dot indicates the direction to R vt1 The black dots represent the bonds toward -C≡C-.

[1265] As A vt2The substituent S in vt1 The substitution position is preferably the following formula (A vt2 -SP-1)~Formula (A vt2 -SP-7) is preferably represented by the following formula (A) from the viewpoint of compatibility with other liquid crystal compounds. vt2 -SP-1)~Formula (A vt2 -SP-5) any one.

[1266] [Chemistry 294]

[1267]

[1268] Formula (A vt2 -SP-1)~Formula (A vt2 -SP-7), white dots represent bonds toward -C≡C-, and black dots represent bonds toward Z vt1 The bond key.

[1269] As A vt3 The substituent S in vt3 The substitution position is preferably the following formula (A vt3 -SP-1)~Formula (A vt3 -SP-8) is preferably represented by the following formula (A vt3 -SP-1)~Formula (A vt3 -SP-5) any one.

[1270] [Chemistry 295]

[1271]

[1272] Formula (A vt3 -SP-1)~Formula (A vt3 -SP-8), the white dot indicates the direction of Z vt1 The black dots represent the bonds to Z vt1 or R vt2 The bond key.

[1273] More specifically, A vt1 Preferably, it is represented by the following formula (A vt1 -1)~Formula (A vt1 -5) any one of.

[1274] [Chemistry 296]

[1275]

[1276] Formula (A vt1 -1)~Formula (A vt1 -5), the white dot indicates the direction to R vt1The black dots represent the bonds toward -C≡C-.

[1277] More specifically, A vt2 Preferably, it is represented by the following formula (A vt2 -1)~Formula (A vt2 -6) any one of.

[1278] [Chemistry 297]

[1279]

[1280] Formula (A vt2 -1)~Formula (A vt2 -6), the white dots represent the bonds towards -C≡C-, and the black dots represent the bonds towards Z vt1 The bond key.

[1281] More specifically, A vt3 Preferably, it is represented by the following formula (A vt3 -1)~Formula (A vt3 -5) any one of.

[1282] [Chemistry 298]

[1283]

[1284] Formula (A vt3 -1)~Formula (A vt3 -5), the white dot indicates the direction Z vt1 The black dots represent the bonds to Z vt1 or R vt2 The bond key.

[1285] In the general formula (vt), Z vt1 Each independently represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[1286] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[1287] The alkylene group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1288] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[1289] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[1290] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1291] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted alkylene groups) include the following: vt1 -1)~Formula(Z vt1 -24) represented by the base, etc.

[1292] [Chemistry 299]

[1293]

[1294] Formula (Z vt1 -1)~Formula(Z vt1 -24), the white dot indicates the direction to A vt2 or A vt3 The black dots indicate the bond to A vt3 The bond key.

[1295] In the general formula (vt), n vt1 It represents an integer of 1-3, and preferably an integer of 1-2.

[1296] In n vt1 When Δn and / or Δε is 1, r From the point of view of Z vt1 Preferably, it represents -C≡C-.

[1297] In addition, in n vt1 When Δn and / or Δε is 2 or 3, r From the point of view of Z vt1 At least one of preferably represents -C≡C-.

[1298] In addition, in the general formula (vt), in A vt3 and Z vt1 When there are plural numbers, these may be the same or different.

[1299] The compound represented by the general formula (vt) is preferably a compound represented by the following general formula (vt-1).

[1300] [Chemistry 300]

[1301]

[1302] In the general formula (vt-1), R vt1 , R vt2 , A vt1 , A vt2 and A vt3 represents the same as R in the general formula (vt) vt1 , R vt2 , A vt1 , A vt2 and A vt3 The same meaning respectively.

[1303] As the compound represented by the general formula (vt-1), compounds represented by the following general formulas (vt-1-1) to (vt-1-3) are preferred.

[1304] [Chemistry 301]

[1305]

[1306] In the general formula (vt-1-1) to the general formula (vt-1-3), R vt1 , R vt2 and S vt1 Each independently represents R in the general formula (vt) vt1 , R vt2 and S vt1 The same meaning respectively.

[1307] Specific examples of the compound represented by the general formula (vt-1-1) include compounds represented by the following structural formulas (vt-1-1.1) to (vt-1-1.24).

[1308] [Chemistry 302]

[1309]

[1310] [Chemistry 303]

[1311]

[1312] [Chemistry 304]

[1313]

[1314] Specific examples of the compound represented by the general formula (vt-1-2) include compounds represented by the following structural formulas (vt-1-2.1) to (vt-1-2.8).

[1315] [Chemistry 305]

[1316]

[1317] Specific examples of the compound represented by the general formula (vt-1-3) include compounds represented by the following structural formulas (vt-1-3.1) to (vt-1-3.4).

[1318] [Chemistry 306]

[1319]

[1320] The types of compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) used in the liquid crystal composition are one or more, preferably one to five, preferably one to four, preferably one to three, preferably one to two, and preferably one.

[1321] The lower limit of the total content of the compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) in 100 mass% of the liquid crystal composition is preferably 0.1 mass% or more, preferably 0.5 mass% or more, and preferably 1 mass% or more.

[1322] The upper limit value of the total content of the compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) in 100 mass% of the liquid crystal composition is preferably 25 mass% or less, preferably 20 mass% or less, and preferably 15 mass% or less.

[1323] Regarding solubility, Δn and / or Δε rFrom the perspective of, the total content of the compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) in 100 mass% of the liquid crystal composition is preferably 0.1 mass% to 25 mass%, preferably 0.5 mass% to 20 mass%, and preferably 1 mass% to 15 mass%.

[1324] The compound represented by the general formula (vt) (including subordinate concepts) can be synthesized using a known synthesis method.

[1325] From the viewpoint of solubility, the liquid crystal composition of the present invention may further contain one or two or more compounds represented by the following general formula (np-1) to general formula (np-3).

[1326] [Chemistry 307]

[1327]

[1328] In the general formula (np-1) to the general formula (np-3), R npi and R npii Each independently represents an alkyl group having 1 to 20 carbon atoms or a halogen atom.

[1329] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1330] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[1331] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1332] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- and / or -C≡C-.

[1333] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[1334] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1335] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1336] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1337] For example, R npi and R npii By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[1338] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1339] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1340] In addition, R npi and R npii By substituting one -CH2- in the above alkyl group with -S-, an alkylthio group (thioalkyl) having 1 to 19 carbon atoms can be represented.

[1341] The alkyl sulfhydryl group is a linear, branched or cyclic alkyl sulfhydryl group, and is preferably a linear alkyl sulfhydryl group.

