TW202206579A - Compound, liquid crystal composition and liquid crystal display element The liquid crystal compound sufficiently satisfying at least one of the following physical properties: High light stability, high clearing point (or high upper limit temperature), low minimum temperature of liquid crystal phase, low viscosity, appropriate optical anisotropy, large dielectric anisotropy, appropriate elastic constant, and phase with other liquid crystal compounds Good capacitance, etc - Google Patents

Abstract

An object of the present invention is to provide a liquid crystal compound, a liquid crystal composition containing the compound, and a liquid crystal display element containing the composition, the liquid crystal compound sufficiently satisfying at least one of the following physical properties: High light stability, high clearing point (or high upper limit temperature), low minimum temperature of liquid crystal phase, low viscosity, appropriate optical anisotropy, large dielectric anisotropy, appropriate elastic constant, and other liquid crystal compounds with good capacitance, etc. The means of the present invention are a compound represented by the formula (1), a liquid crystal composition containing the compound, and a liquid crystal display element containing the composition. In formula (1), R1 and R2 are hydrogen, alkyl, etc.; ring N1 and ring N2 are independently cycloalkylene, etc.; ring A1 and ring A2 are independently 1,4-cyclohexylene, 1,4- phenylene, etc.; Z1, Z2, Z3 and Z4 are independently a single bond, -COO-, etc.; a is 0, 1, 2 or 3, b is 0, 1, 2 or 3, and c is 0 or 1.

Description

Compound, liquid crystal composition and liquid crystal display element

The present invention relates to a liquid crystal compound, a liquid crystal composition and a liquid crystal display element. More specifically, it relates to a liquid crystal compound having a thiophene ring, a liquid crystal composition containing the compound and having a nematic phase, and a liquid crystal display element including the composition.

Liquid crystal display elements are widely used for displays of personal computers, televisions, and the like. The element utilizes physical properties such as optical anisotropy and dielectric anisotropy of liquid crystalline compounds. As the operation mode of the liquid crystal display element, there are phase change (PC) mode, twisted nematic (TN) mode, super twisted nematic (STN) mode, bistable twisted nematic ( bistable twisted nematic (BTN) mode, electrically controlled birefringence (ECB) mode, optically compensated bend (OCB) mode, in-plane switching (IPS) mode, vertical alignment (vertical) Alignment, VA) mode, fringe field switching (fringe field switching, FFS) mode, polymer stable alignment (polymer sustained alignment, PSA) mode and other modes. In the element of the PSA mode, a polymer-containing liquid crystal composition is used. In the composition, the alignment of liquid crystal molecules can be controlled by a polymer.

A liquid crystal composition having suitable physical properties can be used for such a liquid crystal display element. In order to further improve the characteristics of the element, it is preferable that the liquid crystal compound contained in the composition has the physical properties shown in the following (1) to (8). (1) High stability to heat or light, (2) High clearing point, (3) Low lower limit temperature of liquid crystal phase, (4) Low viscosity (η), (5) Optical anisotropy ( Δn) is appropriate, (6) dielectric anisotropy (Δε) is large, (7) elastic constant (K) is appropriate, and (8) compatibility with other liquid crystal compounds is good.

The effects of the physical properties of the liquid crystal compound on the characteristics of the element are as follows. The compound having high stability to heat or light as in (1) improves the voltage holding ratio of the device. Thereby, the life of the element is extended. Compounds with high-definition bright spots like (2) expand the temperature range of usable elements. Compounds having a low minimum temperature of a liquid crystal phase such as a nematic phase and a smectic phase as in (3), particularly a low minimum temperature of the nematic phase, also expand the temperature range of the usable element. Compounds with low viscosity such as (4) shorten the response time of the component.

Depending on the design of the element, a compound having appropriate optical anisotropy, that is, a large optical anisotropy or a small optical anisotropy as in (5) is required. In the case of shortening the response time by reducing the cell gap of the element, a compound having a large optical anisotropy is suitable. The compound having a large dielectric anisotropy as in (6) lowers the threshold voltage of the device. Thereby, the power consumption of the element is reduced. On the other hand, compounds with small dielectric anisotropy shorten the response time of the device by reducing the viscosity of the composition. The compound expands the temperature range in which the element can be used by increasing the upper temperature limit of the nematic phase.

Regarding (7), the compound having a large elastic constant shortens the response time of the element. Compounds with small elastic constants lower the threshold voltage of the element. Therefore, an appropriate spring constant is required according to the characteristics to be improved. A compound having good compatibility with other liquid crystal compounds like (8) is preferable. The reason for this is that the physical properties of the composition are adjusted by mixing liquid crystal compounds having different physical properties.

So far, many liquid crystal compounds have been synthesized. New liquid crystal compounds are still being developed. The reason is that good physical properties that are not present in existing compounds can be expected for novel compounds. And the reason is that a novel compound sometimes imparts an appropriate balance to at least two physical properties of the composition. Under such circumstances, a compound having favorable physical properties and an appropriate balance with respect to the above-mentioned physical properties (1) to (8) is desired.

For example, the following compound (PGT-2-1) is described on page 72 of Patent Document 1.

The following compound 5 is described on page 61 of Patent Document 2.

[現有技術文獻] [專利文獻]The following compound (PUS-3-2) is described on page 80 of patent document 3, page 69 of patent document 4, page 67 of patent document 5, and page 68 of patent document 6.

[Prior Art Document] [Patent Document]

[Patent Document 1] International Publication No. 2009/129915 [Patent Document 2] International Publication No. 2010/094455 [Patent Document 3] International Publication No. 2010/099853 [Patent Document 4] International Publication No. 2012-007096 No. [Patent Document 5] International Publication No. 2012/013281 [Patent Document 6] International Publication No. 2016-146240

[Problems to be Solved by Invention] A first problem is to provide a liquid crystal compound that satisfies at least one of the following physical properties: high stability to heat or light, high clearing point (or high upper limit temperature of nematic phase), and lower limit temperature of liquid crystal phase Low viscosity, suitable optical anisotropy, large dielectric anisotropy, suitable elastic constant, good compatibility with other liquid crystal compounds, etc. Compared with similar compounds, a compound having a high clearing point (or a high upper limit temperature of a nematic phase) and a large dielectric anisotropy is provided. The second problem is to provide a liquid crystal composition containing the compound and sufficiently satisfying at least one of the following physical properties: high thermal or light stability, high upper limit temperature of nematic phase, and lower limit temperature of nematic phase Low, low viscosity, appropriate optical anisotropy, large dielectric anisotropy, large resistivity, appropriate elastic constant, etc. This subject is to provide a liquid crystal composition having an appropriate balance with respect to at least two physical properties. The third problem is to provide a liquid crystal display element containing the composition, which can be used in a wide temperature range, a short response time, a high voltage holding ratio, a low threshold voltage, a high contrast ratio, a low flicker rate, and a long life. [Technical means to solve the problem]

式（1）中， R¹ 為氫、P-Sp-、或碳數1至15的烷基，所述R¹ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但R¹ 不為氟或氯； R² 為氫、氟、氯、-C≡N、-C≡C-C≡N、-NCS、-SCN、-SF₅ 、P-Sp-或碳數1至15的烷基，所述R² 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； P為聚合性基； Sp為間隔基或單鍵； 環N¹ 及環N² 獨立地為碳數3至5的伸環烷基，所述伸環烷基中，至少一個-CH₂ -可經-O-取代，至少一個-CH₂ CH₂ -可經-CH=CH-取代； 環A¹ 及環A² 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、二氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、吡啶-2,5-二基、或嘧啶-2,5-二基，所述環A¹ 及環A² 中，至少一個氫可經氟、氯、-C≡N、-CH₃ 、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₃ 、-OCHF₂ 、或-OCH₂ F取代； Z¹ 、Z² 、Z³ 及Z⁴ 獨立地為單鍵或碳數1至6的伸烷基，所述Z¹ 、Z² 、Z³ 及Z⁴ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； a為0、1、2或3，b為0、1、2或3，c為0或1。 [發明的效果]The present invention relates to a compound represented by formula (1), a liquid crystal composition containing the compound, and a liquid crystal display element containing the composition.

In formula (1), R ¹ is hydrogen, P-Sp-, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine; R ² is hydrogen , fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , P-Sp- or an alkyl group with 1 to 15 carbon atoms, in the R ² , at least one - CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine Substituted; P is a polymerizable group; Sp is a spacer or a single bond; Ring N ¹ and Ring N ² are independently a cycloalkylene group having 3 to 5 carbon atoms, and in the cycloextended alkyl group, at least one -CH ₂ -Can be substituted by -O-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH-; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexylene Alkenyl, 1,4-phenylene, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, the ring In A ¹ and ring A ² , at least one hydrogen may be fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F-substituted; Z ¹ , Z ² , Z ³ and Z ⁴ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in said Z ¹ , Z ² , Z ³ and Z ⁴ , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine ; a is 0, 1, 2 or 3, b is 0, 1, 2 or 3, and c is 0 or 1. [Effect of invention]

The first advantage is to provide a liquid crystal compound that satisfies at least one of the following physical properties: high stability to heat or light, high clearing point (or high upper limit temperature of nematic phase), and lower limit temperature of liquid crystal phase Low viscosity, suitable optical anisotropy, large dielectric anisotropy, suitable elastic constant, good compatibility with other liquid crystal compounds, etc. Compared with similar compounds, a compound having a high clearing point (or a high upper limit temperature of a nematic phase) and a large dielectric anisotropy is provided. The second advantage is to provide a liquid crystal composition containing the compound and sufficiently satisfying at least one of the following physical properties: high thermal or light stability, high upper limit temperature of nematic phase, and lower limit temperature of nematic phase Low, low viscosity, appropriate optical anisotropy, large dielectric anisotropy, large resistivity, appropriate elastic constant, etc. This advantage is to provide a liquid crystal composition having an appropriate balance with respect to at least two physical properties. The third advantage is to provide a liquid crystal display element containing the composition, which can be used in a wide temperature range, short response time, high voltage holding ratio, low threshold voltage, high contrast ratio, low flicker rate, and long life.

How to use the 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. "Liquid crystal compounds" are compounds having liquid crystal phases such as nematic and smectic phases, and compounds that do not have liquid crystal phases but are used for the purpose of adjusting the physical properties of compositions such as upper limit temperature, lower limit temperature, viscosity, and dielectric anisotropy. Generic term for added compounds. The compound has a six-membered ring like 1,4-cyclohexylene or 1,4-phenylene, and its molecular structure is rod-like. A "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 generating a polymer in the composition. The liquid crystal compound having an alkenyl group is not polymerizable in the meaning.

The liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. Additives are added to the composition for the purpose of further adjusting physical properties. Additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a coloring agent, and an antifoaming agent are added as necessary. The liquid crystal compounds or additives are mixed in this order. Even when an additive is added, the ratio (content) of the liquid crystal compound is represented by the weight percentage (% by weight) based on the weight of the additive-free liquid crystal composition. The ratio (addition amount) of the additive is represented by the weight percentage (% by weight) based on the weight of the additive-free liquid crystal composition. 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 (ppm) by weight are also sometimes used. The ratios of the polymerization initiator and the polymerization inhibitor are expressed based on the weight of the polymerizable compound exceptionally.

The "clearing point" is the transition temperature of the liquid crystal phase-isotropic phase of the liquid crystal compound. The "lower limit temperature of the liquid crystal phase" is the transition temperature of the solid-liquid crystal phase (smectic phase, nematic phase) of the liquid crystal compound. The "upper limit temperature of the nematic phase" is the transition temperature between the nematic phase and the isotropic phase of the mixture of the liquid crystal compound and the mother liquid crystal or the liquid crystal composition, and is sometimes simply referred to as the "upper limit temperature". The "lower limit temperature of the nematic phase" is sometimes simply referred to as the "lower limit temperature". The expression "improving the dielectric anisotropy" means that the value increases positively when the dielectric anisotropy is positive, and when the dielectric anisotropy is negative, the value negatively increases Increase. "Large voltage retention ratio" means that the element has a large voltage retention ratio not only at room temperature at the initial stage, but also at a temperature close to the upper limit temperature, and not only at room temperature after long-term use It has a large voltage holding ratio, and also has a large voltage holding ratio at a temperature close to the upper limit temperature. For a composition or element, the characteristics are sometimes investigated before and after a time-dependent test (including an accelerated deterioration test).

The compound represented by formula (1) may be simply referred to as compound (1). At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as compound (1). "Compound (1)" refers to one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. These rules also apply to compounds represented by other formulae. In formulas (1) to (15), symbols such as A ¹ , B ¹ , and C ¹ surrounded by hexagons correspond to rings such as ring A ¹ , ring B ¹ , and ring C ¹ , respectively. Hexagons represent six-membered rings like cyclohexane or benzene. The hexagon sometimes represents a condensed ring like naphthalene or a crosslinked ring like adamantane.

In the chemical formulas of the constituent compounds, the notation of the terminal group R ¹¹ is used for various compounds. In these compounds, the two groups represented by any two R ¹¹ may be the same or different. For example, there is a case where R ¹¹ of the compound (2) is an ethyl group and R ¹¹ of the compound (3) is an ethyl group. There are cases where 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 , Z ¹¹ . In compound (8), when i is 2, two rings D ¹ exist. In the compound, the two groups represented by the two rings D ¹ may be the same or different. When i is greater than 2, it also applies to any two rings D ¹ . This rule also applies to other tokens.

