Polymerizable compound and liquid crystal composition using the same

Abstract

To provide a polymerizable compound which has a sufficiently fast polymerization speed, and enables a pretilt angle to be formed at a shorter ultraviolet radiation period, to provide a polymerizable compound for producing a PSA type or a PSVA type liquid crystal display element having no or very little display failure due to change of the pretilt angle, and having a sufficient pretilt angle and excellent response performance, and to provide a liquid crystal composition including the polymerizable compound.SOLUTION: The present invention provides: a compound having structure which is expressed by a general formula (Y (chemical formula 1)); a liquid crystal composition including the compound; and an element using the liquid crystal composition.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polymerizable compound. [Background technology]

[0002] Liquid crystal display elements using liquid crystal compositions exhibiting a negative dielectric anisotropy Δε are widely used in PSA and PSVA type liquid crystal TVs and liquid crystal monitors, and as liquid crystal compositions suitable for these, various polymerizable compounds and liquid crystal compositions containing the same are disclosed in Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, Patent Document 5, etc.

[0003] However, the properties of conventional polymerizable liquid crystal compositions are insufficient for high-resolution LCD TVs, such as 4K and 8K. Specifically, 4K and 8K LCD display elements require high-resolution pixels, which increase the wiring and light-shielding areas, blocking a significant amount of UV light. As a result, the polymerizable compound does not polymerize sufficiently during the UV irradiation process in the manufacture of PSA and PSVA LCD elements, resulting in a large amount of residual polymerizable compound. This results in insufficient tilt formation, resulting in poor response speed and image retention due to poor alignment. Furthermore, the residual polymerizable compound gradually polymerizes during operation, causing a change in tilt, resulting in a display defect known as image retention (IS).

[0004] For these reasons, PSA or PSVA type liquid crystal display elements for high-definition liquid crystal televisions and liquid crystal monitors are required to have extremely high characteristics that are a world apart from those of conventional technologies, and there is a demand for liquid crystal compositions that can be stably produced using weaker or less UV light than conventional ones. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2016-216747 [Patent Document 2] Patent No. 4803320 [Patent Document 3] Patent No. 6008065 [Patent Document 4] Patent No. 6233550 [Patent Document 5] Patent No. 5743132 Summary of the Invention [Problem to be solved by the invention]

[0006] The problem to be solved by the present invention is to provide a polymerizable compound which has a sufficiently fast polymerization rate and can form a pretilt angle with a shorter UV irradiation time. Another problem to be solved by the present invention is to provide a polymerizable compound for producing a PSA or PSVA type liquid crystal display device which has no or very little display defects due to changes in the pretilt angle, has a sufficient pretilt angle, and is excellent in response performance, and to provide a liquid crystal composition containing the polymerizable compound. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above problems, and as a result have completed the present invention.

[0008] That is, the present invention provides a compound represented by the general formula (Y)

[0009] [ka]

[0010] (In the formula, R y1 and R y2 each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- groups are not adjacent to each other in succession, S y1 and Sy2 each independently represents a single bond or an alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, -CH- in the alkylene group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- groups are not adjacent to each other in succession, Z y1 and Z y2 each independently represents a single bond, -C2H4-, -C4H8-, -C3H6-, -OCH2-, -CHO-, -CO-, -COO-, -OCO-, -OCOOCH2-, -CH2OCOO-, -OCH2CHO-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa=CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO -, -OCO-CRa=CH-OCO-, -COOC2H4-, -OCOC2H4-, -C2H4OCO-, -C2OCO-, -COOCH2-, -OCOCH2-, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2- or -C≡C- (wherein Ra each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), M y1 and M y2 each independently represents a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic group, a divalent fused ring, or a divalent fused polycyclic ring, and a hydrogen atom in these ring structures is L y1 and L y1 represents a halogen atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 30 carbon atoms, wherein a hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group, or a nitro group, and -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-, or -S-, provided that two or more -O- groups are not adjacent to each other in succession; m and n each independently represent an integer of 0 to 3, and the sum of m and n is 1 to 6; P y1 and P y2 represents a polymerizable group. and a liquid crystal composition and a display device containing the compound. [Effects of the Invention]

[0011] The polymerizable compound according to the present invention has a sufficiently high polymerization rate and a sufficiently high pretilt angle, is highly compatible with a liquid crystal composition, and can be easily produced without impairing the storage stability and long-term reliability of the liquid crystal composition. By using a liquid crystal composition using the polymerizable compound according to the present invention, it is possible to provide a liquid crystal display device that exhibits excellent display quality over a long period of time. DETAILED DESCRIPTION OF THE INVENTION

[0012] The polymerizable initiator compound represented by general formula (Y) in the present invention is characterized by having a polymerizable group and a β-dicarbonyl skeleton. In this specification, among initiator compounds, initiator compounds having a polymerizable group are referred to as "polymerizable initiator compounds" and initiator compounds without a polymerizable group are referred to as "non-polymerizable initiator compounds" to distinguish them from each other. Furthermore, among initiator compounds, initiator compounds having a β-dicarbonyl skeleton in their molecular structure are referred to as "β-dicarbonyl initiator compounds" and initiator compounds without a β-dicarbonyl skeleton are referred to as "non-β-dicarbonyl initiator compounds" to distinguish them from each other. That is, since the polymerizable initiator compound represented by general formula (Y) in the present invention has both a polymerizable group and a β-dicarbonyl skeleton, it can be referred to as a "polymerizable β-dicarbonyl initiator compound."

[0013] It should be noted that the polymerization initiator compounds, including the polymerization initiator compound represented by general formula (Y), are not included in the polymerizable compounds described below.

[0014] In recent years, PSA-type LCD devices, such as those for 4K and 8K displays, have required high-resolution pixels. This has resulted in an increase in the number of wiring and light-shielding areas, which blocks a significant amount of UV light. This means that conventional UV irradiation processes can lead to problems such as insufficient tilt formation, insufficient polymerization of the polymerizable compound, and a large amount of the polymerizable compound remaining. This has also resulted in display defects such as image retention (IS), which occurs when the remaining polymerizable compound gradually polymerizes during operation and changes the tilt.

[0015] The polymerization initiator compound of the present invention has a moderately fast polymerization rate and can impart the desired pretilt angle with a short UV irradiation time. Furthermore, the moderately fast polymerization rate can reduce the amount of residual polymerizable compound. This improves the production efficiency of PSA-type liquid crystal display device manufacturing. The polymerization initiator compound represented by general formula (Y) not only functions as a polymerization initiator moiety with a β-dicarbonyl structure, but also has a liquid crystal mesogenic structure, resulting in high solubility and excellent compatibility with liquid crystal compounds. Therefore, the polymerization initiator compound represented by general formula (Y) can achieve the same effect as conventional non-polymerizable initiator compounds at a low content. Furthermore, because it is less likely to precipitate from the liquid crystal composition, it can be added in larger amounts than conventional initiator compounds, achieving sufficient polymerization at a fast rate.

[0016] Furthermore, the liquid crystal composition of the present invention contains a polymerizable initiator compound represented by general formula (Y), which allows for sufficient polymerization at a moderately fast rate and shortens the UV exposure time, thereby suppressing UV-induced degradation of the liquid crystal composition and a decrease in voltage holding ratio (VHR). Specifically, initiator compounds commonly used in conventional liquid crystal compositions lack a polymerization function (i.e., a polymerizable group). While such non-polymerizable initiator compounds accelerate the polymerization rate, the remaining portions of the compound disperse (diffuse) within the liquid crystal layer, acting as ion conduction sources and reducing VHR. On the other hand, the polymerizable compound represented by general formula (Y) contains a polymerizable moiety (polymerizable group), which allows the polymerizable compound represented by general formula (Y) to form a polymer upon UV exposure, and this polymer can be fixed to the substrate interface after UV treatment. This ensures that the polymer of the polymerizable compound represented by general formula (Y) is fixed to the substrate even during panel operation. This allows for improved VHR without the polymerizable initiator compound represented by general formula (Y) itself acting as an ion conduction source.

[0017] The above-mentioned effect is particularly pronounced when a polymerizable compound is included. Manufacturing a liquid crystal display device using polymer stabilization technology involves irradiating a liquid crystal composition containing a polymerizable compound with ultraviolet light to polymerize the polymerizable compound and form a polymer layer composed of a polymer of the polymerizable compound at the substrate interface of the device. When the liquid crystal composition of the present invention contains a polymerizable compound, the β-dicarbonyl structure of the polymerizable compound represented by general formula (Y) functions as a polymerization initiator in the above process, thereby allowing polymerization within the liquid crystal composition to proceed at a moderately fast rate, thereby enabling the formation of a pretilt angle with a short UV irradiation time. Furthermore, it is believed that the polymerizable group of the polymerizable initiator compound represented by general formula (Y) reacts with a portion of the polymerizable compound, resulting in the polymerization of the polymerizable compound into the polymer layer formed by polymerization. The polymerizable initiator compound represented by general formula (Y) incorporated into the polymer layer is fixed to the polymer layer and no longer functions as an ion-conducting source, thereby more effectively suppressing the decrease in VHR compared to when a non-polymerizable initiator compound is used.

