JP7428296B2 - Compounds, liquid crystal compositions and high frequency phase shifters - Google Patents

Description

The present invention relates to a compound, a liquid crystal composition containing the compound, and an element using the liquid crystal composition.

Liquid crystal compositions are used for mobile terminals such as smartphones and tablet devices, and display applications such as TVs and window displays. As a new application of this liquid crystal composition, antennas that transmit and receive radio waves between mobile objects such as cars and communication satellites are attracting attention.
Conventionally, satellite communications have used parabolic antennas, but when used on a mobile object, the parabolic antenna must be oriented toward the satellite at any time, requiring a large movable part. However, in antennas using liquid crystal compositions, the direction of transmitting and receiving radio waves can be changed by operating the liquid crystal, so there is no need to move the antenna itself, and the shape of the antenna can be made flat.
The refractive index anisotropy Δn of the liquid crystal composition required for these uses is, for example, about 0.4, which is much larger than Δn required for display uses. Therefore, the compound added to and used in the liquid crystal composition is required to have a large Δn and high compatibility with the liquid crystal composition. Conventionally, compounds having a thienothiophene structure have been reported as compounds with a large Δn. However, when these compounds are added to a liquid crystal composition for antenna use, they have a problem of low compatibility and precipitation during long-term storage (Non-Patent Document 1, Patent Documents 1 and 2). Furthermore, compounds having a thienothiophene structure and a thioisocyano group have been reported, but these compounds had low dielectric anisotropy in the high frequency region and insufficient phase modulation properties (Patent Document 3- 4). Therefore, there has been a demand for the development of a compound that has a large Δn, is highly compatible with liquid crystal compositions, and exhibits large dielectric anisotropy in a high frequency region.

Chemistry of Materials, 2009, Volume 21, Issue 13, Pages 2727-2732

CN103472116A publication Japanese Patent Application Publication No. 2012-167068 CN106518890A publication WO2020/120586 publication

The problem to be solved by the present invention is to develop a compound that has large refractive index anisotropy (Δn), is highly compatible with liquid crystal compositions, and exhibits large dielectric constant anisotropy (Δε) in a high frequency region. It is an object of the present invention to provide a liquid crystal composition containing the compound and an element using the liquid crystal composition.

The present inventors conducted intensive research to solve the above problems, and as a result, developed a specific compound. That is, the present invention provides the following general formula (I)

（式中、Ｒ^１は水素原子、フッ素原子、塩素原子若しくは炭素原子数１から２０の直鎖状又は分岐状アルキル基を表し、当該アルキル基中の任意の水素原子がハロゲン原子に置換されていても良く、当該アルキル基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良いが、酸素原子同士が結合することはなく、
Ａ^１及びＡ^２は各々独立して置換されていてもよい炭素原子数３から１６の炭化水素環又は複素環を表すが、Ａ^１が複数存在する場合それらは同一であっても異なっていても良く、Ａ^２が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^１、Ｚ^２及びＺ^３は各々独立して二価の連結基又は単結合を表すが、Ｚ^１が複数存在する場合それらは同一であっても異なっていても良く、Ｚ^２が複数存在する場合それらは同一であっても異なっていても良く、
ｍ１及びｍ２は各々独立して０から３の整数を表し、
Ａ^ｘは水素原子、フッ素原子、塩素原子若しくは炭素原子数１から２０の直鎖状又は分岐状アルキル基を表し、当該アルキル基中の任意の水素原子がハロゲン原子に置換されていても良く、当該アルキル基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良いが、酸素原子同士が結合することはなく、あるいはＡ^ｘは下記の式（Ａｘ－１）～（Ａｘ－５）

(In the formula, R ¹ represents a hydrogen atom, a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, and any hydrogen atom in the alkyl group is substituted with a halogen atom. One or more -CH ₂ - in the alkyl group may each independently be -O-, -S-, -CO-, -COO-, -OCO-, -CO-S- , -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C- may be substituted with However, oxygen atoms do not bond with each other,
A ¹ and A ² each independently represent an optionally substituted hydrocarbon ring or heterocycle having 3 to 16 carbon atoms; however, if multiple A ^1s exist, they may be the same or different; and if there are multiple ^A2s , they may be the same or different,
Z ¹ , Z ² and Z ³ each independently represent a divalent linking group or a single bond, but if multiple Z ^1s exist, they may be the same or different, and if multiple Z ^2s exist If so, they may be the same or different;
m1 and m2 each independently represent an integer from 0 to 3,
A ^x represents a hydrogen atom, a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, and any hydrogen atom in the alkyl group may be substituted with a halogen atom, One or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S- Although it may be replaced with CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, the oxygen atom They do not combine with each other, or A ^x is expressed by the following formulas (Ax-1) to (Ax-5)

（式中、破線は結合位置を表し、Ｙ^１は各々独立して水素原子、フッ素原子、塩素原子又は任意の水素原子がフッ素原子に置換されていても良い炭素原子数１から８のアルキル基若しくはアルコキシ基を表し、Ｙ^１が複数存在する場合それらは同一であっても異なっていても良く、Ｙ^２は水素原子、フッ素原子、塩素原子、シアノ基、イソチオシアノ基又は任意の水素原子がフッ素原子に置換されていても良い炭素原子数１から８のアルキル基を表し、当該アルキル基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良いが、酸素原子同士が結合することはない。）からなる群より選ばれる構造を表すが、ここでＡ^ｘが式（Ａｘ－１）～（Ａｘ－５）からなる群から選ばれる構造である場合ｍ１＋ｍ２は０から３の整数を表し、Ａ^ｘが式（Ａｘ－１）～（Ａｘ－５）からなる群から選ばれる構造ではない場合はｍ１＋ｍ２は１から４の整数を表す。）で表される化合物を提供し、当該化合物を含有する液晶組成物及び当該液晶組成物を使用した素子を提供する。

(In the formula, the broken line represents the bonding position, and Y ¹ is each independently a hydrogen atom, a fluorine atom, a chlorine atom, or an alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom. or represents an alkoxy group, and when multiple Y ^1s exist, they may be the same or different, and Y ² is a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or any hydrogen atom is a fluorine atom. Represents an alkyl group having 1 to 8 carbon atoms which may be substituted with an atom, and one or more -CH ₂ - in the alkyl group are each independently -O-, -S-, - CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, - CF=CF- or -C≡C- may be substituted, but the oxygen atoms do not bond to each other), where A ^x has the formula (Ax-1 ) to (Ax-5), m1+m2 represents an integer from 0 to 3, and in a structure where A ^x is selected from the group consisting of formulas (Ax-1) to (Ax-5), If not, m1+m2 represents an integer from 1 to 4. ), a liquid crystal composition containing the compound, and an element using the liquid crystal composition.

The compound of the present invention has a large refractive index anisotropy Δn, is highly compatible with liquid crystal compositions, and exhibits a large dielectric constant anisotropy in a high frequency region. It is useful as a material for elements such as image recognition devices, distance measuring devices, liquid crystal display elements, liquid crystal lenses, and birefringent lenses for stereoscopic image display.

The present invention provides a compound represented by general formula (I), a liquid crystal composition containing the compound, and an element using the liquid crystal composition.

In general formula (I), R ¹ represents a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, and any hydrogen atom in the alkyl group may be substituted with a halogen atom. , one or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S -CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C- may be substituted, but oxygen Atoms do not bond with each other. From the viewpoints of compatibility with the liquid crystal composition, refractive index anisotropy, voltage holding rate, ease of synthesis, and availability of raw materials, R ¹ is a hydrogen atom, and any hydrogen atom in the group is substituted with a halogen atom. One or more -CH ₂ - in the group may each independently be -O-, -S-, -CH=CH-, -CF=CF- or -C≡C-. It is preferable to represent a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted, and R ¹ may be substituted with a fluorine atom for any hydrogen atom in the group. Straight chain or branched chain having 1 to 12 carbon atoms, in which one or more -CH ₂ - may each be independently replaced with -O-, -CH═CH- or -C≡C- More preferably, R ¹ represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms. More preferably, it represents an oxy group or an alkynyl group having 2 to 8 carbon atoms, and R ¹ is an alkyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. Particular preference is given to representing a group or an alkynyl group having 3 to 7 carbon atoms.

In general formula (I), A ¹ and A ² each independently represent an optionally substituted hydrocarbon ring or heterocycle having 3 to 16 carbon atoms; however, if multiple A ^1s exist, they are the same They may be the same or different, and when there is a plurality of ^A2 's, they may be the same or different. From the viewpoint of compatibility with liquid crystal compositions, refractive index anisotropy, dielectric anisotropy, voltage holding rate, ease of synthesis, and availability of raw materials, A ¹ and A ² are each independently unsubstituted. or may be substituted by one or more substituents ^L1 ,
(a) 1,4-cyclohexylene group (one -CH ₂ - or two or more non-adjacent -CH ₂ -s present in this group is replaced with -O- or -S-) is also good.)
(b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in this group may be replaced with -N=)
(c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6- Diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (even if the hydrogen atoms present in these groups are substituted with fluorine or chlorine atoms) Also, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene -1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group -CH= or two or more -CH= may be replaced with -N=.)
(d) Thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= present in this group is replaced with -N= It is preferable to represent a group selected from the group consisting of ⁽ may be a ^group consisting of or 1,4-phenylene group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 5,6,7,8-, which may be substituted with one or more substituents L ¹ Tetrahydronaphthalene-1,4-diyl group, phenanthrene-2,7-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, benzothiazole-2,5-diyl group, benzo A group selected from thiazole-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group or thieno[3,2-b]thiophene-2,5-diyl group It is more preferable to represent A ¹ and A ² when a plurality of them exist, they may be the same or different, and each independently represents the following formula (A-1) to formula (A-17).

（式中、破線は結合位置を表し、Ｌ^１が複数存在する場合それらは同一であっても異なっていても良い。）から選ばれる基を表すことがさらに好ましく、Ａ^１及びＡ^２は複数存在する場合それらは同一であっても異なっていても良く、各々独立して式（Ａ－１）から式（Ａ－７）、式（Ａ－１２）、式（Ａ－１５）及び式（Ａ－１７）から選ばれる基を表すことがさらにより好ましく、Ａ^１及びＡ^２は複数存在する場合それらは同一であっても異なっていても良く、各々独立して式（Ａ－１）、式（Ａ－３）から式（Ａ－７）から選ばれる基を表すことが特に好ましい。

(In the formula, the broken line represents the bonding position, and if there are multiple L ¹ s, they may be the same or different.) It is more preferable to represent a group selected from A ¹ and A ² are multiple L 1 s. When present, they may be the same or different, and each independently represents formula (A-1) to formula (A-7), formula (A-12), formula (A-15) and formula ( It is even more preferable to represent a group selected from A-17), and when a plurality of A ¹ and A ² exist, they may be the same or different, and each independently represents a group selected from formula (A-1), It is particularly preferable to represent a group selected from formulas (A-3) to (A-7).

L ¹ is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropyl Amino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one -CH ₂ - or two or more -CH ₂ - each independently -O-, -S-, -CO-, -COO -, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH 1 to 20 carbon atoms optionally substituted with -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- represents a linear alkyl group or a branched or cyclic alkyl group having 3 to 20 carbon atoms, but the oxygen atoms do not bond directly to each other, and any hydrogen atom in the alkyl group is substituted with a fluorine atom. Represents a group that can be used. From the viewpoint of compatibility with liquid crystal compositions, refractive index anisotropy, dielectric constant anisotropy, voltage holding rate, ease of synthesis, and availability of raw materials, L ¹ is a fluorine atom, a chlorine atom, or a group Any hydrogen atom may be substituted with a fluorine atom, and one -CH ₂ - or two or more -CH ₂ - in the group are each independently -O-, -S-, -CH= Represents a linear alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, which may be substituted with CH-, -CF=CF- or -C≡C-. is preferable, and L ¹ is a fluorine atom, or a carbon atom number of 1 in which any hydrogen atom in the group may be substituted with a fluorine atom, and -CH ₂ - in the group may be substituted with -O-. It is more preferable to represent a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, and L ¹ is a fluorine atom or a linear alkyl group having 1 to 10 carbon atoms or a carbon atom. It is more preferable to represent a branched or cyclic alkyl group having 3 to 10 carbon atoms, and it is particularly preferable that L ¹ represents a fluorine atom or a linear alkyl group having 1 to 8 carbon atoms.

In the general formula (I), Z ¹ , Z ² and Z ³ each independently represent a divalent linking group or a single bond, but when multiple Z ^1s exist, they may be the same or different. If there are multiple ^Z2 's, they may be the same or different. From the viewpoint of compatibility with the liquid crystal composition, refractive index anisotropy, dielectric constant anisotropy, voltage holding rate, ease of synthesis, and availability of raw materials, Z ¹ , Z ² and Z ³ are each independently Single bond, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CHCOO-, -OCOCH=CH-, -CH=C(CH ₃ )COO-, -OCOC(CH ₃ )=CH-, -CH ₂ -CH(CH ₃ )COO-, -OCOCH(CH ₃ )-CH ₂ -, -OCH ₂ CH ₂ O-, -N=N-, -C=N-N=C-, -CH=N-, -N=CH-, -C≡ C-C≡C- or an alkylene group having 2 to 20 carbon atoms, and one or more -CH ₂ - in this alkylene group is -O-, -S-, -COO- or -OCO It is preferable to represent a group which may be substituted with -, and when a plurality of Z ¹ , Z ² and Z ³ exist, they may be the same or different, and each independently represents -OCH ₂ -, - CH ₂ O-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH= It is more preferable to represent N-N=CH-, -CF=CF-, -C≡C-, -C≡C-C≡C- or a single bond, and a plurality of Z ¹ , Z ² and Z ³ exist. In the case, they may be the same or different, each independently -CF ₂ O-, -OCF ₂ -, -CH=CH-, -CF=CF-, -N=N-, -C≡ It is more preferable to represent C-, -C≡C-C≡C- or a single bond, and when a plurality of Z ¹ , Z ² and Z ³ exist, they may be the same or different, each independently It is even more preferable to represent -CF ₂ O-, -OCF ₂ -, -N=N-, -C≡C-, -C≡C-C≡C- or a single bond, and Z ¹ , Z ² When a plurality of Z 3 and Z ³ are present, they may be the same or different, and it is particularly preferred that each independently represent -C≡C- or a single bond.