The expression "at least one 'A'" means that the number of 'A's is arbitrary. The expression "at least one 'A' may be substituted by 'B'" means that when the number of 'A' is one, the position of 'A' is arbitrary, and when the number of 'A' is two or more, these The location can also be selected indefinitely. This rule also applies to the expression "at least one 'A' is substituted with 'B'". The expression "at least one 'A' may be substituted with 'B', 'C' or 'D'" is meant to include any 'A' substituted with 'B', any 'A' substituted with 'C' The case and the case where any 'A' is substituted by 'D', and the case where a plurality of 'A's are substituted by at least two of 'B', 'C' and/or 'D' are further included. For example, "at least one _-CH2 -alkyl group which may be substituted with -O- or -CH=CH-" includes alkyl, alkoxy, alkoxyalkyl, alkenyl, alkoxyalkenyl, Alkenyloxyalkyl. In addition, it is not preferable that two consecutive -CH ₂ - are substituted with -O- to be -OO-. In the alkyl group etc., the case where -CH ₂ - of the methyl moiety (-CH ₂ -H) is substituted by -O- to become -OH is also not preferable.

Sometimes "R ¹¹ and R ¹² are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and among the alkyl and alkenyl groups, at least one -CH ₂ - may be via -O- Substituted, in these groups, at least one hydrogen may be replaced by fluorine". In this expression, "in these bases" can be interpreted according to the meaning of the sentence. In this expression, "these groups" refer to alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, and the like. That is, "these groups" represent all the groups described before the term "in these groups". This common sense interpretation also applies to the term "in these monovalent groups" or "in these divalent groups". For example, "these monovalent groups" means all groups described before the term "in these monovalent groups".

Halogen means fluorine, chlorine, bromine, and iodine. Preferred halogens are fluorine and chlorine. A further preferred halogen is fluorine. The alkyl group of the liquid crystal compound is linear or branched, and does not contain a cyclic alkyl group. Cycloalkyl refers to a cyclic alkyl group. Straight chain alkyl groups are generally preferred over branched alkyl groups. The same applies to terminal groups such as alkoxy groups and alkenyl groups. For the configuration related to 1,4-cyclohexylene, trans is preferred to cis in order to increase the upper temperature limit. The 2-fluoro-1,4-phenylene group refers to the following two divalent groups. In the chemical formula, fluorine can be left (L) or right (R). This rule can also be applied to asymmetric divalent radicals, such as tetrahydropyran-2,5-diyl, generated by removing two hydrogens from the ring. Straight chain alkyl groups are generally preferred over branched alkyl groups. The same applies to terminal groups such as alkoxy groups and alkenyl groups. For the configuration related to 1,4-cyclohexylene, trans is preferred to cis in order to increase the upper temperature limit. The 2-fluoro-1,4-phenylene group refers to the following two divalent groups. In the chemical formula, fluorine can be left (L) or right (R). This rule can also be applied to asymmetric divalent radicals, such as tetrahydropyran-2,5-diyl, generated by removing two hydrogens from the ring.

The present invention is the following items and the like.

式（1）中， R¹ 為氫、P-Sp-、或碳數1至15的烷基，所述R¹ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但R¹ 不為氟或氯； R² 為氫、氟、氯、-C≡N、-C≡C-C≡N、-NCS、-SCN、-SF₅ 、P-Sp-或碳數1至15的烷基，所述R² 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； P為聚合性基； Sp為間隔基或單鍵； 環N¹ 及環N² 獨立地為碳數3至5的伸環烷基，所述伸環烷基中，至少一個-CH₂ -可經-O-取代，至少一個-CH₂ CH₂ -可經-CH=CH-取代； 環A¹ 及環A² 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、二氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、吡啶-2,5-二基、或嘧啶-2,5-二基，所述環A¹ 及環A² 中，至少一個氫可經氟、氯、-C≡N、-CH₃ 、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₃ 、-OCHF₂ 、或-OCH₂ F取代； Z¹ 、Z² 、Z³ 及Z⁴ 獨立地為單鍵或碳數1至6的伸烷基，所述Z¹ 、Z² 、Z³ 及Z⁴ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； a為0、1、2或3，b為0、1、2或3，c為0或1。Item 1. A compound represented by formula (1).

In formula (1), R ¹ is hydrogen, P-Sp-, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine; R ² is hydrogen , fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , P-Sp- or an alkyl group with 1 to 15 carbon atoms, in the R ² , at least one - CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine Substituted; P is a polymerizable group; Sp is a spacer or a single bond; Ring N ¹ and Ring N ² are independently a cycloalkylene group having 3 to 5 carbon atoms, and in the cycloextended alkyl group, at least one -CH ₂ -Can be substituted by -O-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH-; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexylene Alkenyl, 1,4-phenylene, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, the ring In A ¹ and ring A ² , at least one hydrogen may be fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F-substituted; Z ¹ , Z ² , Z ³ and Z ⁴ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in said Z ¹ , Z ² , Z ³ and Z ⁴ , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine ; a is 0, 1, 2 or 3, b is 0, 1, 2 or 3, and c is 0 or 1.

式（1a）中， R¹ 為氫、P-Sp-、或碳數1至15的烷基，所述R¹ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但R¹ 不為氟或氯； R² 為氟、氯、-C≡N、-C≡C-C≡N、-NCS、-SCN、-SF₅ 、P-Sp-、或碳數1至15的烷基，所述R² 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； P為聚合性基； Sp為間隔基或單鍵； 環N¹ 為碳數3至5的伸環烷基，所述環N¹ 中，至少一個-CH₂ -可經-O-取代，至少一個-CH₂ CH₂ -可經-CH=CH-取代； 環A¹ 及環A² 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、二氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、吡啶-2,5-二基、或嘧啶-2,5-二基，所述環A¹ 及環A² 中，至少一個氫可經氟、氯、-C≡N、-CH₃ 、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₃ 、-OCHF₂ 、或-OCH₂ F取代； Z¹ 、Z² 及Z³ 獨立地為單鍵或碳數1至6的伸烷基，所述Z¹ 、Z² 及Z³ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； a為0、1、2或3，b為0、1、2或3。Item 2. The compound according to Item 1, which is represented by formula (1a).

In formula (1a), R ¹ is hydrogen, P-Sp-, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine; R ² is fluorine , chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , P-Sp-, or an alkyl group having 1 to 15 carbon atoms, in the R ² , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine ; P is a polymerizable group; Sp is a spacer or a single bond; Ring N ¹ is a cycloextended alkyl group with 3 to 5 carbon atoms, and in said ring N ¹ , at least one -CH ₂ - may be substituted by -O-, At least one -CH ₂ CH ₂ - may be substituted by -CH=CH-; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-cyclohexylene Phenyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2, 5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, in the ring A ¹ and ring A ² , At least ^one _hydrogen may be substituted with fluorine, chlorine, _-C≡N , _-CH3 , _-CF3 , -CHF2, _-CH2F , _-OCF3 , -OCHF2, or -OCH2F _; Z1, Z ² and Z ³ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in said Z ¹ , Z ² and Z ³ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; a is 0, 1, 2 or 3, b is 0 , 1, 2, or 3.

式（1-1）至式（1-10）中， R¹ 為氫、或碳數1至15的烷基，所述R¹ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但R¹ 不為氟或氯； R² 為氟、氯、-C≡N、-C≡C-C≡N、-NCS、-SCN、-SF₅ 、或碳數1至15的烷基，所述R² 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； 環N¹ 為碳數3至5的伸環烷基，所述環N¹ 中，至少一個-CH₂ -可經-O-取代，至少一個-CH₂ CH₂ -可經-CH=CH-取代； 環A¹ 及環A² 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、吡啶-2,5-二基、或嘧啶-2,5-二基，所述環A¹ 及環A² 中，至少一個氫可經氟、氯、-C≡N、-CH₃ 、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₃ 、-OCHF₂ 、或-OCH₂ F取代； Z¹ 、Z² 及Z³ 獨立地為單鍵或碳數1至6的伸烷基，所述Z¹ 、Z² 及Z³ 中，至少一個-CH₂ -可經-O-、-S-、或-CO-取代，至少一個-CH₂ CH₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。Item 3. The compound according to Item 1 or Item 2, which is represented by any one of Formula (1-1) to Formula (1-10).

In formula (1-1) to formula (1-10), R ¹ is hydrogen, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be through -O-, -S -, or -CO- substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine; R ² is fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , or an alkyl group having 1 to 15 carbon atoms, and in said R ² , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; Ring N ¹ is a cycloextended alkyl group having 3 to 5 carbon atoms, in the ring N ¹ , at least one -CH ₂ - may be substituted by -O-, and at least one -CH ₂ CH ₂ - may be substituted by -CH=CH- Substituted; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyridine pyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, the ring A ¹ and ring In A ² , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; Z ¹ , Z ² and Z ³ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in said Z ¹ , Z ² and Z ³ , at least one -CH ₂ - may be through -O-, -S -, or -CO- substituted, at least one -CH ₂ CH ₂ - may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine.

Item 4. The compound according to Item 3, wherein, in formulas (1-1) to (1-10), R ¹ is hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkoxy group having 1 to 14 carbon atoms. R ² is fluorine, chlorine, -CF ₃ , -OCF ₃ , - C≡N, alkyl having 1 to 15 carbons, alkoxy having 1 to 14 carbons, alkoxyalkyl having 2 to 14 carbons, alkenyl having 2 to 15 carbons, or 2 to 14 carbons alkenyloxy; Ring N ¹ is 1,2-cycloextended propyl, 1,3-cyclobutylene, or 1,3-cyclopentylene; Ring A ¹ and Ring A ² are independently 1,4 -cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, Pyridine-2,5-diyl, or pyrimidine-2,5-diyl, in the divalent group, at least one hydrogen can be through fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F substituted; Z ¹ , Z ² and Z ³ are independently a single bond, -O-, -CH ₂ -, -CO-, - COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH 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 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-.

式（1-1-1）、式（1-2-1）、式（1-3-1）、式（1-4-1）、式（1-5-1）、式（1-6-1）、式（1-7-1）、式（1-8-1）、式（1-8-2）、式（1-9-1）、式（1-9-2）、式（1-10-1）、及式（1-10-2）中， R¹ 為氫、碳數1至15的烷基、碳數1至14的烷氧基、碳數2至14的烷氧基烷基、碳數2至15的烯基、或碳數2至14的烯氧基； R² 為氟、氯、-CF₃ 、-OCF₃ 、-C≡N、碳數1至15的烷基、碳數1至14的烷氧基、碳數2至14的烷氧基烷基、碳數2至15的烯基、或碳數2至14的烯氧基； 環N¹ 為1,2-伸環丙基、1,3-伸環丁基、或1,3-伸環戊基； 環A¹ 及環A² 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、吡啶-2,5-二基、或嘧啶-2,5-二基，所述二價基中，至少一個氫可經氟、氯、-C≡N、-CH₃ 、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₃ 、-OCHF₂ 、或-OCH₂ F取代； Z¹ 、Z² 及Z³ 獨立地為單鍵、-O-、-CH₂ -、-CO-、-COO-、-OCO-、-CH₂ O-、-OCH₂ -、-CF₂ O-、-OCF₂ -、-CH₂ CH₂ -、-CH=CH-、-CF=CH-、-CH=CF-、-CF=CF-、-C≡C-、-(CH₂ )₄ -、-(CH₂ )₂ COO-、-(CH₂ )₂ OCO-、-OCO(CH₂ )₂ -、-COO(CH₂ )₂ -、-(CH₂ )₂ CF₂ O-、-(CH₂ )₂ OCF₂ -、-OCF₂ (CH₂ )₂ -、-CF₂ O(CH₂ )₂ -、-(CH₂ )₃ O-、-O(CH₂ )₃ -、-CH=CH-(CH₂ )₂ -、-(CH₂ )₂ -CH=CH-、-CH=CH-CH₂ O-、或-OCH₂ -CH=CH-。Item 5. The compound according to any one of Items 1 to 4, consisting of formula (1-1-1), formula (1-2-1), formula (1-3-1), formula (1- 4-1), formula (1-5-1), formula (1-6-1), formula (1-7-1), formula (1-8-1), formula (1-8-2), It is represented by any one of Formula (1-9-1), Formula (1-9-2), Formula (1-10-1), or Formula (1-10-2).

Equation (1-1-1), Equation (1-2-1), Equation (1-3-1), Equation (1-4-1), Equation (1-5-1), Equation (1-6) -1), formula (1-7-1), formula (1-8-1), formula (1-8-2), formula (1-9-1), formula (1-9-2), formula In (1-10-1) and formula (1-10-2), R ¹ is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 14 carbons, alkane having 2 to 14 carbons Oxyalkyl, alkenyl with 2 to 15 carbons, or alkenyl with 2 to 14 carbons; R ² is fluorine, chlorine, -CF ₃ , -OCF ₃ , -C≡N, carbon number 1 to 15 alkyl, alkoxy with 1 to 14 carbons, alkoxyalkyl with 2 to 14 carbons, alkenyl with 2 to 15 carbons, or alkenyl with 2 to 14 carbons; Ring N ¹ is 1,2-cyclopropylidene, 1,3-cyclohexylene, or 1,3-cyclopentylene; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4- Cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, Or pyrimidine-2,5-diyl, in the divalent group, at least one hydrogen can be changed through fluorine, chlorine, _-C≡N , _-CH3 , _-CF3 , -CHF2, _-CH2F , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F substituted; Z ¹ , Z ² and Z ³ are independently a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH 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 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-.

