TW202134409A - Liquid crystal composition containing polymeric compound and liquid crystal display element wherein the liquid crystal composition containing polymeric compound contains one or more compounds represented by the general formula (i) and one or more polymeric compounds - Google Patents

Abstract

The subject of the present invention is to provide a polymeric liquid crystal composition and a liquid crystal display element using the same. The polymeric liquid crystal composition can be used to manufacture liquid crystal display elements that can be fully polymerized at a faster speed, can form a tilt with weak or little UV light, and has excellent reliability after the UV irradiation step. The solution of the invention is to provide a liquid crystal composition containing polymeric compound, which contains one or more compounds represented by the general formula (i) and one or more polymeric compounds. The total content of the compounds represented by the 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 element using the liquid crystal composition. 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, the 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 the cell in order to control the pretilt angle of liquid crystal molecules. Because of its high-speed response and high contrast, it has been practically used as a liquid crystal display element. change.

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

In recent years, high-definition pixels are required for liquid crystal display elements of PSA mode such as 4K or 8K. Therefore, due to the increase in the area of the wiring or the light-shielding part, a considerable amount of UV light is cut off. In the same UV irradiation step as in the past, problems such as insufficient tilt formation, insufficient polymerization of polymerizable compounds, and large amounts of polymerizable compounds remain. . In addition, it was confirmed that such things as "deterioration of response speed", "generation of residual images due to deterioration of alignment", and "residual polymerizable compounds gradually polymerized and tilted during driving, resulting in burning (IS) "This kind of display is bad.

From the above, it can be seen that the high-definition PSA mode liquid crystal display element requires a liquid crystal composition that can be stably manufactured using weaker or less UV light than before.

As a method for a liquid crystal composition for polymerizing a liquid crystal composition containing a polymerizable compound with weaker or less UV light than in the past, Patent Document 1 and Patent Document 2 describe the method of containing a triphenyl skeleton or naphthalene The technology of the liquid crystal compound of the skeleton to shorten the polymerization reaction rate, etc. [Prior Technical Literature] [Patent Literature]

Patent Document 1: Japanese Special Form No. 2013-503952 Patent Document 2: International Publication No. 2014/148197

[The problem to be solved by the invention]

As described above, in recent years, for high-definition PSA mode liquid crystal display elements, there is a demand for a polymerizable compound-containing liquid crystal composition that can be stably manufactured with weaker or less UV light than in the past. However, although the polymerizable compound-containing liquid crystal composition containing a liquid crystal compound having a terphenyl skeleton or a naphthalene skeleton described in the examples of Patent Document 1 or Patent Document 2 has a sufficient polymerization rate, the tilt formation is insufficient and the tilt The stability is not high enough. Therefore, there is a need to improve the characteristics of liquid crystal compositions containing polymerizable compounds. The improvement of the characteristics of the polymerizable compound-containing liquid crystal composition is not limited to the use of the PSA mode liquid crystal display device, and it is also required in the polymerizable compound-containing liquid crystal composition used in the liquid crystal display device of other driving modes.

The problem to be solved by the present invention is to provide a liquid crystal composition containing a polymerizable compound, and to provide a liquid crystal display element using the same. , Capable of forming a tilted liquid crystal display element with weak or less UV light and excellent reliability after the UV irradiation step. [Means to solve the problem]

The inventors of the present invention conducted intensive research on the above-mentioned problems and found that a polymerizable compound-containing liquid crystal containing a compound having a specific structure and a polymerizable compound and further setting the content of the above-mentioned compound having a specific structure within a specific range The composition can solve the above-mentioned problems, and the invention of the present application has been completed.

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

(In the formula, R ⁱ¹ and R ⁱ² are independent of each other and represent an alkyl group with 1 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an alkenyl group with 2 to 10 carbon atoms or 2 to 10 carbon atoms For the alkenyloxy group, one or more hydrogen atoms in these groups may be substituted by fluorine atoms. Ring A and ring B are independently selected from the group (a), group (b), The group consisting of group (c) and group (d), (a) 1,4-cyclohexylene (1 -CH ₂ -existing in the group-or 2 or more non-adjacent -CH ₂ -May be substituted by -O-), (b) 1,4-phenylene (1 -CH= or 2 or more not adjacent to each other in the group -CH= may be substituted by -N=), ( c) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (exist in naphthalene-2,6-diyl) Group or one of 1,2,3,4-tetrahydronaphthalene-2,6-diyl group -CH= or two or more not adjacent -CH= can be substituted by -N=), and (d)1 ,4-Cyclohexenylene; The above group (a), group (b), group (c) and group (d) are independent of each other, and may be substituted by the following groups or atoms: carbon atoms that can be substituted by fluorine atoms An alkyl group of 1 to 8, an alkoxy group of 1 to 8 carbon atoms that may be substituted by a fluorine atom, a cyano group, or a fluorine atom, C represents a divalent condensed ring group having one or more benzene rings, the above condensation One or more hydrogen atoms of the cyclic group may be substituted by the following groups or atoms: an alkyl group with 1 to 8 carbon atoms which may be substituted by a fluorine atom, and a carbon atom number of 1 which may be substituted by a fluorine atom Up to 8 alkoxy group or fluorine atom, Z ⁱ¹ and Z ⁱ² are respectively independent, representing -OCH ₂ -, -CH ₂ O-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, －CH ₂ CH ₂ －, －CF ₂ CF ₂ －, －C≡C－ or a single bond, n ⁱ¹ and n ⁱ² are independent, respectively, and represent 0, 1 or 2, in the presence of plural rings A, B, and Z respectively ^{For i1} and Z ⁱ² , they can be the same or different respectively).

In addition, the present invention provides a liquid crystal display element using a liquid crystal composition containing a polymerizable compound, 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. The polymerizable compound-containing liquid crystal composition contains one or more compounds represented by the general formula (i), and one or more polymerizable compounds, the total of the compounds represented by the general formula (i) The content is less than 2.0% by mass. [Effects of Invention]

With the polymerizable compound-containing liquid crystal composition of the present invention, it is possible to fully polymerize at a relatively fast speed, and can form a tilt with weak or less UV light, and can achieve high tilt stability. In addition, the polymerizable compound-containing liquid crystal composition of the present invention can be fully polymerized at a relatively fast speed, and the UV irradiation time can be shortened. Therefore, the deterioration of the liquid crystal composition and the voltage retention rate (VHR) caused by UV irradiation can be suppressed. ) To reduce.

Then, the liquid crystal display element using the polymerizable compound-containing liquid crystal composition of the present invention has a small residual amount of unreacted polymerizable compound, can form a tilt with weak or less UV light, and exhibits high-speed response and high VHR , With high tilt stability, there is no display defects such as poor alignment or residual image caused by changes in the pretilt angle, or the above display defects are suppressed, and excellent display quality can be displayed.

Hereinafter, the polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal display element using the same will be described in detail. Furthermore, the compound represented by general formula (i) may be referred to as a compound of general formula (i) or compound (i). The same is true for other compounds.

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

(In the formula, R ⁱ¹ , R ⁱ² , ring A, ring B, C, Z ⁱ¹ , Z ⁱ² , n ⁱ¹ and n ⁱ² are as defined above respectively).

According to the polymerizable compound-containing liquid crystal composition 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 composition from the general formula (i) The sensitizing effect of the compound represented by) enables the polymerizable compound to fully polymerize at a faster speed, can form a larger tilt with weak or less UV light, and can achieve high tilt stability. Furthermore, according to the polymerizable compound-containing liquid crystal composition of the present invention, since it can be fully polymerized at a relatively fast rate, the UV irradiation time can be shortened, so the deterioration of the liquid crystal composition caused by UV irradiation can be suppressed, and the voltage retention can be suppressed. Rate (VHR) reduction.

In addition, the liquid crystal display element using the polymerizable compound-containing liquid crystal composition of the present invention has a small residual amount of unreacted polymerizable compound, can form a large tilt with weak or less UV light, and exhibits high-speed responsiveness , High VHR, and high tilt stability, there is no display defects such as poor alignment or residual image caused by changes in the pretilt angle, or the above display defects are suppressed, and excellent display quality can be displayed.

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

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

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

In the general formula (i), R ⁱ¹ and R ⁱ² are independent of each other and represent an alkyl group with 1 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an alkenyl group with 2 to 10 carbon atoms, or the number of carbon atoms 2 to 10 alkenyloxy. One or more hydrogen atoms in these groups may be substituted by fluorine atoms.

From the aspect that the effect of reducing _{γ 1 is} ^{high, R i1} and R ^{i2 are} preferably independent of each other, and are an alkyl group with 1 to 5 carbon atoms or an alkenyl group with 2 to 5 carbon atoms, and a carbon atom is particularly preferred. An alkyl group having 1 to 3 or an alkenyl group having 2 to 3 carbon atoms. In addition, the alkyl group and alkenyl group are preferably linear.

Furthermore, in terms of increasing the |Δε| of the polymerizable compound-containing liquid crystal composition, R ⁱ¹ and R ^{i2 are} preferably independent of each other and are alkoxy groups having 1 to 5 carbon atoms or carbon atoms 2 to 5 alkenyloxy.

Furthermore, in terms of the effect of improving the reliability of VHR, etc., R ⁱ¹ and R ^{i2 are} preferably independent of each other and are an alkyl group with 1 to 5 carbon atoms or an alkoxy group with 1 to 5 carbon atoms. , Particularly 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 unsubstituted, and it is preferable that R ⁱ¹ and R ^{i2 are} not substituted by fluorine atoms.

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

The above-mentioned groups (a), group (b), group (c) and group (d) are each independently, and may be substituted by the following groups or atoms: alkyl groups with 1 to 8 carbon atoms that may be substituted by fluorine atoms, An alkoxy group having 1 to 8 carbon atoms, a cyano group or a fluorine atom substituted by 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 preferably 1,4-cyclohexylene, unsubstituted 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3 -Difluoro-1,4-phenylene.

In further detail, from the viewpoint of making the polymerization rate of the polymerizable compound faster, ring A and ring B are preferably independently unsubstituted 1,4-phenylene and 2-fluoro-1. ,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene, especially unsubstituted 1,4-phenylene. The UV absorption band of unsubstituted phenylene is on the longer wavelength side than that of phenylene substituted by other atoms such as fluorine atoms. Thereby, the polymerizable compound-containing liquid crystal composition of the present invention containing the compound represented by the general formula (i) having an unsubstituted phenylene is compared to the liquid crystal composition containing the general formula (i) having a substituent In the case of the compound, the reaction rate of the polymerizable compound can be made faster, and the reduction of VHR can be sufficiently suppressed.

On the other hand, from the viewpoint of further improving the miscibility with other liquid crystal components, it is preferable that ring A and ring B are independently 2-fluoro-1,4-phenylene and 3-fluoro-1,4. -Phenylene or 2,3-difluoro-1,4-phenylene.

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

In the general formula (i), C represents a divalent condensed ring group in which one or more benzene rings are polymerized. Here, the condensed ring group having one or more benzene rings means a group in which a plurality of rings containing at least one benzene ring form a condensed ring. In addition, a condensed ring refers to a ring having a structure in which two or more rings share two or more atoms and are bonded.

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

In addition, among the rings constituting the condensed ring 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 setting the number of benzene rings in the condensed ring group within the above range, it is easier to achieve both an appropriate polymerization rate and high reliability by containing the compound represented by the general formula (i).

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

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

Aliphatic allotropic rings have a cyclic structure composed of only carbon atoms. The aliphatic homotopic ring preferably has 4 to 8 carbon atoms, more preferably 4 to 6 carbon atoms, and still more preferably 5 or 6 carbon atoms. Examples of the above-mentioned aliphatic allocyclic rings include cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclobutene ring, cyclopentene ring, and cyclohexene ring. Ring and so on. Among them, the aliphatic homologous 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 of the aliphatic rings -CH ₂ -are replaced by -O-, -S-, or -NH-. The number of ring members of the aliphatic heterocyclic ring is preferably 4-8, 4-6, 5 or 6. As such an aliphatic heterocyclic ring, a pyrrolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, a piperidine ring, a tetrahydropyran ring, a tetrahydrothiopyran ring, etc. are mentioned, for example.

Aromatic heterocyclic ring is a structure in which one, two or three of the aromatic rings are -CH = substituted by -O-, -S-, or -N-. The number of ring members of the aromatic heterocyclic ring is preferably 4-8, 4-6, 5 or 6. As such an aromatic heterocyclic ring, a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, etc. are mentioned, for example.

Among them, the condensed ring group represented by the above C is preferably a condensed ring group consisting of 2 or 3 benzene rings, or 1 or 2 benzene rings, and is selected from the group consisting of tetrahydrofuran ring, tetrahydropiperan ring, and pyridine ring. A condensed ring consisting of one or two rings in the group consisting of a ring, a pyrrolidine ring, and a tetrahydrothiophene ring.

One or more hydrogen atoms of the condensed ring group represented by C may be substituted by the following groups or atoms: an alkyl group with 1 to 8 carbon atoms that may be substituted by a fluorine atom, or a fluorine atom The substituted alkoxy group having 1 to 8 carbon atoms or fluorine atom, but in terms of the ease of compound synthesis, one or more hydrogen atoms of the condensed ring group represented by the above C is preferred For unsubstituted.

In the condensed ring group represented by C, ^{the bonding position A with Z i1} (when n ⁱ¹ is 0, it is R ⁱ¹ ) and the bonding position B with Z ⁱ² (when n ⁱ² is 0, it is R ⁱ² ) Each is not particularly limited, but it is preferable that the above-mentioned bonding position A and the above-mentioned bonding position B are located in a linear shape.

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

(In the formula, * indicates ^{the bonding point with Z i1} or R ⁱ¹ , and the black dot (●) indicates the bonding point ^{with Z i2} or R ^i2).

Among the above structures, C in the general formula (i) more preferably represents a condensed ring group selected from the following structures.

(In the formula, * indicates ^{the bonding point with Z i1} or R ⁱ¹ , and the black dot (●) indicates the bonding point ^{with Z i2} or R ^i2).

Among the above structures, C in the general formula (i) preferably represents 2,6-naphthalenediyl, because it can further improve the compatibility of high polymerization speed and high reliability.

In the general formula (i), Z ⁱ¹ and Z ⁱ² are independent of each other, representing -OCH ₂ -, -CH ₂ O-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -, -C≡C- or single bond. Among them, Z ⁱ¹ and Z ⁱ² are independent of each other, preferably -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -or a single bond. In order to accelerate the polymerization rate of the polymerizable compound, the single bond is particularly preferred.

In the general formula (i), when there are plural ^Zi1 and ^Zi2 respectively, the plural ^Zi1 and the plural ^Zi2 may be the same or different.

For example, the compound represented by the general formula (i) may be bonded to the condensed ring represented by C via one ring A or B, and Z ⁱ¹ or Z ⁱ² represents any one of the above groups other than a single bond. Makes reliability and solubility better.

In the general formula (i), n ⁱ¹ and n ⁱ² are independent of each other and represent 0, 1, or 2. In terms of good mixing with other liquid crystal molecules, n ⁱ¹ + n ⁱ² preferably represents 1 or 2. In terms of better mixing properties and tilt stability with other liquid crystal molecules, n ⁱ¹ + n ⁱ² preferably represents 1. When n ⁱ¹ + n ⁱ² represents 2, n ^{i1 can} represent 1 and n ^{i2 can} represent 1, ^{or one of n i1} or n ⁱ² can represent 2 and the other can represent 0. Among them, in terms of better mixing with other liquid crystal molecules, it is preferable that one of n ⁱ¹ or n ⁱ² represents 2 and the other represents 0.

In the general formula (i), when there are a plurality of rings A, B, Z ⁱ¹ and Z ⁱ² , respectively, 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).

