TWI886174B - Liquid crystal composition containing polymerizable compound and liquid crystal display element - Google Patents

Abstract

[Topic] Provide a polymerizable liquid crystal composition and a liquid crystal display element using the same, wherein the polymerizable liquid crystal composition can be used to manufacture a liquid crystal display element that can be fully polymerized at a faster speed, can be tilted by weak or less UV light, and has excellent reliability after the UV irradiation step. [Solution] The present invention provides a liquid crystal composition containing a polymerizable compound, which contains one or more compounds represented by general formula (i) and one or more polymerizable compounds, and the total content of the compounds represented by general formula (i) is within a specific range.

Description

Liquid crystal composition containing polymerizable compound and liquid crystal display element

The present invention relates to a liquid crystal composition containing a polymerizable compound and a liquid crystal display device using the same. In addition, in this specification, a liquid crystal composition containing a polymerizable compound is referred to as a liquid crystal composition containing a polymerizable compound. In addition, a polymerizable compound refers to a compound having a polymerizable group.

For example, a PSA (Polymer Sustained Alignment) mode liquid crystal display element has a structure in which a polymer structure is formed in a cell in order to control the pre-tilt angle of liquid crystal molecules. Due to its high-speed response and high contrast, it has been put into practical use as a liquid crystal display element.

The manufacture of a PSA mode liquid crystal display element is carried out in the following manner: a liquid crystal composition containing a polymerizable compound is injected between substrates, a voltage is applied, and UV light is irradiated while the liquid crystal molecules are aligned, so that the polymerizable compound is polymerized and the alignment of the liquid crystal molecules is fixed.

In recent years, high-precision pixels are required in PSA-mode liquid crystal display elements such as 4K and 8K. Therefore, due to the increase in the area of wiring or light-shielding parts, a considerable amount of UV light is intercepted, and in the same UV irradiation step as before, problems such as insufficient tilt formation, insufficient polymerization of polymerizable compounds, and a large amount of polymerizable compound residues occur. In addition, display defects such as "deterioration of response speed", "generation of residual images due to deterioration of alignment", and "burning (IS) caused by the gradual polymerization of residual polymerizable compounds during driving and the change of tilt" have been confirmed.

As can be seen from the above, for high-precision PSA mode liquid crystal display elements, a liquid crystal composition that can be stably manufactured using weaker or less UV light than before is required.

As a method for polymerizing a liquid crystal composition containing a polymerizable compound with weaker or less UV light than before, Patent Documents 1 and 2 disclose a technique for shortening the polymerization reaction rate by containing a liquid crystal compound having a terphenyl skeleton or a naphthalene skeleton. [Prior Technical Document] [Patent Document]

Patent document 1: Japanese Patent Publication No. 2013-503952 Patent document 2: International Publication No. 2014/148197

[The problem that the invention wants to solve]

As described above, in recent years, for high-precision PSA mode liquid crystal display elements, there has been a demand for liquid crystal compositions containing polymerizable compounds that can be stably manufactured with weaker or less UV light than before. However, although the liquid crystal compositions containing polymerizable compounds that include liquid crystal compounds having a terphenyl skeleton or a naphthalene skeleton described in the embodiments of Patent Document 1 or Patent Document 2 have sufficient polymerization speed, the tilt formation is insufficient, and the tilt stability is not high enough. Therefore, it is necessary to improve the properties of the liquid crystal compositions containing polymerizable compounds. Such improvement in the properties of the liquid crystal compositions containing polymerizable compounds is not limited to the use of PSA mode liquid crystal display elements, but is also required in liquid crystal compositions containing polymerizable compounds used in other drive mode liquid crystal display elements.

The problem to be solved by the present invention is to provide a liquid crystal composition containing a polymerizable compound and a liquid crystal display element using the same. The liquid crystal composition containing a polymerizable compound can be used to manufacture a liquid crystal display element that can be fully polymerized at a faster speed, can be tilted by weak or less UV light, and has excellent reliability after the UV irradiation step. [Means for solving the problem]

The inventors of the present invention have conducted in-depth research on the above-mentioned issues and found that the above-mentioned issues can be solved by containing a liquid crystal composition containing a compound with a specific structure and a polymerizable compound and further setting the content of the compound with a specific structure within a specific range, thereby completing the invention of this application.

That is, the present invention provides a liquid crystal composition containing a polymerizable compound, which contains one or more compounds represented by the following general formula (i) and one or more polymerizable compounds, wherein the total content of the compounds represented by the general formula (i) is less than 2.0 mass %.

(In the formula, R ⁱ¹ and R ⁱ² are each independently 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 2 to 10 carbon atoms. One or more hydrogen atoms in these groups may be substituted by fluorine atoms. Ring A and Ring B are each independently a group selected from the group consisting of the following groups (a), (b), (c) and (d): (a) 1,4-cyclohexylene (one -CH ₂ - or two or more non-adjacent -CH ₂ - in the group may be substituted by -O-), (b) 1,4-phenylene (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted by -N＝), (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH＝ or two or more non-adjacent -CH＝ in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N＝), and (d) 1,4-cyclohexenyl; The above groups (a), (b), (c) and (d) are each independent and may be substituted with the following groups or atoms: an alkyl group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, a cyano group, or a fluorine atom. C represents a divalent condensed cyclic group having one or more benzene rings, and one or more hydrogen atoms of the condensed cyclic group may be substituted by the following groups or atoms: an alkyl group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, or a fluorine atom; ^Zi1 and ^Zi2 each independently represent _-OCH2- , _-CH2O- , _-COO- , -OCO-, _-CF2O- , _-OCF2- , _-CH2CH2- , _-CF2CF2- , -C≡C- or a single bond; n ⁱ¹ and n ⁱ² each independently represent 0, 1 or 2; when there are plural rings A, _B , ^Zi1 and ^Zi2 , they may be the same or different.)

In addition, the present invention provides a liquid crystal display element, a liquid crystal display element for active matrix driving, and a liquid crystal display element for PSA mode, PSVA mode, PS-IPS mode or PS-FFS mode using a liquid crystal composition containing a polymerizable compound, wherein the liquid crystal composition containing a polymerizable compound contains one or more compounds represented by the above general formula (i) and one or more polymerizable compounds, and the total content of the compounds represented by the above general formula (i) is less than 2.0% by mass. [Effect of the invention]

The liquid crystal composition containing the polymerizable compound of the present invention can be fully polymerized at a faster speed, and can form a tilt with weak or less UV light, and can achieve high tilt stability. In addition, the liquid crystal composition containing the polymerizable compound of the present invention can be fully polymerized at a faster speed, and the UV irradiation time can be shortened, thereby suppressing the degradation of the liquid crystal composition caused by UV irradiation and the reduction of the voltage holding ratio (VHR).

Then, a liquid crystal display element using a liquid crystal composition containing a polymerizable compound of the present invention has a small amount of unreacted polymerizable compound residues, can form a tilt with weak or less UV light, and exhibits high-speed responsiveness, high VHR, and high tilt stability. There is no display defect such as poor orientation or residual image caused by changes in the pre-tilt angle, or the above-mentioned display defect is suppressed, and excellent display quality can be displayed.

The following is a detailed description of the liquid crystal composition containing a polymerizable compound and a liquid crystal display device using the same. In addition, the compound represented by the general formula (i) is sometimes referred to as the compound of the general formula (i) or compound (i). The same applies to other compounds.

A. Liquid crystal composition containing polymerizable compounds The liquid crystal composition containing polymerizable compounds of the present invention contains one or more compounds represented by general formula (i) and one or more polymerizable compounds, and the total content of the compounds represented by general formula (i) is less than 2.0% by mass.

(wherein, R ⁱ¹ , R ⁱ² , Ring A, Ring B, C, ^Zi1 , ^Zi2 , n ⁱ¹ and n ⁱ² are as defined above, respectively).

According to the liquid crystal composition containing a polymerizable compound of the present invention, by making the content of the compound represented by the general formula (i), that is, the compound containing a condensed ring in the structure, within a specific range, the polymerizable compound can be fully polymerized at a faster rate by utilizing the sensitization effect exerted by the compound represented by the general formula (i), and a larger tilt can be formed with weak or less UV light, and high tilt stability can be achieved. Furthermore, according to the liquid crystal composition containing a polymerizable compound of the present invention, since it can be fully polymerized at a faster rate, the UV irradiation time can be shortened, so that the degradation of the liquid crystal composition caused by UV irradiation can be suppressed, and the reduction of the voltage holding ratio (VHR) can be suppressed.

In addition, a liquid crystal display element using a liquid crystal composition containing a polymerizable compound according to the present invention has a small amount of unreacted polymerizable compound residues, can form a larger tilt with weak or less UV light, and exhibits high-speed responsiveness, high VHR, and high tilt stability. There are no display defects such as poor orientation or residual images caused by changes in the pre-tilt angle, or the above-mentioned display defects are suppressed, and excellent display quality can be displayed.

In particular, in the manufacture of high-precision PSA-mode liquid crystal display elements such as 4K or 8K, if the UV irradiation time becomes longer, the production efficiency will be significantly deteriorated. In contrast, according to the liquid crystal composition containing a polymerizable compound of the present invention, high-precision PSA-mode liquid crystal display elements such as 4K and 8K can be manufactured with a short UV irradiation time, and therefore the industrial utilization value is very high.

In the liquid crystal composition containing a polymerizable compound of the present invention, the composition other than the polymerizable compound and the compound represented by general formula (i) is sometimes referred to as the liquid crystal composition of the present invention. Hereinafter, each component contained in the liquid crystal composition containing a polymerizable compound of the present invention will be described.

[1] Compound represented by general formula (i) The liquid crystal composition containing a polymerizable compound of the present invention contains a compound represented by general formula (i) in a specific content.

In the general formula (i), R ⁱ¹ and R ⁱ² each independently represent 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 2 to 10 carbon atoms. One or more hydrogen atoms in these groups may be substituted by fluorine atoms.

From the viewpoint of high effect of lowering _γ1 , R ⁱ¹ and R ⁱ² are preferably independently an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms. Furthermore, the alkyl group and the alkenyl group are preferably in a straight chain form.

Furthermore, from the viewpoint of increasing |Δε| of a liquid crystal composition containing a polymerizable compound, R ⁱ¹ and R ⁱ² are preferably independently an alkoxy group having 1 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms.

Furthermore, from the viewpoint of increasing the reliability of VHR etc., R ⁱ¹ and R ⁱ² are preferably independently an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms.

One or more hydrogen atoms in the groups of R ⁱ¹ and R ⁱ² may be substituted by fluorine atoms or may be unsubstituted. It is preferred that R ⁱ¹ and R ⁱ² are not substituted by fluorine atoms.

In the general formula (i), ring A and ring B each independently represent a group selected from the group consisting of the following group (a), group (b), group (c) and group (d). (a) 1,4-cyclohexylene (one -CH ₂ - or two or more non-adjacent -CH ₂ - in the group may be substituted by -O-), (b) 1,4-phenylene (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted by -N＝), (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH＝ or two or more non-adjacent -CH＝ in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted by -N＝), and (d) 1,4-cyclohexenyl.

The above-mentioned groups (a), (b), (c) and (d) are each independent and may be substituted by the following groups or atoms: an alkyl group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, a cyano group or a fluorine atom.

Among them, Ring A and Ring B are preferably independent of each other, and preferably represent a group selected from the following structures.

More preferred is 1,4-cyclohexylene, unsubstituted 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene.

To describe in more detail, from the reason that the polymerization rate of the polymerizable compound can be increased, the ring A and the ring B are preferably independently unsubstituted 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene, and unsubstituted 1,4-phenylene is particularly preferred. The UV absorption band of the unsubstituted phenylene is located on the longer wavelength side than that of the phenylene substituted with other atoms such as fluorine atoms. Thus, the liquid crystal composition containing the polymerizable compound of the present invention, which contains the compound represented by the general formula (i) having an unsubstituted phenylene group, can increase the reaction rate of the polymerizable compound and can sufficiently suppress the decrease in VHR, compared with the case of containing the compound represented by the general formula (i) having a substituent.

On the other hand, from the viewpoint of further improving the miscibility with other liquid crystal components, Ring A and Ring B are preferably independently 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene.

When there are plural rings A and B, respectively, the plural rings A and the plural rings B may be the same or different.

In the general formula (i), C represents a divalent condensed cyclic group having one or more benzene rings. Here, a condensed cyclic group having one or more benzene rings refers to a group in which a plurality of rings including at least one benzene ring form a condensed ring. Furthermore, a condensed ring refers to a ring having a structure in which two or more rings are bonded to each other by sharing two or more atoms.

The condensed cyclic group represented by C is preferably a condensed cyclic group formed by condensing 2, 3 or 4 rings. In other words, the condensed cyclic group represented by C is preferably a 2-ring condensed cyclic group, a 3-ring condensed cyclic group or a 4-ring condensed cyclic group. Among them, from the perspective of compatibility with other liquid crystal molecules, a 2-ring condensed cyclic group or a 3-ring condensed cyclic group is more preferred.

Furthermore, among the rings constituting the condensed cyclic group represented by C, the number of benzene rings is preferably 1, 2 or 3, more preferably 2 or 3, and particularly preferably 2. By making the number of benzene rings in the condensed cyclic group within the above range, it is easier to achieve both an appropriate polymerization rate and high reliability due to the inclusion of the compound represented by the general formula (i).

The condensed cyclic group represented by C may be composed only of a benzene ring. Examples of the condensed cyclic group composed only of a benzene ring include naphthyl, anthracenyl, and phenanthrenyl.

Furthermore, the condensed cyclic group represented by C may be composed of one or more benzene rings and one or more rings selected from the group consisting of an aliphatic homocyclic ring, an aromatic heterocyclic ring and an aliphatic heterocyclic ring.

The aliphatic homocyclic ring has a structure in which a cyclic bond is composed only of carbon atoms. The aliphatic homocyclic ring preferably has 4 to 8 carbon atoms, more preferably has 4 to 6 carbon atoms, and even more preferably has 5 or 6 carbon atoms. Examples of the aliphatic homocyclic ring include cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, etc. Among them, the aliphatic homocyclic ring contained in the condensed ring represented by C is preferably a cyclopentane ring or a cyclohexane ring.

The aliphatic heterocyclic ring has a structure in which one, two or three _-CH2- groups in the aliphatic ring are replaced by -O-, -S- or -NH-. The number of ring members of the aliphatic heterocyclic ring is preferably 4 to 8, 4 to 6, 5 or 6. Examples of such aliphatic heterocyclic rings include pyrrolidine ring, tetrahydrofuran ring, tetrahydrothiophene ring, piperidine ring, tetrahydropyran ring and tetrahydrothiopyran ring.

The aromatic heterocyclic ring is a structure in which one, two or three -CH= in an aromatic ring are replaced by -O-, -S- or -N-. The number of ring members of the aromatic heterocyclic ring is preferably 4 to 8, 4 to 6, 5 or 6. Examples of such aromatic heterocyclic rings include pyrrole ring, furan ring, thiophene ring, pyridine ring and the like.

The condensed ring group represented by C is preferably a condensed ring group consisting of 2 or 3 benzene rings, or a condensed ring group consisting of 1 or 2 benzene rings and 1 or 2 rings selected from the group consisting of a tetrahydrofuran ring, a tetrahydropyran ring, a pyridine ring, a pyrrolidine ring, and a tetrahydrothiophene ring.

One or more hydrogen atoms in the condensed cyclic group represented by C may be substituted by the following groups or atoms: an alkyl group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, or a fluorine atom. However, in terms of ease of synthesis of the compound, one or more hydrogen atoms in the condensed cyclic group represented by C are preferably unsubstituted.

In the condensed ring group represented by C, the bonding position A with ^Zi1 (R ⁱ¹ when n ⁱ¹ is 0) and the bonding position B with ^Zi2 (R ⁱ² when n ⁱ² is 0) are not particularly limited, but it is preferred that the bonding position A and the bonding position B are located in a straight line.

Specifically, C in the general formula (i) preferably represents a condensed cyclic group selected from the following structures.

(Wherein, * represents the bond with ^Zi1 or ^Ri1 , and the black dot (●) represents the bond with ^Zi2 or ^Ri2 ).

In the above structures, C in the general formula (i) is more preferably a condensed cyclic group selected from the following structures.

(Wherein, * represents the bond with ^Zi1 or ^Ri1 , and the black dot (●) represents the bond with ^Zi2 or ^Ri2 ).

Among the above structures, C in the general formula (i) is particularly preferably 2,6-naphthalenediyl because the compatibility of high polymerization rate and high reliability can be further improved.

In general formula (i), ^Zi1 and ^Zi2 independently represent _-OCH2- , -CH2O-, -COO-, -OCO-, _-CF2O- , -OCF2-, _-CH2CH2- , _-CF2CF2- , -C≡C-, or a _single bond. _Zi1 ^{and Zi2} independently represent _-OCH2- , _-CH2O- , _-CH2CH2- , or _a single bond, and are particularly preferably a _single bond in order to accelerate the polymerization rate _of the polymerizable compound.

In the general formula (i), when a plurality of ^Zi1 and ^Zi2 exist, the plurality of ^Zi1 and the plurality of ^Zi2 may be the same or different.

For example, the compound represented by the general formula (i) can have better reliability and solubility by allowing ^Zi1 or ^Zi2 bonded to the condensed ring represented by C via one ring A or B to represent any of the above groups other than a single bond.

In the general formula (i), n ⁱ¹ and n ⁱ² are independently 0, 1 or 2. From the perspective of good mixing properties with other liquid crystal molecules, n ⁱ¹ + n ⁱ² is preferably 1 or 2. From the perspective of better mixing properties with other liquid crystal molecules and better tilt stability, n ⁱ¹ + n ⁱ² is more preferably 1. When n ⁱ¹ + n ⁱ² is 2, n ⁱ¹ may be 1 and n ⁱ² may be 1, or one of n ⁱ¹ or n ⁱ² may be 2 and the other may be 0. Among them, from the perspective of better mixing properties with other liquid crystal molecules, it is preferred that one of n ⁱ¹ or n ⁱ² is 2 and the other is 0.

In the general formula (i), when there are plural rings A, B, Z ⁱ¹ and Z ⁱ² , they may be the same or different.

