WO2021193708A1

WO2021193708A1 - Compound, liquid crystal composition, and liquid crystal display element

Info

Publication number: WO2021193708A1
Application number: PCT/JP2021/012218
Authority: WO
Inventors: 稲垣　順一; 木村　敬二; 道子高橋; 秀典相原; 林　和史
Original assignee: Jnc株式会社; Jnc石油化学株式会社; 公益財団法人相模中央化学研究所
Priority date: 2020-03-25
Filing date: 2021-03-24
Publication date: 2021-09-30
Also published as: TW202142678A; JPWO2021193708A1; CN114787130A

Abstract

This compound is represented by formula (1). R¹ and R² are each C1-C15 alkyl or the like; R^a is hydrogen or the like; a ring A¹ and a ring A² are each 1,4-cyclohexylene, 1,4-phenylene, or the like; a ring N¹ and a ring N² are each 1,2-cyclopropylene, 1,3-cyclopentylene, or the like; Z¹, Z², Z³, and Z⁴ are each a single bond or the like; L¹, L², L³, L⁴, L⁵, and L⁶ are each fluorine or the like; and l and o are each 0 or 1 and m and n are each 0, 1, or 2.

Description

Compounds, liquid crystal compositions and liquid crystal display devices

The present invention relates to a liquid crystal compound having a carbazole ring, a liquid crystal composition, and a liquid crystal display element. More specifically, the present invention relates to a liquid crystal compound having a carbazole ring and having a negative dielectric anisotropy, a liquid crystal composition containing the same, and a liquid crystal display element containing the composition.

In the liquid crystal display element, the classification based on the operation mode of the liquid crystal molecule is PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS. (In-plane switching), VA (vertical alignment), FFS (fringe field switching), FPA (field-induced photo-reactive alignment) and other modes. The classifications based on the drive method of the element are PM (passive matrix) and AM (active matrix). PM is classified into static, multiplex, etc., and AM is classified into TFT (thin film transistor), MIM (metal insulator metal), and the like.

A liquid crystal composition is enclosed in this element. The physical characteristics of this composition are related to the properties of the device. Examples of physical properties in the composition are stability to heat and light, temperature range of nematic phase, viscosity, optical anisotropy, dielectric anisotropy, specific resistance, elastic constant and the like. The composition is prepared by mixing many liquid crystal compounds. The physical characteristics required for the compound are high stability to the environment such as water, air, heat and light, wide temperature range of liquid crystal phase, small viscosity, appropriate optical anisotropy, large dielectric anisotropy, appropriate elastic constant. , Good compatibility with other liquid crystal compounds, etc. Compounds with a high upper temperature limit of the nematic phase are preferred. Compounds having a low lower limit temperature in the liquid crystal phase such as the nematic phase and the smectic phase are preferable. Compounds with low viscosities contribute to the short response time of the device. The appropriate value of optical anisotropy depends on the type of operating mode of the device. In order to drive the device at a low voltage, a compound having a large positive or negative dielectric anisotropy is preferable. In order to prepare the composition, a compound having good compatibility with other liquid crystal compounds is preferable. Since the device may be used at a temperature below freezing, a compound having good compatibility at a low temperature is preferable.

So far, many liquid crystal compounds have been synthesized. Development of new liquid crystal compounds is still ongoing. This is because new compounds are expected to have good physical properties that conventional compounds do not have. This is because the novel compound may impart an appropriate balance to at least two physical characteristics in the composition. There are few reports on compounds having the following divalent groups. In the following divalent groups, X is hydrogen or a substituent.

For example, Patent Document 1 discloses compounds having numbers 53, 54, and 56 in Table 4 on page 41, and compounds having numbers 125 and 127 in Table 8 on page 45.

Patent Document 2 discloses the II-a compound of Example 3 on page 10, and the III-a compound of Example 7 on page 14.

International Publication No. 2007/018168 International Publication No. 2017/084231

The first challenge is high stability to heat and light, high transparency (or high upper limit temperature of nematic phase), lower lower limit temperature of liquid crystal phase, small viscosity, proper optical anisotropy, negatively large dielectric constant difference. It is an object of the present invention to provide a liquid crystal compound that satisfies at least one of physical characteristics such as anisotropy, an appropriate elastic constant, and good compatibility with other liquid crystal compounds. It is to provide a compound having a negatively large dielectric anisotropy as compared with a similar compound. The second challenge is that it contains this compound and has high stability to heat and light, high upper limit temperature of nematic phase, lower lower limit temperature of nematic phase, small viscosity, proper optical anisotropy, negatively large dielectric constant difference. It is an object of the present invention to provide a liquid crystal composition that satisfies at least one of physical characteristics such as anisotropy, a large specific resistance, and an appropriate elastic constant. The challenge is to provide a liquid crystal composition having an appropriate balance with respect to at least two physical characteristics. A third challenge is a liquid crystal display that contains this composition and has a wide temperature range in which the device can be used, a short response time, a large voltage retention rate, a low threshold voltage, a large contrast ratio, a small flicker rate, and a long life. It is to provide an element.

The present invention relates to a compound represented by the formula (1), a liquid crystal composition containing this compound, and a liquid crystal display element containing this liquid crystal composition.

In equation (1)
R ¹ is alkyl hydrogen, or from 1 to 15 carbon atoms, in the ^{R 1,} at least one of -CH ₂ -, -O -, - may be replaced by S-, or -CO-, At least _{one- (CH 2} ) _2- may be replaced by -CH = CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine;
R ² is hydrogen, fluorine, chlorine, -C≡N, alkyl of -C≡C-C≡N or 1 to 15 carbon atoms, in the ^{R 2,} at least one of -CH ₂ -, - It may be replaced by O-, -S-, or -CO-, and at least one- (CH ₂ ) _2- may be replaced by -CH = CH- or -C≡C-, at least 1 One hydrogen may be replaced with fluorine or chlorine;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A ¹ and A ² are independently cycloalkylenes having 3 to 5 carbon atoms, and in the rings A ¹ and A ² , at least one -CH _2- can be replaced with -O-. Often, at least _{one-(CH 2} ) _2- may be replaced by -CH = CH-;
Rings N ¹ and N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , Dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2, 5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, benzo [b] b] thiophene-2,6-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, a 9H- xanthene-2,6-diyl or 9H- fluoren-2,7-diyl, the ring ^{N 1} And in ring N ² , at least one hydrogen is replaced by fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH _{2 F.} May;
Z ¹ , Z ² , Z ³ , and Z ⁴ are independently single-bonded or alkylenes with 1 to 6 carbon atoms, and in this Z ¹ , Z ² , Z ³ , and Z ⁴ , at least one -CH. ₂ -may be replaced by -O-, -S-, or -CO-, and at least one- (CH ₂ ) ₂ -is replaced by -CH = CH- or -C≡C-. Also, at least one hydrogen may be replaced with fluorine or chlorine;
L ¹ , L ² , L ³ , L ⁴ , L ⁵ , and L ⁶ independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , It is -OCH ₂ F, or -C≡N,;
When both L ⁵ and L ⁶ are hydrogen, ^{at least one of L 1} , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF _2, be -OCH ₂ F, or -C≡N,;
When L ¹ , L ² , L ³ , and L ⁴ are all hydrogen, ^{at least one of L 5} and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF _2, be -OCH ₂ F, or -C≡N,;
l and o are independently 0, or 1, m and n are independently 0, 1, or 2, and the sum of l, m, n, and o is an integer from 0 to 4. can be;
When l is 0, R ¹ does not become hydrogen, and when o is 0, R ^{2 does not become hydrogen.}

The first advantages are high stability to heat and light, high transparency (or high upper limit temperature of nematic phase), lower lower limit temperature of liquid crystal phase, low viscosity, proper optical anisotropy, negatively large dielectric constant difference. It is an object of the present invention to provide a liquid crystal compound that satisfies at least one of physical characteristics such as anisotropy, an appropriate elastic constant, and good compatibility with other liquid crystal compounds. It is to provide a compound having a negatively large dielectric anisotropy as compared with a similar compound. The second advantage is that it contains this compound and has high stability to heat and light, high upper limit temperature of nematic phase, lower lower limit temperature of nematic phase, small viscosity, proper optical anisotropy, negatively large dielectric constant difference. It is an object of the present invention to provide a liquid crystal composition that satisfies at least one of physical characteristics such as anisotropy, a large specific resistance, and an appropriate elastic constant. This advantage is to provide a liquid crystal composition having an appropriate balance with respect to at least two physical characteristics. The third advantage is that the liquid crystal display contains this composition and has a wide temperature range in which the device can be used, a short response time, a large voltage retention rate, a low threshold voltage, a large contrast ratio, a small flicker rate, and a long life. It is to provide an element.

The usage of terms in this specification is as follows. The terms "liquid crystal compound", "liquid crystal composition", and "liquid crystal display element" may be abbreviated as "compound", "composition", and "element", respectively. The "liquid crystal compound" is a compound having a liquid crystal phase such as a nematic phase or a smectic phase, and a compound having no liquid crystal phase but adjusting the physical properties of a composition such as an upper limit temperature, a lower limit temperature, a viscosity, and a dielectric constant anisotropy. It is a general term for compounds added for the purpose of This compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and its molecular structure is rod-like. "Liquid crystal display element" is a general term for a liquid crystal display panel and a liquid crystal display module. The "polymerizable compound" is a compound added for the purpose of forming a polymer in the composition. Liquid crystal compounds with alkenyl are not polymerizable in that sense.

The liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. Additives are added to this composition for the purpose of further adjusting the physical characteristics. Additives such as polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, UV absorbers, light stabilizers, heat stabilizers, dyes, and defoamers are added as needed. NS. The liquid crystal compounds and additives are mixed in such a procedure. The ratio (content) of the liquid crystal compound is expressed as a weight percentage (% by weight) based on the weight of the liquid crystal composition containing no additive even when the additive is added. The ratio (addition amount) of the additive is expressed as a weight percentage (% by weight) based on the weight of the liquid crystal composition containing no additive. That is, the ratio of the liquid crystal compound or the additive is calculated based on the total weight of the liquid crystal compound. Parts per million by weight (ppm) may also be used. The proportions of polymerization initiators and polymerization inhibitors are exceptionally expressed based on the weight of the polymerizable compound.

The "transparency point" is the transition temperature between the liquid crystal phase and the isotropic phase in the liquid crystal compound. The "lower limit temperature of the liquid crystal phase" is the transition temperature of the solid-liquid crystal phase (smetic phase, nematic phase, etc.) in the liquid crystal compound. The "upper limit temperature of the nematic phase" is the transition temperature of the nematic phase-isotropic phase in the mixture of the liquid crystal compound and the mother liquid crystal or the liquid crystal composition, and may be abbreviated as the "upper limit temperature". The "lower limit temperature of the nematic phase" may be abbreviated as the "lower limit temperature". The expression "increase the dielectric anisotropy" means that when the composition has a positive dielectric anisotropy, its value increases positively, and the composition has a negative dielectric anisotropy. When it is a thing, it means that its value increases negatively. "Large voltage retention" means that the element has a large voltage retention not only at room temperature but also at a temperature close to the upper limit temperature at the initial stage, and after long-term use, it has a large voltage not only at room temperature but also at a temperature close to the upper limit temperature. It means having a retention rate. The characteristics of the composition or device may be examined before and after the aging test (including the accelerated deterioration test).

The compound represented by the formula (1) may be abbreviated as the compound (1). At least one compound selected from the group of compounds represented by the formula (1) may be abbreviated as the compound (1). "Compound (1)" means one compound represented by the formula (1), a mixture of two compounds, or a mixture of three or more compounds. These rules also apply to compounds represented by other formulas. In equations (1) to (15), symbols such as ^{A 1} , B ¹ , and C ¹ enclosed in hexagons correspond to rings such as ^{ring A 1} , ring B ¹ , and ring C ^{1, respectively.} The hexagon represents a six-membered ring such as cyclohexane or benzene. The hexagon may represent a fused ring such as naphthalene or a crosslinked ring such as adamantane.

In the chemical formulas of the component compounds, with symbols of terminal groups R ¹¹ to a plurality of compounds. In these compounds, two groups represented by any two R ¹¹ may be may be the same or different. For example, there are cases where ^{R 11 of} compound (2) ^{is ethyl and R 11} of compound (3) is ethyl. ^{In some cases, R 11 of} compound (2) ^{is ethyl and R 11} of compound (3) is propyl. This rule also applies to symbols such as ^{R 12} , R ¹³ , and Z ^11. In the compound (15), when i is 2, two rings ^{E 1} is present. The two two wherein the ring E ¹ represents the compound may be the same or different. When i is greater than 2, also apply to any two rings E ^1. This rule also applies to other symbols.

The expression "at least one'A'" means that the number of'A's is arbitrary. The expression "at least one'A'may be replaced by'B'" is that when the number of'A's is 1, the position of the'A'is arbitrary and the number of'A's is 2. When more than one, it means that their positions can be selected without limitation. This rule also applies to the expression "at least one'A' has been replaced by a'B'". The expression "at least one'A' may be replaced by'B','C',or'D'" is any'if any'A' is replaced by a'B'. If A'is replaced by'C', and any'A' is replaced by'D', then more than one'A'is'B','C', and / or'D' It means to include the case where it is replaced by at least two. For example, " _{alkyl in which at least one -CH 2-} may be replaced with -O- or -CH = CH-" includes alkyl, alkoxy, alkoxyalkyl, alkoxy, alkoxyalkenyl, alkenyloxyalkyl. It is not preferable that two consecutive -CH _2- are replaced with -O- to become -O-O-. Alkyl such as in, -CH ₂ methyl moiety _(-CH 2 -H) - by is replaced by -O- is not preferred also be the -O-H.

"R ¹¹ and R ¹² are independently alkyls with 1 to 10 carbons or alkenyl with 2 to 10 carbons, in which at least one -CH _2- is replaced with -O-. Often, in these groups, at least one hydrogen may be replaced by fluorine. " In this expression, "in these groups" may be interpreted literally. In this expression, "these groups" means alkyl, alkenyl, alkoxy, alkenyloxy and the like. That is, "these groups" refers to all of the groups described prior to the term "in these groups". This common-sense interpretation also applies to the terms "in these monovalent groups" and "in these divalent groups". For example, "these monovalent groups" refers to all of the groups described prior to the term "in these monovalent groups".

Halogen means fluorine, chlorine, bromine, and iodine. Preferred halogens are fluorine and chlorine. A more preferred halogen is fluorine. The alkyl of the liquid crystal compound is linear or branched and does not contain cyclic alkyl. Linear alkyl is generally preferred over branched alkyl. The same applies to terminal groups such as alkoxy and alkenyl. The configuration for 1,4-cyclohexylene is preferably trans over cis in order to raise the upper temperature limit. 2-Fluoro-1,4-phenylene means the following two divalent groups. In the chemical formula, fluorine may be left-facing (L) or right-facing (R). This rule also applies to asymmetric divalent groups generated by removing two hydrogens from the ring, such as tetrahydropyran-2,5-diyl.

The present invention includes the following items.

Item 1. A compound represented by the formula (1).

In equation (1)
R ¹ is alkyl hydrogen, or from 1 to 15 carbon atoms, in the ^{R 1,} at least one of -CH ₂ -, -O -, - may be replaced by S-, or -CO-, At least _{one- (CH 2} ) _2- may be replaced by -CH = CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine;
R ² is hydrogen, fluorine, chlorine, -C≡N, alkyl of -C≡C-C≡N or 1 to 15 carbon atoms, in the ^{R 2,} at least one of -CH ₂ -, - It may be replaced by O-, -S-, or -CO-, and at least one- (CH ₂ ) _2- may be replaced by -CH = CH- or -C≡C-, at least 1 One hydrogen may be replaced with fluorine or chlorine;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A ¹ and A ² are independently cycloalkylenes having 3 to 5 carbon atoms, and in the rings A ¹ and A ² , at least one -CH _2- can be replaced with -O-. Often, at least _{one-(CH 2} ) _2- may be replaced by -CH = CH-;
Rings N ¹ and N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , Dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl,
Fran-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5- Diyl, benzo [b] thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl, or 9H-fluorene-2,7-diyl. In the rings N ¹ and N ² , at least one hydrogen is fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH _2. May be replaced by F;
Z ¹ , Z ² , Z ³ , and Z ⁴ are independently single-bonded or alkylenes with 1 to 6 carbon atoms, and in this Z ¹ , Z ² , Z ³ , and Z ⁴ , at least one -CH. ₂ -may be replaced by -O-, -S-, or -CO-, and at least one- (CH ₂ ) ₂ -is replaced by -CH = CH- or -C≡C-. Also, at least one hydrogen may be replaced with fluorine or chlorine;
L ¹ , L ² , L ³ , L ⁴ , L ⁵ , and L ⁶ independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , It is -OCH ₂ F, or -C≡N,;
When both L ⁵ and L ⁶ are hydrogen, ^{at least one of L 1} , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF _2, be -OCH ₂ F, or -C≡N,;
When L ¹ , L ² , L ³ , and L ⁴ are all hydrogen, ^{at least one of L 5} and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF _2, be -OCH ₂ F, or -C≡N,;
l and o are independently 0, or 1, m and n are independently 0, 1, or 2, and the sum of l, m, n, and o is an integer from 0 to 4. can be;
When l is 0, R ¹ does not become hydrogen, and when o is 0, R ^{2 does not become hydrogen.}

Item 2. Item 2. The compound according to Item 1, represented by the formulas (1-1) to (1-13).

In equations (1-1) to (1-13),
R ¹ is hydrogen, an alkyl having 1 to 15 carbon atoms, an alkoxy having 1 to 14 carbon atoms, an alkoxy alkyl having 2 to 14 carbon atoms, an alkenyl having 2 to 15 carbon atoms, or an alkenyloxy having 2 to 14 carbon atoms. ;
R ² is hydrogen, fluorine, _chlorine, -CF 3, -OCF _3, -C≡N, alkyl of from 1 to 15 carbon atoms, alkoxy having 1 to 14 carbon atoms, from 2 to 14 carbon atoms in the alkoxyalkyl, carbon atoms 2 to 15 alkenyl, or 2 to 14 carbon alkenyloxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A ¹ and A ² are independently cycloalkylenes having 3 to 5 carbon atoms, and in the rings A ¹ and A ² , at least one -CH _2- can be replaced with -O-. Often, at least _{one-(CH 2} ) _2- may be replaced by -CH = CH-;
Rings N ¹ and N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , Dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2, 5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, benzo [b] b] thiophene-2,6-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, a 9H- xanthene-2,6-diyl or 9H- fluoren-2,7-diyl, the ring ^{N 1} And in ring N ² , at least one hydrogen is replaced by fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH _{2 F.} May;
Z ¹ , Z ² , Z ³ , and Z ⁴ are independently single-bonded or alkylenes with 1 to 6 carbon atoms, and in this Z ¹ , Z ² , Z ³ , and Z ⁴ , at least one -CH. ₂ -may be replaced by -O-, -S-, or -CO-, and at least one- (CH ₂ ) ₂ -is replaced by -CH = CH- or -C≡C-. Also, at least one hydrogen may be replaced with fluorine or chlorine;
L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C ≡ N, and at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ _{, -OCHF 2} , It is -OCH ₂ F, or -C≡N,;
In the formula (1-1), the formula (1-3), the formula (1-5), the formula (1-7), the formula (1-9), the formula (1-11), and the formula (1-13). , R ¹ does not become hydrogen, and formulas (1-1) to (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1). In -13), R ² does not become hydrogen.

Item 3. In the formulas (1-1) to (1-13),
R ¹ and R ² are independently from hydrogen, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or from 2 carbons. 9 alkenyloxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A ¹ and A ² are independently 1,2-cyclopropylene, 1,3-cyclobutylene, or 1,3-cyclopentylene;
Rings N ¹ and N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4- Diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, or benzo [b] thiophene-2,6-diyl In the rings N ¹ and N ² , at least one hydrogen is fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or. It may be replaced by -OCH ₂ F;
Z ¹ , Z ² , Z ³ , and Z ⁴ are independently single-bonded, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-,- _{_{_{OCF 2 -, - (CH 2}}} ) 2 -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF -, - C≡C -, - (CH 2) 4 -, -(CH ₂ ) ₂ COO-,-(CH ₂ ) ₂ OCO-, -OCO (CH ₂ ) _2- , -COO (CH ₂ ) ₂ -,-(CH ₂ ) ₂ CF ₂ O-,-(CH 2) ₂ ) ₂ OCF _2- , -OCF ₂ (CH ₂ ) _2- , -CF ₂ O (CH ₂ ) ₂ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH -(CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH-, -CH = CH-CH ₂ O-, or -OCH _{2-CH = CH-;}
L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, or -C ≡ N, and at least one of L ¹ , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ _{, -OCHF 2} , It is -OCH ₂ F, or -C≡N,;
In the formula (1-1), the formula (1-3), the formula (1-5), the formula (1-7), the formula (1-9), the formula (1-11), and the formula (1-13). , R ¹ does not become hydrogen, and formulas (1-1) to (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1). Item 2. The compound according to Item 2, wherein ^{R 2} does not become hydrogen in -13).