(In the formula, R ⁱ¹¹ , R ⁱ¹² , ring A ⁱ¹ , ring B ⁱ¹ , Z ⁱ¹¹ , Z ⁱ¹² , n ⁱ¹¹ and n ⁱ¹² respectively represent the same as R ⁱ¹ , R ⁱ² , ring A, ring B, Z ⁱ¹ , Z ⁱ² , n ⁱ¹ and n ^{i2 have the} same meaning, n ⁱ¹¹ + n ⁱ¹² represents 1, 2, 3, or 4, and X ⁱ¹¹ to X ⁱ¹⁶ are independent of each other and represent the number of carbon atoms that can be substituted by fluorine atoms 1 Up to 8 alkyl groups, alkoxy groups having 1 to 8 carbon atoms that can be substituted by fluorine atoms, fluorine atoms or hydrogen atoms)

In the general formula (i-1), from the viewpoint of mixing with other liquid crystal molecules, n ⁱ¹¹ + n ^{i12 is} preferably 1 or 2. From the viewpoint of mixing with other liquid crystal molecules and tilt stability In terms of aspect, it is more preferably 1.

In the general formula (i-1), X ⁱ¹¹ to X ⁱ¹⁶ are each 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 It is a fluorine atom or a hydrogen atom, and a hydrogen atom is particularly preferable.

The number of groups X ⁱ¹¹ to X ⁱ¹⁶ that are hydrogen atoms is preferably at least three. Specifically, ^{the number of groups X i11} to X ⁱ¹⁶ that are hydrogen atoms 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), ^{the preferable aspects of R i11} , R ⁱ¹² , ring A ⁱ¹ , ring B ⁱ¹ , Z ⁱ¹¹ and Z i12 can be set as the same as R in the above general formula (i) ^{The preferred aspects of i1} , R ⁱ² , ring A, ring B, Z ⁱ¹ and Z ⁱ² are the same.

In the general formula (i-1), when n ⁱ¹¹ represents 0 and n ⁱ¹² represents 1 or 2, when the ring B ^{i1 directly bonded to R i12} is 2,3-difluoro-1,4-phenylene, R ^{i12 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) in combination is higher than when ^{R i12 is a group other than an alkoxy group.} In this case, R ^{i11 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.

In the general formula (i-1), when n ⁱ¹¹ represents 0 and n ⁱ¹² represents 2, when the ring B ^{i1 directly bonded to R i11} is 1,4-phenylene, R ⁱ¹ and R ^{i2 are} preferred Each is independently 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. This is because compared with ^{the case where one or both of R i1} and R ⁱ² are groups other than the alkyl group, the suppressed voltage retention rate (VHR ) The reduction effect is higher.

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

(In the formula, R ⁱ¹¹¹ , R ⁱ¹¹² , ring A ⁱ¹¹ , ring B ⁱ¹¹ , Z ⁱ¹¹¹ and Z ^{i112 respectively represent the same as R i1} , R ⁱ² , ring A, ring B, Z ⁱ¹ and Z in the above general formula (i) ^{i2 has the} same meaning, Y ⁱ¹¹¹ and Y ⁱ¹¹² are independent of each other and represent an alkyl group with 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group with 1 to 8 carbon atoms which may be substituted by a fluorine atom, a fluorine atom or For the hydrogen atom, n ⁱ¹¹¹ and n ⁱ¹¹² are independent and represent 0 or 1).

In the general formula (i-1-1), Y ⁱ¹¹¹ and Y ⁱ¹¹² are independent of each other, 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, it is 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. One of Y ⁱ¹¹¹ and Y ⁱ¹¹² may be a fluorine atom and the other may be a hydrogen atom, both may represent a fluorine atom, or both may represent a hydrogen atom. The compound represented by the general formula (i-1-1) has a ^{fluorine atom or a hydrogen atom independently represented by Y i111} and Y ⁱ¹¹² respectively, which can make the polymerization rate of the polymerizable compound faster, and can further improve the mixing with other liquid crystal components Performance, high tilt stability can be obtained.

In the general formula (i-1-1), n ⁱ¹¹¹ and n ⁱ¹¹² are independent of each other and represent 0 or 1. From the viewpoint of mixing with other liquid crystal molecules, n ⁱ¹¹¹ + n ^{i112 is} preferably 0 or 1, In terms of better mixing properties with other liquid crystal molecules and tilt stability, 0 is more preferable. When n ⁱ¹¹¹ + n ⁱ¹¹² is 1, n ⁱ¹¹¹ can be 1 and n ⁱ¹¹² can be 0, or n ⁱ¹¹¹ can be 0 and n ⁱ¹¹² can be 1. Among them, n ⁱ¹¹¹ represents 0 and n ⁱ¹¹² represents 1 preferably. This is because the compound represented by the general formula (i-1-1) adopts a molecular structure in which the condensed ring is the center and the ring structure is biased on one side, so that the mixing property with other liquid crystal molecules becomes better.

^{Regarding the preferred aspects} of R i111, R ⁱ¹¹² , ring A ⁱ¹¹ , ring B ⁱ¹¹ , Z ⁱ¹¹¹ and Z ^{i112 in} the general formula (i-1-1), they can be set as the same as those in the above general formula (i) ^{Preferred aspects} of R ⁱ¹ , R ⁱ² , ring A, ring B, Z ⁱ¹ and Z i2 are the same.

In the general formula (i-1-1), when n ⁱ¹¹¹ and n ⁱ¹² respectively represent 0, Y ⁱ¹¹¹ and Y ⁱ¹¹² also represent a fluorine atom, R ^{i112 is} preferably an alkoxy group with 1 to 10 carbon atoms. It is 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-1-1) 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.

Also, in the general formula (i-1-1), when n ⁱ¹¹ represents 0 and n ⁱ¹² represents 1, Y ⁱ¹¹¹ and Y ⁱ¹¹² both represent fluorine atoms, and B ⁱ¹¹ represents 1,4-phenylene, R ⁱ¹¹ and R ^{i12 is} preferably each independently 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. This is because compared with ^{the case where one or both of R i11} and R ⁱ¹² are groups other than the alkyl group, the suppressed voltage retention rate (VHR ) The reduction effect is higher.

The compound represented by general formula (i) is preferably each compound represented by the following general formula (i-1-1-1) to general formula (i-1-1-55). Among them, even more preferable compounds are the general formula (i-1－1-1)～the general formula (i－1-1-6), the general formula (i－1-1-12)～the general formula (i－1－ 1-17), general formula (i－1-1-23) ~ general formula (i－1-1-28), or general formula (i－1-1－34) ~ general formula (i－1-1 －39), the compound represented by the general formula (i-1－1-145) to the general formula (i-1－1-50), more preferably the general formula (i-1－1-1) to the general formula ( i－1-1－4), general formula (i－1-1－34)～general formula (i－1-1－37), or general formula (i－1-1－45)～general formula (i The compound represented by -1-1-48) is particularly preferably a compound represented by general formula (i-1-1-1) to general formula (i-1-1-4).

(In the formula, R ⁱ¹¹¹ and R ⁱ¹¹² respectively represent the same meaning as ^{R i1} and R ⁱ² in the above general formula (i)).

The compound of the general formula (i) can promote the polymerization reaction of the polymerizable compound by its sensitization effect. On the other hand, if the content of the compound of the general formula (i) is too large, it is difficult to form a large enough compound by a short-time reaction. Inclination, VHR reduction, etc. In contrast, the polymerizable compound-containing liquid crystal composition of the present invention can be formed in a short time by adjusting the content of the compound of the general formula (i) within a specific range, allowing the polymerizable compound to be fully polymerized at a relatively fast rate. A sufficiently large inclination can suppress the decrease of VHR caused by UV irradiation, and can satisfy various characteristics with good balance.

Regarding the content of the compound of the general formula (i), as long as the total amount of the polymerizable compound-containing liquid crystal composition of the present invention is less than 2.0% by mass, the upper limit of the content is preferably 1.9% by mass and 1.8% by mass. %, 1.7% by mass, 1.6% by mass, 1.5% by mass, 1.4% by mass, 1.3% by mass, 1.2% by mass, 1.0% by mass, 0.9% by mass, 0.8% by mass, 0.7% by mass, 0.6% by mass, and 0.5% by mass. In addition, the content of the compound of the general formula (i) only needs to exceed 0% by mass in the total amount of the polymerizable compound-containing liquid crystal composition of the present invention. The lower limit of the content is preferably 0.01% by mass, 0.05 Mass%, 0.1% by mass, 0.2% by mass, 0.3% by mass, 0.4% by mass, 0.5% by mass, 0.6% by mass, 0.7% by mass, 0.8% by mass, 0.9% by mass, 1.0% by mass.

As the range of the content of the compound of the general formula (i), more specifically, it is only required to exceed 0% by mass and less than 2.0% by mass, preferably 0.05% to 1.9% by mass, 0.5% to 1.9% by mass , 0.5% by mass to 1.5% by mass, and 0.5% by mass to 1.0% by mass.

[2] Polymeric compound The polymerizable compound-containing liquid crystal composition of the present invention contains one or more polymerizable compounds. The polymerizable compound is a compound having at least one polymerizable group in the molecular structure. By forming a polymer in the manufacturing process of the liquid crystal display element, it can impart a tilt angle to the liquid crystal molecules and can improve the response speed, Tni, Δε And other physical properties.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains at least one of the following polymerizable compound A and the following polymerizable compound B at least one type or two or more types. Hereinafter, the polymerizable compound A and the polymerizable compound B will be described.

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

(In the above general formula (P), R ^p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group with 1 to 15 carbon atoms or -Sp ^p2 -P ^p2 , one of the alkyl groups or the non-adjacent 2 More than one -CH ₂ -is independent of each other, and can also be substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, one of the alkyl groups may be Two or more hydrogen atoms are independent of each other, and may be substituted by cyano, fluorine or chlorine atoms. P ^p1 and P ^p2 are independent of each other, representing any of the general formula (P ^p1 -1) to formula (P ^p1 -9) One.

(In the formula, R ^p11 and R ^p12 are independent of each other and represent a hydrogen atom, an alkyl group with 1 to 5 carbon atoms, or a halogenated alkyl group with 1 to 5 carbon atoms, and W ^p11 represents a single bond, -O-, -COO- , Alkylene with 1 to 5 carbon atoms, t ^p11 represents 0, 1 or 2, and when there are multiple R ^p11 , R ^p12 , W ^p11 and/or t ^p11 in the molecule, they may be the same or different) , Sp ^p1 and Sp ^p2 are independent of each other, indicating a single bond or spacer, Z ^p1 and Z ^p2 are each independent, indicating 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 -, -CF ₂ O-, -OCF ₂ -, -CF ₂ CH ₂ -, -CH ₂ CF ₂ -, -CF ₂ CF ₂ -Or -C≡C- (where z independently represents an integer from 1 to 4, and R ^ZP1 independently represents a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, when there are multiple R ^{ZP1 in the molecule} , They can be the same or different. Moreover, the * in the formula represents ^{the bonding point with Sp p1} or Sp ^p2 ), and A ^p1 and A ^p2 are independent of each other, which means that they are selected from the following groups (a ^p ) and group (b) ^p ), and the group in the group consisting of the group ^{(c p ), (a p} ) 1,4-cyclohexylene (1 -CH ₂ -existing in the group or more than 2 unadjacent -CH ₂ -may be substituted by -O-), (b ^p ) 1,4-phenylene (1 -CH= or 2 or more not adjacent to each other in the group -CH= may be substituted by -N=) , And (c ^p ) naphthalenediyl, 1,2,3,4-tetrahydronaphthalenediyl, decahydronaphthalenediyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl (exist in One of these bases-CH = or two or more non-adjacent ones-CH = OK Is substituted by -N=), A ^p3 represents a group selected from the group consisting of the aforementioned group (a ^p ), group (b ^p ), group (c ^p ), and single bond, and the aforementioned group (a ^p ), group (B ^p ) and the group (c ^p ) are independent of each other, and the hydrogen atoms present in the group may be replaced by a cyano group, a halogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 8 carbon atoms, Alkenyl with 1 to 8 carbon atoms or -Sp ^p2 -P ^p2 substitution, m ^p1 represents 0, 1, 2 or 3, when there are plural Z ^p1 , A ^p2 , Sp ^p2 and/or P ^p2 in the molecule, They may be the same or different. 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 something other than a single bond Base) 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) is not included in the polar group described in the polymerizable compound B below. P ^p1 and P ^p2 are independent of each other, preferably ^{any one of the groups represented by the above general formula (P p1} -1) to formula (P ^p1-3 ), and preferably the above general formula (P ^p1 -1) The base expressed.

^{R p11} and R ^p12 in the general formulas (P ^p1 -1) to (P ^p1 -9) are independent of each other, and are preferably a hydrogen atom or a methyl group.

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

^{W p11} in the general formulas (P ^p1 -1) to (P ^p1 -9) is preferably a single bond or an alkylene group having 1 to 5 carbon atoms. The alkylene 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, preferably 0 or 1.

In the general formula (P), Z ^p1 and Z ^p2 are independent of each other, preferably a single bond, -OCH ₂ -, -CH ₂ O-, -CO-, -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-, -CF ₂ -, -CF ₂ O-,- (CH ₂ ) _z -COO-, -(CH ₂ ) _z -OCO-, -OCO- (CH ₂ ) _z -, -CH=CH-COO-, -COO-CH=CH-, -OCOCH=CH- , -COO- (CH ₂ ) _z -, -OCF ₂ -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 in the molecule is -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-, Others are single bonds, preferably only one in the molecule is -OCH ₂ -, -CH ₂ O-, -C ₂ H ₄ -, -COO- or -OCO-, and the others are single bonds, Preferably, all are single bonds.

Furthermore, it is preferable that ^{only one of Z p1} and Z ^p2 existing in the molecule is selected from -CH=CH-COO-, -COO-CH=CH-, -(CH ₂ ) ₂ -COO-, -( CH ₂ ) ₂ -OCO-, -O-CO- (CH ₂ ) ₂ -, -COO- (CH ₂ ) ₂ -The bonding group in the group consisting of, the others are single bonds.

In the general formula (P), Sp ^p1 and Sp ^p2 are independent of each other and represent a single bond or a spacer. The spacer is preferably an alkylene group with 1 to 30 carbon atoms. The -CH ₂ -in the alkylene group, As long as the oxygen atoms are not directly bonded to each other, they can also be substituted by -O-, -CO-, -COO-, -OCO-, -CH=CH- or -C≡C-, and the hydrogen atom in the alkylene group is also May be substituted by halogen atoms. Among them, Sp ^p1 and Sp ^p2 are independent of each other, and are preferably 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 preferably 2 to 3.

A ^p1 and A ^p2 are independent of each other and represent a base selected from the group consisting of the following (a ^p ), (b ^p ), and (c ^p ). (A ^p ) 1,4-cyclohexylene (1 -CH ₂ -or 2 or more non-adjacent -CH ₂ -may be substituted by -O- in the group), (b ^p )1,4 -Phenylene (one in the group-CH = or 2 or more not adjacent-CH = can be substituted by -N =), and (c ^p ) naphthalenediyl, 1,2,3,4 －Tetrahydronaphthalenediyl, decahydronaphthalenediyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl (exist in one of these groups -CH= or 2 or more not adjacent -CH= can be replaced by -N=). In addition, ^Ap3 represents a group selected from the group consisting of the above-mentioned group (a ^p ), group (b ^p ), group (c ^p ), and single bond.

Here, ^{the naphthalenediyl group and the 1,2,3,4-tetrahydronaphthalenediyl group that A p1} , A ^p2 and A ^p3 may have are groups bonded to two positions selected from positions 1 to 8. Specifically, in the case of A ^p1 , the naphthalenediyl group and 1,2,3,4-tetrahydronaphthalenediyl group are bonded to ^{Sp p1} at one of two positions selected from positions 1 to 8 , In the other position and Z ^p1 or Z ^p2 bonding base, in the case of A ^{p2 , it is bonded to Z p1} in one of the two positions selected from 1 to 8, in the other position The base for bonding with Z ^p1 or Z ^p2 , in the case of A ^{p3 , is bonded to Z p2} at one of the two positions selected from positions 1 to 8, and bonded to ^{R p1 at the other position} The base.

In addition, ^{the decahydronaphthalene diyl group that A p1} , A ^p2 and A ^p3 may have is a group bonded to two positions selected from the 1 to 10 positions. Specifically, in the case of A ^{p1 , the decahydronaphthalenediyl group is 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. The base of the binding, in the case of A ^{p2 , is the base that binds to Z p1} at one of the two positions selected from positions 1 to 10, and ^{binds to Z p1} or Z ^p2 at the other position, if a ^p3 is the case, it is selected from 1 to 10 in two positions of a portion of bonded and Z ^p2, R ^p1, and another portion of the group bonded at.