[1342] The alkylthio group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1343] In addition, R npi and R npii By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[1344] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[1345] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1346] In addition, R npi and R npii By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[1347] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[1348] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1349] In addition, R npiand R npii An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[1350] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[1351] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1352] In addition, R npi and R npii By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[1353] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[1354] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1355] R npi and R npii A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[1356] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[1357] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1358] As R npi and R npii Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: npi / ii -1)~Formula (R npi / ii -36) represented by the base, etc.

[1359] [Chemistry 308]

[1360]

[1361] Formula (R npi / ii -1)~Formula (R npi / ii -36), black dots represent bonds to ring A, ring B, ring C or ring D.

[1362] As R npi and R npiiThe halogen atom in ] includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

[1363] In general formulae (np-1) to (np-3), ring A, ring B, ring C and ring D each independently represent a group selected from the group consisting of the following groups (a), (b), (c) and (d),

[1364] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O-)

[1365] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[1366] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or two or more -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=)

[1367] (d) 1,4-cyclohexenylene, 1,3-dioxane-trans-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl.

[1368] One or more hydrogen atoms in the ring A, ring B, ring C and ring D may be substituted independently by a substituent group S npi1 replace.

[1369] Substituent S npi1 It represents any one of a halogen atom, a cyano group or an alkyl group having 1 to 20 carbon atoms.

[1370] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability and safety, a fluorine atom is preferred.

[1371] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1372] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[1373] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1374] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1375] Furthermore, one or two or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[1376] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1377] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1378] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1379] As a substituent S npi1 , preferably a halogen atom, preferably a fluorine atom.

[1380] In addition, in the substituent S npi1 When there are plural, these may be the same or different.

[1381] As a substituent S in ring A npi1 The substitution position is preferably the following formula (A-SP-1).

[1382] [Chemistry 309]

[1383]

[1384] In formula (A-SP-1), the white dots represent the npi The black dots represent the bonds to Z npi The bond key.

[1385] More specifically, ring A preferably represents any one of the following formula (A-1) to formula (A-3).

[1386] [Chemistry 310]

[1387]

[1388] In formula (A-1) to formula (A-3), the white dots represent the direction of R npi The black dots represent the bonds to Z npi The bond key.

[1389] More specifically, ring B preferably represents any one of the following formula (B-1) to formula (B-2).

[1390] [Chemistry 311]

[1391]

[1392] In formula (B-1) to formula (B-2), the white dots represent the Z direction. npi The black dots indicate the bond to R npii or Z npii The bond key.

[1393] More specifically, ring C preferably represents any one of the following formula (C-1) to formula (C-2).

[1394] [Chemistry 312]

[1395]

[1396] In formula (C-1) to formula (C-2), the white dots represent the Z direction. npii The black dots indicate the bond to R npii or Z npiii The bond key.

[1397] In the general formulas (np-1) to (np-3), Z npi , Z npii and Z npiii Each independently represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[1398] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[1399] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[1400] However, when the alkyl group having 1 to 10 carbon atoms is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1401] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1402] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: npi / ii / iii -1)~Formula(Z npi / ii / iii -24) represented by the base, etc.

[1403] [Chemistry 313]

[1404]

[1405] Formula (Z npi / ii / iii -1)~Formula(Z npi / ii / iii -24), white dots represent bonds to ring A, ring B or ring C, and black dots represent bonds to ring B, ring C or ring D.

[1406] In terms of Δn and / or Δε r From the point of view of Z npi , Z npii and Z npiii Preferably, each independently represents any one of a single bond, -C≡C-, and -CO-O-.

[1407] However, among the compounds represented by the general formulae (np-1) to (np-3), the compounds represented by the general formula (vt) (including subordinate concepts) are excluded.

[1408] As the compound represented by the general formula (np-2), compounds represented by the following general formulas (np-2-1) to (np-2-3) are preferred.

[1409] [Chemistry 314]

[1410]

[1411] In the general formula (np-2-1) to the general formula (np-2-3), R npi , R npii and S npi represents the same as R in the general formula (np-1) to the general formula (np-3) npi , R npii and S npi The same meaning respectively.

[1412] Specific examples of the compound represented by General Formula (np-2-1) include compounds represented by the following Structural Formula (np-2-1.1).

[1413] [Chemistry 315]

[1414]

[1415] Specific examples of the compound represented by general formula (np-2-2) include compounds represented by the following structural formulas (np-2-2.1) to (np-2-2.5).

[1416] [Chemistry 316]

[1417]

[1418] Specific examples of the compound represented by general formula (np-2-3) include compounds represented by the following structural formulas (np-2-3.1) to (np-2-3.5).

[1419] [Chemistry 317]

[1420]

[1421] The types of compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) used in the liquid crystal composition are one or more, preferably one to ten, preferably one to eight, preferably one to six, preferably one to four, and preferably one to two.

[1422] The lower limit of the total content of the compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) in 100 mass% of the liquid crystal composition is preferably 0.1 mass%, preferably 0.5 mass%, and preferably 1 mass%.

[1423] The upper limit value of the total content of the compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) in 100 mass% of the liquid crystal composition is preferably 30 mass%, preferably 20 mass%, and preferably 15 mass%.

[1424] Regarding solubility, Δn and / or Δε r From the perspective of, the total content of the compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) in 100 mass% of the liquid crystal composition is preferably 0.1 mass% to 30 mass%, preferably 0.5 mass% to 20 mass%, and preferably 1 mass% to 15 mass%.

[1425] The compounds represented by the general formula (np-1) to the general formula (np-3) (including subordinate concepts) can be produced by a known method.

[1426] (Liquid Crystal Composition)

[1427] The liquid crystal composition of the present invention can be produced, for example, by mixing the compound represented by the general formula (i), the compound represented by the general formula (ii), and the other compounds and additives as required.

[1428] Examples of additives include stabilizers, pigment compounds, polymerizable compounds, and azotolane compounds.

[1429] Examples of the stabilizer include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, and hindered amines.

[1430] Examples of the hindered phenols include hindered phenol antioxidants represented by the following structural formulas (XX-1) to (XX-3).

[1431] [Chemistry 318]

[1432]

[1433] Examples of the hindered amines include hindered amine-based light stabilizers represented by the following structural formulas (YY-1) and (YY-2).

[1434] [Chemistry 319]

[1435]

[1436] When a stabilizer is used, the type of the stabilizer used in the liquid crystal composition is one or two or more, preferably one to ten, preferably one to eight, preferably one to six, preferably one to four, and preferably one to two.

[1437] When using a stabilizer, the total content of the stabilizer in 100 mass % of the liquid crystal composition is preferably 0.005 mass % to 1 mass %, preferably 0.02 mass % to 0.50 mass %, and preferably 0.03 mass % to 0.35 mass %.