[0018] In general formula (Y), R y1 and R y2 each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- groups are not adjacent to each other in succession, S y1 and S y2 each independently represents a single bond or an alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, -CH- in the alkylene group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- groups are not adjacent to each other in succession, Z y1 and Z y2 each independently represents a single bond, -C2H4-, -C4H8-, -C3H6-, -OCH2-, -CHO-, -CO-, -COO-, -OCO-, -OCOOCH2-, -CH2OCOO-, -OCH2CHO-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa=CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO -, -OCO-CRa=CH-OCO-, -COOC2H4-, -OCOC2H4-, -C2H4OCO-, -C2OCO-, -COOCH2-, -OCOCH2-, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2- or -C≡C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), M y1 and M y2each independently represents a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic group, a divalent fused ring, or a divalent fused polycyclic ring, and a hydrogen atom in these ring structures is L y1 and L y1 represents a halogen atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 30 carbon atoms, wherein a hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group, or a nitro group, and -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-, or -S-, provided that two or more -O- groups are not adjacent to each other in succession; m and n each independently represent an integer of 0 to 3, and the sum of m and n is 1 to 6; P y1 and P y2 represents a polymerizable group. It is preferable that the compound is represented by the following formula:

[0019] R y1 and R y2 preferably each independently represent a straight-chain or branched alkyl group having 1 to 12 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom, or a cyano group, -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, or -OCO-, -OCOO-, -O-, -NH-, or -S-, provided that two or more -O- groups are not adjacent to each other in succession, more preferably each independently represent a straight-chain or branched alkyl group having 1 to 6 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom, or a cyano group, -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, or -OCO-, -OCOO-, or -O-, provided that two or more -O- groups are not adjacent to each other in succession, and further preferably each independently represent a straight-chain or branched alkyl group having 1 to 6 carbon atoms.

[0020] S y1 and S y2preferably each independently represents a single bond or an alkylene group having 1 to 6 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom or a cyano group, and -CH- in the alkylene group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- are not adjacent to each other in succession, and more preferably each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom or a cyano group. In the alkylene group, -CH2- may be substituted with -CH=CH-, -CO-, -O-, -COO- or -OCO-, provided that two or more -O- groups are not adjacent to each other in succession, and more preferably each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, and in the alkylene group, -CH2- may be substituted with -CH=CH-, -O-, -CO-, -COO- or -OCO-, provided that two or more -O- groups are not adjacent to each other in succession, and particularly preferably a single bond, -CH2CH2-, -CHO-, -OCH2-, -COO- or -OCO-.

[0021] Z y1 and Z y2are preferably each independently a single bond, -C2H4-, -C4H8-, -C3H6-, -OCH2-, -C2O-, -CO-, -COO-, -OCO-, -OCOOCH2-, -CH2OCOO-, -OCH2CHO-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa=CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO-, -OCO-CRa=CH-OCO-, -COOC2H4-, -OCOC2H4-, -C2H4 OCO-, -CHOCO-, -COOCH-, -OCOCH-, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CFO-, -OCF-, -CFCH-, -CHCF-, -CFCF- or -C≡C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), more preferably a single bond, -CH-, -CH-, -OCH-, -CHO-, -COO-, -OCO-, -OCOOCH-, -CHOCOO-, -OCHCHO-, -CH=CRa-COO -, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa=CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO-, -OCO-CRa=CH-OCO-, -COOC2H4-, -OCOC2H4-, -C2H4OCO-, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2- or -C≡C- (wherein Ra each independently represents a hydrogen atom or a group having 1 to 4 carbon atoms). represents an alkyl group having 1 to 4 carbon atoms), and more preferably a single bond, -C2H4-, -C4H8-, -OCH2-, -CHO-, -COO-, -OCO-, -OCH2CHO-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COOC2H4-, -OCOC2H4-, -C2H4OCO-, -CH=CH-, -CF=CF-, -CF2O-, -OCF2-, -CF2CF2- or -C≡C- (wherein Ra each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),Particularly preferred are a single bond, -C2H4-, -C4H8-, -OCH2-, -CHO-, -COO-, -OCO-, -OCH2CHO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH- or -C≡C-.

[0022] M y1 and M y2 each independently represents a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic group, a divalent fused ring, or a divalent fused polycyclic ring;

[0023] (a) a 1,4-cyclohexylene group (in which one —CH— or two or more non-adjacent —CH— groups may be replaced by —O—).

[0024] (b) a 1,4-phenylene group, a 1,3-phenylene group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by -N=); and

[0025] (c) A naphthalene-1,4-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= groups in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N=).

[0026] In addition, the above groups (a), (b) and (c) are preferably groups selected from the group consisting of L y1 It is also preferred that it is substituted with

[0027] Also, M y1 and M y2 is more preferably a 1,4-cyclohexylene group, a 1,4-phenylene group, a naphthalene-1,4-diyl group or a naphthalene-2,6-diyl group among the above groups (a), (b) and (c), and these groups are y1It is also preferred that it is substituted with

[0028] L y1 represents a halogen atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 30 carbon atoms, wherein a hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group, or a nitro group, -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-, or -S-, provided that two or more -O- groups are not adjacent to each other in succession, and preferably represents a fluorine atom, a cyano group, or a linear or branched alkyl group having 1 to 6 carbon atoms, wherein a hydrogen atom in the alkyl group may be substituted with a fluorine atom, -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO- or -O-, provided that two or more -O- groups are not adjacent to each other in succession, and more preferably represents a fluorine atom, or a linear or branched alkyl group having 1 to 6 carbon atoms, and a hydrogen atom in the alkyl group may be substituted with a fluorine atom, and -CH2- in the alkyl group may be substituted with -COO-, -OCO- or -O-, provided that two or more -O- groups are not adjacent to each other in succession, and even more preferably represents a fluorine atom, or a linear alkyl group or alkoxy group having 1 to 4 carbon atoms.

[0029] P y1 and P y2 are preferably each independently represented by the following general formula (P-1) to general formula (P-14):

[0030] [ka]

[0031] (where the black dots represent Z y1 or Z y2represents a bond to the group represented by the formula (I), more preferably (P-1), (P-2), (P-4), (P-5), (P-7), (P-9), (P-11), (P-12), and (P-13), still more preferably (P-1), (P-2), (P-7), (P-12), and (P-13), and particularly preferably (P-1) and (P-2).

[0032] Preferably, m and n each independently represent an integer of 0 to 2, more preferably an integer of 1 or 2. The sum of m and n is preferably 1 to 6, more preferably 1 to 4, and particularly preferably 2 to 4.

[0033] The structure represented by general formula (Y) preferably includes the following formula (YA).

[0034] [ka]

[0035] (In the formula, R y1a and R y2a each independently represent a linear or branched alkyl group having 1 to 12 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom or a cyano group, -CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- groups are not adjacent to each other in succession, S y1a and S y2a each independently represents a single bond or an alkylene group having 1 to 6 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom or a cyano group, -CH- in the alkylene group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- groups are not adjacent to each other in succession, Z y1a and Z y2aeach independently represent a single bond, -C2H4-, -C4H8-, -OCH2-, -CHO-, -COO-, -OCO-, -OCH2CHO-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COOC2H4-, -OCOC2H4-, -C2H4OCO-, -CH=CH-, -CF=CF-, -CF2O-, -OCF2-, -CF2CF2- or -C≡C- (wherein each Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), M y1a and M y2a are each independently (a) a 1,4-cyclohexylene group (in which one —CH— or two or more non-adjacent —CH— groups may be replaced by —O—). (b) a 1,4-phenylene group, a 1,3-phenylene group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by -N=); and (c) A naphthalene-1,4-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= groups in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N=). and the hydrogen atoms in these ring structures are selected from the group consisting of L y1a and L y1a represents a fluorine atom, a cyano group, or a linear or branched alkyl group having 1 to 6 carbon atoms, wherein a hydrogen atom in the alkyl group may be substituted with a fluorine atom, and -CH- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO- or -O-, provided that two or more -O- groups are not adjacent to each other in succession; ma and na each independently represent an integer of 0 to 3, where the total number of m+n is 1 to 4; P y1a and P y2arepresents a group represented by the above general formula (P-1) to general formula (P-14).

[0036] As the structure represented by general formula (Y), structures represented by the following formulae (Y-A1) to (Y-A8) are also preferred.

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] (In the formula, R yi1 and R yi2 is R in general formula (Y) y1 and R y2 and S have the same meaning. yi1 and S yi2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. yi1 and Z yi2 is Z in general formula (Y) y1 and Z y2 and M yi1 and M yi2 is M in general formula (Y) y1 and M y2 and P yi1 and P yi2 is P in general formula (Y) y1 and P y2 and mi and ni have the same meanings as m and n in general formula (Y), respectively.

[0041] Specifically, the polymerizable compound represented by general formula (Y) according to the present invention is preferably a compound represented by general formula (Y-1-1) to general formula (Y-16-33).

[0042] [ka]

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[0074] A composition containing one or more compounds represented by general formula (Y) preferably has a liquid crystal phase at room temperature. The compound represented by general formula (Y) is contained in the composition at a concentration of preferably 0.005% or more, more preferably 0.01% or more, more preferably 0.02% or more, more preferably 0.03% or more, more preferably 0.05% or more, more preferably 0.07% or more, more preferably 0.1% or more, more preferably 0.15% or more, more preferably 0.2% or more, more preferably 0.25% or more, more preferably 0.3% or more, more preferably 0.5% or more, and more preferably 1% or more. Furthermore, the upper limit is preferably 5% or less, more preferably 3% or less, more preferably 1% or less, more preferably 0.5% or less, more preferably 0.45% or less, more preferably 0.4% or less, more preferably 0.35% or less, more preferably 0.3% or less, more preferably 0.25% or less, more preferably 0.2% or less, more preferably 0.15% or less, more preferably 0.1% or less, more preferably 0.07% or less, more preferably 0.05% or less, and more preferably 0.03% or less.

