JP2023091998A - Compounds, liquid crystal compositions, liquid crystal display elements using these, sensors, liquid crystal lenses, optical communication devices, and antennas - Google Patents

Abstract

To provide: compounds that can provide liquid crystal compositions with high Tni, large Δn, low Vth, large Δεr, small tanδiso, and good low temperature storage properties; liquid crystal compositions; liquid crystal display elements using these, sensors, liquid crystal lenses, optical communication devices, and antennas.SOLUTION: The compounds are represented by general formula (i) having at least four ring structures and an isothiocyanate group (-NCS). The liquid crystal compositions contain one or more of the compounds.SELECTED DRAWING: None

Description

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

2. Description of the Related Art As a new application of liquid crystals, which are often used for displays, antennas using liquid crystals for transmitting and receiving radio waves between mobile objects such as automobiles and communication satellites are attracting attention. Conventionally, satellite communication uses a parabolic antenna, but when used in a mobile object such as an automobile, the parabolic antenna must be pointed in the direction of the satellite at any time, requiring a large movable part. However, an antenna using a liquid crystal can change the direction of transmission and reception of radio waves by operating the liquid crystal inside the panel. In addition, in order to realize global high-capacity and high-speed communication, studies are progressing on a low-orbit satellite constellation with a large number of low-orbit satellites. A liquid crystal antenna that can easily change the direction of transmission and reception of radio waves is useful for tracking low-orbit satellites that appear to be constantly moving from the ground.
In general, automatic driving of automobiles and the like requires a large amount of data download of high-precision 3D map information. However, if the antenna uses a liquid crystal, it will be possible to download a large amount of data from a communication satellite by installing the antenna in a vehicle without any mechanical moving parts. The frequency band used for satellite communications is about 13 GHz, which is significantly different from the frequencies used for liquid crystal displays up to now. Therefore, the physical properties required for liquid crystals are also greatly different, and Δn required for liquid crystals for antennas is about 0.4, and the operating temperature range is -20 to 120°C.
Also, an infrared laser image recognition/ranging device using a liquid crystal is attracting attention as a sensor for automatic driving of moving bodies such as automobiles. The required liquid crystal for this application has a Δn of 0.3 to 0.6 and an operating temperature range of 10 to 100°C.
Furthermore, it is known that many liquid crystalline compounds constituting liquid crystal compositions exhibiting a high Δn of 0.2 or more have low compatibility. Therefore, it is also important to select a highly compatible liquid crystalline compound.
On the other hand, for example, Japanese Patent Laid-Open No. 2002-100001 is cited as a technique for liquid crystals for antennas.
Non-Patent Document 1 proposes the use of a liquid crystal material as a component of a high-frequency device.

JP 2016-37607 A

D. Dolfi, "Electronics Letters" (UK), 1993, vol. 29, no. 10, p. 926-927

INDUSTRIAL APPLICABILITY The present invention provides a compound which can provide a liquid crystal composition having a high _Tni , a large Δn, a low _Vth , a large Δε _r , a small tan δ _iso , and good storage stability at low temperatures, and a liquid crystal composition. It is another object of the present invention to provide a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device and an antenna using the same.

As a result of intensive studies, the present inventors have found that a liquid crystal composition containing one or more compounds represented by the general formula (i) having four ring structures and an isothiocyanate group (-NCS) has the above problem. can be solved, and the present invention has been completed.
The configuration of the present invention for solving the above problems is as follows.
The compound according to the present invention has the following general formula (i)

（一般式（ｉ）中、
Ｒ^ｉ１は、水素原子、ハロゲン原子、炭素原子数１～２０のアルキル基を表し、
当該アルキル基中の１つ又は２つ以上の－ＣＨ_２－は、それぞれ独立して、－Ｏ－、－Ｓ－、－ＣＯ－及び／又は－ＣＳ－で置換されていてもよく、
当該アルキル基中の１つ又は２つ以上の－ＣＨ_２－ＣＨ_２－は、それぞれ独立して、－ＣＯ－Ｏ－、－Ｏ－ＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－及び／又は－Ｃ≡Ｃ－で置換されていてもよく、
当該アルキル基中の１つ又は２つ以上の－ＣＨ_２－ＣＨ_２－ＣＨ_２－は、それぞれ独立して、－Ｏ－ＣＯ－Ｏ－で置換されていてもよく、
当該アルキル基中の１つ又は２つ以上の水素原子は、それぞれ独立して、ハロゲン原子で置換されていてもよいが、
酸素原子と酸素原子が直接結合することはなく、
Ａ^ｉ１、Ａ^ｉ２、Ａ^ｉ３及びＡ^ｉ４は、それぞれ独立して、炭素原子数３～１６の炭化水素環又は炭素原子数３～１６の複素環のいずれかを表し、
前記Ａ^ｉ１、Ａ^ｉ２、Ａ^ｉ３及びＡ^ｉ４中の１つ又は２つ以上の水素原子は、それぞれ独立して、置換基Ｓ^ｉ１によって置換されていてもよく、
置換基Ｓ^ｉ１は、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルファニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、炭素原子数１～２０のアルキル基のいずれかを表し、
当該アルキル基における１つ又は２つ以上の－ＣＨ_２－は、それぞれ独立して、－Ｏ－、－Ｓ－及び／又は－ＣＯ－で置換されていてもよく、
当該アルキル基における１つ又は２つ以上の－ＣＨ_２－ＣＨ_２－は、それぞれ独立して、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－、－ＣＯ－Ｏ－、－Ｏ－ＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－ＣＯ－ＮＨ－及び／又は－ＮＨ－ＣＯ－で置換されていてもよく、
当該アルキル基における１つ又は２つ以上の－ＣＨ_２－ＣＨ_２－ＣＨ_２－は、それぞれ独立して、－Ｏ－ＣＯ－Ｏ－で置換されていてもよく、
当該アルキル基における１つ又は２つ以上の水素原子は、それぞれ独立して、ハロゲン原子で置換されていてもよいが、
酸素原子と酸素原子が直接結合することはなく、
置換基Ｓ^ｉ１が複数ある場合は、それらは同一であってもよく、異なっていてもよく、
Ｚ^ｉ１、Ｚ^ｉ２及びＺ^ｉ３は、それぞれ独立して、単結合、炭素原子数１～２０のアルキレン基のいずれかを表し、
当該アルキレン基中の１つ又は２つ以上の－ＣＨ_２－は、それぞれ独立して、－Ｏ－、－ＣＦ_２－及び／又は－ＣＯ－で置換されていてもよく、
当該アルキレン基中の１つ又は２つ以上の－ＣＨ_２－ＣＨ_２－は、それぞれ独立して、－ＣＨ_２－ＣＨ（ＣＨ_３）－、－ＣＨ（ＣＨ_３）－ＣＨ_２－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－、－ＣＨ＝Ｃ（ＣＨ_３）－、－Ｃ（ＣＨ_３）＝ＣＨ－、－ＣＨ＝Ｎ－、－Ｎ＝ＣＨ－、－Ｎ＝Ｎ－、－Ｃ≡Ｃ－、－ＣＯ－Ｏ－及び／又は－Ｏ－ＣＯ－で置換されていてもよいが、
酸素原子と酸素原子が直接結合することはない。）
で表される化合物であることを特徴とする。
また、本発明に係る液晶組成物は、上記の化合物の１種又は２種以上を含むことを特徴とする。
また、本発明に係る液晶表示素子は、上述の液晶組成物を用いたことを特徴とする。
また、本発明に係るセンサは、上述の液晶組成物を用いたことを特徴とする。
また、本発明に係る液晶レンズは、上述の液晶組成物を用いたことを特徴とする。
また、本発明に係る光通信機器は、上述の液晶組成物を用いたことを特徴とする。
また、本発明に係るアンテナは、上述の液晶組成物を用いたことを特徴とする。

(in general formula (i),
R ⁱ¹ represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S—, —CO— and/or —CS—;
One or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CO-O-, -O-CO-, -CO-S-, -S-CO-, optionally substituted with -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may each independently be substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms;
one or more hydrogen atoms in A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ may each independently be substituted with a substituent ^Si1 ;
Substituent ^Si1 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S— and/or —CO—;
One or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, - optionally substituted with O—CO—, —CO—S—, —S—CO—, —CO—NH— and/or —NH—CO—,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
When there are multiple substituents ^Si1 , they may be the same or different,
Z ⁱ¹ , Z ⁱ² and Z ⁱ³ each independently represent either a single bond or an alkylene group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkylene group may be independently substituted with —O—, —CF ₂ — and/or —CO—,
One or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, —CH =CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, -C may be substituted with ≡C-, -CO-O- and/or -O-CO-,
Oxygen atoms are never directly bonded to each other. )
It is characterized by being a compound represented by
Further, the liquid crystal composition according to the present invention is characterized by containing one or more of the above compounds.
A liquid crystal display device according to the present invention is characterized by using the liquid crystal composition described above.
A sensor according to the present invention is characterized by using the liquid crystal composition described above.
A liquid crystal lens according to the present invention is characterized by using the liquid crystal composition described above.
Further, an optical communication device according to the present invention is characterized by using the liquid crystal composition described above.
Further, an antenna according to the present invention is characterized by using the liquid crystal composition described above.

According to the present invention, a liquid crystal composition containing one or more compounds represented by the general formula (i) having four ring structures and an isothiocyanate group (-NCS) has a high T _ni and a Δn It is possible to obtain a liquid crystal composition having a large _Vth , a large Δε _r , a small tan δ _iso , and good storage stability at low temperatures. Useful for communication equipment and antennas.

(Compound represented by general formula (i))
The compound according to the present invention is a compound represented by the following general formula (i) having four ring structures and an isothiocyanate group (--NCS).
Further, the liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having four ring structures and an isothiocyanate group (--NCS).

In general formula (i), R ⁱ¹ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 20 carbon atoms.
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms.
The alkyl group is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group is preferably 2-10, preferably 2-6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S—, —CO— and/or —CS—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkyl group are each independently —CO—O—, —O—CO—, —CO—S—, —S—CO -, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
Also, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms. However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
For example, R ⁱ¹ can represent an alkoxy group having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —O—.
The alkoxy group is a linear, branched or cyclic alkoxy group, preferably a linear alkoxy group.
The number of carbon atoms in the alkoxy group is preferably 2-10, preferably 2-6.
Further, R ⁱ¹ can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —S—.
The alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, preferably a linear alkylsulfanyl group.
The number of carbon atoms in the alkylsulfanyl group is preferably 1-10, preferably 1-6.
Further, R ⁱ¹ represents an alkenyl group having 2 to 20 carbon atoms by substituting one or more —CH ₂ —CH ₂ — in the alkyl group with —CH═CH—. be able to.
The alkenyl group is a linear, branched or cyclic alkenyl group, preferably a linear alkenyl group.
The number of carbon atoms in the alkenyl group is preferably 2-10, preferably 2-6.
Further, R ⁱ¹ represents an alkynyl group having 2 to 20 carbon atoms by substituting one or more —CH ₂ —CH ₂ — in the alkyl group with —C≡C—. be able to.
The alkynyl group is a linear, branched or cyclic alkynyl group, preferably a linear alkynyl group.
The number of carbon atoms in the alkynyl group is preferably 2-10, preferably 2-6.
In R ⁱ¹ , one -CH ₂ - in the alkyl group is substituted with -O- and one or more -CH ₂ -CH ₂ - is substituted with -CH=CH- can represent an alkenyloxy group having 2 to 19 carbon atoms.
The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, preferably a linear alkenyloxy group.
The number of carbon atoms in the alkenyloxy group is preferably 2-10, preferably 2-6.
Further, R ⁱ¹ can represent a halogenated alkyl group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.
The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, preferably a linear halogenated alkyl group.
The number of carbon atoms in the halogenated alkyl group is preferably 2-10, preferably 2-6.
R ⁱ¹ is a carbon atom obtained by substituting one —CH ₂ — in the alkyl group with —O— and substituting one or more hydrogen atoms in the alkyl group with a halogen atom. It can represent a halogenated alkoxy group having 1 to 19 atoms.
The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, preferably a linear alkoxy group.
The number of carbon atoms in the halogenated alkoxy group is preferably 2-10, preferably 2-6.
R ⁱ¹ represents an alkenyl group having 2 to 20 carbon atoms by substituting —CH═CH— for one or more —CH ₂ —CH ₂ — in the alkyl group. and one or more hydrogen atoms in the alkenyl group are substituted with halogen atoms to represent a halogenated alkenyl group having 2 to 19 carbon atoms.
The halogenated alkenyl group is a linear, branched or cyclic halogenated alkenyl group, preferably a linear halogenated alkenyl group.
The number of carbon atoms in the alkenyl halide group is preferably 2-10, preferably 2-6.
For example, R ⁱ¹ can represent an alkoxyalkyl group having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —O—.
The alkoxyalkyl group is a linear, branched or cyclic alkoxyalkyl group, preferably a linear alkoxyalkyl group.
The number of carbon atoms in the alkoxyalkyl group is preferably 2-10, preferably 2-6.
Further, R ⁱ¹ can represent an alkylsulfanylalkyl group having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —S—.
The alkylsulfanylalkyl group is a linear, branched or cyclic alkylsulfanyl group, preferably a linear alkylsulfanylalkyl group.
The number of carbon atoms in the alkylsulfanylalkyl group is preferably 1-10, preferably 1-6.
Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) for R ⁱ¹ include groups represented by formulas (R ⁱ¹ -1) to (R ⁱ¹ -44).

In formulas (R ⁱ¹ -1) to (R ⁱ¹ -44), black dots represent bonds to A ⁱ¹ .
From the viewpoint of solubility, R ⁱ¹ is preferably a straight-chain alkyl group having 2 to 6 carbon atoms.

In general formula (i), A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms. .
A hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms is, more specifically, the following group (a), group (b), group (c) and group (d):
(a) a 1,4-cyclohexylene group (one —CH ₂ — or two or more non-adjacent —CH ₂ — present in this group may be replaced with —O— and/or —S—; good.)
(b) a 1,4-phenylene group (one -CH= or two or more -CH= present in this group may be replaced with -N=);
(c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6- diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,4-diyl group, 2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group, one -CH= or two or more -CH= may be replaced with -N=.)
(d) thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl thieno[3,2-b]thiophene-2,5-diyl group, benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group (the 1 A single -CH= or two or more non-adjacent -CH= may be replaced with -N=.)
It is preferred to represent a group selected from the group consisting of

One or more hydrogen atoms in A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ may each independently be substituted with a substituent S ⁱ¹ .
Substituent ^Si1 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or alkyl group having 1 to 20 carbon atoms.
The alkyl group is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group is preferably 1-10, preferably 1-6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S— and/or —CO—.
In addition, one or two or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CH=CH-, -CF=CF-, -C≡C-, -CO-O- , —O—CO—, —CO—S—, —S—CO—, —CO—NH— and/or —NH—CO—.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be substituted with —O—CO—O—.
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
The substituent ^Si1 is preferably a halogen atom, preferably a fluorine atom.
Further, from the viewpoint of solubility, at least one of A ⁱ² , A ⁱ³ and A ⁱ⁴ is preferably substituted with at least one substituent ^Si1 , preferably substituted with a halogen atom, fluorine Atoms are preferred.
When there are a plurality of substituents S ⁱ¹ , they may be the same or different.

The substitution position of the substituent S ⁱ¹ in A ⁱ¹ is preferably any one of the following formulas (A ⁱ¹ -SP-1) to (A ⁱ¹ -SP-2).

In formulas (A ⁱ¹ -SP-1) to (A ⁱ¹ -SP-2), white dots represent bonds to R ⁱ¹ and black dots represent bonds to Z ⁱ¹ .
The substitution position of the substituent S ⁱ¹ in A ⁱ² is preferably any one of the following formulas (A ⁱ² -SP-1) to (A ⁱ² -SP-2).

In formulas (A ⁱ² -SP-1) to (A ⁱ² -SP-2), white dots represent bonds to Z ⁱ¹ and black dots represent bonds to Z ⁱ² .
The substitution position of the substituent S ⁱ¹ in A ⁱ³ is preferably any one of the following formulas (A ⁱ³ -SP-1) to (A ⁱ³ -SP-2).