[1438] In addition, as a combination of compounds used in the liquid crystal composition, solubility, Δn and / or Δε r From the perspective of

[1439] 1) A combination of a compound represented by the general formula (i) (including subordinate concepts) and a compound represented by the general formula (ii) (including subordinate concepts); 2) A combination of a compound represented by the general formula (i) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts), a compound represented by the general formula (ii-3) (including subordinate concepts), a compound represented by the general formula (ii-4) (including subordinate concepts), and a compound represented by the general formula (ii-6) (including subordinate concepts); 3) A combination of a compound represented by the general formula (i-3) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts), a compound represented by the general formula (ii-3) (including subordinate concepts), a compound represented by the general formula (ii-4) (including subordinate concepts), and a compound represented by the general formula (ii-6) (including subordinate concepts); 4) A combination of compounds represented by the general formula (i-2) (including subordinate concepts), compounds represented by the general formula (i-3) (including subordinate concepts), compounds represented by the general formula (i-4) (including subordinate concepts), compounds represented by the general formula (ii-2) (including subordinate concepts), compounds represented by the general formula (ii-3) (including subordinate concepts), compounds represented by the general formula (ii-4) (including subordinate concepts), and compounds represented by the general formula (ii-6) (including subordinate concepts); 5) A combination of compounds represented by the general formula (i-3) (including subordinate concepts), compounds represented by the general formula (ii-1) (including subordinate concepts), compounds represented by the general formula (ii-2) (including subordinate concepts), compounds represented by the general formula (ii-3) (including subordinate concepts), and compounds represented by the general formula (ii-5) (including subordinate concepts).

[1440] <Characteristic values ​​of liquid crystal composition>

[1441] The upper limit temperature of the liquid crystal phase (T ni ) is the temperature at which the liquid crystal composition undergoes a phase transition from the nematic phase to the isotropic phase.

[1442] T ni The measurement is performed by preparing a sample of the liquid crystal composition by sandwiching it between a slide glass and a cover glass, and observing it under a polarizing microscope while heating it on a heating stage.

[1443] Alternatively, the measurement can be performed using differential scanning calorimetry (DSC).

[1444] The unit used is "℃".

[1445] T ni The higher the value, the more the nematic phase can be maintained even at high temperatures, and the wider the driving temperature range can be.

[1446] The upper limit temperature of the liquid crystal phase of the liquid crystal composition of the present invention (T ni ) can be appropriately set according to the use in indoor or car environments where the external temperature of the liquid crystal display element can be controlled, or in the case of outdoor use. From the perspective of the driving temperature range, it is preferably above 100°C, preferably 100°C to 200°C, preferably 110°C to 190°C, and preferably 150°C to 180°C.

[1447] Liquid crystal phase lower limit temperature (T →n ) is the temperature at which a liquid crystal composition undergoes a phase transition from other phases (glass phase, smectic phase, crystalline phase) to the nematic phase.

[1448] T →n The measurement is performed by filling a glass capillary with a liquid crystal composition, immersing the capillary in a -70°C refrigerant, causing the liquid crystal composition to undergo a phase transition to another phase, and observing the phase while increasing the temperature.

[1449] Alternatively, the content can be measured by differential scanning calorimetry (DSC).

[1450] The unit used is "℃".

[1451] T →n The lower the value, the more the nematic phase can be maintained even at low temperatures, thus expanding the driving temperature range.

[1452] From the viewpoint of driving temperature, the lower limit temperature (T →n ) is preferably below 10°C, preferably -70°C to 0°C, and preferably -40°C to -5°C.

[1453] Δn (refractive index anisotropy) is related to Δn in the near-infrared region used in an optical sensor described later.

[1454] The larger Δn is, the greater the phase modulation power of light of the target wavelength is, and therefore it is particularly suitable for optical sensors.

[1455] Δn at 25°C and 589 nm is the anomalous refractive index (n e ) and the constant refractive index (n o ) e -n o ) to find out.

[1456] Alternatively, Δn can be obtained using a phase difference measuring device.

[1457] The relationship of Δn=Re / d holds true between the phase difference Re, the thickness d of the liquid crystal layer, and Δn.

[1458] The liquid crystal composition was injected into a glass cell with a polyimide alignment film having a cell gap (d) of about 3.0 μm and subjected to an antiparallel rubbing treatment, and the in-plane Re was measured using a phase difference film-optical material testing apparatus RETS-100 (manufactured by Otsuka Electronics Co., Ltd.).

[1459] The measurement was performed at 25°C and 589 nm, and there is no unit.

[1460] From the viewpoint of the phase modulation power of light of a certain wavelength, the Δn of the liquid crystal composition of the present invention at 25° C. and 589 nm is preferably 0.38 or more, preferably 0.38 to 0.65, preferably 0.40 to 0.60, and preferably 0.45 to 0.55.

[1461] The rotational viscosity (γ1) is a viscosity ratio related to the rotation of liquid crystal molecules.

[1462] Regarding γ1, the liquid crystal composition is filled in a glass cell having a cell gap of about 10 μm, a voltage of 50 V is applied, and measurement is performed using LCM-2 (manufactured by Toyo Technica).

[1463] In the case of a liquid crystal composition having positive dielectric anisotropy, a horizontal alignment unit is used, and in the case of a liquid crystal composition having negative dielectric anisotropy, a vertical alignment unit is used.

[1464] The measurement was performed at a temperature of 25°C, and the unit used was mPa·s.

[1465] The smaller γ1 is, the faster the response speed of the liquid crystal composition is, and thus it is suitable for any liquid crystal display element.

[1466] From the viewpoint of response speed, the rotational viscosity (γ1) of the liquid crystal composition of the present invention at 25° C. is preferably 150 to 2000 mPa·s, preferably 200 to 1500 mPa·s, and preferably 250 to 1000 mPa·s.

[1467] The higher the dielectric anisotropy in the high-frequency region, the greater the phase modulation force for radio waves in the target frequency band, and thus it is particularly suitable for antenna use.

[1468] In antenna applications, a smaller dielectric loss tangent in a high-frequency region is preferable because the energy loss in a target frequency band is smaller.

[1469] In the liquid crystal composition of the present invention, the dielectric anisotropy Δε at 10 GHz represents the characteristics in the high frequency region. r and the average value of dielectric loss tangent tanδ iso Carry out determination.

[1470] Δε r =(ε r∥ -ε r⊥ ), tanδ iso =(2ε r⊥ tanδ ⊥ +ε r∥ tanδ ∥ ) / (2ε r⊥ +ε r∥ ).

[1471] Here, “ε r " represents the dielectric constant, "tan δ" represents the dielectric loss tangent, the subscript "∥" represents the component in the direction parallel to the orientation direction of the liquid crystal, and "⊥" represents the component in the direction perpendicular to the orientation direction of the liquid crystal.

[1472] Δε r and tanδ iso The measurement can be performed by the following method.

[1473] First, the liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE).

[1474] The capillary used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, and an effective length of 4.0 cm.