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

As the 1,2,3,4-tetrahydronaphthalenediyl group, for example, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene- 1,4-diyl, 1,2,3,4-tetrahydronaphthalene-1,5-diyl, etc. Among them, 1,2,3,4-tetrahydronaphthalene-2,6-diyl is preferred.

As decahydronaphthalenediyl group, decahydronaphthalene-2,6-diyl is preferable.

A ^p1 , A ^p2 and A ^p3 are independent of each other, and are preferably 1,4-phenylene or 1,4-cyclohexylene, and from the viewpoint of reactivity, 1,4-phenylene is preferred. In order to improve the compatibility of the 1,4-phenylene compound with the liquid crystal compound, it is preferable that at least one hydrogen atom in the 1,4-phenylene compound is fluorine atom, an alkyl group with 1 to 8 carbon atoms, or Alkoxy substituted with 1 to 8 carbons.

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

Furthermore, in terms of improving tilt stability, it is preferable that the 1,4-phenylene is unsubstituted, or that at least one hydrogen atom present in the 1,4-phenylene 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, it means that it is selected from The base in the group consisting of the above base (a ^p ), base (b ^p ) and base (c ^{p ).}

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

If the content of the polymerizable compound A represented by the general formula (P) contained in the polymerizable compound-containing liquid crystal composition of the present invention is small, it is difficult to visualize the addition of the polymerizable compound A represented by the general formula (P) As a result, disadvantages such as insufficient tilt formation and deterioration of tilt stability are likely to occur. In addition, problems such as weak alignment control of the liquid crystal composition or weakening with the passage of time are likely to occur. On the other hand, if the above content is too large, problems such as an increase in the amount remaining after curing, a time-consuming curing, and a decrease in the reliability of the liquid crystal will occur. Therefore, by considering the balance of the above and setting the content in combination with the above upper limit value and lower limit value, the polymerizable compound-containing liquid crystal composition of the present invention can impart a tilt to the liquid crystal molecules at a large enough angle, and can maintain the tilt highly for a long time. Stability and alignment control of the liquid crystal composition 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 polymerizable compound-containing liquid crystal composition of the present invention, it is preferably in the range of 0.05% by mass to 10% by mass Within, preferably in the range of 0.1% by mass to 8% by mass, more preferably in the range of 0.1% by mass to 5% by mass, more preferably in the range of 0.1% by mass to 3% by mass, more preferably 0.2% by mass It is in the range of ~2% by mass, preferably in the range of 0.2% by mass to 1.3% by mass, preferably in the range of 0.2% by mass to 1% by mass, and more preferably in the range of 0.2% by mass to 0.56% by mass.

As a preferable example of the polymerizable compound A represented by general formula (P), the compound represented by the following general formula (P-1-1)-general formula (P-1-46) is mentioned.

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

Moreover, as a preferable example of the polymerizable compound A represented by general formula (P), the compound represented by following formula (P-2-1)-formula (P-2-16) is mentioned.

(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)).

Moreover, as a preferable example of the polymerizable compound A represented by general formula (P), the compound represented by following formula (P-3-1)-formula (P-3-15) is mentioned.

(In the formula, P ^p31 , P ^p32 , Sp ^p31 and Sp ^p32 represent the same meanings as ^{P p1} , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P)).

Moreover, as a preferable example of the polymerizable compound A represented by general formula (P), the polymerizable compound represented by following formula (P-4-1)-formula (P-4-21) is mentioned.

(In the formula, P ^p41 , P ^p42 , Sp ^p41 and Sp ^p42 represent the same meanings as ^{P p1} , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P)).

Moreover, as a preferable example of the polymerizable compound represented by general formula (P), the compound represented by following formula (P-5-1)-formula (P-5-37) is mentioned.

(In the formula, P ^p51 , P ^p52 , Sp ^p51 and Sp ^p52 represent 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 formulas (P-1-1) to (P-5-37), the general formula (P-1-1) to the general formula (P-1-34) or the general formula (P －2－10) ~ The compound represented by the general formula (P-2-16), more preferably the general formula (P-1-1) to the general formula (P-1-3), the general formula (P-1 -6) ~ General formula (P-1-7), general formula (P-1-10) ~ general formula (P-1-11), general formula (P-1-23), general formula (P-1 －32) or the compound represented by the general formula (P-2-10), particularly preferably the general formula (P-1-1) to the general formula (P-1-3), the general formula (P-1-6) ~ General formula (P-1-7), general formula (P-1-10) or general formula (P-1-11) represented by the compound.

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

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

The polymerizable compound B has the same functions as the polymerizable compound A, but by having a polar group in the molecular structure, the following functions can be further exerted. That is, in a liquid crystal display element without an alignment film, the polar group possessed by the polymer of the polymerizable compound B interacts with the substrate to impart vertical alignment to the liquid crystal molecules even without the alignment film. Therefore, the polymerizable compound-containing liquid crystal composition of the present invention can be used to manufacture a liquid crystal display element that does not have an alignment film on at least one surface 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 radical compounds present in the liquid crystal layer or in the alignment film , Which can adsorb and trap impurities. Therefore, the polymerizable compound-containing liquid crystal composition of the present invention can suppress the decrease in specific resistance or VHR caused by impurities, and can produce a highly reliable liquid crystal display element. In addition, it is estimated that the function of adsorbing and trapping impurities by the polar group can also be exerted in a liquid crystal display element that does not have an alignment film.

The polymerizable compound B needs only to have a structure having at least one polymerizable group and one or more polar groups. Among them, it preferably has a mesogen group, one or more polymerizable groups, and one or more polymerizable groups. The structure of polar groups. The details of mesogens 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 the general formula (AP-9).

(In the formula, R ^AP1 and R ^AP2 are independent of each other and represent a hydrogen atom, an alkyl group with 1 to 5 carbon atoms, or a halogenated alkyl group with 1 to 10 carbon atoms, one of the alkyl groups or two unadjacent ones The above -CH ₂ -can be substituted by -O- or -CO- in such a way that the oxygen atom is not directly adjacent to each other, and one or two or more hydrogen atoms in the alkyl group are independent and can be substituted by halogen atoms or hydroxyl groups. W ^AP1 represents a single bond, -O-, -COO- or -CH ₂ -. t ^AP1 represents 0, 1, or 2. In the formula, * represents a bonding bond).

Among them, P ^{AP1 is} preferably a group selected from the group represented by the general formula (AP-1) to the general formula (AP-7), and more preferably the following general formula (AP-1) or general formula (AP -2) The base expressed by the general formula (AP-1) is more preferable.

The polymerizable group P ^{AP1 is} preferably bonded to the ^mesogen group via the spacer Sp AP1. The mesogenic group will be described in detail below. The spacer Sp ^AP1 preferably represents a single bond, or a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably represents a single bond or a linear alkylene group having 1 to 20 carbon atoms, and More preferably, it represents a single bond or a linear alkylene group having 2 to 10 carbon atoms. In addition, in the spacer Sp ^AP1 , one of the alkylene groups or two or more non-adjacent -CH ₂ -can also be -CH=CH-, -C≡C- so that the oxygen atom is not directly adjacent to each other. , -O-, -CO-, -COO- or -OCO- replaced. In addition, "substitution by polymerizable group P ^AP1 " may be a state substituted only by a polymerizable group P ^AP1 , or a state substituted by a group P ^AP1 -Sp ^AP1 - ^{containing a spacer 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, still more preferably 2 or more and 4 or less, particularly preferably 2 or 3. The best is 2.

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

P ^AP1 －Sp ^AP1 － can be bonded with polymerizable group, mesogen group or polar group. Among them, P ^{AP1 -Sp AP1} -is preferably bonded to a mesogen group or a polar group.

When there are a plurality of P ^AP1 and/or Sp ^AP1 in the molecule, they may be the same or different.

[Polar group] The polar group of the polymerizable compound B is a group that interacts with the substrate or with impurities contained in the liquid crystal layer or the alignment film, and can act as either a donor or acceptor of protons that sandwich the hydrogen bond The role of the, or can also play the role of both. It is preferably a group containing a "polar element having an atomic group formed by bonding a carbon atom and a heteroatom". In this specification, the polar element refers to a group of atoms formed by direct bonding between carbon atoms and heteroatoms. The heteroatom 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, 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, or trivalent, and may be trivalent or more. In addition, 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 has 1 to 4 polar groups, and still more preferably has 1 to 3 polar groups.

Furthermore, the polymerizable group is not included in the polar group, and the polar group includes ^{the structure in which the hydrogen atom in the polar group is replaced by P AP1} -Sp ^AP1 -and the structure in which the hydrogen atom in the ^{P AP1} -Sp ^{AP1-is replaced by -OH} . P ^AP1 and Sp AP1 are as described in the above paragraphs of "Polymerizing ^{Group" respectively.}

The polar group contains 1 or more polar elements, and is roughly classified into a cyclic base type and a chain base type. The cyclic base type is a form including a cyclic group having a cyclic structure, and the cyclic structure includes a polar element in its structure. The chain base type does not include a "cyclic group with a cyclic structure containing a polar element in its structure", but is a form in which a linear or branched chain base has a polar element, and it may have a part of it Ring structure without polar elements.

The polar group of the cyclic group type means a form having a structure containing at least one polar element in the atomic arrangement of the ring. Furthermore, in this specification, the cyclic group is as described above. Therefore, the cyclic group type polar group only needs to contain a "polar element-containing cyclic group", and the entire polar group may be a branched chain or a straight chain.

On the other hand, the chain-based polar group means a form having the following structure in the molecule: it does not contain a cyclic atomic arrangement containing a polar element, and at least one is included in the linear atomic arrangement (branchable) Polar element.

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

Therefore, the chain-based polar group includes, for example, an alkyl group, an alkenyl group, an alkoxy group, an ester group, an ether group, or a keto group. 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.) )replace. In addition, the chain-based polar group may be either a straight chain or a branched chain.

As the cyclic group type polar group, a heteroaromatic group having 3 to 20 carbon atoms (including a condensed ring) or a heteroalicyclic group having 3 to 20 carbon atoms (including a condensed ring) is preferred, and more preferred is Heteroaromatic group with 3-12 carbon atoms (including condensed ring) or heteroalicyclic group with 3-12 carbon atoms (including condensed ring), more preferably 5-membered heteroaromatic group, 5-membered Ring heteroalicyclic group, 6-membered ring heteroaromatic group or 6-membered ring heteroalicyclic group. Furthermore, the hydrogen atoms in these ring structures may be substituted by halogeno groups, linear or branched alkyl groups or alkoxy groups having 1 to 5 carbon atoms. As the halogeno group, a fluoro group or a chloro group is preferable, and a fluoro group is more preferable.

The chain type polar group is preferably a linear or branched alkyl group having 1 to 20 carbon atoms in _{which the hydrogen atom or -CH 2-in the structure is substituted with a polar element.} Furthermore, one or two or more non-adjacent ones in the alkyl group -CH ₂ -can be -CH=CH-, -C≡C-, -O-, -CO-, so that oxygen atoms are not directly adjacent to each other. -COO-, -OCO- or -OCO-COO- replaced. In addition, the chain-based polar group preferably contains one or two or more polar elements at its end.

One or two or more hydrogen atoms in the polar group may be substituted by a polymerizable group. Regarding the polymerizable group, it is as described in the paragraph of the above-mentioned "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), and polar elements containing phosphorus atoms (hereinafter referred to as Are phosphorus-containing polar elements), boron-containing polar elements (hereinafter referred to as boron-containing polar elements), silicon-containing polar elements (hereinafter referred to as silicon-containing polar elements), or sulfur atoms-containing polar elements (hereinafter referred to as Sulfur polar element). Among them, the polar element is preferably a sulfur-containing polar element, a nitrogen-containing polar element or an oxygen-containing polar element, and more preferably an oxygen-containing polar element. 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 1 selected from the group consisting of a hydroxyl group, an alkylol group, an alkoxy group, a methanoyl group, a carboxyl group, an ether group, a carbonyl group, a carbonate group, and an ester group. The species group or the group to which the carbon atom is bonded.

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

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

The polar group is preferably selected from 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), One or more types of chain groups containing oxygen-containing polar elements (hereinafter referred to as oxygen-containing chain groups) and chain groups with nitrogen-containing polar elements (hereinafter referred to as nitrogen-containing chain groups) The basic body or the foundation that contains the foundation.

As an oxygen-containing cyclic group, it is preferable to contain any one of the following groups which have an oxygen atom in the form of an ether group in a ring structure. The * in the following formula represents a bonding bond.

Moreover, as an oxygen-containing cyclic group, it is preferable to contain any one of the following groups which have an oxygen atom in the form of a carbonyl group, a carbonate group, and an ester group in a ring structure. The * in the following formula represents a bonding bond.

As a nitrogen-containing cyclic group, it is preferable to contain any one of the following groups. The * in the following formula represents a bonding bond.

As an oxygen-containing chain group, it is preferable to contain any one of the following groups.

(In the formula, R ^at1 represents an alkyl group with 1 to 5 carbon atoms. Z ^at1 represents a single bond, a straight or branched chain alkylene with 1 to 15 carbon atoms, or a straight chain with 2 to 18 carbon atoms Or a branched alkenylene group. Among them, one or more than _{two of the} alkylene group or the alkenylene group -CH 2-can be -O-, -COO-,-in such a way that the oxygen atom is not directly adjacent to each other. C(=O)-, -OCO- substituted. X ^at1 represents a hydrogen atom or an alkyl group with 1 to 15 carbon atoms. Among them, one or more of the alkyl group -CH ₂ -can be replaced by an oxygen atom The method of direct adjacent connection is replaced by -O-, -COO-, -C(=O)-, -OCO-. In the formula, * means bonding bond).

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

(In the formula, R ^at , R ^bt , R ^ct and R ^dt are independent of each other and represent a hydrogen atom or an alkyl group with 1 to 5 carbon atoms. The * in the formula represents a bonding bond).

The polar group is preferably bonded to the mesogen group via a spacer. In this case, it is preferable that one or two or more hydrogen atoms in the spacer are substituted with a polymerizable group.

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

(In the formula, Sp ^AT1 represents a single bond or a linear or branched alkylene group with 1 to 25 carbon atoms. One or more hydrogen atoms in the alkylene group can be replaced by -OH, -CN, -W ^AT1 -Z ^AT1 or P ^AP1 -Sp ^AP1 - substituted, or a contiguous extension of the two or more of the alkyl -CH ₂ - can be oxygen atoms are not directly bonded to the embodiment is a cyclic group, - CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- substituted, 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 straight or branched chain alkylene group with 1 to 25 carbon atoms. One or more hydrogen atoms in the alkylene group can be -OH, -CN, or P ^AP1 -Sp ^AP1 - substituted, or adjacent to one or more of the alkylene group in the 2 -CH ₂ - can not directly adjacent oxygen atoms of the group cyclic manner, -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- are substituted. The * in the formula represents a bonding bond). Z ^AT1 represents a monovalent polar group containing polar elements. One ^{or more hydrogen atoms in Z AT1} can be replaced by -OH, -CN or P ^AP1 -Sp ^AP1 -. P ^AP1 represents a polymerizable group, Sp ^AP1 represents a spacer group, and * in the formula represents a bonding bond).

Sp ^WAT1 and Sp ^WAT2 are independent, and preferably represent a single bond or a linear or branched alkylene group with 1-20 carbon atoms, more preferably a single bond or a linear alkylene group with 1-20 carbon atoms, More preferably, it represents a single bond or a linear alkylene group having 2 to 10 carbon atoms.

Sp ^AT1 represents the spacer base. The spacer Sp ^AT1 represents a single bond or a linear or branched alkylene having 1 to 25 carbon atoms, among which, it preferably represents a single bond or a linear or branched alkylene having 1 to 20 carbon atoms. More preferably, it represents a single bond or a straight-chain alkylene having 1 to 20 carbon atoms, and still more preferably represents a single bond or a straight-chain alkylene having 2 to 10 carbon atoms.