In formulas (A ⁱ³ -SP-1) to (A ⁱ³ -SP-2), white dots represent bonds to Z ⁱ² and black dots represent bonds to Z ⁱ³ .
The substitution position of the substituent S ⁱ¹ in A ⁱ⁴ is preferably any one of the following formulas (A ⁱ⁴ -SP-1) to (A ⁱ⁴ -SP-2).

In formulas (A ⁱ⁴ -SP-1) to (A ⁱ⁴ -SP-2), white dots represent bonds to Z ⁱ³ and black dots represent bonds to the isothiocyanate group (-NCS).
More specifically, A ⁱ¹ preferably represents any one of the following formulas (A ⁱ¹ -1) to (A ⁱ¹ -3).

In formulas (A ⁱ¹ -1) to (A ⁱ¹ -3), white dots represent bonds to R ⁱ¹ and black dots represent bonds to Z ⁱ¹ .
A ⁱ¹ particularly preferably represents the formula (A ⁱ¹ -1) from the viewpoint of solubility, Δn and/or Δε _r .
More specifically, A ⁱ² preferably represents any one of the following formulas (A ⁱ² -1) to (A ⁱ² -3).

In formulas (A ⁱ² −1) to (A ⁱ² −3), white dots represent bonds to Z ⁱ¹ and black dots represent bonds to Z ⁱ² .
A ⁱ² particularly preferably represents the formula (A ⁱ² -1) from the viewpoint of Δn and/or Δε _r .
More specifically, A ⁱ³ preferably represents any one of the following formulas (A ⁱ³ -1) to (A ⁱ³ -3).

In formulas (A ⁱ³ -1) to (A ⁱ³ -3), white dots represent bonds to Z ⁱ² and black dots represent bonds to Z ⁱ³ .
A ⁱ³ particularly preferably represents the formula (A ⁱ³ -2) from the viewpoint of Δn and/or Δε _r .
More specifically, A ⁱ⁴ preferably represents any one of the following formulas (A ⁱ⁴ -1) to (A ⁱ⁴ -3).

In formulas (A ⁱ⁴ -1) to (A ⁱ⁴ -3), white dots represent bonds to Z ⁱ³ and black dots represent bonds to an isothiocyanate group (-NCS).
A ⁱ⁴ preferably represents the above formula (A ⁱ⁴ -3) from the viewpoint of Δn and/or Δε _r .

In general formula (i), Z ⁱ¹ , Z ⁱ² and Z ⁱ³ each independently represent either a single bond or an alkylene group having 1 to 20 carbon atoms.
The alkylene group is a linear, branched or cyclic alkylene group, preferably a linear alkylene group.
The number of carbon atoms in the alkylene group is preferably 2-10, preferably 2-6.
One or more —CH ₂ — in the alkylene group may each independently be replaced with —O—, —CF ₂ — and/or —CO—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, -CH=CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, may be substituted with -C≡C-, -CO-O- and/or -O-CO-.
However, when the alkylene group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted ones) include groups represented by formulas (Z ^i1/2/3 -1) to (Z ^i1/2/3 -24) etc.

In the formulas (Z ^i1/2/3 −1) to (Z ^i1/2/3 −24), white dots represent bonds to A ⁱ¹ , A ⁱ² or A ⁱ³ , black dots represent A ⁱ² , A ⁱ³ or A represents the bond to ⁱ⁴ .
From the viewpoint of Δn and/or _Δεr , at least one of Z ⁱ¹ , Z ⁱ² and Z ⁱ³ is preferably a single bond, and all of them are preferably single bonds.

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

In general formula (i-1), R ⁱ¹ , A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ are the same as R ⁱ¹ , A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ in general formula (i) above. mean, and preferred groups are also the same.

Compounds represented by the general formula (i-1) are preferably compounds represented by the following general formulas (i-1-1) to (i-1-46).

In general formulas (i-1-1) to (i-1-46), R ⁱ¹ and S ⁱ¹ each independently have the same meaning as R ⁱ¹ and S ⁱ¹ in general formula (i) above. , and preferred groups are the same.

Specific examples of the compound represented by the general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.3). be done.

Specific examples of the compound represented by the general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.2). be done.

Specific examples of the compound represented by the general formula (i-1-3) include compounds represented by the following structural formulas (i-1-3.1) to (i-1-3.6). be done.

Specific examples of the compound represented by the general formula (i-1-4) include compounds represented by the following structural formulas (i-1-4.1) to (i-1-4.3). be done.

Specific examples of the compound represented by general formula (i-1-5) include compounds represented by the following structural formula (i-1-5.1).

Specific examples of the compound represented by general formula (i-1-6) include compounds represented by the following structural formula (i-1-6.1).

Specific examples of the compound represented by general formula (i-1-7) include compounds represented by the following structural formula (i-1-7.1).

Specific examples of the compound represented by general formula (i-1-8) include compounds represented by the following structural formula (i-1-8.1).

Specific examples of the compound represented by general formula (i-1-9) include compounds represented by the following structural formula (i-1-9.1).

Specific examples of the compound represented by general formula (i-1-10) include compounds represented by the following structural formula (i-1-10.1).

Specific examples of the compound represented by the general formula (i-1-11) include compounds represented by the following structural formulas (i-1-11.1) to (i-1-11.5). be done.

Specific examples of the compound represented by general formula (i-1-12) include compounds represented by the following structural formula (i-1-12.1).

Specific examples of the compound represented by the general formula (i-1-13) include compounds represented by the following structural formulas (i-1-13.1) to (i-1-13.2). be done.

Specific examples of the compound represented by general formula (i-1-14) include compounds represented by the following structural formula (i-1-14.1).

Specific examples of the compound represented by general formula (i-1-15) include compounds represented by the following structural formula (i-1-15.1).

Specific examples of the compound represented by the general formula (i-1-16) include compounds represented by the following structural formulas (i-1-16.1) to (i-1-16.2). be done.

Specific examples of the compound represented by general formula (i-1-17) include compounds represented by the following structural formula (i-1-17.1).

Specific examples of the compound represented by general formula (i-1-18) include compounds represented by the following structural formula (i-1-18.1).

Specific examples of the compound represented by general formula (i-1-19) include compounds represented by the following structural formula (i-1-19.1).

Specific examples of the compound represented by general formula (i-1-20) include compounds represented by the following structural formula (i-1-20.1).

Specific examples of the compound represented by general formula (i-1-21) include compounds represented by the following structural formula (i-1-21.1).

Specific examples of the compound represented by general formula (i-1-22) include compounds represented by the following structural formula (i-1-22.1).

Specific examples of the compound represented by general formula (i-1-23) include compounds represented by the following structural formula (i-1-23.1).

Specific examples of the compound represented by general formula (i-1-24) include compounds represented by the following structural formula (i-1-24.1).

Specific examples of the compound represented by general formula (i-1-25) include compounds represented by the following structural formula (i-1-25.1).

Specific examples of the compound represented by general formula (i-1-26) include compounds represented by the following structural formula (i-1-26.1).

Specific examples of the compound represented by general formula (i-1-27) include compounds represented by the following structural formula (i-1-27.1).

Specific examples of the compound represented by general formula (i-1-28) include compounds represented by the following structural formula (i-1-28.1).

Specific examples of the compound represented by general formula (i-1-29) include compounds represented by the following structural formula (i-1-29.1).

Specific examples of the compound represented by general formula (i-1-30) include compounds represented by the following structural formula (i-1-30.1).

Specific examples of the compound represented by the general formula (i-1-31) include compounds represented by the following structural formulas (i-1-31.1) to (i-1-31.2). be done.

Specific examples of the compound represented by general formula (i-1-32) include compounds represented by the following structural formula (i-1-32.1).

Specific examples of the compound represented by general formula (i-1-33) include compounds represented by the following structural formula (i-1-33.1).

Specific examples of the compound represented by general formula (i-1-34) include compounds represented by the following structural formula (i-1-34.1).

Specific examples of the compound represented by general formula (i-1-35) include compounds represented by the following structural formula (i-1-35.1).

Specific examples of the compound represented by general formula (i-1-36) include compounds represented by the following structural formula (i-1-36.1).

Specific examples of the compound represented by general formula (i-1-37) include compounds represented by the following structural formula (i-1-37.1).

Specific examples of the compound represented by general formula (i-1-38) include compounds represented by the following structural formula (i-1-38.1).

Specific examples of the compound represented by general formula (i-1-39) include compounds represented by the following structural formula (i-1-39.1).

Specific examples of the compound represented by general formula (i-1-40) include compounds represented by the following structural formula (i-1-40.1).

Specific examples of the compound represented by general formula (i-1-41) include compounds represented by the following structural formula (i-1-41.1).

Specific examples of the compound represented by general formula (i-1-42) include compounds represented by the following structural formula (i-1-42.1).

Specific examples of the compound represented by general formula (i-1-43) include compounds represented by the following structural formula (i-1-43.1).

Specific examples of the compound represented by general formula (i-1-44) include compounds represented by the following structural formula (i-1-44.1).

Specific examples of the compound represented by general formula (i-1-45) include compounds represented by the following structural formula (i-1-45.1).

Specific examples of the compound represented by the general formula (i-1-46) include compounds represented by the following structural formulas (i-1-46.1) to (i-1-46.4). be done.

General formula (i), general formula (i-1), general formulas (i-1-1) to (i-1-46), structural formulas (i-1-1.1) to (i-1-1) .3), structural formulas (i-1-2.1) to (i-1-2.2), structural formulas (i-1-3.1) to (i-1-3.6), structural formulas (i-1-4.1) to (i-1-4.3), structural formula (i-1-5.1), structural formula (i-1-6.1), structural formula (i-1 -7.1), structural formula (i-1-8.1), structural formula (i-1-9.1), structural formula (i-1-10.1), structural formula (i-1-11) .1) to (i-1-11.5), structural formula (i-1-12.1), structural formula (i-1-13.1) to (i-1-13.2), structural formula (i-1-14.1), structural formula (i-1-15.1), structural formulas (i-1-16.1) to (i-1-16.2), structural formula (i-1 -17.1), structural formula (i-1-18.1), structural formula (i-1-19.1), structural formula (i-1-20.1), structural formula (i-1-21) .1), structural formula (i-1-22.1), structural formula (i-1-23.1), structural formula (i-1-24.1), structural formula (i-1-25.1 ), structural formula (i-1-26.1), structural formula (i-1-27.1), structural formula (i-1-28.1), structural formula (i-1-29.1), Structural formula (i-1-30.1), structural formulas (i-1-31.1) to (i-1-31.2), structural formula (i-1-32.1), structural formula (i -1-33.1), structural formula (i-1-34.1), structural formula (i-1-35.1), structural formula (i-1-36.1), structural formula (i-1 -37.1), structural formula (i-1-38.1), structural formula (i-1-39.1), structural formula (i-1-40.1), structural formula (i-1-41) .1), structural formula (i-1-42.1), structural formula (i-1-43.1), structural formula (i-1-44.1), structural formula (i-1-45.1 ) or the compounds represented by the structural formulas (i-1-46.1) to (i-1-46.4) are used in the liquid crystal composition is one or more, preferably 1 to 10. , preferably 1 to 5, preferably 1 to 3.

General formula (i), general formula (i-1), general formulas (i-1-1) to (i-1-46), structural formulas (i-1-1.1) to (i-1-1) .3), structural formulas (i-1-2.1) to (i-1-2.2), structural formulas (i-1-3.1) to (i-1-3.6), structural formulas (i-1-4.1) to (i-1-4.3), structural formula (i-1-5.1), structural formula (i-1-6.1), structural formula (i-1 -7.1), structural formula (i-1-8.1), structural formula (i-1-9.1), structural formula (i-1-10.1), structural formula (i-1-11) .1) to (i-1-11.5), structural formula (i-1-12.1), structural formula (i-1-13.1) to (i-1-13.2), structural formula (i-1-14.1), structural formula (i-1-15.1), structural formulas (i-1-16.1) to (i-1-16.2), structural formula (i-1 -17.1), structural formula (i-1-18.1), structural formula (i-1-19.1), structural formula (i-1-20.1), structural formula (i-1-21) .1), structural formula (i-1-22.1), structural formula (i-1-23.1), structural formula (i-1-24.1), structural formula (i-1-25.1 ), structural formula (i-1-26.1), structural formula (i-1-27.1), structural formula (i-1-28.1), structural formula (i-1-29.1), Structural formula (i-1-30.1), structural formulas (i-1-31.1) to (i-1-31.2), structural formula (i-1-32.1), structural formula (i -1-33.1), structural formula (i-1-34.1), structural formula (i-1-35.1), structural formula (i-1-36.1), structural formula (i-1 -37.1), structural formula (i-1-38.1), structural formula (i-1-39.1), structural formula (i-1-40.1), structural formula (i-1-41) .1), structural formula (i-1-42.1), structural formula (i-1-43.1), structural formula (i-1-44.1), structural formula (i-1-45.1 ) or compounds represented by structural formulas (i-1-46.1) to (i-1-46.4) in 100% by mass of the liquid crystal composition, the lower limit of the total content is 0.1% by mass. or more, preferably 0.5% by mass or more, and preferably 1.0% by mass or more.

General formula (i), general formula (i-1), general formulas (i-1-1) to (i-1-46), structural formulas (i-1-1.1) to (i-1-1) .3), structural formulas (i-1-2.1) to (i-1-2.2), structural formulas (i-1-3.1) to (i-1-3.6), structural formulas (i-1-4.1) to (i-1-4.3), structural formula (i-1-5.1), structural formula (i-1-6.1), structural formula (i-1 -7.1), structural formula (i-1-8.1), structural formula (i-1-9.1), structural formula (i-1-10.1), structural formula (i-1-11) .1) to (i-1-11.5), structural formula (i-1-12.1), structural formula (i-1-13.1) to (i-1-13.2), structural formula (i-1-14.1), structural formula (i-1-15.1), structural formulas (i-1-16.1) to (i-1-16.2), structural formula (i-1 -17.1), structural formula (i-1-18.1), structural formula (i-1-19.1), structural formula (i-1-20.1), structural formula (i-1-21) .1), structural formula (i-1-22.1), structural formula (i-1-23.1), structural formula (i-1-24.1), structural formula (i-1-25.1 ), structural formula (i-1-26.1), structural formula (i-1-27.1), structural formula (i-1-28.1), structural formula (i-1-29.1), Structural formula (i-1-30.1), structural formulas (i-1-31.1) to (i-1-31.2), structural formula (i-1-32.1), structural formula (i -1-33.1), structural formula (i-1-34.1), structural formula (i-1-35.1), structural formula (i-1-36.1), structural formula (i-1 -37.1), structural formula (i-1-38.1), structural formula (i-1-39.1), structural formula (i-1-40.1), structural formula (i-1-41) .1), structural formula (i-1-42.1), structural formula (i-1-43.1), structural formula (i-1-44.1), structural formula (i-1-45.1 ) or compounds represented by structural formulas (i-1-46.1) to (i-1-46.4) in 100% by mass of the liquid crystal composition, the upper limit of the total content is 25% by mass or less. preferably 20% by mass or less, preferably 15% by mass or less.