[1475] The capillary tube in which the liquid crystal composition was sealed was introduced into the center of a cavity resonator (manufactured by EM Laboratories, Inc.) having a resonance frequency of 10 GHz.

[1476] The cavity resonator has an outer shape with a diameter of 30 mm and a width of 26 mm.

[1477] Then, a signal was input and the result of the output signal was recorded using a network analyzer (manufactured by Keysight Technologies, Inc.).

[1478] The dielectric constant (ε) at 10 GHz was determined using the difference between the resonance frequency and the resonance frequency of the PTFE capillary tube without the liquid crystal composition and the PTFE capillary tube with the liquid crystal composition. r ) and loss angle (δ).

[1479] Then, the obtained tangent of δ is the dielectric loss tangent (tan δ).

[1480] The resonance frequency and the like using a PTFE capillary tube enclosing a liquid crystal composition are obtained by controlling the alignment of liquid crystal molecules as the value of a characteristic component perpendicular to the alignment direction of the liquid crystal molecules and the value of a characteristic component parallel to the alignment direction of the liquid crystal molecules.

[1481] In order to align the liquid crystal molecules in the vertical direction (perpendicular to the effective length direction) or in the parallel direction (parallel to the effective length direction) of the PTFE capillary, a magnetic field of a permanent magnet or an electromagnet is used.

[1482] Regarding the magnetic field, for example, the distance between magnetic poles is 45 mm, and the intensity of the magnetic field near the center is 0.23 Tesla.

[1483] By rotating the PTFE capillary tube in which the liquid crystal composition is sealed in parallel or perpendicular to the magnetic field, desired characteristic components can be obtained.

[1484] The measurement was carried out at a temperature of 25°C. r and tanδ iso There are no units.

[1485] Δε of the liquid crystal composition of the present invention at 25°C r It is preferably larger, and from the viewpoint of the phase modulation power in the GHz band, it is preferably 0.90 or more, preferably 0.90 to 1.50, preferably 0.95 to 1.45, and preferably 1.00 to 1.40.

[1486] Tan δ of the liquid crystal composition of the present invention at 25°C iso It is preferably smaller, and from the viewpoint of loss in the GHz band, it is preferably 0.025 or less, preferably 0.001 to 0.025, preferably 0.003 to 0.020, preferably 0.005 to 0.017, preferably 0.007 to 0.015, preferably 0.008 to 0.013, and preferably 0.009 to 0.012.

[1487] (Liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment and antennas)

[1488] Hereinafter, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition of the present invention will be described.

[1489] The liquid crystal display element of the present invention is characterized by using the above-mentioned liquid crystal composition and preferably driven by an active matrix system or a passive matrix system.

[1490] Furthermore, the liquid crystal display element of the present invention is preferably a liquid crystal display element in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition.

[1491] The sensor of the present invention is characterized in that the liquid crystal composition is used. For example, as its form, there can be listed: a distance sensor using electromagnetic waves, visible light or infrared light; an infrared sensor using temperature changes; a temperature sensor using changes in the wavelength of reflected light caused by changes in the spacing of cholesterol-type liquid crystals; a pressure sensor using changes in the wavelength of reflected light; an ultraviolet sensor using changes in the wavelength of reflected light caused by changes in composition; an electrical sensor using temperature changes caused by voltage and current; a radiation sensor using temperature changes accompanying the tracks of radioactive particles; an ultrasonic sensor using changes in the arrangement of liquid crystal molecules caused by mechanical vibrations of ultrasonic waves; an electromagnetic field sensor using changes in the wavelength of reflected light caused by temperature changes or changes in the arrangement of liquid crystal molecules caused by electric fields, etc.

[1492] As the distance measuring sensor, LiDAR (Light Detection And Ranging) using a light source is preferred.

[1493] LiDAR is preferably used for artificial satellites, airplanes, unmanned aircraft (drone), automobiles, railways, and ships.

[1494] As for automobile use, use in self-driving cars is particularly preferred.

[1495] The light source is preferably a light-emitting diode (LED) or a laser, preferably a laser.

[1496] The light used for LiDAR is preferably infrared light, and the wavelength is preferably 800nm ​​to 2000nm.

[1497] Infrared lasers with a wavelength of 905 nm or 1550 nm are particularly preferred.

[1498] When emphasis is placed on the cost of the photodetector used or on its all-weather sensitivity, an infrared laser of 905 nm is preferred, and when emphasis is placed on safety with respect to human vision, an infrared laser of 1550 nm is preferred.

[1499] The liquid crystal composition of the present invention exhibits a high Δn, and thus can provide a sensor having a large phase modulation capability in the visible light, infrared light and electromagnetic wave regions and excellent detection sensitivity.

[1500] The liquid crystal lens of the present invention is characterized in that the liquid crystal composition is used, for example, as one of its forms, it includes: a first transparent electrode layer; a second transparent electrode layer; a liquid crystal layer, which is arranged between the first transparent electrode layer and the second transparent electrode layer and contains the liquid crystal composition; an insulating layer, which is arranged between the second transparent electrode layer and the liquid crystal layer; and a high resistance layer, which is arranged between the insulating layer and the liquid crystal layer.

[1501] The liquid crystal lens of the present invention is used as, for example, a two-dimensional (2D) or 3D switching lens, a lens for adjusting the focus of a camera, or the like.

[1502] The optical communication device of the present invention is characterized in that the liquid crystal composition is used. For example, as one of its forms, there can be listed a liquid crystal on silicon (LCOS) having the following structure, which has a liquid crystal layer on a reflective layer (electrode), and the liquid crystals constituting multiple pixels are two-dimensionally arranged in the liquid crystal layer.

[1503] The optical communication device of the present invention is used as a spatial phase modulator, for example.

[1504] The antenna of the present invention is characterized by using the liquid crystal composition.

[1505] More specifically, the antenna of the present invention includes: a first substrate having a plurality of slots; a second substrate facing the first substrate and provided with a power supply portion; a first dielectric layer provided between the first substrate and the second substrate; a plurality of patch electrodes arranged corresponding to the plurality of slots; a third substrate provided with the patch electrodes; and a liquid crystal layer provided between the first substrate and the third substrate, and the liquid crystal layer contains the liquid crystal composition.

[1506] As a liquid crystal composition, one or more liquid crystal compositions are used, which contain a compound represented by the general formula (i) (including subordinate concepts) having a tetracyclic structure, -C≡C- as a linking group between the ring structures, and an isothiocyanate group (-NCS), and T ni High, Δn large, Δε r Large, tanδ iso The antenna is small and has good storage stability at room temperature, so an antenna with high reliability against external stimuli such as heat can be provided.

[1507] This makes it possible to provide an antenna capable of performing greater phase control on microwave or millimeter wave electromagnetic waves.