In addition, in Sp ^AT1 , Sp ^WAT1, and Sp ^WAT2 , one or more than two non-adjacent alkylene groups -CH ₂ -are independent of each other, and can be -CH=CH- in a way that oxygen atoms are not directly bonded. , -C≡C-, -O-, -CO-, -COO- or -OCO- replaced.

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 having 1 to 25 carbon atoms in which at least one hydrogen atom is replaced by P ^AP1 -Sp ^{AP1 -.} Polar group Z ^AT1 Sp ^AT1 and has the substituent group P ^AP1 -Sp ^AP1 - in the polymerizable group P ^AP1 may be located near each other. By having such a structure, the polymerizable compound B can enhance the interaction of the polymer of the polymerizable compound B formed at the interface of the liquid crystal layer and the substrate with the substrate in the liquid crystal display element without the alignment film, and can improve the polymerization. The vertical alignment control power of the liquid crystal molecules caused by the polymer of the sex compound B. In addition, in a liquid crystal display element having an alignment film, it is easy to incorporate impurities adsorbed and trapped by the polar group into the polymer, and it is possible to prevent the impurities from leaking and diffusing into the liquid crystal layer, resulting in a decrease in the physical properties of the liquid crystal layer.

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 linear or branched alkylene group with 1 to 25 carbon atoms. One or more hydrogen atoms in the alkylene group can be replaced by -OH, -CN, ^-Z ZAT11 -R ZAT11 or P ^AP1 -Sp ^AP1 - substituted, or adjacent to one or more of the alkylene group in the 2 -CH ₂ - can be in the oxygen atoms are not directly adjacent manner cyclic group, -O -, -COO-, -C(=O)-, -OCO- or -CH=CH- substitution. Sp ^ZAT12 represents a single bond or a straight or branched chain alkylene group with 1 to 25 carbon atoms. One or more hydrogen atoms in the alkyl group can be substituted by -OH, -CN or P ^AP1 -Sp ^AP1 -, one or more than _two unadjacent ones in the alkylene group -CH 2-can be oxygen Atoms that are not directly adjacent to each other are substituted by cyclic groups, -O-, -COO-, -C(=O)-, -OCO-, -CH=CH- or -Z ^ZAT11 -. Z ^ZAT11 means that it contains polar elements . ring containing polar group represented by ^Z ZAT12 of the structure represents a 5- to 7-membered ring and ^Z ZAT12 ^Z ZAT11 in one of two or more of the hydrogen atoms may be -OH, -CN, or P ^AP1 -Sp ^AP1 -. substituted R ^ZAT11 and R ^ZAT12 are independent of each other and represent a hydrogen atom, a linear or branched alkyl group with 1 to 8 carbon atoms, and one or more hydrogen atoms in the alkyl group can be replaced by -OH, -CN Or P ^AP1 －Sp ^AP1 － substituted, one of the alkyl groups or two or more _{unadjacent －CH 2} － can be cyclic group, －O－, －COO－， -C(=O)-, -OCO-, -CH=CH- or -Z ^ZAT11 -substitution. P ^AP1 represents a polymerizable group, Sp ^AP1 represents a spacer group, and * in the formula represents a bonding bond).

The group represented by the general formula (ZAT1-1) is preferably the 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, respectively, and the hydrogen atom bonded to the carbon atom can be replaced by -OH, -CN or P ^AP1 -Sp ^AP1 -. In the formula, * represents a bonding bond) .

Moreover, as a group represented by general formula (ZAT1-1), the following groups are mentioned preferably.

(In the formula, R ^tc represents a hydrogen atom, a straight or branched chain alkyl group with 1 to 20 carbon atoms, or P ^AP1 -Sp ^AP1 -. One or more hydrogen atoms in the alkyl group may be -OH, -CN, or P ^AP1 -Sp ^AP1 - substituted, or adjacent to one or more of the alkyl group of 2 -CH ₂ - adjacent to the embodiment can not directly to the oxygen atom is a cyclic group, -O-, -COO-, -C(=O)-, -OCO-, -CH=CH- or -Z ^ZAT11 -substitution. The hydrogen atom in the molecule can be replaced by P ^AP1 -Sp ^AP1 -. In the formula, * means bonding key).

The group represented by the general formula (ZAT1-2) is preferably the 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 carbon atoms can be substituted by halogen atoms, -OH, -CN or P ^AP1 -Sp ^AP1 -. In the formula * Indicates a bonding key).

[Mesogen] The polymerizable compound B preferably has a mesogen group. The mesogen group means a group having a rigid part, for example, a group having one or more cyclic groups. Here, "cyclic group" means a group of atoms in which the constituent atoms are bonded to form a ring, including carbocyclic, heterocyclic, saturated or unsaturated cyclic structures, monocyclic, bicyclic structures, polycyclic structures, and aromatics. , Non-aromatic, etc.

The mesogen preferably has a skeleton similar to that of liquid crystal molecules (liquid crystal compounds).

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

When the cyclic group is a single ring, the mesogen group preferably contains two or more single rings.

The cyclic group may contain at least one heteroatom. In addition, the cyclic group may be substituted with at least one substituent. Examples of the above-mentioned substituent include a halogenated group, a polymerizable group, an organic group such as an alkyl group, an alkoxy group, and an aryl group.

The mesogen 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).

(In the formula, 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 with 1 to 20 carbon atoms, one of the alkylene groups One or more than two non-adjacent -CH ₂ -can be cyclic group in a way that oxygen atoms are not directly bonded, -CH=CH-, -C≡C-, -O-, -CO-, -COO- Or -OCO- substitution. A ^AL1 and A ^AL2 are independent of each other and represent a divalent cyclic group. ^{One or more hydrogen atoms of Z AL1} , A ^AL1 and A ^AL2 are independent of each other and may be halogenated, Polar group, -Sp ^AT1 -W ^AT1 -Z ^AT1 , P ^AP1 -Sp ^AP1 -or monovalent organic group substitution. Sp ^AP1 , Sp ^AT1 , P ^AP1 , W ^AT1 and Z ^AT1 each have the same meaning as above. ^AL1 represents an integer from 1 to 5. When m ^AL1 represents an integer from 2 to 5, a plurality of Z ^AL1 may be the same or different, and a plurality of A ^AL1 may be the same or different. The * in the formula respectively represents a bonding bond).

In the general formula (AL), Z ^{AL1 is} preferably a single bond or an alkylene having 2 to 20 carbon atoms, more preferably a single bond or an alkylene having 2 to 10 carbon atoms, and still more preferably a single bond, -(CH ₂ ) ₂ -or-(CH ₂ ) ₄ -. One or two or more of -CH ₂ -in the alkylene can be substituted by -O-, -COO- or -OCO- in such a way that oxygen atoms are not directly adjacent to each other.

When improving the linearity of the polymerizable compound B, Z ^{AL1 is} preferably a single bond, or an even number of atoms directly bonding the ring to the ring and an alkylene group having 2 to 20 carbon atoms. One or two or more non-adjacent -CH ₂ -in the alkylene can be substituted by -O-, -COO- or -OCO- in such a way that oxygen atoms are not directly adjacent to each other. Regarding the number of atoms directly bonding the ring to the ring, for example, in the case of -CH ₂ -CH ₂ COO-, it is 4.

烷－2,5－二基、四氫噻喃－2,5－二基、噻吩－2,5－二基、1,4－雙環（2,2,2）伸辛基、十氫萘－2,6－二基、吡啶－2,5－二基、嘧啶－2,5－二基、吡𠯤－2,5－二基、噻吩－2,5－二基－、1,2,3,4－四氫萘－2,6－二基、2,6－伸萘基、菲－2,7－二基、9,10－二氫菲－2,7－二基、1,2,3,4,4a,9,10a－八氫菲－2,7－二基、1,4－伸萘基、苯并[1,2－b:4,5－b‘]二噻吩－2,6－二基、苯并[1,2－b:4,5－b‘]二硒吩－2,6－二基、[1]苯并噻吩并[3,2－b]噻吩－2,7－二基（[1]benzothieno[3,2－b]thiophene－2,7－diyl）、[1]苯并硒吩并[3,2－b]硒吩－2,7－二基及茀－2,7－二基所組成之群中之1種。當中，更佳為A^AL1 及A^AL2 分別獨立地為1,4－伸苯基、1,4－伸環己基、2,6－伸萘基或菲－2,7－二基，再更佳為1,4－伸苯基或1,4－伸環己基。In the general formula (AL), A ^AL1 and A ^AL2 are independent of each other and represent a divalent cyclic group. The divalent cyclic group is preferably selected from 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, and tetrahydropiperan-2,5-diyl , 1, 3-two

Alkyl-2,5-diyl, tetrahydrothiopyran-2,5-diyl, thiophen-2,5-diyl, 1,4-bicyclo(2,2,2)octyl, decalin- 2,6-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrimidine-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-2,7-diyl, 1,4-naphthylene, benzo[1,2-b:4,5-b']dithiophene-2, 6-diyl, benzo[1,2-b:4,5-b']diselenophen-2,6-diyl, [1]benzothieno[3,2-b]thiophen-2, 7-diyl ([1]benzothieno[3,2-b]thiophene-2,7-diyl), [1]benzoseleno[3,2-b]selenophene-2,7-diyl and One of the group consisting of 茀-2,7-two bases. Among them, it is more preferable that A ^AL1 and A ^AL2 are independently 1,4-phenylene, 1,4-cyclohexylene, 2,6-naphthylene, or phenanthrene-2,7-diyl, and even more preferably It is 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 with 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 with a fluorine atom or a hydroxyl group. Examples of the halogenated group include a fluoro group, a chloro group, and the like, and a fluoro group is preferred.

Here, in the general formula (AL), a monovalent organic group is a group that constitutes a chemical structure of an organic compound by becoming a monovalent group, and means an atomic group obtained 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 alkylene group having 2 to 15 carbon atoms. Base and so on. _{One or more of -CH 2} -of the alkyl group, the alkenyl group, the alkoxy group, and the alkenyloxy group may be -O-, -COO- or -COO- so that the oxygen atom is not directly adjacent to each other. -OCO-Replace.

Among them, the above-mentioned monovalent organic group is preferably an alkyl group with 1 to 15 carbon atoms or an alkoxy group with 1 to 14 carbon atoms, and more preferably an alkyl group with 1 to 8 carbon atoms or 1 to 8 carbon atoms The alkoxy group is more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and particularly preferably an alkyl group having 1 to 3 carbon atoms or an alkyl group having 1 to 2 carbon atoms The alkoxy group is preferably an alkyl group with 1 or 2 carbon atoms or an alkoxy group with 1 carbon atom. _{One or more of -CH 2} -of the alkyl group, the alkenyl group, the alkoxy group, and the alkenyloxy group may be -O-, -COO- or -COO- so that the oxygen atom is not directly adjacent to each other. -OCO-Replace.

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 still more preferably 2 or 3.

As a preferable aspect of the mesogen group, the structures represented by the following formulas (me-1) to (me-44) can be cited.

(In formulas (me-1) to (me-44), the rings at both ends have a bonding bond at a position where any one of the hydrogen atoms bonded to the carbon atoms of the ring is separated).

In the above formulas (me-1)～(me-44), one or more hydrogen atoms in the cyclohexane ring, benzene ring or naphthalene ring are independent and can be halogenated, P ^AP1 －Sp ^AP1 -, monovalent organic group (for example, C1-C15 alkyl group, C1-C14 alkoxy group) or polar group substitution.

The better morphology of the above mesogen is the structure represented by the formulas (me-8)～(me-44), and the better morphology is the formulas (me-8)～(me-10), (me-12)～ (Me-18), formulas (me-22)～(me-24), formulas (me-26)～(me-27) and formulas (me-29)～(me-44), and The better morphology system is (me-12), (me-14), (me-16), (me-22)～(me-24), (me-29), (me-34), (me－ 36) ~ (me-37), and (me-42) ~ (me-44) represents the structure.

The most preferable form of the above mesogen is the structure represented by the following general formula (AL-1) or (AL-2), and the best form is the structure represented by the following general formula (AL-1).

(In the formula, X ^AL101 to X ^AL118 and X ^AL201 to X ^AL214 are each independent, and represent a hydrogen atom, an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 5 carbon atoms, a halogenated group, and P ^APl － Sp ^APl -or polar group. Among them, one of X ^AL101 , X ^AL102 , X ^AL103 , X ^AL117 and X ^AL118 represents a bonding bond, and one of X ^AL108 , X ^AL109 , X ^AL110 , X ^AL111 and X ^AL112 Represents a bonding key, one of X ^AL201 , X ^AL202 , X ^AL203 , X ^AL212, and X ^AL213 represents a bonding key, and one of X ^AL206 , X ^AL207 , X ^AL208 , X ^AL209, and X ^AL210 represents a bonding key Also, ^{any one or more of X AL101} to X ^AL118 and X ^AL201 to X ^AL214 are substituted with polar groups. Polar groups may be substituted with P ^AP1 -Sp ^AP1 -. Ring A ^AL11 , Ring A ^AL12 and Ring A ^AL21 each independently, represent a cyclohexane ring or a benzene ring, in general formula (AL-1) or the general formula (AL-2) having in its molecule one or two or more P ^AP1 -Sp ^APl -.).

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

In the general formula (AL-1), it is preferable that ^{at least one of X AL109} , X ^AL110 and X ^{AL111 is P AP1} -Sp ^AP1 -among the polar groups, or a polar group with polymerizable parts in the structure, More preferably, both or one ^{of X AL109} and X ^{AL111 is P AP1} -Sp ^AP1 -.

In the general formula (AL-1), ^{one or two of X AL104} to X ^AL108 and X ^AL112 to X ^AL116 are independently, preferably alkyl groups with 1 to 5 carbon atoms, and 1 to 5 carbon atoms The alkoxy group or halo group is more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom. ^{Particularly preferably} , X AL105, X ^AL106 or X ^AL107 are each independent, and each is an alkyl group with 1 to 3 carbon atoms or a fluorine atom.

In the general formula (AL-2), preferably ^{at least one of X AL207} , X ^AL208 and X ^AL209 is a polar group, more preferably X ^AL207 and X ^AL208 are both polar groups, or X ^AL208 is a polar group, and then More preferably, X ^AL208 is a polar group.

In the general formula (AL-2), it is preferable that ^{at least one of X AL207} , X ^AL208 and X ^{AL209 is P AP1} -Sp ^AP1 -among the polar groups, or a polar group with polymerizable parts in the structure, More preferably, both or one ^{of X AL207} and X ^{AL209 is P AP1} -Sp ^AP1 -.

In the general formula (AL-2), ^{one or two of X AL202} to X ^AL206 and X ^AL210 to X ^AL214 are independently, preferably alkyl groups with 1 to 5 carbon atoms, and 1 to 5 carbon atoms The alkoxy group or halo group is more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom. ^{Particularly preferably} , X AL204, X ^AL205 or X ^AL206 are independent of each other, and each is an alkyl group with 1 to 3 carbon atoms or a fluorine atom.

[Specific state of polymerizable compound B] The polymerizable compound B preferably has one or more polar groups, one or more polymerizable groups, and a mesogen group. The polymerizable group replaces the mesogen or the polar group directly or via a spacer, and is particularly preferably the above The polymerizable group replaces the mesogen group in the state of being incorporated into the polar group.

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. In addition, one or two or more hydrogen atoms in the polar group may be substituted with a polymerizable group via a spacer.