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

(wherein, R ⁱ¹¹ , R ⁱ¹² , Ring A ⁱ¹ , Ring B ⁱ¹ , Zi ⁱ¹¹ , Zi ⁱ¹² , n ⁱ¹¹ and n ⁱ¹² respectively represent the same meanings as R ⁱ¹ , R ⁱ² , Ring A, Ring B, Zi ⁱ¹ , Zi ⁱ² , n ⁱ¹ and n ⁱ² in the above general formula (i), n ⁱ¹¹ + n ⁱ¹² represents 1, 2, 3 or 4, ^Xi11 to ^Xi16 each independently represent an alkyl group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, a fluorine atom or a hydrogen atom)

In the general formula (i-1), n ⁱ¹¹ +n ⁱ¹² is preferably 1 or 2 from the viewpoint of miscibility with other liquid crystal molecules, and is more preferably 1 from the viewpoint of better miscibility with other liquid crystal molecules and tilt stability.

In the general formula (i-1), ^Xi11 to ^Xi16 are independently preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, preferably a fluorine atom or a hydrogen atom, and particularly preferably a hydrogen atom.

The number of the groups which are hydrogen atoms in ^Xi11 to ^Xi16 is preferably at least 3. Specifically, the number of the groups which are hydrogen atoms in ^Xi11 to ^Xi16 is preferably 3, 4, 5 or 6, preferably 4, 5 or 6, more preferably 5 or 6, and more preferably 6.

In the general formula (i-1), preferred embodiments of R ⁱ¹¹ , R ⁱ¹² , ring A ⁱ¹ , ring B ⁱ¹ , ^Zi11 and ^Zi12 may be the same as the preferred embodiments of R ⁱ¹ , R ⁱ² , ring A, ring B, ^Zi1 and ^Zi2 in the above general formula (i), respectively.

In the general formula (i-1), when n ⁱ¹¹ represents 0 and n ⁱ¹² represents 1 or 2, and the ring ^Bi1 directly bonded to ^Ri12 is a 2,3-difluoro-1,4-phenylene group, ^Ri12 is preferably an alkoxy group having 1 to 10 carbon atoms, preferably an alkoxy group having 1 to 5 carbon atoms, and more preferably an alkoxy group having 1 to 3 carbon atoms. This is because the effect of improving the reactivity of the polymerizable compound by using the compound represented by the general formula (i-1) in combination becomes higher than when ^Ri12 is a group other than an alkoxy group. In this case, ^Ri11 is preferably an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms.

Furthermore, in the general formula (i-1), when n ⁱ¹¹ represents 0 and n ⁱ¹² represents 2, and the ring B ⁱ¹ directly bonded to R ⁱ¹¹ is a 1,4-phenylene group, R ⁱ¹ and R ⁱ² are each independently preferably an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. This is because the effect of suppressing the reduction of the voltage holding ratio ( ^VHR ) by using the compound represented by the general formula (i-1) in combination is higher than when ^one or both of R i1 and R i2 are groups other than an alkyl group.

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

(wherein, R ⁱ¹¹¹ , R ⁱ¹¹² , Ring A ⁱ¹¹ , Ring B ⁱ¹¹ , ^Zi111 and ^Zi112 respectively have the same meanings as R ⁱ¹ , R ⁱ² , Ring A, Ring B, ^Zi1 and ^Zi2 in the above general formula (i); ^Yi111 and ^Yi112 each independently represent an alkyl group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, a fluorine atom or a hydrogen atom; n ⁱ¹¹¹ and n ⁱ¹¹² each independently represent 0 or 1).

In the general formula (i-1-1), ^Yi111 and ^Yi112 are independently preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, more preferably an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom, and particularly preferably a fluorine atom or a hydrogen atom. ^Yi111 and ^Yi112 may be one fluorine atom and the other a hydrogen atom, may both represent fluorine atoms, or may both represent hydrogen atoms. The compound represented by the general formula (i-1-1) can make the polymerization rate of the polymerizable compound faster by ^Yi111 and ^Yi112 independently representing a fluorine atom or a hydrogen atom, can further improve the miscibility with other liquid crystal components, and can obtain high tilt stability.

In the general formula (i-1-1), n ⁱ¹¹¹ and n ⁱ¹¹² are independently 0 or 1. From the perspective of mixing with other liquid crystal molecules, n ⁱ¹¹¹ + n ⁱ¹¹² is preferably 0 or 1. From the perspective of better mixing with other liquid crystal molecules and better tilt stability, it is more preferably 0. When n ⁱ¹¹¹ + n ⁱ¹¹² is 1, n ⁱ¹¹¹ may represent 1 and n ⁱ¹¹² may represent 0, or n ⁱ¹¹¹ may represent 0 and n ⁱ¹¹² may represent 1. Among them, it is preferred that n ⁱ¹¹¹ represents 0 and n ⁱ¹¹² represents 1. This is because the compound represented by the general formula (i-1-1) has better mixing with other liquid crystal molecules by adopting a molecular structure with a condensed ring as the center and a ring structure biased to one side.

Preferred embodiments of R ⁱ¹¹¹ , R ⁱ¹¹² , ring A ⁱ¹¹ , ring B ⁱ¹¹ , ^Zi111 and ^Zi112 in the general formula (i-1-1) may be the same as preferred embodiments of R ⁱ¹ , R ⁱ² , ring A, ring B, ^Zi1 and ^Zi2 in the above general formula (i), respectively.

In the general formula (i-1-1), when n ⁱ¹¹¹ and n ⁱ¹² represent 0 respectively, and when both Y ⁱ¹¹¹ and Y ⁱ¹¹² represent fluorine atoms, R ⁱ¹¹² is preferably an alkoxy group having 1 to 10 carbon atoms, preferably an alkoxy group having 1 to 5 carbon atoms, and preferably an alkoxy group having 1 to 3 carbon atoms. This is because the effect of improving the reactivity of the polymerizable compound by using the compound represented by the general formula (i-1-1) in combination is higher than when R ⁱ¹¹² is a group other than an alkoxy group. In this case, R ⁱ¹¹¹ is preferably an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, and preferably an alkyl group having 1 to 3 carbon atoms.

Furthermore, in the general formula (i-1-1), when n ⁱ¹¹ represents 0 and n ⁱ¹² represents 1, when both Y ⁱ¹¹¹ and Y ⁱ¹¹² represent fluorine atoms, and B ⁱ¹¹ represents 1,4-phenylene, R ⁱ¹¹ and R ⁱ¹² are each independently preferably an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an ^alkyl group having 1 to 3 carbon atoms. This is because the effect of suppressing the reduction of the voltage holding ratio ⁽ VHR) by using the compound represented by the general formula (i-1) in combination is higher than when one or both of R i11 and R i12 are groups other than an alkyl group.

The compound represented by the general formula (i) is preferably a compound represented by the following general formula (i-1-1-1) to general formula (i-1-1-55). Among them, more preferred compounds are general formula (i-1-1-1) to general formula (i-1-1-6), general formula (i-1-1-12) to general formula (i-1-1-17), general formula (i-1-1-23) to general formula (i-1-1-28), or general formula (i-1-1-34) to general formula (i-1-1-39), general formula (i-1-1-45) to general formula (i-1-1-46) The compound represented by the general formula (i-1-1-1) to (i-1-1-4), the general formula (i-1-1-34) to (i-1-1-37), or the general formula (i-1-1-45) to (i-1-1-48) is more preferably a compound represented by the general formula (i-1-1-1) to (i-1-1-4). The compound represented by the general formula (i-1-1-1) to (i-1-1-4) is particularly preferably.

(wherein, R ⁱ¹¹¹ and R ⁱ¹¹² have the same meanings as R ⁱ¹ and R ⁱ² in the above general formula (i) respectively).

The compound of general formula (i) can promote the polymerization reaction of the polymerizable compound by its sensitizing effect. On the other hand, if the content of the compound of general formula (i) is too high, it may be difficult to form a sufficiently large tilt by a short reaction time, VHR may decrease, etc. In contrast, the liquid crystal composition containing the polymerizable compound of the present invention can fully polymerize the polymerizable compound at a faster rate by adjusting the content of the compound of general formula (i) within a specific range, can form a sufficiently large tilt in a short time, can suppress the decrease of VHR caused by UV irradiation, and can satisfy various characteristics in a well-balanced manner.

The content of the compound of general formula (i) may be less than 2.0 mass % in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention, and the upper limit of the above content is preferably 1.9 mass %, 1.8 mass %, 1.7 mass %, 1.6 mass %, 1.5 mass %, 1.4 mass %, 1.3 mass %, 1.2 mass %, 1.0 mass %, 0.9 mass %, 0.8 mass %, 0.7 mass %, 0.6 mass %, 0.5 mass %. In addition, the content of the compound of general formula (i) may be more than 0 mass % in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention, and the lower limit of the above content is preferably 0.01 mass %, 0.05 mass %, 0.1 mass %, 0.2 mass %, 0.3 mass %, 0.4 mass %, 0.5 mass %, 0.6 mass %, 0.7 mass %, 0.8 mass %, 0.9 mass %, or 1.0 mass %.

More specifically, the content of the compound of general formula (i) may be more than 0 mass % and less than 2.0 mass %, preferably 0.05 mass % to 1.9 mass %, 0.5 mass % to 1.9 mass %, 0.5 mass % to 1.5 mass %, 0.5 mass % to 1.0 mass %.

[2] Polymerizable compounds The liquid crystal composition containing polymerizable compounds of the present invention contains one or more polymerizable compounds. A polymerizable compound is a compound having at least one polymerizable group in its molecular structure. By forming a polymer in the manufacturing step of a liquid crystal display element, a tilt angle can be imparted to the liquid crystal molecules, and physical properties such as response speed, Tni, and Δε can be improved.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more of the following polymerizable compound A and at least one of the following polymerizable compound B. The polymerizable compound A and the polymerizable compound B are described below.

[2-1] Polymerizable compound A The liquid crystal composition containing a polymerizable compound of the present invention preferably contains one or more polymerizable compounds A represented by the general formula (P) as polymerizable compounds.

(In the above general formula (P), R ^p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms, or -Sp ^p2 -P ^p2 ; one or two or more non-adjacent -CH ₂ - groups in the alkyl group may independently be substituted by -CH＝CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO-; one or more hydrogen atoms in the alkyl group may independently be substituted by a cyano group, a fluorine atom, or a chlorine atom; P ^p1 and P ^p2 may independently represent any one of the general formulae (P ^p1 -1) to (P ^p1 -9).

(wherein, R ^p11 and R ^p12 are each independently 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 is a single bond, -O-, -COO-, or an alkylene group having 1 to 5 carbon atoms, t ^p11 is 0, 1, or 2. When a plurality of R ^p11 , R ^p12 , W ^p11 , and/or t ^p11 exist in the molecule, they may be the same or different), Sp ^p1 and Sp ^p2 are each independently a single bond or a spacer group, Z ^p1 and Z ^p2 are each independently a single bond, -O-, -S-, -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 - , -CF2O-} , _-OCF2- , -CF2CH2-, _-CH2CF2- , _-CF2CF2- , or -C≡C- (wherein z independently represents an integer of 1 to ₄ , ^RZP1 independently represents a hydrogen atom or an _alkyl group having 1 to 4 carbon atoms, and when a plurality of RZP1 exist in the molecule, they may be the same or different. Furthermore, * in the formula represents a bond with ^Spp1 or ^{Spp2 )} , ^Ap1 and ^Ap2 independently represent a group selected from the group consisting of the following groups (ap), ( ^bp ), and ( ^cp ), ( ^ap ) 1,4-cyclohexyl (one _-CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O-), ( ^{bp )} 1,4-cyclohexyl (one -CH2- or two or more non-adjacent _-CH2- in the group may be substituted with -O-), ) 1,4-phenylene (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted with -N＝), and (c ^p ) naphthalene-2,2,3,4-tetrahydronaphthalene-2,3,4-tetrahydronaphthalene-2,7-diyl or anthracene-2,6-diyl (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted with -N＝), ^Ap3 represents a group selected from the group consisting of the above-mentioned group (ap), group (b ^p ) and group (c ^p ), and a single bond, the above-mentioned group ( ^ap ), group (b ^p ) and group (c ^p ) are each independent ^, and the hydrogen atom in the group may be substituted with 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 , m ^p1 represents 0, 1, 2 or 3. When a plurality of Z ^p1 , A ^p2 , Sp ^p2 and/or P ^p2 exist in the molecule, they may be the same or different. When m ^p1 is 0 and A ^p1 is a group other than naphthalene diyl, phenanthrene-2,7-diyl and anthracene-2,6-diyl, A ^p3 represents a group other than a single bond. In the general formula (P), R ^p1 is preferably -Sp ^p2 -P ^p2 .

In the general formula (P), P ^p1 and P ^p2 each represent a polymerizable group. Here, the polymerizable group in the general formula (P) does not include the polar group described in the polymerizable compound B below. ^{P p1} and P ^p2 are each independently and preferably any one of the groups represented by the general formula (P ^p1 -1) to the formula (P ^p1 -3), and preferably the group represented by the general formula (P ^p1 -1).

In the general formula (P ^p1 -1) to the formula (P ^p1 -9), R ^p11 and R ^p12 are independently and preferably a hydrogen atom or a methyl group.

In the general formula (P ^p1 -1) to the formula (P ^p1 -9), t ^p11 is preferably 0 or 1.

W ^p11 in the general formula (P ^p1 -1) to the formula (P ^p1 -9) is preferably a single bond or an alkylene group having 1 to 5 carbon atoms. The alkylene group having 1 to 5 carbon atoms is preferably a methylene group or an ethylene group.

In the general formula (P), m ^p1 is preferably 0, 1 or 2, more preferably 0 or 1.

In the general formula (P), ^Zp1 and ^Zp2 are independently and preferably a single bond _, -OCH2- _{, -CH2O-} , -CO-, -C2H4- _{, -COO-} , -OCO- _{, -COOC2H4-} , _-OCOC2H4- , -C2H4OCO-, -C2H4COO- _, -CH=CH-, _-CF2- , -CF2O-, -(CH2) _z - _COO- , -(CH2)z _- OCO-, _{-OCO- ( CH2} ) _{z- ,} -CH=CH-COO-, -COO-CH=CH-, -OCOCH=CH-, -COO-( _CH2 ) _{z- , -OCF2-} or -C≡C-, preferably _a single bond, -OCH ₂ -, -CH ₂ O-, -C ₂ H ₄ -, -COO-, -OCO-, -COOC ₂ H ₄ -, -OCOC ₂ H ₄ -, -C 2 H 4 OCO-, -C ₂ H ₄ COO-, -CH＝CH-, -(CH ₂ ) ₂ -COO- _, -(CH ₂ ) ₂ -OCO-, -OCO-(CH ₂ ) _{2 -} , -CH＝CH-COO-, -COO-CH＝CH-, -OCOCH＝CH-, -COO-(CH ₂ ) ₂ -, or -C≡C-; preferably, only one of -OCH ₂ -, -CH ₂ O-, -C ₂ H ₄ -, -COO-, -OCO-, -COOC ₂ H ₄ -, -OCOC ₂ H ₄ -, -C ₂ H ₄ OCO-, -C ₂ H ₄ COO-, -CH＝CH-, -(CH ₂ ) ₂ -COO-, -(CH 2 ) 2 -OCO-, -OCO-(CH ₂ ) ₂ -, -CH＝CH-COO-, -COO _- CH＝CH-, -OCOCH＝CH-, -COO-(CH ₂ ) ₂ -, or -C≡C-, and the others are single bonds. It is preferred that only one of the groups present in the molecule is -OCH ₂ -, -CH _{2 O-} , -C ₂ H ₄ -, -COO-, or -OCO-, and the others are single bonds. It is more preferred that all of them are single bonds.

Furthermore, it is preferred that only one of ^Zp1 and ^Zp2 present in the molecule is a bonding group selected from the group consisting of -CH=CH-COO-, -COO-CH=CH-, -( _CH2 ) _2- COO-, -( _CH2 ) _2- OCO-, -O-CO-( _CH2 ) _2- , and -COO-( _CH2 ) _2- , and the others are single bonds.

In the general formula (P), Sp ^p1 and Sp ^p2 are independently represented by a single bond or a spacer group. The spacer group is preferably an alkylene group having 1 to 30 carbon atoms. The -CH ₂ - in the alkylene group may be substituted by -O-, -CO-, -COO-, -OCO-, -CH=CH- or -C≡C- as long as the oxygen atoms are not directly bonded to each other. The hydrogen atom in the alkylene group may also be substituted by a halogen atom. Among them, Sp ^p1 and Sp ^p2 are independently represented by a linear alkylene group having 1 to 10 carbon atoms or a single bond, and more preferably a single bond.

In the general formula (P), the total number of -Sp ^p1 -P ^p1 and Sp ^p2 -P ^p2 is preferably 2 or more, preferably 2 to 4, and more preferably 2 to 3.

A ^p1 and A ^p2 are each independently a group selected from the group consisting of (a ^p ), (b ^p ) and (c ^p ) below. (a ^p ) 1,4-cyclohexylene (one -CH ₂ - or two or more non-adjacent -CH ₂ - in the group may be substituted by -O-), (b ^p ) 1,4-phenylene (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted by -N＝), and (c ^p ) naphthalenediyl, 1,2,3,4-tetrahydronaphthalenediyl, decahydronaphthalenediyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted by -N＝). Furthermore, A ^p3 represents a group selected from the group consisting of the above-mentioned group (a ^p ), group (b ^p ), group (c ^p ), and a single bond.

Here, the naphthalenediyl group and the 1,2,3,4-tetrahydronaphthalenediyl group which A ^p1 , A ^p2 and A ^p3 may have are groups bonded at two positions selected from positions 1 to 8. Specifically, in the case of A ^p1 , the naphthalenediyl group and the 1,2,3,4-tetrahydronaphthalenediyl group are groups bonded to Sp ^p1 at one of two positions selected from positions 1 to 8 and bonded to Z ^p1 or Z ^p2 at the other position, in the case of A ^p2 , the groups are bonded to Z ^p1 at one of two positions selected from positions 1 to 8 and bonded to Z ^p1 or Z ^p2 at the other position, and in the case of A ^p3 , the groups are bonded to Z ^p2 at one of two positions selected from positions 1 to 8 and bonded to R ^p1 at the other position.

Furthermore, the decahydronaphthalenediyl group which A ^p1 , A ^p2 and A ^p3 may have is a group bonded at two positions selected from positions 1 to 10. Specifically, in the case of A ^p1 , the decahydronaphthalenediyl group is a group bonded to Sp ^p1 at one of the two positions selected from positions 1 to 10 and bonded to Z ^p1 or Z ^p2 at the other position, in the case of A ^p2 , the group is bonded to Z ^p1 at one of the two positions selected from positions 1 to 10 and bonded to Z ^p1 or Z ^p2 at the other position, and in the case of A ^p3 , the group is bonded to Z ^p2 at one of the two positions selected from positions 1 to 10 and bonded to R ^p1 at the other position.

