WO2025035449A1

WO2025035449A1 - Compound and liquid crystal composition, liquid crystal display device, sensor, liquid crystal lens, optical communication device, and antenna using the compound

Info

Publication number: WO2025035449A1
Application number: PCT/CN2023/113521
Authority: WO
Inventors: Jinqiu LI; Masanao Hayashi; Ruiqin ZHAI; Jian ZHUANG
Original assignee: DIC Corp; Dainippon Ink and Chemicals Co Ltd
Current assignee: DIC Corp
Priority date: 2023-08-17
Filing date: 2023-08-17
Publication date: 2025-02-20
Anticipated expiration: 2026-02-17
Also published as: CN121335891A; JP7839461B2; JP2025534189A

Abstract

An object of the present invention is to provide a compound which can provide a liquid crystal composition having large Δn, large Δεr, and good storage property at low temperature, and also provide a liquid crystal composition, a liquid crystal display device, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound. A compound is represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS), and a liquid crystal composition, a liquid crystal display device, a sensor, a liquid crystal lens, an optical communication device, and an antenna each use the compound.

Description

COMPOUND AND LIQUID CRYSTAL COMPOSITION, LIQUID CRYSTAL DISPLAY DEVICE, SENSOR, LIQUID CRYSTAL LENS, OPTICAL COMMUNICATION DEVICE, AND ANTENNA USING THE COMPOUND

Technical Field

The present invention relates to a compound and a liquid crystal composition, a liquid crystal display device, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound.

Background Art

An antenna using a liquid crystal, which transmits and receives radio waves between a moving body, such as an automobile car, and a communication satellite, attracts attention as a novel application of a liquid crystal frequently used for display applications. In general, satellite communication uses a parabolic antenna, but when used for a moving body such as an automobile car, a parabolic antenna is required to be directed at any time to the satellite direction, and thus a large moving portion is required. However, in an antenna using a liquid crystal, the transmitting and receiving direction of radio waves can be changed by operation of a liquid crystal in a panel, and thus the antenna itself need not be moved, and the shape of the antenna can be made planar. Also, in order to realize global large-capacity and high-speed communication, the study of a low-orbit satellite constellation using many low-orbit satellites is progressed. A liquid crystal antenna in which the transmitting and receiving direction of radio waves can be easily changed is useful for following a low-orbit satellite which appears from the ground to constantly move. In general, download of a large amount of data of high-precision 3D map information is required for autonomous driving of an automobile car or the like. However, an antenna using a liquid crystal enables download of a large amount of data from a communication satellite by incorporating the antenna into an automobile car without a mechanical moving portion. The frequency band used for satellite communication is a band of about 13 GHz and is greatly different from the frequency used for usual liquid crystal display application. Therefore, the physical properties required for the liquid crystal are also greatly different, and Δn required for a liquid crystal for an antenna is, for example, about 0.4, and the operation temperature range is, for example, 20℃ to 120℃. In addition, an infrared laser image recognition/distance measuring apparatus using a liquid crystal also attracts attention as a sensor for autonomous driving of a moving body such as an automobile car or the like. In this application, Δn required for a liquid crystal is, for example, about 0.3 to 0.6, and the operation temperature range is, for example, 10℃ to 100℃. Further, it is known that a liquid crystalline compound constituting a liquid crystal composition showing Δn of as high as 0.2 or more frequently has low compatibility. Therefore, it is also important to select a liquid crystal composition having high compatibility. On the other hand, a technique of a liquid crystal for an antenna is disclosed in, for example, PTL 1. Also, NPL 1 proposes the use of a liquid crystal material as a constituent component of a high-frequency device.

Citation List Patent Literature

[PTL 1] Japanese Unexamined Patent Application Publication No. 2016-37607

[Non Patent Literature]

[NPL 1] D. Dolfi, "Electronics Letters" , (England) , 1993, Vol. 29, No. 10, p. 926-928

Summary of Invention Technical Problem

Accordingly, it is an object of the present invention to provide a compound which can provide a liquid crystal composition having large Δn, large Δε_r, and good storage property at low temperature, and also provide a liquid crystal composition, a liquid crystal display device, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound.

Solution to Problem

As a result of earnest investigation, the inventors found that the problem can be solved by a compound represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS) , leading to the achievement of the present invention. An example of the configuration of the present invention which solves the problem is as follows.

Item 1. A compound represented by general formula (i) below,

[Chem. 1]

(in the general formula (i) ,

Rⁱ¹ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, one or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-,

one or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom,

an oxygen atom and an oxygen atom are not directly bonded to each other,

A^ibf/t represents a group selected from the group consisting of groups represented by general formulae (A^ibf-1) to (A^ibf-4) and (A^ibt-1) to (A^ibt-4) below,

[Chem. 2]

(in the general formulae (A^ibf-1) to (A^ibf-4) and (A^ibt-1) to (A^ibt-4) ,

a white point represents a bond to Rⁱ¹,

a black point represents a bond to Zⁱ¹,

Lⁱ¹and Lⁱ²each independently represent any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

one or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-,

one or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom, and

an oxygen atom and an oxygen atom are not directly bonded to each other)

Aⁱ¹and Aⁱ² each independently represent any one of a hydrocarbon ring having 3 to 16 carbon atoms and a heterocyclic ring having 3 to 16,

one or two or more hydrogen atoms in Aⁱ¹and Aⁱ² may be each independently substituted by substituent Sⁱ¹,

the substituent Sⁱ¹ represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

an oxygen atom and an oxygen atom are not directly bonded to each other,

when a plurality of substituents Sⁱ¹ are present, they may be the same or different,

Zⁱ¹and Zⁱ² each independently represent any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

one or two or more -CH₂-in the alkylene group may be each independently substituted by -O-, -CF₂-, and/or -CO-,

one or two or more -CH₂-CH₂-in the alkylene group may be each 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-, and/or -C≡C-,

an oxygen atom and an oxygen atom are not directly bonded to each other,

nⁱ¹ represents an integer of 0 to 3, and

when a plurality of Aⁱ² or Zⁱ² are present, they may be the same or different) .

Item. 2. The compound described in Item 1, in which the compound represented by the general formula (i) is a compound selected from the group consisting of compounds represented by general formulae (i-1) to (i-6) below,

[Chem. 3]
Rⁱ¹-A^ibf/t-Aⁱ¹-NCS (i-1)

Rⁱ¹-A^ibf/t-Aⁱ¹-Aⁱ²-NCS (i-3)

(in the general formulae (i-1) to (i-6) ,

Rⁱ¹, A^ibf/t, Aⁱ¹, and Aⁱ² represent the same meanings as Rⁱ¹, A^ibf/t, Aⁱ¹, and Aⁱ², respectively, in the general formula (i) ) .

Item 3. The compound described in Item 1 or 2, in which Rⁱ¹ represents any one of a linear or branched alkyl group having 2 to 6 carbon atoms, a linear alkoxyalkyl having 1 to 6 carbon atoms, and a linear alkenyl group having 2 to 6 carbon atoms.

Item 4. A liquid crystal composition containing one or more two or more compounds described in any one of Items 1 to 3.

Item 5. A liquid crystal display device using the liquid crystal composition described in Item 4.

Item 6. A sensor using the liquid crystal composition described in Item 4.

Item 7. A liquid crystal lens using the liquid crystal composition described in Item 4.

Item 8. An optical communication device using the liquid crystal composition described in Item 4.

Item 9. An antenna using the liquid crystal composition described in Item 4.

Item 10. The antenna described in Item 9, including

a first substrate provided with 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 disposed 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;

the liquid crystal layer containing the liquid crystal composition described in Item 4.

Advantageous Effects of Invention

According to the present invention, a liquid crystal composition having large Δn, large Δ_εr, and good storage property at low temperature can be obtained by using a compound represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS) . The liquid crystal composition is useful for a liquid crystal display device, a sensor, a liquid crystal lens, an optical communication device, and an antenna.

Description of Embodiments

[Compound represented by general formula (i) ]

A compound according to the present invention is a compound represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS) .

Also, a liquid crystal composition according to the present invention contains one or two or more compounds represented by the general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS) .

[Chem. 4]

In the general formula (i) , Rⁱ¹ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. The alkyl group having 1 to 20 carbon atoms is a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, and preferably a linear alkyl group. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10 or preferably 2 to 6. One or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-. One or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom. Examples of a halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. However, when the alkyl group is substituted by a predetermined group, an oxygen atom and an oxygen atom are not directly bonded to each other. In addition, from the viewpoint of stability of the compound, a sulfur atom and a sulfur atom and/or an oxygen atom and a sulfur atom are preferably not directly bonded to each other. For example, when one -CH₂-in the alkyl group is substituted by -O-, Rⁱ¹ can represent an alkoxy group having 1 to 19 carbon atoms. The alkoxyl group is a linear, branched, or cyclic alkoxyl group, and preferably a linear alkoxyl group. The number of carbon atoms in the alkoxyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one -CH₂-in the alkyl group is substituted by -S-, Rⁱ¹ can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and preferably a linear alkylsulfanyl group. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one or two or more -CH₂-CH₂-in the alkyl group is substituted by -CH=CH-, Rⁱ¹ can represent an alkenyl group having 2 to 20 carbon atoms. The alkenyl group is a linear, branched, or cyclic alkoxyl group, and preferably a linear alkenyl group. The number of carbon atoms in the alkenyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one or two or more -CH₂-CH₂-in the alkyl group is substituted by -C≡C-, Rⁱ¹ can represent an alkynyl group having 2 to 20 carbon atoms. The alkynyl group is a linear, branched, or cyclic alkynyl group, and preferably a linear alkynyl group. The number of carbon atoms in the alkynyl group is preferably 2 to 10 or preferably 2 to 6. From the viewpoint of the ease of synthesis and elongation of a conjugated system, the alkynyl group is preferably an alkynyl group represented by formula (Rⁱ¹-A) below.