Item 4. Item 2. The compound according to Item 1, which is represented by the formulas (1-14) to (1-26).

In equations (1-14) to (1-26),
R ¹ is hydrogen, an alkyl having 1 to 15 carbon atoms, an alkoxy having 1 to 14 carbon atoms, an alkoxy alkyl having 2 to 14 carbon atoms, an alkenyl having 2 to 15 carbon atoms, or an alkenyloxy having 2 to 14 carbon atoms. ;
R ² is hydrogen, fluorine, _chlorine, -CF 3, -OCF _3, -C≡N, alkyl of from 1 to 15 carbon atoms, alkoxy having 1 to 14 carbon atoms, from 2 to 14 carbon atoms in the alkoxyalkyl, carbon atoms 2 to 15 alkenyl, or 2 to 14 carbon alkenyloxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A ¹ and A ² are independently cycloalkylenes having 3 to 5 carbon atoms, and in the rings A ¹ and A ² , at least one -CH _2- can be replaced with -O-. Often, at least _{one-(CH 2} ) _2- may be replaced by -CH = CH-;
Rings N ¹ and N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , Dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2, 5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, benzo [b] b] thiophene-2,6-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, a 9H- xanthene-2,6-diyl or 9H- fluoren-2,7-diyl, the ring ^{N 1} And in ring N ² , at least one hydrogen is replaced by fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH _{2 F.} May;
Z ¹ , Z ² , Z ³ , and Z ⁴ are independently single-bonded or alkylenes with 1 to 6 carbon atoms, and in this Z ¹ , Z ² , Z ³ , and Z ⁴ , at least one -CH. _2- May be replaced by -O-, -S-, or -CO-, and at least one- (CH ₂ ) ₂ -may be replaced by -CH = CH- or -C≡C-. Often, at least one hydrogen may be replaced with fluorine or chlorine;
L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ _{, -OCHF 2} , -OCH ₂ F, or -C ≡ N. At ^{least one of L 5} and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ _{, -OCHF 2} , -OCH ₂ F, or -C ≡ N;
In formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26). , R ¹ does not become hydrogen, and formulas (1-14) to (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1). In -26), R ² does not become hydrogen.

Item 5. In the formulas (1-14) to (1-26),
R ¹ and R ² are independently from hydrogen, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or from 2 carbons. 9 alkenyloxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A ¹ and A ² are independently 1,2-cyclopropylene, 1,3-cyclobutylene, or 1,3-cyclopentylene;
Rings N ¹ and N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4- Diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, or benzo [b] thiophene-2,6-diyl In the rings N ¹ and N ² , at least one hydrogen is fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or. It may be replaced by -OCH ₂ F;
Z ¹ , Z ² , Z ³ , and Z ⁴ are independently single-bonded, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-,- _{_{_{OCF 2 -, - (CH 2}}} ) 2 -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF -, - C≡C -, - (CH 2) 4 -, -(CH ₂ ) ₂ COO-,-(CH ₂ ) ₂ OCO-, -OCO (CH ₂ ) _2- , -COO (CH ₂ ) ₂ -,-(CH ₂ ) ₂ CF ₂ O-,-(CH 2) ₂ ) ₂ OCF _2- , -OCF ₂ (CH ₂ ) _2- , -CF ₂ O (CH ₂ ) ₂ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH -(CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH-, -CH = CH-CH ₂ O-, or -OCH _{2-CH = CH-;}
L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ _{, -OCHF 2} , -OCH ₂ F, or -C ≡ N. At ^{least one of L 5} and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ ,
-OCHF ₂ , -OCH ₂ F, or -C≡N;
In formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26). , R ¹ does not become hydrogen, and formulas (1-14) to (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1). Item 4. The compound according to Item 4, wherein ^{R 2} does not become hydrogen in −26).

Item 6. Formula (1-1-1), formula (1-3-1) to formula (1-3-6), formula (1-5-1) to formula (1-5-4), or formula (1-5-1) The compound according to any one of Items 1 to 3, represented by the formulas (1-9-3) from 9-1).

Equations (1-1-1), equations (1-3-1) to equations (1-3-6), equations (1-5-1) to equations (1-5-4), and equations (1-5-1). In equations (1-9-3) from 9-1)
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z ² and Z ³ are independently single-bonded, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-(CH). ₂ ) _2- , -CH = CH-, -C≡C-,-(CH ₂ ) ₄ -,-(CH ₂ ) ₂ COO-,-(CH ₂ ) ₂ OCO-, -OCO (CH ₂ ) ₂ -, -COO (CH ₂ ) ₂ -,-(CH ₂ ) ₂ CF ₂ O-,-(CH ₂ ) ₂ OCF _2- , -OCF ₂ (CH ₂ ) _2- , -CF ₂ O (CH ₂ ) ₂ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH-, -CH = CH- CH ₂ O- or -OCH _2- CH = CH-;
L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F, and L ¹ , At ^{least one of L 2} , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F;
X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 7. Formulas (1-1-1), formulas (1-3-1) to formulas (1-3-6), formulas (1-5-1) to formulas (1-5-4), formulas (1-5-1) In equations (1-9-3) from 9-1)
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 10 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z ² and Z ³ are independently single-bonded, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-(CH ₂ ) _2- , -CH = CH-,-(CH ₂ ) ₄ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH-, -CH = CH-CH ₂ O-, or -OCH _{2-CH = CH-;}
L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ or -OCF ₃ , and at least one of ^{L 1} , L ² , L ³ , and L ^4. Is fluorine, chlorine, -CF ₃ or -OCF ₃ , and at least two of ^{L 1} , L ² , L ³ and L ^{4 are hydrogen;}
Item 6. The compound according to Item 6, wherein X ¹ and X ^{2 are independently hydrogen, fluorine, or chlorine.}

Item 8. Formulas (1-14-1), formulas (1-16-1) to formulas (1-16-6), formulas (1-18-1) to formulas (1-18-4), or formulas (1-18-1). The compound according to any one of Items 1, 4, and 5, represented by the formulas (1-22-3) from 22-1).

Equations (1-14-1), equations (1-16-1) to equations (1-16-6), equations (1-18-1) to equations (1-18-4), and equations (1-18-1). From 22-1) to equation (1-22-3),
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z ² and Z ³ are independently single-bonded, -O-, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-(CH). ₂ ) _2- , -CH = CH-, -C≡C-,-(CH ₂ ) ₄ -,-(CH ₂ ) ₂ COO-,-(CH ₂ ) ₂ OCO-, -OCO (CH ₂ ) ₂ -, -COO (CH ₂ ) ₂ -,-(CH ₂ ) ₂ CF ₂ O-,-(CH ₂ ) ₂ OCF _2- , -OCF ₂ (CH ₂ ) _2- , -CF ₂ O (CH ₂ ) ₂ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH-, -CH = CH- CH ₂ O- or -OCH _2- CH = CH-;
L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F, and at least one of ^{L 5} and L ^{6 is} , Fluorine, Chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F;
X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 9. Formulas (1-14-1), formulas (1-16-1) to formulas (1-16-6), formulas (1-18-1) to formulas (1-18-4), and formulas (1). From -22-1) to equation (1-22-3),
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z ² and Z ³ are independently single-bonded, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-(CH ₂ ) _2- , -CH = CH-,-(CH ₂ ) ₄ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH-, -CH = CH-CH ₂ O-, or -OCH _{2-CH = CH-;}
L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F, and at least one of ^{L 5} and L ^{6 is} , Fluorine, Chlorine, -CF ₃ , -CHF ₂ , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F;
Item 8. The compound according to Item 8, wherein X ¹ and X ^{2 are independently hydrogen, fluorine, or chlorine.}

Item 10. Item 6. The compound according to any one of Items 1 to 3, 6 and 7, represented by the formula (1-1-1) or the formulas (1-3-1) to (1-3-6).

In the formula (1-1-1), and from the formula (1-3-1) to the formula (1-3-6),
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
Z ² is a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-(CH ₂ ) _2- , -CH = CH- ,-(CH ₂ ) ₄ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH- , -CH = CH-CH ₂ O-, or -OCH _2- CH = CH-;
L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, chlorine, -CF ₃ , or -OCF ₃ , and at least one of ^{L 1} , L ² , L ³ , and L ^4. Is fluorine, chlorine, -CF ₃ , or -OCF ₃ , and at least two of ^{L 1} , L ² , L ³ , and L ^{4 are hydrogen;}
X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 11. Item 2. The item 1, 4, 5, 8 and 9, which is represented by the formula (1-14-1) or the formula (1-16-1) to the formula (1-16-6). Compound.

In equations (1-14-1), and from equations (1-16-1) to equations (1-16-6),
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
Z ² is a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-(CH ₂ ) _2- , -CH = CH- ,-(CH ₂ ) ₄ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH- , -CH = CH-CH ₂ O-, or -OCH _2- CH = CH-;
L ⁵ and L ⁶ are independently hydrogen, fluorine, chlorine, -CF ₃ or -OCF ₃ , and ^{at least one of L 5} and L ⁶ is fluorine, chlorine, -CF ₃ or -OCF ₃ Is;
X ¹ and X ² are independently hydrogen, fluorine, or chlorine.

Item 12. From Eqs. (1-1-1), Eqs. (1-3-1-1) to Eqs. (1-3-1-7), Eqs. (1-3-2-1), Eqs. (1-3-2- 2), Eq. (1-3-3-1), Eq. (1-3-3-2), Eq. (1-3-4-1), Eq. (1-3-4-2), Eq. (1) Items 1 to 3 represented by -3-5-1), Eq. (1-3-5-2), or Eqs. (1-3-6-1) to Eqs. (1-3-6-4). , 6, 7, and 10.

From Eqs. (1-1-1), Eqs. (1-3-1-1) to Eqs. (1-3-1-7), Eqs. (1-3-2-1), Eqs. (1-3-2- 2), Eq. (1-3-3-1), Eq. (1-3-3-2), Eq. (1-3-4-1), Eq. (1-3-4-2), Eq. (1) In the formulas (-3-5-1), formula (1-3-5-2), and formulas (1-3-6-1) to formulas (1-3-6-4),
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
L ¹ , L ² , L ³ , and L ⁴ are independently hydrogen, fluorine, -CF ₃ , or -OCF ₃ , and at least two of ^{L 1} , L ² , L ³ , and L ^{4 are} , Fluorine, -CF ₃ , or -OCF ₃ , and at least one of ^{L 1} , L ² , L ³ , and L ^{4 is hydrogen;}
X ¹ and X ² are independently hydrogen or fluorine.

Item 13. From Eqs. (1-14-1), Eqs. (1-16-1-1) to Eqs. (1-16-1-7), Eqs. (1-16-2-1), Eqs. (1-16-2-) 2), Eq. (1-16-3-1), Eq. (1-16-3-2), Eq. (1-16-4-1), Eq. (1-16-4-2), Eq. (1) Items 1, 4 represented by -16-5-1), Eq. (1-16-5-2), or Eqs. (1-16-6-1) to Eqs. (1-16-6-4). Item 5. The compound according to any one of 5, 8, 9, and 11.

Equations (1-14-1-1), equations (1-16-1-1) to equations (1-16-1-7), equations (1-16-2-1), equations (1-16-) 2-2), Equation (1-16-3-1), Equation (1-16-3-2), Equation (1-16-4-1), Equation (1-16-4-2), Equation In equations (1-16-5-1), equations (1-16-5-2), and equations (1-16-6-1) to equations (1-16-6-4).
R ¹ and R ² are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
^Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
L ⁵ and L ⁶ are independently hydrogen, fluorine, -CF ₃ or -OCF ₃ , and at least one of ^{L 5} and L ⁶ _{is fluorine, -CF 3} or -OCF ₃ . ;
X ¹ and X ² are independently hydrogen or fluorine.

Item 14. Item 6. The compound according to any one of Items 1 to 3, 6, 7, 10, and 12, represented by the formulas (1-1-1-1) to (1-1-1-7).

In equations (1-1-1-1) to (1-1-1-7),
R ¹ and R ² are independently alkyl with 1 to 7 carbons, alkoxy with 1 to 6 carbons, alkoxyalkyl with 2 to 6 carbons, alkenyl with 2 to 7 carbons, or alkenyl with 2 to 7 carbons. Alkoxyoxy.
^Ra is hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms.

Item 15. The item according to any one of Items 1, 4, 5, 8, 9, 11, and 13, which is represented by the formula (1-14-1-1) or the formula (1-14-1-2). Compound.

In the formula (1-14-1-1) or the formula (1-14-1-2),
R ¹ and R ² are independently alkyl with 1 to 7 carbons, alkoxy with 1 to 6 carbons, alkoxyalkyl with 2 to 6 carbons, alkenyl with 2 to 7 carbons, or alkenyl with 2 to 7 carbons. Alkoxyoxy.
^Ra is hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms.

Item 16. A liquid crystal composition containing at least one of the compounds according to any one of Items 1 to 15.

Item 17. Item 6. The liquid crystal composition according to Item 16, which contains at least one compound selected from the group of compounds represented by the formulas (2) to (4).

In equations (2) to (4),
R ¹¹ and ^{R 12} are independently alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in the ^{R 11} and ^{R 12,} at least one -CH ₂ - is replaced by -O- At least one hydrogen may be replaced with fluorine;
Ring B ¹ , Ring B ² , Ring B ³ and Ring B ⁴ are independent, 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro- 1,4-phenylene, or pyrimidine-2,5-diyl;
Z ¹¹ , Z ¹² , and Z ¹³ are independently single-bonded, -COO-,-(CH ₂ ) _2- , -CH = CH-, or -C≡C-.

Item 18. Item 6. The liquid crystal composition according to Item 16 or 17, further containing at least one compound selected from the group of compounds represented by formulas (5) to (13).

In equations (5) to (13),
R ¹³ and ^{R 14} are independently alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in the ^{R 13} and ^{R 14,} at least one -CH ₂ - is replaced by -O- At least one hydrogen may be replaced with fluorine;
R ¹⁵ is hydrogen, fluorine, alkenyl alkyl carbon atoms or 2 to 10 from 10 1 carbon atoms, in the ^{R 15,} at least one -CH ₂ - may be replaced by -O-, at least One hydrogen may be replaced by fluorine;
Ring C ¹ , Ring C ² , Ring C ³ , and Ring C ⁴ may independently replace 1,4-cyclohexylene, 1,4-cyclohexenylene, and at least one hydrogen with fluorine 1, 4-Phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
Ring ^{C 5} and ring ^{C 6} are each independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene, 2,6 -Jeil;
^{^{^{Z 14, Z 15, Z 16}}} , and ^{Z 17} are independently a single _{bond, -COO -, - CH 2 O} -, - OCF 2 -, - (CH 2) 2 -, or -OCF ₂ - (CH ₂ ) _2- is;
L ¹¹ and L ¹² are independently fluorine or chlorine;
S ¹¹ is hydrogen or methyl;
X is -CHF- or -CF _2- ;
j, k, m, n, p, q, r, and s are independently 0 or 1, and the sum of k, m, n, and p is 1 or 2, q, r, and The sum of s is 0, 1, 2, or 3, and t is 1, 2, or 3.

Item 19. Item 6. The liquid crystal composition according to any one of Items 16 to 18, further containing at least one compound selected from the group of compounds represented by the formulas (21) to (23).

In equations (21) to (23),
R ¹⁶ is an alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in this ^{R 16,} at least one -CH ₂ - may be replaced by -O-, at least one hydrogen , May be replaced with fluorine;
X ¹¹ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ ;
Ring D ¹ , Ring D ² , and Ring D ³ are independently 1,4-cyclohexylene, 1,4-phenylene, where at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl. , 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
Z ¹⁸ , Z ¹⁹ and Z ²⁰ are independently single-bonded, -COO-, -CH ₂ O-, -CF ₂ O-, -OCF ₂ -,-(CH ₂ ) _2- , -CH = CH. -, - C≡C-, or - _(CH _{2) 4} - a and;
L ¹³ and L ¹⁴ are independently hydrogen or fluorine.

Item 20. Item 6. The liquid crystal composition according to any one of Items 16 to 19, further containing at least one compound selected from the group of compounds represented by the formula (24).

In equation (24)
R ¹⁷ is an alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in this ^{R 17,} at least one -CH ₂ - may be replaced by -O-, at least one hydrogen May be replaced with fluorine;
X ¹² is -C≡N or -C≡C-C≡N;
Ring E ¹ is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl. , Or pyrimidine-2,5-dioxane;
Z ²¹ is a single bond, -COO-, -CH ₂ O-, -CF ₂ O-, -OCF ₂ -,-(CH ₂ ) _2- , or -C ≡ C-;
L ¹⁵ and L ¹⁶ are independently hydrogen or fluorine;
i is 1, 2, 3, or 4.

Item 21. A liquid crystal display device containing the liquid crystal composition according to any one of Items 16 to 20.

The present invention also includes the following items. (A) The composition described above further comprising at least one optically active compound and / or polymerizable compound. (B) The composition described above further comprising at least one antioxidant and / or UV absorber.

The present invention also includes the following items. (C) One selected from the group of polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, UV absorbers, light stabilizers, heat stabilizers, dyes, and defoamers. The composition described above further comprising two or at least three additives. (D) The upper limit temperature of the nematic phase is 70 ° C. or higher, the optical anisotropy at a wavelength of 589 nm (measured at 25 ° C.) is 0.08 or higher, and the dielectric anisotropy at a frequency of 1 kHz (measured at 25 ° C.). ) Is -2 or less, the above composition.

The present invention also includes the following items. (E) A device containing the above composition and having a mode of PC, TN, STN, ECB, OCB, IPS, VA, FFS, FPA, or PSA. (F) AM device containing the above composition. (G) A transmissive device containing the above composition. (H) Use of the above composition as a composition having a nematic phase. (I) Use as an optically active composition by adding an optically active compound to the above composition.

The aspect of compound (1), the synthesis of compound (1), the liquid crystal composition, and the liquid crystal display element will be described in order.

1. 1. Aspects of Compound (1) Compound (1) is characterized by having a divalent group represented by the following formula. In the following formula, X is hydrogen or a substituent.

This compound is extremely physically and chemically stable under the conditions in which the device is normally used, and has good compatibility with other liquid crystal compounds. Compositions containing this compound are stable under the conditions in which the device is commonly used. This composition has a negatively large dielectric anisotropy. This compound has the general physical properties required for the components of the composition, the appropriate optical anisotropy, and the appropriate dielectric anisotropy.

^{Terminal groups R 1} and R ² , lateral groups ^Ra , ring A ¹ , and ring A ² , ring N ¹ , and ring N ² , binding groups Z ¹ , Z ² , Z ³ , and Z in compound (1). ^4, a preferred embodiment of side groups ^{^{^{L 1, L 2, L 3}}} , L, 4, L 5 and ^{L 6} are as follows. This example also applies to the sub-formula of compound (1). In compound (1), the physical properties can be arbitrarily adjusted by appropriately combining these groups. Because large difference is not in the physical properties of the compound, the compound (1) is, ^{2 H} (deuterium), an isotope such as ^{13 C} may contain more than the amount of natural abundance. The definition of the symbol of compound (1) is as described in Item 1.

In formula (1), ^{R 1} is hydrogen or alkyl of from 1 to 15 carbon atoms, in the ^{R 1,} at least one -CH ₂ - is -O -, - replaced by S-, or -CO- At least one _{of-(CH 2} ) _2- may be replaced by -CH = CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine.
R ² is hydrogen, fluorine, chlorine, -C≡N, alkyl of -C≡C-C≡N or 1 to 15 carbon atoms, in the ^{R 2,} at least one of -CH ₂ -, - It may be replaced by O-, -S-, or -CO-, and at least one- (CH ₂ ) _2- may be replaced by -CH = CH- or -C≡C-, at least 1 One hydrogen may be replaced with fluorine or chlorine.