In general formula (I), m1 and m2 each independently represent an integer from 0 to 3, but preferably m1+m2 is an integer from 0 to 4, especially when A ^x is represented by formulas (Ax-1) to (Ax -5), m1+m2 is preferably an integer from 0 to 3, more preferably an integer from 0 to 2. Furthermore, if A ^x does not have a structure selected from the group consisting of formulas (Ax-1) to (Ax-5), m1+m2 is preferably an integer from 1 to 4, and preferably an integer from 1 to 3. More preferred. From the viewpoint of compatibility with the liquid crystal composition, refractive index anisotropy, dielectric anisotropy, voltage holding rate, ease of synthesis, and availability of raw materials, m1 and m2 are each independently 0, 1, or 2. , m1+m2 preferably represents an integer from 1 to 3, m1 and m2 each independently represent 0, 1 or 2, m1+m2 more preferably represents 1 or 2, m1 and m2 each independently It is more preferable that the number represents 0 or 1, m1+m2 represents 1 or 2, it is particularly preferable that m1 and m2 each independently represent 0 or 1, and m1+m2 represents 1.

The compound represented by general formula (I) contains a thieno[3,2-b]thiophene-2,5-diyl group with a sulfur atom bonded to the 2-position in its structure, so it is derived from three sulfur atoms. The conjugated structure with a high electron density can effectively increase Δn, and exhibits an excellent effect of exhibiting large dielectric anisotropy in a high frequency region. Furthermore, since general formula (I) has a total of two or more ring structures in the molecule, the entire compound forms a rod-shaped molecular structure, which improves liquid crystallinity and increases Tni. When added, the liquid crystal phase temperature range can be effectively expanded while maintaining high compatibility.

In the general formula (I), A ^x represents a hydrogen atom, a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, and any hydrogen atom in the alkyl group is replaced by a halogen atom. It may be substituted, and one or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C- However, the oxygen atoms do not bond with each other, or A ^x can be represented by the following formulas (Ax-1) to (Ax-5).

（式中、破線は結合位置を表し、Ｙ^１は各々独立して水素原子、フッ素原子、塩素原子又は任意の水素原子がフッ素原子に置換されていても良い炭素原子数１から８のアルキル基若しくはアルコキシ基を表し、Ｙ^１が複数存在する場合それらは同一であっても異なっていても良く、Ｙ^２は水素原子、フッ素原子、塩素原子、シアノ基、イソチオシアノ基又は任意の水素原子がフッ素原子に置換されていても良い炭素原子数１から８のアルキル基を表し、当該アルキル基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良いが、酸素原子同士が結合することはない。）からなる群より選ばれる構造を表す。液晶組成物への相溶性、屈折率異方性、誘電率異方性、電圧保持率、合成の容易さ及び原料の入手性の観点から、Ａ^ｘは下記の式（Ａｘ－１－ｉ）～（Ａｘ－５－ｉ）

(In the formula, the broken line represents the bonding position, and Y ¹ is each independently a hydrogen atom, a fluorine atom, a chlorine atom, or an alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom. or represents an alkoxy group, and when multiple Y ^1s exist, they may be the same or different, and Y ² is a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or any hydrogen atom is a fluorine atom. Represents an alkyl group having 1 to 8 carbon atoms which may be substituted with an atom, and one or more -CH ₂ - in the alkyl group are each independently -O-, -S-, - CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, - CF=CF- or -C≡C- may be substituted, but the oxygen atoms do not bond to each other). From the viewpoint of compatibility with the liquid crystal composition, refractive index anisotropy, dielectric anisotropy, voltage holding rate, ease of synthesis, and availability of raw materials, A ^x is expressed by the following formula (Ax-1-i) ～(Ax-5-i)

（式中、破線は結合位置を表し、Ｙ^１１は各々独立して水素原子、フッ素原子又は炭素原子数１から８のアルキル基若しくはアルコキシ基を表し、Ｙ^１１が複数存在する場合それらは同一であっても異なっていても良く、Ｙ^２1は水素原子、フッ素原子、塩素原子、シアノ基、イソチオシアノ基又は任意の水素原子がフッ素原子に置換されていても良い炭素原子数１から８のアルキル基を表し、当該アルキル基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良いが、酸素原子同士が結合することはない。）からなる群より選ばれる構造を表すことが好ましく、式（Ａｘ－１－ｉ）又は（Ａｘ－２－ｉ）を表すことが更に好ましい。また、Ａ^ｘは下記の式（Ａｘ－１－ｉｉ）

(In the formula, the broken line represents the bonding position, each Y ¹¹ independently represents a hydrogen atom, a fluorine atom, or an alkyl group or alkoxy group having 1 to 8 carbon atoms, and if multiple Y ^11s exist, they are the same. ^Y21 is a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or an alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom. represents, and one or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CH=CH-, -CF=CF- or -C≡C- may be substituted, but the oxygen atoms do not bond to each other.) It is preferable to represent a structure selected from the group consisting of, and more preferably to represent the formula (Ax-1-i) or (Ax-2-i). In addition, A ^x is the following formula (Ax-1-ii)

（式中、破線は結合位置を表し、
Ｙ^１３は各々独立して水素原子、フッ素原子又は塩素原子を表す。）から選ばれる基を表すことが特に好ましい。
また、一般式（I）で表される化合物において、液晶組成物への溶解性の観点から

(In the formula, the dashed line represents the bonding position,
Y ¹³ each independently represents a hydrogen atom, a fluorine atom or a chlorine atom. ) is particularly preferred.
In addition, in the compound represented by general formula (I), from the viewpoint of solubility in liquid crystal compositions,

で表される部分構造と、

The substructure represented by

で表される部分構造とが異なる構造であることが好ましい。
一般式（Ｉ）で表される化合物は、液晶相を示す温度範囲の広さ、誘電率異方性、液晶組成物への相溶性、屈折率異方性、誘電率異方性、電圧保持率、合成の容易さ及び原料の入手性の観点から、一般式（Ｉ－ｉ）

It is preferable that the partial structure represented by is a different structure.
The compound represented by the general formula (I) has a wide temperature range exhibiting a liquid crystal phase, dielectric anisotropy, compatibility with liquid crystal compositions, refractive index anisotropy, dielectric anisotropy, and voltage retention. From the viewpoint of efficiency, ease of synthesis, and availability of raw materials, general formula (I-i)

（式中、Ｒ^１１は水素原子、基中の任意の水素原子がハロゲン原子に置換されていても良く、基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良い炭素原子数１から２０の直鎖状又は分岐状アルキル基を表し、
Ａ^１１及びＡ^２１は各々独立して１，４－フェニレン基、ナフタレン－２，６－ジイル基、ナフタレン－１，４－ジイル基、５，６，７，８－テトラヒドロナフタレン－１，４－ジイル基、フェナントレン－２，７－ジイル基、ベンゾチオフェン－２，５－ジイル基、ベンゾチオフェン－２，６－ジイル基、ベンゾチアゾール－２，５－ジイル基、ベンゾチアゾール－２，６－ジイル基、ジベンゾチオフェン－３，７－ジイル基、ジベンゾチオフェン－２，６－ジイル基又はチエノ［３，２－ｂ］チオフェン－２，５－ジイル基を表すが、Ａ^１１が複数存在する場合それらは同一であっても異なっていても良く、Ａ^２１が複数存在する場合それらは同一であっても異なっていても良く、これらの基は無置換であるか又は１つ以上の置換基Ｌ^１１によって置換されていても良く、
Ｌ^１１はフッ素原子、塩素原子又は基中の任意の水素原子がフッ素原子に置換されていても良く、基中の１個の－ＣＨ_２－又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－若しくは－Ｃ≡Ｃ－によって置換されていても良い炭素原子数１から２０の直鎖状アルキル基又は炭素原子数３から２０の分岐状若しくは環状アルキル基を表すが、Ｌ^１１が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^１１、Ｚ^２１及びＺ^３１は各々独立して－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＳＣＨ_２－、－ＣＨ_２Ｓ－、－ＣＨ_２ＣＨ_２－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ＝ＣＨ－、－Ｎ＝Ｎ－、－ＣＨ＝Ｎ－、－Ｎ＝ＣＨ－、－ＣＨ＝Ｎ－Ｎ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－、－Ｃ≡Ｃ－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^１１が複数存在する場合それらは同一であっても異なっていても良く、Ｚ^２１が複数存在する場合それらは同一であっても異なっていても良く、
ｍ１１及びｍ２１は各々独立して０、１又は２を表し、
Ａ^ｘ１は水素原子、基中の任意の水素原子がハロゲン原子に置換されていても良く、基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良い炭素原子数１から２０の直鎖状又は分岐状アルキル基を表し、あるいはＡ^ｘ１は下記の式（Ａｘ－１－ｉ）～（Ａｘ－５－ｉ）

(In the formula, R ¹¹ is a hydrogen atom, any hydrogen atom in the group may be substituted with a halogen atom, and one or more -CH ₂ - in the group are each independently -O- , -S-, -CH=CH-, -CF=CF- or -C≡C- represents a linear or branched alkyl group having 1 to 20 carbon atoms,
A ¹¹ and A ²¹ each independently represent a 1,4-phenylene group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, or a 5,6,7,8-tetrahydronaphthalene-1,4- Diyl group, phenanthrene-2,7-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, benzothiazole-2,5-diyl group, benzothiazole-2,6-diyl group group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, or thieno[3,2-b]thiophene-2,5-diyl group, and when multiple A ^11s exist, they may be the same or different, and when a plurality of A ^21s exist, they may be the same or different, and these groups are unsubstituted or have one or more substituents L ¹¹ may be replaced by
In L ¹¹ , a fluorine atom, a chlorine atom, or any hydrogen atom in the group may be substituted with a fluorine atom, and one -CH ₂ - or two or more -CH ₂ - in the group are each independently A linear alkyl group having 1 to 20 carbon atoms or 3 carbon atoms which may be substituted with -O-, -S-, -CH=CH-, -CF=CF- or -C≡C- represents a branched or cyclic alkyl group represented by 20, but when multiple L ^11s exist, they may be the same or different,
Z ¹¹ , Z ²¹ and Z ³¹ each independently represent -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C-, - It represents C≡C-C≡C- or a single bond, but if there are multiple Z ^11s , they may be the same or different, and if there are multiple Z ^21s , they may be the same or different. You can leave it there,
m11 and m21 each independently represent 0, 1 or 2,
A ^x1 is a hydrogen atom, any hydrogen atom in the group may be substituted with a halogen atom, and one or more -CH ₂ - in the group are each independently -O-, -S- , -CH=CH-, -CF=CF- or -C≡C-, representing a linear or branched alkyl group having 1 to 20 carbon atoms, or A ^x1 is represented by the following formula ( Ax-1-i) ~ (Ax-5-i)

（式中、破線は結合位置を表し、Ｙ^１１は各々独立して水素原子、フッ素原子又は炭素原子数１から８のアルキル基若しくはアルコキシ基を表し、Ｙ^１１が複数存在する場合それらは同一であっても異なっていても良く、Ｙ^２1は水素原子、フッ素原子、塩素原子、シアノ基、イソチオシアノ基又は任意の水素原子がフッ素原子に置換されていても良い炭素原子数１から８のアルキル基を表し、当該アルキル基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良いが、酸素原子同士が結合することはない。）からなる群より選ばれる構造を表すが、ここでＡ^ｘ１が式（Ａｘ－１－ｉ）～（Ａｘ－５－ｉ）からなる群から選ばれる構造である場合、ｍ１１＋ｍ２１は０から３の整数を表し、Ａ^ｘが式（Ａｘ－１－ｉ）～（Ａｘ－５－ｉ）からなる群から選ばれる構造ではない場合はｍ１１＋ｍ２１は１から４の整数を表す。）
であることが好ましい。また、下記の一般式（Ｉ－ｉｉ）

(In the formula, the broken line represents the bonding position, each Y ¹¹ independently represents a hydrogen atom, a fluorine atom, or an alkyl group or alkoxy group having 1 to 8 carbon atoms, and if multiple Y ^11s exist, they are the same. ^Y21 is a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or an alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom. represents, and one or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, It may be replaced by -S-CO-, -O-CO-O-, -CH=CH-, -CF=CF- or -C≡C-, but the oxygen atoms do not bond to each other.) If A ^x1 is a structure selected from the group consisting of formulas (Ax-1-i) to (Ax-5-i), then m11+m21 is an integer from 0 to 3. , and if A ^x does not have a structure selected from the group consisting of formulas (Ax-1-i) to (Ax-5-i), m11+m21 represents an integer from 1 to 4. )
It is preferable that In addition, the following general formula (I-ii)

（式中、Ｒ^１２は基中の任意の水素原子がフッ素原子に置換されていても良く、基中の１個又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－ＣＨ＝ＣＨ－又は－Ｃ≡Ｃ－に置き換えられても良い炭素原子数１から１２の直鎖状又は分岐状アルキル基を表し、
Ａ^１２及びＡ^２２は各々独立して下記の式（Ａ－ｉｉ－１）から式（Ａ－ｉｉ－１７）

(In the formula, R ¹² may have any hydrogen atom in the group substituted with a fluorine atom, and one or more -CH ₂ - in the group are each independently -O-, -CH =CH- or -C≡C- represents a linear or branched alkyl group having 1 to 12 carbon atoms,
A ¹² and A ²² are each independently represented by the following formulas (A-ii-1) to (A-ii-17)

（式中、破線は結合位置を表し、Ｌ^１２が複数存在する場合それらは同一であっても異なっていても良い。）から選ばれる基を表すが、Ａ^１２が複数存在する場合それらは同一であっても異なっていても良く、Ａ^２２が複数存在する場合それらは同一であっても異なっていても良く、
Ｌ^１２はフッ素原子又は基中の任意の水素原子がフッ素原子に置換されていても良く、基中の－ＣＨ_２－が－Ｏ－によって置換されていても良い炭素原子数１から１０の直鎖状アルキル基又は炭素原子数３から１０の分岐状若しくは環状アルキル基を表し、
Ｚ^１２、Ｚ^２２及びＺ^３２は各々独立して－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－SＣＨ_２－、－ＣＨ_２S－、－ＣＨ_２ＣＨ_２－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ＝ＣＨ－、－Ｎ＝Ｎ－、－ＣＨ＝Ｎ－、－Ｎ＝ＣＨ－、－ＣＨ＝Ｎ－Ｎ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－、－Ｃ≡Ｃ－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^１２が複数存在する場合それらは同一であっても異なっていても良く、Ｚ^２２が複数存在する場合それらは同一であっても異なっていても良く、
ｍ１２及びｍ２２は各々独立して０、１又は２を表し、かつｍ１２＋ｍ２２は０から２の整数を表し、
Ａ^ｘ２は式（Ａｘ－１－ｉ）又は（Ａｘ－２－ｉ）のいずれかより選ばれる構造を表す。）で表される化合物であることがより好ましい。また、下記の一般式（Ｉ－ｉｉｉ）