[1508] The antenna of the present invention preferably operates at Ka-band frequencies, or K-band frequencies, or Ku-band frequencies for satellite communications.

[1509] The antenna of the present invention is preferably a structure formed by combining a radial slot array and a patch antenna array.

[1510] As the structure of the antenna of the present invention, for example, the matters described in the pamphlet of International Publication No. 2021 / 157189 can be referred to and applied.

[1511] Examples

[1512] Hereinafter, examples are given to explain the present invention in more detail, but the present invention is not limited by any of the following examples.

[1513] The compositions in the following examples and comparative examples contain each compound in the proportions shown in the table, and the content is described in "mass %".

[1514] In addition, the following abbreviations are used for the description of the compounds.

[1515] In addition, unless otherwise specified, the compound in the cis form and the trans form represents the trans form.

[1516] <Ring structure>

[1517] [Chemical formula 320]

[1518]

[1519] <Terminal structure>[Table 1]

[1520] Abbreviation Chemical Structure -n <![CDATA[-C n H 2n+1 ]]> n- <![CDATA[C n H 2n+1 -]]> -On <![CDATA[-O-C n H 2n+1 ]]> nO- <![CDATA[C n H 2n+1 -O-]]> -Sn <![CDATA[-S-C n H 2n+1 ]]> nS- <![CDATA[C n H 2n+1 -S-]]> -V <![CDATA[-CH=CH2]]> V- <![CDATA[CH2=CH-]]> -V1 <![CDATA[-CH=CH-CH3]]> 1V- <![CDATA[CH3-CH=CH-]]> -2V <![CDATA[-CH2-CH2-CH=CH2]]> V2- <![CDATA[CH2=CH-CH2-CH2-]]> -2V1 <![CDATA[-CH2-CH2-CH=CH-CH3]]> 1V2- <![CDATA[CH3-CH=CH-CH2-CH2-]]> -OCF3 <![CDATA[-O-CF3]]> CF3O- <![CDATA[CF3-O- <!-- 137 -->]]> -H -H H- H- -CN -CN CN- CN- -NCS -NCS NCS- NCS- -(1)4 <![CDATA[-CH2CH2CH(CH3)CH3]]> 4(1)- <![CDATA[CH3CH(CH3)CH2CH2-]]>

[1521] (where n in the table is a natural number)<Linking structure>

[1522] [Table 2]

[1523] Abbreviation Chemical Structure -n- <![CDATA[-C n H 2n -]]> -nO- <![CDATA[-C n H 2n -O-]]> -On- <![CDATA[-O-C n H 2n -]]> -COO- -C(=O)-O- -OCO- -O-C(=O)- -V- -CH=CH- -nV- <![CDATA[-C n H 2n -CH=CH-]]> -VH- <![CDATA[-CH=CH-C n H 2n -]]> -T- -C≡C- -CF2O- <![CDATA[-CF2-O-]]> -OCF2- <![CDATA[-O-CF2-]]> -Az- -N=N-

[1524] (where n in the table is a natural number)

[1525] (Hindered phenol antioxidant)

[1526] [Chemical formula 321]

[1527]

[1528] (Hindered amine light stabilizer)

[1529] [Chemical formula 322]

[1530]

[1531] (Preparation of liquid crystal composition)

[1532] Prepare LC-A to LC-B and LC-01 to LC-07 described in Table 3.

[1533] [Table 3]

[1534] Table 3 LC-A LC-B LC-01 LC-02 LC-03 LC-04 LC-05 LC-06 LC-07 3-T-Pm2-Ph1-Ph-T-Ph3-NCS 5 5 5 5 10 4-T-Pm2-Ph1-Ph-T-Ph3-NCS 10 10 10 5-T-Pm2-Ph1-Ph-T-Ph3-NCS 5 3-T-Pm2-Ph2-Ph-T-Ph3-NCS 5 4-T-Pm2-Ph2-Ph-T-Ph3-NCS 5 4-T-Ph2-Pm2-T-Ph-Ph3-NCS 5 4-T-Ph-T-Pm2-Ph-T-Ph3-NCS 5 4-Ph-Ph-Ph-T-Ph3-NCS 5 4-Pm2-Ph1-Ph-T-Ph3-NCS 5 3-In-Ph-T-Ph3-NCS 10 5 4-In-T-Ph1-T-Ph3-NCS 5 3-Tet3-T-Ph-T-Ph1-NCS 7 7 7 4-T-Ph-T-Ph-Ph3-NCS 5 5 5 5 5-T-Ph-T-Ph-Ph3-NCS 3 4-T-Ph-T-Ph1-Ph3-NCS 5 5 5 5 5 5 5-T-Ph-T-Ph1-Ph3-NCS 5 5 7 5 4-T-Ph-Ph2-T-Ph3-NCS 10 10 5 10 10 10 3-T-Pm2-Ph-T-Ph3-NCS 5 5 5 5 5 4-T-Pm2-Ph-T-Ph3-NCS 10 10 4 10 10 10 5-T-Pm2-Ph-T-Ph3-NCS 5 5 5 5 4-T-Ph2-T-Ph-Ph3-NCS 10 10 5 10 4-T-Ph1-Ph-T-Ph3-NCS 4 5-T-Ph1-Ph-T-Ph3-NCS 7 5-Ph3-T-Ph-Ph3-NCS 5 3-Cy-T-Ph-T-Ph3-NCS 5 6 5 5 5 6 4-Cy-T-Ph-T-Ph3-NCS 5 6 5 5 5 6 5-Cy-Ph-NCS 6 5 4-Ph-T-Pc1-NCS 11 9 4O-Ph2-T-Ph-NCS 5 4 5O-Ph2-T-Ph-NCS 5 4 5-Ph-T-Ph1-NCS 5 4 2-Ph-T-Ph3-NCS 10 10 10 10 10 3-Ph-T-Ph3-NCS 13 13 8 15 10 8 4-Ph-T-Ph3-NCS 13 5-Ph-T-Ph3-NCS 11 5 13 5 2-Cy-Ph-Ph3-NCS 12 10 4-Cy-Ph-Ph3-NCS 12 10 4-Cy-Ph-T-Ph1-NCS 16 12 5-Cy-Ph-T-Ph1-NCS 13 10 4-Cy-Ph-T-Ph3-NCS 14 5-Cy-Ph-T-Ph3-NCS 20 CF3O-Ph-Ph-Ph3-NCS 24 4-Ph-Ph-T-Ph3-NCS 6 5-Ph-Ph-T-Ph3-NCS 12 5-Ph-Ph5-T-Ph1-NCS 15 12 Total [mass %] 100 100 100 100 100 100 100 100 100

[1535] (Examples 1 to 37 and Comparative Examples 1 to 2)

[1536] Liquid crystal compositions listed in Tables 4 to 9 were prepared using LC-A to LC-B and LC-01 to LC-07, hindered phenol antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2), and their physical properties were measured and a <storage test> was performed. The results are shown in Tables 4 to 9. In Comparative Example 1, since the crystallization occurred at room temperature, no high frequency characteristics (Δε r and tanδ iso ) determination.