Examples of the naphthalenediyl group include naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, and naphthalene-2,7-diyl. Among them, naphthalene-1,4-diyl or naphthalene-2,6-diyl is preferred.

Examples of the 1,2,3,4-tetrahydronaphthalene diyl group include 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-1,4-diyl, and 1,2,3,4-tetrahydronaphthalene-1,5-diyl. Among them, 1,2,3,4-tetrahydronaphthalene-2,6-diyl is preferred.

The decahydronaphthalenediyl group is preferably decahydronaphthalene-2,6-diyl.

A ^p1 , A ^p2 and A ^p3 are each independently preferably 1,4-phenylene or 1,4-cyclohexylene. From the viewpoint of reactivity, 1,4-phenylene is preferred. In order to improve the compatibility of 1,4-phenylene with the liquid crystal compound, at least one hydrogen atom in the 1,4-phenylene is preferably substituted with a fluorine atom, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms.

From the viewpoint of reducing the residual amount of the polymerizable compound A after UV light irradiation, it is preferred that at least one hydrogen atom present in the 1,4-phenylene group is substituted by an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, preferably by an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and preferably by an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms. As an example of the alkyl group, a methyl group is more preferred, and as an example of the alkoxy group, a methoxy group is more preferred.

Furthermore, from the viewpoint of improving the tilt stability, it is preferred that the 1,4-phenylene group is unsubstituted or at least one hydrogen atom in the 1,4-phenylene group is substituted with a fluorine atom.

When m ^p1 is 0 and A ^p1 is naphthalenediyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl, A ^p3 may also represent a single bond.

When m ^p1 is 0 and A ^p1 is a group other than naphthalenediyl, phenanthrene-2,7-diyl and anthracene-2,6-diyl, A ^p3 represents a group other than a single bond, that is, a group selected from the group consisting of the above-mentioned group (a ^p ), group (b ^p ) and group (c ^p ).

The preferred lower limit of the content of the polymerizable compound A represented by the general formula (P) is 0.01 mass%, 0.03 mass%, 0.05 mass%, 0.08 mass%, 0.1 mass%, 0.15 mass%, 0.2 mass%, 0.25 mass%, and 0.3 mass% in the total amount of the polymerizable compound-containing liquid crystal composition of the present invention. Moreover, the preferred upper limit of the content of the polymerizable compound A represented by the general formula (P) is 10 mass%, 8 mass%, 5 mass%, 3 mass%, 1.5 mass%, 1.2 mass%, 1 mass%, 0.8 mass%, and 0.5 mass% in the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

If the content of the polymerizable compound A represented by the general formula (P) contained in the liquid crystal composition containing the polymerizable compound of the present invention is small, it is difficult to show the effect of adding the polymerizable compound A represented by the general formula (P), and it is easy to produce undesirable conditions such as insufficient tilt formation and deterioration of tilt stability. In addition, it is easy to produce problems such as weak alignment control of the liquid crystal composition or weakening over time. On the other hand, if the above content is too much, there will be problems such as the amount remaining after curing increases, curing takes time, and the reliability of the liquid crystal is reduced. Therefore, by considering the balance and combining the above upper limit and lower limit to set the content, the liquid crystal composition containing the polymerizable compound of the present invention can give the liquid crystal molecules a tilt at a large enough angle, can maintain the tilt stability and the alignment control of the liquid crystal composition for a long time, and can show high reliability.

As a specific range of the content of the polymerizable compound A represented by the general formula (P), for example, in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention, it is preferably in the range of 0.05 mass% to 10 mass%, preferably in the range of 0.1 mass% to 8 mass%, preferably in the range of 0.1 mass% to 5 mass%, preferably in the range of 0.1 mass% to 3 mass%, preferably in the range of 0.2 mass% to 2 mass%, preferably in the range of 0.2 mass% to 1.3 mass%, preferably in the range of 0.2 mass% to 1 mass%, preferably in the range of 0.2 mass% to 0.56 mass%.

Preferred examples of the polymerizable compound A represented by the general formula (P) include compounds represented by the following general formulas (P-1-1) to (P-1-46).

(In the formula, P ^p11 , P ^p12 , Sp ^p11 and Sp ^p12 have the same meanings as P ^p1 , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P)).

Furthermore, as preferred examples of the polymerizable compound A represented by the general formula (P), there can be cited compounds represented by the following formulas (P-2-1) to (P-2-16).

(In the formula, P ^p21 , P ^p22 , Sp ^p21 and Sp ^p22 have the same meanings as P ^p1 , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P)).

Furthermore, as preferred examples of the polymerizable compound A represented by the general formula (P), there can be cited compounds represented by the following formulas (P-3-1) to (P-3-15).

(wherein, P ^p31 , P ^p32 , Sp ^p31 and Sp ^p32 have the same meanings as P ^p1 , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P)).

Furthermore, as preferred examples of the polymerizable compound A represented by the general formula (P), there can be cited polymerizable compounds represented by the following formulas (P-4-1) to (P-4-21).

(wherein, P ^p41 , P ^p42 , Sp ^p41 and Sp ^p42 have the same meanings as P ^p1 , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P)).

Furthermore, as preferred examples of the polymerizable compound represented by the general formula (P), there can be cited compounds represented by the following formulas (P-5-1) to (P-5-37).

(wherein, P ^p51 , P ^p52 , Sp ^p51 and Sp ^p52 have the same meanings as P ^p1 , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P)).

Among the compounds represented by the general formula (P-1-1) to (P-5-37), more preferred are compounds represented by the general formula (P-1-1) to (P-1-34) or the general formula (P-2-10) to (P-2-16), still more preferred are compounds represented by the general formula (P-1-1) to (P-1-3), the general formula (P-1-6) to (P-1-7), the general formula (P-1-10) to (P-1-11), the general formula (P-1-23), the general formula (P-1-32) or the general formula (P-2-10), and particularly preferred are compounds represented by the general formula (P-1-1) to (P-1-3), the general formula (P-1-6) to (P-1-7), the general formula (P-1-10) or the general formula (P-1-11).

[2-2] Polymerizable compound B The liquid crystal composition containing a polymerizable compound of the present invention preferably further contains one or more "polymerizable compound B having one or more polymerizable groups and one or more polar groups in its molecular structure" as a polymerizable compound.

The polymerizable compound B is a compound having a different structure from the polymerizable compound A, and is different from the polymerizable compound A in having a polar group.

The polymerizable compound B has the same function as the polymerizable compound A, but by having a polar group in the molecular structure, it can further exert the following function. That is, in a liquid crystal display element without an alignment film, the polar group of the polymer of the polymerizable compound B interacts with the substrate, and the liquid crystal molecules can be given vertical alignment even without an alignment film. Therefore, the liquid crystal composition containing a polymerizable compound of the present invention can manufacture a liquid crystal display element that does not have an alignment film on at least one side of the liquid crystal layer. In addition, in a liquid crystal display element with an alignment film, the polar group of the polymer of the polymerizable compound B interacts with impurities such as polar compounds, ionic compounds, and free radical compounds present in the liquid crystal layer or the alignment film, thereby adsorbing and capturing impurities. Therefore, the liquid crystal composition containing the polymerizable compound of the present invention can suppress the decrease of specific resistance or VHR caused by impurities, and can manufacture liquid crystal display elements with high reliability. In addition, it is speculated that the adsorption and capture function of the polar group on impurities can also be exerted in liquid crystal display elements without an alignment film.

The polymerizable compound B may have a structure having at least one polymerizable group and one polar group, and preferably has a structure having a mesogen group, one polymerizable group, and one polar group. The details of the mesogen group are described below.

[Polymerizable Group] The polymerizable group possessed by the polymerizable compound B is represented by P ^AP1 . P ^AP1 is preferably a group selected from the group represented by the following general formula (AP-1) to general formula (AP-9).

(In the formula, R ^AP1 and R ^AP2 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 10 carbon atoms. One or more non-adjacent -CH ₂ - in the alkyl group can be substituted by -O- or -CO- in a manner that the oxygen atom is not directly adjacent. One or more hydrogen atoms in the alkyl group are each independently substituted by a halogen atom or a hydroxyl group. W ^AP1 is a single bond, -O-, -COO- or -CH ₂ -. t ^AP1 is 0, 1 or 2. The * in the formula represents a bond).

Among them, P ^AP1 is preferably a group selected from the group represented by the above general formula (AP-1) to the general formula (AP-7), more preferably a group represented by the following general formula (AP-1) or general formula (AP-2), and even more preferably a group represented by the general formula (AP-1).

The polymerizable group P ^AP1 is preferably bonded to the mesogen group via the spacer group Sp ^AP1 . The mesogen group will be described in detail below. The spacer group Sp ^AP1 is preferably a single bond, or a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably a single bond or a linear alkylene group having 1 to 20 carbon atoms, and even more preferably a single bond or a linear alkylene group having 2 to 10 carbon atoms. In the spacer group Sp ^AP1 , one or two or more non-adjacent -CH ₂ - in the alkylene group may be substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO- in a manner that the oxygen atom is not directly adjacent. Furthermore, "substituted by the polymerizable group P ^AP1 " may be a state of being substituted only by the polymerizable group P ^AP1 or a state of being substituted by a group P ^AP1 -Sp ^AP1 - containing a spacer group Sp ^AP1 . The same applies to other polymerizable groups.

In the polymerizable compound B, the number of P ^AP1 -Sp ^AP1 - is preferably 1 or more and 5 or less, more preferably 1 or more and 4 or less, further preferably 2 or more and 4 or less, particularly preferably 2 or 3, and most preferably 2.

The hydrogen atom in P ^AP1 -Sp ^AP1 - may also be substituted by a polymerizing group or a polar group.

P ^AP1 -Sp ^AP1 - may bond to a polymerizable group, a mesogen group or a polar group. Among them, P ^AP1 -Sp ^AP1 - preferably bonds to a mesogen group or a polar group.

When there are multiple P ^AP1s and/or Sp ^AP1s in a molecule, they may be the same or different.

[Polar group] The polar group possessed by the polymerizable compound B is a group that interacts with the substrate, or interacts with the impurities contained in the liquid crystal layer or the alignment film, and can play the role of either a donor or an acceptor of protons sandwiching hydrogen bonds, or can also play the role of both. Preferably, it is a group containing "a polar element having an atomic group formed by bonding carbon atoms and impurity atoms". In this specification, the polar element refers to an atomic group formed by direct bonding of carbon atoms and impurity atoms. As the impurity atom, it is preferably at least one selected from the group consisting of N, O, S, P, B and Si, more preferably at least one selected from the group consisting of N, O and S, and even more preferably at least one selected from the group consisting of N and O, and O is particularly preferred.

In the polymerizable compound B, the valence of the polar element is not particularly limited, and may be monovalent, divalent, trivalent, or trivalent or more. Also, the number of polar elements in the polar group is not particularly limited.

The polymerizable compound B preferably has 1 to 8 polar groups in one molecule, more preferably 1 to 4 polar groups, and even more preferably 1 to 3 polar groups.

Furthermore, the polymerizable group is not included in the polar group, and the polar group includes a structure in which the hydrogen atom in the polar group is replaced by P ^AP1 -Sp ^AP1 - and a structure in which the hydrogen atom in P ^AP1 -Sp ^AP1 - is replaced by -OH. P ^AP1 and Sp ^AP1 are respectively described in the above paragraph "Polymeric group".

Polar groups contain 1 or more polar elements and are roughly divided into cyclic groups and chain groups. The cyclic group type is a form that includes a cyclic group having a cyclic structure, and the cyclic structure includes a polar element in its structure. The chain group type does not include "a cyclic group having a cyclic structure containing a polar element in its structure", but is a form that has a polar element in a straight chain or branched chain group, and may also have a cyclic structure without a polar element in a part of it.

A cyclic radical type polar group means a structure having at least one polar element in a cyclic atomic arrangement. In this specification, a cyclic radical is as described above. Therefore, a cyclic radical type polar group only needs to contain a "cyclic radical containing a polar element", and the polar group as a whole may be a branched chain or a straight chain.

On the other hand, a polar group of a chain group type means a form having a structure in a molecule that does not include a cyclic atomic arrangement containing a polar element and includes at least one polar element in a linear atomic arrangement (which may be branched).

Furthermore, in this specification, a chain group means an atomic arrangement that does not contain a ring in the structural formula, and the atoms that constitute it are bonded into a linear (branchable) atomic group, which is called a non-cyclic group. In other words, a chain group means a straight chain or branched aliphatic group, which may contain either a saturated bond or an unsaturated bond.

Thus, the polar groups of the chain group type include, for example, alkyl, alkenyl, alkoxy, ester, ether or ketone groups. Furthermore, the hydrogen atoms in these groups may be substituted by at least one substituent (reactive functional groups (vinyl, acryl, methacryl, etc.), chain organic groups (alkyl, cyano, etc.)). In addition, the polar groups of the chain group type may be either straight chain or branched chain.

As the polar group of the cyclic group type, a heteroaromatic group (including a condensed ring) having 3 to 20 carbon atoms or a heteroalicyclic group (including a condensed ring) having 3 to 20 carbon atoms is preferred, a heteroaromatic group (including a condensed ring) having 3 to 12 carbon atoms or a heteroalicyclic group (including a condensed ring) having 3 to 12 carbon atoms is more preferred, and a 5-membered heteroaromatic group, a 5-membered heteroalicyclic group, a 6-membered heteroaromatic group or a 6-membered heteroalicyclic group is further preferred. Furthermore, the hydrogen atoms in the ring structures may be substituted by a halogen group, a linear or branched alkyl group or an alkoxy group having 1 to 5 carbon atoms. The halogenated group is preferably a fluoro group or a chloro group, more preferably a fluoro group.

The polar group of the chain group type is preferably a straight or branched alkyl group having 1 to 20 carbon atoms in which a hydrogen atom or _-CH2- in the structure is substituted with a polar element. Furthermore, one or two or more non-adjacent _-CH2- in the alkyl group may be substituted with -CH=CH-, -C≡C-, -O-, -CO-, -COO-, -OCO- or -OCO-COO- in a manner that the oxygen atom is not directly adjacent. Furthermore, the polar group of the chain group type preferably contains one or two or more polar elements at its end.

One or more hydrogen atoms in the polar group may be replaced by a polymerizable group. The polymerizable group is as described in the above paragraph "polymerizable group".

Specific examples of polar elements include polar elements containing oxygen atoms (hereinafter referred to as oxygen-containing polar elements), polar elements containing nitrogen atoms (hereinafter referred to as nitrogen-containing polar elements), polar elements containing phosphorus atoms (hereinafter referred to as phosphorus-containing polar elements), polar elements containing boron atoms (hereinafter referred to as boron-containing polar elements), polar elements containing silicon atoms (hereinafter referred to as silicon-containing polar elements), or polar elements containing sulfur atoms (hereinafter referred to as sulfur-containing polar elements). Among them, the polar elements are preferably sulfur-containing polar elements, nitrogen-containing polar elements, or oxygen-containing polar elements, and more preferably oxygen-containing polar elements. The reason is that the interaction between these polar elements and the substrate or impurities is higher than that of other polar elements.

The oxygen-containing polar element is preferably at least one group selected from the group consisting of a hydroxyl group, an alkylol group, an alkoxy group, a formyl group, a carboxyl group, an ether group, a carbonyl group, a carbonate group and an ester group, or a group in which the group is bonded to a carbon atom.

The nitrogen-containing polar element is preferably at least one group selected from the group consisting of a cyano group, a primary amino group, a secondary amino group, a tertiary amino group, a pyridyl group, a carbamoyl group and a urea group, or a group in which the group is bonded to a carbon atom.

The phosphorus-containing polar element is preferably at least one group selected from the group consisting of a phosphinyl group and a phosphoric acid group, or a group in which the group is bonded to a carbon atom.

The polar group is preferably a group consisting of one or more groups selected from the group consisting of a cyclic group having an oxygen-containing polar element (hereinafter referred to as an oxygen-containing cyclic group), a cyclic group having a nitrogen-containing polar element (hereinafter referred to as a nitrogen-containing cyclic group), a chain group having an oxygen-containing polar element (hereinafter referred to as an oxygen-containing chain group) and a chain group having a nitrogen-containing polar element (hereinafter referred to as a nitrogen-containing chain group), or a group containing such a group.

As the oxygen-containing cyclic group, any of the following groups containing an oxygen atom in the form of an ether group in the ring structure is preferred. In the following formula, * represents a bond.

Furthermore, as the oxygen-containing cyclic group, any of the following groups containing an oxygen atom in the form of a carbonyl group, a carbonate group, and an ester group in the ring structure is preferred. In the following formula, * represents a bond.

The nitrogen-containing cyclic group preferably contains any of the following groups: In the following formula, * represents a bond.

As the oxygen-containing chain group, any of the following groups is preferably contained.

(In the formula, R ^at1 represents an alkyl group having 1 to 5 carbon atoms. Z ^at1 represents a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms. In particular, one or more -CH ₂ - in the alkylene group or the alkenylene group can be substituted by -O-, -COO-, -C(=O)-, or -OCO- in a manner that the oxygen atom is not directly adjacent to the alkylene group. X ^at1 represents a hydrogen atom or an alkyl group having 1 to 15 carbon atoms. In particular, one or more -CH ₂ - in the alkylene group can be substituted by -O-, -COO-, -C(=O)-, or -OCO- in a manner that the oxygen atom is not directly adjacent to the alkylene group. In the formula, * represents a bond).

As the nitrogen-containing chain group, it is preferred to contain any of the following groups.

(In the formula, R ^at , R ^bt , R ^ct and R ^dt each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. The * in the formula represents a bond).

The polar group is preferably bonded to the mesogen group via a spacer group. In this case, it is preferred that one or more hydrogen atoms in the spacer group are replaced by a polymerizable group.

The polymerizable compound B preferably has one or more groups represented by the following general formula (AT).

(Wherein, Sp ^AT1 represents a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted by -OH, -CN, -W ^AT1 -Z ^AT1 or P ^AP1 -Sp ^AP1 -, one or more non-adjacent -CH ₂ - in the alkylene group may be substituted by a cyclic group, -CH＝CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- in a manner that the oxygen atom is not directly bonded to the oxygen atom, W ^AT1 represents a single bond or the following general formula (WAT1) or (WAT2).

