TW202248403A - Compound, liquid crystal composition and high-frequency phase shifter - Google Patents

Abstract

The present invention provides a compound represented by the general formula (I), which contains, in its structure, a thieno[3,2-b]thiophene-2,5-diyl group having a sulfur atom bonded at the 2-position; and provides a liquid crystal composition containing the compound and a device using the liquid crystal composition. The compound of the present invention has a large refractive index anisotropy Δn and a high compatibility with a liquid crystal composition, and exhibits a large dielectric constant anisotropy in a high frequency region; and therefore, it is useful as a material for a device of a high-frequency phase shifter, a phased array antenna, an image recognition device, distance measuring equipment, a liquid crystal display device, a liquid crystal lens, a birefringent lens for stereoscopic image display, or the like.

Description

Compounds, Liquid Crystal Compositions and High Frequency Phase Shifters

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

Liquid crystal compositions are used in mobile terminals, such as smartphones and tablet devices; and display applications, such as TVs and window displays. As a new application of such liquid crystal compositions, antennas for transmitting and receiving radio waves between communication satellites and moving bodies such as automobiles are attracting attention.

Conventionally, satellite communications use parabolic dish antennas; however, when used for moving bodies, parabolic dish antennas must be pointed at the satellite at all times and need to have large movable parts. However, an antenna using a liquid crystal composition can change the transmission-reception direction of radio waves by manipulating liquid crystals, and therefore, the antenna itself does not need to move and allows the antenna to have a planar shape.

The refractive index anisotropy Δn of liquid crystal compositions required for such applications is, for example, about 0.4, which is much larger than Δn required for display applications. Therefore, it is required that the compound used in the liquid crystal composition has a large Δn and high compatibility with the liquid crystal composition. Conventionally, compounds having a thienothiophene structure have been reported as compounds having a large Δn. However, these compounds are disadvantageous in that they have low compatibility when added to liquid crystal compositions for antennas, and cause precipitation in long-term storage (Non-Patent Document 1 and Patent Documents 1 and 2). In addition, compounds having a thienothiophene structure and a thioisocyano group have been reported, but these compounds have low dielectric constant anisotropy in a high frequency region and insufficient phase modulation characteristics (Patent Documents 3 and 4). Therefore, it is necessary to develop a compound that has a large Δn and high compatibility with liquid crystal compositions, and exhibits a large dielectric constant anisotropy in the high frequency region. [list of citations] [Non-patent literature] [Non-Patent Document 1] Chemistry of Materials, 2009, Volume 21, Issue 13, Pages 2727-2732 [Patent Document] [Patent Document 1] CN103472116A [Patent Document 2] JP2012-167068A [Patent Document 3] CN106518890A [Patent Document 4] WO2020/120586A1

[Problem to be solved by the present invention]

The problem to be solved by the present invention is to provide: a kind of material with large refractive index anisotropy (Δn) and high compatibility with liquid crystal composition, and exhibits large dielectric constant anisotropy (Δε) in the high frequency region A compound; a liquid crystal composition containing the compound; and a device using the liquid crystal composition. [means to solve the problem]

（在該式中，R ¹表示氫原子、氟原子、氯原子或具有1至20個碳原子之直鏈或分支鏈烷基，其中烷基中之任意氫原子可經鹵素原子取代，且烷基中之一個-CH ₂-或兩個或更多個-CH ₂-各自獨立地且視情況經-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-、-CF=CF-或-C≡C-取代，其限制條件為氧原子彼此不鍵結； A ¹及A ²各自獨立地表示可經取代之具有3至16個碳原子之烴環或雜環；當存在多個A ¹時，A ¹可相同或不同；且當存在多個A ²時，A ²可相同或不同； Z ¹、Z ²及Z ³各自獨立地表示二價連接基團或單鍵；當存在多個Z ¹時，Z ¹可相同或不同；且當存在多個Z ²時，Z ²可相同或不同； m1及m2各自獨立地表示0至3之整數；及 A ^x表示氫原子、氟原子、氯原子或具有1至20個碳原子之直鏈或分支鏈烷基，其中烷基中之任意氫原子視情況經鹵素原子取代；烷基中之一個-CH ₂-或兩個或更多個-CH ₂-各自獨立地且視情況經-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-、-CF=CF-或-C≡C-取代，其限制條件為氧原子彼此不鍵結；或A ^x表示選自由(Ax-1)至(Ax-5)組成之群的結構，

（在該等式中，虛線表示鍵結位置，且Y ¹各自獨立地表示氫原子、氟原子、氯原子或具有1至8個碳原子之烷基或烷氧基，其中任意氫原子可經氟原子取代，且當存在多個Y ¹時，其可相同或不同；Y ²表示氫原子、氟原子、氯原子、氰基、異硫氰基或具有1至8個碳原子之烷基，其中任意氫原子可經氟原子取代，且烷基中之一個-CH ₂-或兩個或更多個-CH ₂-可各自獨立地經-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-、CF=CF-或-C≡C-取代，其限制條件為氧原子彼此不鍵結），其中當A ^x為選自由式(Ax-1)至(Ax-5)組成之群的結構時，m1+m2表示0至3之整數；而當A ^x不為選自由式(Ax-1)至(Ax-5)組成之群的結構時，m1+m2表示1至4之整數）； 且提供含有該化合物之液晶組成物及使用該液晶組成物之裝置。 [本發明之有利效果] As a result of intensive research to solve the above-mentioned problems, the present inventors have developed a specific compound. That is, the present invention provides a compound represented by the following general formula (I), [Chemical Formula 1]

(In this formula, R ¹ represents a hydrogen atom, a fluorine atom, a chlorine atom or a linear or branched chain alkyl group having 1 to 20 carbon atoms, wherein any hydrogen atom in the alkyl group may be substituted by a halogen atom, and the alkane One of the groups -CH ₂ - or two or more -CH ₂ - each independently and optionally through -O-, -S-, -CO-, -COO-, -OCO-, -CO-S -, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, the restrictions Oxygen atoms are not bonded to each other; A ¹ and A ² each independently represent a hydrocarbon ring or a heterocyclic ring with 3 to 16 carbon atoms that may be substituted; when there are multiple A ^1s , A ¹ may be the same or different; And when there are multiple A ^2s , A ² can be the same or different; Z ¹ , Z ² and Z ³ each independently represent a divalent linking group or a single bond; when there are multiple Z ^1s , Z ¹ can be the same or Different; and when there are a plurality of Z ² , Z ² can be the same or different; m1 and m2 each independently represent an integer of 0 to 3; and A ^x represents a hydrogen atom, a fluorine atom, a chlorine atom or has 1 to 20 carbon A straight-chain or branched-chain alkyl group of atoms, wherein any hydrogen atom in the alkyl group is optionally substituted by a halogen atom; one -CH ₂ - or two or more -CH ₂ - in the alkyl group are each independently and optionally In case of -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH -CO-, -CH=CH-, -CF=CF- or -C≡C-substitution, the limitation is that the oxygen atoms are not bonded to each other; or A ^x represents a group selected from (Ax-1) to (Ax-5 ) consists of the structure of the group,

(In this equation, the dotted line represents the bonding position, and Y each independently represents ^a hydrogen atom, a fluorine atom, a chlorine atom or an alkyl or alkoxy group having 1 to 8 carbon atoms, wherein any hydrogen atom can be A fluorine atom is substituted, and when there are multiple ^Y1s , 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 with 1 to 8 carbon atoms, Any hydrogen atom may be replaced by a fluorine atom, and one -CH ₂ - or two or more -CH ₂ - in the alkyl group may be independently replaced by -O-, -S-, -CO-, -COO -, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, CF=CF-, or - C≡C-substitution, the restriction is that the oxygen atoms are not bonded to each other), wherein when A ^x is a structure selected from the group consisting of formulas (Ax-1) to (Ax-5), m1+m2 represents 0 to an integer of 3; and when A ^x is not a structure selected from the group consisting of formulas (Ax-1) to (Ax-5), m1+m2 represents an integer of 1 to 4); and a liquid crystal composition containing the compound is provided and devices using the liquid crystal composition. [Advantageous Effects of the Present Invention]

The compound of the present invention has a large refractive index anisotropy Δn and high compatibility with liquid crystal compositions, and exhibits a large dielectric constant anisotropy in the high-frequency region; and therefore, it can be used as a high-frequency phase shifter Materials for devices, phased array antennas, image recognition devices, distance measuring devices, liquid crystal display devices, liquid crystal lenses, birefringent lenses for stereoscopic image displays, or similar devices.

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

In the general formula (I), R ¹ represents a hydrogen atom, a linear or branched chain alkyl group having 1 to 20 carbon atoms; and any hydrogen atom in the alkyl group may be substituted by a halogen atom and one of the alkyl group- CH ₂ - or two or more -CH ₂ - can each independently pass through -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO- , -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, wherein the oxygen atoms are not bonded to each other. From the viewpoints of compatibility with liquid crystal compositions, refractive index anisotropy, voltage retention, ease of synthesis, and availability of raw materials, R1 preferably represents a hydrogen atom or a compound having ¹ to 20 carbon atoms. Straight-chain or branched-chain alkyl, wherein any hydrogen atom in the group may be substituted by a halogen atom and one -CH ₂ - or two or more -CH ₂ - in the group may each independently be replaced by - O-, -S-, -CH=CH-, -CF=CF- or -C≡C-substituted; R ¹ more preferably represents a straight chain or branched chain alkyl group with 1 to 12 carbon atoms, wherein the group Any hydrogen atom in the group may be replaced by a fluorine atom, and one -CH ₂ - or two or more -CH ₂ - in the group may be independently replaced by -O-, -CH=CH- or -C ≡C-substituted; R ¹ further preferably represents an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 7 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkenyl group with 2 to 7 carbon atoms Alkenyloxy with carbon atoms or alkynyl with 2 to 8 carbon atoms; and R especially preferably represents alkyl with ² to 5 carbon atoms, alkoxy with 1 to 4 carbon atoms, Alkenyl having 2 to 5 carbon atoms or alkynyl having 3 to 7 carbon atoms.

In the general formula (I), A ¹ and A ² each independently represent a hydrocarbon ring or a heterocyclic ring having 3 to 16 carbon atoms that may be substituted, wherein: when there are multiple A ^1s , they may be the same or different ; and when there are multiple A ^2s , they may be the same or different. From the viewpoints of compatibility with liquid crystal compositions, refractive index anisotropy, dielectric constant anisotropy, voltage retention, ease of synthesis, and availability ^of raw materials, A1 and ^A2 can be independently Unsubstituted or substituted by ^one or more substituents L, and preferably represents a group selected from the group consisting of: (a) 1,4-cyclohexylene (wherein one of the groups- CH ₂ - or two or more non-adjacent -CH ₂ - may be substituted by -O- or -S-); (b) 1,4-phenylene (wherein one of the groups- CH= or two or more non-adjacent -CH= may be substituted by -N=); (c) 1,4-cyclohexenyl, bicyclo[2.2.2]octane-1,4-bis base, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene -1,4-diyl, decalin-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2, 7-diyl (wherein the hydrogen atoms present in these groups may be replaced by fluorine or chlorine atoms, and present in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2, 3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl One of -CH= or two or more -CH= in anthracene-9,10-diyl or phenanthrene-2,7-diyl can be substituted by -N=); and (d) thiophene-2 ,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl group or thieno[3,2-b]thiophene-2,5-diyl (where one -CH= or two or more non-adjacent -CH= present in the group can be passed through -N= replace). When there are ^a plurality of A1 and ^A2 , they may be the same or different, and they may each independently be unsubstituted or substituted by ^one or more substituents L1; and it more preferably represents a group selected from the following: 1,4-phenylene, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, phenanthrene-2,7 -diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl, diphenyl Dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl or thieno[3,2-b]thiophene-2,5-diyl. When there are ^a plurality of A1 and A2, they may be the same or different; and further preferably, each independently represents a group selected from the following formulas (A- ¹ ) to (A-17). [chemical formula 2]

(In this formula, the dotted line indicates the bonding position, and when there are multiple L ¹ , they may be the same or different.) When there are multiple A ¹ and A ² , they may be the same or different; and further more preferably , A ¹ and A ² each independently represent a group selected from formulas (A-1) to (A-7), (A-12), (A-15) and (A-17). When there are a plurality of A ¹ and A ² , they may be the same or different; and especially preferably, A ¹ and A ² each independently represent formulas (A-1) and (A-3) to (A- 7) The group.