Item 6. The compound according to Item 5, wherein the formula (1-1-1), the formula (1-2-1), the formula (1-3-1), the formula (1-4-1), the formula (1-5-1), formula (1-6-1), formula (1-7-1), formula (1-8-1), formula (1-8-2), formula (1-9- 1), in formula (1-9-2), formula (1-10-1), or formula (1-10-2), R ¹ is hydrogen, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms. 9 alkoxy, 2 to 9 carbon alkoxyalkyl, 2 to 10 carbon alkenyl, or 2 to 9 carbon alkenyl; R ² is fluorine, -CF ₃ , -OCF ₃ , -C≡N, 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 2 carbons Alkenyloxy to 9; Ring N ¹ is 1,2-cyclopropylidene, 1,3-cyclobutylene, or 1,3-cyclopentylene; Ring A ¹ and Ring A ² are independently 1 ,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5- Diradical, in the divalent radical, at least one hydrogen can be through fluorine, chlorine, _-C≡N , _-CH3 , _-CF3 , -CHF2, _-CH2F , _-OCF3 , _-OCHF2 , or -OCH ₂ F substituted; Z ¹ , Z ² and Z ³ are independently a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, -CH=CH-, -C≡C-, -(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 -.

式（1-2-1-1）、式（1-3-1-1）至式（1-3-1-6）、及式（1-4-1-1）至式（1-4-1-18）中， R¹ 為氫、碳數1至10的烷基、碳數1至9的烷氧基、碳數2至9的烷氧基烷基、碳數2至10的烯基、或碳數2至9的烯氧基； R² 為氟、-CF₃ 、-OCF₃ 、-C≡N、碳數1至10的烷基、碳數1至9的烷氧基、碳數2至9的烷氧基烷基、碳數2至10的烯基、或碳數2至9的烯氧基； 環N¹ 為1,2-伸環丙基、1,3-伸環丁基、或1,3-伸環戊基； Z¹ 為單鍵、-O-、-CH₂ -、-CO-、-COO-、-OCO-、-CH₂ O-、-OCH₂ -、-CF₂ O-、-OCF₂ -、-CH₂ CH₂ -、-CH=CH-、-(CH₂ )₄ -、-(CH₂ )₃ O-、-O(CH₂ )₃ -、-CH=CH-(CH₂ )₂ -、-(CH₂ )₂ -CH=CH-、-CH=CH-CH₂ O-、或-OCH₂ -CH=CH-。Item 7. The compound according to any one of Items 1 to 6, consisting of formula (1-2-1-1), formula (1-3-1-1) to formula (1-3-1-6) ), or formula (1-4-1-1) to formula (1-4-1-18).

Equation (1-2-1-1), Equation (1-3-1-1) to Equation (1-3-1-6), and Equation (1-4-1-1) to Equation (1-4) -1-18), R ¹ is hydrogen, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkene with 2 to 10 carbons R ² is fluorine, -CF ₃ , -OCF ₃ , -C≡N, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, Alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons, or alkenyl having 2 to 9 carbons; Ring N ¹ is 1,2-cycloextended propyl, 1,3-extended Cyclobutyl, or 1,3-cyclopentylene; Z ¹ is a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, -CH=CH-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH2) _2- , -( _CH2 ) ₂ - _CH =CH-, -CH= _CH - _CH2O- , or -OCH2-CH=CH-.

Item 8. The compound according to Item 7, wherein the formula (1-2-1-1), the formula (1-3-1-1) to the formula (1-3-1-6), or the formula (1) -4-1-1) to formula (1-4-1-18), R ¹ is hydrogen, alkyl having 1 to 6 carbons, alkoxy having 1 to 5 carbons, alkoxy having 2 to 5 carbons alkoxyalkyl, alkenyl with 2 to 6 carbons, or alkenyl with 2 to 5 carbons; R ² is fluorine, -OCF ₃ , -C≡N, alkyl with 1 to 6 carbons, carbon alkoxy with 1 to 5 carbons, alkoxyalkyl with 2 to 5 carbons, alkenyl with 2 to 6 carbons, or alkenyloxy with 2 to 5 carbons; Ring N ¹ is 1,2-extended Cyclopropyl, 1,3-cyclobutylene, or 1,3-cyclopentylene; Z ¹ is a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, _-CH2O- , _-OCH2- , _-CF2O- , _-OCF2- , _-CH2CH2- , or -CH= _CH- .

Item 9. A liquid crystal composition containing at least one compound according to any one of Items 1 to 8.

式（2）至式（4）中， R¹¹ 及R¹² 獨立地為碳數1至10的烷基或碳數2至10的烯基，所述R¹¹ 及R¹² 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代； 環B¹ 、環B² 、環B³ 、及環B⁴ 獨立地為1,4-伸環己基、1,4-伸苯基、2-氟-1,4-伸苯基、2,5-二氟-1,4-伸苯基、或嘧啶-2,5-二基； Z¹¹ 、Z¹² 、及Z¹³ 獨立地為單鍵、-COO-、-CH₂ CH₂ -、-CH=CH-、或-C≡C-。Item 10. The liquid crystal composition according to Item 9, further comprising at least one compound selected from the group of compounds represented by formula (2) to formula (4).

In formulas (2) to (4), R ¹¹ and R ¹² are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹¹ and R ¹² , at least one -CH ₂ - may be substituted by -O-, at least one hydrogen may be substituted by fluorine; Ring B ¹ , Ring B ² , Ring B ³ , and Ring B ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene group, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; Z ¹¹ , Z ¹² , and Z ¹³ independently is a single bond, -COO-, -CH ₂ CH ₂ -, -CH=CH-, or -C≡C-.

式（5）至式（7）中， R¹³ 為碳數1至10的烷基或碳數2至10的烯基，所述R¹³ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代； X¹¹ 為氟、氯、-OCF₃ 、-OCHF₂ 、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₂ CHF₂ 、或-OCF₂ CHFCF₃ ； 環C¹ 、環C² 、及環C³ 獨立地為1,4-伸環己基、1,4-伸苯基、至少一個氫經氟取代的1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、或嘧啶-2,5-二基； Z¹⁴ 、Z¹⁵ 、及Z¹⁶ 獨立地為單鍵、-COO-、-OCO-、-CH₂ O-、-OCH₂ -、-CF₂ O-、-OCF₂ -、-CH₂ CH₂ -、-CH=CH-、-C≡C-、或-(CH₂ )₄ -； L¹¹ 及L¹² 獨立地為氫或氟。Item 11. The liquid crystal composition according to Item 9 or Item 10, further comprising at least one compound selected from the group of compounds represented by formula (5) to formula (7).

In formulas (5) to (7), R ¹³ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹³ , at least one -CH ₂ - may be substituted by -O- , at least one hydrogen can be substituted 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 ; Ring C ¹ , Ring C ² , and Ring C ³ are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene with at least one hydrogen substituted with fluorine, tetrahydropyran -2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ¹⁴ , Z ¹⁵ , and Z ¹⁶ are independently a single bond, -COO _- , -OCO-, _-CH2O- , _-OCH2- , -CF2O-, _-OCF2- , _-CH2CH2- , -CH= _CH- , -C≡C-, or -( CH ₂ ) ₄ -; L ¹¹ and L ¹² are independently hydrogen or fluorine.

式（8）中， R¹⁴ 為碳數1至10的烷基或碳數2至10的烯基，所述R¹⁴ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代； X¹² 為-C≡N或-C≡C-C≡N； 環D¹ 為1,4-伸環己基、1,4-伸苯基、至少一個氫經氟取代的1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、或嘧啶-2,5-二基； Z¹⁷ 為單鍵、-COO-、-OCO-、-CH₂ O-、-OCH₂ -、-CF₂ O-、-OCF₂ -、-CH₂ CH₂ -、或-C≡C-； L¹³ 及L¹⁴ 獨立地為氫或氟； i為1、2、3、或4。Item 12. The liquid crystal composition according to any one of Items 9 to 11, further comprising at least one compound selected from the group of compounds represented by formula (8).

In formula (8), R ¹⁴ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹⁴ , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen may be substituted by -O-. Substituted by fluorine; X ¹² is -C≡N or -C≡CC≡N; Ring D ¹ is 1,4-cyclohexylene, 1,4-phenylene, 1,4- at least one hydrogen substituted by fluorine phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ¹⁷ is a single bond, -COO- , -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, or -C≡C-; L ¹³ and L ¹⁴ are independently hydrogen or fluorine; i is 1, 2, 3, or 4.

式（11）至式（19）中， R¹⁵ 、R¹⁶ 、及R¹⁷ 獨立地為碳數1至10的烷基或碳數2至10的烯基，所述R¹⁵ 、R¹⁶ 、及R¹⁷ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代，而且，R¹⁷ 可為氫或氟； 環E¹ 、環E² 、環E³ 、及環E⁴ 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、至少一個氫經氟取代的1,4-伸苯基、四氫吡喃-2,5-二基、或十氫萘-2,6-二基； 環E⁵ 及環E⁶ 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、四氫吡喃-2,5-二基、或十氫萘-2,6-二基； Z¹⁸ 、Z¹⁹ 、Z²⁰ 、及Z²¹ 獨立地為單鍵、-COO-、-OCO-、-CH₂ O-、-OCH₂ -、-CF₂ O-、-OCF₂ -、-CH₂ CH₂ -、-CF₂ OCH₂ CH₂ -、或-OCF₂ CH₂ CH₂ -； L¹⁵ 及L¹⁶ 獨立地為氟或氯； S¹¹ 為氫或甲基； X為-CHF-或-CF₂ -； j、k、m、n、p、q、r、及s獨立地為0或1，k、m、n、及p的和為1或2，q、r、及s的和為0、1、2、或3，t為1、2、或3。Item 13. The liquid crystal composition according to any one of Items 9 to 12, further comprising at least one compound selected from the group of compounds represented by Formula (11) to (19).

In formula (11) to formula (19), R ¹⁵ , R ¹⁶ , and R ¹⁷ are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and the R ¹⁵ , R ¹⁶ , and Among R ¹⁷ , at least one -CH ₂ - may be substituted with -O-, at least one hydrogen may be substituted with fluorine, and R ¹⁷ may be hydrogen or fluorine; ring E ¹ , ring E ² , ring E ³ , and ring E ⁴ is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene with at least one hydrogen substituted with fluorine, tetrahydropyran- 2,5-diyl, or decahydronaphthalene-2,6-diyl; Ring E ⁵ and Ring E ⁶ are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4 -phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl; Z ¹⁸ , Z ¹⁹ , Z ²⁰ , and Z ²¹ are independently a single bond, -COO- , _-OCO- , _-CH2O- , _-OCH2- , _-CF2O- , _{-OCF2- , -CH2CH2- , -CF2OCH2CH2-} , _{or -OCF2CH2CH 2-} ; L ¹⁵ and L ¹⁶ 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, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2, or 3.

Item 14. A liquid crystal display element comprising the liquid crystal composition according to any one of Items 9 to 13.

The present invention also includes the following items. (a) The composition further comprising a polymer selected from the group consisting of a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a pigment, and an antifoaming agent One, two or at least three of the group of additives. (b) The liquid crystal composition, wherein the upper limit temperature of the nematic phase is 70°C or higher, the optical anisotropy (measured at 25°C) at a wavelength of 589 nm is 0.07 or higher, and the dielectric at a frequency of 1 kHz is Anisotropy (measured at 25°C) is 2 or more. (c) The liquid crystal display element, wherein the operation mode of the liquid crystal display element is TN mode, ECB mode, OCB mode, IPS mode, VA mode, FFS mode, or field-induced photo-reactive alignment (field-induced photo-reactive alignment, FPA) mode, the driving mode of the liquid crystal display element is Active Matrix (AM) mode.

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

1. Form of compound (1) The compound (1) of the present invention has a structure of a thiophene ring and a three-membered ring, a four-membered ring, or a five-membered ring. The compound (1) is characterized by having a high clearing point (or a high upper limit temperature of the nematic phase) and a large dielectric anisotropy (refer to Comparative Example 1) as compared with similar compounds. Preferred examples of compound (1) will be described. Terminal group R ¹ and terminal group R ² , P, Sp, ring N ¹ , ring N ² , ring A ¹ and ring A ² , bonding group Z ¹ , bonding group Z ² , bonding group in compound (1) Preferred examples of the group Z ³ and the bonding group Z ⁴ , a, b and c are also applicable to the lower formula of the compound (1). In the compound (1), physical properties can be arbitrarily adjusted by appropriately combining these groups. Since there is no significant difference in the physical properties of the compounds, the compound (1) may contain isotopes such as ² H (deuterium) and ¹³ C in a larger amount than the naturally occurring ratio. In addition, the definition of the symbol of compound (1) is as described in item 1.

In formula (1), R ¹ is hydrogen, P-Sp-, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine. R ² is hydrogen, fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , P-Sp- or an alkyl group having 1 to 15 carbon atoms, in the R ² , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted Substituted by fluorine or chlorine.

Preferred R1 or R2 are ^hydrogen , P ^- Sp-, alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkenyl, alkenyloxy, alkenoxyalkyl, alkoxy Alkenyl, alkylthio, alkylthioalkyl, alkenylthio, alkenylthioalkyl, alkylthioalkenyl, alkenyl, alkenyl, alkenyloxy, alkenyloxyalkyl, alkoxy carbonyl, alkynyl, and alkynyloxy. In these groups, at least one hydrogen may be substituted with fluorine or chlorine. The examples include groups in which at least two hydrogens are substituted with both fluorine and chlorine. Of these bases, straight chains are preferred to branched chains. Even if R ¹ or R ² is a branched chain, it is preferable when it is optically active. In addition to these groups, R ² may be fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, and -SF ₅ . Further preferred R ¹ or R ² is an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, an alkenyl group, an alkenyloxy group, an alkenyloxyalkyl group, or an alkoxyalkenyl group. In addition to these groups, R ² may also be fluorine, chlorine, -C≡N, -C≡CC≡N, and -NCS. Particularly preferred ^R1 or ^R2 are alkyl, alkoxy, alkoxyalkyl, alkenyl, or alkenyloxy. In addition to these groups, R ² may also be fluorine, chlorine, and -C≡N.