(In the formula, Sp ^WAT1 and Sp ^WAT2 are independent and represent a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms. One or more hydrogen atoms in the alkylene group may be substituted by -OH, -CN or P ^AP1 -Sp ^AP1 -. One or more non-adjacent -CH ₂ - in the alkylene group may be substituted by a cyclic group, -CH＝CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- in a manner that the oxygen atom is not directly adjacent. The * in the formula represents a bond.) Z ^AT1 represents a monovalent polar group containing a polar element. One or more hydrogen atoms in Z ^AT1 may be substituted by -OH, -CN or P ^AP1 -Sp ^AP1 -. P ^AP1 represents a polymerizing group, Sp ^AP1 represents a spacer group, and the * in the formula represents a bond).

Sp ^WAT1 and Sp ^WAT2 are each independently, and preferably represent a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably represent a single bond or a linear alkylene group having 1 to 20 carbon atoms, and even more preferably represent a single bond or a linear alkylene group having 2 to 10 carbon atoms.

Sp ^AT1 represents a spacer group. The spacer group Sp ^AT1 represents a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, preferably a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably a single bond or a linear alkylene group having 1 to 20 carbon atoms, and even more preferably a single bond or a linear alkylene group having 2 to 10 carbon atoms.

Furthermore, in Sp ^AT1 , Sp ^WAT1 and Sp ^WAT2 , one or two or more non-adjacent -CH ₂ - in the alkylene group can be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- in a manner that the oxygen atom is not directly bonded.

The hydrogen atoms in Sp ^AT1 and Sp ^WAT1 are independent and can be replaced by -W ^AT1 -Z ^AT1 or P ^AP1 -Sp ^AP1 -.

Among them, Sp ^AT1 is preferably a linear or branched alkylene group with 1 to 25 carbon atoms in which at least one hydrogen atom is replaced by P ^AP1 -Sp ^AP1 -. The polar group Z ^AT1 and the polymerizable group P ^AP1 in the substituent P ^AP1 -Sp ^AP1 - of Sp ^AT1 can be located near each other. By having such a structure, the polymerizable compound B can enhance the interaction of the polymerizable compound B formed at the interface between the liquid crystal layer and the substrate with the substrate in a liquid crystal display element without an alignment film, and can improve the vertical alignment control of the polymerizable compound B on the liquid crystal molecules. In addition, in a liquid crystal display element with an alignment film, impurities adsorbed and captured by the polar group are easily incorporated into the polymer, which can prevent the impurities from leaking out and diffusing into the liquid crystal layer, thereby preventing the physical properties of the liquid crystal layer from being degraded.

Z ^AT1 represents a monovalent polar group containing a polar element, and among them, a group represented by the following general formula (ZAT1-1) or (ZAT1-2) is preferred.

(In the formula, Sp ^ZAT11 represents a single bond or a straight or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted by -OH, -CN, -Z ^ZAT11 -R ^ZAT11 or P ^AP1 -Sp ^AP1 -, one or more non-adjacent -CH ₂ - in the alkylene group may be substituted by a cyclic group, -O-, -COO-, -C(＝O)-, -OCO- or -CH＝CH- in a manner that the oxygen atom is not directly adjacent to the cyclic group, -O-, -COO-, -C(＝O)-, -OCO- or -CH＝CH-. Sp ^ZAT12 represents a single bond or a straight or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted by -OH, -CN or P ^AP1 -Sp ^AP1 -, one or more non-adjacent -CH ₂ - can be substituted by a cyclic group, -O-, -COO-, -C(=O)-, -OCO-, -CH=CH- or -Z ^ZAT11 - in a manner where the oxygen atom is not directly adjacent. Z ^ZAT11 represents a polar group containing a polar element. The structure represented by the ring including Z ^ZAT12 represents a 5- to 7-membered ring. One or more hydrogen atoms in Z ^ZAT11 and Z ^ZAT12 may be substituted by -OH, -CN or P ^AP1 -Sp ^AP1 -. R ^ZAT11 and R ^ZAT12 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, one or more hydrogen atoms in the alkyl group may be substituted by -OH, -CN or P ^AP1 -Sp ^AP1 -, one or more non-adjacent -CH ₂ - can be substituted by a cyclic group, -O-, -COO-, -C(=O)-, -OCO-, -CH=CH- or -Z ^ZAT11 - in a manner that the oxygen atom is not directly bonded. P ^AP1 represents a polymerizing group, Sp ^AP1 represents a spacer group, and the * in the formula represents a bond).

The group represented by the general formula (ZAT1-1) is preferably a group represented by the following general formulas (ZAT1-1-1) to (ZAT1-1-30).

(In the formula, Sp ^ZAT11 and R ^ZAT11 have the same meanings as above, and the hydrogen atom bonded to the carbon atom may be replaced by -OH, -CN or P ^AP1 -Sp ^AP1 -. In the formula, * represents a bond).

Furthermore, as the group represented by the general formula (ZAT1-1), the following groups can be preferably exemplified.

(In the formula, R ^tc represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or P ^AP1 -Sp ^AP1 -. One or more hydrogen atoms in the alkyl group may be substituted by -OH, -CN or P ^AP1 -Sp ^AP1 -. One or more non-adjacent -CH ₂ - groups in the alkyl group may be substituted by a cyclic group, -O-, -COO-, -C(＝O)-, -OCO-, -CH＝CH- or -Z ^ZAT11 - in a manner where the oxygen atom is not directly adjacent. The hydrogen atom in the molecule may be substituted by P ^AP1 -Sp ^AP1 -. In the formula, * represents a bond).

The group represented by the general formula (ZAT1-2) is preferably a group represented by the following general formulas (ZAT1-2-1) to (ZAT1-2-9).

(In the formula, Sp ^ZAT12 has the same meaning as above, and one or more hydrogen atoms bonded to the carbon atom may be replaced by a halogen atom, -OH, -CN or P ^AP1 -Sp ^AP1 -. In the formula, * represents a bond).

[Mesogen] The polymerizable compound B preferably has a mesogen. A mesogen means a group having a rigid portion, such as a group having one or more cyclic groups. Here, "cyclic group" means an atomic group whose atoms are bonded to form a ring, including a carbon ring, a heterocyclic ring, a saturated or unsaturated cyclic structure, a monocyclic ring, a bicyclic structure, a polycyclic structure, an aromatic group, a non-aromatic group, etc.

The liquid crystal primordium preferably has a skeleton similar to that of a liquid crystal molecule (liquid crystal compound).

The liquid crystal group preferably has 2 to 4 cyclic groups, and more preferably has 3 to 4 cyclic groups. The cyclic groups can be linked by a single bond or a bonding group.

When the cyclic group is a monocyclic group, the mesogen group preferably contains two or more monocyclic groups.

The cyclic group may contain at least one heteroatom. The cyclic group may be substituted by at least one substituent. Examples of the substituent include halogenated groups, polymerizable groups, alkyl groups, alkoxy groups, aryl groups and other organic groups.

The mesogen group can be represented by the general formula (AL), for example. In the present invention, the polymerizable compound B preferably has a group represented by the general formula (AL).

(wherein Z ^AL1 represents a single bond, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -CF ₂ O-, -OCF ₂ -, -CH=CHCOO-, -OCOCH=CH-, -CH ₂ -CH ₂ COO-, -OCOCH 2 -CH ₂ -, -CH=C(CH ₃ )COO-, _-OCOC (CH ₃ )=CH-, -CH ₂ -CH(CH ₃ )COO-, -OCOCH(CH ₃ )-CH ₂ -, -OCH ₂ CH ₂ O-, or an alkylene group having 1 to 20 carbon atoms, wherein one or two or more non-adjacent -CH ₂ - can be substituted by a cyclic group, -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- in a manner that the oxygen atom is not directly bonded. A ^AL1 and A ^AL2 each independently represent a divalent cyclic group. One or more hydrogen atoms in Z ^AL1 , A ^AL1 and A ^AL2 each independently may be substituted by a halogenated group, a polar group, -Sp ^AT1 , -W ^AT1 , -Z ^AT1 , P ^AP1 , -Sp ^AP1 , or a monovalent organic group. Sp ^AP1 , Sp ^AT1 , P ^AP1 , W ^AT1 and Z ^AT1 each have the same meanings as described above. m ^AL1 represents an integer from 1 to 5. When m ^AL1 represents an integer from 2 to 5, a plurality of Z ^AL1s may be the same or different, and a plurality of A AL1s may be the same or different. ^AL1 may be the same or different. The * in the formula represents a key bond respectively).

In the general formula (AL), Z ^AL1 is preferably a single bond or an alkylene group having 2 to 20 carbon atoms, more preferably a single bond or an alkylene group having 2 to 10 carbon atoms, and even more preferably a single bond, -(CH ₂ ) ₂ - or -(CH ₂ ) ₄ -. One or more -CH ₂ - in the alkylene group may be substituted by -O-, -COO- or -OCO- in a manner that the oxygen atom is not directly adjacent to the -CH 2 -.

In order to improve the linearity of the polymerizable compound B, Z ^AL1 is preferably a single bond or an alkylene group having 2 to 20 carbon atoms with an even number of atoms directly bonding rings. One or two or more non-adjacent -CH ₂ - in the alkylene group may be substituted with -O-, -COO- or -OCO- in a manner that the oxygen atom is not directly adjacent. The number of atoms directly bonding rings is, for example, 4 in the case of -CH ₂ -CH ₂ COO-.

In the general formula (AL), A ^AL1 and A ^AL2 are each independently a divalent cyclic group. The divalent cyclic group is preferably selected from 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenyl, tetrahydropyran-2,5-diyl, 1,3-dihydropyran-2,5-diyl, alkane-2,5-diyl, tetrahydrothiopyran-2,5-diyl, thiophene-2,5-diyl, 1,4-bicyclo(2,2,2)octylene, decahydronaphthalene-2,6-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, thiophene-2,5-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6-naphthylene, phenanthrene-2,7-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 1,2,3,4,4a,9,10a-octahydrophenanthrene-2, AAL1 is a member selected from the group consisting of 1,4-phenylene, 1,4-cyclohexylene, 2,6-naphthylene or phenanthrene-2,7-diyl, and 1,4-phenylene or 1,4-cyclohexylene. ^AAL2 is preferably selected from the group consisting of 1,4-phenylene, 1,4-cyclohexylene, 2,6-naphthylene or phenanthrene-2,7-diyl, and more preferably 1,4- ^phenylene or 1,4-cyclohexylene.

The divalent cyclic group may be unsubstituted, or one or more hydrogen atoms in the cyclic group may be substituted by a substituent. Examples of the substituent include a halogenated group, a polar group, P ^AP1 -Sp ^AP1 -, or a monovalent organic group. When the monovalent organic group is an alkyl group, the alkyl group may be substituted by a fluorine atom or a hydroxyl group. Examples of the halogenated group include a fluoro group, a chloro group, etc., and a fluoro group is preferred.

Here, in the general formula (AL), the monovalent organic group is a group that forms a chemical structure of an organic compound in the form of a monovalent group, and means an atomic group formed by removing one hydrogen atom from an organic compound. Examples of the monovalent organic group include an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, and an alkenyloxy group having 2 to 15 carbon atoms. One or more -CH ₂ - in the above-mentioned alkyl group, the above-mentioned alkenyl group, the above-mentioned alkoxy group, and the above-mentioned alkenyloxy group may be substituted with -O-, -COO-, or -OCO-, respectively, in a manner that the oxygen atom is not directly adjacent to the -CH 2 - group.

The monovalent organic group is preferably an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, still more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, particularly preferably an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 2 carbon atoms, and most preferably an alkyl group having 1 or 2 carbon atoms or an alkoxy group having 1 carbon atom. One or more _-CH2- groups in the alkyl group, the alkenyl group, the alkoxy group, and the alkenyloxy group may be substituted with -O-, -COO-, or -OCO-, respectively, in a manner that the oxygen atom is not directly adjacent to the group.

In the above general formula (AL), m ^AL1 is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and even more preferably 2 or 3.

As preferred forms of the above-mentioned liquid crystal primitives, structures represented by the following formulae (me-1) to (me-44) can be cited.

(In formulas (me-1) to (me-44), the rings at both ends have bonds at positions where any one of the hydrogen atoms bonded to the carbon atoms constituting the ring is detached).

In the above formulae (me-1) to (me-44), one or more hydrogen atoms in the cyclohexane ring, benzene ring or naphthyl ring may be independently substituted by a halogen group, P ^AP1 -Sp ^AP1 -, a monovalent organic group (e.g., an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms) or a polar group.

A more preferred form of the above-mentioned liquid crystal base is a structure represented by formula (me-8) to (me-44), a more preferred form is a structure represented by formula (me-8) to (me-10), formula (me-12) to (me-18), formula (me-22) to (me-24), formula (me-26) to (me-27) and formula (me-29) to (me-44), and a further more preferred form is a structure represented by formula (me-12), (me-14), (me-16), (me-22) to (me-24), (me-29), (me-34), (me-36) to (me-37), and (me-42) to (me-44).

The most preferred form of the liquid crystal base is the structure represented by the following general formula (AL-1) or (AL-2), and the most preferred form is the structure represented by the following general formula (AL-1).

(In the formula, ^XAL101 to ^XAL118 and ^XAL201 to ^XAL214 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogenated group, ^PAP1 - ^SpAP1- , or a polar group. Among them, one of ^XAL101 , ^XAL102 , ^XAL103 , ^XAL117 , and ^XAL118 represents a bond, one of ^XAL108 , ^XAL109 , ^XAL110 , ^XAL111 , and ^XAL112 represents a bond, one of ^XAL201 , ^XAL202 , ^XAL203 , ^XAL212 , and ^XAL213 represents a bond, and ^XAL206 , ^XAL207 , ^XAL208 , ^XAL209 and ^XAL210 represent a bond. Furthermore, any one or more of ^XAL101 to ^XAL118 and ^XAL201 to ^XAL214 are substituted by a polar group. The polar group may be substituted by ^PAP1 - ^SpAP1- . Ring ^AAL11 , Ring ^AAL12 and Ring ^AAL21 each independently represent a cyclohexane ring or a benzene ring. General formula (AL-1) or general formula (AL-2) has one or more ^PAP1 - ^SpAP1- ) in its molecule.

In the general formula (AL-1), at least one of X ^AL109 , X ^AL110 and X ^AL111 is preferably a polar group, more preferably both X ^AL109 and X ^AL110 are polar groups, or X ^AL110 is a polar group, and even more preferably X ^AL110 is a polar group.

In the general formula (AL-1), at least one of ^XAL109 , ^XAL110 and ^XAL111 is preferably ^PAP1 - ^SpAP1- among polar groups or a polar group having a polymerizable site in its structure, and more preferably both or one of ^XAL109 and ^XAL111 is ^PAP1 - ^SpAP1- .

In the general formula (AL-1), one or two of ^XAL104 to ^XAL108 and ^XAL112 to ^XAL116 are independently preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogenated group, more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom. It is particularly preferred that ^XAL105 , ^XAL106 or ^XAL107 are independently an alkyl group having 1 to 3 carbon atoms or a fluorine atom.

In the general formula (AL-2), it is preferred that at least one of X ^AL207 , X ^AL208 and X ^AL209 is a polar group, more preferably both X ^AL207 and X ^AL208 are polar groups, or X ^AL208 is a polar group, and even more preferably X ^AL208 is a polar group.

In the general formula (AL-2), at least one of ^XAL207 , ^XAL208 and ^XAL209 is preferably ^PAP1 - ^SpAP1- among polar groups or a polar group having a polymerizable site in its structure, and more preferably both or one of ^XAL207 and ^XAL209 is ^PAP1 - ^SpAP1- .

In the general formula (AL-2), one or two of ^XAL202 to ^XAL206 and ^XAL210 to ^XAL214 are independently preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogenated group, more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom. It is particularly preferred that ^XAL204 , ^XAL205 or ^XAL206 are independently an alkyl group having 1 to 3 carbon atoms or a fluorine atom.

[Specific state of polymerizable compound B] Preferably, polymerizable compound B has one or more polar groups, one or more polymerizable groups, and liquid crystal groups, wherein the polymerizable groups directly or via spacers replace the liquid crystal groups or the polar groups, and it is particularly preferred that the polymerizable groups replace the liquid crystal groups while being incorporated into the polar groups.

One or two or more hydrogen atoms in the spacer group of the polymerizable group of the polymerizable compound B may be substituted with a polar group. Furthermore, one or two or more hydrogen atoms in the polar group may be substituted with a polymerizable group via a spacer group.

The polymerizable compound B is preferably a polar element contained in the polar group, or a polar element contained in the polymerizable group is locally present. By the polar group and the polymerizable group being adjacent, the interaction with the substrate or impurities can be improved, and good solubility in the liquid crystal composition can be shown. Specifically, the polymerizable compound B is preferably a form having a polymerizable group and a polar group on the same ring. This form includes: a form in which one or more polymerizable groups and one or more polar groups are respectively bonded to the same ring; and a form in which at least one of the one or more polymerizable groups or at least one of the one or more polar groups is bonded to another and has a polymerizable group and a polar group on the same ring.

The polymerizable compound B is preferably a compound represented by the following general formula (SAL).

(In the formula, R ^AK1 represents a linear or branched alkyl group having 1 to 20 carbon atoms, one or more non-adjacent -CH ₂ - in the alkyl group can be replaced by -CH＝CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- in a manner not directly bonded to an oxygen atom, and one or more hydrogen atoms in the alkyl group can be replaced by a halogen atom, each independently. A ^AL1 and A ^AL2 are each independently and have the same meanings as A ^AL1 and A ^AL2 in the general formula (AL). Z ^AL1 has the same meaning as Z ^AL1 in the general formula (AL). m ^AL1 has the same meaning as m ^AL1 in the general formula (AL). Sp ^AT1 has the same meaning as Sp ^AT1 in the general formula (AT). W ^AT1 has the same meaning as W AT1 in the general formula (AT) ( ^{A AL1} , A AL2 , Z ^{AL1 , Z AT1} , Sp AT1 , W ^AT1 , P ^AP1 , and Sp ^AP1 , when there are a plurality of R ^AK1 , A ^AL1 , A ^AL2 , Z ^AL1 , Z ^AT1 , Sp ^AT1 , W ^AT1 , P ^AP1 , and Sp ^AP1 , they may be the same or different.)

R ^AK1 preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, more preferably a linear alkyl group having 1 to 20 carbon atoms, and even more preferably a linear alkyl group having 1 to 8 carbon atoms. One or two or more non-adjacent -CH ₂ - in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- in a manner that the oxygen atom is not directly adjacent. Furthermore, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom. The halogen atom is preferably a fluorine atom or a chlorine atom, and more preferably a fluorine atom.