[1537] <Storage Test>

[1538] 0.5 g of the liquid crystal composition was weighed in a 1 mL sample bottle (manufactured by Maruemu), and degassed at 150 Pa to 250 Pa for 10 minutes. Then, it was rinsed with dry nitrogen and covered with a prepared cover. It was stored in a temperature-controlled thermostatic bath (manufactured by Espec, SH-241) at 25° C. for 2 weeks, and the crystallization of the liquid crystal composition was visually confirmed every week.

[1539] [Table 4]

[1540]

[1541] [Table 5]

[1542]

[1543] [Table 6]

[1544]

[1545] [Table 7]

[1546]

[1547] [Table 8]

[1548]

[1549] [Table 9]

[1550]

[1551] According to Examples 1 to 7, the liquid crystal composition using the compound represented by the general formula (i) is T ni High, large Δn, Δε r Large, tanδ iso A liquid crystal composition having a small size and good storage stability at room temperature.

[1552] In particular, in Example 1, Example 2, and Example 5, Δn and Δε r Particularly great results.

[1553] On the other hand, according to Comparative Examples 1 and 2, the liquid crystal compositions not using the compound represented by the general formula (i) crystallized at room temperature or had a small result of Δn less than 0.38.

[1554] Furthermore, according to Examples 8 to 37, even when a hindered phenol antioxidant or a hindered amine light stabilizer is used in combination, T ni High, large Δn, Δε r Large, tanδ iso Small size, good storage at room temperature.

[1555] The synthesis of the compound represented by the general formula (i) is described below.

[1556] (Synthesis Example 1) Preparation of the compound represented by formula (I-1)

[1557] [Chemistry 323]

[1558]

[1559] Under nitrogen environment, 50g of compound represented by formula (I-1-1), 1.4g of copper iodide (I), 2.5g of bis(triphenylphosphine) palladium dichloride (II), 53.7g of triethylamine and 125mL of tetrahydrofuran were added to the reaction container at room temperature. Next, a solution in which 30.0g of compound represented by formula (I-1-2) was dissolved in 125mL of tetrahydrofuran was added dropwise while stirring at room temperature, and stirred at room temperature for 1 hour. After the reaction was completed, a saturated aqueous solution of ammonium chloride was injected into the reaction solution and extracted with toluene. After the organic layer was washed with saturated brine, it was refined by column chromatography (amino silica gel, toluene / hexane = 1 / 8 to 1 / 0) to obtain 50.3g of compound represented by formula (I-1-3).

[1560] Next, under a nitrogen environment, 42.0 g of the compound represented by formula (I-1-3), 36.3 g of bis(pinacol)diboron, 40.1 g of potassium acetate, 2.2 g of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct, and 420 mL of dimethyl sulfoxide were added to the reaction container at room temperature and stirred at 90 ° C. After the reaction was completed, a saturated aqueous ammonium chloride solution was injected into the reaction solution and extracted with toluene. After the organic layer was washed with saturated brine, it was refined by column chromatography (alumina silica gel, toluene) to obtain 36.6 g of the compound represented by formula (I-1-4).

[1561] Next, under a nitrogen atmosphere, 6.3 g of the compound represented by formula (I-1-5), 7.5 g of the compound represented by formula (I-1-4), 0.1 g of bis(triphenylphosphine)palladium(II) dichloride, 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to a reaction vessel at room temperature, and the mixture was stirred at 75 °C for 2 hours. After completion of the reaction, filtration was carried out, and purification was performed by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0), whereby 6.5 g of the compound represented by formula (I-1-6) was obtained.

[1562] Next, under a nitrogen atmosphere, 6.5 g of the compound represented by formula (I-1-6), 3.6 g of the compound represented by formula (I-1-7), 0.1 g of bis(triphenylphosphine)palladium(II) dichloride, 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to a reaction vessel at room temperature, and the mixture was stirred at 75 °C for 2 hours. After completion of the reaction, filtration was carried out, and purification was performed by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0), whereby 6 g of the compound represented by formula (I-1-8) was obtained.

[1563] Next, under a nitrogen atmosphere, 6 g of the compound represented by formula (I-1-8), 17 mL of dichloromethane, and 2.5 g of 1,1'-thiocarbonyldiimidazole were added to a reaction vessel at room temperature, and the mixture was stirred at room temperature. After completion of the reaction, the organic layer was washed with saturated brine, and purification was performed by column chromatography (silica gel, toluene), and then by recrystallization (toluene / hexane = 1 / 1), whereby 5 g of the compound represented by formula (I-1) was obtained.

[1564] Mass spectrometry (MS) (electron impact (EI)): m / z = 521

[1565] (Synthesis Example 2) Production of the compound represented by formula (I-2)

[1566] [Chemical Formula 324]

[1567]

[1568] Under a nitrogen atmosphere, 6.5 g of the compound represented by formula (I-2-1), 3.7 g of the compound represented by formula (I-2-2), 0.1 g of bis(triphenylphosphine)palladium(II) dichloride, 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to a reaction vessel at room temperature, and the mixture was stirred at 75 °C for 2 hours. After completion of the reaction, filtration was carried out, and purification was performed by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0), whereby 6.2 g of the compound represented by formula (I-2-3) was obtained.

[1569] Next, under a nitrogen atmosphere, 6.2 g of the compound represented by formula (I-2-3), 17 mL of dichloromethane, and 2.6 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel at room temperature, and the mixture was stirred at room temperature. After completion of the reaction, the organic layer was washed with saturated brine and then purified by column chromatography (silica gel, toluene) and then by recrystallization (toluene / hexane = 1 / 1) to obtain 5.3 g of the compound represented by formula (I-2).

[1570] MS(EI): m / z = 535

[1571] (Synthesis Example 3) Preparation of the compound represented by formula (I-3)

[1572] [Chemical formula 325]

[1573]

[1574] Under a nitrogen atmosphere, 6.5 g of the compound represented by formula (I-3-1), 3.8 g of the compound represented by formula (I-3-2), 0.1 g of bis(triphenylphosphine)palladium(II) dichloride, 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to a reaction vessel at room temperature, and the mixture was stirred at 75 °C for 2 hours. After completion of the reaction, filtration was carried out, and purification was carried out by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0) to obtain 6.3 g of the compound represented by formula (I-1-3).

[1575] Next, under a nitrogen atmosphere, 6.3 g of the compound represented by formula (I-3-3), 17 mL of dichloromethane, and 2.6 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel at room temperature, and the mixture was stirred at room temperature. After completion of the reaction, the organic layer was washed with saturated brine and then purified by column chromatography (silica gel, toluene) and then by recrystallization (toluene / hexane = 1 / 1) to obtain 5.5 g of the compound represented by formula (I-3).