The polymerizable compound B is preferably a form in which a polar element contained in a polar group or a polar element contained in a polymerizable group is locally present. By adjoining the polar group and the polymerizable group, the interaction with the substrate or impurities can be improved, and the liquid crystal composition can exhibit good solubility. Specifically, the polymerizable compound B is preferably in a form having a polymerizable group and a polar group on the same ring. In this form, it includes: a form in which more than one polymerizable group and one or more polar groups are respectively bonded to the same ring; and at least one of more than one polymerizable group, or more than one polar group Among at least one of them, one is bonded to the other and has a form of 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 with 1 to 20 carbon atoms. One of the alkyl groups or two or more unadjacent ones-CH ₂ -can be directly bonded with oxygen atoms The way is replaced by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, and one or more hydrogen atoms in the alkyl group are independent, which can be substituted with a halogen atom. a ^AL1 a ^AL2 and each independently represents general formula (AL) in the a and a ^{AL2 AL1} same meaning. ^AL1 Z represents the general formula (AL) ^AL1 in the same meaning as Z. m ^AL1 as in the formula (AL) of the same meaning as m ^AL1. Sp ^AT1 are represented by the general formula Sp ^AT1 (AT) the same meaning. W ^AT1 formula W ^AT1 represents the same meanings as in the (AT). Z ^AT1 represents the same meaning as ^{Z AT1} in the general formula (AT) ^{. P AP1} represents a polymerizable group. Sp ^AP1 represents a spacer group. In the formula, there are plural R ^AK1 , A ^AL1 , A ^AL2 , Z ^AL1 , Z ^AT1 , Sp ^AT1 , W ^AT1 , P ^AP1 , Sp ^AP1 , they can be the same or different respectively)

R ^AK1 preferably represents a linear or branched alkyl group with 1 to 20 carbon atoms, more preferably represents a linear alkyl group with 1 to 20 carbon atoms, still more preferably a linear alkyl group with 1 to 8 carbon atoms base. One of the alkyl groups or two or more non-adjacent -CH ₂ -s can be independently -CH=CH-, -C≡C-, -O-,-in such a way that oxygen atoms are not directly adjacent to each other. Replace with CO-, -COO- or -OCO-. In addition, one or two or more hydrogen atoms in the alkyl group are each independent and may be substituted by halogen atoms. As the halogen atom, a fluorine atom or a chlorine atom is preferable, and a fluorine atom is more preferable.

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 the compound represented by the following formulas (SAL-1.1) to (SAL-2.10).

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

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 express the effect of adding the polymerizable compound B. On the other hand, if the above content is too large, problems such as an increase in the amount remaining after curing, a time-consuming curing, and a decrease in the reliability of the liquid crystal will occur. Therefore, it is preferable to set the content by combining the above upper limit value and the lower limit value while considering the balance of these.

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

[2－3] Other details about polymerizable compounds The polymerizable compound-containing liquid crystal composition 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 Compound 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 the polymerizable compound A and the polymerizable compound B, compared with the case where each polymerizable compound is contained separately, the effect of suppressing the decrease in VHR caused by UV irradiation is higher, and a higher level can be achieved. Tilt stability.

In addition, the polymerizable compound-containing liquid crystal composition of the present invention may contain polymerizable compounds other than the above-mentioned polymerizable compounds A and B.

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

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

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

(In the formula, R ^L1 and R ^L2 are independent of each other and represent an alkyl group with 1 to 8 carbon atoms. One or two or more of the alkyl groups that are not adjacent to each other -CH ₂ -may be independently controlled by -CH= CH－, －C≡C－, －O－, －CO－, －COO－ or －OCO－ replace, n ^L1 means 0, 1, 2 or 3, and A ^L1 , A ^L2 and A ^L3 are independent respectively, which means selection Free radicals in the group consisting of bases (a), bases (b) and bases (c), (a) 1,4-cyclohexylene (1 -CH ₂ -existing in the base or not adjacent 2 or more -CH ₂ -can be substituted by -O-), (b) 1,4-phenylene (1 -CH= or 2 or more non-adjacent ones -CH= can be -N = substitution), and (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (exist One in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl -CH= or two or more not adjacent -CH= can be -N= Substitution) The above groups (a), group (b) and group (c) are each independently, and may be substituted by a cyano group, a fluorine atom or a chlorine atom. Z ^L1 and Z ^L2 are each independent and represent 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-, when n ^L1 is 2 or 3 and there are multiple A ^L2s , they can be the same or different, and n ^L1 is 2 or 3 When there are a plurality of Z ^L2s , they may be the same or different. However, the compound represented by the general formula (i) is not included).

The compound represented by the general formula (L) corresponds to a compound that is almost neutral in terms of dielectric (Δε value is -2 to 2). Therefore, it is preferable to set the number of polar groups such as halogen contained in the molecule to two or less, more preferably to one or less, and it is preferable not to have the above-mentioned polar group. In addition, the number of halogen atoms present in the molecule is preferably 0, 1, 2, or 3, preferably 0 or 1, and preferably 1 when compatibility with other liquid crystal molecules is important.

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

Regarding the content of the compound represented by the general formula (L), it can be determined by solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, drip marks, afterimages, dielectric conductivity, etc. The required performance can be adjusted appropriately.

The preferable 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% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, and 50% by mass %, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, and 80% by mass. The upper limit of the preferred content is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, and 25% by 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 higher in the lower limit value and higher in the upper limit value. When the Tni of the liquid crystal composition of the present invention is kept high and a composition with excellent temperature stability is required, the content of the compound represented by the general formula (L) is preferably such that the lower limit value is high and the upper limit value is high. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, the content of the compound represented by the general formula (L) is preferably such that the lower limit value is low and the upper limit value is low.

In the above general formula (L), R ^L1 and R ^L2 are independent of each other and represent an alkyl group having 1 to 8 carbon atoms. One of the alkyl groups or two or more non-adjacent -CH ₂ -may be independently -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO -replace. Among them, R ^L1 and R ^L2 are independent of each other, and preferably represent 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.

If described in further detail, when reliability is important, it is preferable that both R ^L1 and R ^L2 are an alkyl group having 1 to 8 carbon atoms. Moreover, when emphasis is placed on reducing the volatility of the compound, it is preferable that both R ^L1 and R ^L2 are alkoxy groups having 1 to 8 carbon atoms. Moreover, when attaching importance to reducing viscosity, it is preferable ^{that at least one of R L1} and R ^L2 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), respectively, R ^L1 and R ^L2 preferably each represent a straight chain An 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. 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, piperan, and dioxane, respectively, R ^L1 and R ^{L2 are preferred} They are a linear alkyl group with 1 to 5 carbon atoms, a linear alkoxy group with 1 to 4 carbon atoms, and a linear alkenyl group with 2 to 5 carbon atoms. In order to stabilize the nematic phase, R ^L1 and R ^L2 preferably have a total of 5 or less carbon atoms and oxygen atoms, and are preferably linear.

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

In the above general formula (L), when Δn needs to be increased, A ^L1 , A ^L2 and A ^{L3 are} preferably aromatic, and in order to improve the response speed, they are preferably aliphatic. A ^L1 , A ^L2 and A ^L3 are independent of each other, and 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, 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-1 ,4-diyl, naphthalene-2,6-diyl, decalin-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, more preferably the following structure.

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

In the above general formula (L), when the response speed is important, Z ^L1 and Z ^{L2 are} preferably single bonds, respectively.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more compounds in which ^{at least one of R L1} and R ^L2 in the general formula (L) represents an alkenyl group having 2 to 8 carbon atoms ( The compound represented by the following general formula (L-a)).

(In formula (L-a), R ^L1a and R ^L2a are independent, respectively, and represent an alkyl group having 1 to 8 carbon atoms. One or two or more of the alkyl groups that are not adjacent to each other -CH ₂ -may be independent of each other Ground is substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, ^{and at least one of R L1a} and R ^L2a is an alkenyl group with 2-8 carbon atoms , A ^L1a , A ^L2a , A ^L3a , Z ^L1a , Z ^L2a, and n ^L1a respectively represent 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 accelerate the response speed in the liquid crystal display element. On the other hand, it is easy to be degraded by UV irradiation when polymerizing the polymerizable compound, and the voltage retention rate (VHR) of the liquid crystal display element is easy reduce. In contrast, the liquid crystal composition containing a polymerizable compound in the present invention contains a compound represented by the general formula (i) in addition to the polymerizable compound, so that the UV irradiation time required for the polymerization reaction of the polymerizable compound can be shortened. As a result, the effect of suppressing the deterioration of the compound represented by the general formula (L-a) and the reduction of the voltage holding ratio (VHR) can be improved.

Therefore, the polymerizable compound-containing liquid crystal composition of the present invention contains the compound represented by the general formula (i) and the polymerizable compound as well as the compound represented by the general formula (L-a), which can produce high-speed response Liquid crystal display element with higher compatibility and high VHR.

Regarding the compound represented by the general formula (La), either R ^L1 or R ^{L2 in} the general formula (La) may represent an alkenyl group, or both R ^L1 and R ^{L2 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 selected from the formula (R1) to the formula (R5), and is preferably a group represented by the formula (R1) or the formula (R2). (The black dots in each formula represent the carbon atoms in the ring structure)

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

(In the formula, 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 is} independent of each other and represents an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 8 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, or an alkenyloxy group with 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 independent, It is preferably 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 5 carbon atoms.

R ^NU11 , R ^NU21 , R ^NU31 , R ^NU41 and R ^{NU51 are} preferably compounds each independently containing one or more kinds of alkenyl groups having 2 to 8 carbon atoms. That is, the compound represented by general formula (L-a) is preferably R ^NU11 , R ^NU21 , R ^NU31 , R ^NU41 and R ^{NU51 in} general formula (NU-01) to general formula (NU-08) independently Ground is an alkenyl compound having 2 to 8 carbon atoms. The reason is that these compounds help increase the response speed. The alkenyl group preferably includes alkenyl groups represented by formula (R1) to formula (R5).

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

Among them, 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) .

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

(In the above formulas, R ^NU12a , R ^NU22a , R ^NU32a , R ^NU42a , and R NU52a are independent of each other and represent an alkyl group with 1 to 8 carbon atoms. One of the alkyl groups or two or more ^{unadjacent ones-} CH ₂ -, as long as the oxygen atoms are not adjacent, it can also be substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, one of the alkyl groups Or two or more hydrogen atoms may be substituted by halogen atoms, and n1 to n5 are independent of each other and represent an integer from 0 to 6).

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

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

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

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

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

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

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

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

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

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

Regarding the content of the compound represented by the general formula (NU-01), it is preferably 1-60% by mass in the total amount of the liquid crystal composition, more preferably 10-50% by mass, and still more preferably 20-40 quality%.

Regarding the content of the compound represented by the general formula (NU-02), it is preferably 0-40% by mass in the total amount of the liquid crystal composition, more preferably 5-25% by mass, and still more preferably 5-20 quality%.

Regarding the content of the compound represented by the general formula (NU-03), it is preferably 0-30% by mass in the total amount of the liquid crystal composition, more preferably 1-20% by mass, and still more preferably 3-15 quality%.

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

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

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

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

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

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

(In the formula, R ^N11 and R ^N12 are independent of each other and represent an alkyl group with 1 to 8 carbon atoms. One or two or more of the alkyl groups that are not adjacent to each other -CH ₂ -may be independently controlled by -CH= CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO- substituted, A ^N11 and A ^N12 are independent of each other, indicating that they are selected from the following groups (a), (b), and (C) and the group of the group (d), (a) 1,4-cyclohexylene (1 -CH ₂ -existing in the group or 2 or more non-adjacent -CH _2- Can be substituted by -O-), (b) 1,4-phenylene (1 -CH= or 2 or more non-adjacent -CH= can be substituted by -N= in the group), (c ) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (exist in naphthalene-2,6-diyl Or one of the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group -CH= or two or more unadjacent -CH= can be substituted by -N=), and (d)1, 4-cyclohexenylene group, the above-mentioned groups (a), group (b), group (c) and group (d) are independent of each other, and may be substituted by a cyano group, a fluorine atom or a chlorine atom. Z ^N11 and Z ^N12 are respectively Independent, indicating 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-, n ^N11 and n ^N12 are independent and represent an integer from 0 to 3, n ^N11 +n ^N12 is 1, 2, or 3, when there are a plurality of A ^N11 ～A ^N12 , Z ^N11 ～Z ^N12 , they may be the same or different. Among them, the compound represented by general formula (i) and general formula (L) is not included ).

The compound represented by the general formula (N-1) is equivalent to a compound that is negative in terms of dielectric (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 in which Δε is negative and its absolute value is greater than 3.

In the general formula (N-1), R ^N11 and R ^N12 are independent and represent an alkyl group with 1 to 8 carbon atoms. One of the alkyl groups or two or more non-adjacent ones-CH ₂ -may be separate Independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-. Among them, R ^N11 and R ^{N12 are} preferably each 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 alkenyl group having 2 to 8 carbon atoms. The alkenyloxy group of 8 is preferably an alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 5 carbon atoms, an alkenyl group with 2 to 5 carbon atoms or an alkenyloxy group with 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.

In addition, when ^{the ring structure to which R N11} and R ^N12 are bonded is a phenyl group (aromatic), it is preferably a linear alkyl group with 1 to 5 carbon atoms, and a linear chain with 1 carbon atom. ˜4 alkoxy and 4 to 5 alkenyl groups. When ^{the ring structure to which R N11} and R ^N12 are bonded is a saturated ring structure such as cyclohexane, piperan, and dioxane, they are preferably linear alkyl groups with 1 to 5 carbon atoms, straight Chain alkoxy with 1 to 4 carbon atoms and linear alkenyl with 2 to 5 carbon atoms. In order to stabilize the nematic phase, R ^N11 and R ^N12 preferably have a total of carbon atoms and oxygen atoms in the presence of 5 or less, and are preferably linear.

As the alkenyl group, a group represented by any one selected from the formula (R1) to the formula (R5) is preferred.

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

In the general formula (N-1), A ^N11 and A ^N12 are independent of each other and represent the group of the following groups (a), (b), (c), and (d), (a ) 1,4-cyclohexylene (1 -CH ₂ -or 2 or more unadjacent -CH ₂ -can be substituted by -O- in the group), (b) 1,4-phenylene (One -CH= or two or more non-adjacent -CH= may be substituted by -N= in the group), (c) naphthalene-2,6-diyl, 1,2,3,4- Tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (exist in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl One -CH= or two or more non-adjacent -CH= may be substituted by -N=) in the group, and (d) 1,4-cyclohexenylene.

The group (a), group (b), group (c), and group (d) are independent of each other, and may be substituted with a cyano group, a fluorine atom, or a chlorine atom.

A ^N11 and A ^N12 are independent of each other. When Δn needs to be increased, they are preferably aromatic, and in order to improve the response speed, they are preferably aliphatic. The above 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]octyl, piperidine-1,4-diyl, naphthalene-2,6-diyl, decalin-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, more preferably represents the following structure.

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

In the general formula (N-1), Z ^N11 and Z ^N12 are independent, respectively, representing 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-, among them, it is better to indicate -CH ₂ O-, -CF ₂ O-, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -or single bond, more preferably -CH ₂ O-, -CH ₂ CH ₂ -or single bond, especially preferred It is -CH ₂ O- or a single bond.

In the general formula (N-1), n ^N11 and n ^N12 are independent of each other and represent an integer of 0-3. In addition, n ^N11 + n ^N12 are independent of each other and are 1, 2, or 3. Among them, n ^N11 + n ^{N12 is} preferably 1 or 2. In this case, n ^N11 is preferably a combination of 1 and n ^N12 is 0, n ^N11 is 2 and n ^N12 is a combination of 0, n ^N11 is 1 and n ^N12 It is a combination of 1, n ^N11 is 2 and n ^N12 is a combination of 1.

The preferable lower limit values 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 are 1% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, and 80% by mass. The upper limit of the preferable content is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, and 20% by 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 preferable that the above-mentioned 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 excellent temperature stability is required, it is preferable that the above-mentioned lower limit value is low and the upper limit value is low. Moreover, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the above-mentioned lower limit value is high and the upper limit value is high.

Examples of the compound represented by the general formula (N-1) include those selected from the following general formulas (N-01), (N-02), (N-03), (N-04) and (N-05) A compound in the indicated compound group.

(In the formula, R ²¹ and R ²² are independent of each other and represent an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 8 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, and 2 to 8 carbon atoms. For the alkenyloxy group, Z ^{1 is} independent and represents a single bond, -CH ₂ CH ₂ -, -OCH ₂ -or -CH ₂ O-, and m is independent and represents 1 or 2)

R ^{21 is} preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and still more preferably an alkyl group having 2 to 4 carbon atoms. Among them, when Z ¹ represents other than a single bond, R ^{21 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, More preferably, it is an alkoxy group having 1 to 4 carbon atoms.

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

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

It is more ^{preferable that Z 1} is a single bond, -CH ₂ CH ₂ -or -CH ₂ O- independently of each other.

When m is 1, Z ^{1 is} preferably a single bond or -CH ₂ O-.