[Chem. 5]

In the formula (Rⁱ¹-A) , R^i1A represents an alkyl group having 1 to 18 carbon atoms. The alkyl group having 1 to 18 carbon atoms is a linear, branched, or cyclic alkyl group and preferably a linear alkyl group. The number of carbon atoms in the alkyl group having 1 to 18 carbon atoms is preferably 1 to 8. One or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-. One or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom. Examples of a halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted by a predetermined group, an oxygen atom and an oxygen atom are not directly bonded to each other. In addition, from the viewpoint of stability of the compound, a sulfur atom and a sulfur atom and/or an oxygen atom and a sulfur atom are preferably not directly bonded to each other. In addition, in the formula (Rⁱ¹-A) , a black point represents a bond to Aⁱ¹. In addition, when one -CH₂-in the alkyl group is substituted by -O-and one or two or more -CH₂-CH₂-in the alkyl group are each substituted by -CH=CH-, Rⁱ¹ can represent an alkenyloxy group having 2 to 19 carbon atoms. The alkenyloxy group is a linear, branched, or cyclic alkenyloxy group, and preferably a linear alkenyloxy group. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10 or preferably 2 to 6. In addition, when one or two or more hydrogen atoms in the alkyl group are each substituted by a halogen atom, Rⁱ¹ can represent a halogenated alkyl group having 1 to 20 carbon atoms. The halogenated alkyl group is a linear, branched, or cyclic halogenated alkyl group and preferably a linear halogenated alkyl group. The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one -CH₂-in the alkyl group is substituted by -O-and one or two or more hydrogen atoms in the alkyl group are each substituted by a halogen atom, Rⁱ¹ can represent a halogenated alkoxy group having 1 to 19 carbon atoms. The halogenated alkoxy group is a linear, branched, or cyclic halogenated alkoxy group and preferably a linear halogenated alkoxy group. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10 or preferably 2 to 6. For example, when one -CH₂-in the alkyl group is substituted by -O-, Rⁱ¹ can represent an alkoxyalkyl group having 1 to 19 carbon atoms. The alkoxyalkyl group is a linear, branched, or cyclic alkoxyalkyl group and preferably a linear alkoxyalkyl group. The number of carbon atoms in the alkoxyalkyl group is preferably 2 to 10 or preferably 2 to 6. Examples of the alkyl group (including a substituted alkyl group) having 1 to 20 carbon atoms in Rⁱ¹ include groups represented by formulae (R^il-1) to (Rⁱ¹-46) below.

[Chem. 6]

[Chem. 7]

In the formulae (R^il-1) to (Rⁱ¹-46) , a black point represents a bond to A^ibf/t. From the viewpoint of Δn and compatibility with another liquid crystal composition, Rⁱ¹ is preferably a linear or branched alkyl group having 2 to 6 carbon atoms, a linear alkoxyalkyl group having 1 to 6 carbon atoms, or a linear alkenyl group having 2 to 6 carbon atoms.

In the general formula (i) , A^ibf/t represents a group selected from the group consisting of groups represented by general formulae (A^ibf-1) to (A^ibf-4) and (A^ibt-1) to (A^ibt-4) below.

[Chem. 8]

In the general formulae (A^ibf-1) to (A^ibf-4) and (A^ibt-1) to (A^ibt-4) , a white point represents a bond to Rⁱ¹, and a black point represents a bond to Zⁱ¹. In the general formulae (A^ibf-1) to (A^ibf-4) and (A^ibt-1) to (A^ibt-4) , Lⁱ¹ and Lⁱ² each independently represent any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms. The alkyl group having 1 to 20 carbon atoms is a linear, branched, or cyclic alkyl group and preferably a linear alkyl group. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10 or preferably 2 to 6. One or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-. One or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. However, when the alkyl group is substituted by a predetermined group, an oxygen atom and an oxygen atom are not directly bonded to each other. In addition, from the viewpoint of stability of the compound, a sulfur atom and a sulfur atom and/or an oxygen atom and a sulfur atom are preferably not directly bonded to each other. For example, when one -CH₂-in the alkyl group is substituted by -O-, Lⁱ¹ and Lⁱ² can represent an alkoxy group having 1 to 19 carbon atoms. The alkoxy group is a linear, branched, or cyclic alkoxy group, and preferably a linear alkoxy group. The number of carbon atoms in the alkoxy group is preferably 2 to 10 or preferably 2 to 6. In addition, when one -CH₂-in the alkyl group is substituted by -S-, Lⁱ¹ and Lⁱ² can each represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and preferably a linear alkylsulfanyl group. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one or two or more -CH₂-CH₂-in the alkyl group is substituted by -CH=CH-, Lⁱ¹ and Lⁱ² can each represent an alkenyl group having 2 to 20 carbon atoms. The alkenyl group is a linear, branched, or cyclic alkoxyl group, and preferably a linear alkenyl group. The number of carbon atoms in the alkenyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one or two or more -CH₂-CH₂-in the alkyl group is substituted by -C≡C-, Lⁱ¹ and Lⁱ² can each represent an alkynyl group having 2 to 20 carbon atoms. The alkynyl group is a linear, branched, or cyclic alkynyl group, and preferably a linear alkynyl group. The number of carbon atoms in the alkynyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one -CH₂-in the alkyl group is substituted by -O-and one or two or more -CH₂-CH₂-in the alkyl group are each substituted by -CH=CH-, Lⁱ¹ and Lⁱ² can each represent an alkenyloxy group having 2 to 19 carbon atoms. The alkenyloxy group is a linear, branched, or cyclic alkenyloxy group, and preferably a linear alkenyloxy group. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10 or preferably 2 to 6. In addition, when one or two or more hydrogen atoms in the alkyl group are each substituted by a halogen atom, Lⁱ¹ and Lⁱ² can each represent a halogenated alkyl group having 1 to 20 carbon atoms. The halogenated alkyl group is a linear, branched, or cyclic halogenated alkyl group and preferably a linear halogenated alkyl group. The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10 or preferably 2 to 6. In addition, when one -CH₂-in the alkyl group is substituted by -O-and one or two or more hydrogen atoms in the alkyl group are each substituted by a halogen atom, Lⁱ¹ and Lⁱ² can each represent a halogenated alkoxy group having 1 to 19 carbon atoms. The halogenated alkoxy group is a linear, branched, or cyclic halogenated alkoxy group and preferably a linear halogenated alkoxy group. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10 or preferably 2 to 6.

Examples of an alkyl group (including a substituted group) having 1 to 20 carbon atoms in Lⁱ¹ and Lⁱ² include groups represented by formulae (L^i1/2-1) to (L^i1/2-36) below.

[Chem. 9]

In the formulae (L^i1/2-1) to (L^i1/2-36) , a black point represents a bond to a benzofuran structure or a benzothiophene structure. From the viewpoint of solubility and viscosity, at least one of Lⁱ¹ and Lⁱ² is preferably a hydrogen atom or a fluorine atom, and Lⁱ¹ and Lⁱ² are more preferably hydrogen atoms or fluorine atoms. More specifically, A^ibf/t preferably represents any one of groups represented by formulae (A^ibf/t-1) to (A^ibf/t-10) below.

[Chem. 10]

In the formulae (A^ibf/t-1) to (A^ibf/t-10) , a white point represents a bond to Rⁱ¹, and a black point represents a bond to Zⁱ¹.

In the general formula (i) , Aⁱ¹ and Aⁱ² each independently represent any one of a hydrocarbon ring having 3 to 16 and a heterocyclic ring having 3 to 16 carbon atoms. The hydrocarbon ring having 3 to 16 or heterocyclic ring having 3 to 16 carbon atoms preferably represents a group selected from the group consisting of group (a) , group (b) , group (c) , and group (d) below,

(a) a 1, 4-cyclohexylene group (one -CH₂-or two or more non-adjacent -CH₂-present in the group may be substituted by -O-or -S-) ;

(b) a 1, 4-phenylene group (one -CH= or two or more non-adjacent -CH= present in the group may be substituted by -N=) ;

(c) a 1, 4-cyclohexenylene group, a bicyclo [2.2.2] octane-1, 4-diyl group, a naphthalene-2, 6-diyl group, a naphthalene-1, 4-diyl group, a 1, 2, 3, 4-tetrahydronaphthalene-2, 6-diyl group, a 5, 6, 7, 8-tetrahydronaphthalene-1, 4-diyl group, a decahydronaphthalene-2, 6-diyl group, an anthracene-2, 6-diyl group, an anthracene-1, 4-diyl group, an anthracene-9, 10-diyl group, and a phenanthrene-2, 7-diyl group (one -CH= or two or more -CH= present in a naphthalene-2, 6-diyk group, a naphthalene-1, 4-diyl group, a 1, 2, 3, 4-tetrahydronaphthalene-2, 6-diyl group, a 5, 6, 7, 8-tetrahydronaphthalene-1, 4-diyl group, an anthracene-2, 6-diyl group, an anthracene-1, 4-diyl group, an anthracene-9, 10-diyl group, or a phenanthrene-2, 7-diyl group may be substituted by -N=) ;

(d) a thiophene-2, 5-diyl group, a benzothiophene-2, 5-diyl group, a benzothiophene-2, 6-diyl group, a dibenzothiophene-3, 7-diyl group, a dibenzothiophene-2, 6-diyl group, and a thieno [3, 2-b] thiophene-2, 5-diyl group (one -CH= or two or more non-adjacent -CH= present in the group may be substituted by -N=) .