Specific R ¹ or R ² is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy , hexyloxy, heptyloxy, methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl , propoxyethyl, butoxymethyl, butoxyethyl, pentoxymethyl, pentoxyethyl, 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-heptenyl, 5-hexenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptene 2-propenyloxy, 2-butenyloxy, 2-pentenyloxy, 2-hexenyloxy, 1-propynyl, and 1-butynyl.

Specific R ¹ or R ² is also 2-fluoroethyl, 3-fluoropropyl, 2,2,2-trifluoroethyl, 2-fluorovinyl, 2,2-difluorovinyl, 2-fluoro -2-ethenyl, 3-fluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 4-fluoro-1-propenyl, and 4,4-difluoro-3-butene base.

Specific R ² is fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH 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 , -OCF ₂ CH ₂ F, -OCF ₂ CF ₂ CF ₃ , -OCF ₂ CHFCF ₃ , and -OCHFCF ₂ CF ₃ .

Further preferred R ¹ or R ² is methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, methoxymethyl group, 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, 2-pentenyloxy. In addition, more preferable R ² is fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, -CF ₂ CF ₃ , -CF ₂ CHF ₂ , -CF ₂ CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F, -OCF ₂ CF ₃ , -OCF ₂ CHF ₂ , and -OCF ₂ CH ₂ F. The most preferred R ¹ or R ² are methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, methoxymethyl group, ethoxymethyl, propoxymethyl, butoxymethyl, vinyl, 1-propenyl, 3-butenyl, 3-pentenyl. Besides, the most preferred R ² are fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , and -OCH ₂ F.

When R ¹ is linear, the temperature range of the liquid crystal phase is wide and the viscosity is low. When R ¹ is a branched chain, compatibility with other liquid crystal compounds is good. Compounds in which R ¹ is optically active are effective as chiral dopants. By adding this compound to the composition, a reverse twisted domain (reverse twisted domain) generated in a liquid crystal display element can be prevented. R ¹ is not an optically active compound effectively used as a component of the composition. When R1 is alkenyl, the preferred stereoconfiguration depends ^on the position of the double bond. The alkenyl compound having a preferred stereoconfiguration has a low viscosity, a high upper limit temperature, or a wide temperature range of the liquid crystal phase.

The preferred steric configuration of -CH=CH- in an alkenyl group depends on the position of the double bond. Such as -CH=CHCH ₃ , -CH=CHC ₂ H ₅ , -CH=CHC ₃ H ₇ , -CH=CHC ₄ H ₉ , -C ₂ H ₄ CH=CHCH ₃ and -C ₂ H ₄ CH=CHC ₂ Among the alkenyl groups having double bonds at odd positions like H ₅ , the trans configuration is preferred. Among alkenyl groups having a double bond at an even position, such as -CH ₂ CH=CHCH ₃ , -CH ₂ CH=CHC ₂ H ₅ and -CH ₂ CH=CHC ₃ H ₇ , the cis configuration is preferred. The alkenyl compound having a preferred stereoconfiguration has a high clearing point or a wide temperature range of the liquid crystal phase. In "Molecular Crystals and Liquid Crystals (Mol. Cryst. Liq. Cryst.)" (1985, 131, 109) and "Molecular Crystals and Liquid Crystals (Mol. Cryst. Liq. Cryst.)" (1985, 131, 327) Detailed description.

In formula (1), P is a polymerizable group; Sp is a spacer or a single bond.

The polymerizable group P is, for example, a group suitable for a polymerization reaction such as radical or ionic chain polymerization, addition polymerization, or polycondensation, or a polymer-like reaction, for example, addition or condensation to the main chain. Particularly preferred are groups for chain polymerization, particularly groups containing a C≡C double bond or a C≡C triple bond, and groups suitable for ring-opening polymerization such as oxetane and epoxide groups.

、 CH₂ =CW² -(O)_k3 -、CH₃ -CH=CH-O-、(CH₂ =CH)₂ CH-OCO-、(CH₂ =CH-CH₂ )₂ CH-OCO-、(CH₂ =CH)₂ CH-O-、(CH₂ =CH-CH₂ )₂ N-、(CH₂ =CH-CH₂ )₂ N-CO-、HO-CW² W³ -、HS-CW² W³ -、HW² N-、HO-CW² W³ -NH-、CH₂ =CW¹ -CO-NH-、CH₂ =CH-(COO)_k1 -Phe-(O)_k2 -、CH₂ =CH-(CO)_k1 -Phe-(O)_k2 -、Phe-CH=CH-、HOOC-、OCN-及W⁴ W⁵ W⁶ Si-，式中，W¹ 表示H、F、Cl、CN、CF₃ 、苯基或具有1個～5個C原子的烷基，尤其表示H、F、Cl或CH₃ ，W² 及W³ 分別獨立地表示H或具有1個～5個C原子的烷基，尤其表示H、甲基、乙基或正丙基，W⁴ 、W⁵ 及W⁶ 分別獨立地表示Cl、具有1個～5個C原子的氧雜烷基或氧雜羰基烷基，W⁷ 及W⁸ 分別相互獨立地表示H、Cl、具有1個～5個C原子的烷基，Phe表示可經如以上定義的一個以上的基L取代的1,4-伸苯基，k1、k2及k3分別相互獨立地代表0或1，k3優選表示1。Preferred radicals P are selected from CH ₂ =CW ¹ -COO-, CH ₂ =CW ¹ -CO-,

, CH ₂ =CW ² -(O) _k3 -, CH ₃ -CH=CH-O-, (CH ₂ =CH) ₂ CH-OCO-, (CH ₂ =CH-CH ₂ ) ₂ CH-OCO-, (CH ₂ =CH) ₂ CH-O-, (CH ₂ =CH-CH ₂ ) ₂ N-, (CH ₂ =CH-CH ₂ ) ₂ N-CO-, HO-CW ² W ³ -, HS- CW ² W ³ -, HW ² N-, HO-CW ² W ³ -NH-, CH ₂ =CW ¹ -CO-NH-, CH ₂ =CH-(COO) _k1 -Phe-(O) _k2 -, CH ₂ =CH-(CO) _k1 -Phe-(O) _k2 -, Phe-CH=CH-, HOOC-, OCN- and W ⁴ W ⁵ W ⁶ Si-, in the formula, W ¹ represents H, F, Cl, CN, CF ₃ , phenyl or alkyl group having 1 to 5 C atoms, especially H, F, Cl or CH ₃ , W ² and W ³ each independently represent H or have 1 to 5 atoms C-atom alkyl, especially H, methyl, ethyl or n-propyl, W ⁴ , W ⁵ and W ⁶ each independently represent Cl, oxaalkyl or oxa having 1 to 5 C atoms Carbonyl alkyl, W ⁷ and W ⁸ each independently represent H, Cl, an alkyl group having 1 to 5 C atoms, and Phe represents a 1,4-extendable group substituted with one or more groups L as defined above. In the phenyl group, k1, k2 and k3 each independently represent 0 or 1, and k3 preferably represents 1.

。Particularly preferred radicals P are CH ₂ =CW ¹ -COO-, especially CH ₂ =CH-COO-, CH ₂ =C(CH ₃ )-COO- and CH ₂ =CF-COO-, further CH ₂ = CH-O-, (CH ₂ =CH) ₂ CH-OCO-, (CH ₂ =CH) ₂ CH-O-,

.

Especially very preferred radicals P are vinyloxy, acrylates, methacrylates, fluoroacrylates, chloroacrylates, oxetanes and epoxides.

The "spacer" described as "Sp" in the specification of the present application is known to those skilled in the art and described in the literature, for example, refer to "Pure and Applied Chemistry, Pure Appl.Chem .)" Vol. 73 (No. 5), p. 888 (2001) and C. Tschierske, G. Pelzl, S. Diller Diele), Angewandte Chemie, Angew. Chem. (2004), Vol. 116, pp. 6340-6368. As long as nothing else is indicated, above and below, the term "spacer" or "spacer" refers to the interconnection of the mesogen group and the polymeric group(s) in a polymeric liquid crystal or mesogenic compound Soft base.

The preferred spacer Sp is a single bond, and is selected from the formula Sp'-X' in such a manner that the group P-Sp corresponds to the formula P-Sp'-X'-, where Sp' represents one to 20, It is preferably an alkylene group of 1 to 12 C atoms, which can be mono- or polysubstituted by F, Cl, Br, I or CN, but, in addition, one or more non-adjacent CH ₂ groups Also independently of each other via -O-, -S-, -NH-, -NR ⁰ -, -SiR ⁰⁰ R ⁰⁰⁰ -, -CO-, -COO-, -OCO-, -OCO-O-, - S-CO-, -CO-S-, -NR ⁰⁰ -CO-O-, -O-CO-NR ⁰⁰ -, -NR ⁰⁰ -CO-NR ⁰⁰ -, -CH=CH- or -C≡C- substituted so that the O and/or S atoms are not directly linked to each other,

X' means -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR ⁰⁰ -, -NR ⁰⁰ -CO-, -NR ⁰⁰ -CO-NR ⁰⁰ -, -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, -CF ₂ S-, -SCF ₂ -, -CF ₂ CH ₂ -, -CH ₂ CF ₂ -, -CF ₂ CF ₂ -, -CH=N-, -N=CH-, -N=N-, -CH=CR ⁰ -, -CY ² =CY ³ - , -C≡C-, -CH=CH-COO-, -OCO-CH=CH- or a single bond, R ⁰ , R ⁰⁰ and R ⁰⁰⁰ independently represent H or a compound having 1 to 12 C atoms. The alkyl group, and Y ² and Y ³ each independently represent H, F, Cl or CN. X' is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR ⁰ -, -NR ⁰ -CO-, -NR ⁰ -CO- NR ⁰ - or single bond.

Typical spacers Sp' are for example -(CH ₂ ) _p1 -, -(CH ₂ CH ₂ O) _q1 -CH ₂ CH ₂ -, -CH ₂ CH ₂ -S-CH ₂ CH ₂ -, -CH ₂ CH ₂ -NH-CH ₂ CH ₂ - or -(SiR ⁰⁰ R ⁰⁰⁰ -O) _p1 -, where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R ⁰⁰ and R ⁰⁰⁰ have the above-mentioned meaning.

Particularly preferred groups -X'- _Sp'- are -( _CH2 )pi-, -O-( _CH2 ) _pi- , -OCO-( _CH2 ) _pi- , -OCOO-( _CH2 ) _pi- .

Particularly preferred radicals Sp' are in each case linear ethylidene, propylidene, butylene, pentylidene, hexylidene, heptylidene, octylidene, nonylidene, decylidene , Undecyl, dodecyl, octadecyl, vinyloxyethylidene, methyleneoxybutylene, vinylthioethylidene, ethylene-N-methyliminoethylidene group, 1-methyl alkylene group, vinylidene group, propenylene group and butenylene group.

In formula (1), ring N ¹ and ring N ² are independently a cycloextended alkyl group having ₃ to 5 carbon atoms. -CH ₂ CH ₂ - may be substituted with -CH=CH-.

Examples of preferable ring N ¹ or ring N ² are divalent groups represented by the following formulae (25-1) to (25-27). Further preferable examples are the divalent groups represented by formula (25-1) to formula (25-17). Particularly preferable examples are the divalent groups represented by the formulae (25-1) to (25-3) and the formulae (25-13) to (25-17). The most preferable examples are the divalent groups represented by formula (25-1) to formula (25-3).

In formula (1), ring A ¹ and ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl , 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane Alkane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, in these divalent groups, at least one hydrogen can be changed to fluorine, chlorine, -C≡N, -CH ₃ , _-CF3 , _-CHF2 , _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2F substitution.

"In these divalent groups, at least one hydrogen can be converted to fluorine, chlorine, _-C≡N , _-CH3 , _-CF3 , -CHF2, _-CH2F , _-OCF3 , _-OCHF2 , or _-OCH2 Preferred examples of "F-substituted" are divalent groups represented by the following formulae (26-1) to (26-71). Further preferred examples are formula (26-1) to formula (26-4), formula (26-6), formula (26-10) to formula (26-15), and formula (26-54) to formula ( 26-59) represented by the divalent base.

Further preferred ring A ¹ or ring A ² is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-Difluoro-1,4-phenylene, 2,6-difluoro-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, 3-fluoropyridine-2,5-diyl, or Pyrimidine-2,5-diyl. Regarding the stereo configuration of 1,4-cyclohexylene and 1,3-dioxane-2,5-diyl, trans is better than cis.

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

When ring A ¹ or ring A ² is 1,4-cyclohexylene, the clearing point is high and the viscosity is low. When Ring A ¹ or Ring A ² is a 1,4-phenylene group or a 1,4-phenylene group in which at least one hydrogen is substituted with fluorine, the optical anisotropy is large, and the orientational order parameter relatively bigger. When the ring A ¹ or the ring A ² is a 1,4-phenylene group in which at least one hydrogen is substituted with fluorine, the dielectric anisotropy is large.

In formula (1), Z ¹ , Z ² , Z ³ and Z ⁴ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the alkylene group, at least one -CH ₂ - may be through -O -, -S-, or -CO- substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, in these divalent groups, at least one hydrogen can be substituted by fluorine or chlorine .

Specific examples of Z ¹ , Z ² , Z ³ , or Z ⁴ are a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ - , -CF ₂ O-, -OCF ₂ -, -CH ₂ CH 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-, or - OCH ₂ -CH=CH-. Regarding the steric configuration related to the double bond of the bonding group such as -CH=CH-, -CF=CF-, -CH=CH-CH ₂ O-, -OCH ₂ -CH=CH-, trans is preferred. in cis.