However, in the formula (1), when l is 0, R ¹ does not become hydrogen, and when o is 0, R ^{2 does not become hydrogen.}

Preferred R ¹ or R ² are alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkylthio, alkylthioalkoxy, acyl, acylalkyl, acyloxy, acyloxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkenyl, alkenyloxy, alkenyloxyalkyl, alkoxy. Alkoxy, alkynyl, and alkynyloxy. In this R ¹ or R ² , at least one hydrogen may be replaced with fluorine or chlorine. This example contains a group in which at least two hydrogens have been replaced with both fluorine and chlorine. Groups in which at least one hydrogen is replaced with fluorine alone are even more preferred. In R ¹ or R ² , a straight chain is preferable to a branched chain. Even if R ¹ or R ² is a branched chain, it is preferable when it is optically active. More preferred R ¹ or R ² are alkyl, alkoxy, alkoxyalkyl, alkenyl, monofluoroalkyl, polyfluoroalkyl, monofluoroalkoxy, and polyfluoroalkoxy. R ² may be fluorine, chlorine, -C≡N, or -C≡C-C≡N in addition to the above groups.

The preferred configuration of -CH = CH- in alkenyl depends on the position of the double bond. Trans-configuration is preferred for alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl, 3-hexenyl. The cis configuration is preferred for alkenyl such as 2-butenyl, 2-pentenyl, 2-hexenyl.

Specific R ¹ or R ² are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, methoxymethyl. , Methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl, propoxyethyl, butoxymethyl, butoxyethyl, pentoxymethyl, pentoxyethyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-Buthenyl, 3-Butenyl, 1-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Heptenyl, 2 -Heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, 2-propenyloxy, 2-butenyloxy, 2-pentenyloxy, 2-hexenyloxy, and 1-propynyl.

Specific R ¹ or R ² is 2-fluoroethyl, 3-fluoropropyl, 2,2,2-trifluoroethyl, 2-fluorovinyl, 2,2-difluorovinyl, 2-fluoro-2-vinyl, 3-Fluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 4-fluoro-1-propenyl, and 4,4-difluoro-3-butenyl.

Specific R ² is, in addition to the above groups, fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -CF ₂ CF ₃ , -CF ₂ CHF ₂ , -CF. ₂ CH ₂ F, -CF ₂ CF ₂ CF ₃ , -CF ₂ CHFCF ₃ , -CHFCF ₂ CF ₃ , -OCF ₃ , -OCHF ₂ , -OCH ₂ F, -OCF ₂ CF ₃ , -OCF ₂ CHF ₂ , It may be _{-OCF 2} CH ₂ F, -OCF ₂ CF ₂ CF ₃ , -OCF ₂ CHFCF ₃ , and -OCHFCF ₂ CF _3.

More preferred R ¹ or R ² are ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methoxymethyl, ethoxymethyl, ethoxyethyl, propoxymethyl, propoxyethyl, Butoxymethyl, pentoxymethyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2 -Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 2-propenyloxy, 2-butenyloxy, and 2-pentenyloxy. In addition, more preferably ^R 2 _{_{_{is, -OCF 3, -OCHF 2, -OCH}}} 2 F, -OCF 2 CF 3, -OCF 2 CHF 2, -OCF 2 CH 2 F, -OCF 2 CF 2 CF 3, - OCF ₂ CHFCF ₃ , -OCHFCF ₂ CF ₃ , fluorine, chlorine, and -C≡N. The most preferred R ¹ or R ² are ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, vinyl, 1-propenyl, 3 -Butenyl, and 3-pentenyl. In addition, the most preferred ^R 2 _{_{_{_{is, -OCF 3, -OCHF 2, -CF}}}} 3, -CHF 2, -CH 2 F, -OCF 2 CHF 2, -OCF 2 CHFCF 3, fluorine, and -C≡N be.

^Ra is hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms.

Preferred ^Ras are methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, sec-butyl, pentane-2-yl, hexane-2-yl, pentane-3-yl, hexane-3-yl, tert-butyl. , Tert-pentyl, 3-methylpentane-3-yl, and 3-ethylpentane-3-yl. More preferred ^Ra are methyl, ethyl, propyl, butyl, isopropyl, sec-butyl, and tert-butyl. Particularly preferred ^Ra are methyl, ethyl, propyl, and isopropyl. The most preferred ^Ra are methyl and ethyl.

In the formula (1), the ring A ¹ and the ring A ² are independently cycloalkylenes having 3 to 5 carbon atoms, and in the ring A ¹ and the ring A ² , at least one -CH _2- is -O. It may be replaced with −, and at least one − (CH ₂ ) ₂ − may be replaced with −CH = CH−.

An example of a preferred ring A ¹ or ring A ² is a divalent group represented by the following formulas (25-1) to (25-27). A more preferable example is a divalent group represented by the formulas (25-1) to (25-17). Particularly preferred examples are divalent groups represented by formulas (25-1) to (25-3) and formulas (25-13) to formulas (25-17). The most preferable example is a divalent group represented by the formulas (25-1) to (25-3).

In formula (1), ring N ¹ and ring N ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4. -Tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran -2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4- Diyl, furan-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2, With 5-diyl, benzo [b] thiophene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl, or 9H-fluorene-2,7-diyl Yes, in rings N ¹ and N ² , at least one hydrogen is fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH. _It may be replaced by 2F.

"In Ring N ¹ and Ring N ² , at least one hydrogen is fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH _2. A preferred example of "may be replaced by F" is a divalent group represented by the following formulas (26-1) to (26-71). More preferred examples are equations (26-1) to (26-4), equations (26-6), equations (26-10) to (26-15), and equations (26-54) to (26). It is a divalent group represented by -59).

More preferred ring N ¹ or ring N ² is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1, 4-Phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2,3,5-trifluoro-1 , 4-Phenylene, pyridine-2,5-diyl, 3-fluoropyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridazine-2,5-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and naphthalene-2,6-diyl. The configuration of 1,4-cyclohexylene and 1,3-dioxane-2,5-diyl is preferably trans over cis.

Particularly preferred ring N ¹ or ring N ² is 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-. Difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyridine-2,5-diyl, and pyrimidine-2,5-diyl. .. The most preferred ring N ¹ or ring N ² is 1,4-cyclohexylene and 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene.

In formula (1), Z ¹ , Z ² , Z ³ , and Z ⁴ are independently single-bonded or alkylenes with 1 to 6 carbon atoms, in Z ¹ , Z ² , Z ³ , and Z ⁴ . , At least one -CH _2- may be replaced with -O-, -S-, -CO-, or -SiH _2- , and at least _{one- (CH 2} ) ₂ -is -CH = CH. -Or -C≡C- may be replaced, and at least one hydrogen may be replaced with fluorine or chlorine.

Specific examples of Z ¹ , Z ² , Z ³ , or Z ⁴ are single bond, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-(CH ₂ ) _2- , -CH = CH-, -CF = CH-, -CH = CF-, -CF = CF-, -C≡C-, -CH ₂ CO-, -COCH _2- ,-(CH ₂ ) ₄ -,-(CH ₂ ) ₂ COO-,-(CH ₂ ) ₂ OCO-, -OCO (CH ₂ ) _2- , -COO (CH ₂ ) ₂ -,-(CH ₂ ) ₂ CF ₂ O-,-(CH ₂ ) ₂ OCF _2- , -OCF ₂ (CH ₂ ) _2- , -CF ₂ O (CH ₂ ) ₂ -,-(CH ₂ ) ₃ O-, -O (CH) ₂ ) _3- , -CH = CH- (CH ₂ ) ₂ -,-(CH ₂ ) ₂ -CH = CH-, -CH = CH-CH ₂ O-, and -OCH _{2-CH = CH-.} .. Trans is preferred over cis for the configuration of the double bond of the linking group such as -CH = CH-, -CF = CF-, -CH = CH-CH ₂ O-, -OCH _{2-CH = CH-.}

Preferred Z ¹ , Z ² , Z ³ or Z ⁴ are single bonds, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF ₂ -,-( CH ₂ ) _2- , -CH = CH-,-(CH ₂ ) ₄ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) _2- , -(CH ₂ ) ₂ -CH = CH-, -CH = CH-CH ₂ O-, and -OCH _{2-CH = CH-.} More preferred Z ¹ , Z ² or Z ³ are single bonds, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF _2- , -CH = CH- ,-(CH ₂ ) ₂ -,-(CH ₂ ) ₄ -,-(CH ₂ ) ₃ O-, -O (CH ₂ ) _3- , -CH = CH- (CH ₂ ) _2-, and-( CH ₂ ) _2- CH = CH-. The most preferred Z ¹ , Z ² , Z ³ or Z ⁴ are single bonds, -CH ₂ O- or -OCH _2- .

In formula (1), L ¹ , L ² , L ³ , L ⁴ , L ⁵ , and L ⁶ independently contain hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, and -OCF. _3, -OCHF _2, a -OCH ₂ F or -C≡N,.

In formula (1), ^{when both L 5} and L ⁶ are hydrogen, ^{at least one of L 1} , L ² , L ³ , and L ⁴ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH. ₂ F, -OCF ₃ _{, -OCHF 2} , -OCH ₂ F, or -C ≡ N, and at least one of ^{L 1} , L ² , L ³ , and L ^{4 may be hydrogen.} More preferred L ¹ , L ² , L ³ and L ⁴ are fluorine or -CF ₃ . Particularly preferred L ¹ , L ² , L ³ and L ⁴ are fluorine.

In formula (1), when L ¹ , L ² , L ³ , and L ⁴ are all hydrogen, ^{at least one of L 5} and L ⁶ is fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH. ₂ F, -OCF ₃ _{, -OCHF 2} , -OCH ₂ F, or -C ≡ N, and at least one of ^{L 5} and L ^{6 may be hydrogen.} More preferred L ⁵ and L ⁶ are fluorine or -CF ₃ . Particularly preferred L ⁵ and L ⁶ are fluorine.

In formula (1), l and o are independently 0, or 1, and m, and n are independently 0, 1, or 2, and the sum of l, m, n, and o. Is an integer from 0 to 4. Compound (1) has five rings from one part. These rings include fused rings and crosslinked 6-membered rings in addition to the usual 6-membered rings. When the compound (1) has one or two rings, the compatibility with other liquid crystal compounds is good and the viscosity is low. When compound (1) has three or four rings, the upper limit temperature is high. When compound (1) has four rings, the temperature range of the liquid crystal phase is wide.

By appropriately selecting the terminal group, ring and bonding group of compound (1), it is possible to arbitrarily adjust physical properties such as optical anisotropy and dielectric anisotropy. The effects of the types of terminal groups R ¹ and R ² , rings A ¹ and A ² , binding groups Z ¹ , Z ² , Z ³ and Z ⁴ on the physical properties of compound (1) will be described below.

In compound (1), when R ¹ or R ² is linear, the temperature range of the liquid crystal phase is wide and the viscosity is low. When R ¹ or R ² is a branched chain, the compatibility with other liquid crystal compounds is good. Compounds in which R ¹ or R ² are optically active groups are useful as chiral dopants. By adding this compound to the composition, it is possible to prevent the reverse twisted domain generated in the device. Compounds in which R ¹ or R ² is not an optically active group are useful as components of the composition. When R ¹ or R ² is alkenyl, the preferred configuration depends on the position of the double bond. Alkenyl compounds with a preferred configuration have a high upper temperature limit or a wide temperature range of the liquid crystal phase. Mol. Cryst. Liq. Cryst., 1985, 131, 109 and Mol. Cryst. Liq. Cryst., 1985, 131, 327 have detailed explanations.

Ring A ¹ or ring A ² may have at least one hydrogen substituted with fluorine or chlorine 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, or pyridazine-3. When it is 6,6-diyl, the optical anisotropy is large. When the ring is 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,3-dioxane-2,5-diyl, the optical anisotropy is small.

When at least two rings are 1,4-cyclohexylene, the upper limit temperature is high, the optical anisotropy is small, and the viscosity is small. When at least one ring is 1,4-phenylene, the optical anisotropy is relatively large and the orientation parameter is large. When at least two rings are 1,4-phenylene, the optical anisotropy is large, the temperature range of the liquid crystal phase is wide, and the upper limit temperature is high.

Bonding group ^Z ^1, Z 2, ^{Z 3} or ^{Z 4} is a single _{_{bond,, -CH 2 O -, -}} CF 2 O -, - OCF 2 -, - (CH 2) 2 -, - CH = CH -, - CF = CF-, or - _(CH _{2) 4} - is when the viscosity is small. The viscosity is smaller when the binding group is a single bond, -OCF _2- , -CF ₂ O-,-(CH ₂ ) _2- , or -CH = CH-. When the bonding group is −CH = CH−, the temperature range of the liquid crystal phase is wide, and the elastic constant ratio K ₃₃ / K ₁₁ (K ₃₃ : bend elastic constant, K ₁₁ : spray elastic constant) is large. When the bonding group is −C≡C−, the optical anisotropy is large.

When compound (1) has one or two rings, the viscosity is low. When compound (1) has four or five rings, the upper limit temperature is high. As described above, a compound having the required physical properties can be obtained by appropriately selecting the type of terminal group, ring, and bonding group, and the number of rings. Therefore, compound (1) is useful as a component of compositions used in devices having modes such as PC, TN, STN, ECB, OCB, IPS, and VA.

In formula (1), this compound is when ^{both L 5} and L ⁶ are hydrogen, and when L ¹ , L ² , L ³ or L ⁴ is fluorine, chlorine, -CF ₃ , or -CHF _2. preferable. This compound is even more preferred when both L ⁵ and L ⁶ are hydrogen and when L ¹ , L ² , L ³ or L ^{4 is fluorine or chlorine.} This compound is most preferred when both L ⁵ and L ⁶ are hydrogen and when L ¹ , L ² , L ³ or L ^{4 is fluorine.}

In formula (1), when L ¹ , L ² , L ³ , and L ⁴ are all hydrogen, and L ⁵ or L ⁶ is fluorine, chlorine, -CF ₃ , or -CHF ₂ , this compound is preferable. This compound is even more preferred when L ¹ , L ² , L ³ , and L ⁴ are all hydrogen, and when L ⁵ or L ^{6 is fluorine or chlorine.} This compound is most preferred when L ¹ , L ² , L ³ , and L ⁴ are all hydrogen, and when L ⁵ or L ^{6 is fluorine.}

Preferred examples of the compound (1) are the compounds (1-1) to (1-26) described in Items 2 and 4. A more preferable example is the compound represented by the lower formula in Items 6 and 8. Compound (1) is suitable for devices having modes such as VA, IPS, and PSA.

2. Synthesis of Compound (1) A method for synthesizing compound (1) will be described. Compound (1) can be synthesized by appropriately combining the methods of synthetic organic chemistry. The methods for introducing the required end groups, rings and binding groups into the starting material are "Organic Syntheses" (John Wiley & Sons, Inc.), "Organic Reactions" (John Wiley & Sons). , Inc.), "Comprehensive Organic Synthesis" (Pergamon Press), "New Experimental Chemistry Course" (Maruzen), etc.

2-1. From generation bonding group Z ¹ of the bonding group Z on how to generate Z ^4, illustrating a first scheme. Next, the reactions described in the scheme according to the methods (1) to (11) will be described. In this scheme, MSG ¹ (or MSG ² ) is a monovalent organic group having at least one ring. The monovalent organic groups represented by the plurality of MSG ¹ (or MSG ² ) used in the scheme may be the same or different. Compounds (1A) to (1J) correspond to compound (1).

(1) Generation of single bond A compound by reacting arylboric acid (31) and a halide (32) synthesized by a known method in the presence of a catalyst such as carbonate and tetrakis (triphenylphosphine) palladium. (1A) is synthesized. This compound (1A) is prepared by reacting a halide (33) synthesized by a known method with n-butyllithium and then zinc chloride, and in the presence of a catalyst such as dichlorobis (triphenylphosphine) palladium. It is also synthesized by reacting (32).

(2) Production of -COO- The halide (33) is reacted with n-butyllithium and then carbon dioxide to obtain a carboxylic acid (34). Compound (1B) is synthesized by dehydrating compound (35) and carboxylic acid (34) synthesized by a known method in the presence of DDC (1,3-dicyclohexylcarbodiimide) and DMAP (4-dimethylaminopyridine). do.

(3) -Production of -CF ₂ O- Compound (1B) is treated with a sulfurizing agent such as Lawesson's reagent to obtain thionoester (36). The thionoester (36) is fluorinated with a hydrogen fluoride pyridine complex and NBS (N-bromosuccinimide) to synthesize compound (1C). See M. Kuroboshi et al., Chem. Lett., 1992, 827. Compound (1C) is also synthesized by fluorinating thionoester (36) with DAST ((diethylamino) sulfur trifluoride). See W. H. Bunnelle et al., J. Org. Chem. 1990, 55, 768. It is also possible to generate this linking group by the method described in Peer. Kirsch et al., Angew. Chem. Int. Ed. 2001, 40, 1480.

(4) Production of -CH = CH- The halide (32) is treated with n-butyllithium and then reacted with DMF (N, N-dimethylformamide) to obtain an aldehyde (38). The phosphonium salt (37) synthesized by a known method is treated with a base such as potassium t-butoxide to generate phosphorus irid. This phosphorus irid is reacted with aldehyde (38) to synthesize compound (1D). Since a cis form is produced depending on the reaction conditions, the cis form is isomerized to a trans form by a known method if necessary.

(5)-(CH ₂ ) _2- Production Compound (1E) is synthesized by hydrogenating compound (1D) in the presence of a catalyst such as palladium carbon.

(6)-(CH ₂ ) _4- Formation A phosphonium salt (39) is used instead of the phosphonium salt (37), _{and a compound having- (CH 2} ) _2- CH = CH-is prepared according to the method of method (4). obtain. This is catalytically hydrogenated to synthesize compound (1F).

(7) -CH ₂ CH = CHCH _2- Formation A compound according to the method (4), using a phosphonium salt (40) instead of the phosphonium salt (37) and an aldehyde (41) instead of the aldehyde (38). (1G) is synthesized. Since a trans form is produced depending on the reaction conditions, the trans form is isomerized to a cis form by a known method if necessary.

(8) Production of -C≡C- After reacting the halide (33) with 2-methyl-3-butin-2-ol in the presence of a catalyst of dichloropalladium and copper halide, under basic conditions. Deprotection with to give compound (32). Compound (42) is reacted with a halide (32) in the presence of a catalyst of dichloropalladium and copper halide to synthesize compound (1H).

(9) Production of -CF = CF-The halide (33) is treated with n-butyllithium and then reacted with tetrafluoroethylene to obtain compound (43). The halide (32) is treated with n-butyllithium and then reacted with the compound (43) to synthesize the compound (1I).

(10) -Production of -OCH _2- The aldehyde (38) is reduced with a reducing agent such as sodium borohydride to obtain the compound (44). Compound (44) is bromide with hydrobromic acid or the like to obtain bromide (45). In the presence of a base such as potassium carbonate, the bromide (45) is reacted with the compound (46) to synthesize the compound (1J).

(11)-(CF ₂ ) _2- Generation of diketone (-COCO-) in the presence of hydrogen fluoride catalyst according to the method described in J. Am. Chem. Soc., 2001, 123, 5414. Fluorination with sulfur fluoride gives a compound _{having- (CF 2} ) _2-.

2-2. Generated from ring ^{A 1} of ^{A 3} and ring ^{N 1} Next, a production method related to ^{A 3} and ring ^{N 1} illustrating the rings ^{A 1.} 1,4-Cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, pyridine-2 For rings such as, 5-dioxane and pyrimidine-2,5-dioxane, starting materials are commercially available or the production method is well known. Therefore, the compounds (64), (67), and (71) shown below will be described.

Decahydronaphthalen-2,6-dione (64) is a starting material for compounds having decahydronaphthalen-2,6-diyl. This compound (64) is obtained by catalytically reducing diol (63) with ruthenium oxide in the presence of ruthenium oxide and further oxidizing with chromium oxide according to the method described in JP-A-2000-239564. This compound is converted to compound (1) by a usual method.

The structural unit of 2,3- (bistrifluoromethyl) phenylene is synthesized by the method described in Org. Lett., 2000, 2 (21), 3345. Aniline (66) is synthesized by reacting furan (65) with 1,1,1,4,4,4-hexafluoro-2-butin at a high temperature in a Diels-Alder type reaction. This compound is subjected to a Sandmeyer-type reaction according to the method described in Org. Synth. Coll., Vol. 2, 1943, 355 to obtain an iodide (67). This compound is converted to compound (1) by a usual method.