[0075] More specifically, the content is preferably 0.01 to 5 mass%, more preferably 0.01 to 0.3 mass%, further preferably 0.02 to 0.3 mass%, and particularly preferably 0.05 to 0.25 mass%. More specifically, when emphasis is placed on suppressing precipitation at low temperatures, the content is preferably 0.01 to 0.1 mass%.

[0076] The composition containing the compound represented by general formula (Y) may contain, in addition to the compound represented by general formula (Y), a compound having a liquid crystal phase, or may contain a compound not having a liquid crystal phase.

[0077] In the present invention, the compound represented by general formula (Y) can be produced as follows: Of course, the gist and scope of the present invention are not limited to these production examples.

[0078] (Compound manufacturing method-1)

[0079] [ka]

[0080] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 and mx and nx have the same meanings as m and n in general formula (Y), respectively.

[0081] The target compound of general formula (Y)-1 having a methacryloyl group as a polymerizable group can be obtained by a transesterification reaction between the hydroxyl group of the compound represented by general formula (S-1) and ethyl methacrylate using a tin catalyst.

[0082] (Compound manufacturing method-2)

[0083] [ka]

[0084] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in general formula (Y), R s1 represents an alkyl group having 1 to 6 carbon atoms, and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0085] A compound represented by general formula (S-2) can be reduced to obtain a compound represented by general formula (S-3). Examples of reducing agents include diisobutylaluminum hydride. Alternatively, a compound represented by general formula (S-2) can be reduced to an alcohol, which can then be oxidized to an aldehyde to obtain a compound represented by general formula (S-3). Examples of reducing agents include lithium aluminum hydride, diisobutylaluminum hydride, and sodium bis(2-methoxyethoxy)aluminum hydride. Examples of oxidizing agents include pyridinium chlorochromate and oxalyl chloride. A compound represented by general formula (S-6) can be obtained by reacting a compound represented by general formula (S-3) with a compound represented by general formula (S-4) or (S-5) (wherein X represents chlorine, bromine, or iodine). An example of the reaction is the Wittig reaction, in which a base is reacted with a compound represented by general formula (S-4) or (S-5) to form a phosphorus ylide, which is then reacted with a compound represented by general formula (S-3). In this case, examples of the base include potassium t-butoxide. Furthermore, when Pg is a benzyl group, catalytic hydrogen reduction in the presence of 5% palladium carbon can be used to obtain a hydroxyl group-containing compound represented by general formula (S-7). Next, a deacetalization reaction can be carried out under acidic conditions using dilute hydrochloric acid or the like to obtain a compound represented by (S-8). Next, a transesterification reaction of the generated hydroxyl group with ethyl acrylate using a tin catalyst can be carried out to obtain the target compound of general formula (Y)-2 having an acryloyl group as a polymerizable group.

[0086] (Compound manufacturing method-3)

[0087] [ka]

[0088] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning.i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0089] A compound of general formula (S-12) can be obtained by reacting a compound of general formula (S-9) with compounds of general formulas (S-10) and (S-11). Reaction examples include the Williamson reaction, in which the hydroxyl group of general formula (S-9) is converted into a leaving group by reacting with p-toluenesulfonyl chloride, methylsulfonyl chloride, or the like, and then reacted with (S-10) and (S-11) in the presence of a base. Examples of bases include potassium carbonate and cesium carbonate. Another example is the Mitsunobu reaction, in which the hydroxyl group is activated with an azocarboxylic acid ester and triphenylphosphine, followed by reaction with an alcohol. Examples of azocarboxylic acid esters include diethyl azodicarboxylate and diisopropyl azodicarboxylate. Furthermore, when Pg is a benzyl group, a hydroxyl-containing compound of general formula (S-13) can be obtained by catalytic hydrogen reduction in the presence of 5% palladium on carbon. Then, the resulting hydroxyl group is subjected to a transesterification reaction with ethyl methacrylate using a tin catalyst to obtain the target compound of formula (Y)-3 having a methacryloyl group as the polymerizable group.

[0090] (Compound manufacturing method-4)

[0091] [ka]

[0092] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0093] A compound represented by general formula (S-14) can be reacted with compounds represented by general formulas (S-10) and (S-11) to obtain a compound represented by general formula (S-15). For example, a halogenating agent is applied to the carboxyl group of general formula (S-14) to form an acid halide, which is then reacted with compounds represented by general formulas (S-10) and (S-11) to obtain a compound represented by general formula (S-15). Examples of halogenating agents include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride, and phosphorus tribromide. Another example is the esterification reaction of a carboxyl group with an alcohol using a dehydration condensation agent such as dicyclohexylcarbodiimide. Furthermore, when Pg is a benzyl group, a hydroxyl-containing compound represented by general formula (S-16) can be obtained by catalytic hydrogen reduction in the same manner as in Production Method 3. Then, the resulting hydroxyl group is transesterified with ethyl methacrylate using a tin catalyst to obtain the target compound of formula (Y)-4 having a methacryloyl group as the polymerizable group.

[0094] (Compound manufacturing method-5)

[0095] [ka]

[0096] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0097] A compound represented by general formula (S-17) can be reacted with compounds represented by general formulas (S-18) and (S-19) to obtain a compound represented by general formula (S-20). For example, a hydrogen atom of a compound represented by general formula (S-17) can be abstracted with a base to form an enolate, which can then be reacted with compounds represented by general formulas (S-18) and (S-19) to obtain a compound represented by general formula (S-20) by a Michael addition reaction. Examples of bases include triethylamine and diazabicycloundecene. Furthermore, when Pg is a benzyl group, catalytic hydrogen reduction can be performed in the same manner as in Production Method 3 to obtain a hydroxyl group-containing compound represented by general formula (S-21). The resulting hydroxyl group can then be transesterified with ethyl methacrylate using a tin catalyst to obtain the target compound represented by general formula (Y)-5, which has a methacryloyl group as a polymerizable group.

[0098] (Compound manufacturing method-6)

[0099] [ka]

[0100] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in general formula (Y), R s1 represents an alkyl group having 1 to 6 carbon atoms, and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0101] A compound represented by general formula (S-23) can be obtained by reducing a compound represented by general formula (S-22) in the same manner as in Production Method 2. Alternatively, a compound represented by general formula (S-22) can be reduced to an alcohol, and then oxidized to an aldehyde, in the same manner as in Production Method 2, to obtain a compound represented by general formula (S-23). ​​A compound represented by general formula (S-24) can be obtained by reacting a compound represented by general formula (S-23) with a compound represented by general formula (S-4) in the same manner as in Production Method 2 (wherein X represents chlorine, bromine, or iodine). Furthermore, when Pg is a benzyl group, a hydroxyl-containing compound represented by general formula (S-25) can be obtained by catalytic hydrogen reduction in the same manner as in Production Method 2. Subsequently, a compound represented by general formula (S-26) can be obtained by transesterification of the generated hydroxyl group with ethyl methacrylate using a tin catalyst. The compound represented by general formula (S-26) can be reacted with the compound represented by general formula (S-19) in the same manner as in Production Method 5 to obtain the compound represented by general formula (S-27). Furthermore, when Pg is a tetrahydropyranyl group, a deacetalization reaction can be carried out under acidic conditions using dilute hydrochloric acid or the like to obtain the compound represented by (S-28). The target compound, general formula (Y)-6, can then be obtained by transesterification of the resulting hydroxyl group with ethyl acrylate using a tin catalyst.

[0102] (Compound manufacturing method-7)

[0103] [ka]

[0104] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Zi2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 In the formula (Y), mx and nx have the same meanings as m and n, respectively, in general formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg. Similarly to Production Method 3, a compound represented by general formula (S-29) can be reacted with a compound represented by general formula (S-10) to obtain a compound represented by general formula (S-30). Furthermore, when Pg is a benzyl group, a hydroxyl-containing compound represented by general formula (S-31) can be obtained by catalytic hydrogen reduction, similar to Production Method 3. Subsequently, a compound represented by general formula (S-32) can be obtained by transesterification of the generated hydroxyl group with ethyl methacrylate using a tin catalyst. Similarly to Production Method 5, a compound represented by general formula (S-32) can be obtained by reacting a compound represented by general formula (S-19) with a compound represented by general formula (S-33). Furthermore, when Pg is a tetrahydropyranyl group, a compound represented by (S-34) can be obtained by deacetalization under acidic conditions using dilute hydrochloric acid or the like. The resulting hydroxyl group is then subjected to a transesterification reaction with ethyl acrylate using a tin catalyst to obtain the target compound of general formula (Y)-7.

[0105] (Compound manufacturing method-8)

[0106] [ka]

[0107] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0108] In the same manner as in Production Method 4, a compound represented by general formula (S-35) can be reacted with a compound represented by general formula (S-10) to obtain a compound represented by general formula (S-36). Furthermore, when Pg is a benzyl group, catalytic hydrogen reduction can be performed in the same manner as in Production Method 3 to obtain a hydroxyl-containing compound represented by general formula (S-37). Subsequently, a compound represented by general formula (S-38) can be obtained by a transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst. Similarly to Production Method 5, a compound represented by general formula (S-39) can be obtained by reacting the compound represented by general formula (S-38) with a compound represented by general formula (S-19). Furthermore, when Pg is a tetrahydropyranyl group, a compound represented by (S-40) can be obtained by a deacetalization reaction under acidic conditions using dilute hydrochloric acid or the like. Subsequently, the target compound, general formula (Y)-8, can be obtained by a transesterification reaction of the generated hydroxyl group with ethyl acrylate using a tin catalyst.