Preferably Z ¹ , Z ² , Z ³ , or Z ⁴ is a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, -CH=CH-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-( _CH2 ) _2- , -( _CH2 ) ₂ -CH=CH-, -CH= _CH - _CH2O- , or -OCH2-CH=CH-. Further preferred Z ¹ , Z ² , Z ³ , or Z ⁴ is a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ - , -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, -CH=CH-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ - , -CH=CH-(CH ₂ ) ₂ -, and -(CH ₂ ) ₂ -CH=CH-. Most preferably Z ¹ , Z ² , Z ³ , or Z ⁴ is a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ - , -CH ₂ CH ₂ -, or -CH=CH-.

When Z ¹ , Z ² , Z ³ , or Z ⁴ is a single bond, the chemical stability is high and the viscosity is low. When Z ¹ , Z ² , Z ³ , or Z ⁴ is -COO-, -OCO-, -CF ₂ O- or -OCF ₂ -, the viscosity is low, the dielectric anisotropy is large, and the upper limit temperature is high.

In formula (1), a is 0, 1, 2 or 3, b is 0, 1, 2 or 3, and c is 0 or 1. Preferred a are 0, 1, 2. Preferred b are 0, 1, 2. Preferably c is zero. The sum of a and b is preferably 1, 2 or 3.

In addition to the usual six-membered rings, these rings also include condensed rings or cross-linked six-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 the compound (1) has a tricyclic or tetracyclic ring, the upper limit temperature is high. When the compound (1) has a tetracyclic ring or a pentacyclic ring, the temperature range of the liquid crystal phase is wide.

More preferable examples of formula (1) are formulas (1-2) to (1-8) described in item 3. Further preferred examples of the formula (1) are the formula (1-2-1), the formula (1-3-1), the formula (1-4-1), the formula (1-5-1) described in the item 5 , formula (1-6-1), formula (1-7-1), formula (1-8-1), and formula (1-8-2). The most preferable examples of formula (1) are formula (1-2-1-1), formula (1-3-1-1) to formula (1-3-1-3), formula ( 1-4-1-1) to formula (1-4-1-7), formula (1-4-1-14) to formula (1-4-1-16).

From the viewpoint of high stability to heat or light and low viscosity, the formula (1-2-1-1) is preferred. From the viewpoint of high clearing point and good compatibility, the formulae (1-3-1-1) to (1-3-1-3) are preferred. From the viewpoint of a high clearing point and a large optical anisotropy, the formulae (1-4-1-1) to (1-4-1-4) are preferred. From the viewpoint of high clearing point, the formulae (1-4-1-5) to (1-4-1-7) and the formulae (1-4-1-14) to (1-4) are preferable -1-16).

2. Synthesis of compound (1) The synthesis method of compound (1) is demonstrated. Compound (1) can be synthesized by appropriately combining methods of synthetic organic chemistry. Methods for introducing the desired end groups, rings, and bonding groups into starting materials are described in Organic Syntheses (John Wiley & Sons, Inc.), Organic Reactions Reactions (John Wiley & Sons, Inc.), Comprehensive Organic Synthesis (Pergamon Press), Lectures on New Experimental Chemistry (Maruzen) ), etc. are recorded in the book.

2-1. Generation of Bonding Group Z As for the method of generating the bonding group Z ¹ to the bonding group Z ³ , the flow is first shown. Next, the reactions described in the schemes in the method (1) to the method (11) will be described. In the scheme, MSG ¹ (or MSG ² ) is a monovalent organic group having at least one ring. The monovalent organic groups represented by a plurality of MSG ¹ (or MSG ² ) used in the scheme may be the same or different. Compound (1A) to compound (1J) correspond to compound (1).

(1) Generation of a single key Compound (1A) is synthesized by reacting arylboronic acid (31) synthesized by a known method with halide (32) in the presence of a catalyst such as carbonate and tetrakis(triphenylphosphine)palladium. The halide (33) synthesized by a known method is reacted with n-butyllithium and then with zinc chloride, and then reacted with the halide in the presence of a catalyst such as dichlorobis(triphenylphosphine)palladium. The compound (1A) can also be synthesized by carrying out the reaction of (32).

(2) Generation of -COO- The halide (33) is reacted with n-butyllithium, and then reacted with carbon dioxide to obtain the carboxylic acid (34). Compound (35) synthesized by a known method and carboxylic acid (34) were prepared in 1,3-dicyclohexylcarbodiimide (1,3-Dicyclohexylcarbodiimide, DCC) and 4-dimethylaminopyridine ( Compound (1B) was synthesized by dehydration in the presence of 4-Dimethylaminopyridine, DMAP.

(3) Generation of -CF ₂ O- Thioester ( 36 ) is obtained by treating compound ( 1B ) with a sulfurizing agent such as Lawesson's reagent. Compound (1C) is synthesized by fluorination of thioester (36) using hydrogen fluoride pyridine complex and N-bromosuccinimide (NBS). See M. Kuroboshi et al., Chem. Lett. (1992, 827). Compound (1C) can also be synthesized by fluorinating thioester (36) with (Diethylamino)sulfur trifluoride (DAST). See J. Org. Chem., WH Bunnelle et al. (1990, 55, 768). This bonding group can also be produced by the method described in Peer. Kirsch et al., "Angew. Chem. Int. Ed." (2001, 40, 1480).

(4) Generation of -CH=CH- The halide (32) is treated with n-butyllithium and then reacted with a formamide such as N,N-Dimethylformamide (DMF) to give the aldehyde (38). Phosphorus ylide is produced by treating the phosphonium salt (37) synthesized by a known method with a base such as potassium tert-butoxide. Compound (1D) is synthesized by reacting the phosphorus ylide with aldehyde (38). Depending on the reaction conditions, a cis isomer is produced, and if necessary, the cis isomer is isomerized into a trans isomer by a known method.

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

(6) Production of -(CH ₂ ) ₄ - Using the phosphonium salt (39) in place of the phosphonium salt (37), the compound having -(CH ₂ ) ₂ -CH=CH- was obtained according to the method of the method (4). This is subjected to catalytic hydrogenation to synthesize compound (1F).

(7) Generation of -CH ₂ CH=CHCH ₂ - Phosphonium salt (40) was used instead of phosphonium salt (37), and aldehyde (41) was used instead of aldehyde (38), and the compound was synthesized according to the method of method (4). (1G). Depending on the reaction conditions, a trans isomer is produced, and if necessary, the trans isomer is isomerized into a cis isomer by a known method.

(8) Generation of -C≡C- Compound (32) is obtained by reacting 2-methyl-3-butyn-2-ol with halide (33) in the presence of a catalyst of dichloropalladium and copper halide, followed by deprotection under basic conditions . Compound (1H) is synthesized by reacting compound (42) with halide (32) in the presence of a catalyst of dichloropalladium and copper halide.

(9) Generation of -CF=CF- The halide (33) is treated with n-butyllithium, and then reacted with tetrafluoroethylene to obtain the 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 compound (44) is obtained by reducing the aldehyde (38) with a reducing agent such as sodium borohydride. Bromide (45) is obtained by brominating compound (44) with hydrobromic acid or the like. Compound (1J) is synthesized by reacting bromide (45) with compound (46) in the presence of a base such as potassium carbonate.

(11) Generation of -CF ₂ CF ₂ - According to the method described in "J. Am. Chem. Soc." (2001, 123, 5414.), in the presence of a hydrogen fluoride catalyst, using The diketone (-COCO-) is fluorinated by sulfur fluoride to obtain a compound having -(CF ₂ ) ₂ -.

2-2. The formation of ring A ¹ and ring A ² is related to, for example, 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,6-difluoro- 1,4-phenylene-like ring, the starting material is commercially available or the formation method is widely known. For the production of tetrahydropyran-2,5-diyl, refer to paragraphs 0084 to 0107 of Japanese Patent Laid-Open No. 2013-241397. For the production of 1,3-dioxane-2,5-diyl group, refer to paragraphs 0096 to 0119 of Japanese Patent Laid-Open No. 2009-132927. For the production of pyrimidine-2,5-diyl and pyridine-2,5-diyl, refer to paragraphs 0086 to 0094 of International Publication No. WO 2010/047260.

2-3. Method for synthesizing compound (1) Examples of the method for synthesizing compound (1) are as follows. (52) is obtained by reacting (51) synthesized by a known method with n-BuLi and then reacting with pinacol isopropoxyboronic acid. (53) is obtained by reacting (52) in the presence of trimethylolethane and sodium hydroxide. (55) is obtained by halogenating (54). Compound (1) is synthesized by subjecting (55) and (53) to a Suzuki coupling reaction. In these compounds, the definitions of symbols such as R ¹ and ring A ¹ are the same as those of the symbols described in Item 1.

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

Table 1. Dielectric anisotropy of constituent compounds composition Ingredient compounds Dielectric Anisotropy Ingredient A Compound (1) positive Ingredient B Compound (2) to Compound (4) little Ingredient C Compound (5) to Compound (7) positive Ingredient D Compound (8) positive Ingredient E Compound (11) to Compound (19) negative big

The composition contains compound (1) as component A, and preferably further contains a liquid crystal compound selected from the group consisting of component B, component C, component D, and component E shown in Table 1. When preparing the composition, it is preferable to select Component B, Component C, Component D, and Component E in consideration of the positive and negative and the magnitude of the dielectric anisotropy. The composition may contain a liquid crystal compound different from the compound (1) to the compound (8) and the compound (11) to the compound (19). The composition may not contain such a liquid crystal compound.

Component B is a compound whose two terminal groups are alkyl groups or the like. Preferred examples of component B include compound (2-1) to compound (2-11), compound (3-1) to compound (3-19), and compound (4-1) to compound (4-7) ). In these compounds, R ¹¹ and R ¹² are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the alkyl and alkenyl groups, at least one -CH ₂ - may be through -O- Substituted, in these groups, at least one hydrogen may be substituted with fluorine.

Component B has a small dielectric anisotropy. Ingredient B is close to neutral. Compound (2) has the effect of reducing viscosity or adjusting optical anisotropy. The compound (3) and the compound (4) have the effect of widening the temperature range of the nematic phase and adjusting the optical anisotropy by increasing the upper limit temperature.

As the content of component B increases, 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, the higher the content, the better. When preparing compositions for modes such as IPS and VA, the content of Component B is preferably 30% by weight or more, and more preferably 40% by weight or more, based on the weight of the liquid crystal composition.

Component C is a compound having a halogen or fluorine-containing group at the right terminal. Preferred examples of component C include compound (5-1) to compound (5-16), compound (6-1) to compound (6-116), compound (7-1) to compound (7-59) ). In these compounds, R ¹³ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and among the alkyl and alkenyl groups, at least one -CH ₂ - may be substituted by -O-, among these groups , at least one hydrogen can 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 C has positive dielectric anisotropy and very good stability to heat or light, so it is used in the preparation of compositions for modes such as IPS, FFS, and OCB. The content of the component C is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, further preferably in the range of 40% by weight to 95% by weight, based on the weight of the liquid crystal composition . When adding Component C to a composition having a negative dielectric anisotropy, the content of Component C is preferably 30% by weight or less. By adding the component C, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

Component D is a compound (8) whose right terminal group is -C≡N or -C≡CC≡N. Preferable examples of component D include compound (8-1) to compound (8-64). In these compounds, R ¹⁴ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and among the alkyl and alkenyl groups, at least one -CH ₂ - may be substituted by -O-, among these groups , at least one hydrogen can be replaced by fluorine. X ¹² is -C≡N or -C≡CC≡N.

The dielectric anisotropy of Component D is positive and its value is large, so it is used in the case of preparing a composition for modes such as TN. By adding the component D, the dielectric anisotropy of the composition can be improved. Component D has the effect of expanding the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. Component D is also useful for adjustment of the voltage-transmittance curve of the element.

In the case of preparing a composition for modes such as TN, the content of the component D is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, based on the weight of the liquid crystal composition, Further preferred is the range of 40% by weight to 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, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

Ingredient E is compound (11) to compound (19). These compounds have a phenylene substituted with two halogens in the lateral position like 2,3-difluoro-1,4-phenylene. Preferred examples of component E include compound (11-1) to compound (11-9), compound (12-1) to compound (12-19), compound (13-1), and compound (13-2) , compound (14-1) to compound (14-3), compound (15-1) to compound (15-3), compound (16-1) to compound (16-11), compound (17-1) to Compound (17-3), Compound (18-1) to Compound (18-3), and Compound (19-1). In these compounds, R ¹⁵ , R ¹⁶ , and R ¹⁷ are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and among the alkyl and alkenyl groups, at least one -CH ₂ -may be Substituted with -O-, in these groups, at least one hydrogen may be substituted with fluorine, and R ¹⁷ may be hydrogen or fluorine.

The dielectric anisotropy of the component E is negative and large. Component E is used in the preparation of modal compositions such as IPS, VA, and PSA. As the content of component E increases, the dielectric anisotropy of the composition becomes negative and increases, but the viscosity increases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the content is preferably as small as possible. Considering that the dielectric anisotropy is about -5, the content is preferably 40% by weight or more in order to perform sufficient voltage driving.

Among the components E, since the compound (11) is a bicyclic compound, it has the effect of reducing the viscosity, adjusting the optical anisotropy, or improving the dielectric anisotropy. The compound (12) and the compound (13) are tricyclic compounds, and the compound (14) is a tetracyclic compound, and therefore have the effect of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. Compounds (15) to (19) have an effect of increasing the dielectric anisotropy.