One or two or more hydrogen atoms in Aⁱ¹ and Aⁱ² may be each independently substituted by substituent Sⁱ¹. The substituent Sⁱ¹ represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms. The alkyl group is a linear, branched, or cyclic alkyl group and preferably a linear alkyl group. The number of carbon atoms in the alkyl group is preferably 2 to 10 or preferably 3 to 6. One or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-. One or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom. Examples of a halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted by a predetermined group, an oxygen atom and an oxygen atom are not directly bonded to each other. In addition, from the viewpoint of stability of the compound, a sulfur atom and a sulfur atom and/or an oxygen atom and a sulfur atom are preferably not directly bonded to each other. The substituent Sⁱ¹ is preferably a linear alkyl group having 1 to 10 carbon atoms, a chlorine atom, or a fluorine atom. At least one of Aⁱ¹ and Aⁱ² is preferably substituted by at least one substituent Sⁱ¹. In addition, Aⁱ² is preferably substituted by at least one substituent Sⁱ¹. When a plurality of substituents Sⁱ¹ are present, they may be the same or different.

The substitution position of the substituent Sⁱ¹ in Aⁱ¹ is preferably any one of formulae (Aⁱ¹-SP-1) to (Aⁱ¹-SP-4) below.

[Chem. 11]

In the formulae (Aⁱ¹-SP-1) to (Aⁱ¹-SP-4) , a white point represents a bond to Zⁱ¹, and a black point represents a bond to Zⁱ² or an isothiocyanate group (-NCS) . The substitution position of the substituent Sⁱ¹ in Aⁱ² is preferably any one of formulae (Aⁱ²-SP-1) to (Aⁱ²-SP-4) below.

[Chem. 12]

In the formulae (Aⁱ²-SP-1) to (Aⁱ²-SP-4) , a white point represents a bond to Zⁱ², and a black point represents a bond to Zⁱ² or an isothiocyanate group (-NCS) . More specifically, Aⁱ¹ is preferably any one of formulae (Aⁱ¹-1) to (Aⁱ¹-10) below.

[Chem. 13]

In the formulae (Aⁱ¹-1) to (Aⁱ¹-10) , a white point represents a bond to Zⁱ¹, and a black point represents a bond to Zⁱ² or an isothiocyanate group (-NCS) . More specifically, Aⁱ² is preferably any one of formulae (Aⁱ²-1) to (Aⁱ²-8) below.

[Chem. 14]

In the formulae (Aⁱ²-1) to (Aⁱ²-8) , a white point represents a bond to Zⁱ², and a black point represents a bond to Zⁱ² or an isothiocyanate group (-NCS) .

In the general formula (i) , Zⁱ¹and Zⁱ² each independently represent any one of a single bond and an alkylene group having 1 to 20 carbon atoms. The alkylene group is a linear, branched, or cyclic alkylene group and preferably a linear alkylene group. The number of carbon atoms in the alkylene group is preferably 2 to 10 or preferably 2 to 6. One or two or more -CH₂-in the alkylene group may be each independently substituted by -O-, -CF₂-, and/or, -CO-. One or two or more -CH₂-CH₂-in the alkylene group may be each 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-, and/or -C≡C-. However, when the alkylene group is substituted by a predetermined group, an oxygen atom and an oxygen atom is not directly bonded to each other. Specific examples (including substituted ones) of the alkylene group having 2 to 20 carbon atoms include groups represented by formulae (Z^i1/2-1) to (Z^i1/2-24) below.

[Chem. 15]

In the formulae (Z^i1/2-1) to (Z^i1/2-24) , a white point represents a bond to A^ibf/t, Aⁱ¹, or Aⁱ², and a black point represents a bond to Aⁱ¹ or Aⁱ². From the viewpoint of Δn, at least one of Zⁱ¹ and Zⁱ² is preferably -C=C-.

In the general formula (i) , nⁱ¹ present an integer of 0 to 3 and preferably an integer of 1 to 2. When a plurality of Aⁱ² or Zⁱ² are present, they may be the same or different.

The compound represented by the general formula (i) is preferably a compound selected from the group consisting of compounds represented by general formulae (i-1) to (i-6) below.

[Chem. 16]
Rⁱ¹-A^ibf/t-Aⁱ¹-NCS (i-1)

Rⁱ¹-A^ibf/t-Aⁱ¹-Aⁱ²-NCS (i-3)

In the general formulae (i-1) to (i-6) , Rⁱ¹, A^ibf/t, Aⁱ¹, and Aⁱ² represent the same meanings as Rⁱ¹, A^ibf/t, Aⁱ¹, and Aⁱ², respectively, in the general formula (i) .

The compound represented by the general formula (i-1) is preferably a compound represented by general formulae (i-1-1) to (i-1-4) below.

[Chem. 17]

In the general formulae (i-1-1) to (i-1-4) , Rⁱ¹ and Sⁱ¹ represent the same meanings as Rⁱ¹ and Sⁱ¹, respectively, in the general formula (i) , and preferred groups are the same as in the general formula (i) .

Specific examples of the compound represented by the general formula (i-1-1) include compounds represented by structural formulae (i-1-1.1) to (i-1-1.4) below.

[Chem. 18]

Specific examples of the compound represented by the general formula (i-1-2) include compounds represented by structural formulae (i-1-2.1) to (i-1-2.4) below.

[Chem. 19]

Specific examples of the compound represented by the general formula (i-1-3) include compounds represented by structural formulae (i-1-3.1) to (i-1-3.4) below.

[Chem. 20]

Specific examples of the compound represented by the general formula (i-1-4) include compounds represented by structural formulae (i-1-4.1) to (i-1-4.4) below.

[Chem. 21]

The compound represented by the general formula (i-2) is preferably a compound represented by general formulae (i-2-1) to (i-2-4) below.

[Chem. 22]

In the general formulae (i-2-1) to (i-2-4) , Rⁱ¹ and Sⁱ¹ represent the same meanings as Rⁱ¹ and Sⁱ¹, respectively, in the general formula (i) , and preferred groups are the same as in the general formula (i) . Specific examples of the compound represented by the general formula (i-2-1) include compounds represented by structural formulae (i-2-1.1) to (i-2-1.4) below.

[Chem. 23]

Specific examples of the compound represented by the general formula (i-2-2) include compounds represented by structural formulae (i-2-2.1) to (i-2-2.4) below.

[Chem. 24]

Specific examples of the compound represented by the general formula (i-2-3) include compounds represented by structural formulae (i-2-3.1) to (i-2-3.4) below.

[Chem. 25]

Specific examples of the compound represented by the general formula (i-2-4) include compounds represented by structural formulae (i-2-4.1) to (i-2-4.4) below.

[Chem. 26]

The compound represented by the general formula (i-3) is preferably a compound represented by general formulae (i-3-1) to (i-3-2) below.

[Chem. 27]

In the general formulae (i-3-1) to (i-3-2) , Rⁱ¹ and Sⁱ¹ represent the same meanings as Rⁱ¹ and Sⁱ¹, respectively, in the general formula (i) , and preferred groups are the same as in the general formula (i) . Specific examples of the compound represented by the general formula (i-3-1) include compounds represented by structural formulae (i-3-1.1) to (i-3-1.4) below.

[Chem. 28]

Specific examples of the compound represented by the general formula (i-3-2) include compounds represented by structural formulae (i-3-2.1) to (i-3-2.4) below.

[Chem. 29]

The compound represented by the general formula (i-4) is preferably a compound represented by general formulae (i-4-1) to (i-4-9) below.

[Chem. 30]

[Chem. 31]

In the general formulae (i-4-1) to (i-4-9) , Rⁱ¹, Lⁱ¹, and Sⁱ¹ represent the same meanings as Rⁱ¹, Lⁱ¹, and Sⁱ¹, respectively, in the general formula (i) , and preferred groups are the same as in the general formula (i) . Specific examples of the compound represented by the general formula (i-4-1) include compounds represented by structural formulae (i-4-1.1) to (i-4-1.4) below.

[Chem. 32]

Specific examples of the compound represented by the general formula (i-4-2) include compounds represented by structural formulae (i-4-2.1) to (i-4-2.4) below.

[Chem. 33]

Specific examples of the compound represented by the general formula (i-4-3) include compounds represented by structural formulae (i-4-3.1) to (i-4-3.4) below.

[Chem. 34]

Specific examples of the compound represented by the general formula (i-4-4) include compounds represented by structural formulae (i-4-4.1) to (i-4-4.4) below.

[Chem. 35]

Specific examples of the compound represented by the general formula (i-4-5) include compounds represented by structural formulae (i-4-5.1) and (i-4-5.2) below.

[Chem. 36]

Specific examples of the compound represented by the general formula (i-4-6) include compounds represented by structural formulae (i-4-6.1) and (i-4-6.2) below.

[Chem. 37]

Specific examples of the compound represented by the general formula (i-4-7) include compounds represented by structural formulae (i-4-7.1) and (i-4-7.2) below.

[Chem. 38]

Specific examples of the compound represented by the general formula (i-4-8) include compounds represented by structural formulae (i-4-8.1) and (i-4-8.2) below.

[Chem. 39]

Specific examples of the compound represented by the general formula (i-4-9) include compounds represented by structural formulae (i-4-9.1) and (i-4-9.2) below.

[Chem. 40]

The compound represented by the general formula (i-5) is preferably a compound represented by general formulae (i-5-1) to (i-5-12) below.

[Chem. 41]

[Chem. 42]

In the general formulae (i-5-1) to (i-5-12) , Rⁱ¹ and Sⁱ¹ represent the same meanings as Rⁱ¹ and Sⁱ¹, respectively, in the general formula (i) , and preferred groups are the same as in the general formula (i) . Specific examples of the compound represented by the general formula (i-5-1) include compounds represented by structural formulae (i-5-1.1) and (i-5-1.2) below.

[Chem. 43]

Specific examples of the compound represented by the general formula (i-5-2) include compounds represented by structural formulae (i-5-2.1) and (i-5-2.2) below.