(In the formula, the broken line represents the bonding position, and when there are multiple L ^12s , they may be the same or different.) However, when there are multiple A ^12s , they are the same. may be the same or different, and if there are multiple ^A22s , they may be the same or different,
L ¹² is a fluorine atom or a straight carbon atom having 1 to 10 carbon atoms, in which any hydrogen atom in the group may be substituted with a fluorine atom, and -CH ₂ - in the group may be substituted with -O-. Represents a chain alkyl group or a branched or cyclic alkyl group having 3 to 10 carbon atoms,
Z ¹² , Z ²² and Z ³² are each independently -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C-, - It represents C≡C-C≡C- or a single bond, but if there are multiple Z ^12s , they may be the same or different, and if there are multiple Z ^22s , they may be the same or different. You can leave it there,
m12 and m22 each independently represent 0, 1 or 2, and m12 + m22 represents an integer from 0 to 2,
A ^x2 represents a structure selected from either formula (Ax-1-i) or (Ax-2-i). ) is more preferable. In addition, the following general formula (I-iii)

（式中、Ｒ^１３は炭素原子数１から８のアルキル基、炭素原子数１から７のアルコキシ基、炭素原子数２から８のアルケニル基、炭素原子数２から７のアルケニルオキシ基又は炭素原子数２から８のアルキニル基を表し、
Ａ^１３及びＡ^２３は各々独立して下記の式（Ａ－ｉｉｉ－１）から式（Ａ－ｉｉｉ－７）、式（Ａ－ｉｉｉ－１２）、式（Ａ－ｉｉｉ－１５）及び式（Ａ－ｉｉｉ－１７）

(In the formula, R ¹³ is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 7 carbon atoms, or a carbon atom represents an alkynyl group of numbers 2 to 8,
A ¹³ and A ²³ each independently represent the following formulas (A-iii-1) to (A-iii-7), formula (A-iii-12), formula (A-iii-15), and formula ( A-iii-17)

（式中、破線は結合位置を表し、Ｌ^１３が複数存在する場合それらは同一であっても異なっていても良い。）から選ばれる基を表し、
Ｌ^１３はフッ素原子又は炭素原子数１から１０の直鎖状アルキル基又は炭素原子数３から１０の分岐状若しくは環状アルキル基を表し、
Ｚ^１３、Ｚ^２３及びＺ^３３は各々独立して－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－Ｎ＝Ｎ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－、－Ｃ≡Ｃ－Ｃ≡Ｃ－又は単結合を表し、
ｍ１３及びｍ２３は各々独立して０又は１を表し、
Ｙ^１３は各々独立して水素原子、フッ素原子又は塩素原子を表す。）で表される化合物であることがさらに好ましい。特に、下記の一般式（Ｉ－ｉｖ－１）又は一般式（Ｉ－ｉｖ－２）

(In the formula, the broken line represents the bonding position, and if there are multiple L ^13s , they may be the same or different.)
L ¹³ represents a fluorine atom, a linear alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms,
Z ¹³ , Z ²³ and Z ³³ each independently represent -CF ₂ O-, -OCF ₂ -, -N=N-, -CH=CH-, -CF=CF-, -C≡C-, -C ≡C-C≡C- or represents a single bond,
m13 and m23 each independently represent 0 or 1,
Y ¹³ each independently represents a hydrogen atom, a fluorine atom or a chlorine atom. ) is more preferable. In particular, the following general formula (I-iv-1) or general formula (I-iv-2)

（式中、Ｒ^１４は炭素原子数２から５のアルキル基、炭素原子数１から４のアルコキシ基、炭素原子数２から５のアルケニル基又は炭素原子数３から７のアルキニル基を表し、
Ａ^２４は下記の式（Ａ－ｉｖ－１）、式（Ａ－ｉｖ－３）から式（Ａ－ｉｖ－７）

(In the formula, ^R14 represents an alkyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 3 to 7 carbon atoms,
^A24 is the following formula (A-iv-1), formula (A-iv-3) to formula (A-iv-7)

（式中、破線は結合位置を表し、Ｌ^１４が複数存在する場合それらは同一であっても異なっていても良い。）から選ばれる基を表し、
Ｌ^１４はフッ素原子又は炭素原子数１から８の直鎖状アルキル基を表し、
Ｚ^２４及びＺ^３４は各々独立して－Ｃ≡Ｃ－、－Ｃ≡Ｃ－Ｃ≡Ｃ－又は単結合を表し、
Ｙ^１４及びＹ^３４は各々独立して水素原子又はフッ素原子を表す。）で表される化合物であることが特に好ましい。
一般式（Ｉ）で表される化合物として具体的には、下記の式（Ｉ－１）から式（Ｉ－６９）で表される化合物が挙げられる。

(In the formula, the broken line represents the bonding position, and if there are multiple L ^14s , they may be the same or different.)
L ¹⁴ represents a fluorine atom or a linear alkyl group having 1 to 8 carbon atoms,
Z ²⁴ and Z ³⁴ each independently represent -C≡C-, -C≡C-C≡C- or a single bond,
Y ¹⁴ and Y ³⁴ each independently represent a hydrogen atom or a fluorine atom. ) is particularly preferred.
Specific examples of the compound represented by the general formula (I) include compounds represented by the following formulas (I-1) to (I-69).

本発明の化合物は以下の製法で製造することができる。
（製法１）下記式（ｓ－５）で表される化合物の製造

The compound of the present invention can be manufactured by the following manufacturing method.
(Production method 1) Production of a compound represented by the following formula (s-5)

（式中、Ｒ^１ｓ、Ａ^１ｓ、Ａ^２ｓ、Ｚ^１ｓ、Ｚ^２ｓ、Ｚ^３ｓ、ｍ１ｓ、ｍ２ｓ及びA^xsは前記一般式（Ｉ）におけるＲ^１、Ａ^１、Ａ^２、Ｚ^１、Ｚ^２、Ｚ^３、ｍ１、ｍ２及びA^xと同じ意味を表す。）
式（ｓ－１）で表される化合物を式（ｓ－１５）で表される化合物及び硫黄と反応させることにより式（ｓ－２）で表される化合物を得ることができる。
式（ｓ－２）で表される化合物を例えばＮ－ブロモスクシンイミドと反応させることにより式（ｓ－３）で表される化合物を得ることができる。
式（ｓ－３）で表される化合物をトリメチルシリルアセチレンと反応させた後、テトラフルオロアンモニウムフルオライド（ＴＢＡＦ）と反応させることにより一般式（ｓ－４）で表される化合物を得ることができる。反応方法としては例えばパラジウム触媒、銅触媒及び塩基を用いた薗頭カップリング反応が挙げられる。パラジウム触媒の具体例としてはテトラキス（トリフェニルホスフィン）パラジウム（０）等が挙げられる。銅触媒の具体例としてはヨウ化銅（Ｉ）が挙げられる。塩基の具体例としてはトリエチルアミン等が挙げられる。
式（ｓ－４）で表される化合物を式（ｓ－１６）で表される化合物と反応させることにより一般式（ｓ－５）で表される化合物を得ることができる。反応方法としては例えばパラジウム触媒、銅触媒及び塩基を用いた薗頭カップリング反応が挙げられる。パラジウム触媒の具体例としては上記のものが挙げられる。銅触媒の具体例としてはヨウ化銅（Ｉ）が挙げられる。塩基の具体例としてはトリエチルアミン等が挙げられる。
（製法２）下記式（ｓ－１０）で表される化合物の製造

(In the formula, R ^1s , A ^1s , A ^2s , Z ^1s , Z ^2s , Z ^3s , m1s, m2s and A ^xs are R ¹ , A ¹ , A ² , Z ¹ , Z ² in the general formula (I)) , Z ³ , m1, m2 and A ^x .)
A compound represented by formula (s-2) can be obtained by reacting a compound represented by formula (s-1) with a compound represented by formula (s-15) and sulfur.
A compound represented by formula (s-3) can be obtained by reacting a compound represented by formula (s-2) with, for example, N-bromosuccinimide.
A compound represented by general formula (s-4) can be obtained by reacting a compound represented by formula (s-3) with trimethylsilylacetylene and then reacting with tetrafluoroammonium fluoride (TBAF). . Examples of the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of palladium catalysts include tetrakis(triphenylphosphine)palladium(0) and the like. A specific example of the copper catalyst is copper(I) iodide. Specific examples of the base include triethylamine and the like.
A compound represented by general formula (s-5) can be obtained by reacting a compound represented by formula (s-4) with a compound represented by formula (s-16). Examples of the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of palladium catalysts include those listed above. A specific example of the copper catalyst is copper(I) iodide. Specific examples of the base include triethylamine and the like.
(Production method 2) Production of a compound represented by the following formula (s-10)

（式中、Ｒ^１ｓ、Ａ^１ｓ、Ｚ^１ｓ、ｍ１ｓ及びＹ^１ｓは前記一般式（Ｉ）におけるＲ^１、Ａ^１、Ｚ^１、ｍ１及びＹ^１と同じ意味を表す。）
式（ｓ－３）で表される化合物を一般式（ｓ－６）で表される化合物と反応させることにより一般式（ｓ－７）で表される化合物を得ることができる。反応方法としては例えば金属触媒及び塩基存在下、クロスカップリングさせる方法が挙げられる。金属触媒の具体例としては［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド、酢酸パラジウム（ＩＩ）、ジクロロビス［ジ－ｔｅｒｔ－ブチル（ｐ－ジメチルアミノフェニル）ホスフィノ］パラジウム（ＩＩ）、テトラキス（トリフェニルホスフィン）パラジウム（０）等が挙げられる。金属触媒として酢酸パラジウム（ＩＩ）を使用する場合、トリフェニルホスフィン、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル等の配位子を添加してもよい。塩基の具体例としては炭酸カリウム、リン酸カリウム、炭酸セシウム等が挙げられる。
一般式（ｓ－７）で表される化合物を例えばヒドロキシルアミンと反応させることにより一般式（ｓ－８）で表される化合物を得ることができる。
一般式（ｓ－８）で表される化合物を例えばＮ－クロロスクシンイミドと反応させることにより一般式（ｓ－９）で表される化合物を得ることができる。
一般式（ｓ－９）で表される化合物を例えばチオ尿素と反応させることにより一般式（ｓ－１０）で表される化合物を得ることができる。
なお、上記製法１には前記一般式（Ｉ）においてＡ^ｘが前記式（Ａｘ－１）で表される化合物の製法を記しているが、前記一般式（Ｉ）においてＡ^ｘが前記式（Ａｘ－２）で表される化合物についても、一般式（ｓ－１０）で表される化合物と同様の方法で合成することができる。
（製法３）下記式（ｓ－１４）で表される化合物の製造

(In the formula, R ^1s , A ^1s , Z ^1s , m1s and Y ^1s have the same meanings as R ¹ , A ¹ , Z ¹ , m1 and Y ¹ in the general formula (I).)
A compound represented by general formula (s-7) can be obtained by reacting a compound represented by formula (s-3) with a compound represented by general formula (s-6). Examples of the reaction method include a method of cross-coupling in the presence of a metal catalyst and a base. Specific examples of metal catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, and dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium. (II), tetrakis(triphenylphosphine)palladium(0), and the like. When palladium (II) acetate is used as a metal catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl may be added. Specific examples of the base include potassium carbonate, potassium phosphate, cesium carbonate, and the like.
A compound represented by general formula (s-8) can be obtained by reacting a compound represented by general formula (s-7) with, for example, hydroxylamine.
A compound represented by general formula (s-9) can be obtained by reacting a compound represented by general formula (s-8) with, for example, N-chlorosuccinimide.
A compound represented by general formula (s-10) can be obtained by reacting a compound represented by general formula (s-9) with, for example, thiourea.
Note that the above Production Method 1 describes a method for producing a compound in which A ^x in the general formula ( ^I ) is represented by the above formula (Ax-1); The compound represented by Ax-2) can also be synthesized in the same manner as the compound represented by general formula (s-10).
(Production method 3) Production of a compound represented by the following formula (s-14)

式（ｓ－１）で表される化合物を例えばｎ－ブチルリチウム存在下で、硫黄と反応させることにより式（ｓ－１１）で表される化合物を得ることができる。
式（ｓ－１１）で表される化合物を例えばＮ－ブロモスクシンイミドと反応させることにより式（ｓ－１２）で表される化合物を得ることができる。
式（ｓ－１２）で表される化合物をトリメチルシリルアセチレンと反応させた後、テトラフルオロアンモニウムフルオライド（ＴＢＡＦ）と反応させることにより一般式（ｓ－１３）で表される化合物を得ることができる。反応方法としては例えばパラジウム触媒、銅触媒及び塩基を用いた薗頭カップリング反応が挙げられる。パラジウム触媒の具体例としてはテトラキス（トリフェニルホスフィン）パラジウム（０）等が挙げられる。銅触媒の具体例としてはヨウ化銅（Ｉ）が挙げられる。塩基の具体例としてはトリエチルアミン等が挙げられる。
式（ｓ－１３）で表される化合物同士を１，８－ジアザビシクロ[５，５，０]ウンデカ－７－エン（ＤＢＵ）、Ｎ，Ｎ，Ｎ‘，Ｎ’－テトラメチルエチレンジアミン、ヨウ化銅と反応させることにより一般式（ｓ－１４）で表される化合物を得ることができる。

A compound represented by formula (s-11) can be obtained by reacting a compound represented by formula (s-1) with sulfur, for example, in the presence of n-butyllithium.
A compound represented by formula (s-12) can be obtained by reacting a compound represented by formula (s-11) with, for example, N-bromosuccinimide.
A compound represented by general formula (s-13) can be obtained by reacting a compound represented by formula (s-12) with trimethylsilylacetylene and then reacting with tetrafluoroammonium fluoride (TBAF). . Examples of the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of palladium catalysts include tetrakis(triphenylphosphine)palladium(0) and the like. A specific example of the copper catalyst is copper(I) iodide. Specific examples of the base include triethylamine and the like.
The compounds represented by formula (s-13) are combined with 1,8-diazabicyclo[5,5,0]undec-7-ene (DBU), N,N,N',N'-tetramethylethylenediamine, iodination A compound represented by general formula (s-14) can be obtained by reacting with copper.