The detailed descriptions of A ^AL1 , A ^AL2 , Z ^AL1 , Z ^AT1 , Sp ^AT1 , W ^AT1 , P ^AP1 and Sp ^AP1 are as described previously.

The compound represented by the general formula (SAL) is preferably a compound represented by the following formulas (SAL-1.1) to (SAL-2.10).

The preferred lower limit of the content of the polymerizable compound B is 0.01 mass%, 0.03 mass%, 0.05 mass%, 0.08 mass%, 0.1 mass%, 0.15 mass%, 0.2 mass%, 0.25 mass%, and 0.3 mass% of the total weight of the polymerizable compound-containing liquid crystal composition of the present invention. Moreover, the preferred upper limit of the content of the polymerizable compound B is 10 mass%, 8 mass%, 5 mass%, 3 mass%, 1.5 mass%, 1.2 mass%, 1 mass%, 0.8 mass%, and 0.5 mass% of the total weight of the polymerizable compound-containing liquid crystal composition of the present invention.

If the content of the polymerizable compound B contained in the polymerizable compound-containing liquid crystal composition of the present invention is small, it is difficult to show the effect of adding the polymerizable compound B. On the other hand, if the above content is too much, there will be problems such as the amount of residue after curing increases, curing takes time, and the reliability of the liquid crystal decreases. Therefore, it is preferable to set the content by combining the above upper limit value and lower limit value while considering the balance.

As a specific range of the content of the polymerizable compound B, for example, in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention, it is preferably in the range of 0.05 mass % to 10 mass %, preferably in the range of 0.1 mass % to 8 mass %, preferably in the range of 0.1 mass % to 5 mass %, preferably in the range of 0.1 mass % to 3 mass %, preferably in the range of 0.2 mass % to 2 mass %, preferably in the range of 0.2 mass % to 1.3 mass %, preferably in the range of 0.2 mass % to 1 mass %, preferably in the range of 0.2 mass % to 0.56 mass %.

[2-3] Other details about polymerizable compounds The liquid crystal composition containing polymerizable compounds of the present invention may contain only one or more polymerizable compounds A, may contain only one or more polymerizable compounds B, or may contain one or more polymerizable compounds A and one or more polymerizable compounds B.

Among them, the polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more polymerizable compounds A and one or more polymerizable compounds B. The reason is that by containing both polymerizable compounds A and polymerizable compounds B, the effect of suppressing the reduction of VHR caused by UV irradiation is higher than that of containing each polymerizable compound alone, and higher tilt stability can be achieved.

Furthermore, the polymerizable compound-containing liquid crystal composition of the present invention may also contain polymerizable compounds other than the polymerizable compounds A and B described above.

The preferred lower limit of the content of the polymerizable compound is 0.01 mass %, 0.02 mass %, 0.03 mass %, 0.05 mass %, 0.08 mass %, 0.1 mass %, 0.15 mass %, 0.2 mass %, 0.25 mass %, and 0.3 mass % of the total amount of the liquid crystal composition containing the polymerizable compound of the present invention.

Moreover, the preferred upper limit value of the content of the polymerizable compound is 10 mass%, 8 mass%, 5 mass%, 3 mass%, 1.5 mass%, 1.2 mass%, 1 mass%, 0.8 mass%, 0.6 mass% and 0.5 mass% in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention.

[3] Compounds represented by general formula (L) The liquid crystal composition containing a polymerizable compound of the present invention preferably contains one or more compounds represented by general formula (L).

(wherein, ^RL1 and ^RL2 are independently an alkyl group having 1 to 8 carbon atoms, one or two or more non-adjacent _{-CH2- groups} in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, ^nL1 is 0, 1, 2 or 3, ^AL1 , ^AL2 and ^AL3 are independently a group selected from the group consisting of the following groups (a), (b) and (c), (a) 1,4-cyclohexyl (one _-CH2- or two or more non-adjacent _-CH2- groups in the group may be substituted by -O-), (b) 1,4-phenylene (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted with -N＝), and (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH＝ or two or more non-adjacent -CH＝ in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N＝) The above group (a), group (b) and group (c) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom. Z ^L1 and Z ^L2 are each independently substituted with a single bond, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -OCH ₂ -, -CH ₂ O-, -COO-, -OCO-, -OCF ₂ -, _-CF2O- , -CH=N-N=CH-, -CH=CH-, -CF=CF- or -C≡C-, when ^nL1 is 2 or 3 and there are plural A ^L2s , they may be the same or different, when ^nL1 is 2 or 3 and there are plural Z ^L2s , they may be the same or different. The compounds represented by the general formula (i) are not included).

The compound represented by the general formula (L) is equivalent to a dielectrically almost neutral compound (Δε value is -2 to 2). Therefore, it is preferred to set the number of polar groups such as halogens in the molecule to 2 or less, preferably 1 or less, and preferably no such polar groups. In addition, the number of halogen atoms in the molecule is preferably 0, 1, 2 or 3, preferably 0 or 1, and when the compatibility with other liquid crystal molecules is important, it is preferably 1.

The compounds represented by the general formula (L) can be used alone or in combination. The types of the compounds that can be combined are not particularly limited, and they are appropriately combined and used according to the desired performance such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence. Regarding the types of compounds used, for example, as one embodiment of the present invention, there is one type. Alternatively, in other embodiments of the present invention, there are 2, 3, 4, 5, 6, 7, 8, 9, 10 or more types.

The content of the compound represented by the general formula (L) can be appropriately adjusted according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, drop marks, afterimages, dielectric anisotropy, etc.

The preferred lower limit of the content of the compound represented by the general formula (L) in the total amount of the liquid crystal composition of the present invention is 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass%. The preferred upper limit of the content is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%.

When the viscosity of the liquid crystal composition of the present invention is kept low and a composition with a fast response speed is required, the content of the compound represented by the general formula (L) is preferably a high lower limit value and a high upper limit value. When the Tni of the liquid crystal composition of the present invention is kept high and a composition with good temperature stability is required, the content of the compound represented by the general formula (L) is preferably a high lower limit value and a high upper limit value. In order to keep the driving voltage low and increase the dielectric anisotropy, the content of the compound represented by the general formula (L) is preferably a low lower limit value and a low upper limit value.

In the above general formula (L), ^RL1 and ^RL2 are independently an alkyl group having 1 to 8 carbon atoms. One or two or more non-adjacent _-CH2- groups in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-. In the above general formula (L), ^RL1 and ^RL2 are independently 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.

To describe in more detail, when reliability is important, it is preferred that both ^RL1 and ^RL2 are alkyl groups having 1 to 8 carbon atoms. Furthermore, when reducing the volatility of the compound is important, it is preferred that both ^RL1 and ^RL2 are alkoxy groups having 1 to 8 carbon atoms. Furthermore, when reducing viscosity is important, it is preferred that at least one of ^RL1 and ^RL2 is an alkenyl group having 2 to 8 carbon atoms.

In the above general formula (L), when the ring structures of A ^L1 and A ^L3 to which R ^L1 and R ^L2 are bonded are phenylene (aromatic), R ^L1 and R ^L2 are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, or alkenyl groups having 4 to 5 carbon atoms. On the other hand, when the ring structures (A ^L1 and A ^L3 ) to which R ^L1 and R ^L2 are bonded are saturated ring structures such as cyclohexane, pyran and dioxane, R ^L1 and R ^L2 are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, or linear alkenyl groups having 2 to 5 carbon atoms. In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms of ^RL1 and ^RL2 is preferably less than 5, and a linear chain is preferred.

In the above general formula (L), when the response speed is important, n ^L1 is preferably 0, preferably 2 or 3 to improve the upper temperature limit of the nematic phase, and preferably 1 to achieve a balance. In addition, in order to satisfy the characteristics required as a composition, it is preferred to combine compounds with different n ^L1 values.

In the above general formula (L), when Δn needs to be increased, A ^L1 , A ^L2 and A ^L3 are preferably aromatic, and are preferably aliphatic in order to improve the response speed. ^{A L1} , A ^L2 and A ^L3 are each independently preferably trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, 1,4-cyclohexenyl, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and more preferably represent the following structure.

Particularly preferably, it represents trans-1,4-cyclohexylene or 1,4-phenylene.

In the above general formula (L), when emphasis is placed on response speed, Z ^L1 and Z ^L2 are preferably single keys, respectively.

The liquid crystal composition containing a polymerizable compound of the present invention preferably contains one or more compounds in which at least one of ^RL1 and ^RL2 in the general formula (L) represents an alkenyl group having 2 to 8 carbon atoms (compounds represented by the following general formula (L-a)).

(In formula (L-a), R ^L1a and R ^L2a each independently represent an alkyl group having 1 to 8 carbon atoms, one or two or more non-adjacent -CH ₂ - in the alkyl group may be independently substituted by -CH＝CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, at least one of R ^L1a and R ^L2a is an alkenyl group having 2 to 8 carbon atoms, A ^{L1a ,} A ^L2a , A L3a , Z ^L1a , Z ^L2a and n ^L1a each have the same meanings as A ^L1 , A ^L2 , A ^L3 , Z ^L1 , Z ^L2 and n ^L1 in formula (L))

The compound represented by the general formula (L-a) can increase the response speed in a liquid crystal display element, but on the other hand, it is easy to deteriorate due to UV irradiation when the polymerizable compound is polymerized, and the voltage holding ratio (VHR) of the liquid crystal display element is easy to decrease. In contrast, the liquid crystal composition containing the polymerizable compound in the present invention can shorten the UV irradiation time required for the polymerization reaction of the polymerizable compound by containing the compound represented by the general formula (i) in addition to the polymerizable compound, and as a result, the effect of suppressing the degradation of the compound represented by the general formula (L-a) and the decrease in the voltage holding ratio (VHR) can be improved.

Therefore, the liquid crystal composition containing a polymerizable compound of the present invention can produce a liquid crystal display element with higher high-speed responsiveness and high VHR compatibility by containing a compound represented by general formula (i) and a compound represented by general formula (L-a) in addition to the polymerizable compound.

Regarding the compound represented by the general formula (L-a), either ^RL1 or ^RL2 in the general formula (L-a) may represent an alkenyl group, or both ^RL1 and ^RL2 may represent an alkenyl group. The number of carbon atoms in the alkenyl group may be 2 to 8, preferably 2, 3, 4, or 5, and more preferably 2 or 3.

The alkenyl group is preferably a group represented by any one of formula (R1) to formula (R5), and is preferably a group represented by formula (R1) or formula (R2). (The black dots in each formula represent carbon atoms in the ring structure)

The compound represented by the general formula (L) is preferably a compound selected from the group consisting of compounds represented by the general formula (NU-01) to the general formula (NU-08).

(wherein, R ^NU11 , R ^NU12 , R ^NU21 , R ^NU22 , R ^NU31 , R ^NU32 , R ^NU41 , R ^NU42 , R ^NU51 , R ^NU52 , R ^NU61 , R ^NU62 , R ^NU71 , R ^NU72 , R ^NU81 and R ^NU82 independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms).

R ^NU11 , R ^NU12 , R ^NU21 , R ^NU22 , R ^NU31 , R ^NU32 , R ^NU41 , R ^NU42 , R ^NU51 , R ^NU52 , R ^NU61 , R ^NU62 , R ^NU71 , R ^NU72 , R ^NU81 and R ^NU82 are independently preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms.

R ^NU11 , R ^NU21 , R ^NU31 , R ^NU41 and R ^NU51 are preferably compounds each independently containing one or more alkenyl groups having 2 to 8 carbon atoms. That is, the compound represented by general formula (L-a) is preferably a compound in which R ^NU11 , R NU21 , R ^NU31 , R ^NU41 and R ^NU51 in general formula (NU-01) to general formula ( ^NU -08) are each independently alkenyl groups having 2 to 8 carbon atoms. This is because such compounds contribute to improving the response speed. Preferred alkenyl groups include alkenyl groups represented by formula (R1) to formula (R5).

(The black dots in the formulas represent carbon atoms in the ring structure).

Among them, preferably, R ^NU11 , R ^NU21 , R ^NU31 , R ^NU41 and R ^NU51 are each independently an alkenyl group having 2 to 3 carbon atoms, preferably an alkenyl group represented by formula (R1) or formula (R2).

The liquid crystal composition of the present invention preferably contains one or more compounds selected from the group consisting of compounds represented by the following general formula (NU-01A) to (NU-05A) as the group of compounds represented by the following general formula (NU-01) to (NU-08). That is, the compound represented by the general formula (L-a) is preferably a compound selected from the group consisting of compounds represented by the following general formula (NU-01A) to (NU-05A). The reason is that by containing one or more of these compounds, the response speed can be made faster.

(In the above formulae, R ^NU12a , R ^NU22a , R ^NU32a , R ^NU42a , and R ^NU52a each independently represent an alkyl group having 1 to 8 carbon atoms; one or more non-adjacent -CH ₂ - in the alkyl group may be substituted by -CH＝CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO-, as long as the oxygen atoms are non-adjacent; one or more hydrogen atoms in the alkyl group may be substituted by a halogen atom; n1 to n5 each independently represent an integer from 0 to 6).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-02).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-03).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03) and a compound represented by the general formula (NU-04).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03) and a compound represented by the general formula (NU-05).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-06).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-07).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-08).

The liquid crystal composition of the present invention more preferably contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-02), and a compound represented by the general formula (NU-04).

The liquid crystal composition of the present invention more preferably contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-03), and a compound represented by the general formula (NU-05).

The liquid crystal composition of the present invention more preferably contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-02), a compound represented by the general formula (NU-03), and a compound represented by the general formula (NU-05).

The content of the compound represented by the general formula (NU-01) is preferably 1 to 60 mass %, more preferably 10 to 50 mass %, and even more preferably 20 to 40 mass % based on the total amount of the liquid crystal composition.

The content of the compound represented by the general formula (NU-02) is preferably 0 to 40 mass %, more preferably 5 to 25 mass %, and even more preferably 5 to 20 mass % based on the total amount of the liquid crystal composition.

The content of the compound represented by the general formula (NU-03) is preferably 0 to 30 mass %, more preferably 1 to 20 mass %, and even more preferably 3 to 15 mass % based on the total amount of the liquid crystal composition.

The content of the compound represented by the general formula (NU-04) is preferably 0 to 30 mass %, more preferably 0 to 20 mass %, and even more preferably 0 to 10 mass % in the total amount of the liquid crystal composition.

The content of the compound represented by the general formula (NU-05) is preferably 0 to 30 mass %, more preferably 1 to 20 mass %, and even more preferably 3 to 20 mass % in the total amount of the liquid crystal composition.

The content of the compound represented by the general formula (NU-06) is preferably 0 to 30 mass %, more preferably 0 to 20 mass %, and even more preferably 0 to 10 mass % in the total amount of the liquid crystal composition.

The content of the compound represented by the general formula (NU-07) is preferably 0 to 30 mass %, more preferably 0 to 20 mass %, and even more preferably 0 to 10 mass % in the total amount of the liquid crystal composition.

The content of the compound represented by the general formula (NU-08) is preferably 0 to 30 mass %, more preferably 0 to 20 mass %, and even more preferably 0 to 10 mass % in the total amount of the liquid crystal composition.

[4] Compounds represented by the general formula (N-1) The liquid crystal composition containing a polymerizable compound of the present invention preferably contains one or more compounds selected from the compounds represented by the general formula (N-1).

(In the formula, R ^N11 and R ^N12 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent -CH ₂ - groups in the alkyl group may each independently be substituted by -CH＝CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, A ^N11 and A ^N12 each independently represent a group selected from the group consisting of the following groups (a), (b), (c) and (d), (a) 1,4-cyclohexylene (one -CH ₂ - or two or more non-adjacent -CH ₂ - groups in the group may be substituted by -O-), (b) 1,4-phenylene (one -CH＝ or two or more non-adjacent -CH＝ groups in the group may be substituted by -N＝), (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH＝ or two or more non-adjacent -CH＝ in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N＝), and (d) 1,4-cyclohexenyl. The above groups (a), (b), (c) and (d) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom. Z ^N11 and Z ^N12 are each independently substituted with a single bond, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -OCH ₂ -, -CH ₂ O-, -COO-, -OCO-, -OCF ₂ -, -CF ₂ O-, -CH=N-N=CH-, -CH=CH-, -CF=CF- or -C≡C-, ^nN11 and ^nN12 are each independently an integer from 0 to 3, ^nN11 + ^nN12 is 1, 2 or 3, and when there are a plurality of A ^N11 ～A ^N12 , Z ^N11 ～Z ^N12 , they may be the same or different. The compounds represented by the general formula (i) and the general formula (L) are not included).

The compound represented by the general formula (N-1) is equivalent to a dielectrically negative compound (the sign of Δε is negative and its absolute value is greater than 2). Among them, the compound represented by the general formula (N-1) is preferably a compound having a negative Δε and its absolute value is greater than 3.

In the general formula (N-1), ^RN11 and ^RN12 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent _{-CH2- groups} in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-. Among them, ^RN11 and ^RN12 are preferably independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, 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 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and particularly preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms.

Furthermore, when the ring structure to which ^RN11 and ^RN12 are bonded is a phenyl (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. When the ring structure to which ^RN11 and ^RN12 are bonded is a saturated ring structure such as cyclohexane, pyran, or dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, it is preferred that the total number of carbon atoms and oxygen atoms, when present, of ^RN11 and ^RN12 is 5 or less, and it is preferably a linear chain.

The alkenyl group is preferably a group represented by any one of formula (R1) to formula (R5).

(The black dots in the formulas represent carbon atoms in the ring structure).

In the general formula (N-1), A ^N11 and A ^N12 each independently represent a group selected from the group consisting of the following groups (a), (b), (c) and (d): (a) 1,4-cyclohexylene (one -CH ₂ - or two or more non-adjacent -CH ₂ - in the group may be substituted by -O-), (b) 1,4-phenylene (one -CH＝ or two or more non-adjacent -CH＝ in the group may be substituted by -N＝), (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=), and (d) 1,4-cyclohexenyl.

The above-mentioned group (a), group (b), group (c) and group (d) are each independent and may be substituted by a cyano group, a fluorine atom or a chlorine atom.

A ^N11 and A ^N12 are independent of each other and are preferably aromatic when Δn needs to be increased, and are preferably aliphatic in order to improve the response speed. The above-mentioned group (a), group (b), group (c) and group (d) preferably represent trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 1,4-cyclohexenyl, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and more preferably represent the following structure.