When preparing compositions for modes such as IPS, VA, and PSA, the content of Component E is preferably 40% by weight or more, and more preferably 50% by weight to 95% by weight, based on the weight of the liquid crystal composition. When the component E is added to the composition having positive dielectric anisotropy, the content of the component E is preferably 30% by weight or less. By adding the component E, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

By appropriately combining Component B, Component C, Component D, and Component E in compound (1), a liquid crystal composition that satisfies at least one of the following physical properties, which are high stability to heat or light, an upper limit, can be prepared. High temperature, low minimum temperature, low viscosity, appropriate optical anisotropy (i.e., large optical anisotropy or small optical anisotropy), large dielectric anisotropy, large resistivity, appropriate elastic constant (i.e., large elastic constant or small elastic constant) etc. A device comprising such a composition can be used in a wide temperature range, a short response time, a high voltage holding ratio, a low threshold voltage, a high contrast ratio, a low flicker rate, and a long life.

If the device is used for a long time, flicker (flicker) may occur on the display screen. The flicker rate (%) can be represented by (|brightness when a positive voltage is applied-brightness when a negative voltage is applied|)/average brightness)×100. Even if the device is used for a long time, it is difficult for a device with a flicker rate in the range of 0% to 1% to cause flicker (flicker) on the display screen. It is presumed that the flicker is associated with an afterimage of the image, and that the flicker occurs when a difference occurs between the electric potential of the positive frame and the electric potential of the negative frame when driving with alternating current. The composition containing compound (1) is also useful for reducing the generation of flicker.

3-2. Additives The liquid crystal composition is prepared by a known method. For example, the component compounds are mixed and dissolved in each other by heating. Additives may be added to the composition according to the application. Examples of additives are polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, antifoaming agents, and the like. Such additives are well known to those skilled in the art and are described in the literature.

In a liquid crystal display element having a polymer sustained alignment (PSA; polymer stabilized alignment) mode, the composition contains a polymer. The polymerizable compound is added for the purpose of generating a polymer in the composition. A polymer is generated in the composition by irradiating ultraviolet rays in a state where a voltage is applied between the electrodes to polymerize the polymerizable compound. With this method, an appropriate pretilt angle can be achieved, so that a device with reduced response time and improved image afterimage can be produced.

Preferred examples of the polymerizable compound are acrylates, methacrylates, vinyl compounds, vinyloxy compounds, acryl ethers, epoxy compounds (oxiranes, oxetanes), and vinyl ketones. Further preferred examples are compounds having at least one acryloxy group and compounds having at least one methacryloyloxy group. Further preferred examples include compounds having both acryloxy and methacryloyloxy groups.

Further preferred examples are compound (M-1) to compound (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 an alkyl group having 1 to 5 carbon atoms, and R ³² , R ³³ , and R ³⁴ are independently At least one is an alkyl group having 1 to 5 carbon atoms; v, w, and x are independently 0 or 1; u and y are independently an integer of 1 to 10. 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 the remaining polymerizable compound can be reduced. Examples of photo-radical polymerization initiators are TPO, 1173 and 4265 from the Darocur series from BASF, 184, 369, 500, 651, 784 from the Irgacure series , 819, 907, 1300, 1700, 1800, 1850 and 2959.

Additional examples of photo-radical polymerization initiators are 4-methoxyphenyl-2,4-bis(trichloromethyl)triazine, 2-(4-butoxystyryl)-5-trichloro Methyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzophenazine, benzophenone/Michler's ketone mixture, hexaarylbiimidazole/mercaptobenzimidazole mixture , 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, benzalkonium dimethyl ketal, 2-methyl-1-[4-(methylthio) ) Phenyl]-2-morpholinopropan-1-one, 2,4-diethylxanthone/p-dimethylaminobenzoic acid methyl ester mixture, benzophenone/methyltriethanolamine mixture .

Polymerization can be performed by adding a photoradical polymerization initiator to the liquid crystal composition, and then irradiating ultraviolet rays in a state where an electric field is applied. However, the unreacted polymerization initiator or the decomposition product of the polymerization initiator is likely to cause poor display such as image afterimage in the element. In order to prevent this, photopolymerization may be performed without adding a polymerization initiator. A preferred wavelength of light for irradiation is in the range of 150 nm to 500 nm. A further preferred wavelength is in the range of 250 nm to 450 nm, and the most preferred wavelength is in the range of 300 nm to 400 nm.

When storing the polymerizable compound, a polymerization inhibitor may be added in order 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 methyl hydroquinone, 4-tert-butylcatechol, 4-methoxyphenol, phenothiazine, and the like.

The optically active compound has an effect of preventing reverse torsion by imparting a necessary torsion angle by inducing a helical structure to liquid crystal molecules. By adding optically active compounds, the helical spacing can be adjusted. Two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the helical 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 group having 1 to 10 carbon atoms. *Marks indicate asymmetric carbons.

Antioxidants are effective for maintaining a large voltage holding ratio. Preferable examples of antioxidants include the following compounds (AO-1) and compounds (AO-2); Irganox 415, Irganox 565, Irganox ( Irganox 1010, Irganox 1035, Irganox 3114 and Irganox 1098 (trade names; BASF). The ultraviolet absorber is effective for preventing the lowering of the upper limit temperature. Preferable examples of the ultraviolet absorber are benzophenone derivatives, benzoate derivatives, triazole derivatives, and the like, and specific examples include the following compound (AO-3) and compound (AO-4) ; Tinuvin 329, Tinuvin P, Tinuvin 326, Tinuvin 234, Tinuvin 213, Tinuvin 400, Tinuvin Tinuvin 328, and Tinuvin 99-2 (trade names; BASF Corporation); and 1,4-Diazabicyclo[2.2.2]octane (1,4-Diazabicyclo [2.2.2] octane, DABCO).

Light stabilizers such as sterically hindered amines are preferable because they maintain a large voltage holding ratio. Preferred examples of the light stabilizer include the following compound (AO-5), compound (AO-6), compound (AO-7), compound (AO-8), and compound (AO-9); Tinuvin 144, Tinuvin 765, Tinuvin 770DF, Tinuvin 780 (trade name; BASF); LA-52, LA-57, LA -77Y, and LA-77G (trade name; ADEKA). A thermal stabilizer is also effective for maintaining a large voltage holding ratio, and as a preferable example, Irgafos 168 (trade name; BASF) can be mentioned. Dichroic dyes such as azo-based dyes and anthraquinone-based dyes are added to the composition in order to be suitable for a guest host device. Antifoaming agents are effective in preventing foaming. Preferred examples of the antifoaming agent are dimethyl silicone oil, methyl phenyl silicone oil, and the like.

In compound (AO-1), R ⁴⁰ is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, -COOR ⁴¹ or -CH ₂ CH ₂ COOR ⁴¹ , where R ⁴¹ is a carbon number 1 to 20 alkyl groups. In compound (AO-2) and compound (AO-5), R ⁴² is an alkyl group having 1 to 20 carbon atoms. In 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 compound (AO-8), ring G ² is 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene with at least one hydrogen substituted by fluorine; compound (AO-5 ), compound (AO-7), and compound (AO-8), z is 1, 2, or 3.

4. Liquid crystal display element The liquid crystal composition can be used for a liquid crystal display element which has operation modes such as PC, TN, STN, OCB, and PSA, and is driven by an active matrix method. The composition can also be used for a liquid crystal display element which has operation modes such as PC, TN, STN, OCB, VA, and IPS, and is driven in a passive matrix manner. These elements can be applied to any of reflection type, transmission type, and semi-transmission type.

The composition is also suitable for nematic curvilinear aligned phase (NCAP) elements, where the composition is microencapsulated. The composition can also be used for a polymer dispersed liquid crystal display element (Polymer Dispersed Liquid Crystal Display, PDLCD) or a polymer network liquid crystal display element (Polymer Network Liquid Crystal Display, PNLCD). A large amount of a polymerizable compound is added to these compositions. On the other hand, when the ratio of the polymerizable compound is 10% by weight or less based on the weight of the liquid crystal composition, a PSA mode liquid crystal display element is produced. A preferred ratio 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 elements of the PSA mode can be driven by a driving method such as an active matrix method or a passive matrix method. This type of element can also be applied to any of reflective, transmissive, and semi-transmissive types. [Example]

1. Examples of compound (1) The present invention will be further described in detail through examples. The examples are typical examples, and thus the present invention is not limited by the examples. Compound (1) was synthesized by the following procedure. The synthesized compounds were identified by nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) analysis and other methods. The physical properties of the compound or composition and the properties of the element were measured by the following methods.

NMR analysis: JNM-ECZS (500 MHz) manufactured by JEOL was used for the measurement. In the measurement of ¹ H-NMR, the sample is dissolved in a deuterated solvent such as CDCl ₃ , and the measurement is performed at room temperature at 500 MHz and 16 cumulative times. Tetramethylsilane was used as an internal standard. In the measurement of ¹⁹ F-NMR, CFCl ₃ was used as an internal standard, and the number of accumulations was performed 24 times. In the description of NMR spectra, s means singlet, d means doublet, t means triplet, q means quartet, and quin means quintet (quintet), sext refers to sextet (sextet), m refers to multiplet (multiplet), br refers to broad peak (broad).

Gas chromatographic analysis: A GC-2010 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. As carrier gas, helium (1 mL/min) was used. The temperature of the sample vaporization chamber was set to 300°C, and the temperature of the detector (Flame Ionization Detector (FID)) was set to 300°C. The sample was dissolved in acetone to prepare a 1 wt % solution, and 1 μl of the obtained solution was injected into the sample vaporization chamber. As the recorder, a GCSolution system manufactured by Shimadzu Corporation or the like was used.

Gas chromatograph mass analysis: A QP-2010Ultra gas chromatograph mass analyzer 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. As carrier gas helium (1 ml/min) was used. 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 radiation current was set to 150 uA. The sample was dissolved in acetone to prepare a 1 wt % solution, and 1 μl of the obtained solution was injected into the sample vaporization chamber. The recorder used the GCMSsolution system manufactured by Shimadzu Corporation.

High Performance Liquid Chromatography (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 size 5 μm) manufactured by YMC was used. The eluate is preferably mixed with acetonitrile and water. As a detector, an ultraviolet light (UltraViolet, UV) detector, a refractive index (Refractive Index, RI) detector, a corona (CORONA) detector, etc. are used suitably. In the case of using a UV detector, the detection wavelength was set to 254 nm. The sample was dissolved in acetonitrile to prepare a 0.1 wt % solution, and 1 μL of the solution was introduced into the sample chamber. The recorder used C-R7Aplus manufactured by Shimadzu Corporation.

Ultraviolet-visible spectroscopic analysis: PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used for the measurement. Set the detection wavelength from 190 nm to 700 nm. The sample was dissolved in acetonitrile to prepare a solution of 0.01 mmol/L, put into a quartz cell (optical path length 1 cm), and measured.

Measurement sample: When measuring the phase structure and transition temperature (clearing point, melting point, polymerization initiation temperature, etc.), the compound itself is used as a sample. When measuring the 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 is used as a sample.

In the case of using a sample in which the compound and mother liquid crystal were mixed, the extrapolated value was calculated by the following equation, and the value was described. <Extrapolated value>=(100×<measured value of sample>-<weight% of mother liquid crystal>×<measured value of mother liquid crystal>)/<weight% of compound>.

Mother liquid crystal (A): When the dielectric anisotropy of the compound is zero or positive, the following mother liquid crystal (A) is used. The ratio of each component is shown in % by weight.

The ratio of the compound to the mother liquid crystal (A) was 15% by weight: 85% by weight. When a crystal (or a smectic phase) is precipitated at 25° C. at this ratio, the ratio of the compound to the mother liquid crystal (A) is changed to 10% by weight: 90% by weight, 5% by weight: 95% by weight, and 1% by weight in this order %: 99% by weight, the sample was measured at a ratio at which no crystal (or smectic phase) was precipitated at 25°C. In addition, unless otherwise specified, the ratio of the compound to the mother liquid crystal (A) is 15% by weight: 85% by weight.

Mother liquid crystal (B): Mother liquid crystal (B) containing the following fluorine-based compound as a component was also used. The ratio of the components of the mother liquid crystal (B) is shown in % by weight.

The ratio of the compound to the mother liquid crystal (B) was 20% by weight: 80% by weight. When a crystal (or a smectic phase) is precipitated at 25° C. at this ratio, the ratio of the compound to the mother liquid crystal (B) is changed to 15% by weight: 85% by weight, 10% by weight: 90% by weight, and 5% by weight in this order %: 95% by weight, 1% by weight: 99% by weight, and the physical properties of the samples were measured at a ratio at which no crystals (or smectic phases) were precipitated at 25°C. In addition, unless otherwise specified, the ratio of the compound to the mother liquid crystal (B) is 20% by weight: 80% by weight.

Measurement method: Physical properties were measured by the following methods. Most of these methods are described in JEITA standards (JEITA·ED-2521B) reviewed and formulated by the Japan Electronics and Information Technology Industries Association (JEITA). A method of modifying it is also used. A thin film transistor (TFT) was not mounted on the TN element used for the measurement.

(1) Phase structure: The sample was placed on a hot plate (Mettler FP-52 type hot stage) equipped with a melting point measuring device with a polarizing microscope. While heating the sample at a rate of 3° C./min, the phase state and its change were observed with a polarizing microscope to determine the type of phase.

(2) Transition temperature (°C): The scanning calorimeter Diamond DSC system manufactured by Perkin Elmer or the high-sensitivity differential scanning calorimeter X- manufactured by SII Nanotechnology was used for the measurement. DSC7000. The sample was heated and lowered at a rate of 3°C/min, and the starting point of the endothermic peak or the exothermic peak accompanying the phase change of the sample was obtained by extrapolation to determine the transition temperature. The melting point and polymerization initiation temperature of the compound were also measured using the apparatus. The temperature at which the compound is transformed from a solid to a smectic phase or a nematic phase liquid crystal phase is sometimes simply referred to as "the lower limit temperature of the liquid crystal phase". The temperature at which a compound transitions from a liquid crystal phase to a liquid is sometimes simply referred to as the "clearing point".