Reaction conditions other than those described in each step include, for example, Experimental Chemistry Course (edited by the Chemical Society of Japan, published by Maruzen Co., Ltd.), Organic Syntheses (A John Wiley & Sons, Inc., Publication), Beilstein Handbook of Organic Chemistry ( Beilstein- Institut für Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co.K), Fiesers' Reagents for Org anic synthesis (John Wiley & Sons, Inc.) or SciFinder (Chemical Abstracts Service, American Chemical Society), Reaxys (Elsevier Ltd.), and other databases.
Functional groups can be protected in each step as necessary. As a protecting group, for example, GREENE'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS ((Fourth Edition), co-authored by PETER G. M. WUTS, THEODORA W. GREENE, A John Wiley & So. ns, Inc., Publication) etc. Examples include groups.
Further, purification can be performed in each step as necessary. Examples of purification methods include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid separation treatment. Specific examples of purifying agents include silica gel, alumina, and activated carbon.

The compound represented by general formula (I) is preferably used by being added to a liquid crystal composition. When the liquid crystal composition contains a compound represented by general formula (I), it may contain one compound represented by general formula (I), or multiple compounds represented by general formula (I). It may contain. When the liquid crystal composition of the present invention contains a compound represented by general formula (I), the total content of the compound represented by general formula (I) in the liquid crystal composition is 5% by mass or more. is preferably 10% by mass or more and 95% by mass or less, still more preferably 15% by mass or more and 90% by mass or less, and 20% by mass or more and 85% by mass or less. is particularly preferred. Here, "total content of compounds represented by general formula (I)" means, when the liquid crystal composition contains one compound represented by general formula (I), When the liquid crystal composition contains multiple compounds represented by the general formula (I), the total content of the multiple compounds represented by the general formula (I) is means.

The liquid crystal composition containing the compound represented by the general formula (I) preferably has a refractive index anisotropy (Δn, measurement wavelength 589 nm) of 0.15 or more and 1.00 or less. From the viewpoint of the liquid crystal phase temperature range, driving voltage, rotational viscosity, and elastic modulus of the liquid crystal composition, the refractive index anisotropy (Δn) is preferably 0.20 or more and 0.95 or less, and 0.25 or more. and is more preferably 0.90 or less, further preferably 0.30 or more and 0.85 or less, particularly preferably 0.35 or more and 0.80 or less.

A liquid crystal composition containing a compound represented by general formula (I) can be used in a high frequency phase shifter, a phased array antenna, an image recognition device, a distance measuring device, a liquid crystal display element, a liquid crystal lens, or a birefringent lens for stereoscopic image display. When used, the liquid crystal composition containing the compound represented by the general formula (I) preferably has a dielectric anisotropy (Δε(1kHz)) of 2 or more and 60 or less at 1kHz. From the viewpoint of the liquid crystal phase temperature range, storage stability, weather resistance, driving voltage, rotational viscosity, and elastic modulus of the liquid crystal composition, the dielectric constant anisotropy (Δε (1kHz)) at 1kHz is 2.5 or more and 50 or less. It is preferably 3 or more and 40 or less, and particularly preferably 3.5 or more and 30 or less.

A liquid crystal composition containing a compound represented by general formula (I) is preferably used for a high frequency element. The frequency range is preferably 1 MHz or more and 1 THz or less, more preferably 1 GHz or more and 500 GHz or less, even more preferably 2 GHz or more and 300 GHz or less, and 5 GHz or more and 150 GHz or less. It is particularly preferable that there be.

A liquid crystal composition containing a compound represented by general formula (I) is represented by the following general formula (VI).

（式中、Ｒ^２は炭素原子数１から８のアルキル基、炭素原子数１から７のアルコキシ基、炭素原子数２から８のアルケニル基又は炭素原子数２から７のアルケニルオキシ基を表し、
Ａ^３は下記の式（Ａ６－１）から式（Ａ６－８）

(In the formula, ^R2 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms,
^A3 is the following formula (A6-1) to formula (A6-8)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^３が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４は－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_２－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＯＣＯ－ＮＨ－、－ＮＨ－ＣＯＯ－、－ＮＨ－ＣＯ－ＮＨ－、－ＮＨ－Ｏ－、－Ｏ－ＮＨ－、－ＳＣＨ_２－、－ＣＨ_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_２－ＯＣＯ－、－ＣＯＯ－ＣＨ_２－、－ＯＣＯ－ＣＨ_２－、－ＣＨ_２－ＣＯＯ－、－ＣＨ_２－ＯＣＯ－、－ＣＨ＝ＣＨ－、－Ｎ＝Ｎ－、－ＣＨ＝Ｎ－、－Ｎ＝ＣＨ－、－ＣＨ＝Ｎ－Ｎ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^４が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３は１から４の整数を表し、
Ａ^ｙは下記の式（Ａｙ－１）及び式（Ａｙ－２）

(In the formula, the broken line represents the bonding position.) Represents a group selected from (in the formula, the broken line represents the bonding position), but if multiple ^A3s exist, they may be the same or different,
Z ⁴ is -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -CO-, -COO-, -OCO-, -CO-S-, -S- CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, - O-NH-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, -CF ₂ S-, -SCF ₂ -, -CH=CH-COO-, -CH=CH -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO-, -COO-CH ₂ -, -OCO-CH ₂ -, -CH ₂ -COO-, -CH ₂ -OCO-, -CH=CH-, -N=N-, -CH=N -, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or a single bond, but if multiple ^Z4s exist, even if they are the same It is okay to be different,
m3 represents an integer from 1 to 4,
A ^y is the following formula (Ay-1) and formula (Ay-2)

（式中、破線は結合位置を表し、Ｙ^７、Ｙ^９、Ｙ^１０及びＹ^１２は各々独立して水素原子、フッ素原子又は塩素原子を表し、Ｙ^８及びＹ^１１は各々独立してフッ素原子、塩素原子、シアノ基、チオイソシアノ基、ニトロ基、ペンタフルオロスルファニル基、任意の水素原子がフッ素原子に置換された炭素原子数１から８のアルキル基、任意の水素原子がフッ素原子に置換された炭素原子数１から７のアルコキシ基、任意の水素原子がフッ素原子に置換された炭素原子数２から８のアルケニル基又は任意の水素原子がフッ素原子に置換された炭素原子数２から７のアルケニルオキシ基を表すが、ここで１個の－ＣＨ_２－又は２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－若しくは－Ｃ≡Ｃ－によって置換されていても良い。）から選ばれる基を表す。）で表される化合物を含有することが好ましい。

(In the formula, the broken line represents the bonding position, Y ⁷ , Y ⁹ , Y ¹⁰ and Y ¹² each independently represent a hydrogen atom, fluorine atom or chlorine atom, and Y ⁸ and Y ¹¹ each independently represent a fluorine atom. , chlorine atom, cyano group, thioisocyano group, nitro group, pentafluorosulfanyl group, alkyl group having 1 to 8 carbon atoms in which any hydrogen atom is substituted with a fluorine atom, any hydrogen atom in which any hydrogen atom is substituted with a fluorine atom An alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms in which any hydrogen atom is substituted with a fluorine atom, or an alkenyl group having 2 to 7 carbon atoms in which any hydrogen atom is substituted with a fluorine atom. represents an oxy group, where one -CH ₂ - or two or more -CH ₂ - each independently represent -O-, -S-, -CO-, -COO-, -OCO-, - CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO- represents a group selected from (optionally substituted with CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-). ) is preferably contained.

From the viewpoint of the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity, and elastic modulus of the liquid crystal composition, the compound represented by the general formula (VI) has the following general formula (VI-i)

（式中、Ｒ^２１は炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基、炭素原子数２から５のアルケニル基又は炭素原子数２から４のアルケニルオキシ基を表し、
Ａ^３１は上記の式（Ａ６－１）から式（Ａ６－６）から選ばれる基を表すが、Ａ^３１が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４１は－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_２－、－ＣＯＯ－、－ＯＣＯ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＨ＝Ｎ－Ｎ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｎ＝Ｎ－、－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^４１が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３１は１から３の整数を表し、
Ａ^ｙ１は下記の式（Ａｙ－１－ｉ）及び式（Ａｙ－２－ｉ）

(In the formula, ^R21 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms,
A ³¹ represents a group selected from the above formulas (A6-1) to (A6-6), but when multiple A ^31s exist, they may be the same or different,
Z ⁴¹ is -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH=CH-COO-, -OCO -CH=CH-, -CH=CH-, -CH=N-N=CH-, -CF=CF-, -N=N-, -C≡C- or a single bond, but if Z ⁴¹ is plural If present, they may be the same or different;
m31 represents an integer from 1 to 3,
A ^y1 is the following formula (Ay-1-i) and formula (Ay-2-i)

（式中、破線は結合位置を表し、Ｙ^７１、Ｙ^９１、Ｙ^１０１及びＹ^１２１は各々独立して水素原子、フッ素原子又は塩素原子を表し、Ｙ^８１及びＹ^１１１は各々独立してフッ素原子、塩素原子、シアノ基、チオイソシアノ基、ニトロ基、ペンタフルオロスルファニル基、任意の水素原子がフッ素原子に置換されていてもよい炭素原子数１から８のアルキル基、任意の水素原子がフッ素原子に置換されていてもよい炭素原子数１から７のアルコキシ基、任意の水素原子がフッ素原子に置換されていてもよい炭素原子数２から８のアルケニル基又は任意の水素原子がフッ素原子に置換されていてもよい炭素原子数２から７のアルケニルオキシ基を表す。）から選ばれる基を表す。）で表される化合物であることが好ましく、一般式（ＶＩ）で表される化合物は下記の一般式（ＶＩ－ｉｉ）

(In the formula, the broken line represents the bonding position, Y ⁷¹ , Y ⁹¹ , Y ¹⁰¹ and Y ¹²¹ each independently represent a hydrogen atom, fluorine atom or chlorine atom, and Y ⁸¹ and Y ¹¹¹ each independently represent a fluorine atom. , chlorine atom, cyano group, thioisocyano group, nitro group, pentafluorosulfanyl group, alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom, any hydrogen atom replaced with a fluorine atom An optionally substituted alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms which may have any hydrogen atom substituted with a fluorine atom, or an optional hydrogen atom substituted with a fluorine atom. Represents a group selected from (alkenyloxy group having 2 to 7 carbon atoms which may be substituted). ), and the compound represented by general formula (VI) is preferably a compound represented by general formula (VI-ii) below.

（式中、Ｒ^２２は炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基、炭素原子数２から５のアルケニル基又は炭素原子数２から４のアルケニルオキシ基を表し、
Ａ^３２は上記の式（Ａ６－１）から式（Ａ６－５）から選ばれる基を表すが、Ａ^３２が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４２は－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｎ＝Ｎ－、－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^４２が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３２は１、２又は３を表し、
Ｙ^７２及びＹ^９２は各々独立して水素原子、フッ素原子又は塩素原子を表し、Ｙ^８２はフッ素原子、塩素原子、シアノ基、チオイソシアノ基、ニトロ基、ペンタフルオロスルファニル基、任意の水素原子がフッ素原子に置換されていてもよい炭素原子数１から８のアルキル基、任意の水素原子がフッ素原子に置換されていてもよい炭素原子数１から７のアルコキシ基、任意の水素原子がフッ素原子に置換されていてもよい炭素原子数２から８のアルケニル基又は任意の水素原子がフッ素原子に置換されていてもよい炭素原子数２から７のアルケニルオキシ基を表す。）で表される化合物であることがより好ましく、一般式（ＶＩ）で表される化合物は下記の一般式（ＶＩ－ｉｉｉ）

(In the formula, ^R22 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms,
A ³² represents a group selected from the above formulas (A6-1) to (A6-5), but when multiple A ^32s exist, they may be the same or different,
Z ⁴² represents -CF ₂ O-, -OCF ₂ -, -CH=CH-, -CF=CF-, -N=N-, -C≡C- or a single bond, but multiple Z ^42s exist they may be the same or different,
m32 represents 1, 2 or 3;
Y ⁷² and Y ⁹² each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom; Y ⁸² represents a fluorine atom, a chlorine atom, a cyano group, a thioisocyano group, a nitro group, a pentafluorosulfanyl group; An alkyl group having 1 to 8 carbon atoms which may be substituted with an atom, an alkoxy group having 1 to 7 carbon atoms which may have any hydrogen atom substituted with a fluorine atom, or an alkyl group having 1 to 7 carbon atoms which may have any hydrogen atom substituted with a fluorine atom. It represents an optionally substituted alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms, in which any hydrogen atom may be substituted with a fluorine atom. ), and the compound represented by the general formula (VI) is preferably a compound represented by the following general formula (VI-iii).

（式中、Ｒ^２３は炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基又は炭素原子数２から５のアルケニル基を表し、
Ａ^３３は上記の式（Ａ６－１）から式（Ａ６－５）から選ばれる基を表すが、Ａ^３３が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４３は－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－Ｎ＝Ｎ－、－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^４３が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３３は１、２又は３を表し、
Ｙ^７３及びＹ^９３は各々独立して水素原子、フッ素原子又は塩素原子を表し、Ｙ^８３はフッ素原子、塩素原子、シアノ基又はチオイソシアノ基を表す。）で表される化合物であることがさらに好ましく、一般式（ＶＩ）で表される化合物は下記の一般式（ＶＩ－ｉｖ－１）から一般式（ＶＩ－ｉｖ－２１）

(In the formula, ^R23 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms,
A ³³ represents a group selected from the above formulas (A6-1) to (A6-5), but when multiple A ^33s exist, they may be the same or different,
Z ⁴³ represents -CF ₂ O-, -OCF ₂ -, -N=N-, -C≡C-, or a single bond, but if multiple Z ^43s exist, they may be the same or different. well,
m33 represents 1, 2 or 3;
Y ⁷³ and Y ⁹³ each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom, and Y ⁸³ represents a fluorine atom, a chlorine atom, a cyano group, or a thioisocyano group. ) is more preferable, and the compound represented by the general formula (VI) is a compound represented by the following general formulas (VI-iv-1) to (VI-iv-21).

（式中、Ｒ^６１４は炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基又は炭素原子数２から５のアルケニル基を表す。）で表される化合物であることが特に好ましい。

(In the formula, R ⁶¹⁴ represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.) preferable.

A liquid crystal composition containing a compound represented by general formula (I) has the following general formula (III):

（式中、Ｒ^３１及びＲ^３２は各々独立して炭素原子数１から８のアルキル基、炭素原子数１から７のアルコキシ基、炭素原子数２から８のアルケニル基又は炭素原子数２から７のアルケニルオキシ基を表し、
Ａ^３１及びＡ^３２は各々独立して下記の式（Ａ３－１）から式（Ａ３－８）

(In the formula, R ³¹ and R ³² are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms. represents an alkenyloxy group,
A ³¹ and A ³² are each independently expressed by the following formula (A3-1) to formula (A3-8)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^３２が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３１は１から４の整数を表す。）で表される化合物を含有してもよい。

(In the formula, the broken line represents the bonding position.) Represents a group selected from (wherein, the broken line represents the bonding position); however, when multiple A ^32s exist, they may be the same or different;
m31 represents an integer from 1 to 4. ) may also contain a compound represented by.