[Chem. 44]

Specific examples of the compound represented by the general formula (i-5-3) include compounds represented by structural formulae (i-5-3.1) and (i-5-3.2) below.

[Chem. 45]

Specific examples of the compound represented by the general formula (i-5-4) include compounds represented by structural formulae (i-5-4.1) and (i-5-4.2) below.

[Chem. 46]

Specific examples of the compound represented by the general formula (i-5-5) include compounds represented by structural formulae (i-5-5.1) to (i-5-5.3) below.

[Chem. 47]

Specific examples of the compound represented by the general formula (i-5-6) include compounds represented by structural formulae (i-5-6.1) and (i-5-6.2) below.

[Chem. 48]

Specific examples of the compound represented by the general formula (i-5-7) include compounds represented by structural formulae (i-5-7.1) and (i-5-7.2) below.

[Chem. 49]

Specific examples of the compound represented by the general formula (i-5-8) include compounds represented by structural formulae (i-5-8.1) and (i-5-8.2) below.

[Chem. 50]

Specific examples of the compound represented by the general formula (i-5-9) include compounds represented by structural formulae (i-5-9.1) and (i-5-9.2) below.

[Chem. 51]

Specific examples of the compound represented by the general formula (i-5-10) include compounds represented by structural formulae (i-5-10.1) and (i-5-10.2) below.

[Chem. 52]

Specific examples of the compound represented by the general formula (i-5-11) include compounds represented by structural formulae (i-5-11.1) and (i-5-11.2) below.

[Chem. 53]

Specific examples of the compound represented by the general formula (i-5-12) include compounds represented by structural formulae (i-5-12.1) and (i-5-12.2) below.

[Chem. 54]

The compound represented by the general formula (i-6) is preferably a compound represented by general formulae (i-6-1) to (i-6-12) below.

[Chem. 55]

[Chem. 56]

In the general formulae (i-6-1) to (i-6-12) , Rⁱ¹ and Sⁱ¹ represent the same meanings as Rⁱ¹ and Sⁱ¹, respectively, in the general formula (i) , and preferred groups are the same as in the general formula (i) . Specific examples of the compound represented by the general formula (i-6-1) include compounds represented by structural formulae (i-6-1.1) to (i-6-1.4) below.

[Chem. 57]

Specific examples of the compound represented by the general formula (i-6-2) include compounds represented by structural formulae (i-6-2.1) to (i-6-2.5) below.

[Chem. 58]

[Chem. 59]

Specific examples of the compound represented by the general formula (i-6-3) include compounds represented by structural formulae (i-6-3.1) to (i-6-3.4) below.

[Chem. 60]

Specific examples of the compound represented by the general formula (i-6-4) include compounds represented by structural formulae (i-6-4.1) to (i-6-4.4) below.

[Chem. 61]

Specific examples of the compound represented by the general formula (i-6-5) include compounds represented by structural formulae (i-6-5.1) to (i-6-5.5) below.

[Chem. 62]

[Chem. 63]

Specific examples of the compound represented by the general formula (i-6-6) include compounds represented by structural formulae (i-6-6.1) to (i-6-6.4) below.

[Chem. 64]

Specific examples of the compound represented by the general formula (i-6-7) include compounds represented by structural formulae (i-6-7.1) to (i-6-7.4) below.

[Chem. 65]

Specific examples of the compound represented by the general formula (i-6-8) include compounds represented by structural formulae (i-6-8.1) to (i-6-8.4) below.

[Chem. 66]

Specific examples of the compound represented by the general formula (i-6-9) include compounds represented by structural formulae (i-6-9.1) to (i-6-9.4) below.

[Chem. 67]

Specific examples of the compound represented by the general formula (i-6-10) include compounds represented by structural formulae (i-6-10.1) to (i-6-10.4) below.

[Chem. 68]

Specific examples of the compound represented by the general formula (i-6-11) include compounds represented by structural formulae (i-6-11.1) to (i-6-11.4) below.

[Chem. 69]

Specific examples of the compound represented by the general formula (i-6-12) include compounds represented by structural formulae (i-6-12.1) to (i-6-12.4) below.

[Chem. 70]

The liquid crystal composition uses one or two or more, preferably one to ten, preferably one to five, or preferably one to three of the compounds represented by the general formula (i) , the general formulae (i-1) to (i-6) , the general formulae (i-1-1) to (i-1-4) , the general formulae (i-2-1) to (i-2-4) , the general formulae (i-3-1) to (i-3-2) , the general formulae (i-4-1) to (i-4-9) , the general formulae (i-5-1) to (i-5-12) , the general formulae (i-6-1) to (i-6-12) , the structural formulae (i-1-1.1) to (i-1-1.4) , the structural formulae (i-1-2.1) to (i-1-2.4) , the structural formulae (i-1-3.1) to (i-1-3.4) , the structural formulae (i-1-4.1) to (i-1-4.4) , the structural formulae (i-2-1.1) to (i-2-1.4) , the structural formulae (i-2-2.1) to (i-2-2.4) , the structural formulae (i-2-3.1) to (i-2-3.4) , the structural formulae (i-2-4.1) to (i-2-4.4) , the structural formulae (i-3-1.1) to (i-3-1.4) , the structural formulae (i-3-2.1) to (i-3-2.4) , the structural formulae (i-4-1.1) to (i-4-1.4) , the structural formulae (i-4-2.1) to (i-4-2.4) , the structural formulae (i-4-3.1) to (i-4-3.4) , the structural formulae (i-4-4.1) to (i-4-4.4) , the structural formulae (i-4-5.1) to (i-4-5.2) , the structural formulae (i-4-6.1) to (i-4-6.2) , the structural formulae (i-4-7.1) to (i-4-7.2) , the structural formulae (i-4-8.1) to (i-4-8.2) , the structural formulae (i-4-9.1) to (i-4-9.2) , the structural formulae (i-5-1.1) to (i-5-1.2) , the structural formulae (i-5-2.1) to (i-5-2.2) , the structural formulae (i-5-3.1) to (i-5-3.2) , the structural formulae (i-5-4.1) to (i-5-4.2) , the structural formulae (i-5-5.1) to (i-5-5.3) , the structural formulae (i-5-6.1) to (i-5-6.2) , the structural formulae (i-5-7.1) to (i-5-7.2) , the structural formulae (i-5-8.1) to (i-5-8.2) , the structural formulae (i-5-9.1) to (i-5-9.2) , the structural formulae (i-5-10.1) to (i-5-10.2) , the structural formulae (i-5-11.1) to (i-5-11.2) , the structural formulae (i-5-12.1) to (i-5-12.2) , the structural formulae (i-6-1.1) to (i-6-1.4) , the structural formulae (i-6-2.1) to (i-6-2.5) , the structural formulae (i-6-3.1) to (i-6-3.4) , the structural formulae (i-6-4.1) to (i-6-4.4) , the structural formulae (i-6-5.1) to (i-6-5.5) , the structural formulae (i-6-6.1) to (i-6-6.4) , the structural formulae (i-6-7.1) to (i-6-7.4) , the structural formulae (i-6-8.1) to (i-6-8.4) , the structural formulae (i-6-9.1) to (i-6-9.4) , the structural formulae (i-6-10.1) to (i-6-10.4) , the structural formulae (i-6-11.1) to (i-6-11.4) , or the structural formulae (i-6-12.1) to (i-6-12.4) .

With respect to compounds represented by the general formula (i) , the general formulae (i-1) to (i-6) , the general formulae (i-1-1) to (i-1-4) , the general formulae (i-2-1) to (i-2-4) , the general formulae (i-3-1) to (i-3-2) , the general formulae (i-4-1) to (i-4-9) , the general formulae (i-5-1) to (i-5-12) , the general formulae (i-6-1) to (i-6-12) , the structural formulae (i-1-1.1) to (i-1-1.4) , the structural formulae (i-1-2.1) to (i-1-2.4) , the structural formulae (i-1-3.1) to (i-1-3.4) , the structural formulae (i-1-4.1) to (i-1-4.4) , the structural formulae (i-2-1.1) to (i-2-1.4) , the structural formulae (i-2-2.1) to (i-2-2.4) , the structural formulae (i-2-3.1) to (i-2-3.4) , the structural formulae (i-2-4.1) to (i-2-4.4) , the structural formulae (i-3-1.1) to (i-3-1.4) , the structural formulae (i-3-2.1) to (i-3-2.4) , the structural formulae (i-4-1.1) to (i-4-1.4) , the structural formulae (i-4-2.1) to (i-4-2.4) , the structural formulae (i-4-3.1) to (i-4-3.4) , the structural formulae (i-4-4.1) to (i-4-4.4) , the structural formulae (i-4-5.1) to (i-4-5.2) , the structural formulae (i-4-6.1) to (i-4-6.2) , the structural formulae (i-4-7.1) to (i-4-7.2) , the structural formulae (i-4-8.1) to (i-4-8.2) , the structural formulae (i-4-9.1) to (i-4-9.2) , the structural formulae (i-5-1.1) to (i-5-1.2) , the structural formulae (i-5-2.1) to (i-5-2.2) , the structural formulae (i-5-3.1) to (i-5-3.2) , the structural formulae (i-5-4.1) to (i-5-4.2) , the structural formulae (i-5-5.1) to (i-5-5.3) , the structural formulae (i-5-6.1) to (i-5-6.2) , the structural formulae (i-5-7.1) to (i-5-7.2) , the structural formulae (i-5-8.1) to (i-5-8.2) , the structural formulae (i-5-9.1) to (i-5-9.2) , the structural formulae (i-5-10.1) to (i-5-10.2) , the structural formulae (i-5-11.1) to (i-5-11.2) , the structural formulae (i-5-12.1) to (i-5-12.2) , the structural formulae (i-6-1.1) to (i-6-1.4) , the structural formulae (i-6-2.1) to (i-6-2.5) , the structural formulae (i-6-3.1) to (i-6-3.4) , the structural formulae (i-6-4.1) to (i-6-4.4) , the structural formulae (i-6-5.1) to (i-6-5.5) , the structural formulae (i-6-6.1) to (i-6-6.4) , the structural formulae (i-6-7.1) to (i-6-7.4) , the structural formulae (i-6-8.1) to (i-6-8.4) , the structural formulae (i-6-9.1) to (i-6-9.4) , the structural formulae (i-6-10.1) to (i-6-10.4) , the structural formulae (i-6-11.1) to (i-6-11.4) , or the structural formulae (i-6-12.1) to (i-6-12.4) , the lower limit of the total content is preferably 0.1%by mass or more, preferably 0.5%by mass or more, or preferably 1% by mass or more relative to 100%by mass of the liquid crystal composition.