The structural unit of 2-difluoromethyl-3-fluorophenylene is synthesized by the following method. The hydroxyl group of compound (68) is protected with an appropriate protecting group to obtain compound (69). P means protecting group. Compound (69) is reacted with s-butyllithium followed by N, N-dimethylformamide (DMF) to give aldehyde (70). This compound is fluorinated with diethylaminosulfur trifluoride (DAST) and subsequently deprotected to give phenol (71). This compound is converted to compound (1) by a usual method.

Formation of 2-3.3,6-dihydro-2H-pyran ring A method for forming this ring is carried out using compounds (1a) and (1b) having a divalent group represented by the formula (pr-1). explain. A compound having a divalent group represented by the formula (pr-2) can also be synthesized by this method. The synthetic scheme of compound (1a) is as follows.

Compound (s-1) is synthesized according to the method described in JP-A-2011-136924. Compound (s-1) is reduced with a reducing agent such as sodium borohydride to obtain compound (s-2). This compound is halogenated with triphenylphosphine and carbon tetrahalogenate, and treated with a dehalogenating agent such as diazabicycloundecene (DBU) to obtain the target compound (1a).

The synthesis scheme of compound (1b) is as described above. Compound (s-4) is obtained by reacting compound (s-3) with aldehyde (17) in the presence of a Lewis acid such as boron trifluoride diethyl ether complex, and then hydrogenating the compound (s-3). This compound is reduced with a reducing agent such as lithium aluminum hydride to obtain compound (s-5). Compound (1b) is obtained by halogenating this compound with triphenylphosphine and carbon tetrahalogenate and treating it with a dehalogenating agent such as diazabicycloundecene (DBU).

2-4. Carbazole ring formation The synthetic schemes of the compounds (1c) to (1f) are as follows.

Compound (s-6), compound (s-7), Pd (amphos) Cl2, and t-butoxysodium are reacted to obtain compound (s-8). P means protecting group. Deprotection of this compound is performed to obtain compound (s-9). This compound is reacted with palladium acetate in acetic acid to obtain (1c). Alkylation of this compound is carried out to obtain compound (1d). In these compounds, ^{the definitions of L 1} , L ² , L ³ and L ⁴ are the same as the definitions of the symbols described in Item 1. The definition of RA ¹ or RA ² is the same as the definition of ^{R 1} or R ² ^{described in MSG 1} and Item 1.

Compound (s-10), compound (s-11), Pd (amphos) Cl2, and t-butoxysodium are reacted to obtain compound (s-12). P means protecting group. Deprotection of this compound is performed to obtain compound (s-13). This compound is reacted with palladium acetate in acetic acid to obtain (1e). Alkylation of this compound is carried out to obtain compound (1f). In these compounds, ^{the definitions of L 5} and L ⁶ are the same as the definitions of the symbols described in Item 1. The definition of RA ¹ or RA ² is the same as the definition of ^{R 1} or R ² ^{described in MSG 1} and Item 1.

3. 3. Liquid crystal composition 3-1. Ingredients Compounds The liquid crystal composition of the present invention will be described. This composition contains at least one compound (1) as a component (a). The composition may contain two or more compounds (1). The component of the composition may be only compound (1). The composition preferably contains at least one of the compound (1) in the range of 1% by weight to 99% by weight in order to exhibit good physical properties. In the composition having a negative dielectric anisotropy, the preferable content of the compound (1) is in the range of 5% by weight to 60% by weight. In the composition having a positive dielectric anisotropy, the preferable content of the compound (1) is 30% by weight or less.

This composition contains compound (1) as component (a). The composition preferably further contains a liquid crystal compound selected from the components (b) to (e) shown in Table 1. When preparing this composition, it is preferable to select the components (b) to (e) in consideration of the positive and negative of the dielectric anisotropy and the magnitude. This composition may contain liquid crystalline compounds different from compounds (1) to (13) and (21) to (24). This composition does not have to contain such a liquid crystal compound.

Component (b) is a compound having two terminal groups such as alkyl. Preferred examples of the component (b) include compounds (2-1) to (2-11), compounds (3-1) to (3-19), and compounds (4-1) to (4-7). be able to. In these compounds, R ¹¹ and R ¹² are independently alkyls with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, and in these R ¹¹ and R ¹² , at least one -CH _2- It may be replaced with —O—, and at least one hydrogen may be replaced with fluorine.

Component (b) has a small dielectric anisotropy. Component (b) is close to neutral. Compound (2) has the effect of lowering the viscosity or adjusting the optical anisotropy. Compounds (3) and (4) have the effect of widening the temperature range of the nematic phase or adjusting the optical anisotropy by raising the upper limit temperature.

As the content of the component (b) is increased, the viscosity of the composition decreases, but the dielectric anisotropy decreases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, it is preferable that the content is large. When preparing a composition for a mode such as IPS or VA, the content of the component (b) is preferably 30% by weight or more, more preferably 40% by weight or more, based on the weight of the liquid crystal composition. be.

The component (c) is a compound (5) to (13). These compounds have phenylene in which the lateral position is replaced by two halogens, such as 2,3-difluoro-1,4-phenylene. Preferred examples of the component (c) include compounds (5-1) to (5-9), compounds (6-1) to (6-19), compounds (7-1) and (7-2), compounds ( 8-1) to (8-3), compounds (9-1) to (9-3), compounds (10-1) to (10-11), compounds (11-1) to (11-3), Compounds (12-1) to (12-3), and compound (13-1) can be mentioned. In these compounds, R ¹³ and R ¹⁴ are independently alkyls with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, and in these R ¹³ and R ¹⁴ , at least one -CH _2- may be replaced by -O-, at least one hydrogen may be replaced by fluorine, R ¹⁵ is hydrogen, fluorine, alkenyl alkyl or 2 to 10 carbon atoms from 10 1 carbon atoms, In this R ¹⁵ , at least one -CH _2- may be replaced by -O-, and in this R ¹⁵ , at least one hydrogen may be replaced by fluorine.

Component (c) has a large negative dielectric anisotropy. Ingredient (c) is used when preparing compositions for modes such as IPS, VA, PSA. As the content of the component (c) is increased, the dielectric anisotropy of the composition becomes negatively large, but the viscosity becomes large. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the content is preferably small. Considering that the dielectric anisotropy is about −5, the content is preferably 40% by weight or more in order to drive the voltage sufficiently.

Of the component (c), the compound (5) is a bicyclic compound, and therefore has the effects of lowering the viscosity, adjusting the optical anisotropy, or increasing the dielectric anisotropy. Since the compounds (6) and (7) are tricyclic compounds and the compound (8) is a tetracyclic compound, they have the effect of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. be. Compounds (9) to (13) have the effect of increasing the dielectric anisotropy.

When preparing a composition for a mode such as IPS, VA, PSA, the content of the component (c) is preferably 40% by weight or more, more preferably 50% based on the weight of the liquid crystal composition. It ranges from% to 95% by weight. When the component (c) is added to a composition having a positive dielectric anisotropy, the content of the component (c) is preferably 30% by weight or less. By adding the component (c), it is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the device.

Component (d) is a compound having a halogen or fluorine-containing group at the right end. Preferred examples of the component (d) include compounds (21-1) to (21-16), compounds (22-1) to (22-116), and compounds (23-1) to (23-59). Can be done. In these ^{compounds, R 16} is alkenyl having 2 to 10 carbon alkyl or C 1 to 10 carbon atoms, in the ^{R 16,} at least one -CH ₂ - may be replaced by -O-, at least One hydrogen may be replaced by fluorine. X ¹¹ is fluorine, chlorine, -OCF ₃ , -OCHF ₂ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ .

Component (d) has a positive dielectric anisotropy and very good stability against heat and light, and is therefore used when preparing a composition for modes such as IPS, FFS, and OCB. The content of the component (d) is preferably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, more preferably from 40% by weight, based on the weight of the liquid crystal composition. It is in the range of 95% by weight. When the component (d) is added to a composition having a negative dielectric anisotropy, the content of the component (d) is preferably 30% by weight or less. By adding the component (d), it is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the device.

Component (e) is compound (24) whose right terminal group is -C≡N or -C≡C-C≡N. Preferred examples of the component (e) include compounds (24-1) to (24-64). In these ^{compounds, R 17} is alkenyl having 2 to 10 carbon alkyl or C 1 to 10 carbon atoms, in the ^{R 17,} at least one -CH ₂ - may be replaced by -O-, At least one hydrogen may be replaced with fluorine. X ¹² is -C ≡ N or -C ≡ C-C ≡ N.

The component (e) has a positive dielectric anisotropy and a large value, and is therefore used when preparing a composition for a mode such as TN. By adding this component (e), the dielectric anisotropy of the composition can be increased. The component (e) has the effect of widening the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. The component (e) is also useful for adjusting the voltage-transmittance curve of the device.

When preparing a composition for a mode such as TN, the content of the component (e) is preferably in the range of 1% by weight to 99% by weight, preferably 10% by weight, based on the weight of the liquid crystal composition. % To 97% by weight, more preferably 40% to 95% by weight. When the component (e) is added to a composition having a negative dielectric anisotropy, the content of the component (e) is preferably 30% by weight or less. By adding the component (e), it is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the device.

High stability to heat and light, high upper limit temperature, lower lower limit temperature, small viscosity, suitable optical anisotropy by combining the compound appropriately selected from the above components (b) to (e) and the compound (1). Directionality (ie, large optical anisotropy or small optical anisotropy), positive or negative large dielectric anisotropy, large specific resistance, appropriate elastic constants (ie, large elastic constants or small elastic constants), etc. A liquid crystal composition satisfying at least one of the physical characteristics can be prepared. Devices containing such compositions have a wide temperature range in which the device can be used, short response times, high voltage retention, low threshold voltage, high contrast ratio, low flicker rate, and long lifetime.

If the element is used for a long time, flicker may occur on the display screen. The flicker rate (%) can be expressed by (| brightness when a positive voltage is applied-brightness when a negative voltage is applied | / average brightness) x 100. An element having a flicker rate in the range of 0% to 1% is less likely to cause flicker on the display screen even if the element is used for a long time. This flicker is related to image burn-in and is presumed to be caused by the potential difference between the positive and negative frames when driven by alternating current. The composition containing the compound (1) is also useful for reducing the occurrence of flicker.

3-2. Additives The liquid crystal composition is prepared by a known method. For example, the constituent compounds are mixed and dissolved by heating. Additives may be added to this composition depending on the application. Examples of additives are polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, dyes, defoamers and the like. Such additives are well known to those of skill in the art and are described in the literature.

In a liquid crystal display element having a PSA (polymer sustained alignment) mode, the composition contains a polymer. The polymerizable compound is added for the purpose of forming a polymer in the composition. A polymer is produced in the composition by irradiating ultraviolet rays with a voltage applied between the electrodes to polymerize the polymerizable compound. By this method, an appropriate pre-tilt is achieved, so that the response time is shortened and the device with improved image burn-in is produced.

Preferred examples of the polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxylane, oxetane), and vinyl ketone. More preferred examples are compounds having at least one acryloyloxy and compounds having at least one methacryloyloxy. More preferred examples also include compounds having both acryloyloxy and methacryloyloxy.

More preferred examples are compounds (M-1) to (M-18). In these compounds, R ²⁵ to R ³¹ are independently hydrogen or methyl; R ³² , R ³³ , and R ³⁴ are independently hydrogen or alkyl having 1 to 5 carbon atoms, R ³² , At ^{least one of R 33} , and R ³⁴ is an alkyl having 1 to 5 carbon atoms; v, w, and x are 0 or 1 independently; u and y are independently 1 to 10 It is an integer. L ²¹ to L ²⁶ are independently hydrogen or fluorine; L ²⁷ and L ²⁸ are independently hydrogen, fluorine, or methyl.

The polymerizable compound can be rapidly polymerized by adding a polymerization initiator. By optimizing the reaction conditions, the amount of residual polymerizable compound can be reduced. Examples of photoradical polymerization initiators are TPO, 1173, and 4265 from BASF's DaroCure series and 184,369,500,651,784,819,907,1300,1700,1800,1850 from the Irgacure series. , And 2959.

Additional examples of photoradical polymerization initiators include 4-methoxyphenyl-2,4-bis (trichloromethyl) triazine, 2- (4-butoxystylyl) -5-trichloromethyl-1,3,4-oxadiazole, 9-Phenylaclysine, 9,10-benzphenazine, benzophenone / Michler's ketone mixture, hexaarylbiimidazole / mercaptobenzimidazole mixture, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, benzyl Dimethylketal, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, 2,4-diethylxanthone / p-dimethylaminomethyl benzoate mixture, benzophenone / methyltriethanolamine mixture Is.

After adding a photoradical polymerization initiator to the liquid crystal composition, polymerization can be carried out by irradiating ultraviolet rays with an electric field applied. However, unreacted polymerization initiators or degradation products of the polymerization initiators may cause display defects such as image burn-in on the device. In order to prevent this, photopolymerization may be carried out without adding a polymerization initiator. The preferred wavelength of the emitted light is in the range of 150 nm to 500 nm. More preferred wavelengths are in the range of 250 nm to 450 nm, and most preferred wavelengths are in the range of 300 nm to 400 nm.

When storing the polymerizable compound, a polymerization inhibitor may be added to prevent polymerization. The polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of polymerization inhibitors are hydroquinone, hydroquinone derivatives such as methylhydroquinone, 4-t-butylcatechol, 4-methoxyphenol, phenothiazine and the like.

The optically active compound has the effect of preventing reverse twisting by inducing a helical structure in the liquid crystal molecule to give a necessary twist angle. The spiral pitch can be adjusted by adding an optically active compound. Two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the spiral pitch. Preferred examples of the optically active compound include the following compounds (Op-1) to (Op-18). In compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, and R ²⁸ is an alkyl having 1 to 10 carbon atoms. * Marks represent asymmetric carbon.

Antioxidants are effective in maintaining a large voltage retention rate. Preferred examples of the antioxidant include the following compounds (AO-1) and (AO-2); Irganox415, Irganox565, Irganox1010, Irganox1035, Irganox3114, and Irganox1098 (trade name: BASF). The ultraviolet absorber is effective for preventing a decrease in the upper limit temperature. Preferred examples of the UV absorber are benzophenone derivatives, benzoate derivatives, triazole derivatives and the like, and specific examples thereof include the following compounds (AO-3) and (AO-4); Tinuvin 328, and Tinuvin 99-2 (trade name; BASF); and 1,4-diazabicyclo [2.2.2] octane (DABCO) can be mentioned.

A light stabilizer such as amine with steric hindrance is preferable in order to maintain a large voltage holding ratio. Preferred examples of light stabilizers are the following compounds (AO-5), (AO-6), (AO-7), (AO-8), and (AO-9); Product name; BASF); LA-52, LA-57, LA-77Y, and LA-77G (trade name: ADEKA) can be mentioned. A heat stabilizer is also effective for maintaining a large voltage holding ratio, and Irgafos 168 (trade name; BASF) can be mentioned as a preferable example. Dichroic dyes such as azo dyes, anthraquinone dyes, etc. are added to the composition to accommodate devices in GH (guest host) mode. Defoamers are effective in preventing foaming. Preferred examples of the defoaming agent are dimethyl silicone oil, methyl phenyl silicone oil and the like.

In compound (AO-1), R ⁴⁰ is an alkyl having 1 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, -COOR ⁴¹ , or-(CH ₂ ) _2- COOR ⁴¹ , where R ⁴¹ is carbon. Alkoxy of numbers 1 to 20. In compounds (AO-2) and (AO-5), R ⁴² is an alkyl having 1 to 20 carbon atoms. In the compound ^{(AO-5), R 43} is hydrogen, methyl or O ^· (oxygen radical); ring ^{G 1} is 1,4-cyclohexylene or 1,4-phenylene; Compound (AO-7) and In (AO-8), ring G ² is 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen has been replaced with fluorine; compound (AO-5),. In (AO-7) and (AO-8), z is 1, 2, or 3.

4. Liquid crystal display element The liquid crystal composition has an operation mode such as PC, TN, STN, OCB, PSA, and can be used for a liquid crystal display element driven by an active matrix method. This composition has an operation mode such as PC, TN, STN, OCB, VA, and IPS, and can also be used for a liquid crystal display element driven by a passive matrix method. These elements can be applied to any type of reflective type, transmissive type, and semitransparent type.

This composition is also suitable for NCAP (nematic curvilinear aligned phase) devices, where the composition is microencapsulated. This composition can also be used in a polymer-dispersed liquid crystal display element (PDLCD) and a polymer network liquid crystal display element (PNLCD). In these compositions, a large amount of the polymerizable compound is added. On the other hand, when the proportion of the polymerizable compound is 10% by weight or less based on the weight of the liquid crystal composition, a liquid crystal display element in PSA mode is produced. The preferred proportion is in the range of 0.1% by weight to 2% by weight. A more preferable ratio is in the range of 0.2% by weight to 1.0% by weight. The PSA mode element can be driven by a drive system such as an active matrix system or a passive matrix system. Such an element can be applied to any type of reflective type, transmissive type, and semitransparent type.

1. 1. Examples of Compound (1) The present invention will be described in more detail by way of examples. The present invention is not limited by the examples, as the examples are typical. Compound (1) was synthesized by the following procedure. The synthesized compound was identified by a method such as NMR analysis. The physical characteristics of the compound or composition and the characteristics of the device were measured by the following methods.

NMR analysis: DRX-500 manufactured by Bruker Biospin Co., Ltd. was used for the measurement. ^{1 In the 1} H-NMR measurement, the sample _{was dissolved in a deuterated solvent such as CDCl 3} and measured at room temperature, 500 MHz, and the number of integrations was 16 times. Tetramethylsilane was used as an internal standard. ^{19 In the} F-NMR measurement, CFCl ₃ was used as an internal standard, and the number of integrations was 24. In the description of the nuclear magnetic resonance spectrum, s means singlet, d means doublet, t means triplet, q means quartet, quin means quintet, sext means sextet, m means multiplet, and br means broad.

Gas chromatograph analysis: A GC-2010 type gas chromatograph manufactured by Shimadzu Corporation was used for the measurement. As the column, a capillary column DB-1 (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc. was used. Helium (1 mL / min) was used as the carrier gas. The temperature of the sample vaporization chamber was set to 300 ° C., and the temperature of the detector (FID) was set to 300 ° C. The sample was dissolved in acetone to prepare a 1% by weight solution, and 1 μL of the obtained solution was injected into the sample vaporization chamber. A GC Solution system manufactured by Shimadzu Corporation was used as the recorder.

Gas chromatograph mass spectrometry: A QP-2010 Ultra type gas chromatograph mass spectrometer manufactured by Shimadzu Corporation was used for the measurement. As the column, a capillary column DB-1 (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc. was used. Helium (1 mL / min) was used as the carrier gas. The temperature of the sample vaporization chamber was set to 300 ° C., the temperature of the ion source was set to 200 ° C., the ionization voltage was set to 70 eV, and the emission current was set to 150 uA. The sample was dissolved in acetone to prepare a 1% by weight solution, and 1 μL of the obtained solution was injected into the sample vaporization chamber. A GCMS solution system manufactured by Shimadzu Corporation was used as the recorder.

HPLC analysis: Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used for the measurement. As the column, YMC-Pack ODS-A (length 150 mm, inner diameter 4.6 mm, particle diameter 5 μm) manufactured by YMC was used. The eluate used was an appropriate mixture of acetonitrile and water. As the detector, a UV detector, an RI detector, a CORONA detector and the like were appropriately used. When a UV detector was used, the detection wavelength was 254 nm. The sample was prepared to dissolve in acetonitrile to form a 0.1% by weight solution, and 1 μL of this solution was introduced into the sample chamber. As a recorder, C-R7Aplus manufactured by Shimadzu Corporation was used.

Ultraviolet-visible spectroscopic analysis: For the measurement, PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used. The detection wavelength was 190 nm to 700 nm. The sample was prepared by dissolving it in acetonitrile to form a solution of 0.01 mmol / L, and placed in a quartz cell (optical path length 1 cm) for measurement.

Measurement sample: When measuring the phase structure and transition temperature (transparency point, melting point, polymerization start temperature, etc.), the compound itself was used as a sample. When measuring physical properties such as the upper limit temperature, viscosity, optical anisotropy, and dielectric anisotropy of the nematic phase, a mixture of the compound and the mother liquid crystal was used as a sample.