^L1 represents fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuryl group, nitro group, cyano group, isocyano group, amine group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group Amino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group or straight chain alkyl group with 1 to 20 carbon atoms or with 3 to 20 carbon atoms Branched chain or cyclic alkyl, wherein one -CH ₂ - or two or more -CH ₂ - can be independently modified by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO -CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-substitution, the limitation is that the oxygen atoms are not directly bonded to each other, and one of the alkyl groups Any hydrogen atom represents a group which may be substituted by a fluorine atom. From the viewpoints of compatibility with liquid crystal compositions, refractive index anisotropy, dielectric constant anisotropy, voltage retention, ease of synthesis, and availability of raw materials, L1 preferably represents ^a fluorine atom, chlorine atom or a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein any hydrogen atom in the group may be substituted by a fluorine atom and in the group One -CH ₂ - or two or more -CH ₂ -s may be independently substituted by -O-, -S-, -CH=CH, -CF=CF- or -C≡C-. L more preferably represents ^a fluorine atom or a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein any hydrogen atom in the group can be replaced by a fluorine atom Substituted and -CH ₂ - in this group may be substituted by -O-. L ¹ further preferably represents a fluorine atom or a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms. L ¹ especially preferably represents a fluorine atom or a linear alkyl group having 1 to 8 carbon atoms.

In general formula (I), Z ¹ , Z ² and Z ³ each independently represent a divalent linking group or a single bond, but when there are multiple Z ^1s , they may be the same or different; and when there are multiple Z ² , they can be the same or different. From the viewpoints of compatibility with liquid crystal compositions, refractive index anisotropy, dielectric constant anisotropy, voltage retention, ease of synthesis, and availability of raw materials, Z ¹ , Z ² , and Z ³ each Independently preferably represents 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=NN=C-, -CH=N-, -N=CH-, -C≡CC≡C- or an alkylene group with 2 to 20 carbon atoms, wherein one of the alkylene groups -CH ₂ - or two or more -CH ₂ - means that -O-, - A group substituted by S-, -COO- or -OCO-. When there are multiple Z ¹ , Z ² and Z ³ , they may be the same or different; and more preferably, they each independently represent -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡ C-, -C≡CC≡C- or a single bond. When there are multiple Z ¹ , Z ² and Z ³ , they may be the same or different; and further preferably, they each independently represent -CF ₂ O-, -OCF ₂ -, -CH=CH-, -CF =CF-, -N=N-, -C≡C-, -C≡CC≡C- or a single bond. When there are multiple Z ¹ , Z ² and Z ³ , they may be the same or different; and further preferably, they each independently represent -CF ₂ O-, -OCF ₂ -, -N=N-, -C ≡C-, -C≡CC≡C- or a single bond. When there are a plurality of Z ¹ , Z ² and Z ³ , they may be the same or different; and especially preferably, they each independently represent -C≡C- or a single bond.

In the general formula (I), m1 and m2 each independently represent an integer of 0 to 3, and m1+m2 is preferably an integer of 0 to 4; specifically, when A ^x is selected from the formula (Ax-1) For the structure of the group consisting of (Ax-5), m1+m2 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2. In addition, when A ^x is not a structure selected from the group consisting of (Ax-1) to (Ax-5), m1+m2 is preferably an integer of 1 to 4, more preferably an integer of 1 to 3. From the viewpoints of compatibility with liquid crystal compositions, refractive index anisotropy, dielectric constant anisotropy, voltage retention, ease of synthesis, and availability of raw materials, preferably, m1 and m2 are independent of each other represents 0, 1 or 2 and m1+m2 represents an integer from 1 to 3; more preferably, m1 and m2 independently represent 0, 1 or 2 and m1+m2 represents 1 or 2; further preferably, m1 and m2 each independently represents 0 or 1, and m1+m2 represents 1 or 2; and particularly preferably, m1 and m2 each independently represent 0 or 1, and m1+m2 represents 1.

Since the compound represented by the general formula (I) includes a thieno[3,2-b]thiophene-2,5-diyl group with a sulfur atom bonded at the 2-position in the structure, it can be attributed to 3 sulfur atoms The resulting conjugated structure with high electron density effectively increases Δn, and at the same time exhibits the excellent effect of exhibiting large dielectric constant anisotropy in the high frequency region. In addition, since the general formula (I) has a total of two or more ring structures in the molecule, it forms a rod-like molecular structure as a whole compound, thereby improving liquid crystallinity and increasing Tni, so it is added to the liquid crystal composition It can effectively broaden the liquid crystal phase temperature range 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 chain alkyl group having 1 to 20 carbon atoms, and any hydrogen atom in the alkyl group may be substituted by a halogen atom and One of the -CH ₂ - or two or more -CH ₂ - in the alkyl group can each independently undergo -O-, -S-, -CO-, -COO-, -OCO-, -CO-S- , -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, the restrictions are Oxygen atoms are not bonded to each other. Alternatively, ^Ax represents a structure selected from the group consisting of the following formulas (Ax-1) to (Ax-5).

(In this equation, the dotted line represents the bonding position, and Y each independently represents ^a hydrogen atom, a fluorine atom, a chlorine atom or an alkyl or alkoxy group having 1 to 8 carbon atoms, wherein any hydrogen atom can be replaced by fluorine Atom substitution, wherein: when there are multiple ^Y1 , ^Y1 can 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 with 1 to 8 carbon atoms , wherein any hydrogen atom may be substituted by a fluorine atom and one -CH ₂ - or two or more -CH ₂ - in the alkyl group may each independently be replaced by -O-, -S-, -CO-, -COO -, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF-, or -C≡C-substitution, the limit condition is that the oxygen atoms are not bonded to each other.) Compatibility with liquid crystal composition, refractive index anisotropy, dielectric constant anisotropy, voltage retention, synthesis simplicity and From the viewpoint of availability of raw materials, A ^x preferably represents a structure selected from the group consisting of the following formulas (Ax-1-i) to (Ax-5-i).

（在該式中，虛線表示鍵結位置；及 Y ¹³各自獨立地表示氫原子、氟原子或氯原子）。 (In this formula, the dotted line represents the bonding position, and Y ¹¹ each independently represent a hydrogen atom, a fluorine atom, or an alkyl or alkoxy group having 1 to 8 carbon atoms, wherein when there are a plurality of Y ¹¹ , it may are the same or different, and ^Y 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, wherein any hydrogen atom may be substituted by a fluorine atom and any of the alkyl groups One -CH ₂ - or two or more -CH ₂ - can each independently pass through -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S- CO-, -O-CO-O-, -CH=CH-, -CF=CF-, or -C≡C-, provided that the oxygen atoms are not bonded to each other). A ^x further preferably represents the formula (Ax-1-i) or (Ax-2-i). In addition, A ^x particularly preferably represents a group selected from the following formula (Ax-1-ii). [chemical formula 3]

(In this formula, dotted lines represent bonding positions; and Y ¹³ each independently represent a hydrogen atom, a fluorine atom or a chlorine atom).

及由下式表示之部分結構 [化學式5]

較佳彼此不同。 In addition, among the compounds represented by the general formula (I), from the viewpoint of solubility in the liquid crystal composition, the partial structure represented by the following formula [Chemical formula 4]

and a partial structure represented by the following formula [chemical formula 5]

Preferably they are different from each other.

（在該式中，R ¹¹表示氫原子或具有1至20個碳原子之直鏈或分支鏈烷基，其中該基團中之任意氫原子視情況經鹵素原子取代且該基團中之一個-CH ₂-或兩個或更多個-CH ₂-各自獨立地且視情況經-O-、-S-、-CH=CH-、-CF=CF-或-C≡C-取代； A ¹¹及A ²¹各自獨立地表示1,4-伸苯基、萘-2,6-二基、萘-1,4-二基、5,6,7,8-四氫萘-1,4-二基、菲-2,7-二基、苯并噻吩-2,5-二基、苯并噻吩-2,6-二基、苯并噻唑-2,5-二基、苯并噻唑-2,6-二基、二苯并噻吩-3,7-二基、二苯并噻吩-2,6-二基或噻吩并[3,2-b]噻吩-2,5-二基，其中當存在多個A ¹¹時，其可相同或不同；當存在多個A ²¹時，其可相同或不同；且此等基團可未經取代或經一或多個取代基L ¹¹取代； L ¹¹表示氟原子、氯原子或具有1至20個碳原子之直鏈烷基或具有3至20個碳原子之分支鏈或環狀烷基，其中該基團中之任意氫原子視情況經氟原子取代且該基團中之一個-CH ₂-或兩個或更多個-CH ₂-各自獨立地且視情況經-O-、-S-、-CH=CH-、-CF=CF-或-C≡C-取代，其中當存在多個L ¹¹時，L ¹¹視情況相同或不同； Z ¹¹、Z ²¹及Z ³¹各自獨立地表示-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-或單鍵，其中：當存在多個Z ¹¹時，Z ¹¹視情況相同或不同；且當存在多個Z ²¹時，Z ²¹視情況相同或不同； m11及m21各自獨立地表示0、1或2； A ^x1表示氫原子或具有1至20個碳原子之直鏈或分支鏈烷基，其中該基團中之任意氫原子視情況經鹵素原子取代且該基團中之一個-CH ₂-或兩個或更多個-CH ₂-各自獨立地視情況經-O-、-S-、-CH=CH-、-CF=CF-或-C≡C-取代，或A ^x1表示選自由以下式(Ax-1-i)至(Ax-5-i)組成之群的結構，

（在該式中，虛線表示鍵結位置；Y ¹¹各自獨立地表示氫原子、氟原子或具有1至8個碳原子之烷基或烷氧基，其中當存在多個Y ¹¹時，Y ¹¹可相同或不同；且Y ²¹表示氫原子、氟原子、氯原子、氰基、異硫氰基或具有1至8個碳原子之烷基，其中任意氫原子視情況經氟原子取代且烷基中之一個-CH ₂-或兩個或更多個-CH ₂-可各自獨立地經-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CH=CH-、-CF=CF-或-C≡C-取代，其限制條件為氧原子彼此不鍵結），其中：當A ^x1為選自由式(Ax-1-i)至(Ax-5-i)組成之群的結構時，m11+m21表示0至2之整數；而當A ^x1不為選自由式(Ax-1-i)至(Ax-5-i)組成之群的結構時，m11+m21表示1至3之整數）。 From the point of view of the width of the temperature range of the liquid crystal phase, the anisotropy of the dielectric constant, the compatibility with the liquid crystal composition, the anisotropy of the refractive index, the voltage retention, the ease of synthesis, and the availability of raw materials , the compound represented by the general formula (I) is preferably a compound represented by the following general formula (Ii), [Chemical formula 6]