When M is 2, Z ^{1 is} preferably a single bond, -CH ₂ CH ₂ -or -CH ₂ O-.

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

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

The liquid crystal composition of the present invention preferably contains a compound represented by general formula (N-01-1) or a compound represented by 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 formula (N-02-1) to general formula (N-02-3) as general formula (N -02) The compound indicated.

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

The liquid crystal composition of the present invention preferably contains a compound represented by general formula (N-02-1) or a compound represented by 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 general formula (N-03-1).

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

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

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

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

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

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

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

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

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

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

When the polymerizable compound-containing liquid crystal composition of the present invention emphasizes the stability to UV irradiation, relative to the total mass of the above composition, it is preferable to set the content of the compound substituted by chlorine atoms to 15% by mass or less. It is preferably 10% by mass or less, more preferably 8% by mass or less, more preferably 5% by mass or less, more preferably 3% by mass or less, and still more preferably substantially free of compounds substituted with chlorine atoms.

The polymerizable compound-containing liquid crystal composition of the present invention preferably has a high content of compounds in which the ring structure in the molecule is six-membered ring. Relative to the total mass of the above composition, it is preferable that the ring structure in the molecule is uniform. The content of the six-membered ring compound is set to 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, and most preferably, only the ring structure in the molecule is substantially six-membered The compound of the ring constitutes the composition.

In order to suppress the degradation caused by the oxidation of the liquid crystal composition, the polymerizable compound-containing liquid crystal composition of the present invention preferably has a low content of the compound having a cyclohexenylene group as a ring structure, relative to the total mass of the above composition , It is preferable to set the content of the compound having a cyclohexenylene group to 10% by mass or less, more preferably to 8% by mass or less, more preferably to 5% by mass or less, and more preferably to 3% by mass or less, and It is more preferable that the compound having a cyclohexenylene group is not substantially contained.

When focusing on the improvement of viscosity and the improvement of Tni, the polymerizable compound-containing liquid crystal composition of the present invention preferably has 2-methylbenzene-1,4-two in which hydrogen atoms can be substituted with halogens in the molecule. The content of the compound of the "group" is small, and it is preferable to set the content of the compound having 2-methylbenzene-1,4-diyl group in the molecule to 10% by mass in the total amount of the liquid crystal composition of the present invention. Hereinafter, it is preferably 8% by mass or less, more preferably 5% by mass or less, more preferably 3% by mass or less, and still more preferably not substantially containing 2-methylbenzene-1,4-in the molecule. Two-base compound.

In addition, the term "substantially not containing" in this specification means not containing unless it is intended to be contained.

The polymerizable compound-containing liquid crystal composition of the present invention may contain normal nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, etc., in addition to the above-mentioned compounds.

[6] Additives The polymerizable compound-containing liquid crystal composition of the present invention may contain antioxidants, ultraviolet absorbers, light stabilizers, infrared absorbers, and the like. Among them, the polymerizable compound-containing liquid crystal composition of the present invention preferably contains an antioxidant and does not undergo polymerization during the heat treatment, which is one of the manufacturing steps of the liquid crystal display element.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains antioxidants represented by general formula (H-1) to general formula (H-4), and the lower limit of its content is preferably 10 mass ppm, preferably 20 The mass ppm is preferably 50 mass ppm, and the upper limit thereof is preferably 10,000 mass ppm, preferably 1,000 mass ppm, preferably 500 mass ppm, and more preferably 100 mass ppm.

In general formula (H-1) to general formula (H-3), R ^{H1 is} independent of each other and represents an alkyl group having 3 to 7 carbon atoms. ^{More specifically, R H1 in the} general formula (H-1) represents an alkyl group having 7 carbon atoms. ^{R H1 in the} general formula (H-2) represents an alkyl group with 3 carbon atoms. ^{R H1 in the} general formula (H-3) represents an alkyl group with 3 carbon atoms.

In the general formula (H-4), M ^H1 represents an alkylene group with 4 to 10 carbon atoms (one or more than _two in the alkylene group-CH 2-can also be blocked by oxygen atoms that are not directly adjacent to each other. -COO- or -OCO- substitution), single bond, 1,4-phenylene (any hydrogen atom in 1,4-phenylene can also be substituted by fluorine atom) or trans-1,4-phenylene Cyclohexyl, M ^H1 preferably represents an alkylene group having 4 to 8 carbon atoms.

[7] Other The polymerizable compound-containing liquid crystal composition of the present invention may also contain one or more compounds represented by the general formula (i), one or more polymerizable compounds A, 1 represented by the 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 general formulas (NU-01) to (NU The compound in the compound group represented by -08), the compound represented by the above general formula (i) may 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), and one or more polymerizable compounds represented by the general formula (P) Compound A, one or more than two kinds selected from general formula (N-01-1), (N-01-3), (N-01-4), (N-02-1), (N-03 -1) and (N-04-1) compounds in the group of compounds, and one or two or more selected from the general formula (NU-01), (NU-02), (NU-03) and (NU-05) A compound in the compound group indicated by (NU-05).

The polymerizable compound-containing liquid crystal composition of the present invention may also contain one or two or more compounds represented by the general formula (i), one or two or more polymerizable compounds B, and one or more selected from Compounds in 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) Among the compounds in the above combination, the compound represented by the above 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), and one or more polymerizable compounds represented by the general formula (SAL) Compound B, one or more than two types selected from general formula (N-01-1), (N-01-3), (N-01-4), (N-02-1), (N-03 -1) and (N-04-1) compounds in the group of compounds, and one or two or more selected from the general formula (NU-01), (NU-02), (NU-03) and (NU-05) A compound in the compound group indicated by (NU-05).

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

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), and one or more polymerizable compounds represented by the general formula (P) Compound A, one or more types of polymerizable compound B represented by general formula (SAL), one or more types selected from general formula (N-01-1), (N-01-3), ( N-01-4), (N-02-1), (N-03-1) and (N-04-1) the compounds in the group of compounds, and one or two or more selected from the group Compounds in the group of compounds represented by formulas (NU-01), (NU-02), (NU-03) and (NU-05).

The polymerizable compound-containing liquid crystal composition of the present invention is composed of only the compound represented by the general formula (i), a polymerization selected from the group consisting of the polymerizable compound A and the polymerizable compound B represented by the general formula (P) Compound, 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 components of the compound is preferably 100% by mass, 99% by mass, 98% by mass, 97% by mass, or 96% by mass in the total amount of the polymerizable compound-containing liquid crystal composition of the present invention. %, 95% by mass, 94% by mass, 93% by mass, 92% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, and 84% by mass.

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

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

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

For LCD TV applications, Tni is preferably 70 to 80°C, for mobile phones, Tni is preferably 80 to 90°C, and for outdoor display applications such as PID (Public Information Display), Tni is preferably 90 to 110°C .

The refractive index anisotropy (Δn) of the polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal composition of the present invention at 20° C. is 0.08 to 0.14, more preferably 0.09 to 0.13, and particularly preferably 0.09 to 0.12. In further detail, in the case of a thin cell gap, it is preferably 0.10 to 0.13, and in a case of a thick cell gap, it is preferably 0.08 to 0.10. 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 rotational viscosity (γ 1} ) of the polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal composition of the present invention at 20°C is 50 to 160 mPa･s, preferably 55 to 160 mPa･s, preferably 60 to 160mPa･s, preferably 80 to 150mPa･s, preferably 90 to 140mPa･s, preferably 90 to 130mPa･s, preferably 90 to 115mPa･s.

The Δε of the polymerizable compound-containing liquid crystal composition 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, more preferably -2.6 To -3.6.

B. Liquid crystal display element Next, the liquid crystal display element of the present invention will be described. The liquid crystal display element of the present invention is a liquid crystal display element using the polymerizable compound-containing liquid crystal composition described in the paragraph of "A. Polymerizable compound-containing liquid crystal composition". That is, the liquid crystal display element of the present invention uses "comprising one or more compounds represented by the general formula (i) and one or more polymerizable compounds, and the compound represented by the general formula (i) A liquid crystal display element of a polymerizable compound-containing liquid crystal composition whose total content 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 a polymerizable compound, and the residual amount of the polymerizable compound in the liquid crystal display element after polymerization is small, and 4K or 8K is high. The fine PSA mode liquid crystal display element will not produce display defects such as after-image (IS), or can significantly suppress display defects. In addition, in the production of high-definition PSA mode liquid crystal display elements such as 4K or 8K, if the UV irradiation time becomes longer, the deterioration of the liquid crystal composition may result in a decrease in VHR or a significant deterioration in production efficiency. Since the liquid crystal display element of the invention uses the above-mentioned polymerizable compound-containing liquid crystal composition, it becomes a liquid crystal display element of the PSA mode with a short UV irradiation time and high definition, and its industrial utility value is very high.

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

The liquid crystal display element of the present invention can be formed into a general structure, for example, can be formed to have "a first substrate and a second substrate arranged oppositely", "a common electrode provided on the first substrate or the second substrate", The structure of "a pixel electrode provided on the first substrate or the second substrate and having thin film transistors" and "a liquid crystal layer provided 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 the compound represented by general formula (i), the liquid crystal composition contained in the polymerizable compound-containing liquid crystal composition, and the polymer of the polymerizable compound.

The liquid crystal display element of the present invention may each have an alignment film 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.

The liquid crystal display element of the present invention may have an alignment film 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 alignment film is a member in contact with the liquid crystal layer, and has a function of aligning liquid crystal molecules contained in the liquid crystal layer. In this case, the polymerizable compound-containing liquid crystal composition 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. In the liquid crystal display element of the present invention, polymers of the polymerizable compound A and/or the polymerizable compound B are separately concentrated on the first substrate side interface and the second substrate side interface of the liquid crystal layer, and the polymerizable compound A can be used. The polymer and/or the polymer of the polymerizable compound B impart a pretilt angle to the liquid crystal molecules. In addition, when the polymer containing the polymerizable compound B, the impurities present in the liquid crystal layer or the alignment film will be adsorbed and trapped by the polar groups possessed by the polymerizable compound B and incorporated into the polymer of the polymerizable compound B Therefore, the liquid crystal display element of the present invention can suppress the decrease in VHR caused by the presence of impurities, and can have high reliability.

As the alignment film, a known alignment film such as a rubbing alignment film or a photo-alignment film can be used. In addition, the alignment film can 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 can be set to be the same as that of a well-known alignment film, and examples thereof include polyimide, polyamide, polysiloxane, and mixtures thereof. Among them, polyimide is preferred. The polyimine may be a photocrosslinkable polyimine or a decomposable polyimine. The thickness of the alignment film can be set to a thickness widely used in liquid crystal display devices.

In addition, 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 commonly referred to as PI-less. In this case, the polymerizable compound-containing liquid crystal composition used in the production of the liquid crystal display element of the present invention preferably contains at least the polymerizable compound B. The polymerizable compound B is formed as a polymer and is concentrated on the first substrate side interface and the second substrate side interface of the liquid crystal layer, respectively, and the polar group of the polymer of the polymerizable compound B interacts with the substrate surface, thereby, Even if the liquid crystal display element of the present invention does not have an alignment film, the liquid crystal molecules in the liquid crystal layer can be vertically aligned.

The first substrate and the second substrate (sometimes collectively referred to as a substrate) in the liquid crystal display element of the present invention may be flexible substrates or rigid substrates. In addition, the substrate may be transparent or opaque, and is preferably transparent. Examples of the material of the substrate include glass, resin, metal, silicon and the like.

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

The shape 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 preferable that one of the first substrate and the second substrate is provided with a common electrode formed on the entire surface of a transparent conductor and arranged in a matrix on the other substrate The gate electrode and the source electrode are provided with TFT elements and pixel electrodes in the part 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 a chemical vapor deposition (CVD) method, or a physical vapor deposition (PVD) method such as a sputtering method, an ion plating method, and a vacuum vapor deposition method.

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

In order to adjust the separation distance between the first substrate and the second substrate, that is, the thickness of the liquid crystal layer, the liquid crystal display element of the present invention may have a spacer between the first substrate and the second substrate. Examples of the spacer include glass particles, plastic particles, alumina particles, and photoresist materials.

The liquid crystal display element of the present invention may also have a polarizing plate. When a polarizing plate is provided, it is preferable to adjust the product of the refractive index anisotropy Δn of the liquid crystal composition and the cell thickness d to maximize the contrast. Moreover, when there are two polarizing plates, the polarization axis of each polarizing plate can also be adjusted to adjust the viewing angle or contrast to be good. Furthermore, a retardation film for expanding the viewing angle can also be used.

The liquid crystal display element of this invention can also fix a 1st board|substrate and a 2nd board|substrate with a sealing compound. Examples of the sealing agent include epoxy-based thermosetting compositions.

The liquid crystal display element of this invention can be manufactured by a well-known method. As a manufacturing method of the liquid crystal display element of this invention, the following examples can be mentioned. First, make the surface of the first substrate on the side where the alignment film is placed and the surface of the second substrate on the side where the alignment film is placed face each other, and bond them with spacers and sealing parts to make the desired cell gap. Empty cell. Next, using a vacuum injection method or an ODF method, etc., the polymerizable compound-containing liquid crystal composition of the present invention is sandwiched between the first substrate and the second substrate of the empty cell, and the sealing portion is cured to seal the liquid crystal composition in Between the first and second substrates. Next, UV light is irradiated to polymerize the polymerizable compound contained in the polymerizable compound-containing liquid crystal composition, 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.) when polymerizing the polymerizable compound can be appropriately set.

The present invention is not limited to the above-mentioned embodiment. The above-mentioned embodiments are exemplified, and those having substantially the same constitution as the technical idea described in the scope of the patent application of the present invention and exhibiting the same functions and effects are included in the technical scope of the present invention no matter what. [Example]

Examples are listed below to further describe the present invention in detail, but the present invention is not limited by these examples.

For the description of the compounds in the following Examples and Comparative Examples, the following codes are used.

(Side chain) －n －C _n H _2n+1 linear alkyl group with carbon number n n－ C _n H _2n+1 － linear alkyl group with carbon number n －On －OC _n H _{2n+ 1} straight-chain alkoxy group V- CH ₂ ＝CH－ 1V－ CH ₃ －CH＝CH－ －V －CH＝CH ₂ －V1 －CH＝CH－CH ₃ (bonding group) － 1O－ －CH ₂ －O－ －2－ －CH ₂ －CH ₂ －

(Ring structure)

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

T _ni : nematic phase-isotropic liquid phase transition temperature (°C) Δn: refractive index anisotropy _{at 20°C γ 1} : rotational viscosity at 20°C (mPa･s) Δε: medium at 20°C The manufacturing method and evaluation method of the liquid crystal display element in the following Examples and Comparative Examples are as follows.

(Method of manufacturing liquid crystal display element) First, a liquid crystal composition containing a polymerizable compound described later is injected into a "liquid crystal cell with a cell gap of 3.5 μm containing a substrate with ITO" by a vacuum injection method, and the above-mentioned substrate with ITO is coated Polyimide alignment film that induces vertical alignment and is rubbed. After that, the liquid crystal cell in which the liquid crystal composition containing the polymerizable compound is injected is irradiated with ultraviolet rays for an arbitrary period of time using a fluorescent UV lamp to obtain a liquid crystal display element. At this time, adjust the fluorescent UV lamp to: the illuminance measured under the condition of the center wavelength of 313nm is 3mW/cm ² .

(Method for evaluating the residual amount of polymerizable compound) Under the above-mentioned irradiation conditions, measure the liquid crystal display after 15 minutes, 30 minutes, 45 minutes, 60 minutes, 75 minutes, 90 minutes, and 115 minutes of irradiation with ultraviolet rays by the following method The residual amount of polymerizable compound in the device [ppm]. First, the decomposed liquid crystal display element and acetonitrile are added to the test tube, shaken and filtered to obtain an acetonitrile solution containing the eluted components of the liquid crystal composition, polymer, and unreacted polymerizable compound. Analyze it with a high performance liquid chromatograph (column: reverse phase non-polar tube; developing solvent: a mixed solvent of 70% by volume of acetonitrile and 30% by volume of water) to calculate the peak area of each component. The amount of the remaining polymerizable compound is determined based on 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 originally added. In addition, the detection limit of the residual amount of the polymerizable compound is 200 ppm. At this time, the UV irradiation time when the residual amount of the polymerizable compound does not reach the lower limit of detection is defined as T _ND [minutes].