Crystals are denoted as C. When two kinds of crystals can be distinguished, they are represented by C ₁ or C ₂ , respectively. The smectic phase is denoted S and the nematic phase is N. When the phases are distinguished like the smectic A phase, the smectic _B phase, the smectic _C phase, and the smectic _F phase, they are represented as _SA , SB, SC, and SF, respectively. Liquid (isotropic) is denoted I. The transition temperature is expressed, for example, as "C 50.0 N 100.0 I". It means that the transition temperature from crystallization to nematic phase is 50.0°C, and the transition temperature from nematic phase to liquid is 100.0°C.

(3) Compatibility of the compound: The mother liquid crystal was mixed with the compound so that the proportion of the compound was 20% by weight, 15% by weight, 10% by weight, 5% by weight, 3% by weight, or 1% by weight to prepare a sample . The sample is put into a glass bottle and stored in a freezer at -20°C or -30°C for a fixed period. Observe whether the nematic phase of the sample is maintained, or whether crystals (or smectic phases) are precipitated. The condition under which the nematic phase is maintained is used as the criterion for compatibility. The ratio of the compound or the temperature of the freezer may also be changed as necessary.

(4) Upper limit temperature of nematic phase (T _NI or NI; °C): The 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 changes from a nematic phase to an isotropic liquid is measured. When the sample is a mixture of compound (1) and mother liquid crystal, it is represented by the symbol T _NI . When the sample is a mixture of compound (1) and a compound selected from compound (2) to compound (15), it is represented by the symbol NI. The upper limit temperature of the nematic phase is sometimes simply referred to as the "upper limit temperature".

(5) Lower limit temperature of nematic phase (TC; ° _C ): put the sample with nematic phase into a glass bottle, and heat it at 0 °C, -10 °C, -20 °C, -30 °C and -40 °C After storing in a refrigerator for 10 days, the liquid crystal phase was observed. For example, when a sample maintains a nematic phase at -20°C and changes to a crystalline or smectic phase at -30°C, it is stated as T _C < -20°C. The lower limit temperature of the nematic phase is sometimes simply referred to as the "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) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa s): The measurement is based on "Molecular Crystals and Liquid Crystals" by M. Imai et al. (Vol. . 259, 37 (1995)) described in the method. The sample was placed in a TN device with a twist angle of 0° and a gap (cell gap) between two glass substrates of 5 μm. A voltage was applied to the element in steps of 0.5 V within a range of 16 V to 19.5 V. After no application for 0.2 seconds, the application was repeated under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current (peak current) and peak time (peak time) of the transient current (transient current) generated by the application were measured. The value of rotational viscosity was obtained from these measured values and equation (8) on page 40 of the paper by M. Imai et al. The value of the dielectric anisotropy required for the above calculation was obtained by the method described below using the element that measured the rotational viscosity.

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

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

(10) Elastic constant (K; measured at 25° C.; pN): An LCR meter HP4284A manufactured by Yokogawa Hewlett-Packard Co., Ltd. was used for the measurement. A sample was placed in a horizontal alignment element with a gap (cell gap) between two glass substrates of 20 μm. A charge of 0 V to 20 V was applied to the element, and the capacitance (C) and the applied voltage (V) were measured. Using equation (2.98) and equation (2.101) described on page 75 of "liquid crystal device handbook" (Nikkan Kogyo Shimbun), these measured values were fitted, and the equation (2.99) to obtain the values of K ₁₁ and K ₃₃ . Next, in Equation (3.18) described on page 171, K ₂₂ is calculated using the values of K ₁₁ and K ₃₃ obtained just now. The elastic constant K is represented by the average value of K ₁₁ , K ₂₂ , and K ₃₃ obtained as described above.

(11) Threshold voltage (Vth; measured at 25° C.; V): For the measurement, a liquid crystal display (LCD) 5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source is a halogen lamp. A sample was placed in a normally white mode TN element with an interval (cell gap) between two glass substrates of 0.45/Δn (μm) and a twist angle of 80 degrees. The voltage (32 Hz, rectangular wave) applied to the element was increased stepwise from 0 V to 10 V in units of 0.02 V. At this time, the element was irradiated with light from a vertical direction, and the amount of light transmitted through the element was measured. A voltage-transmittance curve was prepared in which the transmittance was 100% when the light amount reached the maximum, and the transmittance was 0% when the light amount was the minimum. The threshold voltage is expressed as the voltage at which the transmittance reaches 90%.

(12) Voltage holding ratio (VHR-1; measured at 25° C.; %): The TN element used for the measurement had a polyimide alignment film, and the interval (cell gap) between two glass substrates was 5 μm. The elements are sealed with an adhesive that hardens with UV light after sample addition. The element was charged by applying a pulse voltage (5 V, 60 microseconds) at 25°C. The decaying voltage was measured with a high-speed voltmeter in a period of 16.7 milliseconds, and the area A between the voltage curve per unit cycle and the horizontal axis was obtained. Area B is the area without attenuation. Voltage retention is expressed as a percentage of area A relative to area B.

(13) Voltage holding ratio (VHR-2; measured at 80° C.; %): The voltage holding ratio was measured by the above method except that the measurement was performed at 80° C. instead of 25° C. The obtained result is represented by the symbol VHR-2.

(14) Resistivity (ρ; measured at 25° C.; Ωcm): 1.0 mL of a sample was injected into a container equipped with an electrode. A DC voltage (10 V) was applied to the container, and the DC current after 10 seconds was measured. The resistivity was calculated according to the following equation. (resistivity)={(voltage)×(capacitance of container)}/{(DC current)×(dielectric constant of vacuum)}

(15) Response time (τ; measured at 25° C.; ms): LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source is a halogen lamp. Set the Low-pass filter to 5 kHz. A sample was placed in a normally white mode TN element with an interval (cell gap) between two glass substrates of 5.0 μm and a twist angle of 80 degrees. A rectangular wave (60 Hz, 5 V, 0.5 sec) was applied to the element. At this time, the element was irradiated with light from a vertical direction, and the amount of light transmitted through the element was measured. When the light amount reaches the maximum, the transmittance is regarded as 100%, and when the light amount is the minimum, the transmittance is regarded as 0%. Rise time (τr: rise time; milliseconds) is the time required for the transmittance to change from 90% to 10%. Fall time (τf: fall time; milliseconds) is the time required for the transmittance to change from 10% to 90%. The response time is represented by the sum of the rise time and the fall time obtained in the manner described above.

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

Raw material: Solmix (registered trademark) A-11 is a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (1.1%), obtained from Nippon Alcohol Sales Co., Ltd. Tetrahydrofuran is sometimes referred to as THF (Tetrahydrofuran). Tetrabutylammonium bromide is sometimes abbreviated as TBAB (Tetrabutylammonium Bromide). Sometimes N,N-dimethylformamide is abbreviated as DMF (Dimethyl Formamide). 2-Propanol is sometimes abbreviated as IPA (Iso Propyl Alcohol). 1,2-Dimethoxyethane is sometimes abbreviated as DME (1,2-Dimethoxyethane). Potassium hexamethyldisilazane is sometimes abbreviated as KHMDS.

[Synthesis Example 1] Synthesis of Compound (a-6)

first step Under nitrogen atmosphere, 2-ethylthiophene (5.00 g, 43.2 mmol) and THF (25 ml) were placed in the reactor and cooled to -70°C. An n-BuLi hexane solution (1.55 mol/L, 32.1 mL, 49.7 mmol) was added dropwise thereto, and the mixture was stirred at -70°C for 1 hour. Next, a solution of pinacol isopropoxyborate (9.74 g, 49.7 mmol) in THF (10 ml) was slowly added dropwise, and the temperature was raised to room temperature after the dropwise addition. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The prepared organic layer was washed with water and saturated brine in this order, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane/ethyl acetate=9/1, volume ratio) to obtain compound (t-1) (7.84 g, yield 76.1%).

second step Compound (t-1) (7.84 g, 32.9 mmol), trimethylolethane (4.04 g, 32.9 mmol), sodium hydroxide (1.36 g, 32.9 mmol), water (1.78 mL, 98.8 mmol), and 1,4-Dioxane (165 ml) was placed in the reactor, heated to 60°C, and stirred for 6 hours. After standing to cool to room temperature, 200 mL of heptane was added and stirred. The precipitate was collected by filtration, washed with heptane, and dried to obtain Compound (t-2) (9.43 g, 99.9% yield).

third step Under nitrogen atmosphere, 1-bromo-4-iodobenzene (27.8 g, 98.3 mmol) and THF (250 mL) were placed in the reactor and cooled to -50°C. A solution of isopropylmagnesium chloride-lithium chloride complex (1.3 mol/L, 74.1 mL, 98.3 mmol) was added dropwise thereto, and the mixture was stirred at -40°C for 2 hours. Next, cyclopentanone (6.89 g, 81.9 mmol) was added dropwise, and the temperature was raised to room temperature after the dropwise addition. The reaction mixture was poured into an aqueous ammonium chloride solution, and the aqueous layer was extracted with ethyl acetate. The prepared organic layer was washed with water and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (toluene) to obtain Compound (t-3) (15.1 g, yield 87.0%).

Fourth step Under nitrogen atmosphere, compound (t-3) (13.1 g, 54.4 mmol), 3,5-difluorophenylboronic acid (10.3 g, 65.3 mmol), tetrakis(triphenylphosphine)palladium (1.94 g), Potassium carbonate (15.1 g, 109 mmol), tetrabutylammonium bromide (5.37 g, 16.3 mmol), toluene (130 mL), 2-propanol (130 mL) and water (65 mL) were put into the reactor and carried out The mixture was heated to reflux for 3 hours, and allowed to cool to room temperature after completion of the reaction. The reaction mixture was poured into water, and the aqueous layer was extracted with toluene. The prepared organic layer was washed with sodium bicarbonate water and saturated brine in this order, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (toluene) to obtain Compound (t-4) (7.68 g, yield 51.4%).

Fifth step Under nitrogen atmosphere, compound (t-4) (7.68 g, 28.0 mmol) and dichloromethane (40 mL) were put into the reactor, and cooled to -70°C. A solution of triethylsilane (6.71 mL, 42.0 mmol) in dichloromethane (40 mL) was added dropwise thereto, and then boron trifluoride-diethyl ether complex (5.30 mL, 42.0 mmol) was added dropwise, and the temperature was raised to room temperature. The reaction mixture was poured into sodium bicarbonate water, and the aqueous layer was extracted with toluene. The prepared organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane) to obtain Compound (t-5) (8.05 g, yield 99.9%).

sixth step Under nitrogen atmosphere, compound (t-5) (8.05 g, 31.2 mmol) and THF (60 ml) were put into the reactor and cooled to -70°C. An n-BuLi hexane solution (1.60 mol/L, 29.8 mL, 49.7 mmol) was added dropwise thereto, and the mixture was stirred at -70°C for 1 hour. Next, a solution of iodine (12.1 g, 47.7 mmol) in THF (120 ml) was slowly added dropwise, and the temperature was raised to room temperature after the dropwise addition. The reaction mixture was poured into an aqueous sodium sulfite solution and stirred, and the aqueous layer was extracted with toluene. The prepared organic layer was washed with an aqueous sodium sulfite solution and saturated brine in this order, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane) and recrystallization (Solmix/heptane=10/1, volume ratio) to obtain the compound ( t-6) (9.01 g, 75.2% yield).

Seventh step Under nitrogen atmosphere, (t-6) (4.88 g, 12.7 mmol), (t-2) (7.33 g, 28.0 mmol), palladium acetate (0.0856 g, 0.380 mmol), (t-7) (0.228 g) were mixed together , 0.760 mmol) and DMF (75 mL) were put into the reactor and stirred at 50 °C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water, and the aqueous layer was extracted with toluene. The prepared organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography (heptane). After purification, it was placed in a reactor with 5% palladium on carbon (0.123 g), toluene (25 mL) and 2-propanol (25 mL) under hydrogen atmosphere and stirred for 4 hours. After the reaction, 5% palladium carbon was filtered and separated, the filtrate was concentrated, and the residue was analyzed by silica gel column chromatography (heptane) and recrystallization (Solmix/ethyl acetate=10/3, volume ratio). Purification was performed to obtain compound (a-6) (1.99 g, yield 42.5%).

¹ H-NMR (ppm; CDCl ₃ ): δ 7.51 (d, J=8.0 Hz, 2H)､ 7.41 (d, J=4.0 Hz, 1H)､ 7.33 (d, J=8.0 Hz, 2H)､ 7.23- 7.19 (m, 2H)､ 6.85 (d, J=3.5 Hz､ 1H)､ 3.08-3.01 (m, 1H)､ 2.91 (q､ J=7.5 Hz､ 2H)､ 2.14-2.07 (m､ 2H)､ 1.88 -1.58 (m､ 6H)､ 1.37 (t､ J=7.5 Hz､ 3H). Transition temperature: C 77.5 N 105.1 I. Upper limit temperature (T _NI )=105.0℃; dielectric anisotropy (Δε)=6.9; Optical anisotropy (Δn)=0.270; Viscosity (η)=39.8 mPa･s.

[Comparative Example 1] The following compound (S-1) was selected as a comparative compound. The compound was the compound (PUS-3-2) described in International Publication No. WO 2010/099853, and was synthesized according to the method described in the publication.