(In this formula, R ¹¹ represents a hydrogen atom or a linear or branched chain alkyl group having 1 to 20 carbon atoms, wherein any hydrogen atom in the group is optionally substituted by a halogen atom and one of the groups -CH ₂ - or two or more -CH ₂ - each independently and optionally substituted by -O-, -S-, -CH=CH-, -CF=CF- or -C≡C-; A ¹¹ and A ²¹ each independently represent 1,4-phenylene, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 5,6,7,8-tetrahydronaphthalene-1,4- Diyl, phenanthrene-2,7-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2 ,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl or thieno[3,2-b]thiophene-2,5-diyl, where when When there are multiple A ¹¹ , they can be the same or different; when there are multiple A ²¹ , they can be the same or different; and these groups can be unsubstituted or substituted by one or more substituents L ¹¹ ; L ¹¹ Represents a fluorine atom, a chlorine atom, or a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein any hydrogen atom in the group is optionally replaced by a fluorine atom Substituted and one -CH ₂ - or two or more -CH ₂ - in the group are each independently and optionally through -O-, -S-, -CH=CH-, -CF=CF- or -C≡C-substitution, wherein when there are multiple L ¹¹ , L ¹¹ are the same or different as appropriate; 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=NN=CH-, -CF=CF-, -C≡C-, -C≡CC≡C- or a single bond, wherein: when there are multiple Z ¹¹ , Z ¹¹ are the same or different as appropriate; and When there are a plurality of Z ²¹ , Z ²¹ is the same or different as the case may be; m11 and m21 each independently represent 0, 1 or 2; A ^x1 represents a hydrogen atom or a linear or branched chain alkyl group having 1 to 20 carbon atoms , wherein any hydrogen atom in the group is optionally substituted by a halogen atom and one -CH ₂ - or two or more -CH ₂ - in the group are independently optionally replaced by -O-, -S -, -CH=CH-, -CF=CF- or -C≡C-substituted, or A ^x1 represents a structure selected from the group consisting of the following formulas (Ax-1-i) to (Ax-5-i),

(In this formula, the dotted line represents the bonding position; Y ¹¹ each independently represent a hydrogen atom, a fluorine atom, or an alkyl or alkoxy group having 1 to 8 carbon atoms, wherein when there are multiple Y ¹¹ , Y ¹¹ may be the same or different; and ^Y 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, wherein any hydrogen atom is optionally substituted by a fluorine atom and the alkyl group One of -CH ₂ - or two or more -CH ₂ - can each independently pass through -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, - S-CO-, -O-CO-O-, -CH=CH-, -CF=CF- or -C≡C-substitution, the restriction is that the oxygen atoms are not bonded to each other), where: when A ^x1 is When selected from the structure of the group consisting of formula (Ax-1-i) to (Ax-5-i), m11+m21 represents an integer from 0 to 2; and when A ^x1 is not selected from formula (Ax-1-i ) to (Ax-5-i) group structure, m11+m21 represents an integer from 1 to 3).

（在該式中，R ¹²表示具有1至12個碳原子之直鏈或分支鏈烷基，其中該基團中之任意氫原子可經氟原子取代，且該基團中之一個-CH ₂-或兩個或更多個-CH ₂-可各自獨立地經-O-、-CH=CH-或-C≡C-取代； A ¹²及A ²²各自獨立地表示選自以下式(A-ii-1)至(A-ii-17)之基團， [化學式8]

（在該等式中，虛線表示鍵結位置，且當存在多個L ¹²時，L ¹²視情況相同或不同），其中：當存在多個A ¹²時，A ¹²視情況相同或不同；且當存在多個A ²²時，A ²²視情況相同或不同； L ¹²表示氟原子或具有1至10個碳原子之直鏈烷基或具有3至10個碳原子之分支鏈或環狀烷基，其中該基團中之任意氫原子視情況經氟原子取代且該基團中之-CH ₂-視情況經-O-取代； Z ¹²、Z ²²及Z ³²各自獨立地表示-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-或單鍵，其中：當存在多個Z ¹²時，Z ¹²視情況相同或不同；且當存在多個Z ²²時，Z ²²視情況相同或不同； m12及m22各自獨立地表示0、1或2，且m12+m22表示0至2之整數； A ^x2表示選自式(Ax-1-i)及(Ax-2-i)之結構）。由通式(I)表示之化合物進一步較佳為由以下通式(I-iii)表示之化合物， [化學式9]

（在該式中，R ¹³表示具有1至8個碳原子之烷基、具有1至7個碳原子之烷氧基、具有2至8個碳原子之烯基、具有2至7個碳原子之烯氧基或具有2至8個碳原子之炔基； A ¹³及A ²³各自獨立地表示下式(A-iii-1)至(A-iii-7)、(A-iii-12)、(A-iii-15)及(A-iii-17)； [化學式10]

（在該等式中，虛線表示鍵結位置，且當存在多個L ¹³時，L ¹³視情況相同或不同）； L ¹³表示氟原子或具有1至10個碳原子之直鏈烷基或具有3至10個碳原子之分支鏈或環狀烷基； Z ¹³、Z ²³及Z ³³各自獨立地表示-CF ₂O-、-OCF ₂-、-N=N-、-CH=CH-、-CF=CF-、-C≡C-、-C≡C-C≡C-或單鍵； m13及m23各自獨立地表示0或1； Y ¹³各自獨立地表示氫原子、氟原子或氯原子）。特定言之，由通式(I)表示之化合物尤其較佳為由以下通式(I-iv-1)或(I-iv-2)表示之化合物， [化學式11]

（在該等式中，R ¹⁴表示具有2至5個碳原子之烷基、具有1至4個碳原子之烷氧基、具有2至5個碳原子之烯基或具有3至7個碳原子之炔基； A ²⁴表示選自以下式(A-iv-1)及(A-iv-3)至(A-iv-7)之基團； [化學式12]

（在該等式中，虛線表示鍵結位置，且當存在多個L ¹⁴時，其可相同或不同）； L ¹⁴表示氟原子或具有1至8個碳原子之直鏈烷基； Z ²⁴及Z ³⁴獨立地表示-C≡C-、-C≡C-C≡C-或單鍵；及 Y ¹⁴及Y ³⁴各自獨立地表示氫原子或氟原子）。 In addition, the compound represented by the general formula (I) is more preferably a compound represented by the following general formula (I-ii), [Chemical formula 7]

(In this formula, R ¹² represents a linear or branched chain alkyl group having 1 to 12 carbon atoms, wherein any hydrogen atom in the group may be substituted by a fluorine atom, and one of the groups -CH ₂ - or two or more -CH ₂ - may be independently substituted by -O-, -CH=CH- or -C≡C-; A ¹² and A ²² each independently represent a group selected from the following formula (A- The group of ii-1) to (A-ii-17), [Chemical Formula 8]

(In this equation, the dotted line represents the bonding position, and when there are multiple L ^12s , the L ^12s are the same or different as appropriate), wherein: when there are multiple A ^12s , the A ^12s are the same or different as the case may be; and When there are multiple A ²² , A ²² is the same or different as the case may be; L ¹² represents a fluorine atom or a straight-chain alkyl group with 1 to 10 carbon atoms or a branched chain or cyclic alkyl group with 3 to 10 carbon atoms , wherein any hydrogen atom in the group is optionally substituted by a fluorine atom and -CH ₂ - in the group is optionally substituted by -O-; Z ¹² , Z ²² and Z ³² 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=NN=CH-, -CF=CF-, -C≡C-, -C≡CC≡C- or a single bond, wherein: when there are multiple Z ¹² , Z ¹² is the same or different as the case may be; and when there are multiple Z ^22s , Z ²² is the same or different as the case may be; 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 formulas (Ax-1-i) and (Ax-2-i)). The compound represented by the general formula (I) is further preferably a compound represented by the following general formula (I-iii), [Chemical formula 9]

(In this formula, R 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, an alkenyl group having 2 to 7 carbon atoms An alkenyloxy group or an alkynyl group having 2 to 8 carbon atoms; A ¹³ and A ²³ each independently represent the following formulas (A-iii-1) to (A-iii-7), (A-iii-12) , (A-iii-15) and (A-iii-17); [chemical formula 10]

(In this equation, the dotted line represents the bonding position, and when there are multiple L ¹³ , L ¹³ is the same or different as the case may be); L ¹³ represents a fluorine atom or a linear alkyl group having 1 to 10 carbon atoms or A branched or cyclic alkyl group with 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≡CC≡C- or a single bond; m13 and m23 each independently represent 0 or 1; Y13 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom) . Specifically, the compound represented by the general formula (I) is especially preferably a compound represented by the following general formula (I-iv-1) or (I-iv-2), [Chemical formula 11]

(In this equation, R 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 alkenyl group having 3 to 7 carbon atoms Atom alkynyl; A ²⁴ represents a group selected from the following formulas (A-iv-1) and (A-iv-3) to (A-iv-7); [chemical formula 12]

(In this equation, the dotted line represents the bonding position, and when there are multiple L ¹⁴ , they may be the same or different); L ¹⁴ represents a fluorine atom or a linear alkyl group with 1 to 8 carbon atoms; Z ²⁴ and Z ³⁴ independently represent -C≡C-, -C≡CC≡C- or a single bond; and Y ¹⁴ and Y ³⁴ each independently represent a hydrogen atom or a fluorine atom).

[化學式14]

[化學式15]

[化學式16]

[化學式17]

[化學式18]

[化學式19]

[化學式20]

[化學式21]

[化學式22]

Specific examples of the compound represented by the general formula (I) include compounds represented by the following formulas (I-1) to (I-69). [chemical formula 13]

[chemical formula 14]

[chemical formula 15]

[chemical formula 16]

[chemical formula 17]

[chemical formula 18]

[chemical formula 19]

[chemical formula 20]

[chemical formula 21]

[chemical formula 22]

（在該等式中，R ^1s、A ^1s、A ^2s、Z ^1s、Z ^2s、Z ^3s、m1s、m2s及A ^xs具有與上述通式(I)中之R ¹、A ¹、A ²、Z ¹、Z ²、Z ³、m1、m2及A ^x相同的含義。） The compound of the present invention can be produced by the following production methods. (Production method 1) Production of a compound represented by the following formula (s-5) [Chemical formula 23]

(In this equation, R ^1s , A ^1s , A ^2s , Z ^1s , Z ^2s , Z ^3s , m1s, m2s and A ^xs have the same characteristics as R ¹ , A ¹ , A ² , Z ¹ , Z ² , Z ³ , m1, m2 and A ^x have the same meaning.)

The compound represented by formula (s-1) is reacted with the compound represented by formula (s-15) and sulfur to obtain the compound represented by formula (s-2).

The compound represented by formula (s-2) is reacted with, for example, N-bromosuccinimide to obtain the compound represented by formula (s-3).

The compound represented by the formula (s-3) is reacted with trimethylsilylacetylene, and then reacted with tetrafluoroammonium fluoride (TBAF), thereby obtaining the compound represented by the general formula (s-4). 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). Specific examples of copper catalysts include copper(I) iodide. Specific examples of bases include triethylamine.

（在該等式中，R ^1s、A ^1s、Z ^1s、m1s及Y ^1s具有與上述通式(I)中之R ¹、A ¹、Z ¹、m1及Y ¹相同的含義。） The compound represented by formula (s-4) is reacted with the compound represented by formula (s-16) to obtain the compound represented by general formula (s-5). Examples of the reaction method include Zonou coupling reaction using a palladium catalyst, a copper catalyst and a base. Specific examples of palladium catalysts include those mentioned above. Specific examples of copper catalysts include copper(I) iodide. Specific examples of bases include triethylamine. (Production method 2) Production of a compound represented by the following formula (s-10) [Chemical formula 24]

(In this equation, 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 above general formula (I).)