When a sample in which the compound was mixed with the mother liquid crystal was used, the measurement was performed as follows. A sample was prepared by mixing 15% by weight of the compound and 85% by weight of the mother liquid crystal display. Extrapolated values were calculated from the measured values of this sample according to the following equation, and these values are described. <Extrapolation value> = (100 x <measured value of sample>-<weight% of mother liquid crystal> x <measured value of mother liquid crystal>) / <weight% of compound>

When crystals (or smectic phase) are precipitated at this ratio at 25 ° C., the ratio of the compound to the mother liquid crystal is 10% by weight: 90% by weight, 5% by weight: 95% by weight, 1% by weight: 99% by weight. The physical properties of the sample were measured at the rate at which the crystals (or smectic phase) did not precipitate at 25 ° C. Unless otherwise specified, the ratio of the compound to the mother liquid crystal display is 15% by weight: 85% by weight.

When the dielectric anisotropy of the compound was zero or positive, the following mother liquid crystal display (A) was used. The ratio of each component was expressed in% by weight.

When the dielectric anisotropy of the compound was zero or negative, the following mother liquid crystal display (B) was used. The ratio of each component was expressed in% by weight.

Mother liquid crystal (C): A mother liquid crystal (C) containing the following fluorine-based compounds as components was also used. The ratio of the components of the mother liquid crystal display (C) was expressed in% by weight.

The ratio of the compound and the mother liquid crystal display (C) was 20% by weight: 80% by weight. When crystals (or smectic phase) are precipitated at this ratio at 25 ° C., the ratio of the compound to the mother liquid crystal (C) is 15% by weight: 85% by weight, 10% by weight: 90% by weight, 5% by weight. The changes were made in the order of: 95% by weight, 1% by weight: 99% by weight, and the physical characteristics of the sample were measured at a rate at which crystals (or smectic phase) did not precipitate at 25 ° C. Unless otherwise specified, the ratio of the compound to the mother liquid crystal display (C) is 20% by weight: 80% by weight.

Measurement method: The physical properties were measured by the following method. Many of these are described in the JEITA standard (JEITA ED-2521B), which is deliberated and enacted by the Japan Electronics and Information Technology Industries Association (JEITA). A modified method was also used. A thin film transistor (TFT) was not attached to the TN element used for the measurement.

(1) Phase structure: A sample was placed on a hot plate (FP-52 type hot stage manufactured by METTLER CORPORATION) of a melting point measuring device equipped with a polarizing microscope. The phase state and its change were observed with a polarizing microscope while heating this sample at a rate of 3 ° C./min to identify the type of phase.

(2) Transition temperature (° C.): A scanning calorimeter manufactured by PerkinElmer, a Diamond DSC system, or a high-sensitivity differential scanning calorimeter manufactured by SII Nanotechnology, X-DSC7000 was used for the measurement. The temperature of the sample was raised and lowered at a rate of 3 ° C./min, and the start point of the endothermic peak or the exothermic peak accompanying the phase change of the sample was determined by extrapolation to determine the transition temperature. The melting point of the compound and the polymerization initiation temperature were also measured using this device. The temperature at which a compound transitions from a solid to a liquid crystal phase such as a smectic phase or a nematic phase may be abbreviated as "lower limit temperature of the liquid crystal phase". The temperature at which a compound transitions from the liquid crystal phase to a liquid may be abbreviated as "transparency point".

The crystal was represented as C. When the crystals can be distinguished into two types, each is represented _{as C 1} or C _2. The smectic phase was represented as S and the nematic phase was represented as N. Smectic A phase, a smectic B phase, a smectic C phase, and if can be distinguished phases such as smectic F phase, represented respectively _S _A, S B, _{S C,} and the _{S F.} The liquid (isotropic) was represented as I. The transition temperature is expressed as, for example, "C 50.0 N 100.0 I". This indicates that the transition temperature from the crystal to the nematic phase is 50.0 ° C. and the transition temperature from the nematic phase to the liquid is 100.0 ° C.

(3) Compatibility of compounds: A sample in which a mother liquid crystal and a compound are mixed so that the ratio of the compound is 20% by weight, 15% by weight, 10% by weight, 5% by weight, 3% by weight, or 1% by weight. Was prepared. The sample was placed in a glass bottle and stored in a freezer at −10 ° C. or −20 ° C. for a certain period of time. It was observed whether the nematic phase of the sample was maintained or whether crystals (or smectic phase) were precipitated. The conditions under which the nematic phase was maintained were used as a measure of compatibility. The proportion of compounds and the temperature of the freezer may be changed as needed.

(4) Upper limit temperature of nematic phase ( _TNI or NI; ° C.): A sample was placed on a hot plate of a melting point measuring device equipped with a polarizing microscope and heated at a rate of 1 ° C./min. The temperature at which a part of the sample changed from the nematic phase to the isotropic liquid was measured. When the sample was a mixture of compound (1) and the mother liquid crystal display, it was indicated by the _{TNI symbol.} When the sample was a mixture of compound (1) and a compound selected from compounds (2) to (15), it was indicated by the symbol NI. The upper limit temperature of the nematic phase may be abbreviated as "upper limit temperature".

(5) Minimum Temperature of a Nematic Phase _{(T C;} ° C.): A sample having a nematic phase was put in a glass bottle, 0 ℃, -10 ℃, -20 ℃, -30 ℃, and -40 ℃ for 10 days in a freezer After storage, the liquid crystal phase was observed. _{For example, TC} was described as <-20 ° C. when the sample remained in the nematic phase at −20 ° C. and changed to a crystalline or smectic phase at −30 ° C. The lower limit temperature of the nematic phase may be abbreviated as "lower limit temperature".

(6) Viscosity (bulk viscosity; η; measured at 20 ° C.; mPa · s): An E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd. was used for the measurement.

(7) Optical anisotropy (refractive index anisotropy; measured at 25 ° C.; Δn): The measurement was performed using light having a wavelength of 589 nm and using an Abbe refractometer with a polarizing plate attached to the eyepiece. After rubbing the surface of the main prism in one direction, the sample was dropped onto the main prism. The refractive index (n∥) was measured when the direction of polarization was parallel to the direction of rubbing. The refractive index (n⊥) was measured when the direction of polarization was perpendicular to the direction of rubbing. The value of optical anisotropy (Δn) was calculated from the equation of Δn = n∥−n⊥.

(8) Specific resistance (ρ; measured at 25 ° C; Ωcm): 1.0 mL of the sample was injected into a container equipped with an electrode. A DC voltage (10 V) was applied to this container, and the DC current after 10 seconds was measured. The specific resistance was calculated from the following equation. (Specific resistance) = {(voltage) x (capacitance of container)} / {(DC current) x (vacuum permittivity)}.

(9) Voltage retention rate (VHR-1; measured at 25 ° C.;%): The TN element used for the measurement had a polyimide alignment film, and the distance (cell gap) between the two glass substrates was 5 μm. .. This device was sealed with an adhesive that cures with ultraviolet light after the sample was placed. A pulse voltage (60 microseconds at 5 V) was applied to this device to charge it. The decaying voltage was measured with a high-speed voltmeter for 16.7 milliseconds, and the area A between the voltage curve and the horizontal axis in a unit period was determined. Area B was the area when there was no attenuation. The voltage holding ratio is expressed as a percentage of the area A with respect to the area B.

(10) Voltage retention rate (VHR-2; measured at 80 ° C.;%): The voltage retention rate was measured by the above method except that the measurement was performed at 80 ° C. instead of 25 ° C. The results obtained are indicated by the symbol VHR-2.

(11) Flicker rate (measured at 25 ° C.;%): A multimedia display tester 3298F manufactured by Yokogawa Electric Corporation was used for the measurement. The light source was an LED. The sample was placed in an FFS element in a normally black mode in which the distance (cell gap) between the two glass substrates was 3.5 μm and the rubbing direction was antiparallel. This element was sealed with an UV curable adhesive. A voltage was applied to this device, and the voltage at which the amount of light transmitted through the device was maximized was measured. While applying this voltage to the element, the sensor unit was brought close to the element and the displayed flicker rate was read.

The method of measuring physical properties may differ between a sample with a positive dielectric anisotropy and a sample with a negative dielectric anisotropy. The measuring method when the dielectric anisotropy is positive is described in measurement (12a) to measurement (16a). When the dielectric anisotropy was negative, it was described in measurement (12b) to measurement (16b).

(12a) Viscosity (rotational viscosity; γ1; measured at 25 ° C; mPa · s; sample with positive dielectric anisotropy): Measurement was performed by M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, The method described in 37 (1995) was followed. The sample was placed in a TN device having a twist angle of 0 degrees and a distance (cell gap) between the two glass substrates of 5 μm. A stepwise application of 16 V to 19.5 V was applied to this device in 0.5 V increments. After no application for 0.2 seconds, application was repeated under the conditions of only one square wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of the transient current generated by this application were measured. These measurements and M.I. Rotational viscosity values were obtained from the paper by Imai et al., Equation (8) on page 40. The value of the dielectric anisotropy required for this calculation was obtained by the method described below using the device for which the rotational viscosity was measured.

(12b) Viscosity (rotational viscosity; γ1; measured at 25 ° C; mPa · s; sample with negative dielectric anisotropy): Measurement was performed by M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, The method described in 37 (1995) was followed. The sample was placed in a VA element having a distance (cell gap) between two glass substrates of 20 μm. A stepwise application of 39 V to 50 V was applied to this device in 1 V increments. After no application for 0.2 seconds, application was repeated under the conditions of only one square wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of the transient current generated by this application were measured. These measurements and M.I. Rotational viscosity values were obtained from the paper by Imai et al., Equation (8) on page 40. The permittivity anisotropy required for this calculation was measured in the section of permittivity anisotropy below.

(13a) Dielectric anisotropy (Δε; measured at 25 ° C; sample with positive permittivity anisotropy): The distance between the two glass substrates (cell gap) is 9 μm, and the twist angle is 80 degrees. A sample was placed in a TN element. A sine wave (10 V, 1 kHz) was applied to this device, and after 2 seconds, the dielectric constant (ε∥) of the liquid crystal molecule in the long axis direction was measured. A sine wave (0.5 V, 1 kHz) was applied to this element, and after 2 seconds, the permittivity (ε⊥) of the liquid crystal molecule in the minor axis direction was measured. The value of permittivity anisotropy was calculated from the equation of Δε ＝ ε∥－ε⊥.

(13b) Permittivity anisotropy (Δε; measured at 25 ° C; sample with negative permittivity anisotropy): The value of permittivity anisotropy was calculated from the equation Δε = ε∥−ε⊥. .. The permittivity (ε∥ and ε⊥) was measured as follows.
1) Measurement of permittivity (ε∥): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) was applied to a well-washed glass substrate. After rotating the glass substrate with a spinner, it was heated at 150 ° C. for 1 hour. A sample was placed in a VA element in which the distance (cell gap) between the two glass substrates was 4 μm, and this element was sealed with an adhesive that cures with ultraviolet rays. A sine wave (0.5 V, 1 kHz) was applied to this element, and after 2 seconds, the dielectric constant (ε∥) of the liquid crystal molecule in the long axis direction was measured.
2) Measurement of permittivity (ε⊥): A polyimide solution was applied to a well-cleaned glass substrate. After firing this glass substrate, the obtained alignment film was subjected to a rubbing treatment. The sample was placed in a TN element in which the distance (cell gap) between the two glass substrates was 9 μm and the twist angle was 80 degrees. A sine wave (0.5 V, 1 kHz) was applied to this element, and after 2 seconds, the permittivity (ε⊥) of the liquid crystal molecule in the minor axis direction was measured.

(14a) Elastic constant (K; measured at 25 ° C.; pN; sample with positive dielectric anisotropy): An HP4284A type LCR meter manufactured by Yokogawa Hewlett-Packard Co., Ltd. was used for the measurement. The sample was placed in a horizontally oriented element in which the distance (cell gap) between the two glass substrates was 20 μm. An electric charge of 0 V to 20 V was applied to this device, and the capacitance (C) and the applied voltage (V) were measured. These measured values are fitted using the equation (2.98) and equation (2.11) on page 75 of the "LCD Device Handbook" (Nikkan Kogyo Shimbun), and from the equation (2.99). Values for K ₁₁ and K ₃₃ were obtained. _{Next, K 22} was calculated using the values of _{K 11} and K ₃₃ obtained earlier in the equation (3.18) on page 171. The elastic constant K is represented by the average value of _{K 11} , K ₂₂ , and K _{33 thus obtained.}

(14b) Elastic constants (K ₁₁ and K ₃₃ ; measured at 25 ° C; pN; sample with negative dielectric anisotropy): An EC-1 type elastic constant measuring device manufactured by Toyo Technica Co., Ltd. was used for the measurement. .. The sample was placed in a vertically oriented element in which the distance (cell gap) between the two glass substrates was 20 μm. An electric charge of 20 V to 0 V was applied to this device, and the capacitance (C) and the applied voltage (V) were measured. These values are fitted using the equation (2.98) and equation (2.11) on page 75 of the "LCD Device Handbook" (Nikkan Kogyo Shimbun), and from the equation (2.10). The value of the elastic constant was obtained.

(15a) Threshold voltage (Vth; measured at 25 ° C.; V; sample with positive dielectric anisotropy): An LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The sample was placed in a normally white mode TN element in which the distance (cell gap) between the two glass substrates was 0.45 / Δn (μm) and the twist angle was 80 degrees. The voltage (32 Hz, square wave) applied to this device was gradually increased by 0.02 V from 0 V to 10 V. At this time, the element was irradiated with light from the vertical direction, and the amount of light transmitted through the element was measured. A voltage-transmittance curve was created in which the transmittance was 100% when the amount of light was maximum and the transmittance was 0% when the amount of light was minimum. The threshold voltage is expressed as the voltage when the transmittance reaches 90%.

(15b) Threshold voltage (Vth; measured at 25 ° C.; V; sample with negative dielectric anisotropy): An LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. A sample is placed in a VA element in normally black mode where the distance (cell gap) between the two glass substrates is 4 μm and the rubbing direction is anti-parallel, and an adhesive that cures this element with ultraviolet rays is applied. Sealed using. The voltage (60 Hz, square wave) applied to this device was gradually increased by 0.02 V from 0 V to 20 V. At this time, the element was irradiated with light from the vertical direction, and the amount of light transmitted through the element was measured. A voltage-transmittance curve was created in which the transmittance was 100% when the amount of light was maximum and the transmittance was 0% when the amount of light was minimum. The threshold voltage is expressed as the voltage when the transmittance reaches 10%.

(16a) Response time (τ; measured at 25 ° C.; ms; sample with positive dielectric anisotropy): An LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. The sample was placed in a normally white mode TN element in which the distance (cell gap) between the two glass substrates was 5.0 μm and the twist angle was 80 degrees. A square wave (60 Hz, 5 V, 0.5 seconds) was applied to this device. At this time, the element was irradiated with light from the vertical direction, and the amount of light transmitted through the element was measured. It was considered that the transmittance was 100% when the amount of light was maximum, and the transmittance was 0% when the amount of light was minimum. The rise time (τr: rise time; millisecond) is the time required for the transmittance to change from 90% to 10%. The fall time (τf: fall time; millisecond) is the time required for the transmittance to change from 10% to 90%. The response time was expressed as the sum of the rise time and the fall time obtained in this way.

(16b) Response time (τ; measured at 25 ° C.; ms; sample with negative dielectric anisotropy): An LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. The sample was placed in a normally black mode PVA element in which the distance between the two glass substrates (cell gap) was 3.2 μm and the rubbing direction was antiparallel. This element was sealed with an UV curable adhesive. A voltage slightly exceeding the threshold voltage was applied to this device for 1 minute, and then 23.5 mW / cm ² ultraviolet rays were irradiated for 8 minutes while applying a voltage of 5.6 V. A square wave (60 Hz, 10 V, 0.5 seconds) was applied to this device. At this time, the element was irradiated with light from the vertical direction, and the amount of light transmitted through the element was measured. It was considered that the transmittance was 100% when the amount of light was maximum, and the transmittance was 0% when the amount of light was minimum. The response time was expressed as the time required for the transmittance to change from 90% to 10% (fall time; fall time; millisecond).

[Synthesis Example 1]
Synthesis of compound (a-71)

First step: Synthesis of compound (t-2) Commercially available compound (t-1) (10.0 g, 68.2 mmol), iodoethane (12.8 g, 81.9 mmol), potassium carbonate (18.9 g, 136 mmol) Was dissolved in N, N-dimethylformamide (100 mL) and stirred at 70-80 ° C. for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 4: 1) to give compound (t-2) (9.83 g, 56.3 mmol) as a colorless liquid.

Second step: Synthesis of compound (t-4) Compound (t-3) (10.0 g, 63.7 mmol), 1-iodobutane (14.1 g, 76.4 mmol), potassium carbonate (17.6 g, 127 mmol) Was dissolved in DMF (100 mL) and stirred at 70-80 ° C. for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 1: 1) to give compound (t-4) (13.2 g, 61.9 mmol) as a yellow liquid.

Third step: Synthesis of compound (t-5) Compound (t-4) (13.2 g, 61.9 mmol) is dissolved in 2-propanol (140 mL) and 5% palladium-carbon (0.660 g) is added. And hydrogenated. The catalyst was filtered off, concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to give compound (t-5) (4.50 g, 24.6 mmol) as a brown solid.

Fourth step: Synthesis of compound (t-6) Compound (t-2) (4.29 g, 24.6 mmol), compound (t-5) (4.50 g, 24.6 mmol), t-butoxysodium (3) .54 g, 36.8 mmol) and Pd (amphos) Cl2 (0.174 g) were dissolved in xylene (50 mL) and stirred at 110 ° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 4: 1) to give compound (t-6) (4.67 g, 14.5 mmol) as a pink liquid.

Fifth step: Synthesis of compound (a-71) Compound (t-6) (4.67 g, 14.5 mmol) was dissolved in acetic acid (80 mL), palladium acetate (3.91 g, 17.4 mmol) was added, and the mixture was added. The mixture was heated under reflux for 50 minutes. After completion of the reaction, the mixture was cooled to room temperature, filtered through Floridil / Celite, poured into water, and extracted 3 times with toluene. The combined organic layers were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 1: 1) to give compound (a-71) (1.61 g, 5.04 mmol) as a colorless solid.

^{1 1} H-NMR (CDCl ₃ ; δppm): 8.13 (brs, J = 8.13Hz, 1H), 7.58 (d, J = 8.6Hz, 2H), 6.89 (ddd, J = 7) 9.9,7.8,1.1Hz, 2H), 4.21 (q, J = 7.0Hz, 2H), 4.14 (t, J = 6.6Hz, 2H), 1.84 (quin, quin, J = 6.7Hz, 2H), 1.54 (sex, J = 7.5Hz, 2H), 1.48 (t, J = 7.1Hz, 3H), 1.00 (t, J = 7.4Hz) , 3H).

Phase transition temperature: C 92.4 I. Upper limit temperature (NI) = −45.7 ° C.; Dielectric constant anisotropy (Δε) = −1.48; Optical anisotropy (Δn) = 0.147; Viscosity (η) = 127.4 mPa · s.

[Synthesis Example 2]
Synthesis of compound (a-74)

Compound (a-71) (0.710 g, 2.22 mmol) was dissolved in N, N-dimethylformamide (10 mL), ice-cooled, and sodium hydride (0.196 g, 4.49 mmol) was added little by little. The mixture was stirred for 30 minutes. Methyl iodide (0.821 g, 2.59 mmol) was added dropwise, and the mixture was stirred for 1 hour while cooling with ice. After completion of the reaction, the mixture was poured into water and extracted with toluene three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 1: 1) to give compound (a-74) (0.52 g, 1.56 mmol) as a colorless solid.

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.56 (d, J = 8.5Hz, 2H), 6.86 (dd, J = 7.8, 7.8, 1.4Hz, 1H), 4 .21 (s, 3H), 4.20 (q, J = 7.0Hz, 2H), 4.12 (t, J = 6.6Hz, 2H), 1.84 (quin, J = 6.6Hz, 2H), 1.55 (sext, J = 7.4Hz, 2H), 1.48 (t, J = 7.0Hz, 3H), 1.00 (t, J = 7.4Hz, 3H).

Phase transition temperature: C 71.0 I. Upper limit temperature (NI) = 37.0 ° C.; Dielectric constant anisotropy (Δε) =-3.14; Optical anisotropy (Δn) = 0.194; Viscosity (η) = 54.1 mPa · s.

[Synthesis Example 3]
Synthesis of compound (a-5)

First step: Synthesis of compound (t-8) Commercially available compound (t-7) (12.5 g, 64.1 mmol) and potassium carbonate (11.6 g, 83.4 mmol) were added to N, N-dimethylformamide (125 mL). ) Was dissolved and the temperature was raised to 60 ° C. A solution of iodoethane (11.2 g, 70.6 mmol) in N, N-dimethylformamide (20 mL) was added dropwise, and the mixture was stirred at 60 ° C. for 6 and a half hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with 1N- NaOH aqueous solution and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by short silica gel chromatography (heptane) to give compound (t-8) (12.5 g, 56.9 mmol) as a colorless liquid.