[0109] (Compound manufacturing method-9)

[0110] [ka]

[0111] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning.i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0112] The compound represented by general formula (S-25) can be reacted with the compound represented by general formula (S-19) in the same manner as in Production Method 5 to obtain the compound represented by general formula (S-41). The resulting hydroxyl group can then be transesterified with ethyl acrylate using a tin catalyst to obtain the compound represented by general formula (S-42). Furthermore, when Pg is a tetrahydropyranyl group, a deacetalization reaction can be carried out under acidic conditions using dilute hydrochloric acid or the like to obtain the compound represented by (S-43). The resulting hydroxyl group can then be transesterified with ethyl methacrylate using a tin catalyst to obtain the target compound, general formula (Y)-9.

[0113] (Compound manufacturing method-10)

[0114] [ka]

[0115] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning.i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and M i1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0116] A compound represented by general formula (S-31) can be reacted with a compound represented by general formula (S-19) in the same manner as in Production Method 5 to obtain a compound represented by general formula (S-44). The resulting hydroxyl group can then be transesterified with ethyl acrylate using a tin catalyst to obtain a compound represented by general formula (S-45). Furthermore, when Pg is a tetrahydropyranyl group, a deacetalization reaction can be carried out under acidic conditions using dilute hydrochloric acid or the like to obtain a compound represented by (S-46). The resulting hydroxyl group can then be transesterified with ethyl methacrylate using a tin catalyst to obtain the target compound, general formula (Y)-10.

[0117] (Compound manufacturing method-11)

[0118] [ka]

[0119] (In the formula, R i1 and R i2 is R in general formula (Y) y1 and R y2 and S have the same meaning. i1 and S i2 is S in general formula (Y) y1 and S y2 and Z have the same meaning. i1 and Z i2 is Z in general formula (Y) y1 and Z y2 and Mi1 and M i2 is M in general formula (Y) y1 and M y2 mx and nx have the same meanings as m and n in formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.

[0120] A compound represented by general formula (S-37) can be reacted with a compound represented by general formula (S-19) in the same manner as in Production Method 5 to obtain a compound represented by general formula (S-47). The resulting hydroxyl group can then be transesterified with ethyl acrylate using a tin catalyst to obtain a compound represented by general formula (S-48). Furthermore, when Pg is a tetrahydropyranyl group, a deacetalization reaction can be carried out under acidic conditions using dilute hydrochloric acid or the like to obtain a compound represented by (S-49). The target compound, general formula (Y)-11, can then be obtained by transesterification with the resulting hydroxyl group and ethyl methacrylate using a tin catalyst.

[0121] Examples of reaction conditions other than those described in each step include those described in literature such as Experimental Chemistry Lectures (edited by the Chemical Society of Japan, published by Maruzen Co., Ltd.), Organic Syntheses (A John Wiley & Sons, Inc., Publication), Beilstein Handbook of Organic Chemistry (Beilstein-Institut für Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co.K), and Fiesers' Reagents for Organic Synthesis (John Wiley & Sons, Inc.), or those listed in databases such as SciFinder (Chemical Abstracts Service, American Chemical Society) and Reaxys (Elsevier Ltd.).

[0122] In addition, a reaction solvent can be used appropriately in each step. Specific examples of the solvent include ethanol, tetrahydrofuran, toluene, dichloromethane, water, etc. When the reaction is carried out in a two-phase system of an organic solvent and water, a phase transfer catalyst can be added. Specific examples of the phase transfer catalyst include benzyltrimethylammonium bromide, tetrabutylammonium bromide, etc.

[0123] In addition, purification can be carried out in each step as necessary. Purification methods include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid separation. Specific examples of purification agents include silica gel, NH2 silica gel, alumina, and activated carbon.

[0124] (Liquid Crystal Composition)

[0125] The compound represented by general formula (Y) can be added to a liquid crystal composition. One or more compounds represented by general formula (Y) of the present invention may be added to the liquid crystal composition, and the liquid crystal composition may further contain, in addition to the compound represented by general formula (Y), a known polymerizable compound, an antioxidant, etc., which are used in liquid crystal compositions.

[0126] When two or more types of liquid crystal molecules are mixed and used, various combinations are possible, but at least one type must contain the following general formula (II), and if the liquid crystal composition has a positive dielectric anisotropy, it may further contain the following general formula (IIIa), (IIIb), or (IIIc), and if the liquid crystal composition has a negative dielectric anisotropy, it may contain a compound represented by the following general formula (IVa), (IVb), or (IVc).

[0127] The compounds represented by general formula (II) are shown below.

[0128] [ka]

[0129] (In the formula, R 21 and R 22each independently represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in which one methylene group or two or more non-adjacent methylene groups may be substituted with -O- or -S-, and one or more hydrogen atoms in these groups may be substituted with a fluorine atom or a chlorine atom, M 21 , M 22 and M 23 are independent of each other (a) a trans-1,4-cyclohexylene group (in which one methylene group or two or more non-adjacent methylene groups may be replaced by -O- or -S-), (b) a 1,4-phenylene group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by a nitrogen atom), a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, and (c) 1,4-cyclohexenylene group, 1,4-bicyclo[2.2.2]octylene group, piperidine-2,5-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group and 1,2,3,4-tetrahydronaphthalene-2,6-diyl group represents a group selected from the group consisting of o represents 0, 1 or 2; L 21 and L 22 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CHO-, -OCF2-, -CF2O-, -CH=CH-, -CH=NN=CH-, or -C≡C-; L 22 If there are multiple, they may be the same or different, and M 23 If there are multiple, they may be the same or different.)

[0130] In the compound represented by general formula (II), R 21 and R 22are each independently preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms (including groups in which one methylene group or two or more non-adjacent methylene groups are replaced by -O- or -S-, and groups in which one or more hydrogen atoms are replaced by fluorine atoms or chlorine atoms), more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 6 carbon atoms, and particularly preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

[0131] M 21 , M 22 and M 23 are each independently a trans-1,4-cyclohexylene group (including a group in which one CH2 group or two non-adjacent CH2 groups are replaced by an oxygen atom), a 1,4-phenylene group (including a group in which one or more CH groups are replaced by a nitrogen atom), a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2 [2.2.2]octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is preferred, trans-1,4-cyclohexylene group, 1,4-phenylene group, or 1,4-bicyclo[2.2.2]octylene group is more preferred, and trans-1,4-cyclohexylene group or 1,4-phenylene group is particularly preferred. o is preferably 0, 1, or 2, and more preferably 0 or 1. L 21 and L 22 are each independently preferably a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CHO-, -OCF2-, -CF2O-, -CH=CH-, -CH=NN=CH- or -C≡C-, more preferably a single bond, -CH2CH2-, -(CH2)4-, -OCH2- or -CHO-, and even more preferably a single bond or -CH2CH2-.

[0132] Among the structures formed by combining the above options, -CH=CH-CH=CH-, -C≡CC≡C-, and -CH=CH-C≡C- are undesirable due to their chemical stability. Furthermore, structures in which hydrogen atoms in these structures are replaced with fluorine atoms are also undesirable. Furthermore, structures in which oxygen atoms are bonded to each other, structures in which sulfur atoms are bonded to each other, and structures in which a sulfur atom and an oxygen atom are bonded are also undesirable. Furthermore, structures in which nitrogen atoms are bonded to each other, structures in which a nitrogen atom and an oxygen atom are bonded, and structures in which a nitrogen atom and a sulfur atom are bonded are also undesirable.

[0133] More specifically, the general formula (II) is preferably a compound represented by the group consisting of the following general formulas (II-A) to (II-P) as specific structures.

[0134] [ka]

[0135] (In the formula, R 23 and R 24 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms.

[0136] R 23 and R 24 are each independently more preferably an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. From the viewpoint of increasing the response speed, an alkenyl group having 1 to 5 carbon atoms is preferred.

[0137] Among the compounds represented by general formulas (II-A) to (II-P), compounds represented by general formula (II-A), general formula (II-B), general formula (II-C), general formula (II-E), general formula (II-H), general formula (II-I), general formula (II-I) or general formula (II-K) are preferred, and compounds represented by general formula (II-A), general formula (II-C), general formula (II-E), general formula (II-H) or general formula (II-I) are more preferred.

[0138] In the present invention, at least one compound represented by general formula (II) is contained, preferably 1 to 10 types, and particularly preferably 2 to 8 types. The lower limit of the content of the compound represented by general formula (II) is preferably 5 mass%, more preferably 10 mass%, even more preferably 20 mass%, and particularly preferably 30 mass%, and the upper limit is preferably 80 mass%, more preferably 70 mass%, and even more preferably 60 mass%.

[0139] When the dielectric anisotropy of the liquid crystal composition is positive, the liquid crystal composition further contains a compound represented by the general formula (IIIa), the general formula (IIIb) and the general formula (IIIc)

[0140] [ka]

[0141] (In the formula, R 31 , R 32 and R 33 each independently represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in which one methylene group or two or more non-adjacent methylene groups may be substituted with -O- or -S-, and one or more hydrogen atoms in these groups may be substituted with a fluorine atom or a chlorine atom, M 31 , M 32 , M 33 , M 34 , M 35 , M 36 , M 37 and M 38are independent of each other, (d) a trans-1,4-cyclohexylene group (in which one methylene group or two or more non-adjacent methylene groups may be replaced by -O- or -S-), (e) a 1,4-phenylene group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by -N=), a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, and (f) 1,4-cyclohexenylene group, 1,4-bicyclo[2.2.2]octylene group, piperidine-2,5-diyl group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and decahydronaphthalene-2,6-diyl group wherein a hydrogen atom contained in the group (d), group (e) or group (f) may be substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a chlorine atom; L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 and L 38 each independently represents a single bond, -COO-, -OCO-, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-; M 32 , M 34 , M 35 , M 37 , M 38 , L 31 , L 33 , L 35 , L 36 and / or L 38 When there are multiple, they may be the same or different, X 31 , X 32 , X 33 , X 34 , X 35 , X 36 and X 37each independently represents a hydrogen atom or a fluorine atom, Y 31 , Y 32 and Y 33 each independently represents a fluorine atom, a chlorine atom, a cyano group, a thiocyanato group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or a difluoromethoxy group; p, q, r, s and t each independently represent 0, 1 or 2, provided that q+r and s+t is 2 or less.