Particularly preferably, it represents trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-phenylene.

In the general formula (N-1), ^ZN11 and ^ZN12 independently represent a single bond, _-CH2CH2- , -( _CH2 ) _4- , _-OCH2- , _-CH2O- , -COO-, -OCO-, _-OCF2- , _-CF2O- , -CH ₌ N-N=CH-, -CH=CH-, -CF=CF- or -C≡C-, among which _-CH2O- , -CF2O-, _-CH2CH2- , _-CF2CF2- or a single bond is preferred, _-CH2O- , _-CH2CH2- or a _single bond is _more preferred, and _-CH2O- or a _{single bond} is particularly preferred.

In the general formula (N-1), ^nN11 and ^nN12 are each independently an integer from 0 to 3. Furthermore, ^nN11 + ^nN12 are each independently 1, 2 or 3. Among them, ^nN11 + ^nN12 is preferably 1 or 2. In this case, the combination of ^nN11 being 1 and ^nN12 being 0, the combination of ^nN11 being 2 and ^nN12 being 0, the combination of ^nN11 being 1 and ^nN12 being 1, and the combination of ^nN11 being 2 and ^nN12 being 1 are preferred.

The preferred lower limit of the content of the compound represented by the general formula (N-1) in the total amount of the liquid crystal composition of the present invention is 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass%. The preferred upper limit of the content is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%.

When the viscosity of the liquid crystal composition of the present invention is kept low and a composition with a fast response speed is required, it is preferred that the above lower limit value is low and the upper limit value is low. When the Tni of the liquid crystal composition is kept high and a composition with good temperature stability is required, it is preferred that the above lower limit value is low and the upper limit value is low. In addition, in order to keep the driving voltage low and increase the dielectric anisotropy, it is preferred that the above lower limit value is high and the upper limit value is high.

Examples of the compound represented by the general formula (N-1) include compounds selected from the group of compounds represented by the following general formulae (N-01), (N-02), (N-03), (N-04) and (N-05).

(In the formula, R ²¹ and R ²² are independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms; Z ¹ is independently a single bond, -CH ₂ CH ₂ -, -OCH ₂ - or -CH ₂ O-; m is independently 1 or 2)

^R21 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and even more preferably an alkyl group having 2 to 4 carbon atoms. When ^Z1 represents other than a single bond, ^R21 is preferably an alkyl group having 1 to 3 carbon atoms.

R ²² is preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and even more preferably an alkoxy group having 1 to 4 carbon atoms.

When R ²¹ and R ²² are independently alkenyl, the alkenyl is preferably of formula (R1) to formula (R5), more preferably of formula (R1) or formula (R2).

(The black dots in the formulas represent carbon atoms in the ring structure).

More preferably, Z ¹ is independently a single bond, -CH ₂ CH ₂ - or -CH ₂ O-.

When m is 1, ^Z1 is preferably a single bond or _-CH2O- .

When M is 2, ^Z1 is preferably _a single bond, _-CH2CH2- or _-CH2O- .

The liquid crystal composition of the present invention preferably contains one or more compounds selected from the group consisting of compounds represented by general formulae (N-01-1) to (N-01-4) as the compound represented by general formula (N-01).

(In the formula, R ²⁴ each independently represents an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ²³ each independently represents an alkoxy group having 1 to 4 carbon atoms).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-01-1) or a compound represented by the general formula (N-01-4).

The liquid crystal composition of the present invention preferably contains one or more compounds selected from the group of compounds represented by general formulae (N-02-1) to (N-02-3) as the compound represented by general formula (N-02).

(In the formula, R ²⁴ each independently represents an alkyl group having 1 to 5 carbon atoms, and R ²³ each independently represents an alkoxy group having 1 to 4 carbon atoms).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-02-1) or a compound represented by the general formula (N-02-3).

The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (N-03-1) as the compound represented by the general formula (N-03).

(In the formula, R ²⁴ represents an alkyl group having 1 to 5 carbon atoms, and R ²³ represents an alkoxy group having 1 to 4 carbon atoms).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-03-1).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-03-1) and a compound represented by the general formula (N-01-4).

The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (N-04-1) as the compound represented by the general formula (N-04).

(In the formula, R ²⁴ represents an alkyl group having 1 to 5 carbon atoms, and R ²³ represents an alkoxy group having 1 to 4 carbon atoms).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-04-1).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-04-1) and a compound represented by the general formula (N-01-4).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-01-4), and a compound represented by the general formula (N-03-1).

The liquid crystal composition of the present invention may also contain a compound selected from the group of compounds represented by formula (N-05-1) to formula (N-05-3) as the compound represented by general formula (N-05).

In the total amount of the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by the general formula (N-01) is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass%; the preferred upper limit of the content is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%.

In the total amount of the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by the general formula (N-02) is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass%; the preferred upper limit of the content is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%.

In the total amount of the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by the general formula (N-03) is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass%; the preferred upper limit of the content is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%.

In the total amount of the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by the general formula (N-04) is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass%; the preferred upper limit of the content is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%.

In the total amount of the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by formula (N-05) is 0 mass%, 2 mass%, 5 mass%, 8 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, and 20 mass%; the preferred upper limit of the content is 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, and 13 mass%.

[5] Other compounds The liquid crystal composition containing a polymerizable compound of the present invention may also contain one or more compounds having positive dielectric anisotropy as described in paragraphs 0236 to 0509 of Patent No. 6233550.

The liquid crystal composition containing a polymerizable compound of the present invention preferably does not contain "a compound having a structure in which oxygen atoms are bonded to each other, such as a peroxide (-CO-OO-) structure, in the molecule". When the reliability and long-term stability of the liquid crystal composition are important, the content of the compound having a carbonyl group is preferably set to 5% by mass or less, more preferably to 3% by mass or less, and even more preferably to 1% by mass or less, and it is best to substantially not contain a compound having a carbonyl group.

When the liquid crystal composition containing a polymerizable compound of the present invention is concerned with stability to UV irradiation, the content of the compound substituted by chlorine atoms is preferably set to 15 mass % or less, preferably 10 mass % or less, preferably 8 mass % or less, more preferably 5 mass % or less, more preferably 3 mass % or less, and even more preferably substantially no compound substituted by chlorine atoms is contained in the composition.

The liquid crystal composition containing a polymerizable compound of the present invention preferably has a high content of compounds whose ring structures in the molecules are all six-membered rings. Relative to the total mass of the above-mentioned composition, it is preferably set to 80 mass% or more, more preferably to 90 mass% or more, and even more preferably to 95 mass% or more. The best is that the composition is substantially composed only of compounds whose ring structures in the molecules are all six-membered rings.

In order to suppress the deterioration caused by oxidation of the liquid crystal composition, the liquid crystal composition containing the polymerizable compound of the present invention preferably has a low content of compounds having a cyclohexenyl group as a ring structure. Relative to the total mass of the above-mentioned composition, it is preferred to set the content of compounds having a cyclohexenyl group to 10 mass % or less, more preferably to set it to 8 mass % or less, more preferably to set it to 5 mass % or less, more preferably to set it to 3 mass % or less, and it is even more preferred that it does not substantially contain compounds having a cyclohexenyl group.

When the improvement of viscosity and Tni is emphasized, the liquid crystal composition containing the polymerizable compound of the present invention preferably has a low content of the compound having "a 2-methylbenzene-1,4-diyl group in which the hydrogen atom may be substituted by a halogen" in the molecule. It is preferred that the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is set to 10 mass % or less, preferably 8 mass % or less, more preferably 5 mass % or less, more preferably 3 mass % or less, and it is even more preferred that the compound having a 2-methylbenzene-1,4-diyl group in the molecule is substantially free of the total amount of the liquid crystal composition of the present invention.

Furthermore, the phrase “substantially not containing” in this specification means not containing anything except what is intentionally contained.

The liquid crystal composition containing a polymerizable compound of the present invention may contain, in addition to the above-mentioned compounds, conventional nematic liquid crystals, lamellar liquid crystals, cholesteric liquid crystals, and the like.

[6] Additives The liquid crystal composition containing a polymerizable compound of the present invention may contain an antioxidant, an ultraviolet absorber, a light stabilizer or an infrared absorber. Among them, the liquid crystal composition containing a polymerizable compound of the present invention preferably contains an antioxidant and does not polymerize during the heat treatment which is one of the manufacturing steps of the liquid crystal display element.

The liquid crystal composition containing a polymerizable compound of the present invention preferably contains an antioxidant represented by general formula (H-1) to general formula (H-4), and the lower limit of the content is preferably 10 mass ppm, preferably 20 mass ppm, preferably 50 mass ppm, and the upper limit is preferably 10000 mass ppm, preferably 1000 mass ppm, preferably 500 mass ppm, and preferably 100 mass ppm.

In general formulae (H-1) to (H-3), ^RH1 independently represents an alkyl group having 3 to 7 carbon atoms. More specifically, ^RH1 in general formula (H-1) represents an alkyl group having 7 carbon atoms. ^RH1 in general formula (H-2) represents an alkyl group having 3 carbon atoms. ^RH1 in general formula (H-3) represents an alkyl group having 3 carbon atoms.

In the general formula (H-4), ^MH1 represents an alkylene group having 4 to 10 carbon atoms (one or more _-CH2- in the alkylene group may be substituted by -COO- or -OCO- in a manner where the oxygen atom is not directly adjacent to the group), a single bond, a 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be substituted by a fluorine atom), or a trans-1,4-cyclohexylene group. ^MH1 preferably represents an alkylene group having 4 to 8 carbon atoms.

[7] Others The liquid crystal composition containing a polymerizable compound of the present invention may also contain one or more compounds represented by general formula (i), one or more polymerizable compounds A represented by general formula (P), one or more compounds selected from the group of compounds represented by general formulas (N-01) to (N-05), and one or more compounds selected from the group of compounds represented by general formulas (NU-01) to (NU-08). The compound represented by general formula (i) may also be a compound represented by general formula (i-1-1).

The polymerizable compound-containing liquid crystal composition of the present invention may also contain one or more compounds represented by the general formula (i-1-1), one or more polymerizable compounds A represented by the general formula (P), one or more compounds selected from the group of compounds represented by the general formulas (N-01-1), (N-01-3), (N-01-4), (N-02-1), (N-03-1) and (N-04-1), and one or more compounds selected from the group of compounds represented by the general formulas (NU-01), (NU-02), (NU-03) and (NU-05).

The liquid crystal composition containing a polymerizable compound of the present invention may also contain one or more compounds represented by the general formula (i), one or more polymerizable compounds B, one or more compounds selected from the group of compounds represented by the general formulas (N-01) to (N-05), and one or more compounds selected from the group of compounds represented by the general formulas (NU-01) to (NU-08). In the above combination, the compound represented by the general formula (i) may also be a compound represented by the general formula (i-1-1).

The polymerizable compound-containing liquid crystal composition of the present invention may also contain one or more compounds represented by the general formula (i-1-1), one or more polymerizable compounds B represented by the general formula (SAL), one or more compounds selected from the group of compounds represented by the general formulas (N-01-1), (N-01-3), (N-01-4), (N-02-1), (N-03-1) and (N-04-1), and one or more compounds selected from the group of compounds represented by the general formulas (NU-01), (NU-02), (NU-03) and (NU-05).

The liquid crystal composition containing a polymerizable compound of the present invention may also contain one or more compounds represented by general formula (i), one or more polymerizable compounds A represented by general formula (P), one or more polymerizable compounds B, one or more compounds selected from the group of compounds represented by general formulas (N-01) to (N-05), and one or more compounds selected from the group of compounds represented by general formulas (NU-01) to (NU-08). In the above combination, the compound represented by general formula (i) may also be a compound represented by general formula (i-1-1).

The polymerizable compound-containing liquid crystal composition of the present invention may also contain one or more compounds represented by the general formula (i-1-1), one or more polymerizable compounds A represented by the general formula (P), one or more polymerizable compounds B represented by the general formula (SAL), one or more compounds selected from the group of compounds represented by the general formulae (N-01-1), (N-01-3), (N-01-4), (N-02-1), (N-03-1) and (N-04-1), and one or more compounds selected from the group of compounds represented by the general formulae (NU-01), (NU-02), (NU-03) and (NU-05).

The liquid crystal composition containing a polymerizable compound of the present invention is composed only of a compound represented by the general formula (i), a polymerizable compound selected from the group consisting of a polymerizable compound A and a polymerizable compound B represented by the general formula (P), a compound selected from the group of compounds represented by the general formulas (N-01) to (N-05), and a compound selected from the group of compounds represented by the general formulas (NU-01) to (NU-08). The upper limit of the proportion of the component in the total weight of the liquid crystal composition containing the polymerizable compound of the present invention is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, or 84 mass%.

Furthermore, the liquid crystal composition containing a polymerizable compound of the present invention is composed only of a compound represented by the general formula (i), a polymerizable compound selected from the group consisting of a polymerizable compound A and a polymerizable compound B represented by the general formula (P), a compound selected from the group of compounds represented by the general formulas (N-01) to (N-05), and a compound selected from the group of compounds represented by the general formulas (NU-01) to (NU-08). The lower limit of the proportion is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, or 99 mass% in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention.

The liquid crystal composition containing a polymerizable compound of the present invention comprises only a compound represented by the general formula (i-1-1), a polymerizable compound A represented by the general formula (P), a polymerizable compound B represented by the general formula (SAL), a compound selected from the group consisting of compounds represented by the general formulae (N-01-1), (N-01-3), (N-01-4), (N-02-1), (N-03-1) and (N-04-1), and a compound selected from the group consisting of compounds represented by the general formulae (NU-01), (NU-02), (NU-03-1) and (N-04-1). The upper limit of the proportion of the components constituted by the compounds in the compound group represented by (NU-03) and (NU-05) in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%. Moreover, the lower limit of the above ratio is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, or 99 mass% in the total amount of the liquid crystal composition containing the polymerizable compound of the present invention.

The nematic-isotropic liquid phase transition temperature (Tni) of the liquid crystal composition containing the polymerizable compound and the liquid crystal composition of the present invention is 60° C. to 120° C., more preferably 70° C. to 100° C., and even more preferably 70° C. to 85° C. In the present invention, 60° C. or more is indicated as a high Tni.

When used in LCD TVs, Tni is preferably 70 to 80°C, when used in mobile phones, Tni is preferably 80 to 90°C, and when used in outdoor displays such as PID (Public Information Display), Tni is preferably 90 to 110°C.

The liquid crystal composition containing a polymerizable compound and the liquid crystal composition of the present invention have a refractive index anisotropy (Δn) of 0.08 to 0.14 at 20°C, preferably 0.09 to 0.13, and particularly preferably 0.09 to 0.12. If further described, it is preferably 0.10 to 0.13 for a thin cell gap, and preferably 0.08 to 0.10 for a thick cell gap. Furthermore, the liquid crystal composition of the present invention preferably has a refractive index anisotropy (Δn) of 0.098 to 0.118 at 20°C.

The liquid crystal composition containing the polymerizable compound of the present invention and the liquid crystal composition of the present invention have a rotational viscosity (γ ₁ ) at 20° C. of 50 to 160 mPa·s, preferably 55 to 160 mPa·s, preferably 60 to 160 mPa·s, preferably 80 to 150 mPa·s, preferably 90 to 140 mPa·s, preferably 90 to 130 mPa·s, preferably 90 to 115 mPa·s.

The Δε of the liquid crystal composition containing the polymerizable compound of the present invention and the liquid crystal composition of the present invention is -1.7 to -4.0, preferably -2.5 to -3.8, more preferably -2.7 to -3.7, and even more preferably -2.6 to -3.6.

B. Liquid crystal display element Next, the liquid crystal display element of the present invention is described. The liquid crystal display element of the present invention is a liquid crystal display element using a liquid crystal composition containing a polymerizable compound as described in the above paragraph "A. Liquid crystal composition containing a polymerizable compound". That is, the liquid crystal display element of the present invention is a liquid crystal display element using a liquid crystal composition containing a polymerizable compound "containing one or more compounds represented by general formula (i) and one or more polymerizable compounds, and the total content of the compounds represented by the above general formula (i) is within a specific range".

The liquid crystal display element of the present invention can obtain a sufficiently large tilt angle by using the above-mentioned liquid crystal composition containing polymerizable compounds, and the residual amount of polymerizable compounds in the liquid crystal display element after polymerization is small. The high-precision PSA mode liquid crystal display element such as 4K or 8K will not produce display defects such as residual images (IS), or the display defects can be significantly suppressed. In addition, in the manufacture of high-precision PSA mode liquid crystal display elements such as 4K or 8K, if the UV irradiation time becomes longer, it can be seen that the VHR decreases or the production efficiency is significantly deteriorated due to the deterioration of the liquid crystal composition. However, since the liquid crystal display element of the present invention uses the above-mentioned liquid crystal composition containing polymerizable compounds, it becomes a high-precision PSA mode liquid crystal display element with a short UV irradiation time, and its industrial utilization value is very high.

The liquid crystal display element of the present invention is particularly useful for active matrix driven liquid crystal display elements. In addition, the liquid crystal display element of the present invention can be suitably used for liquid crystal display elements with a driving mode of PSA mode, PSVA mode, VA mode, PS-IPS mode or PS-FFS mode, and can be suitably used for liquid crystal display elements with PSA mode or PSVA mode.

The liquid crystal display element of the present invention can be formed into a universal structure, for example, it can be formed into a structure having "a first substrate and a second substrate arranged opposite to each other", "a common electrode disposed on the first substrate or the second substrate", "a pixel electrode disposed on the first substrate or the second substrate and having a thin film transistor", and "a liquid crystal layer disposed between the first substrate and the second substrate". In the liquid crystal display element of the present invention, the liquid crystal layer contains at least a compound represented by general formula (i), a liquid crystal composition contained in a liquid crystal composition containing a polymerizable compound, and a polymer of the polymerizable compound.

The liquid crystal display device of the present invention may have alignment films on the surface of the first substrate on the liquid crystal layer side and the surface of the second substrate on the liquid crystal layer side, respectively.