General formula (i), general formula (i-1), general formulas (i-1-1) to (i-1-46), structural formulas (i-1-1.1) to (i-1-1) .3), structural formulas (i-1-2.1) to (i-1-2.2), structural formulas (i-1-3.1) to (i-1-3.6), structural formulas (i-1-4.1) to (i-1-4.3), structural formula (i-1-5.1), structural formula (i-1-6.1), structural formula (i-1 -7.1), structural formula (i-1-8.1), structural formula (i-1-9.1), structural formula (i-1-10.1), structural formula (i-1-11) .1) to (i-1-11.5), structural formula (i-1-12.1), structural formula (i-1-13.1) to (i-1-13.2), structural formula (i-1-14.1), structural formula (i-1-15.1), structural formulas (i-1-16.1) to (i-1-16.2), structural formula (i-1 -17.1), structural formula (i-1-18.1), structural formula (i-1-19.1), structural formula (i-1-20.1), structural formula (i-1-21) .1), structural formula (i-1-22.1), structural formula (i-1-23.1), structural formula (i-1-24.1), structural formula (i-1-25.1 ), structural formula (i-1-26.1), structural formula (i-1-27.1), structural formula (i-1-28.1), structural formula (i-1-29.1), Structural formula (i-1-30.1), structural formulas (i-1-31.1) to (i-1-31.2), structural formula (i-1-32.1), structural formula (i -1-33.1), structural formula (i-1-34.1), structural formula (i-1-35.1), structural formula (i-1-36.1), structural formula (i-1 -37.1), structural formula (i-1-38.1), structural formula (i-1-39.1), structural formula (i-1-40.1), structural formula (i-1-41) .1), structural formula (i-1-42.1), structural formula (i-1-43.1), structural formula (i-1-44.1), structural formula (i-1-45.1 ) or compounds represented by structural formulas (i-1-46.1) to (i-1-46.4) in 100% by mass of the liquid crystal composition, the solubility, Δn and/or Δε From the viewpoint of _r , it is preferably 0.1 to 25% by mass, preferably 0.5 to 20% by mass, and preferably 1 to 15% by mass.

Compounds represented by general formula (i) (including subordinate concepts) can be synthesized using known synthesis methods, and some of them are exemplified below.
(Production method 1) Production of a compound represented by the following formula (s-7)

(In the formula, R ⁱ¹ and S ⁱ¹ have the same meanings as R ⁱ¹ and S ⁱ¹ in the general formula (I).)
First, a compound represented by general formula (s-3) can be obtained by reacting a compound represented by general formula (s-1) with a compound represented by general formula (s-2).
Examples of the reaction method include Suzuki coupling reaction using a palladium catalyst and a base.
Specific examples of palladium catalysts include [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium (II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0) and the like.
Specific examples of bases include potassium carbonate, potassium phosphate, sodium acetate, sodium carbonate and the like.
Next, the compound represented by general formula (s-4) can be obtained by reacting the compound represented by general formula (s-3) in the presence of trifluoromethanesulfonic anhydride and triethylamine.
Next, a compound represented by general formula (s-6) can be obtained by Suzuki coupling reaction with the compound represented by general formula (s-5) using a palladium catalyst and a base.
Specific examples of palladium catalysts and bases include those described above.
Then, the target compound represented by general formula (s-7) can be obtained by reaction with 1,1-thiocarbonyldiimidazole.
(Production method 2) Production of a compound represented by the following formula (s-14)

(In the formula, R ⁱ¹ and S ⁱ¹ have the same meanings as R ⁱ¹ and S ⁱ¹ in the general formula (I).)
First, a compound represented by general formula (s-10) can be obtained by reacting a compound represented by general formula (s-8) with a compound represented by general formula (s-9).
Examples of the reaction method include Suzuki coupling reaction using a palladium catalyst and a base.
Specific examples of palladium catalysts include [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium (II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0) and the like.
Specific examples of bases include potassium carbonate, potassium phosphate, sodium acetate, sodium carbonate and the like.
Next, the compound represented by the general formula (s-10) is reacted with butyllithium at −78° C., and then iodine is added to obtain the compound represented by the general formula (s-11). can.
Next, the compound represented by the general formula (s-12) is subjected to Suzuki coupling reaction, and the nitro group is reduced with iron powder to obtain the compound represented by the general formula (s-13). can.
Specific examples of the palladium catalyst and base used in the Suzuki coupling reaction include those described above.
Then, the target compound represented by the general formula (s-14) can be obtained by reacting the compound represented by the general formula (s-13) with, for example, thiourea.
(Production method 3) Production of a compound represented by the following formula (s-21)

(In the formula, R ⁱ¹ and S ⁱ¹ have the same meanings as R ⁱ¹ and S ⁱ¹ in the general formula (I).)
First, a compound represented by general formula (s-17) can be obtained by reacting a compound represented by general formula (s-15) with a compound represented by general formula (s-16).
Examples of the reaction method include Suzuki coupling reaction using a palladium catalyst and a base.
Specific examples of palladium catalysts include [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium (II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0) and the like.
Specific examples of bases include potassium carbonate, potassium phosphate, sodium acetate, sodium carbonate and the like.
Next, a compound represented by general formula (s-18) can be obtained by reacting the compound represented by general formula (s-17) in the presence of trifluoromethanesulfonic anhydride and triethylamine.
Then, a compound represented by general formula (s-20) can be obtained by Suzuki coupling reaction with the compound represented by general formula (s-19) using a palladium catalyst and a base.
Specific examples of palladium catalysts and bases include those described above.
Then, the target compound represented by general formula (s-21) can be obtained by reaction with 1,1-thiocarbonyldiimidazole.
(Production method 4) Production of a compound represented by the following formula (S-27)

(In the formula, R ⁱ¹ and S ⁱ¹ have the same meanings as R ⁱ¹ and S ⁱ¹ in the general formula (I).)
First, a compound represented by the general formula (s-23) can be obtained by reacting the compound represented by the general formula (s-22) with a 1,3-diol compound using p-toluenesulfonic acid as a catalyst. I can.
Next, the compound represented by general formula (s-24) can be obtained by reacting with N-bromosuccinimide.
Next, a compound represented by general formula (s-26) can be obtained by reacting a compound represented by general formula (s-24) with a compound represented by general formula (s-25). .
Examples of the reaction method include Suzuki coupling reaction using a palladium catalyst and a base.
Specific examples of palladium catalysts include [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium (II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0) and the like.
Specific examples of bases include potassium carbonate, potassium phosphate, sodium acetate, sodium carbonate and the like.
Furthermore, the target compound represented by general formula (s-27) can be obtained by reaction with 1,1-thiocarbonyldiimidazole.

(Other compounds)
(Compound represented by general formula (ii))
From the viewpoint of solubility, Δn and/or _Δεr , the liquid crystal composition according to the present invention further includes one or more compounds represented by the following general formula (ii) having an isothiocyanate group (—NCS). may include

In general formula (ii), R ⁱⁱ¹ represents an alkyl group having 1 to 20 carbon atoms.
The alkyl group is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group is preferably 2-10, preferably 2-6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S—, —CO— and/or —CS—.
In addition, one or more -CH ₂ -CH ₂ - in the alkyl group is -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S- It may be substituted with CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be substituted with —O—CO—O—.
Also, one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
For example, R ⁱⁱ¹ can represent an alkoxy group having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —O—.
The alkoxy group is a linear, branched or cyclic alkoxy group, preferably a linear alkoxy group.
The number of carbon atoms in the alkoxy group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱ¹ can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —S—.
The alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, preferably a linear alkylsulfanyl group.
The number of carbon atoms in the alkylsulfanyl group is preferably 1-10, preferably 1-6.
R ⁱⁱ¹ represents an alkenyl group having 2 to 20 carbon atoms by substituting —CH═CH— for one or more —CH ₂ —CH ₂ — in the alkyl group. be able to.
The alkenyl group is a linear, branched or cyclic alkenyl group, preferably a linear alkenyl group.
The number of carbon atoms in the alkenyl group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱ¹ represents an alkynyl group having 2 to 20 carbon atoms by substituting one or more —CH ₂ —CH ₂ — in the alkyl group with —C≡C—. be able to.
The alkynyl group is a linear, branched or cyclic alkynyl group, preferably a linear alkynyl group.
The number of carbon atoms in the alkynyl group is preferably 2-10, preferably 2-6.
In R ⁱⁱ¹ , one -CH ₂ - in the alkyl group is substituted with -O- and one or more -CH ₂ -CH ₂ - is substituted with -CH=CH- can represent an alkenyloxy group having 2 to 19 carbon atoms.
The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, preferably a linear alkenyloxy group.
The number of carbon atoms in the alkenyloxy group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱ¹ can represent a halogenated alkyl group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.
The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, preferably a linear halogenated alkyl group.
The number of carbon atoms in the halogenated alkyl group is preferably 2-10, preferably 2-6.
In addition, R ⁱⁱ¹ is obtained by substituting one —CH ₂ — in the alkyl group with —O— and substituting one or more hydrogen atoms in the alkyl group with a halogen atom. , can represent a halogenated alkoxy group having 1 to 19 carbon atoms.
The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, preferably a linear halogenated alkoxy group.
The number of carbon atoms in the halogenated alkoxy group is preferably 2-10, preferably 2-6.
Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) for R ⁱⁱ¹ include groups represented by formulas (R ⁱⁱ¹ -1) to (R ⁱⁱ¹ -39).

In formulas (R ⁱⁱ¹ -1) to (R ⁱⁱ¹ -39), black dots represent bonds to A ⁱⁱ¹ .
When the ring structure to which R ⁱⁱ¹ is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a carbon atom An alkenyl group having a number of 4 to 5 is preferable, and when the ring structure to which R ⁱ¹ is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a linear A linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferred.
In order to stabilize the nematic phase, R ⁱⁱ¹ preferably has a total of 5 or less carbon atoms and, if present, oxygen atoms, and is preferably linear.
From the viewpoint of solubility, R ⁱⁱ¹ includes a linear alkyl group having 2 to 8 carbon atoms, a linear alkoxy group having 2 to 8 carbon atoms, and a linear group having 2 to 8 carbon atoms. A hexagonal halogenated alkoxy group or a straight-chain alkylsulfanyl group having 1 to 6 carbon atoms is preferred.

In general formula (ii), A ⁱⁱ¹ and A ⁱⁱ² are each independently the following group (a), group (b), group (c) and group (d):
(a) a 1,4-cyclohexylene group (one —CH ₂ — or two or more non-adjacent —CH ₂ — present in this group may be replaced with —O— and/or —S—; good.)
(b) a 1,4-phenylene group (one -CH= or two or more -CH= present in this group may be replaced with -N=);
(c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6- diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,4-diyl group, 2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group, one -CH= or two or more -CH= may be replaced with -N=.)
(d) thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl thieno[3,2-b]thiophene-2,5-diyl group, benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group (the 1 One -CH= or two or more -CH= may be replaced with -N=.)
represents a group selected from the group consisting of

One or more hydrogen atoms in A ⁱⁱ¹ and A ⁱⁱ² may each independently be substituted with a substituent S ⁱⁱ¹ .
Substituent S ⁱⁱ¹ is a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, represents either a dimethylsilyl group, a thioisocyano group or an alkyl group having 1 to 20 carbon atoms;
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S—, —CO— and/or —CS—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkyl group are each independently —CO—O—, —O—CO—, —CO—S—, —S—CO -, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-.
One or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
Also, one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
A fluorine atom or a chlorine atom is preferable as the substituent S ⁱⁱ¹ .
Further, at least one of A ⁱⁱ¹ or A ⁱⁱ² is preferably substituted with at least one substituent S ⁱⁱ¹ , preferably substituted with a halogen atom, preferably substituted with a fluorine atom. .
In addition, when there are a plurality of substituents ^Sii1 , they may be the same or different.

The substitution position of the substituent S ⁱⁱ¹ in A ⁱⁱ¹ is preferably any one of the following formulas (A ⁱⁱ¹ -SP-1) to (A ⁱⁱ¹ -SP-5).

In formulas (A ⁱⁱ¹ -SP-1) to (A ⁱⁱ¹ -SP-5), white dots represent bonds to R ⁱⁱ¹ or Z ⁱⁱ¹ and black dots represent bonds to Z ⁱⁱ¹ .
The substitution position of the substituent S ⁱⁱ¹ in A ⁱⁱ² is preferably any one of the following formulas (A ⁱⁱ² -SP-1) to (A ⁱⁱ² -SP-8).

In formulas (A ⁱⁱ² -SP-1) to (A ⁱⁱ² -SP-8), white dots represent bonds to Z ⁱⁱ¹ and black dots represent bonds to an isothiocyanate group (-NCS).
More specifically, A ⁱⁱ¹ preferably represents any one of the following formulas (A ⁱⁱ¹ -1) to (A ⁱⁱ¹ -21).

In formulas (A ⁱⁱ¹ -1) to (A ⁱⁱ¹ -21), white dots represent bonds to R ⁱⁱ¹ or Z ⁱⁱ¹ and black dots represent bonds to Z ⁱⁱ¹ .
More specifically, A ⁱⁱ² preferably represents any one of the following formulas (A ⁱⁱ² -1) to (A ⁱⁱ² -8).

In formulas (A ⁱⁱ² -1) to (A ⁱⁱ² -8), white dots represent bonds to Z ⁱⁱ¹ and black dots represent bonds to the isothiocyanate group (--NCS).

In general formula (ii), Z ⁱⁱ¹ represents either a single bond or an alkylene group having 1 to 20 carbon atoms.
One or more —CH ₂ — in the alkylene group may be independently substituted with —O—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, -CH=CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, may be substituted with -C≡C-, -CO-O- and/or -O-CO-.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
However, when an alkyl group having 1 to 10 carbon atoms is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted ones) include groups represented by formulas (Z ⁱⁱ¹ -1) to (Z ⁱⁱ¹ -24).

In formulas (Z ⁱⁱ¹ −1) to (Z ⁱⁱ¹ −24), white dots represent bonds to A ⁱⁱ¹ and black dots represent bonds to A ⁱⁱ¹ or A ⁱⁱ² .

In general formula (ii), ⁿⁱⁱ¹ represents an integer of 1-4, preferably 1-2.
When n ⁱⁱ¹ is 1, Z ⁱⁱ¹ preferably represents a single bond or -C≡C- from the viewpoint of Δn and/or Δε _r .
Further, when n ⁱⁱ¹ is 2, Z ⁱⁱ¹ preferably represents a single bond or -C≡C- from the viewpoint of Δn and/or _Δεr .
In general formula (ii), when there are a plurality of A ⁱⁱ¹ and Z ⁱⁱ¹ , they may be the same or different.
However, among the compounds represented by general formula (ii), compounds represented by general formula (i) (including subordinate concepts) are excluded.

Compounds represented by general formula (ii) are preferably compounds represented by the following general formulas (ii-1) to (ii-6).

In general formulas (ii-1) to (ii-6), R ⁱⁱ¹ , A ⁱⁱ¹ and A ⁱⁱ² have the same meanings as R ⁱⁱ¹ , A ⁱⁱ¹ and A ⁱⁱ² in general formula (ii) above.
In general formulas (ii-3) to (ii-6), the definition of A ^ii1-2 is the same as the definition of A ⁱⁱ¹ in general formula (ii) above.
The compound represented by general formula (ii-1) is preferably a compound represented by general formula (ii-1-1) below.

In general formula (ii-1-1), each R ⁱⁱ¹ independently has the same meaning as R ⁱⁱ¹ in general formula (ii) above.
Specific examples of the compound represented by general formula (ii-1-1) include compounds represented by the following structural formula (ii-1-1.1).

Compounds represented by general formula (ii-2) are preferably compounds represented by general formulas (ii-2-1) to (ii-2-7) below.

In general formulas (ii-2-1) to (ii-2-7), R ⁱⁱ¹ and S ⁱⁱ¹ each independently have the same meaning as R ⁱⁱ¹ and S ⁱⁱ¹ in general formula (i) above. .
Specific examples of the compound represented by the general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.10). be done.

Specific examples of the compound represented by the general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.2). be done.

Specific examples of the compound represented by the general formula (ii-2-3) include compounds represented by the following structural formulas (ii-2-3.1) to (ii-2-3.7). be done.

Specific examples of the compound represented by the general formula (ii-2-4) include compounds represented by the following structural formulas (ii-2-4.1) to (ii-2-4.4). be done.

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

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

Specific examples of the compound represented by the general formula (ii-2-7) include compounds represented by the following structural formulas (ii-2-7.1) to (ii-2-7.4). be done.

Compounds represented by general formula (ii-3) are preferably compounds represented by general formulas (ii-3-1) to (ii-3-12) below.

In general formulas (ii-3-1) to (ii-3-12), R ⁱⁱ¹ and S ⁱⁱ¹ each independently have the same meaning as R ⁱⁱ¹ and S ⁱⁱ¹ in general formula (ii) above. .
Specific examples of the compound represented by the general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.4). be done.