The compound represented by the formula (s-3) is reacted with the compound represented by the general formula (s-6) to obtain the compound represented by the general formula (s-7). 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, dichlorobis[di-tertiary-butyl(p-di Methylaminophenyl)phosphino]palladium(II) and tetrakis(triphenylphosphine)palladium(0). When palladium(II) acetate is used as the metal catalyst, ligands such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. Specific examples of bases include potassium carbonate, potassium phosphate, and cesium carbonate.

The compound represented by the general formula (s-7) is reacted with, for example, hydroxylamine to obtain the compound represented by the general formula (s-8).

The compound represented by the general formula (s-8) is reacted with, for example, N-chlorobutanediimide to give the compound represented by the general formula (s-9).

The compound represented by the general formula (s-9) is reacted with, for example, thiourea to give the compound represented by the general formula (s-10).

The above-mentioned production method 1 shows the production method of the compound in which Ax in the above-mentioned general formula (I) ^is represented by the above-mentioned formula (Ax-1), but Ax in the above-mentioned general formula (I) ^is represented by the above-mentioned formula (Ax-2) The compound of can be synthesized by the same method as the compound represented by the general formula (s-10). (Production method 3) producing a compound represented by the following formula (s-14) [chemical formula 25]

The compound represented by formula (s-1) is reacted with sulfur in the presence of, for example, n-butyllithium to obtain the compound represented by formula (s-11).

The compound represented by formula (s-11) is reacted with, for example, N-bromosuccinimide to give the compound represented by formula (s-12).

The compound represented by the formula (s-12) is reacted with trimethylsilylacetylene, and then reacted with tetrafluoroammonium fluoride (TBAF), whereby the compound represented by the general formula (s-13) can be obtained. Examples of the reaction method include Zonou coupling reaction using a palladium catalyst, a copper catalyst and a base. Specific examples of palladium catalysts include tetrakis(triphenylphosphine)palladium(0). Specific examples of copper catalysts include copper(I) iodide. Specific examples of bases include triethylamine.

The compound represented by formula (s-13) and 1,8-diazabicyclo[5,5,0]undec-7-ene (DBU), N,N,N',N'-tetramethylethane Diamine and copper iodide are mutually reacted together, whereby the compound represented by the general formula (s-14) can be obtained.

Examples of reaction conditions other than those described in each step include 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 fuer Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co.K), Fiesers' Reagents for Organic Synthesis (John Wiley & Sons, Inc.) or similar Reaction conditions as described in the literature of , or in databases such as SciFinder (Chemical Abstracts Service, American Chemical Society), Reaxys (Elsevier Ltd.) or the like.

In each step, a functional group may be protected as necessary. Examples of protecting groups include those described in GREENE'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS (4th Edition), co-authored by PETER G.M. WUTS and THEODORA W. GREENE, A John Wiley & Sons, Inc., Publication) or the like. base.

In addition, purification may be performed as necessary in each step. Examples of purification methods include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid separation treatments. Specific examples of purifying agents include silica gel, alumina, and activated carbon.

The compound represented by the general formula (I) is preferably used by being added to a liquid crystal composition. When the liquid crystal composition contains the compound represented by the general formula (I), it may contain one compound represented by the general formula (I), or it may contain plural kinds of compounds represented by the general formula (I). When the liquid crystal composition of the present invention contains the compound represented by the general formula (I), the total content of the compound represented by the general formula (I) in the liquid crystal composition is preferably 5% by mass or more, more preferably 10% by mass % or more and 95% by mass or less, further preferably 15% by mass or more and 90% by mass or less, and especially preferably 20% by mass or more and 85% by mass or less. When the liquid crystal composition contains a compound represented by the general formula (I), the "total content of the compound represented by the general formula (I)" as used herein means the content of the compound represented by the general formula (I); and when When the liquid crystal composition contains a plurality of compounds represented by the general formula (I), it means the sum of the contents of the plurality of compounds represented by the general formula (I).

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 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, more preferably 0.25 or larger and 0.90 or smaller, further preferably 0.30 or larger and 0.85 or smaller, and especially preferably 0.35 or larger and 0.80 or smaller.

When the liquid crystal composition containing the compound represented by the general formula (I) is used in a high-frequency phase shifter, a phase array antenna, an image recognition device, a distance measurement device, a liquid crystal display device, a liquid crystal lens, or a double In the case of a refractive lens, the dielectric constant anisotropy (Δε (1 kHz)) at 1 kHz of the liquid crystal composition containing the compound represented by the general formula (I) is preferably 2 or more and 60 or less. From the point of view of 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 (1 kHz)) at 1 kHz is higher than that of It is preferably 2.5 or more and 50 or less, more preferably 3 or more and 40 or less, and especially preferably 3.5 or more and 30 or less.

A liquid crystal composition containing a compound represented by the general formula (I) is preferably used in high-frequency devices. 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, further preferably 2 GHz or more and 300 GHz or less, and especially Preferably 5 GHz or more and 150 GHz or less.

（在該式中，R ²表示具有1至8個碳原子之烷基、具有1至7個碳原子之烷氧基、具有2至8個碳原子之烯基或具有2至7個碳原子之烯氧基； A ³表示選自以下式(A6-1)至(A6-8)之基團； [化學式27]

（在該等式中，虛線表示鍵結位置），其中當存在多個A ³時，其可相同或不同；及 Z ⁴表示-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-或單鍵，其中當存在多個Z ⁴時，其可相同或不同； m3表示1至4之整數；及 A ^y表示選自以下式(Ay-1)及(Ay-2)之基團 [化學式28]

（在該式中，虛線表示鍵結位置，Y ⁷、Y ⁹、Y ¹⁰及Y ¹²各自獨立地表示氫原子、氟原子或氯原子，且Y ⁸及Y ¹¹各自獨立地表示氟原子、氯原子、氰基、硫代異氰基、硝基、五氟硫基、其中任意氫原子經氟原子取代之具有1至8個碳原子之烷基、其中任意氫原子經氟原子取代之具有1至7個碳原子之烷氧基、其中任意氫原子經氟原子取代之具有2至8個碳原子之烯基或其中任意氫原子經氟原子取代之具有2至7個碳原子之烯氧基，其中一個-CH ₂-或兩個或更多個-CH ₂-各自獨立地且視情況經-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-或-C≡C-取代））。 The liquid crystal composition containing the compound represented by the general formula (I) preferably contains the compound represented by the following general formula (VI). [chemical formula 26]

(In this ^formula , R 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 The alkenyloxy group; A ³ represents a group selected from the following formulas (A6-1) to (A6-8); [Chemical formula 27]

(In this equation, the dotted line indicates the bonding position), wherein when there are multiple A ³ , they may be the same or different; and Z ⁴ represents -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=NN=CH-, -CF=CF -, -C≡C- or a single bond, wherein when there are multiple Z ⁴ , they may be the same or different; m3 represents an integer from 1 to 4; and A ^y represents a group selected from the following formulas (Ay-1) and (Ay -2) the group [chemical formula 28]

(In this formula, the dotted line indicates the bonding position, Y ⁷ , Y ⁹ , Y ¹⁰ and Y ¹² each independently represent a hydrogen atom, a fluorine atom or a chlorine atom, and Y ⁸ and Y ¹¹ each independently represent a fluorine atom, a chlorine atom Atom, cyano group, thioisocyano group, nitro group, pentafluorosulfanyl group, alkyl group with 1 to 8 carbon atoms in which any hydrogen atom is replaced by fluorine atom, and alkyl group with 1 to 8 carbon atoms in which any hydrogen atom is replaced by fluorine atom An alkoxy group of up to 7 carbon atoms, an alkenyl group of 2 to 8 carbon atoms in which any hydrogen atom is substituted by a fluorine atom, or an alkenyloxy group of 2 to 7 carbon atoms in which any hydrogen atom is substituted by a fluorine atom , wherein one -CH ₂ - or two or more -CH ₂ - each independently and optionally via -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-substituted)).

（在該式中，R ²¹表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基、具有2至5個碳原子之烯基或具有2至4個碳原子之烯氧基； A ³¹表示選自式(A6-1)至(A6-6)之基團，其中當存在多個A ³¹時，其視情況相同或不同； Z ⁴¹表示-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-或單鍵，其中當存在多個Z ⁴¹時，其可相同或不同； m31表示1至3之整數；及 A ^y1表示選自以下式(Ay-1-i)及(Ay-2-i)之基團， [化學式30]

（在該等式中，虛線表示鍵結位置，Y ⁷¹、Y ⁹¹、Y ¹⁰¹及Y ¹²¹各自獨立地表示氫原子、氟原子或氯原子，且Y ⁸¹及Y ¹¹¹各自獨立地表示氟原子、氯原子、氰基、硫代異氰基、硝基、五氟硫基、其中任意氫原子可經氟原子取代之具有1至8個碳原子之烷基、其中任意氫原子可經氟原子取代之具有1至7個碳原子之烷氧基、其中任意氫原子可經氟原子取代之具有2至8個碳原子之烯基或其中任意氫原子可經氟原子取代之具有2至7個碳原子之烯氧基））。由通式(VI)表示之化合物更佳為由以下通式(VI-ii)表示之化合物， [化學式31]

（在該式中，R ²²表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基、具有2至5個碳原子之烯基或具有2至4個碳原子之烯氧基； A ³²表示選自上述式(A6-1)至(A6-5)之基團，其中當存在多個A ³²時，其可相同或不同； Z ⁴²表示-CF ₂O-、-OCF ₂-、-CH=CH-、-CF=CF-、-N=N-、-C≡C-或單鍵，其中當存在多個Z ⁴²時，其可相同或不同； m32表示1、2或3； Y ⁷²及Y ⁹²各自獨立地表示氫原子、氟原子或氯原子，且Y ⁸²表示氟原子、氯原子、氰基、硫代異氰基、硝基、五氟硫基、其中任意氫原子可經氟原子取代之具有1至8個碳原子之烷基、其中任意氫原子可經氟原子取代之具有1至7個碳原子之烷氧基、其中任意氫原子可經氟原子取代之具有2至8個碳原子之烯基或其中任意氫原子可經氟原子取代之具有2至7個碳原子之烯氧基）。由通式(VI)表示之化合物進一步較佳為由以下通式(VI-iii)表示之化合物， [化學式32]

（在該式中，R ²³表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基或具有2至5個碳原子之烯基， A ³³表示選自上述式(A6-1)至(A6-5)之基團，其中當存在多個A ³³時，其可相同或不同； Z ⁴³表示-CF ₂O-、-OCF ₂-、-N=N-、-C≡C-或單鍵，其中當存在多個Z ⁴³時，其可相同或不同； m33表示1、2或3；及 Y ⁷³及Y ⁹³各自獨立地表示氫原子、氟原子或氯原子，且Y ⁸³表示氟原子、氯原子、氰基或硫代異氰基）。由通式(VI)表示之化合物尤其較佳為由以下通式(VI-iv-1)至(VI-iv-21)表示之化合物， [化學式33]

[化學式34]

[化學式35]

[化學式36]

[化學式37]

（在該等式中，R ⁶¹⁴表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基或具有2至5個碳原子之烯基）。 From the viewpoint of liquid crystal phase temperature range, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, the compound represented by the general formula (VI) is preferably represented by the following general formula The compound represented by (VI-i), [Chemical Formula 29]