With respect to compounds represented by the general formula (i) , the general formulae (i-1) to (i-6) , the general formulae (i-1-1) to (i-1-4) , the general formulae (i-2-1) to (i-2-4) , the general formulae (i-3-1) to (i-3-2) , the general formulae (i-4-1) to (i-4-9) , the general formulae (i-5-1) to (i-5-12) , the general formulae (i-6-1) to (i-6-12) , the structural formulae (i-1-1.1) to (i-1-1.4) , the structural formulae (i-1-2.1) to (i-1-2.4) , the structural formulae (i-1-3.1) to (i-1-3.4) , the structural formulae (i-1-4.1) to (i-1-4.4) , the structural formulae (i-2-1.1) to (i-2-1.4) , the structural formulae (i-2-2.1) to (i-2-2.4) , the structural formulae (i-2-3.1) to (i-2-3.4) , the structural formulae (i-2-4.1) to (i-2-4.4) , the structural formulae (i-3-1.1) to (i-3-1.4) , the structural formulae (i-3-2.1) to (i-3-2.4) , the structural formulae (i-4-1.1) to (i-4-1.4) , the structural formulae (i-4-2.1) to (i-4-2.4) , the structural formulae (i-4-3.1) to (i-4-3.4) , the structural formulae (i-4-4.1) to (i-4-4.4) , the structural formulae (i-4-5.1) to (i-4-5.2) , the structural formulae (i-4-6.1) to (i-4-6.2) , the structural formulae (i-4-7.1) to (i-4-7.2) , the structural formulae (i-4-8.1) to (i-4-8.2) , the structural formulae (i-4-9.1) to (i-4-9.2) , the structural formulae (i-5-1.1) to (i-5-1.2) , the structural formulae (i-5-2.1) to (i-5-2.2) , the structural formulae (i-5-3.1) to (i-5-3.2) , the structural formulae (i-5-4.1) to (i-5-4.2) , the structural formulae (i-5-5.1) to (i-5-5.3) , the structural formulae (i-5-6.1) to (i-5-6.2) , the structural formulae (i-5-7.1) to (i-5-7.2) , the structural formulae (i-5-8.1) to (i-5-8.2) , the structural formulae (i-5-9.1) to (i-5-9.2) , the structural formulae (i-5-10.1) to (i-5-10.2) , the structural formulae (i-5-11.1) to (i-5-11.2) , the structural formulae (i-5-12.1) to (i-5-12.2) , the structural formulae (i-6-1.1) to (i-6-1.4) , the structural formulae (i-6-2.1) to (i-6-2.5) , the structural formulae (i-6-3.1) to (i-6-3.4) , the structural formulae (i-6-4.1) to (i-6-4.4) , the structural formulae (i-6-5.1) to (i-6-5.5) , the structural formulae (i-6-6.1) to (i-6-6.4) , the structural formulae (i-6-7.1) to (i-6-7.4) , the structural formulae (i-6-8.1) to (i-6-8.4) , the structural formulae (i-6-9.1) to (i-6-9.4) , the structural formulae (i-6-10.1) to (i-6-10.4) , the structural formulae (i-6-11.1) to (i-6-11.4) , or the structural formulae (i-6-12.1) to (i-6-12.4) , the upper limit of the total content of is preferably 95%by mass or less, preferably 90%by mass or less, preferably 85%by mass or less, 30%by mass or less, or 20%by mass or less relative to 100%by mass of the liquid crystal composition.

With respect to compounds represented by the general formula (i) , the general formulae (i-1) to (i-6) , the general formulae (i-1-1) to (i-1-4) , the general formulae (i-2-1) to (i-2-4) , the general formulae (i-3-1) to (i-3-2) , the general formulae (i-4-1) to (i-4-9) , the general formulae (i-5-1) to (i-5-12) , the general formulae (i-6-1) to (i-6-12) , the structural formulae (i-1-1.1) to (i-1-1.4) , the structural formulae (i-1-2.1) to (i-1-2.4) , the structural formulae (i-1-3.1) to (i-1-3.4) , the structural formulae (i-1-4.1) to (i-1-4.4) , the structural formulae (i-2-1.1) to (i-2-1.4) , the structural formulae (i-2-2.1) to (i-2-2.4) , the structural formulae (i-2-3.1) to (i-2-3.4) , the structural formulae (i-2-4.1) to (i-2-4.4) , the structural formulae (i-3-1.1) to (i-3-1.4) , the structural formulae (i-3-2.1) to (i-3-2.4) , the structural formulae (i-4-1.1) to (i-4-1.4) , the structural formulae (i-4-2.1) to (i-4-2.4) , the structural formulae (i-4-3.1) to (i-4-3.4) , the structural formulae (i-4-4.1) to (i-4-4.4) , the structural formulae (i-4-5.1) to (i-4-5.2) , the structural formulae (i-4-6.1) to (i-4-6.2) , the structural formulae (i-4-7.1) to (i-4-7.2) , the structural formulae (i-4-8.1) to (i-4-8.2) , the structural formulae (i-4-9.1) to (i-4-9.2) , the structural formulae (i-5-1.1) to (i-5-1.2) , the structural formulae (i-5-2.1) to (i-5-2.2) , the structural formulae (i-5-3.1) to (i-5-3.2) , the structural formulae (i-5-4.1) to (i-5-4.2) , the structural formulae (i-5-5.1) to (i-5-5.3) , the structural formulae (i-5-6.1) to (i-5-6.2) , the structural formulae (i-5-7.1) to (i-5-7.2) , the structural formulae (i-5-8.1) to (i-5-8.2) , the structural formulae (i-5-9.1) to (i-5-9.2) , the structural formulae (i-5-10.1) to (i-5-10.2) , the structural formulae (i-5-11.1) to (i-5-11.2) , the structural formulae (i-5-12.1) to (i-5-12.2) , the structural formulae (i-6-1.1) to (i-6-1.4) , the structural formulae (i-6-2.1) to (i-6-2.5) , the structural formulae (i-6-3.1) to (i-6-3.4) , the structural formulae (i-6-4.1) to (i-6-4.4) , the structural formulae (i-6-5.1) to (i-6-5.5) , the structural formulae (i-6-6.1) to (i-6-6.4) , the structural formulae (i-6-7.1) to (i-6-7.4) , the structural formulae (i-6-8.1) to (i-6-8.4) , the structural formulae (i-6-9.1) to (i-6-9.4) , the structural formulae (i-6-10.1) to (i-6-10.4) , the structural formulae (i-6-11.1) to (i-6-11.4) , or the structural formulae (i-6-12.1) to (i-6-12.4) , from the viewpoint of solubility, Δn, and Δε_r, the total content of is preferably 0.1%to 95%by mass, preferably 0.5%to 90%by mass, preferably 1%to 85%by mass, 1%to 30%by mass, or 1%to 20%by mass relative to 100%by mass of the liquid crystal composition.

The compound (including more specific concepts ) represented by the general formula (i) can be synthesized by using a known synthesis method, and some examples thereof are described below.

(Production method 1: Production of compound represented by formula (s-3) below)

[Chem. 71]

In general formulae (s-1) to (s-3) , Rⁱ¹, Aⁱ¹, and Lⁱ¹ represent the same meanings as Rⁱ¹, Aⁱ¹, and Lⁱ¹, respectively, in the general formula (i) . First, a compound represented by the general formula (s-3) can be obtained as an object compound by reacting a compound represented by the general formula (s-1) with a compound represented by the general formula (s-2) . The reaction method is, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base, or the like. Examples of the palladium catalyst include [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, palladium (II) acetate, dichlorobis [di-tert-butyl (p-dimethylaminophenyl) phosphino] palladium (II) , dichlorobis (triphenylphosphine) palladium (II) , tetrakis (triphenylphosphine) palladium (0) , and the like. When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine, 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl, or the like may be added. Examples of the copper catalyst include copper (I) iodide. Examples of the base include triethylamine and the like.

(Production method 2: Production of compound represented by formula (s-7) below)

[Chem. 72]

In general formulae (s-4) to (s-7) , Rⁱ¹, Aⁱ¹, and Lⁱ¹ represent the same meanings as Rⁱ¹, Aⁱ¹, and Lⁱ¹, respectively, in the general formula (i) . A compound represented by the general formula (s-5) is obtained by reacting a compound represented by the general formula (s-4) with bispinacol diborane, and then a compound represented by the general formula (s-7) can be obtained by reaction with a compound represented by the general formula (s-6) . The reaction method is, for example, Suzuki coupling reaction using a palladium catalyst and a base, or the like. Examples of the palladium catalyst include [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, palladium (II) acetate, dichlorobis [di-tert-butyl (p-dimethylaminophenyl) phosphino] palladium (II) , dichlorobis (triphenylphosphine) palladium (II) , tetrakis (triphenylphosphine) palladium (0) , and the like. Examples of the base include potassium carbonate, sodium carbonate, potassium phosphate, and the like.