Second step: Synthesis of compound (t-9) Commercially available compound (t-7) (12.5 g, 65.5 mmol), 1-bromobutane (9.86 g, 72.0 mmol), potassium carbonate (11.8 g, 85.1 mmol) was dissolved in N, N-dimethylformamide (125 mL) and stirred at 80 ° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with a 2N-NaOH aqueous solution and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by short silica gel chromatography (heptane) to give compound (t-9) (14.2 g, 57.5 mmol) as a light brown liquid.

Third step: Synthesis of compound (t-10) Compound (t-9) (14.0 g, 56.7 mmol), benzylamine (7.29 g, 68.0 mmol), t-butoxysodium (8.17 g, 85). .0 mmol) was dissolved in toluene (196 mL), degassed under reduced pressure, palladium (0) bis (dibenzylideneacetone) (0.652 g), 2- (di-t-butylphosphino) biphenyl (0.676 g, 2.27 mmol) was added, and the mixture was heated and stirred at 60 ° C. When the heat generation had subsided, the temperature was gradually raised to the reflux temperature, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: ethyl acetate = 9: 1) to give compound (t-10) (15.0 g, 54.9 mmol) as a brown liquid.

Fourth step: Synthesis of compound (t-11) Compound (t-10) (11.0 g, 40.2 mmol), compound (t-8) (8.82 g, 40.2 mmol), t-butoxysodium (5). .80 g, 60.4 mmol) and Pd (amphos) Cl2 (0.0285 g) were dissolved in toluene (330 mL) and refluxed by heating for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 1: 1) to give compound (t-11) (11.6 g, 28.2 mmol) as a colorless liquid.

Fifth step: Synthesis of compound (t-12) Compound (t-11) (11.6 g, 28.2 mmol) was dissolved in toluene (30 mL) and 2-propanol (60 mL), and palladium hydroxide (0. 580 g) was added and hydrogenated. The catalyst was filtered off, concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane: ethyl acetate = 4: 1) to turn compound (t-12) (7.70 g, 24.0 mmol) into a brown liquid. Obtained.

Sixth step: Synthesis of compound (a-5) Compound (t-12) (6.70 g, 20.9 mmol) is dissolved in acetic acid (110 mL), palladium acetate (5.61 g, 25.0 mmol) is added, and the mixture is added. The mixture was heated under reflux for 50 minutes. After completion of the reaction, the mixture was cooled to room temperature, filtered through Floridil / Celite, poured into water, and extracted 3 times with toluene. The combined organic layers were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 1: 1) to give compound (a-5) (1.34 g, 4.20 mmol) as a colorless solid.

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.80 (brs, 1H), 7.56 (dd, J = 11.0, 2.1Hz, 2H), 6.94 (d, J = 6.9Hz) , 1H), 4.15 (q, J = 7.0Hz, 2H), 4.08 (t, J = 6.6Hz, 2H), 1.86 (quin, J = 6.6, 2H), 1 .54 (sext, J = 7.5Hz, 2H), 1.50 (t, J = 7.0Hz, 3H), 1.00 (t, J = 7.4Hz, 3H).

Phase transition temperature: C 217.3 I. Upper limit temperature (NI) = 71.0 ° C.; Dielectric constant anisotropy (Δε) = -22.5; Optical anisotropy (Δn) = 0.220; Viscosity (η) = 202.9 mPa · s.

[Synthesis Example 4]
Synthesis of compound (a-11)

Compound (a-5) (0.26 g, 0.81 mmol) was dissolved in N, N-dimethylformamide (5.0 mL), ice-cooled, and sodium hydride (0.0718 g, 1.64 mmol) was added little by little. In addition, it was stirred for 30 minutes. Methyl iodide (0.301 g, 2.11 mmol) was added dropwise, and the mixture was stirred with ice for 3 hours. After completion of the reaction, the mixture was poured into water and extracted with toluene three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 1: 1) to give compound (a-11) (0.20 g, 0.600 mmol) as a colorless solid.

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.58 (dd, J = 11.0, 2.3Hz, 2H), 6.86 (d, J = 6.8Hz, 1H), 4.21 (q) , J = 7.0Hz, 2H), 4.13 (t, J = 6.6Hz, 2H), 3.75 (s, 3H), 1.88 (quin, J = 6.6Hz, 2H), 1 .56 (sext, J = 7.5Hz, 2H), 1.52 (t, J = 7.0Hz, 3H), 1.01 (t, J = 7.4Hz, 3H).

Phase transition temperature: C 142.5 I. The physical property value could not be measured because 3% was not dissolved.

[Synthesis Example 5]
Synthesis of compound (a-36)

First step: Synthesis of compound (t-14) N, N of commercially available compound (t-13) (25.0 g, 120 mmol), iodoethane (20.5 g, 132 mmol), potassium carbonate (21.5 g, 156 mmol) -Dimethylformamide (250 mL) was dissolved and stirred at 80 ° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with a 2N-NaOH aqueous solution and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by short silica gel chromatography (toluene) to give compound (t-14) (25.8 g, 109 mmol) as a brown liquid.

Second step: Synthesis of compound (t-16) Compound (t-15) (18.0 g, 72.8 mmol), benzylamine (9.37 g, 87.4 mmol), t-butoxysodium (10.5 g, 109 mmol) ) Is dissolved in toluene (252 mL), degassed under reduced pressure, and palladium (0) bis (dibenzylideneacetone) (0.838 g), 2- (di-t-butylphosphino) biphenyl (0.870 g, 2. 91 mmol) was added, and the mixture was heated and stirred at 60 ° C. When the heat generation had subsided, the temperature was gradually raised to the reflux temperature, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: ethyl acetate = 9: 1) to give compound (t-16) (15.6 g, 57.1 mmol) as a brown liquid.

Third step: Synthesis of compound (t-17) Compound (t-14) (13.0 g, 54.9 mmol), compound (t-16) (15.0 g, 54.9 mmol), t-butoxysodium (7) .91 g, 82.3 mmol) was dissolved in toluene (450 mL), degassed under reduced pressure, Pd (amphos) Cl2 (0.0389 g) was added, and the mixture was heated and stirred at 60 ° C. When the heat generation had subsided, the temperature was gradually raised to the reflux temperature, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: toluene = 2: 1) to give compound (t-17) (15.0 g, 34.9 mmol) as a brown liquid.

Fourth step: Synthesis of compound (t-18) Compound (t-17) (15.0 g, 34.9 mmol) is dissolved in toluene (37.5 mL) and 2-propanol (75 mL), and palladium hydroxide (palladium hydroxide (15.0 g)) is dissolved in 2-propanol (75 mL). 0.75 g) was added and hydrogenated. The catalyst was filtered off, concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to give compound (t-18) (13.1 g, 38.6 mmol) as a light brown liquid.

Fifth step: Synthesis of compound (a-36) Compound (t-18) (12.0 g, 35.4 mmol) and potassium carbonate (0.489 g, 3.54 mmol) are dissolved in pivalic acid (120 mL) to acetic acid. Palladium (0.794 g) was added, and the mixture was heated under reflux in air for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and extracted with toluene three times. The combined organic layers were neutralized with sodium carbonate, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: ethyl acetate = 3: 1) to give compound (a-36) (1.50 g, 4.45 mmol) as a colorless solid.

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.83 (brs, 1H), 7.74 (d, J = 10.5Hz, 1H), 6.94 (d, J = 6.5Hz, 1H), 6.72 (d, J = 5.5Hz, 1H), 4.16 (q, J = 7.0Hz, 2H), 4.08 (t, J = 6.5Hz, 2H), 1.86 (quin) , J = 7.1, 2H), 1.55 (sex, J = 7.5Hz, 2H), 1.50 (t, J = 7.0Hz, 3H), 1.00 (t, J = 7. 5Hz, 3H).

Phase transition temperature: C 187.5 I. Upper limit temperature (NI) = 84.3 ° C.; Dielectric constant anisotropy (Δε) = -21.5; Optical anisotropy (Δn) = 0.187; Viscosity (η) = 149.4 mPa · s.

[Comparative experiment]
The dielectric anisotropy of compound (a-5) and comparative compound (Ref-1) was compared as follows. The comparative compound (Ref-1) is compound (1-2-5) described in paragraph [0143] of WO 2015/129412. The synthesis was carried out according to the method of paragraphs [0143] to [0154] of International Publication No. 2015/129412.
The dielectric anisotropy (Δε) of the compound (a-5) obtained by the synthesis of the compound (3) and the comparative compound (Ref-1) was compared. It was found that the dielectric anisotropy of compound (a-5) was much larger in the negative. Therefore, it can be concluded that compound (1) is superior to similar compounds.

It is possible to synthesize the compounds shown below by referring to the method described in the synthesis example and the section "2. Synthesis of compound (1)".

The following compounds were synthesized with reference to the method described in the synthesis example and the section "2. Synthesis of compound (1)".

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.79 (brs, 1H), 7.62 (d, J = 10.9Hz, 1H), 7.50 (d, J = 10.3Hz, 1H), 7.15 (d, J = 6.3Hz, 1H), 6.94 (d, J = 6.9Hz, 1H), 4.17 (q, J = 6.9Hz, 2H), 2.76 (t) , J = 7.5Hz, 2H), 1.67 (quin, J = 7.5Hz, 2H), 1.51 (t, J = 6.9Hz, 3H), 1.40-1.32 (m, 4H), 0.90 (t, J = 7.5Hz, 3H).

The physical characteristics of compound (a-4) were as follows.
Transition temperature: C 173.7 I.
Maximum temperature _(T NI) = 47.3 ℃; optical anisotropy (Δn) = 0.187; dielectric anisotropy (Δε) = - 15.18; Viscosity (η) = 258.2mPa · s.

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.64 (d, J = 11.5Hz, 1H), 7.53 (d, J = 9.7Hz, 1H), 7.10 (d, J = 6) .3Hz, 1H), 6.87 (d, J = 6.9Hz, 1H), 4.22 (q, J = 6.9Hz, 2H), 3.77 (s, 3H), 2.80 (t) , J = 7.5Hz, 2H), 1.70 (quin, J = 7.5Hz, 2H), 1.53 (t, J = 6.9Hz, 3H), 1.41-1.35 (m, 4H), 0.91 (t, J = 7.5Hz, 3H).

The physical characteristics of compound (a-9) were as follows.
Transition temperature: C 73.4 I.
Maximum temperature _{(T NI) = - 44.7 ℃} ; optical anisotropy (Δn) = 0.127; dielectric anisotropy (Δε) = - 7.72; viscosity (η) = 145.7mPa · s ..

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.79 (brs, 1H), 7.57 (d, J = 4.0Hz, 1H), 7.55 (d, J = 3.5Hz, 1H), 6.95 (d, J = 6.3Hz, 1H), 6.94 (d, J = 6.3Hz, 1H), 4.17 (q, J = 6.9Hz, 2H), 3.88 (d) , J = 6.3Hz, 2H), 1.98-1.94 (m, 2H), 1.87-1.80 (m, 3H), 1.51 (t, J = 6.9Hz, 3H) , 1.37-1,16 (m, 5H), 1.09 (dq, J = 2.9, 12.6Hz, 2H), 0.96 (dq, J = 2.9, 12.6Hz, 2H) ), 0.89 (t, J = 7.5Hz, 3H).

The physical characteristics of compound (b-7) were as follows.
Transition temperature: C 233.1 I.
Maximum temperature _(T NI) = 114.3 ℃; optical anisotropy (Δn) = 0.187; dielectric anisotropy (Δε) = - 10.5; Viscosity (η) = 99.4mPa · s.

^{1 1} H-NMR (CDCl ₃ ; δppm): 7.59 (d, J = 3.5Hz, 1H), 7.57 (d, J = 4.0Hz, 1H), 6.87 (d, J = 6) .9Hz, 1H), 6.85 (d, J = 6.9Hz, 1H), 4.21 (q, J = 6.9Hz, 2H), 3.91 (d, J = 6.3Hz, 2H) 3.75 (s, 3H), 2.00-1.96 (m, 2H), 1.91-1.81 (m, 3H), 1.52 (t, J = 6.9Hz, 3H) , 1.37-1,17 (m, 5H), 1.11 (dq, J = 3.5, 12.6Hz, 2H), 0.97 (dq, J = 3.5, 12.6Hz, 2H) ), 0.89 (t, J = 7.5Hz, 3H).

The physical characteristics of compound (b-19) were as follows.
Transition temperature: C 170.9 I.
Maximum temperature _(T NI) = 84.3 ℃; optical anisotropy (Δn) = 0.187; dielectric anisotropy (Δε) = - 11.5; Viscosity (η) = 145.4mPa · s.

2. Examples of Composition The present invention will be described in more detail by way of examples. The present invention is not limited by the examples, as the examples are typical. For example, the present invention includes, in addition to the composition of Examples, a mixture of the composition of Example 1 and the composition of Example 2. The present invention also includes a mixture prepared by mixing at least two of the compositions of Examples. The compounds in the use cases are represented by symbols based on the definitions in Table 2 below. In Table 2, the configuration for 1,4-cyclohexylene is trans. In use cases, the number in parentheses after the symbol represents the chemical formula to which the compound belongs. The symbol (-) means a liquid crystal compound different from the compounds (1) to (15). The proportion (percentage) of the liquid crystal compound is a weight percentage (% by weight) based on the weight of the liquid crystal composition containing no additives. Finally, the physical characteristics of the composition are summarized. The physical properties were measured according to the method described above, and the measured values were described as they were (without extrapolation).

[Usage example 1]
2O-Ca (3F, 6F) -O4 (a-5) 3%
1-BB-3 (2-8) 7%
1-BB-5 (2-8) 8%
2-BTB-1 (2-10) 3%
3-HHB-1 (3-1) 8%
3-HHB-O1 (3-1) 5%
3-HHB-3 (3-1) 14%
3-HHB-F (22-1) 4%
2-HHB (F) -F (22-2) 7%
3-HHB (F) -F (22-2) 7%
5-HHB (F) -F (22-2) 7%
3-HHB (F, F) -F (22-3) 2%
3-HHEB-F (22-10) 4%
5-HHEB-F (22-10) 4%
2-HB-C (24-1) 5%
3-HB-C (24-1) 12%
NI = 95.7 ° C; η = 22.1 mPa · s; Δn = 0.112; Δε = 3.8.

[Usage example 2]
4O-Ca (1F, 8F) -O2 (a-71) 8%
3-HH-4 (2-1) 12%
7-HB-1 (2-5) 3%
5-HB-O2 (2-5) 2%
5-HBB (F) B-2 (4-5) 7%
5-HBB (F) B-3 (4-5) 6%
3-HB-CL (21-2) 5%
3-HHB (F, F) -F (22-3) 3%
3-HBB (F, F) -F (22-24) 30%
5-HBB (F, F) -F (22-24) 24%
NI = 73.6 ° C.; η = 32.5 mPa · s; Δn = 0.125; Δε = 5.2.

[Usage example 3]
2O-Ca (3F, 6F, 9Me) -O4 (a-11) 3%
1V2-HH-1 (2-1) 3%
1V2-HH-3 (2-1) 4%
7-HB (F, F) -F (21-4) 3%
2-HHB (F) -F (22-2) 10%
3-HHB (F) -F (22-2) 10%
5-HHB (F) -F (22-2) 7%
2-HBB-F (22-22) 4%
3-HBB-F (22-22) 4%
5-HBB-F (22-22) 3%
2-HBB (F) -F (22-23) 9%
3-HBB (F) -F (22-23) 9%
5-HBB (F) -F (22-23) 16%
3-HBB (F, F) -F (22-24) 5%
5-HBB (F, F) -F (22-24) 10%

[Usage example 4]
4O-Ca (1F, 8F, 9Me) -O2 (a-74) 10%
2-HH-3 (2-1) 4%
3-HH-4 (2-1) 12%
1O1-HBBH-5 (4-1) 3%
5-HB-CL (21-2) 16%
3-HHB-F (22-1) 4%
3-HHB-CL (22-1) 3%
4-HHB-CL (22-1) 4%
3-HHB (F) -F (22-2) 5%
4-HHB (F) -F (22-2) 4%
5-HHB (F) -F (22-2) 9%
7-HHB (F) -F (22-2) 8%
5-HBB (F) -F (22-23) 4%
3-HHBB (F, F) -F (23-6) 2%
4-HHBB (F, F) -F (23-6) 3%
5-HHBB (F, F) -F (23-6) 3%
3-HH2BB (F, F) -F (23-15) 3%
4-HH2BB (F, F) -F (23-15) 3%
NI = 106.7 ° C; η = 21.6 mPa · s; Δn = 0.101; Δε = 2.7.

[Usage example 5]
2O-Ca (3F, 4F, 6F) -O4 (a-36) 2%
V-HBB-2 (3-4) 10%
1O1-HBBH-4 (4-1) 4%
1O1-HBBH-5 (4-1) 2%
3-HHB (F, F) -F (22-3) 9%
3-H2HB (F, F) -F (22-15) 8%
4-H2HB (F, F) -F (22-15) 8%
5-H2HB (F, F) -F (22-15) 8%
3-HBB (F, F) -F (22-24) 11%
5-HBB (F, F) -F (22-24) 20%
3-H2BB (F, F) -F (22-27) 10%
5-HHBB (F, F) -F (23-6) 3%
3-HH2BB (F, F) -F (23-15) 3%
5-HHEBB-F (23-17) 2%
NI = 103.0 ° C.; η = 34.3 mPa · s; Δn = 0.123; Δε = 7.8.

[Usage example 6]
2O-Ca (3F, 4F, 6F) -4 (a-232) 3%
5-HBBH-3 (4-1) 3%
3-HB (F) BH-3 (4-2) 3%
5-HB-F (21-2) 9%
6-HB-F (21-2) 9%
7-HB-F (21-2) 7%
2-HHB-OCF3 (22-1) 7%
3-HHB-OCF3 (22-1) 7%
4-HHB-OCF3 (22-1) 7%
5-HHB-OCF3 (22-1) 5%
3-HHB (F, F) -OCF2H (22-3) 4%
3-HHB (F, F) -OCF3 (22-3) 5%
3-HH2B-OCF3 (22-4) 4%
5-HH2B-OCF3 (22-4) 4%
3-HH2B (F) -F (22-5) 3%
3-HBB (F) -F (22-23) 10%
5-HBB (F) -F (22-23) 10%

[Usage example 7]
2O-Ca (3F, 6F) -5 (a-4) 3%
2-HH-5 (2-1) 5%
3-HH-4 (2-1) 4%
5-B (F) BB-2 (3-8) 4%
5-HB-CL (21-2) 11%
3-HHB (F, F) -F (22-3) 8%
3-HHEB (F, F) -F (22-12) 7%
4-HHEB (F, F) -F (22-12) 3%
5-HHEB (F, F) -F (22-12) 3%
3-HBB (F, F) -F (22-24) 20%
5-HBB (F, F) -F (22-24) 15%
2-HBEB (F, F) -F (22-39) 3%
3-HBEB (F, F) -F (22-39) 5%
5-HBEB (F, F) -F (22-39) 3%
3-HHBB (F, F) -F (23-6) 6%

[Usage example 8]
2O-Ca (3F, 4F) -4 (a-233) 3%
V2-HHB-1 (3-1) 5%
3-HB-CL (21-2) 6%
5-HB-CL (21-2) 4%
3-HHB-OCF3 (22-1) 5%
5-HHB (F) -F (22-2) 5%
V-HHB (F) -F (22-2) 5%
3-H2HB-OCF3 (22-13) 5%
5-H2HB (F, F) -F (22-15) 5%
5-H4HB-OCF3 (22-19) 12%
5-H4HB (F, F) -F (22-21) 7%
3-H4HB (F, F) -CF3 (22-21) 8%
5-H4HB (F, F) -CF3 (22-21) 10%
2-H2BB (F) -F (22-26) 5%
3-H2BB (F) -F (22-26) 10%
3-HBEB (F, F) -F (22-39) 5%

[Usage example 9]
2O-Ca (6F) -5 (a-234) 3%
3-HH-4 (2-1) 10%
3-HH-5 (2-1) 5%
3-HB-O2 (2-5) 15%
3-HHB-1 (3-1) 8%
3-HHB-O1 (3-1) 5%
5-HB-CL (21-2) 14%
7-HB (F, F) -F (21-4) 3%
2-HHB (F) -F (22-2) 7%
3-HHB (F) -F (22-2) 7%
5-HHB (F) -F (22-2) 7%
3-HHB (F, F) -F (22-3) 6%
3-H2HB (F, F) -F (22-15) 5%
4-H2HB (F, F) -F (22-15) 5%

[Usage example 10]
5-HCa (3F, 6F) -3 (b-1) 3%
3-HH-4 (2-1) 9%
3-HH-5 (2-1) 10%
3-HHB-3 (3-1) 10%
5-HB-CL (21-2) 3%
7-HB (F) -F (21-3) 7%
2-HHB (F, F) -F (22-3) 4%
3-HHB (F, F) -F (22-3) 5%
3-HHEB-F (22-10) 8%
5-HHEB-F (22-10) 8%
3-HHEB (F, F) -F (22-12) 10%
4-HHEB (F, F) -F (22-12) 5%
3-GHB (F, F) -F (22-109) 5%
4-GHB (F, F) -F (22-109) 6%
5-GHB (F, F) -F (22-109) 7%
NI = 82.6 ° C.; η = 21.7 mPa · s; Δn = 0.068; Δε = 5.9.