(In this formula, R ²¹ 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 alkenyl group having 2 to 4 carbon atoms The alkenyloxy group; A ³¹ represents a group selected from formulas (A6-1) to (A6-6), wherein when there are multiple A ³¹ , they are the same or different as appropriate; Z ⁴¹ represents -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=NN=CH-, -CF=CF-, -N=N-, -C≡C- or a single bond, wherein when there are multiple Z ⁴¹ , they can be the same or different; m31 represents An integer of 1 to 3; and A ^y1 represents a group selected from the following formulas (Ay-1-i) and (Ay-2-i), [Chemical formula 30]

(In this equation, the dotted line represents the bonding position, Y ⁷¹ , Y ⁹¹ , Y ¹⁰¹ and Y ¹²¹ each independently represent a hydrogen atom, a fluorine atom or a 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 with 1 to 8 carbon atoms, wherein any hydrogen atom may be substituted by fluorine atom, any hydrogen atom may be substituted by 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 may be substituted by a fluorine atom, or an alkenyl group having 2 to 7 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom atom of alkenyloxy)). The compound represented by the general formula (VI) is more preferably a compound represented by the following general formula (VI-ii), [Chemical formula 31]

(In this 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 alkenyl group having 2 to 4 carbon atoms The alkenyloxy group; A ³² represents a group selected from the above formulas (A6-1) to (A6-5), wherein when there are multiple A ³² , 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, wherein when there are multiple Z ⁴² , they can 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, and Y ⁸² represents a fluorine atom, a chlorine atom, a cyano group, a thioisocyano group, a nitro group, a pentafluorothio group , an alkyl group having 1 to 8 carbon atoms wherein any hydrogen atom may be substituted by a fluorine atom, an alkoxy group having 1 to 7 carbon atoms wherein any hydrogen atom may be substituted by a fluorine atom, wherein any hydrogen atom may be substituted by a fluorine atom an alkenyl group having 2 to 8 carbon atoms substituted with a fluorine atom or an alkenyloxy group having 2 to 7 carbon atoms in which any hydrogen atom may be substituted by a fluorine atom). The compound represented by the general formula (VI) is further preferably a compound represented by the following general formula (VI-iii), [Chemical formula 32]

(In this formula, R ²³ 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 formula (A6-1) to (A6-5), wherein when there are a plurality of A ³³ , they may be the same or different; Z ⁴³ represents -CF ₂ O-, -OCF ₂ -, -N=N-, -C≡C- or a single bond, wherein when there are a plurality of Z ⁴³ , they may be the same or different; m33 represents 1, 2 or 3; and 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). The compound represented by the general formula (VI) is especially preferably a compound represented by the following general formulas (VI-iv-1) to (VI-iv-21), [Chemical formula 33]

[chemical formula 34]

[chemical formula 35]

[chemical formula 36]

[chemical formula 37]

(In this equation, 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).

（在該式中，R ³¹及R ³²各自獨立地表示具有1至8個碳原子之烷基、具有1至7個碳原子之烷氧基、具有2至8個碳原子之烯基或具有2至7個碳原子之烯氧基；及 A ³¹及A ³²各自獨立地表示選自以下式(A3-1)至(A3-8)之基團， [化學式39]

（在該等式中，虛線表示鍵結位置），其中當存在多個A ³²時，其可相同或不同；及 m31表示1至4之整數）。 The liquid crystal composition containing the compound represented by the general formula (I) may contain the compound represented by the following general formula (III), [Chemical formula 38]

(In this formula, R ³¹ and R ³² each independently represent 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 Alkenyloxy groups of 2 to 7 carbon atoms; and A ³¹ and A ³² each independently represent a group selected from the following formulas (A3-1) to (A3-8), [Chemical Formula 39]

(In this equation, the dotted line represents the bonding position), wherein when there are a plurality of ^A32 , they may be the same or different; and m31 represents an integer of 1 to 4).

（在該式中，R ³¹¹及R ³²¹各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基、具有2至5個碳原子之烯基或具有2至4個碳原子之烯氧基；及 A ³¹¹及A ³²¹各自獨立地表示選自以下式(A31-1)至(A31-6)之基團， [化學式41]

（在該等式中，虛線表示鍵結位置），其中當存在多個A ³²¹時，其可相同或不同；及 m311表示1至3之整數）。由通式(III)表示之化合物更佳為由以下通式(III-ii)表示之化合物， [化學式42]

（在該式中，R ³¹²及R ³²²各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基、具有2至5個碳原子之烯基或具有2至4個碳原子之烯氧基； A ³¹²及A ³²²各自獨立地表示選自以下式(A32-1)至(A32-4)之基團， [化學式43]

（在該等式中，虛線表示鍵結位置），其中當存在多個A ³²²時，其可相同或不同；及 m312表示1或2）。由通式(III)表示之化合物進一步較佳為由以下通式(III-iii)表示之化合物，

（在該式中，R ³¹³及R ³²³各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基或具有2至5個碳原子之烯基； A ³¹³及A ³²³各自獨立地表示選自以下式(A33-1)及(A33-2)之基團， [化學式44]

（在該等式中，虛線表示鍵結位置），其中當存在多個A ³²³時，其可相同或不同；及 m313表示1或2））。由通式(III)表示之化合物尤其較佳為由以下通式(III-iv-1)至(III-iv-10)表示之化合物， [化學式45]

[化學式46]

（在該等式中，R ³¹⁴及R ³²⁴各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基或具有2至5個碳原子之烯基）。 From the viewpoint of liquid crystal phase temperature range, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, the compound represented by the general formula (III) is preferably represented by the following general formula The compound represented by (III-i), [Chemical Formula 40]

(In this formula, R ³¹¹ and R ³²¹ each independently represent 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 Alkenyloxy groups of 2 to 4 carbon atoms; and A ³¹¹ and A ³²¹ each independently represent a group selected from the following formulas (A31-1) to (A31-6), [Chemical Formula 41]

(In this equation, the dotted line represents the bonding position), wherein when there are a plurality of A ³²¹ , they may be the same or different; and m311 represents an integer of 1 to 3). The compound represented by the general formula (III) is more preferably a compound represented by the following general formula (III-ii), [Chemical formula 42]

(In this formula, R ³¹² and R ³²² each independently represent 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 Alkenyloxy groups of 2 to 4 carbon atoms; A ³¹² and A ³²² each independently represent a group selected from the following formulas (A32-1) to (A32-4), [chemical formula 43]

(In this equation, the dotted line represents the bonding position), where when there are multiple A ³²² , they may be the same or different; and m312 represents 1 or 2). The compound represented by the general formula (III) is further preferably a compound represented by the following general formula (III-iii),

(In this 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 ^A323 each independently represent a group selected from the following formulas (A33-1) and (A33-2), [chemical formula 44]

(In this equation, the dotted line represents the bonding position), wherein when there are multiple A ³²³ , they may be the same or different; and m313 represents 1 or 2)). The compound represented by the general formula (III) is especially preferably a compound represented by the following general formulas (III-iv-1) to (III-iv-10), [Chemical formula 45]

[chemical formula 46]

(In this equation, 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) .

In addition, the compound represented by the general formula (I) can be added to and used in a liquid crystal composition having a neutral or negative dielectric constant anisotropy (Δε). In this case, the liquid crystal composition containing the compound represented by the general formula (I) preferably has a dielectric constant anisotropy (Δε) of -20 or more and 2 or less. From the viewpoint of 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) is preferably -15 or more and 1.5 or less, more preferably -10 or more and 1 or less, and especially preferably -5 or more and 0.5 or less.

（在該式中，R ⁴¹及R ⁴²各自獨立地表示具有1至8個碳原子之烷基、具有1至7個碳原子之烷氧基、具有2至8個碳原子之烯基或具有2至7個碳原子之烯氧基； A ⁴¹及A ⁴²各自獨立地表示選自以下式(A4-1)至(A4-11)之基團， [化學式48]

（在該等式中，虛線表示鍵結位置），其中：當存在多個A ⁴¹時，其可相同或不同；且當存在多個A ⁴²時，其可相同或不同； Z ⁴¹及Z ⁴²各自獨立地表示-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-或單鍵，其中：當存在多個Z ⁴¹時，其可相同或不同；且當存在多個Z ⁴²時，其可相同或不同； m41及m42各自獨立地表示0至3之整數，且m41+m42表示1至3之整數）。 When the liquid crystal composition containing the compound represented by the general formula (I) has neutral or negative dielectric constant anisotropy (Δε), the liquid crystal composition may contain the compound represented by the following general formula (IV), [Chemical formula 47 ]

(In this formula, R ⁴¹ and R ⁴² each independently represent 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 Alkenyloxy groups of 2 to 7 carbon atoms; A ⁴¹ and A ⁴² each independently represent a group selected from the following formulas (A4-1) to (A4-11), [chemical formula 48]

(In this equation, the dotted line represents the bonding position), wherein: when there is a plurality of A ⁴¹ , it may be the same or different; and when there is a plurality of A ⁴² , it may be the same or different; Z ⁴¹ and Z ⁴² Each independently represents -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=NN=CH-, -CF=CF-, -C≡C- or a single bond, wherein: when there are multiple Z ⁴¹ , they can be the same or different; and when When there are a plurality of Z ⁴² , they may be the same or different; m41 and m42 each independently represent an integer of 0 to 3, and m41+m42 represent an integer of 1 to 3).

（在該式中，R ⁴¹¹及R ⁴²¹各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基、具有2至5個碳原子之烯基或具有2至4個碳原子之烯氧基； A ⁴¹¹及A ⁴²¹各自獨立地表示選自式(A4-1)至(A4-9)之基團，其中：當存在多個A ⁴¹¹時，其可相同或不同；且當存在多個A ⁴²¹時，其可相同或不同； Z ⁴¹¹及Z ⁴²¹各自獨立地表示-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-或單鍵，其中：當存在多個Z ⁴¹¹時，其可相同或不同；且當存在多個Z ⁴²¹時，其可相同或不同； m411及m421各自獨立地表示0至3之整數且m411+m421表示1至3之整數）。由通式(IV)表示之化合物更佳為由以下通式(IV-ii)表示之化合物， [化學式50]

（在該式中，R ⁴¹²及R ⁴²²各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基、具有2至5個碳原子之烯基或具有2至4個碳原子之烯氧基； A ⁴¹²及A ⁴²²各自獨立地表示選自式(A4-1)至(A4-7)之基團，其中：當存在多個A ⁴¹²時，其可相同或不同；且當存在多個A ⁴²²時，其可相同或不同； Z ⁴¹²及Z ⁴²²各自獨立地表示-OCH ₂-、-CH ₂O-、-CH ₂CH ₂-、-COO-、-OCO-、-CF ₂O-、-OCF ₂-或單鍵，其中：當存在多個Z ⁴¹²時，其可相同或不同；且當存在多個Z ⁴²²時，其可相同或不同； m412及m422各自獨立地表示0、1或2且m412+m422表示1或2）。由通式(IV)表示之化合物進一步較佳由以下通式(IV-iii)表示之化合物， [化學式51]

（在該式中，R ⁴¹³及R ⁴²³各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基或具有2至5個碳原子之烯基； A ⁴¹³及A ⁴²³各自獨立地表示選自式(A4-1)至(A4-5)之基團，其中當存在多個A ⁴¹³時，其可相同或不同；且當存在多個A ⁴²³時，其可相同或不同； Z ⁴¹³及Z ⁴²³各自獨立地表示-OCH ₂-、-CH ₂O-、-CH ₂CH ₂-或單鍵，其中：當存在多個Z ⁴¹³時，其可相同或不同；且當存在多個Z ⁴²³時，其可相同或不同；及 m413及m423獨立地表示0、1或2且m413+m423表示1或2）。由通式(IV)表示之化合物尤其較佳為由以下通式(IV-iv-1)至(IV-iv-8)表示之化合物， [化學式52]