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

(VHR evaluation method) The liquid crystal cell injected with the polymerizable compound-containing liquid crystal composition was irradiated with _{UV of T ND} [minutes] under the above irradiation conditions, and the VHR was determined under the conditions of 1V, 0.6Hz, and 60°C.

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

[Table 1]

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

Add 3 parts by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 97 parts by mass of the liquid crystal composition LC-001, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition" obtained from the polymerizable compound A represented by the formula (RM-A1) is referred to as Comparative Example 2.

Add 2 parts by mass of the compound represented by the formula (i-1-1-1A) as a compound of formula (i) to 98 parts by mass of the liquid crystal composition LC-001, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition" obtained from the polymerizable compound A represented by the formula (RM-A1) is referred to as Comparative Example 3.

Add 1.5 parts by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 98.5 parts by mass of the liquid crystal composition LC-001, and 0.3 parts by mass as a polymerizable compound "The polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is referred to as Example 1.

Add 1 part by mass of the compound represented by the formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-001, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is referred to as Example 2.

Add 0.5 parts by mass to 99.5 parts by mass of the liquid crystal composition LC-001 as a compound represented by formula (i) and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is referred to as Example 3.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 1 to 3 and Examples 1 to 3, the UV irradiation time T _ND [minutes] when the residual amount of the polymerizable compound did not reach the lower limit of detection, and the VHR after UV irradiation _{with T ND} [%] and the amount of pretilt angle change [°] when irradiated with UV for 200 seconds are shown in Table 2 below. The content (mass%) of the compound of formula (i) in the total amount of the polymerizable compound-containing liquid crystal composition is {parts by mass of the compound of formula (i)/(parts by mass of the liquid crystal composition + part of the compound of formula (i)) Parts by mass + parts by mass of polymerizable compound (A and B))}×100 calculated value. The following is the same.

[Table 2] Comparative example 1 Comparative example 2 Comparative example 3 Example 1 Example 2 Example 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 Polymeric 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 compound 100.3 100.3 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 60 30 30 30 30 45 VHR after UV irradiation with T _ND[%] 96 95 95 95 95 96 Pretilt angle change when irradiating UV for 200 seconds [°] 1.5 3.2 3.5 5.2 6.0 4.0

According to Table 2, _{the VHR [%] after UV irradiation with T ND are all high enough values, but the UV irradiation time T ND} [minutes] when the residual amount of polymerizable compound does not reach the lower limit of detection is compared with comparison Example 1, Comparative Examples 2 to 3, and Examples 1 to 2 have a relatively short time. Regarding the pretilt angle change [°] when irradiated with UV for 200 seconds, Comparative Examples 2 to 3 are larger than Comparative Example 1, but Examples 1 to 3 show larger values than Comparative Examples 1 to 3. Examples 1 to 3 can form a larger pretilt angle with a shorter UV irradiation time than that of Comparative Examples 1 to 3. In addition, for _{the liquid crystal display element after UV irradiation with T ND} , using OPTIPRO manufactured by Shintec Corporation, the display failure caused by the change of the pretilt angle before and after the change of the pretilt angle before and after 3 hours of applying a 30V voltage at a frequency of 100 Hz while irradiating the backlight for 3 hours Image) Evaluation", as a result, Examples 1 to 3 showed high tilt stability.

(Comparative Examples 4 to 5, Example 4, and Example 4-2) Let "a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of the polymerizable compound A represented by the formula (RM-A1) as a polymerizable compound to 100 parts by mass of the liquid crystal composition LC-002" For Comparative Example 4.

Add 3 parts by mass of the compound represented by the formula (i-1-1-1A) as a compound of formula (i) to 97 parts by mass of the liquid crystal composition LC-002, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition" obtained from the polymerizable compound A represented by the formula (RM-A1) is referred to as Comparative Example 5.

Add 1 part by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 part by mass as a polymerizable compound "The polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is set to Example 4.

Add 0.5 parts by mass to 99.5 parts by mass of the liquid crystal composition LC-002 as a compound represented by formula (i) and 0.3 parts by mass as a polymerizable compound "The polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is referred to as Example 4-2.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 4 to 5 and Examples 4 and 4-2, the residual amount of polymerizable compound did not reach the lower limit of detection for UV irradiation time T _ND [minutes], after _{UV irradiation with T ND} The VHR [%] and the pretilt angle change [°] when irradiated with UV for 200 seconds are shown in Table 3 below.

[table 3] Comparative example 4 Comparative example 5 Example 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 Polymeric compound A Formula (RM－A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compound 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 105 30 30 60 VHR after UV irradiation with T _ND[%] 76 93 93 85 Pretilt angle change when irradiating UV for 200 seconds [°] 0.2 1.3 2.2 1.9

_{According to Table 3, with regard to the UV irradiation time T ND} [minutes] when the residual amount of the polymerizable compound did not reach the lower limit of detection, compared with Comparative Example 4, Comparative Example 5 and Example 4 had a shorter time. Regarding the VHR [%] after UV irradiation with T _ND , compared with Comparative Example 4, Comparative Example 5 and Example 4 are sufficiently high values. In addition, regarding the pretilt angle change [°] when irradiated with UV for 200 seconds, Comparative Example 5 is greater than that of Comparative Example 4. However, Example 4 shows a larger value, and it can be seen that it can be shorter than that of Comparative Examples 4 to 5. UV irradiation time to form the pretilt angle. In addition, for _{the liquid crystal display element after UV irradiation with T ND} , using OPTIPRO manufactured by Shintec Corporation, the display failure caused by the change of the pretilt angle before and after the change of the pretilt angle before and after 3 hours of applying a 30V voltage at a frequency of 100 Hz while irradiating the backlight for 3 hours Image) Evaluation", as a result, Example 4 showed high tilt stability.

In addition, the T _{ND of} Example 4-2 was shorter than that of Comparative Example 4, the VHR was higher than that of Comparative Example 4, and the amount of change in the pretilt angle was 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 ratio of γ1 of the liquid crystal composition LC-002 is not included. The value of γ1 in the other liquid crystal composition of "3-Cy-Cy-V" is small. 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 Example 1 and Comparative Example 4, the T _{ND of the} liquid crystal composition LC-002 is longer than that of the liquid crystal composition LC-001 that does not contain "3-Cy-Cy-V". Furthermore, the liquid crystal composition LC The VHR of -002 after UV irradiation with T _{ND is} significantly lower than that of the liquid crystal composition LC-001. Therefore, the liquid crystal composition containing the alkenyl compound exhibits a _{long T ND} and a decrease in VHR due to UV irradiation.

It shows that by adding the compound of formula (i) to this liquid crystal composition LC-002, T _ND is shortened and the reduction of VHR can be suppressed. Furthermore, by setting the content of the compound of formula (i) in a specific range, even if it is short Time UV irradiation can also increase the pretilt angle change [°].

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

Add 1 part by mass of a compound represented by formula (i-1-1-37A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-001, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is referred to as Example 6.

Regarding the polymerizable compound-containing liquid crystal compositions of Examples 5 to 6, the UV irradiation time T _ND [minutes] when the residual amount of the polymerizable compound did not reach the lower limit of detection, the VHR [%] after UV irradiation _{with T ND, and the irradiation} The amount of pretilt angle change [°] in UV for 200 seconds is shown in Table 4 below.

[Table 4] Example 5 Example 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 Polymeric compound A Formula (RM－A1) 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compound 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 45 45 VHR after UV irradiation with T _ND[%] 94 95 Pretilt angle change when irradiating UV for 200 seconds [°] 3.6 4.0

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

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

Add 1 part by mass of a compound represented by formula (i-1-1-37A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 parts by mass as a polymerizable compound "The polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is set to Example 8.

Add 1 part by mass of a compound represented by formula (i-1-1-4B) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is set to Example 9.

Add 1 part by mass of a compound represented by formula (i-1-1-48A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 parts by mass as a polymerizable compound "The polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is set to Example 10.

Add 1 part by mass of the compound represented by formula (i-1-1-1B) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 part by mass as a polymerizable compound "The polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is set to Example 11.

Add 1 part by mass of the compound represented by the formula (i-1-1-2A) as a compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-002, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound A represented by the formula (RM-A1)" is set to Example 12.

Regarding the polymerizable compound-containing liquid crystal compositions of Examples 7 to 12, the UV irradiation time T _ND [minutes] when the residual amount of the polymerizable compound did not reach the lower limit of detection, the VHR [%] after UV irradiation _{with T ND, and the irradiation} The amount of pretilt angle change [°] in UV for 200 seconds is shown in Table 5 below.

[table 5] Example 7 Example 8 Example 9 Example 10 Example 11 Example 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－1-2A) 0 0 0 0 0 1 Polymeric 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 compound 100.3 100.3 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 60 60 60 60 30 60 VHR after UV irradiation with T _ND[%] 85 87 85 85 92 87 Pretilt angle change when irradiating UV for 200 seconds [°] 1.1 1.3 1.1 1.4 1.2 1.2

Regarding the polymerizable compound-containing liquid crystal compositions of Examples 7 to 12, compared with Comparative Example 4 in which the compound of formula (i) is not added to LC-002, T _{ND is} shorter, the value of VHR is higher, and the pretilt angle is higher. The amount of change is large. Among them, in Example 11 containing the compound of formula (i-1-1B), compared with other Examples 7-10 and 12, T _{ND was} smaller and the value of VHR after UV irradiation was higher. This is presumably because the compound of formula (i) does not have a substituent on the ring adjacent to the condensed ring, so that the UV irradiation time can be shortened, and the deterioration due to UV irradiation is suppressed.

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

"To 100 parts by mass of the liquid crystal composition LC-002 is added 0.3 parts by mass of the polymerizable compound (RM-A1) and 0.4 parts by mass of the polymerizable compound (RM-B1) as a polymerizable compound. The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound B" is referred to as Comparative Example 7.

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

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

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 6-7 and Examples 13-14, the UV irradiation time T _ND [minutes] when the residual amount of the polymerizable compound did not reach the lower limit of detection, and the VHR after UV irradiation _{with T ND} [%] and the pretilt angle change [°] when irradiated with UV for 200 seconds are shown in Table 6 below. The content (mass%) of the compound of formula (i) in the total amount of the polymerizable compound-containing liquid crystal composition is {parts by mass of the compound of formula (i)/(parts by mass of the liquid crystal composition + part of the compound of formula (i)) Parts by mass + parts by mass of polymerizable compound (A and B))}×100 calculated value.

[Table 6] Comparative example 6 Comparative example 7 Example 13 Example 14 Liquid crystal composition LC－002 100 100 99 99 Compound of formula (i) Formula (i－1－1－4A) 0 0 1 1 Polymeric compound A Formula (RM－A1) 0.7 0.3 0.7 0.3 Polymeric compound B Formula (RM－B1) 0 0.4 0 0.4 Total amount of liquid crystal composition containing polymerizable compound 100.7 100.7 100.7 100.7 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 105 105 60 60 VHR after UV irradiation with T _ND[%] 78 92 87 96 Pretilt angle change when irradiating UV for 200 seconds [°] 0.6 2.8 1.8 3.6

_{Regarding the UV irradiation time T ND} [minutes] in which the residual amount of the polymerizable compound did not reach the lower limit of detection, compared to Comparative Examples 6 to 7, Examples 13 to 14 had a shorter time. Regarding the VHR [%] after UV irradiation with T _ND , compared with Comparative Example 6, Example 13 was a sufficiently high value, and compared with Comparative Example 7, Example 14 was also a sufficiently high value. Regarding the pretilt angle change amount [°] when irradiated with UV for 200 seconds, the value of Example 13 is greater than that of Comparative Example 6, and the value of Example 14 is greater than that of Comparative Example 7.

Example 14 obtained by substituting 0.7 parts by mass of the compound of formula (RM-A1) in Example 13 with 0.4 parts by mass of the compound of formula (RM-B1) has a higher VHR than that of Example 13, and contains polymerization Example 14 of the compound A, the polymerizable compound B, and the compound of formula (i) is a sufficiently high value relative to Comparative Examples 6 to 7 and Example 13. From this result, it can be seen that by containing both the polymerizable compound A and the 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 general formula (i) is within a specific range, can quickly and fully polymerize, can form a larger angle of inclination with weaker or less UV light, and after UV irradiation The VHR also shows a higher value. In addition, it can be seen that the occurrence of display defects (after-images) caused by backlight exposure is also suppressed, showing high tilt stability.

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

Add 1 part by mass of the compound represented by the formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-001, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A3)" is referred to as Example 16.

Add 1 part by mass of the compound represented by the formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-001, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A4)" was set to Example 17.

Add 1 part by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-001, and 0.5 part by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A1)" is referred to as Example 18.

Add 1 part by mass of the compound represented by the formula (i-1-1-1A) as the compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-001, and 0.2 part by mass as the polymerizable compound The polymerizable compound represented by the formula (RM-A1) and 0.1 parts by mass of the polymerizable compound as the polymerizable compound represented by the formula (RM-A5) are obtained by the polymerizable compound-containing liquid crystal composition" as implemented Example 19.

The same evaluations as in Example 1 were also performed on the polymerizable compound-containing liquid crystal compositions of Examples 15-19. As a result, the polymerizable compound-containing liquid crystal compositions of Examples 15 to 19 are also the same as those of Example 1. It was confirmed that the problem of the present invention was solved, and it was taught that regardless of the type of polymerizable compound, the formula ( i) Compounds can exert the effects of the present invention.

(Examples 20-24) Add 1 part by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 part by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A2)" is referred to as Example 20.

Add 1 part by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 part by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A3)" was set to Example 21.

Add 1 part by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.3 part by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A4)" is referred to as Example 22.

Add 1 part by mass of the compound represented by formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of liquid crystal composition LC-002, and 0.5 part by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A1)" is referred to as Example 23.

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

The same evaluations as in Example 4 were also performed on the polymerizable compound-containing liquid crystal compositions of Examples 20-24. As a result, the polymerizable compound-containing liquid crystal compositions of Examples 20 to 24 are also the same as in Example 4. It was confirmed that the problem of the present invention was solved, and it was taught that regardless of the type of polymerizable compound, the formula ( i) The compound can exhibit the effects of the present invention even when it contains an alkenyl compound.

(Examples 25-27) Add 1 part by mass of the compound represented by the formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-003, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A1)" is referred to as Example 25.

Add 1 part by mass of the compound represented by the formula (i-1-1-1A) as the compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-004, and 0.3 parts by mass as the polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A3)" is referred to as Example 26.

Add 1 part by mass of the compound represented by the formula (i-1-1-1A) as a compound of formula (i) to 99 parts by mass of the liquid crystal composition LC-005, and 0.3 parts by mass as a polymerizable compound The "polymerizable compound-containing liquid crystal composition obtained from the polymerizable compound represented by the formula (RM-A4)" is referred to as Example 27.

The same evaluations as in Example 1 were also performed on the polymerizable compound-containing liquid crystal compositions of Examples 25-27. As a result, the polymerizable compound-containing liquid crystal compositions of Examples 25-27 are also the same as those of Example 1. It is confirmed that the problem of the present invention is solved, and the teaching is that regardless of the composition of the liquid crystal composition of the present invention and the type of polymerizable compound By containing a specific amount of the compound of formula (i), the effects of the present invention can be exerted.

(Examples 28 to 31) Let "the polymerizable compound-containing liquid crystal composition obtained in Example 2 further add 0.005 parts by mass of the antioxidant represented by the formula (H-2-1) to the polymerizable compound-containing liquid crystal composition" For Example 28.

The "polymerizable compound-containing liquid crystal composition obtained by further adding 0.005 parts by mass of the antioxidant represented by the formula (H-4-1) to the polymerizable compound-containing liquid crystal composition obtained in Example 2" is set For Example 29.

The "polymerizable compound-containing liquid crystal composition obtained by further adding 0.005 parts by mass of the antioxidant represented by the formula (H-2-1) to the polymerizable compound-containing liquid crystal composition obtained in Example 4" For Example 30.