Specific examples of the compound represented by general formula (ii-3-2) include compounds represented by the following structural formula (ii-3-2.1).

Specific examples of the compound represented by the general formula (ii-3-3) include compounds represented by the following structural formulas (ii-3-3.1) to (ii-3-3.3). be done.

Specific examples of the compound represented by the general formula (ii-3-4) include compounds represented by the following structural formulas (ii-3-4.1) to (ii-3-4.6). be done.

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

Specific examples of the compound represented by the general formula (ii-3-6) include compounds represented by the following structural formulas (ii-3-6.1) to (ii-3-6.7). be done.

Specific examples of the compound represented by the general formula (ii-3-7) include compounds represented by the following structural formulas (ii-3-7.1) to (ii-3-7.5). be done.

Specific examples of the compound represented by the general formula (ii-3-8) include compounds represented by the following structural formulas (ii-3-8.1) to (ii-3-8.5). be done.

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

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

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

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

Compounds represented by general formula (ii-4) are preferably compounds represented by general formulas (ii-4-1) to (ii-4-25) below.

In general formulas (ii-4-1) to (ii-4-25), R ⁱⁱ¹ and S ⁱⁱ¹ each independently have the same meaning as R ⁱⁱ¹ and S ⁱⁱ¹ in general formula (ii) above. .
Specific examples of the compound represented by the general formula (ii-4-1) include compounds represented by the following structural formulas (ii-4-1.1) to (ii-4-1.3). be done.

Specific examples of the compound represented by the general formula (ii-4-2) include compounds represented by the following structural formulas (ii-4-2.1) to (ii-4-2.3). be done.

Specific examples of the compound represented by the general formula (ii-4-3) include compounds represented by the following structural formulas (ii-4-3.1) to (ii-4-3.3). be done.

Specific examples of the compound represented by the general formula (ii-4-4) include compounds represented by the following structural formulas (ii-4-4.1) to (ii-4-4.3). be done.

Specific examples of the compound represented by the general formula (ii-4-5) include compounds represented by the following structural formulas (ii-4-5.1) to (ii-4-5.3). be done.

Specific examples of the compound represented by the general formula (ii-4-6) include compounds represented by the following structural formulas (ii-4-6.1) to (ii-4-6.3). be done.

Specific examples of the compound represented by the general formula (ii-4-7) include compounds represented by the following structural formulas (ii-4-7.1) to (ii-4-7.3). be done.

Specific examples of the compound represented by the general formula (ii-4-8) include compounds represented by the following structural formulas (ii-4-8.1) to (ii-4-8.3). be done.

Specific examples of the compound represented by the general formula (ii-4-9) include compounds represented by the following structural formulas (ii-4-9.1) to (ii-4-9.5). be done.

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

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

Specific examples of the compound represented by the general formula (ii-4-12) include compounds represented by the following structural formulas (ii-4-12.1) to (ii-4-12.8). be done.

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

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

Specific examples of the compound represented by general formula (ii-4-15) include compounds represented by the following structural formula (ii-4-15.1).

Specific examples of the compound represented by general formula (ii-4-16) include compounds represented by the following structural formula (ii-4-16.1).

Specific examples of the compound represented by the general formula (ii-4-17) include compounds represented by the following structural formulas (ii-4-17.1) to (ii-4-17.5). be done.

Specific examples of the compound represented by the general formula (ii-4-18) include compounds represented by the following structural formulas (ii-4-18.1) to (ii-4-18.5). be done.

Specific examples of the compound represented by the general formula (ii-4-19) include compounds represented by the following structural formulas (ii-4-19.1) to (ii-4-19.4). be done.

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

Specific examples of the compound represented by the general formula (ii-4-21) include compounds represented by the following structural formulas (ii-4-21.1) to (ii-4-21.6). be done.

Specific examples of the compound represented by the general formula (ii-4-22) include compounds represented by the following structural formulas (ii-4-22.1) to (ii-4-22.4). be done.

Specific examples of the compound represented by the general formula (ii-4-23) include compounds represented by the following structural formulas (ii-4-23.1) to (ii-4-23.5). be done.

Specific examples of the compound represented by the general formula (ii-4-24) include compounds represented by the following structural formulas (ii-4-24.1) to (ii-4-24.4). be done.

Specific examples of the compound represented by the general formula (ii-4-25) include compounds represented by the following structural formulas (ii-4-25.1) to (ii-4-25.4). be done.

Compounds represented by general formula (ii-5) are preferably compounds represented by general formulas (ii-5-1) to (ii-5-5) below.

In general formulas (ii-5-1) to (ii-5-5), R ⁱⁱ¹ and S ⁱⁱ¹ each independently have the same meaning as R ⁱⁱ¹ and S ⁱⁱ¹ in general formula (ii) above. .
Specific examples of the compound represented by the general formula (ii-5-1) include compounds represented by the following structural formulas (ii-5-1.1) to (ii-5-1.4). be done.

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

Specific examples of the compound represented by the general formula (ii-5-3) include compounds represented by the following structural formulas (ii-5-3.1) to (ii-5-3.3). be done.

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

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

Compounds represented by general formula (ii-6) are preferably compounds represented by general formulas (ii-6-1) to (ii-6-32) below.

In general formulas (ii-6-1) to (ii-6-32), R ⁱⁱ¹ and S ⁱⁱ¹ each independently have the same meaning as R ⁱⁱ¹ and S ⁱⁱ¹ in general formula (ii) above. .
Specific examples of the compound represented by the general formula (ii-6-1) include compounds represented by the following structural formulas (ii-6-1.1) to (ii-6-1.4). be done.

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

Specific examples of the compound represented by general formula (ii-6-3) include compounds represented by the following structural formulas (ii-6-3.1) to (ii-6-3.4). be done.

Specific examples of the compound represented by the general formula (ii-6-4) include compounds represented by the following structural formulas (ii-6-4.1) to (ii-6-4.8). be done.

Specific examples of the compound represented by the general formula (ii-6-5) include compounds represented by the following structural formulas (ii-6-5.1) to (ii-6-5.2). be done.

Specific examples of the compound represented by the general formula (ii-6-6) include compounds represented by the following structural formulas (ii-6-6.1) to (ii-6-6.5). be done.

Specific examples of the compound represented by the general formula (ii-6-7) include compounds represented by the following structural formulas (ii-6-7.1) to (ii-6-7.4). be done.

Specific examples of the compound represented by general formula (ii-6-8) include compounds represented by the following structural formula (ii-6-8.1).

Specific examples of the compound represented by the general formula (ii-6-9) include compounds represented by the following structural formulas (ii-6-9.1) to (ii-6-9.20). be done.

Specific examples of the compound represented by the general formula (ii-6-10) include compounds represented by the following structural formulas (ii-6-10.1) to (ii-1-10.4). be done.

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

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

Specific examples of the compound represented by the general formula (ii-6-13) include compounds represented by the following structural formulas (ii-1-13.1) to (ii-6-13.5). be done.

Specific examples of the compound represented by the general formula (ii-6-14) include compounds represented by the following structural formulas (ii-6-14.1) to (ii-6-14.8). be done.

Specific examples of the compound represented by the general formula (ii-6-15) include compounds represented by the following structural formulas (ii-6-15.1) to (ii-6-15.5). be done.

Specific examples of the compound represented by the general formula (ii-6-16) include compounds represented by the following structural formulas (ii-6-16.1) to (ii-6-16.16). be done.

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

Specific examples of the compound represented by general formula (ii-6-18) include compounds represented by the following structural formula (ii-6-18.1).

Specific examples of the compound represented by the general formula (ii-6-19) include compounds represented by the following structural formulas (ii-6-19.1) to (ii-6-19.5). be done.

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

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

Specific examples of the compound represented by the general formula (ii-6-22) include compounds represented by the following structural formulas (ii-6-22.1) to (ii-6-22.20). be done.

Specific examples of the compound represented by the general formula (ii-6-23) include compounds represented by the following structural formulas (ii-6-23.1) to (ii-6-23.5). be done.

Specific examples of the compound represented by the general formula (ii-6-24) include compounds represented by the following structural formulas (ii-6-24.1) to (ii-6-24.14). be done.

Specific examples of the compound represented by the general formula (ii-6-25) include compounds represented by the following structural formulas (ii-6-25.1) to (ii-6-25.4). be done.

Specific examples of the compound represented by general formula (ii-6-26) include compounds represented by the following structural formula (ii-6-26.1).

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

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

Specific examples of the compound represented by the general formula (ii-6-29) include compounds represented by the following structural formulas (ii-6-29.1) to (ii-6-29.3). be done.

Specific examples of the compound represented by the general formula (ii-6-30) include compounds represented by the following structural formulas (ii-6-30.1) to (ii-6-30.4). be done.

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

Specific examples of the compound represented by the general formula (ii-6-32) include compounds represented by the following structural formulas (ii-6-32.1) to (ii-6-32.4). be done.

The compound represented by general formula (ii-1), general formula (ii-1-1) or structural formula (ii-1-1.1) is preferably used in the liquid crystal material in one or more types. is 1 to 20, preferably 1 to 15, preferably 1 to 10, preferably 1 to 5.
The total content of the compounds represented by general formula (ii-1), general formula (ii-1-1) or structural formula (ii-1-1.1) in 100% by mass of the liquid crystal material is compatible From the viewpoint, it is preferably 0.1 to 25% by mass, preferably 0.5 to 20% by mass, and preferably 1 to 15% by mass.

General formula (ii-2), general formulas (ii-2-1) to (ii-2-7), structural formulas (ii-2-1.1) to (ii-2-1.10), structural formulas (ii-2-2.1) ~ (ii-2-2.2), structural formula (ii-2-3.1) ~ (ii-2-3.7), structural formula (ii-2-4 .1) to (ii-2-4.4), structural formulas (ii-2-5.1) to (ii-2-5.4), structural formulas (ii-2-6.1) to (ii -2-6.4) or compounds represented by structural formulas (ii-2-7.1) to (ii-2-7.4) are used in the liquid crystal material, preferably one or more. is 1 to 20, preferably 1 to 15, preferably 1 to 10, preferably 1 to 5.
General formula (ii-2), general formulas (ii-2-1) to (ii-2-7), structural formulas (ii-2-1.1) to (ii-2-1.10), structural formulas (ii-2-2.1) ~ (ii-2-2.2), structural formula (ii-2-3.1) ~ (ii-2-3.7), structural formula (ii-2-4 .1) to (ii-2-4.4), structural formulas (ii-2-5.1) to (ii-2-5.4), structural formulas (ii-2-6.1) to (ii -2-6.4) or the total content of the compounds represented by structural formulas (ii-2-7.1) to (ii-2-7.4) in 100% by mass of the liquid crystal material is compatible From the viewpoint, it is preferably 5 to 45% by mass, preferably 10 to 40% by mass, and preferably 15 to 35% by mass.

General formula (ii-3), general formulas (ii-3-1) to (ii-3-12), structural formulas (ii-3-1.1) to (ii-3-1.4), structural formulas (ii-3-2.1), structural formulas (ii-3-3.1) to (ii-3-3.3), structural formulas (ii-3-4.1) to (ii-3-4 .6), structural formulas (i-3-5.1) to (i-3-5.4), structural formulas (ii-3-6.1) to (ii-3-6.7), structural formulas (ii-3-7.1) ~ (ii-3-7.5), structural formula (ii-3-8.1) ~ (ii-3-8.5), structural formula (ii-3-9 .1) to (ii-3-9.4), structural formulas (ii-3-10.1) to (ii-3-10.3), structural formulas (ii-3-11.1) to (ii -3-11.3) or compounds represented by structural formulas (ii-3-12.1) to (ii-3-12.3) are used in the liquid crystal material, preferably one or more. is 1 to 20, preferably 1 to 15, preferably 1 to 10, preferably 1 to 5.
General formula (ii-3), general formulas (ii-3-1) to (ii-3-12), structural formulas (ii-3-1.1) to (ii-3-1.4), structural formulas (ii-3-2.1), structural formulas (ii-3-3.1) to (ii-3-3.3), structural formulas (ii-3-4.1) to (ii-3-4 .6), structural formulas (i-3-5.1) to (i-3-5.4), structural formulas (ii-3-6.1) to (ii-3-6.7), structural formulas (ii-3-7.1) ~ (ii-3-7.5), structural formula (ii-3-8.1) ~ (ii-3-8.5), structural formula (ii-3-9 .1) to (ii-3-9.4), structural formulas (ii-3-10.1) to (ii-3-10.3), structural formulas (ii-3-11.1) to (ii -3-11.3) or the total content of the compounds represented by structural formulas (ii-3-12.1) to (ii-3-12.3) in 100% by mass of the liquid crystal material is compatible From the viewpoint, it is preferably 25 to 65% by mass, preferably 30 to 60% by mass, and preferably 35 to 55% by mass.

General formula (ii-4), general formulas (ii-4-1) to (ii-4-25), structural formulas (ii-4-1.1) to (ii-4-1.3), structural formulas (ii-4-2.1) ~ (ii-4-2.3), structural formula (ii-4-3.1) ~ (ii-4-3.3), structural formula (ii-4-4 .1) to (ii-4-4.3), structural formulas (ii-4-5.1) to (ii-4-5.3), structural formulas (ii-4-6.1) to (ii -4-6.3), structural formulas (ii-4-7.1) ~ (ii-4-7.3), structural formulas (ii-4-8.1) ~ (ii-4-8.3) ), structural formulas (ii-4-9.1) to (ii-4-9.5), structural formulas (ii-4-10.1) to (ii-4-10.4), structural formula (ii -4-11.1) ~ (ii-4-11.5), structural formulas (ii-4-12.1) ~ (ii-4-12.8), structural formula (ii-4-13.1) ) to (ii-4-13.4), structural formulas (ii-4-14.1) to (ii-4-14.4), structural formulas (ii-4-15.1), structural formulas (ii -4-16.1), structural formulas (ii-4-17.1) ~ (ii-4-17.5), structural formulas (ii-4-18.1) ~ (ii-4-18.5) ), structural formulas (ii-4-19.1) to (ii-4-19.4), structural formulas (ii-4-20.1) to (ii-4-20.4), structural formula (ii -4-21.1) ~ (ii-4-21.6), structural formulas (ii-4-22.1) ~ (ii-4-22.4), structural formula (ii-4-23.1) ) ~ (ii-4-23.5), structural formulas (ii-4-24.1) ~ (ii-4-24.4) or structural formulas (ii-4-25.1) ~ (ii-4 -25.4) are used for the liquid crystal material, 1 or 2 or more, preferably 1 to 20, preferably 1 to 15, preferably 1 to 10, preferably 1 to There are 5 types.
General formula (ii-4), general formulas (ii-4-1) to (ii-4-25), structural formulas (ii-4-1.1) to (ii-4-1.3), structural formulas (ii-4-2.1) ~ (ii-4-2.3), structural formula (ii-4-3.1) ~ (ii-4-3.3), structural formula (ii-4-4 .1) to (ii-4-4.3), structural formulas (ii-4-5.1) to (ii-4-5.3), structural formulas (ii-4-6.1) to (ii -4-6.3), structural formulas (ii-4-7.1) ~ (ii-4-7.3), structural formulas (ii-4-8.1) ~ (ii-4-8.3) ), structural formulas (ii-4-9.1) to (ii-4-9.5), structural formulas (ii-4-10.1) to (ii-4-10.4), structural formula (ii -4-11.1) ~ (ii-4-11.5), structural formulas (ii-4-12.1) ~ (ii-4-12.8), structural formula (ii-4-13.1) ) to (ii-4-13.4), structural formulas (ii-4-14.1) to (ii-4-14.4), structural formulas (ii-4-15.1), structural formulas (ii -4-16.1), structural formulas (ii-4-17.1) ~ (ii-4-17.5), structural formulas (ii-4-18.1) ~ (ii-4-18.5) ), structural formulas (ii-4-19.1) to (ii-4-19.4), structural formulas (ii-4-20.1) to (ii-4-20.4), structural formula (ii -4-21.1) ~ (ii-4-21.6), structural formulas (ii-4-22.1) ~ (ii-4-22.4), structural formula (ii-4-23.1) ) ~ (ii-4-23.5), structural formulas (ii-4-24.1) ~ (ii-4-24.4) or structural formulas (ii-4-25.1) ~ (ii-4 -25.4), the total content in 100% by mass of the liquid crystal material is preferably 0.1 to 25% by mass, more preferably 0.5 to 20% by mass, from the viewpoint of compatibility. preferably 1 to 15% by mass.