[化學式53]

（在該等式中，R ⁴¹⁴及R ⁴²⁴各自獨立地表示具有1至5個碳原子之烷基、具有1至4個碳原子之烷氧基或具有2至5個碳原子之烯基）。 From the viewpoint of liquid crystal phase temperature range, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, the compound represented by general formula (IV) is preferably represented by the following general formula The compound represented by (IV-i), [Chemical Formula 49]

(In this formula, R ⁴¹¹ and R ⁴²¹ each independently represent 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 Alkenyloxy groups of 2 to 4 carbon atoms; A ⁴¹¹ and A ⁴²¹ each independently represent a group selected from formulas (A4-1) to (A4-9), wherein: when there are multiple A ⁴¹¹ , it can be the same or different; and when there are multiple A ^421s , 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=NN=CH-, -CF=CF- , -C≡C- or a single bond, wherein: when there are a plurality of Z ⁴¹¹ , they may be the same or different; and when there are a plurality of Z ⁴²¹ , they may be the same or different; m411 and m421 each independently represent 0 to an integer of 3 and m411+m421 represents an integer of 1 to 3). The compound represented by the general formula (IV) is more preferably a compound represented by the following general formula (IV-ii), [Chemical formula 50]

(In this formula, R ⁴¹² and R ⁴²² each independently represent 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 Alkenyloxy groups of 2 to 4 carbon atoms; A ⁴¹² and A ⁴²² each independently represent a group selected from formulas (A4-1) to (A4-7), wherein: when there are multiple A ⁴¹² , it can be the same or different; and when there are a plurality of A ⁴²² , 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, wherein: 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 and m412+m422 represent 1 or 2). The compound represented by the general formula (IV) is further preferably a compound represented by the following general formula (IV-iii), [Chemical formula 51]

(In this 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 formulas (A4-1) to (A4-5), wherein when there are multiple A ^413s , they may be the same or different; and when there are multiple A ^423s , 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, wherein: when there are multiple Z ⁴¹³ , they may be the same or different; and when there are a plurality of Z ⁴²³ , they may be the same or different; and m413 and m423 independently represent 0, 1 or 2 and m413+m423 represent 1 or 2). The compound represented by the general formula (IV) is especially preferably a compound represented by the following general formulas (IV-iv-1) to (IV-iv-8), [Chemical formula 52]

[chemical formula 53]

(In this equation, 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) .

（在該式中，Sp ^x1表示具有1至20個碳原子之伸烷基，其中一個-CH ₂-或兩個或更多個非相鄰-CH ₂-可各自獨立地經-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-或-C≡C-取代，或單鍵；A ^x1表示選自以下式(Ax1-1)至(Ax1-8)之基團， [化學式55]

（在該等式中，虛線表示鍵結位置），其中當存在多個A ^x1時，其可相同或不同； Z ^x1表示-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-或單鍵，其中當存在多個Z ^x1時，其可相同或不同；及 mx1表示0或1且 mx2表示0至4之整數）。 A stabilizer can be added to the liquid crystal composition containing the compound represented by the general formula (I) to improve its storage stability. Examples of stabilizers that can be used therein include hydroquinone, hydroquinone monoalkyl ether, tertiary butylcatechol, pyrogallol, thiophenol, nitro compounds, β-naphthylamine, β-naphthol, and ethylene glycol. Nitro compounds. When a stabilizer is used, the amount added to the composition is preferably within a range of 0.005% by mass to 1% by mass, more preferably 0.02% by mass to 0.8% by mass, and further preferably 0.03% by mass to 0.5% by mass. In addition, one kind of stabilizer may be used, or two or more kinds of stabilizers may be used in combination. Examples of stabilizers include compounds represented by the following general formula (X1), [Chemical Formula 54]

(In this formula, Sp ^x1 represents an alkylene group having 1 to 20 carbon atoms, in which one -CH ₂ - or two or more non-adjacent -CH ₂ - can each independently pass through -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH =CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-, or A single bond; Ax1 represents a group selected from the following formulas ( ^Ax1-1 ) to (Ax1-8), [Chemical Formula 55]

(In this equation, the dotted line represents the bonding position), wherein when there are multiple A ^x1 , they may be the same or different; Z ^x1 represents -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=NN=CH-, -CF=CF- , -C≡C- or a single bond, wherein when there are a plurality of Z ^x1 , they may be the same or different; and mx1 represents 0 or 1 and mx2 represents an integer from 0 to 4).

（在該式中，Sp ^x11表示具有1至20個碳原子之伸烷基，其中一個-CH ₂-或兩個或更多個非相鄰-CH ₂-可各自獨立地經-O-、-COO-或-OCO-取代，或單鍵； A ^x11表示選自以下式(Ax11-1)及(Ax11-2)之基團， [化學式57]

（在該等式中，虛線表示鍵結位置），其中當存在多個A ^x11時，其可相同或不同； Z ^x11表示-COO-、-OCO-、-OCO-CH ₂CH ₂-、-CH ₂CH ₂-COO-或單鍵，其中當存在多個Z ^x11時，其可相同或不同；及 mx11表示0或1且 mx21表示0或1）。由通式(X1)表示之化合物尤其較佳為由以下通式(X1-ii-1)至(X1-ii-4)表示之化合物， [化學式58]

（在該等式中，Sp ^x12表示具有1至20個碳原子之伸烷基或單鍵）。 From the viewpoint of voltage retention and compatibility with liquid crystal compositions, the compound represented by the general formula (X1) is preferably a compound represented by the following general formula (X1-i), [Chemical formula 56]

(In this formula, Sp ^x11 represents an alkylene group having 1 to 20 carbon atoms, in which one -CH ₂ - or two or more non-adjacent -CH ₂ - can each independently pass through -O-, -COO- or -OCO-substituted, or a single bond; A ^x11 represents a group selected from the following formulas (Ax11-1) and (Ax11-2), [chemical formula 57]

(In this equation, the dotted line represents the bonding position), wherein when there are multiple A ^x11 , they may be the same or different; Z ^x11 represents -COO-, -OCO-, -OCO-CH ₂ CH ₂ -, - CH ₂ CH ₂ —COO— or a single bond, wherein when there are a plurality of Z ^x11 , they may be the same or different; and mx11 represents 0 or 1 and mx21 represents 0 or 1). The compound represented by the general formula (X1) is particularly preferably a compound represented by the following general formulas (X1-ii-1) to (X1-ii-4), [Chemical Formula 58]

(In this equation, Sp ^x12 represents an alkylene group having 1 to 20 carbon atoms or a single bond).

（在該式中，R ^x21、R ^x22、R ^x23及R ^x24各自獨立地表示氫原子、氧原子、羥基、具有1至20個碳原子之烷基或具有1至20個碳原子之烷氧基； Sp ^x21、Sp ^x22、Sp ^x23及Sp ^x24各自獨立地表示間隔基團或單鍵；及 mx21表示0或1， mx22表示0或1，且 mx23表示0或1）。 Examples of the liquid crystal composition containing the compound represented by the general formula (I) include compounds represented by the following general formula (X2), [Chemical Formula 59]

(In this formula, ^Rx21 , ^Rx22 , ^Rx23 , and ^Rx24 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 group; Sp ^x21 , Sp ^x22 , Sp ^x23 and Sp ^x24 each independently represent a spacer group or a single bond; and mx21 represents 0 or 1, mx22 represents 0 or 1, and mx23 represents 0 or 1).

（在該式中，R ^x211、R ^x221、R ^x231及R ^x241各自獨立地表示氫原子、氧原子、羥基、具有1至10個碳原子之烷基或具有1至10個碳原子之烷氧基； Sp ^x211、Sp ^x221、Sp ^x231及Sp ^x224各自獨立地表示具有1至20個碳原子之直鏈或分支鏈伸烷基，其中該基團中之任意氫原子可經氟原子取代，且一個-CH ₂-或兩個或更多個非相鄰-CH ₂-可各自獨立地經-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-、-CF=CF-或-C≡C-取代，或單鍵；及 mx211表示0或1， mx221表示0或1，且 mx231表示0或1）。由通式(X2)表示之化合物更佳為由以下通式(X2-ii)表示之化合物， [化學式61]

（在該式中，R ^x212及R ^x222各自獨立地表示氫原子、具有1至10個碳原子之烷基或具有1至10個碳原子之烷氧基； Sp ^x212及Sp ^x222各自獨立地表示具有1至10個碳原子之直鏈伸烷基，其中一個-CH ₂-或兩個或更多個非相鄰-CH ₂-可各自獨立地經-O-、-COO-或-OCO-取代，或單鍵；及 mx212表示0或1）。由通式(X2)表示之化合物尤其較佳為由以下通式(X2-iii)表示之化合物， [化學式62]

（在該式中，R ^x213及R ^x223各自獨立地表示氫原子、具有1至10個碳原子之烷基或具有1至10個碳原子之烷氧基；及 Sp ^x213表示具有1至10個碳原子之直鏈伸烷基，其中一個-CH ₂-或兩個或更多個非相鄰-CH ₂-可各自獨立地經-COO-或-OCO-取代）。 From the viewpoint of voltage retention and compatibility with liquid crystal compositions, the compound represented by the general formula (X2) is preferably a compound represented by the following general formula (X2-i), [Chemical Formula 60]

(In this 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 base; Sp ^x211 , Sp ^x221 , Sp ^x231 and Sp ^x224 each independently represent a linear or branched chain alkylene group having 1 to 20 carbon atoms, wherein any hydrogen atom in the group may be substituted by a fluorine atom, and One -CH ₂ - or two or more non-adjacent -CH ₂ - can each independently pass through -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C- substitution, or a single bond; and mx211 represents 0 or 1, mx221 represents 0 or 1, and mx231 represents 0 or 1). The compound represented by the general formula (X2) is more preferably a compound represented by the following general formula (X2-ii), [Chemical formula 61]

(In this 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 represent A straight-chain alkylene group having 1 to 10 carbon atoms, in which one -CH ₂ - or two or more non-adjacent -CH ₂ - can each independently pass through -O-, -COO- or -OCO- substitution, or a single bond; and mx212 for 0 or 1). The compound represented by the general formula (X2) is especially preferably a compound represented by the following general formula (X2-iii), [Chemical formula 62]

(In this 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; and Sp ^x213 represents a group having 1 to 10 straight-chain alkylene group of carbon atoms, in which one -CH ₂ - or two or more non-adjacent -CH ₂ - may be independently substituted by -COO- or -OCO-).

烷-2,5-二基中所含之環結構各自可呈反式及順式中之任一者。然而，自液體結晶性之觀點來看，對於上述基團中之每一者，反式之含量較佳高於順式之含量，環結構中反式之含量更佳為80%或更大；環結構中反式之含量進一步較佳為90%或更大；環結構中反式之含量進一步更佳為95%或更大；且環結構中反式之含量尤其較佳為98%或更大。此外，在本發明中，以下符號(CY-1)表示1,4-伸環己基之反式及/或順式。 [化學式63]

（在該式中，虛線表示鍵結位置。） In the present invention, 1,4-cyclohexylene, decalin-2,6-diyl and 1,3-di

Each ring structure contained in the alkane-2,5-diyl group may be either trans or cis. However, from the viewpoint of liquid crystallinity, for each of the above-mentioned groups, the content of the trans form is preferably higher than that of the cis form, and the content of the trans form in the ring structure is more preferably 80% or more; The content of trans in the ring structure is further preferably 90% or greater; the content of trans in the ring structure is further preferably 95% or greater; and the content of trans in the ring structure is especially preferably 98% or more big. In addition, in the present invention, the following symbol (CY-1) represents the trans form and/or the cis form of 1,4-cyclohexylene. [chemical formula 63]

(In this formula, the dotted line indicates the bonding position.)