From the viewpoint of the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity, and elastic modulus of the liquid crystal composition, the compound represented by the general formula (III) has the following general formula (III-i)

（式中、Ｒ^３１１及びＲ^３２１は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基、炭素原子数２から５のアルケニル基又は炭素原子数２から４のアルケニルオキシ基を表し、
Ａ^３１１及びＡ^３２１は各々独立して下記の式（Ａ３１－１）から式（Ａ３１－６）

(In the formula, R ³¹¹ and R ³²¹ are each independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms. represents an alkenyloxy group,
A ³¹¹ and A ³²¹ are each independently expressed by the following formulas (A31-1) to (A31-6)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^３２１が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３１１は１から３の整数を表す。）で表される化合物であることが好ましく、一般式（ＩＩＩ）で表される化合物は下記の一般式（ＩＩＩ－ｉｉ）

(In the formula, the broken line represents the bonding position.) Represents a group selected from (wherein, the broken line represents the bonding position), but if multiple A ^321s exist, they may be the same or different,
m311 represents an integer from 1 to 3. ) The compound represented by the general formula (III) is preferably a compound represented by the following general formula (III-ii)

（式中、Ｒ^３１２及びＲ^３２２は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基、炭素原子数２から５のアルケニル基又は炭素原子数２から４のアルケニルオキシ基を表し、
Ａ^３１２及びＡ^３２２は各々独立して下記の式（Ａ３２－１）から式（Ａ３２－４）

(In the formula, R ³¹² and R ³²² are each independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms. represents an alkenyloxy group,
A ³¹² and A ³²² are each independently expressed by the following formulas (A32-1) to (A32-4)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^３２２が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３１２は１又は２を表す。）で表される化合物であることがより好ましく、一般式（ＩＩＩ）で表される化合物は下記の一般式（ＩＩＩ－ｉｉｉ）

(In the formula, the broken line represents the bonding position.) Represents a group selected from (wherein, the broken line represents the bonding position), but if multiple A ^322s exist, they may be the same or different,
m312 represents 1 or 2. ) is more preferable, and the compound represented by general formula (III) is preferably a compound represented by the following general formula (III-iii).

（式中、Ｒ^３１３及びＲ^３２３は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基又は炭素原子数２から５のアルケニル基を表し、
Ａ^３１３及びＡ^３２３は各々独立して下記の式（Ａ３３－１）及び式（Ａ３３－２）

(In the formula, R ³¹³ and R ³²³ each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms,
A ³¹³ and A ³²³ are each independently represented by the following formula (A33-1) and formula (A33-2)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^３２３が複数存在する場合それらは同一であっても異なっていても良く、
ｍ３１３は１又は２を表す。）で表される化合物であることがさらに好ましく、一般式（ＩＩＩ）で表される化合物は下記の一般式（ＩＩＩ－ｉｖ－１）から一般式（ＩＩＩ－ｉｖ－１０）

(In the formula, the broken line represents the bonding position.) Represents a group selected from (wherein, the broken line represents the bonding position); however, when multiple A ^323s exist, they may be the same or different;
m313 represents 1 or 2. ) is more preferable, and the compound represented by general formula (III) is a compound represented by general formula (III-iv-1) to general formula (III-iv-10) below.

（式中、Ｒ^３１４及びＲ^３２４は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基又は炭素原子数２から５のアルケニル基を表す。）で表される化合物であることが特に好ましい。

(In the formula, R ³¹⁴ and R ³²⁴ each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.) Particularly preferred are compounds that

Further, the compound represented by the general formula (I) may be used by being added to a liquid crystal composition having a neutral or negative dielectric anisotropy (Δε). In that case, the liquid crystal composition containing the compound represented by the general formula (I) preferably has a dielectric anisotropy (Δε) of -20 or more and 2 or less. From the viewpoint of the liquid crystal phase temperature range, storage stability, weather resistance, driving voltage, rotational viscosity and elastic modulus of the liquid crystal composition, the dielectric constant anisotropy (Δε) should be -15 or more and 1.5 or less. It is preferably -10 or more and 1 or less, more preferably -5 or more and 0.5 or less.
When the dielectric anisotropy (Δε) of the liquid crystal composition containing the compound represented by the general formula (I) is neutral or negative, the liquid crystal composition contains the compound represented by the general formula (IV).

（式中、Ｒ^４１及びＲ^４２は各々独立して炭素原子数１から８のアルキル基、炭素原子数１から７のアルコキシ基、炭素原子数２から８のアルケニル基又は炭素原子数２から７のアルケニルオキシ基を表し、
Ａ^４１及びＡ^４２は各々独立して下記の式（Ａ４－１）から式（Ａ４－１１）

(In the formula, R ⁴¹ and R ⁴² are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms. represents an alkenyloxy group,
^A41 and ^A42 are each independently expressed by the following formula (A4-1) to formula (A4-11)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^４１が複数存在する場合それらは同一であっても異なっていても良く、Ａ^４２が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４１及びＺ^４２は各々独立して－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_２－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＯＣＯ－ＮＨ－、－ＮＨ－ＣＯＯ－、－ＮＨ－ＣＯ－ＮＨ－、－ＮＨ－Ｏ－、－Ｏ－ＮＨ－、－ＳＣＨ_２－、－ＣＨ_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_２－ＯＣＯ－、－ＣＯＯ－ＣＨ_２－、－ＯＣＯ－ＣＨ_２－、－ＣＨ_２－ＣＯＯ－、－ＣＨ_２－ＯＣＯ－、－ＣＨ＝ＣＨ－、－Ｎ＝Ｎ－、－ＣＨ＝Ｎ－、－Ｎ＝ＣＨ－、－ＣＨ＝Ｎ－Ｎ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^４１が複数存在する場合それらは同一であっても異なっていても良く、Ｚ^４２が複数存在する場合それらは同一であっても異なっていても良く、
ｍ４１及びｍ４２は各々独立して０から３の整数を表すが、ｍ４１＋ｍ４２は１から３の整数を表す。）で表される化合物を含有しても良い。

(In the formula, the broken line represents the bonding position.) When there are multiple A ^41s , they may be the same or different, and when there are multiple A ^42s , they may be the same. may be or be different;
Z ⁴¹ and Z ⁴² are each independently -O- _, -S-, -OCH 2 -, -CH ₂ O-, -CH ₂ CH ₂ -, -CO-, -COO-, -OCO-, -CO -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, -CF ₂ S-, -SCF ₂ -, -CH=CH- COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO-, -COO _- CH 2 -, -OCO-CH ₂ -, -CH ₂ -COO-, -CH ₂ -OCO-, -CH=CH-, -N= Represents N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or a single bond, but when multiple Z ^41s exist They may be the same or different, and if there are multiple ^Z42s , they may be the same or different,
m41 and m42 each independently represent an integer from 0 to 3, and m41+m42 represents an integer from 1 to 3. ) may also contain a compound represented by.

From the viewpoint of the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity, and elastic modulus of the liquid crystal composition, the compound represented by the general formula (IV) has the following general formula (IV-i)

（式中、Ｒ^４１１及びＲ^４２１は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基、炭素原子数２から５のアルケニル基又は炭素原子数２から４のアルケニルオキシ基を表し、
Ａ^４１１及びＡ^４２１は各々独立して上記の式（Ａ４－１）から式（Ａ４－９）から選ばれる基を表すが、Ａ^４１１が複数存在する場合それらは同一であっても異なっていても良く、Ａ^４２１が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４１１及びＺ^４２１は各々独立して－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_２－、－ＣＯＯ－、－ＯＣＯ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＨ＝Ｎ－Ｎ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^４１１が複数存在する場合それらは同一であっても異なっていても良く、Ｚ^４２１が複数存在する場合それらは同一であっても異なっていても良く、
ｍ４１１及びｍ４２１は各々独立して０から３の整数を表すが、ｍ４１１＋ｍ４２１は１から３の整数を表す。）で表される化合物であることが好ましく、一般式（ＩＶ）で表される化合物は下記の一般式（ＩＶ－ｉｉ）

(In the formula, R ⁴¹¹ and R ⁴²¹ are each independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms. represents an alkenyloxy group,
A ⁴¹¹ and A ⁴²¹ each independently represent a group selected from the above formulas (A4-1) to (A4-9), but when multiple A ^411s exist, they may be the same or different. may be the same, and if there are multiple ^A421s , they may be the same or different;
Z ⁴¹¹ and Z ⁴²¹ each independently represent -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH= CH-COO-, -OCO-CH=CH-, -CH=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or a single bond, but Z ⁴¹¹ When there are multiple Z 421s, they may be the same or different; when there are multiple Z ^421s , they may be the same or different;
m411 and m421 each independently represent an integer from 0 to 3, and m411+m421 represents an integer from 1 to 3. ), and the compound represented by general formula (IV) is preferably a compound represented by general formula (IV-ii) below.

（式中、Ｒ^４１２及びＲ^４２２は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基、炭素原子数２から５のアルケニル基又は炭素原子数２から４のアルケニルオキシ基を表し、
Ａ^４１２及びＡ^４２２は各々独立して上記の式（Ａ４－１）から式（Ａ４－７）から選ばれる基を表すが、Ａ^４１２が複数存在する場合それらは同一であっても異なっていても良く、Ａ^４２２が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４１２及びＺ^４２２は各々独立して－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_２－、－ＣＯＯ－、－ＯＣＯ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－又は単結合を表すが、Ｚ^４１２が複数存在する場合それらは同一であっても異なっていても良く、Ｚ^４２２が複数存在する場合それらは同一であっても異なっていても良く、
ｍ４１２及びｍ４２２は各々独立して０、１又は２を表すが、ｍ４１２＋ｍ４２２は１又は２を表す。）で表される化合物であることがより好ましく、一般式（ＩＶ）で表される化合物は下記の一般式（ＩＶ－ｉｉｉ）

(In the formula, R ⁴¹² and R ⁴²² are each independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms. represents an alkenyloxy group,
A ⁴¹² and A ⁴²² each independently represent a group selected from the above formulas (A4-1) to (A4-7), but when multiple A ^412s exist, they may be the same or different. may be the same, and if there are multiple ^A422s , they may be the same or different;
Z ⁴¹² and Z ⁴²² each independently represent -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ - or a single bond. However, when there are multiple Z ^412s , they may be the same or different, and when there are multiple Z ^422s , they may be the same or different,
m412 and m422 each independently represent 0, 1 or 2, but m412+m422 represents 1 or 2. ) is more preferable, and the compound represented by general formula (IV) is preferably a compound represented by the following general formula (IV-iii).

（式中、Ｒ^４１３及びＲ^４２３は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基又は炭素原子数２から５のアルケニル基を表し、
Ａ^４１３及びＡ^４２３は各々独立して上記の式（Ａ４－１）から式（Ａ４－５）から選ばれる基を表すが、Ａ^４１３が複数存在する場合それらは同一であっても異なっていても良く、Ａ^４２３が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^４１３及びＺ^４２３は各々独立して－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_２－又は単結合を表すが、Ｚ^４１３が複数存在する場合それらは同一であっても異なっていても良く、Ｚ^４２３が複数存在する場合それらは同一であっても異なっていても良く、
ｍ４１３及びｍ４２３は各々独立して０、１又は２を表すが、ｍ４１３＋ｍ４２３は１又は２を表す。）で表される化合物であることがさらに好ましく、一般式（ＩＶ）で表される化合物は下記の一般式（ＩＶ－ｉｖ－１）から一般式（ＩＶ－ｉｖ－８）

(In the formula, R ⁴¹³ and R ⁴²³ each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms,
A ⁴¹³ and A ⁴²³ each independently represent a group selected from the above formulas (A4-1) to (A4-5), but when multiple A ^413s exist, they may be the same or different. may be the same, and if there are multiple ^A423s , they may be the same or different;
Z ⁴¹³ and Z ⁴²³ each independently represent -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ - or a single bond, but if multiple Z ^413s exist, they may be the same or different. If there are multiple Z ^423s , they may be the same or different,
m413 and m423 each independently represent 0, 1 or 2, but m413+m423 represents 1 or 2. ) It is more preferable that the compound represented by the general formula (IV) is a compound represented by the following general formula (IV-iv-1) to general formula (IV-iv-8).

（式中、Ｒ^４１４及びＲ^４２４は各々独立して炭素原子数１から５のアルキル基、炭素原子数１から４のアルコキシ基又は炭素原子数２から５のアルケニル基を表す。）で表される化合物であることが特に好ましい。

(In the formula, R ⁴¹⁴ and R ⁴²⁴ each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.) Particularly preferred are compounds that

A stabilizer may be added to the liquid crystal composition containing the compound represented by the general formula (I) in order to improve its storage stability. Examples of stabilizers that can be used include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, and nitroso compounds. It will be done. When using a stabilizer, the amount added is preferably in the range of 0.005% by mass to 1% by mass, more preferably 0.02% by mass to 0.8% by mass, and 0.03% by mass. to 0.5% by mass is more preferable. Moreover, one type of stabilizer may be used, or two or more types of stabilizers may be used in combination. As a stabilizer, the following general formula (X1)

（式中、Ｓｐ^ｘ１は１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－によって置換されても良い炭素原子数１から２０のアルキレン基又は単結合を表し、Ａ^ｘ１は下記の式（Ａｘ１－１）から式（Ａｘ１－８）

(In the formula, Sp ^x1 is one -CH ₂ - or two or more non-adjacent -CH ₂ - each independently -O-, -S-, -CO-, -COO-, -OCO -, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, an alkylene group or monocarbon group having 1 to 20 carbon atoms; Represents a bond, and A ^x1 is from the following formula (Ax1-1) to formula (Ax1-8)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^ｘ１が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^ｘ１は－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_２－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＯＣＯ－ＮＨ－、－ＮＨ－ＣＯＯ－、－ＮＨ－ＣＯ－ＮＨ－、－ＮＨ－Ｏ－、－Ｏ－ＮＨ－、－ＳＣＨ_２－、－ＣＨ_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_２－ＯＣＯ－、－ＣＯＯ－ＣＨ_２－、－ＯＣＯ－ＣＨ_２－、－ＣＨ_２－ＣＯＯ－、－ＣＨ_２－ＯＣＯ－、－ＣＨ＝ＣＨ－、－Ｎ＝Ｎ－、－ＣＨ＝Ｎ－、－Ｎ＝ＣＨ－、－ＣＨ＝Ｎ－Ｎ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－又は単結合を表すが、Ｚ^ｘ１が複数存在する場合それらは同一であっても異なっていても良く、
ｍｘ１は０又は１を表し、
ｍｘ２は０から４の整数を表す。）で表される化合物が挙げられる。

(In the formula, the broken line represents the bonding position.) Represents a group selected from (wherein, the broken line represents the bonding position), but if multiple A ^x1s exist, they may be the same or different,
Z ^x1 is -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -CO-, -COO-, -OCO-, -CO-S-, -S- CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, - O-NH-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, -CF ₂ S-, -SCF ₂ -, -CH=CH-COO-, -CH=CH -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO-, -COO-CH ₂ -, -OCO-CH ₂ -, -CH ₂ -COO-, -CH ₂ -OCO-, -CH=CH-, -N=N-, -CH=N -, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or a single bond, but if there are multiple Z ^x1s , even if they are the same It is okay to be different,
mx1 represents 0 or 1,
mx2 represents an integer from 0 to 4. ) can be mentioned.