[1576] MS(EI): m / z = 549

[1577] (Synthesis Example 4) Preparation of the compound represented by formula (I-4)

[1578] [Chemical formula 326]

[1579]

[1580] Under nitrogen atmosphere, 6.3 g of the compound represented by formula (I-4-1), 7.5 g of the compound represented by formula (I-4-2), 0.1 g of bis(triphenylphosphine)palladium(II) dichloride, 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to the reaction container at room temperature, and stirred for 2 hours at 75° C. After the reaction was completed, the mixture was filtered and purified by column chromatography (amino silica gel, toluene / hexane=2 / 3 to 1 / 0) to obtain 6.8 g of the compound represented by formula (I-4-3).

[1581] Next, under a nitrogen atmosphere, 6.8 g of the compound represented by formula (I-4-3), 3.5 g of the compound represented by formula (I-4-4), 0.1 g of bis(triphenylphosphine)palladium(II) dichloride, 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to the reaction container at room temperature, and stirred for 2 hours at 75° C. After the reaction was completed, the mixture was filtered and purified by column chromatography (amino silica gel, toluene / hexane=2 / 3 to 1 / 0) to obtain 6.5 g of the compound represented by formula (I-4-5).

[1582] Next, under a nitrogen atmosphere, 6.5 g of the compound represented by formula (I-4-5), 17 mL of dichloromethane, and 2.4 g of 1,1-thiocarbonyldiimidazole were added to the reaction container at room temperature and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and then by recrystallization (toluene / hexane = 1 / 1), thereby obtaining 5.5 g of the compound represented by formula (I-4).

[1583] MS (EI): m / z = 521

[1584] (Synthesis Example 5) Preparation of the compound represented by formula (I-5)

[1585] [Chemistry 327]

[1586]

[1587] Under nitrogen atmosphere, 6.8 g of the compound represented by formula (I-5-1), 3.7 g of the compound represented by formula (I-5-2), 0.1 g of bis(triphenylphosphine)palladium dichloride (II), 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to the reaction container at room temperature, and stirred at 75° C. for 2 hours. After the reaction was completed, the mixture was filtered and purified by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0) to obtain 6.8 g of the compound represented by formula (I-5-3).

[1588] Next, under a nitrogen environment, 6.8 g of the compound represented by formula (I-5-3), 17 mL of dichloromethane, and 2.7 g of 1,1-thiocarbonyldiimidazole were added to the reaction container at room temperature and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and then by recrystallization (toluene / hexane = 1 / 1), thereby obtaining 6 g of the compound represented by formula (I-5).

[1589] MS (EI): m / z = 535

[1590] (Synthesis Example 6) Preparation of the compound represented by formula (I-6)

[1591] [Chemistry 328]

[1592]

[1593] Under nitrogen environment, 10g of compound represented by formula (I-6-1), 0.25g of copper iodide (I), 1g of bis(triphenylphosphine) palladium dichloride (II), 25g of triethylamine, and 50mL of tetrahydrofuran were added to the reaction container at room temperature. Next, while stirring at room temperature, a solution in which 8.3g of compound represented by formula (I-6-2) was dissolved in 25mL of tetrahydrofuran was added dropwise, and stirred at room temperature for 1 hour. After the reaction was completed, a saturated aqueous solution of ammonium chloride was injected into the reaction solution and extracted with toluene. After the organic layer was washed with saturated brine, it was refined by column chromatography (amino silica gel, toluene / hexane = 1 / 8 to 1 / 0) to obtain 10.5g of compound represented by formula (I-6-3).

[1594] Next, under a nitrogen atmosphere, 10.5 g of the compound represented by formula (I-6-3), 6.0 g of the compound represented by formula (I-6-4), 0.2 g of bis(triphenylphosphine)palladium(II) dichloride, 6.5 g of sodium carbonate, 50 mL of tetrahydrofuran, and 25 mL of water were added to the reaction container at room temperature, and stirred for 2 hours at 75° C. After the reaction was completed, the mixture was filtered and purified by column chromatography (amino silica gel, toluene / hexane=2 / 3 to 1 / 0) to obtain 10.2 g of the compound represented by formula (I-6-5).

[1595] Next, under a nitrogen environment, 10.2 g of the compound represented by formula (I-6-5), 30 mL of dichloromethane, and 4.4 g of 1,1-thiocarbonyldiimidazole were added to the reaction container at room temperature and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and then by recrystallization (toluene / hexane = 1 / 1), thereby obtaining 8.7 g of the compound represented by formula (I-6).

[1596] MS (EI): m / z = 535

[1597] (Synthesis Example 7) Preparation of the compound represented by formula (I-7)

[1598] [Chemical Formula 329]

[1599]

[1600] Under a nitrogen atmosphere, at room temperature, 10 g of the compound represented by formula (I-7-1), 7.7 g of the compound represented by formula (I-7-2), 0.2 g of bis(triphenylphosphine)palladium(II) dichloride, 7 g of sodium carbonate, 50 mL of tetrahydrofuran, and 25 mL of water were added to a reaction vessel, and the mixture was stirred at 75 °C for 2 hours. After completion of the reaction, filtration was carried out, and purification was performed by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0), whereby 10.5 g of the compound represented by formula (I-7-3) was obtained.

[1601] Next, under a nitrogen atmosphere, at room temperature, 10.5 g of the compound represented by formula (I-7-3), 0.2 g of copper(I) iodide, 0.4 g of bis(triphenylphosphine)palladium(II) dichloride, 25 g of triethylamine, and 50 mL of tetrahydrofuran were added to a reaction vessel. Next, while stirring at room temperature, a solution prepared by dissolving 7 g of the compound represented by formula (I-7-4) in 15 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and extraction was carried out with toluene. After washing the organic layer with saturated brine, purification was performed by column chromatography (amino silica gel, toluene / hexane = 1 / 8 to 1 / 0), whereby 10.3 g of the compound represented by formula (I-7-5) was obtained.

[1602] Next, under a nitrogen atmosphere, at room temperature, 10.3 g of the compound represented by formula (I-7-5), 25 mL of dichloromethane, and 4 g of 1,1'-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was stirred at room temperature. After completion of the reaction, the organic layer was washed with saturated brine, and purification was performed by column chromatography (silica gel, toluene), and then by recrystallization (toluene / hexane = 1 / 1), whereby 5 g of the compound represented by formula (I-7) was obtained.