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

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

The extrapolated value of the refractive index anisotropy (Δn, measurement wavelength: 589 nm) was obtained by using host liquid crystal N composed of the following compound and adding it in an amount of 5%. (Main 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) to produce a compound represented by formula (I-1) [chemical formula 64]

Under a nitrogen atmosphere, 15 g of the compound represented by formula (I-1-1) and 40 mL of tetrahydrofuran (THF) were charged into a reaction vessel. With the reaction vessel cooled 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. Subsequently, 4 g of sulfur were added little by little and the mixture was stirred for another 1 hour at -78°C. Furthermore, 1-bromopentane was slowly added dropwise at -78°C and the mixture was stirred at -30°C for 1 hour. To the reaction solution, 2 ml of ethyl acetate was added dropwise; the reaction solution was returned to 0° C.; a saturated aqueous ammonium chloride solution was poured; ethyl acetate was added; The organic layer was washed with brine and purified by column chromatography (silica gel, dichloromethane/hexane), thereby obtaining 20 g of the compound represented by formula (I-1-2).

20 g of the compound represented by formula (I-1-2) and 99 mL of dichloromethane were charged into the reaction vessel. Under ice-cooling, 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 treatment. The organic layer was washed with brine and purified by column chromatography (silica gel, dichloromethane/hexane), thereby obtaining 24 g of the compound represented by formula (I-1-3).

Under a nitrogen atmosphere, 24 g of a compound represented by formula (I-1-3), 0.2 g of copper(I) iodide, 1 g of tetraphenylphosphine palladium, 15 mL of triethylamine and 100 mL of N,N - Dimethylformamide (DMF) was charged to the reaction vessel. Under 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. The organic layer was washed successively with water and brine, and purified by column chromatography (silica gel, toluene/hexane) and activated carbon treatment. Then, 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 extraction was performed with toluene. The organic layer was sequentially washed with water and brine, and then purified by column chromatography (silica gel, toluene/hexane); thus obtaining 13 g of a compound represented by formula (I-1-4).

Under a nitrogen atmosphere, 9 g of a compound represented by formula (I-1-5), 0.15 g of copper(I) iodide, 0.5 g of tetraphenylphosphine palladium, 15 mL of triethylamine and 60 mL of DMF were charged in the reaction vessel. Under heating at 80°C, 30 ml of DMF containing 13 g of the compound represented by formula (I-1-4) 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. The organic layer was sequentially washed with water and brine, and then subjected to column chromatography (silica gel, toluene/hexane) and activated carbon treatment; thereby obtaining 18 g of the 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 charged into the reaction vessel. 3 g of hydroxylamine hydrochloride were added at room temperature, and the mixture was stirred for 10 hours. The reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed successively with water, saturated aqueous sodium bicarbonate solution and brine, followed by distilling off the solvent and drying; thereby obtaining 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 charged into the reaction vessel. Under ice cooling, 6.7 g of N-chlorobutadiimide was added, and the mixture was heated and stirred at 40° C. for 2 hours. The reaction solution was cooled and poured into water, and extracted with dichloromethane. The organic layer was sequentially washed with water and brine, followed by distilling off the solvent and drying; thereby obtaining 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 charged into the reaction vessel. Under ice cooling, 15 g of triethylamine was added dropwise, and the mixture was heated and stirred at 40° C. for 5 hours. The reaction solution was cooled and poured into water, and extracted with toluene. The organic layer was washed with water and brine successively, and then purified by column chromatography (silica gel, toluene/hexane), activated carbon treatment and recrystallization (toluene/ethanol); thus obtained 12 g of indicated compound. MS(EI): m/z=435 melting point 113°C phase transition temperature Cr113 N 227 Iso (Example 2) to produce a compound represented by formula (I-2) [chemical formula 65]

5 g of the compound represented by formula (I-2-1), 0.05 g of copper iodide (I), 0.15 g of tetraphenylphosphine palladium, 7 mL of triethylamine and 50 mL of N,N -Dimethylformamide (DMF). Under heating at 70°C, a 10 ml DMF solution containing 3.2 g 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 sequentially washed with water and brine, and then purified by column chromatography (silica gel, toluene/hexane) and activated carbon treatment; thereby producing a compound represented by formula (I-2). Characteristics: oily MS (EI): m/z=420 (Example 3) to produce the compound represented by formula (I-3) [chemical formula 66]

Except that the compound represented by formula (I-2-2) is replaced by the compound represented by formula (I-3-4) in Example 2, by the same method as in Example 2, the compound produced by formula (I-3) ) represented by the compound. MS(EI): m/z=512 melting point 65°C phase transition temperature Cr65N 101 Iso (Example 4) to produce a compound represented by formula (I-4) [chemical formula 67]

Under a nitrogen atmosphere, 10 g of a compound represented by formula (I-4-1) and 15 g of a compound represented by formula (I-4-2) were reacted with each other in the same manner as in Example 1; 11 g of N-bromosuccinimide was added little by little in the same manner as in Example 1; and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into water and subjected to liquid separation treatment. The organic layer was washed with brine and purified by column chromatography (silica gel, dichloromethane/hexane); thereby obtaining 19 g of a compound represented by formula (I-4-4).

Under a nitrogen atmosphere, 19 g of a compound represented by formula (I-4-4), 14 g of potassium acetate, 14 g of bis(pinacolyl)diboron, 90 mL of dimethylsulfoxide, and 0.4 g of [1, 1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct was charged into a reaction vessel, 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); thus obtaining 17 g of a compound represented by formula (I-4-5).

Under a nitrogen atmosphere, 17 g of a 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, 15 mL of water and 0.2 g of bis(triphenylphosphine)palladium(II) dichloride were charged to the reaction vessel, and the mixture was heated and refluxed 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 (silica gel, toluene/hexane) and recrystallization (toluene/ethanol); thereby obtaining 13 g of a compound represented by formula (I-4) . MS (EI): m/z=440 (embodiment 5) manufactures the compound represented by formula (I-5) [chemical formula 68]

The compound represented by formula (I-5-2) was produced by the method described in WO2010/115279A1. Under a nitrogen atmosphere, 10 g of a compound represented by formula (I-5-1), 9.5 g of a compound represented by formula (I-5-2), 13.5 g of potassium carbonate, 0.1 g of dichlorobis[two-tri Butyl(p-dimethylaminophenyl)phosphino]palladium(II), 80 mL of toluene, 30 mL of ethanol, and 20 mL of water were charged into a reaction vessel, and the mixture was heated and refluxed 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 (silica gel, toluene/hexane) and recrystallization (toluene/ethanol); thus obtained 10 g of compound.

Except that the compound represented by formula (I-1-6) was replaced by the compound represented by formula (I-5-3) in Example 1, 7 g of 5) The compound represented. MS(EI):m/z=423 (Example 6) Production of the compound represented by formula (I-6) [chemical formula 69]

5 g of the compound represented by formula (I-6-1), 0.05 g of copper iodide (I), 0.25 g of tetraphenylphosphine palladium, 25 mL of triethylamine and 25 mL of N,N -Dimethylformamide (DMF). 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 purified by column chromatography (silica gel, toluene/hexane) and activated carbon treatment; thus producing 2.4 g of the compound represented by formula (I-6). Melting point 96°C MS(EI):m/z=530 (Examples 7 to 15 and Comparative Examples 1 to 8)

（側鏈結構） 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 （連接基團） -          單鍵 -T-      -C≡C- 製備由以下化合物構成之主體液晶N。 （主體液晶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% The following abbreviations are used to describe liquid crystal compounds in Examples. (ring structure) [Chemical Formula 70]

(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- Preparation Host liquid crystal N composed of the following compounds. (Main 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%

（液晶組成物(M-1)） 主體液晶N                            90.0% 由式(I-1)表示之化合物        10.0% （液晶組成物(M-2)） 主體液晶N                            90.0% 由式(I-2)表示之化合物        10.0% （液晶組成物(M-3)） 主體液晶N                            90.0% 由式(I-3)表示之化合物        10.0% （液晶組成物(M-4)） 主體液晶N                            90.0% 由式(I-4)表示之化合物        10.0% （液晶組成物(M-5)） 主體液晶N                            90.0% 由式(I-5)表示之化合物        10.0% （液晶組成物(M-6)） 主體液晶N                            90.0% 由式(I-6)表示之化合物        10.0% The compounds represented by formulas (I-1) to (I-6) synthesized in the examples were added to host liquid crystal N to prepare liquid crystal compositions (M-1) to (M-6) for evaluation. In addition, the compound represented by the formula (R-1) described in Non-Patent Document 1, the compounds represented by the formulas (R-2) and (R-3) described in Patent Document 1, and the compounds represented by Formula (R-3) described in Patent Document 3 were added The compound represented by formula (R-4) was used to prepare liquid crystal compositions (RM-1) to (RM-4) for comparison. [chemical formula 71]

(Liquid Crystal Composition (M-1)) Host Liquid Crystal N 90.0% Compound represented by Formula (I-1) 10.0% (Liquid Crystal Composition (M-2)) Host Liquid Crystal N 90.0% Formula (I-2) Compound 10.0% (liquid crystal composition (M-3)) Host liquid crystal N 90.0% Compound represented by formula (I-3) 10.0% (liquid crystal composition (M-4)) Host liquid crystal N 90.0% Formula (I -4) compound represented by 10.0% (liquid crystal composition (M-5)) host liquid crystal N 90.0% compound represented by formula (I-5) 10.0% (liquid crystal composition (M-6)) host liquid crystal N 90.0% Compound represented by formula (I-6) 10.0%

Each compound evaluated was evaluated for storage stability. For storage stability, 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, and then its state was visually evaluated. The evaluation results are shown in the table below. [Table 1] Liquid crystal composition Δn storage stability Example 7 M-1 0.358 constant Example 8 M-2 0.341 constant Example 9 M-3 0.350 constant Example 10 M-4 0.332 constant Example 11 M-5 0.353 constant Example 12 M-6 0.364 Precipitation for 3 weeks Liquid crystal composition Δn storage stability Comparative example 1 RM-1 0.341 Precipitation for 1 week Comparative example 2 RM-2 0.352 Precipitation for 1 week Comparative example 3 RM-3 0.322 constant Comparative example 4 RM-4 0.350 constant

From the above results, it was found that the compound of the present invention is less likely to cause precipitation when added to the liquid crystal composition, and has high compatibility with the liquid crystal composition.

Next, the characteristics in the high frequency region of each compound to be evaluated were evaluated. For measurement, a propagation delay mode backcut type stripline method and a relative permittivity/dielectric loss tangent measuring device (manufactured by KEYCOM Corporation) were used. The dielectric anisotropy of each of the prepared liquid crystal compositions was measured at 13.17 GHz and 20°C, and the dielectric anisotropy Δε of each compound used for evaluation was calculated by extrapolation (13.17 GHz). The evaluation results are shown in Table 2. [Table 2] Compounds used for evaluation Δε (13.17 GHz) Example 13 I-1 1.42 Example 14 I-3 0.90 Example 15 I-5 1.25 Example 16 I-6 0.95 Comparative Example 5 R-1 0.01 Comparative example 6 R-2 0.01 Comparative Example 7 R-3 0.43 Comparative Example 8 R-4 0.81

From the above results, it was found that all the compounds of the present invention exhibit large dielectric constant anisotropy in the high frequency region. Since the compounds of the present invention form extensive conjugated systems via ring structures and linking groups, it is considered that these compounds exhibit large dielectric constant anisotropy in the high-frequency region.