From the viewpoint of voltage holding rate and compatibility with liquid crystal compositions, the compound represented by general formula (X1) is the following general formula (X1-i):

（式中、Ｓｐ^ｘ１１は１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－ＣＯＯ－又は－ＯＣＯ－によって置換されても良い炭素原子数１から２０のアルキレン基又は単結合を表し、Ａ^ｘ１１は下記の式（Ａｘ１１－１）及び式（Ａｘ１１－２）

(In the formula, Sp ^x11 is a carbon in which one -CH ₂ - or two or more non-adjacent -CH ₂ - may each be independently substituted with -O-, -COO- or -OCO-) Represents an alkylene group or single bond having 1 to 20 atoms, and A ^x11 is the following formula (Ax11-1) and formula (Ax11-2)

（式中、破線は結合位置を表す。）から選ばれる基を表すが、Ａ^ｘ１１が複数存在する場合それらは同一であっても異なっていても良く、
Ｚ^ｘ１１は－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－又は単結合を表すが、Ｚ^ｘ１１が複数存在する場合それらは同一であっても異なっていても良く、
ｍｘ１１は０又は１を表し、
ｍｘ２１は０又は１を表す。）で表される化合物であることが好ましく、一般式（Ｘ１）で表される化合物は下記の一般式（Ｘ１－ｉｉ－１）から一般式（Ｘ１－ｉｉ－４）

(In the formula, the broken line represents the bonding position.) represents a group selected from ^A
Z ^x11 represents -COO-, -OCO-, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, or a single bond, but when multiple Z ^x11s exist, they are different even if they are the same. You can leave it there,
mx11 represents 0 or 1,
mx21 represents 0 or 1. ), and the compound represented by general formula (X1) is preferably a compound represented by general formula (X1-ii-1) to general formula (X1-ii-4) below.

（式中、Ｓｐ^ｘ１２は炭素原子数１から２０のアルキレン基又は単結合を表す。）で表される化合物であることが特に好ましい。
また、一般式（Ｉ）で表される化合物を含有する液晶組成物は、下記の一般式（Ｘ２）

(In the formula, Sp ^x12 represents an alkylene group having 1 to 20 carbon atoms or a single bond.) A compound represented by the following is particularly preferred.
In addition, a liquid crystal composition containing a compound represented by general formula (I) can be expressed by the following general formula (X2).

（式中、Ｒ^ｘ２１、Ｒ^ｘ２２、Ｒ^ｘ２３及びＲ^ｘ２４は各々独立して水素原子、酸素原子、ヒドロキシル基、炭素原子数１から２０のアルキル基又は炭素原子数１から２０のアルコキシ基を表し、
Ｓｐ^ｘ２１、Ｓｐ^ｘ２２、Ｓｐ^ｘ２３及びＳｐ^ｘ２４は各々独立してスペーサー基又は単結合を表し、
ｍｘ２１は０又は１を表し、
ｍｘ２２は０又は１を表し、
ｍｘ２３は０又は１を表す。）で表される化合物が挙げられる。

(In the formula, R ^x21 , R ^x22 , R ^x23 and R ^x24 each independently represent a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms. ,
Sp ^x21 , Sp ^x22 , Sp ^x23 and Sp ^x24 each independently represent a spacer group or a single bond,
mx21 represents 0 or 1,
mx22 represents 0 or 1,
mx23 represents 0 or 1. ) can be mentioned.

From the viewpoint of voltage holding rate and compatibility with liquid crystal compositions, the compound represented by general formula (X2) is the following general formula (X2-i).

（式中、Ｒ^ｘ２１１、Ｒ^ｘ２２１、Ｒ^ｘ２３１及びＲ^ｘ２４１は各々独立して水素原子、酸素原子、ヒドロキシル基、炭素原子数１から１０のアルキル基又は炭素原子数１から１０のアルコキシ基を表し、
Ｓｐ^ｘ２１１、Ｓｐ^ｘ２２１、Ｓｐ^ｘ２３１及びＳｐ^ｘ２２４は各々独立して、基中の任意の水素原子がフッ素原子に置換されても良く、１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられても良い炭素原子数１から２０の直鎖状又は分岐状アルキレン基又は単結合を表し、
ｍｘ２１１は０又は１を表し、
ｍｘ２２１は０又は１を表し、
ｍｘ２３１は０又は１を表す。）で表される化合物であることが好ましく、一般式（Ｘ２）で表される化合物は下記の一般式（Ｘ２－ｉｉ）

(In the formula, R ^x211 , R ^x221 , R ^x231 and R ^x241 each independently represent a hydrogen atom, an oxygen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms. ,
Sp ^x211 , Sp ^x221 , Sp ^x231 and Sp ^x224 each independently may have any hydrogen atom in the group substituted with a fluorine atom, one -CH ₂ - or two or more non-adjacent -CH ₂ - each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, - A linear or branched alkylene group having 1 to 20 carbon atoms, which may be replaced with CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, or represents a single bond,
mx211 represents 0 or 1,
mx221 represents 0 or 1,
mx231 represents 0 or 1. ), and the compound represented by general formula (X2) is preferably a compound represented by general formula (X2-ii) below.

（式中、Ｒ^ｘ２１２及びＲ^ｘ２２２は各々独立して水素原子、炭素原子数１から１０のアルキル基又は炭素原子数１から１０のアルコキシ基を表し、
Ｓｐ^ｘ２１２及びＳｐ^ｘ２２２は各々独立して、１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－ＣＯＯ－又は－ＯＣＯ－に置き換えられても良い炭素原子数１から１０の直鎖状アルキレン基又は単結合を表し、
ｍｘ２１２は０又は１を表す。）で表される化合物であることがより好ましく、一般式（Ｘ２）で表される化合物は下記の一般式（Ｘ２－ｉｉｉ）

(In the formula, R ^x212 and R ^x222 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms,
Sp ^x212 and Sp ^x222 each independently have one -CH ₂ - or two or more non-adjacent -CH ₂ -s each independently replaced with -O-, -COO- or -OCO-. represents a linear alkylene group or single bond having 1 to 10 carbon atoms, which may be
mx212 represents 0 or 1. ), and the compound represented by the general formula (X2) is preferably a compound represented by the following general formula (X2-iii).

（式中、Ｒ^ｘ２１３及びＲ^ｘ２２３は各々独立して水素原子、炭素原子数１から１０のアルキル基又は炭素原子数１から１０のアルコキシ基を表し、
Ｓｐ^ｘ２１３は１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－ＣＯＯ－又は－ＯＣＯ－に置き換えられても良い炭素原子数１から１０の直鎖状アルキレン基を表す。）で表される化合物であることが特に好ましい。

(In the formula, R ^x213 and R ^x223 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms,
Sp ^x213 is a straight chain with 1 to 10 carbon atoms in which one -CH ₂ - or two or more non-adjacent -CH ₂ -s may each be independently replaced with -COO- or -OCO- represents an alkylene group. ) is particularly preferred.

In the present invention, the ring structure contained in the 1,4-cyclohexylene group, the decahydronaphthalene-2,6-diyl group, and the 1,3-dioxane-2,5-diyl group may be either a trans form or a cis form, respectively. However, from the viewpoint of liquid crystallinity, it is preferable that the content of the trans isomer is higher than the content of the cis isomer, and it is more preferable that the content of the trans isomer in the ring structure is 80% or more. It is more preferable that the trans isomer content in the ring structure is 90% or more, it is even more preferable that the trans isomer content in the ring structure is 95% or more, and the trans isomer content in the ring structure is 98% or more. % or more is particularly preferable. In addition, in the present invention, the following notation (CY-1)

（式中、破線は結合位置を表す。）は１，４－シクロヘキシレン基のトランス体及び／又はシス体を意味する。
また、本願発明において、各元素は同じ元素の同位体に置き換えられていても良い。

(In the formula, the broken line represents the bonding position.) means the trans isomer and/or the cis isomer of the 1,4-cyclohexylene group.
Furthermore, in the present invention, each element may be replaced with an isotope of the same element.

The present invention will be further described below with reference to Examples, but the present invention is not limited to these Examples. Moreover, "%" in the compositions of the following examples and comparative examples means "mass %". When handling substances unstable to oxygen and/or moisture in each step, it is preferable to perform the work in an inert gas such as nitrogen gas or argon gas. The purity of each compound was determined by UPLC (Waters ACQUITY UPLC, BEH C ₁₈ (100 x 2.1 mm x 1.7 μm), acetonitrile/water or acetonitrile/water containing 0.1% formic acid, PDA, column temperature 40 °C), GPC ( Shimadzu HPLC Prominence, Shodex KF-801 (300 mm x 8 mm x 6 μm) + KF-802 (300 mm x 8 mm x 6 μm), tetrahydrofuran, RI, UV (254 nm), column temperature 40°C), GC (Agilent 6890A, J&W DB- 1, 30 m x 0.25 mm x 0.25 μm, carrier gas He, FID, 100 °C (1 minute) → temperature increase 10 °C/min → 300 °C (12 minutes)) or determined by ¹ H NMR (JEOL, 400 MHz) did.

Further, the extrapolated value of the refractive index anisotropy (Δn, measurement wavelength 589 nm) was obtained by adding 5% of the base liquid crystal N composed of the following compound.
(Material liquid crystal N)
2-Ph3-T-PhPh-3 20.0%
4-Ph3-T-PhPh-3 36.0%
3-Ph1Ph1Ph-Cl 10.0%
5-Ph1Ph1Ph-Cl 20.0%
5-CyPhPh1Ph-2 7.0%
5-CyPhPh1Ph-3 7.0%
(Example 1) Production of compound represented by formula (I-1)

窒素雰囲気下、反応容器に式（Ｉ－１－１）で表される化合物１５ｇ、テトラヒドロフラン（ＴＨＦ）４０ｍＬを加えた。反応容器を－７８℃に冷却しながら、ｎ－ブチルリチウム（２．６ｍｏｌ／ｌ）を５０ｍｌゆっくり滴下し、－７８℃で３０分攪拌した。次いで硫黄４ｇを少量ずつ加え、－７８℃で更に１時間攪拌した。更に－７８℃で１－ブロモペンタンをゆっくり滴下し、－３０℃で１時間撹拌した。反応液に酢酸エチル２ｍｌを滴下し、反応液を０℃に戻し、飽和塩化アンモニウム水溶液を注ぎ、酢酸エチルを加え分液処理した。有機層を食塩水で洗浄し、カラムクロマトグラフィー（シリカゲル、ジクロロメタン／ヘキサン）により精製を行うことによって、式（Ｉ－１－２）で表される化合物２０ｇを得た。
反応容器に式（Ｉ－１－２）で表される化合物２０ｇ、ジクロロメタン９９ｍＬを加えた。氷冷しながら、Ｎ－ブロモスクシンイミド１５ｇを少量ずつ加え、室温で５時間撹拌した。反応液を水に注ぎ、分液処理した。有機層を食塩水で洗浄し、カラムクロマトグラフィー（シリカゲル、ジクロロメタン／ヘキサン）により精製を行うことによって、式（Ｉ－１－３）で表される化合物２４ｇを得た。
窒素雰囲気下、反応容器に式（Ｉ－１－３）で表される化合物２４ｇ、ヨウ化銅（Ｉ）０．２ｇ、テトラキストリフェニルフォスフィンパラジウム１ｇ、トリエチルアミン１５ｍＬ、Ｎ，Ｎ－ジメチルホルムアミド（ＤＭＦ）１００ｍＬを加えた。７０℃で加熱しながら、トリメチルシリルアセチレン９．０ｇを滴下し、７０℃で４時間加熱撹拌した。反応液を水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）及び活性炭処理により精製を精製した。次いでメタノール１２０ｍＬ、炭酸カリウム４．５ｇを加え、室温で８時間撹拌した。反応液に水を加え、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）により精製を行うことによって、式（Ｉ－１－４）で表される化合物１３ｇを得た。
窒素雰囲気下、反応容器に式（Ｉ－１－５）で表される化合物９ｇ、ヨウ化銅（Ｉ）０．１５ｇ、テトラキストリフェニルフォスフィンパラジウム０．５ｇ、トリエチルアミン１５ｍＬ、ＤＭＦ６０ｍＬを加えた。８０℃で加熱しながら、式（Ｉ－１－４）で表される化合物１３ｇのＤＭＦ３０ｍｌを滴下し、８０℃で４時間加熱撹拌した。反応液を水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）及び活性炭処理を行うことによって、式（Ｉ－１－６）で表される化合物１８ｇを得た。
反応容器に式（Ｉ－１－６）で表される化合物１８ｇ、酢酸ナトリウム３．６ｇ、メタノール７４ｍＬを加えた。室温で塩酸ヒドロキシルアミン３ｇを加え、１０時間撹拌した。反応液を水に注ぎ、ジクロロメタンで抽出した。有機層を水、飽和炭酸水素ナトリウム水溶液及び食塩水で順次洗浄した後、溶媒を留去し乾燥させることによって、式（Ｉ－１－７）で表される化合物１５ｇを得た。
反応容器に式（Ｉ－１－７）で表される化合物１５ｇ、ＤＭＦ １００ｍＬを加えた。氷冷しながらＮ－クロロスクシンイミド ６．７ｇを加え、４０℃で２時間加熱撹拌した。反応液を冷却し水に注ぎ、ジクロロメタンで抽出した。有機層を水及び食塩水で順次洗浄した後、溶媒を留去し乾燥させることによって、式（Ｉ－１－８）で表される化合物１５ｇを得た。
反応容器に式（Ｉ－１－８）で表される化合物１５ｇ、チオ尿素６．６ｇ、テトラヒドロフラン１１０ｍＬを加えた。氷冷しながらトリエチルアミン１５ｇを滴下し、４０℃で５時間加熱撹拌した。反応液を冷却し水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）、活性炭処理及び再結晶（トルエン／エタノール）により精製を行うことによって、式（Ｉ－１）で表される化合物１２ｇを得た。
ＭＳ（ＥＩ）：ｍ／ｚ＝４３５
融点 １１３℃
相転移温度 Ｃｒ１１３ Ｎ ２２７Ｉｓｏ
（実施例２）式（Ｉ－２）で表される化合物の製造