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

The same evaluations as in Example 1 were also performed on the polymerizable compound-containing liquid crystal compositions of Examples 28-29. As a result, the polymerizable compound-containing liquid crystal compositions of Examples 28 to 29 are also the same as Example 1, and it was confirmed that the problem of the present invention was solved.

In addition, the same evaluations as in Example 4 were also performed on the polymerizable compound-containing liquid crystal compositions of Examples 30 to 31. As a result, the polymerizable compound-containing liquid crystal compositions of Examples 30 to 31 are also the same as Example 4, and it was confirmed that the problem of the present invention was solved.

(Examples 32-46) In the same manner as LC-001 to LC-005, the liquid crystal composition LC-006 to LC-010 before adding the compound of formula (i) and the polymerizable compound was prepared, and in the same manner as LC-001 to LC-005 Measure its physical properties. The structure of the liquid crystal compositions LC-006 to LC-010 and the results of their physical properties 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, a polymerizable compound-containing liquid crystal composition was prepared in the same manner as in Example 1, and Let it be Examples 32-46.

Then, the same evaluations as in Example 1 were performed for the polymerizable compound-containing liquid crystal compositions of Examples 32 to 46. The evaluation test results of Examples 32 to 46 are shown in Tables 8-12. Compare Examples 32 to 34 with Comparative Example 8, compare Examples 35 to 37 with Comparative Example 9, compare Examples 38 to 40 with Comparative Example 10, compare Examples 41 to 43 with Comparative Example 11, and implement Examples 44 to 46 were compared with Comparative Example 12. As a result, it was the same as Example 1, and it was confirmed that the problem of the present invention was solved.

[Table 8] Comparative example 8 Example 32 Example 33 Example 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 Polymeric compound A Formula (RM－A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compound 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 105 45 35 30 VHR after UV irradiation with T _ND[%] 76 80 90 93 Pretilt angle change when irradiating UV for 200 seconds [°] 0.2 0.7 1.2 1.4

[Table 9] Comparative example 9 Example 35 Example 36 Example 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 Polymeric compound A Formula (RM－A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compound 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 105 45 35 30 VHR after UV irradiation with T _ND[%] 77 79 89 94 Pretilt angle change when irradiating UV for 200 seconds [°] 0.2 0.6 1.2 1.5

[Table 10] Comparative example 10 Example 38 Example 39 Example 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 Polymeric compound A Formula (RM－A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compound 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 105 45 35 30 VHR after UV irradiation with T _ND[%] 76 82 90 93 Pretilt angle change when irradiating UV for 200 seconds [°] 0.3 0.7 1.1 1.4

[Table 11] Comparative example 11 Example 41 Example 42 Example 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 Polymeric compound A Formula (RM－A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compound 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 105 45 35 30 VHR after UV irradiation with T _ND[%] 75 80 91 94 Pretilt angle change when irradiating UV for 200 seconds [°] 0.2 0.7 1.2 1.4

[Table 12] Comparative example 12 Example 44 Example 45 Example 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 Polymeric compound A Formula (RM－A1) 0.3 0.3 0.3 0.3 Total amount of liquid crystal composition containing polymerizable compound 100.3 100.3 100.3 100.3 The 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 when} the residual amount of polymerizable compound does not reach the lower limit of detection [minutes] 105 45 35 30 VHR after UV irradiation with T _ND[%] 73 78 91 92 Pretilt angle change when irradiating UV for 200 seconds [°] 0.2 0.7 1.2 1.4

(Examples 47-76) "To the polymerizable compound-containing liquid crystal compositions used in Examples 32 to 46, respectively, 0.005 parts by mass of the antioxidant represented by the formula (H-2-1) was further added to prepare the polymerizable compound-containing compound "Liquid crystal composition" is referred to as Examples 47 to 61.

In addition, the polymerizable compound-containing liquid crystal composition used in Examples 32 to 46 was prepared by further adding 0.005 parts by mass of the antioxidant represented by the formula (H-4-1). "Liquid crystal composition of compound" is referred to as Examples 62 to 76.

Then, the same evaluations as in Example 1 were also performed on the polymerizable compound-containing liquid crystal compositions of Examples 47 to 76. As a result, the polymerizable compound-containing liquid crystal compositions of Examples 47 to 76 were also the same as those of Example 1, and it was confirmed that these were superior to the comparative examples. Thus, it was confirmed that the problem of the present invention was solved.

without

without

Claims (12)

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

(In the formula, R ⁱ¹ and R ⁱ² are independent of each other and represent an alkyl group with 1 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an alkenyl group with 2 to 10 carbon atoms or 2 to 10 carbon atoms For the alkenyloxy group, one or more hydrogen atoms in these groups may be substituted by fluorine atoms. Ring A and ring B are independently selected from the group (a), group (b), The group consisting of group (c) and group (d), (a) 1,4-cyclohexylene (1 -CH ₂ -existing in the group-or 2 or more non-adjacent -CH ₂ -May be substituted by -O-), (b) 1,4-phenylene (1 -CH= or 2 or more not adjacent to each other in the group -CH= may be substituted by -N=), ( c) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (exist in naphthalene-2,6-diyl) Group or one of 1,2,3,4-tetrahydronaphthalene-2,6-diyl group -CH= or two or more not adjacent -CH= can be substituted by -N=), and (d)1 ,4-Cyclohexenylene; The above group (a), group (b), group (c) and group (d) are independent of each other, and may be substituted by the following groups or atoms: carbon atoms that can be substituted by fluorine atoms An alkyl group of 1 to 8, an alkoxy group of 1 to 8 carbon atoms that may be substituted by a fluorine atom, a cyano group, or a fluorine atom, C represents a divalent condensed ring group having one or more benzene rings, the above condensation One or more hydrogen atoms of the cyclic group may be substituted by the following groups or atoms: an alkyl group with 1 to 8 carbon atoms which may be substituted by a fluorine atom, and a carbon atom number of 1 which may be substituted by a fluorine atom Up to 8 alkoxy group or fluorine atom, Z ⁱ¹ and Z ⁱ² are respectively independent, representing -OCH ₂ -, -CH ₂ O-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, －CH ₂ CH ₂ －, －CF ₂ CF ₂ －, －C≡C－ or a single bond, n ⁱ¹ and n ⁱ² are independent, respectively, and represent 0, 1 or 2, in the presence of plural rings A, B, and Z respectively ^{For i1} and Z ⁱ² , they can be the same or different respectively). The polymerizable compound-containing liquid crystal composition of claim 1, wherein the compound represented by the general formula (i) is a compound represented by the general formula (i-1),

(In the formula, R ⁱ¹¹ , R ⁱ¹² , ring A ⁱ¹ , ring B ⁱ¹ , Z ⁱ¹¹ , Z ⁱ¹² , n ⁱ¹¹ and n ⁱ¹² respectively represent the same as R ⁱ¹ , R ⁱ² , ring A, ring B, Z ⁱ¹ , Z ⁱ² , n ⁱ¹ and n ^{i2 have the} same meaning, n ⁱ¹¹ + n ⁱ¹² represents 1, 2, 3, or 4, and X ⁱ¹¹ to X ⁱ¹⁶ are independent of each other and represent the number of carbon atoms that can be substituted by fluorine atoms 1 To 8 alkyl groups, alkoxy groups with 1 to 8 carbon atoms that may be substituted by fluorine atoms, fluorine atoms or hydrogen atoms). The polymerizable compound-containing liquid crystal composition of claim 1 or 2, which contains one or more polymerizable compounds A represented by the general formula (P) as the polymerizable compound,

(In the above general formula (P), R ^p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group with 1 to 15 carbon atoms or -Sp ^p2 -P ^p2 , one of the alkyl groups or the non-adjacent 2 More than one -CH ₂ -is independent of each other, and can also be substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, one of the alkyl groups may be Two or more hydrogen atoms are independent of each other, and may be substituted by cyano, fluorine or chlorine atoms. P ^p1 and P ^p2 are independent of each other, representing any of the general formula (P ^p1 -1) to formula (P ^p1 -9) One,

(In the formula, R ^p11 and R ^p12 are independent of each other and represent a hydrogen atom, an alkyl group with 1 to 5 carbon atoms, or a halogenated alkyl group with 1 to 5 carbon atoms, and W ^p11 represents a single bond, -O-, -COO- , Alkylene with 1 to 5 carbon atoms, t ^p11 represents 0, 1 or 2, and when there are multiple R ^p11 , R ^p12 , W ^p11 and/or t ^p11 in the molecule, they may be the same or different) , Sp ^p1 and Sp ^p2 are independent of each other, indicating a single bond or spacer, Z ^p1 and Z ^p2 are each independent, indicating 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 -, -CF ₂ O-, -OCF ₂ -, -CF ₂ CH ₂ -, -CH ₂ CF ₂ -, -CF ₂ CF ₂ -Or -C≡C- (where z independently represents an integer from 1 to 4, and R ^ZP1 independently represents a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, when there are multiple R ^{ZP1 in the molecule} , Which can be the same or different; in addition, the * in the formula represents the bonding point ^{with Sp p1} or Sp ^{p2 ), A p1} and A ^p2 are independent of each other, which means that they are selected from the following groups (a ^p ) and group (b ^p ), and the group in the group consisting of the group ^{(c p ), (a p} ) 1,4-cyclohexylene (1 -CH ₂ -existing in the group or more than 2 unadjacent -CH ₂ -may be substituted by -O-), (b ^p ) 1,4-phenylene (1 -CH= or 2 or more not adjacent to each other in the group -CH= may be substituted by -N=) , And (c ^p ) naphthalenediyl, 1,2,3,4-tetrahydronaphthalenediyl, decahydronaphthalenediyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl (exist in One of these bases-CH = or two or more non-adjacent ones-CH = OK Is substituted by -N=), A ^p3 represents a group selected from the group consisting of the aforementioned group (a ^p ), group (b ^p ), group (c ^p ), and single bond, and the aforementioned group (a ^p ), group (B ^p ) and the group (c ^p ) are independent of each other, and the hydrogen atoms present in the group may be replaced by a cyano group, a halogen atom, an alkyl group with 1 to 8 carbon atoms, an alkoxy group with 1 to 8 carbon atoms, Alkenyl with 1 to 8 carbon atoms or -Sp ^p2 -P ^p2 substitution, m ^p1 represents 0, 1, 2 or 3, when there are plural Z ^p1 , A ^p2 , Sp ^p2 and/or P ^p2 in the molecule, They may be the same or different. When m ^p1 is 0 and A ^p1 is a group other than naphthalenediyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl, A ^p3 represents something other than a single bond base). The polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 3, which further contains one or more compounds selected from the compounds represented by the general formula (L):

(In the formula, R ^L1 and R ^L2 are independent of each other and represent an alkyl group with 1 to 8 carbon atoms. One or two or more of the alkyl groups that are not adjacent to each other -CH ₂ -may be independently controlled by -CH= CH－, －C≡C－, －O－, －CO－, －COO－ or －OCO－ replace, n ^L1 means 0, 1, 2 or 3, and A ^L1 , A ^L2 and A ^L3 are independent respectively, which means selection Free radicals in the group consisting of bases (a), bases (b) and bases (c), (a) 1,4-cyclohexylene (1 -CH ₂ -existing in the base or not adjacent 2 or more -CH ₂ -can be substituted by -O-), (b) 1,4-phenylene (1 -CH= or 2 or more non-adjacent ones -CH= can be -N = substitution), and (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (exist One in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl -CH= or two or more not adjacent -CH= can be -N= Substitution), the above group (a), group (b) and group (c) are each independent, and may be substituted by a cyano group, a fluorine atom or a chlorine atom. Z ^L1 and Z ^L2 are each independent, representing 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-, when n ^L1 is 2 or 3 and there are multiple A ^L2s , they can be the same or different, and n ^L1 is 2 or 3 When there are a plurality of Z ^L2s , they may be the same or different; wherein, the compound represented by the general formula (i) is not included). The polymerizable compound-containing liquid crystal composition of any one of claims 1 to 4, which further contains one or two or more compounds selected from the compounds represented by the general formula (N-1),

(In the formula, R ^N11 and R ^N12 are independent of each other and represent an alkyl group with 1 to 8 carbon atoms. One or two or more of the alkyl groups that are not adjacent to each other -CH ₂ -may be independently controlled by -CH= CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO- substituted, A ^N11 and A ^N12 are independent of each other, indicating that they are selected from the following groups (a), (b), and (C) and the group of the group (d), (a) 1,4-cyclohexylene (1 -CH ₂ -existing in the group or 2 or more non-adjacent -CH _2- Can be substituted by -O-), (b) 1,4-phenylene (1 -CH= or 2 or more non-adjacent -CH= can be substituted by -N= in the group), (c ) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (exist in naphthalene-2,6-diyl Or one of the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group -CH= or two or more unadjacent -CH= can be substituted by -N=), and (d)1, 4-cyclohexenylene group, the above-mentioned groups (a), group (b), group (c) and group (d) are independent of each other, and may be substituted by a cyano group, a fluorine atom or a chlorine atom. Z ^N11 and Z ^N12 are respectively Independent, indicating 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-, n ^N11 and n ^N12 are independent and represent an integer from 0 to 3, n ^N11 +n ^N12 is 1, 2 or 3, when there are multiple A ^N11 ～A ^N12 , Z ^N11 ～Z ^N12 , they may be the same or different; Among them, the compound represented by general formula (i) and general formula (L) is not included ). The liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 5, wherein the general formula (i) is selected from compounds of the general formula (i-1-1),

(In the formula, R ⁱ¹¹¹ , R ⁱ¹¹² , ring A ⁱ¹¹ , ring B ⁱ¹¹ , Z ⁱ¹¹¹ and Z ^{i112 respectively represent the same as R i1} , R ⁱ² , ring A, ring B, Z ⁱ¹ and Z in the above general formula (i) ^{i2 has the} same meaning, Y ⁱ¹¹¹ and Y ⁱ¹¹² are independent of each other and represent an alkyl group with 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group with 1 to 8 carbon atoms which may be substituted by a fluorine atom, a fluorine atom or For the hydrogen atom, n ⁱ¹¹¹ and n ⁱ¹¹² are independent and represent 0 or 1). The polymerizable compound-containing liquid crystal composition of any one of claims 1 to 6, which contains one or more types ^{of at least one of R L1} and R ^L2 in the above general formula (L) represents the number of carbon atoms 2 to 8 alkenyl compounds. The liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 7, which further contains one or more polymerizable compounds having one or more polymerizable groups and one or more polar groups in the molecular structure B is the above-mentioned polymerizable compound. The polymerizable compound-containing liquid crystal composition of claim 8, wherein the polymerizable compound B is a group represented by the general formula (AT),

(In the formula, Sp ^AT1 represents a single bond or a linear or branched alkylene group with 1 to 25 carbon atoms. One or more hydrogen atoms in the alkylene group can be replaced by -OH, -CN, -W ^AT1 -Z ^AT1 or P ^AP1 -Sp ^AP1 - substituted, or a contiguous extension of the two or more of the alkyl -CH ₂ - can be oxygen atoms are not directly bonded to the embodiment is a cyclic group, - CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- substitution, 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 straight or branched chain alkylene group with 1 to 25 carbon atoms. One or more hydrogen atoms in the alkylene group can be -OH, -CN, or P ^AP1 -Sp ^AP1 - substituted, or adjacent to one or more of the alkylene group in the 2 -CH ₂ - can not directly adjacent oxygen atoms of the group cyclic manner, -CH = CH－, －C≡C－, －O－, －CO－, －COO－ or －OCO－ substituted, where * means bonding bond), Z ^AT1 means a monovalent polar group containing polar elements, Z ^AT1 One or more of the hydrogen atoms can be substituted by -OH, -CN, or P ^AP1 -Sp ^AP1 -; P ^AP1 represents a polymerizable group, Sp ^AP1 represents a spacer group, and * in the formula represents a bonding bond). A liquid crystal display element using the polymerizable compound-containing liquid crystal composition of any one of claims 1 to 9. A liquid crystal display element for active matrix driving, which uses a polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 9. A liquid crystal display element for PSA mode, PSVA mode, PS-IPS mode, or PS-FFS mode, which uses the polymerizable compound-containing liquid crystal composition of any one of claims 1 to 9.