[0142] In the compounds represented by general formula (IIIa), general formula (IIIb) and general formula (IIIc), R 31 , R 32 and R 33 are each independently preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, a linear alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms (including groups in which one methylene group or two or more non-adjacent methylene groups are substituted with -O- or -S-, and groups in which one or more hydrogen atoms are substituted with fluorine atoms or chlorine atoms), more preferably a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and particularly preferably a linear alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.

[0143] M 31 , M 32 , M 33 , M 34 , M 35 , M 36 , M 37 and M 38are each independently a trans-1,4-cyclohexylene group (including cases in which one methylene group or two or more non-adjacent methylene groups in this group are replaced by -O- or -S-), a 1,4-phenylene group (including cases in which one -CH= or two or more non-adjacent -CH= groups are replaced by nitrogen atoms), a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2, Preferred are groups represented by a 6-diyl group and a decahydronaphthalene-2,6-diyl group (each of which includes groups in which a hydrogen atom is substituted by a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorine atom), more preferred are a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 3-fluoro-1,4-phenylene group, or a 3,5-difluoro-1,4-phenylene group, still more preferred are a trans-1,4-cyclohexylene group or a 1,4-phenylene group, and particularly preferred is a trans-1,4-cyclohexylene group.

[0144] L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 and L 38 are each independently preferably a single bond, -OCO-, -COO-, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-, more preferably a single bond, -CH2CH2-, -(CH2)4- or -C≡C-, particularly preferably a single bond or -CH2CH2-. 31 , X 32 , X 33 , X 34 , X 35 , X 36 and X 37 are each independently a hydrogen atom or a fluorine atom, and Y 31 , Y 32 and Y 33preferably each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a thiocyanato group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a difluoromethoxy group, or an alkyl group having 1 to 12 carbon atoms, more preferably a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, or an alkyl group having 1 to 12 carbon atoms, particularly preferably a fluorine atom. p, q, r, s, and t each independently represent 0, 1, or 2, provided that q+r and s+t are 2 or less.

[0145] Among the structures formed by combining the above options, -CH=CH-CH=CH-, -C≡CC≡C-, and -CH=CH-C≡C- are undesirable due to their chemical stability. Furthermore, structures in which hydrogen atoms in these structures are replaced with fluorine atoms are also undesirable. Furthermore, structures in which oxygen atoms are bonded to each other, structures in which sulfur atoms are bonded to each other, and structures in which a sulfur atom and an oxygen atom are bonded are also undesirable. Furthermore, structures in which nitrogen atoms are bonded to each other, structures in which a nitrogen atom and an oxygen atom are bonded, and structures in which a nitrogen atom and a sulfur atom are bonded are also undesirable.

[0146] Specifically, it is preferable that the structure be represented by the following general formula (IIIa-1).

[0147] [ka]

[0148] (In the formula, R 34 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, and L 39 and L 40 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-; M 38 represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and X 32represents a hydrogen atom or a fluorine atom, p1 represents 0 or 1, Y 34 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxy group.

[0149] More specifically, the following general formulae (IIIa-2a) to (IIIa-4d)

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] (In the formula, R 34 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms; X 31 and X 32 each independently represents a hydrogen atom or a fluorine atom, Y 31 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxy group.

[0154] [ka]

[0155] (In the formula, R 34 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms; Y 31represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group or a trifluoromethoxy group. ) is also preferred.

[0156] The general formula (IIIb) has the following general formula as a specific structure:

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] (In the formula, R 35 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms; Y 35 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxy group.

[0161] The general formula (IIIc) has the following general formula as a specific structure:

[0162] [ka]

[0163] [ka]

[0164] [ka]

[0165] (In the formula, R 36 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms; Y 36 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group or a trifluoromethoxy group.

[0166] The composition contains at least one compound selected from the group consisting of compounds represented by general formula (IIIa), general formula (IIIb), and general formula (IIIc), preferably 1 to 10 compounds, and particularly preferably 2 to 8 compounds. The lower limit of the content of the group consisting of compounds represented by general formula (IIIa), general formula (IIIb), and general formula (IIIc) is preferably 5% by mass, more preferably 10% by mass, and preferably 20% by mass, and the upper limit is preferably 80% by mass, preferably 70% by mass, preferably 60% by mass, and even more preferably 50% by mass.

[0167] When the dielectric anisotropy of the liquid crystal composition is negative, the liquid crystal composition further contains a compound represented by the general formula (IVa), the general formula (IVb) and the general formula (IVc)

[0168] [ka]

[0169] (R in the formula 41 , R 42 , R 43 , R 44 , R 45 and R 46 each independently represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in which one methylene group or two or more non-adjacent methylene groups may be substituted with -O- or -S-, and one or more hydrogen atoms in these groups may be substituted with a fluorine atom or a chlorine atom, M 41 , M 42 , M 43 , M44 , M 45 , M 46 , M 47 , M 48 and M 49 are independent of each other, (g) a trans-1,4-cyclohexylene group (in which one methylene group or two or more non-adjacent methylene groups may be replaced by -O- or -S-), (h) a 1,4-phenylene group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by a nitrogen atom); and (i) 1,4-cyclohexenylene group, 1,4-bicyclo[2.2.2]octylene group, piperidine-2,5-diyl group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and decahydronaphthalene-2,6-diyl group wherein a hydrogen atom contained in the group (g), group (h) or group (i) may be substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a chlorine atom; L 41 , L 42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 and L 49 each independently represents a single bond, -COO-, -OCO-, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-; M 42 , M 43 , M 45 , M 46 , M 48 , M 49 , L 41 , L 43 , L 44 , L 46 , L 47 and / or L 49 When there are multiple, they may be the same or different, X 41 , X 42, X 43 , X 44 , X 45 , X 46 , X 47 and X 48 each independently represents a hydrogen atom, a trifluoromethyl group, a trifluoromethoxy group, or a fluorine atom, and X 41 and X 42 represents a fluorine atom, and X 43 , X 44 and X 45 represents a fluorine atom, and X 46 , X 47 and X 48 represents a fluorine atom, but X 46 and X 47 does not simultaneously represent a fluorine atom, and X 46 and X 48 does not simultaneously represent a fluorine atom, G represents a methylene group or -O-, and u, v, w, x, y, and z each independently represent 0, 1, or 2, provided that u+v, w+x, and y+z are 2 or less.

[0170] In addition, in the compounds represented by general formula (IVa), general formula (IVb), and general formula (IVc), R 41 , R 42 , R 43 , R 44 , R 45 and R 46 are each independently preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, a linear alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms (including groups in which one methylene group or two or more non-adjacent methylene groups are substituted with -O- or -S-, and groups in which one or more hydrogen atoms are substituted with fluorine atoms or chlorine atoms), more preferably a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and particularly preferably a linear alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms. 41 , M42 , M 43 , M 44 , M 45 , M 46 , M 47 , M 48 and M 49 are each independently a trans-1,4-cyclohexylene group (including those in which one methylene group or two or more non-adjacent methylene groups are replaced by -O- or -S-), a 1,4-phenylene group (including those in which one -CH= or two or more non-adjacent -CH= are replaced by -N=), a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6- Groups represented by a diyl group and a decahydronaphthalene-2,6-diyl group (including groups in which the hydrogen atoms contained in each group are substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorine atom) are preferred, a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 3-fluoro-1,4-phenylene group, or a 2,3-difluoro-1,4-phenylene group is more preferred, a trans-1,4-cyclohexylene group or a 1,4-phenylene group is even more preferred, and a trans-1,4-cyclohexylene group is particularly preferred. 41 , L 42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 and L 49 are each independently a single bond, -CH2CH2-, -(CH2)4-, -OCO-, -COO-, -OCH2-, -CHO-, -OCF2-, -CF2O- or -C≡C-, and are preferably a single bond, -CH2CH 2 -, -OCH2- or -CH2O- is more preferred. X 41 , X 42 , X 43 , X 44 , X 45 , X 46 and X 47are each independently a hydrogen atom or a fluorine atom, G is a methylene group or -O-, u, v, w, x, y, and z are each independently 0, 1, or 2, provided that u+v, w+x, and y+z are 2 or less.

[0171] Among the structures formed by combining the above options, -CH=CH-CH=CH-, -C≡CC≡C-, and -CH=CH-C≡C- are undesirable due to their chemical stability. Furthermore, structures in which hydrogen atoms in these structures are replaced with fluorine atoms are also undesirable. Furthermore, structures in which oxygen atoms are bonded to each other, structures in which sulfur atoms are bonded to each other, and structures in which a sulfur atom and an oxygen atom are bonded are also undesirable. Furthermore, structures in which nitrogen atoms are bonded to each other, structures in which a nitrogen atom and an oxygen atom are bonded, and structures in which a nitrogen atom and a sulfur atom are bonded are also undesirable.