Under a nitrogen atmosphere, 15 g of the compound represented by formula (I-1-1) and 40 mL of tetrahydrofuran (THF) were added to the reaction vessel. While cooling the reaction vessel to -78°C, 50 ml of n-butyllithium (2.6 mol/l) was slowly added dropwise, and the mixture was stirred at -78°C for 30 minutes. Next, 4 g of sulfur was added little by little, and the mixture was further stirred at -78°C for 1 hour. Furthermore, 1-bromopentane was slowly added dropwise at -78°C, and the mixture was stirred at -30°C for 1 hour. 2 ml of ethyl acetate was added dropwise to the reaction solution, the temperature of the reaction solution was returned to 0° C., a saturated ammonium chloride aqueous solution was poured thereinto, and ethyl acetate was added thereto for liquid separation. The organic layer was washed with brine and purified by column chromatography (silica gel, dichloromethane/hexane) to obtain 20 g of a compound represented by formula (I-1-2).
20 g of the compound represented by formula (I-1-2) and 99 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 15 g of N-bromosuccinimide was added little by little, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into water and subjected to liquid separation. The organic layer was washed with brine and purified by column chromatography (silica gel, dichloromethane/hexane) to obtain 24 g of the compound represented by formula (I-1-3).
Under a nitrogen atmosphere, 24 g of the compound represented by formula (I-1-3), 0.2 g of copper(I) iodide, 1 g of tetrakistriphenylphosphine palladium, 15 mL of triethylamine, and N,N-dimethylformamide ( 100 mL of DMF) was added. While heating at 70°C, 9.0 g of trimethylsilylacetylene was added dropwise, and the mixture was heated and stirred at 70°C for 4 hours. The reaction solution was poured into water and extracted with toluene. After sequentially washing the organic layer with water and brine, it was purified by column chromatography (silica gel, toluene/hexane) and activated carbon treatment. Next, 120 mL of methanol and 4.5 g of potassium carbonate were added, and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction solution, and the mixture was extracted with toluene. The organic layer was sequentially washed with water and brine, and then purified by column chromatography (silica gel, toluene/hexane) to obtain 13 g of a compound represented by formula (I-1-4).
Under a nitrogen atmosphere, 9 g of the compound represented by formula (I-1-5), 0.15 g of copper (I) iodide, 0.5 g of tetrakistriphenylphosphine palladium, 15 mL of triethylamine, and 60 mL of DMF were added to the reaction vessel. While heating at 80°C, 13g of the compound represented by formula (I-1-4) in 30ml of DMF was added dropwise, and the mixture was heated and stirred at 80°C for 4 hours. The reaction solution was poured into water and extracted with toluene. After sequentially washing the organic layer with water and brine, column chromatography (silica gel, toluene/hexane) and activated carbon treatment were performed to obtain 18 g of a compound represented by formula (I-1-6).
18 g of the compound represented by formula (I-1-6), 3.6 g of sodium acetate, and 74 mL of methanol were added to the reaction vessel. 3 g of hydroxylamine hydrochloride was added at room temperature and stirred for 10 hours. The reaction solution was poured into water and extracted with dichloromethane. After sequentially washing the organic layer with water, a saturated aqueous sodium bicarbonate solution, and brine, the solvent was distilled off and dried to obtain 15 g of a compound represented by formula (I-1-7).
15 g of the compound represented by formula (I-1-7) and 100 mL of DMF were added to the reaction vessel. While cooling with ice, 6.7 g of N-chlorosuccinimide was added, and the mixture was heated and stirred at 40° C. for 2 hours. The reaction solution was cooled, poured into water, and extracted with dichloromethane. After sequentially washing the organic layer with water and brine, the solvent was distilled off and dried to obtain 15 g of a compound represented by formula (I-1-8).
15 g of the compound represented by formula (I-1-8), 6.6 g of thiourea, and 110 mL of tetrahydrofuran were added to the reaction vessel. 15 g of triethylamine was added dropwise while cooling with ice, and the mixture was heated and stirred at 40° C. for 5 hours. The reaction solution was cooled, poured into water, and extracted with toluene. After sequentially washing the organic layer with water and brine, purification was performed by column chromatography (silica gel, toluene/hexane), activated carbon treatment, and recrystallization (toluene/ethanol). By doing so, 12 g of a compound represented by formula (I-1) was obtained.
MS (EI): m/z=435
Melting point 113℃
Phase transition temperature Cr113N227Iso
(Example 2) Production of compound represented by formula (I-2)

反応容器に式（Ｉ－２－１）で表される化合物 ５ｇ、ヨウ化銅（Ｉ）０．０５ｇ、テトラキストリフェニルフォスフィンパラジウム０．１５ｇ、トリエチルアミン７ｍＬ、Ｎ，Ｎ－ジメチルホルムアミド（ＤＭＦ）５０ｍＬを加えた。７０℃で加熱しながら、式（Ｉ－２－２）で表される化合物 ３．２ｇのＤＭＦ溶液１０ｍｌを滴下し、７０℃で４時間加熱撹拌した。反応液を水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）及び活性炭処理により精製を精製し式（Ｉ－２）で表される化合物を製造した。
性状：油状
ＭＳ（ＥＩ）：ｍ／ｚ＝４２０
（実施例３）式（Ｉ－３）で表される化合物の製造

In a reaction vessel, 5 g of the compound represented by formula (I-2-1), 0.05 g of copper (I) iodide, 0.15 g of tetrakistriphenylphosphine palladium, 7 mL of triethylamine, and N,N-dimethylformamide (DMF). Added 50 mL. While heating at 70°C, 10ml of a DMF solution containing 3.2g of the compound represented by formula (I-2-2) was added dropwise, and the mixture was heated and stirred at 70°C for 4 hours. The reaction solution was poured into water and extracted with toluene. The organic layer was washed successively with water and brine, and then purified by column chromatography (silica gel, toluene/hexane) and activated carbon treatment to produce a compound represented by formula (I-2).
Properties: Oil MS (EI): m/z=420
(Example 3) Production of compound represented by formula (I-3)

実施例２において式（Ｉ－２－２）で表される化合物を式（Ｉ－３－４）で表される化合物に置き換えた以外は同様の方法によって、式（Ｉ－３）で表される化合物を製造した。
ＭＳ（ＥＩ）：ｍ／ｚ＝５１２
融点 ６５℃
相転移温度 Ｃｒ６５ Ｎ １０１ Ｉｓｏ
（実施例４）式（Ｉ－４）で表される化合物の製造

A compound represented by formula (I-3) was prepared in the same manner as in Example 2 except that the compound represented by formula (I-2-2) was replaced with a compound represented by formula (I-3-4). A compound was prepared.
MS (EI): m/z=512
Melting point 65℃
Phase transition temperature Cr65 N 101 Iso
(Example 4) Production of compound represented by formula (I-4)

窒素雰囲気下、実施例１と同様に式（Ｉ－４－１）で表される化合物１０ｇと式（Ｉ－４－２）で表される化合物１５ｇを反応させて後、実施例１と同様にＮ－ブロモスクシンイミド１１ｇを少量ずつ加え、室温で５時間撹拌した。反応液を水に注ぎ、分液処理した。有機層を食塩水で洗浄し、カラムクロマトグラフィー（シリカゲル、ジクロロメタン／ヘキサン）により精製を行うことによって、式（Ｉ－４－４）で表される化合物１９ｇを得た。
窒素雰囲気下、反応容器に式（Ｉ－４－４）で表される化合物１９ｇ、酢酸カリウム１４ｇ、ビス（ピナコラト）ジボロン１４ｇ、ジメチルスルホキシド９０ｍＬ、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド ジクロロメタン付加物０．４ｇを加え、８０℃で６時間加熱撹拌した。反応液を水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（アルミナ、ジクロロメタン）により精製を行うことによって、式（Ｉ－４－５）で表される化合物１７ｇを得た。
窒素雰囲気下、反応容器に式（Ｉ－４－５）で表される化合物１７ｇ、炭酸カリウム８ｇ、１－ブロモ－３，４，５－トリフルオロベンゼン ８．５ｇ、トルエン６０ｍＬ、エタノール２０ｍＬ、水１５ｍＬ、ビス（トリフェニルホスフィン）パラジウム（ＩＩ）ジクロリド０．２ｇを加え、６時間加熱還流させた。反応液を水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）及び再結晶（トルエン／エタノール）により精製を行うことによって、式（Ｉ－４）で表される化合物１３ｇを得た。
ＭＳ（ＥＩ）：ｍ／ｚ＝４４０
（実施例５）式（Ｉ－５）で表される化合物の製造

Under a nitrogen atmosphere, 10 g of the compound represented by formula (I-4-1) and 15 g of the compound represented by formula (I-4-2) were reacted in the same manner as in Example 1, and then in the same manner as in Example 1. 11 g of N-bromosuccinimide was added little by little to the mixture, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into water and subjected to liquid separation. The organic layer was washed with brine and purified by column chromatography (silica gel, dichloromethane/hexane) to obtain 19 g of the compound represented by formula (I-4-4).
Under a nitrogen atmosphere, 19 g of the compound represented by formula (I-4-4), 14 g of potassium acetate, 14 g of bis(pinacolato)diboron, 90 mL of dimethyl sulfoxide, and [1,1'-bis(diphenylphosphino)ferrocene] were placed in a reaction container. ] 0.4 g of palladium (II) dichloride dichloromethane adduct was added, and the mixture was heated and stirred at 80° C. for 6 hours. The reaction solution was poured into water and extracted with toluene. The organic layer was sequentially washed with water and brine, and then purified by column chromatography (alumina, dichloromethane) to obtain 17 g of a compound represented by formula (I-4-5).
Under a nitrogen atmosphere, 17 g of the compound represented by formula (I-4-5), 8 g of potassium carbonate, 8.5 g of 1-bromo-3,4,5-trifluorobenzene, 60 mL of toluene, 20 mL of ethanol, and water were placed in a reaction container. 15 mL and 0.2 g of bis(triphenylphosphine)palladium(II) dichloride were added, and the mixture was heated under reflux for 6 hours. The reaction solution was poured into water and extracted with toluene. After sequentially washing the organic layer with water and brine, purification was performed by column chromatography (silica gel, toluene/hexane) and recrystallization (toluene/ethanol) to obtain 13 g of the compound represented by formula (I-4). I got it.
MS (EI): m/z=440
(Example 5) Production of compound represented by formula (I-5)

ＷＯ２０１０／１１５２７９Ａ１号公報に記載の方法によって、式（Ｉ－５－２）で表される化合物を製造した。窒素雰囲気下、反応容器に式（Ｉ－５－１）で表される化合物１０ｇ、式（Ｉ－１２－２）で表される化合物９．５ｇ、炭酸カリウム１３．５ｇ、ジクロロビス［ジ－ｔ－ブチル（ｐ－ジメチルアミノフェニル）ホスフィノ］パラジウム（ＩＩ）０．１ｇ、トルエン８０ｍＬ、エタノール３０ｍＬ、水２０ｍＬを加え、６時間加熱還流させた。反応液を水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）及び再結晶（トルエン／エタノール）により精製を行うことによって、式（Ｉ－５－３）で表される化合物１０ｇを得た。
実施例１において式（Ｉ－１－６）で表される化合物を式（Ｉ－５－３）で表される化合物に置き換えた以外は同様の方法によって、式（Ｉ－５）で表される化合物７ｇを製造した。
ＭＳ（ＥＩ）：ｍ／ｚ＝４２３
（実施例６）式（Ｉ－６）で表される化合物の製造

A compound represented by formula (I-5-2) was produced by the method described in WO2010/115279A1. Under a nitrogen atmosphere, 10 g of the compound represented by formula (I-5-1), 9.5 g of the compound represented by formula (I-12-2), 13.5 g of potassium carbonate, dichlorobis[di-t 0.1 g of -butyl(p-dimethylaminophenyl)phosphino]palladium(II), 80 mL of toluene, 30 mL of ethanol, and 20 mL of water were added, and the mixture was heated under reflux for 6 hours. The reaction solution was poured into water and extracted with toluene. After sequentially washing the organic layer with water and brine, purification is performed by column chromatography (silica gel, toluene/hexane) and recrystallization (toluene/ethanol) to obtain a compound represented by formula (I-5-3). 10 g of compound was obtained.
A compound represented by formula (I-5) was prepared in the same manner as in Example 1 except that the compound represented by formula (I-1-6) was replaced with a compound represented by formula (I-5-3). 7 g of the compound was prepared.
MS (EI): m/z=423
(Example 6) Production of compound represented by formula (I-6)

反応容器に式（Ｉ－６－１）で表される化合物 ５ｇ、ヨウ化銅（Ｉ）０．０５ｇ、テトラキストリフェニルフォスフィンパラジウム０．２５ｇ、トリエチルアミン２５ｍＬ、Ｎ，Ｎ－ジメチルホルムアミド（ＤＭＦ）２５ｍＬを加えた。８０℃で４時間加熱撹拌した。反応液を水に注ぎ、トルエンで抽出した。有機層を水及び食塩水で順次洗浄した後、カラムクロマトグラフィー（シリカゲル、トルエン／ヘキサン）及び活性炭処理により精製を精製し式（Ｉ－６）で表される化合物を２．４ｇ製造した。
融点 ９６℃
ＭＳ（ＥＩ）：ｍ／ｚ＝５３０

In a reaction vessel, 5 g of the compound represented by formula (I-6-1), 0.05 g of copper (I) iodide, 0.25 g of tetrakistriphenylphosphine palladium, 25 mL of triethylamine, and N,N-dimethylformamide (DMF). Added 25 mL. The mixture was heated and stirred at 80°C for 4 hours. The reaction solution was poured into water and extracted with toluene. The organic layer was sequentially washed with water and brine, and then purified by column chromatography (silica gel, toluene/hexane) and activated carbon treatment to produce 2.4 g of the compound represented by formula (I-6).
Melting point 96℃
MS (EI): m/z=530

(Example 7 to Example 15 and Comparative Examples 1 to 8)
In the examples, the following abbreviations are used to describe liquid crystal compounds.
(ring structure)

（側鎖構造）
２－ ＣＨ_３ＣＨ_２－
３－ ＣＨ_３（ＣＨ_２）_２－
４－ ＣＨ_３（ＣＨ_２）_３－
５－ ＣＨ_３（ＣＨ_２）_４－
－２ －ＣＨ_２ＣＨ_３
－３ －（ＣＨ_２）_２ＣＨ_３
－４ －（ＣＨ_２）_３ＣＨ_３
－５ －（ＣＨ_２）_４ＣＨ_３
－Ｃｌ －Ｃｌ
（連結基）
－ 単結合
－Ｔ－ －Ｃ≡Ｃ－

(Side chain structure)
2- CH ₃ CH ₂ -
3- CH ₃ (CH ₂ ) ₂ -
4- CH ₃ (CH ₂ ) ₃ -
5- CH ₃ (CH ₂ ) ₄ -
-2 -CH ₂ CH ₃
-3 -(CH ₂ ) ₂ CH ₃
-4 -(CH ₂ ) ₃ CH ₃
-5 -(CH ₂ ) ₄ CH ₃
-Cl -Cl
(linking group)
- Single bond -T- -C≡C-

A base liquid crystal N composed of the following compounds was prepared.
(Material liquid crystal N)
2-Ph3-T-PhPh-3 20.0%
4-Ph3-T-PhPh-3 36.0%
3-Ph1Ph1Ph-Cl 10.0%
5-Ph1Ph1Ph-Cl 20.0%
5-CyPhPh1Ph-2 7.0%
5-CyPhPh1Ph-3 7.0%

Compounds represented by formulas (I-6) from (I-1) synthesized in Examples were added to the base liquid crystal N, and liquid crystal compositions (M- 6) was prepared. In addition, the compound represented by the formula (R-1) described in Non-Patent Document 1, the compound represented by the formula (R-2) described in Patent Document 1, the compound represented by (R-3), and A liquid crystal composition (RM-4) was prepared from a comparative liquid crystal composition (RM-1) by adding a compound represented by formula (R-4) described in Patent Document 3.