[1603] MS (EI): m / z = 535

[1604] (Synthesis Example 8) Preparation of the compound represented by formula (I-8)

[1605] [Chemical Formula 330]

[1606]

[1607] Under nitrogen atmosphere, 10 g of the compound represented by formula (I-8-1), 7.9 g of the compound represented by formula (I-8-2), 0.2 g of bis(triphenylphosphine)palladium(II) dichloride, 7 g of sodium carbonate, 50 mL of tetrahydrofuran, and 25 mL of water were added to the reaction container at room temperature, and stirred at 75°C for 2 hours. After the reaction was completed, the mixture was filtered and purified by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0) to obtain 10.4 g of the compound represented by formula (I-8-3).

[1608] Next, under a nitrogen environment, 10.4 g of the compound represented by formula (I-8-3), 25 mL of dichloromethane, and 5 g of 1,1-thiocarbonyldiimidazole were added to the reaction container at room temperature and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and then by recrystallization (toluene / hexane = 1 / 1), thereby obtaining 9.8 g of the compound represented by formula (I-8).

[1609] MS (EI): m / z = 478

[1610] (Synthesis Example 9) Preparation of the compound represented by formula (I-9)

[1611] [Chemistry 331]

[1612]

[1613] Under nitrogen atmosphere, 10 g of the compound represented by formula (I-9-1), 7.8 g of the compound represented by formula (I-9-2), 0.2 g of bis(triphenylphosphine)palladium(II) dichloride, 7 g of sodium carbonate, 50 mL of tetrahydrofuran, and 25 mL of water were added to the reaction container at room temperature, and stirred for 2 hours at 75°C. After the reaction was completed, the mixture was filtered and purified by column chromatography (amino silica gel, toluene / hexane = 2 / 3 to 1 / 0) to obtain 10.7 g of the compound represented by formula (I-9-3).

[1614] Next, under a nitrogen environment, 10.7 g of the compound represented by formula (I-9-3), 25 mL of dichloromethane, and 4.4 g of 1,1-thiocarbonyldiimidazole were added to the reaction container at room temperature and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and then by recrystallization (toluene / hexane = 1 / 1), thereby obtaining 10.5 g of the compound represented by formula (I-9).

[1615] MS (EI): m / z = 511

[1616] Industrial Applicability

[1617] The compound and liquid crystal composition of the present invention can be used for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices and antennas.

Claims

1. A liquid crystal composition comprising one or more compounds represented by the following general formula (i), [Chemistry 1] R i1 -A i1 -Z i1 -A i2 -Z i2 -A i3 -Z i3 -A i4 -NCS (i) (In general formula (i), R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. A i1 , A i2 , A i3 and A i4 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, The A i1 , A i2 , A i3 and A i4 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace, Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. In the substituent S i1 When there are multiple, these may be the same or different, Z i1 , Z i2 and Z i3 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, Z i1 , Z i2 and Z i3 At least one representation of -C≡C-, One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, But oxygen atoms do not bond directly to each other).

2. The liquid crystal composition according to claim 1, wherein R i1 The alkyl group represents an alkynyl group having 2 to 20 carbon atoms when one or two or more -CH2-CH2- are replaced by -C≡C-.

3. The liquid crystal composition according to claim 1 or 2, wherein Z i3 It means -C≡C-.

4. The liquid crystal composition according to claim 1 or 2, further comprising one or more compounds represented by the following general formula (ii): [Chemistry 2] (In general formula (ii), R ii1 each independently represents an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms. However, oxygen atoms do not bond directly to each other. A ii1 and A ii2 Each independently represents a group selected from the group consisting of the following group (a), group (b), group (c) and group (d), (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- and / or -S-) (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=) (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene-2,7-diyl, 2,3-dihydroindane-2,5-diyl, 2,3-dihydroindane-1,5-diyl, 2,3-dihydroindane-3,5-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=) (d) thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl, benzo[1,2-b:4,5-b']dithiophene-2,6-diyl (one -CH= or two or more -CH= in the above group may be substituted with -N=) The A ii1 and A ii2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S ii1 replace, Substituent S ii1 represents any one of a halogen atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms. However, oxygen atoms do not bond directly to each other. In the substituent S ii1 When there are multiple, these may be the same or different. Z ii1 represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, Oxygen atoms do not bond directly to each other. n ii1 represents an integer from 1 to 4, In A ii1 and Z ii1 Where there are multiple, these may be the same or different; in, (excluding compounds represented by general formula (i)).

5. The liquid crystal composition according to claim 4, wherein the compound represented by the general formula (ii) is selected from the group consisting of compounds represented by the following general formulas (ii-1) to (ii-8), [Chemistry 3] R ii1 -A ii1 -A ii2 -NCS (ii-1) R ii1 -A ii1 -A ii1-2 -A ii2 -NCS (ii-5) R ii1 -A ii1 -A ii1-2 -A ii1-3 -A ii2 -NCS (ii-8) (In general formula (ii-1) to general formula (ii-8), R ii1 , A ii1 and A ii2 represents the same as R in the general formula (ii) ii1 , A ii1 and A ii2 The same meaning respectively, In the general formula (ii-3) to the general formula (ii-8), A ii1-2 and A ii1-3 The definitions of are independently the same as those of A in the general formula (ii). ii1 ) The liquid crystal composition according to claim 1 or 2, wherein Δn at 25°C and 589 nm is 0.38 or more.

7. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 6.

8. The liquid crystal display element according to claim 7, which is driven by an active matrix method or a passive matrix method. 9 . A liquid crystal display element that reversibly switches a dielectric constant by reversibly changing the alignment direction of liquid crystal molecules of the liquid crystal composition according to claim 1 .

10. A sensor using the liquid crystal composition according to any one of claims 1 to 6.

11. A liquid crystal lens using the liquid crystal composition according to any one of claims 1 to 6.

12. An optical communication device using the liquid crystal composition according to any one of claims 1 to 6.

13. An antenna using the liquid crystal composition according to any one of claims 1 to 6.

14. The antenna according to claim 13, comprising: A first substrate having a plurality of grooves; A second substrate, facing the first substrate and provided with a power supply portion; A first dielectric layer is disposed between the first substrate and the second substrate; a plurality of patch electrodes, arranged corresponding to the plurality of grooves; A third substrate, provided with the patch electrode; as well as A liquid crystal layer is disposed between the first substrate and the third substrate. The liquid crystal layer contains the liquid crystal composition according to any one of claims 1 to 6.

15. A compound represented by the following general formula (i): [Chemistry 4] R i1 -A i1 -Z i1 -A i2 -Z i2 -A i3 -Z i3 -A i4 -NCS (i) (In general formula (i), R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. A i1 , A i2 , A i3 and A i4 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, The A i1 , A i2 , A i3 and A i4 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace, Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. In the substituent S i1 When there are multiple, these may be the same or different, Z i1 , Z i2 and Z i3 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, Z i1 , Z i2 and Z i3 At least one representation of -C≡C-, One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, But oxygen atoms do not bond directly to each other).

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