In addition, it was found that the liquid crystal compositions (M-1) to (M-6) containing the compound of the present invention all exhibited a material characteristic (ηε) of 20 or more. The material properties (ηε) are defined as follows. ε⊥ =(3εaverage-ε∥)/2 tanδ⊥ =(3εaverage tanδaverage-ε∥tanδ∥)/2ε⊥ Adjustable variability (τ) = (ε∥-ε⊥)/ε ∥ Material property (ηε) = τ/(max(tanδ∥, tanδ⊥))

According to the above results, the compound of the present invention has a large refractive index anisotropy Δn and high compatibility with liquid crystal compositions, and exhibits a large dielectric constant anisotropy in a high frequency region; and therefore, it can be used as a high Materials for frequency phase shifters, phase array antennas, image recognition devices, distance measuring devices, liquid crystal display devices, liquid crystal lenses, birefringent lenses for displaying stereoscopic images, or similar devices.

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Claims (12)

A compound represented by the following general formula (I), [Chemical Formula 1]

(In this formula, R represents ^a hydrogen atom, a fluorine atom, a chlorine atom or a linear or branched chain alkyl group having 1 to 20 carbon atoms, wherein any hydrogen atom in the alkyl group may be substituted by a halogen atom, and One -CH ₂ - or two or more -CH ₂ - in the alkyl group are each independently and optionally through -O-, -S-, -CO-, -COO-, -OCO-, -CO -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-substituted, which The limiting condition is that the oxygen atoms are not bonded to each other; A1 and A2 each independently represent ^a hydrocarbon ring or ^a heterocyclic ring with ³ to 16 carbon atoms substituted as the case may be ^; when there are multiple A1, these A1 The same or different as the case may be; and when there are multiple A ^2s , the A ^2s are the same or different as the case may be; Z ¹ , Z ² and Z ³ each independently represent a divalent linking group or a single bond; when there are multiple When Z ¹ , these Z ¹ are the same or different depending on the situation; and when there are multiple Z ² , these Z ² are the same or different depending on the situation; m1 and m2 each independently represent an integer from 0 to 3; and 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, wherein any hydrogen atom in the alkyl group is optionally substituted by a halogen atom; one of the alkyl groups -CH ₂ - or two or more -CH ₂ - each independently and optionally via -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO- , -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- or -C≡C-, the limitation is that the oxygen atoms are not bonded to each other or A ^x represents a structure selected from the group consisting of (Ax-1) to (Ax-5),

(In this equation, the dotted line represents the bonding position; and Y each independently represents ^a hydrogen atom, a fluorine atom, a chlorine atom or an alkyl or alkoxy group having 1 to 8 carbon atoms, wherein any hydrogen atom is optionally Substituted by a fluorine atom, and when there are multiple ^Y1s , these ^Y1s are the same or different as appropriate; ^Y2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyano group, or a group with 1 to 8 carbons An alkyl group of atoms, wherein any hydrogen atom is optionally substituted by a fluorine atom, and one -CH ₂ - or two or more -CH ₂ - in the alkyl group are each independently and optionally replaced by -O-, - S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH= CH-, CF=CF- or -C≡C-, the restriction is that the oxygen atoms are not bonded to each other), wherein: when A ^x is selected from the equation (Ax-1) to (Ax-5) When the structure of the group, m1+m2 represents an integer from 0 to 3; and when A ^x is not a structure selected from the group consisting of the equations (Ax-1) to (Ax-5), m1+m2 represents 1 integers up to 4). The compound as claimed in item 1, wherein in the general formula (I), A ¹ and A ² each independently represent a group selected from the group consisting of: (a) 1,4-cyclohexyl (one of which is -CH ₂ - or two or more non-adjacent -CH ₂ - substituted by -O- or -S- as appropriate); (b) 1,4-phenylene (where one -CH= or two or more multiple non-adjacent -CH= optionally substituted with -N=); (c) 1,4-cyclohexenyl, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2, 6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl base, decalin-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl (where The hydrogen atoms present in these groups are optionally substituted by fluorine or chlorine atoms, and present in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetra Hydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9 , 10-diyl or phenanthrene-2,7-diyl -CH= or two or more -CH= as the case may be substituted by -N=); and (d) thiophene-2,5-di base, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl or thieno [3,2-b]thiophene-2,5-diyl (where one -CH= or two or more non-adjacent -CH= present in such groups are optionally substituted by -N=) , wherein the selected group is optionally unsubstituted or substituted by one or more substituents L ¹ , L ¹ represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a nitro group, a cyano group, an iso Cyano, Amino, Hydroxy, Mercapto, Methylamino, Dimethylamino, Diethylamino, Diisopropylamino, Trimethylsilyl, Dimethylsilyl, Thioisocyanate or a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein one -CH ₂ - or two or more -CH ₂ - are each independently and optionally via -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-, provided that the oxygen atoms are not directly bonded to each other, and any hydrogen atom in the alkyl group is optionally substituted by a fluorine atom. The compound according to claim 1 or 2, wherein in the general formula (I), Z ¹ , Z ² and Z ³ each independently represent 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=NN=C-, -CH=N-, -N=CH-, -C≡CC≡C- or alkylene having 2 to 20 carbon atoms, wherein the alkylene One -CH ₂ - or two or more -CH ₂ - in the group are optionally substituted by -O-, -S-, -COO- or -OCO-, provided that the oxygen atoms are not directly bonded to each other . The compound according to any one of claim items 1 to 3, wherein the above general formula (I) is represented by the following general formula (Ii), [chemical formula 2]

(In this formula, R ¹¹ represents a hydrogen atom or a linear or branched chain alkyl group having 1 to 20 carbon atoms, wherein any hydrogen atom in the group is optionally substituted by a halogen atom and one of the groups -CH ₂ - or two or more -CH ₂ - each independently and optionally substituted by -O-, -S-, -CH=CH-, -CF=CF- or -C≡C-; A ¹¹ and A ²¹ each independently represent 1,4-phenylene, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 5,6,7,8-tetrahydronaphthalene-1,4- Diyl, phenanthrene-2,7-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2 ,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl or thieno[3,2-b]thiophene-2,5-diyl, where when When there are multiple ^A11s , these ^A11s are the same or different as appropriate; when there are multiple ^A21s , these ^A21s are the same or different as appropriate; and these groups are optionally unsubstituted or modified by one or more A substituent L ¹¹ is substituted; L ¹¹ represents a fluorine atom, a chlorine atom, or a straight-chain alkyl group with 1 to 20 carbon atoms or a branched chain or cyclic alkyl group with 3 to 20 carbon atoms, wherein in the group Any hydrogen atom in the group is optionally replaced by a fluorine atom, and one -CH ₂ - or two or more -CH ₂ - in the group are independently and optionally replaced by -O-, -S-, -CH= CH-, -CF=CF- or -C≡C-substitution, wherein when there are multiple L ¹¹ , these L ¹¹ are the same or different as appropriate; 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=NN=CH-, -CF=CF-, -C≡C-, -C≡CC≡C- or a single bond, wherein: when there are multiple Z ¹¹ When , these Z ¹¹ are the same or different depending on the situation; and when there are multiple Z ²¹ , these Z ²¹ are the same or different depending on the situation; m11 and m21 each independently represent 0, 1 or 2; A ^x1 represents a hydrogen atom or A straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, wherein any hydrogen atom in the group is optionally substituted by a halogen atom and one of the groups -CH ₂ - or two or more - CH ₂ - are each independently optionally substituted by -O-, -S-, -CH=CH-, -CF=CF- or -C≡C-, or A ^x1 represents a group selected from the following formula (Ax-1-i ) to the structure of the group consisting of (Ax-5-i),

(In this equation, the dotted line represents the bonding position, and Y ¹¹ each independently represent a hydrogen atom, a fluorine atom, or an alkyl or alkoxy group having 1 to 8 carbon atoms, wherein when there are a plurality of Y ¹¹ , the Etc. Y ¹¹ is the same or different as appropriate; Y ²¹ represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, an isothiocyanate group or an alkyl group having 1 to 8 carbon atoms, wherein any hydrogen atom is optionally substituted by a fluorine atom , wherein one -CH ₂ - or two or more -CH ₂ - in the alkyl group are each independently and optionally through -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CH=CH-, -CF=CF-, or -C≡C-, provided that the oxygen atoms are not bonded to each other) , wherein: when A ^x1 is a structure selected from the group consisting of the equations (Ax-1-i) to (Ax-5-i), m11+m21 represents an integer from 0 to 2; and when A ^x1 is not When the structure selected from the group consisting of the equations (Ax-1-i) to (Ax-5-i), m11+m21 represents an integer of 1 to 3). The compound according to any one of claim items 1 to 4, wherein the above general formula (I) is represented by the following general formula (I-ii), [chemical formula 3]

(In this formula, R ¹² represents a linear or branched chain alkyl group having 1 to 12 carbon atoms, wherein any hydrogen atom in the group is optionally substituted by a fluorine atom, and one of the groups -CH ₂ - or two or more -CH ₂ - each independently and optionally substituted by -O-, -CH═CH- or -C≡C-; A ¹² and A ²² each independently represent a group selected from the following formula (A-ii-1) to (A-ii-17) groups, [chemical formula 4]

(In this equation, the dotted line represents the bonding position, and when there are multiple L ^12s , the L ^12s are the same or different as appropriate), wherein: when there are multiple A ^12s , the A ^12s are the same as the case may be or different; and when there are multiple A ²² , these A ²² are the same or different as the case may be; L ¹² represents a fluorine atom or a straight-chain alkyl group with 1 to 10 carbon atoms or a branch with 3 to 10 carbon atoms Chain or cyclic alkyl, wherein any hydrogen atom in the group is optionally substituted by a fluorine atom and -CH ₂ - in the group is optionally substituted by -O-; 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=NN=CH-, -CF=CF-, -C≡C-, -C≡CC≡C- or a single bond, where: when When there are multiple Z ¹² , these Z ¹² are the same or different as appropriate; and when there are multiple Z ²² , these Z ²² are the same or different as appropriate; 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 any one of the equations (Ax-1-i) and (Ax-2-i)). The compound according to any one of claims 1 to 5, wherein the above-mentioned general formula (I) is represented by the following general formula (I-iii), [chemical formula 5]

(In this formula, R 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, an alkenyl group having 2 to 7 carbon atoms An alkenyloxy group or an alkynyl group having 2 to 8 carbon atoms; A ¹³ and A ²³ each independently represent a group selected from the following formulas (A-iii-1) to (A-iii-7), (A-iii- 12), the group of (A-iii-15) and (A-iii-17); [chemical formula 6]

(In this equation, the dotted line represents the bonding position, and when there are multiple L ¹³ , these L ¹³ are the same or different as appropriate); L ¹³ represents a fluorine atom or a straight-chain alkane having 1 to 10 carbon atoms or a branched or cyclic alkyl group with 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≡CC≡C- or a single bond; m13 and m23 each independently represent 0 or 1; Y13 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom). A composition comprising the compound according to any one of claims 1-6. A liquid crystal composition comprising the compound according to any one of claims 1 to 6. The liquid crystal composition according to Claim 8, wherein the refractive index anisotropy is 0.15 or greater. The liquid crystal composition according to claim 8, wherein the dielectric constant anisotropy is 2 or greater. The liquid crystal composition according to claim 8, wherein the dielectric constant anisotropy is 2 or less. A high-frequency phase shifter, phase array antenna, image recognition device, distance measurement device, liquid crystal display device, liquid crystal lens or birefringent lens for stereoscopic image display, which uses the liquid crystal composition according to claims 8 to 11.