[0172] Specifically, the compound represented by general formula (IVa) preferably has a structure represented by the following general formula (IVa-1).

[0173] [ka]

[0174] (In the formula, R 47 and R 48 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms; L 50 , L 51 and L 52 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-; M 50 represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and u1 and v1 each independently represent 0 or 1.

[0175] More specifically, the following general formulae (IVa-2a) to (IVa-3i)

[0176] [ka]

[0177] [ka]

[0178] (In the formula, R 47 and R 48 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms. 47 and R 48 are each independently an alkyl group having 1 to 8 carbon atoms or an alkoxyl group having 1 to 8 carbon atoms.

[0179] Specifically, the compound represented by general formula (IVb) preferably has a structure represented by the following general formula (IVb-1).

[0180] [ka]

[0181] (In the formula, R 49 and R 50 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms; L 52 , L 53 and L 54 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-; M 51 , M 52 and M 53 represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and w1 and x1 independently represent 0, 1, or 2, provided that w1+x1 is 2 or less.

[0182] More specifically, the following general formulae (IVb-2a) to (IVb-3l)

[0183] [ka]

[0184] [ka]

[0185] (In the formula, R 49 and R 50 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms.) is preferred.

[0186] Specifically, the compound represented by general formula (IVc) preferably has the structure represented by the following general formula (IVc-1a) and general formula (IVc-1b).

[0187] [ka]

[0188] (In the formula, R 51 and R 52 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms; L 56 , L 57 and L 58 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-; M 54 , M 55 and M 56 represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, y1 and z1 independently represent 0, 1 or 2, provided that y1 + z1 is 2 or less.

[0189] More specifically, the following general formulae (IVc-2a) to (IVc-2g)

[0190] [ka]

[0191] (In the formula, R 51 and R 52 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms.

[0192] The third component contains at least one compound selected from the group consisting of compounds represented by general formula (IIIa), general formula (IIIb), and general formula (IIIc) or compounds selected from the group consisting of compounds represented by general formula (IVa), general formula (IVb), and general formula (IVc), preferably 2 to 10 types, particularly preferably 2 to 8 types, and the lower limit of the content is preferably 5 mass%, more preferably 10 mass%, and more preferably 20 mass%, and the upper limit is preferably 80 mass%, preferably 70 mass%, preferably 60 mass%, and preferably 50 mass%.

[0193] In the liquid crystal composition containing the polymerizable compound of the present invention, Δn is preferably in the range of 0.08 to 0.25.

[0194] In the liquid crystal composition containing the polymerizable compound of the present invention, a liquid crystal composition having a positive or negative Δε can be used depending on the display mode of the liquid crystal display device. In a VA mode liquid crystal display device, a liquid crystal composition having a negative Δε is used. In this case, Δε is preferably -1 or less, more preferably -2 or less.

[0195] A liquid crystal composition containing the polymerizable compound of the present invention has a wide liquid crystal phase temperature range (the absolute value of the difference between the liquid crystal phase minimum temperature and the liquid crystal phase maximum temperature), and the liquid crystal phase temperature range is preferably 100°C or higher, more preferably 120°C or higher. The liquid crystal phase maximum temperature is preferably 70°C or higher, more preferably 80°C or higher. Furthermore, the liquid crystal phase minimum temperature is preferably -20°C or lower, more preferably -30°C or lower. In addition to the above compounds, the liquid crystal composition of the present invention may contain nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, etc. for STN liquid crystals.

[0196] In the present invention, the polymerization initiator compound of the present invention may be used alone, but in order to improve the alignment stability of the liquid crystal, it is preferable to use a polymerizable compound having a mesogenic structure in combination. The polymerizable compound may be a known polymerizable compound used in liquid crystal compositions. As an example of the polymerizable compound, it is preferable to contain one or more compounds represented by general formula (P).

[0197] [ka]

[0198] (In the above general formula (P), R p1 is a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms, or -Sp p2 -P p2 wherein one or two or more non-adjacent -CH2- groups in the alkyl group are each independently optionally substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, and one or two or more hydrogen atoms in the alkyl group are each independently optionally substituted by a cyano group, a fluorine atom or a chlorine atom; P p1 and P p2 are each independently represented by the general formula (P p1 -1) to the formula (P p1 -9):

[0199] [ka]

[0200] (In the formula, R p11 and R p12 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms; W p11 represents a single bond, -O-, -COO-, or an alkylene group having 1 to 5 carbon atoms; t p11 represents 0, 1 or 2, but R p11 , R p12 , W p11 and / or t p11 When there are a plurality of groups, they may be the same or different. Sp p1 and Sp p2 each independently represents a single bond or a spacer group, Z p1 and Z p2 are each independently a single bond, -O-, -S-, -CH2-, -OCH2-, -CH2O-, -CO-, -C2H4-, -COO-, -OCO-, -OCOOCH2-, -CH2OCOO-, -OCH2CH2O-, or -CO-NR ZP1 -, -NR ZP1 -CO-, -SCH2-, -CH2S-, -CH=CR ZP1 -COO-, -CH=CR ZP1 -OCO-, -COO-CR ZP1 =CH-, -OCO-CR ZP1 =CH-, -COO-CR ZP1 =CH-COO-, -COO-CR ZP1 =CH-OCO-, -OCO-CR ZP1 =CH-COO-, -OCO-CR ZP1 =CH-OCO-, -(CH2) z -COO-, -(CH2) z -OCO-, -OCO-(CH2) z -, -(C=O)-O-(CH2) z-, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2- or -C≡C- (wherein z's each independently represent an integer of 1 to 4, and R ZP1 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, but if R ZP1 When there are multiple, they may be the same or different. p1 or Sp p2 ) represents A p1 and A p2 are each independently (a p ) a 1,4-cyclohexylene group (in which one —CH2— or two or more non-adjacent —CH2— groups may be replaced by —O—); (b p ) a 1,4-phenylene group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by -N=); and (c p a naphthalenediyl group, a 1,2,3,4-tetrahydronaphthalenediyl group, a decahydronaphthalenediyl group, a phenanthrene-2,7-diyl group, or an anthracene-2,6-diyl group (in which one -CH= or two or more non-adjacent -CH= groups may be replaced by -N=). represents a group selected from the group consisting of A p3 is the above group (a p ), group (b p ) and group (c p ), and a single bond; The above group (a p ), group (b p ) and group (c p ) each independently represent that a hydrogen atom in this group is replaced by a cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, or -Sp p2 -Pp2 may be substituted with m p1 represents 0, 1, 2 or 3, and Z p1 , A p2 , Sp p2 and / or P p2 When there are multiple, they may be the same or different, m p1 is 0 and A p1 is a group other than a naphthalenediyl group, a phenanthrene-2,7-diyl group, or an anthracene-2,6-diyl group, A p3 represents a group other than a single bond. Specific examples of the polymerizable liquid crystal compound represented by general formula (P) are shown in (P-2-1) to (P-2-25), where a and b represent integers of 2 to 10.

[0201] [ka]

[0202] [ka]

[0203] [ka]

[0204] Although the liquid crystal composition containing the polymerizable compound of the present invention undergoes polymerization even in the absence of a photopolymerization initiator, the composition may contain a photopolymerization initiator to promote polymerization. Examples of the photopolymerization initiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, and acylphosphine oxides.Particularly preferred are acetophenones and benzil ketals, such as 1-hydroxycyclohexyl phenyl ketone (Omnirad 184), 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one (Omnirad 1173), 2-methyl-1-[(methylthio)phenyl]-2-morpholinopropane-1 (Omnirad 907), and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone. "Omnirad 369"), 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholino-phenyl)butan-1-one "Omnirad 379", 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(2,4,6-trimethylbenzoyl)-diphenylphosphine oxide "Omnirad TPO", 2,4,6-trimethylbenzoyl-phenyl-phosphine oxide "Omnirad 819" (IGM Resins Co., Ltd.), 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)], 2,2-dimethoxy-1,2-diphenylethan-1-one (Irgacure 651), ethanone (Irgacure OXE01), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (Irgacure OXE02), and (Irgacure OXE04) (BASF Ltd.) ), "ADEKA ARCLES NCI-831", "ADEKA ARCLES NCI-930", "ADEKA ARCLES N-1919" (manufactured by ADEKA Corporation), a mixture of 2,4-diethylthioxanthone ("Kayacure DETX" manufactured by Nippon Kayaku Co., Ltd.) and ethyl p-dimethylaminobenzoate ("Kayacure EPA" manufactured by Nippon Kayaku Co., Ltd.), a mixture of isopropylthioxanthone ("Cantacure-ITX" manufactured by Ward Prekinsop Co., Ltd.) and ethyl p-dimethylaminobenzoate, "Esacure ONE", "Esacure KIP150", "Esacure KIP160", "Esacure 1001M", "Esacure A198", "Esacure KIP IT", "Esacure KTO46", "Esacure TZT" (manufactured by Lamberti Co., Ltd.), "Speedcure BMS", "Speedcure PBZ", and "Benzophenone" (manufactured by LAMBSON Co., Ltd.).Furthermore, a photoacid generator can be used as the photocationic initiator, and examples of the photoacid generator include diazodisulfone compounds, triphenylsulfonium compounds, phenylsulfone compounds, sulfonylpyridine compounds, triazine compounds, and diphenyliodonium compounds.