(Production method 3: Production of compound represented by formula (s-12) below)

[Chem. 73]

In general formulae (s-8) to (s-12) , Rⁱ¹, Aⁱ¹, Lⁱ¹, and Sⁱ¹ represent the same meanings as Rⁱ¹, Aⁱ¹, Lⁱ¹, and Sⁱ¹. respectively, in the general formula (i) . A compound represented by the general formula (s-10) can be obtained by reacting a compound represented by the general formula (s-8) with a compound represented by the general formula (s-9) . The reaction method is, for example, Suzuki coupling reaction using a palladium catalyst and a base, or the like. Examples of the palladium catalyst include [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, palladium (II) acetate, dichlorobis [di-tert-butyl (p-dimethylaminophenyl) phosphino] palladium (II) , dichlorobis (triphenylphosphine) palladium (II) , tetrakis (triphenylphosphine) palladium (0) , and the like. Examples of the base include potassium carbonate, sodium carbonate, potassium phosphate, and the like. Next, a compound represented by the general formula (s-12) can be obtained by reacting the compound represented by the general formula (s-10) with a compound represented by the general formula (s-11) . The reaction method is, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and base, or the like. Examples of the palladium catalyst include [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, palladium (II) acetate, dichlorobis [di-tert-butyl (p-dimethylaminophenyl) phosphino] palladium (II) , dichlorobis (triphenylphosphine) palladium (II) , tetrakis (triphenylphosphine) palladium (0) , and the like. When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine, 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl, or the like may be added. Examples of the copper catalyst include copper (I) iodide. Examples of the base include triethylamine and the like.

(Production method 4: Production of compound represented by formula (s-18) below)

[Chem. 74]

In general formulae (s-13) to (s-18) , Rⁱ¹, Aⁱ², Lⁱ¹, and Sⁱ¹ represent the same meanings as Rⁱ¹, Aⁱ², Lⁱ¹, and Sⁱ¹, respectively, in the general formula (i) . A compound represented by the general formula (s-14) can be obtained by reacting a compound represented by the general formula (s-13) with trimethylsilylacetylene and then reacting with potassium carbonate in methanol. The reaction method is, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base, or the like. Examples of the palladium catalyst include [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, palladium (II) acetate, dichlorobis [di-tert-butyl (p-dimethylaminophenyl) phosphino] palladium (II) , dichlorobis (triphenylphosphine) palladium (II) , tetrakis (triphenylphosphine) palladium (0) , and the like. When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine, 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl, or the like may be added. Examples of the copper catalyst include copper (I) iodide. Examples of the base include triethylamine and the like. Further, a compound represented by the general formula (s-16) can be obtained by reacting the compound represented by the general formula (s-14) with a compound represented by the general formula (s-15) . The reaction method is, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base, or the like. Next, a compound represented by the general formula (s-18) as an object compound can be obtained by reacting the compound represented by the general formula (s-16) with a compound represented by the general formula (s-17) . The reaction method is, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base, or the like.

Examples of reaction conditions other than those described in each of the steps include those described in Experimental Chemistry (edited by the Chemical Society of Japan, issued by Maruzen Co., Ltd. ) , documents such as Organic Syntheses (AJohn Wiley &Sons, Inc., Publication) , Beilstein Handbook of Organic Chemistry (Beilstein-Institut fuer Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH &Co. K) , Fiesers'Reagents for Organic Synthesis (John Wiley &Sons, Inc. ) , and the like; and those included in database of SciFinder (Chemical Abstracts Service, American Chemical Society) , Reaxys (Elsevier Ltd. ) , and the like. When oxygen and/or a material unstable to water is handled in each of the steps, the operation is preferably performed in inert gas such as nitrogen gas, argon gas, or the like. If required, a functional group can be protected in each of the steps. Examples of the protective group include protective groups described in GREENE'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS ( (Fourth Edition) , co-written by PETER G. M. WUTS, and THEODORA W. GREENE, A John Wiley &Sons, Inc., Publication) , and the like. If required, purification may be performed in each of the steps. Examples of a purification method include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, liquid separation treatment, and the like. Specific examples of a purifying agent include silica gel, alumina, activated carbon, and the like.

The characteristic values of the compound (including more specific concepts) represented by the general formula (i) can be measured as follows. First, the compound (including more specific concepts) represented by the general formula (i) is added to a mother liquid crystal to prepare a liquid crystal composition containing each of 0%by mass, 5%by mass, and 10%by mass of the compound represented by the general formula (i) in 100%by mass of the liquid crystal composition, and Δn (refractive index anisotropy) and Δε_r of each of the liquid crystal compositions are measured. Then, Δn (refractive index anisotropy) and Δε_r of 100%by mass of the compound (including more specific concepts) represented by the general formula (i) , that is, the compound represented by the general formula (i) , are determined from extrapolation values using a least square method.

Δn (refractive index anisotropy) correlates with Δn in the near-infrared region used in an optical sensor described later. The light phase modulation force at an objective wavelength increases with increasing Δn, and thus larger Δn is particularly suitable for optical sensors. Δn at 25℃ and 589 nm is determined from a difference (n_e -n_o) between the extraordinary refractive index (n_e) and ordinary refractive index (n_o) of the liquid crystal composition by using an Abbe refractometer. Also, Δn can be determined by a phase difference measuring apparatus. The relation Δn = Re/d is established between the phase difference Re, thickness d of a liquid crystal layer, and Δn. The liquid crystal composition is injected into a glass cell which has a cell gap (d) of about 3.0 μm and a polyimide alignment film treated by antiparallel rubbing, and in-plane Re is measured by retardation film/optical material inspection device RETS-100 (manufactured by Otsuka Electronics Co., Ltd. ) . The measurement is performed under the conditions including a temperature of 25℃ and 589 nm and has no unit. From the viewpoint of the light phase modulation force at the wavelength, Δn of the compound at 25℃ and 589 nm of the compound (including more specific concepts) represented by the general formula (i) according to the present invention is preferably 0.35 or more, preferably 0.40 to 0.60, preferably 0.43 to 0.57, or preferably 0.45 to 0.55.

The phase modulation force to radio waves in the objective frequency band increases with increasing dielectric anisotropy in a high frequency region, and thus high dielectric anisotropy is particularly suitable for antenna application. In addition, in antenna application, the energy loss in the objective frequency band desirably decreases with decreasing dielectric loss tangent in a high frequency region. With respect to the compound (including more specific concepts) represented by the general formula (i) according to the present invention, dielectric anisotropy Δε_r at 10 GHz was measured as a representative of the characteristics in a high frequency region.

Δε_r = (ε_r//-ε_r⊥)

In this formula, "ε_r" is the dielectric constant, and the suffix "//" represents a component in the direction parallel to the liquid crystal alignment direction, and "⊥" represents a component in the direction perpendicular to the liquid crystal alignment direction.

Δε_r can be measured by the following method. First, the liquid crystal composition is introduced into a capillary made of polytetrafluoroethylene (PTFE) . The capillary used has an internal radius of 0.80 mm, an external radius of 0.835 mm, and an effective length of 4.0 cm. The capillary in which the liquid crystal composition is sealed is introduced into a center of a cavity resonator (manufactured by EM Labo Co., Ltd. ) having a resonance frequency of 10 GHz. The cavity resonator has an outer shape having a diameter of 30 mm and a width of 26 mm. Then, a signal is input, and the result of output signal is recorded by using a network analyzer (manufactured by Keysight Technologies Inc. ) . The dielectric constant (ε_r) at 10 GHz is determined by using a difference between the resonance frequency or the like of the PTFE capillary not having the liquid crystal composition sealed therein and the resonance frequency or the like of the PTFE capillary having the liquid crystal composition sealed therein. The resonance frequency or the like using the PTFE capillary having the liquid crystal composition sealed therein is determined as a value of a characteristic component perpendicular to the alignment direction of liquid crystal molecules and a value of a characteristic component parallel to the alignment direction by controlling the alignment of liquid crystal molecules. In addition, the magnetic field of a permanent magnet or an electromagnet is used for aligning liquid crystal molecules in the perpendicular direction (perpendicular to the effective length direction) of the PTFE capillary and aligning liquid crystal molecules in the parallel direction (parallel to the effective length direction) . The magnetic field has, for example. a magnetic pole distance of 45 mm and a magnetic field strength of 0.23 Tesla near the center. Desired characteristic components are obtained by rotating the PTFE capillary having the liquid crystal composition sealed therein parallel or perpendicularly to the magnetic field. The measurement is performed at a temperature of 25℃, and Δε_r has no unit.

Δε_r at 25℃ of the compound (including more specific concepts) represented by the general formula (i) according to the present invention is preferably larger, but from the viewpoint of phase modulation force in the GHz band, Δε_r is preferably 0.30 or more, preferably 0.30 to 0.65, preferably 0.31 to 0.60, preferably 0.32 to 0.55, preferably 0.33 to 0.50, preferably 0.34 to 0.45, or preferably 0.35 to 0.40.

(Liquid crystal composition)

The liquid crystal composition according to the present invention can be produced by, for example. mixing the compound (including more specific concepts) represented by the general formula (i) and, if required, other liquid crystal compounds and additives.

Examples of additives include a stabilizer, a pigment compound, a polymerizable compound, an azotolane compound, and the like.

Examples of the stabilizer include hydroquinones, hydroquinone monoalkyl ethers, tertiary butyl catechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, hindered amines, and the like. Examples of hindered phenols include hindered phenol-based antioxidants represented by structural formulae (XX-1) to (XX-3) below and the like.

[Chem. 75]

Examples of hindered amines include hindered amine-based photostabilizers represented by structural formulae (YY-1) to (YY-2) below and the like.