¹ H-NMR (ppm; CDCl ₃ ): δ 7.51-7.49 (m, 2H)､ 7.41 (d, J=3.5 Hz, 1H)､ 7.26 (d, J=8.0 Hz, 2H)､ 7.23-7.19 (m , 2H)､ 6.84 (td, J=1.0, 3.5 Hz､ 1H)､ 2.91 (q､ J=7.5 Hz､ 2H)､ 2.63 (t､ J=7.5 Hz､ 2H)､ 1.68 (sext､ J=7.5 Hz ､ 2H)､ 1.36 (t､ J=7.5 Hz､ 3H)､ 0.971 (t､ J=7.5 Hz､ 3H). Transition temperature: C 44.7 N 89.1 I. Upper limit temperature (T _NI )=101℃; Anisotropy (Δε)=6.87; Optical Anisotropy (Δn)=0.270; Viscosity (η)=17.4 mPa･s.

（a-6）

（S-1） 上限溫度（T_NI ） 105.0℃ 101℃ Comparison of physical properties Table 2, physical properties of compound (a-6) and comparative compound (S-1)

(a-6)

(S-1) Upper limit temperature (T _NI ) 105.0℃ 101℃

Table 2 summarizes the physical properties of the compound (a-6) obtained in Synthesis Example 1 and the comparative compound (S-1). As can be seen from Table 2, the compound (a-6) is favorable in that the upper limit temperature is high.

2. Synthesis of compound (1) Compound (1) was synthesized according to "2. Synthesis of Compound (1)" and the synthesis example described above. Examples of such compounds include compounds (a-1) to (a-96) and compounds (b-1) to (b-92) shown below.

[工業上的可利用性]

[Industrial Availability]

The liquid crystal compound of the present invention has good physical properties. The liquid crystal composition containing the compound can be widely used for liquid crystal display elements used in personal computers, televisions, and the like.

without

Claims (14)

A compound represented by formula (1),

In formula (1), R ¹ is hydrogen, P-Sp-, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine; R ² is hydrogen , fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , P-Sp- or an alkyl group with 1 to 15 carbon atoms, in the R ² , at least one - CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine Substituted; P is a polymerizable group; Sp is a spacer or a single bond; Ring N ¹ and Ring N ² are independently a cycloalkylene group having 3 to 5 carbon atoms, and in the cycloextended alkyl group, at least one -CH ₂ -Can be substituted by -O-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH-; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexylene Alkenyl, 1,4-phenylene, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, the ring In A ¹ and ring A ² , at least one hydrogen may be fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F-substituted; Z ¹ , Z ² , Z ³ and Z ⁴ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in said Z ¹ , Z ² , Z ³ and Z ⁴ , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine ; a is 0, 1, 2 or 3, b is 0, 1, 2 or 3, and c is 0 or 1. The compound as claimed in claim 1, represented by formula (1a),

In formula (1a), R ¹ is hydrogen, P-Sp-, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine; R ² is fluorine , chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , P-Sp-, or an alkyl group having 1 to 15 carbon atoms, in the R ² , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine ; P is a polymerizable group; Sp is a spacer or a single bond; Ring N ¹ is a cycloextended alkyl group with 3 to 5 carbon atoms, and in said ring N ¹ , at least one -CH ₂ - may be substituted by -O-, At least one -CH ₂ CH ₂ - may be substituted by -CH=CH-; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-cyclohexylene Phenyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2, 5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, in the ring A ¹ and ring A ² , At least ^one _hydrogen may be substituted with fluorine, chlorine, _-C≡N , _-CH3 , _-CF3 , -CHF2, _-CH2F , _-OCF3 , -OCHF2, or -OCH2F _; Z1, Z ² and Z ³ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in said Z ¹ , Z ² and Z ³ , at least one -CH ₂ - may be via -O-, -S-, or - CO-substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; a is 0, 1, 2 or 3, b is 0 , 1, 2, or 3. The compound according to claim 1 or claim 2, represented by any one of formula (1-1) to formula (1-10),

In formula (1-1) to formula (1-10), R ¹ is hydrogen, or an alkyl group having 1 to 15 carbon atoms, and in said R ¹ , at least one -CH ₂ - may be through -O-, -S -, or -CO- substituted, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but R ¹ is not fluorine or chlorine; R ² is fluorine, chlorine, -C≡N, -C≡CC≡N, -NCS, -SCN, -SF ₅ , or an alkyl group having 1 to 15 carbon atoms, and in said R ² , at least one -CH ₂ - can be substituted by -O-, -S-, or -CO-, at least one -CH ₂ CH ₂ - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; Ring N ¹ is a cycloextended alkyl group having 3 to 5 carbon atoms, in the ring N ¹ , at least one -CH ₂ - may be substituted by -O-, and at least one -CH ₂ CH ₂ - may be substituted by -CH=CH- Substituted; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyridine pyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, or pyrimidine-2,5-diyl, the ring A ¹ and ring In A ² , at least one hydrogen may be substituted by fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F; Z ¹ , Z ² and Z ³ are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in said Z ¹ , Z ² and Z ³ , at least one -CH ₂ - may be through -O-, -S -, or -CO- substituted, at least one -CH ₂ CH ₂ - may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine. The compound according to claim 3, wherein, in formulas (1-1) to (1-10), R ¹ is hydrogen, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, Alkoxyalkyl having 2 to 14 carbons, alkenyl having 2 to 15 carbons, or alkenyloxy having 2 to 14 carbons; R ² is fluorine, chlorine, -CF ₃ , -OCF ₃ , -C≡ N, alkyl having 1 to 15 carbons, alkoxy having 1 to 14 carbons, alkoxyalkyl having 2 to 14 carbons, alkenyl having 2 to 15 carbons, or alkene having 2 to 14 carbons oxy; Ring N ¹ is 1,2-cycloextended propyl, 1,3-cyclobutylene, or 1,3-cyclopentylene; Ring A ¹ and Ring A ² are independently 1,4-extended Cyclohexyl, 1,4-cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine- 2,5-diyl, or pyrimidine-2,5-diyl, in the divalent group, at least one hydrogen can be replaced by fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F substituted; Z ¹ , Z ² and Z ³ are independently a single bond, -O-, -CH ₂ -, -CO-, -COO- , -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH 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 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-. The compound according to claim 1 or claim 2 is composed of formula (1-1-1), formula (1-2-1), formula (1-3-1), formula (1-4-1), Equation (1-5-1), Equation (1-6-1), Equation (1-7-1), Equation (1-8-1), Equation (1-8-2), Equation (1-9) -1), formula (1-9-2), formula (1-10-1), or any one of formula (1-10-2) represents,

Equation (1-1-1), Equation (1-2-1), Equation (1-3-1), Equation (1-4-1), Equation (1-5-1), Equation (1-6) -1), formula (1-7-1), formula (1-8-1), formula (1-8-2), formula (1-9-1), formula (1-9-2), formula In (1-10-1) and formula (1-10-2), R ¹ is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 14 carbons, alkane having 2 to 14 carbons Oxyalkyl, alkenyl with 2 to 15 carbons, or alkenyl with 2 to 14 carbons; R ² is fluorine, chlorine, -CF ₃ , -OCF ₃ , -C≡N, carbon number 1 to 15 alkyl, alkoxy with 1 to 14 carbons, alkoxyalkyl with 2 to 14 carbons, alkenyl with 2 to 15 carbons, or alkenyl with 2 to 14 carbons; Ring N ¹ is 1,2-cyclopropylidene, 1,3-cyclohexylene, or 1,3-cyclopentylene; Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4- Cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, Or pyrimidine-2,5-diyl, in the divalent group, at least one hydrogen can be changed through fluorine, chlorine, _-C≡N , _-CH3 , _-CF3 , -CHF2, _-CH2F , -OCF ₃ , -OCHF ₂ , or -OCH ₂ F substituted; Z ¹ , Z ² and Z ³ are independently a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH 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 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-. The compound according to claim 5, wherein formula (1-1-1), formula (1-2-1), formula (1-3-1), formula (1-4-1), formula (1) -5-1), formula (1-6-1), formula (1-7-1), formula (1-8-1), formula (1-8-2), formula (1-9-1) , formula (1-9-2), formula (1-10-1), or formula (1-10-2), R ¹ is hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 9 carbon atoms Alkoxy, alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons, or alkenyloxy having 2 to 9 carbons; R ² is fluorine, -CF ₃ , -OCF ₃ , - C≡N, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons, or 2 to 9 carbons alkenyloxy; Ring N ¹ is 1,2-cycloextended propyl, 1,3-cyclobutylene, or 1,3-cyclopentylene; Ring A ¹ and Ring A ² are independently 1,4 -cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl , in the divalent group, at least one hydrogen can be through fluorine, chlorine, -C≡N, -CH ₃ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F substituted; Z ¹ , Z ² and Z ³ are independently a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, -CH=CH-, -C≡C-, -(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-. The compound according to claim 1 or claim 2, comprising formula (1-2-1-1), formula (1-3-1-1) to formula (1-3-1-6), or formula ( 1-4-1-1) to formula (1-4-1-18),

Equation (1-2-1-1), Equation (1-3-1-1) to Equation (1-3-1-6), and Equation (1-4-1-1) to Equation (1-4) -1-18), R ¹ is hydrogen, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, alkoxyalkyl with 2 to 9 carbons, alkene with 2 to 10 carbons R ² is fluorine, -CF ₃ , -OCF ₃ , -C≡N, alkyl with 1 to 10 carbons, alkoxy with 1 to 9 carbons, Alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons, or alkenyl having 2 to 9 carbons; Ring N ¹ is 1,2-cycloextended propyl, 1,3-extended Cyclobutyl, or 1,3-cyclopentylene; Z ¹ is a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, -CH=CH-, -(CH ₂ ) ₄ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-(CH2) _2- , -( _CH2 ) ₂ - _CH =CH-, -CH= _CH - _CH2O- , or -OCH2-CH=CH-. The compound of claim 7, wherein the formula (1-2-1-1), the formula (1-3-1-1) to the formula (1-3-1-6), or the formula (1-4) In -1-1) to formula (1-4-1-18), R ¹ is hydrogen, alkyl having 1 to 6 carbons, alkoxy having 1 to 5 carbons, alkoxy having 2 to 5 carbons alkyl, alkenyl with 2 to 6 carbons, or alkenyl with 2 to 5 carbons; R ² is fluorine, -OCF ₃ , -C≡N, alkyl with 1 to 6 carbons, 1 carbon alkoxy group to 5, alkoxyalkyl group of carbon number 2 to 5, alkenyl group of carbon number 2 to 6, or alkenyloxy group of carbon number 2 to 5; Ring N ¹ is 1,2-cyclopropylene Z ¹ is a single bond, -O-, -CH ₂ -, -CO-, -COO-, -OCO-, -CH _2O- , _-OCH2- , _-CF2O- , _-OCF2- , _-CH2CH2- , or -CH= _CH- . A liquid crystal composition containing at least one compound according to any one of claim 1 to claim 8. The liquid crystal composition according to claim 9, further comprising at least one compound selected from the group of compounds represented by formula (2) to formula (4),

In formulas (2) to (4), R ¹¹ and R ¹² are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹¹ and R ¹² , at least one -CH ₂ - may be substituted by -O-, at least one hydrogen may be substituted by fluorine; Ring B ¹ , Ring B ² , Ring B ³ , and Ring B ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene group, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; Z ¹¹ , Z ¹² , and Z ¹³ independently is a single bond, -COO-, -CH ₂ CH ₂ -, -CH=CH-, or -C≡C-. The liquid crystal composition according to claim 9 or claim 10, further comprising at least one compound selected from the group of compounds represented by formula (5) to formula (7),

In formulas (5) to (7), R ¹³ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹³ , at least one -CH ₂ - may be substituted by -O- , at least one hydrogen can be substituted 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 ; Ring C ¹ , Ring C ² , and Ring C ³ are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene with at least one hydrogen substituted with fluorine, tetrahydropyran -2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ¹⁴ , Z ¹⁵ , and Z ¹⁶ are independently a single bond, -COO _- , -OCO-, _-CH2O- , _-OCH2- , -CF2O-, _-OCF2- , _-CH2CH2- , -CH= _CH- , -C≡C-, or -( CH ₂ ) ₄ -; L ¹¹ and L ¹² are independently hydrogen or fluorine. The liquid crystal composition according to claim 9 or claim 10, further comprising at least one compound selected from the group of compounds represented by formula (8),

In formula (8), R ¹⁴ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹⁴ , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen may be substituted by -O-. Substituted by fluorine; X ¹² is -C≡N or -C≡CC≡N; Ring D ¹ is 1,4-cyclohexylene, 1,4-phenylene, 1,4- at least one hydrogen substituted by fluorine phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; Z ¹⁷ is a single bond, -COO- , -OCO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, or -C≡C-; L ¹³ and L ¹⁴ are independently hydrogen or fluorine; i is 1, 2, 3, or 4. The liquid crystal composition according to claim 9 or claim 10, further comprising at least one compound selected from the group of compounds represented by formula (11) to formula (19),

In formula (11) to formula (19), R ¹⁵ , R ¹⁶ , and R ¹⁷ are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and the R ¹⁵ , R ¹⁶ , and Among R ¹⁷ , at least one -CH ₂ - may be substituted with -O-, at least one hydrogen may be substituted with fluorine, and R ¹⁷ may be hydrogen or fluorine; ring E ¹ , ring E ² , ring E ³ , and ring E ⁴ is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene with at least one hydrogen substituted with fluorine, tetrahydropyran- 2,5-diyl, or decahydronaphthalene-2,6-diyl; Ring E ⁵ and Ring E ⁶ are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4 -phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl; Z ¹⁸ , Z ¹⁹ , Z ²⁰ , and Z ²¹ are independently a single bond, -COO- , _-OCO- , _-CH2O- , _-OCH2- , _-CF2O- , _{-OCF2- , -CH2CH2- , -CF2OCH2CH2-} , _{or -OCF2CH2CH 2-} ; L ¹⁵ and L ¹⁶ 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, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2, or 3. A liquid crystal display element comprising the liquid crystal composition according to any one of claim 9 to claim 13.