The liquid crystal display element of the present invention may also have an alignment film on the surface on the liquid crystal layer side of the above-mentioned first substrate and the surface on the liquid crystal layer side of the above-mentioned second substrate. The alignment film is a component in contact with the liquid crystal layer, and is a component having the function of aligning the liquid crystal molecules contained in the liquid crystal layer. In this case, the liquid crystal composition containing polymerizable compounds used to manufacture the liquid crystal display element of the present invention preferably contains at least one of polymerizable compound A and polymerizable compound B. The liquid crystal display element of the present invention can use the polymer of polymerizable compound A and/or polymerizable compound B to give a pre-tilt angle to the liquid crystal molecules by having the polymers of polymerizable compound A and/or polymerizable compound B separately concentrated on the first substrate side interface and the second substrate side interface of the liquid crystal layer. Furthermore, when the polymer contains polymerizable compound B, impurities present in the liquid crystal layer or the alignment film will be adsorbed and captured by the polar groups of the polymerizable compound B and incorporated into the polymer of the polymerizable compound B. Therefore, the reduction in VHR of the liquid crystal display element of the present invention caused by the presence of impurities is suppressed, and high reliability can be achieved.

The alignment film may use a known alignment film such as a friction alignment film or a photo alignment film. In addition, the alignment film may be appropriately selected as a vertical alignment film or a horizontal alignment film according to the driving mode of the liquid crystal display element. The material constituting the alignment film may be set to be the same as the material of the known alignment film, for example, polyimide, polyamide, polysiloxane, and mixtures thereof. Among them, polyimide is preferred. Polyimide may be a photocrosslinking type polyimide or a decomposable type polyimide. The thickness of the alignment film may be set to a thickness widely used in liquid crystal display elements.

Furthermore, the liquid crystal display element of the present invention may not have an alignment film on at least one of the first substrate and the second substrate. That is, the liquid crystal display element of the present invention may also be an element of a mode generally referred to as PI-less. In this case, the liquid crystal composition containing polymerizable compounds used in the manufacture of the liquid crystal display element of the present invention preferably contains at least polymerizable compound B. The polymerizable compound B forms a polymer and is concentrated on the first substrate side interface and the second substrate side interface of the liquid crystal layer, respectively. The polar group of the polymer of the polymerizable compound B interacts with the substrate surface, thereby, the liquid crystal display element of the present invention can vertically align the liquid crystal molecules in the liquid crystal layer even if it does not have an alignment film.

The first substrate and the second substrate (sometimes collectively referred to as substrates) in the liquid crystal display element of the present invention can be flexible substrates or rigid substrates. Furthermore, the substrates can be transparent or opaque, preferably transparent. Examples of the materials of the substrates include glass, resin, metal, silicon, etc.

The liquid crystal display element of the present invention has a common electrode on either the first substrate or the second substrate, and has a pixel electrode on the other. The common electrode and the pixel electrode are respectively arranged on the surface of the liquid crystal layer side of the substrate. Preferably, the common electrode is arranged on the substrate with a color filter, and the pixel electrode is arranged on the substrate without a color filter. The pixel electrode has active elements such as TFT, thin film diode, metal insulator metal ratio resistor element, etc. The common electrode and the pixel electrode can be formed with materials commonly used for electrodes of liquid crystal display elements. Among them, it is preferred that at least the common electrode is formed with a transparent conductor, and it is more preferred that both the common electrode and the pixel electrode are formed with a transparent conductor. Examples of the transparent conductor include oxide semiconductors such as indium-doped tin oxide (ITO), zinc oxide (ZnO), tin oxide (SnO ₂ ), InGaZnO, SiGe, GaAs, IZO (Indium Zinc Oxide), TiO, and AZTO (AlZnSnO).

The shapes of the common electrode and the pixel electrode can be selected to match the driving mode of the liquid crystal display element. Among them, when the liquid crystal display element of the present invention is driven by an active matrix, it is preferred that: one of the first substrate and the second substrate is provided with a whole-surface common electrode formed by a transparent conductor, and the gate electrode and the source electrode are arranged in a matrix on the other substrate, and the TFT element and the pixel electrode are provided in the portion surrounded by the gate electrode and the source electrode.

The common electrode and the pixel electrode can be formed by a known method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) such as sputtering, ion plating, and vacuum evaporation.

The liquid crystal display element of the present invention may also be provided with a color filter on the first substrate or the second substrate. The color filter is preferably provided on the substrate provided with the common electrode. The color filter may be formed, for example, using a pigment dispersion method (color resist method, etching method), a printing method, an inkjet method, or the like.

The liquid crystal display element of the present invention may also have a spacer between the first substrate and the second substrate in order to adjust the spacing distance between the first substrate and the second substrate, that is, the thickness of the liquid crystal layer. Examples of the spacer include glass particles, plastic particles, aluminum oxide particles, photoresist materials, etc.

The liquid crystal display element of the present invention may also have a polarizing plate. When a polarizing plate is provided, it is preferred to adjust the product of the refractive index anisotropy Δn of the liquid crystal composition and the cell thickness d in such a way that the contrast is maximized. Furthermore, when two polarizing plates are provided, the polarization axis of each polarizing plate may be adjusted to achieve a good viewing angle or contrast. Furthermore, a phase difference film for expanding the viewing angle may also be used.

The liquid crystal display device of the present invention can also use a sealant to fix the first substrate and the second substrate. Examples of the sealant include epoxy-based thermosetting compositions.

The liquid crystal display element of the present invention can be manufactured using a known method. As a manufacturing method of the liquid crystal display element of the present invention, the following example can be cited. First, the surface of the first substrate on which the orientation film is arranged is opposed to the surface of the second substrate on which the orientation film is arranged, and they are bonded together through a spacer and a sealing portion to form an expected cell gap, thereby manufacturing an empty cell. Secondly, a vacuum injection method or an ODF method is used to clamp the liquid crystal composition containing a polymerizable compound of the present invention between the first substrate and the second substrate of the empty cell, and the sealing portion is hardened to seal the liquid crystal composition between the first and second substrates. Then, UV light is irradiated to polymerize the polymerizable compound contained in the liquid crystal composition containing a polymerizable compound, thereby obtaining the liquid crystal display element of the present invention. The UV light irradiation conditions (temperature, light source, wavelength, applied voltage, irradiation method, irradiation time, irradiation intensity, etc.) for polymerizing the polymerizable compound can be appropriately set.

The present invention is not limited to the above-mentioned embodiments. The above-mentioned embodiments are illustrative, and any device having substantially the same structure and the same effect as the technical idea described in the patent application scope of the present invention is included in the technical scope of the present invention. [Embodiment]

The present invention is further described in detail with the following embodiments, but the present invention is not limited to these embodiments.

The following codes are used to describe the compounds in the following Examples and Comparative Examples.

(Side chain) -n -C _n H _2n+1 straight chain alkyl with n carbon atoms -C _n H _2n+1 - straight chain alkyl with n carbon atoms -On -OC _n H _2n+1 straight chain alkoxy with n carbon atoms V - CH ₂ =CH - 1V - CH ₃ -CH=CH - -V -CH=CH ₂ -V1 -CH=CH -CH ₃ (Bond group) -1O - -CH ₂ -O - -2 - -CH ₂ -CH ₂ -

(Ring structure)

The properties measured in the following embodiments and comparative examples are as follows.

T _ni : Nematic-isotropic liquid phase transition temperature (°C) Δn : Refractive index anisotropy at 20°C γ ₁ : Rotational viscosity at 20°C (mPa･s) Δε : Dielectric conductivity at 20°C The manufacturing method and evaluation method of the liquid crystal display device in the following examples and comparative examples are as follows.

(Manufacturing method of liquid crystal display element) First, the liquid crystal composition containing a polymerizable compound described later is injected into a "liquid crystal cell with a cell gap of 3.5μm containing an ITO-attached substrate" by vacuum injection. The above-mentioned ITO-attached substrate is coated with a polyimide alignment film that induces vertical alignment and is rubbed. After that, the liquid crystal cell injected with the liquid crystal composition containing a polymerizable compound is irradiated with ultraviolet light for an arbitrary time using a fluorescent UV lamp to obtain a liquid crystal display element. At this time, the fluorescent UV lamp is adjusted to an illumination of 3mW/ ^cm2 measured under the condition of a central wavelength of 313nm.

(Evaluation method of residual amount of polymerizable compounds) Under the above irradiation conditions, the residual amount of polymerizable compounds in the liquid crystal display element after irradiation with ultraviolet light for 15 minutes, 30 minutes, 45 minutes, 60 minutes, 75 minutes, 90 minutes, and 115 minutes was measured by the following method. First, the decomposed liquid crystal display element and acetonitrile were added to the test tube, and the tube was shaken and filtered to obtain an acetonitrile solution containing the eluted components of the liquid crystal composition, polymer, and unreacted polymerizable compounds. It was analyzed using a high-performance liquid chromatography instrument (column: reverse phase nonpolar column; developing solvent: a mixed solvent of 70 volume % acetonitrile and 30 volume % water) to calculate the peak area of each component. The amount of the residual polymerizable compound is determined by the ratio of the peak area of the liquid crystal compound as an index to the peak area of the unreacted polymerizable compound. The residual amount of the polymerizable compound is determined based on this value and the amount of the polymerizable compound initially added. Furthermore, the detection limit of the residual amount of the polymerizable compound is 200 ppm. At this time, the UV irradiation time at which the residual amount of the polymerizable compound does not reach the detection lower limit is set as T _ND [minutes].

(Evaluation method of pre-tilt angle variation (tilt impartability)) The pre-tilt angle variation [°] of a liquid crystal display element before and after irradiation with ultraviolet rays for 200 seconds under the above-mentioned irradiation conditions is measured by the following method. First, the pre-tilt angle of the liquid crystal display element is measured, and is referred to as the pre-tilt angle (initial). The liquid crystal display element is irradiated with ultraviolet rays for 200 seconds while applying a voltage of 10V at a frequency of 100Hz. Then, the pre-tilt angle is measured, and is referred to as the pre-tilt angle (after UV). The value obtained by subtracting the pre-tilt angle (after UV) from the measured pre-tilt angle (initial) is referred to as the pre-tilt angle variation [°]. The pre-tilt angle is measured using OPTIPRO manufactured by Shintec. The larger the pre-tilt angle variation [°], the higher the tilt give.

(Method for evaluating VHR) The liquid crystal cell into which the liquid crystal composition containing the polymerizable compound was injected was irradiated with UV for T _ND [minutes] under the above-mentioned irradiation conditions, and the VHR was measured under the conditions of 1 V, 0.6 Hz, and 60° C.

(Preparation and physical properties of liquid crystal compositions) Prepare liquid crystal compositions LC-001 to LC-005 before adding the compound of formula (i) and the polymerizable compound, and measure their physical properties. The composition and physical properties of the liquid crystal compositions LC-001 to LC-005 are shown in Table 1.

[Table 1]

(Comparative Examples 1 to 3, Examples 1 to 3) “A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of a polymerizable compound A represented by the formula (RM-A1) as a polymerizable compound to 100 parts by mass of a liquid crystal composition LC-001” is referred to as Comparative Example 1.

A “liquid crystal composition containing a polymerizable compound obtained by adding 3 parts by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 97 parts by mass of the liquid crystal composition LC-001” was designated as Comparative Example 2.

A “liquid crystal composition containing a polymerizable compound obtained by adding 2 parts by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 98 parts by mass of the liquid crystal composition LC-001” was designated as Comparative Example 3.

Example 1 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1.5 parts by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 98.5 parts by mass of a liquid crystal composition LC-001”.

Example 2 is a “liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-001”.

Example 3 is “a liquid crystal composition containing a polymerizable compound obtained by adding 0.5 parts by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99.5 parts by mass of a liquid crystal composition LC-001”.

Regarding the liquid crystal compositions containing polymerizable compounds of Comparative Examples 1 to 3 and Examples 1 to 3, the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound does not reach the detection limit, the VHR [%] after UV irradiation at T _ND , and the change in pre-tilt angle [°] after 200 seconds of UV irradiation are shown in Table 2 below. The content (mass %) of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound is a value calculated by {mass part of the compound of formula (i)/(mass part of the liquid crystal composition + mass part of the compound of formula (i) + mass part of the polymerizable compound (A and B))}×100. The same applies to the following.

[Table 2] Comparative example 1 Comparative example 2 Comparative example 3 Embodiment 1 Embodiment 2 Embodiment 3 Liquid crystal composition LC-001 100 97 98 98.5 99 99.5 Compound of formula (i) Formula (i-1-1-1A) 0 3 2 1.5 1 0.5 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0 3.0 2.0 1.5 1.0 0.5 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 60 30 30 30 30 45 VHR after UV exposure with T _ND [%] 96 95 95 95 95 96 Pre-tilt angle change after 200 seconds of UV irradiation [°] 1.5 3.2 3.5 5.2 6.0 4.0

According to Table 2, VHR [%] after UV irradiation with T _ND is sufficiently high, but the UV irradiation time T _ND [min] at which the residual amount of the polymerizable compound does not reach the detection limit is shorter in Comparative Example 1, Comparative Examples 2-3 and Examples 1-2 than in Comparative Example 1. In addition, the change in pre-tilt angle [°] when irradiated with UV for 200 seconds is greater in Comparative Example 2-3 than in Comparative Example 1, but Examples 1-3 show a greater value than Comparative Examples 1-3, indicating that Examples 1-3 can form a larger pre-tilt angle with a shorter UV irradiation time than Comparative Examples 1-3. In addition, for the liquid crystal display elements after irradiation with UV by T _ND , OPTIPRO manufactured by Shintec was used to conduct "display defect (afterimage) evaluation caused by the change of pre-tilt angle before and after irradiation with backlight for 3 hours while applying 30V voltage at a frequency of 100Hz". The results showed that Examples 1 to 3 showed high tilt stability.

(Comparative Examples 4-5, Example 4, Example 4-2) “A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 100 parts by mass of a liquid crystal composition LC-002” is referred to as Comparative Example 4.

A “liquid crystal composition containing a polymerizable compound obtained by adding 3 parts by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 97 parts by mass of the liquid crystal composition LC-002” is set as Comparative Example 5.

Example 4 is a “liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002”.

Example 4-2 is “a liquid crystal composition containing a polymerizable compound obtained by adding 0.5 parts by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99.5 parts by mass of a liquid crystal composition LC-002”.

Regarding the liquid crystal compositions containing polymerizable compounds in Comparative Examples 4 to 5 and Examples 4 and 4-2, the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound does not reach the detection limit, the VHR [%] after UV irradiation at T _ND , and the change in pre-tilt angle [°] when irradiated with UV for 200 seconds are shown in the following Table 3, respectively.

[Table 3] Comparative example 4 Comparative example 5 Embodiment 4 Example 4-2 Liquid crystal composition LC-002 100 97 99 99.5 Compound of formula (i) Formula (i-1-1-1A) 0 3 1 0.5 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0 3.0 1.0 0.5 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 105 30 30 60 VHR after UV exposure with T _ND [%] 76 93 93 85 Pre-tilt angle change after 200 seconds of UV irradiation [°] 0.2 1.3 2.2 1.9

According to Table 3, the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound does not reach the detection limit is shorter in Comparative Example 4, Comparative Example 5 and Example 4 than in Comparative Example 4. Regarding VHR [%] after UV irradiation at T _ND , Comparative Example 5 and Example 4 are sufficiently high values compared to Comparative Example 4. In addition, regarding the change in pre-tilt angle [°] when irradiated with UV for 200 seconds, Comparative Example 5 is greater than Comparative Example 4, but Example 4 shows a larger value, which shows that the pre-tilt angle can be formed with a UV irradiation time shorter than that of Comparative Examples 4 and 5. In addition, for the liquid crystal display element after irradiation with UV by T _ND , OPTIPRO manufactured by Shintec was used to conduct "evaluation of display defects (afterimages) caused by changes in the pre-tilt angle before and after irradiation with backlight for 3 hours while applying a voltage of 30V at a frequency of 100Hz". The results showed that Example 4 showed high tilt stability.

In addition, the T _ND of Example 4-2 is shorter than that of Comparative Example 4, the VHR thereof is higher than that of Comparative Example 4, and the variation of the pre-tilt angle thereof is greater than that of Comparative Example 5.

In addition, the liquid crystal composition LC-002 is a composition containing an alkenyl compound represented by "3-Cy-Cy-V". As shown in Table 1, the value of γ1 of the liquid crystal composition LC-002 is smaller than the value of γ1 of other liquid crystal compositions not containing "3-Cy-Cy-V". The smaller the value of γ1, the faster the response speed. Therefore, the liquid crystal composition shows that the response speed becomes faster due to the inclusion of the alkenyl compound. On the other hand, according to the results of Comparative Examples 1 and 4, the T _ND of the liquid crystal composition LC-002 is longer than that of the liquid crystal composition LC-001 not containing "3-Cy-Cy-V". Furthermore, the VHR of the liquid crystal composition LC-002 after irradiation with UV with T _ND is significantly lower than that of the liquid crystal composition LC-001. Therefore, the liquid crystal composition containing the alkenyl compound shows a long T _ND and a decreased VHR due to UV irradiation.

It is shown that by adding the compound of formula (i) to the general liquid crystal composition LC-002, T _ND is shortened and the reduction of VHR can be suppressed. Furthermore, by regulating the content of the compound of formula (i) within a specific range, the change in pre-tilt angle [°] can be increased even with short-term UV irradiation.

(Examples 5-6) “A liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-4A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-001” is set as Example 5.

Example 6 is a “liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-37A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-001”.

Regarding the liquid crystal composition containing a polymerizable compound in Examples 5 to 6, the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound does not reach the detection limit, the VHR [%] after UV irradiation at T _ND , and the change in pre-tilt angle [°] when irradiated with UV for 200 seconds are shown in Table 4 below.

[Table 4] Embodiment 5 Embodiment 6 Liquid crystal composition LC-001 99 99 Compound of formula (i) Formula (i-1-1-4A) 1 0 Formula (i-1-1-37A) 0 1 Polymerizable compound A Formula (RM-A1) 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 1.0 1.0 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 45 45 VHR after UV exposure with T _ND [%] 94 95 Pre-tilt angle change after 200 seconds of UV irradiation [°] 3.6 4.0

The same evaluation as in Example 1 was performed on the liquid crystal compositions containing polymerizable compounds in Examples 5 and 6. As a result, the liquid crystal compositions containing polymerizable compounds in Examples 5 and 6 were the same as in Example 1, and it was confirmed that the problem of the present invention was solved.

(Examples 7 to 12) “A liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-4A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002” is set as Example 7.

Example 8 is a “liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-37A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002”.

Example 9 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-4B) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002”.

Example 10 is a “liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-48A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002”.

Example 11 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1B) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002”.

Example 12 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-2A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002”.

Regarding the liquid crystal compositions containing polymerizable compounds of Examples 7 to 12, the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound does not reach the detection limit, the VHR [%] after UV irradiation at T _ND , and the change in pre-tilt angle [°] when irradiated with UV for 200 seconds are shown in the following Table 5.