[Chem. 76]

When the stabilizer is used, the number of types of stabilizers used in the liquid crystal composition is preferably 1 or 2 or more, preferably 1 to 10, preferably 1 to 8, preferably 1 to 6, preferably 1 to 4, or preferably 1 to 2. When the stabilizer is used, the total content of the stabilizer in 100%by mass of the liquid crystal composition is preferably 0.005%to 1%by mass, preferably 0.02%to 0.50%by mass, or preferably 0.03%to 0.35%by mass.

(Liquid crystal display device, sensor, liquid crystal lens, optical communication device, and antenna)

Described below are a liquid crystal display device, sensor, liquid crystal lens, optical communication device, and antenna each using the liquid crystal composition according to the present invention.

A liquid crystal display device according to the present invention is characterized by using the liquid crystal composition described above and is preferably driven by an active matrix system or a passive matrix system. Also, the liquid crystal display device according to the present invention is preferably a liquid crystal display device in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of liquid crystal molecules of the liquid crystal composition.

A sensor according to the present invention is characterized by using the liquid crystal composition described above, and examples of the form thereof include a ranging sensor using electromagnetic waves, visible light, or infrared light, an infrared sensor using a temperature change, a temperature sensor using a change in reflected light wavelength with a pitch change of a cholesteric liquid crystal, a pressure sensor using a change in reflected light wavelength, an ultraviolet sensor using a change in reflected light wavelength with a change in composition, an electric sensor using a temperature change with a voltage or a current, a radiation sensor using a temperature change in association with the track of radiation particles, an ultrasonic sensor using an arrangement change of liquid crystal molecules with mechanical vibration of ultrasonic waves, an electromagnetic field sensor using a change in reflected light wavelength with a temperature3 change or an arrangement change of liquid crystal molecules by an electric field, and the like. The ranging sensor is preferably used for LiDAR (Light Detection And Ranging) using a light source. LiDAR is preferably used for an artificial satellite, an aircraft, an uninhabited aircraft (drone) , an automobile, a railroad, or a ship. Automobile use is particularly preferably use for an autonomous driving automobile. The light source is preferably LED or a laser or preferably a laser. The light used in LiDAR is preferably infrared light and preferably has a wavelength of 800 to 2000 nm. In particular, an infrared laser having a wavelength of 905 nm or 1550 nm is preferred. When the cost of the photodetector used and the sensitivity in all weathers are considered to be important, an infrared laser with 905 nm is preferred, while when human visual safety is considered to be important, an infrared layer with 1550 nm is preferred. The liquid crystal composition according to the present invention shows high Δn and thus can provide a sensor having large phase modulation force in the visible light, infrared light, and electromagnetic wave regions and excellent detection sensitivity.

A liquid crystal lens according to the present invention is characterized by using the liquid crystal composition described above, and an example of the form thereof has a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer provided between the first transparent electrode layer and the second transparent electrode layer and containing the liquid crystal composition described above, an insulating layer provided between the second transparent electrode layer and the liquid crystal layer, and a high-resistance layer provided between the insulating layer and the liquid crystal layer. The liquid crystal lens according to the present invention is used for, for example, a 2D-3D switchable lens, a lens for camera focus adjustment, and the like.

An optical communication device according to the present invention is characterized by using the liquid crystal composition described above, and an example of the form thereof is LCOS (Liquid crystal on silicon) including a liquid crystal layer disposed on a reflective layer (electrode) and having a two-dimensionally arranged liquid crystal constituting each of a plurality of pixels. The optical communication device according to the present invention is used as, for example, a special phase modulator.

An antenna according to the present invention is characterized by using the liquid crystal composition described above. More specifically, the antenna according to the present invention includes a first substrate provided with a plurality of slots, a second substrate facing the first substrate and being provided with a power supply portion, a first dielectric layer provided between the first substrate and the second substrate, a plurality of patch electrodes disposed 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, the liquid crystal layer containing the liquid crystal composition described above. When a liquid crystal composition containing one or two or more compounds (including more specific concepts) represented by the general formula (i) having a benzofuran structure or a benzothiophene structure and a thioisocyanate group (-NCS) is used as the liquid crystal composition, an antenna having high reliability to external stimuli such as heat and the like can be provided because of large Δn, large Δε_r, and good storage property at a low temperature. Therefore, an antenna enabling larger phase control for electromagnetic waves of micro waves or milli waves can be provided. The antenna according to the present invention is preferably operated with a Ka-band frequency, K-band frequency, or Ku-band frequency used for satellite communication. The antenna according to the present invention is preferably configured by a combination of a radial line slot array and a patch antenna array. For example, the items and the like described in International Publication No. 2021/157189 pamphlet or the like are taken into consideration for a structure which can be applied to the antenna according to the present invention.

[EXAMPLES]

The present invention is further described by giving examples, but the present invention is not limited to these examples. A composition of each of the examples and comparative examples contains each compound at a ratio shown in a table, and the content is represented by "%by mass" . A compound which can take a cis isomer and a trans isomer is described as the trans isomer unless otherwise specified.

(EXAMPLE 1: Production of compound represented by formula (I-1) )

[Chem. 77]

In a nitrogen atmosphere in a reactor, 110 mL of a 1 mol/L tetrahydrofuran (THF) solution of lithium isopropylamide (LDA) was charged and cooled to -60℃ or less, and a solution prepared by dissolving 20 g of a compound represented by formula (I-1-1) in 30 mL of THF was slowly dropped. After the composition of dropping, the resultant mixture was stirred at -60℃ or less for 1 hour and then reacted at 0℃ for 1 hour. Next, the reactor was cooled to -78℃, and then a solution prepared by dissolving 17 g of 1-iodopropane in 20 mL of THF was slowly dropped. After the completion of dropping, the mixture was reacted at -60℃ for 1 hour. After the completion of reaction, 10%by mass of hydrochloric acid was poured into the reaction solution, followed by extraction with toluene. An organic layer was washed with saturated saline and then purified by column chromatography (silica gel, hexane) , thereby producing 22.5 g of a compound represented by formula (I-1-2) . Next, in a nitrogen atmosphere in a reactor, 22.5 g of the compound represented by the formula (I-1-2) , 0.7 g of copper (I) iodide, 1.2 g of bis (triphenylphosphine) palladium (II) dichloride, 50 mL of triethylamine, and 150 mL of N, N-dimethylformamide (DMF) were added. Then, a solution prepared by dissolving 14 g of a compound represented by formula (I-1-3) in 15 mL of N, N-dimethylformamide was dropped under heating at 80℃, and stirred at 80℃ for 2 hours. After the completion of reaction, a saturated aqueous ammonium chloride solution was poured to the reaction solution, followed by extraction with ethyl acetate. An organic layer was washed with saturated saline and then re-crystallized with toluene, producing 24.5 g a compound represented by formula (I-1-4) . In a reactor, 24.5 of the compound represented by the formula (I-1-4) , 100 mL of dichloromethane, and 13.4 g of 1, 1-thiocarbonyldiimidazole were added and heated under reflux for 2 hours. After the completion of reaction, an organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) and re-crystallization (toluene/hexane = 2/1) , thereby producing 23 g of a compound represented by formula (I-1) .

MS (EI) : m/z = 369

(EXAMPLE 2: Production of compound represented by formula (I-2) )

[Chem. 78]

In a nitrogen atmosphere in a reactor, 27 g of a compound represented by formula (I-2-1) , 30 g of potassium acetate, 28 g of a compound represented by formula (I-2-2) , 1.6 g of [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, and 250 mL of DMF were added and reacted for 3 hours under heating of the reactor at 80℃. After the completion of reaction, 10%by mass of hydrochloric acid was poured to the reaction solution, followed by extraction with toluene. An organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) , thereby producing 27 g a compound represented by formula (I-2-3) . Next, in a nitrogen atmosphere in a reactor, 27 g of the compound represented by the formula (I-2-3) , 1.1 g of tetrakis (triphenylphosphine) palladium, 20 g of potassium carbonate, 29 g of a compound represented by formula (1-2-4) , 250 mL of THF, and 50 mL of water were added, and the reactor was heated to 70℃. After the completion of reaction, 10%by mass of hydrochloric acid was poured into the reaction solution, followed by extraction with ethyl aetate. An organic layer was washed with saturated saline and then the solvent was distilled off. Then, the residue was dispersed and washed with toluene, producing 31 g of a compound represented by formula (I-2-5) . Next, in a reactor, 31 g of the compound represented by the formula (I-2-5) , 200 mL of dichloromethane, and 15.4 g of 1, 1, 1-thiocarbonyldiimidazole were added, and then heated under reflux for 2 hours. After the completion of reaction, an organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) and re-crystallization (toluene/hexane = 2/1) , thereby producing 29 g of a compound represented by formula (I-2) .

MS (EI) : m/z = 473

(EXAMPLE 3: Production of compound represented by formula (I-3) )

[Chem. 79]

In a nitrogen atmosphere in a reactor, 26 g of a compound represented by formula (I-3-1) , 0.7 g of copper (I) iodide, 1.2 g of bis (triiphenylphosphine) palladium (II) dichloride, 50 mL of triethylamine, and 100 mL of DMF were added. Then, a solution prepared by dissolving 12 g of trimethylsilylacetylene in 15 mL of N, N-dimethylformamide was dropped under heating of the reaction solution at 60℃, and then stirred at 60℃ for 2 hours. After the completion of reaction, a saturated ammonium chloride solution was poured to the reaction solution, followed by extraction with toluene. An organic layer was washed with saturated saline and then toluene was distilled off. Then, 100 mL of methanol and 14 g of potassium carbonate were added to the concentrated product and stirred under heating at 50℃ for 2 hours. After the completion of reaction, pure water was poured into the reaction solution, followed by extraction with ethyl acetate. An organic layer was washed with saturated saline, and then the solvent was distilled off. Then, the residue was purified by column chromatography (silica gel, hexane) , producing 17 g of a compound represented by formula (I-3-2) . Next, in a nitrogen atmosphere in a reactor, 22 g of a compound represented by formula (I-3-3) , 1 g of tetrakis (triphenylphosphine) palladium, 50 mL of triethylamine, and 100 mL of DMF were added. Then, a solution prepared by dissolving 17 g of the compound represented by the formula (I-3-2) in 15 mL of N, N-dimethylformamide was dropped under heating of the reaction solution at 80℃, and then stirred at 80℃ for 2 hours. After the completion of reaction, a saturated aqueous ammonium chloride solution was poured to the reaction solution, followed by extraction with ethyl acetate. An organic layer was washed with saturated saline and re-crystallized with toluene, producing 27 g of a compound represented by formula (I-3-4) . Next, in a reactor, 27 g of the compound represented by the formula (I-3-4) , 200 mL of dichloromethane, and 15 g of 1, 1'-thiocarbonyl-di-2 (1H) pyridone were added and reacted at room temperature for 2 hours. After the completion of reaction, an organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) and re-crystallization (toluene/hexane = 2/1) , thereby producing 29 g of a compound represented by formula (I-3) .