General formula (ii-5), general formulas (ii-5-1) to (ii-5-5), structural formulas (ii-5-1.1) to (ii-5-1.4), structural formulas (ii-5-2.1) ~ (ii-5-2.4), structural formula (ii-5-3.1) ~ (ii-5-3.3), structural formula (ii-5-4 .1) to (ii-5-4.3) or the compound represented by the structural formula (ii-5-5.1) is used in the liquid crystal material is one or more, preferably 1 to 20 species, preferably 1 to 15 species, preferably 1 to 10 species, preferably 1 to 5 species.
General formula (ii-5), general formulas (ii-5-1) to (ii-5-5), structural formulas (ii-5-1.1) to (ii-5-1.4), structural formulas (ii-5-2.1) ~ (ii-5-2.4), structural formula (ii-5-3.1) ~ (ii-5-3.3), structural formula (ii-5-4 .1) ~ (ii-5-4.3) or the total content of the compounds represented by the structural formula (ii-5-5.1) in 100 mass% of the liquid crystal material, from the viewpoint of compatibility, 0 .5 to 50% by mass, preferably 1 to 45% by mass, preferably 5 to 40% by mass.

General formula (ii-6), general formulas (ii-6-1) to (ii-6-32), structural formulas (ii-6-1.1) to (ii-6-1.4), structural formulas (ii-6-2.1) ~ (ii-6-2.4), structural formula (ii-6-3.1) ~ (ii-6-3.4), structural formula (ii-6-4 .1) to (ii-6-4.8), structural formulas (ii-6-5.1) to (ii-6-5.2), structural formulas (ii-6-6.1) to (ii -6-6.5), structural formulas (ii-6-7.1) to (ii-6-7.4), structural formulas (ii-6-8.1), structural formulas (ii-6-9 .1) to (ii-6-9.20), structural formulas (ii-6-10.1) to (ii-1-10.4), structural formulas (ii-6-11.1) to (ii -6-11.4), structural formulas (ii-6-12.1) to (ii-6-12.4), structural formulas (ii-1-13.1) to (ii-6-13.5 ), structural formulas (ii-6-14.1) to (ii-6-14.8), structural formulas (ii-6-15.1) to (ii-6-15.5), structural formula (ii -6-16.1) ~ (ii-6-16.16), structural formulas (ii-6-17.1) ~ (ii-6-17.4), structural formula (ii-6-18.1) ), structural formulas (ii-6-19.1) to (ii-6-19.5), structural formulas (ii-6-20.1) to (ii-6-20.4), structural formula (ii -6-21.1) to (ii-6-21.4), structural formulas (ii-6-22.1) to (ii-6-22.20), structural formulas (ii-6-23.1 ) to (ii-6-23.5), structural formulas (ii-6-24.1) to (ii-6-24.14), structural formulas (ii-6-25.1) to (ii-6 -25.4), structural formula (ii-6-26.1), structural formula (ii-6-27.1), structural formulas (ii-6-28.1) to (ii-6-28.5 ), structural formulas (ii-6-29.1) to (ii-6-29.3), structural formulas (ii-6-30.1) to (ii-6-30.4), structural formulas (ii -6-31.1) to (ii-6-31.5) or types of compounds represented by structural formulas (ii-6-32.1) to (ii-6-32.4) used in liquid crystal materials is 1 or 2 or more, preferably 1 to 20, preferably 1 to 15, preferably 1 to 10, preferably 1 to 5.
General formula (ii-6), general formulas (ii-6-1) to (ii-6-32), structural formulas (ii-6-1.1) to (ii-6-1.4), structural formulas (ii-6-2.1) ~ (ii-6-2.4), structural formula (ii-6-3.1) ~ (ii-6-3.4), structural formula (ii-6-4 .1) to (ii-6-4.8), structural formulas (ii-6-5.1) to (ii-6-5.2), structural formulas (ii-6-6.1) to (ii -6-6.5), structural formulas (ii-6-7.1) to (ii-6-7.4), structural formulas (ii-6-8.1), structural formulas (ii-6-9 .1) to (ii-6-9.20), structural formulas (ii-6-10.1) to (ii-1-10.4), structural formulas (ii-6-11.1) to (ii -6-11.4), structural formulas (ii-6-12.1) to (ii-6-12.4), structural formulas (ii-1-13.1) to (ii-6-13.5 ), structural formulas (ii-6-14.1) to (ii-6-14.8), structural formulas (ii-6-15.1) to (ii-6-15.5), structural formula (ii -6-16.1) ~ (ii-6-16.16), structural formulas (ii-6-17.1) ~ (ii-6-17.4), structural formula (ii-6-18.1) ), structural formulas (ii-6-19.1) to (ii-6-19.5), structural formulas (ii-6-20.1) to (ii-6-20.4), structural formula (ii -6-21.1) to (ii-6-21.4), structural formulas (ii-6-22.1) to (ii-6-22.20), structural formulas (ii-6-23.1 ) to (ii-6-23.5), structural formulas (ii-6-24.1) to (ii-6-24.14), structural formulas (ii-6-25.1) to (ii-6 -25.4), structural formula (ii-6-26.1), structural formula (ii-6-27.1), structural formulas (ii-6-28.1) to (ii-6-28.5 ), structural formulas (ii-6-29.1) to (ii-6-29.3), structural formulas (ii-6-30.1) to (ii-6-30.4), structural formulas (ii -6-31.1) to (ii-6-31.5) or 100% by mass of the liquid crystal material of the compounds represented by the structural formulas (ii-6-32.1) to (ii-6-32.4) From the viewpoint of compatibility, the total content is preferably 10 to 55% by mass, preferably 15 to 50% by mass, and preferably 20 to 45% by mass.
Compounds represented by general formula (ii) (including subordinate concepts) can be synthesized using known synthesis methods.

From the viewpoint of Δn and/or _Δεr , the liquid crystal composition according to the present invention further includes one or two compounds represented by the following general formula (iii) having at least one —C≡C— as a linking group. It may include the above.

In general formula (iii), R ⁱⁱⁱ¹ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S—, —CO— and/or —CS—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkyl group are each independently —CO—O—, —O—CO—, —CO—S—, —S—CO -, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
Also, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
For example, R ⁱⁱⁱ¹ can represent an alkoxy group having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —O—.
The alkoxy group is a linear, branched or cyclic alkoxy group, preferably a linear alkoxy group.
The number of carbon atoms in the alkoxy group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱⁱ¹ can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —S—.
The alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, preferably a linear alkylsulfanyl group.
The number of carbon atoms in the alkylsulfanyl group is preferably 1-10, preferably 1-6.
R ⁱⁱⁱ¹ represents an alkenyl group having 2 to 20 carbon atoms by substituting -CH=CH- for one or more -CH ₂ -CH ₂ - in the alkyl group. be able to.
The alkenyl group is a linear, branched or cyclic alkenyl group, preferably a linear alkenyl group.
The number of carbon atoms in the alkenyl group is preferably 2-10, preferably 2-6.
R ⁱⁱⁱ¹ represents an alkynyl group having 2 to 20 carbon atoms by substituting one or more —CH ₂ —CH ₂ — in the alkyl group with —C≡C— be able to.
The alkynyl group is a linear, branched or cyclic alkynyl group, preferably a linear alkynyl group.
The number of carbon atoms in the alkynyl group is preferably 2-10, preferably 2-6.
In R ⁱⁱⁱ¹ , one -CH ₂ - in the alkyl group is substituted with -O-, and one or more -CH ₂ -CH ₂ - is substituted with -CH=CH- can represent an alkenyloxy group having 2 to 19 carbon atoms.
The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, preferably a linear alkenyloxy group.
The number of carbon atoms in the alkenyloxy group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱⁱ¹ can represent a halogenated alkyl group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.
The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, preferably a linear halogenated alkyl group.
The number of carbon atoms in the halogenated alkyl group is preferably 2-10, preferably 2-6.
In addition, R ⁱⁱⁱ¹ is obtained by substituting one —CH ₂ — in the alkyl group with —O— and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. , can represent a halogenated alkoxy group having 1 to 19 carbon atoms.
The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, preferably a linear halogenated alkoxy group.
The number of carbon atoms in the halogenated alkoxy group is preferably 2-10, preferably 2-6.
Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) for R ⁱⁱⁱ¹ include groups represented by formulas (R ⁱⁱⁱ¹ -1) to (R ⁱⁱⁱ¹ -36).

In formulas (R ⁱⁱⁱ¹ -1) to (R ⁱⁱⁱ¹ -36), black dots represent bonds to A ⁱⁱⁱ¹ .
R ⁱⁱⁱ¹ is preferably an alkyl group having 1 to 12 carbon atoms when emphasizing the reliability of the entire liquid crystal composition, and when emphasizing the reduction of the viscosity of the entire liquid crystal composition, a carbon atom It is preferably an alkenyl group of number 2-8.
When the ring structure to which R ⁱⁱⁱ¹ is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a carbon atom An alkenyl group having a number of 4 to 5 is preferable, and when the ring structure to which R ⁱⁱⁱ¹ is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a linear A linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferred.
In order to stabilize the nematic phase, R ⁱⁱⁱ¹ preferably has a total of 5 or less carbon atoms and, if present, oxygen atoms, and is preferably linear.
From the viewpoint of solubility, R ⁱⁱⁱ¹ is preferably a straight-chain alkyl group having 2 to 6 carbon atoms or a straight-chain alkylsulfanyl group having 1 to 6 carbon atoms.

In general formula (iii), R ⁱⁱⁱ² is a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methyl represents either an amino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group or an alkyl group having 1 to 20 carbon atoms;
The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group is preferably 2-10, preferably 2-6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S—, —CO— and/or —CS—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkyl group are each independently —CO—O—, —O—CO—, —CO—S—, —S—CO -, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
Also, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
For example, R ⁱⁱⁱ² can represent an alkoxy group having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —O—.
The alkoxy group is a linear, branched or cyclic alkoxy group, preferably a linear alkoxy group.
The number of carbon atoms in the alkoxy group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱⁱ² can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —S—.
The alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, preferably a linear alkylsulfanyl group.
The number of carbon atoms in the alkylsulfanyl group is preferably 1-10, preferably 1-6.
R ⁱⁱⁱ² represents an alkenyl group having 2 to 20 carbon atoms by substituting -CH=CH- for one or more -CH ₂ -CH ₂ - in the alkyl group. be able to.
The alkenyl group is a linear, branched or cyclic alkenyl group, preferably a linear alkenyl group.
The number of carbon atoms in the alkenyl group is preferably 2-10, preferably 2-6.
R ⁱⁱⁱ² represents an alkynyl group having 2 to 20 carbon atoms by substituting one or more —CH ₂ —CH ₂ — in the alkyl group with —C≡C— be able to.
The alkynyl group is a linear, branched or cyclic alkynyl group, preferably a linear alkynyl group.
The number of carbon atoms in the alkynyl group is preferably 2-10, preferably 2-6.
In R ⁱⁱⁱ² , one -CH ₂ - in the alkyl group is substituted with -O- and one or more -CH ₂ -CH ₂ - is substituted with -CH=CH- can represent an alkenyloxy group having 2 to 19 carbon atoms.
The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, preferably a linear alkenyloxy group.
The number of carbon atoms in the alkenyloxy group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱⁱ² can represent a halogenated alkyl group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.
The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, preferably a linear halogenated alkyl group.
The number of carbon atoms in the halogenated alkyl group is preferably 2-10, preferably 2-6.
Further, R ⁱⁱⁱ² is obtained by substituting one —CH ₂ — in the alkyl group with —O— and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. , can represent a halogenated alkoxy group having 1 to 19 carbon atoms.
The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, preferably a linear halogenated alkoxy group.
The number of carbon atoms in the halogenated alkoxy group is preferably 2-10, preferably 2-6.
Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) for R ⁱⁱⁱ² include groups represented by formulas (R ⁱⁱⁱ² -1) to (R ⁱⁱⁱ² -36).

In formulas (R ⁱⁱⁱ² -1) to (R ⁱⁱⁱ² -36), black dots represent bonds to A ⁱⁱⁱ³ .
When the ring structure to which R ⁱⁱⁱ² is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a carbon atom An alkenyl group having a number of 4 to 5 is preferable, and when the ring structure to which R ⁱⁱⁱ² is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a linear A linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferred.
In order to stabilize the nematic phase, R ⁱⁱⁱ² preferably has a total of 5 or less carbon atoms and, if present, oxygen atoms, and is preferably linear.
From the viewpoint of solubility, Δn and/or _Δεr , R ⁱⁱⁱ² includes a fluorine atom, a cyano group, a linear alkyl group having 2 to 6 carbon atoms, and a linear alkyl group having 1 to 6 carbon atoms. or a linear alkylsulfanyl group having 1 to 6 carbon atoms.

In general formula (iii), A ⁱⁱⁱ¹ , A ⁱⁱⁱ² and A ⁱⁱⁱ³ each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms.
The hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms is, more specifically, the following group (a), group (b), group (c) and group (d):
(a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more non-adjacent —CH ₂ — may be replaced with —O— or —S—; good.)
(b) 1,4-phenylene group (one -CH= or two or more -CH= present in this group may be replaced with -N=)
(c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6- diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,4-diyl group, 2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group, one -CH= or two or more -CH= may be replaced with -N=.)
(d) thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more -CH= present in this group may be replaced with -N=).
It is preferred to represent a group selected from the group consisting of

One or more hydrogen atoms in A ⁱⁱⁱ¹ , A ⁱⁱⁱ² and A ⁱⁱⁱ³ may each independently be substituted with a substituent S ^vi1 .
Substituent S ⁱⁱⁱ¹ is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or alkyl group having 1 to 20 carbon atoms.
The alkyl group is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group is preferably 2-10, preferably 3-6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S— and/or —CO—.
In addition, one or two or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CH=CH-, -CF=CF-, -C≡C-, -CO-O- , —O—CO—, —CO—S—, —S—CO—, —CO—NH— and/or —NH—CO—.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be substituted with —O—CO—O—.
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
The substituent S ⁱⁱⁱ¹ is preferably a fluorine atom or a linear alkyl group having 1 to 3 carbon atoms.
At least one of A ⁱⁱⁱ¹ , A ⁱⁱⁱ² and A ⁱⁱⁱ³ is preferably substituted with at least one substituent S ⁱⁱⁱ¹ .
In addition, A ⁱⁱⁱ¹ is preferably substituted with at least one substituent S ⁱⁱⁱ¹ .
In addition, when there are multiple substituents ^Siii1 , they may be the same or different.

The substitution position of the substituent S ⁱⁱⁱ¹ in A ⁱⁱⁱ¹ is preferably any one of the following formulas (A ⁱⁱⁱ¹ -SP-1) to (A ⁱⁱⁱ¹ -SP-3).

In formulas (A ⁱⁱⁱ¹ -SP-1) to (A ⁱⁱⁱ¹ -SP-3), white dots represent bonds of R ⁱⁱⁱ¹ and black dots represent bonds to -C≡C-.
The substitution position of the substituent S ⁱⁱⁱ¹ in A ⁱⁱⁱ² is preferably any one of the following formulas (A ⁱⁱⁱ² -SP-1) to (A ^vi2 -SP-7), and is compatible with other liquid crystal compounds. From this point of view, any one of the following formulas (A ⁱⁱⁱ² -SP-1) to (A ⁱⁱⁱ² -SP-7) is preferably represented.