[Usage example 11]
3-H1OCa (3F, 6F) -3 (b-227) 3%
3-HH-VFF (2-1) 5%
5-HH-VFF (2-1) 25%
2-BTB-1 (2-10) 7%
3-HHB-1 (3-1) 4%
VFF-HHB-1 (3-1) 8%
VFF2-HHB-1 (3-1) 11%
3-H2BTB-2 (3-17) 5%
3-H2BTB-3 (3-17) 4%
3-H2BTB-4 (3-17) 4%
3-HB-C (24-1) 18%
1V2-BEB (F, F) -C (24-15) 6%

[Usage example 12]
2O-Ca (3F, 6F) -O4 (a-5) 4%
3-HH-V (2-1) 35%
3-HH-V1 (2-1) 5%
5-HH-V (2-1) 5%
3-HHB-1 (3-1) 4%
V-HHB-1 (3-1) 5%
2-BB (F) B-3 (3-6) 5%
3-HHEH-5 (3-13) 3%
1V2-BB-F (21-1) 3%
3-BB (F, F) XB (F, F) -F (22-97) 6%
3-BB (2F, 3F) XB (F, F) -F (22-114) 3%
3-HHBB (F, F) -F (23-6) 3%
3-HBBXB (F, F) -F (23-32) 3%
5-HB (F) B (F, F) XB (F, F) -F (23-41) 5%
3-BB (F) B (F, F) XB (F, F) -F (23-47) 3%
4-BB (F) B (F, F) XB (F, F) -F (23-47) 5%
5-BB (F) B (F, F) XB (F, F) -F (23-47) 3%
NI = 81.0 ° C.; η = 18.0 mPa · s; Δn = 0.102; Δε = 3.5.

[Usage example 13]
4O-Ca (1F, 8F) -O2 (a-71) 10%
3-HH-V (2-1) 31%
3-HH-V1 (2-1) 7%
V-HH-V1 (2-1) 6%
3-HHB-1 (3-1) 4%
V-HHB-1 (3-1) 5%
1-BB (F) B-2V (3-6) 4%
3-HHEH-5 (3-13) 3%
1V2-BB-F (21-1) 3%
3-BB (F, F) XB (F, F) -F (22-97) 3%
3-HHXB (F, F) -CF3 (22-100) 3%
3-GB (F, F) XB (F, F) -F (22-113) 2%
3-GB (F) B (F, F) -F (22-116) 2%
3-HHBB (F, F) -F (23-6) 3%
3-BB (F) B (F, F) XB (F, F) -F (23-47) 3%
4-BB (F) B (F, F) XB (F, F) -F (23-47) 5%
5-BB (F) B (F, F) XB (F, F) -F (23-47) 3%
3-GB (F) B (F, F) XB (F, F) -F (23-57) 3%
NI = 72.3 ° C.; η = 19.9 mPa · s; Δn = 0.106; Δε = 3.7.

[Usage example 14]
2O-Ca (3F, 6F, 9Me) -O4 (a-11) 5%
3-HH-V (2-1) 30%
3-HH-V1 (2-1) 5%
3-HHB-1 (3-1) 4%
V-HHB-1 (3-1) 5%
3-HBB-2 (3-4) 5%
V2-BB (F) B-1 (3-6) 5%
3-HHEH-3 (3-13) 3%
3-HHEH-5 (3-13) 3%
1V2-BB-F (21-1) 3%
3-BB (F, F) XB (F, F) -F (22-97) 4%
3-GB (F, F) XB (F, F) -F (22-113) 3%
3-HHBB (F, F) -F (23-6) 3%
3-HBB (F, F) XB (F, F) -F (23-38) 3%
3-BB (F) B (F, F) XB (F) -F (23-46) 3%
4-BB (F) B (F, F) XB (F, F) -F (23-47) 3%
5-BB (F) B (F, F) XB (F, F) -F (23-47) 3%
3-GB (F) B (F, F) XB (F, F) -F (23-57) 5%
4-GB (F) B (F, F) XB (F, F) -F (23-57) 3%
5-GB (F) B (F, F) XB (F, F) -F (23-57) 2%

[Usage example 15]
4O-Ca (1F, 8F, 9Me) -O2 (a-74) 9%
3-HH-V (2-1) 25%
3-HH-V1 (2-1) 4%
3-HHB-1 (3-1) 5%
V-HHB-1 (3-1) 4%
V2-BB (F) B-1 (3-6) 4%
3-HHEH-5 (3-13) 3%
3-HHEBH-3 (4-6) 4%
1V2-BB-F (21-1) 4%
3-BB (F) B (F, F) -F (22-69) 3%
3-BB (F, F) XB (F, F) -F (22-97) 5%
3-HHBB (F, F) -F (23-6) 3%
5-HB (F) B (F, F) XB (F, F) -F (23-41) 4%
4-BB (F) B (F, F) XB (F, F) -F (23-47) 5%
5-BB (F) B (F, F) XB (F, F) -F (23-47) 3%
2-dhBB (F, F) XB (F, F) -F (23-50) 2%
3-dhBB (F, F) XB (F, F) -F (23-50) 3%
3-GBB (F) B (F, F) -F (23-55) 3%
4-GBB (F) B (F, F) -F (23-55) 3%
3-BB (F, F) XB (F) B (F, F) -F (23-56) 4%
NI = 83.2 ° C; η = 25.5 mPa · s; Δn = 0.115; Δε = 5.5.

[Usage example 16]
2O-Ca (3F, 4F, 6F) -O4 (a-36) 2%
3-HH-V (2-1) 33%
3-HH-V1 (2-1) 5%
3-HHB-1 (3-1) 4%
V-HHB-1 (3-1) 5%
V2-BB (F) B-1 (3-6) 5%
3-HHEH-5 (3-13) 3%
1V2-BB-F (21-1) 3%
3-BB (F) B (F, F) -CF3 (22-69) 3%
3-BB (F, F) XB (F, F) -F (22-97) 5%
3-HHXB (F, F) -F (22-100) 5%
3-GB (F, F) XB (F, F) -F (22-113) 3%
3-GB (F) B (F) -F (22-115) 3%
3-HHBB (F, F) -F (23-6) 3%
5-HB (F) B (F, F) XB (F, F) -F (23-41) 3%
3-GB (F) B (F, F) XB (F, F) -F (23-57) 3%
3-GBB (F, F) XB (F, F) -F (23-58) 3%
4-GBB (F, F) XB (F, F) -F (23-58) 3%
5-GBB (F, F) XB (F, F) -F (23-58) 3%
3-GB (F) B (F) B (F) -F (23-59) 3%
NI = 81.9 ° C; η = 19.0 mPa · s; Δn = 0.096; Δε = 5.4.

[Usage example 17]
2O-Ca (3F, 4F, 6F) -4 (a-232) 4%
3-HH-4 (2-1) 5%
3-HB-O1 (2-5) 15%
3-HHB-1 (3-1) 6%
3-HB (2F, 3F) -O2 (5-1) 12%
5-HB (2F, 3F) -O2 (5-1) 12%
2-HHB (2F, 3F) -1 (6-1) 8%
3-HHB (2F, 3F) -1 (6-1) 12%
3-HHB (2F, 3F) -O2 (6-1) 13%
5-HHB (2F, 3F) -O2 (6-1) 13%

[Usage example 18]
2O-Ca (3F, 6F) -5 (a-4) 2%
2-HH-5 (2-1) 3%
3-HH-4 (2-1) 15%
3-HH-5 (2-1) 4%
3-HB-O2 (2-5) 12%
3-HHB-1 (3-1) 3%
3-HHB-3 (3-1) 4%
3-HHB-O1 (3-1) 3%
3-H2B (2F, 3F) -O2 (5-4) 15%
5-H2B (2F, 3F) -O2 (5-4) 13%
2-HBB (2F, 3F) -O2 (6-7) 3%
3-HBB (2F, 3F) -O2 (6-7) 9%
5-HBB (2F, 3F) -O2 (6-7) 9%
3-HHB (2F, 3Cl) -O2 (6-12) 5%

[Usage example 19]
2O-Ca (3F, 4F) -4 (a-233) 4%
2-HH-3 (2-1) 16%
2-HH-5 (2-1) 5%
3-HH-4 (2-1) 9%
3-HB-O2 (2-5) 2%
1-BB-3 (2-8) 9%
3-HHB-1 (3-1) 5%
3-HHB-O1 (3-1) 3%
5-B (F) BB-2 (3-8) 2%
3-BB (2F, 3F) -O2 (5-3) 9%
5-BB (2F, 3F) -O2 (5-3) 6%
2-HH1OB (2F, 3F) -O2 (6-5) 13%
3-HH1OB (2F, 3F) -O2 (6-5) 17%

[Usage example 20]
2O-Ca (6F) -5 (a-234) 3%
2-HH-3 (2-1) 16%
7-HB-1 (2-5) 10%
5-HB-O2 (2-5) 8%
5-HBB (F) B-2 (4-5) 7%
5-HBB (F) B-3 (4-5) 10%
3-HB (2F, 3F) -O2 (5-1) 17%
5-HB (2F, 3F) -O2 (5-1) 16%
3-HHB (2F, 3Cl) -O2 (6-12) 3%
4-HHB (2F, 3Cl) -O2 (6-12) 3%
5-HHB (2F, 3Cl) -O2 (6-12) 2%
3-HH1OCro (7F, 8F) -5 (10-6) 5%

[Usage example 21]
5-HCa (3F, 6F) -3 (b-1) 3%
3-HH-V (2-1) 29%
1-BB-3 (2-8) 10%
3-HHB-1 (3-1) 8%
5-B (F) BB-2 (3-8) 6%
3-BB (2F, 3F) -O2 (5-3) 13%
2-HH1OB (2F, 3F) -O2 (6-5) 17%
3-HH1OB (2F, 3F) -O2 (6-5) 14%

[Usage example 22]
3-H1OCa (3F, 6F) -3 (b-227) 2%
2-HH-3 (2-1) 6%
3-HH-V1 (2-1) 9%
1V2-HH-1 (2-1) 7%
1V2-HH-3 (2-1) 6%
4-HH-V (2-1) 3%
3-HHB-1 (3-1) 3%
3-HHB-3 (3-1) 2%
3-BB (2F, 3F) -O2 (5-3) 8%
5-BB (2F, 3F) -O2 (5-3) 4%
3-H1OB (2F, 3F) -O2 (5-5) 7%
3-HDhB (2F, 3F) -O2 (6-3) 7%
2-HH1OB (2F, 3F) -O2 (6-5) 8%
3-HH1OB (2F, 3F) -O2 (6-5) 17%
2-BB (2F, 3F) B-3 (7-1) 11%

[Usage example 23]
2O-Ca (3F, 6F) -O4 (a-5) 3%
3-HH-4 (2-1) 5%
3-HH-VFF (2-1) 4%
3-HB-O1 (2-5) 15%
1-BB-5 (2-8) 4%
3-HHB-1 (3-1) 6%
5-HB (2F, 3F) -O2 (5-1) 9%
V-HB (2F, 3F) -O2 (5-1) 4%
2-HHB (2F, 3F) -1 (6-1) 12%
3-HHB (2F, 3F) -1 (6-1) 12%
3-HHB (2F, 3F) -O2 (6-1) 13%
5-HHB (2F, 3F) -O2 (6-1) 13%
NI = 88.1 ° C.; η = 37.4 mPa · s; Δn = 0.096; Δε = −3.5.

[Usage example 24]
4O-Ca (1F, 8F) -O2 (a-71) 5%
2-HH-3 (2-1) 16%
7-HB-1 (2-5) 8%
5-HB-O2 (2-5) 7%
5-HBB (F) B-2 (4-5) 9%
5-HBB (F) B-3 (4-5) 10%
3-HB (2F, 3F) -O2 (5-1) 13%
5-HB (2F, 3F) -O2 (5-1) 11%
2-H1OB (2F, 3F) -O2 (5-5) 2%
3-H1OB (2F, 3F) -O2 (5-5) 2%
2OB (2F, 3F) B (F) -O2 (5-9) 2%
4OB (2F, 3F) B (F) -O2 (5-9) 2%
V-HHB (2F, 3F) -O2 (6-1) 5%
V2-HHB (2F, 3F) -O2 (6-1) 4%
5-HHB (2F, 3Cl) -O2 (6-12) 2%
3-HH1OCro (7F, 8F) -5 (10-6) 2%
NI = 74.1 ° C.; η = 24.6 mPa · s; Δn = 0.108; Δε = -2.4.

[Usage example 25]
2O-Ca (3F, 6F, 9Me) -O4 (a-11) 3%
2-HH-5 (2-1) 3%
3-HH-4 (2-1) 15%
3-HH-5 (2-1) 4%
3-HB-O2 (2-5) 12%
3-HHB-1 (3-1) 3%
3-HHB-3 (3-1) 4%
3-HHB-O1 (3-1) 3%
3-DhB (2F, 3F) -O2 (5-2) 3%
2-BB (2F, 3F) -O2 (5-3) 9%
5-H2B (2F, 3F) -O2 (5-4) 9%
3-HH2B (2F, 3F) -O2 (6-4) 3%
3-HBB (2F, 3F) -O2 (6-7) 9%
5-HBB (2F, 3F) -O2 (6-7) 9%
V-HBB (2F, 3F) -O2 (6-7) 3%
3-HHB (2F, 3Cl) -O2 (6-12) 5%
2OB (2F, 3F) B (F) H-3 (6-19) 3%

[Usage example 26]
4O-Ca (1F, 8F, 9Me) -O2 (a-74) 12%
2-HH-3 (2-1) 6%
3-HH-V1 (2-1) 10%
1V2-HH-1 (2-1) 8%
1V2-HH-3 (2-1) 7%
V-HHB-1 (3-1) 3%
V2-HHB-1 (3-1) 3%
3-HHB-1 (3-1) 3%
3-HHB-3 (3-1) 2%
5-BB (2F, 3F) -O2 (5-3) 4%
V2-BB (2F, 3F) -O2 (5-3) 4%
3-H1OB (2F, 3F) -O2 (5-5) 7%
3-HDhB (2F, 3F) -O2 (6-3) 7%
3-HH1OB (2F, 3F) -O2 (6-5) 13%
3-dhBB (2F, 3F) -O2 (6-9) 3%
3-HchB (2F, 3F) -O2 (6-18) 3%
2-BB (2F, 3F) B-3 (7-1) 5%
NI = 84.1 ° C.; η = 20.7 mPa · s; Δn = 0.114; Δε = -3.7.

[Usage example 27]
2O-Ca (3F, 4F, 6F) -O4 (a-36) 2%
2-HH-3 (2-1) 21%
3-HH-4 (2-1) 9%
3-HB-O2 (2-5) 2%
1-BB-3 (2-8) 5%
3-HHB-1 (3-1) 3%
3-HHB-O1 (3-1) 3%
V-HBB-2 (3-4) 3%
5-B (F) BB-2 (3-8) 3%
3-BB (2F, 3F) -O2 (5-3) 9%
5-BB (2F, 3F) -O2 (5-3) 6%
2-HH1OB (2F, 3F) -O2 (6-5) 13%
3-HH1OB (2F, 3F) -O2 (6-5) 13%
3-HB (2F, 3F) B-2 (7-2) 4%
V-HH2BB (2F, 3F) -O2 (8-3) 4%
NI = 76.8 ° C.; η = 17.2 mPa · s; Δn = 0.100; Δε = -3.2.

[Usage example 28]
2O-Ca (3F, 4F, 6F) -4 (a-232) 4%
3-HH-V (2-1) 28%
1-BB-3 (2-8) 7%
3-HHB-1 (3-1) 8%
5-B (F) BB-2 (3-8) 6%
3-BB (2F, 3F) -O2 (5-3) 12%
2-HH1OB (2F, 3F) -O2 (6-5) 15%
3-HH1OB (2F, 3F) -O2 (6-5) 14%
3-H2BBB (2F, 3F) -O2 (8-1) 3%
5-HFLF4-3 (13-1) 3%

The liquid crystal compound of the present invention has good physical characteristics. Liquid crystal compositions containing this compound can be widely used in liquid crystal display elements such as personal computers and televisions.

Claims

A compound represented by the formula (1).

In equation (1)
R 1 is alkyl hydrogen, or from 1 to 15 carbon atoms, in the R 1, at least one of -CH 2 -, -O -, - may be replaced by S-, or -CO-, At least one- (CH 2 ) 2- may be replaced by -CH = CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine;
R 2 is hydrogen, fluorine, chlorine, -C≡N, alkyl of -C≡C-C≡N or 1 to 15 carbon atoms, in the R 2, at least one of -CH 2 -, - It may be replaced by O-, -S-, or -CO-, and at least one- (CH 2 ) 2- may be replaced by -CH = CH- or -C≡C-, at least 1 One hydrogen may be replaced with fluorine or chlorine;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A 1 and A 2 are independently cycloalkylenes having 3 to 5 carbon atoms, and in the rings A 1 and A 2 , at least one -CH 2- can be replaced with -O-. Often, at least one-(CH 2 ) 2- may be replaced by -CH = CH-;
Rings N 1 and N 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , Dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2, 5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, benzo [b] b] thiophene-2,6-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, a 9H- xanthene-2,6-diyl or 9H- fluoren-2,7-diyl, the ring N 1 And in ring N 2 , at least one hydrogen is replaced by fluorine, chlorine, -C≡N, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , or -OCH 2 F. May;
Z 1 , Z 2 , Z 3 , and Z 4 are independently single-bonded or alkylenes with 1 to 6 carbon atoms, and in this Z 1 , Z 2 , Z 3 , and Z 4 , at least one -CH. 2 -may be replaced by -O-, -S-, or -CO-, and at least one- (CH 2 ) 2 -is replaced by -CH = CH- or -C≡C-. Also, at least one hydrogen may be replaced with fluorine or chlorine;
L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , It is -OCH 2 F, or -C≡N,;
When both L 5 and L 6 are hydrogen, at least one of L 1 , L 2 , L 3 , and L 4 is fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2, be -OCH 2 F, or -C≡N,;
When L 1 , L 2 , L 3 , and L 4 are all hydrogen, at least one of L 5 and L 6 is fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 ,
It is -OCH 2 F, or -C≡N,;
l and o are independently 0, or 1, m and n are independently 0, 1, or 2, and the sum of l, m, n, and o is an integer from 0 to 4. can be;
When l is 0, R 1 does not become hydrogen, and when o is 0, R 2 does not become hydrogen.
The compound according to claim 1, which is represented by formulas (1-1) to (1-13).