[0205] Other stabilizers may also be added to the liquid crystal composition containing the polymerizable compound of the present invention to improve its storage stability. Examples of stabilizers that can be used include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols such as those shown below in (AD-1) to (AD-11), and hindered amines other than those of the present invention. When a stabilizer is used, the amount added is preferably 0.005 to 1% by mass, more preferably 0.02 to 0.5% by mass, and particularly preferably 0.03 to 0.1% by mass, based on the liquid crystal composition. Specific structures of the stabilizers are shown below in (AD-1) to (AD-11).

[0206] [ka]

[0207] [ka]

[0208] (Liquid crystal display element)

[0209] The liquid crystal composition of this embodiment is applied to a liquid crystal display element. The liquid crystal display element may be an active matrix driven liquid crystal display element. The liquid crystal display element may be a PSA type, PSVA type, VA type, IPS type, FFS type, or ECB type liquid crystal display element, and is preferably a PSA type or PSVA type liquid crystal display element. [Example]

[0210] The present invention will be further described below with reference to examples, but the present invention is not limited to these examples. In the compositions of the following examples and comparative examples, "%" means "% by mass." The purity of the compounds was analyzed by GC or UPLC. The abbreviations for the compounds and reaction solvents are as follows: tetrahydrofuran (THF), N,N-dimethylformamide (DMF), diazabicycloundecene (DBU), potassium carbonate (K2CO3), triethylamine (NEt3), 4,4-dimethylamino-pyridine (DMAP), dibutyltin oxide (Bu2SnO), tetrakistriphenylphosphine palladium (Pd(PPh3)4), 5% palladium on carbon (Pd / C), and diisopropylcarbodiimide (DIC).

[0211] Example 1: Preparation of Compound (RM-1)

[0212] 20 g of (4'-((tetrahydro-2H-pyran-2-yl)oxy)-[1,1'-biphenyl]-4-yl) acrylic acid, 5.9 g of acetylacetone, 4.5 g of DBU, and 200 mL of THF were added to a reaction vessel equipped with a stirrer, a condenser, and a thermometer, and the mixture was reacted at room temperature for 3 hours. After the reaction was completed, the mixture was cooled, 300 mL of ethyl acetate was added, and the organic layer was washed with water and saturated saline solution to distill off the solvent. Then, the mixture was purified using an alumina column, and after the solvent was distilled off, the mixture was dissolved in 100 mL of tetrahydrofuran, 20 mL of 2N hydrochloric acid was added at room temperature, and the mixture was stirred for 6 hours. After the reaction was completed, 200 mL of ethyl acetate was added, and the mixture was washed with water and saturated saline solution, and the solvent was distilled off. Then, the mixture was dispersed and washed in toluene, and purified using a silica gel column to obtain 27.1 g of compound (1).

[0213] [ka]

[0214] Under a nitrogen atmosphere, 10 g of the above compound (1), 5 g of ethyl methacrylate, 200 mg of dibutyltin oxide, and 150 mL of THF were added to a reaction vessel equipped with a stirrer, thermometer, condenser, and Dean-Stark tube, and the mixture was heated under reflux for 4 hours to carry out a transesterification reaction. After completion of the reaction, the organic layer was washed with water and saturated brine, and the solvent was distilled off. The mixture was then dispersed and washed in toluene, and purified using an amino silica gel column to obtain 8.7 g of the target compound (RM-1).

[0215] [ka]

[0216] GC-MS: m / z 717 Melting point: 144°C 1 H-NMR (solvent: deuterated chloroform): δ:2.04-2.07(m,6H),2.22(s,6H),2.37-2.54(m,8H), 5.75-5.77(m,2H),6.34-6.37(m,2H),7.13-7.27(m,8H),7.53-7.56(m,8H)

[0217] Example 2: Preparation of Compound (RM-2)

[0218] 10 g of the compound (1), 4.3 g of triethylamine, 4.5 g of acrylic acid chloride, and 100 mL of dichloromethane were added to a reaction vessel equipped with a stirrer, a condenser, and a thermometer, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, the organic layer was washed with saturated ammonium chloride solution, water, and saturated brine, and the solvent was distilled off. The concentrate was purified using an alumina column to obtain 9.1 g of the target compound (RM-2).

[0219] [ka]

[0220] GC-MS: m / z 689 Melting point: 144°C 1H-NMR (solvent: deuterated chloroform): δ:2.21(s,6H),2.38-2.52(m,8H),6.00(m,1H),6.03(m,1H) ,6.30-6.40(m,2H),6.59(m,1H),6.64(m,1H)7.12-7.22(m,8H),7.50-7.59(m,8H)

[0221] Examples 3 to 9 were produced according to the following synthesis route using the same reaction as in Example 1 and, if necessary, methods based on known methods.

[0222] Example 3: Preparation of Compound (RM-3)

[0223] [ka]

[0224] GC-MS: m / z 772

[0225] Example 4: Preparation of compound (RM-4)

[0226] [ka]

[0227] GC-MS: m / z 804

[0228] Example 5: Preparation of Compound (RM-5)

[0229] [ka]

[0230] GC-MS: m / z 632

[0231] (Example 6) Preparation of Compound (RM-6)

[0232] [ka]

[0233] GC-MS: m / z 420

[0234] (Example 7) Preparation of Compound (RM-7)

[0235] [ka]

[0236] GC-MS: m / z 572

[0237] (Example 8) Preparation of Compound (RM-8)

[0238] [ka]

[0239] GC-MS: m / z 750

[0240] Example 9: Preparation of Compound (RM-9)

[0241] [ka]

[0242] GC-MS: m / z 750

[0243] <Preparation and evaluation of liquid crystal compositions> In the following examples, the following abbreviations are used to describe compounds. (side chain) -n -C n H 2n+1 A straight-chain alkyl group with n carbon atoms n-C n H 2n+1 - a linear alkyl group with n carbon atoms -On -OC n H 2n+1 A straight-chain alkoxy group with n carbon atoms nO-C n H 2n+1O- Straight-chain alkoxy group with n carbon atoms -V -CH=CH2 V- CH2=CH- -V1 -CH=CH-CH3 1V- CH3-CH=CH- -F -F -OCF3 -OCF3

[0244] (linking group) -1O- -CH2-O- -O1- -O-CH2- -2- -CH2-CH2- -COO- -COO- -OCO- -OCO- - Single bond

[0245] (ring structure)

[0246] [ka]

[0247] In the examples, the measured properties are as follows: T ni : Nematic-isotropic liquid phase transition temperature (℃) Δn: Refractive index anisotropy at 20°C η: Viscosity at 20°C (mPa·s) γ1: Rotational viscosity at 20°C (mPa·s) Δε: Dielectric anisotropy at 20°C K 33 : Elastic constant K at 20℃ 33 (pN)

[0248] (Method of manufacturing a liquid crystal display element)

[0249] First, a liquid crystal composition containing a polymerizable compound, which will be described later, was injected by vacuum injection into a liquid crystal cell having a cell gap of 3.5 μm, which included an ITO-attached substrate coated with a polyimide alignment film that induces vertical alignment and then rubbed.

[0250] Thereafter, the liquid crystal cell into which the polymerizable compound-containing liquid crystal composition had been injected was irradiated with ultraviolet light using a fluorescent UV lamp for 90 minutes to obtain a liquid crystal display device. At this time, the illuminance measured under the condition of a central wavelength of 313 nm was 3 mW / cm. 2 The fluorescent UV lamp was adjusted so that

[0251] (Method for evaluating residual amount of polymerizable compounds)

[0252] The residual amount of polymerizable compound (ppm) in the liquid crystal display element after 150 seconds of UV irradiation under the above-mentioned irradiation conditions was measured. The method for measuring the residual amount of polymerizable compound is described below. First, the disassembled liquid crystal display element and acetonitrile were placed in a test tube, shaken, and filtered to obtain an acetonitrile solution containing the liquid crystal composition, polymer, and unreacted polymerizable compound. This was analyzed by high-performance liquid chromatography, and the peak area of ​​each component was calculated. The residual amount of polymerizable compound was determined from the ratio of the peak area of ​​the liquid crystal compound used as an indicator to the peak area of ​​the unreacted polymerizable compound and the amount of polymerizable compound initially added. The detection limit for the residual amount of polymerizable compound was 100 ppm.

[0253] (Method for evaluating pretilt angle)

[0254] First, the pretilt angle of a liquid crystal cell into which a polymerizable compound-containing liquid crystal composition had been injected was measured and defined as the pretilt angle (before UV irradiation). This liquid crystal cell was irradiated with UV light for 150 seconds under the above-mentioned irradiation conditions while applying a voltage of 10 V at a frequency of 100 Hz. Thereafter, the pretilt angle was measured and defined as the pretilt angle (after UV irradiation). The value obtained by subtracting the pretilt angle (after UV irradiation) from the measured pretilt angle (before UV irradiation) was defined as the pretilt angle change [°] due to UV irradiation. The pretilt angle was measured using an OPTIPRO manufactured by Shintech.

[0255] (VHR evaluation method)

[0256] A liquid crystal cell filled with a polymerizable compound-containing liquid crystal composition was irradiated with ultraviolet light for 60 minutes under the above-mentioned irradiation conditions, and VHR was measured under conditions of 1 V, 0.6 Hz, and 60° C. Values ​​of 95% or more were rated A, values ​​less than 95% and 90% or more were rated B, values ​​less than 90% to 80% or more were rated C, and values ​​less than 80% were rated D.

[0257] (Preparation of liquid crystal composition and evaluation results)

[0258] Liquid crystal compositions LC-001 to LC-008 were prepared and their physical properties were measured. The constitutions of the liquid crystal compositions and the results of their physical properties are shown in Table 1.