In formulas (A ⁱⁱⁱ² -SP-1) to (A ⁱⁱⁱ² -SP-7), white dots represent bonds of -C≡C-, and black dots represent bonds to Z ⁱⁱⁱ¹ .
The substitution position of the substituent S ⁱⁱⁱ¹ in A ⁱⁱⁱ³ is preferably any one of the following formulas (A ⁱⁱⁱ³ -SP-1) to (A ⁱⁱⁱ³ -SP-8), and from the viewpoint of solubility, the following formula ( Any one of A ⁱⁱⁱ³ -SP-1) to (A ⁱⁱⁱ³ -SP-5) is preferably represented.

In formulas (A ⁱⁱⁱ³ -SP-1) to (A ⁱⁱⁱ³ -SP-8), white dots represent bonds to Z ⁱⁱⁱ¹ and black dots represent bonds to Z ⁱⁱⁱ¹ or R ⁱⁱⁱ² .
More specifically, A ⁱⁱⁱ¹ preferably represents any one of the following formulas (A ⁱⁱⁱ¹ -1) to (A ⁱⁱⁱ¹ -5).

In formulas (A ⁱⁱⁱ¹ -1) to (A ⁱⁱⁱ¹ -5), white dots represent bonds of R ^vi1 and black dots represent bonds to -C≡C-.
More specifically, A ⁱⁱⁱ² preferably represents any one of the following formulas (A ⁱⁱⁱ² -1) to (A ⁱⁱⁱ² -5).

In formulas (A ⁱⁱⁱ² -1) to (A ⁱⁱⁱ² -5), white dots represent bonds of -C≡C-, and black dots represent bonds to Z ⁱⁱⁱ¹ .
More specifically, A ⁱⁱⁱ³ preferably represents any one of the following formulas (A ⁱⁱⁱ³ -1) to (A ⁱⁱⁱ³ -5).

In formulas (A ⁱⁱⁱ³ -1) to (A ⁱⁱⁱ³ -5), white dots represent bonds to Z ⁱⁱⁱ¹ and black dots represent bonds to Z ⁱⁱⁱ¹ or R ⁱⁱⁱ² .

In general formula (iii), each Z ⁱⁱⁱ¹ independently represents either a single bond or an alkylene group having 1 to 20 carbon atoms.
The alkylene group is a linear, branched or cyclic alkylene group, preferably a linear alkylene group.
The number of carbon atoms in the alkylene group is preferably 2-10, preferably 2-6.
One or more —CH ₂ — in the alkylene group may each independently be replaced with —O—, —CF ₂ — and/or —CO—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, -CH=CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, may be substituted with -C≡C-, -CO-O- and/or -O-CO-.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
However, when the alkylene group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted ones) include groups represented by formulas (Z ⁱⁱⁱ¹ -1) to (Z ⁱⁱⁱ¹ -24).

In formulas (Z ⁱⁱⁱ¹ -1) to (Z ⁱⁱⁱ¹ -24), white dots represent bonds to A ⁱⁱⁱ² or A ⁱⁱⁱ³ , and black dots represent bonds to A ⁱⁱⁱ³ .

In general formula (iii), ⁿⁱⁱⁱ¹ represents an integer of 1-3, preferably an integer of 1-2.
When n ⁱⁱⁱ¹ is 1, Z ⁱⁱⁱ¹ preferably represents -C≡C- from the viewpoint of Δn and/or _Δεr .
Further, when ⁿⁱⁱⁱ¹ is 2 or 3, at least one of ^Ziii1 preferably represents -C≡C- from the viewpoint of Δn and/or _Δεr .
In general formula (iii), when there are a plurality of A ⁱⁱⁱ³ and Z ⁱⁱⁱ¹ , they may be the same or different.

The compound represented by general formula (iii) is preferably a compound represented by general formula (iii-1) below.

In general formula (iii-1), R ⁱⁱⁱ¹ , R ⁱⁱⁱ² , A ⁱⁱⁱ¹ , A ⁱⁱⁱ² and A ⁱⁱⁱ³ are R ⁱⁱⁱ¹ , R ⁱⁱⁱ² , A ⁱⁱⁱ¹ , A ⁱⁱⁱ² and A ⁱⁱⁱ³ in general formula (iii-1) Each has the same meaning.
The compound represented by general formula (iii-1) is preferably a compound represented by general formula (iii-1-1) below.

In general formula (iii-1-1), R ⁱⁱⁱ¹ , R ⁱⁱⁱ² and S ⁱⁱⁱ¹ each independently have the same meaning as R ⁱⁱⁱ¹ , R ⁱⁱⁱ² and S ⁱⁱⁱ¹ in general formula (iii) above.
Specific examples of the compound represented by the general formula (iii-1-1) include compounds represented by the following structural formulas (iii-1-1.1) to (iii-1-1.24). be done.

Compounds represented by general formula (iii), general formula (iii-1), general formula (iii-1-1) or structural formulas (iii-1-1.1) to (iii-1-1.24) The types used in the liquid crystal composition are 1 or 2 or more, preferably 1 to 5, preferably 1 to 4, preferably 1 to 3, preferably 1 to 2, preferably 1. .

Compounds represented by general formula (iii), general formula (iii-1), general formula (iii-1-1) or structural formulas (iii-1-1.1) to (iii-1-1.24) in 100% by mass of the liquid crystal composition is preferably 0.5 to 25% by mass, preferably 1 to 20% by mass, from the viewpoint of solubility, Δn and/or _Δεr . , 3 to 15% by mass.

Compounds (including subordinate concepts) represented by general formula (iii) can be synthesized using known synthesis methods.

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

In general formulas (np-1) to (np-3), R ^npi and R ^npii each independently represent either an alkyl group having 1 to 20 carbon atoms or a halogen atom.
The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S—, —CO— and/or —CS—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkyl group are each independently —CO—O—, —O—CO—, —CO—S—, —S—CO -, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- and/or -C≡C- good too.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
Also, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
For example, R ^npi and R ^npii can represent an alkoxy group having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —O—.
The alkoxy group is a linear, branched or cyclic alkoxy group, preferably a linear alkoxy group.
The number of carbon atoms in the alkoxy group is preferably 2-10, preferably 2-6.
Further, R ^npi and R ^npii can represent an alkylsulfanyl group (thioalkyl group) having 1 to 19 carbon atoms by substituting one —CH ₂ — in the alkyl group with —S—. .
The alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, preferably a linear alkylsulfanyl group.
The number of carbon atoms in the alkylsulfanyl group is preferably 2-10, preferably 2-6.
In addition, R ^npi and R ^npii are alkenyl having 2 to 20 carbon atoms by substituting one or more —CH ₂ —CH ₂ — in the alkyl group with —CH═CH—. group.
The alkenyl group is a linear, branched or cyclic alkenyl group, preferably a linear alkenyl group.
The number of carbon atoms in the alkenyl group is preferably 2-10, preferably 2-6.
In addition, R ^npi and R ^npii are alkynyls having 2 to 20 carbon atoms obtained by substituting one or more —CH ₂ —CH ₂ — in the alkyl group with —C≡C—. group.
The alkynyl group is a linear, branched or cyclic alkynyl group, preferably a linear alkynyl group.
The number of carbon atoms in the alkynyl group is preferably 2-10, preferably 2-6.
In R ^npi and R ^npii , one —CH ₂ — in the alkyl group is substituted with —O—, and one or more —CH ₂ —CH ₂ — are —CH═CH— can represent an alkenyloxy group having 2 to 19 carbon atoms.
The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, preferably a linear alkenyloxy group.
The number of carbon atoms in the alkenyloxy group is preferably 2-10, preferably 2-6.
Further, R ^npi and R ^npii can represent a halogenated alkyl group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom. .
The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, preferably a linear halogenated alkyl group.
The number of carbon atoms in the halogenated alkyl group is preferably 2-10, preferably 2-6.
In R ^npi and R ^npii , one —CH ₂ — in the alkyl group is substituted with —O—, and one or more hydrogen atoms in the alkyl group are substituted with halogen atoms. can represent a halogenated alkoxy group having 1 to 19 carbon atoms.
The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, preferably a linear halogenated alkoxy group.
The number of carbon atoms in the halogenated alkoxy group is preferably 2-10, preferably 2-6.
Specific examples of alkyl groups (including substituted ones) having 1 to 20 carbon atoms in R ^npi and R ^npii are represented by formulas (R ^npi/ii -1) to (R ^npi/ii -36). and the like.

In formulas (R ^npi/ii -1) to (R ^npi/ii -36), the black dot represents a bond to ring A, ring B, ring C or ring D.
Halogen atoms in R ^npi and R ^npii include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

In general formulas (np-1) to (np-3), ring A, ring B, ring C and ring D are each independently the following group (a), group (b), group (c) and (d):
(a) 1,4-cyclohexylene group (one —CH ₂ — or two or more non-adjacent —CH ₂ — present in this group may be replaced with —O—);
(b) a 1,4-phenylene group (one -CH= or two or more -CH= present in this group may be replaced with -N=);
(c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or One —CH= or two or more —CH= present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N=.)
(d) selected from the group consisting of 1,4-cyclohexenylene group, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group and pyridine-2,5-diyl group; represents a group.

One or more hydrogen atoms in Ring A, Ring B, Ring C and Ring D may each independently be substituted with a substituent ^Snpi1 .
The substituent S ^npi1 represents either a halogen atom, a cyano group or an alkyl group having 1 to 20 carbon atoms.
The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and from the viewpoint of stability and safety, a fluorine atom is preferred.
The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, preferably a linear alkyl group.
The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
One or more —CH ₂ — in the alkyl group may each independently be substituted with —O—, —S—, —CO— and/or —CS—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkyl group are each independently —CO—O—, —O—CO—, —CO—S—, —S—CO -, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-.
One or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
Also, one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
However, when the alkyl group is substituted with a predetermined group, the oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
From the viewpoint of V _th , the substituent ^Snpi1 is preferably a halogen atom, preferably a fluorine atom.
In addition, when there are multiple substituents ^Snpi1 , they may be the same or different.

The substitution position of the substituent S ^npi1 on the ring A is preferably the following formula (A-SP-1).

In formula (A-SP-1), white dots represent bonds to R ^npi and black dots represent bonds to Z ^npi .
More specifically, ring A preferably represents any one of the following formulas (A-1) to (A-3).

In formulas (A-1) to (A-3), white dots represent bonds to R ^npi , and black dots represent bonds to Z ^npi .
More specifically, ring B preferably represents any one of the following formulas (B-1) to (B-2).

In formulas (B-1) and (B-2), white dots represent bonds to ^Znpi , and black dots represent bonds to ^Rnpii or ^Znpii .
More specifically, ring C preferably represents any one of the following formulas (C-1) to (C-2).

In formulas (C-1) and (C-2), white dots represent bonds to Z ^npii , and black dots represent bonds to R ^npii or Z ^npiii .

In general formulas (np-1) to (np-3), Z ^npi , Z ^npii and Z ^npiii each independently represent either a single bond or an alkylene group having 1 to 20 carbon atoms.
One or more —CH ₂ — in the alkylene group may be independently substituted with —O—.
In addition, one or two or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, -CH=CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, may be substituted with -C≡C-, -CO-O- and/or -O-CO-.
Also, one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—.
However, when an alkyl group having 1 to 10 carbon atoms is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.
From the viewpoint of compound stability, it is preferred that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms are not directly bonded.
Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted ones) include groups represented by formulas (Z ^npi/ii/iii -1) to (Z ^npi/ii/iii -24) etc.

In formulas (Z ^npi/ii/iii -1) to (Z ^npi/ii/iii -24), white dots represent a bond to ring A, ring B or ring C, black dots represent ring B, ring C or represents a bond to ring D;
From the viewpoint of Δn and/or Δε _r , it is preferred that Z ^npi , Z ^npii and Z ^npiii each independently represent a single bond, —C≡C— and —CO—O—.
However, among the compounds represented by general formulas (np-1) to (np-3), compounds represented by general formula (iii) (including subordinate concepts) are excluded.
The compound represented by the general formula (np-1) is preferably a compound represented by the following general formula (np-1-1).

R ^npi and R ^npii in general formula (np-1-1) have the same meanings as R ^npi and R ^npii in general formulas (np-1) to (np-3) above, respectively.
Specific examples of the compound represented by the general formula (np-1-1) include compounds represented by the following structural formulas (np-1-1.1) to (np-1-1.2). be done.

The compound represented by the general formula (np-2) is preferably a compound represented by the following general formula (np-2-1).

R ^npi and R ^npii in general formula (np-2-1) have the same meanings as R ^npi and R ^npii in general formulas (np-1) to (np-3) above, respectively.
Specific examples of the compound represented by the general formula (np-2-1) include compounds represented by the following structural formulas (np-2-1.1) to (np-2-1.3). be done.

General formulas (np-1) to (np-3), general formulas (np-1-1), general formulas (np-2-1), structural formulas (np-1-1.1) to (np-1 -1.2) or the compounds represented by the structural formulas (np-2-1.1) to (np-2-1.3) are used in the liquid crystal composition is one or more, preferably 1 to 10 types, preferably 1 to 8 types, preferably 1 to 6 types, preferably 1 to 4 types, preferably 1 to 2 types.

General formulas (np-1) to (np-3), general formulas (np-1-1), general formulas (np-2-1), structural formulas (np-1-1.1) to (np-1 -1.2) or the total content of the compounds represented by the structural formulas (np-2-1.1) to (np-2-1.3) in 100% by mass of the liquid crystal composition, the solubility, Δn and/or from the viewpoint of _Δεr , it is preferably 0.5 to 45% by mass, preferably 1 to 35% by mass, and preferably 3 to 25% by mass.

Compounds represented by general formulas (np-1) to (np-3) (including subordinate concepts) can be produced by known methods.

(Liquid crystal composition)
The liquid crystal composition according to the present invention is, for example, the compound represented by the above general formula (i) (including subordinate concepts), the above-described other compounds (including subordinate concepts), and additives. It can be manufactured by

Additives include stabilizers, dye compounds, polymerizable compounds, azotran compounds, cyano compounds, and the like.

Examples of stabilizers include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols. and hindered amines.
Hindered phenols include hindered phenol-based antioxidants represented by the following structural formulas (XX-1) to (XX-3).

Hindered amines include hindered amine light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

When a stabilizer is used, the total content of the stabilizer in 100% by mass of the liquid crystal composition is preferably 0.005 to 1% by mass, preferably 0.02 to 0.50% by mass. , 0.03 to 0.35% by mass.

From the viewpoint of solubility, Δn and/or _Δεr , the combination of compounds used in the liquid crystal composition includes: 1) a compound represented by general formula (i) (including subordinate concepts) and general formula (ii-1 ) represented by a compound (including a subordinate concept), a compound represented by the general formula (ii-2) (including a subordinate concept), and a compound represented by the general formula (ii-3) (a subordinate concept ) and a compound represented by general formula (ii-5) (including subordinate concepts), 2) a compound represented by general formula (i) (including subordinate concepts), and general formula (ii -2) a compound represented by (including a subordinate concept), a compound represented by the general formula (ii-4) (including a subordinate concept), and a compound represented by the general formula (ii-5) (subordinate concept) with a compound represented by general formula (ii-6) (including subordinate concepts) is preferred.

From the viewpoint of Δn and/or Δεr, the liquid crystal composition according to the present invention comprises one or more compounds (including subordinate concepts) represented by general formula (i) and general formula (ii). It preferably contains three or more compounds (including subordinate concepts).
Further, from the viewpoint of solubility, the liquid crystal composition according to the present invention includes one or more compounds represented by general formula (i) (including subordinate concepts), general formula (ii-3) and / Or it preferably contains three or more compounds represented by general formula (ii-5) (including subordinate concepts).
Further, from the viewpoint of low viscosity, the liquid crystal composition according to the present invention includes one or more compounds represented by general formula (i) (including subordinate concepts) and general formula (np-1) ~ Compounds represented by (np-3) (including subordinate concepts) containing one or more compounds represented by the general formulas (np-1) to (np-3) (subordinate concepts ) in 100% by mass of the liquid crystal composition is preferably 1 to 30% by mass, preferably 5 to 25% by mass.