[Table 5] Embodiment 7 Embodiment 8 Embodiment 9 Embodiment 10 Embodiment 11 Embodiment 12 Liquid crystal composition LC-002 99 99 99 99 99 99 Compound of formula (i) Formula (i-1-1-4A) 1 0 0 0 0 0 Formula (i-1-1-37A) 0 1 0 0 0 0 Formula (i-1-1-4B) 0 0 1 0 0 0 Formula (i-1-1-48A) 0 0 0 1 0 0 Formula (i-1-1-1B) 0 0 0 0 1 0 Formula (i-1-1-2A) 0 0 0 0 0 1 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 1.0 1.0 1.0 1.0 1.0 1.0 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 60 60 60 60 30 60 VHR after UV exposure with T _ND [%] 85 87 85 85 92 87 Pre-tilt angle change after 200 seconds of UV irradiation [°] 1.1 1.3 1.1 1.4 1.2 1.2

The liquid crystal compositions containing polymerizable compounds of Examples 7 to 12 also have shorter T _ND , higher VHR, and larger pre-tilt angle variation compared to Comparative Example 4 in which the compound of formula (i) is not added to LC-002. Among them, Example 11 containing the compound of formula (i-1-1B) has smaller T _ND and higher VHR after UV irradiation compared to other Examples 7 to 10 and 12. It can be inferred that this is because the compound of formula (i) has no substituent on the ring adjacent to the condensed ring, so the UV irradiation time can be shortened, and the degradation caused by UV irradiation is suppressed.

(Comparative Examples 6-7, Examples 13-14) The "liquid crystal composition containing a polymerizable compound obtained by adding 0.7 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 100 parts by mass of the liquid crystal composition LC-002" is referred to as Comparative Example 6.

A “liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of a polymerizable compound A represented by the formula (RM-A1) and 0.4 parts by mass of a polymerizable compound B represented by the formula (RM-B1) as polymerizable compounds to 100 parts by mass of the liquid crystal composition LC-002” is set as Comparative Example 7.

A “liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-4A) as a compound of formula (i) and 0.7 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-002” is referred to as Comparative Example 13.

Example 14 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-4A) as a compound of formula (i), 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1) as a polymerizable compound, and 0.4 parts by mass of a polymerizable compound B represented by formula (RM-B1) to 99 parts by mass of a liquid crystal composition LC-002”.

Regarding the liquid crystal compositions containing polymerizable compounds of Comparative Examples 6-7 and Examples 13-14, the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound does not reach the detection limit, the VHR [%] after UV irradiation at T _ND , and the change in pre-tilt angle [°] after UV irradiation for 200 seconds are shown in the following Table 6. The content (mass %) of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound is a value calculated by {mass part of the compound of formula (i)/(mass part of the liquid crystal composition + mass part of the compound of formula (i) + mass part of the polymerizable compounds (A and B))}×100.

[Table 6] Comparative example 6 Comparative example 7 Embodiment 13 Embodiment 14 Liquid crystal composition LC-002 100 100 99 99 Compound of formula (i) Formula (i-1-1-4A) 0 0 1 1 Polymerizable compound A Formula (RM-A1) 0.7 0.3 0.7 0.3 Polymerizable compound B Formula (RM-B1) 0 0.4 0 0.4 Total amount of liquid crystal composition containing polymerizable compounds 100.7 100.7 100.7 100.7 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0% 0.0% 1.0% 1.0% UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 105 105 60 60 VHR after UV exposure with T _ND [%] 78 92 87 96 Pre-tilt angle change after 200 seconds of UV irradiation [°] 0.6 2.8 1.8 3.6

Regarding the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound does not reach the detection limit, Examples 13 and 14 have shorter times than Comparative Examples 6 and 7. Regarding VHR [%] after UV irradiation at T _ND , Example 13 has a sufficiently high value compared to Comparative Example 6, and Example 14 has a sufficiently high value compared to Comparative Example 7. Regarding the change in pre-tilt angle [°] when irradiating UV for 200 seconds, Example 13 has a value greater than that of Comparative Example 6, and Example 14 has a value greater than that of Comparative Example 7.

In Example 14, in which 0.4 mass parts of the compound of formula (RM-A1) in 0.7 mass parts of Example 13 was replaced with the compound of formula (RM-B1), the VHR was higher than that of Example 13. Example 14 containing polymerizable compound A, polymerizable compound B, and the compound of formula (i) was sufficiently higher than that of Comparative Examples 6 to 7 and Example 13. From this result, it can be seen that by containing both polymerizable compound A and polymerizable compound B, the decrease in VHR can be further suppressed.

According to the results of the above-mentioned examples and comparative examples, the content of the compound of formula (i) within a specific range can be quickly and fully polymerized, and a larger angle of tilt can be formed with weaker or less UV light, and the VHR after UV irradiation also shows a higher value. In addition, it can be seen that the occurrence of display defects (afterimages) caused by backlight exposure is also suppressed, showing high tilt stability.

(Examples 15 to 19) “A liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A2) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-001” is set as Example 15.

Example 16 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A3) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-001”.

Example 17 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A4) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-001”.

Example 18 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.5 parts by mass of a polymerizable compound represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-001”.

Example 19 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i), 0.2 parts by mass of a polymerizable compound represented by formula (RM-A1) as a polymerizable compound, and 0.1 parts by mass of a polymerizable compound represented by formula (RM-A5) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-001”.

The liquid crystal compositions containing polymerizable compounds of Examples 15 to 19 were also evaluated in the same manner as in Example 1. As a result, the liquid crystal compositions containing polymerizable compounds of Examples 15 to 19 were also the same as in Example 1, and it was confirmed that the problem of the present invention was solved, and it was taught that the effect of the present invention can be exerted by containing a specific amount of the compound of formula (i) regardless of the type of polymerizable compound.

(Examples 20 to 24) “A liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A2) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-002” is set as Example 20.

Example 21 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A3) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-002”.

Example 22 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A4) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-002”.

Example 23 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.5 parts by mass of a polymerizable compound represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-002”.

Example 24 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i), 0.2 parts by mass of a polymerizable compound represented by formula (RM-A1) as a polymerizable compound, and 0.1 parts by mass of a polymerizable compound represented by formula (RM-A5) to 99 parts by mass of the liquid crystal composition LC-002”.

The liquid crystal compositions containing polymerizable compounds of Examples 20 to 24 were also evaluated in the same manner as in Example 4. As a result, the liquid crystal compositions containing polymerizable compounds of Examples 20 to 24 were also similar to those of Example 4, and it was confirmed that the problem of the present invention was solved, and it was taught that regardless of the type of polymerizable compound, by containing a specific amount of the compound of formula (i), the effect of the present invention can be exerted even when an alkenyl compound is contained.

(Examples 25 to 27) “A liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A1) as a polymerizable compound to 99 parts by mass of a liquid crystal composition LC-003” is set as Example 25.

Example 26 is a “liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A3) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-004”.

Example 27 is “a liquid crystal composition containing a polymerizable compound obtained by adding 1 part by mass of a compound represented by formula (i-1-1-1A) as a compound of formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A4) as a polymerizable compound to 99 parts by mass of the liquid crystal composition LC-005”.

The liquid crystal compositions containing polymerizable compounds of Examples 25 to 27 were also evaluated in the same manner as in Example 1. As a result, the liquid crystal compositions containing polymerizable compounds of Examples 25 to 27 were also similar to those of Example 1, and it was confirmed that the problem of the present invention was solved, and it was taught that the effect of the present invention can be exerted by containing a specific amount of the compound of formula (i) regardless of the composition of the liquid crystal composition of the present invention and the type of the polymerizable compound.

(Examples 28 to 31) “A liquid crystal composition containing a polymerizable compound obtained by further adding 0.005 parts by weight of an antioxidant represented by formula (H-2-1) to the liquid crystal composition containing a polymerizable compound obtained in Example 2” is set as Example 28.

Example 29 is referred to as “a liquid crystal composition containing a polymerizable compound obtained by further adding 0.005 parts by mass of an antioxidant represented by the formula (H-4-1) to the liquid crystal composition containing a polymerizable compound obtained in Example 2”.

Example 30 is referred to as “a liquid crystal composition containing a polymerizable compound obtained by further adding 0.005 parts by mass of an antioxidant represented by the formula (H-2-1) to the liquid crystal composition containing a polymerizable compound obtained in Example 4”.

Example 31 is “a liquid crystal composition containing a polymerizable compound obtained by further adding 0.005 parts by mass of an antioxidant represented by formula (H-4-1) to the liquid crystal composition containing a polymerizable compound obtained in Example 4”.

The liquid crystal compositions containing polymerizable compounds of Examples 28 to 29 were also evaluated in the same manner as in Example 1. As a result, the liquid crystal compositions containing polymerizable compounds of Examples 28 to 29 were the same as in Example 1, and it was confirmed that the problem of the present invention was solved.

The polymerizable compound-containing liquid crystal compositions of Examples 30 and 31 were also evaluated in the same manner as in Example 4. As a result, the polymerizable compound-containing liquid crystal compositions of Examples 30 and 31 were the same as in Example 4, and it was confirmed that the problem of the present invention was solved.

(Examples 32 to 46) In the same manner as LC-001 to LC-005, liquid crystal compositions LC-006 to LC-010 were prepared before adding the compound of formula (i) and the polymerizable compound, and their physical properties were measured in the same manner as LC-001 to LC-005. The composition and physical properties of the liquid crystal compositions LC-006 to LC-010 are shown in Table 7.

[Table 7] LC-006 LC-007 LC-008 LC-009 LC-010 3-Cy-Cy-2 7.5 3-Cy-Cy-V 29.5 29.5 29.5 29.5 29.5 3-Cy-Ph-O1 12 10 11.5 3-Ph-Ph-1 11 3-Ph-Ph-O1 5 3-Cy-Ph-Ph-1 8 7 7 5.5 7 3-Cy-Ph-Ph-2 5 3-Cy-1O-Ph5-O1 4 4 4 3-Cy-1O-Ph5-O2 13.5 12 12 12 14.5 3-Cy-Cy-1O-Ph5-O2 20.5 V－Cy－Cy－1O－Ph5－O2 6.5 7 5 2-Cy-Ph-Ph5-O2 6 6 6 3-Cy-Ph-Ph5-O2 13 13 13 9 2-Ph-2-Ph-Ph5-O2 7 3-Ph-2-Ph-Ph5-O2 11 9.5 9.5 9.5 7 3-Cy-Cy-Ph5-O2 9 8 4.5 Total(wt%) 100 100 100 100 100 Tni [℃] 75.2 73.2 76.7 74.4 74.7 Δn 0.109 0.1086 0.1087 0.1071 0.1091 Δε -3.24 -2.95 -2.94 -2.96 -2.74 γ1 [mPa･s] 90 82 82 78 75

Next, except that the compound of formula (i) and polymerizable compound A were added to LC-006 to LC-010 as shown in Tables 8 to 12, liquid crystal compositions containing polymerizable compounds were prepared in the same manner as in Example 1, and these were designated as Examples 32 to 46.

Then, the liquid crystal compositions containing polymerizable compounds of Examples 32 to 46 were evaluated in the same manner as in Example 1. The evaluation test results of Examples 32 to 46 are shown in Tables 8 to 12. Examples 32 to 34 were compared with Comparative Example 8, Examples 35 to 37 were compared with Comparative Example 9, Examples 38 to 40 were compared with Comparative Example 10, Examples 41 to 43 were compared with Comparative Example 11, and Examples 44 to 46 were compared with Comparative Example 12. The results were the same as in Example 1, and it was confirmed that the problem of the present invention was solved.

[Table 8] Comparative example 8 Embodiment 32 Embodiment 33 Embodiment 34 Liquid crystal composition LC-006 100 99.8 99.5 99 Compound of formula (i) Formula (i-1-1-1B) - 0.2 0.5 1 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0 0.2 0.5 1.0 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 105 45 35 30 VHR after UV exposure with T _ND [%] 76 80 90 93 Pre-tilt angle change after 200 seconds of UV irradiation [°] 0.2 0.7 1.2 1.4

[Table 9] Comparative example 9 Embodiment 35 Embodiment 36 Embodiment 37 Liquid crystal composition LC-007 100 99.8 99.5 99 Compound of formula (i) Formula (i-1-1-1B) - 0.2 0.5 1 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0 0.2 0.5 1.0 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 105 45 35 30 VHR after UV exposure with T _ND [%] 77 79 89 94 Pre-tilt angle change after 200 seconds of UV irradiation [°] 0.2 0.6 1.2 1.5

[Table 10] Comparative example 10 Embodiment 38 Embodiment 39 Embodiment 40 Liquid crystal composition LC-008 100 99.8 99.5 99 Compound of formula (i) Formula (i-1-1-1B) - 0.2 0.5 1 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0 0.2 0.5 1.0 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 105 45 35 30 VHR after UV exposure with T _ND [%] 76 82 90 93 Pre-tilt angle change after 200 seconds of UV irradiation [°] 0.3 0.7 1.1 1.4

[Table 11] Comparative example 11 Embodiment 41 Embodiment 42 Embodiment 43 Liquid crystal composition LC-009 100 99.8 99.5 99 Compound of formula (i) Formula (i-1-1-1B) - 0.2 0.5 1 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0 0.2 0.5 1.0 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 105 45 35 30 VHR after UV exposure with T _ND [%] 75 80 91 94 Pre-tilt angle change after 200 seconds of UV irradiation [°] 0.2 0.7 1.2 1.4

[Table 12] Comparative example 12 Embodiment 44 Embodiment 45 Embodiment 46 Liquid crystal composition LC-010 100 99.8 99.5 99 Compound of formula (i) Formula (i-1-1-1B) - 0.2 0.5 1 Polymerizable compound A Formula (RM-A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compounds 100.3 100.3 100.3 100.3 Content of the compound of formula (i) in the total amount of the liquid crystal composition containing the polymerizable compound [mass %] 0.0 0.2 0.5 1.0 UV irradiation time T _ND [min] when the residual amount of polymerizable compounds does not reach the detection limit 105 45 35 30 VHR after UV exposure with T _ND [%] 73 78 91 92 Pre-tilt angle change after 200 seconds of UV irradiation [°] 0.2 0.7 1.2 1.4

(Examples 47 to 76) “The liquid crystal composition containing a polymerizable compound prepared by further adding 0.005 parts by mass of an antioxidant represented by formula (H-2-1) to the liquid crystal composition containing a polymerizable compound used in Examples 32 to 46” is set as Examples 47 to 61.

Examples 62 to 76 were used as “liquid crystal compositions containing a polymerizable compound prepared by further adding 0.005 parts by mass of an antioxidant represented by formula (H-4-1) to the liquid crystal compositions containing a polymerizable compound used in Examples 32 to 46”.

Then, the liquid crystal compositions containing polymerizable compounds of Examples 47 to 76 were evaluated in the same manner as in Example 1. The results showed that the liquid crystal compositions containing polymerizable compounds of Examples 47 to 76 were superior to those of Example 1. Thus, it was confirmed that the problem of the present invention was solved.

without

without

Claims (7)

A liquid crystal composition containing a polymerizable compound, comprising one or more compounds represented by the general formula (i-1-1-1), wherein the total content of the compounds represented by the general formula (i-1-1-1) is 0.05 mass % to 1.9 mass %, In formula (i-1-1-1), R ⁱ¹¹¹ and R ⁱ¹¹² independently represent 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 2 to 10 carbon atoms, and one or more hydrogen atoms in these groups may be substituted by fluorine atoms; and a polymerizable compound A represented by formula (RM-A1) and a polymerizable compound B represented by formula (RM-B1) . The liquid crystal composition containing a polymerizable compound as claimed in claim 1, further comprising one or more compounds selected from the compounds represented by the general formula (L): (wherein, ^RL1 and ^RL2 are each independently an alkyl group having 1 to 8 carbon atoms, one or two or more non-adjacent _-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, ^nL1 is 0, 1, 2 or 3, ^AL1 , ^AL2 and ^AL3 are each independently a group selected from the group consisting of the following groups (a), (b) and (c), (a) 1,4-cyclohexyl (one _-CH2- or two or more non-adjacent _-CH2- in the group may be substituted by -O-), (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=), and (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in the naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=), wherein the above group (a), group (b) and group (c) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom, and Z ^L1 and Z ^L2 are each independently substituted with a single bond, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -OCH ₂ -, -CH ₂ O-, -COO-, -OCO-, -OCF ₂ -, -CF ₂ O-, -CH=NN=CH-, -CH=CH-, -CF=CF- or -C≡C-, when n ^L1 is 2 or 3 and there are plural A ^L2s , they may be the same or different, when n ^L1 is 2 or 3 and there are plural Z ^L2s , they may be the same or different; wherein the compounds represented by the general formula (i) are not included). The liquid crystal composition containing a polymerizable compound as claimed in claim 1, further comprising one or more compounds selected from the compounds represented by the general formula (N-1), (In the formula, R ^N11 and R ^N12 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent -CH ₂ - groups in the alkyl group may each independently be substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, A ^N11 and A ^N12 each independently represent a group selected from the group consisting of the following groups (a), (b), (c) and (d), (a) 1,4-cyclohexylene (one -CH ₂ - or two or more non-adjacent -CH ₂ - groups in the group may be substituted by -O-), (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted by -N=), (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=), and (d) 1,4-cyclohexenyl. The above groups (a), (b), (c) and (d) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom. Z ^N11 and Z ^N12 are each independently substituted with a single bond, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -OCH ₂ -, -CH ₂ O-, -COO-, -OCO-, -OCF ₂ -, -CF ₂ O-, -CH=NN=CH-, -CH=CH-, -CF=CF- or -C≡C-, n ^N11 and n ^N12 are independent of each other and represent integers from 0 to 3, n ^N11 +n ^N12 is 1, 2 or 3, and when there are multiple A ^N11 ~A ^N12 , Z ^N11 ~Z ^N12 , they may be the same or different; wherein, the compounds represented by the general formula (i) and the general formula (L) are not included). The liquid crystal composition containing a polymerizable compound as claimed in claim 3 contains one or more compounds in which at least one of ^RL1 and ^RL2 in the above general formula (L) represents an alkenyl group having 2 to 8 carbon atoms. A liquid crystal display element using the liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 6. An active matrix driven liquid crystal display element uses a liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 6. A liquid crystal display element for a PSA mode, PSVA mode, PS-IPS mode or PS-FFS mode, which uses a liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 6.