In equations (1-1) to (1-13),
R 1 is hydrogen, an alkyl having 1 to 15 carbon atoms, an alkoxy having 1 to 14 carbon atoms, an alkoxy alkyl having 2 to 14 carbon atoms, an alkenyl having 2 to 15 carbon atoms, or an alkenyloxy having 2 to 14 carbon atoms. ;
R 2 is hydrogen, fluorine, chlorine, -CF 3, -OCF 3, -C≡N, alkyl of from 1 to 15 carbon atoms, alkoxy having 1 to 14 carbon atoms, from 2 to 14 carbon atoms in the alkoxyalkyl, carbon atoms 2 to 15 alkenyl, or 2 to 14 carbon alkenyloxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A 1 and A 2 are independently cycloalkylenes having 3 to 5 carbon atoms, and in the rings A 1 and A 2 , at least one -CH 2- can be replaced with -O-. Often, at least one-(CH 2 ) 2- may be replaced by -CH = CH-;
Rings N 1 and N 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , Dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2, 5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, benzo [b] b] thiophene-2,6-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, a 9H- xanthene-2,6-diyl or 9H- fluoren-2,7-diyl, the ring N 1 And in ring N 2 , at least one hydrogen is replaced by fluorine, chlorine, -C≡N, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , or -OCH 2 F. May;
Z 1 , Z 2 , Z 3 , and Z 4 are independently single-bonded or alkylenes with 1 to 6 carbon atoms, and in this Z 1 , Z 2 , Z 3 , and Z 4 , at least one -CH. 2 -may be replaced by -O-, -S-, or -CO-, and at least one- (CH 2 ) 2 -is replaced by -CH = CH- or -C≡C-. Also, at least one hydrogen may be replaced with fluorine or chlorine;
L 1 , L 2 , L 3 , and L 4 are independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F, or -C ≡ N, and at least one of L 1 , L 2 , L 3 , and L 4 is fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , It is -OCH 2 F, or -C≡N,;
In the formula (1-1), the formula (1-3), the formula (1-5), the formula (1-7), the formula (1-9), the formula (1-11), and the formula (1-13). , R 1 does not become hydrogen, and formulas (1-1) to (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1). In -13), R 2 does not become hydrogen.
In the formulas (1-1) to (1-13),
R 1 and R 2 are independently from hydrogen, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or from 2 carbons. 9 alkenyloxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A 1 and A 2 are independently 1,2-cyclopropylene, 1,3-cyclobutylene, or 1,3-cyclopentylene;
Rings N 1 and N 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4- Diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, or benzo [b] thiophene-2,6-diyl In the rings N 1 and N 2 , at least one hydrogen is fluorine, chlorine, -C≡N, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , or. It may be replaced by -OCH 2 F;
Z 1 , Z 2 , Z 3 , and Z 4 are independently single-bonded, -O-, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-,- OCF 2 -, - (CH 2 ) 2 -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF -, - C≡C -, - (CH 2) 4 -, -(CH 2 ) 2 COO-,-(CH 2 ) 2 OCO-, -OCO (CH 2 ) 2- , -COO (CH 2 ) 2 -,-(CH 2 ) 2 CF 2 O-,-(CH 2) 2 ) 2 OCF 2- , -OCF 2 (CH 2 ) 2- , -CF 2 O (CH 2 ) 2 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH -(CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH-, -CH = CH-CH 2 O-, or -OCH 2-CH = CH-;
L 1 , L 2 , L 3 , and L 4 are independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F, or -C ≡ N, and at least one of L 1 , L 2 , L 3 , and L 4 is fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , It is -OCH 2 F, or -C≡N,;
In the formula (1-1), the formula (1-3), the formula (1-5), the formula (1-7), the formula (1-9), the formula (1-11), and the formula (1-13). , R 1 does not become hydrogen, and formulas (1-1) to (1-5), formula (1-8), formula (1-9), formula (1-12), and formula (1). -13) The compound according to claim 2, wherein R 2 does not become hydrogen.
The compound according to claim 1, which is represented by the formulas (1-14) to (1-26).

In equations (1-14) to (1-26),
R 1 is hydrogen, an alkyl having 1 to 15 carbon atoms, an alkoxy having 1 to 14 carbon atoms, an alkoxy alkyl having 2 to 14 carbon atoms, an alkenyl having 2 to 15 carbon atoms, or an alkenyloxy having 2 to 14 carbon atoms. ;
R 2 is hydrogen, fluorine, chlorine, -CF 3, -OCF 3, -C≡N, alkyl of from 1 to 15 carbon atoms, alkoxy having 1 to 14 carbon atoms, from 2 to 14 carbon atoms in the alkoxyalkyl, carbon atoms 2 to 15 alkenyl, or 2 to 14 carbon alkenyloxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A 1 and A 2 are independently cycloalkylenes having 3 to 5 carbon atoms, and in the rings A 1 and A 2 , at least one -CH 2- can be replaced with -O-. Often, at least one-(CH 2 ) 2- may be replaced by -CH = CH-;
Rings N 1 and N 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , Dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2, 5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, benzo [b] b] thiophene-2,6-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, a 9H- xanthene-2,6-diyl or 9H- fluoren-2,7-diyl, the ring N 1 And in ring N 2 , at least one hydrogen is replaced by fluorine, chlorine, -C≡N, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , or -OCH 2 F. May;
Z 1 , Z 2 , Z 3 , and Z 4 are independently single-bonded or alkylenes with 1 to 6 carbon atoms, and in this Z 1 , Z 2 , Z 3 , and Z 4 , at least one -CH. 2- May be replaced by -O-, -S-, or -CO-, and at least one- (CH 2 ) 2 -may be replaced by -CH = CH- or -C≡C-. Often, at least one hydrogen may be replaced with fluorine or chlorine;
L 5 and L 6 are independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F, or -C ≡ N. At least one of L 5 and L 6 is fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F, or -C ≡ N;
In formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26). , R 1 does not become hydrogen, and formulas (1-14) to (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1). In -26), R 2 does not become hydrogen.
In the formulas (1-14) to (1-26),
R 1 and R 2 are independently from hydrogen, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or from 2 carbons. 9 alkenyloxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Rings A 1 and A 2 are independently 1,2-cyclopropylene, 1,3-cyclobutylene, or 1,3-cyclopentylene;
Rings N 1 and N 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,4-diyl, furan-2,5-diyl, thiophene-2,4- Diyl, thiophene-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, benzo [b] thiophene-2,5-diyl, or benzo [b] thiophene-2,6-diyl In the rings N 1 and N 2 , at least one hydrogen is fluorine, chlorine, -C≡N, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , or. It may be replaced by -OCH 2 F;
Z 1 , Z 2 , Z 3 , and Z 4 are independently single-bonded, -O-, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-,- OCF 2 -, - (CH 2 ) 2 -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF -, - C≡C -, - (CH 2) 4 -, -(CH 2 ) 2 COO-,-(CH 2 ) 2 OCO-, -OCO (CH 2 ) 2- , -COO (CH 2 ) 2 -,-(CH 2 ) 2 CF 2 O-,-(CH 2) 2 ) 2 OCF 2- , -OCF 2 (CH 2 ) 2- , -CF 2 O (CH 2 ) 2 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH -(CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH-, -CH = CH-CH 2 O-, or -OCH 2-CH = CH-;
L 5 and L 6 are independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F, or -C ≡ N. At least one of L 5 and L 6 is fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F, or -C ≡ N;
In formula (1-14), formula (1-16), formula (1-18), formula (1-20), formula (1-22), formula (1-24), and formula (1-26). , R 1 does not become hydrogen, and formulas (1-14) to (1-18), formula (1-21), formula (1-22), formula (1-25), and formula (1). -26), the compound according to claim 4, wherein R 2 does not become hydrogen.
Formula (1-1-1), formula (1-3-1) to formula (1-3-6), formula (1-5-1) to formula (1-5-4), or formula (1-5-1) The compound according to any one of claims 1 to 3, represented by the formulas (1-9-3) from 9-1).

Equations (1-1-1), equations (1-3-1) to equations (1-3-6), equations (1-5-1) to equations (1-5-4), and equations (1-5-1). In equations (1-9-3) from 9-1)
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z 2 and Z 3 are independently single-bonded, -O-, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2 -,-(CH). 2 ) 2- , -CH = CH-, -C≡C-,-(CH 2 ) 4 -,-(CH 2 ) 2 COO-,-(CH 2 ) 2 OCO-, -OCO (CH 2 ) 2 -, -COO (CH 2 ) 2 -,-(CH 2 ) 2 CF 2 O-,-(CH 2 ) 2 OCF 2- , -OCF 2 (CH 2 ) 2- , -CF 2 O (CH 2 ) 2 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH- (CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH-, -CH = CH- CH 2 O- or -OCH 2- CH = CH-;
L 1 , L 2 , L 3 , and L 4 are independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -OCF 3 , -OCHF 2 , or -OCH 2 F, and L 1 , At least one of L 2 , L 3 , and L 4 is fluorine, chlorine, -CF 3 , -CHF 2 , -OCF 3 , -OCHF 2 , or -OCH 2 F;
X 1 and X 2 are independently hydrogen, fluorine, or chlorine.
Formulas (1-1-1), formulas (1-3-1) to formulas (1-3-6), formulas (1-5-1) to formulas (1-5-4), formulas (1-5-1) In equations (1-9-3) from 9-1)
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 10 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z 2 and Z 3 are independently single-bonded, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2 -,-(CH 2 ) 2- , -CH = CH-,-(CH 2 ) 4 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH- (CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH-, -CH = CH-CH 2 O-, or -OCH 2-CH = CH-;
L 1 , L 2 , L 3 , and L 4 are independently hydrogen, fluorine, chlorine, -CF 3 or -OCF 3 , and at least one of L 1 , L 2 , L 3 , and L 4. Is fluorine, chlorine, -CF 3 or -OCF 3 , and at least two of L 1 , L 2 , L 3 and L 4 are hydrogen;
The compound according to claim 6, wherein X 1 and X 2 are independently hydrogen, fluorine, or chlorine.
Formula (1-14-1), formula (1-16-1) to formula (1-16-6), formula (1-18-1) to formula (1-18-4), or formula (1-18-1) The compound according to any one of claims 1, 4, and 5, represented by the formulas (1-22-3) from 22-1).

Equations (1-14-1), equations (1-16-1) to equations (1-16-6), equations (1-18-1) to equations (1-18-4), and equations (1-18-1). From 22-1) to equation (1-22-3),
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z 2 and Z 3 are independently single-bonded, -O-, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2 -,-(CH). 2 ) 2- , -CH = CH-, -C≡C-,-(CH 2 ) 4 -,-(CH 2 ) 2 COO-,-(CH 2 ) 2 OCO-, -OCO (CH 2 ) 2 -, -COO (CH 2 ) 2 -,-(CH 2 ) 2 CF 2 O-,-(CH 2 ) 2 OCF 2- , -OCF 2 (CH 2 ) 2- , -CF 2 O (CH 2 ) 2 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH- (CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH-, -CH = CH- CH 2 O- or -OCH 2- CH = CH-;
L 5 and L 6 are independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -OCF 3 , -OCHF 2 , or -OCH 2 F, and at least one of L 5 and L 6 is , Fluorine, Chlorine, -CF 3 , -CHF 2 , -OCF 3 , -OCHF 2 , or -OCH 2 F;
X 1 and X 2 are independently hydrogen, fluorine, or chlorine.
Formulas (1-14-1), formulas (1-16-1) to formulas (1-16-6), formulas (1-18-1) to formulas (1-18-4), and formulas (1). From -22-1) to equation (1-22-3),
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 6 carbon atoms, or a branched chain alkyl having 3 to 6 carbon atoms;
Z 2 and Z 3 are independently single-bonded, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2 -,-(CH 2 ) 2- , -CH = CH-,-(CH 2 ) 4 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH- (CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH-, -CH = CH-CH 2 O-, or -OCH 2-CH = CH-;
L 5 and L 6 are independently hydrogen, fluorine, chlorine, -CF 3 , -CHF 2 , -OCF 3 , -OCHF 2 , or -OCH 2 F, and at least one of L 5 and L 6 is , Fluorine, Chlorine, -CF 3 , -CHF 2 , -OCF 3 , -OCHF 2 , or -OCH 2 F;
The compound according to claim 8, wherein X 1 and X 2 are independently hydrogen, fluorine, or chlorine.
The compound according to any one of claims 1 to 3, 6 and 7, represented by the formula (1-1-1) or the formulas (1-3-1) to (1-3-6). ..

In the formula (1-1-1), and from the formula (1-3-1) to the formula (1-3-6),
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
Z 2 is a single bond, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2 -,-(CH 2 ) 2- , -CH = CH- ,-(CH 2 ) 4 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH- (CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH- , -CH = CH-CH 2 O-, or -OCH 2- CH = CH-;
L 1 , L 2 , L 3 , and L 4 are independently hydrogen, fluorine, chlorine, -CF 3 , or -OCF 3 , and at least one of L 1 , L 2 , L 3 , and L 4. Is fluorine, chlorine, -CF 3 , or -OCF 3 , and at least two of L 1 , L 2 , L 3 , and L 4 are hydrogen;
X 1 and X 2 are independently hydrogen, fluorine, or chlorine.
To any one of claims 1, 4, 5, 8 and 9, which is represented by the formula (1-14-1) or the formula (1-16-1) to the formula (1-16-6). The compound described.

In equations (1-14-1), and from equations (1-16-1) to equations (1-16-6),
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
Z 2 is a single bond, -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CF 2 O-, -OCF 2 -,-(CH 2 ) 2- , -CH = CH- ,-(CH 2 ) 4 -,-(CH 2 ) 3 O-, -O (CH 2 ) 3- , -CH = CH- (CH 2 ) 2 -,-(CH 2 ) 2 -CH = CH- , -CH = CH-CH 2 O-, or -OCH 2- CH = CH-;
L 5 and L 6 are independently hydrogen, fluorine, chlorine, -CF 3 or -OCF 3 , and at least one of L 5 and L 6 is fluorine, chlorine, -CF 3 or -OCF 3 Is;
X 1 and X 2 are independently hydrogen, fluorine, or chlorine.
From Eqs. (1-1-1), Eqs. (1-3-1-1) to Eqs. (1-3-1-7), Eqs. (1-3-2-1), Eqs. (1-3-2- 2), Eq. (1-3-3-1), Eq. (1-3-3-2), Eq. (1-3-4-1), Eq. (1-3-4-2), Eq. (1) From claim 1 which is represented by the formula (1-3-6-1), the formula (1-3-5-2), or the formula (1-3-6-1) to the formula (1-3-6-4). The compound according to any one of 3, 6, 7, and 10.

From Eqs. (1-1-1), Eqs. (1-3-1-1) to Eqs. (1-3-1-7), Eqs. (1-3-2-1), Eqs. (1-3-2- 2), Eq. (1-3-3-1), Eq. (1-3-3-2), Eq. (1-3-4-1), Eq. (1-3-4-2), Eq. (1) In the formulas (-3-5-1), formula (1-3-5-2), and formulas (1-3-6-1) to formulas (1-3-6-4),
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
L 1 , L 2 , L 3 , and L 4 are independently hydrogen, fluorine, -CF 3 , or -OCF 3 , and at least two of L 1 , L 2 , L 3 , and L 4 are , Fluorine, -CF 3 , or -OCF 3 , and at least one of L 1 , L 2 , L 3 , and L 4 is hydrogen;
X 1 and X 2 are independently hydrogen or fluorine.
From Eqs. (1-14-1), Eqs. (1-16-1-1) to Eqs. (1-16-1-7), Eqs. (1-16-2-1), Eqs. (1-16-2-) 2), Eq. (1-16-3-1), Eq. (1-16-3-2), Eq. (1-16-4-1), Eq. (1-16-4-2), Eq. (1) -16-5-1), formula (1-16-5-2), or formula (1-16-6-1) to formula (1-16-6-4), claim 1, 4. The compound according to any one of 5, 8, 9, and 11.

Equations (1-14-1-1), equations (1-16-1-1) to equations (1-16-1-7), equations (1-16-2-1), equations (1-16-) 2-2), Equation (1-16-3-1), Equation (1-16-3-2), Equation (1-16-4-1), Equation (1-16-4-2), Equation In equations (1-16-5-1), equations (1-16-5-2), and equations (1-16-6-1) to equations (1-16-6-4).
R 1 and R 2 are independently alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkenyl with 2 to 10 carbons, or alkenyl with 2 to 9 carbons. Alkoxyoxy;
Ra is a hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms;
L 5 and L 6 are independently hydrogen, fluorine, -CF 3 or -OCF 3 , and at least one of L 5 and L 6 is fluorine, -CF 3 or -OCF 3 . ;
X 1 and X 2 are independently hydrogen or fluorine.
The compound according to any one of claims 1 to 3, 6, 7, 10, and 12, represented by formulas (1-1-1-1) to (1-1-1-7).

In equations (1-1-1-1) to (1-1-1-7),
R 1 and R 2 are independently alkyl with 1 to 7 carbons, alkoxy with 1 to 6 carbons, alkoxyalkyl with 2 to 6 carbons, alkenyl with 2 to 7 carbons, or alkenyl with 2 to 7 carbons. Alkoxyoxy.
Ra is hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms.
13. Compound.

In the formula (1-14-1-1) or the formula (1-14-1-2),
R 1 and R 2 are independently alkyl with 1 to 7 carbons, alkoxy with 1 to 6 carbons, alkoxyalkyl with 2 to 6 carbons, alkenyl with 2 to 7 carbons, or alkenyl with 2 to 7 carbons. Alkoxyoxy.
Ra is hydrogen, a linear alkyl having 1 to 4 carbon atoms, or a branched chain alkyl having 3 or 4 carbon atoms.
A liquid crystal composition containing at least one of the compounds according to any one of claims 1 to 15.
The liquid crystal composition according to claim 16, which contains at least one compound selected from the group of compounds represented by formulas (2) to (4).

In equations (2) to (4),
R 11 and R 12 are independently alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in the R 11 and R 12, at least one -CH 2 - is replaced by -O- At least one hydrogen may be replaced with fluorine;
Ring B 1 , Ring B 2 , Ring B 3 and Ring B 4 are independent, 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro- 1,4-phenylene, or pyrimidine-2,5-diyl;
Z 11 , Z 12 , and Z 13 are independently single-bonded, -COO-,-(CH 2 ) 2- , -CH = CH-, or -C≡C-.
The liquid crystal composition according to claim 16 or 17, further comprising at least one compound selected from the group of compounds represented by formulas (5) to (13).

In equations (5) to (13),
R 13 and R 14 are independently alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in the R 13 and R 14, at least one -CH 2 - is replaced by -O- At least one hydrogen may be replaced with fluorine;
R 15 is hydrogen, fluorine, alkenyl alkyl carbon atoms or 2 to 10 from 10 1 carbon atoms, in the R 15, at least one -CH 2 - may be replaced by -O-, At least one hydrogen may be replaced by fluorine;
Ring C 1 , Ring C 2 , Ring C 3 , and Ring C 4 may independently replace 1,4-cyclohexylene, 1,4-cyclohexenylene, and at least one hydrogen with fluorine 1, 4-Phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
Ring C 5 and ring C 6 are each independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene, 2,6 -Jeil;
Z 14, Z 15, Z 16 , and Z 17 are independently a single bond, -COO -, - CH 2 O -, - OCF 2 -, - (CH 2) 2 -, or -OCF 2 - (CH 2 ) 2- is;
L 11 and L 12 are independently fluorine or chlorine;
S 11 is hydrogen or methyl;
X is -CHF- or -CF 2- ;
j, k, m, n, p, q, r, and s are independently 0 or 1, and the sum of k, m, n, and p is 1 or 2, q, r, and The sum of s is 0, 1, 2, or 3, and t is 1, 2, or 3.
The liquid crystal composition according to any one of claims 16 to 18, further comprising at least one compound selected from the group of compounds represented by formulas (21) to (23).

In equations (21) to (23),
R 16 is an alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in this R 16, at least one -CH 2 - may be replaced by -O-, at least one hydrogen , May be replaced with fluorine;
X 11 is fluorine, chlorine, -CF 3 , -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCF 2 CHF 2 , or -OCF 2 CHFCF 3 ;
Ring D 1 , Ring D 2 , and Ring D 3 are independently 1,4-cyclohexylene, 1,4-phenylene, where at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl. , 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
Z 18 , Z 19 and Z 20 are independently single-bonded, -COO-, -CH 2 O-, -CF 2 O-, -OCF 2 -,-(CH 2 ) 2- , -CH = CH. -, - C≡C-, or - (CH 2) 4 - a and;
L 13 and L 14 are independently hydrogen or fluorine.
The liquid crystal composition according to any one of claims 16 to 19, further containing at least one compound selected from the group of compounds represented by the formula (24).

In equation (24)
R 17 is an alkenyl alkyl carbon atoms or 2 to 10 1 to 10 carbons, and in this R 17, at least one -CH 2 - may be replaced by -O-, at least one hydrogen May be replaced with fluorine;
X 12 is -C≡N or -C≡C-C≡N;
Ring E 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl. , Or pyrimidine-2,5-dioxane;
Z 21 is a single bond, -COO-, -CH 2 O-, -CF 2 O-, -OCF 2 -,-(CH 2 ) 2- , or -C ≡ C-;
L 15 and L 16 are independently hydrogen or fluorine;
i is 1, 2, 3, or 4.
A liquid crystal display device containing the liquid crystal composition according to any one of claims 16 to 20.