(Liquid crystal composition (M-1))
Base liquid crystal N 90.0%
Compound represented by formula (I-1) 10.0%
(Liquid crystal composition (M-2))
Base liquid crystal N 90.0%
Compound represented by formula (I-2) 10.0%
(Liquid crystal composition (M-3))
Base liquid crystal N 90.0%
Compound represented by formula (I-3) 10.0%
(Liquid crystal composition (M-4))
Base liquid crystal N 90.0%
Compound represented by formula (I-4) 10.0%
(Liquid crystal composition (M-5))
Base liquid crystal N 90.0%
Compound represented by formula (I-5) 10.0%
(Liquid crystal composition (M-6))
Base liquid crystal N 90.0%
Compound represented by formula (I-6) 10.0%
Storage stability was evaluated for each compound to be evaluated. Storage stability was evaluated visually after 2 mL of each prepared liquid crystal composition was sealed in a glass vial under an argon atmosphere and stored at 10° C. for 4 weeks. The evaluation results are shown in the table below.

上記の結果から、本発明の化合物は液晶組成物へ添加した場合に析出が起こりにくく、液晶組成物への相溶性が高いことがわかる。

From the above results, it can be seen that the compound of the present invention hardly causes precipitation when added to a liquid crystal composition, and has high compatibility with the liquid crystal composition.

Next, the characteristics of each compound to be evaluated in the high frequency region were evaluated. For the measurement, a transmission delay type cut back type strip line method relative dielectric constant/dielectric loss tangent measuring instrument (manufactured by KEYCOM) was used. The dielectric anisotropy at 13.17 GHz and 20° C. was measured for each of the prepared liquid crystal compositions, and the dielectric anisotropy Δε (13.17 GHz) of each compound to be evaluated was calculated by extrapolation. The evaluation results are shown in Table 2 below.

上記の結果から、本発明の化合物はいずれも高周波数領域において大きな誘電率異方性を示すことがわかる。本発明の化合物は、環構造及び連結基を介して広い共役系を形成しているため、高周波数領域において大きな誘電率異方性を示すと考えられる。
また、本発明の化合物を含有する液晶組成物（Ｍ－１）から（Ｍ－６）について、材料特性（ηε）がいずれも２０以上を示すことがわかった。材料特性（ηε）は下記のように定義される。

The above results show that all the compounds of the present invention exhibit large dielectric anisotropy in the high frequency region. Since the compound of the present invention forms a wide conjugated system through a ring structure and a connecting group, it is thought that it exhibits large dielectric constant anisotropy in a high frequency region.
Furthermore, it was found that the liquid crystal compositions (M-1) to (M-6) containing the compound of the present invention all exhibited material properties (ηε) of 20 or more. The material properties (ηε) are defined as follows.

ε _⊥ = (3ε _average −ε _∥ )/2
tanδ _⊥ = (3ε _average tanδ _average −ε _∥ tanδ _∥ )/2ε _⊥
Modulation ability (τ) = (ε _∥ - ε _⊥ )/ε _∥
Material properties (ηε) = τ/(max(tanδ _∥ , tanδ _⊥ ))

From the above results, the compound of the present invention has a large refractive index anisotropy Δn, is highly compatible with liquid crystal compositions, and exhibits a large dielectric constant anisotropy in a high frequency region. It is useful as a material for elements such as a container, a phased array antenna, an image recognition device, a distance measuring device, a liquid crystal display element, a liquid crystal lens, or a birefringent lens for stereoscopic image display.

Claims (10)

General formula (I) below

(In the formula,
R ¹ represents a hydrogen atom, a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms,
Any hydrogen atom in the alkyl group may be substituted with a halogen atom,
One or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S- Although it may be replaced with CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-,
Oxygen atoms do not bond with each other,
A ¹ and A ² are each independently,
(a) 1,4-cyclohexylene group (one -CH ₂ - or two or more non-adjacent -CH ₂ -s present in this group is replaced with -O- or -S-) is also good.)
(b) 1,4-phenylene group (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1 ,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6- diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (the hydrogen atoms present in these groups are fluorine may be substituted with an atom or a chlorine atom, and naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5 , 6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7- One -CH= or two or more -CH= present in the diyl group may be replaced with -N=.)
(d) Thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= present in this group is replaced with -N= )
represents a group selected from the group consisting of,
These groups may be unsubstituted or substituted with one or more substituents ^L1 ,
L ¹ is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropyl Amino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one -CH ₂ - or two or more -CH ₂ - each independently -O-, -S-, -CO-, -COO -, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH 1 to 20 carbon atoms optionally substituted with -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- represents a linear alkyl group or a branched or cyclic alkyl group having 3 to 20 carbon atoms,
Oxygen atoms do not bond directly to each other,
Any hydrogen atom in the alkyl group may be substituted with a fluorine atom,
If there are multiple ^A1s , they may be the same or different;
If there are multiple ^A2s , they may be the same or different;
Z ¹ , Z ² and Z ³ are each independently a single bond, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -CH ₂ O -, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CHCOO-, -OCOCH=CH-, -CH=C(CH ₃ )COO-, -OCOC(CH ₃ )=CH- , -CH ₂ -CH(CH ₃ )COO-, -OCOCH(CH ₃ )-CH ₂ -, -OCH ₂ CH ₂ O-, -N=N-, -C≡C-C≡C- or carbon atom represents an alkylene group of numbers 2 to 20,
One or more -CH ₂ - in this alkylene group may be substituted with -O-, -S-, -COO- or -OCO-,
Oxygen atoms do not bond directly to each other,
If there are multiple Z ^1s , they may be the same or different,
If there are multiple ^Z2s , they may be the same or different,
m1 and m2 each independently represent an integer from 0 to 3,
A ^x represents a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms,
Any hydrogen atom in the alkyl group may be substituted with a halogen atom,
One or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S- Although it may be replaced with CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, the oxygen atom They do not combine with each other,
Alternatively, A ^x can be expressed using the following formulas (Ax-1) to (Ax-5)

(In the formula,
The dashed line represents the bond position;
Y ¹ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or an alkyl group or alkoxy group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom,
If there are multiple Y ^1s , they may be the same or different,
^Y2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or an alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom,
One or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S- Although it may be replaced with CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, the oxygen atom They cannot be combined with each other. )
represents a structure selected from the group consisting of,
Here, when A ^x has a structure selected from the group consisting of formulas (Ax-1) to (Ax-5), m1+m2 represents an integer from 0 to 3,
When A ^x does not have a structure selected from the group consisting of formulas (Ax-1) to (Ax-5), m1+m2 represents an integer from 1 to 4. )
A compound represented by The above general formula (I) is replaced by the following general formula (I-i)

(In the formula,
R ¹¹ is a hydrogen atom, any hydrogen atom in the group may be substituted with a halogen atom, and one or more -CH ₂ - in the group are each independently -O-, -S- , -CH=CH-, -CF=CF- or -C≡C- represents a linear or branched alkyl group having 1 to 20 carbon atoms,
A ¹¹ and A ²¹ each independently represent a 1,4-phenylene group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, or a 5,6,7,8-tetrahydronaphthalene-1,4- Diyl group, phenanthrene-2,7-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group group or thieno[3,2-b]thiophene-2,5-diyl group,
If there are multiple ^A11s , they may be the same or different;
If there are multiple ^A21s , they may be the same or different;
These groups may be unsubstituted or substituted with one or more substituents ^L11 ,
In L ¹¹ , a fluorine atom, a chlorine atom, or any hydrogen atom in the group may be substituted with a fluorine atom, and one -CH ₂ - or two or more -CH ₂ - in the group are each independently A linear alkyl group having 1 to 20 carbon atoms or 3 carbon atoms which may be substituted with -O-, -S-, -CH=CH-, -CF=CF- or -C≡C- represents 20 branched or cyclic alkyl groups,
When multiple L ^11s exist, they may be the same or different;
Z ¹¹ , Z ²¹ and Z ³¹ each independently represent -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -N=N-, -CF=CF- , -C≡C-, -C≡C-C≡C- or a single bond,
When multiple Z ^11s exist, they may be the same or different;
If there are multiple ^Z21s , they may be the same or different,
m11 and m21 each independently represent 0, 1 or 2,
In A ^x1 , any hydrogen atom in the group may be substituted with a halogen atom, and one or more -CH ₂ - in the group are each independently -O-, -S-, -CH =CH-, -CF=CF- or -C≡C- represents a linear or branched alkyl group having 1 to 20 carbon atoms,
Or A ^x1 is the following formula (Ax-1-i) ~ (Ax-5-i)

(In the formula,
The dashed line represents the bond position;
Y ¹¹ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group or alkoxy group having 1 to 8 carbon atoms,
If there are multiple ^Y11s , they may be the same or different,
^Y21 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or an alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom,
One or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S- Although it may be replaced with CO-, -O-CO-O-, -CH=CH-, -CF=CF- or -C≡C-,
Oxygen atoms do not bond with each other. )
represents a structure selected from the group consisting of,
Here, when A ^x1 has a structure selected from the group consisting of formulas (Ax-1-i) to (Ax-5-i), m11+m21 represents an integer from 0 to 2,
If A ^x does not have a structure selected from the group consisting of formulas (Ax-1-i) to (Ax-5-i), m11+m21 represents an integer from 1 to 3. )
The compound according to claim 1, which is represented by: The above general formula (I) is replaced by the following general formula (I-ii)

(In the formula,
In R ¹² , any hydrogen atom in the group may be substituted with a fluorine atom, and one or more -CH ₂ - in the group are each independently -O-, -CH=CH-, or -C≡C- represents a linear or branched alkyl group having 1 to 12 carbon atoms, which may be replaced by C≡C-;
A ¹² and A ²² are each independently represented by the following formulas (A-ii-1) to (A-ii-17)

(In the formula,
The dashed line represents the bond position;
When a plurality of L ^12s exist, they may be the same or different. )
represents a group selected from,
If there are multiple ^A12s , they may be the same or different;
If there are multiple ^A22s , they may be the same or different;
L ¹² is a fluorine atom or a straight carbon atom having 1 to 10 carbon atoms, in which any hydrogen atom in the group may be substituted with a fluorine atom, and -CH ₂ - in the group may be substituted with -O-. Represents a chain alkyl group or a branched or cyclic alkyl group having 3 to 10 carbon atoms,
Z ¹² , Z ²² and Z ³² are each independently -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -N=N-, -CF=CF- , -C≡C-, -C≡C-C≡C- or a single bond,
When multiple Z ^12s exist, they may be the same or different;
When multiple ^Z22s exist, they may be the same or different;
m12 and m22 each independently represent 0, 1 or 2, and m12 + m22 represents an integer from 0 to 2,
A ^x2 is the formula (Ax-1-i) or (Ax-2-i)

(In the formula,
The dashed line represents the bond position;
Y ¹¹ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group or alkoxy group having 1 to 8 carbon atoms,
If there are multiple ^Y11s , they may be the same or different,
^Y21 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or an alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom,
One or more -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S- Although it may be replaced with CO-, -O-CO-O-, -CH=CH-, -CF=CF- or -C≡C-,
Oxygen atoms do not bond with each other. )
Represents a structure selected from either. )
The compound according to claim 1, which is represented by: The above general formula (I) is replaced by the following general formula (I-iii)

(In the formula,
^R13 is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms. represents an alkynyl group,
A ¹³ and A ²³ each independently represent the following formulas (A-iii-1) to (A-iii-7), formula (A-iii-12), formula (A-iii-15), and formula ( A-iii-17)

(In the formula,
The dashed line represents the bond position;
When a plurality of L ^13s exist, they may be the same or different. )
represents a group selected from
L ¹³ represents a fluorine atom, a linear alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms,
Z ¹³ , Z ²³ and Z ³³ each independently represent -CF ₂ O-, -OCF ₂ -, -N=N-, -CH=CH-, -CF=CF-, -C≡C-, -C ≡C-C≡C- or represents a single bond,
m13 and m23 each independently represent 0 or 1,
Y ¹³ each independently represents a hydrogen atom, a fluorine atom or a chlorine atom. )
The compound according to claim 1, which is represented by: A composition containing a compound according to any one of claims 1 to 4. A liquid crystal composition containing the compound according to any one of claims 1 to 4. The liquid crystal composition according to claim 6, having a refractive index anisotropy of 0.15 or more. The liquid crystal composition according to claim 6, having a dielectric anisotropy of 2 or more. The liquid crystal composition according to claim 6, having a dielectric anisotropy of 2 or less. A high frequency phase shifter, a phased array antenna, an image recognition device, a distance measuring device, a liquid crystal display element, a liquid crystal lens, or a birefringent lens for stereoscopic image display, using the liquid crystal composition according to claims 6 to 9.