<Characteristic value of liquid crystal composition>
The liquid crystal phase upper limit temperature (T _ni ) is the temperature at which the liquid crystal composition transitions from the nematic phase to the isotropic phase.
T _ni is measured by preparing a preparation in which a liquid crystal composition is sandwiched between a slide glass and a cover glass, and observing it with a polarizing microscope while heating it on a hot stage.
It can also be measured by differential scanning calorimetry (DSC).
Use "°C" as the unit.
The higher the _Tni , the more the nematic phase can be maintained even at high temperatures, and the wider the operating temperature range can be taken.
The upper limit temperature (T _ni ) of the liquid crystal phase of the liquid crystal composition according to the present invention is appropriately set depending on whether the liquid crystal display element is used indoors or in an automobile, or outdoors in which the external temperature of the liquid crystal display element can be controlled. However, from the viewpoint of the driving temperature range, it is preferably 155°C or higher, preferably 155 to 200°C, and more preferably 160 to 180°C.

The liquid crystal phase lower limit temperature (T _→n ) is the temperature at which the liquid crystal composition transitions from other phases (glass, smectic phase, crystal phase) to nematic phase.
T _→n is measured by filling a glass capillary with a liquid crystal composition, immersing it in a coolant of −70° C. to cause a phase transition of the liquid crystal composition to another phase, and observing while increasing the temperature.
It can also be measured by differential scanning calorimetry (DSC).
Use "°C" as the unit.
As T _→n is lower, the nematic phase can be maintained even at a low temperature, so a wide operating temperature range can be obtained.
The liquid crystal phase lower limit temperature (T _{→ n} ) of the liquid crystal composition according to the present invention is preferably 10°C or less, preferably −70 to 0°C, from the viewpoint of driving temperature, and −40 to −5. °C is preferred.

Δn (refractive index anisotropy) correlates with Δn in the near-infrared region used in an optical sensor described later.
As the Δn increases, the phase modulation power of the light of the target wavelength increases, so it is particularly suitable for optical sensors.
Δn at 25° C. and 589 nm is obtained from the difference (n _e −n _o ) between the extraordinary refractive index (n _e ) and the ordinary refractive index (n _o ) of the liquid crystal composition using an Abbe refractometer.
Δn can also be obtained from a phase difference measuring device.
The relationship Δn=Re/d holds between the retardation Re, the thickness d of the liquid crystal layer, and Δn.
A liquid crystal composition was injected into a glass cell with a polyimide alignment film that had a cell gap (d) of about 3.0 μm and was subjected to anti-parallel rubbing treatment, and in-plane Re was measured with a retardation film and optical material inspection device RETS-100 ( manufactured by Otsuka Electronics Co., Ltd.).
The measurement is performed at a temperature of 25° C. and a temperature of 589 nm, and has no unit.
Δn of the liquid crystal composition according to the present invention at 25° C. and 589 nm is preferably 0.37 or more, preferably 0.375 to 0.60, from the viewpoint of the phase modulation power of light with a wavelength. It is preferably 0.38 to 0.55, preferably 0.40 to 0.50.

Rotational viscosity (γ ₁ ) is the viscosity associated with the rotation of liquid crystal molecules.
γ ₁ can be measured by filling a liquid crystal composition in a glass cell with a cell gap of about 10 μm and using LCM-2 (manufactured by Toyo Technica).
A horizontally aligned cell is used for a liquid crystal composition with a positive dielectric anisotropy, and a vertically aligned cell is used for a liquid crystal composition with a negative dielectric anisotropy.
The measurement is performed at a temperature of 25° C., and the unit is mPa·s.
The smaller _γ1 is, the faster the response speed of the liquid crystal composition is, so it is suitable for any liquid crystal display device.
The rotational viscosity (γ ₁ ) of the liquid crystal composition of the present invention at 25° C. is preferably 150 to 2000 mPa·s, more preferably 200 to 1500 mPa·s, from the viewpoint of response speed. , 250 to 1000 mPa·s.

The threshold voltage (V _th ) correlates with the driving voltage of the liquid crystal composition.
V _th can be determined from the transmittance when a TN cell with a gap of 8.3 μm is filled with a liquid crystal composition and a voltage is applied.
The measurement is performed at a temperature of 25° C., and the unit is “V”.
The lower _the Vth, the lower the voltage that can be driven.
V _th of the liquid crystal composition according to the present invention at 25° C. is preferably 3.0 V or less, more preferably 0.3 to 3.0 V, more preferably 0.5 to 2.0 V, from the viewpoint of driving voltage. It is preferably 7 V, preferably 0.7 to 2.5 V, preferably 0.9 to 2.3 V, preferably 1.1 to 2.1 V, preferably 1.3 to It is preferably 2.1V.

The higher the dielectric anisotropy in the high-frequency region, the greater the phase modulation power for radio waves in the target frequency band, so it is particularly suitable for antenna applications.
Also, in antenna applications, the smaller the dielectric loss tangent in the high frequency range, the smaller the energy loss in the target frequency band, which is preferable.
For the liquid crystal composition according to the present invention, the dielectric anisotropy Δε _r and the average value tan δ _iso of the dielectric loss tangent at 10 GHz were measured as representative characteristics in the high frequency region.
Δε _r =(ε _r∥ −ε _r⊥ ) and tanδ _iso =(2ε _r⊥ tan δ _⊥ +ε _r∥ tan _δ∥ )/(2ε _r⊥ +ε _r∥ ).
Here, “εr” is the dielectric constant, “tanδ” is the dielectric loss tangent, the subscript “∥” is the direction parallel to the alignment direction of the liquid crystal, and “⊥” is the direction perpendicular to the alignment direction of the liquid crystal. Indicates that it is a component.

Δε _r and tan δ _iso can be measured by the following methods.
First, a liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE).
The capillary tube used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm with an effective length of 4.0 cm.
A capillary tube containing a liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Lab Co., Ltd.) having a resonance frequency of 10 GHz.
This cavity has a diameter of 30 mm and a profile width of 26 mm.
A signal is then input, and the result of the output signal is recorded using a network analyzer (manufactured by Keysight Technologies, Inc.).
The dielectric constant (ε _r ) and the loss angle (δ) at 10 GHz are determined using the difference between the resonant frequency of the PTFE capillary tube without the liquid crystal composition and the resonant frequency of the PTFE capillary tube with the liquid crystal composition.
The tangent of δ obtained is the dielectric loss tangent (tan δ).
The resonance frequency using the PTFE capillary tube containing the liquid crystal composition is obtained as the value of the characteristic component perpendicular to the alignment direction of the liquid crystal molecules and the value of the characteristic component parallel to the alignment direction of the liquid crystal molecules by controlling the alignment of the liquid crystal molecules.
A magnetic field of a permanent magnet or an electromagnet is used to align the liquid crystal molecules in the vertical direction (perpendicular to the effective length direction) or the parallel direction (parallel to the effective length direction) of the PTFE capillary.
As for the magnetic field, for example, the distance between the magnetic poles is 45 mm, and the strength of the magnetic field near the center is 0.23 tesla.
A desired characteristic component is obtained by rotating the PTFE capillary tube containing the liquid crystal composition in parallel or perpendicularly to the magnetic field.
Measurements were made at a temperature of 25° C., and both Δε _r and tan δ _iso are unitless.

The Δε _r of the liquid crystal composition according to the present invention at 25° C. is preferably larger, but from the viewpoint of the phase modulation power in the GHz band, it is preferably 0.80 or more, and is 0.80 to 1.50. is preferably 0.85 to 1.45, preferably 0.90 to 1.40, preferably 1.00 to 1.35, preferably 1.10 to 1.30 is preferably
The tan δ _iso at 25° C. of the liquid crystal composition according to the present invention is preferably smaller, but from the viewpoint of loss in the GHz band, it is preferably 0.025 or less, preferably 0.001 to 0.025. preferably 0.003 to 0.023, preferably 0.005 to 0.020, preferably 0.007 to 0.015, preferably 0.008 to 0.013 is preferred, and 0.009 to 0.012 is preferred.

(Liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment and antennas)
A liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition according to the present invention will be described below.

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

A sensor according to the present invention is characterized by using the liquid crystal composition described above. Temperature sensor that uses reflected light wavelength change due to liquid crystal pitch change, Pressure sensor that uses reflected light wavelength change, UV sensor that uses reflected light wavelength change due to composition change, Electric sensor that uses temperature change due to voltage and current, Radiation sensors that use temperature changes that accompany the tracks of radiation particles, ultrasonic sensors that use liquid crystal molecular alignment changes due to mechanical vibration of ultrasonic waves, reflected light wavelength changes due to temperature changes, or liquid crystal molecular alignment changes due to electric fields. An electromagnetic field sensor etc. are mentioned.
The ranging sensor is preferably for LiDAR (Light Detection And Ranging) using a light source.
LiDAR is preferably used for artificial satellites, aircraft, unmanned aircraft (drones), automobiles, railroads, and ships.
As for automobiles, those for automatic driving automobiles are particularly preferable.
The light source is preferably an LED or a laser, preferably a laser.
The light used for LiDAR is preferably infrared light, preferably with a wavelength of 800-2000 nm.
Infrared lasers with a wavelength of 905 nm or 1550 nm are particularly preferred.
A 905 nm infrared laser is preferred when the cost of the photodetector used and sensitivity in all weathers are important, and a 1550 nm infrared laser is preferred when safety regarding human vision is important.
Since the liquid crystal composition according to the present invention exhibits a high Δn, it has a large phase modulation power in the visible light, infrared light, and electromagnetic wave regions, and can provide a sensor with excellent detection sensitivity.

A liquid crystal lens according to the present invention is characterized by using the liquid crystal composition described above. For example, as one aspect thereof, a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the above liquid crystal composition provided between the transparent electrode layer and the second transparent electrode layer; an insulating layer provided between the second transparent electrode layer and the liquid crystal layer; An insulating layer and a high resistance layer provided between the liquid crystal layers.
The liquid crystal lens according to the present invention is used, for example, as a lens for switching between 2D and 3D, a lens for adjusting the focus of a camera, and the like.

An optical communication device according to the present invention is characterized by using the liquid crystal composition described above. An LCOS (Liquid crystal on silicon) having a structure having a two-dimensionally arranged liquid crystal layer can be given.
An optical communication device according to the present invention is used, for example, as a spatial phase modulator.

An antenna according to the present invention is characterized by using the liquid crystal composition described above.
More specifically, the antenna according to the present invention includes: a first substrate having a plurality of slots; a second substrate facing the first substrate and provided with a feeding portion; a first dielectric layer provided between two substrates, a plurality of patch electrodes arranged corresponding to the plurality of slots, a third substrate provided with the patch electrodes, and the first substrate. and a liquid crystal layer provided between the third substrate, wherein the liquid crystal layer contains the liquid crystal composition described above.
As the liquid crystal composition, use a liquid crystal composition containing one or more compounds (including subordinate concepts) represented by the general formula (i) having four ring structures and an isothiocyanate group (-NCS). Due to the high T _ni , large Δn, low V _th , large Δε _r , small tan δ _iso , and good storage stability at low temperatures, it has high reliability against external stimuli such as heat. Antenna can be provided.
This makes it possible to provide an antenna capable of greater phase control with respect to microwave or millimeter wave electromagnetic waves.
The antenna according to the invention preferably operates in the Ka-band frequencies or K-band or Ku-band frequencies used for satellite communications.
The antenna according to the present invention preferably has a configuration in which a radial line slot array and a patch antenna array are combined.
For the structure of the antenna according to the present invention, for example, the matters described in the pamphlet of International Publication No. 2021/157189 can be taken into consideration and applied.

EXAMPLES The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples.
The compositions of the following examples and comparative examples contain each compound in the proportion shown in the table, and the content is described in "% by mass".
In addition, the following abbreviations are used for the description of compounds. A compound that can take a cis-form and a trans-form represents a trans-form unless otherwise specified.
<Ring structure>

<Terminal structure>

（ただし、表中のｎは自然数である。）

(However, n in the table is a natural number.)

<Connection structure>

（ただし、表中のｎは自然数である。）

(However, n in the table is a natural number.)

(Hindered phenolic antioxidant)

(Hindered amine light stabilizer)

(Preparation of liquid crystal composition)
LC-01 to 04 listed in Table 3 were prepared.

(Examples 1 to 21 and Comparative Example 1)
Using LC-01 to 04, hindered phenol antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2), Table 5 to 7 was prepared, the physical properties thereof were measured, and a <storage stability test> was performed. The results are shown in Tables 4-7.
<Storage stability test>
0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruem Co., Ltd.) and defoamed by degassing at 150 to 250 Pa for 10 minutes. It was then purged with dry nitrogen and capped with the provided lid. This was stored for 2 weeks in a temperature-controlled constant temperature bath (manufactured by Espec Co., Ltd., SH-241) at 0° C., and the occurrence of crystallization of the liquid crystal composition was visually confirmed every week.

実施例１～３より、一般式（ｉ）で表される化合物を用いた液晶組成物は、Ｔ_ｎｉが高く、Δｎが大きく、Ｖ_ｔｈが低く、Δε_ｒが大きく、ｔａｎδ_ｉｓｏが小さく、低温での保存性が良好な液晶組成物であった。
一方、比較例１より、一般式（ｉ）で表される化合物を用いなかった液晶組成物は、Δｎが０．３７未満であることが確認された。
更に、実施例４～２１より、ヒンダードフェノール系酸化防止剤やヒンダードアミン系光安定剤を併用した場合においても、Ｔ_ｎｉが高く、Δｎが大きく、Ｖ_ｔｈが低く、Δε_ｒが大きく、ｔａｎδ_ｉｓｏが小さく、低温での保存性が良好であることが確認された。

From Examples 1 to 3, the liquid crystal composition using the compound represented by the general formula (i) had a high T _ni , a large Δn, a low V _th , a large Δε _r , a small tan δ _iso , and a low temperature. It was a liquid crystal composition having good storage stability at room temperature.
On the other hand, from Comparative Example 1, it was confirmed that the liquid crystal composition that did not use the compound represented by general formula (i) had Δn of less than 0.37.
Furthermore, from Examples 4 to 21, even when a hindered phenol-based antioxidant or a hindered amine-based light stabilizer was used in combination, T _ni was high, Δn was large, V _th was low, Δε _r was large, and tan δ _iso It was confirmed that the storage stability at low temperatures was good.