MS (EI) : m/z = 469

(EXAMPLE 4: Production of compound represented by formula (I-4) )

[Chem. 80]

A compound represented by formula (I-4) was produced by the same method as in Example 3 except that the compound represented by the formula (I-3-1) was replaced by a compound represented by formula (I-4-1) , and the compound represented by the formula (I-3-3) was replaced by a compound represented by formula (I-4-3) .

MS (EI) : m/z = 483

(EXAMPLE 5: Production of compound represented by formula (I-5) )

[Chem. 81]

A compound represented by formula (I-5) was produced by the same method as in Example 3 except that the compound represented by the formula (I-3-1) was replaced by a compound represented by formula (I-5-1) , and the compound represented by the formula (I-3-3) was replaced by a compound represented by formula (I-5-3) .

MS (EI) : m/z = 483

(EXAMPLE 6: Production of compound represented by formula (I-6) )

[Chem. 82]

A compound represented by formula (I-6) was produced by the same method as in Example 3 except that the compound represented by the formula (I-3-1) was replaced by a compound represented by formula (I-6-1) , and the compound represented by the formula (I-3-3) was replaced by a compound represented by formula (I-6-3) .

MS (EI) : m/z = 467

(EXAMPLE 7: Production of compound represented by formula (I-7) )

[Chem. 83]

A compound represented by formula (I-7) was produced by the same method as in Example 3 except that the compound represented by the formula (I-3-1) was replaced by a compound represented by formula (I-7-1) , and the compound represented by the formula (I-3-3) was replaced by a compound represented by formula (I-7-3) .

MS (EI) : m/z = 497

(EXAMPLE 8: Production of compound represented by formula (I-8) )

[Chem. 84]

A compound represented by formula (I-8) was produced by the same method as in Example 3 except that the compound represented by the formula (I-3-1) was replaced by a compound represented by formula (I-8-1) , and the compound represented by the formula (I-3-3) was replaced by a compound represented by formula (I-8-3) .

MS (EI) : m/z = 481

(EXAMPLE 9: Production of compound represented by formula (I-9) )

[Chem. 85]

A compound represented by formula (I-9) was produced by the same method as in Example 3 except that the compound represented by the formula (I-3-1) was replaced by a compound represented by formula (I-9-1) , and the compound represented by the formula (I-3-3) was replaced by a compound represented by formula (I-9-3) .

MS (EI) : m/z = 483

(EXAMPLE 10: Production of compound represented by formula (I-10) )

[Chem. 86]

A compound represented by formula (I-10) was produced by the same method as in Example 3 except that the compound represented by the formula (I-3-1) was replaced by a compound represented by formula (I-10-1) , and the compound represented by the formula (I-3-3) was replaced by a compound represented by formula (I-10-3) .

MS (EI) : m/z = 483

[Preparation and evaluation of liquid crystal composition]

A mother liquid crystal (LC-1) showing physical values described below was prepared. All values are actual measurement values.

T_n-I (nematic phase-isotropic liquid phase transition temperature) : 74.0℃

Δε (dielectric anisotropy at 25℃ and 1kHz) : 5.11

Δn (refractive index anisotropy at 25℃ and 589 nm) : 0.141

γ₁ (rotational viscosity coefficient at 25℃) : 107 mPa·s

Each of the compounds (I-1) to (I-10) produced in the examples and each of the compounds represented by formulae (C-1) and (C-2) using neither a benzofuran structure nor a benzothiophene structure were added to the mother liquid crystal (LC-1) , preparing a liquid crystal composition containing each of 0%by mass, 5%by mass, and 10%by mass of each of the compounds in 100%by mass of the liquid crystal composition. Then, Δn and Δε_r of 100%by mass of the compound were determined from extrapolation values using a least square method. The results are shown in Table 1. With respect to the compound (C-2) , extrapolation values of Δn and Δε_r could not be determined because it was not precipitated.

[Storage stability test]

Each of the compounds (I-1) to (I-10) produced in the examples and each the compounds represented by formulae (C-1) and (C-2) using neither a benzofuran structure nor a benzothiophene structure were added to the mother liquid crystal (LC-1) , preparing a liquid crystal composition containing 5%by mass of each of the compounds in 100%by mass of the liquid crystal composition. In a 1 mL sample bottle (manufactured by Maruem Corporation) , 0.5 g of the liquid crystal composition prepared as described above was weighed and then defoamed by degassing at 150℃ and 250 Pa for 10 minutes. Then, the bottle was purged with dry nitrogen and sealed with a cap equipped therein. The bottle was stored for 2 weeks in a temperature control-type constant temperature bath (SH-241, manufactured by Espec Corp. ) of 0℃, and the occurrence of crystallization of the liquid crystal composition was visually observed every other day. When crystallization was not visually observed for one week or more, the composition was evaluated as "○" , when crystallization was visually observed on the 4th day or later, the composition was evaluated as "Δ" , and when crystallization was visually observed until the 3rd day, the composition was evaluated as "×" . The results are shown in Table 1.

[Chem. 87]

[Table 1]

It was confirmed from Examples 11, Comparative Example 1, Examples 17 and 18, and Comparative Example 2 that the compound represented by the general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate structure has large Δn, large Δε_r, and relatively good storage stability at a low temperature.

[Industrial Applicability]

The compound of the present invention can be used for a liquid crystal composition, a liquid crystal display device, a sensor, a liquid crystal lens, an optical communication device, and an antenna.

Claims

A compound represented by general formula (i) below,

[Chem. 1]

(in the general formula (i) ,

Rⁱ¹ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, one or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-,

one or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom,

an oxygen atom and an oxygen atom are not directly bonded to each other,

A^ibf/t represents a group selected from the group consisting of groups represented by general formulae (A^ibf-1) to (A^ibf-4) and (A^ibt-1) to (A^ibt-4) below,

[Chem. 2]

(in the general formulae (A^ibf-1) to (A^ibf-4) and (A^ibt-1) to (A^ibt-4) ,

a white point represents a bond to Rⁱ¹,

a black point represents a bond to Zⁱ¹,

Lⁱ¹and Lⁱ²each independently represent any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

one or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, -CO-, and/or -CS-,

one or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom, and

an oxygen atom and an oxygen atom are not directly bonded to each other)

Aⁱ¹and Aⁱ² each independently represent any one of a hydrocarbon ring having 3 to 16 carbon atoms and a heterocyclic ring having 3 to 16,

one or two or more hydrogen atoms in Aⁱ¹and Aⁱ² may be each independently substituted by substituent Sⁱ¹,

the substituent Sⁱ¹ represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

one or two or more -CH₂-in the alkyl group may be each independently substituted by -O-, -S-, and/or -CO-,

one or two or more -CH₂-CH₂-in the alkyl group may be each 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 two or more hydrogen atoms in the alkyl group may be each independently substituted by a halogen atom,

an oxygen atom and an oxygen atom are not directly bonded to each other,

when a plurality of substituents Sⁱ¹ are present, they may be the same or different,

Zⁱ¹and Zⁱ² each independently represent any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

one or two or more -CH₂-in the alkylene group may be each independently substituted by -O-, -CF₂-, and/or -CO-,

one or two or more -CH₂-CH₂-in the alkylene group may be each 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-, and/or -C≡C-,

an oxygen atom and an oxygen atom are not directly bonded to each other,

nⁱ¹ represents an integer of 0 to 3, and

when a plurality of Aⁱ² or Zⁱ² are present, they may be the same or different) .
The compound according to Claim 1, in which the compound represented by the general formula (i) is a compound selected from the group consisting of compounds represented by general formulae (i-1) to (i-6) below,

[Chem. 3]

(in the general formulae (i-1) to (i-6) ,

Rⁱ¹, A^ibf/t, Aⁱ¹, and Aⁱ² represent the same meanings as Rⁱ¹, A^ibf/t, Aⁱ¹, and Aⁱ², respectively, in the general formula (i) ) .
The compound according to Claim 1 or 2, in which Rⁱ¹ represents any one of a linear or branched alkyl group having 2 to 6 carbon atoms, a liner alkoxyalkyl having 1 to 6 carbon atoms, and a linear alkenyl group having 2 to 6 carbon atoms.
A liquid crystal composition comprising one or more two or more compounds according to any one of Claims 1 to 3.
A liquid crystal display device comprising the liquid crystal composition according to Claim 4.
A sensor comprising the liquid crystal composition according to Claim 4.
A liquid crystal lens comprising the liquid crystal composition according to Claim 4.
An optical communication device comprising the liquid crystal composition according to Claim 4.
An antenna comprising the liquid crystal composition according to Claim 4.
The antenna according to Claim 9, comprising:

a first substrate provided with 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 disposed 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,

wherein

the liquid crystal layer contains the liquid crystal composition according to Claim 4.