[0259] [Table 1]

[0260] (Comparative Examples 1 to 12) For Comparative Examples 1 and 2, 3000 ppm of polymerizable compound (RM-R1) was added to liquid crystal compositions (LC-001) and (LC-002), respectively, to prepare liquid crystal compositions. For Comparative Examples 3 to 10, 2700 ppm of polymerizable compound (RM-R1) and 300 ppm of initiator compound (R-1) were added to liquid crystal compositions (LC-001) to (LC-008), respectively, to prepare liquid crystal compositions. For Comparative Examples 11 and 12, 2700 ppm of polymerizable compound (RM-R1) and 300 ppm of initiator compound (R-2) were added to liquid crystal compositions (LC-001) and (LC-002), respectively, to prepare liquid crystal compositions. These liquid crystal compositions were each injected into a liquid crystal cell, and the various evaluations described above were performed. The evaluation results for Comparative Examples 1 to 12 are shown in Table 2.

[0261] [ka]

[0262] (Examples 10 to 37)

[0263] In Examples 10 to 18, 2700 ppm of the polymerizable compound (RM-R1) was added to a liquid crystal composition (LC-001), and 300 ppm of each of the polymerization initiator compounds (RM-1) to (RM-9) obtained in Examples 1 to 9 was added to each liquid crystal composition to prepare a liquid crystal composition. In Examples 19 to 27, 2700 ppm of the polymerizable compound (RM-R1) was added to a liquid crystal composition (LC-002), and 300 ppm of each of the polymerization initiator compounds (RM-1) to (RM-9) was added to each liquid crystal composition to prepare a liquid crystal composition. In Examples 28 to 33, 2700 ppm of the polymerizable compound (RM-R1) and 300 ppm of the polymerization initiator compound (RM-1) were added to liquid crystal compositions (LC-003) to (LC-008), to prepare liquid crystal compositions. In addition, for Examples 34 to 37, 3000 ppm of the polymerizable compound (RM-R1) and 1000 ppm of the polymerization initiator compound (RM-1) or (RM-2) were added to liquid crystal compositions (LC-001) and (LC-002), respectively, to prepare liquid crystal compositions. In addition, for Examples 38 to 41, 2700 ppm of the polymerizable compound (RM-R2) or (RM-R3) and 300 ppm of the polymerization initiator compound (RM-1) were added to liquid crystal compositions (LC-001) and (LC-002), respectively, to prepare liquid crystal compositions. These liquid crystal compositions were each injected into a liquid crystal cell, and the various evaluations described above were performed. The evaluation results for Examples 10 to 41 are shown in Table 2.

[0264] [Table 2]

[0265] In Examples 10 to 41, which are liquid crystal compositions containing a polymerizable initiator compound of the present invention, the amount of polymerizable compound remaining after UV irradiation was smaller than in Comparative Examples 1 to 12, indicating that the polymerization rate of the polymerizable compound was sufficiently fast. Furthermore, the amount of pretilt angle change due to UV irradiation was larger than in Comparative Examples 1 to 12, indicating that the pretilt angle could be formed in a short time. Furthermore, it was confirmed that the VHR after UV irradiation was sufficiently high.

[0266] These results demonstrate that the compound of the present invention has a sufficiently fast polymerization rate without impairing the reliability of the responsive liquid crystal composition, and is effective in forming a pretilt angle with a shorter UV irradiation time.

Claims

1. A compound represented by general formula (Y): 【Chemistry 1】 (In the formula, R ｙ１ and R ｙ２ each independently represents methyl; S ｙ１ is a single bond, (☆) -OCH ２ - or (☆) -OCOC ２ H ４ - and S ｙ２ is a single bond, -CH ２ O-(※) or -C ２ H ４ COO-(※) When m and n are 1 or 2, the (☆) is M ｙ１ represents a bonding point to M ｙ２ represents the attachment point to Z ｙ１ and Z ｙ２ each independently represents a single bond, -C ２ H ４ -, -C ４ H ８ -, -C ３ H ６ --, --OCH ２ --, --CH ２ O-, -CO-, -COO-, -OCO-, -OCOOCH ２ --, --CH ２ OCOO-,-OCH ２ CH ２ O-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa= CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO-, -OCO-CRa=CH-OCO-, -COOC ２ H ４ --, --OCOC ２ H ４ -, -C ２ H ４ OCO-, -CH ２ OCO-, -COOCH ２ --, --OCOCH ２ -, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF ２ O-, -OCF ２ -, -CF ２ CH ２ --, --CH ２ CF ２ -, -CF ２ CF ２ - or -C≡C- (wherein each Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), M in formula (Y) ｙ１ and M. ｙ２ But each independently (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced with -O-. (b) 1,4-phenylene group, 1,3-phenylene group, and (c) a naphthalene-1,4-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH=s present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N=). The above groups (a), (b) and (c) are groups selected from the group consisting of L ｙ１ may be substituted with P in formula (Y) ｙ１ and P ｙ２ Each of them independently represents the following general formula (P-1) to general formula (P-14): 【Chemistry 2】 (Wherein, the black dots represent Z ｙ１ Or Z ｙ２ represents a bond to A compound represented by the general formula (Y), wherein m and n each independently represent an integer of 1 or 2, and the total number of m+n is 2 to 4.

2. P in formula (Y) ｙ１ and P ｙ２ The compound according to claim 1, represented by general formula (P-1) or general formula (P-2):

3. A liquid crystal composition comprising one or more compounds according to claim 1 or 2.

4. 4. The liquid crystal composition according to claim 3, comprising one or more polymerizable compounds A having a structure different from that of the compound represented by formula (Y).

5. The polymerizable compound A is represented by the general formula (P): 【Chemistry 3】 (In the above general formula (P), R ｐ１ is a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms, or -Sp ｐ２ -P ｐ２ wherein the alkyl group has one or more non-adjacent —CH ２ - may be each independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, and one or more hydrogen atoms in the alkyl group may each independently be replaced by a cyano group, a fluorine atom or a chlorine atom; P ｐ１ and P ｐ２ each independently represents a general formula (P ｐ１ −1) to the formula (P ｐ１ -9): 【Chemistry 4】 (In the formula, R ｐ１１ and R ｐ１２ each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms; W ｐ１１ represents a single bond, —O—, —COO—, or an alkylene group having 1 to 5 carbon atoms; t ｐ１１ represents 0, 1 or 2, but R ｐ１１ , R ｐ１２ , W ｐ１１ And / or t ｐ１１ When there are a plurality of, they may be the same or different. Sp ｐ１ and Sp ｐ２ each independently represents a single bond or a spacer group; Z ｐ１ and Z ｐ２ each independently represents a single bond, —O—, —S—, or —CH ２ --, --OCH ２ --, --CH ２ O-, -CO-, -C ２ H ４ -, -COO-, -OCO-, -OCOOCH ２ --, --CH ２ OCOO-,-OCH ２ CH ２ O-, -CO-NR ＺＰ１ --, --NR ＺＰ１ -CO-, -SCH ２ --, --CH ２ S-, -CH=CR ＺＰ１ -COO-, -CH=CR ＺＰ１ -OCO-, -COO-CR ＺＰ１ =CH-, -OCO-CR ＺＰ１ =CH-, -COO-CR ＺＰ１ =CH-COO-, -COO-CR ＺＰ１ =CH-OCO-, -OCO-CR ＺＰ１ =CH-COO-, -OCO-CR ＺＰ１ =CH-OCO-, -(CH ２ ) ｚ -COO-, -(CH ２ ) ｚ -OCO-, -OCO-(CH ２ ) ｚ -, -(C=O)-O-(CH ２ ) ｚ -, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF ２ -, -CF ２ O-, -OCF ２ -, -CF ２ CH ２ --, --CH ２ CF ２ -, -CF ２ CF ２ - or -C≡C- (wherein z is independently an integer of 1 to 4, R ＺＰ１ Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, ＺＰ１ When there are a plurality of, they may be the same or different. ｐ１ Or Sp ｐ２ represents the point of attachment to represents, ｐ１ and A ｐ２ are each independently (a ｐ ) 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced with -O-. (b ｐ 1,4-phenylene group (in which one -CH= or two or more non-adjacent -CH= may be replaced by -N=); (c ｐ a naphthalenediyl group, a 1,2,3,4-tetrahydronaphthalenediyl group, a decahydronaphthalenediyl group, a phenanthrene-2,7-diyl group, or an anthracene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= in these groups may be replaced by -N=). represents a group selected from the group consisting of A ｐ３ is the above group (a ｐ ), group (b ｐ ) and group (c ｐ ), and a single bond; The above group (a ｐ ), group (b ｐ ) and group (c ｐ ) each independently represents a hydrogen atom present in this group, a cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, or -Sp ｐ２ -P ｐ２ may be substituted with m ｐ１ represents 0, 1, 2 or 3, and Z ｐ１ , A ｐ２ , Sp ｐ２ and / or P ｐ２ When there are a plurality of groups, they may be the same or different, but m ｐ１ is 0 and A ｐ１ is a group other than a naphthalenediyl group, a phenanthrene-2,7-diyl group, or an anthracene-2,6-diyl group, A ｐ３ represents a group other than a single bond.) 5. The liquid crystal composition according to claim 4, comprising one or more polymerizable compounds A represented by the following formula:

6. A liquid crystal display device using the liquid crystal composition according to any one of claims 3 to 5.

7. 6. An active matrix liquid crystal display device using the liquid crystal composition according to claim 3.

8. 6. A liquid crystal display element for PSA mode, PSVA mode, PS-IPS mode or PS-FFS mode, which uses the liquid crystal composition according to claim 3.

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