Synthesis of the compound represented by formula (i) is described below.
(Synthesis Example 1) Production of Compound Represented by Formula (I-1)

Under a nitrogen atmosphere at room temperature, 19 g of 4-bromo-2-fluorophenol, 24 g of 4-(4-propylcyclohexyl)phenylboric acid, 20 g of potassium carbonate, 300 mL of tetrahydrofuran, and 40 mL of water were added to a reaction vessel equipped with a reflux tube. , 1 g of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated at 65°C. After completion of the reaction, the reaction mixture was post-treated with water and 10% by mass hydrochloric acid, and then extracted with 200 mL of ethyl acetate. Then, purification was performed by silica gel column chromatography (toluene/ethyl acetate=10/1 to 3/1) to obtain 23 g of the compound represented by formula (1-1-1).
Next, 23 g of the compound represented by formula (I-1-1), 10 g of pyridine, and 150 mL of dichloromethane were added to the reaction vessel at room temperature under a nitrogen atmosphere, and the mixture was cooled to 10° C. or below. Then, 34 g of trifluorotansulfonic anhydride was slowly added dropwise, and after completion of the dropwise addition, reaction was allowed to proceed at room temperature for 2 hours. After completion of the reaction, the organic layer was washed with 10% by mass hydrochloric acid and saturated brine, and the organic layer was concentrated to obtain 28 g of the compound represented by formula (I-1-2).
Next, in a nitrogen atmosphere at room temperature, 10 g of the compound represented by formula (I-1-2) and 5.5 g of the compound represented by formula (I-1-3) were placed in a reaction vessel equipped with a reflux tube. , 9.5 g of potassium phosphate, 80 mL of tetrahydrofuran, and 20 mL of water were added and stirred at room temperature. After completion of the reaction, the reaction mixture was post-treated with water and saturated aqueous ammonium chloride, and then extracted with 100 mL of ethyl acetate. Then, purification was performed by silica gel column chromatography (toluene/ethyl acetate=10/1) to obtain 6.2 g of the compound represented by formula (1-1-4).
Next, in a nitrogen atmosphere at room temperature, 6.2 g of the compound represented by formula (1-1-4), 50 ml of dichloromethane, and 4.5 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel and stirred at room temperature. Agitation was performed. After completion of the reaction, the organic layer was washed with saturated brine, and purified by silica gel column chromatography (dichloromethane) and recrystallization (toluene/hexane=1/2) to give the compound represented by formula (I-1). 4.5 g of a compound of
MS (EI): m/z = 465
(Synthesis Example 2) Production of Compound Represented by Formula (I-2)

Under a nitrogen atmosphere, 21 g of 4-bromo-2,6-difluorophenol, 28 g of 4-(4-propylcyclohexyl)-2-fluorophenylboric acid, 21 g of potassium carbonate, 300 mL of tetrahydrofuran, and 40 mL of water were placed in a reaction vessel equipped with a reflux tube. was added and stirred at room temperature, 1 g of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated at 65°C. After completion of the reaction, the reaction mixture was post-treated with water and 10% by mass hydrochloric acid, and then extracted with 200 mL of ethyl acetate. Then, purification was performed by silica gel column chromatography (toluene/ethyl acetate=10/1 to 3/1) to obtain 27 g of the compound represented by formula (1-2-1).
Next, 27 g of the compound represented by formula (I-2-1), 9 g of pyridine, and 150 mL of dichloromethane were added to the reaction vessel at room temperature under a nitrogen atmosphere, and the mixture was cooled to 10° C. or below. Then, 27 g of trifluorotansulfonic anhydride was slowly added dropwise, and after completion of the dropwise addition, reaction was allowed to proceed at room temperature for 2 hours. After completion of the reaction, the organic layer was washed with 10% by mass hydrochloric acid and saturated brine, and the organic layer was concentrated to obtain 37 g of the compound represented by formula (I-2-2).
Next, in a nitrogen atmosphere at room temperature, 10 g of the compound represented by formula (I-2-2) and 5.5 g of the compound represented by formula (I-2-3) were placed in a reaction vessel equipped with a reflux tube. , 7.5 g of potassium phosphate, 80 mL of tetrahydrofuran, and 20 mL of water were added and stirred at room temperature. After completion of the reaction, the reaction mixture was post-treated with water and saturated aqueous ammonium chloride, and then extracted with 100 mL of ethyl acetate. Then, purification was performed by silica gel column chromatography (toluene/ethyl acetate=2/1) to obtain 6.7 g of the compound represented by formula (1-2-4).
Next, in a nitrogen atmosphere at room temperature, 6.2 g of the compound represented by formula (1-2-4), 50 ml of dichloromethane, and 3.5 g of 1,1-thiocarbonyldiimidazole are added to a reaction vessel and stirred at room temperature. did After completion of the reaction, the organic layer was washed with saturated brine, and purified by silica gel column chromatography (dichloromethane) and recrystallization (toluene/hexane = 1/1) to obtain the compound represented by formula (I-2). 5.5 g of a compound of
MS (EI): m/z = 465
(Synthesis Example 3) Production of Compound Represented by Formula (I-3)

Under a nitrogen atmosphere at room temperature, 13 g of magnesium and 20 ml of tetrahydrofuran were added to a reaction vessel equipped with a reflux tube, and 17 g of the compound represented by formula (I-3-1) was dissolved while being careful of heat generation. 100 mL of tetrahydrofuran was slowly added dropwise. After the dropwise addition was completed, the reaction vessel was heated to 45° C. and reacted for 1 hour. Then, the reactor was cooled to room temperature, and 50 mL of tetrahydrofuran in which 7.8 g of 4-propylcyclohexanone was dissolved was slowly added dropwise. After the dropwise addition was completed, the reaction vessel was heated to 50° C. to complete the reaction. After completion of the reaction, the reaction solution was cooled, 10% by mass hydrochloric acid was added, and the solution was extracted with 150 mL of ethyl acetate. After washing the organic layer with saturated brine, purification was performed by silica gel column chromatography (dichloromethane/ethyl acetate=2/1) to obtain 14.5 g of the compound represented by formula (1-3-2).
Next, 14.5 g of the compound represented by the formula (I-3-2), 8 g of pyridine, and 100 mL of tetrahydrofuran were added to the reaction vessel at room temperature under a nitrogen atmosphere, and the mixture was cooled to 0° C. or below. Then, 15 mL of tetrahydrofuran in which 4.5 g of triphosgene was dissolved was slowly added dropwise. After completion of the reaction, it was washed with water, 10% by mass hydrochloric acid, and saturated brine, and then purified by silica gel column chromatography (dichloromethane/ethyl acetate = 3/1) and dispersion washing (toluene) to obtain formula (1-3- 11 g of the compound represented by 3) was obtained.
Next, 11 g of the compound represented by formula (I-3-3), 4 g of pyridine, and 100 mL of dichloromethane were added to the reaction vessel at room temperature under a nitrogen atmosphere, and the mixture was cooled to 10° C. or below. Then, 12 g of trifluorotansulfonic anhydride was slowly added dropwise, and after completion of the dropwise addition, reaction was allowed to proceed at room temperature for 2 hours. After completion of the reaction, the reaction mixture was washed with 10% by mass hydrochloric acid and saturated brine, and the organic layer was concentrated to obtain 15 g of the compound represented by formula (I-3-4).
Next, in a nitrogen atmosphere at room temperature, 15 g of the compound represented by the formula (I-3-4) and 8.7 g of the compound represented by the formula (I-3-5) were placed in a reaction vessel equipped with a reflux tube. , 7 g of potassium carbonate, 80 mL of tetrahydrofuran, and 20 mL of water were added and stirred at room temperature. After completion of the reaction, the reaction mixture was post-treated with water and saturated aqueous ammonium chloride, and then extracted with 150 mL of ethyl acetate. Then, purification was performed by silica gel column chromatography (toluene/ethyl acetate=10/1) to obtain 12.4 g of the compound represented by formula (1-3-6).
Next, under a nitrogen atmosphere at room temperature, 12.4 g of the compound represented by formula (1-3-4), 100 ml of dichloromethane, and 6.3 g of 1,1-thiocarbonyldiimidazole are added to a reaction vessel and stirred at room temperature. did After completion of the reaction, the organic layer was washed with saturated brine, and purified by silica gel column chromatography (dichloromethane) and recrystallization (toluene/hexane=1/2) to give the compound represented by formula (I-3). 9.5 g of a compound of
MS (EI): m/z = 465
(Synthesis Example 4) Production of Compound Represented by Formula (I-4)

Under a nitrogen atmosphere at room temperature, 30 g of the compound represented by formula (I-4-1), 1 g of p-toluenesulfonic acid, 2-pentyl-1,3- 14 g of diol, 150 mL of toluene were added and heated to reflux for 6 hours. After completion of the reaction, the reaction solution was cooled and extracted with 300 mL of ethyl acetate. After the organic layer was washed with water and saturated brine, the organic layer was concentrated to obtain 28 g of the compound represented by formula (I-4-2).
Next, 28 g of the compound represented by the formula (I-4-2), 200 mL of tetrahydrofuran, 50 mL of ethanol, and 1 g of 5 mass% palladium carbon (hydrous product) were added to a 1 L autoclave, and the mixture was heated at 50°C under hydrogen of 0.4 KPa. and catalytic hydrogen reduction was carried out for 6 hours. After completion of the reaction, palladium carbon was removed by filtration and concentrated to obtain 21 g of the compound represented by formula (I-4-3).
Next, 21 g of the compound represented by formula (I-4-3), 7.5 g of pyridine, and 150 mL of dichloromethane were added to the reaction vessel at room temperature under a nitrogen atmosphere, and the mixture was cooled to 10° C. or below. Then, 21 g of trifluorotansulfonic anhydride was slowly added dropwise, and after completion of the dropwise addition, reaction was allowed to proceed at room temperature for 2 hours. After completion of the reaction, the organic layer was washed with 10% by mass hydrochloric acid and saturated brine, and the organic layer was concentrated to obtain 28 g of the compound represented by formula (I-4-4).
Next, under a nitrogen atmosphere at room temperature, 28 g of the compound represented by the formula (I-4-4), 15.3 g of the compound represented by the formula (I-4-5), and carbonic acid were placed in a reflux tube and a reaction vessel. 12 g of potassium, 200 mL of tetrahydrofuran, and 40 mL of water were added, and the mixture was stirred at room temperature. After completion of the reaction, the reaction mixture was post-treated with water and saturated aqueous ammonium chloride, and then extracted with ethyl acetate. Then, purification was performed by silica gel column chromatography (toluene/ethyl acetate=5/1 to 3/1) to obtain 22 g of the compound represented by formula (1-4-6).
Next, in a nitrogen atmosphere at room temperature, 22 g of the compound represented by formula (1-4-6), 150 ml of dichloromethane, and 14 g of 1,1-thiocarbonyl-di-2(1H)pyridone were added to the reaction vessel. Stirring was performed with After completion of the reaction, the organic layer was washed with saturated brine, and purified by silica gel column chromatography (dichloromethane) and recrystallization (toluene/hexane = 1/1) to obtain the compound represented by formula (I-4). 18 g of the compound of
MS (EI): m/z = 479

The compounds and liquid crystal compositions of the present invention can be used for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices and antennas.

Claims (14)

The following general formula (i)

(in general formula (i),
R ⁱ¹ represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S—, —CO— and/or —CS—;
One or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CO-O-, -O-CO-, -CO-S-, -S-CO-, optionally substituted with -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may each independently be substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms;
one or more hydrogen atoms in A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ may each independently be substituted with a substituent ^Si1 ;
Substituent ^Si1 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S— and/or —CO—;
One or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, - optionally substituted with O—CO—, —CO—S—, —S—CO—, —CO—NH— and/or —NH—CO—,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
When there are multiple substituents ^Si1 , they may be the same or different,
Z ⁱ¹ , Z ⁱ² and Z ⁱ³ each independently represent either a single bond or an alkylene group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkylene group may be independently substituted with —O—, —CF ₂ — and/or —CO—,
One or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, —CH =CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, -C may be substituted with ≡C-, -CO-O- and/or -O-CO-,
Oxygen atoms are never directly bonded to each other. )
A liquid crystal composition containing one or more compounds represented by: The compound represented by the general formula (i) is the following general formula (i-1)

(In the general formula (i-1),
R ⁱ¹ , A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ have the same meanings as R ⁱ¹ , A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ in the general formula (i) above. )
2. The liquid crystal composition according to claim 1, which is selected from the group consisting of compounds represented by: Furthermore, the following general formula (ii)

(In general formula (ii),
R ⁱⁱ¹ each independently represents an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S—, —CO— and/or —CS—;
One or more —CH ₂ —CH ₂ — in the alkyl group are each independently —CH═CH—, —CO—O—, —O—CO—, —CO—S—, optionally substituted with -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-;
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may each independently be substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
A ⁱⁱ¹ and A ⁱⁱ² are each independently the following group (a), group (b), group (c) and group (d):
(a) a 1,4-cyclohexylene group (one —CH ₂ — or two or more non-adjacent —CH ₂ — present in this group may be replaced with —O— and/or —S—; good.)
(b) a 1,4-phenylene group (one -CH= or two or more -CH= present in this group may be replaced with -N=);
(c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6- diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,4-diyl group, 2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group, one -CH= or two or more -CH= may be replaced with -N=.)
(d) thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl thieno[3,2-b]thiophene-2,5-diyl group, benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group (the 1 One -CH= or two or more -CH= may be replaced with -N=.)
represents a group selected from the group consisting of
one or more hydrogen atoms in A ⁱⁱ¹ and A ⁱⁱ² may each independently be substituted with a substituent S ⁱⁱ¹ ;
Substituent S ⁱⁱ¹ is a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, represents either a dimethylsilyl group, a thioisocyano group or an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S—, —CO— and/or —CS—;
One or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CO-O-, -O-CO-, -CO-S-, -S-CO-, optionally substituted with -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may each independently be substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
When there are multiple substituents S ⁱⁱ¹ , they may be the same or different,
Z ⁱⁱ¹ represents either a single bond or an alkylene group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkylene group may each independently be substituted with —O—,
One or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, —CH =CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, -C optionally substituted with ≡C-, -CO-O- and/or -O-CO-,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may each independently be substituted with —O—CO—O—,
There is no direct bond between oxygen atoms and oxygen atoms,
n ⁱⁱ¹ represents an integer from 1 to 4,
When there are multiple ^Aii1 and ^Zii1 , they may be the same or different.
However, compounds represented by general formula (i) are excluded. )
3. The liquid crystal composition according to claim 1, which contains one or more compounds represented by: The compound represented by the general formula (ii) is represented by the following general formulas (ii-1) to (ii-6)

(In the general formulas (ii-1) to (ii-6),
R ⁱⁱ¹ , A ⁱⁱ¹ and A ⁱⁱ² have the same meanings as R ⁱⁱ¹ , A ⁱⁱ¹ and A ⁱⁱ² in general formula (ii) above,
In general formulas (ii-3) to (ii-6), the definition of A ^ii1-2 is the same as the definition of A ⁱⁱ¹ in general formula (ii) above. )
4. The liquid crystal composition according to claim 3, which is selected from the group consisting of compounds represented by: 5. The liquid crystal composition according to claim 1, wherein Δn at 25° C. and 589 nm is 0.37 or more. A liquid crystal display device using the liquid crystal composition according to any one of claims 1 to 5. 7. The liquid crystal display element according to claim 6, driven by an active matrix system or a passive matrix system. 6. A liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition according to claim 1. A sensor using the liquid crystal composition according to any one of claims 1 to 5. A liquid crystal lens using the liquid crystal composition according to any one of claims 1 to 5. An optical communication device using the liquid crystal composition according to any one of claims 1 to 5. An antenna using the liquid crystal composition according to any one of claims 1 to 5. 13. An antenna according to claim 12,
a first substrate with a plurality of slots;
a second substrate facing the first substrate and provided with a power feeding portion;
a first dielectric layer provided between the first substrate and the second substrate;
a plurality of patch electrodes arranged corresponding to the plurality of slots;
a third substrate provided with the patch electrode;
a liquid crystal layer provided between the first substrate and the third substrate;
An antenna, wherein the liquid crystal layer contains the liquid crystal composition according to any one of claims 1 to 9. The following general formula (i)

(in general formula (i),
R ⁱ¹ represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S—, —CO— and/or —CS—;
One or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CO-O-, -O-CO-, -CO-S-, -S-CO-, optionally substituted with -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and/or -C≡C-,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may each independently be substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms;
one or more hydrogen atoms in A ⁱ¹ , A ⁱ² , A ⁱ³ and A ⁱ⁴ may each independently be substituted with a substituent ^Si1 ;
Substituent ^Si1 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkyl group may be independently substituted with —O—, —S— and/or —CO—;
One or more -CH ₂ -CH ₂ - in the alkyl group are each independently -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, - optionally substituted with O—CO—, —CO—S—, —S—CO—, —CO—NH— and/or —NH—CO—,
one or more —CH ₂ —CH ₂ —CH ₂ — in the alkyl group may be independently substituted with —O—CO—O—,
One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,
There is no direct bond between oxygen atoms and oxygen atoms,
When there are multiple substituents ^Si1 , they may be the same or different,
Z ⁱ¹ , Z ⁱ² and Z ⁱ³ each independently represent either a single bond or an alkylene group having 1 to 20 carbon atoms,
one or more —CH ₂ — in the alkylene group may be independently substituted with —O—, —CF ₂ — and/or —CO—,
One or more —CH ₂ —CH ₂ — in the alkylene group are each independently —CH ₂ —CH(CH ₃ )—, —CH(CH ₃ )—CH ₂ —, —CH =CH-, -CF=CF-, -CH=C(CH ₃ )-, -C(CH ₃ )=CH-, -CH=N-, -N=CH-, -N=N-, -C may be substituted with ≡C-, -CO-O- and/or -O-CO-,
Oxygen atoms are never directly bonded to each other. )
A compound represented by